United States
Environmental Protection
Agency
Office of
Pesticides and Toxic Substances
Washington DC 20460
August 1981
xvEPA Dialifor
(O, O-diethyl S-(2-chloro
1-phthalimidoethyl)
phosphorodithioate)
Pesticide Registration
Standard
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DIALIPOR
Pesticide Registration Standard
Denise Keehner Project Manager (SPRD)
Daniel Byrd • PhD (SPS, BED)
George Beusch Chemist (RGB, BED)
M. Ferretti Chemist (RCBr HED)
Lionel Richardson Environmental Chemist (EFB, HED)
Chad Sandusky lexicologist (TOX, HED)
William Rabert Fish & Wildlife Biologist (EEB, HED)
Robert Hoist Plant Physiologist (EEB, HED)
Mark Dow Entomologist (ASIB, BFSD)
Kate Devine Economist (EAB, BFSD)
June, 1981
Office of Pesticides and Toxic Substances
Environmental Protection Agency
401 M Street, SW
Washington, DC 20460
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TABLE OF CONTENTS
Page
Chapter One
How to Register Under a Registration Standard 1-1
Chapter Two
Agency Position on Dialifor
Regulatory Position for Dialifor 2-1
Criteria for Registration under this Standard
A. Manufacturing-use Dialifor 2-5
1. Acceptable Ranges and Limits
2. Required Labeling
3. Tolerance Reassessment
B. Bnulsifiable Concentrate Dialifor 2-7
1. Acceptable Ranges and Limits
2. Required Labeling
3. Regulatory Rationale
C. Wettable Powder Dialifor 2-11
1. Acceptable Ranges and Limits
2. Required Labeling
3. Regulatory Rationale
Chapter Three
Data Requirements and Data Gaps 3-1
Introduction
A. Manufacturing-use Dialifor 3-1
B. Emulsifiable Concentrate Dialifor 3-4
C. Wettable Powder Dialifor 3-5
Chapter Four
Product Chemistry of Dialifor 4-1
Introduction
A. Manufacturing-use Dialifor 4-2
1. Product Chemistry Profile
2. Topical Discussions
B. Bnulsifiable Concentrate Dialifor 4-6
1. Product Chemistry Profile
2. Topical Discussions
C. Vfettable Powder Dialifor 4-6
1. Product Chemistry Profile
2. Topical Discussions
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Chapter Five
Environmental Fate of Dial if or 5-1
Use Profile
A. Manufacturing-use Dialifor 5-3
1. Environmental Fate Profile
2. Exposure Profiles
3. Topical Discussions
Chapter Six
Toxicology of Dialifor 6-1
A. Manufacturing-use Dialifor 6-2
1. Toxicology Profile
2. Topical Discussions
B. Emulsifiable Concentrate Dialifor 6-15
1. Toxicology Profile
2. Topical Discussions
C. Wettable Powder Dialifor 6-17
1. Toxicology Profile
2. Topical Discussions
Chapter Seven
Residue Chemistry of Dialifor 7-1
A. Manufacturing-use Dialifor 7-1
1. Residue Chemistry Profile
2. Topical Discussions
B. Formulations of Dialifor 7-27
1. Data Requirements for New Uses
2. Required Labeling
Chapter Eight
Ecological Effects of Dialifor 8-1
A. Manufacturing-use Dialifor 8-1
1. Ecological Effects Profile
2. Topical Discussions
B. Emulsifiable Concentrate Dialifor 8-6
1. Ecological Effects Profile
2. Hazard Assessment
3. Topical Discussions
C. Wettable Powder Dialifor 8-6
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Chapter Nine
Case Bibliography
Guide to Use of Bibliography
A. Section I.,
B. Section II.
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HOW TO REGISTER
UNDER A REGISTRATION STANDARD
Organization of the Standard
Purpose of the Standard
Requirement to Re-register Under the Standard
"Product Specific" Data and "Generic" Data
Data Compensation Requirements under FIFRA 3(c) (1) (D)
Obtaining Data to Fill " Data Gaps"; FIFRA 3(c) (2) (B)
Amendments to the Standard
Organization of_ the Standard
This first chapter explains the purpose of a Registration Standard and
summarizes the legal principles involved in registering or re-registering under
a Standard. The second chapter sets forth the requirements that must be met to
obtain or retain registration for products covered by this particular
Registration Standard. In the remaining chapters, the Agency reviews the
available data by scientific discipline, discusses the Agency's concerns with
the identified potential hazards, and logically develops the conditions and
requirements that would reduce those hazards to acceptable levels.
Purpose of the Standard
Section 3 of the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA)
provides that "no person in any State may distribute, sell, offer for sale,
hold for sale, ship, deliver for shipment, or receive (and having so received)
deliver or offer to deliver, to any person any pesticide which is not
registered with the Administrator [of EPA]." To approve the registration of a
pesticide, the Administrator must find, pursuant to Section 3(c) (5) that:
"(A) its composition is such as to warrant the proposed claims for it;
(8) its labeling and other material required to be submitted comply
with the requirements of this Act;
(C) it will perform its intended function witbout unreasonable adverse
effects on the environment; and
(D) when used in accordance with widespread and commonly recognized
practice it will not generally cause unreasonable adverse effects
on the environment."
In making these findings, the Agency reviews a wide range of data which
registrants are required to submit, and assesses the risks and benefits
associated with the use of the proposed pesticide. But the established
approach to making these findings has been found to be defective on two counts:
First, EPA and its predecessor agency, the United States Department of
Agriculture (USDA), routinely reviewed registration applications on a 'product
by product' basis, evaluating each product-specific application somewhat
Independently. In the review of products containing similar components, there
was little opportunity for a retrospective review of the full range of
pertinent data 'available in Agency files and in the public literature. Thus
the 'product by product' approach was often inefficient and sometimes resulted
in inconsistent or incomplete regulatory judgments.
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Second, over the years, as a result of inevitable and continuing advances
in scientific knowledge, methodology, and policy, the data base for many
pesticides came to be considered inadequate by current scientific and
regulatory standard's. Given the long history of pesticide regulation in
several agencies, it is even likely that materials may have been lost from
the data files. When EPA issued new requirements for registration in 1975
(40 CFR 162) and proposed new guidelines for hazard testing in 1978 (43 FR
29686, July 10, 1978 and 43 FR 37336, August 2, 1978), many products that
had already been registered for years were being sold and used without the
same assurances of human and environmental safety as was being required for
new products. Because of this inconsistency, Congress directed EPA to re-
register all previously registered products, so as to bring their
registrations and their data bases into compliance with current requirements
(See FIFRA Section 3(g)).
Facing the enormous job of re-reviewing and calling-in new data for the
approximately 35,000 current registrations, and realizing the inefficiencies of
the 'product by product' approach, the Agency decided that a new, more
effective method of review was needed.
A new review procedure has been developed. Under it, EPA publishesdocuments
called Registration Standards, each of which discusses a particular pesticide
active ingredient. Each Registration Standard summarizes all the data
available to the Agency on a particular active ingredient and its current uses,
and sets forth the Agency's comprehensive position on the conditions and
requirements for registration of all existing and future products which contain
that active ingredient. These conditions and requirements, all of which must
be met to obtain or retain full registration or re-registration under Section
3(c) (5) of FIFRA, include the submission of needed scientific data which the
Agency does not now have, compliance with standards of toxicity, composition,
labeling, and packaging, and satisfaction of the data compensation provisions
of FIFRA Section 3(c) (1) (B).
The Standard will also serve as a tool for product classification. As part
of the registration of a pesticide product, EPA may classify each product for
"general use" or "restricted use" [FIFRA Section 3(d)]. A pesticide is
classified for "restricted use" when some special regulatory restriction is
needed to ensure against unreasonable adverse effects to man or the
environment. Many such risks of unreasonable adverse effects can be lessened
if expressly-designed label precautions are strictly followed. Thus the
special regulatory restriction for a "restricted use" pesticide is usually a
requirement that it be applied only by, or under the supervision of, an
applicator who has been certified by the State or Federal government as being
competent to use pesticide safely, responsibly, and in accordance with label
directions. A restricted-use pesticide can have other regulatory restrictions
[40 CFR 162.11(c) (5)] instead of, or in addition to, the certified applicator
requirement. These other regulatory restrictions may include such actions as
seasonal or regional limitations on use, or a requirement for the monitoring of
residue levels after use. A pesticide classified for "general use," or not
classified at all, is available for use by any individual who is in compliance
with State or local regulations. The Registration Standard review compares
information about potential adverse effects of specific uses of the pesticide
with risk criteria listed In 40 CFR 162.11(c), and thereby determines whether a
product needs to be classified for "restricted use." If the Standard does
classify a pesticide for "restricted use," this determination is stated in the
second chapter.
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Requirement £o Re-register Under the Standard
FIFRA Section 3(g), as amended in 1978, directs EPA to re-register allcurrently
registered products as expeditiously as possible. Congress also agreed that re-
registration should be accomplished by the use of Registration Standards.
Each registrant of a currently registered product to which this Standard
applies, and who wishes to continue to sell or distribute his product in
commerce, must apply for re-registration. His application must contain
proposed labeling that complies with this Standard.
EPA will issue a notice of intent to cancel the registration of any currently
registered product to which this Standard applies if the registrant fails to
comply with the procedures for re-registration set forth in the Guidance
Package which accompanies this Standard.
"Product Specific" Data and "Generic" Data
In the course of developing this Standard, EPA has determined the types of
data needed for evaluation of the properties and effects of products to which
the Standard applies, in the disciplinary areas of Product Chemistry,
Environmental Fate, Toxicology, Residue Chemistry, and Ecological Effects.
These determinations are based primarily on the data Guidelines proposed in
1978 (A3 FR 29696, July 10, 1978, and 43 FR 37336, August 22, 1978), as applied
to the use patterns of the products to which this Standard applies. Where it
appeared that data from a normally applicable Guidelines requirement was
actually unnecessary to evaluate these products, the Standard indicates that
the requirement has been waived. On the other hand, in some cases studies not
required by the Guidelines may be needed because of the particular composition
or use pattern of products the Standard covers; if so, the Standard explains
the Agency's reasoning. Data guidelines have not yet been proposed for the
Residue Chemistry discipline, but the requirements for such data have been in
affect for some time and are, the Agency belives, relatively familiar to
registrants. Data which we have found are needed to evaluate the
registrability of some products covered by the Standard may not be needed for
the evaluation of other products, depending upon the composition, formulation
type, and intended uses of the product in question. The Standard states which
data requirements apply to which product categories. (See the second chapter.)
The various kinds of data normally required for registration of a pesticide
product can be divided into two basic groups:
(A) data that is " product specific ," i.e., data that relates only
to the properties or effects of a product with a particular
composition (or a group of products with closely similar
composition); and
(B) "generic" data that pertains to the properties or effects of a
particular Ingredient, and thus is relevant to an evaluation of
the risks and benefits of all products containing that ingredient
(or all such products having a certain use pattern), regardless of
any such product's unique composition.
The Agency requires certain "product specific" data for each product to
characterize the product's particular composition and physical/chemical
properties (Product Chemistry), and to characterize the product's acute
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toxicity (which is a function of its total composition). The applicant for
registration or re-registration of any product, whether it is a manufactur- ing-
use or end-use product, and without regard to its intended use pattern, must
submit or cite enough of this kind of data to allow EPA to evaluate the
product. For such purposes, "product specific" data on any product other than
the applicant's is irrelevant, unless the other product is closely similar in
composition to the applicant's. (Where it has been found practicable to group
similar products for purposes of evaluating, with a single set of tests, all
products in the group, the Standard so indicates.) "Product specific" data on
the efficacy of particular end-use products is also required where the exact
formulation may affect efficacy and where failure of efficacy could cause
public health problems.
All other data needed to evaluate pesticide products concerns the properties
or effects of a particular ingredient of products (normally a pesticidally
active ingredient, but in some cases a pesticidally inactive, or "inert,"
ingredient). Some data in this "generic" category are required to evaluate the
properties and effects of all products containing that ingredient [e.g., the
acute LD-50 of the active ingredient in its technical or purer grade; see
proposed 40 CFR 163.81-l(a), 43 FR 37355].
Other "generic" data are required to evaluate all products which both
contain a particular ingredient and are intended for certain uses (see, e.g.,
proposed 40 CFR 163.82-1, 43 FR 37363, which requires subchronic oral testing
of the active ingredient with respect to certain use patterns only). Where a
particular data requirement is use-pattern dependent, it will apply to each end-
use product which is to be labeled for that use pattern (except where such end-
use product is formulated from a registered manufacturing-use product
permitting such formulations) and to each manufacturing-use product with
labeling that allows it to be used to make end-use products with that use
pattern. Thus, for example, a subchronic oral dosing study is needed to
evaluate the safety of any manufacturing-use product that legally could be used
to make an end-use, food-crop pesticide. But if an end-use product's label
specified it was for use only in ways that involved no food/feed exposure and
no repeated human exposure, the subchronic oral dosing study would not be
required to evaluate the product's safety; and if a manufacturing-use product's
label states that the product is for use only in making end-use products not
involving food/feed use or repeated human exposure, that subchronic oral study
would not be relevant to the evaluation of the manufacturing-use product either,
If a registrant of a currently registered manufacturing-use or end-use
product wishes to avoid the costs of data compensation [under FIFRA Section
3(c) (1) (D)] or data generation [under Section 3(c) (2) (B)] for "generic"
data that is required only with respect to some use patterns, he may elect to
delete those use patterns from his labeling at the time he re-registers his
product. An applicant for registration of a new product under this Standard
may similarly by request approval for only certain use patterns.
Data Compensation Requirements under FIFRA 3(c) (1) (D)
Under FIFRA Section 3(c) (1) (D), an applicant for registration, re-
registration, or amended registration must offer to pay compensation for
certain existing data the Agency has used in developing the Registration
Standard. The data for which compensation must be offered is all data which is
described by all the following criteria:
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(1) the data were first submitted to EPA (or to its predecessor
agencies, USDA or FDA), on or after January 1, 1970;
(2) the data were submitted to EPA (or USDA or FDA) by some other
applicant or registant in support of an application for an
experimental use permit, an amendment adding a new use to a
registration, or for registration, or to support or maintain in
effect an existing registration.
(3) they are the kind of data which are relevant to the Agency's
decision to register or re-register the applicant's product under
the Registration Standard, taking into account the applicant's
product's composition and intended use pattern(s);
(4) the Agency has found the data to be valid and usable in reaching
regulatory conclusions; and
(5) they are not data for which the applicant has been exempted by
FIFRA Section 3(c) (2) (D) from the duty to offer to pay
compensation. (This exemption applies to the "generic" data con-
cerning the safety of an active ingredient of the applicant's
product, not to "product specific" data. The exemption is
available only to applicants whose product is labeled for end-
uses for which the active ingredient in question is present in the
applicant's product because of his use of another registered
product containing that active ingredient which he purchases from
another producer.)
An applicant for re-registration of an already registered product under this
Standard, or for registration of a new product under this Standard, accordingly
must determine which of the data used by EPA in developing the Standard must be
the subject of an offer to pay compensation, and must submit with his
application the appropriate statements evidencing his compliance with FIFRA
Section 3(c) (1) (D).
An applicant would never be required to offer to pay for "product specific"
data submitted by another firm. In many, if not in most cases, data which is
specific to another firm's product will not suffice to allow EPA to evaluate
the applicant's product, that is, will not be useful to the Agency in
determining whether the applicant's product is registrable. There may be
cases, however, where because of close similarities between the composition of
two or more products, another firm's data may suffice to altow EPA to evaluate
so-ie or all of the "product specific" aspects of the applicant's product. In
such a case, the applicant may choose to cite that data instead of submitting
data from tests on his own product, and if he chooses that option, he would
have to comply with the offer-to-pay requirements of Section 3(C) (1) (D) for
that data.
Each applicant for registration or re-registration of a manufacturing-use
product, and each applicant for registration or re-registration of an end-use
product, who is not exempted by FIFRA Section 3(c) (2) (D), must comply with
the Section 3(c) (1) (D) requirements with respect to each item of "generic"
data that relates to his product's intended uses.
A detailed description of the procedures an applicant must follow in
applying for rerregistration (or new registration) under this Standard is found
in the Guidance Package for this Standard.
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Obtaining Data t£ Fill "Data Gaps"; FIFRA 3(c) (2) (B)
Some of the kinds of data EPA needs for its evaluation of the properties and
effects of products to which this Standard applies have never been submitted to
the Agency (or, if submitted, have been found to have deficiencies rendering
them inadequate fo'r making registrability decisions) and have not been located
in the published literature search that EPA conducted as part of preparing this
Standard. Such instances of missing but required data are referred to in the
Standard as "data gaps".
FIFRA Section 3(c) (2) (B), added to FIFRA by the Congress in 1978, authorizes
EPA to require registrants to whom a data requirement applies to generate (or
otherwise produce) data to fill such "gaps" and submit those data to EPA. EPA
must allow a reasonably sufficient period for this to be accomplished. If a
registrant fails to take appropriate and timely steps to fill the data gaps
identified by a section 3(c) (2) (B) order, his product's registration may be
suspended until the data is submitted. A mechanism is provided whereby two or
more registrants may agree to share in the costs of producing data for which
they are both responsible.
The Standard lists, in its summary second chapter, the "generic" data gaps
and notes the classes of products to which these data gaps pertain. The
Standard also points out that to be registrable under the Standard, a product
must be supported by certain required "product specific" data. In some cases,
the Agency may posses sufficient "product specific" data on one currently
registered product, but may lack such data on another. Only those Standards
which apply to a very small number of currently registered products will
attempt to state definitively the " product specific" data gaps on a 'product
by product' basis. (Although the Standard will in some cases note which data
that EPA does possess would suffice to satisfy certain "product specific" data
requirements for a category of products with closely similar composition
characteristics.)
As part of the process of re-registering currently registered products, EPA
will issue Section 3(c) (2) (B) directives requiring the registrants to take
appropriate steps to fill all identified data gaps — whether the data in
question is "product specific" or "generic" — in accordance with a schedule.
Persons who wish to obtain registrations for new products under this Standard
will be required to submit (or cite) sufficient "product specific" data before
their applications are approved. Upon registration, they will be required
under Section 3(c) (2) (B) to take appropriate steps to submit data needed to
fill "generic" data gaps. (We expect they will respond to this requirement by
entering into cost-sharing agreements with other registrants who previously
have been told they must furnish the data.) The Guidance Package for this
Standard details the steps that must be taken by registrants to comply with
Section 3(c) (2) (B).
Amendments to the Standard
Applications for registration which propose uses or formulations that are not
presently covered by the Standard, or which present product compositions,
product chemistry data, hazard data, toxicity levels, or labeling that do not
meet the requirements of the Standard, will automatically be considered by the
Agency to be requests for amendments to the Standard. In response to such
applications, the Agency may request additional data to support the proposed
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amendment to the Standard, or may deny the application for registration on the
grounds that the proposed product would cause unreasonable adverse effects to
the environment. In the former case, when additional data have been
satisfactorily supplied, and providing that the data do not indicate the
potential for unreasonable adverse effects, the Agency will then amend the
Standard to cover the new registration.Each Registration Standard is based upon
all data and Information available to the Agency's reviewers on a particular
date prior to the publication date. This "cut-off" date is stated at the
beginning of the second chapter. Any subsequent data submissions and any
approved amendments will be incorporated into the Registration Standard by
means of addenda,- which are available for inspection at EPA in Washington,
D.C., or copies of which may be requested from the Agency. When all the
present "data gaps" have been filled and the submitted data have been reviewed,
the Agency will revise the Registration Standard. Thereafter, when the Agency
determines that the internally maintained addenda have significantly altered
the conditions for registration under the Standard, the document will be
updated and re-issued for publication.
While the Registration Standard discusses only the uses and hazards of products
containing the designated active ingredient(s), the Agency is also concerned
with the potential hazards of some inert ingredients and impurities.
Independent of the development of any one Standard, the Agency has initiated
the evaluation of some inert pesticide ingredients. Where the Agency has
indentified inert ingredients of concern in a specific product to which the
Standard applies, these ingredients will be pointed out in the Guidance Package.
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CHAPTER II
AGENCY POSITION ON DIALIPOR
Introduction
This chapter describes in detail the Agency's regulatory position on products
which contain dialifor as the sole active ingredient. The regulatory position
adopted by the Agency incorporates a number of considerations. Foremost among
these considerations is an analysis of the registrability of products
containing dialifor based on the risk criteria found in Section 162.11(a) of
Title 40 of the U.S. Code of Federal Regulations. The Agenc;/ s determination
is presented below, and the rationale for this basic decision follows the
position.
In addition to this decision, standards of product composition, acute toxicity,
and use are established. The rationale for establishing a particular standard
follows the presentation of the standard. Regulatory actions such as
establishing farmworker safety (reentry) intervals are prescribed, and
additional data are requested. The basis for any regulatory action can be
found by first reading the rationale for the action, which follows the chosen
regulatory option. Further information, on the scientific basis for an action,
can be found by reading the various disciplinary chapters which present
summaries of available scientific data on the safety of dialifor.
In general, the basis for establishing a data requirement can be found in the
topical discussion portion of a disciplinary chapter. References to Agency
guidelines for testing are provided when appropriate.
Description of Chemical
Dialifor is an insecticide used for the control of a variety of mites, spiders
and scales on grapes, pecans, citrus and apples. Dialifor is the common name
for O,O-Diethyl S-(2-chloro-l-phthalimidoethyl) phosphorodithioate. There is
only one currently registered manufacturing-use product.
Dialifor end-use products are marketed under the trade name TorakS' These
products are available in emulsifiable concentrate and wettable powder
formulations.
Regulatory Position for Products Containing Dialifor
Dialifor (O,O-Diethyl S-(2-chloro-l-phthalimidoethyl) phosphorodithioate) as
described in this standard may be registered for sale, distribution,
reformulation, and use in the United States. Considering all information
available to the Agency from the open literature and provided to the Agency by
registrants, as of October 5, 1980, the Agency finds that none of the risk
criteria found- in Section 162.11(a) of Title 40 of the U.S. Code of Federal
Regulations were met or exceeded for pesticide products containing dialifor.
Available data indicate that the use of dialifor will not result in
unreasonable adverse effects to man or his environment. Gaps in the data
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base preclude the completion of the Agency's risk assessment. Currently
registered dialifor products may be reregistered subject to the conditions
imposed. New products may be registered under this Standard and are subject to
the same requirements.
Regulatory Rationale for Dialifor
Dialifor is a phthalophosphate insecticide used for the control of a variety of
spiders, mites, and scales on citrus, grapes and pecans. Because of the
phthalimido radical in the structure of dialifor, the Agency is concerned about
potential teratogenic effects. Thalidomide, responsible for the world-wide
increase in the incidence of phocomelia (a shortening or complete absence of
the limbs) in the early 1960's, also contained the phthalimido radical.
Dialifor's chemical similarity to Thalidomide is discussed in more detail in
the Toxicology chapter of this Standard.
The Agency screened three unaudited teratogenicity studies on dialifor
completed by Industrial Biotest Laboratories (IBT), and reviewed one study,
identified in the open literature, completed by Jane Robens. None of these
studies report significant teratogenic or fetotoxic effects. While no
definitive conclusions can be reached on the teratogenic and fetotoxic
properties of dialifor, two of the IBT studies and the Robens study do suggest
that dialifor may cause teratogenic and fetotoxic effects.
Additional testing on the potential teratogenicity of dialifor is required.
The species selected for testing is of special concern, because the teratogenic
effects of Thalidomide are more reliably reproduced in rabbits. Because
dialifor is structurally similar to Thalidomide, there is a good possibility
that the mode of action may be similar, and that testing in rabbits would
provide more accurate information.
Dialifor, like many organophosphate insecticides, causes acetyl cholinesterase
depression. The potential hazards to farmworkers posed by dialifor residues in
the agricultural workplace have been the subject of considerable concern over
the past decade in the State of California. Concern focused on the existence
of the potentially more potent cholinesterase inhibitor dialifor-oxon as a
residue in California vineyards, two field worker poisoning incidents
(considered to be siginificant by State authorities) and reports of its
ineffectiveness as a pesticide.
This concern culminated in the imposition of a 75-day reentry period in
California, for the use of dialifor on grapes, by the Department of Food and
Agriculture for the State of California. In addition, this Department
requested the completion of a reentry study on humans by the manufacturer.
Available data indicate that such a study was never completed. Communication
with the California Department of Food and Agriculture indicated that the
registrant subsequently submitted a voluntary cancellation for this use pattern
in California.
The Department of Food and Agriculture for the State of California was also
concerned about residue levels in treated commodities at the time of harvest.
This Department expressed some concern that residue levels, although within
Federal tolerance limits, were too high given the toxicity of dialifor and
d ialifor-oxon.
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Valid safety data available to the Agency is scarce, and the Agency is unable
to set a No Observed Effect Level (NOEL) for red blood cell and plasma
cholinesterase depression for dialifor or for dialifor-oxon. This precludes
the completion of a formal risk assessment. However, the Agency does recognize
that dialifor is-a cholinesterase inhibitor, and that sane regulatory action is
warranted based on the existence of reports of accidents involving fieldworkers
exposed to weathered residues of dialifor.
The first poisoning incident (1973 in Fowler, California) involved 32 pickers
who harvested grapes 42 days after application of dialifor. Workers were
exposed to residues of both dialifor and phosalone (another organophosphate
insecticide). The second poisoning incident, (September of 1976 in Madera,
California) involved 118 grape pickers exposed to residues of dialifor and
phosalone. Available information on this incident indicates that reentry
occurred approximately 15 days following application of dialifor.
Data summarized in the Environmental Fate and Residue Chemistry Chapters
indicate that the oxygen analog of dialifor is formed by photolysis, and that
this metabolite may be present in quantities up to 12.5% of weathered residues
on crops (see Residue Chemistry Chapter). Data are not available to quantify
the exact amount of dialifor-oxon residues present over time, or to establish
the persistence of this metabolite, or dialifor itself, in the field. It is
highly likely that the characteristically hot, arid climate of California
increases the persistence of this oxon. The possibility of several
toxicologically significant chemicals in the weathered residue greatly
complicates an analysis of the relationship between application rate, remainir.c
residues, and dose and response.
The foliar residues of dialifor and its oxygen analog are suspected of playing
the principal role in farmworker exposure. These residues are dislodged by th
activity of the workers, become airborne, and "fall out" over the surface of
the worker's clothing and exposed skin. The amount of available foliar residu
is influenced by chemical characteristics, crop type, and weather conditions
following application.
A reentry study completed in 1980 involving the use of dialifor on grapes
supports a farmworker safety interval of at least 65 days for this use in the
State of California. The official reentry interval for this use in-California
is 75 days.
Section 3(c)8 of the Federal Insecticide, Fungicide and Rodenticide Act (FIFRA;
directs the Agency not to initiate a Rebuttable Presumption Against
Registration action unless the action is based on a validated test or other
significant evidence raising prudent concerns of unreasonable adverse effects
to man or the environment. Available data do not indicate that the use of
dialifor will result in unreasonable adverse effects. However, numerous gaps
in the data base preclude the completion of quantitative risk assessments.
In the interim, pending receipt of data to complete the risk assessment, the
Agency has decided to adopt the 75-day reentry interval imposed by the
Department of Food and Agriculture for the State of California for the use of
dialifor on grapes, as a federally accepted farmworker safety interval for this
use pattern. Data, to establish safe reentry intervals for other registered
crops, are being requested.
2-3
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Data to determine acceptable reentry intervals for the use of dialifor on
citrus, pecans, and apples do not exist, and available reentry data on grapes
cannot be extrapolated to other use patterns.
Preharvest intervals have been reviewed and have been found to be adequate to
insure residue levels in raw agricultural commodities below tolerance limits at
harvest. A full battery of acute, subchronic, and chronic toxicity testing is
requested on dialifor, as well as acute oral and acute dermal toxicity testing
of dialifor-oxon. These toxicology data, when submitted, will be used to
reassess current tolerance limits.
If dialifor-oxon is found to be significantly more toxic than dialifor, an
analytical method (of appropriate sensitivity as determined from toxicity data)
and a full compliment of crop residue data specific to the oxon will be
required.
Data available to the Agency indicate that dialifor is applied to less than 1%
of registered crops. The Agency is, however, very concerned about potential
hazards to the general population (through ingestion of dialifor treated
crops), to applicators (through spray application of liquid formulations), and
to farmworkers (through harvesting of dialifor treated crops) exposed to this
pesticide. Available data suggest a high acute toxicity and a potential for
inducing teratogenic effects.
Because of these and other toxicological considerations, the Agency is
requiring a full battery of acute, subchronic, and chronic testing, as well as
data on fish and wildlife effects and fate of this pesticide in the environment.
Criteria for Registration Under this Standard
To be subject to this Standard, dialifor products must:
1. contain dialifor as the sole active ingredient;
2. be within acceptable standards of composition;
3. be within acceptable acute toxicity limits;
4. be labeled for acceptable end-uses; and
5. bear required labeling.
Manufacturing-use dialifor products must bear label directions for formulation
into acceptable end-uses.
Applicants for registration or reregistration of dialifor products under this
Standard must comply with all terms and conditions described in the following
sections, including commitment to fill data gaps on a time schedule specified
by the Agency and when applicable offer to pay compensation to the extent
required by 3(c)(l)(D) and 3(c)(2)(D) of the Federal Insecticide, Fungicide and
Rodenticide Act (FIFRA), as amended, 7 U.S.C. 136(c)(l)(D) and 136(c)(2)(D).
As discussed in Chapter I, applicants for the registration of dialifor products
under this Standard must contact the Agency for specific instructions,
including updated information on data requirements and companies whose data
must be cited and to whan compensation must be offered.
2-4
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A. Manufacturing-use Dialifor
1. Acceptable Ranges and Limits
a. Product Composition Standards
The only currently registered manufacturing-use dialifor product contains 90%
dialifor. To be covered under this Standard, manufacturing-use dialifor
products must contain dialifor as the sole active ingredient. Any percentage
of active ingredient is acceptable with appropriate certification of limits.
The Agency has determined that information on the physical/chemical properties
of technical grade dialifor cannot be used to fulfill product chemistry
requirements for the currently registered manufacturing-use product. Data are
required on the physical/chemical properties of both technical grade dialifor
and the currently registered manufacturing-use product.
b. Acute Toxicity Limits
The Agency will consider registration of manufacturing-use dialifor products
which have established acute toxicity category I-IV ratings for each of the
following effects:
Acute Oral Toxicity
Acute Dermal Toxicity
Acute Inhalation Toxicity
Primary Eye Irritation
Primary Dermal Irritation
c. Use Patterns
To be covered under this Standard, manufacturing-use dialifor products must be
labeled for formulation into end-use pesticides which are intended for outdoor
nondomestic terrestrial applications (food or non food uses).
Dialifor is currently registered for use only in agricultural applications.
Tolerances have been established for dialifor use on grapes, citrus, apples and
pecans. Tolerances have also been established for residues of dialifor in meat
(red), milk, poultry, and eggs.
The Agency will consider additional tolerances on food or feed crops provided
that applicants for the registration of the additional crop(s) submit a
petition(s) proposing a tolerance level for each crop, supply appropriate
residue data, and demonstrate that the addition of the tolerance will not
result in an unacceptable risk to the general population. Applicants must also
demonstrate that the additional food-use pattern(s) will not result in an
unacceptable risk to applicators or to fieldworkers.
The Agency will also consider non-food (non domestic) terrestrial outdoor uses
of dialifor provided any additional required data are submitted for the
registration of the use and provided the use pattern will not result in an
unacceptable risk to applicators.
Dialifor cannot be registered for (general) domestic use under this standard
because of potent cholinesterase inhibiting properties, and high dermal
toxicity (Category II) of currently registered end-use products. The
2-5
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application of dialifor involves the mixing and spraying of liquid formulation
upwards onto the foliaqe of apples, citrus, grapes, and pecans. Application is
made, in some cases, until the crop is soaked and dripping with dialifor. Hie
homeowner-applicator cannot be reasonably expected to exert the effort needed
to eliminate the possibility of exposure to potentially toxic quantities of
dialifor by the dermal route as a result of application.
2. Required Labeling
All manufacturing-use dialifor products must bear appropriate labeling as
specified in 40 CFR 162.10.
3. Tolerance Reassessment
Tolerances have been established for combined residues of dialifor and its
oxygen analog in or on raw agricultural commodities as indicated: 1.5 ppm in or
on apples, 3 ppm in or on citrus fruits, 1 ppm in or on grapes, .01 ppm in or
on pecans, .15 ppm in meat, fat, and meat byproducts of cattle, goats and
sheep, .15 ppm in milk fat, .05 ppm in meat, fat, and meat byproducts of
poultry, and .01 ppm in eggs (40 CFR 180.326).
The theoretical maximum residue contribution (TMRC) of dialifor to the human
diet is calculated to be .265 mg/day. This figure is based on average adult
eating patterns and on the assumption that each commodity contains residues
which meet the established tolerance level.
The Agency is unable to set a No Observed Effect Level (NOEL) for dialifor or
for dialifor-oxon. Thus, tolerance levels cannot be reassessed at this time.
2-6
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B. Emulsifiable Concentrate Dialifor
1. Acceptable Ranges and Limits
a. Product Composition Standards
Currently registered dialifor emulsifiable concentrate products include three
products containing 4 pounds per gallon of dialifor. The Agency has determined
that existing emulsifiable concentrate products are substantially similar.
Emulsifiable concentrate dialifor products containing up to 50% active
ingredient are acceptable (with appropriate certification of limits), as long
as application rates (on a per acre basis) remain the same.
The Agency has placed this upper limit on the percentage of active ingredient
because available acute dermal toxicity testing of the manufacturing-use
product (containing 90% active ingredient) suggests high toxicity. Available
acute dermal toxicity testing of the 50% wettable powder product indicates that
this product falls into Category II which is acceptable for general, non
domestic use.
Inert ingredients in food-use formulations must be cleared for such use under
40 CFR 180.1001.
b. Acute Toxicity Limits
To be registered for nondomestic use under this Standard, an emulsifiable
concentrate dialifor product must have an (a):
Acute Oral Toxicity of Category I-IV;
Acute Dermal Toxicity of Category II-IV;
Acute Inhalation Toxicity of Category I-IV;
Primary Eye Irritation of Category II-IV; and
Primary Dermal Irritation of Category II-IV.
Rationale: Emulsifiable Concentrate products with acute oral LD50 values in
Category I are acceptable for general use under this Standard. The Agency has-
determined that appropriate label warnings (against consumption of-food and
smoking during application and prior to the washing of hands and face following
application) will significantly decrease the possibility of ingesting fatal
quantities of dialifor. In addition, under normal use conditions, it is
unlikely that applicators will be orally exposed to fatal quantities of
dialifor.
Emulsifiable Concentrate products with acute inhalation LC50 values in Category
I are also acceptable for general use under this Standard. The Agency has
determined that labeling (in accordance with 40 CFR 162.10) and formulation
type (liquid) can be reasonably expected to eliminate the possibility of the
inhalation of fatal quantities of dialifor.
c. Use Patterns and Application Methods
To be registered under this Standard, emulsifiable concentrate products of
dialifor may only be used nondomestically, as insecticide-acaricides on apples,
citrus, grapes and pecans.
2-7
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Reentry Intervals
The Agency has accepted the California State reentry interval of 75 days (the
longest existing State reentry interval) for the use of emulsifiable
concentrate dialifor products on grapes when applied at an application rate of
1 pound dialifor (or less) per acre. This is an interim measure, pending the
completion and implementation of Agency reentry guidelines. A reassessment of
this interval may become necessary following the completion of the Agency's
reentry guidelines.
Registrants of emulsifiable concentrate dialifor products have the option of
accepting the California reentry interval of 75 days for the use of dialifor on
grapes, or of petitioning for relief based upon local exposure and residue data.
Federally recommended reentry intervals for the use of dialifor on apples,
citrus, and pecans cannot be established at this time due to extensive gaps in
the data base, and the inability to extrapolate data on grapes to other crops.
Data to establish safe reentry intervals for these other crops are required.
Reentry intervals may need to be reassessed following the completion of Agency
reentry guidelines.
Preharvest Intervals
Preharvest intervals for the use of dialifor on apples, grapes, citrus,
raisins, and pecans remain in effect. These intervals have been reassessed and
appear to be adequate to insure residue levels in raw agricultural commodities
below tolerance limits at harvest. The currently recommended preharvest
intervals are as follows:
Crop Preharvest Interval
Citrus 7 days
Grapes 35 days*
Apples 60 days
Raisins 70 days
* NOTE: Although the current preharvest interval for the use of dialifor on
grapes is sufficient to insure residue levels below tolerance limits at
harvest, because of worker safety concerns, reentry into treated fields
is prohibited within 75 days of application. Registrants have the
option of accepting this restriction or of petitioning for relief based
upon local exposure and residue data.
Application Rates
The Agency finds that it must limit application rates to current levels. This
is an interim measure which may need to be reassessed following the receipt of
required data to complete the Agency's risk assessment. Available residue data
indicate that application rates cannot exceed: 1.0 pound per acre on grapes,
2.0 pounds per acre on pecans, 2.25 pounds per acre on apples, and 5.0 pounds
per acre on citrus, at current preharvest intervals.
2-8
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Most applicators are certified or work under the supervision of certified
applicators. However, the use of dialifor is not restricted to certified
applicators or to supervision by certified applicators at this time.
Additional Uses
The addition of similar crops, ie. within the same crop groupings, as
registered uses would be considered under this standard provided petitions
proposing tolerances, required residue data, safety data, use information, and
reentry studies are submitted and found to be acceptable.
Group Commodities therein
Citrus fruits Citrus citron, grapefruit, kumquats, lemons, limes,
oranges, tangelos, tangerines, and hybrids of these.
Small fruits Blackberries, blueberries, boysenberries,
cranberries, currants, dewberries, elderberries,
gooseberries, grapes, hickleberries, loganberries,
strawberries, youngberries, and rasberries.
Pome fruits Apples, crabapples, pears, and quinces.
Nuts Almonds, Brazil nuts, bush nuts, butternuts,
cashews, chestnuts, filberts, hazelnuts, hickory
nuts, macadamia nuts, pecans, and walnuts.
Emulsifiable concentrate dialifor cannot be registered for (general) domestic
use under this standard because of potent cholinesterase inhibiting properties
and acute dermal toxicity in Category II (see Toxicology Chapter). The
application of dialifor involves the mixing and spraying of a liquid
formulation upwards onto the foliage of apples, grapes, citrus, and pecans.
Application is made, in some cases, until the crop is soaked and dripping with
dialifor. The homeowner-applicator cannot be expected to exert the effort
needed to eliminate the possibility of exposure to potentially toxic quantities
of dialifor during application.
2. Required Labeling
All emulsifiable concentrate dialifor products must bear appropriate labeling
as specified in 40 CFR 162.10.
Reentry
All emulsifiable concentrate dialifor products intended for application on
grapes must include the following precaution:
"Reentry into treated fields is prohibited within 75 days of application."
All labels and labeling intended for agricultural use products must bear the
following statement: "This product must be applied in accordance with 40 CFR
Part 170." Registrants may state the contents of 40 CFR Part 170 or additional
statements.
2-9
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Additional Restrictions and Precautionary Statements
In addition, emulsifiable concentrate products must bear the following
restriction:
"Not for use or storage in or around the home"
All labels and labeling for emulsifiable concentrate products must bear the
following (or equivalent) statements:
"Do not eat or smoke during exposure. Wash hands and face
before eating or smoking"
All labels and labeling for emulsifiable concentrate products must bear the
following statement:
"Do not apply directly to water"
2-10
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C. Wettable Powder Dialifor
1. Acceptable Ranges and Limits
a. Product Composition Standards
The currently registered dialifor wettable powder product contains 50% dialifor
as the active ingredient. Wettable powder dialifor products containing up to
50% active ingredient are acceptable (with appropriate certification of
limits), as long as application rates (on a per acre basis) remain the same.
The Agency has placed this upper limit on the percentage of active ingredient
because available acute dermal toxicity testing of the manufacturing-use
product suggests that this product (containing 90% active ingredient) is very
toxic. Acute dermal toxicity testing of the currently registered wettable
powder product places this product in Category II, which is acceptable for
general, non domestic use.
Inert ingredients in food-use formulations must be cleared for such use under
40 CFR 180.1001.
b. Acute Toxicity Limits
To be registered for nondomestic use under this Standard, a wettable powder
dialifor product must have an (a):
Acute Oral Toxicity of Category I-IV;
Acute Dermal Toxicity of Category II-IV;
Acute Inhalation Toxicity of Category I-IV;
Primary Eye Irritation of Category I-IV; and
Primary Dermal Irritation of Category I-IV.
Rationale: Wettable Powder products with acute oral LD50 values in Category I
are acceptable for general use under this Standard. The Agency has determined
that appropriate label warnings (i.e. against the consumption of food and
smoking during during application and prior to the washing of hands and face
following application) will significantly decrease the possibility of ingestion
of fatal quantities of dialifor. In addition, under use conditions', it is
unlikely that applicators will be orally exposed to fatal quantities of
dialifor.
Wettable Powder products with acute inhalation toxicity values in Category I
are also acceptable for general use under this Standard. The Agency has
determined that labeling (in accordance with 40 CFR 162.10) and formulation
type (liquid) can reasonably be expected to eliminate the possibility of
exposure to fatal quantities of dialifor.
c. Use Patterns and Application Methods
To be registered under this Standard, wettable powder products of dialifor may
only be used nondomestically, as insecticide-acaracides on apples.
Wettable powder dialifor is currently registered for use on apples.
2-11
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Reentry Intervals
Federally accepted reentry intervals for the use of wettable powder dialifor on
apples cannot be established at this time due to extensive gaps in the data
base. Reentry data on the use of dialifor on grapes cannot be extrapolated to
other use patterns.
Preharvest Intervals
The current preharvest interval of 60 days for the use of wettable powder
dialifor on apples remains in effect.
Application Rates
The Agency finds that it must limit application rates to current levels. This
is an interim measure which may need to be reassessed following the submission
of required data to complete the risk assessment. Available residue data
indicate that the application rate cannot exceed 2.25 pounds per acre on apples.
Additional Uses
The addition of grapes, citrus, and pecans (and other crops within the same
crop groupings, see page 2-9), as registered use patterns for wettable powder
dialifor products would be considered under this Standard provided petitions
proposing tolerances, required residue chemistry data, safety data, use
information, and reentry studies are submitted, and found to be acceptable.
Because the amount of available dislodgeable residues is influenced by
formulation type, the reentry interval for the use of emulsifiable concentrate
dialifor on grapes is not directly applicable to wettable powder formulations.
Additional data are required.
Wettable powder dialifor cannot be registered for (general) domestic use under
this Standard because of cholinesterase inhibiting properties, and acute dermal
toxicity in Category II (see Toxicology Chapter). The application of dialifor
involves the mixing and spraying of a liquid formulation upwards onto the
foliage of grapes, apples, citrus, and pecans. Application is made, in some
cases, until the crop is soaked and dripping with dialifor. The homeowner-
applicator cannot be expected to exert the effort needed to eliminate the
possibility of accidental exposure to potentially toxic quantities of dialifor
during application.
2. Required Labeling
All wettable powder dialifor products must bear appropriate labeling as
specified in 40 CFR 162.10.
Reentry
All labels and labeling intended for agricultural use products must bear the
following statement: "This product must be applied in accordance with 40 CFR
Part 170". Registrants may state the contents of 40 CFR Part 170 or additional
statements.
2-12
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All labels and labeling for wettable powder products must bear the following
(or equivalent) statements:
"Do not eat or smoke during exposure. Wash hands and face before
eating or smoking"
"Do not apply directly to water"
In addition, wettable powder products must bear the following restriction:
"Not for use or storage in or around the home"
2-13
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CHAPTER III
DATA REQUIREMENTS AND DATA GAPS
A. Manufacturing-use Dialifor
The majority of chronic, subchronic, and acute toxicity data on manufacturing-
use dialifor were generated by Industrial Biotest Laboratories (IBT). These
studies are currently under review in the E.P.A. Laboratory Audit Program.
The Agency's policy in the Registration Standards Program is to review IBT
studies for indications of adverse effects resulting from administration of the
test substance. Any identified adverse effect data are then discussed in the
Standard.
If adverse effects are not identified during the Registration Standard review,
these studies are considered invalid for registration purposes. Their status
as invalid will continue until they have been validated by registrants and the
Agency through the Laboratory Audit Program.
A number of studies have not completed the validation process through the
Laboratory Audit Program. Thus, some company submitted toxicology data have
been declared invalid for registration purposes. These categories of data are
identified in the Standard as data gaps.
Table A, entitled: GENERIC DATA REQUIREMENTS AND DATA GAPS FOR MANIFACTURING-
USE DIALIFOR PRODUCTS includes those data that pertain to the properties or
effects of dialifor as an active ingredient. Thus, these data are relevant to
an evaluation of the risks and benefits of all products containing dialifor.
Providing data to fill indicated data gaps is the primary responsibility of the
manufacturing-use product registrant(s). Registrants of end-use products which
are not exempted by FIFRA Section 3(c)(2)(D) are also responsible for the
submission of these data. Applicants for the registration or reregistration of
manufacturing-use dialifor products must acknowledge reliance on existing data
which fill indicated data requirements under FIFRA 3(c)(l)(D). These data are
listed under the column entitled: Bibliographic Citation in this table.
Product Chemistry Data
Certain data on the physical/chemical properties of technical grade dialifor
are required for the registration of any manufacturing-use product.
Toxicology Data
For purposes of acute oral and dermal toxicity testing, technical grade
dialifor has been determined to be equivalent to the currently registered
Manufacturing-use product.
3-1
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Acute oral and dermal toxicity testing of the oxygen-analog of dialifor is
required because data indicate that this degradation product may be present in
significant amounts in weathered residues in food and in the field. The Agency
must be able to quantify the toxicity of this oxon.
Residue Chemistry Data
A petition proposing a tolerance of 110 ppm in citrus oil is needed.
Pending the receipt of data on the toxicity of dialifor-oxon, a full compliment
of residue data (including an analytical method of appropriate sensitivity) on
the oxygen analog may be required.
3-2
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Table Br entitled: PRODUCT SPECIFIC DATA REQUIREMENTS AND DATA GAPS FOR
MANDFACTRING-USE DIALIFOR PRODUCTS includes those data that relate only to the
properties or effects of a product with a specific composition. Thus, these
data are required of each product to characterize the product's particular
composition and physical/chemical properties, and to characterize the product's
acute toxicity. Providing data to fulfill these data requirements for a
particular product is the responsibility of each applicant for the registration
or reregistration of a manufacturing-use dial if or product. If the Agency has
in its possession product specific data which fulfill a data requirement for a
particular product, this is indicated in the guidance package accompanying this
Standard.
Applicants for the registration of new manufacturing-use dialifor products must
submit all required product specific data or establish that the proposed
product is substantially similar to another product for which the Agency has
received acceptable product specific data.
If the Agency has determined that one or more existing manufacturing-use
dialifor products are substantially similar, then this too is indicated.
Product specific data need not be acknowledged under FIFRA 3(c)(l)(D) unless
the Agency or a registrant has established that a product is substantially
similar to another product for which the Agency has received acceptable product
specific data. If this should occur, the registrant(s) of the former
product(s) is required to acknowledge reliance on these data.
Product Chemistry Data
Data requirements 163.61-3 through 163.61-7 (product composition data) apply to
each proposed or currently registered manufacturing-use product.
Data requirements 163.61-8(7) through 163.61-8(18) (physical/chemical
properties data) apply to manufacturing-use products which are not the same as
the technical grade of the active ingredient. These data are required on
manufacturing-use dialifor.
Toxicology Data
Data requirements 163.81-1 and 163.81-2 (acute oral and dermal toxicity) apply
to manufacturing-use products which are not toxicologically equivalent to the
technical grade of the active ingredient. Technical grade dialifor has been
determined to be equivalent to the currently registered manufacturing-use
product.
Data requirements 163.81-3 through 163.81-6 apply to each manufacturing-use
product or substantially similar product.
3-3
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B. Emulsifiable Concentrate Dialifor
The Agency has determined that existing emulsifiable concentrate dialifor
products are substantially similar.
Registrants of end-use emulsifiable concentrate dialifor products not exempted
by FIFRA Section 3(c)(2)(D) are responsible for the submission of "generic"
data described in Table A in section III. A of this chapter, in addition to the
product specific data listed in Table C.
Registrants of all end-use emulsifiable concentrate products are advised that
if data are not generated to fill generic data requirements for the
^annfacturing-use product(s), these registrations will be suspended. If
continued availability of the manufacturing-use product is desired, these data
must be supplied.
Table C, entitled: PRODUCT SPECIFIC DATA REQUIREMENTS AND DATA GAPS FOR
EMULSIFIABLE CONCENTRATE PRODUCTS includes those data that relate only to the
properties or effects of an emulsifiable concentrate product with a specific
composition. Thus, these data are required of each emulsifiable concentrate
dialifor end-use product to characterize the product's particular composition,
physical/chemical properties, and acute toxicity. Providing data to fulfill
these data requirements is the responsibility of each applicant for the
registration or reregistration of an emulsifiable concentrate dialifor product.
Applicants for the registration of new emulsifiable concentrate dialifor
products must submit all required product specific data or establish that the
proposed product is substantially similar to another product for which the
Agency has received acceptable product specific data.
If the Agency has received acceptable product chemistry and/or acute toxicity
data for any existing emulsifiable concentrate dialifor product(s), this is
indicated in Table C, and the specific product(s) is identified in the guidance
package accompanying this Standard. In addition, in the column entitled:
Bibliographic Citation , the Identification Numbers of the acceptable studies
are provided. These acceptable data are also summarized in the Topical
Discussion sections of this Standard. If the Agency has established that a
particular product is substantially similar to another product for which the
Agency has received acceptable product chemistry and/or acute toxicity data,
then this too is indicated.
Product specific data need not be acknowledged under FIFRA Section 3(c)(l)(D)
unless the Agency or a registrant has established that a product is
substantially similar to another product for which the Agency has received
acceptable product specific data. If this should occur, the registrant(s) of
the former product(s) is required to acknowledge reliance on these data.
3-4
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C. Wettable Powder Dialifor
Registrants of end-use wettable powder dialifor products not exempted form
FIFRA Section 3(c)(2)(D) are responsible for the submission of "generic" data
described in Tables A and B in Section III.A of this chapter, in addition to
the product specific data listed in Table D.
Registrants of all end-use wettable powder dialifor products are advised that
if data are not generated to fill generic data requirements for the
manufacturing-use product(s), these registrations will be suspended. If
continued availability of the manufacturing-use product is desired, these data
must be supplied.
Table D, entitled: PRODUCT SPECIFIC DATA REQUIREMENTS FOR WETTABLE POWDER
PRODUCTS includes those data that relate only to the properties or effects of
a wettable powder product with a specific composition. Thus, these data are
required of each wettable powder dialifor end-use product to characterize the
product's particular composition, physical/chemical properties, and acute
toxicity. Providing data to fulfill these data requirements is the
responsibility of each applicant for the registration or reregistration of a
wettable powder dialifor product.
Applicants for the registration of new wettable powder dialifor products must
submit all required product specific data or establish that the proposed
product is substantially similar to another product for which the Agency has
received acceptable product specific data.
If the Agency has received acceptable product chemistry and/or acute toxicity
data for the existing wettable powder dialifor product(s), this is indicated in
Table Dr and the specific product(s) is identified in the guidance package
accompanying this Standard. In addition, in the column entitled: Bibliographic
Citation , identification numbers of the acceptable studies are provided.
These acceptable data are also summarized in the Topical Discussion sections of
this Standard. If the Agency has established that a particular product is
substantially similar to another product for which the Agency has received
acceptable product chemistry and/or acute toxicity data, then this too is
indicated.
Product specific data need not be acknowledged under FIFRA Section 3(c)(l)(D)
unless the Agency or a registrant has established that a- product is
substantially similar to another product for which the Agency has received
acceptable product specific data. If this should occur, the registrant(s) of
the former product(s) is required to.acknowledge reliance on these data. There
is only one currently registered wettable powder product.
3-5
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TABLE-A
GENERIC DATA REQUIREMOfrS AND DATA GAPS
FOR MANUFACTURING-USE DIALIFOR
Gulduline
Citation
Name of Are Data Test
Teat Required? Substances
Does EPA Have Data to Bibliographic
Partially or Totally Citation
Satisfy Requirement?
Must Additional Data be Submit try!
under FIFRA 1(c)(2)(B)7 If so,
dnadllns for submission.
PRODUCT CHEMISTRY
163. 61 -3 (b)
163.
163.
163.
163.
163.
163.
163.
163.
163.
163.
61-8(1)
61-8(2)
61-8(3)
61-8(4)
61-8(5)
61-8(6)
61-8(7)
61-8(8)
614(10)
61 8(11)
Identification
Color
Odor
Malting Point
Solubility
Stability
Octanol/Water
Partition
Coefficient
Physical State
Density or
Specific Gravity
Vapor Pressure
PH
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Tech.
Tech.
Tech.
Tech.
Tech.
Tech.
Tech.
Toch*
Tech.
Tech.
Tech.
Grade*
Grade
Grade
Grade
Grade
Grade
Grade
Grade
Grade
Grade
Grade
Yes
Yes
No
Yes
Partial
No
No
Yes
No
Yes
No
Itercules,
Hercules ,
Hercules,
Hercules,
Hercules,
Hercules,
Hercules,
Hercules,
Hercules,
Hercules,
Harcules,
Hercules,
19707,
1970?,
1970?,
19707,
19707,
19707,
19707,
19707,
19707,
19707,
19707,
19707,
00001982
00001942
00001992
00001942
00001932
00001942
00001982
00001942
00001982
00001942
00001982
00001942
No
No
Yea:
No
Yes:
Yes:
Yes:
No
Yes:
No
Yes:
6 months
6 months
6 months
6 months
6 months
6 month.?
T2=hnlcal Grad* Dial 1 for
Data Requirements Current
as of June 1911. Refer to
Guidance Package for Updated
Requirements.
-------
TABLE-A (con)
GENERIC DATA RBQUIRMEttTS AND DATA GAPS
FOR MANUFACTURING-USE DIALIFOR
Guidel Ina
Citation
ENV
163.
163.
163.
163.
163.
163.
163.
163.
163.
163.
IRONMEMfA
62-7 (b)
62-7 (c)
62 -8 (b)
62-9 (b)
62-9 (c)
62-9 (d)
62-9 (e)
62-10 (b)
62-11 (d)
62-12
Name of Are Data
Test Required?
L FATE
Hydrolysis
Photodcgradntion
Aerobic Soil
Metabolism
Leaching
Volatility
Adsorp./Desorp.
Water Dispersal
Terrestrial Field
Dissipation
Fish Accumulation
Reentry
Yes
Yes
Yes
Yes1
Yes
Yes
No
Yes
Yes3
Yes4
Test Does EPA Have Data to
Substance Partially or Totally
Satisfy Requirement?
Tech.
Tech.
Tech.
Tech.
T ich.
Tech.
Grade*
Grade
Grade
Grade
Grade
Grade
Representative
Form. Types**
Tech.
Grade
Itopresentatl ve
Form. Types
No
Partial5 1
Partial5
Partial5
No
No
Partial
No
Partial
Bibliographic Must Additional Data be Submitted
Citation under FIFRA 3(c)(2)(B)7 If so,
deadline for submission.
Ford, 1971
Hercules,
Ford, 1971
Ford, 1970
Ford, 1971
, 00001956
1968, 00002003
. 00001953
, 00001970
, C0001953
Knaak, 1978, 05003635
Wintorlln, 1978, 05001343
Yes:
Yes:
Yes:
Yes:
Yes:
No2
Yes:
Yes:
Yes:
24 months
24
24
24
24
24
24
24
months
months
months
months
6
months
months
months
* Radio labeled analytical grade or non-radio labeled technical grade.
** 151 Emulslfiable Concentrate nnd 50% Wottable Powder.
1 For terrestrial noncrop uses, orchard crop usos, field or vegetable crop
uses, and forestry uses, the mobility of the test substance and its
dcgradates In soil shall be assessed either by soil thin layer
chromntography, soil column, or batch equilibrium (adsorption/desorptlon).
2- Requested data on leaching will fulfill tills requirement.
3- Flow through only.
4- Need data on apples, pecans, and citrus.
S- Protocols used In testing not acceptable.
6- Tree fruit and nut crop use only.
Data Requirements Current as of
June, 1981. Refer to Guidance
Package for Updated Requirements.
-------
TABLE-A (con)
GENERIC DATA REQUIREMENTS AND DATA GAPS
FOR MANUFACTURING-USE DIALIFOR
Guideline
Citation
TOXICOLOGY
163.B1--1
163.81-2
163.81-7
163.82-1
163.B2-2
1G3.B3-1
163.83-2
163.83-3
163.83-4
163.84-1-4
163.85-1
Name of Test Are Data
Tost Required?
Acute Oral Yes
Toxlclty
Acute Dermal Yos
Toxlclty
Acute Delayed Yes
Neurotoxlclty
Gubchronlc Oral Yes
Toxtclty
Subchronlc Yes
(21-day) Dermal Toxlclty
Qironlc Feeding Yes
Oncogenlclty Yes
Teratogenlcity Yes
Reproduction Yes
Mutagenlclty Yes
HetabollsM Yes
Test
Substance
Dlalifor
t Oxon*
Dlallfor
t Oxon*
lech. Grade**
Tech. Grade
Tech. Grade
Tech. Grade
Tech. Grade
'lech. Grade
Tech. Grade
Tech. Grade
Tech. Grade
Does EPA Have Data to Bibliographic Must Additional Data be Submitted
Partially or Totally Citation under FIFRA 3(c)(2)(B)7 If so,
Satisfy Requirement? deadline Cor submission.
Dial! for: No1
Oxon: No
Dlalifort No1
Oxon: No
No
No
Partial2
No
No
No1
No
No
Partial
Jackson, 1966, 00002044 f Yesi 6 Booths
Shounig, 1966, 000020431
Shoenlg, 1966, 0000204 31 Yes: 6 months
Yes: 12 Months
Yes: 12 montlis
Nastri, 1969,000019462 Yes: 24 months
Yes: 48 months
Yes: 48 Months
Kennedy, 1966, 00002054* Yes: 24 montlis
Kennedy, 1966, 000020551
Yes: 48 montlis
Yes: 24 montlts
Bourke, 1970, 00001972 Yes: 24 months
Ford t Priant, 1971, 00001957
* Technical Dlallfor and the oxygen analog of Dlallfor.
•* Technical Grade Dlallfor.
1 Studies have not yet completed validation throujh Laboratory Audit Program, and are considered Invalid for purposes of this Standard.
Consult with EPA Laboratory Audit Program prior to initiating studies.
2- Study determined to be supplemental under Laboratory Audit Program, additional testing is required.
Data Requirements Current as of
June, 1981. Refer to Guidance
Package for Updated Requirements.
-------
TABLE-A (con)
GENERIC DATA REQUIREMENTS AND DATA GAPS
FOR MANUFACTURING-USE DIALIFOR
Name of Test
Test
Are Data Test Does EPA Have Data to Bibliographic
Required? Substance Partially or Totally Citation
Satisfy Requirement?
Must Additional Data be Submitted
under FIFRA 3(c) (2)(B)? IE so,
deadline for submission.
RESIDUE CHEMISTRY
Metabolism In Plants
Yes
Rep. Fora.*
Yes
Metabolism In Animals
Analytical Methods
Yes
Yes
Rep. Form.
Rep. Form.
Yes
Yes
Bourke, 1970, 00001972 Ho
Ford, 1971, 00001958
Ford, 1971, 00002|27
Hercules, 1968, 00002032
Hercules, 1972?, 00002125
Ford, 1971, 0000195*;
Bourke, 1970, 00001972 No
Ford, 1969, 00002024
Ford, 1968?, 00002022
St. John, nd, 05001830
Ford, 19?? 00002005 No
ttercules.1968, 00002037
Eastman, 19687, 00002027
* from application of representative formulations (45% B.C. and 50% W.P.).
-------
TABLE-A (con)
GENERIC DATA REQUIREMDtrS AND DATA G\PS
FCn MANUFACTURING-USE DIALIFOR
N-mie of Teat
Tost
Are Data
(Inquired?
Test
Substance
Does BPA Have Data to
Partially or Totally
Satisfy Requirement?
Bibliographic
Citation
Must Additloivil Dita bn riibmltted
under FIFRA 3(c)(2)(B)7 If so,
deadline for submission.
RESIDUE CHEMISTRY (con)
Residua Data: RAC
Pecans
Citrus Fruits
Grapes
n/ilsins
Apples
Storage Data
Yes
Yes
Yes
Yes
Yes
Yes
Rep. Form.*
Rap. Farm.
Rep. Form.
Rap. Form.
Rep. Form.
Rep. Fora.
Yes
Yes
Yes
Yes
Yes
Yes
Ford, 1969, 00001990
Ford, 1972, 00002130
Ford, 1959, 00001990
Ibrcules,
Hercules,
Hercules,
Hercules,
Relinking,
Westlake,
19687, 00002032
19597, 00001967
19687, 00001968
19697, 00001969
19737, 00002138
1971, 05001345
Ford, 1970, 00001984
Ford, 1972, 00002127
Hercules, 19697, 00001994
Ford, 1970, 00001934
Ford, 1973, 00002127
Hercules, 19697, 00002034
Ford, 1972, 00001961
Ford, 1972, 00001993
Hercules, 19687 00002032
No
No
No
No
No
Residue Data;
Processed Foods
Citrus Pulp, Molasses.
Citrus Oil Yes
Raisins YDS
Raisin Waste Yos
Grape Juice
k Ponaco YOS
Rep. Form.
Rep. Form.
Rep. Form.
Rap. Form.
Partial1
Yos
Yes
Yes
Vfestlake, 1971, 05001345
Hercules, 19697, 00002033
Hercules, 19717, 000019%
Ford, 1970, 00001914
ttercules, 1973. 00002117
Hsrculcs, 1973, 00002117
Ford, 1972, 00002127
Ford, 1970, 00001934
Yes: 24 months
-------
TABLE-A (con)
GENERIC DATA REQUIREMENT AND DVTA GAPS
FOR MANUFACTURING-USE DIALIFOR
Name of Test
Tost
Are Data Test Does EPA I lave Data to Bibliographic
Required? Substance Partially or Totally Citation
Satisfy Requirement?
Mush Additional frita be Submitted
undor 'FIFRA 3(c)(2)(B)7 1C so,
deadline for submission.
RESIDUE CHEMISTRY (con)
Residue Data:
Apple Juice
6 Pomace
Yes
Rep. Form.
Yes
Ford, 1972, 00001993
No
Residues in Meat, Milk,
Poultry, and Eggs Yes
Rep. Form.
Yes
Itercules. 19727, 00002125
St. John, nd, 00002260
St. John, nd, 05001830
Ford, 19687, 00002022
Ford, 19697, 00002024
Taylor, 1969, 00002038
Ford, 1972, 00002129
No
1- Need petition proposing a food additive tolerance of 110 ppm in citrus oil.
Data Requirements are Current
as of June, 1981. Refer to
Guidance Package for Updated
Requirements.
-------
TABLB-A (con)
GENERIC DATA REQUIREMENTS AND DATA GAPS
FOR MANUFACrURIKj-USB DIALIFOR
Guideline
Citation
Name of Test Are Data Test Does EPA Have Data to
Test Required? Substance Partially or Totally
Satisfy Requirement?
Bibliographic Must Additional Data be Submitted
Citation under FIFIW 3(c)(2)(R)? If so,
deadline for submission.
ECOLOGICAL EFFECTS
103.71 -1
163.71-2
16J.71-4
163.72-1
163.72-2
163.72-3
163.72-4
163.122-1
163.122-1
163.122-2
Avian Single Yes Toch. Grade* No
Dose Oral LD50
Avian Dietary Yes Tech. Grade Partial! Waterfowl
LC50
Avian Yes Tech. Grade No
Reproduction
Fish Acute Yes Tech. Grade No
LC50
Acute Toxlcity Yes Tech. Grade No
to Aquatic
Invertebrates
Acute Toxlcity Yes: Citrus Tech. Grade Partial: Shrimp
to Estuarlne & Use
Marine Organisms
EMbryolarvae & No1
Life-Cycle
Seed Germination Yes Tech. Grade No
Vegetative Vigor Yes Tech. Grade Yes
Growth of Yes Tech. Grade No
Aquatic Plants
Yes: 6 months
Beavers, 1977, 00002139 Yes: 6 months
Yes: 18 months
Yes: 6 months
Yes: 6 months
Sleight, 1972, 00002191 Yes: 6 months
Yes: 24 months
Ishitani, 1975, 05006342 No
Yes: 24 months
* Testing required on Technical Grade Dialifor.
1- Testing may be required ponding receipt am) results of mobility and
persistence studies.
Data Requirements Current as of
June, 1981. Refer to Guidance
Package for updated
Requirements.
-------
TABLE-B
PRODUCT-SPECIFIC DATA REQUIREMENT AND DATA GAPS
FOR MANUFACTURING-USE DIALIFOR PRODUCTS
Guideline Name of Are Data
Citation Test Required?
PRODUCT CHEMISTRY
163.151 3 Prcxl. Identity Yes
and Disclosure of
Ingredients
163.61-4 Description of Yes
Manufacturing Process
16J.61-5 Disc, of Formation Yes
of Unint. Ingredients
163.61-6 Declaration Yes
of Ingredient Limits
163.61-7 Product Analyt. Yes
Methods and Data
163.61-8(7) Physical State Yes
163. months
6 months
6 months
6 months
6 months
6 months
6 months
* For Currently Registered Product.
** Required for each Manufacturing-use Product.
*** Required for Manufacturing-use Products which are not the same as tha
Technical Grade of the Active Ingredient. These data are required for
Mriiuifa'jturing-use Dial!for.
Data Requirements are Current as of
June, 1981. Refer to Guidance Package-
for Updated Requirements.
-------
TABLE-B (con)
PRODUCT-SPECIFIC DATA REQUIREMENTS AND DATA GAPS
FOR MANUFACTURING-USE DIAUFOn PRODUCTS
Guideline Name of Arc Data Test Does EPA Have Data to Bibliographic Must Additional Data be Submitted
Citation Test Required? Substance Partially or Totally Citation under FIFRA 3(c) (2) (B>? 1C so.
Satisfy Requirement?* deadline Cor submission.
TOXICOLOGY
163.81-1
163.81-2
163.B1-3
163.81-4
163.81-5
163.81-6
* lor
*• Reo\
Acute Oral Yes HUP** No1
Toxic ity
Acute Dental Yes HUP** No1
Toxlclty
Acute Inhal. Yes HUP*" No
Toxlclty
Prim. Kye Yes HUP*** No
Irritation****
Primary Dermal Yes HUP*** No
Irritation
Dermal Yes MUP*** No
Sensltlzatlon
Currently Registered Product.
ilred Cor Manufactur Ira-use Products «4ilch are i»t tha nri^i as
Jackson, 1966, 00002044 \ Yes: 6 months
Schoenlg, 1966, 00002043*
Schoenlg, 1966, 0000204 3 * Yes: 6 Months
Yes: 6 months
Yes: 6 months
Yes: 6 months
Yes: 6 months
tha
Technical Grade of the Active Ingredient.
**• Each Manufacturing-use Product or Substantially Similar Product.
**•* A demonstration of pit between 1 and 3, or 12 and 14 or a demonstration
of dermal Irritability will bo sufficient to categorize a product as an
ocular irritant, and additional testing will not be required.
1- Data not yet completed validation through Laboratory Audit Program, considered invalid for purposes of this Standard.
Consult with EPA Laboratory Audit Program prior to initiating testing.
-------
TABLE-C
PRODUCT-SPECIFIC DATA REQUIREMENTS AND DMA GAPS
FOR EMULSIFIABLE CONCENTRATE DIAL!FOR PRODUCTS
Guideline
Citation
Name of Are Data
Test Required?
Test Does EPA Have Data to Bibliographic Must Additional Dtta Be Submitted
Substance Partially or Totally Citation under FIFIW l(c) (2) (BJ? If so.
Satisfy Requirement?* deadline for submission.
• PRODUCT CHEMISTRY
163.61-6
Declaration
Yes
Each B.C. Product**
No
Yes:
6
months
of Ingredient Limits
1G3.61-7
103.01-8(1)
K,3.61-8(2)
161.61 0(7)
K.3.61 8(8)
163.61-8(9)
ir,3. 61-0(10)
163.61-8(11)
163.61-8(12)
163.61-6(13)
163.61 8(14)
163.61-8(15)
163.61-8(16)
163.61 8(17)
163.61 8(18)
Product Analyt.
Methods and Data
Color
Odor
Physical State
Density or
Specific Gravity
Boiling Point
Vapor Pressure
PH
Storage Stab.
FlauMbtllty
Oxidizing or
Reducing Action
Exploslveness
Nisclblllty
Viscosity
Corrosion
Characteristics
* For Currently Registered
•* Each Bau
laiflable Concent
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Products
rate Produ
Each B.C. Product
Bach B.C. Product
Each B.C. Product
Each B.C. Product
EC***
EC
EC
EC
EC
EC
EC
EC
EC
EC
EC
Ct
No
No
No
Yes
No
No
No
No
No
No
No
No
No
No
No
Yes:
Yes:
Yes:
Yes:
Yes:
Yos:
Yes:
Yes:
Yos:
Yes:
Yes:
Yes:
Yes:
Yos:
6
6
6
6
6
6
6
6
6
6
6
6
6
6
months
months
months
months
months
months
months
months
months
months
months
months
months
months
*** Each Enulsifiable Concentrate Products or Substantially Similar Product
Data Requirements are Current
as of June, 1981. Refer to
Guidance Package for Updated
Requirements.
-------
TADLE-C (con)
PROOUCT-SPBCIFIC DATA REQUIRfMEMir, AND DATA GAPS
FOR DWJLSIFIABLE CONCENrRATB DIALIFOR PRODUCTS
Guld.il Ina
Citation
Name oC Arc Data Tost Does EPA Have Data to Bibliographic Must Additional Onta be Submitted
Test Required? Substance Partially or Totally Citation under FIFRA 3(c) (2) (B)? tf so.
Satisfy Requirement?* dead Una for submission.
TOXICOLOGY
163
1G3
163
163
163
163
.81-1
.81-2
.81 3
.81 -4
.81-5
.81-6
Acute Oral Yes EC** No
Toxlclty
Acuto Dormal Yes EC** Yes
Toxic! ty
Acute Inhal. Yes EC** No
Toxlclty
Prim. Bye Yes EC** No
Irritation
Primary Dermal Yes EC** No
Irritation
Dermal Yes EC** No
Yes: 6 months
Nastrl, 1969, 00002269 No
Yes: 6 months
Yes: 6 months
Yea: 6 months
Yes: 6 months
Smsltlzatton
* Par currently Higlstored Products
** Bach Qnulsieiablu Concentrate Products or Substantially Similar Product.
Data Roquiremonts are Currant as of
June, 1931. Refer to Guidance'
Package for Updated Itoqulreonnts.
-------
TABLE-D
PRODUCT-SPECIFIC DATA REQUIREMENTS AND DMA GAP1
FOR WETTAQLE POWDER DIALIFOR PRODUCTS
Guideline Name of Are Data
Citation Test Required?
PRODUCT CHEMISTRY
163. 61-6 Declaration
Yes
Test Does EPA Have Data to Bibliographic Must Addition*! Data Bo Suhmltt~1
Substance Partially or Totally Citation under FIFRA l(c)(2)(B)7 1C so.
Satisfy Riqulrcment?* deadline Cor submission.
Each W.P. Product**
No
Yes:
!i months
of Ingredient Limits
163. 61 -7 Product Analyt.
Methods and Data
169.61-8(1) Color
163.61-3(2) Odor
163.61-8(7) Physical State
163.61-8(8) Density or
Specific Gravity
163.61-8(10) Vapor Pressure
163.61-8(11) pH
163.61-6(12) Storage Stab.
163.61-3(13) Flamablllty
163.61 i (14) Oxidizing or
Reducing Action
163.61-8(15) Explosiveness
163.61-8(16) Misclblllty
163.61-8(17) Viscosity
163.61-3(18) Corrosion
diaracterlstics
• fot Currently Registered
** Bach tfettable Powder Prod
Yes
Yes
Yes
Yes
Yes
Yos
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Product.
uct.
Each H.P. Product
Each W.P. Product
Each H.P. Product
Each W.P. Product
HP***
WP
WP
WP
WP
WP
WP
WP
WP
WP
No
No
No
Yes
No
No
No
No
No
No
No
No
No
No
Yes:
Yes:
Yes:
Yes:
Yes:
Yes:
Yes:
Yes:
Yes:
Yes:
Yes:
Yos:
Yes:
6 months
6 nonths
6 nonths
6 months
6 nonths
6 nonths
6 months
6 months
6 months
-------
TABLE-0 (con)
PRODUCT-SPECIFIC DATA REQUIREMENTS AND DATA GM>S
FOR HETTABLB POWDER DIALIFOR PRODUCTS
Guideline
Citation
TOXICOLOGY
163.81-1
163.81-2
163.81-3
163.81-4
163.81-5
163.81-6
Name of
Teat
Acute Oral
Toxlclty
Acute Denial
Toxlclty
Acute Inhal.
Toxlclty
Prim. Eye
Irritation
Primary Danul
Irritation
Dermal
Are Data
Required?
Yes
Yes
Yes
Yes
Yes
Yes
Test
Substance
WP»*
HP**
*••••
»•*
*•>••
HP**
Does EPA Have Data to
Partially or Totally
Satisfy Requirement?*
/
No '
Yes
No
No
No
No
Bibliographic Must Additional Data be Submitted
Citation under FIFRA 3(c)(?MB)7 If so,
deadline for sujiusslon.
'
Yes: 6 months
Mastrl, 1969, 00003280 No
Yes: 6 months1
Yesi 6 months
Yes: 6 months
Yes: 6 months
Sensltlxatlon
* tot Currently Registered Product.
•• Each Mettable Powder Product or Substantially Similar Product.
1 Testing of the Nanufacturing-use Product is sufficient to satisfy the data requirement.
-------
CHAPTER IV
PRODUCT CHEMISTRY OF DIALIPOR
Introduction
FIFRA 3(c)(2).(A) requires the Agency to establish guidelines for registering
pesticides in the United States. The Agency requires registrants to provide
quantitative data on all added ingredients, active and inert, which are equal
to or greater than .1% of the product by weight.
To establish the composition of products proposed for registration, the Agency
requires data and information not only on the manufacturing and formulation
processes but also a discussion on the formation of manufacturing impurities
and other product ingredients, intentional and unintentional. Further, to
assure that the composition of the product as marketed will not vary from the
composition evaluated at the time of registration, applicants are required to
submit a statement certifying upper and lower composition limits for the added
ingredients, or upper limits only for some unintentional ingredients. Subpart
D of the Proposed Guidelines (43 FR 29696, July 10, 1978) suggests specific
precision limits for ingredients based on the percentage of ingredient and the
standard deviation of the analytical method.
In addition to the data on product composition, the Agency guidelines also
require data to establish the physical and chemical properties of both the
pesticide active ingredient and its formulations. For example, data are needed
concerning the identity and physical state of the active ingredient (e.g.
melting point, boiling point, ambient vapor pressure, and solubility). Data
are also required on the properties of the formulated product to establish
labeling cautions (e.g. flammability, corrosiveness, or storage stability).
The Agency uses these data to characterize each pesticide and to determine its
environmental and health hazards.
4-1
-------
Product Chemistry; Manufacturing-use Dialifor
Product Chemistry Profile
Dialifor is the common name for O,O-Diethyl S-(2-chloro-l-pthalimideoethyl)
phosphorodithioate). In early phases of development, dialifor was referred to
as Hercules 14503. Manufacturing-use and end-use products are marketed under
the trade name Tbrak.
Manufacturing-use dialifor contains a minimum of 90% O,O-Diethyl S-(2-chloro-l-
phthalimidoethyl) phosphorodithioate. Dialifor (pure chemical) is a white,
crystalline solid with a melting point of 67-69 C, and vapor pressure of less
than .001 mm Hg at 35 C. Dialifor is practically insoluble in water, ethyl
alcohol, and hexane, but soluble in several organic solvents. Manufacturing-
use dialifor is a brown liquid.
Pure or isolated dialifor is not an item of commerce. Commercial, or
manufacturing-use dialifor is sold in the form of 90% pure dialifor mixed with
some xylene-range aromatic solvents.
A detailed manufacturing procedure has not been submitted to the Agency. This
is essential because the presence of manufacturing impurities is dependent upon
the nature of the manufacturing process. The sole registrant, Hercules, Inc.,
did, however, report some iinpurities which could be present in technical grade
dialifor. Methods for the determination of dialifor in both manufacturing-use
and end-use products have been submitted. These methods are lacking in
analytical data necessary for the Agency to make a determination on their
adequacy.
Product Chemistry Topical Discussions
Chemical Identity
The Agency requires identifying information including chemical names, product
names, and numerical codes of all substances known or assumed to be present in
pesticide products.
"Dialifor" is the common name accepted by the American National Standards
Institute (ANSI) for the chemical 0,0-diethyl S-(2 chloro-1-pthalimidoethyl)
phosphorodithioate. The chemical formula is C.4H,_O4NS2PCL, and the
molecular weight is 393.5. The structural formula is:
0—CH7 CHj
Dialifor
4-2
-------
Manufacturing-use dial if or is also known by the trade name "Torak" and the
company number Hercules 14503. Other synonyms used include: dialifos (ISO) and
ENT 27320. Hercules, Inc. is the sole domestic manufacturer of manufacturing-
use dialifor. The Chemical Abstracts Registry (CAS) number fc 3ialifor is
10311-84-9. The EPA Shaughnessy number is 102501. The common name, dialifor,
will be used throughout this standard in lieu of other chemical or trade names.
The nomenclature of dialifor has been adequately defined for the purpose of
this Standard.
Manufacturing Processes
A detailed description of the manufacturing process is required because the
chemical reactions employed in the manufacturing process and/or the purification
of the active ingredient may suggest the presence or absence of potential
harmful impurities.
Because this type of information is considered to be confidential business
information, a discussion of the specific procedures, equipment and
manufacturing conditions required for commercial production of dialifor cannot
be published in this Standard. The manufacturing process as submitted by
Hercules, Inc., and the identification of impurities, are detailed separately
in confidential appendix B.
The procedure submitted by Hercules, Inc. is not sufficiently detailed to
satisfy Agency requirements.
Sittig (1977) cites U.S. Patent 3,355,353 by J. D. Jameson (November 23, 1967);
assigned to Hercules, Inc. The manufacture of dialifor includes the following
procedures:
(a) chloridizing N-vinyl phthalimide to N-(l,2-dichloroethyl)
phthalimide,
(b) reacting N-(l,2-dichloroethyl) pthalimide with ammonium diethyl
dithiophosphate in acetonitrile, at 25 C initially, then at
50°C,
(c) and cooling and filtering the product, redissolving it in benzene,
then washing it with water, until neutral and free of water-
soluble materials.
Formation of Unintentional Ingredients
Hercules, Inc. has submitted a confidential statement of ingredients for
manufacturing-use dialifor. This too is confidential business information and
cannot be discussed here. It is however, discussed in confidential appendix
B. The statement provided by Hercules, Inc. is missing required information on
a portion of the manufacturing-use product. These data are required.
Manufacturing-use dialifor has been analyzed for the presence of N-nitrosamines
(Morrison, 1978, 00004153). The sensitivity of the test was .3 ppm. A Varian
chrcmatograph was used, with a thermal energy analyzer, and the recovery values
were in the range of 62%. No polar nitrosamines were detected.
4-3
-------
Active Ingredient Limits in Pesticide Products
Manufacturing-use dialifor is comprised of 90% minimum of the active ingredient
OfO-Diethyl S-(2-chloro-l-phthalimidoethyl) phosphorodithioate. Hercules,
Inc. has certified the lower limit of the active ingredient as a 90% racemic (d
and 1) mixture of the isomers of dialifor. Depending on the manufacturing
process conditions, up to 10% of technical impurities can be expected.
Product Analytical Methods and Data
Ultraviolet analytical methods for the identification and quanitification of
dialifor in the manufacturin7-use product and end-use products have been
submitted (Hercules, Inc., 1967, 00002008 and 1972?, 00002194). In both cases,
a suitable amount of sample is dissolved in methylene chloride and then
isolated from interfering materials on a silicic acid chromatographic column.
The absorbance is then measured in an ultraviolet spectre-photometer at 300 urn.
The peak is then compared with an internal standard.
The second method (Hercules, Inc., 1972, 00002194) describes fractionation in
two different solvents and the subsequent measurement of the ultraviolet
absorption of each fraction. In xylene, any unreacted N-(l,2-dichloroethyl)
pthalimide (N-DCEP), dialifor and an unidentified column "residue" (which
includes the oxygen analog of dialifor) are separated and measured in the
appropriate fractions.
Two other methods regarded as technically satisfactory for the determination of
dialifor and its impurities have been described (Hercules, 1972, 00002279).
One is a liquid chromatographic method that uses an ultraviolet photometric
detector, and the other method employs gas chromatography. The latter is used
exclusively for the determination of impurities. In both cases, internal
standards are used and the peak areas for dialifor and the internal standard
(corrected for a response factor obtained by calibration with a known mixture)
are used to calculate the percentage of dialifor.
Although the referenced methods for the identification and quantification of
dialifor in products are regarded as satisfactory, required analytical data
(recoveries, background, sensitivity, etc.) are lacking. Therefore, the Agency
is unable to determine whether or not these methods are fully acceptable.
Physical and Chemical Properties
For every pesticide product, the Agency requires data on certain physical and
chemical properties useful for identification purposes or for evaluation of
hazard potential. These data are required on the technical grade of the active
ingredient, and on the manufacturing-use product, if different. Certain data
are required on pure or isolated dialifor, as well as on the manufacturing-use
product.
The physical and chemical properties of technical grade dialifor have been
reported (Hercules, 1970?, 00001982, 00001942):
Physical State, Color: crystalline white
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Solubility (grains for 100 g solution at 20°C)
Water Less than 1 g
Acetone 76 g
Chloroform 62 g
Ethyl Alcohol Less than 1 g
Ethyl Ether 50 g
Hexane Less than 1 g
Isophorone 40 g
Xylene 57 g
The lack of quantitative solubility data (expressed in g/100 ml of. the solvent
at 20 C or in terms of ppm in distilled water or solvents commonly used for
pesticides) in some solvents constitutes the data gap described for the
solubility of technical grade dialifor.
Melting Point: 67°-69°C
Vapor Pressure: 0.0001 mm Hg at 35 by Menzie's method
Explosiveness: may explode if heated at 70 C
Little data are available on the physical/chemical properties of manufacturing-
use dialifor:
Physical State: liquid
Color: brown
Flammability: flash point above 200 F
4-5
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Product Chemistry; End-use Formulations
Product Chemistry Profile
End-use dialifor products are available in emulsifiable concentrate and
wettable powder formulations. Emulsifiable concentrates contain 45% dialifor
(and related compounds) and wettable powders contain 50% dialifor (and related
compounds). The analytical methods described in the manufacturing-use section
of this chapter apply to these end-use formulations as well. Data were not
available on the physical/chemical properties of any end-use product.
Product Chemistry Topical Discussions: End-Use Products
Chemical Identity
ilifor end-vise products are marketed under the trade names Torak-P^ Torak-
"r and
Active Ingredients in Pesticide Products
Three 4 pound per gallon emulsifiable concentrates containing dialifor as the
sole active ingredient are currently registered. These products contain 45%
dialifor (and related compounds). One 50% wettable powder is also registered.
Product Analytical Methods and Data
See discussion in manufacturing-use section for details.
Physical and Chemical Properties
The only data available is the physical state. Emulsifiable concentrates are
liquids and wettable powders are solids.
4-6
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CHAPTER V
ENVIRONMENTAL FATE OF DIALIFOR
Use Pattern Profile
Dialifor is an insecticide-acaracide registered for control of:
1. apple maggot, plum curculio, and red tended leaf roller on apples,
2. pacific spidermite and grape leafhopper on grapes,
3. citrus rust mite, citrus red mite, texas citrus mite, citrus snow scale,
and brown soft scale on citrus, and
4. black pecan aphid, hickory shuckworm, pecan nut case bearer, pecan
weevil, spittle bugs, yellow pecan aphid, and serpentine leadminer on
pecans.
Dialifor is formulated as a 50% wettable powder, and a 4 Ib./gallon
emulsifiable concentrate. The wettable powder is registered for use as a
foliar spray on apples. The 4 Ib./gallon emulsifiable concentrate is
registered for use as a foliar spray on grapes, citrus, and pecans.
On apples, applications can be made at 7-14 day intervals for nearly an entire
season (1-6 applications per season). Applications are made beginning at petal
fall. The dialif or product registered for use on apples was never placed on
the market.
On grapes, applications can be made at 1-4 month intervals for up to 2 times
per year. Applications are made in early April or May and July or August (when
needed). Most appplicators are certified or work under the supervision of
certified applicators. Current labels on emulsifible concentrate dialifor
products intended for application on grapes restrict use of Dialifor to
California.
On citrus, applications can be made at 3 month intervals if fruit is present at
first application, for up to 2 times per year. Applications are made post-
bloom and in summer. Most applicators are certified or work under the
supervision of certified applicators.
On pecans, applications can be made at 7-10 days intervals for up to 12 times
per year. Applications are made beginning in February-March in southern
states, and continuing through late summer. Applicators are certified or are
supervised by certified applicators.
The major site for dialifor use was on citrus during the early 1970's. Pecans
began to account for an increasing amount of total poundage throughout the mid
and later 1970's.
5-1
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Most dialifor usage today is on citrus and pecans. However, the only existing
dialifor products are those which were manufactured 1-3 years ago and are still
being marketed. Available data indicate that dialifor is applied to less than
1 percent of citrus, pecan, grape, and apple acreage in the United States.
Registered application rates are listed below:
TYPE OF APPLICATION
FORMULATION SITE APPLICATION RATE
Wettable Powder Apples Foliar 1.5-
(50%) 2.25 Ib
AI/A
Emulsifiable Grapes Foliar 1.0 Ib AI/A
Concentrate
(4 Ib/gal)
Citrus Foliar 1.25-
5.0 Ib AI/A
Pecans Foliar 1.0-
2.0 Ib AI/A
5-2
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Environmental Fate; Dialifor
Environmental Fate Profile
Preliminary data suggest that dialif or does not leach through clay or loamy
sand soils. More than 96% of the applied dialifor remained in the upper 1 inch
and 99% remained in the upper 2 inches of these soils after they were eluted
with 2.5 acre-inches of water. A linear decline of subsurface applied dialifor
was reported under greenhouse conditions with a half-life of about 28 days. In
this study, the. oxygen analog of dialifor was present in unknown amounts
throughout a 99-day period. Dialifor was more persistent in a moist Willamette
soil maintained in sealed containers in the dark at 20 C. Under these
conditions the half-life of dialifor, at 0.1 and 1 ppm, was about 5 months.
The field dissipation of dialifor is biphasic, with an initial rapid rate of
decline followed by a slower decline rate. Levels of residues recovered from
the top 4 inches of California loam, Mississippi fine sandy loam, and Nebraska
and Delaware slit loams ranged from 5.8 to 57% of the applied amount 9 weeks
after treatment with emulsifiable concentrates of dialifor at 5 Ib ai/A. The
amount of dialifor that dissipated after 9 weeks varied from 0% over the
following 5.5 months, to 50% over the following 3.5 months.
In a photolysis study, dialifor oxygen-analog, phthalamide, phthalamic and o
phthalic acids, N-(8-chlorovinyl) phthalamide, and phosphorothioate derivatives
were detected in preparations containing dialifor. The mechanisms of formation
of these compounds cannot be determined based on the available information.
Exposure Profile
Dialifor is registered as an insecticide/acaracide for use on agricultural
crops. An emulsifiable concentrate containing 45% dialifor (and related
compounds) is registered for use on grapes, pecans, and citrus. A wettable
powder containing 50% dialifor (and related compounds) is registered for use on
apples. Both formulations are applied as sprays for foliar treatment.
All Formulations
The use of airblast machines (which direct the spray upward) increases the
potential for exposure via spray drift to humans, livestock or wildlife outside
the application site. Although the extent to which airblast machines are used
for dialifor application is not known, available data indicate that worker
exposure will occur primarily through the dermal route.
Data are insufficient to establish the potential for groundwater contamination,
or bioaccumulation.
Emulsifiable Concentrates
In studies using an emulsifiable concentrate, dialifor was applied to oranges
at a rate of 3.75 pounds active ingredient per acre with a commercial sprayer.
Respirator cartridges and filters were used to measure exposure to gaseous and
particulate dialifor, respectively. Air samples were also taken from operator
breathing zones. Dermal exposure was measured by analyzing dialifor residues
on shirts worn by the operators for timed intervals.
5-3
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Results showed that respiratory exposure to gaseous and participate dialifor
would be <0.01 and 0.143 mg/8-nour workday, respectively. Analysis of air
samples taken from operator breathing zones showed a potential inhalation
exposure of approximately 0.05 rog/day during hard work (respiratory rate of 11
liters per minute). Total potential dermal exposure to dialifor under the same
conditions ranged from 49 to 66 mg/8-hour workday (mean 58 mg/day).
Wettable Powder
Exposure studies conducted with the wettable powder formulation of dialifor
also showed that operator exposure would be predominantly dermal. These
studies were conducted under conditions similar to those used in the
emulsifiable concentrate studies, except that dialifor was applied to apples at
2.0 Ib ai/A. Tests were conducted on two different days at the same location.
Data from the first spraying showed that respiratory exposure to gaseous and
particulate dialifor would be <0.01 and 0.03 mg/8 hour workday, respectively.
Air samples taken from the breathing zone of the operator showed that
approximately .029 mg/day would be available for absorption by inhalation
during hard work. Total dermal exposure was approximately 38 mg/8-hour
workday. Data from the second spraying supported the initial observation that
respiratory exposure to gaseous and particulate dialifor would be < 0.01 and
0.03 mg/8-hour workday. Breathing zone measurements showed approximately 0.01
mg/day available for inhalation. Total dermal exposure resulting from the
second spraying was about 15 mg/8-hour workday.
5-4
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Farmworker Exposure
A number of field studies have been conducted to measure fieldworker exposure
to residues of dialifor in grapes, and to measure dislodgeable residue
concentrations after application. Many of these studies were initiated
following reports of worker illness after reentry into treated areas.
Summary Table
Crop/ Residue Levels Dislodgeable
location Application Rate Skin Clothing Interval Residues
Madera, Grapes; 1 Ib ai/A
California
Trousers: Unknown Unknown
.42-1.6 ug/cm
Lodi, Grapes; 1 Ib ai/A 1.24 ug/cm^
California
50 days Unknown
Fresno, Grapes; 1 Ib ai/A 1.54 ug/cm
California
71 days Unknown
Madera,
California
Grapes; 1 Ib ai/A
(airblast)
0 days 2.32ug/
cm
Madera,
California
Grapes; 1 Ib ai/A
Soledad,
California
Lodi,
California
Grapes; 2@ 1 Ib ai/A*
Grapes; 1 Ib ai/A
(boom sprayer)
Grapes; 1 Ib ai/A
(speed sprayer)
60 days dialiforz
107 ng/cm
oxon: 2
21.6 ng/cm
60 days dialifor:.,
60.3 ng/cm
oxon: ,,
22.7 ng/cm
60 days dialifor:-
99.6 ng/cm
oxon: 2
26.2 ng/cm
2
0 days 2.1 ug/cm
0 days .41 ug/cm
5-5
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2
Fowler, Grapes; 1 Ib ai/A 42 days .09 ug/on
California
2
San Joaquin, Grapes; 1 Ib ai/A at .13 ug/cm
California harvest
* one application 2 months and one three months before harvest
Half-lives ranged from 9-15 days. The Agency is unable to determine what
foliar dislodgeable residue levels are safe for reentry because of extensive
gaps in the toxicology data base. However, the Agency has decided to accept
the 75-day reentry interval established by the State >f California for the use
of dialifor on grapes. This reentry interval corresponds to what California
believes is a safe foliar dislodgeable residue level of 0.06 ug/cm .
5-6
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"topical Discussions: Manufacturing-use Dialif or
Physico-chemical Transformation
Metabolism
Mobility
Field Dissipation
Accumulation
Reentry
Physico-chemical Transformation 163.62-7
Hydrolysis
Hydrolysis data are required to support the registration of all manufacturing-
use chemicals regardless of the intended end uses of products formulated from
the manufacturing-use product.
Four studies were reviewed; however, no valid data on the hydrolysis of
dialifor were available.
All studies specified in Section 163.62-7(b) are needed to assess the
hydrolysis properties of manufacturing-use dialifor.
Photolysis
A photodegradation study in water is required to support the registration of
each formulated end-use product intended for terrestrial (except greenhouse and
domestic outdoor), aquatic, and forestry use and for any aquatic impact use
which results in direct discharges into the aquatic environment. Such a study
is also required to support the registration of each manufacturing-use product
which legally could be used to make such an end-use product.
Photodegradation studies on soil surfaces are required to support the
registration of each formulated end-use product intended for crop uses and
forestry uses. Such studies are also required to support the registration of
each manufacturing-use product which legally could be used to make such an end-
use product.
Two related studies were reviewed and considered invalid because the studies
did not indicate if dark controls were employed. In addition, the purity of
the starting materials were not specified. However, one of these studies
(Ford, 1971, 00001956) contains valid data on dialifor degradation products.
The identified compounds are: dialifor oxygen-analog, phthalamid, o-phthalic
acid, phthalamic acid, N(B-chlorovinyl)phthalamide, and phosphorothioate
derivatives.
Due to the deficiencies in protocol followed in these studies, the
mechanism(s)of formation of these compounds cannot be determined. All data
specified in Section 163.62-7(c) are needed to determine the effect of light on
dialifor.
Metabolism 163.62-8
Data on metabolism are required to determine the nature and availability of
pesticide residues to rotational crops and to help in the.assessment of
potential disposal and reentry hazards.
5-7
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Soil
Aerobic soil metabolism studies are required to support the registration of all
products intended for terrestrial end-uses or terrestrial/aquatic (forest) end-
uses.
Two soil metabolism studies were reviewed and provide preliminary data on the
degradation of dialifor in soil. An acetone solution of dialifor was applied
to topsoil in pots under greenhouse conditions in a manner designed to minimize
volatilization and photodegradation (Hercules, Inc., 1968, 00002003). The half-
life of dialifor was approximately 28 days; 8% was recovered after 99 days.
The oxygen analog of dialifor was present throughout this period in quantities
that cannot be verified. In a related study (Freed et al., 1979, 05008242),
the half-life of dialifor, at applications of .1 and 1 ppm, was determined to
be about 5 months in moist Willamette soil maintained in sealed containers.
However, this study did not indicate whether aerobic or anaerobic conditions
prevailed. This decreases the value of the study for determining the aerobic
metabolism of dialifor in soil.
All data specified in Section 163.62-8(b) are needed to determine the aerobic
metabolism of dialifor in soil. Anaerobic soil metabolism data are not
required because dialifor is not used for field and vegetable crops.
Mobility 163.62-9
Data on mobility are required to determine pesticide residue movement in the
environment.
Leaching
Data are required to support the registration of products intended for the
following end-uses: domestic outdoor use, greenhouse use, terrestrial noncrop
use, orchard crop use, field or vegetable crop use, forestry use, aquatic use,
and aquatic impact use involving direct discharge only.
For terrestrial noncrop uses, orchard crop uses, field or vegetable crop uses,
and forestry uses, the mobility of the test substance and its degradates in
soil shall be assessed either by soil thin layer chromatography, soil column,
or batch equilibrium (adsorption/desorption). For domestic outdoor uses,
greenhouse uses, aquatic uses, and aquatic impact uses, the mobility of the
test substance and its degradates in soil shall be assessed only by batch
equilibrium (adsorption/desorption).
The leaching potential of dialifor (6 Ib/gal emulsifiable concentrate) was
studied in three soils (characteristics given in Table 1) in 6-inch aluminum
leaching columns eluted with 2.5 inches of water (Ford, 1971, 00001953). Gas
chrcmatographic analysis of dialifor residues showed that 96% of the applied
dialifor remained in the upper 1 inch and more than 99% remained in the upper 2
inches of soil. Dialifor does not appear to leach through clay or loamy sand
soils. For registration purposes, these results must be regarded as
preliminary, studies in soil leaching require the use of 30-on columns leached
with 20-acre-inches of water on four soil types.
All studies specified in Section 163.62-9(b) are needed to determine the
leaching potential of dialifor and its degradation products.
5-8
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Table 1. Characteristics of Soils Used for Leaching Studies
Soil Sand Silt Clay
Origin (%) (%) (%)
Nebraska3 20 30 46
Florida 82 16 2
Delaware 28 28 44
Organic Matter
3.60
0.68
1.60
The percentage of sand, silt, and clay added up to only 96%, not 100%.
However, the texture classification is considered appropriate. Adapted from
Ford, 1971, 00001953.
Volatility
Laboratory volatility studies using nonradioiostopic analytical techniques are
required to support the registration of all products intended for greenhouse
use and to evaluate reentry hazards from cholinesterase-inhibiting pesticides.
No data on the volatility of dialif or are available.
Dialifor is a cholinesterase inhibiting pesticide and the possibility of a
reentry hazard exists with current uses of dialifor. Consequently, all data
specified in Section 163.63-9(c) are needed to determine the volatility of
dialifor.
Adsorption/Desorption
A laboratory study using radiosiotopic or nonradioisotopic analytical
techniques is required to support the registration of all products intended for
terrestrial end-uses, terrestrial/aquatic (forest) end-uses, aquatic end-
uses,and aquatic impact end-uses (if the pesticides are discharged directly
into the aquatic environment).
No data were available. Data necessary to meet this requirement will be met by
data requested on leaching.
Water Dispersal
Data on the water dispersal of dialifor are not required because dialifor is
not registered for an aquatic use.
5-9
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Field Dissipation 163.62-10
Field dissipation studies under actual use conditions are required to support
the registrations of all products intended for terrestrial (except greenhouse)
end-uses, aquatic end-uses, and terrestrial/aquatic (forest) end-uses.
Terrestrial
Terrestrial field dissipation studies using representative formulated products
are required to support the registration of each product intended for
terrestrial (except greenhouse) end-uses.
Three field dissipation studies were reviewed and two were considered valid.
Dialifor residues were determined in the top 4 inches of field plots treated
with emulsifiable concentrates (EC's) of dialifor (Ford, 1970, 00001970).
Residue levels 9 weeks after treatment of Delaware silt loam with a 6 Ib/gal
EC, at 1 to 5 Ib ai/A, were 0.57 and 2.1 ppm, respectively. Residue levels
remained unchanged 5 months later in the soil treated at 1 Ib ai/A. Residue
levels 9 weeks after treatment of Nebraska silt loam with 4 and 6 Ib/gal EC at
5 Ib ai/A were 1.6 and 1.9 ppm, respectively. Residue levels dissipated an
additional 50% 5 months later in the soil treated with 4 Ib/gal EC. Residue
levels in Mississippi fine sandy loam and California loam were 0.43 and 0.47
ppm 9 weeks after treatment with 4 Ib/gal EC at 5 Ib ai/A.
Similar field dissipation data were collected 1 year later using the same soils
described above after treatment at a rate of 5 Ib ai/A with an unspecified type
of emulsifiable concentrate (Ford, 1971, 00001953). Residue levels 9 weeks
after treatment were 0.04, 0.78, 0.24, and 0.55 ppm in the California,
Mississippi, Nebraska, and Delaware soils, respectively. Residue levels in the
latter two soils 5.5 months post treatment were 0.12 and 0.15 ppm, respectively.
In both of the above studies, preapplication and immediate postapplication data
were not obtained; therefore, reliable half-life estimates cannot be derived
from the data. The data indicated that dialifor dissipation is a Diphasic
phenomenon with an initial rapid rate of decline followed by a slower decline
rate.
These data alone are insufficient to assess the rate or the impact of the
dissipation of dialifor in the field. Additional data are needed in the
following use area.
o Tree fruit and nut crop - Section 163.62-10(b)(2)
Data are needed to determine the dissipation rate of the following formulations
of dialifor:
45% ai emulsifiable concentrate
50% ai wettable powder
Accumulation 163.62-11
Fish
A laboratory study employing radioisotopic or nonradioisotopic analytical
techniques is required to support the registration of all products intended for
terrestrial noncrop, tree fruit/nut crop, and field/vegetable crop end-uses;
5-10
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aquatic food crop and noncrop end-uses; terrestrial/aquatic (forest) end-uses;
and aquatic impact (indirect discharge) end-uses.
No data on the accumulation of dialifor in fish are available. Registrants
have the option of supplying the required fish accumulation study or of
establishing that dialifor will not reach water and will not persist in water
(ie. a nominal half-life of 4 days or less), and that dialifor possesses an
octanol/water partition coefficient of less than 1,000.
Data specified in Section 163.62-11(d) for flow through study only are needed
to determine if dialifor will accumulate in fish.
Reentry 163.62-12
Reentry intervals are required to support the registration of all products for
which the Agency has determined that a reentry hazard exists for persons
reentering treated sites. Dialifor is an acetyl-cholinesterase inhibiting
pesticide which presents a hazard to persons reentering treated fields.
According to Knaak et al. (1978, 05003635), the half-life of dialifor residues
on grape leaves varies with the dilution rate; e.g., initial dislodgeable
residues at 2 ug/cm had half-lives of 9 and 13 days when sprayed (1 pound
active ingredient per acre) in 100 and 25 gallons of water, respectively.
Workers became ill when they entered treated vineyards 39 days after
application; highly significant (P<0.001) lower blood cholinesterase levels
were found in workers 1 and 6 days after the reported illness. California's
Department of Food and Agriculture (unpublished communication) indicates that
an interval of 65 days is generally required2to reach a safe dislodgeable
foliar residue level of less than 0.06 ug/cm when the initial dislodgeable
residue level is as high as 2.3 ug/cm . Because field data are highly
variable, onsite residue tests, performed prior to reentry may be necessary.
In another study of the same fields where the above worker illness occurred
(Winterlin et al. 1978, 05001343), dislodgeable residues of dialifor and its
oxygen analog were 0.06-0.107 ug/cm (5.6-9.9 ppm) and 0.022-0.027
ug/cm (1.7-2.6 ppm), respectively, 59 days after application at 1 pound
active ingredient per acre.
For each crop, the registrant is required to propose an acceptable reentry
interval. This proposed interval may be based on any of the following:
a. the longest (most restrictive) existing interval;
b. data on dissipation of foliar residues (decline curve),
on human exposure to those residues; and on the inherent
toxicity of dialifor;
c. a determination of the time after which no detectable foliar
residues occur under appropriate climactic conditions, in the
geographical area in which dialifor will be applied.
The Agency is adopting the 75 day reentry interval established by the State of
California for the use of dialifor on Grapes (California Administrative Code,
January 4, 1979, Article 23, 2479 (H), Field Worker Safety). Registrants have
t is option of accepting the 75 day reentry interval or of supplying exposure
data, a dislodgeable residue decline curve and establishing an appropriate
reentry interval based on this data
5-11
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Reentry data must be submitted for the use of dialifor on citrus, pecans, and
apples.
5-12
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CHAPTER VI
TOXICOLOGY OF DIALIFOR
Introduction
The first section of this chapter discusses the toxicity of dialifor as an
active ingredient. The data discussed here pertain to the properties or
effects of dialifor as an active ingredient, and are relevant to an evaluation
of the risks and benefits of all products containing dialifor. This type of
data is referred to as "generic" data. "Generic" data gaps in the Toxicology
data base are discussed in this section. Product-specific Toxicology data gaps
(in acute toxicity testing) for currently registered manufacturing-use dialifor
products are also identified here.
The second section of this chapter discusses the toxicity of products currently
formulated from manufacturing-use dialifor. These products are grouped by type
of formulation and the toxicity of each type of formulation is discussed
separately. The toxicity of emulsifiable concentrate dialifor products is
discussed first, followed by a discussion of the toxicity of wettable powder
dialifor products.
"Generic" data on the toxicity of dialifor, as an active ingredient, normally
supplies sufficient information to establish the subchronic and chronic
toxicities of formulated products. However, acute toxicity data on each end-
use product, or substantially similar product, is required and must be
supplied. If these data are available, they are discussed in the formulation
sections. If gaps in the acute toxicity data base exist, they are identified.
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A. Manufacturing-use Dialifor
As discussed in Chapter III, the majority of company submitted toxicology
studies on dialifor were completed by Industrial Biotest Laboratories (IBT). A
number of these studies have been validated through the Laboratory Audit
Program and the results of the audit are presented in the topical discussions.
Some studies have not yet been validated through the Laboratory Audit Program,
and this too is indicated. However, all IBT studies have been screened for
indications of possible dialifor related adverse effects. IBT studies which do
not indicate adverse effects are considered invalid for purposes of
registration (fulfilling Agency testing requirements) until they have completed
the validation process in the Laboratory Audit Program. Registrants are
encouraged to consult with the EPA laboratory Audit Program prior to initiating
this category of testing.
Manufacturing-use Dialifor Toxicology Profile
Acute Toxicity
Single dose oral toxicity testing of dialifor shows a sex difference in rats
that is characteristic of many O,O-Diethyl phosphate derivatives. This sex
difference is not as significant in other (non rat) test species. Available
data indicate that manufacturing-use dialifor is acutely toxic, with reported
oral LD50 values ranging from 5-71 mgAg body weight in rats. In rabbits,
reported oral LD50 values range from 35-79 mgAg body weight. In mice,
reported oral LD50 values range from 39-64 mgAg body weight, and in dogs the
reported oral LD50 value is 97 mgAg.
This suggests that dialifor is very acutely toxic by the oral route. Symptoms
observed (salivation, diarrhea, sedation and tremors) are typical of
parasympathomimetic action and are similar to those observed for other members
of the organic phosphate family.
All acute oral toxicity testing on technical grade dialifor was conducted by
Industrial Biotest Laboratories (IBT) and has not yet completed validation
through the Laboratory Audit Program. For purposes of this Standard, these
data do not fulfill Agency testing requirements. Therefore, acute oral
toxicity testing on technical grade dialifor is a data gap.
In addition, acute oral toxicity testing of the oxygen analog of dialifor is
required because the Agency has established that this degradation product may
constitute up to 12.5% of weathered residues on food and in the field. Oxygen
analogs of organophosphate insecticides are also traditionally more toxic than
the parent compounds.
Available data on the dermal toxicity of technical dialifor suggest that the
dermal LD50 in rabbits is 145 mgAg body weight. This suggests that technical
grade dialifor is very acutely toxic by the dermal route.
The acute dermal toxicity testing discussed above was conducted by Industrial
Biotest Laboratories (IBT) and has not yet completed validation through the
Laboratory Audit Program. For purposes of this Standard, these data are
considered invalid and a data gap exists for acute dermal toxicity testing of
technical grade dialifor.
6-2
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In addition, acute dermal toxicity testing of the oxygen analog of dialifor is
required because the Agency has established that this degradation product may
constitute up to 12.5% of weathered residues on food and in the field. Oxygen
analogs of organophosphate insecticides are also traditionally more toxic than
the parent compounds.
Available data demonstrate that both atropine sulfate and 2-PAM have antidotal
action on acute oral dialifor toxicity.
Chronic Toxicity
Because dialifor is structurally similar to the human teratogen Thalidomide,
teratogenicity testing of dialifor is of particular concern. Three studies,
conducted by Industrial Biotest Laboratories, assessing the possible
teratogenic effects resulting from administration of dialifor to rabbits and
monkeys were reviewed. These studies have not yet completed validation through
the Laboratory Audit Program, and are therefore considered to be invalid for
purposes of this Standard. The Agency did screen these studies for indications
of adverse effects. The studies do suggest that dialifor may be fetotoxic and
teratogenic in rabbits. However, no definitive conclusions can be reached on
the teratogenicity of dialifor.
In addition to the three IBT studies on dialifor, the Agency also reviewed a
teratogenicity study in hamsters conducted by Jane Robens. This study also
indicated that dialifor may be teratogenic. However, the reported results were
not considered to be significant due to a high rate of maternal mortality. No
definitive conclusions can be drawn on the teratogenic potential of dialifor.
The Agency reviewed several animal metabolism studies which provide insight
into the fate of ingested dialifor in animals. The majority of ingested
dialifor appears to be excreted in the urine and feces. The results of
biochemical analyses indicate that the primary metabolic fate of dialifor
involves the conversion to phthalamic acid, which is excreted in the urine
rather than dialifor itself.
Clinical Trials
The Agency reviewed one study involving the oral administration of dialifor to
male and female humans. At dosages of .03 mgAg/day, 20-30% inhibition of
blood cholinesterase and aliesterase activities occurred. ND effects were
noted at dosages of .01 mgAg/day. This study was conducted by Industrial
Biotest Laboratories and has been determined to be supplemental through the
Laboratory Audit Program.
Accident Reports
The Agency has reviewed an accident report documenting a fieldworker poisoning
incident in the State of California. In addition, through communication with
the State of California, the Agency identified an earlier record of a
farmworker poisoning incident in 1973 involving worker exposure to dialifor and
phosalone residues. The first poisoning incident (1973 in Fowler California)
involved 32 grape pickers who harvested grapes 42 days after application of
dialifor. The second poisoning incident (1976 in Madera California) involved
118 grape pickers. Available data indicate that reentry occurred 15 days after
application. In both instances, workers, were exposed to residues of both
dialifor and phosalone (another organophosphate insecticide).
6-3
-------
In both incidents, fieldworkers were treated for cholinesterase poisoning and
no fatalities were reported.
"topical Discussions: Manufacturing-use Dialif or
Acute Toxicity
Acute Oral Toxicity (163.81-1)
The minimum data required for establishing the acute oral toxicity of
manufacturing-use dialifor (LD50) is one test on the technical chemical and on
each manufacturing-use product, preferably using the laboratory rat. Because
available residue chemistry data indicate that dialifor-oxon may form in the
field and may constitute a significant amount of residues in food, the Agency
is also requiring acute oral toxicity testing on this degradation product.
Technical grade dialifor, for purposes of acute oral toxicity testing is
considered to be equivalent to manufacturing-use dialifor. Requested testing
on technical grade dialifor will fulfill requirements for the currently
registered manufacturing-use product.
Several studies were available to assess the acute toxicity of technical grade
dialifor, and the results of these studies are summarized in the following
table:
Species
rabbits
rats
mice
rabbits
dogs
Sex
F
M
M
M
F
M
F
M
F
M
Dose Range
16-79
35-118
23-79
35-118
3-10
23-79
35-118
35-118
35-118
53-178
# animals
per dose
Toxicity
Category*
4
4
4
4
4
4
4
53 + 6
43 + 6
71 + 7
5 + 1
39+7
64 + 4
58+6
79+7
97+5
MRTD»
Reference
Jackson,
1966,
00002044
Schoenig,
1966,
00002043
N
H
N
N
II
* These studies are unaudited 1ST studies. The Agency is unable to establish
Toxicity Categories for this type of data.
Signs of toxicity in rabbits (Jackson, 1966, 00002044) included diarrhea,
salivation, sedation, and tremors preceding death (all signs of anti-
6-4
-------
cholinesterase poisoning). Necropsy of rabbits that died showed inflammation
of the muoosal lining of the stomach and small intestine. No changes were
found in the animals surviving the 14-day observation period. Similar findings
at necropsy were observed in rabbits by Schoenig (1966, 00002043).
Signs of toxicity noted by Schoenig (1966, 00002043) were similar in rats, mice
and dogs. These were typical symptoms of anti-cholinesterase poisoning.
However, there were no gross pathological findings at necropsy in any of the
three species tested.
An additional study on the acute oral toxicity of "recrystallized AC14503"
reported LD50 values in male and female rats of 69 mgAg and 5 mgAg
respectively. Because the test substance was not fully identified, the value
of this study is diminished. However, the LD50 values reported in this study
are in general agreement with those reported in other studies on the same
species utilizing technical grade dialifor.
All of the studies discussed above were conducted by Industrial Biotest
Laboratories. These studies have not yet completed validation through the
Laboratory Audit Program. Therefore, these studies must be considered invalid
for purposes of this Standard.
No testing of the acute oral toxicity of dialifor-oxon was available.
Acute Dermal Toxicity (163.81-2)
The minimum data required for establishing the acute dermal toxicity of
manufacturing-use dialifor is one test on technical dialifor and on each
manufacturing-use product, preferably using the albino rabbit. Because
dialifor-oxon may constitute a significant portion of weathered residues in
food and in the field, the Agency is also requiring testing on the oxon.
Technical grade dialifor, for purposes of acute dermal toxicity testing is
equivalent to the currently registered manufacturing-use product. Requested
testing on technical grade dialifor will fulfill requirements for acute dermal
toxicity testing on the currently registered manufacturing-use product.
One study was available to assess the acute dermal toxicity of technical grade
dialifor. This study is summarized below:
Single dermal
Sex dose range LD50 Tbxicity
Species (t/dose) (mgAg) Skin (mgAg) Category* Reference
rabbit M (2) 79-267 clipped 145 + 8 Schoenig,
intact 1966,
00002043
rabbit M (2) 79-267 clipped 145+8
abraded
* These studies are unaudited IBT studies. The Agency is unable to establish
Tbxicity Categories for this type of data.
6-5
-------
Signs of toxicity in this study were typical of anti-cholinesterase poisoning,
e.g. lethargy, salivation, and tremors.
Local skin reactions in all animals consisted of slight to moderate erythema.
This study was conducted by Industrial Biotest Laboratories and has not yet
completed validation through the Laboratory Audit Program. Therefore, this
study must be considered invalid for purposes of this Standard.
No testing was available on the oxygen analog.
Acute Inhalation Toxicity (163.81-3)
The minimum testing required to establish the acute inhalation toxicity of
manufacturing-use dialifor is one test on technical grade dialifor and on each
manufacturing-use product preferably in the laboratory rat. This testing is
required if technical dialifor causes a respirable vapor, or if 20% or more of
the aerodynamic equivalent is composed of particles not larger than 10 microns.
Technical grade dialifor, for purposes of acute inhalation toxicity testing is
equivalent to the currently registered manufacturing-use product. Requested
testing on technical grade dialifor will fulfill requirements for acute
inhalation toxicity testing on the currently registered manufacturing-use
product.
Acute inhalation testing is required and is unavailable on technical grade
dialifor. Registrants have the option of supplying the test or of
demonstrating that dialifor will not cause a respirable vapor, or that if a
respirable vapor is produced, the equivalent aerodynamic diameter of 20% of the
particulate is less than 10 microns.
Primary Eye Irritation (163.81-4)
The minimum testing required to establish the irritability of manufacturing-use
dialifor to the eye is one test on the manufacturing-use product, preferably
using the albino rabbit.
This testing need not be completed if data are submitted which indicate that
manufacturing-use dialifor is either a dermal irritant or possesses a pH of 1-3
or 12-14. A test substance that causes dermal irritation or that has a pH of 1-
3 or 12-14 will be judged corrosive to the eye..
One study was available to assess the primary eye irritation potential of
technical dialifor (Shoenig, 1966, 00002043). Using albino rabbits, both
undiluted dialifor (100 mg) and a 5% [w/v] suspension in propylene glycol (0.1
ml) was tested for eye irritation potential. Washing versus not washing the
test material after 1 minute of contact was also tested. In all animals, there
were no visible effects on the cornea. Irritation of both the iris and
conjunctiva was noted within 1 hour, but all effects were reversible within 72
hours to 7 days. The primary deficiencies in this study were the small number
of animals used and that both eyes were treated. This study will not satisfy
guideline requirements because of flaws in protocol followed in this study.
6-6
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Primary Dermal Irritation (163.81-5)
The minimum testing needed to establish the irritability of manufacturing-use
dialifor to the skin is one test on the manufacturing-use product preferably
using the albino rabbit.
This testing need not be conducted if data are submitted which establish that
the pH of manufacturing-use dialifor is 1-3 or 12-14. A product with a
demonstrated pH of 1-3 or 12-14 will be considered corrosive.
One study was available to assess the primary dermal irritation of
manufacturing-use dialifor (Shoenig, 1966, 00002043). The results indicate
that dialifor was only mildly irritating to the skin of rabbits.
However, because of errors in protocol and reporting, this study cannot be
considered valid.
Dermal Sensitization (163.81-6)
The minimum testing required to assess dermal sensitization for the
manufacturing-use product is an intradermal test on the manufacturing-use
product preferably using the guinea pig.
No testing is available, and testing is required.
Acute Delayed Neurotoxicity (163.81-7)
The minimum testing required for acute delayed neurotoxicity is one test on
technical dialifor. This testing is required because dialifor is known to
cause esterase depression.
One study was available to assess the acute delayed neurotoxicity of technical
dialifor (Jackson, 1968, 00001998). However, this study was conducted by
Industrial Biotest Laboratories and has been invalidated by the Laboratory
Audit Program.
Testing is required.
Subchronic Effects
Subchronic Oral Toxicity (163.81-1)
The minimum testing needed is one test on technical grade dialifor in two
mammalian species, preferably the rat and dog.
There are six subchronic oral toxicity tests on technical grade dialifor.
Three of these studies were conducted in dogs and three were conducted in
rats. The following table summarizes these studies:
6-7
-------
Species (#/dose)
Dose
Level Tested
Duration
Classification/
Deficiencies
Results
Reference
MRID
dog
M-F
(1)
0, 20, 100
500 ppm
14 days
Supplementary**
1) too few animals
used
2) no control groups
3) too few variations
monltered
4) observation period
too short for dog
sub-chronic stucjy
1) RBC + Plasma
ChE Inhibited
at all dose
levels (lowest
= 20 ppm)
2) Decreased food
Intake (all
doses)
3) Decreased body-
weight at high
dose (500 ppm)
4) No gross patho-
logy observed
*Schoen1g,
1966
MRID#
00002048
rats
M-F
(3)
0, 10, 20,
50, 100,
200, 500,
1000 ppm
14 days
Supplementary**
1) too few animals
used/dose
2) too few variables
morltered
3) observation period
too short for rat
sub-chronic study
1) dose related
decrease 1n RBC,
plasma + brain
ChE at all doses
(lowest dose
tested = 10 ppm)
2) 100 ppm and above
produced gross
signs of ant1-ChE
poisoning and
mortality (33%,
50%, 67%, 100%)
3) depressed weight
gain at higher
doses
*Wolf,
1966
MRID#
00002047
rats
M-F
(10)
0, 20,
50 ppm
90 days
Invalid by IBT Audit
*Wolf,
1966
MRID#
00002049
-------
Species
Sex
U/dose)
Dose
Level Tested
Duration
Classification/
Deficiencies
Results
Reference
MRTD
dogs
M-F
(2)
0, 1, 3,
10, 30,
100 ppm
98 days
Supplementary**
1) too few animals
used/dose
2) 98 days 1s too
short for a dog
subchronlc oral
study
1) ChE depression; *Baran,
NOEL for RBC and 1966
plasma 1 ppm, MRID#
for brain 300 ppm 00002051
2) At 100 ppm,
muscular weak-
ness, hyper-
sensitivity
3) All other para-
meters normal
(blood, urine,
gross + necro-
scopy)
rats
M-F
(21)
0, 0.3,
1, 3, 10,
30 ppm
90 days Supplementary (deter-
(28 day mined by IBT Audit)
recovery) 1) IBT Audit Final
2) Too few animals
used for ChE
measuremetns
(only 6/measure-
ment)
3) ChE only measured.
Other variables
not monltered.
1) ChE depression; *Wolf, 1966
NOEL for RBC and MRID#
plasma = 3 ppm; 00002050
brain = 10 ppm
2) plasma ChE
depression fully
recovered 1n 28
days
3) RBC and brain ChE
only partial
recovery In 4
weeks
4) Results con-
firmed by repeat
study using 6M-F
and measuring ChE
activity after
3 and 13 weeks.
dogs
M-F
0, 50,
100 ppm
2 years
Invalid by Audit
*Baran, 1968
MRID#00002028
*A"I1 studies conducted by IBT. Validations have been completed on MR1D000002050 (supplementary), MRID#00002028
(Invalid); and MRID000002049 (Invalid).
**Pend1ng Final IBT Audit
-------
The three dog studies were conducted by Industrial Biotest Laboratories. Of
these three studies, only one (Baran, 1968, 00002028) has completed validation
through the Laboratory Audit Program. This study has been determined to be
invalid.
The other two studies utilizing dogs as the test species were screened for
indications of dialifor-related adverse effects. Schoenig (1966, 00002048)
showed cholinesterase (ChE) inhibition in red blood cells (RBC) and plasma at
all doses tested (down to 20 ppm in the diet). No gross pathology was
observed. However, this study was of only 14 days duration, too short for a
subchronic study in dogs. Furthermore, too few animals were tested, there were
no control groups, and too few variables were monitored. This study was
inadequate as a subchronic oral test, although ChE depression was noted down to
20 ppm. In another study, Baran (1966, 00002051) also fed technical dialifor
to dogs and noted ChE depression in red blood cells (NOEL 1 ppm), plasma (NOEL
1 ppm) and brain (NOEL 30 ppm). All other parameters were normal (blood counts
and chemistry, urinalysis, gross pathology and microscopy).
These studies are flawed and do not satisfy Agency testing requirements.
All rat subchronic studies were conducted by Industrial Biotest Laboratories.
Wolf (1965, 00002047) fed rats technical grade dialifor for 14 days and
observed dose related decreases in RBC, plasma and brain ChE at all doses (down
to 10 ppm). Gross signs of anti-ChE poisoning and mortality (increasing with
dose) were noted at 100 ppm and above. This study is flawed and does not
fulfill Agency requirements.
In a subsequent study, Wolf (1966, 00002049) fed rats technical dialifor for 90
days. This study has completed validation through the Laboratory Audit Program
and has been determined to be invalid.
In a separate 90 day ChE study (Wolf, 1966, 00002050) rats were fed technical
dialifor and NOEL's were established for ChE inhibition as follows: RBC= 3 ppm,
plasma= 3ppm, brain= 10 ppm. Plasma ChE recovered in 28 days and there was
partial recovery of RBC and brain ChE in the same time frame. This study has
completed validation through the Laboratory Audit Program and has been
determined to be supplemental. It will not fulfill Agency requirements for
subchronic testing in the rat.
Although data do indicate that dialifor is a cholinesterase inhibiting
pesticide, the Agency is unable to set a No Observed Effect Level (NOEL) at
this time. Additional testing is required.
Subchronic 21-Day Dermal Toxicity (163.82-2)
The minimum data required for subchronic 21-day dermal toxicity is one test
utilizing technical grade dialifor, preferably in the albino rabbit.
There were no data available on technical grade dialifor. However, testing was
completed utilizing the emulsifiable concentrate product (Mastri, 1969,
00001946). The clipped, intact backs of rabbits (3/sex/dose) were exposed to
0, 1, 5 and 25 mgAg of emulsifiable concentrate dialifor (4 Ibs./gal) for a
total of 22 applications (30 days) at 6 hours/application. Test results are
summarized in the following table:
6-8
-------
Dose ChE Levels (Percent of Cbntrols)
(mgAq) Mortality Plasma RBC Brain
0 0/6 100% 100% 100%
1 0/6 102% 90% 76%
5 IF/6* 71% 35% 50%
25 1M, 2F/6* 31% 25% 21%
* Gross signs of anti-cholinesterase poisoning were salivation and diarrhea.
The data in the table show that brain ChE was depressed to varying degrees at
all dose levels (NOEL not determined); both RBC and plasma ChE NOEL's were 1
mgAg. Gross signs of anti-cholinesterase poisoning and mortality were
observed at higher doses. Slight irritation and erythema were noted at the
application site.
The "negative" results reported on the other parameters which were measured,
i.e. hematology, urinalysis, necropsy and histopathology, were questioned in
the Laboratory Audit Report. These negative findings cannot be regarded as
valid, and this study must be considered only supplementary.
Additional testing is required.
Subchronic Neurotoxicity (163.82-5)
The minimum data required for subchronic neurotoxicity testing is one test on
the technical grade chemical, using either the adult hen or a mammalian
species. This testing may be required if the results of the requested acute
delayed neurotoxicity test is positive.
Subchronic 90-Day Dermal Toxicity (163.82-3)
Testing is not required because the use of dialifor does not involve purposeful
application to skin or result in significant human dermal exposure.
Subchronic Inhalation Toxicity (163.82-4)
Testing is required if the results of the requested acute inhalation toxicity
test indicate that repeated exposure at a concentration that is likely ::o be
toxic occurs under normal conditions of use.
Chronic Effects
Chronic Feeding (163.83-1)
The minimum data required for an assessment of the chronic toxicity of dialifor
is one test on the technical grade chemical, preferably using the laboratory
rat.
6-9
-------
One two-year chronic feeding study in rats was available (Wolf, 1968,
00002021). However, this study was conducted by Industrial Biotest
Laboratories and has been determined to be invalid through the Laboratory Audit
Program.
Additional testing is required.
Oncogenicity (163.83-2)
The minimum data required to assess the potential oncogenic effects of dialifor
is testing on the technical grade chemical in two mammalim species, preferably
the rat and mouse.
No data were available. Testing is required.
Reproductive Effects
Teratogenicity (163.83-3)
The minimum data required to assess the potential teratogenic effects of
dialifor is testing in two mammalian species using the technical chemical.
Dialifor is structurally related to the known human teratogen Thalidomide (see
Figure 1), therefore testing of dialifor is of special concern.
There are four studies which were available to assess the teratogenic potential
of dialifor. Three of these studies were conducted by Industrial Biotest
Laboratories and have not yet completed validation through the Laboratory Audit
Program. These studies therefore, do not fulfill teratogenic testing
requirements for dialifor.
A screen of these studies for indications of adverse effects provided seme
useful information.
In one study (Kennedy, 1966, 00002054), groups (N=10) of rabbits were given 1,
3, 10 and 25 mgAg dialifor, 75 mgAg Thalidonide (positive control) or 260
mgAg corn oil on days 6 through 18 (inclusive) of gestation. High maternal
mortality was noted in the 10 mg/kg (70%) and 25 mgAg (100%) dialifor treated
groups. No "abnormal" young (based on a limited number of parameters) were
noted in controls or at 1 or 10 mgAg dialifor. Thirty "abnormal" young were
observed in the Thalidomide positive controls. The abnormality described was
severe clubbing of the extremeties. In addition, in the 3 mgAg dialifor
treatment group three of the young showed umbilical hernias (examination for
skeletal development did show normally formed skeletal structures) and one was
partial acranius. At doses of 1, 3 and 10 mgAg dialifor, a decrease in fetal
viability was seen, and at 10 mgAgf son increase in fetal resorption occurred.
These results suggest possible dialifor related teratogenic and adverse
reproductive effects. However, no definitive conclusions can be made regarding
the teratogenicity of dialifor.
In a similar study, also conducted by Industrial Biotest Laboratories, Jackson
and Kennedy (1966, 00002055) repeated the experiment described above using 1
and 3 mgAg dosages of dialifor. In the Thalidomide treated positive control
group (75 mgAg)r twenty four "abnormal" young (severe clubbing of the
extremeties and talipes varus) were reported. No abnormalities were reported
6-10
-------
I!
A
/ N
I
THALIDOMIDE
S CK •
CHj-ci
DIALIPOR
^Figure I
-------
in the untreated controls or the test, groups receiving dialifor. There was no
evidence of maternal mortality in any group, although the number of resorption
sites was greater in the test groups receiving dialifor than in the untreated
controls. This suggests a possible dialifor related reproductive effect.
There was also a slight decrease in the number of viable young in the dialifor
treated groups, suggesting possible fetotoxic effects. However, no definitive
conclusions can be made regarding the teratogenicity and fetotoxicity of
dialifor.
In a third study, also conducted by Industrial Biotest Laboratories, female
stumptailed macques were used to test the teratogenic potential of dialifor
(Vondruska, 1969, 00001976). The design and execution of this study was
severly flawed ( e.g. no controls, limited anatomical observations, etc.). The
monkeys were given dialifor (1 mgAg; N=10) or Thalidomide (5 or 10 mg/kg; N=3
and 6) during gestation (days 23-21; 24-30; 23-30). Monkeys given dialifor
showed an average depression of 35% in RBC and plasma ChE activity, but no
gross effects were noted in any of, the seven major organs or major bones
examined. All of the fetuses in the Thalidomide treated groups displayed
anomalies of the appendages, but no gross changes were observed in major organs
examined.
The final study reviewed by the Agency on the teratogenic potential of dialifor
was conducted by Jane Robens (1970, 05001994). The test species used was
hamsters. Dosages in the dialifor treated groups ranged from 0 to 500 mg/kgf
and dosages in the Thalidomide positive control groups ranged from 300-1200
mg/kg. The results suggest possible dialifor related reproductive effects.
However, this study cannot be considered a valid test for the teratogenic
potential of dialifor because maternal mortality was significant at all
dialifor dose levels, the Thalidomide positive controls did not produce dose
related teratogenic effects, and only gross external signs of teratology were
monitored.
Additional testing is required. One of the species tested must be either
rabbits or monkeys. The species chosen for teratogenicity testing of dialifor
is of special concern because the teratogenic effects of Thalidomide are more
reliably reproduced in rabbits and monkeys. Because dialifor is structurally
similar to Thalidomide, there is a good possibility that the mode of action may
be similar, and that testing in rabbits (more economically feasible than
testing in monkeys) would provide better information.
Reproduction (163.83-4)
The minimum data required to assess the reproductive effects of dialifor is
testing in one mammalian species, preferably the laboratory rat, using
technical grade dialifor and lasting for two generations.
A three generation rat reproduction study, conducted by Industrial Biotest
Laboratories, was reviewed by the Laboratory Audit Program and has been
determined to be invalid (Arnold, 1968, 00002029).
Testing is required.
6-11
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Mutagenicity
The following studies represent only the minimum requirements for data on the
potential heritable effects of technical dialifor.
1. A mammalian j.n vitro point mutation test.
2. A sensitive submammalian point mutation test (bacteria, fungi,
insect).
3. A primary ENA damage test (i.e., sister chromatid exchange or
unscheduled ENA synthesis).
4. A mammalian in vitro cytogenetic test. If this test suggests a
positive result, a dominant lethal or heritable translocation test may
be required.
After results from these test systems and other Toxicology disciplines have
been considered, additional testing may be required to further characterize or
quantify the potential genetic risks.
These requirements should be considered as an interim guide and not final
Agency policy.
Metabolism
Metabolism (163.85-1)
The minimum data required to assess the metabolic fate of dialifor is a single
dose test using the analytically pure grade of the active ingredient in a
radioactively labeled form.
Although some data were available which provide insight into the metabolic fate
of dialifor, none of the studies are adequate to fulfill Agency requirements.
In one study (Bourke, et al ., 1970, 00001972), rats were given a single oral
dose (1 mg/kg) of C labeled dialifor. Within 50 hours most of the
radioactivity (80%) was recovered in the urine and feoes. Of the remaining 20%
in the animal, 7-13% was associated with the digestive tract, with only .2%-.!%
remaining in the liver and kidney. In another part of this study, five male
and five female rats were given 1 mgAg of labeled dialifor. Excreta were
collected for 7 days. The results were similar to those reported in the 50-
hour study, with 50% of the radioactivity present in the urine, and 40% in the
feces within 48 hours. The radioactivity in the urine was "tentatively"
identified as phthalamic acid (by R and infrared spectral analysis).
In another report, also utilizing rats. Ford and Friant (1971, 00001957)
attempted to identify dialifor metabolites in urine. Each of 16 rats were
given 4 mg of radiolabeled dialifor in corn oil via stomach tube. Urine was
collected for 24 hours and was subject to numerous biochemical procedures to
identify the compounds containing the radioactive label. The results suggest
that the primary metabolic fate of dialifor involves conversion to phthalamic
acid, which is excreted in the urine rather than dialifor itself.
6-12
-------
The studies described above are not adequate becaus«4the purity of the test
material was not specified, the specific labeling ( C) of dialifor was not
given, no time course of radioactive label recovery or total recovery was
reported (only in Ford and Friant, 1971, 00001957), and identification of the
metabolites was insufficient.
Additional testing is required.
Clinical Trials'
The Agency reviewed a study assessing the effects of dialifor (unspecified
formulation) on plasma and RBC ChE activity and plasma aliesterase activity in
humans (Greco, 1970, 00001950). Oral administration of dialifor to male and
female human subjects caused 20-30% inhibition of blood cholinesterase and
aliesterase activities at doses of .03 mgAg/day for four weeks to .10
mgAg/day for ten days. At these doses, partial to complete recovery occurred
within seven weeks. No effects were noted (NOEL) at .01 mgAg/day for two
weeks. No changes were observed in any of the hematological variables measured
at any of the dose regimens tested.
This study was conducted by Industrial Biotest Laboratories and has been
determined to be supplemental.
Antidotes
The Agency reviewed one study (Mastri, 1968, 00002020) which assessed the
efficacy of atropine sulfate and 2-PAM as antidotes in rats. This study is
summarized below:
Treatment Schedule Oral LD50 (mgAg)
a. Technical Grade Dialifor alone (35-119 mgAg) 71 + 7.3
b. Technical Grade Dialifor (52-400 mgAg) approx. 140
+ 30 minutes
Atropine Sulfate (17.5 mgAg)
c. Technical Grade Dialifor (118-400 mgAg) 266 + 31.3
+ 30 minutes
2-PAM Cl (50 mgAg)
d. Technical Grade Dialifor (79-267 mgAg) 177 + 21
+ 30 minutes
Atropine Sulfate (17.5 mgAg)
2-PAM Cl (50 mgAg)
Toxic signs noted were typical of anti-ChE poisoning. No gross pathologic
findings were noted in any of the animals at necropsy.
6-13
-------
This study is adequate to establish an acute oral LD50 for technical grade
dial if or in male rats of 71 + 7 mgAg* It is also adequate to demonstrate that
both atropine sulfate and 2-PAM have antidotal action (increases the LD50) on
the acute oral toxicity of dialifor. 2-PAM was more effective as an antidote
than atropine sulfate.
This study was conducted by Industrial Biotest laboratories and has not yet
completed validation through the Laboratory Audit Program. The LD50 value
reported in this study cannot be considered valid.
6-14
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B. Emulsifiable Concentrate Dialif or
Emulsifiable Concentrate Dialifor Toxicology Profile
As discussed in Chapter III, the majority of toxicity testing on dialifor was
conducted by Industrial Biotest Laboratories. A number of these studies have
completed validation through the Laboratory Audit Program, and this is
indicated in the topical discussions where applicable. Several studies have
not yet completed this validation step, and this too is indicated. For
purposes of this Standard, these studies do not fulfill Agency requirements for
testing.
Acute Toxicity
Data discussed in the manufacturing-use dialifor portion of this chapter
suggest that technical grade dialifor is extremely toxic via the oral route.
No acute oral toxicity data are available on any end-use emulsifiable
concentrate product. The Agency assumes that existing emulsifiable concentrate
dialifor products are also extremely toxic via the oral route. The acute
dermal toxicity of emulsifiable concentrate dialifor places these products in
category II.
Topical Discussions: Emulsifiable Concentrate Dialifor
Acute Toxicity
Acute Oral Toxicity (163.81-1)
No data were available to assess the acute oral toxicity of any currently
registered emulsifiable concentrate product. The Agency will assume, based on
acute testing of technical grade dialifor, that existing emulsifiable
concentrate dialifor products are extremely toxic. Testing is required.
Acute Dermal Toxicity (163.81-22)
One study was available to assess the acute dermal toxicity of emulsifiable
concentrate formulations containing dialifor. The LD50 in male rabbits is 326
+ 18 mg/kg when applied to intact skin (Mastri, 1969, 00002269). Signs of
toxicity were typical of anti-cholinesterase poisoning, e.g., ataxia,
salivation, tremors, fibrillations, diarrhea and lethargy. Pale red erythema
and edema were noted at the application site in all groups. Necropsy revealed
no other gross pathologic alterations.
This study has been certified by the Laboratory Audit Program and is of
sufficient quality to fulfill testing requirements. The dermal LD50 value
places EC formulations in category II, corresponding to a moderate acute dermal
toxicity potential. No additional testing is required
6-15
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Acute Inhalation Toxicity (163.81-3)
An acute inhalation toxicity test is required on each EC formulation unless
evidence is submitted indicating that the particular product will not produce a
respirable vapor or that if a respirable vapor is produced, the equivalent
aerodynamic diameter of 20% of the particulate is less than 10 microns.
One study (Hathaway, 1969, 00001974) was reviewed and was found to be
inadequate because of numerous serious flaws in protocol and study conduct.
Additional testing is required.
Primary Eye Irritation (163.81-4)
No data were available to assess the eye irritation potential of any EC
product. Testing is required.
Primary Dermal Irritation (163.81-5)
No data were available to assess dermal irritability of any EC product.
Testing is required.
Dermal Sensitization (163.81-6)
No intradermal tests for dermal sensitization in laboratory animals are
available on any EC formulation. Testing is required.
6-16
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C. Wettable Powder Dialifor
As described in Chapter III, the majority of toxicity testing of dialifor was
conducted by Industrial Biotest Laboratories. A number of these studies have
completed validation through the Laboratory Audit Program, and this is
indicated in the topical discussions where applicable. Several studies have
not yet completed validation, and this too is indicated. For purposes of this
Standard, these studies do not fulfill Agency requirements for testing.
Wettable Powder Dialifor Toxicology Profile
Acute Toxicity
Data discussed in the manufacturing-use portion of this chapter suggest that
technical grade dialifor is extremely toxic via the oral route. No data were
available to assess the acute oral toxicity of the wettable powder product.
The Agency will assume that it too is extremely toxic via the oral route.
Acute dermal toxicity testing has been provided and the results place wettable
powder dialifor in category II.
Topical Discussions: Wettable Powder Dialifor
Acute Toxicity
Acute Oral Toxicity (163.81-1)
No data were available to assess the acute oral toxicity of wettable powder
dialifor. Testing is required.
Acute Dermal Toxicity (163.81-2)
One study was available to assess the acute dermal toxicity of wettable powder
dialifor. The LD50 determined in this study for male rabbits (Mastri, 1969,
00003280) is 735 + 213 mgAg on intact skin. Signs of toxicity were typical
of anti-cholinesterase poisoning and skin reactions were mild. Necropsy
revealed no other pathologic alterations.
This study has been certified by the Laboratory Audit Program and is considered
to be adequate for Agency testing requirements. The reported LD50 value places
wettable powder dialifor in toxicity category II, corresponding to a moderate
acute dermal toxicity. No additional testing is required.
Acute Inhalation Toxicity (163.81-3)
An acute inhalation study is required en the wettable powder product unless
evidence is submitted showing that either the wettable powder product will not
produce a respirable vapor, or that if a respirable vapor is produced, the
equivalent aerodynamic diameter of at least 20% of the particulate is less than
10 microns.
6-17
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One study was reviewed and found to be inadequate (Hathaway, 1969, 00001975)
because of numerous serious flaws in protocol and study conduct.
Testing on the manufacturing-use product will fulfill requirements for this
wettable powder product.
Primary Eye Irritation (163.81-4)
No data were available on the wettable powder product. Testing is required.
Primary Dermal Irritation (163.81-5)
No data were available on the wettable powder product. Testing is required.
Dermal Sensitization (163.81-6)
No int -adermal testing is available for the wettable powder product. Testing
is required.
6-18
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CHAPTER VII
RESIDUE CHEMISTRY
A. Introduction
For any pesticide which has uses that may directly result in residues on
food or feed, the Agency sets an allowable residue level, or tolerance, for
each commodity on which it may occur. A tolerance level for a particular
chemical on a particular commodity is a function of the chemical's
toxicity, the percentage of an average daily diet comprised by the
commodity, and the amount of residue that can be expected to occur on that
commodity at the maximum directed rate of application. The total amount of
chemical to which a person may be exposed from all sources should always be
less than the toxicological estimate of a safe "Allowable Daily Intake."
The insecticide dialifor is used in the control of a variety of spiders,
mites, and scales in the following food crops: citrus fruits, apples,
grapes, and pecans. The majority of its current use is in pecans.
Tolerance levels of 3.0 ppm (citrus), 1.5 ppm (apples), 1 ppm (grapes), and
.01 ppm (pecans) have been established (CFR 180.326). In addition,
tolerance levels of 0.15 ppm (red meat), .006 ppm (milk and dairy
products), .05 ppm (poultry), and .01 ppm (eggs) have also been established.
B. Manufacturing use Dialifor
1. Residue Chemistry Profile
Dialifor is an insecticide-acaricide used to protect citrus fruits, apples
grapes and pecans.
Dialifor is not considered to be systemic in plants, although its residues
will penetrate into the peel or rind of fruit. The residues consist
primarily of dialifor and of lesser amounts of the oxygen analog.
Available data indicate that up to 12.5% of remaining residues consist of
the oxygen analog.
The oxygen analog is thought to form through photodegradation. The amounts
of the oxygen analog" which are present in different crops indicate that
hydrolysis, not oxidation, is the favored route of metabolic degradation.
The two initial fragments which result from hydrolysis are N-l-hydroxy-2-
chloroethyl phthalimide and O,O-Diethyl thiophosphoric acid. The phthaloyl
moiety is extensively metabolized to phthalamic and o-phthalic acids which
are found it plants in the form of salts. The thiophosphoric moiety is
metabolized to thiophosphoric and phosphoric acids which are reabsorbed and
enter into the cellular pool.
The metabolism in animals appears to be similar to that which occurs in
plants. However, whereas plants retain their metabolic products, animals
eliminate the majority of them in the urine. In addition, animals are
unable to completely degrade the parent compound, which is found intact in
the feces.
7-1
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Adequate dialifor-specific and dialifor-oxon-specific analytical methods
are available for detection of residues on citrus fruits, apples, grapes,
and their derived by-products: meat, milk, poultry and eggs. Data are
available on residues in these commodities.
Available residue data show that the combined residues of dialifor and
dialifor-oxon found in and on the above commodities, resulting from
presently registered uses, do not exceed the established tolerances in 40
CFR 180.326. The use of currently recommended application rates and
preharvest intervals will insure residue levels below tolerance limits on
the raw agricultural commodities at harvest. There are no records of
regulatory incidents involving the enforcement of these tolerances.
2. Required Labeling
Labels of dialifor wettable powder and emulsifiable concentrate products
must contain the following restrictions:
Grapes, Apples, citrus,, and Pecans: "Do not combine emulsifiable
concentrate formulations with Bordeaux mixtures. Do not feed or allow
livestock to graze on cover crops grown in treated areas. Do not
contaminate food or feedstuffs (storage and disposal). Do not apply when
weather conditions favor drift from treated areas."
Topical Discussions
a. Uptake, Distribution, and Metabolism in Plants
In addition to what may remain of an original application of the chemical,
residues may also consist of the chemical's metabolites, as formed by the
plant crop to which it was applied. The major and minor pathways of the
chemical's absorption, transformation, and distribution can be deduced
experimentally from the analysis of radiolabeled applications.
Applications by various routes, for example to the roots or leaves, will
show differences in absorption rates. The distribution of the chemical and
its metabolites can be examined by measuring the radioactivity present in
various plant fractions. Isolated metabolites can then be characterized by
chromatography, partitioning, or electrophoresis. Metabolic
transformations often result in an increase of polarity of the foreign
chemical to facilitate elimination. Metabolites characterized as highly
polar may have undergone conjugation with naturally occurring amino acids,
sugars, or sugar acids. Further chemical analysis can help identify the
exact nature of the conjugations. Other possible major transformations can
occur by hydrolysis, oxidation/reductions, or the breaking of unstable
bonds. The absorption, distribution, and metabolic fate of the chemical
determine the potential quantity and identity of pesticide residues in
plants used for food or feed.
Dialifor is a foliar insecticide and acaricide, and its use is primarily
directed to leaves. The absorption, distribution, and metabolic fate of
^jalifor was investigated by J.B. Bourke et al (1970, 00001972). When
C-ring labeled dialifor is applied to a surface of bean or tomato leaf
7-2
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or injected into the plant stem, the bulk of radioactivity remains at the
site of application. Autoradiograms show that the slight movement that has
occurred after 18 days of application is primarily through the leaf veins,
thus indicating that such movement was in the form of water insoluble
metabolites moving in the xylem. Direct injection into tomato fruit did
not show any movement of the pesticide through the parent plant, thus
proving that dialifor does not kill insects or mites by systemic action.
Additional studies on isotopic dilution techniques were conducted on citrus
plants by J.J. Ford et al .(1971, 00001958, 1972, 00002127, and Hercules,
1968, 00002032), in support of the preceding radioautography data. Four
miniature orange trees (Calamondin), in full leaf and fruit were sprayed to
runoff with C-ring labeled dialifor in methylene chloride and the
recovered runoff was assayed. Samples of leaves and fruits were Soxhlet-
extracted with acetone for internal residues, and all the residues were
identified by thin layer chromatography.
Residues of dialifor were also determined by GLC. Distribution of
radioactivity in samples taken at 1-, 4-, 8-, 12-, and 14-week intervals
indicated the presence of dialifor per se ,its oxygen analog, and two
metabolites, the phthalamic acid and the o-phthalic acid.
14
Immediately after application, 83% of the total C-labeled residue was
identified as dialifor. The following changes were observed:
Dialifor 65% of the total labeled material after 1 week.
51% of the toal labeled material after 14 weeks.
Dialifor-oxon 17% of the total labeled material after 1 week.
9% of the total labeled material after 14 weeks.
Phthalamic and 18% of the total labeled material after 1 week.
o-phthalic acids 39% of the total labeled material after 14 weeks.
The level of radioactivity on the leaves was found to be 15-20 times larger
than that on the fruits. No radioactivity was detected in the fruit pulp
or in the new growth after 12 weeks. Whatever internal residues were found
did not decrease appreciably after 14 weeks; therefore, they did not
undergo complete degradation.
Dialifor shows little tendency to translocate from foliar deposits or to be
absorbed into fruit pulp. Residues are found primarily in the peel or
rind, and they tend to be extremely persistent, as shown by decline curves.
In vitro hydrolysis and photogegradation studies (Ford, 1971, 00001956)
show that the decomposition products are phthalamic and o-phthalic acids.
The major pathway of metabolic degradation of dialifor in plants begins
with the formation by hydrolysis of N-l-hydroxy-2-chloroethyl phthalimide
and O,O-diethyldithiophosphororic acid-. The former is metabolized to
phthalamic acid and o-phthalic acids, found in the plant in the form of
salts. The minor pathway involves the formation by oxidation of the oxygen
analog, which is generally detected in amounts up uo 12.5% of the total
residue (Hercules, 1972?, 00002125). The fate of the thiophosphate
fragment has been thoroughly studies by R.J. O'Brien, who found that
thiophosphoric and phosphoric acids are reabsorbed and become part of the
cellular pool.
7-3
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The residues in apples, apple pcmace, oranges, orange pulp, orange oil,
grapes, grape pomace, and raisins which are open to toxicological
considerations are dialifor per se and its oxygen analog (Eastmen, 1968?,
00002027). No oxygen analog as component of the total residue has been
reported for pecans.
b. Metabolism in Animals
From one feeding study with rats (Burke et al ., 1970, 00001972), using
radio-labeled material, it was indicated that the metabolism of dilaifor in
animals apparently proceeds in a manner similar to that in plants, with its
conversion to dialkyldithiophosphoric acids and to compounds containing the
phthalic acid moiety. Small amounts of dialifor per ^e are transferred to
the tissues.
14
C radiotracer studies involving the ingestion of dialifor by large
ruminants (cows, goats) have not been submitted. Feeding studies using
unlabeled dialifor show that animals are unable to completely degrade the
parent pesticide. Thus, beef calves maintained from 2 to 8 weeks on a dry
diet containing an excessive level of 60 ppm of dialifor (J.J. Ford, 1969,
00002024) showed up to 0.4 ppm of dialifor per se in fat tissues and up to
0.30 ppm in liver tissues.
In another study, dairy cows maintained for three weeks on a diet
containing 40 ppm dialifor showed 0.0001 ppm to 0.013 ppm of dialifor per
se in milk (Ford, 1968? 00002022). Based on these data, maximum residues
in milk should be slightly above 0.01 ppm or 0.26 ppm on a fat basis.
In a final study by St. John et al .(1971, 05001830), dialifor was fed to a
dairy cow at a level of 5 ppm for 4 days. Neither dialifor nor its oxygen
analog were found in milk. Dialifor was absent in the urine, and about 3%
of the total dialifor fed was found in the feces. The metabolism of
dialifor in animals appears to be similar to that in plants. Overall, the
fate of dialifor in animals is adequately described.
c. Analytical Methods
Metabolism data indicate that dialifor per se and up to 12.5% of its oxygen
analog comprise the bulk of the residue found in plants and animals.
The regulatory method for the analysis of dialifor in crops is contained in
Vol. II of the Pesticide Analytical Manual, as Method I, and was submitted
by Hercules (J.J. Ford, 19??, 000020005). In this method, 200 g of ground
apple or orange peel or juiced orange pulp samples are extracted 3 times
with 400 ml. each of acetone in a Waring blender at high speed for 5
minutes. The extracts are filtered through a coarse fritted funnel,
combined and concentrated to a volume of 900 ml. of acetone. Following a
multistep cleanup procedure, the dialifor residues can be detected by gas
liquid chrcmatography employing a phosphorus-specific potassium chloride
thermionic detector. The sequence of this clean-up is as follows:
1- Methylene chloride water partition
2- 5 Component absorbent material
3- Celite partition column
4- Acetonitrile-hexane partition
5- Alumina column
7-4
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Appropriate clean-up procedures are selected depending on the commodity
undergoing analysis. For instance, for apples, steps 1,2, and 3 are only
applied; for oranges, steps 1, 4, and 5 are applied. When operated as
described (Ford, 1968, 00002005) the thermionic detector responds to
dialifor at the one nanogram level. The sensitivity of the method is 0.01
ppm. This method is also so specific that none of the other common
organophosphorus pesticides interfere (the retention time of dialifor is
considerably greater than that of any of these materials).
The method was validated by the Food and Drug Administration laboratory in
Los Angeles, California, and by EPA (1971). The average recovery obtained
by EPA for dialifor in orange samples fortified at 1.5 to 3 ppm was 92.2%,
and individual values varied from 84% to 98%. Recoveries were slightly
higher at the same levels before final clean-up steps were preformed.
This method has only been validated for dialifor per jse but is said to be
capable of detecting the oxygen analog with good sensitivity.
A thin layer chromatography-cholinesterase inhibition method has been
described as suitable for detecting residues of dialifor and its oxygen
analog in foods (Hercules, 1968, 00002037). Briefly, the technique
utilizes enzymatic inhibition as the detection system in conjunction with 5-
bromoindoxyl acetate as the chromogenic agent.
The procedure is capable of detecting 2-3 ng of dialifor and it oxygen
analog. The method was validated (Eastmen, 1968, 00002027). Recovery
studies of the oxygen analog on apples fortified at levels of 0.02-0.08 ppm
ranged from 82% to 100%. Recoveries of the oxygen analog on oranges
fortified at levels of 0.04-0.20 ppm ranged from 85-100%.
Acceptable methods for the determination of dialifor in beef tissues and
milk were submitted by Hercules and are published in the Pesticide
Analytical Manual, Vol. II, as Method II and Method III.
Method II consists of extracting the residue from meat, fat and meat by-
products with an acetone-chloroform mixture. An aliquot is evaporated to
dryness and the residue dissolved in hexane-acetonitrile. After
partitioning and evaporation, the residue is cleaned up on an alumina
column. The residue is determined using the gas chrbmatographic parameters
specified in Method I. This method was subject to a method trial in EPA
laboratories with beef suet. Levels of fortification were at 0.12 ppm and
0.06 ppm of dialifor with recoveries ranging from 96% to 104% in the first
case, and 80% to 96% in the second case. The sensitivity of the method is
0.005 ppm.
In Method III, the milk fat is extracted with potassium oxalate,
isopropanolr ether and n-hexane solvents. The organic solvent with the
pesticide residue is dissolved in benzene and passed through an alumina
column before determination by gas liquid chromatography using a thermionic
detector. The method was validated by EPA: analysis of fortified milk
samples indicated recoveries of 80% and 88% at the 2.5 ppb level, and of
90% to 102% at the 5.0 ppb level. The sensitivity of the method is 0.5 ppb
for milk fat.
7-5
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The above methods have been validated, have adequate specificity, and are
satisfactory for enforcement purposes.
d. Residue Data
Field residue data for dialifor should reflect the registered use with
regard to application rate, mode of application, number and timing of
treatments, formulations used, and geographical areas represented.
Because the oxygen analog may have an increased cholinergic potency, it
is important to establish the levels of this oxon likely to be found in the
combined residues on agricultural crops.
Some data were available to assess the proportions likely to be found in
these crops. Residues of the oxygen-analog were determined in 52 selected
samples of apples, orange peels, orange oil, orange (by-product dried)
pulp, peaches, grapes, cottonseed, potatoes, and soil, using the TLC-enzyme
inhibition procedure previously described. Residues of dialifor were
determined by a GLC procedure (Eastmen, 1968?, 00002027).
Residues of the oxygen analog were found in almost every sample containing
the parent compound, dialifor, and ranged up to 0.13 ppm (except for higher
values of 0.45 ppm and 0.60 ppm in orange oil due to concentration and
processing). Of the 52 samples, only three contained an oxygen analog
residue exceeding 10% of the combined residues (e.g. 10.2%, 12.5%, and
17.2%; the last value is derived from inconsistent and questionable data).
The preponderance of values show that the oxygen analog represents up to
12.5% of the combined residue of dialifor per se and dialifor-oxon.
Previously this value had been rounded off to 10%.
If dialifor alone is determined, the combined residue residue can be
calculated as follows:
ppm dialifor = ppm combined residue
0.875
The stability of dialifor residues during storage were also considered.
Fortified acetone extracts of orange peels were reanalyzed after intervals
of 1 to 5 months. The analytical data show that residues of dialifor
persist unchanged in frozen extracts for periods of up to 25 weeks. For
apple extracts they are stable up to 43 weeks (Hercules, 1968?, 00002032).
These data are considered adequate for the crops discussed in this Standard.
Pecans
The directions for use of dialifor emulsifiable concentrates on pecans call
for a) foliar application up to shuck split, b) single or multiple spray
applications at a maximum rate of 0.45 Ib ai/100 gallons (not to exceed 5.4
Ib ai/acre/application), and c) different frequencies of application
depending upon the type of pest to be controlled.
The available residue data for pecans (J.J. Ford, 1969, 00001990) reflect 3
single 0.5 Ib ai/100 gallon spray applications to foliage of 10 pecan trees
at 2-week intervals in Albany, Georgia. The interval between last spray
and harvest was 35 days. Nut samples were analyzed by either a surface
7-6
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stripping analysis or nut-meat analysis. The regulatory method I (PAM
Vol. II), slightly modified, was used to detect dialifor residues on these
samples. The reported residue stripped from the pecan surface ranged from
0.006 ppm to 0.016 ppm with anaverage of 0.009 ppm. Crop blanks are
reported as 0.000 ppm (sensitivity of this method is 0.004 ppm). The
residue in the edible nut-meats averaged 0.005 ppm based on the analysis of
10 samples. Crop blanks are reported as 0.003 ppm (method sensitivity
0.003 ppm).
Additional data for residues of dialifor in pecans were presented (J.J.
Ford, 1972, 00002130). A total of 33 samples from 6 tests located in 3
different states were analyzed. An average of 16 to 17 trees were sprayed
to run-off with emulsions at concentrations of 0.5 Ib to 1 Ib of ai/100
gallons. The number of applications ranged from 2 to 6. The intervals
between last spray and harvest varied from 14 to 121 days. The maximum
residue in the nut-meats was less than 0.005 ppm, the detection limit of
the analytical method used.
Unshelled nuts (meat plus shell, but excluding the husk) showed a maximum
residue of 0.016 ppm at 35 days PHI (Ford, 1969, 00001990). Therefore, the
shell is not a potential source of contamination of the nut-meat. Adequate
recovery (120%) at 0.005 ppm fortification level was cited. The only real
residue found on pecans was on the husk or shuck, but a tolerance is not
required for the shuck because it is not used as animal feed or human food.
The submitted residue data are adequate to support a 0.01 ppm tolerance for
combined residues of dialifor and dialifor-oxon in pecans. Data on levels
of dialifor-oxon in pecans are not required due to the low levels of
combined residues reported.
Citrus Fruits and Processed Citrus Products
Oranges
Use directions for the application of dialifor on oranges call for foliar
spray applications up to seven days before harvest (PHI). Several kinds of
applications are offered: single yearly applications at a maximum rate of
0.45 lbs/100 gallon and at a mimimum rate of 0.113 lbs/100 gallons, or
double yearly applications at a maximum rate of 0.36 lbs/100 gallons and at
a minimum rate of 0.113 lbs/100 gallons.
Summary Table
Crop Rate of Application PHI Residues Reference
Valencia 6-double .25 Ib ai/100 gal. 3 days .7 ppm Hercules, 1968,
Oranges (second application 3 7 days .69 ppm 00002032
months after first) 84 days .37 ppm
6-double .5 Ib ai/100 gal. 3 days 1.3 ppm "
(second application 3 7 days 1.2 ppm
months after first) 84 days .61 ppm
Residue data obtained for these samples indicate a half-life of
approximately 70 days at each of the two dosages studied. The decrease of
7-7
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residue with time is a function of weathering and of growth of mature
fruits. Since, in this study, mature oranges were used, the residues found
represent the maximum that would occur from the given applications. In
addition, the study confirms that dialifor residues are not confined
entirely to the peel of the orange, because the residue does not penetrate
into the edible portion of the fruit even after exposure for periods of 12
weeks. The reported residues are calculated values based on analyses of
peel fractions and adjustment to the whole fruit basis. Crop blanks were
reported as 0.0 ppm (sensitivity of the method, 0.01 ppm).
Summary Table
3 & Rate of Application PHI
Residues Reference
Pineapple
Oranges
3@ .29 Ib ai/100 gal.
(first application at
petal fall; final 5
months later)
3@ .5 Ib ai/100 gal.
(first application at
petal fall; final 5
months later)
3
84
days
days
3 days
84 days
1.4 ppm
.59 ppm
1.9 ppm
1.1 ppm
Hercules,
1969?,
00001967
Hercules,
1968?,
00001968
Hercules,
1969?,
00001969
The analyses reported above were done at Pesticide Research Laboratory,
University of Florida, The studies utilized three instead of the maximum
of 2 treatments. However, in each case where applications were made, the
first was made at petal fall when the fruit had just started to form. Thus
for this evaluation we can equate the treatments in the residue studies to
the recommended dual applications.
The residue data obtained from pineapple oranges indicated a half-life of
80 to 85 days. The residue levels reported are on a whole fruit basis.
Recovery studies with pineapple orange peel samples showed an average value
of 90.6% at a 5.83 ppm dialifor fortification level. These data are not in
perfect agreement with the residue levels in Hercules, 1968, 00002032,
because the reported residue values show a maximum level of 1.2 ppm at 7
days after the last application at the higher spray rate in 00002032.
7-8
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Summary Table
Valencia
Oranges
_# £ Rate of Application
4 single @ 5 oz./lOO gal.
water/full coverage spray
4 single @ 10 oz./lOO gal.
water/full coverage spray
4 single @
water /acre
5 Ib ai/50 gal.
PHI
3 days
125 days
3 days
125 days
3 days
125 days
4 single @ 10 Ib ai/50 gal. 3 days
water/acre 125 days
4 double @ 5 Ib ai/50 gal. 3 days
water/acre 125 days
4 double @ 5 oz./lOO gal. 3 days
water/full coverage spray 125 days
Residues
4.9 ppm
.7 ppm
6.7 ppm
1.4 ppm
9.1 ppm
2.5 ppm
18.5 ppm
4.3 ppm
14 ppm
3.6 ppm
7.4 ppm
2.4 ppm
Reference
Vfestlake,
1971,
05001345
1 single @ 5 oz./lOO gal.
water/full coverage spray
1 single @ 10 oz./lOO gal.
water/full coverage spray
7 days 1.2 ppm
7 days 2.4 ppm
Decline curves were submitted and showed a residue half-life of 60 days for
the concentrated spray (5 Ib and 10 Ib ai/50 gallon water acre), and a
residue half-life of 40 days for the dilute spray (5 oz. and 10 oz./lOO
gallon water/full coverage spray). The difference was attributed to the
two types of applications (blast spray for concentrated and manual for the
diluted).
Analysis of the pulp of the samples collected at 7r 21, 42, 75, and 125-day
intervals showed no detectable residue, showing that the pesticide did not
penetrate into the pulp. Recovery data were good for the determination of
residues in rind and pulp of oranges using the GLC method developed by
Hercules (J.J. Ford, 1968, 00002005). At a .5 ppm fortification level the
orange pulp gave a recovery of 91 + 9%. At a 3 ppm fortification level the
orange rind gave a recovery of 105 + 3%/ Good recoveries of 110% were also
obtained for ground rinds fortified with 3 ppm.
7-9
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Summary Table
Valencia
Oranges
f & Rate of Application PHI Residue Reference
Single .5 lb/100 gal. spray
3 days
7 days
14 days
28 days
56 days
84 days
1.7 ppm
1.8 ppm
1.7 ppm
1.4 ppm
1.2 ppm
.88 ppm
Reinking ,
1973?,
00002138
Blanks are reported as 0.0 ppm. Sensitivity of a modification of the GLC
method developed by Hercules was 0.01 ppm.
Grapefruit
The directions for application of dialifor to grapefruit are basically the
same as those for application to oranges. However, when double application
is called for, one must be done in the spring (post blossom) and the other
in the summer.
Summary Table
Crop
Ruby
Grapefruit
£ £ Rate of Application
30 .29 Ib ai/100 gal.
3@ .5 Ib ai/100 gal.
PHI
3 days
84 days
3 days
84 days
Residue
.64 ppm
.62 ppm
1.2 ppm
1.1 ppm
Reference
Hercules,
1969?,
00001967
Hercules,
1968?,
00001968
Hercules,
1969?,
00001969
Ruby
Grapefruit
Single @ .5 lb/100 gal.
spray
3 days
7 days
14 days
28 days
56 days
84 days
1.8 ppm
1.9 ppm
1.8 ppm
1.7 ppm
1.6 ppm
1.4 ppm
Reinking,
1973?,
00002138
Recovery studies with grapefruit peels (00001967, 00001968, 00001969),
showed an average value of 98.8% at a 2.9 ppm dialifor fortification
level. All blanks were reported as 0.0 ppm. These values are in agreement
with reported levels in oranges in Hercules, 1968, 00002032.
Within the limits of experimental error, residues of dialifor in grapefruit
did not change from the third day after the last treatment until the final
sampling at the 84th day. Even at the higher rate they were below the
established tolerance of 3 ppm for combined residues of dialifor and its
oxon in citrus fruits.
7-10
-------
lemons
directions for use of dialifor in on lemons call for foliar
applications up to seven days before harvest. Several types of application
are offered, single and double (spring and summer spray), at a maximum rate
of 0.45 Ib ai/100 gallons and a minimum rate of 0.113 Ib ai/100 gallons.
Summary Table
# & Rate of Application PHI Residues Reference
Lemons 3@ .29 Ib ai/100 gal. 3 days .25 ppm Hercules,
65 days .08 ppm 1969?,
00001967
Hercules,
3@ .5 Ib ai/100 gal. 3 days .38 ppm 1968?,
65 days .24 ppm 00001968
Hercules,
1969?,
00001969
Recovery studies with lemon peels showed an average value of 91.73% at a
1.41 ppm dialifor fortification level. All blanks were reported as 0.05
ppm.
Summary Table
Crop # & Rate of Application PHI Residues Reference
Lemons Single 10 oz. ai/100 gal. 6 days 1.53 ppm Westlake,
1971,
05001345
Analysis of the pulp of the samples collected at 7, 21, 42, 75, and 125-day
intervals showed no detectable residue, showing that the pesticide did not
penetrate into the pulp. Recovery data were good for the determination of
residues in rind and pulp using the GLC method developed by Hercules (J.J.
Ford, 1968, 00002005). At a .5 ppm fortification level the lemon pulp gave
a recovery of 99 _+ 19%. At a 3 ppm fortification level the lemon rind gave
a recovery of 110 +_ 9%. Good recoveries of 110% were also obtained for
ground rinds fortified with 3 ppm dialifor.
7-11
-------
Citrus Pulp, Molasses, and Citrus Oil
Two pilot plant studies reported in 00002033 and 00001966 show residue data
for orange and grapefruit by-products such as juice, citrus oil, molasses,
and dried citrus pulp. Molasses and dried citrus pulp constitute part of
conmercial cattle feed and deserve special consideration. Valencia Oranges
and Ruby Red Grapefruit were commercially processed at Lake Alfred, Florida.
Summary Table
# & Rate
Crop of Application PHI
Valencia .25 Ib ai/100 gal. 21 days
Oranges
.5 Ib ai/100 gal. 21 days
Ruby Red .25 Ib ai/100 gal. 20 days
Grapefruit
.5 Ib ai/100 gal. 20 days
Residues
Reference
RAC: .52 ppm Hercules,
Juice: None found 1969,
Chopped Peels: .76 ppm 00002033
Molasses: .16 ppm Hercules,
Dried Citrus Pulp: 2.7 ppm 1971?,
Orange Oil: 6.4 ppm 00001966
RAC: .86 ppm "
Juice: None found
Chopped Peels: 1.6 ppm
Molasses: 1.3 ppm
Dried Citrus Pulp: 5.5 ppm
Orange Oil: 12 ppm
RAC: .55 ppm "
Juice: None found
Chopped Peels: .85 ppm
Molasses: .14 ppm
Dried Citrus Pulp: 2.6 ppm
Grapefruit Oil: 20 ppm
RAC: 1.2 ppm "
Juice: None found
Chopped Peels: 1.6 ppm
Molasses: .25 ppm
Dried Citrus Pulp: 6.1 ppm
Grapefruit Oil: 37 ppm
In processing unwashed oranges to dry pulp, the concentration factor was
2.7/0.52 = 5.1 at the lower spray rate and 5.5/0.86 = 6.4 at the higher
spraying rate.
In processing grapefruit to dry pulp, the conversion factor was 2.6/0.55 =
4.7 at the lower spraying rate and 6.1/1.2 = 5.1 at the higher spraying
rate.
These studies show concentration factors from unwashed orchard fruit to
dried citrus pulp of from 4.7-6.4. When the feed item is reconstituted
7-12
-------
with molasses at 2/3rd dried pulp and l/3rd molasses, the maximum in the
reconstituted feed would be:
2^ (6.4 x 3) + _! x 1.3 = 13.2 ppm dialifor
3 3
Therefore, a food additive tolerance is needed, and a level of 15 ppm for
combined residues of dialifor and its oxygen analog in dried citrus pulp is
considered appropriate.
The highest residues were found in citrus oil samples, amounting to 6.4 ppm
to 12 ppm for orange oil and 20 ppm to 37 ppm for grapefruit oil. This is
because the oil fraction represents the more solubilizing vehicle for the
pesticide residue, as well as being the smallest fraction of the original
fruit. The results of both studies are in agreement. A tolerance is
needed for citrus oil.
In the recovery of the citrus oil, the following concentration factors were
observed: 6.4/0.52 = 12.3; 12/0.86 = 14.0; 20/0.55 = 36.4 and 37/1.2 =
30.8. The maximum level likely to occur would be 36.4 x 3 = 109.2 ppm
combined residue. Therefore, a Food Additive tolerance of 110 ppm is
considered appropriate for combined residues of dialifor and its oxygen
analog in citrus oil.
Grapes
The directions for use of dialifor on grapes call for two foliar spray
applications per season, one before and one after the shotberry stage, at a
rate of 0.9 Ibs. ai/15-120 gal. water/acre (35 days PHI are indicated).
The label limits use to California.
Summary Table
Crop
t & Rate of Application
PHI
Residue
Reference
Thompson 3 double @ .5 Ib ai/acre
Seedless
Grapes
3 double § 1 Ib ai/acre
34 days .54 ppm Ford, 1970,
48 days .36 ppm 00001984
62 days .23 ppm
34 days 1.2 ppm "
48 days .7 ppm
62 days .94 ppm
Concord 1 double @ 1 Ib ai/acre
Grapes
78 days 2.2 ppm "
Crop blanks are quoted as 0.00 ppm. Sensitivity of the method is 0.2 ppm.
Additional residue data from two decline studies and two terminal residue
studies from San Joaquin Valley, California were reported. Decline studies:
7-13
-------
Summary Table
Crop
ft & Rate of Application PHI
Residues Reference
Thompson
Seedless
Grapes
1-3 § 1 Ib ai/acre
1-3 @ 2 Ibs ai/acre
0 days
7 days
14 days
28 days
56 days
112 days
0 days
7 days
14 days
28 days
56 days
112 days
1.27 ppm
.26 ppm
.76 ppm
.68 ppm
.63 ppm
.08 ppm
2.63 ppm
1.79 ppm
2.46 ppm
1.65 ppm
2.26 ppm
.25 ppm
Etord, 1972,
00002127
Blanks were quoted as 0.0 ppm and the sensitivity of the method was 0.01
ppm.
Terminal residue studies:
Summary Table
Crop » & Rate of Application
Carignane Single @ 1 Ib ai/acre
& Emperor
Single @ 2 Ibs ai/acre
PHI
2 days
7 days
13 days
27 days
48 days
68 days
2 days
7 days
13 days
27 days
48 days
68 days
Residues Reference
1.8 ppm
.86 ppm
.80 ppm
.41 ppm
1.0 ppm
.42 ppm
1.8 ppm
1.1 ppm
.87 ppm
.53 ppm
.59 ppm
.37 ppm
Ec-rd, 1972,
00002127
More recent residue data from a field study conducted in California have
been submitted.
7-14
-------
Summary Table
Crop
t & Rate of Application PHI
Grapes 3 @ 1 Ib ai/acre
Grapes 3, @ 1 Ib ai/acre
Residues Reference
35 days .67 ppm Hercules,
40 days .83 ppm 1973,
00002117
34 days 1.2 ppm Hercules,
1969?,
00001994
The data presented on residues of dialif or in or on grapes demonstrate that
the established 1 ppm tolerance for combined residues of dialifor and
dialifor oxon on or on fresh grapes will not be exceeded when dialifor is
applied as directed (with a 35 day preharvest interval). Only one sample
showed a maximum residue value of 1.2 ppm.
The decline curves of residues on Carignane and Bnperor grapes showed
little initial deposits from two sprays of about 2.0 ppm at the rate of 2
Ibs. ai/acre, a steady decline for 25-30 days to about 0.4 ppm, and finally
a leveling off with little additional loss until harvest. The pattern of
residue decline coincides with the growth of the grapes, there being
practically no growth dilution over the last 20-25 days before harvest.
Sprays of the final application are the ones that affect the value of the
final residue. Recovery studies on grapes indicate an average value of 93%
at a fortification level ranging from 0.3 ppm tp 0.5 ppm. The tolerance of
1 ppm for combined residues of dialifor and its oxygen analog is therefore
considered adequate for fresh grapes.
Raisins and Raisin Waste
The recommended treatment to harvest interval for raisins is 60-70 days in
place of 35 days for fresh grapes. Raisins are, in fact, harvested several
weeks later than the fresh fruit because they need additional time to
develop their high sugar content.
7-15
-------
Residue studies of dialifor levels found on raisins made from dialifor
treated grapes are summarized below:
Summary Table
Crop
# & Rate of Application
PHI
Residues Reference
Thompson
Seedless
Raisins
Thompson
Seedless
Raisins
.5 Ib ai/acre
1 Ib ai/acre
.5 Ib ai/acre
1 Ib ai/acre
62 days
62 days
62 days
62 days
.37 ppm
1.2 ppm
.30 ppm
1.2 ppm
Ford,
1970,
00001984
1- Unprocessed raisins, field dried, fumigated with methyl bromide and
cured.
2- Processed raisins, field dried, washed, de-stemmed, and sorted for size.
The concentration factor was 1.44 at both application rates.
Summary Table
Crop
» & rate of Application PHI
Raisins Double @ 1 Ib ai/acre
Single @ 3 Ibs ai/acre
Residues Reference
41 days
71 days
49 days
1.4 ppm
1.6 ppm
4.3 ppm
Ford, 1972,
00002127
The average concentration factor was quoted as 3.2, ranging from 1.8 to
4.3, respectively; however, that for Thompson seedless grapes (average of
2) was 4.1.
7-16
-------
Residue data from a 1973 field study conducted in California are presented
below and support a concentration factor of 1.6 from grapes to processed
raisins:
Sumnary Table
Crop » & Rate of Application PHI
Residues
Reference
Raisins 3 @ 1 Ib ai/acre
2 @ 1 Ib ai/acre
35-40 days
70 days
.98 ppm
.2 ppn
Hercules,
1973,
00002117
Owing to the effect of processing, the concentration factor is considered
to be 1.6, and the maximum of combined residues in raisins is 1.6 ppm. The
established Food Additive Tolerance of 2 ppm is therefore appropriate for
combined residues of dialifor and its oxygen analog in or on raisins.
Raisin waste, which contains imperfect raisins and associated trash
obtained as a by-product of raisin production, was found to contain up to
2.8 ppm of dialifor. The raisins, containing an average residue of 1.2
ppm, were the source of the waste, giving a concentration factor of 2.3.
Fresh grapes, bearing residues of dialifor at 1 ppm, could therefore yield
processed raisins at 2 ppm and raisin waste at 4.6 ppm combined residues.
The Food Additive Tolerance of 10 ppm for combined residues of dialifor and
its oxygen analog in raisin waste is more than ample. However, because of
the variation of residues in trash, a change (reduction) in the level of
this tolerance is not recommended.
Grape Juice and Pomace
Summary Table
Crop f & Rate of Application PHI
Residues
Reference
Emperor Single § 1 Ib ai/acre Unknown
Grapes Single @ 1.8 Ib ai/acre Unknown
Juice: .005 ppm
Juice: .008 ppm
Ford, 1972,
00002127
The dialifor residue on these grapes was about 0.4 ppm, indicating that the
residue detected in the juice was 1/50 of that in fresh grapes. Juice of
grapes bearing a dialifor residue of 1.0 ppm (tolerance level) would
therefore contain no more than 0.02 ppm.
7-17
-------
Summary Table
Crop * & Rate of Application PHI Residues Reference
Grapes 1 Ib ai/acre 68 days Pomace: .57 ppm Ford, 1972,
1.8 Ibs. ai/acre 68 days Pomace: 1.4 ppm 00002127
Based on the residues on the fresh grapes estimated from the decline curve,
the concentration factors for grapes to wet pomace are the same as those
for grapes to unprocessed raisins, 4.3. Because 27% of the weight of the
fresh grapes was converted to the pomace remaining after juice extraction,
a concentration factor of 1/0.27 = 3.7 would be expected if the residue on
the fresh fruit were entirely retained in the pomace. For Thompson
Seedless Grapes, the concentration factor is 4.1.
Thus, the combined residue of dialifor and its oxon in wet grape pomace is
considered to be about 5 ppm.
In 00001984 a concentration factor of up to 4 from wet grape pomace to
dried grape pomace can be calculated. Thus, the maximum overall
concentration factor from fresh grapes to dried pomace is 1 x 4.3 x4 = 17.2.
Based on the tolerance in grapes of 1 ppm, the Food Additive tolerance of
20 ppm for combined residues of dialifor and its oxygen analog is
appropriate for dried grape pomace.
Apples, Pomace, and Juice
The directions for use on apples call for multiple foliar spray
applications (no more than 6) up to 60 days before harvest in states
bordering on or east of the Mississipi River. Two types of application are
recommended: multiple .75 and .5 Ibs a.i./lOO gallons water in spray
applications, using the 50% W.P. formulation. The most commonly used
method of application is to point of runoff, and the maximum amount
actually applied per acre is indicated as 2.26 Ibs. dialifor/acre (at the
.75 Ib application level) and 1.5 Ibs. dialifor/acre (at the .5 Ib
application level).
7-18
-------
Sunnary Table
Crap t & Rate of Application PHI Residues Reference
Apples 6 50% WP @ .5 Ib ai/100 gal.
Pennsylvannia
Apples 6 4% EC @ 1 Ib ai/100 gal.
Wisconsin
6 4% EC @ 1.5 Ib ai/100 gal.
Apples Multiple 50% WP
New York @ .5 Ib ai/100 gal.
Apples 1 50% WP @ .25 Ib ai/100 gal.
England 1 50% WP @ .5 Ib ai/100 gal.
1 50% WP @ 1 Ib ai/100 gal.
41 days 1.0 ppm
27 days 1.7 ppm
27 days 4.3 ppm
37 days .85 ppm
Hercules,
1968,
00002034
80 days
80 days
80 days
.07 ppm
.01 ppm
.21 ppm
Crop blanks were 0.00 ppm and the sensitivity of the method was 0.01 ppm.
Eight studies with field apples, seven in Eastern States and one in Western
States (Washington), showed the following:
Sunnary Table
Terminal Residue Studies
Location # & Rate of Application
PHI Resi
-------
Sunmary Table
Decline Studies
Location
t & Rate of Application PHI
Residues
Reference
Arendtsville 6 WP @ .5 Ib ai/100 gal.
Pennsylvania "
6 WP @ 1 Ib ai/100 gal,
N
II
II
Yakima 3 EC @ 1 Ib ai/100 gal.
Washington "
0 days
7 days
14 days
28 days
52 days
0 days
7 days
14 days
28 days
52 days
0 days
7 days
14 days
21 days
28 days
42 days
58 days
3.4 ppm
3.2 ppm
1.6 ppm
1.1 ppm
.66 ppm
4.8 ppm
4.4 ppm
2.2 ppm
1.4 ppm
1.1 ppm
7.8 ppm
7.5 ppm
4.9 ppm
4.6 ppm
4.9 ppm
3.2 ppm
3.2 ppm
Pord,
1969,
00001961
Control samples showed no detectable residues. The decline curves from the
Pennsylvania study and the Washington study show a very similar rate of
decline in residues, with a change in slope at 32 and 28 days
respectively. The two corresponding half-lives for dialif or calculated
from the second half of the decline curves were 40 days and 65 days
respectively. Growth dilution was found to be the principal factor in the
reduction of dialifor residues on apple fruit in Washington.
In Pennsylvania, where the wettable powder was used, additional losses
attributed to climactic factors were observed. Another cause of higher
residues was the method of application (to full runoff). This study shows
that dialifor is a persistent pesticide because little residue is lost
after the initial period. It also shows that the 50% wettable powder gives
lower residues than the emulsifiable concentrate, and, that in the western
states, the residues are higher. Recoveries of dialifor ranged from 88% to
94% at .5 to 2.5 ppm fortification levels.
7-20
-------
WP @
.5 Ib ai/100 gal.
n
li
n
n
n
63 days
n
n
n
n
n
1.4 ppm
.43 ppm
1.16 ppm
.18 ppm
1.44 ppm
1.10 ppm
Ford,
1972,
00001993
Twenty additional studies on field apples were submitted:
Summary Table
Location # & Rate of Application PHI Residues Reference
Yakima, WA 6
Winchester, VA
Arendstville, PA
Hancock, MD
Fennville, MI
Geneva, NY .
Winchester, VA 6 WP @ 1 Ib ai/100 gal. 63 days .77 ppm
Yakima, WA " " 2.04 ppm
Arendtsville, PA " " 2.32 ppm
Fennville, MI " "2.3 ppm
Geneva, NY H " 1.5 ppm
These studies confirm that dialifor forms a persistent residue on apples,
and that its half-life ranges from 17 days to more than 70 days for the
wettable powder formulation, with an average of 46 days.
Doubling the proposed rate does not result in a proportional residue
increase. The data are adequate to support the established tolerance of
1.5 ppm for combined residues of dialifor and its oxon in or on fresh
apples at the recommended application rate and preharvest interval.
Apple Juice and Pomace
Summary Table
Crop ft & Rate of Application PHI Residues Reference
Apples 50% WP @ 1 Ib ai/100 gal. Unknown RAC: .63 ppm Ford,
Juice: .04 ppm 1972,
00001993
The magnitude of the residue detected in the juice was less than 1/10 the
residue on the whole fruit. Fortification and recovery experiments for the
juice samples yielded an average recovery of 99% over a fortification range
of 0.025 to 0.20 ppm.
The apples were processed in small quantities to produce apple pomace.
Data reported show that there are variable concentrations between the
harvested apples and wet pomace, ranging iron 1.6-3.8. When apples are
pressed for juice the yield is usually 22 or 25% wet pomace by weight, the
concentration factor being 4.5 or 4, assuming no losses. This is in
reasonably good agreement with the highest observed factor of 3.8. Using
7-21
-------
this observed factor, the combined residues of dialifor and its oxon in wet
apple pomace is 1.5 x 3.8 = 5.7 ppm (6 ppm). The factor between wet and
dried pomace was not determined experimentally. However, it has been
calculated with wide variations up to 7.5.
The usual concentration factor between fresh fruit and dried pomace is 25.
With this factor, the residue in dried pomace, given the established
tolerance of 1.5 ppm for residues in apples, is 1.5 x 25 = 37.5 ppm for
combined residues of dialifor and its oxon. Thus, the Food Additive
tolerance of 40 ppm in dried apple pomace is considered appropriate.
Animal Feeds Using Citrus, Apple and Grape By-Products
Wet and dried apple pomace, dry citrus pulp, dried grape pomace and raisin
waste are sometimes utilized as components of cattle feed. Dried grape
pcmace is also fed to poultry. Hercules (1972?, 00002125) reports the
maximum percentages that are incorporated in the total animal diet and the
accompanying contributions can be calculated as follows:
Product
Maximum as
Combined Residues
Maximum Payment
in Tbtal Diet
Maximum Combined
Residues Contributed
to Total Diet
Citrus Pulp 15 ppm
dry
Apple Pomace 6 ppm
wet
Apple Pomace 40 ppm
dry
Grape Pomace
wet
6 ppm
Grape Pomace 20 ppm
dry
Raisin Waste
10 ppm
30% (cattle)
30% (cattle)
50% (cattle)
50% (cattle)
20% (cattle)
5% (poultry)
10 % (cattle)
4.5 ppm
1.8 ppm
20.0 ppm
3.0 ppm
4.0 ppm
1.0 ppm
1.0 ppm
Meat, Milk, Poultry and Eggs
It is a well-known agricultural practice to feed dry apple pomace, dry
citrus pulp and dry grape pomace to farm animals such as cattle, goats,
sheep and poultry. The following studies were conducted to determine
whether or not residues would transfer from feed to meat, milk, poultry and
eggs.
7-22
-------
No residue studies are reported for treated cover crops in fruit orchards
where cattle may be grazaed.
There are no registered uses for dialifor on primary forage crops.
Milk
A study on three dairy cows fed at a rate of 45 ppm dialifor for three
weeks (9 times the normal feeding level). Residues in whole milk were
found to be dialifor per se and ranged from 0.001 to 0.013 ppm. The
average value for three cows throughout the period was 0.0008 ppm. One
value of 0.035 ppm was considered aberrant and was discarded. Analyses of
the milk samples were performed with Regulatory Method III, PAM Vol. II.
Recoveries of milk samples fortified at 8 to 41 ppb were 90%. Sensitivity
of the method is 1-2 ppb. For milk containing 4% fat, 0.01 ppm dialifor is
equivalent to 0.01 x 100 =0.25 ppm on a milk fat basis.
4"
Milk was also analyzed in a feeding experiment performed on a Hblstein cow
that was fed dialifor daily at a level of 5 pprj for a period of 4 days
(St. John and Lisk, 1971, 00002268, 05001830). Samples of milk from this
animal were collected during the feeding period and for 6 days thereafter.
No residues of dialifor or its oxygen analog were found in any of these
samples, analyzed by a slightly modified version of the method mentioned
above (electron affinity gas chromatography was the detection system).
Samples of milk fortified with 0.05 ppm of dialifor gave a recovery of 80-
92%. Samples of milk fortified with 0.05 ppm of the oxygen analog gave a
recovery of 62-78%. Sensitivity of the method was 0.01 ppm.
The maximum amount of dialifor residues which can be transferred from
different animal feeds to milk fat are presented in the following table
from 00002022:
Dietary Residues Maximum Dialifor Milk Fat
Product Dialifor Level in Milk Contributed Basis
Dry Citrus Pulp 45 ppm 0.01 ppm 4.5 ppm .025 ppm
Wet or Dry 45 ppm 0.01 ppm 20 ppm .11 ppm
Apple Pomace
Wet or Dry 45 ppm 0.01 ppm 4.0 ppm .022 ppm
Grape Pomace
Raisin 45 ppm 0.01 ppm 1.0 ppm .05 ppm
Waste
The tolerance of 0.15 ppm for residues of dialifor in milk is adequate.
7-23
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Meat
In a feeding study (Ford, 1969, 00002024) three beef calves were maintained
on a dry diet containing 60 ppn of dialifor administered for different
intervals of time; 2, 4, and 8 weeks for each calf. A fourth calf served
as the control. At the end of the feeding period, the animals were
sacrificed, and the tissues were analyzed. Lean muscle, liver, kidney and
fat tissues were analyzed by TLC and gas chrcmatographic procedures.
Regulatory method II was used. Sensitivity of the method is 0.005 ppm.
All residues except those in liver and fat were said to be non-detectable
«0.1 ppm). Residues in the liver of the animals sacrificed at 4 and 8
weeks ranged from 0.1 to 0.3 ppm. However, 1 ppm was found in the liver of
the animal sacrificed at 2 weeks. The latter value is not typical and was
probably influenced by illness contracted by the calf. As to fat, maximum
residues of 0.4 ppm occurred. All tissues were also analyzed by TLC for
residues of oxygen analog but no significant quantities were reported. In
two samples of liver and fat tissues the residues were close to the method
sensitivity (3-5 ppb).
In order to obtain additional information, 9 beef calves were fed 0, 2.0,
and 4.0 ppm of dialifor (Taylor, 1969, 00002038). The animals were killed
and samples of tissues were taken at 12 and 28 days. No dialifor was
detected in liver, kidney, fat and lean muscle tissues taken at 12 days,
and residue values in the range of the sensitivity of the method (2-3 ppb)
were detected in 5 of the 24 tissue samples taken at 28 days. No dialifor
was detected in the remaining 19 tissue samples. Recovery was uniformly
greater than 87% for the method used.
Based on the above data, the maximum which can be transferred from
different feeds to animal tissues can be calculated:
Contribution Transfer to:
Product to Total Diet Liver Fat
Cry Citrus 4.5 ppm .023 ppm .03 ppm
Pulp
Dry Apple 20 ppm .1 ppm .13 ppm
Ponace
Dry Qrape 4.0 ppm .02 ppm .027 ppm
Pomace
Raisin Waste 1.0 ppm .0005 ppm .0007 ppm
The tolerance of .15 ppm for residues in meat, fat and meat by-products of
cattle, goat and sheep is adequate.
Poultry
Residues in poultry and eggs are determined in an 8-week feeding study
using 18 laying hens divided into 6 groups of 3 birds each (Ford, 1972,
00002129). Two groups were fed dialifor at 3.7 ppm, 2 groups at 11.2 ppm
7-24
-------
and 2 groups served as controls. Egg samples were collected every 96
hours, shelled, blended and analyzed. They showed no residue. One bird
from each group was sacrificed after 4 weeks and tissue samples were
analyzed. The remaining birds were sacrificed at the end of the 8-week
period. Method II with a sensitivity of 5 ppb was used. Average
recoveries of 90% are quoted at the 3 microgram dialifor fortification
level.
The available data are contradictory because some controls showed apparent
residues of dialifor, indicating contamination of the feed. In addition,
there was no apparent dose-response; a considerable percentage of the birds
showed no detectable residues regardless of dose level. Highest net
residues were 0.05 ppm in several of the organs. These data show that
trace residues can be transferred to the tissues of poultry and are covered
by the tolerances of 0.05 ppm for poultry and 0.01 ppm for eggs.
Current Tolerances
Tolerances have been established in the United States as follows for
residues of dialifor and its oxygen analog pursuant to 40 CFR 180.326 (FR
39:9964, March 15, 1974; and FR 39:13073, April, 1974):
at; in;
3 ppm or on citrus
1.5 ppm or on apples
1 ppm or on grapes
0.15 ppm (N) meat, fat and meat by-products of
cattle, goat and "sheep
0.15 ppm (N) milk fat (reflecting negligible
residues in whole milk)
0.05 ppm (N) meat, fat, and meat by-products
of poultry
0.01 ppm (N) eggs
0.01 ppm (N) pecans
N= negligible residue tolerance
Permanent Food Additive Tolerances have been established for residues of
dialifor and its oxygen analog pursuant to 21 CFR 123.130 and 561.140:
at; in;
40 ppm apple pomace, dried
15 ppm citrus pulp, dried
20 ppm grape pomace, dried
2 ppm raisins
10 ppm raisin waste
7-25
-------
Theoretical Maximum Residue Contribution
The TMPC (Theoretical Maximum Residue Contribution) of dialifor to the
human diet is currently .265 mg/day.
Crop
Citrus Fruits
Apples
Grapes
(inc. raisins)
Meat (red)
Milk & Dairy
Products
Poultry
Eggs
Pecans
Tolerance
Pood Factor
3.0 ppm
1.5 ppm
1.0 ppm
0.150 ppm
0.006 ppm
0.050 ppm
0.010 ppm
0.010 ppm
3.81
2.53
0.49
10.81
28.62
2.94
2.77
0.03
mg/day (1.5 kg)
0.17154
0.05693
0.00736
0.02433
0.00258
0.00221
0.00042
0.00000
Codex Tolerances
TMRC: 0.2654 mg/day (1.5 kg)
Maximum residue limits in the form of tolerances have been recommended by
the Codex Alimentarius Commission for residues of dialifor and its oxygen
analogue (sic), expressed as dialifor. Because these recommendations are
currently in Step 8, this country can expect a request to accept them.
These are:
Maximum Residue Limit Type of Limit
Tnig/kg)
at
40
2
«
3
15
20
1
.2 (carcase fat)
.01*
.2 (fat basis)
Z
.01*
.05*
.05*
I
.2 (carcase fat)
T
T
T
T
T
T
T
T
T
T
T
T
T
T
T
in
Apple Pomace (Dried)
Apples
Cattle, Carcase Meat
Citrus Fruit
Citrus Pulp (dried)
Eggs
Grape Pomace (dried)
Grapes
Milk
Pears
Pecans
Poultry, Fat
Poultry, Carcase Meat
Raisins
Sheep, Carcase Meat
* Level at or about the limit of detection.
7-26
-------
"tolerances have been established in Canada as follows for residues of
dialifor:
at ^n
2.0 ppm citrus fruits, raisins
1.5 ppm apples
1.0 ppm grapes
.1 ppm pecans
When the Codex MRL's are advanced to Step 9 of the Codex approval process,
the following changes in this country's tolerances will be implemented,
toxicological considerations permitting:
Apples: increase the tolerance from 1.5 to 2.0 ppm
Meat, fat and meat byproducts of cattle (with or without goats)
and sheep: increase the tolerance from .15 to .2 ppm
Milk Fat: increase the tolerance from .15 to .2 ppm
These changes would increase the TMRC from .265 to .295 mg/day.
Regulatory Incidents
No report was made of any action taken by FDA, even though dialifor is
looked for; and none by APHIS (USDA).
C. Dialifor End-Use Formulations
1. Registration Requirements
For future registration of a product for use on a food or feed crop not
covered by this Standard, the Agency must be provided with a petition for
tolerance, a full range of data including a validated method for analysis
of residues in or on the raw agricultural commodity, data on metabolism of
dialifor in plants and (when appropriate) in animals, and residue data
reflecting the proposed use of the pesticide on the crop.
7-27
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CHAPTER VIII
ECOLOGICAL EFFECTS OF DIALIFOR
Ecological Effects Profile
Available information suggests that dialifor is no more than moderately toxic
to wild waterfowl, very highly toxic to estuarine invertebrates* and low in
toxicity to honey bees. Data on the toxicity of dialifor to non-target
organisms is scant. The only valid studies available were a subacute dietary
LC50 test on the mallard duck; a 96-hour LC50 test on two estuarine
invertebrates (grass shrimp and mud crab); and contact and oral LD50 tests on
honey bees.
The subacute avian dietary study contained sufficient information to
characterize dialifor as no more than moderately toxic to wild waterfowl with
no mortality occurring in mallard ducks feeding on 464 ppm. Excessive food
rejection at higher dosages precluded calculation of an LC50 value.
The acute 96-hour LC50 toxicity studies on the estuarine grass shrimp and mud
crab contained sufficient information to characterize dialifor as very highly
toxic to estuarine invertebrates, with LC50 values of 3.56 ppb and 33.5 ppb
respectively.
Laboratory studies on the honey bee contained sufficient information to
characterize dialifor as generally low in oral (LD50: 29.2 ug/bee) and contact
toxicity (LD50: 9.5 to 34.45 ug/bee).
Topical Discussions
Data on the effects of dialifor on non-target species are required due to the
outdoor, terrestrial end-uses of products formulated from manufacturing-use
dialifor.
Effects on Birds
Acute Toxicity
Avian acute oral LD50 data on either wild waterfowl or upland game birds are
required. One study (Fletcher, 1972, 00002192) on the mallard duck was
reviewed and found to be scientifically unsound, because dose levels resulting
in regurgitation were not identified. The LD50 value was reported as 940 (752-
1175) mgAg.
This study was conducted by Industrial Biotest Laboratories. This study was
reviewed in EPA's Laboratory Audit Program, and has been invalidated.
8-1
-------
Subacute Dietary Toxicity
Waterfowl
Data on the subacute dietary toxicity of dialifor to mallard ducks were
available. In a study completed by Beavers (Beavers, 1977, 00002139) the NEL
(No Effect Level) was established as greater than 464 ppm. in mallard ducks.
There is sufficient information to characterize dialifor as no more than
moderately toxic to wild waterfowl. No mortality occurred at 464 ppm.
Excessive food rejection at higher dosages precludes the calculation of the
LC50 value. No additional data are required.
Upland Game Bird
Avian dietary LC50 data on one species of upland game bird are required. One
study (Wolvin, 1969, 00002176) utilizing the bobwhite quail, was reviewed and
was determined to be invalid because the birds tested were 9 weeks old rather
than 10-17 days old (more sensitive age). The bobwhite dietary LC50 was
reported as greater than 5620 ppm with some food rejection at all test
concentrations.
This study was conducted by Industrial Biotest Laboratories. This study was
reviewed in EPA's Laboratory Audit Program, and has been invalidated.
Chronic Toxicity
An avian reproduction study on one species of upland game bird (preferably the
bobwhite quail) and one wild waterfowl (preferably the mallard duck) is
required because the use of dialifor can result in repeated exposure. No avian
reproduction data were available. These data are needed.
Effects on Fish
Acute Toxicity
Coldwater Fish
96-hour LC50 data on one species of coldwater fish are required. Two studies
were available to assess the LC50 of dialifor in rainbow trout (Schoenig, 1966,
00002057; Shoenig, 1967, 00002058). LC50 values of 0.55 ppm and 1.08
ppm,respectively, were reported. Both of these studies were completed by
Industrial Biotest Laboratories. These studies have been reviewed in EPA's
Laboratory Audit Program, and have been invalidated. Testing is needed.
Warmwater Fish
96-hour LC50 data on one species of warmwater fish are required. Two studies
were available to assess the LC50 of dialifor in bluegill sunfish (Schoenig,
1966, 00002057; Schoenig, 1967, 00002058). LC50 values of 0.064 (0.058-0.070)
and 0.0224 ppm, respectively, were reported. Both of these studies were
completed by Industrial Biotest Laboratories. These studies have been reviewed
in EPA's Laboratory Audit Program, and have been invalidated. Testing is
needed.
8-2
-------
Chronic Tbxicity
Embryolarvae studies on one fish species (preferably bluegill), and one aquatic
invertebrate life-cycle study (preferably on daphnia) may be required pending
the receipt and results of mobility and persistence studies.
Effects on Aquatic Invertebrates
Acute Toxicity
Data on the acute toxicity of dialifor to one species of aquatic invertebrates
is required but were not available.
Effects on Estuarine Organisms
Acute Tbxicity
Estuarine Invertebrates
The following data were available to assess the acute toxicity of dialifor to
estuarine invertebrates:
Species; Test Substance: LC50; Citation;
Grass Shrimp Technical 3.56 ppb Sleight, 00002191
Palaemonetes vulgaris (3.02-4.19)
Mud Crab Technical 33.5 ppb Sleight, 00002191
Neopanope texana (23.9-46.9)
There is sufficient information to characterize dialifor as very highly toxic
to estuarine invertebrates. No additional data are required, except to support
the registration of products used on citrus. Due to the proximity of citrus
crops to estuarine areas, toxicity tests are also required on an estuarine fish
(96-hour LC50). In addition, either a 48-hour EC50 embryo-larvae or 96-hour
EC50 shell deposition test in molluscs is also required.
Effects on Nontarget Soil and Surface Invertebrates
Acute Oral and Contact Toxicity
Honey bees
The following data were availble to assess the acute oral and contact toxicity
of dialifor to honey bees:
8-3
-------
Species; Test Substance; Results: Citation;
Honey bee Technical Oral LD50: 29.2 ug/bee Stevenson, J.H.;
( Apis mellifera ) Contact LD50: 9.5- 05001991
28.6 ug/bee
Honey bee EC At 1 Ib./lOO gal., Johansen, C.,
( Apis mellifera ) highly toxic as direct Eves, J.;
application, low in 00001949
toxicity as 3 hr. residue
Honey bee Unk. Relatively non-toxic Atkins, L.,
( Apis mellifera ) Contact LD50: 34.5 ug/ Anderson, L.D.;
bee 00001999
There is sufficient information to characterize dialifor as generally low in
toxicity to honey bees except when applied directly to bees as an emulsifiable
concentrate. No additional data are required.
Predators and Parasites
The following data were available to assess the toxicity of dialifor to
predator species:
Species: Test Substance: Results: Citation;
Lady beetle 6 Ib/gallon EC At .375 Ibs. ai per Colburn, R.,
( Stethorus 100 gal., highly toxic Asquith, D;
) unctum~T to larvae and eggs, 05004007
moderately toxic to
adults and non-toxic to
pupae.
Predatory Mite Unknown Moderately to highly AliNiazee, M.,
( Metaseiulus suitable for IPM in 05001683
occidentalis ) grapes.
There is sufficient information to characterize dialifor as variable in
toxicity to insect predators. Toxicity is variable depending upon species and
life stage.
8-4
-------
Ecological Effects Profile: Emulsifiable Concentrate Dialifor
The maximum recommended rate (1 Ib ai/acre) of dialifor formulated as a 4 pound
per gallon emulsifiable concentrate was shown to cause temporary spotting and
chlorosis on grapes. A second study tested an unspecified 40% dialifor
formulation which is assumed to be the 4 Ib per gallon emulsifiable
concentrate. This study showed that a 5000 ppm ai aqueous spray of dialifor
(equivalent to 4 Ib ai/acre) caused no damage to bean, pea, tomato, cucumber,
melon, or spinach. A 1000 ppm spray (equivalent to .8 Ib ai/acre) caused no
damage to the above crops as well as no damage to corn, soybeans, radish, or
Chinese cabbage. The equivalent rates per acre were calculated from test
concentrations assuming an application of 100 gallon of spray per acre.
Ecological Effects Hazard Assessment: Emulsifiable Concentrate Dialifor
A limited plant hazard assessment can be completed for only the plants tested.
Grapes can be expected to suffer only temporary phytotoxic injury when exposed
to dialifor at the recommended rate. Beans, peas, tomato, cucumber, melon, and
spinach should suffer no phytotoxicity when exposed to .8 Ib ai/acre, and corn,
soybean, radish, and Chinese cabbage should suffer no damage at rates up to 4
pounds ai/acre.
Topical Discussions
Effects on Algae, Fungi, and Aquatic Macrophytes
Data were not available on the effects of dialifor on algae, fungi, or aquatic
macrophytes. Data are required on the effects of dialifor on growth of aquatic
plants (163.122-2).
Effects on Terrestrial Macrophytes
Based on the available data, the following information is known about the
toxicity of dialifor to terrestrial macrophytes:
Species Formulation No-effect Level Author/Date ID*
Grape 4 Ib/gallon EC 1 Ib. ai/A Frost-1970 00002069
-The 1 pound rate caused some leaf spotting and chlorosis, but no
-damage was apparent 3 weeks after treatment. -
Corn 40%
Soybean
• *~J^^J 1v«^ W^»4» t_4. V—W» V«*tlV>l < ^. •
1000 ppm ai= 8 Ib/A Ishitani-1975 05006342
^yuecui 1000 ppm ai= 8 lb/A " "
Bean " 5000 ppm ai= 4 lb/A
Pea " 5000 ppm ai= 4 lb/A
Tomato " 5000 ppm ai= 4 lb/A
Cucumber " 5000 ppm ai= 4 lb/A " "
Melon " 5000 ppm ai= 4 lb/A
Radish " 1000 ppm ai= 8 lb/A
Chinese Cabbage " 1000 ppm ai= 8 lb/A "
Spinach " 5000 ppm ai= 4 lb/A
8-5
-------
All plants were sprayed with aqueous solutions until thoroughly wet, and rated
1-10 days after treatment. The equivalent rates in pounds per acre were
calculated based on use of 100 gallons of spray per acre. Based on the labels
of registered diali,for products, this 40% material is probably the 4 Ib/gallon
emulsifiable concentrate. Testing is required on the effects of dialifor on
seed germination/seedling emergence.
No data were available on the wettable powder formulation of dialifor.
8-6
-------
IX. CASE BIBLIOGRAPHY
Guide to Use of This Bibliography
1. Content of Bibliography. This bibliography contains citations of alJ the
studies reviewed by EPA in arriving at the positions and conclusions stated
elsewhere in this standard. Primary sources for studies in this
bibliography have been the body of data submitted to EPA and its
predecessor aqencies in support of past regulatory decisions, and the
published technical .literature.
2. Units of Entry. Tine unit of entry in this bibliography is called a
"study". In the case of published materials, this corresponds closely to
an article. In the case of unpublished materials submitted to the Agency,
the Agency has sought to identify documents at a level parallel to a
published article from within the tyoically larger volumes in which they
were submitted. The resulting "studies" generally have a distinct title
(or at least a single subject), can stand alone for purposes of review, and
can be described with a conventional biblioqraphic citation. The Agency
has attempted also to unite basic documents and commentaries upon them,
treating them as a single study.
3. Identification of Entries. Tine entries in this bibliography are sorted
by author, date of the document, and title. Each entry bears, to the left
of the citation proper, a nine-digit numeric identifier. This number is
unique to the citations and should be used at any time specific reference
is required. This number is called the "Master Record Identifier" or
"MRID". It is not related to the six-digit "Accession Number", which has
been used to identify volumes of submitted data; see paragraph 4(d)(4)
below for a further explanation. In a few cases, entries added to the
bibliography late in the review may he preceded by a nine-character
temporary identifier. This is also to be used whenever a specific
reference is needed.
4. Form of the Entry. In addition to the Master Record Identifier (MRID),
each entry consists of a bibliographic citation containing standard
elements followed, in the case of materials submitted to EPA, by a
description of the earliest known submission. The bibliographic
conventions used reflect the standards of the American National Standards
Institute (ANSI), expanded to provide for certain special needs. Some
explanatory notes of specific elements follow:
a. Author. Whenever the Agency could confidently identify one, the
Agency has chosen to show a personal author. When no individual was
identified, the Agency has shown an identifiable laboratory or testing
facility as author. As a last resort, the Agency has shown the first
known submitter as author.
b. Document Date. When the date appears as four digits with no
question marks, the Agency took it directly from the document. When a
four-digit date is followed by a question mark, the bibliographer
deduced the date from evidence in the document. When the date appears
as (19??'), the Agency was unable to determine or estimate the date of
the document.
-------
c. Title. This is the third element in the citation. In some cases it
has been necessary for .Agency bibliographers to create or enhance a
document title. Any such editorial insertions are contained between
square brackets.
d. Trailing Parentheses. For studies submitted to us in the past, the
trailing parentheses include (in addition to any self-explanatory
text) the following elements describing the earliest known
submissions:
(1) Submission Date. Immediately following the word 'received'
appears the date of the earliest known submission, at the time
that particular document was processed into the Pesticide
Document Management System.
(2) Administrative Number. The next element, immediately following
the word 'under1, is the registration number, experimental permit
number, petition number, or other administrative number
associated with the earliest known submission, at the time that
particular document was processed into the Pesticide Document
Management System.
(3) Submitter. The third element is the submitter, following the
phrase 'submitted by'. When authorship is defaulted to the
submitter, this element is omitted.
(4) Volume Identification. The final element in the trailing.
parenthesis identifies the EPA accession number of the volume in
which the original submission of the study appears. The six-
digit accession number follows the symbol 'CDL', standing for
"Company Data Library". This accession number is in turn
followed by an alphabetic suffix which shows the relative
position of the study within the volume. For example, within
accession number 123456, the first study would be 123456-A; the
second, 123456-B; the 26th, 123456-Z; and the 27th,123456-AA.
-------
OFFICE OF PESTICIDE PROGRAMS
REGISTRATION STANDARD BIBLIOGRAPHY
Citations Considered to be Part of the Data Base Supporting
Registrations Under the Standard
Case: GSrOOlO Dialifor
MRID # CITATION
005001683 AliNiazee, M.T.; Stafford, E.M.; Kidc, H. (1974) Management of
grape pests in central California vineyards: toxicity of some
commonly used chemicals to Tetranychus pacificus and its
predator, Metaseiulus occidentalis . Journal of Economic
Entomology 67(4):543-547.
000001999 Atkins, L., Jr.; Anderson, L.D. (1967) Toxicity of Pesticides and
Other Agricultural Chemicals to Honey Bees: Laboratory Studies.
(Unpublished study received Jan 30, 1969 under 9G0802; prepared
by Univ. of California—Riverside, Dept. of Entomology, sub-
mitted by Hercules, Inc., Agricultural Chemicals, Wilmington,
Del.; CDL:093111-D)
000002139 Beavers, J.B.; Fink, R. (1977) Eight-Day Dietary LC50—Mallard
Duck: Torak X-21314-24 (Hercules Manufacture): Final Report:
Project No. 114-104. (Unpublished study including letter dated
Sep 7, 1977 from K.D. Ihde to Franklin D.R. Gee and assay
report, received Sep 9, 1977 under 891-180; prepared by Wildlife
International, Ltd., submitted by Hercules, Inc., Agricultural
Chemicals, Wilmington, Del.; CDL:231595-A)
000001972 Bourke, J.B.; Marafioti, R.A.; Landschoot, R.L.; Stoewsand, G.S.
(1970) The Metabolism of Torak. (Unpublished study received
Sep 15, 1971 under 1F1032; prepared by New York State Agri-
cultural Experiment Station, received Sep 15, 1971 under
1F1032; submitted by Hercules, Inc., Wilmington Del.; CDL:
091917-Q)
005004007 Colburn, R.; Asquith, D. (1971) Tolerance of the stages
of Stethorus punctum to selected insecticides and miticides.
.Journal of Economic Entomology 64(5):1072-1074.
000002027 Eastman, G.E. (1968?) AC 14503 Oxygen Analog Residues on Various
Crops. (Unpublished study received Apr 25, 1969 under 9G0802;
submitted by Hercules, Inc., Agricultural Chemicals, Wilmington,
Del.; CDL:091383-G)
000002005 Ford, J.J. (19??) Analytical Method for Hercules 14503 Residues.
Method dated Apr 23, 1968. (Unpublished study received Jan 30,
1969 under 9G0802; submitted by Hercules, Inc., Agricultural
Chemicals, Wilmington, Del.; CDL:093111-K)
000002022 Ford,' J.J. (1968?) Torak Residues in Milk. (Unpublished study
Apr 25, 1969 under 9G0802; submitted by Hercules, Inc.,
Agricultural Chemicals, Wilmington, Del.; CDL:091383-B)
-------
000002024 Ford, J.J. (1969?) Tissue Residue Studies on Beef Calves Fed a Diet
Containing Torak: Appendix C-3. (Unpublished study received
Apr 25, 1969 under 9G0802; submitted by Hercules, Inc., Agricul-
tural Chemicals, Wilmington, Del.; CDL:091383-D)
000001961 Ford, J.J. (1969) Hercules 14503 Residues on Apples—1968. (Unpub-
lished study received Sep 9, 1971 under 1F1032; submitted by
Hercules, Inc., Wilmington, Del.; CDL:091916-K)
000001990 Ford, J.J. (1969) Tbrak Residues on Pecans. (Unpublished study
received Mar 3, 1970 under OG0943; submitted by Hercules, Inc.,
Wilmington, Del.; CDL:091612-M)
000001970 Ford, J.J. (1970?) Persistence of Torak in Soil. (Unpublished
study received Sep 15, 1971 under 1F1032; submitted by Hercules,
Inc., Wilmington, Del.; CDL:091917-N)
000001984 Ford, J.J. (1970) Residue Study of Ibrak on Grapes and Raisins—
1968 Tests. (Unpublished study including report, received
1970 under OG0943; submitted by Hercules, Inc., Wilmington,
Del.; CDL:097625-M)
000001953 Ford, J.J. (1971) Persistence and Leaching Properties of Torak in
Soil. (Unpublished study received Sep 9, 1971 under 1F1032;
submitted by Hercules, Inc., Wilmington, Del.; CDL:091916-C)
000001993 Ford, J.J. (1972) Persistence of Torak on Apples and Related Torak
Residue Studies. (Unpublished study received on unknown date
under 9G0802; submitted by Hercules, Inc., Agricultural Chemi-
cals, Wilmington, Del.; CDL:093110-B)
000002127 Ford, J.J. (1972) Persistence of Torak on Grapes and Related Torak
Residue Studies: RI 04180. (Unpublished study received Aug 3,
1972 under 3F1298; submitted by Hercules, Inc., Wilmington,
Del.; CDL:095878-D)
000002130 Ford, J.J. (1972) Torak Residue on Pecans (1971). (Unpublished
study received Aug 3, 1972 under 3F1298; submitted by Hercules,
Inc., Wilmington, Del.; CDL:095878-T)
000002129 Ford, J.J. (1972) Torak Residues in Poultry and Eggs. (Unpublished
study received Aug 3, 1972 under 3F1298; submitted by Hercules,
Inc., Wilmington, Del.; CDL:095878-R)
000001957 Ford, J.J.; Friant, R.J. (1971) Identification of Torak Metabolites
Present in Rat Urine. (Unpublished study received Sep 9, 1971
under 1F1032; submitted by Hercules, Inc., Wilmington, Del.;
CDL:091916-G)
000001958 Ford, J.J.; Kangas, L.R. (1971) A Metabolic Study of Torak on
Citrus. (Unpublished study received Sep 9, 1971 under 1F1032;
submitted by Hercules, Inc., Wilmington, Del.; CDL:091916-H)
-------
000001956 Ford, J.J.; Schranz, R.E.; Shearer, P.W. (1971) Identification of
the Products Resulting from the Hydrolysis and Photodegradation
of Torak. (Unpublished study received Sep 9, 1971 under 1F1032;
submitted by Hercules, Inc., Wilmington, Del.; CDL:091916-F)
000002069 Frost, M.H. (1970) An Evaluation of the Compatibility and Phytotox-
ic Characteristics of Torak in Combination with the Principal
Commercially Available Materials Used on Grapes in Central Cali-
fornia: I-B-5. (Unpublished study received Aug 3, 1972 under
3F1298; submitted by Hercules, Inc., Wilmington, Del.; CDL:
094715-M)
000001950 Greco, R.A. (1970) Report to Hercules Incorporated: Effects of
AC14503 on Plasma and Erythrocyte Cholinesterase and Plasma
Aliesterase Activity in Human Volunteers: IBT Nos. F7110 and
F7493. (Unpublished study received Sep 15, 1971 under 1F1032;
prepared by Industrial Bio-Test Laboratories, Inc., submitted
by Hercules, Inc., Wilmington, Del.; CDL:091917-1)
000002276 Hercules, Incorporated (19??) Practical Methods for Removing Resi-
dues That Exceed Any Proposed Tolerance: [Torak]. (Unpublished
study received Feb 6, 1973 under 3F1298; CDL:094668-S)
000002008 Hercules, Incorporated (1967) AC 14503: [Analytical Method].
Method dated May 26, 1967. (Unpublished study received Jan 30,
1969 under 9G0802; CDL:093111-P)
000002034 Hercules, Incorporated (1968?) AC 14503 Residues on Apples—1967.
(Unpublished study received Apr 28, 1969 under 7G0580; CDL:
091385-L)
000002032 Hercules, Incorporated (1968?) Persistence of AC 14503 on Florida-
Grown "Valencia" Oranges. (Unpublished study received Apr 28,
1969 under 7G0580; CDL:091385-J)
000001968 Hercules, Incorporated (1968?) Torak (Hercules 14503) Grapefruit—
Lake Alfred. (Unpublished study received Sep 15, 1971 under
1F1032; CDL:091917-L)
000002003 Hercules, Incorporated (1968) Stability of AC 14503 in Soil.
(Unpublished study including report, received Jan 30, 1969
under 9G0802; CDL:093111-H)
000002037 Hercules, Incorporated (1968) The Detection of AC 14503—Oxygen
Analog by Thin-Layer Chromatography-Enzyme Inhibition. (Unpub-
lished study including metabolism studies, received Apr 28, 1969
under 7G0580; CDL:091385-N)
000002033 Hercules, Incorporated (1969?) Survival and Distribution of AC
14503 Residues in Processed Citrus Products. (Unpublished study
received Apr 28, 1969 under 7G0580; CDL:091385-K)
000001994 Hercules, Incorporated (1969?) The Name, Chemical Identity and Com-
position of the Pesticide Chemical [and Method of Application:
Torak]. (Unpublished study received Jan 30, 1969 under 9G0802;
CDL:093110-C)
-------
000001969 Hercules, Incorporated (1969?) Tbrak (Hercules 14503) Lemons-
Homestead (1968). (Unpublished study received Sep 15, 1971
under 1F1032; CDL:091917-M)
000001967 Hercules, Incorporated (1969?) Tbrak (Hercules 14503) Oranges—Lake
Alfred (1968). (Unpublished study received Sep 15, 1971 under
1F1032; CDL:091917-K)
000001942 Hercules, Incorporated (1970?) Hercules Torak: The Name, Chemical
Identity and Composition of the Pesticide Chemical.
(Unpublished study received Aug 31, 1970 under 1F1032; CDL:
093341-J)
000001982 Hercules, Incorporated (1970?) The Name, Chemical Identity and
Composition of the Pesticide Chemical: Hercules Torak. (Unpub-
lished study received Jan 27, 1970 under OG0943; CDL:093249-J)
000001966 Hercules, Incorporated (1971?) Survival and Distribution of Torak
Residues in Processed Citrus Products from Grapefruit. (Unpub-
lished study received Sep 15, 1971 under 1F1032; CDL:091917-J)
000002194 Hercules, Incorporated (1972?) Assay Method for Torak Formulations.
Method dated Feb 11, 1969. (Unpublished study received Jun 26,
1972 under 891-EX-23; CDL:126402-E)
000002125 Hercules, Incorporated (1972?) Results of Tests on the Amount of
Residue Remaining, Including Description of the Analytical
Method Used: [Torak]. Summary of studies 095878-B through
095878-T. (Unpublished study received Aug 3, 1972 under 3F1298;
CDL:095878-A)
000002117 Hercules, Incorporated (1973) Torak Residues on California Grapes:
1973 Tests. (Unpublished study received on unknown date under
3F1298; CDL:095877-B)
005006342 Ishitani, A.; Yukimoto, M.; Yoshida, K. (1975) Nogaku no
kakushusakubutsu ni taisuru yakugai ni tsuite: II. Yuki rinkei
satchuzai. [Phytotoxicities of agricultural chemicals to
crops: II. Qrganophosphorus insecticides.] Noyaku Kensasho
Hokoku. [Bulletin of the Agricultural Chemicals Inspection
Station.] (15):92-97.
000002044 Jackson, G.L. (1966) Report to Hercules Incorporated: Acute Toxi-
city Study on Technical AC14503: Female Dutch Belted Rabbits:
WCRF: 161 (J4313). (Unpublished study received Mar 2, 1967
under 7G0580; prepared by Industrial Bio-Test Laboratories,
Inc., submitted by Hercules, Inc., Wilmington, Del.; CDL:0
090742-D)
000002055 Jackson, G.L.; Kennedy, G. (1966) Report to Hercules Incorporated:
Rabbit Teratogenic Study—AC14503: IBT No. J-4529. (Unpublished
study received Mar 2, 1967 under 7G0580; prepared by Industrial
Bio-Test Laboratories, Inc., submitted by Hercules, Inc.,
Wilmington, Del.; CDL:090742-O)
-------
000001949 Johansen, C.; Eves, J. (1969) Bee Research Investigations, 1969:
Small-scale Bee Poisoning Tests with Honey Bees (HB) and
Alfalfa Leafcutter Bees (LB). (Unpublished study received Sep
15, 1971 under 1F1032; prepared by Washington State Univ., sub-
mitted by Hercules, Inc., Wilmington, Del.; CDL:091917-H)
0000002054 Kennedy, G. (1966) Report to Hercules Incorporated: Rabbit Terato-
genic Study—AC14503: WCRF 158. (Unpublished study received
Mar 2, 1967 under 7G0580; prepared by Industrial Bio-Test
Laboratories, Inc., submitted by Hercules Inc., Wilmington,
Del.; CDL:090742-N)
005003635 Knaak, J.B.; Peoples, S.A.; Jackson, T.J.; Fredrickson, A.S.;
Enos, R.; Maddy, K.T.; Blair Bailey, J.; Duesch, M.E.; Gunther,
F.A.; Winterlin, W.L. (1978) Reentry problems involving the use
of dialifor on grapes in the San Joaquin Valley of California.
Archives of Environmental Contamination and Toxicology
7(4):465-481.
000038298 Knaak, J.B.; Peoples, S.A.; Jackson, T.J.; et al. (1978) Reentry
Problems Involving the Use of Torak (Dialifor) on Grapes in the
San Joaquin (Central) Valley of California in 1976: ACF-59-335.
(California, Dept. of Food and Agriculture and Univ. of Cali-
fornia; unpublished study)
005021646 Knaak, J.B.; Schlocker, P.; Ackerman, C.R.; Seiber, J.N. (1980)
Reentry research: establishment of safe pesticide levels on
foliage. Bulletin of Environmental Contamination and
Toxicology 24(5):796-804.
000002268 Lisk, D.J. (19??) Torak Residues in the Milk, Urine and Rumen
Fluid of a Lactating Cow. (Unpublished study received Sep 15,
1971 under 1F1032; prepared by Cornell Univ., Dept. of Entomo-
logy, Pesticide [Residue] Laboratory, submitted by Hercules,
Inc., Wilmington, Del.; CDL:091917-P)
000037644 Maddy, K.T. (1978) Problems with the Use of Dialifor (Torak) as a
Pesticide in California: ACF 59-437. (California, Dept. of Food
and Agriculture, Worker Health and Safety Unit, unpublished
study)
000002269 Mastri, C. (1969) Report to Hercules Incorporated: Acute Dermal
Toxicity Study on Torak (Hercules 14503) in Male Albino Rabbits:
IBT No. A7306. (Unpublished study received 1970 under OG0943;
prepared by Industrial Bio-Test Laboratories, Inc., submitted by
Hercules, Inc., Wilmington, Del.; CDL:097625-C)
000003280 Mastri, C. (1969) Report to Hercules Incorporated: Acute Dermal
Toxicity Study on Torak (Hercules 14503) in Male Albino Rabbits:
IBT No. A7307. (Unpublished study received 1970 under OG0943;
prepared by Industrial Bio-Test Laboratories, Inc., submitted by
Hercules, Inc., Wilmington, Del.; CDL:097625-E)
-------
0000001946 Mastri, C. (1969) Report to Hercules Incorporated: 30-Day Subacute
Dermal Toxicity Study on Torak E.G. in Albino Rabbits: IBT
No. A7308. (Unpublished study received Sep 15, 1971 under
1P1032; prepared by Industrial Bio-Test Laboratories, Inc.,
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000004153 Morrison, J. (1978) Formal Report of Analysis. (Unpublished study
including letter dated Apr 18, 1978 from K.D. Ihde to Libby
Zink, received Apr 25, 1978 under 891-EX-30>» prepared by Thermo
Electron Corp., submitted by Hercules, Inc., Agricultural
Chemicals, Wilmington, Del.; CDL:097073-A)
000002138 Reinking, R.B. (1973?) Application of Torak to Citrus for Residue
Determination. (Unpublished study received Aug 1, 1973 under
891-155; prepared in cooperation with Texas A & I Univ., Citrus
and Vegetable Training Center, submitted by Hercules, Inc.,
Agricultural Chemicals, Wilmington, Del.; CDL:009059-C)
000002043 Schoenig, G. (1966) Report to Hercules Powder Company: Acute Toxi-
city Studies on Technical AC14503. (Unpublished study received
Mar 2, 1967 under 7G0580; prepared by Industrial Bio-Test Lab-
oratories, Inc., submitted by Hercules, Inc., Wilmington, Del.;
CDL:090742-C)
000002191 Sleight, B.H., III (1972) Acute Toxicity of Torak to Grass Shrimp
( Paleomonetes vulgaris ) and Mud Crab ( Neopanope tex -
ana ): Bioassay Report. (Unpublished study received Jun 26,
1972 under 891-EX-23; prepared by Bionomics, Inc., submitted by
Hercules, Inc., Agricultural Chemicals, Wilmington, Del.; CDL:
130709-A)
St. John, L.E., Jr.; Gutenmann, W.H.; Lisk, D.J. (1971) Metabolism
studies with Torak insecticide in a dairy cow. Journal of
Agricultural and Food Chemistry 19(5):900-903.
Stevenson, J.H. (1978) The acute toxicity of unformulated
pesticides to worker honey bees ( Apis mellifera L.). Plant
Pathology 27(1):38-40.
Taylor, R.E. (1969) Cholinesterase and Tissue Residue Study Using
Hercules #14503 on Beef Animals. Includes undated method.
(Unpublished study received Apr 25, 1969 under 9G0802; prepared
by Harris Laboratories, Inc., submitted by Hercules, Inc.,
Agricultural Chemicals, Wilmington, Del.; CDL:091384-K)
000033018 U.S. Environmental Protection Agency (1979) Summary of Reported
Pesticide Incidents Involving Dialifor: Report No. 136. (U.S.
EPA, Office of Pesticide Programs, Benefits and Field Studies
Div., Human Effects Monitoring Branch, unpublished study.)
005001345 Westlake, W.E.; Duesch, M.E.; Gunther, F.A.; Jeppson, L.R. (1971)
Persistence of O,O-diethyl
S-(2-c^loro-l-phthalimidoethyl)-phosphorodithioate (Torak) on
and in lemons, oranges, and dried citrus pulp cattle feed, and
toxicity of the residues to mites. Journal of Agricultural and
Food Chemistry 19(6):1191-1195.
005001830
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-------
005001343 Winterlin, W.; Kilgore, W.; Mourer, C.; Mull, R.; Walker, G.;
Knaak, J.; Maddy, K. (1978) Dislodgable residues of dialifor
and phosalone and their oxygen analogs following a reported
worker-injury incident in the San Joaquin Valley, California.
Bulletin of Environmental Contamination and Toxicology
20(2):255-260.
-------
OFFICE OF PESTICIDE PROGRAMS
REGISTRATION STANDARD BIBLIOGRAPHY
Citations Reviewed and Considered to be Inappropriate
for use in the Registration Standard
GS0010
DIALIFOR
MRID ft CITATION
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-------
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-------
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Harris, M.K. (1975) Field Evaluation of Certain Insecticides for
Controlling Pecan Nut Casebearer in 1975: Project H-2881.
(Unpublished study received Mar 19, 1976 under 891-178; prepared
Texas Agricultural Experiment Station, Dept. of Entomology,
Pecan Insects Laboratory, submitted by Hercules, Inc., Agri-
cultural Chemicals, Wilmington, Del.; CDL:224102-Q)
Harris, M.K. (1976) Field Evaluation of Selected Insecticides for
Controlling Pecan Nut Nut [sic] Casebearer, Pecan Weevil and
Hickory Shuckworm at Hamilton, Texas in 1975: Project H-2881.
(Unpublished study received Mar 19, 1976 under 891-178; prepared
Texas Agricultural Experiment Station, Dept. of Entomology,
Pecan Insects Laboratory, submitted by Hercules, Inc., Agri-
cultural Chemicals, Wilmington, Del.; CDL:224102-J)
Harris, M.K.; Cutler, B. (1975) Walnut Caterpillar Response to
Insecticides. College Station, Tex.: Texas Agricultural
Experiment Station. (Texas Agricultural Experiment Station
progess report PR-3314(Abstr.))
-------
000001975 Hathaway, D. (1969) Report to Hercules Incorporated: Acute Dust
Inhalation Toxicity Study on Torak 50% Wettable Powder: IBT
No. N7309. (Unpublished study received 1970 under OG0943;
prepared by Industrial Bio-Test Laboratories, Inc., submitted
by Hercules, Inc., Wilmington, Del.; CDL:097625-F)
000001974 Hathaway, D. (1969) Report to Hercules Incorporated: Acute Vapor
Inhalation Toxicity Study on Torak 47% Emulsifiable Concentrate:
IBT No. N7321. (Unpublished study received 1970 under OG0943;
prepared*by Industrial Bio-Test laboratories, Inc., submitted by
Hercules, Inc., Wilmington, Del.; CDL:097625-D)
000001947 Hathaway, D. (1969) Report to Hercules Incorporated: Two-Week Sub-
acute Aerosol Inhalation Toxicity Study on Torak Emulsifiable
Concentrate: IBT No. N7310. (Unpublished study received Sep
15, 1971 under 1F1032; prepared by Industrial Bio-Test Labora-
tories, Inc., submitted by Hercules, Inc., Wilmington, Del.;
CDL:091917-F)
000001948 Hathaway, D. (1970) Report to Hercules Incorporated: Two-Week Sub-
acute Aerosol Inhalation Toxicity Study on Torak Emulsifiable
Concentrate: IBT No. N7799. (Unpublished study received Sep
15, 1971 under 1F1032; prepared by Industrial Bio-Test Labora-
tories, Inc., submitted by Hercules, Inc., Wilmington, Del.;
CDL:091917-G)
000002040 Hercules, Incorporated (19??) [Study: Analytical Method: Dialifor].
(Unpublished study received Jan 30, 1969 under 9G0802; CDL:
093111-T)
000027588 Hercules, Incorporated (19??) [Torak Tests]. (Unpublished study
received on unknown date under 891-155; CDL:240818-A)
000002004 Hercules, Incorporated (19??) Compatibility Studies with Hercules
14503. (Unpublished study received Jan 30, 1969 under 9G0802;
CDL:093111-1)
000001992 Hercules, Incorporated (19??) Full Reports of Investigations Made
with Respect to Safety of Torak. (Unpublished study received on
unknown date under OG0943; CDL:093249-K)
000002159 Hercules, Incorporated (19??) Hercules Torak G Application for
Experimental Use Permit for Experimental Application to Walnuts:
Identity: Physical and Chemical Properties. (Unpublished study
received Jan 16, 1976 under unknown admin, no.; CDL:225833-A)
000001973 Hercules, Incorporated (19??) Petition for a Temporary Tolerance on
Grapes and Pecans: Torak (Hercules 14503). (Unpublished study
received 1970 under OG0943; CDL:097625-A)
00002131 Hercules, Incorporated (19??) Reasonable Grounds in Support of
This Petition: [Dialifor]. (Unpublished study received
« .Aug 3, 1972 under 3F1298; CDL:095877-U)
-------
000026493
000002041
000002061
000002059
000001983
000002060
000002163
000001991
000001977
000002001
000002002
Hercules, Incorporated (19??) Torak' 'insecticide and Acaracide.
Rev. Wilmington, Del.: Hercules. (Bulletin AP-122; also In
unpublished submission received Mar 24, 1977 under 891-180; CDL:
240760-A)
Hercules, Incorporated (1967?) Full Reports of Investigations Made
with Respect to Safety of AC14503. (Unpublished study received
Mar 2, 1967 under 7G0580; CDL:090742-A)
Hercules, Incorporated (1967?) Reasonable Grounds in Support of
the Petition: [Hercules 14503]: Lint-bearing Cottonseed.
(Unpublished study received Mar 14, 1967 under 7G0580; CDL:
092858-C)
Hercules, Incorporated (1967?) Results of Tests on the Amount of
Residue Remaining, Including a Description of the Analytical
Method Used: [Hercules 14503], (Unpublished study received
Feb 28, 1967 under 7G0580; CDL:090743-A)
Hercules, Incorporated (1967?) The Amount, Frequency and Time of
Application of the Pesticide Chemical: [Torak]. (Unpublished
study received 1970 under OG0943; CDL:097625-L)
Hercules, Incorporated (1967?) The Name, Chemical Identity, and
Composition of the Pesticide Chemical: "Hercules 14503".
(Unpublished study received Mar 14, 1967 under 7G0580; CDL:
092868-A)
Hercules, Incorporated (1968?) Hercules 14503, 4 Ibs./Gallon EC for
Alfalfa Weevil Control: 891-EXP-14G. (Unpublished study
received Jan 2, 1969 under 891-EX-14; CDL:126389-A)
Hercules, Incorporated (1968?) Reasonable Grounds in Support of
this Petition: [Torak]. (Unpublished study received 1970 under
OG0943; CDL:097625-U)
Hercules, Incorporated (1968?) Result of Tests on the Amount of
Residue Remaining, Including Description of the Analytical
Method Used: [Dialifor]. (Unpublished study including letter
dated Feb 3, 1970 from E.N. Woodbury to U.S. Food and Drug
Administration, Petitions Control Branch, received 1970 under
OG0943; CDL:097625-J)
Hercules, Incorporated (1968?) Summary of Data for Hercules 14503—
Citrus. (Unpublished study including letter dated Apr 22, 1969
from R.B. Johnson to T.M. Ritchie, letter dated Sep 9, 1969 from
R.B. Johnson to Ralph Hansen, letters dated Oct 12, 1970 and
Aug 31, 1970 from J.R. Christie to W. Alan Weeks, letter dated
Feb 1, 1971 from R.B. Johnson to E.W. Woodbury, received Jan 30,
1969 under 9G0802; CDL:093111-F)
Hercules, Incorporated (1968?) Summary of Field Test Data for
Hercules 14503 on Apples. (Unpublished study received Jan 30,
1969 under 9G0802; CDL:093111-G)
-------
000002031 Hercules, Incorporated (1968) AC 14503 Residue on Lint-Bearing
Cotton Seed. (Unpublished study received Apr 28, 1969 under
7G0580; CDL:091385-1)
000002092 Hercules, Incorporated (1968) Agricultural Chemicals Laboratory
Orchard Data. (Unpublished study including report, received
Aug 3, 1972 under 3F1298; CDL:094667-H)
000002000 Hercules, Incorporated (1968) Sunrnary of Field Tests of Hercules
14503 for the Control of Mites on Cotton. (Unpublished study
received Jan 30, 1969 under 9G0802; CDL:093111-E)
000002007 Hercules, Incorporated (1969?) [Hercules 14503: Chemical Composi-
tion] . (Unpublished study received Jan 30, 1969 under 9G0802;
CDL:093111-0)
000001971 Hercules, Incorporated (1969?) Analysis of Milk for Residues of
Tbrak-Oxygen Analog. (Unpublished study received Sep 15, 1971
under 1F1032; CDL:091917-O)
000001978 Hercules, Incorporated (1969?) Effectiveness Data: [Torak (Hercules
14503)]. (Unpublished study received 1970 under OG0943; CDL:
097625-K)
000002012 Hercules, Incorporated (1969?) Effectiveness Data: [Torak].
(Unpublished study received Apr 25, 1969 under 9G0802; CDL:
091384-A)
000002013 Hercules, Incorporated (1969?) Effectiveness: [Torak].
(Unpublished study received Apr 25, 1969 under 9G0802; CDL:
091384-C)
000002019 Hercules, Incorporated (1969?) Full Reports of Investigations Made
with Respect to Safety of Torak. (Unpublished study received
Apr 28, 1969 under 7G0580; CDL:091385-A)
000002018 Hercules, Incorporated (1969?) Full Reports of Investigations Made
with Respect to Safety of Torak. (Unpublished study received
Apr 25, 1969 under 9G0802; CDL:091384-1)
000002270 Hercules, Incorporated (1969?) Full Reports of Investigations Made
with Respect to Safety of Torak. (Unpublished study received
Mar 3, 1970 under OG0943; CDL:091612-A)
000001995 Hercules, Incorporated (1969?) Hercules Torak: The Name, Chemical
Identity and Composition of the Pesticide Chemical. (Unpub-
lished study received Jan 30, 1969 under 9G0802; CDL:093110-D)
000002010 Hercules, Incorporated (1969?) Reasonable Grounds in Support of
This Application: [Hercules 14503]. (Unpublished study received
Jan 30, 1969 under 9G0802; CDL:093111-R)
000002011 Hercules, Incorporated (1969?) Request for an Extension of Tempo-
rary Tolerances of the Insecticide Torak on Apples and Citrus.
(Unpublished study received Apr 25, 1969 under 9G0802; CDL:
091383-A)
-------
000002030
000001964
000002009
000002036
000001979
000002168
000002006
000002180
000001943
000001944
000001937
000001981
000002175
Hercules, Incorporated (1969?) Result of Tests on the Amount of
Residue Remaining, Including Description of the Analytical
Method Used: [Hercules 14503]. (Unpublished study received Apr
28, 1969 under 7G0580; CDL:091385-H)
Hercules, Incorporated (1969?) Summary of Data for Hercules 14503—
Citrus. (Unpublished study received Sep 14, 1971 under 1F1032;
CDL:091915-E)
Hercules, Incorporated (1969?) The Amount, Frequency and Time of
Application of Hercules 14503. (Unpublished study received
Jan 30, 1969 under 9G0802; CDL:093111-Q)
Hercules, Incorporated (1969?) The Amount, Frequency and Time of
Application: [Torak]. (Unpublished study received Jan 30, 1969
under 9G0802; CDL:093110-E)
Hercules, Incorporated (1969?) Torak Residues on Apples from the
Application of Torak 50% Wettable Powder: Table 1. (Unpublished
study received Aug 12, 1972 under OG0943; CDL:091611-B)
Hercules, Incorporated (1969) Pesticide Petition No. 9G0802:
Reasonable Grounds in Support of this Application: [Dialifor]:
Amended 5/5/69. (Unpublished study received May 8, 1969 under
891-EX-17; CDL:126394-B)
Hercules, Incorporated (1969) Reasonable Grounds in Support of This
Application: Amended 5/5/69: [Hercules 14503]. (Unpublished
study received Jan 30, 1969 under 9G0802; CDL:093111-N)
Hercules, Incorporated (1969) Results of Tests with 14503 for
Hercules Incorporated. (Unpublished study including letter
dated Oct 8, 1969 from E.N. Woodbury to Harold G. Alford,
received Mar 25, 1970 under 891-EX-19; CDL:126396-D)
Hercules, Incorporated (1970?) Reasonable Grounds in Support of
This Petition: [Torak]. (Unpublished study including summary
of Torak efficacy data on Florida citrus, received Aug 31, 1970
under 1F1032; CDL:093341-K)
Hercules, Incorporated (1970?) Reasonable Grounds in Support of
This Petition: [Torak]. (Unpublished study received Aug 31,
1970 under 1F1032; CDL:093341-M)
Hercules, Incorporated (1970?) Summary of Efficacy Data for Her-
cules Torak—Citrus. (Unpublished study including appendices
EXP.l - EXP.4, received Sep 14, 1971 under 1F1032; CDL:091915-C)
Hercules, Incorporated (1970?) The Name, Chemical Identity and Com-
position of the Pesticide Chemical: Hercules Torak. (Unpub-
lished study received Jan 27, 1970 under OG0943; CDL:093249-G)
Hercules, Incorporated (1970) [Test Data from Applications of Torak
on Citrus in Florida and Texas]. (Unpublished study received
Mar 29, 1971 under 891-EX-18; CDL:126395-G)
-------
000002179 Hercules, Incorporated (1970) Torak1 'Tree Fruit Data Sheet [and
Orchard Evaluation]. (Unpublished study received May 11, 1971
under 891-EX-19; CDL:126395-C)
m\
000002107 Hercules, Incorporated (1970) Torak Tree Fruit Data Sheet[s].
(Unpublished study received Aug 3, 1972 under 3F1298; CDL:
094667-AC)
000001963 Hercules, Incorporated (1971?) Efficacy Data for Hercules Torak on
Florida Citrus. (Unpublished study received Sep 14, 1971 under
1F1032; CDL:091915-D)
000002197 Hercules, Incorporated (1971?) Hercules Torak: The Name, Chemical
Identity and Composition of the Pesticide Chemical. (Unpub-
lished study received Nov 22, 1971 under 891-EX-26; CDL:
126406-A)
000001952 Hercules, Incorporated (1971?) Hydrolysis of Torak. (Unpublished
study received Sep 9, 1971 under 1F1032; CDL:09191S-A)
000001945 Hercules, Incorporated (1971?) Result of Tests on the Amount of
Residue Remaining, Including Description of the Analytical
Method Used: [Torak]. (Unpublished study received Sep 15, 1971
under 1F1032; CDL:091917-B)
000002185 Hercules, Incorporated (1971) [Torak 6 Lb./Gal. EC for the Control
of Arthropod Pests on Commercial Grape Plantings in California].
(Unpublished study received Nov 5, 1971 under 891-EX-22;
CDL:126400-A)
000002071 Hercules, Incorporated (1971) Torak Field Data Sheet[s]—Grapes.
(Unpublished study received Aug 3, 1972 under 3F1298; CDL:
094715-R)
000002062 Hercules, Incorporated (1972?) Efficacy of Torak against Arthropod
Pests of Grapes. Summary of studies 094715-B through 094715-S.
(Unpublished study including summary table, received Aug 3, 1972
under 3F1298; CDL:094715-A)
000002122 Hercules, Incorporated (1972?) Emulsifiability of Torak 4 Pound per
Gallon E.G. Stored at 50°C. (Unpublished study received
Aug 3, 1972 under 3F1298; CDL:095877-K)
000002123 Hercules, Incorporated (1972?) Emulsifiability of Torak 6 Pound per
Gallon E.G. Stored in 80-110°F Test Chamber in Pigmented Baked
Phenolic Lined Can. (Unpublished study received Aug 3, 1972
under 3F1298; CDL:095877-L)
000002086 Hercules, Incorporated (1972?) Summary of Efficacy Data for Torak
on Apples, Pears and Plums. Summary of studies 094657-B through
094667-AM. (Unpublished study including appended summary table,
received Aug 3, 1972 under 3F1293; CDL:0946S7-A)
-------
000002124 Hercules, Incorporated (1972?) Summary of Full Reports of Investi-
gations Made with Respect to Safety of Torak. Summary of stud-
ies 095877-Q through 095877-T. (Unpublished study received
Aug 3, 1972 under 3F1298; CDL:095877-P)
000002073 Hercules, Incorporated (1972?) Summary: Efficacy of Torak against
Insect Pests of Pecans. Summary of studies 094715-U through
094715-AE. (Unpublished study received Aug 3, 1972 under
3F1298; CDL:094715-T)
000002121 Hercules, Incorporated (1972?) Tbrak Stability Studies. (Unpub-
lished study received Aug 3, 1972 under 3F1298; CDL:095877-J)
000002145 Hercules, Incorporated (1972) Air vs. Ground Application. (Unpub-
lished study received Mar 19, 1976 under 891-178; CDL:224102-B)
000002146 Hercules, Incorporated (1972) Pecan Weevil 1 Day Interval Tests.
(Unpublished study received Mar 19, 1976 under 891-178;
CDL:224102-C)
000002120 Hercules, Incorporated (1973?) Hercules Torak: The Name, Chemical
Identity and Composition of the Pesticide Chemical. (Unpub-
lished study received Aug 3, 1972 under 3F1298; CDL:095877-F)
000002190 Hercules, Incorporated (1973?) Hercules Torak: The Name, Chemical
Identity and Composition of the Pesticide Chemical. (Unpub-
lished study received Apr 25, 1973 under 891-EX-25; CDL:
210111-A)
000002147 Hercules, Incorporated (1973) Pecan Weevil-fTennille & Other Loca-
tions. (Unpublished study received Mar 19, 1976 under 891-178;
CDL: 224102-D)
000002119 Hercules, Incorporated (1973) Reasonable Grounds in Support of This
Petition: [Dialifor]. Rev. (Unpublished study received on
unknown date under 3F1298; CDL:098577-E)
000002116 Hercules, Incorporated (1973) Reasonable Grounds in Support of This
Petition: [Dialifor]. Rev. (Unpublished study received on
unknown date under 3F1298; CDL:094668-G)
000002831 Hercules, Incorporated (1973) Reasonable Grounds in Support of This
Petition: [Dialifor]. (Unpublished study received on unknown
date under 3F1298; CDL:092198-H)
000002132 Hercules, Incorporated (1973) Torak Field Data Sheet[s]—Pecans.
(Unpublished study received on unknown date under 3F1298; CDL:
094668-V)
000002118 Hercules, Incorporated (1973) Torak Residues in Raisins. (Unpub-
lished study received on unknown date under 3F1298; CDL:
095877-D)
-------
000002160
000002161
000002133
000002134
000002152
000002196
000002189 Hercules, Incorporated (1973) Torak* ^ Organophosphate Pesticide
(Dialifor): Summary of Toxicological Investigations: Bulletin
T-121. (Unpublished study received Jul 1, 1973 under unknown
admin, no.; CDL:140101-A)
Hercules, Incorporated (1974?) Torak Insecticide and Acaracide:
Description and Properties. (Unpublished study received 1974
under unknown admin, no.; CDL:123975-A)
Hercules, Incorporated (1974?) Toxicology: [Torak]. (Unpublished
study received 1974 under unknown admin, no.; CDL.-123975-B)
Hercules, Incorporated (1974) Summary—1974 Torak Field Evalua-
tion—Texas Citrus. (Unpublished study received Apr 7,- 1975
under 891-155; CDL:222045-A)
Hercules, Incorporated (1975?) [Efficacy Data of Torak]. (Unpub-
lished study received May 16, 1975 under 891-155; CDL:222143-A)
Hercules, Incorporated (1975) [Aerial Sprays for Control of Certain
Pecan Insects]. (Unpublished study received Mar 19, 1976 under
391-178; CDL:224102-K)
(R)
Hercules, Incorporated (1975) Torak Organophosphate Pesticide
(Dialifor): Summary of Toxicological Investigations: Bulletin
T-121B (Supersedes T-121A). (Unpublished study received Jan 16,
1976 under 891-EX-29; CDL:226513-C)
000002195 Hercules, Incorporated (1976?) Supplemental Directions for the
Experimental Use of Torak G Emulsifiable Concentrate Insecticide
(EPA Reg. No. 891-179) on Walnuts in California. (Unpublished
study received Jan 16f 1976 under 891-EX-29; CDL:226513-B)
000002144 Hercules, Incorporated (1976) Efficacy of Torak P against the Pecan
Weevil, Pecan Nut Casebearer and Pecan Spittlebug. Summary of
studies 224102-B through 224102-R. (Unpublished study received
Mar 19, 1976 under 891-178; CDL:224102-A)
000002140 Hercules, Incorporated (1976) Efficacy: [Evaluation of Torak].
(Unpublished study received Apr 1, 1977 under 891-178; CDL:
096068-A)
000002142 Hercules, Incorporated (1977?) Results of Tests on the Amount of
Residue Remaining, Including Description of the Analytical Meth-
od Used: [Torak]. (Unpublished study including report, received
Apr 1, 1977 under 891-178; CDL:096069-1)
000002143 Hercules, Incorporated (1977?) Safety of Proposed Tolerance on Wal-
nuts: Reasonable Grounds in Support of This Petition: [Torak].
Includes method dated Dec 21, 1976. (Unpublished study received
Apr 1, 1977 under 891-178; CDL: 096069^1)
000002141 Hercules, Incorporated (1977?) The Amount, Frequency and Time of
Application: [Torak]. (Unpublished study received Apr 1, 1977
under 891-178; CDL:096069-G)
-------
000002188 Hercules, Incorporated, Agricultural Chemicals (1969?) Assay Method
for Tbrak Formulations: [Dialifor]. Method dated Feb 11,
1969. (Unpublished study received Jun 26, 1972 under unknown
admin, no.; CDL:128241-A)
000006301 Hiddleson, L. (1966) Report No. 074566-047. (Unpublished study re-
ceived Mar 24, 1976 under 359-620; submitted by Rhone-Poulenc,
Inc., Monmouth Junction, N.J.; CDL:095197-J)
000006297 Hiddleson, L.; Adler, V.; Steinhaiier, A.L. (1965) Summary Report:
Report No. 071965-023. (Unpublished study received Mar 24, 1976
under 359-620; prepared in cooperation with U.S. Dept. of Agri-
culture, Alfalfa Weevil Investigations Laboratory and Univ. of
Maryland, Dept. of Entomology for Chipman Chemical Co., Inc.,
submitted by Rhone-Poulenc, Inc., Monmouth Junction, N.J.; CDL:
095197-E)
000006312 Hiddleson, L.; Bishop, J.L. (1967) Report No. 074567-025. (Unpub-
lished study received Mar 24, 1976 under 359-620; prepared in
cooperation with Virginia Polytechnic Institute and State Univ.,
submitted by Rhone-Poulenc, Inc., Monmouth Junction, N.J.; CDL:
095197-U)
000006759 Hiddleson, L.; Blickenstaff, C.C. (1966) Report No. 071966-018.
(Unpublished study received Mar 24, 1976 under 359-620; prepared
in cooperation with U.S. Dept. of Agriculture, Alfalfa Weevil
Investigations Laboratory and Univ. of Maryland, Dept. of Ento-
mology for Chipman Chemical Co., Inc., submitted by Rhone-
Poulenc, Inc., Monmouth Junction, N.J.; CDL:095197-G)
000002095 Hill, C.H. (1969) Report for the 1969 Cumberland-Shenandoah Fruit
Workers Conference: Summary of Results of Acaricide Tests. (Un-
published study received Aug 3, 1972 under 3F1298; prepared by
Virginia Polytechnic Institute [and State Univ.], Winchester
Fruit Research Laboratory, submitted by Hercules, Inc., Wilming-
ton, Del.; CDL:094667-L)
000012456 Hofmaster, R.N.;, Waterfield, R.L. (1968) Cooperator Research Re-
port: Potato Insecticide Tests. (Unpublished study received Nov
10, 1972 under 3F1323; prepared by Virginia Truck Experiment
Station, Eastern Shore Branch, submitted by Ciba-Geigy Corp.,
Greensboro, N.C.; CDL:093552-AP)
000008304 Hofmaster, R.N.; Waterfield, R.L. (1968) Foliage Schedule to Con-
trol Insect Pests of Fall Irish Potatoes: Colorado Potato Bee-
tles and Cabbage Loopers. (Unpublished study received Jan 21,
1970 under OF0886; prepared by Virginia Truck Experiment Sta-
tion, Eastern Shore Branch, submitted by E.I. du Pont de Nemours
& Co., Inc., Wilmington, Del.; CDL:091530-AA)
000009790 Hofmaster, R.N.; Waterfield, R.L. (1968) Foliage Schedule to Con-
trol Insect Pests of Fall Irish Potatoes: Green Peach Aphids and
Yields. (Unpublished study received Nov 16, 1971 under 352-342;
prepared by Virginia Truck Experiment Station, Eastern Shore
Branch, submitted by E.I. du Pont de Nemours & Co., Wilmington,
Del.; CDL:003031-S)
-------
000010326 Hofmaster, R.N.; Waterfield, R.L. (1968) Foliage Schedule to Con-
trol Insect Pests of Fall Irish Potatoes: Potato Tuberworms:
Table 6-B. (Unpublished study received Jan 21, 1970 under
OF0886; prepared by Virginia Truck Experiment Station, Eastern
Shore Branch, submitted by E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:091530-Q)
000008771 Hofmaster, R.N.; Waterfield, R.L. (1968) Reduction in European Corn
Borer Damage to N&K Code 199 Sweet Corn Ears Following a Regular
Corn Earworm Control Schedule: Table 12. (Unpublished study re-
ceived Nov 16, 1971 under 352-342; prepared by Virginia Truck
Experiment Station, Eastern Shore Branch, submitted by E.I. du
Pont de Nemours & Co., Wilmington, Del.; CDL:003037-L)
000008058 Hbfinaster, R.N.; Waterfield, R.L. (1968) Screening Trials to Con-
trol Tobacco Hornworms in Marion Tomatoes: Painter, Va., 1968:
Table 9. (Unpublished study received Jan 29, 1970 under 352-
342; prepared by Virginia Truck Experiment Station, Eastern
Shore Branch, submitted by E.I. du Pont de Nemours & Co., Wil-
mington, Del.; CDL:003010-J)
000008642 Hofmaster, R.N.; Waterfield, R.L. (1969) Foliage Schedule to Con-
trol the Potato Tuberworm, Tobacco Flea Beetle, European Corn
Borer & Green Peach Aphid in Fall Irish Potatoes: Table #6.
(Unpublished study received Nov 16, 1971 under 352-342; prepared
by Virginia Truck Experiment Station, Eastern Shore Branch, sub-
mitted by E.I. du Pont de Nemours & Co., Wilmington, Del.; CDL:
003031-Y)
000008293 Hofmaster, R.N.; Waterfield, R.L. (1969) Insecticides to Control
Mexican Bean Beetles on Hill Soybeans: Table 22. (Unpublished
study received Jun 16, 1971 under 1F1021; prepared by Virginia
Truck Experiment Station, Eastern Shore Branch, submitted by
E.I. du Pont de Nemours & Co., Inc., Wilmington, Del.; CDL:
091071-AU)
005004744 Hofmaster, R.N.; Waterfield, R.L. (1972) Insecticide control of
the potato tuberworm in late-crop potato foliage. American
Potato Journal 49(10):383-390.
000006955 Hogue, C.W.; Calcote, V.R.; Bogent, J.L. (1972) Final Report: Dis-
trict Project No. 201772-012. (Unpublished study received Jun
9, 1977 under 359-620; prepared by Rhodia, Inc. in cooperation
with U.S. Dept. of Agriculture, Pecan Laboratory and Louisiana
State Univ., submitted by Rhone-Poulenc, Inc., Monmouth Junc-
tion, N.J.; CDL:230375-F)
000002094 Howitt, A.J.; Gertz, R.; Pshea, A. (1968) Entomological Research on
Small and Tree Fruits in 1968. (Unpublished study received Aug
3, 1972 under 3F1298; prepared by Michigan State Univ., Dept. of
Entomology, submitted by Hercules, Inc., Wilmington, Del.; CDL:
094667-J)
-------
000008148 Hudon, M. (1971?) Chemical Control of the European Corn Borer on
Sweet Corn in Southwestern Quebec. (Unpublished study received
Mar 5, 1974 under 352-342; prepared by Canada, Dept. of Agricul-
ture, Research Station, submitted by E.I. du Pont de Nemours &
Co., Wilmington, Del.; CDL:023294-E)
005001688 Hudon, M.; Martel, P. (1977) Field experiments with spray
insecticides for the control of the European corn border (sic.
borer), on sweet corn in Quebec. Phytoprotection
58(2/3):59-62.
000002082 Ihde, K.D. (1972) Effectiveness of Torak, Hercules 16801 and Hercu-
les 24108 against Apple Pests. (Unpublished study received on
unknown date under 3F1298; submitted by Hercules, Inc., Wilming-
ton, Del.; CDL:094666-D)
000002085 Ihde, K.D. (1972) Field Test to Determine Phytotoxicity of High
Rate of Torak to Apples. (Unpublished study received on unknown
date under 3F1298; submitted by Hercules, Inc., Wilmington,
Del.; CDL:094666-G)
005011210 Imamura, K.; Nabekawa, S.; Takada, M., inventors; Nippon Chemical
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-------
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-------
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-------
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*U S GOVERNMENT PRINTING OFFICE: 1981 341-085/4472
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