v>EPA
Unitad States
Environmental Protection
Agency
Office of
Pesticides and Toxic Substanc
Washington DC 20460
September 1980
Pesticides
1, 4-dichloro-2,5
-dimethoxybenzene
Chloroneb
Pesticide Registration
Standard
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CHLORONEB
Pesticide Registration Standard
Rose Allison Project Manager (SPRD)
Henry Appleton Environmental Chemist ((HED)
Raymond Kent Residue Chemist (HED)
Bob Panebianco Product Manager (RD)
Mary Quaife lexicologist (HED)
John Tice Wildlife Ecologist (HED)
Greg Ueidemann Plant Sciences Specialist (BFSD)
September 1980
Office of Pesticides and Toxic Substances
Environmental Protection Agency
401 M Street. SW
Washington, DC 20460
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TABLE OF CONTENTS
Page No.
Chapter One
How to Register Under a Registration Standard.... 1
Chapter Two
Agency Position on Chloroneb
Regulatory Position for Chloroneb....
Criteria for Registration under
a Standard
A. Manufacturing-use Chloroneb 9
1. Acceptable Ranges and Limits
2. Data Requirements and Data Gaps
3. Required Labeling
4. Tolerance Reassessment
5. Regulatory Rationale
B. Wettable Powder Chloroneb 20
1. Acceptable Ranges and Limits
2. Data Requirements and Data Gaps
3. Required Labeling
4. Regulatory Rationale
C. Granular Chloroneb 26
1. Acceptable Ranges and Limits
2. Data Requirements and Data Gaps
3. Required Labeling
4. Regulatory Rationale
D. Dust Chloroneb 33
1. Acceptable Ranges and Limits
2. Data Requirements and Data Gaps
3. Required Labeling
4. Regulatory Rationale
Chapter Three
Product Chemistry of Chloroneb
A. Introduction 40
B. Manufacturing-use Chloroneb 40
1. Product Chemistry Profile
2. Data Requirements and Data Gaps
3. Topical Discussions
C. Wettable Powder Chloroneb 46
1. Data Gaps
2. Topical Discussions
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Page No,
D. Granul ar Chi oroneb 48
1. Data Gaps
2. Topical Discussions
E. Dust Chloroneb 49
1. Data Gaps
2. Topical Discussions
F. Bibliography 52
Chapter Four
Environmental Fate of Chloroneb
A. Use Profile 53
B. Manufacturing-use Chloroneb 53
1. Environmental Fate Profile
2. Exposure Profile
3. Data Gaps
4. Topical Discussions
C. Formulations of Chloroneb 64
1. Exposure Profi1es
D. Bibliography 66
Chapter Five
Toxicology of Chloroneb
A. Manufacturing-use Chloroneb 67
1. Toxicology Profile
2. Human and Domestic Animal Hazard
Assessment
3. Data Requirements and Data Gaps
4. Required Labeling
5. Topical Discussions
B. Wettable Powder Chloroneb 81
1. Toxicology Profile
2. Data Gaps
3. Human and Domestic Animal Hazard
Assessment
4. Topical Discussions
C. Granular Chloroneb 85
1. Toxicology Profile
2. Data Gaps
3. Human and Domestic Animal Hazard
Assessment
4. Topical Discussions
ii
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Page No,
D. Dust Chloroneb 89
1. Toxicology Profile
2. Data Gaps
3. Human and Domestic Animal Hazard
Assessment
4. Topical Discussions
E. Bibliography 92
Chapter Six
Residue Chemistry of Chloroneb
A. Manufacturing-use Chloroneb 94
1. Residue Chemistry Profile
2. Data Gaps
3. Topical Discussions
B. Formulations of Chloroneb 108
1. Data Requirements
2. Required Labeling
C. Bibliography 110
Chapter Seven
Ecological Effects of Chloroneb
A. Manufacturing-use Chloroneb 113
1. Ecological Effects Profile
2. Data Gaps
3. Topical Discussions
B. Wettable Powder Chloroneb 116
1. Ecological Effects Profile
2. Topical Discussions
C. Granular Chloroneb 116
1. Ecological Effects Profile
2. Topical Discussions
D. Dust Chloroneb 117
1. Ecological Effects Profile
2. Topical Discussions
E. Bibliography 118
Case Bibliography
A. Guide to Use of the Bibliography 119
Section 1 122
Section II 129
ill
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Chapter 1
HOW TO REGISTER
UNDER A REGISTRATION STANDARD
Organization of tha 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 or_ 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;
(B) its labeling and other material required to be submitted comply with
the requirements of this Act;
(C) it will perform its intended function without 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 product1 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 product1 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 standards. Given the long history- of pesticide regulation in
several agencies, it is even likely that materials may have been lost from the
data files, '//hen 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, 1973 and 43 FR 37336, August 2, 1973), 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)l.
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 publishes
documents 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 ana 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(O(1)(D).
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 pesticides 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 I62.11(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 Jto Re-register Under the Standard
FIFRA Section 3(g), as amended in 1978, directs EPA to re-register all
currently 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-regisration. 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 (43 FR 29686, July 10, 1978, and 43 FR 37336, August 2, 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
effect for some time and are, the Agency believes, 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
toxicity (which is a function of its total composition). The applicant for
registration or re-registration of any product, whether it is a manufacturing-
use or end-use product, and without regard to its intended use pattern, must
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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-Ka), 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 seme 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 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 <»hich is
described by all the following criteria:
(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 registrant in support of an application for an
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experimental use permit, an amendment adding a new use to a
registration, or for re-registration, or to support or maintain in
effect an existing registration;
(3) the data 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 data are determined by EPA to be valid and usable in reaching
regulatory conclusions; and
(5) the data are not those 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 concerning 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 are
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 determin-
ing whether the applicant's product is registrable. There may be cases, how-
ever, where because of close similarities between the composition of two or
more products, another firm's data may suffice to allow EPA to evaluate some 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 re-registration (or new registration) under this Standard is found
in the Guidance Package for this Standard.
Obtaining Data to 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 for making registrability decisions) and 'nave 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".
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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 are 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 spe^fic" data. In some cases,
the Agency may possess 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 that 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
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.G., or copies of which may be .requested from
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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
identified 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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II. AGENCY POSITION ON CHLORONEB
Regulatory Position for Chloroneb
Chloroneb (1,4-dichloro-2,5-dimethoxybenzene) as described
in this Standard may be registered for sale, distribution,
reformulation and use in the United States. Considering all
available information on products registered on or before
May 15, 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 Chloroneb.
The Agency has determined that Chloroneb does not cause an
unreasonable adverse effect with proper label directions and
precautions. Chloroneb products currently registered may be
reregistered subject to the conditions imposed for data
requirements. New products may be registered under this
Standard and are subject to the same requirements.
Criteria for Registration Under the Standard
To be subject to this Standard, Chloroneb products must meet
the following conditions:
- contain Chloroneb as the sole active ingredient;
- bear required labeling; and
- be within acute toxicity limits.
Manufacturing-use Chloroneb products must bear label directions
for formulation into acceptable end-uses.
The applicant for registration or reregistration of Chloroneb
products subject to this Standard must comply with all terms
and conditions described in this Standard 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).
The following registrants have submitted data in support of
Chloroneb registrations, and have not waived their rights to
compensation for this data: E.I. duPont de Nemours and Co.,
Inc. and O.M. Scott and Sons Co.
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A. Manufacturing-use Chloroneb
1. Acceptable Ranges and Limits
a. Product Composition Standard
To be covered under this Standard, manufacturing-use
chloroneb products with any percentage of active ingredient
are acceptable with appropriate certification of limits.
The Agency identified the possibility of chlorinated dioxin
formation, including TCDD, during manufacture of chloroneb.
To be covered under this standard, applicants for registration
of manufacturing-use chloroneb products must demonstrate
that the manufacturing process will not result in the
formation of 2,3,7,8-tetrachlorobenzo-£-dioxin (TCDD).
b. Acute Toxicity Limits
The Agency will consider registration of manufacturing-use
chloroneb products which have established Toxicity Category
1 through IV ratings for each of the following acute effects:
Acute Oral Toxicity;
Acute Dermal Toxicity
Acute Inhalation Toxicity;
Primary Eye Irritation; and
Primary Dermal Irritation.
c. Use Patterns
To be covered under this Standard, manufacturing-use chloroneb
must be formulated into end-use fungicides which are intended
for outdoor nondomestic terrestrial uses (food or nonfood).
2. Data Requirements and Data Gaps
Applicants for registration of manufacturing-use chloroneb
products with all acceptable end-uses must cite or submit
the following information on the physical/chemical properties,
composition, fate and toxicity of the proposed product.
Data in this Standard that satisfy registration requirements
may be cited, if the applicant establishes that the proposed
product is substantially similar to another product for
which the Agency has received acceptable acute toxicity
tests. Data may be cited provided compensation has been
offered to the submitters of these studies. The Agency
will consider both active and inert ingredients in the
determination of substantially similar products. Before
each requirement is listed the section of the Proposed
Guidelines which describes that type of data and when it is
required [43 FR, No. 132, 29696 of July 10, 1978; and 43 FR,
No. 163, 37336 .of August 22, 1978]. Applicants for the
reregistration of manufacturing-use chloroneb must sumbit
all information identified as data gaps (see charts).
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PRODUCT CHEMISTRY
Data Gaps
Data Requirements
163.61-3 Product Identity
163.61-4 Composition Starting
Materials
163.61-4 Manuf. Process
163.61-3 Disc, of Ingred.
163.61-5 Disc, of Unint.
Ingredients
163.61-6 Certification of
Limits
163.61-7 Analyt. Meth./Data
163.61-8 Color
163.61-8 Odor
163.61-8 Melting Point
163.61-8 Solubility
163.61-8 Stability
163.61-8 Oct./Water Part.
Coefficient
163.61-8 Physical State
163.61-8 Density or Specific
Gravity
163.61-8 Vapor Pressure
163.61-8 pH
163.61-8 Storage Stability
163.61-8 Flammability
163.61-8 Oxidizing/Reducing
Action
163.61-8 Explosiveness
163.61-8 Corrosion
Food
Use
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
Nonfood
Use
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
Food Nonfood
Use Use
X
X
X
X(data)
X
X
X
X
X
X
X
X
X
X
X(data)
X
X
X
X
X
X
X
Test
Substance
Technical Grade
Technical Grade
Manufacturing-
use Product
Technical Grade
and/or Manufac-
turing-use Produc
Technical Grade
Technical Grade
and/or Manufac-
turing-use Produc
Manufacturing- use
Product
Manufacturing-use
Product
Manufacturing-use
Product
Manufacturing-use
Product
Manufacturing-use
Characteristics
Product
10
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TOXICOLOGY
Data Requirements
Food
Use
Nonfood
Use
Data Gaps
Food Nonfood
Use Use
Data Which
Must be Cited
163.81-1 Acute Oral Tox.
163.81-2 Acute Dermal Tox.
163.81-3 Acute Inhal. Tox.
163.81-4 Primary Eye
Irritation*
163.81-5 Primary Dermal
Irritation
163.81-6 Skin Sensitization
163.82-1 Subchronic Oral Tox.
163.82-2 Subchronic (21 day)
Dermal Tox.
163.83-1 Chronic Feeding
163.83-2 Oncogenicity
163.83-3 Teratogenicity
163.83-4 Reproduction
163.83-1 Mutagencity
through -4
163.85-1 Metabolism
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
GS0007-010
GS0007-011
GS0007-012
X
X
*Primary Eye Irritation test or_ demonstration of pH between 1 and 3 or 12 and 14 or^
demonstration of dermal irritation of Category I.
11
-------
ENVIRONMENTAL FATE
Data Requirements
163.62-7 Hydrolysis
163.62-7 Photolysis
163.62-8 Aerobic/Anerobic
Soil Metab.
163.62-8 Microbes on Chloroneb
163.62-8 Chloroneb on Microbes
163.62-8 Activated Sludge
Metabolism
163.62-9 Leaching
163.62-9 Adsorption/Desorption
163.62-10 Terrestrial Field
Di ssi p.
163.62-11 Rotational Crop
163.62-11 Fish Accumulation
Food
Use
X
X
X
X
X
X
X
X
X
X
X
Nonfood
Use
X
X
X(aerobic)
X
X
X
X
X
X
X
Data
Food
Use
X
X
X
X
X
X
X
X
X
Gaps
Nonfood
Use
X
Data Which
Must be Cited
X (aerobic)
X
X
X
X
X
X
00001426
GS0007-007
12
-------
RESIDUE CHEMISTRY
Data Requirements (Food Use) Data Gaps Data Which Must be Cited
Metabolism in Plants
Metabolism in Animals X
Analytical Methods
Residue Data: Crops
Snap Beans/Dried Beans X(Beans/Bean Vines)
Soybeans X(and Soybean Vines)
Sugarbeets X
Cottonseed/Cotton Forge X
Residue Data: Processed Crops
Cottonseed X
Soybeans X
Sugarbeets X
Residue Data:
Milk and Meat X
Storage and Stability X
13
-------
Residue Chemistry Data Gaps
1) Data on the metabolism of chloroneb in food animals.
Available data- are qualitative, whereas quantitative as well
as qualitative data on the disposition of chloroneb in food
animals are required.
2) Data on residues in beans and bean vines (forage),
soybeans and soybean vines (forage), cottonseed and cotton
forage, and sugarbeets (roots and tops). Available data
were not submitted in raw* form and, with the exception of
the data on beans, were obtained on an inadequate number of
samples.
3) Information on the storage of agricultural commodities
between sampling and residue analysis. Data on storage
conditions and on the stability of residues during sample
storage are required. No data are available.
4) Data on residues in fractions of processed cottonseed,
soybeans, and sugarbeets. No data are available. The
data would not be required if residues in raw agricultural
commodities are low enough that residues in processed
commodities would not likely exceed 0.1 ppm, the tolerance
on the raw commodities. The Agency assumes a maximum
concentration factor of 5 in processing cottonseed and
soybeans to oil, and a factor of 20 in processing sugarbeets
to dried pulp. Therefore, fractionation studies would not
be required if residues on cottonseed and soybeans were less
than .02 ppm (.lppm/5), and residues on sugarbeets were less
than .005 ppm (.lppm/20).
5) Data on whether residues are transferred from items
of animal feed to meat and milk. Available data were
obtained on too few animals, and were not submitted in
raw* form.
*Raw data are data which are uncorrected for reagent
blanks, untreated crop blanks, and recovery of fortified
samples.
14
-------
ECOLOGICAL EFFECTS
Data Requirements
Data Gaps
Food Nonfood Food Nonfood
Use Use Use Use
Data Which
Must be Cited
163.72-1 Freshwater Fish LC50
Coldwater
Warmwater
163.71-1 Bird Single Dose
Oral LD50
163.71-2 Bird Subacute
Dietary LC50
163.72-2 Aquatic Invertebrates
X
X
X
X
X
X
X
X
X
X
X
X
GS0007-003
GS0007-004
GSOOO7-002
GS0007-001
GS0007-005
15
-------
3. Required Labeling
All manufacturing-use chloroneb products must bear appropriate
labeling as specified in 40 CFR 162.10.
a. Use Pattern Statements
All manufacturing-use chloroneb products must list on the
label the intended end-uses of formulated products produced
from the manufacturing-use products. In accordance with
data to be submitted or cited, all chloroneb product
labels must bear one of the following statements:
"For Formulation into End-Use Fungicide Products
Intended Only for Nondomestic, Food, Outdoor Use"';
or
"For Formulation into End-Use Fungicide Products
Intended
or
for Nondomestic, Nonfood, Outdoors Use"
"For Formulation into End-Use Fungicide Products
Intended Only for Nondomestic, Food or Nonfood, Outdoors
Use".
16
-------
Presented below are the types of statements which must
appear on manufacturing-use chloroneb labels. See 40 CFR
162.10 for specific required labeling for manufacturing-use
products.
PRODUCT NAME
"For Formulation into End-Use Fungicide
Products Intended Only for Nondomestic,
Food, Outdoor Use.""
ACTIVE INGREDIENT:
Chloroneb (1,4-dichloro-2 ,5-
dimethoxybenzene) %(min)
INERT INGREDIENTS: %
100%
CAUTION
! PRECAUTIONARY STATEMENTS
•
. Hazards to Humans and Domestic Animals
•
•
. May irritate eyes, nose, throat, and skin. Avoid
. breathing dust. Avoid contact with skin, eyes and
. c 1 ot h i n g .
•
. First Aid Statement: In case of contact, immediately
. flush skin or eyes with plenty of water. Get medical
. attention if irritation persists.
•
. Environmental Hazards
•
. Do not discharge into lakes, streams, ponds, or public
. waters unless in accordance with an NPDES permit. For
. guidance, contact your regional office of EPA.
17
-------
. Directions for Use
•
. It is a violation of federal law to use this product
. in a manner inconsistent with its labeling. Refer to
. technical bullet in.
•
. Storage and Disposal
•
. Do not contaminate water, food, or feed by storage or
. disposal. Do not re-use empty container; bury in a
. safe place away from water supplies. Consult federal,
. state, or local disposal authories for approved
. alternative procedures such as limited open burning.
. Open dumping is prohibited.
•
. EPA Registration No.
. Establishment No.
. Net Wt. or Measure
Name and Address of the producer, registrant, or
person for whom produced.
18
-------
4. Tolerance Reassessment
Tolerances have been established for residues of chloroneb
and its metabolite, 2,5-dichloro-4-methoxyphenol (calculated
as chloroneb), in or on raw agricultural commodities as
indicated: 2 ppm in or on cotton forage, bean vines, and
soybean vines; 0.2 ppm in or on meat, fat, and meat by-products
of cattle, goats, hogs, horses, and sheep; 0.1 ppm (neglible
residue) in or on beans, cottonseed, soybeans, and sugarbeets
(roots and tops); and 0.05 ppm (negible residue) in milk (40
CFR 180.257).
The theoretical maximum residue contribution (TMRC) of
chloroneb to the human diet is calculated to be .064 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 has calculated a tentative acceptable daily
intake (ADI) value of .125 milligrams of chloroneb per
kilogram of body weight per day. This value is based on a
"no-observed-effect" level (NOEL) of 500 ppm established in
a two year dog study, and the incorporation of a 100 fold
safety factor in translating the data from animal to man.
This ADI value can only be considered tentative until the
Agency is able to verify the NOEL through the submission of
additional required chronic effects data (see Toxicology
data gap.s).
From available data, the Agency has established a maximum
permissible intake (MPI) value of 7.5 mg/day for an average
(60 kg.) adult (ADI X 60 kg = MPI).
*•- »
The theoretical maximum residue contribution of chloroneb to
the diet is less than the maximum permissible intake (.064
mg/day is less than 7.5 mg/day). Current tolerance levels
appear to be more than adequate.
5. Regulatory Rationale
a. Data Gaps
Data on physical and chemical properties and acute toxicity
are required for all chloroneb manufacturing-use products.
Chloroneb's food use and the need for tolerances for those
uses is the basis for chloroneb's chronic toxicology data
requirements. The nonfood-nondomestic use pattern of
chloroneb requires subchronic testing and teratogenicity,
and mutagenicity data. Chronic studies for the nonfood,
nondomestic use.pattern are not currently required because
the use pattern is not expected to result in repeated
exposure over a significant portion of the human li fe
span.
19
-------
B. Wettable Powder Chloroneb
]. Acceptable Ranges and Limits
a. Product Composition Standard
To be covered under this Standard, wettable powder chloroneb
products with any percentage of ingredients are acceptable
with appropriate certification of limits.
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,
wettable powder chloroneb products must have Toxicity
Category II through IV ratings for each of the following
acute effects:
Acute Oral Toxicity;
Acute Dermal Toxicity
Acute Inhalation Toxicity;
Primary Eye Irritation; and
Primary Dermal Irritation.
c. Use Patterns and Application Methods
To be registered under this Standard, WP products of
chloroneb may be used only as a fungicide on cotton, beans,
soybeans, and sugarbeets or ornamental turf.
The Agency considers chloroneb use as a seed treatment on
cotton, beans, soybeans, and sugarbeets, and in-furrow soil
treatment for cotton, beans, and soybeans to be a food use.
The use on ornamental turfgrass does not constitute a food
use with the restriction that grazing or feeding of clippings
from treated areas to livestock is prohibited.
The Agency finds that current dosage rates and application
methods are acceptable under this Standard.
2. Data Requirements and Data Gaps
Applicants for registration of wettable powder chloroneb
products must cite or submit the following information
on the physical/chemical properties, composition, and acute
toxicity of the proposed product. If the appl icant. establi shes
that a product is substantially similar to another product,
for which the Agency has received acceptable acute toxicity
tests, these data may be cited provided compensation has been
offered to the submitters of these studies. The Agency will
consider both active and inert ingredients in making the
determination of substantially similar products.
20
-------
The Agency has not received acceptable acute toxicity data
or product chemistry data for any wettable powder chloroneb
product. The Agency has determined that no existing wettable
powder chloroneb product is substantially similar to another.
Therefore, all required acute toxicity tests and product
chemistry data are needed for each currently registered
wettable powder product.
Applicants are hereby advised that if the Agency does not
receive commitments, within the specified time frame, from
maufacturing-use chloroneb producers to fill data gaps
identified for the manufacturing-use product, manufacturing-use
product registrations will be suspended. Formulators must
then bear the burden of supplying the data if formulators
want the manufacturing-use product to be available.
21
-------
WETTABLE POWDER
Data Requirements
Food Nonfood
Use Use
Data Gaps
Food Nonfood
Use Use
Data Which
Must be Cited
Product Chemistry
163.61-7 Analytical Methods X
and Data
163.61-6 Certification of X
Limits
163.61-8 Color X
163.61-8 Odor X
163.61-8 Density or X
Specific Gravity
163.61-8 pH X
163.61-8 Storage Stability X
163.61-8 Flamtnability X
163.61-8 Oxidizing/Reducing X
Action
163.61-8 Explosiveness X
163.61-8 Corrosion X
Characteristics
Toxicology
163.81-1 Acute Oral Toxicity X
163.81-2 Acute Dermal Toxicity X
163.81-3 Acute Inhalation X
Toxicity ,
163.81-4 Primary Eye Irritation X
163.81-5 Primary Dermal X
Irritation
163.81-6 Skin Sensitization X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
A demonstration of pH between 1 and 3 or 12 and 14 mi a demonstration of dermal
corrosiveness will allow the Agency to establish that a product is corrosive to the
eye, an an eye irritation test need not be performed.
22
-------
3. Required Labeli ng
All wettable powder chloroneb products must bear appropriate
labeling as specified in 40 CFR 162.10.
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.
23
-------
Presented below are types of statements which must appear on
wettable powder chloroneb labels. See 40 CFR 162.10 for
specific required labeling for formulated products.
PRODUCT NAME
•
ACTIVE INGREDIENT:
•
Chloroneb (1 ,4-dichloro-2,5-
dimethoxybenzene) %(min)
! INERT INGREDIENTS: %
100%
•
•
Keep out of reach of children.
•
CAUTION
! PRECAUTIONARY STATEMENTS
•
. Hazards to Humans and Domestic Animals
•
. May irritate eyes, nose, throat, and skin. Avoid
. breathing dust. Avoid contact with skin, eyes and
. c 1 ot h i n g.
•
. Other Prohibitions
•
. Seed Treatment
Do not use treated seed for food, feed, or oil.
purposes.
•
For use on beans and soybeans: Do not graze on
treated plants within 45 days of planting.
•
. Ornamental Turf
Do not allow grazing or feeding of clippings from
treated areas to livestock.
24
-------
Directions for Use
It is a violation of federal law to use this product
in a manner inconsistent with its labeling.
Registered Appplication Rates
Site
seed
Formu-
1 a t i o n
Type of Application rate
App1ic. (Ib. or oz. a.i.)
Wettable
Powder
(65%)
cotton
furrow
sugarbeets seed
beans
soybeans
turf
seed
furrow
seed
furrow
f o 1 i ar
3.9 oz/100 Ib seed
6.5 oz/100 Ib seed
1.3-1.9 Ib/A
3.9 oz/100 Ib seed
2.6 oz/100 Ib seed
.98 Ib/A
2.6 oz/100 Ib seed
.98 Ib/A
7.08 Ib/A for Pythium
blight
10.6-15.9 Ib/A for
snow mold
Storage and Disposal
Do not contaminate water, food, or feed by storage
or disposal. Do not re-use empty container; bury in
a safe place away from water supplies. Consult
federal, state, or local disposal authories for
approved alternative procedures such as limited open
burning. Open dumping is prohibited.
.
Name and Address of the producer, registrant, or person .
for whom produced.
EPA Registration No. !
Establishment No.
Net Wt. or Measure
25
-------
4. Regulatory Rationale
Wettable powder chloroneb may be registered for use in the
United States. The registration is dependent upon filling
the data gaps identified in the disciplinary chapters of
wettable powder chloroneb and upon meeting standards for
nondomestic use.
a. Acceptable Ranges and Limits
Product Composition Standards
The Agency will consider for registration wettable powder
chloroneb products which contain chloroneb as the sole
active ingredient if the products meet the acute toxicity
standards for nondomestic use, and if the inert ingredients
in food-use formulations have been cleared under 40 CFR
180.1001.
Acute Toxicity Limits
The Agency will register wettable powder chloroneb products
for nondomestic use that have acute toxicity category II
through IV ratings because the nondomestic user can be
expected to take precautions associated with Category II
pesticides.
Use Patterns and Application Methods
Wettable powder chloroneb products may be registered for
nondomestic use as a fungicide seed or infurrow soil
treatment only for cotton, soybeans, and beans, and as a
seed treatment only on sugarbeets. It may also be registered
for nondomestic use on ornamental turf.
The Agency finds that currently registered dosage rates and
application methods are acceptable pending submission of
required residue chemistry data listed in the manufacturing-
use standard. There is no data to suggest that maximum
dosage rates on currently registered labels would produce
residues that would exceed tolerances set for chloroneb.
C. Granular Chloroneb
1. Acceptable Ranges and Limits
a. Product Composition Standards
To be covered under this Standard, granular chloroneb
products with any percentage of ingredients are acceptable
with appropriate certification of limits.
26
-------
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 non-domestic use under this Standard,
granular chl-oroneb products must have Toxicity Category II
through IV ratings for each of the following acute effects:
Acute Oral Toxicity;
Acute Dermal Toxicity
Acute Inhalation Toxicity;
Primary Eye Irritation; and
Primary Dermal Irritation.
c. Use Patterns and Application Methods
To be registered under this Standard, granular products of
chloroneb may be used only as a fungicide on cotton, beans,
soybeans or ornamental turf.
The Agency considers chloroneb use as an in-furrow soil
treatment for cotton, beans, and soybeans to be a food use.
The use on ornamental turfgrass does not constitute a food
use with the restriction that grazing or feeding of clippings
from treated areas to livestock is prohibited.
The Agency finds that current dosage rates and application
methods are acceptable under this Standard.
2. Data Requirements and Data Gaps
Applicants for registration of granular chloroneb products
must cite or submit the following information on the physical/
chemical properties, composition and acute toxicity of the
proposed product. Data in this Standard that satisfy
registration requirements may be cited, if the applicant
establishes that the proposed product Is substantially
similar to another product for which the Agency has acceptable
acute toxicity tests. Data may be cited provided compensation
has been offered to the submitters of these studies. The
Agency will consider both active and inert ingredients in
making determinations of substantial similarity.
The Agency has received acceptable acute toxicity data for
some categories of tests for one granular product (see
Topical Discussions). No product chemistry data were
available. The Agency has determined that no existing
granular chloroneb product is substantially similar to
another. Therefore, all acute toxicity tests and product
27
-------
chemistry data are required of each product. The guidance
package accompanying this standard identifies the single
product for which the Agency has received acceptable acute
toxicity data.
Applicants are hereby advised that if the Agency does
not receive commitments, within the specified time frame,
from manufacturing-use chl oroneb producers to fill data gaps
identified for the manufacturing-use material, the registrations
of manufacturing-use products will be suspended. Formulators
must then bear the burden of supplying this data if continued
availability of the manufacturing-use product is desired.
28
-------
GRANULAR
Data Gaps
Food Nonfood Food Nonfood Data Which
Data Requirements Use Use Use Use Must be Cited
Product Chemistry
163.61-7 Analytical Methods XX XX
and Data
163.61-6 Certification of X X X X
Limits
163.61-8 Color XX XX
163.61-8 Odor XX XX
163.61-8 Density or X X X X
Specific Gravity
163.61-8 pH X X X X
163.61-8 Storage Stability XX XX
163.61-8 Flammability XX XX
163.61-8 Oxidizing/Reducing XX XX
Action
163.61-8 Explosiveness XX XX
163.61-8 Corrosion XX XX
Characteristics
Toxicology
163.81-1 Acute Oral Toxicity1 XX XX
163.81-2 Acute Dermal Toxicity XX XX
163.81-3 Acute Inhalation XX XX
Toxicity ,
163.81-4 Primary Eye Irritation XX XX
163.81-5 Primary Dermal XX XX
Irritation
163.81-6 Skin Sensitization XX XX
The Agency has received acceptable acute oral LD50 data and primary dermal irritation
data for one registered granular product. See guidance package accompanying this Standard
for information on the identity of this product.
2
A demonstration of pH between 1 and 3 or 12 and 14 j)r a demonstration of dermal
corrosiveness will allow the Agency to establish that a product is corrosive to the eye,
and an eye irritation test need not be performed.
29
-------
3. Required Labeling
All granular chloroneb products must bear appropriate
labeling as specified in 40 CFR 162.10. 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 my state the
contents of 40 CFR Part 170 or additional statements.
30
-------
Presented below are types of statements which must appear on
granular chloroneb labels. See 40 CFR 162.10 for specific
required labeling for formulated products.
PRODUCT NAME
•
! ACTIVE INGREDIENT:
•
Chloroneb (1,4-dichloro-2 ,5-
dimethoxybenzene) %(min)
! INERT INGREDIENTS: %
100%
•
•
Keep out of reach of children.
•
CAUTION
PRECAUTIONARY STATEMENT
•
. Hazards to Humans and Domestic Animals
•
. May irritate eyes, nose, throat, and skin. Avoid
. breathing dust. Avoid contact with skin, eyes and
. clothing.
*
. Other Prohibitions
. Seed Treatment
Do not use treated seed for food, feed, or oil
purposes.
•
For use on beans and soybeans: Do not graze on
treated plants within 45 days of planting.
•
. Ornamental Turf
Do not allow grazing or feeding of clippings from
treated areas to livestock.
31
-------
. Directions for Use
•
. It is a violation of federal law to use this product
. in a manner inconsistent with its labeling.
•
. Registered Appplication Rates
•
. Formu- Type of Application rate
. 1 atipn Site App1ic. (1b. or oz. a.i.)
•
. Granular turf foliar 7.1-16.6 1b/A
. (1.015-10%)
•
cotton furrow 1-2 Ib/A
•
beans furrow 1 1b/A
•
soybeans furrow 1 Ib/A
•
. Storage and Disposal
•
. Do not contaminate water, food, or feed by storage
. or disposal. Do not re-use empty container; bury in
. a safe place away from water supplies. Consult
. federal, state, or local disposal authorities for
. approved alternative procedures such as limited open
. burning. Open dumping is prohibited.
Name and Address of the producer, registrant, or person .
for whom produced.
•
EPA Registration No. ___,
Establishment No.
Net Wt. or Measure
32
-------
4. Regulatory Rationale
Granular chloroneb may be registered for nondomestic use in
the United States. The registration is dependent upon filling
the data gaps identified in the disciplinary chapters of granular
chloroneb and upon meeting standards for nondomestic use.
Acceptable Ranges and Limits
Product Composition Standards
The Agency will consider for registration granular chloroneb
products which contain chloroneb as an active ingredient if
the products meet the acute toxicity standards for non-
domestic general use, and if inert ingredients in food-use
formulations have been cleared under 40 CFR 180.1001.
Acute Toxicity Limits
The Agency will register granular chloroneb products
for nondomestic use that have acute toxicity category
II through IV ratings because the nondomestic user can be
expected to take precautions associated with Category II
pesticides.
Use Patterns and Application Methods
Granular chloroneb products may be registered for nondomestic
use as a fungicide infurrow soil treatment only for cotton,
soybeans, and beans. - It may also be registered for nondomestic
use on ornamental turf.
The Agency finds current dosage rates and application
methods acceptable. There are no data to suggest that
maximum dosage rates on currently registered labels would
produce residues that would exceed tolerances set for
chloroneb.
D. Dust Chloroneb
1. Acceptable Ranges and Limits
a. Product Composition Standards
To be covered under this Standard, dust chloroneb products
with any percentage of ingredients are acceptable with
appropriate certification of limits.
Inert ingredients in food-use formulations must be cleared for
such use under 40 CFR 180.1001.
33
-------
b. Acute Toxlcity Limits
To be registered for nondomestic use under this Standard,
dust chloroneb products must have Toxicity Category II
through IV ratings for each of the following acute effects:
1) Acute Oral Toxicity;
2) Acute Dermal Toxicity;
3) Acute Inhalation Toxicity;
4) Primary Eye Irritation; and
5) Primary Dermal Irritation.
c. Use Patterns and Application Methods
To be under this Standard, dust products of chloroneb may be
used only as a fungicide on cotton, beans or soybeans.
The Agency considers chloroneb use as a seed treatment or
in-furrow soil treatment to be a food use.
The Agency finds that dosage rates and application methods
on currently registered labels are acceptable under this
Standard.
2. Data Requirements and Data Gaps
Applicants for registration of dust chloroneb products must
cite or submit the following information on the physical/
chemical properties, composition, and acute toxicity of the
proposed product. If the applicant establishes that a
product is substantially similar to another product for
which the Agency has received acceptable acute toxicity
tests, this data may be cited provided compensation has been
offered to the submitters of these studies. Both active and
inert ingredients will be considered in making determination
of substantial similarity.
The Agency has not received acceptable acute toxicity-or
product chemistry data for any category of test, for any
dust chloroneb product. The Agency has determined that no
existing dust chloroneb product is substantially similar to
another. Therefore, all acute toxicity tests and product
chemistry data are required of each dust chloroneb product.
Applicants are hereby advised that if the Agency does not
receive commitments, within the specified time frame, from
manufacturing-use chloroneb producers to fill gaps identified
for the manufacturing-use material, the registrations of
manufacturing-use products will be suspended. Formulators
must then bear the burden of supplying this data if continued
availability pf the manufacturing-use product is desired.
34
-------
DUST
Data Requirements
Food
Use
Nonfood
Use
Data Gaps
Food Nonfood
Use Use
Data Which
Must be Cited
Product Chemistry
163.61-7 Analytical Methods X
and Data
163.61-6 Certification of X
Limits
163.61-8 Color X
163.61-8 Odor X
163.61-8 Density or X
Specific Gravity
163.61-8 pH X
163.61-8 Storage Stability X
163.61-8 Flammability X
163.61-8 Oxidizing/Reducing X
Action
163.61-8 Explosiveness X
163.61-8 Corrosion X
Characteristics
Toxicology
163.81-1 Acute Oral Toxicity X
163.81-2 Acute Dermal Toxicity X
163.81-3 Acute Inhalation X
Toxicity ,
163.81-4 Primary Eye Irritation1 X
163.81-5 Primary Dermal X
Irritation
163.81-6 Skin Sensitization X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
A demonstration of pH between 1 and 3 or 12 and 14 ^r a demonstration of dermal
corrosiveness will allow the Agency to establish that a product is corrosive to the eye,
and an eye irritation test need not be performed.
35
-------
3. Requi red Label ing
All dust chloroneb products must bear appropriate labeling
as specified in 40 CFR 162.10. All labels and labeling
intended for agricultural use products must bear the following
statement: "This proudct must be applied in accordance with
40 CFR Part 170." Registrants may state the contents of the
40 CFR Part 170 or additional statements.
36
-------
Presented below are types of statements which must appear on
dust chloroneb labels. Refer to 40 CFR 162.10 for specific
labeling requirements for formulated products.
PRODUCT NAME
•
! ACTIVE INGREDIENT:
•
Chloroneb (1,4-dichloro-2,5-
dimethoxybenzene) %(min)
INERT INGREDIENTS: %
100%
•
•
Keep out of reach of children.
•
! CAUTION
'. PRECAUTIONARY STATEMENTS
•
. Hazards to Humans and Domestic Animals
•
. May irritate eyes, nose, throat, and skin. Avoid
. breathing dust. Avoid contact with skin, eyes and
. clothing.
• v
. Other Prohibitions
•
. Seed Treatment
Do not use treated seed for food, feed, or oil
purposes.
•
For use on beans and soybeans: Do not graze on
treated plants within 45 days of planting.
37
-------
Direction for Use
It is a violation of federal law to use this product
in a manner inconsistent with its labeling.
. Registered Appplication Rates
F o rm u -
1 ation
Dust
(10%)
Site
cotton
beans
soybeans
Type of
A p p 1 i c .
seed
furrow
seed
furrow
seed
furrow
(Ib. or oz. a.i.)
.5 lb/100 Ib seed
1-2 Ib/A
.2 lb/100 Ib seed
1 Ib/A
.2 lb/100 Ib seed
1 Ib/A
Storage and Disposal
. Do not contaminate water, food, or feed by storage or
. disposal. Do not re-use empty container; bury in a
. safe place away from water supplies. Consult federal,
. state, or local disposal authories for approved alter-
. native procedures such as limited open burning. Open
. dumping is prohibited.
• •
. Name and Address of the producer, registrant, or person .
. for whom produced.
• •
. EPA Registration No.
. Establishment No.
. Net Wt. or Measure
38
-------
4. Regulatory Rationale
Dust chloroneb may be registered for nondomestic use in the
United States. The registration is dependent upon filling
the data gaps identified in the disciplinary chapters of
dust chloroneb and upon meeting description of nondomestic
use.
a. Acceptable Ranges and Limits
Product Composition Standards
The Agency will consider for registration dust chloroneb
products which contain chloroneb as the sole active ingredient
if the products meet the acute toxicity standards for
nondomestic use, and if the inert ingredients in food-use
formulations have been cleared under 40 CFR 180.1001.
Acute Toxicity Limits
The Agency will register dust chloroneb products for nondomestic
use that have acute toxicity category II through IV
ratings because the nondomestic user can be expected to take
precautions associated with Category II pesticides.
Use Patterns and Application Methods
Dust chloroneb products may be registered for nondomestic
use as a fungicide seed or infurrow soil treatment only for
cotton, soybeans, and beans.
The Agency finds that currently registered dosage rates and
application methods are acceptable pending submission of
required residue chemistry data listed in the manufacturing-
use standard. There is no data to suggest that maximum
dosage rates on currently registered labels would produce
residues that would exceed tolerances set for chloroneb.
39
-------
III. PRODUCT CHEMISTRY
Intreduction
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 0.1% 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 uninten
tional 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 and boiling point data, ambient vapor pressure
and solubility). Data are also required on the properties
of the formulated product to establish labeling cautions
(e.g., fl ammabi 1 ity , corrosiveness or storage stability). /'
The Agency uses these data to characterize each pesticide
and to determine its environmental and health hazards.
Product Chemistry - Manufacturing-Use Chloroneb
Product Chemistry Profile
One manufacturing use product containing approximately 90%
chloroneb is currently registered.
A detailed manufacturing procedure was not available to the
Agency. The two major routes by which technical chloroneb
could be synthesized involve either direct chlorination of
1,4-dimethoxy-benzene, or chlorination of quinone or hydro-
quinone followed by methylation. With either of these
routes there exists the possibility of chlorinated' dioxin
formation including TCDD depending on the reaction conditions
and on the purity of starting materials.
40
-------
Methods for the determination of chloroneb in wettable
powder formulations, the determination of chloroneb in the
technical chemical, and the determination of volatile
impurities in the technical chemical have been submitted to
the Agency.
A small amount of data are available on the physical and
chemical properties of technical chloroneb.
Data Requirements
Listed below are Product Chemistry data needed to adequately
support the registration of any manufacturing-use chloroneb
product. Following each data requirement is the section
in the Proposed Guidelines for the Registration of Pesticides
in the United States (43 FR 29696, July 10, 1978) that
describes the type of data required. The applicant for
registration must submit or cite the following information.
For Manufacturi ng-Use Chioroneb:
1) Product Identity 163.61-3(a)
2) Identification of all impurities
exceeding 0.1% of the weight of the
technical chloroneb product 163.61-3(c)
3) Composition of the starting materials
used to manufacture technical ehloroneb...163.61-4(a)
4) Detailed manufacturing process for
technical chl oroneb 163.61-4(b)
5) Discussion on the formation of
unintentional ingredients during the
manufacture of technical chloroneb 163.61-5
6) Declaration of Limits 163.61-6(a)
7) Certification that limits on the active
ingredient and impurities in technical
chloroneb will be maintained for all
quantities of the product sold or
distributed in interstate commerce 163.61-6(b)
8) Analytical method and data on the compo-
sition of technical chloroneb. Data on
the active ingredient and each identifiable
impurity exceeding 0.1% of the product
weight are to. be obtained on five or
more samples of the product 163.61-7(b)
41 .
-------
9) Physical and chemical properties.
a) Color 163.61-8(c) (1)
b) Odor 163.61- (c)(2)
c) Melting point 1 63. 61-8(c) (3 )
d) Solubility (in quantitative terms)...163.61-8(c)(4)
e) Stability 1 63. 61-8(c) (5 )
f) Octanol/water partition coefficient..163.61-8(c)(6)
g) Physical state 1 63. 61-8(c) (7 )
h) Density or Specific Gravity 1 63.61-8(c) (8)
i) Boiling Point 1 63. 61-8(c) (9)
j) Vapor Pressure 1 63. 61-8(c) (10)
k) pH 163.61-8(c)(11)
i) Storage Stability 163.61-8(c)(1 2)
m) Flammability 163.61-8(c)(13)
n) Oxidizing and Reducing Action 163.61-8(c)(14)
o) Explosiveness 1 63.61-8(c) (1 5)
p) Corrosion Characteristics 163.61-8(c)(18)
Data Gaps
Manufacturing Process 163.61-4
Formation of Unintentional Ingredients 163.61-5
Active Ingredient Limits 163.61-6
Data Obtained from Analytical Methods 163.61-7
Physical/Chemi cal Properties 163.61-8
Octanol/Water Partition
Coefficient
PH
Storage Stability
Flammabi1ity
Oxidizing/Reducing Action
Explosiveness
Corrosion Characteristics
-\
/
Topical Discussions
Corresponding to each of the Topical Discussions listed
below is the number of the section in the 'Proposed Guidelines
for Registering Pesticides' in the United States (43 FR
29696, July 10, 1978) which explains the minimum data
that the Agency requires in order to adequately assess
Product Chemistry of manufacturing-use chloroneb products.
Also, under each of the following topics is a reference to
the appropriate section in the 'Proposed Guidelines'.
Guidelines Section
Chemical Identity 163.61-3
Manufacturing Processes 163.61-4
Formation of Unintentional
Ingredients 163.61-5
42
-------
Active Ingredient Limits in
Pesticide Products 163.61-6
Product Analytical Methods and Data 163.61-7
Physical/Chemical Properties 163.61-8
Chemical Identity
The Proposed Guidelines require identifying information
includ-ing chemical names, product names, and numerical
codes of all substances known or assumed to be present
in pesticide products. [163.61-3(c)]
"Chloroneb" is the common name accepted by the American
National Standards Institute (ANSI) for the chemical
1,4-dichloro-2,5-dimethoxybenzene. (Fig. 1). Chloroneb is
also known by the trade names "Demosan", Soil Fungicide
1823, and "Tersan". The Chemical Abstracts Registry (CAS)
number for chloroneb is 2675-77-6, and the EPA Shaughnessy
number is 027301. The common name will be used throughout
this standard in lieu of other chemical or trade names.
Manufacturing Processes
Because the route by which a pesticide is synthesized
determines the nature and amount of potentially toxic
impurities, a detailed description of the manufacturing
process is required. [163.61-4]
Technical chloroneb could be synthesized by two major routes
which involve either direct chlorination of 1,4-dimethoxy-
benzene or chlorination of quinone or hydroquinone followed
by methylation. Two patent applications (Alvarez 1968, GS
0007-015; Haglid 1979, 05013181) describe several chloroneb
manufacturing processes in sufficient detail to satisfy
Proposed Guidelines requirements. However, the Agency has
no information to indicate which if any of the processes are
used presently to manufacture technical chloroneb. A
description of the manufacturing process has been submitted to
the Agency. This description is not sufficiently detailed
to satisfy Guidelines requirements. Company submitted data
on manufacture of technical chloroneb is contained in the
Confidential Discussion Appendix.
Formation jvF Unintentional Ingredients
Section 163.61-5 of the Proposed Guidelines requires
registrants of manufacturing-use and of formulated products
to submit a theoretical discussion of the formation of
unintended substances in the product. Of particular relevance
to chloroneb would be a discussion of dioxin formation
incident to the manufacture of technical chloroneb.
43
-------
Manufacturing processes for chloroneb found in the patent
literature could result in dioxin formation. In one patent
application (Scribner and Soboczenski 1966, GS0007-009), six
routes by which chloroneb could be synthesized were outlined.
In four of these routes, the initial step is chlorination of
quinone or hydroqui none. A polychl orinated phenol with
a -Cl ortho to an -OH is an intermediate in these syntheses,
and thus,depending on reaction conditions, a variety of
dioxins may be formed. One of these routes involves
basic hydrolysis of 1,2,4,5-tetrachloro-benzene and could
thus result in formation of 2,3,7,8-tetrachlorodibenzo-p-dioxin
(TCDD).
The remaining routes discussed in Scribner and Soboczenski
(1966, GS0007-009) and the synthetic routes discussed in
other patent applications (Alvarez 1968, GS0007-015; Haglid
1979, 05013181), involve direct chlorination of 1,4 dimethoxy-
benzene and would be less likely to result in dioxin by-products
unless there were significant amounts of phenols in manufactur-
ing grade 1,4-dimethoxybenzene.
A theoretical discussion of the formation of unintended
substances is required and has not been submitted for
technical chloroneb. Such a discussion is required for each
technical.
Acti ve Ingredient Limits jji Pesticide Products
The Guidelines require that upper and lower limits be
established for each active ingredient and each intentionally
added inert in a pesticide product [163.61-6]. Technical
chloroneb contains approximately 90% of the pure chemical.
Upper and lower limits have not been established and certified ^
for technical chloroneb.
Product Analytical Methods and Data
The Guidelines require submission of, or reference to,
analytical methods for measuring each active ingredient
in a pesticide product. [163.61-7]
Section 163.61-7 of the Proposed Guidelines also require
that applications for registration of pesticide products
contain analytical data obtained by methods supplied to the
Agency.
Acceptable methods for the determination of chloroneb
and impurities in technical chloroneb are contained in
the Confidential Discussion Appendix. Data obtained by the
method are not available.
44
-------
Physical and Chemical Properties
For every pesticide product, the Proposed Guidelines
require data on certain physical and chemical
properties useful for identification purposes or for
evaluation of hazard potential [163.61-8].
A small amount of data are available on the physical and
chemical properties of chloroneb. Available data on purified
chloroneb (du Pont 1977, 00001444) are as follows:
Col or: White
Odor: Musty (technical chemical).
Melting point: 133-135°C
Boiling point: 268°C
Density or Specific Gravity: 1.66
lysic.
Hid.
Physical State: Purified chloroneb is a crystalline
so
Solubility: The solubilities of purified chloroneb in
selected solvents are as follows: 8 ppm in water at
25°C, 13.3% in methylene chloride, 11.8% in dimethyl
formamide, 11.5% in acetone, 8.9% in xylene.
Stabi1ity: Chloroneb is temperature stable at least up
to the boiling point; stable in water and common organic
solvents; stable in the presence of dilute acid or alkali;
and subject to microbial decomposition under moist condi-
tions in the soil.
Octanol/Water Partition Coefficient: No data are avail-
able.
VapprpPressure: " The vapor pressure of purified chloroneb
3x10 mm Hg at 25°C.
pH: There are no data available.
Storage Stability: There are no data available.
Flammability: There are no data available.
Oxidizing or Reducing Action: There are no data available.
Explosi veness: There are no data available.
Corrosion Characteristics: There are no data available
for technicalchloroneb.
45
-------
Available data on physical and chemical properties
of the purified chemical were submitted in tabular
form. Methods by which the data were obtained, and
individual values were not submitted.
Product Chemistry - Wett.able Powder Chloroneb
Data Gaps
1) Color 163.61-8(c)(l)
2) Odor 163.61-8(c)(2)
3) Density or Specific Gravity 163.61-8)c)(8)
4) pH 163.61-8(c)(ll)
5) Storage Stability 1 63. 61-8(c) (1 2)
6) Flammability 1 63. 61-8(c) (13)
7) Oxidizing or Reducing
Action 163.61-8(c)(14)
8) Expl osiveness 1 63. 61-8(c) (15)
9) Corrosion Characteristics ". 163.61-8(c)(18)
10) For each product an analy-
tical method for the determi-
nation of chloroneb if produced
by an integrated formulation system 163.61-7(a)(3)
11) Data obtained by use of the above method
on representative samples of
the product 163.61-7(5) (1)
12) Declaration and certification of the upper
and lower limits for each active ingredient
and intentionally added inert ingredient,
and the upper limit for each impurtiy,
reaction product, and degradation
product 163.61-6
Topical Discussions ?
The product chemistry of chloroneb has been dealt with in
the Manufacturing-Use Chloroneb section of this chapter.
The following are data required of all wettable powder
formulated products of chloroneb.
Active Ingredient Limits in Pesticide Products
For all pesticide products, the Guidelines would require
that upper and lower limits be established for each active
ingredient, impurity, reaction product, and degradation
product. [163.61-5]
i
Current registrations of wettable powder chloroneb contain
65% a.i.
For no wettable powder formulation of chloroneb has an upper
and lower limit been established.
46
-------
Product Analytical Methods and Data
The Guidelines would require submission of, or reference to,
analytical methods measuring each active ingredient in a
pesticide product. [163.61-7]
A method for the determination of chloroneb in 65% wettable
powder formulations has been submitted (du Pont 1977,
00001444). A sample of the formulated product is slurried
with chloroform and filtered through sintered glass. The
filtrate is mixed with an internal standard (biphenyl) and
aliquots analyzed by gas chromatography on columns of 20%
SE-30 on 60-80 mesh Diatoport S. Chloroneb concentration is
determined by comparison of the sample area ratio (sample
peak area divided by internal standard peak area) to the
corresponding ratio determined with a standard solution
consisting of chloroneb and biphenyl.
Section 163.61-7 of the Proposed Guidelines would require
that applications for registration of pesticide products
contain analytical data obtained by methods supplied to the
Agency. Data obtained by the method described above have
not been submitted.
Section 163.61-7 of the Proposed Guidelines would also
require that registrants of formulated products produced by
an integrated formulation system (Proposed Guidelines,
section 163.61-1) submit methods not only for the active
ingredient, but for each identifiable impurity associated
with manufacture of the technical chemical. Such methods
have not been submitted for any chloroneb formulation.
Physical and Chemical Properties
For every pesticide product, the Proposed Guidelines
would require data on certain physical and chemical properties
useful for identification purposes or for evaluation of
hazard potential [163.61-8].
The following physical and chemical properties are required
for all wettable powder products of chloroneb. There are no
data except storage stability of Demosan 65W Fungicide (du
Pont). Refer to the Confidential Appendix for this storage
stability data.
Required Physical/Chemical Properties: Color, odor, density
or specific gravity, pH, storage stability, f1ammabi1ity,
oxidizing or reducing action, explosiveness, and corrosion
characteristics.
47
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Product Chemistry - Granular Chloroneb
Data Gaps
1) Color 163.61-8(c)(l)
2) Odor 163.61-8(c)(2)
3) Density or Specific Gravity 163.61-8)c)(8)
4) pH 163.61-8(c) (11)
5) Storage Stability 1 63.61 -8(c) (12)
6) Flammability 163.61-8(c)(13)
7) Oxidizing or Reducing
Action 163.61-8(c) (14)
8) Explosiveness 163.61-8(c)(15)
9) Corrosion Characteristics 1 63.61 -8(c) (1 8)
10) For each product an analy-
tical method for the determi-
nation of chloroneb if produced
by an integrated formulation
system 163.61 -7( a) (3 ) (4)
11) Data obtained by use of the above
method on representative samples of
the product 1 63. 61-7 (b) (1 )
12) Declaration and certification of the upper
and lower limits for each active ingredient
and intentionally added inert ingredient,
and the upper limit for each impurtiy,
reaction product, and degradation
product 163.61-6
Topical Discussions
The product chemistry of chloroneb per se has been dealt
with in the Manufacturing-use Chloroneb section of this
chapter. The following are data required of all granular
formulated products of chloroneb.
Active Ingredient Limits in Pesticide Products
For all pesticide products, the Guidelines would require
that upper and lower limits be established for each active
ingredient, impurity, reaction product, and degradation
product. [163.61-5]
Current federal reoistrations of granular chloroneb contain
6.25% to 10% a.i.
For no granular formulation of chloroneb has an upper
and lower limit been established.
48
-------
Product Analytical Methods and Data
The Guidelines would require submission of, or reference to,
analytical methods measuring each active ingredient in a
pesticide product. [163.61-7]
Section 163.61-7 of the Proposed Guidelines would require
that applications for registration of pesticide products
contain analytical data obtained by methods supplied to the
Agency.
Section 163.61-7 of the Proposed Guidelines would also
require that registrants of formulated products produced by
an integrated formulation system (Proposed Guidelines,
section 163.61-1) submit methods not only for the active
ingredient, but for each identifiable impurity associated
with manufacture of the technical chemical. Such methods
have not been submitted for any chloroneb formulation.
Methods for the determination of chloroneb in granular
formulations have not been submitted.
Physical and Chemical Properties
For every pesticide product, the Proposed Guidelines would
require data on certain physical and chemical properties
useful for identification purposes or for evaluation of
hazard potential [163.61-8].
The following physical and chemical properties are required
for all granular products of chloroneb. There are no
data.
Required Physical/Chemical Properties: Color, odor, density
or specific gravity, pH, storage stability, fl ammabi 1 i ty ,
oxidizing or reducing action, explosiveness, and corrosion
characteristics.
Product Chemistry - Dust Chloroneb
Data Gaps
1) Color 163.61-8(c) (1)
2) Odor 163.61-8(c)(2)
3) Density or Specific Gravity 1 63. 61-8(c) (8)
4) pH 163.61-8(c)(ll)
5) Storage Stability 163.61-8(c)(1 2)
6) Flammability 163.61-8(c) (13)
7) Oxidizing or Reducing Action 163.61-8(c)(14)
8) Expl osi veness 163.61-8(c)(1 5)
9) Corrosion Characteristics 163.61-8(c)(1 8)
49
-------
10) For each product an analytical
method for the determination of
chloroneb if produced by an
inegrated formulation system 1 63.61-7(a) (3), (4)
11) Data obtained by use of the above
method on representative samples
of the product 1 63. 61-7(b) (1)
12) Declaration and certification of the upper
and lower limits for each active ingredient
and intentionally added inert ingredient,
and the upper limit for each impurtiy,
reaction product, and degradation
•product 163.61-6
Topical Discussions
The product chemistry of chloroneb per se has been dealt
with in the Manufacturing-use Chloroneb section of this
chapter. The following is data required of all dust formulated
products of chloroneb.
Acti ve Ingredient Limits j_n_ Pesticide Products
For all pesticide products, the Guidelines require that
upper and lower limits be established for each active
ingredient, impurity, reaction product, and degradation
product. [163.61-5]
Current registrations of dust chloroneb contain 10% a.i.
For no dust formulation of chloroneb has an upper and lower
limit been established.
Product Analytical Methods and Data "
The Guidelines require submission of, or reference to,
analytical methods measuring each active ingredient in a
pesticide product. [163.61-7]
Section 163.61-7 of the Proposed Guidelines would require
that applications for registration of pesticide products
contain analytical data obtained by methods supplied to the
Agency.
Section 163.61-7 of the Proposed Guidelines would also
require that registrants of formulated products produced by
an integrated formulation system (Proposed Guidelines,
section 163.61-1) submit methods not only for the active
ingredient, but for each identifiable impurity associated
with manufacture of the technical chemical. Such methods
have not been submitted for any chloroneb formulation.
Methods for the determination of chloroneb in dust
formulations have not been submitted or cited.
50
-------
Physical and Chemical Properties
For every pesticide product, the Proposed Guidelines
require data on certain physical and chemical properties
useful for identification purposes or for evaluation of
hazard potential [163.61-8].
The following physical and chemical properties are required
for all dust products of chloroneb.
Required Physical/Chemical Properties: Color, odor, density
or specific gravity, pH, storage stability, fl ammabi 1 ity,
oxidizing or reducing action, explosiveness, and corrosion
characteristics.
51
-------
Bi bl iography
Manufacturing-Use
-MRID CITATION
GS0007-015
Alvarez, J.R., inventor; E.I. du Pont de
Nemours and Co., assignee (1968) Process for
Preparing 1,4 dichl oro-2 ,5-dimethosybenzene
US. patent 3,363,005, Jan. 9
00001428
I. duPont de
(1967) Name
Chloroneb.
Nemours & Company,
Chemical Identity
(Unpublished study
Incorporated
, and Composition
received
00001444
05013181
GS007-009
Oct. 16, 1967 under 8F0657; CDL:092951 -F)
E.I. duPont de Nemours & Company, Incorporated
(1977) "Demosan" 65W Fungicide: Product
Chemistry. Includes method dated October
15, 1976 and undated method. (Unpublished
study received May 27, 1977 under 352-312;
CDL:232274-A)
Haglid, F.R., inventor; E.I. duPont de Nemours
and Co., assignee (1979) Process for
preparing 1 ,4- dichl oro- 2, 5-d i met ho xy benzene,
U.S. patent 4,159,391. Jun 26. 3 p.
Int. CL 2 C 07C 41/001 U.S. Cl . 568/649^
Scribner, R.M.; Soboczenski, E.J. ; inventor;
(1966) Methods for Protecting Plants and
Seeds from Fungi. United States plant
patent 3,265,564. Aug 9
Bib! iography
Wettable Powder
00001444 E
I. duPont de Nemours & Company, Incorporated
(1977) "Demosan" 65W Fungicide: Product
Chemistry. Includes method dated Oct. 15,
1976 and undated method. (Unpublished
study received May 27, 1977 under 352-312;
CDL:232274-A) 0000 1444
52
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IV. ENVIRONMENTAL FATE
4
A. Use Profile
Chloroneb is a fungicide registered for control of:
1. damping-off and seedling blight of cotton, beans,
soybeans, and sugarbeets caused by Pythium spp.; 2. soreshin
of cotton caused by Scleroti urn rolfsii ; and 3. Pythi urn
blight and grey snow mold (Typhula spp.) of turfgrass.
Chloroneb is formulated as a 65% active ingredient wettable
powder, 10% active ingredient dust, or 1.015-10% active
ingredient granulars. The wettable powder is registered
for use as a slurry seed treatment or in-furrow spray on
cotton, beans, and soybeans and as a slurry seed treatment
on sugarbeets. The wettable powder is also registered as a
foliar spray on turfgrass. The dust formulation is registered
as a planter box seed treatment or in-furrow application on
cotton, beans, and soybeans. The granular formulations are
registered as in-furrow applications on cotton, beans, and
soybeans or as a foliar application on turfgrass.
On turfgrass applications can be made to 5-7 day intervals
for Pythium blight control on established turf and 7-10 day
intervals on new seedings. Applications to turf for snow
mold control can be made prior to the first heavy snowfall,
during a midwinter thaw, and in early spring as snow is
melting. Seed treatments and in-furrow applications
on other sites are made at planting.
The major use sites for Chloroneb are co'tton and turf.
Use is less extensive on sugarbeets, beans, and soybeans.
On the order of 500,000 pounds of active ingredient are
produced yearly. Of that, the majority of active ingredient
is used on cotton and turf. Use on sugarbeets, beans, and
soybeans is less extensive.
Registered application rates are listed in Table 1.
B. Environmental Fate - Manufacturing-Use Chloroneb
Environmental Fate Profi1e
Chloroneb is very resistant to hydrolysis, with no detectable
hydrolysis of either the manufacturing-use chemical or the
65% wettable powder formulation occurring over 30 days at an
environmental pH range of 5 to 9, and temperatures of 25 and
35°C.
53
-------
Table 1. Registered application rates of chloroneb.
Type of
Application rate
Formul ation
Dust
(10%)
Granul ar
(1.015-10%)
Site
cotton
beans
soybeans
turf
cotton
beans
soybeans
Appl ication
seed
furrow
seed
furrow
seed
furrow
fol i ar
furrow
furrow
furrow
( 1 b. or oz
.5 lb/100
1-2 Ib/A
.2 lb/100
1 Ib/A
.2 Ib seed
1 Ib/A
7.1-16.6 1
1-2 Ib/A
1 Ib/A
1 Ib/A
. a . i . )
Ib seed
Ib seed
b/A
Wettable
Powder
(65%)
cotton
sugarbeets
beans
soybeans
turf
-East of the Rocky Mountains
West of the Rocky Mountains
seed
furrow
seed
seed
furrow
seed
furrow
foliar
3.9 oz/100 Ib seed,
6.5 oz/100 Ib seed'
1.3-1.9 Ib/A
3.9 oz/100 Ib seed
2.6 oz/100 Ib seed
.98 Ib/A
2.6 oz/100 Ib seed
.98 Ib/A
7.08 Ib/A3 .
10.6-15.9
Snow mold
54
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Several common soil fungi are capable of transforming
chloroneb to 2,5-dichloro-4-methoxyphenol (DCMP) in vitro.
Of the 20 soil fungi studied, 12 were able to transform
up to 60% of chloroneb to DCMP within 10 days in a chloroneb-
amended medium (5 g/ml) basal medium. The most active
species included Fusari urn solani, Sclerotina sclerotiorum,
Mucor ramannianus. and He!minthosporiurn victoriae. In
addition, 10 of the species studied were capable of converting
DCMP to chloroneb. This indicates that dissipation of
chloroneb may not be a simple function of conversion to
DCMP. The growth of several of the fungi in the above
metabolic survey was reduced 10-50% relative to controls,
confirming the fungicidal action of chloroneb.
Chloroneb at concentrations of 0.1 to 7.0 ppm had no
effect on the growth of effluent microorganisms in a
model activated sludge unit. At higher chloroneb levels
(70 and 100 ppm), the system became overloaded with insoluble
chloroneb, and microbial populations were reduced to 10-20%
of control levels. After an acclimation period, sludge
nncroorganisms readily metabolized 40-50% of the applied
C-chloroneb to C02 within 3 weeks of the initial
treatment. The chloroneb metabolites DCMP and 2 ,5-dichl orohydro-
quinone were recovered from the effluent and accounted for
89% and 4%, respectively, of the effluent radioactivity at
day 16 of the study. At day 19. however, the relative
proportion of metabolite in the effluent declined, with 47%
of the radioactivity present in the form of unchanged
chloroneb, even though no change in chloroneb initial
concentration had occurred. The degradates are believed to
be intermediates in the total degradation of chloroneb.
Therefore, it appears that under moderate chloroneb concentra-
tion (7.0 ppm or less) an activated sludge system is capable
of degrading the majority of introduced chloroneb. However,
the inhibition seen at higher concentrations could pose
problems in the event that manufacturing-use chloroneb
i s -di scharged directly into an activated sludge treatment
system, since chloroneb acting alone in high concentra-
tions or in concert with other discharged chemicals could
have an adverse effect on the treatment process.
In a preliminary investigation on the field dissipation of
ring-labeled [ C] chloroneb, 48% of the applied radioactivity
was lost from the soil within a 3 month period following
an application of 2 Ib/acre to a Delaware soil. Only 21% of
the C in the soil was extractable. This extractable
material was identified as chloroneb. Therefore, there is
a possibility that a portion of the chloroneb or its
metabolite(s) forms a bound residue in the soil. Since
no free degradation products were noted, it is possible
55
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14
that the observed dissipation of C-labelled material
was due to movement of chloroneb or its degradates
(including C02) away from application sites by
volatilization or leaching.
In summary, although there is insufficient information
to form a comprehensive profile of the fate of chloroneb
in the environment, the information available suggests
that, under some circumstances, chloroneb may present
a persistence problem. Chloroneb does not hydrolyze to
a measurable degree under environmental conditions, which
could enhance its persistence if entry into aquatic environ-
ments occurs. Although chloroneb can be converted to
a number of degradation products by certain soil fungi and
by activated sludge microorganisms, the rates of these
processes are relatively slow. In fact, in the case of
an activated sludge system, a substantial portion of the
introduced chemical may escape the system undegraded.
The fate and effects of the various phenolic degradates
are unknown, and the observed ability of some fungi to
reconvert degradation products to chloroneb by methylation
has to be considered in predicting the long term fate
of the chemical. Also, although there are data indicating
that chloroneb dissipates slowly in soil, there is no
evidence to indicate what percentage of the dissipation
is the result of degradation by soil microorganisms, or
is due rather to physico-chemical mechanisms or movement
from the application site. The relatively slow rate
of dissipation observed raises the possibility that chloroneb
residues may accumulate in soil if applications are frequently
repeated.
->
Exposure Profile (Manufacturing-Use Chloroneb)
Because of the scarcity of data on the environmental presence
or fate of chloroneb, it is impossible to quantitatively
assess exposure of human and wildlife to manufacturing-use
chloroneb. However, provided that chloroneb enters water-
ways as a result of manufacture, a potential for food-chain
accumulation of chloroneb and subsequent human and wildlife
exposure may be dictated by the low solubility of chloroneb
in water (8 ppm).
Data Gaps
To support the registration of all formulated chloroneb
products, it is necessary to submit or cite the following
data:
56
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Food Use (Terrestrial Field-Vegetable Crop)
Photodegradation studies 163.62-7(c)
Soil metabolism studies-aerobic and
anaerobic 163.62-8(b,c)
Metabolism studies-effects of microbes
on chloroneb except fungi 163. 62-8(f) (2)
Metabolism studies-effects of chloroneb
on microbes 1 63. 62-8 (f) (3)
Leaching and adsorption/desorption studies..163.62-9(b,d)
Terrestrial Field Dissipation studies 163.62-10(b)(1,4)
Rotational Crop and Fish Accumulation
studies 163.62-1l(b,d)
Nonfood Use (Terrestrial Noncrop)
All above environmental fate topics are required
except Anaerobic soil metabolism (163.62-8(c) and
Rotational Crop studies (163.62-11(b).
Topical Discussions
Corresponding to each of the Topical Discussions listed
below is the number of the section in the 'Proposed Guide-
lines for Registering Pesticides' in the United States (43
FR 29696, July 10, 1978) which explains the minimum data
that the Agency requires in order to adequately assess
a pesticide's Environmental Fate.
All topics related to the Environmental Fate of chloroneb
as an active ingredient are discussed under Manufacturing-Use,
Chioroneb.
Guide!ines Section
Physico-Chemi cal Transformation 163.62-7
Metabolism (Soil, Aquatic
and Mi crobiol ogical) 163.63-8
Mobility 163.62-9
Field Dissipation 163.62-10
Accumul at ion 163.62-11
PHYSICO-CHEMICAL TRANSFORMATION 163.62-7
Hydrolysis
Hydrolysis data are required to support the registration
of all manufacturing-use products regardless of the
intended end uses of products formulated from the
manufacturing-use product.
57
-------
Data from a single study (Harvey 1979, GS0007-6) indicate
that chloroneb will not hydrolyze under typical environ-
mental conditions. No chloroneb degradation products
were identified by high-pressure liquid chromatography
within 30 days when [ C]chloroneb (4 ppm) was maintained
in distilled water or at buffered pH 5-7 and 25 or 35 C.
No hydrolysis products were detected when a 650 ppm aqueous
solution of a chloroneb formulation (Tersan SP, 65% chloroneb)
was maintained under the same conditions. Similarly,
no degradation was observed when the same chloroneb formulation
was maintained in acid (0.1 N HC1) or base (0.1 N NaOH) for
44 hours.
This study is adequate to assess chloroneb hydrolysis and
fulfill the data requirements in Section 163.62-7(b) of
EPA's Proposed Guidelines for Registering Pesticides (July
1978). No data gaps were identified.
Photolysi s
Photodegradation studies in water are required to support
the registration of all formulated chloroneb products
intended for terrestrial uses.
Studies in soil are required to support the registration of
all chloroneb formulated products intended for crop uses.
No data on the photolysis of chloroneb are available.
All data specified in Section 163.62-7(c) are needed to
determine the effect of light on chloroneb.
METABOLISM 163.62-8
Data on metabolism are required to determine the nature of
pesticide residues and their availability to rotational
crops, and to help in the assessment of potential disposal
and reentry hazards.
Soil Metabolism
Aerobic metabolism studies are required to support the
registration of all formulated chloroneb products intended
for terrestrial uses. Anaerobic soil metabolism studies are
required to support the registration of all formulated
products intended for field and vegetable crop uses.
No data on the metabolism of chloroneb in soil are available.
All data specified in Section 163.62-8(b,c) are
needed to determine the metabolism of chloroneb
in soil .
58
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Aquatic Metabolism
No data are required on the aquatic metabolism of
chloroneb because the use pattern indicates that direct
discharge into the aquatic environment is unlikely.
Microbiological Metabolism
Data on the effects of microbes on pesticide degradation
and effects of pesticides on microbes are required to
support the registration of all chloroneb formulated products
intended for terrestrial uses.
Microbiological Metabolism - Effects of Microbes on Pesticides
Two valid studies relating to the effects of microbes
on pesticides were reviewed. The first (Hock and Sisler 1969,
05001155) assessed the ability of selected microbes
to metabolize [ C]chloroneb within 24 hours. The metabolite
2,5-dichloro-4-methoxyphenol (DCMP) accounted for greater
than 50% of the medium radioactivity when Rhizoctonia
solani was incubated in the presence of either methyl-or
ring-1 abeled [ C]chloroneb at 5, 8, or 15>j/g/ml for 24
h
-------
These studies show that several common soil microorganisms
species are capable of degrading chloroneb to DCMP in
vitro. Some soil microbes are also capable of resynthesizing
chloroneb from DCMP- Therefore, the rate of chloroneb
degradation in soil will be related to the relative popula-
tions of microorganism species capable of degrading or
resynthesizing chloroneb.
It can be concluded from these studies that many soil
fungi are capable of demethylat ing chloroneb to DCMP and
degrading chloroneb to other unidentified degradation
products.
Additional studies are needed using the procedures outlined
in Section 163.62-8(f)(2) to determine the effects of
bacteria and algae on chloroneb.
Microbiological Metabolism - Effects of Pesticides on Microbes
Four valid studies were reviewed. Wiese and Vargas (1973,
05001170) observed that growth of R_._ s o 1 a n i was completely
inhibited by chloroneb at 5//g/ml. Growth of several
other fungal species was also reduced 10-50% in the presence
of chloroneb at low concentrations.
Studies by Kappas (1978, 05001167) and Georgopoulos et al.
(1976, 05001308) showed that chloroneb inhibits the growth
of Aspergillus nidulans. At 20-40 M chloroneb, the
former investigator observed 30-61% growth inhibition in
complete media over 3 days, whereas the latter investigators
observed a 36-67% growth inhibition at 24-38 ^/M in complete
media over 5 days. Azevedo et al. (1977, 05001292) also
observed drastic growth inhibition by chloroneb in chloroneb-
sensitive strains of A. nidulans at 50 ppm, while 400 ppm
was required to inhibTF growth of resistant strains. The
frequency of mitotic recombination was increased and haploidi
ration of a diploid strain was decreased, as well. Under
very limited conditions and species, chloroneb is capable
of affecting growth and genetic characteristics of microbes.
All data specified in Section 163.62-8(f)(3) are needed
to determine the effects of chloroneb on microorganisms.
Activated Sludge Metabolism
A laboratory study of the effects of pesticides on the
wastewater treatment process is required to support the
registration of all manufacturing-use products and all
formulated products that are indirectly discharged into
wastewater treatment systems or are used as treatments
in wastewater treatment systems.
60
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Harvey (1979, GS0007-7) studied the fate and effects of
[ C]chloroneb in a simulated wastewater treatment
system. Chloroneb added daily for 29 days to a closed
aerated system in increments between 0.1 and 100 ppm had
no effect (determined by plate counts) on the growth of
effluent microorganisms at concentrations of 7 ppm or
less. AT 70 ppm or above, the system became overloaded
with insoluble chloroneb and colony sizes were 10-20%
of control levels. After a lag period of about 10 days,
sludge microorganisms readily metabolized the applied
chloroneb. Approximately-, 40-45% of the chloroneb applied
daily was metabolized to COp after 3 weeks. High-
pressure liquid chromatography of the effluent sampled
identified two metabolites, 2,5-dichloro-4-methoxyphenol
(DCMP) and 2,5-dichlorohydroquinone (DCHQ), which reached
maximum concentrations, respectively, of 89 and 4% of the
effluent radioactivity, respectively, on the 16th day of
the study.
This study is considered adequate to assess the effects
and fate of chloroneb in waste treatment facilities as
specified in Section 163.62-8(g). No data gaps were
identi fied.
MOBILITY 163.62-9
Data on mobility are required to determine pesticide
residue movement in the environment.
Leaching
Leaching data are required to support registration of
formulated products intended for terrestrial noncrop and
field/vegetable crop uses.
All data specified in Section 163.62-9(b) are needed to
determine the susceptibility of chloroneb to leaching.
Volatility
No data are required on the volatility of chloroneb because
the use pattern of chloroneb does not include a greenhouse
use.
Adsorption/Desorption
A laboratory study using radioisotopic or nonradioisotopic
analytical techniques is required to support the registra-
tion of all chloroneb formulated products intended for terrestrial
uses.
61
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No valid data on the adsorption/desorption of chloroneb
are avail able.
All data specified in Section 163.62-9(d) are needed
to determine the adsorption/desorption of chloroneb.
Water Dispersal
No data are required on the water dispersal of chloroneb
because the use pattern indicates that direct introduction
into the aquatic environment is unlikely to occur.
FIELD DISSIPATION 163.62-10
A field dissipation study using representative formulations
under actual use conditions is required to support the
registration of all chloroneb formulated products intended
for terrestrial uses.
Terrestrial
The study reviewed below provides preliminary data on
terrestrial field dissipation of chloroneb.
Rhodes (1968, 00001426) studied the dissipation of ring-
labeled [ C]-chloroneb in a Delaware soil. At various
sampling intervals up to 6 months following application
(2 Ib ai/A), the soils were Soxhlet extracted with acetone
and the extracts,were analyzed by thin-layer chromatography.
The extractable C (about 21% of C present at 3
months) was identified as chloroneb. No free chloroneb
degradation products were observed within a depth of 1-3
inches. Approximately 28% of the applied radioactivity
dissipated from the soil by 1 month following application.
Further loss of radioactivity from the soil continued over
the next 2 months. However, the remaining 52% of radioactivity
showed no further decline. No loss of radioactivity was
detectable during the 3-6 month interval; this may be
partially attributed to the fact that the earth was frozen,
creating unfavorable conditions for chloroneb dissipation.
Most of the recovered radioactivity remained within the
1-3 inch soil depth throughout the experiment.
Additional studies are needed as specified in Section
163.62-10(b) in the following areas:
• Four studies in field and vegetable crop use
areas using granular and wettable powder
formulations of chloroneb as specified in
Section 163.62-10(b)(1)
62
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• Two studies in turf use areas using granular
and wettable powder formulations of chloroneb
as specified in Section 163.62-10(b) (4)
Aquatic Dissipation
No data are required on the aquatic dissipation of chloroneb
because the use pattern indicates that direct introduction
into the aquatic environment is unlikely to occur.
Terrestrial/Aquatic (Forest)
No data are required on the terrestrial/aquatic dissipation
of chloroneb because the use pattern indicates that direct
introduction into a forest environment is unlikely to
occur.
Aquatic Impact Uses
No data are required on the aquatic impact of chloroneb
because the use pattern indicates that direct introduction
into the aquatic environment is unlikely to occur-
ACCUMULATION 163.62-11
Data on accumulation are required to determine accumulation
in food webs.
Rotational Crops
Rotational crop studies are required to support the registra-
tion of all chloroneb formulated products intended for
field/ vegetable uses.
No data on the accumulation of chloroneb in rotational crops
are available.
All data specified in Section 163.62-ll(b) are needed to
determine the accumulation of chloroneb (granular and
wettable powder) in rotational crops.
Irrigated Crops
No data are required on the accumulation of chloroneb in
irrigated crops because the use pattern indicates that
chloroneb is not used on irrigated crops.
Fish
This laboratory study employing radidisotopic or nonradio-
isotopic analytical techniques is required to support
63
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the registration of all chloroneb formulated products
intended for terrestrial noncrop and field/vegetable crop
uses.
No data on the accumulation of chloroneb in fish are
avai1 able.
All data specified in Section 163.62-11(4) are needed
to determine the accumulation of chloroneb in fish.
Formulated Chloroneb - Exposure Profile
A11 Formulat ions
The relatively high vapor pressure of chloroneb creates the
potential of exposure by inhalation of the volatilized
chemical in all its formulations. Chloroneb formulations
are not applied a.erially, thereby greatly reducing the
possibilities for contamination of persons, livestock, and
wildlife outside of application sites. Because soil mobility
data are lacking, the potential exposure of humans to
chloroneb through contamination of drinking water cannot
be assessed. For the same reason, the potential for exposure
of aquatic organisms is unknown.
Dissipation of chloroneb in soil cannot be assumed to
eliminate use-associated hazards because chlorophenol s
are major products of soil microbial metabolism of chloroneb.
The principal sites of usage of chloroneb appear to be
cotton and turf (predominantly golf-courses), and the
principal regions of exposure are expected to be the Mid-West
and the cotton belt.
Wettable Powder Formulations
Inhalation of volatilized chloroneb may be considerable in
view of its relatively high vapor pressure. This may be
particularly true for the turf treatment use of chloroneb
65% wettable powder on golf course fairways and greens where
weekly treatments of 7 Ib. a.i. per acre may be used.
Significant human exposure may also occur by dermal or
ocular routes from splashing during the dilution, tank-mixing,
and loading of spray equipment with the wettable powder.
Exposure of applicators by breathing of spray droplets could
be important for these formulations.
Granular Formulations
No significant exposures to humans which are unique to the
granular formulations are foreseen. Availability of granular
chloroneb may differ from other formulations to terrestrial
wildlife and birds.
64
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Dust Formulati ons
Inhalation of a dust formulation or dermal contact with it
are the primary routes of exposure.
65
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Bibliography
-MRID CITATION
05001292 Azevedo, J.L., E.P. Santana, and R. Bonatelli, Jr.
1977. Resistance and mitotic instability
to chloroneb and 1,4-oxathiin in Aspergi11 us
nidulans. Mutation Res. 48(2):163-172
05001308 Georgopoulos, S.G. , A. Kappas, and A.C. Hastie.
1976. Induced sectoring in diploid Aspergi11 us
nidulans as a criterion of fungitoxi city by
interference with hereditary processes.
Phytopath. 66(2):217-220
GS0007-006 Harvey, J. 1979. Stability of C14C]chloroneb
in water at various pH values. (Unpublished
study received Dec. 13, 1979, under 352-GIA;
submitted by E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del. CDL:241500.)
GS0007-007 Harvey, J. 1979. ..Activated sewage sludge
metabolism of [ C]chloroneb. (Unpublished
study received Dec. 13, 1979, under 352-GIA;
submitted by E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del. CDL:241500.)
05001155 Hock, W.K., and H.D. Sisler. 1969. Metabolism
of chloroneb by Rhizpctgnia sol am' and
other fungi. J. Agri. Food Chem. 17(1):123-128
05001167 Kappas, A. 1978. On the mechanisms of
induced somatic recombination by certain ^
fungicides in Aspergi1lus hi dulans.
Mutation Res. 51(2):189-197
14
00001426 Rhodes, R.C. 1968. Disappearance of C-ring-
labeled chloroneb from soil. (Unpublished
study received July 8, 1968, under 8F0657;
submitted by E.I. du Pont de Nemours &
Co., Inc., Wilmington, Del. CDL:091147-J.)
05001170 Wiese, M.V., and J.M. Vargas, Jr. 1973.
Interconversion of chloroneb and 2,5-dichloro-
4-methoxyphenol by soil microorganisms.
Pesticide Biochem. Physiol. 3(2):214-222.
66
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V. TOXICOLOGY
Toxicology - Manufacturing-Use Chloroneb
Toxicology Profile
The high acute oral LD5Q of 90% technical chloroneb in rats
(greater than 5 g/kg) Suggests a very low acute oral hazard
to human beings. Gross changes included heavy livers (in
two of five females) and kidneys with hydronephrosis (in two
of five males). Based on the high 4-hour LC5Q (25.2
mg/liter) in male rats, a low acute inhalation hazard in
human beings is expected, pending receipt of data on female
rats. Technical chloroneb (90%) is not expected to irritate human
eyes, based on studies conducted with rabbits. No eye
irritation was noted when this compound was instilled into
rabbit eyes. Technical chloroneb (90%) has a low potential for
primary dermal irritation in human beings. It was only
slightly irritating to rabbit skin.
No subchronic dermal, subchronic oral, or chronic feeding
studies are available on the technical product. Adequate
subchronic tests are available on 65 and 75% wettable powder
formulations, which contained 90 or 98% pure chloroneb,
respectively. Presently, these satisfy Agency requirements
for the technical product. The known chloroneb impurities
or inert formulation ingredients should not significantly
affect the toxicity of the active ingredient. Nor should
extrapolation of results underestimate hazard to human
beings or to domestic animals.
In general, new toxicologic studies might be required if
the Agency determines that previously uncharacterized, toxic
impurities are present in techical chloroneb. Chlorinated
dibenzodioxins, theoretically, could be present. A detailed
description of chemicals present in any technical chloroneb
used as a test substance, therefore, it necessary for
realistic evaluation of key chloroneb toxicologic studies
(including subchronic and chronic). Likewise, new toxicologic
information may be needed should unknown or inadequately
tested chloroneb metabolites be found in pesticide residues
in treated foods or feeds or food animals.
Repeated application of technical chloroneb to human
skin may not result in systemic effects, based on results of
a subchronic dermal test on a 75% wettable powder formulation
of chloroneb. In rabbits, subchronic dermal application of
as much as 5 g/kg (as active ingredient) did not result in
observed clinical or pathological change, except for a
slightly lower weight gain.
67
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Data from subchronic and chronic oral studies on 65 or
75% wettable powder formulations of chloroneb indicate
that high oral doses of technical chloroneb primarily
affect the liver, kidney, stomach, and thyroid.
Ninety-day feeding of the 65 or 75% wettable powder in rats
resulted in increased weight of the liver and kidney and
histopathologic changes in these organs. The observed
increased urine sugar supports the findings of kidney
damage. The "no-observed effect level" (NOEL) for the study
is 500 ppm.
Two-year feeding to dogs of 2,500-10,000 ppm resulted (as 65
or 75% wettable powders) in gastritis and in pathological
alterations and weight increases in the liver. The elevated
Scrum glutamic-pyruvic transaminase activity (SGPT) seen at
18 months, supports the finding of liver damage. Liver
damage was not noted in rats fed up to 2,500 ppm chloroneb
for 2 years. Morphologic changes in the thyroid were noted
in rats at 1 year and dogs at 2 years, indicating a moderate
increase in activity. The kidney was not affected in these
studies in either rat or dog. The high levels of chloroneb
intake also caused reduced body-weight gain in rats and
weight loss in dogs. For these 2-year studies, the NOEL is
500 ppm for both dog and rat. These NOEL's correspond to
12.5 mg/kg body weight/day of chloroneb for the dog and
25 mg/kg body weight/day of chloroneb for the rat. The dog
study meets Agency requirements for a non-rodent subchronic
feeding study.
A final judgment as to adequacy of this rat study as a
chronic feeding study cannot.be made until detailed chemical
characterization of the test substances (technical chloronebs
90 and 98% pure) is provided. In addition to this requirement,
further information and classification of neoplastic and
non-neoplastic lesions found in the study must be provided
before it can be evaluated for acceptability as an oncogenicity
study.
To assess oncogenic potential, an oncogenicity test in an
acceptable mammalian species other than the rat is needed.
As noted above, a new oncogenicity study may be needed in
the rat.
Chloroneb has not been evaluated for mutagenicity. Acceptable
mutagenicity tests (see Guidelines of August 22, 1978, 40 FR
Part 163) must be submitted or cited to support registration
of any proposed end-use. Because of possible exposure of
women of child-bearing age, teratogenicity studies in two
species are needed to support all existing end-uses.
68
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Limited tissue residue data indicate that both chloroneb
and a metabolite, 2 ,5-dichloro-4-methoxyphenol, show a
very low order of bioaccumulation in mammalian tissues
after long-term dietary exposure to chloroneb. In rats and
dogs fed chloroneb (as a 65 or 75% wettable powder) for 2
years, the parent compound occurred primarily in body fat,
and the metabolite occurred chiefly in liver and kidney.
Dogs eliminate the metabolite in urine and, to a lesser
extent, in feces. The metabolite also occurs in rat urine.
Rats feces were not analyzed. To fulfill Agency requirements
on metabolism, single-dose testing of chloroneb is required.
The available data are insufficient to assess the mammalian
metabolism of chloroneb.
Additional tests that must be conducted to assess the
toxicity of technical chloroneb are listed in the section on
Data Gaps.
Data Requirements
The following are toxicology data requirements. Listed
after each requirement is the section in the Proposed
Guidelines of August 22, 1978, (43 FR, No. 163 37336) that
describes the type of data required.
All applicants, regardless of end-use, must submit or cite
the following data:
Category of Test Guideline Number
Acute Oral Toxicity (rat) 163.81-1
Acute Dermal Toxicity (rabbit) 163.81-2
Acute Inhalation Toxicity (rat) 163.81-3
Primary Eye Irritation (rabbit) 163.81-4
or Demonstration of pH 1-3 or 12-14
or Demonstration of Dermal Irritation
of Category I
Primary Dermal Irritation (rabbit) 163.81-5
Skin Sensi tization (guinea pig) ...163.81-6
Data Gaps
The following data are required for the reregistration of
manufacturing-use chloroneb:
Acute Toxicity
Acute Dermal Toxicity 163.81-2
Acute Inhalation Toxicity (Female Rats) 163.81-3
Skin Sensi tization 163.81-6
69
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Food Use (Requires a Tolerance or Exemption)
All applicants for registration or reregistration of technical
products which are formulated into end-use products intended
for use on food must submit or cite the following:
Chronic Feeding
Oncogenic ity
Teratogenicity
Reproduction
Mutagenicity
Metabol ism
A two year feeding study 163.83-1
in the rat is required.
The available rat study is
inadequate, pending evaluation
of the chemical composition
of technical chloroneb,
including minor impurities.
An oncogenicity study in 163.83-2
each of two suitable
mammalian species is
required. Registrants may
cite the referenced two-year
rat study provided that they
also submit the appropriate
supplementary data.
Teratogenicity testing
in two mammalian species
is required.
A two-generation reproduc-
tion study, preferably in the
rat is required. A summar-
ized reproduction study is in
Agency files.
s
A mammalian in vitro point 163.81-1
mutation test; a sensitive through
sub-mammalian point mutation 163.81-4
test; a primary DMA damage
test; a mammalian in vitro
cytogenetics test.
A general metabolism study 163.85-1
in one mammalian species
is required.
163.83-3
163.83-4
Non-Food Use (Nondomestic, Outdoor)
All applicants for registration or reregistration of technical
products which are formulated into end-use products intended
for non-food, nondomestic, outdoor uses must submit or cite
the following:
70
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Teratogen iticy Teratogenicity testing 163.83.3
in two mammalian species
is required.
Mutagenicity A mammalian in vitro point 163.83-1
mutation test; a sensitive through
sub-mammalian point mutation 163.83-4
test; a primary DNA damage
test; a mammalian in vitro
cytogenetics test.
Human and Domestic Animal Hazard Assessment
The chloroneb exposure profile (see Exposure Profile
in the Environmental Fate Chapter) reveals that persons
who handle, store, or ship technical chloroneb will be
exposed, principally, by inhalation. Without taking
proper precautions, they may get it on the skin and in the
eyes.
Single exposure by any of these routes to technical chloroneb
may be of low hazard. Technical chloroneb (90%) showed
relatively high acute inhalation toxicity (tested in males,
only). Applied once to skin or eyes, it caused little or no
primary irritation. Limited skin application may not cause
systemic hazard; since, on repeated, daily skin contact with
large doses of chloroneb (as 75% wettable powder), only
reduced body-weight gain was noted. Swallowing a lethal
dose of technical chloroneb by accident seems unlikely,
based on the relatively high acute oral LD50 shown by
technical chloroneb (90%).
Required Labeling
Precautionary labeling of each product must correspond to the
toxicity categories determined by five acute toxicity tests.
Acceptable categories of acute toxicity and the corresponding
required labeling appear in the Regulatory Chapter of this
Standard.
Topical Discussions
Corresponding to each of the Topical Discussions listed
below is the number of the section(s) in the 'Proposed
Guidelines' of August 22, 1978 (43 FR, No. 163 37336 which
explain(s) the minimum data that the Agency usually requires
in order to adequately assess chloroneb's toxicology. Where
no section number is listed, a minimum requirement has not
been set for such information. Also under each of the
topics is a reference to the section in the 'Proposed
Guidelines1.
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Acute Testing Guidelines Section(s)
Acute Oral Toxicity 163.81-1
Acute Dermal Toxicity 163.81-2
Acute Inhalation Toxicity 163.81-3
Primary Eye Irritation 163.81-4
Primary Dermal Irritation 163.81-5
Skin Sensitization 163.81-6
Acute Delayed Neurotoxicity 163.81-7
Subchronic Testing
Subchronic Oral Toxicity 163.82-1
Subchronic 21-Day Dermal Toxicity 163.82-2
Subchronic 90-Day Dermal Toxicity 163.82-3
Subchronic Inhalation Toxicity 163.82-4
Subchronic Neurotoxicity 163-82-5
Dermal Sensitization 163.82-6
Chronic Testing
Chronic Feedi ng 1 63.83-1
Oncogenicity 163.83-2
Reproduction Testing
Teratology 163.83-3
Reproduction 163.83- 4
Mutagenicity 163.83-1 to 4
Metabolism in Laboratory Animals 163.85-1
Clinical Trials
Emergency Treatment
The following topical discussions describe available
toxicity data on technical chloroneb and its formulations
and state whether they are adequate for Agency regulatory
purposes.
Acute Testing
Acute Oral Toxicity (163.81-1)
The minimum testing needed on acute oral toxicity is one
test, in the laboratory rat, on the technical chemical
and on each manufacturing-use product.
The LDcn of technical chloroneb (90% active ingredient)
exceedlu5 g/kg in male and female rats (Hinckle 1979, GS0007-010)
Clinical signs included diarrhea, stained face and perineal
area, and weight loss. Gross pathologic changes included
heavy liver (two of five females), kidneys with hydronephrosis
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(two of five males), cornea! opacity (one of five males),
and lungs that were dull-red, gray mottled with gray foci in
one to three animals (not further described). This study is
sufficient to assess the acute oral toxicity of technical
chloroneb and to place it in Category IV, corresponding to a
very low acute oral hazard.
Acute Dermal Toxicity (163.81-2)
The minimum testing needed on acute dermal toxicity is
one test, preferably in the albino rabbit, on the technical
chemical and on each manufacturing-use product.
No tests on technical chloroneb are available.
Acute Inhalation Toxicity (163.81-3)
The minimum data requirement for acute inhalation toxicity is
one test, preferably in the albino rat, on the technical
chemical and on each manufacturing-use product.
The 4-hour LCcg of chloroneb aerosol (formed from a melt
of particulate chloroneb) was 25.2 mg/liter in male rats
(Kwon 1965, 00004982). Lethal concentrations resulted in
hyperemia, unresponsiveness, mydriasis, and respiratory
irregularities. Hyperemia and hyperpnea were observed at
sublethal concentrations. This is an adequate determination
in males, which would place particulate chloroneb in Category
IV, indicating a very low acute inhalation hazard. Testing
in females, however, must be conducted to adequately assess
inhalation toxicity.
Primary Eye Irritation (163.81-4)
The minimum testing needed to evaluate eye irritation
potential is one test, in albino rabbits, on each manufacturing
use product. If the test substance has a pH of 1-3 or 12-14,
however, it will be judged corrosive, and an eye irritation
test is not needed. If the test substance has been judged
to be dermally corrosive, an eye irritation test is not
needed.
Technical chloroneb (90% active ingredient) was not irritating
to the eyes of rabbits (Ferenz 1979a, GS0007-011). Instilla-
tion of 0.1 ml (50 mg) of the test product resulted in no
corneal opacity, iritis, or conjunctival irritation in
either washed or unwashed eyes. The study meets Agency
requirements for a primary eye irritation test and is
adequate to place this technical chloroneb product in
Category IV, indicating a very low eye irritation potential.
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Primary Dermal Irritation (163.81-5)
The minimum testing needed to evaluate dermal irritation
potential is one test, preferably on the albino rabbit,
on each manufacturing use product.
Technical chloroneb (90% active ingredient) was very
slightly irritating to intact and abraded rabbit skin at
either 24 or 72 hours (Ferenz 1979b, GS0007-012). The study
is adequate to place technical chloroneb in Category IV,
indicating a very low potential for dermal irritation.
Skin Sensitization (163.81-6)
The minimum requirement for assessing skin sensitization is
an interdermal test in one mammalian species, preferably the
guinea pig, on each manufacturing-use product.
No testing is available for manufacturing-use chloroneb.
Acute Delayed Neurotoxicity (163.81-7)
An acute delayed neurotoxicity evaluation is not required
because chloroneb is not expected to cause acetylcholinesterase
depression, nor is its chemical structure related to that
of substances that induce delayed neurotoxicity.
Subchronic Testing
Subchronic Oral Toxicity (163.82-1)
The minimum testing needed to assess Subchronic oral
toxicity is one test in each of two mammalian species,
a rodent and a non-rodent, on the technical chemical.
No adequate Subchronic oral test of the technical product
itself is available. However, a 90-day feeding study
in rats on a 75% formulation of chloroneb (Sherman 1964a,
00001446; described below) is judged adequate to fulfill
Agency requirements for a rodent study, and a 2-year-feeding
study in dogs on a 65 or 75% wettable powder (Busey and
Kundzins 1967, 00001421, described below) satisfies the
requirement for a non-rodent study, tthe known impurities
and inerts in the 65 or 75% wettable powder formulations are
not expected to decrease the toxicity of technical chloroneb
in such studies or correspondingly, to cause underestimation
of human hazard.
A summary of a 90-day rat feeding study on a mixture
of substances that comprise the impurities (10%) in technical
(90%) chloroneb (as determined in 1967) is in Agency files.
It will be reviewed when details of the study become available.
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In preliminary testing, Sherman (19646, 00004980) gave
each of two male rats technical chloroneb at 3.400 mg/kg
body weight/day as a suspension in peanut oil, 5 days a
week, for 2 weeks. The only toxic sign was salivation
during the second week of dosing.
In a preliminary study, six rats were dosed repeatedly
with a wettable powder formulation containing 75% of active
ingredient (Sherman 1964b, 00004980). Cumulative oral
toxicity was observed in these rats, each of which received
orally 5 g/kg body weight/day (based on active ingredient),
5 days a week, for 2 weeks. They lost weight and showed
diarrhea during the first week and showed weakness and
semi-prostration during the second week. Two of six rats
died after eight doses. Pathologic findings included conges-
tion of organs, injury to blood cells and blood-forming
organs (spleen and bone marrow), slight injury to kidneys,
and large liver with cytoplasmic and nuclear irregularities.
The compound appeared to affect the hematopoietic system,
liver, and kidneys.
A 90-day feeding study was conducted in rats using a wettable
powder formulation containing 75% active ingredient at 0, 50,
500, and 5,000-7,500 ppm (based on the active ingredient) in
the diet (Sherman 1964a, 00001446). There was no behavioral,
hematologic, or nutritional evidence of toxicity. Increased
sugar was present in the urine of male and female rats fed
the highest dose. In rats on this dose, the urine sediment
contained large numbers of epithelial cells (males) and
leukocytes (females). Increased liver and kidney weights in
male rats and increased liver weights in female rats were
recorded in the highest-dosage groups. Histopathologic
examination revealed tubular degeneration in the kidneys and
centri1obular enlargement of hepatic cells with unequal
hypertrophy of the hepatic cell nuclei in livers of male
rats fed the highest dose. The "no-observed-effect level"
(NOEL) for the study is 500 ppm (25 mg/kg body weight/day).
This study is judged adequate to fulfill Agency requirements
for a subchronic rodent study.
In a 2-year feeding study, beagle dogs received chloroneb
(as a 65 or 75% wettable powder) in the diet at 0, 100,
500, or 2,500-10,000 ppm of active ingredient (Busey and
Kundzins 1967, 00001421). Loss of body weight occurred in
dogs in the high-level group when fed 7,500, 8,750, or
10,000 ppm. In three of six high-dose dogs at 18 months,
serum glutamic-pyruvic transaminase and/or alkaline phosphatase
activities were moderately-to-markedly elevated. At necropsy,
the mean and relative liver weights of the high-dose dogs
were moderately elevated over those of controls. Histopathologic
changes were found in. dogs of this group after 2 years
on test. Changes in the thyroid, indicative of a moderate
75
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increase in activity, were characterized by uniform, small-to-
me di urn- si zed follicles that were lined by medium-to-high
cuboidal epithelium in four of six dogs. The livers from
four of six dogs had moderate-to-severe pigmentation consisting
of small yellowish-brown granules in hepatocytes. A moderate
subacute-to-chronic catarrhal gastritis was observed in
stomachs from four of six dogs.
As judged by appearance, behavior, appetite, elimination,
body weight changes, clinical laboratory values, organ
weights, organ-weight/body-weight ratios, and gross necropsy
and histopathologic findings, chloroneb at either 100 or
500 ppm chloroneb in the diet, fed for 2 years, did not
adversely affect these dogs. The NOEL for the study is 500
ppm (12.5 mg/kg body weight/day). This study is judged
adequate to comply with the requirement for a non-rodent
subchronic oral study-
Subchronic 21-Day Dermal Toxicity (163.82-2)
The minimum requirement to assess subchronic 21-day dermal
toxicity is one study preferably in the albino rabbit, on
the technical product. This study is required for all
uses of chloroneb.
No studies of subchronic dermal toxicity have been conducted
using technical chloroneb itself. However, a test on a
formulated product (Hood 1965, 00001445, described below) is
judged adequate to fulfill Agency requirements for a subchronic
dermal test on the technical product.
A study by Hood (1965, 00001445) was conducted on a 75% *
wettable powder formulation containing 75% active ingredient
using groups of five male and five female rabbits. A 55%
aqueous paste of the formulation was kept on abraded skin of
each rabbit, during each of fifteen, daily 5-hour periods,
over 3 weeks, at 5 g/kg body weight (as active ingredient).
One control group was untreated. In the other control
group, each application of the wettable powder formulation-
without-chloroneb was made at 1 g/kg body weight. Except
for slightly lower weight gain in test rabbits, there were
no apparent effects of chloroneb on clinical signs, organ
weights, relative organ weights, or histopathologic findings.
The study is judged adequate to comply with Agency requirements
for subchronic 21-day dermal test on the technical product.
Subchronic 90-Day Dermal Toxicity (163.82-3)
A subchronic 90-day dermal toxicity test is not required
because chloroneb is not purposely applied to skin, and
its use will not result in human exposure comparable to,
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for example, the exposure of swimmers to swimming pool
additives or garment wearers to pesticide-impregnated
fabric.
Subchronic Inhalation (163.82-4)
A subchronic inhalation study is required if pesticidal
use may result in repeated inhalation exposure at a concentra-
tion that is likely to be toxic, as determined from results
of acute inhalation testing. Acute inhalation testing on
chloroneb is incomplete, so a final determination on the
requirement for a subchronic inhalation test cannot be made
at this time.
Subchronic Neurotoxicity (163.82-5)
A subchronic neurotoxicity evaluation is not required
on chloroneb because it is not expected to induce neuropathy
or delayed neurotoxicity, and because it does not have a
molecular structure closely related to that of a compound
that is known to induce neuropathy or delayed neurotoxicity.
Chronic Testing
Chronic Feeding (163.83)
A chronic feeding study is required for all food uses in one
mammalian species, preferably the laboratory rat, using the
technical product. The study is required for all food uses
of chloroneb.
No chronic tests are available on technical chloroneb.
At present, a study in rats on a wettable powder containing
65 or 75% chloroneb (Busey et al. 1967, 00001422, described.
below) will not satisfy Agency requirements for a chronic
test because the test substances are inadequately characterized
The test chemicals were 98 and 90% pure chloroneb, formulated
as 75 and 65% wettable powders, respectively. The study
cannot be judged for adequacy as a chronic feeding study
until the test substances (90 and 98% pure technical chloroneb)
have been adequately characterized. This includes the
characterization of minor impurities.
In this study, a wettable powder containing 65 or 75%
chloroneb was fed to rats at dietary levels of 0, 100, 500,
and 2,500 ppm (based on active ingredient) for 2 years
(Busey et al. 1967, 00001422). Marked growth suppression
and reduced food consumption occurred in the females, and
moderate growth suppression occurred in the males given the
highest dose. No abnormalities were noted in physical
appearance, behavior, or extent of survival in any test
group. Hematology, clinical biochemistry, urinalysis, and
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gross necropsy evaluations did not reveal effects that were
judged to be compound-related. In male rats on 2,500 ppm
which were killed after 1 year of feeding (but not in those
killed after 2 years), there was microscopic evidence of
increased thyroid activity. Female rats on 2,500 ppm which
were killed at 2 years showed significantly increased
organ-weight/ body-weight values for brain and thyroid and
decreased spleen weights. The NOEL for the study is 500 ppm
(25 mg/kg body weight/day).
Provisionally, the study does not meet Agency requirements
for a chronic feeding study. It will be judged for adequacy
when the detailed composition of the test chemicals (98 and
90% chloronebs) fed in the study is provided.
Oncogenicity (163.83-2)
Oncogenicity tests using the technical material are required
in two mammalian species, normally the rat and the mouse.
The studies are required for all food uses.
The two-year rat study (Busey et al . 1967, 00001422) does
not meet the Agency requirements for an Oncogenicity test.
The study does not contain information on incidence of
neoplastic and non-neoplastic lesions observed in the study
and it does not state the composition of the two chloronebs
fed to the test animals. The Agency requires this additional
information to evaluate the study. Registrants may cite
this study as one of the two required Oncogenicity studies
provided that the registrants submits the missing lesion
incidence and product composition data. The Agency will
determine the validity of the study when the deficiencies
are corrected.
Reproduction Testing
Teratology (163.83-3)
The minimum requirement for evaluating a pesticide for
teratogenicity is testing in two mammalian species. It is
required for both food and nonfood uses of chloroneb. No
tests are available on chloroneb to assess teratogenic
effects.
Reproduction (163.83-4)
The minimum requirement for measuring effects on reproduction
is one test in the rat, lasting two generations. This is
required for all food uses. No adequate studies assessing
the effects of chloroneb on reproduction are available at
this time. A rat reproduction study (Kundzin 1967, 00001423)
78
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containing summary data only is in Agency files. To satisfy
this requirement, registrants may submit the referenced
study (not the summary) provided it is supplemented by
individual test animal data. The Agency will determine the
validity of the study when the full data are submitted.
available in detailed form.
Mutagenicity (163.84-1 through 4)
The following studies represent the minimum requirements for
data on the potential heritable effects of chloroneb.
1. A mammalian in vitro point mutation test.
2. A sensitive sub-mammalian point mutation test.
(Bacteria, fungi, insect)
3. A primary DMA damage test (i.e. sister chromatid
exchange or unscheduled DNA synthesis).
4. A mammalian in vitro cytogenics 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.
Although the Agency mutagenic testing requirements are not
final, the standards for these tests should be based on the
principles set forth there in FR 43, No. 163, Tuesday Augst
22, 1978. Protocols and choices of test systems should be
accompanied by a scientific rationale. Substitution of test
systems for those listed above will be considered after
discussion with the Agency.
These requirements should be considered an interim guide and
not final Agency policy. However, the Agency does not
consider the above testing scheme to be a reasonable minimum
requirement.
No adequate mutagenicity studies on chloroneb are available
to the Agency.
Metabolism in Laboratory Animals (163.85-1)
A general metabolism study on chloroneb must be carried
out to fulfill Agency requirements. A metabolism study
is required because chronic studies are required for all
food uses of chloroneb.
A metabolite of chloroneb, 2,5-dichloro-4-methoxyphenol
(DCMP), has been identified in feces of dogs and in tissues
and urine of rats and dogs fed chloroneb (Rhodes and Pease
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1971, 05001159; du Pont 1967, 00001424). Both compounds
showed a very low order of bioaccumulation in mammalian
tissues.
Residues were measured in tissues and excreta of dogs
and in tissues of rats fed chloroneb, as 65 or 75% wettable
powders, in the diet for 2 years (du Pont 1967, 00001424).
Liver, kidney, fat, muscle, spleen, testis, and brain were
sampled from dogs and rats. In addition, blood and excreta
were sampled from dogs. All samples were analyzed for
content of chloroneb and its metabolite, DCMP, by the
microcoulometric gas chromatographic method of Pease.
In dogs fed chloroneb for 2 years (at 7,500 ppm active
ingredient for the last 19 weeks), up to 8 ppm chloroneb
occurred in fat, and 2-6 ppm DCMP occurred in liver and
kidney. In other tissues and in blood, respective contents
of chloroneb and of DCMP did not exceed 1 or 0.4 ppm.
Chloroneb was excreted in feces (2,300 ppm), and DCMP was
excreted in urine (2,400 ppm) and in feces (560 ppm). In
dogs fed 500 ppm for 2 years, chloroneb was found in fat
(0.08 ppm), and its metabolite was found in liver and kidney
(0.1-0.3 ppm). Dogs fed 100 ppm showed no chloroneb (less
than 0.08 ppm) in tissues and DCMP (0.05 ppm) only in
kidney. DCMP was excreted in urine and feces by dogs at
both dietary levels, as was the parent compound in feces of
mid-level dogs.
High-level (2,500-ppm) rats, similarly, showed more chloroneb
(24 ppm) in fat and more metabolite in the kidneys (13 ppm)
than in other tissues. This pattern held true in rats on
500 and 100 ppm chloroneb. Chloroneb occurred in fat (1.6
and 0.13 ppm), and the metabolite occurred in kidneys (5 and
1.4 ppm) of mid- and low-level rats, respectively. Otherwise,
the compounds were generally undetectable (at detectability
limits of 0.1 ppm and less) in other tissues of these rats.
Other unidentified chlorine-containing compounds were
detected in minor amounts in a few samples from dogs and
rats at the high dietary level only.
DCMP is a metabolite of chloroneb in cows, also. Gutenmann
and Lisk (1969, 05001156) identified this compound in
hydrolyzed samples of cow urine and in a 10,000-G supernatant
fraction of beef liver incubated with chloroneb. No chloroneb
(that is, less than 0.02 ppm) was found in the milk of
either of two cows fed chloroneb for 30 days, one at 2 ppm
and one at 50 ppm (Rhodes and Pease 1971, 05001159). DCMP
was detected in the milk (0.2-0.4 ppm) of the cow fed the
higher dose. After withdrawal of chloroneb from the diet,
no metabolite (that is, less than 0.02 ppm) was detected in
milk on the second day.
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The extent of mammalian metabolism of chloroneb and the
presence of other metabolites have not been investigated
sufficiently. Single-dose testing on metabolism and pharmaco-
kinetics of chloroneb must be carried out to comply with
Agency requirements.
Clinical Trails
No clinical
chloroneb.
studies in humans have been conducted using
Emergency Treatment
No information on the prevention and treatment of chloroneb
intoxication is available.
Toxicology - Wettable Powder Chloroneb
Toxicology Profi1e
No adequate tests are available to assess either the acute
toxicity or possible skin or eye effects of wettable powder
chloroneb formulations. Available data on wettable powder
formulations containing 65 and 75% chloroneb are adequate to
assess subchronic oral and subchronic dermal toxicity.
Repeated application to human skin of wettable powder
formulations are not expected t result in systemic effects,
based on results of a subchronic dermal toxicity test in
rabbits on the 75% formulation. See the Manufacturing-use
Chloroneb Section of this chapter for a discussion of
subchronic oral and dermal toxicity and chronic toxicity of
chloroneb.
Data Gaps
Category of Test
Acute Oral
Acute Dermal
Acute Inhalation
Data Requirement
An acute oral toxicity
test in male and female
rats is required for
each wettable powder.
An acute dermal toxicity
study, preferably in the
albino rabbit, is required
for each wettable powder.
An acute inhalation study
in the rat is required for
each wettable powder.
Guideline Number
163.81-1
163.81-2
163.81-3
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Primary Eye A primary eye irritation 163.81-4
Irritation test, preferably in the albino
rabbit, is required for each
wettable powder unless it has
a pH of either 1-3 or 12-14 or
if the product has been judge"?
to be dermally corrosive.
If so, it wi 1 be regulated as a
corrosive substance.
Primary Dermal A primary dermal irritation 163.81-5
Irritation test, preferably in the albino
rabbit, is required for each
wettable powder.
Skin A skin sensitization 163.81-6
Sensitization test in the guinea pig is
required for each wettable
powder formulation.
Human and Domestic Animal Hazard Assessment
All Formulations
Due to its appreciable vapor pressure, chloroneb in all
formulations may be inhaled to a considerable extent by
handlers or applicators (or domestic animals) at the appli-
cation site. Whether it might contaminate drinking water
has not been determined. Exposure to chloroneb-treated soil
may involve contact with both chloroneb and its chlorophenol
metabolites.
Wettable Powder Formulations (65%)
Considerable inhalation and skin absorption of chloroneb
in a 65% wettable powder could occur. This is true,
especially of grounds-keepers and golfers on golf fairways
and greens. It could be true of applicators, especially if
the formulation is used in excess of label directions (in
severe fungal outbreaks). It might be spilled on the skin or
in eyes of persons who dilute, tank-mix, or load spray
equipment. Applicators could breathe spray droplets.
Test results suggest, indirectly, that a person (or domestic
animal) should encounter only low systemic hazard from
acute oral, acute dermal, or acute inhalation exposure to
registered 65% wettable powders. However, further acute
testing is needed on this and any other wettable powder
formulations.
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The potential for long-term repeated exposure to chloroneb
-by any route- to harm human beings or domestic animals
cannot be assessed fully because of its presently incomplete
chemical and toxicologic characterization. Two-year dietary
intake of pure chloroneb at 12.5 mg/kg body weight/day
resulted in no observed harmful effect in rats and dogs.
The test substance was first 98% chloroneb, then 90%
administered as a 75% or 65% wettable powder. Increasing
the intake by ten-fold or more suppressed growth and,
variously, caused adverse effects on liver, kidney, stomach,
or thyroid. At no level of intake did these animals accumulate
significant amounts of chloroneb in body tissues examined,
relative to degree of exposure, nor did they accumulate its
chief known metabolite.
Adequate testing of technical chloroneb for teratogenic,
carcinogenic and mutagenic potential; for effects on reproduc-
tion; and for mammalian metabolism/pharmcokinetics is not
available. Such testing must not be done until the chemical
composition of technical chloroneb is determined adequately
as judged by the Agency.
Topical Discussions
For information concerning subchronic and chronic studies
using a 65% and 75% wettable powder refer to the Manufacturing-
use Chloroneb section of this chapter-
Topics
Acute Oral Toxicity
Acute Dermal Toxicity
Acute Inhalation Toxicity
Primary Eye Irritation
Primary Dermal Irritation
Skin Sensitization
Subchronic Dermal (21-Day) Toxicity
Acute Testing
Acute Oral Toxicity (163.81-1)
The minimum testing needed on acute oral toxicity is one
test in the laboratory rat on each formulated wettable
powder product.
No acute oral tests are available on wettable powders
containing chloroneb.
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k
Acute Dermal Toxicity (163.81-2)
The minimum testing needed on acute dermal toxicity is
one test in the albino rabbit on each formulated wettable
powder product.
No adequate test on a wettable powder formulation is available.
Acute Inhalation Toxicity (163.81-3)
An acute inhalation toxicity test is required on a wettable
powder formulation if it causes a respirable vapor, or if
20% or more of the aerodynamic equivalent is composed of
particles not larger than 10 microns.
Chloroneb has a relatively high vapor pressure and should
provide a respirable vapor. Therefore, a test will be
needed on each chloroneb wettable powder. No tests of acute
inhalation toxicity are available on this formulation
type.
Primary Eye Irritation (163.81-4)
The minimum testing needed to evaluate eye irritation
potential is one test, in albino rabbits for each wettable
powder formulated product. If the test substance has a pH
of 1-3 or 12-14, however, it will be judged corrosive, and
an eye irritation test is not needed. If the test substance
is judged to be dermally corrosive, an eye irritation test
is not needed.
No tests are available on wettable powder formulations
containing chloroneb.
Primary Dermal Irritation
The minimum testing needed to evaluate dermal irritation
potential is one test preferably in the albino rabbit, on
each wettable powder formulated product.
No testing is available for wettable powder formulations
containing chloroneb.
Skin Sensitization (163.81-6)
L
The minimum requirement for assessing skin sensitization is
an intradermal test in one mammalian species, preferably the
guinea pig, on each wettable powder product.
No adequate test for skin sensitization has been done on any
chloroneb wettable powder product.
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Subchrom'c Testing
Subchronic 21-Day Dermal Toxicity
The minimum requirement to assess subchronic 21-day dermal
toxicity is one study, perferably in the albino rabbit, on
each wettable powder formulation of chloroneb if any of its
constituents is likely to increase skin absorption or to
potentiate toxic and pharmacologic effects. The Agency will
evaluate need for this study on a case-by-case basis.
No 21-day dermal study on a wettable powder formulation of
chloroneb is available.
Toxicology - Granular
Toxico19gy Profi1e
Limited data are available on one granular formulation
containing chloroneb as the only active ingredient. Both
very low acute oral hazard and very low potential for
primary dermal irritation are expected in humans for a
granular formulation containing 6.75% chloroneb, based on
the high acute oral LD5Q in male rats (greater than 5 g/kg)
and on the absence of dermal irritation on intact or
abraded rabbit skin. Female rats, however, must be tested
before a final assessment of acute oral hazard can be made
on the 6.75% granular formulation. The acute oral or dermal
hazard for other granular formulations cannot be assessed.
Testing that must be conducted on granular formulations,
including additional tests required on the 6.75% formulation,
is described in the section on Data Gaps.
Data Gaps
Category of Test Data Requirement Guide!ine Number
Acute Oral An acute oral toxicity 163.81-1
test in male and female
rats is required for
each granular, except that
only females must be tested
for one 6.75% granular
formulati on.
Acute Dermal An acute dermal toxicity 163.81-2
study, preferably in the
albino rabbit, is required
for each granular.
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Acute Inhalation An acute inhalation study 163.81-3
in the rat is required for
each granular.
Primary Eye A primary eye irritation 163.81-4
Irritation test in the albino rabbit
is required for each granular
unless it has a pH of either
1-3 or 12-14 or if the dermal
substance is corrosive. If so,
it will be regulated as a
corrosive substance.
Primary Dermal A primary dermal irritation 163.81-5
Irritation test, preferably in the albino
rabbit, is required for each
granular formulation, except
for one 6.75% granular formulation.
Skin A skin sensitization test in 163.81-6
Sensitization the guinea pig is required on
each granular product.
Human and Domestic Animal Hazard Assessment
Granular Formulations
No significant exposure unique to granular formulations for
humans is foreseen.
Based on test results, very low acute oral hazard and very
low potential for primary skin irritations are expected in
persons exposed to one 6.75% granular formulation, based on
test results.
Further acute testing which is needed on this and other
granular formulations is described in the preceding section,
Data Gaps.
The potential for long-term repeated exposure to chloroneb
-by any route- to harm human beings or domestic animals
cannot be assessed fully because of its presently incomplete
chemical and toxicologic characterization. Two-year dietary
intake of pure chloroneb at 12.5 mg/kg body weight/day
resulted in no observed harmful effect in rats and dogs.
The test substance was first 98% chloroneb, then 90%
administered as a 75% or 65% wettable powder. Increasing
the intake by ten-fold or more suppressed growth and,
variously, caused adverse effects on liver, kidney, stomach,
or thyroid. At no level of intake did these animals accumulate
significant amounts of chloroneb in body tissues examined,
relative to degree of exposure, nor did they accumulate its
chief known metabolite.
86
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Adequate testing of technical chloroneb for tetratogeni c,
carcinogenic and mutagenic potential; for effects on reproduc-
tion; and for mammalian metabol i sm/pharmcoki neti cs is not
available. Such testing must not be done until the chemical
composition of technical chloroneb is determined adequately
as judged by the Agency.
Topical Discussions
Acute Oral Toxicity
Acute Dermal Toxicity
Acute Inhalation Toxicity
Primary Eye Irritation
Primary Dermal Irritation
Skin Sensi tization
Subchronic Dermal (21-Day) Toxicity
Acute Testi ng
Acute Oral Toxicity
The minimum testing needed on acute oral toxicity is -one
test in the laboratory rat on each formulated granular
product.
One study is available on a granular formulation containing
6.75% chloroneb (WARF 1971, 00001495). The acute oral
LDj-n of this formulation exceeds 5 g/kg in male rats. At
this level, no deaths occurred. Because only males were
tested, the acute oral toxicity of this formulation cannot
be adequately assessed. For males, the data are adequate
to pi ace 6.75% chloroneb in toxicity Category IV, indicating
a very low acute oral hazard. To complete the assessment,
testing must also be conducted in female rats.
Acute Dermal Toxicity
The minimum testing needed on acute dermal toxicity is
one test, perferably in the albino rabbit on, each formulated
granular product.
No acute dermal tests are available on granular formulations
containing chloroneb.
Acute Inhalation Toxicity
An acute inhalation toxicity test is required on a granular
formulation if it causes a respirable vapor or if 20% or
more of the aerodynamic equivalent is composed of particles
not larger than 10 microns. Chloroneb has a relatively high
87
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vapor pressure and should provide a respirable vapor.
Therefore, a test will be needed on each granular formulation
of chloroneb. No tests of acute inhalation toxicity are
available on this formulation type.
Primary Eye Irritation
The minimum testing needed to evaluate eye irritation
potential is one test, in albino rabbits, on each granular
formulated product. If the test substance has a pH of 1-3
or 12-14, however, it will be judged corrosive, and an eye
irritation test is not needed. If the test substance is
dermally corrosive, it will be judged corrosive to the eye,
and an eye irritation test is not needed..
No test are available on granular formulations containing
chl oroneb.
Primary Dermal Irritation
The minimum testing needed to evaluate dermal irritation
potential is one test preferably in the albino rabbit on
each granular formulated product.
A granular formulation containing 6.75% chloroneb was not
irritating to intact to abraded rabbit skin (WARF 1971,
00001495). No erythema or edema was noted at 24 or 72
hours. The study is adequate to place 6.75% chloroneb in
Category IV, indicating a very low potential for dermal
irritation.
Skin Sensitization
The minimum requirement for assessing dermal sensitization
is an intradermal test in one mammalian species, perferably
the guinea pig, on each granular formulation of chloroneb.
None is available.
Subchronic Testing
Subchronic 21-Day Dermal Toxicity
The minimum requirement to assess subchronic 21-day dermal
toxicity is one study, perferably in the albino rabbit, on
each granular formulation of chloroneb if any of its
constituents is likely to increase skin absorption or to
potentiate toxic and pharmacologic effects. The Agency will
evaluate need for this study on a case-by-cse basis.
No 21-day dermal study on a granular formulation of chloroneb
is available.
88
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Toxicology - Dust
Toxicology Profile
Since no testing is available on dust chloroneb, no summary
can be made. The required tests are listed in the section
on Data Gaps.
Data Gaps
Category of Test
Acute Oral
Acute Dermal
Acute Inhalati on
Primary Eye
Irritation
Primary Dermal
Irritati on
Skin
Sensitization
Data Requirement
Guideli ne Number
An acute oral toxicity 163.81-1
test in male and female
rats is required for
each dust product.
An acute dermal toxicity 163.81-2
study, preferably in the
albino rabbit, is required
for each dust product.
An acute inhalation study 163.81-3
in the rat is required for
each dust product.
A primary eye irritation 163.81-4
test in the albino rabbit
is required for each dust
product unless it has
a pH of either 1-3 or 12-14.
or unless it has been
judged dermally corrosive.
If so, it will be regulated
as a corrosive substance.
A primary dermal irritation 163.81-5
test, preferably in the albino
rabbit, is required for each
dust product.
A skin sensitization test is 163.81-6
is required for each dust
formulat ion.
Human and Domestic Animal Hazard Assessment
Dust Formulations
Contact with any dust formulation by inhalation or skin
adsorption is possible.
89
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No tests on a dust formulation are contained in Agency
files. Therefore, the acute hazard of exposure to dust
chloroneb cannot be assessed.
The potential for long-term repeated exposure to chloroneb
-by any route- to harm human beings or domestic animals
cannot be assessed fully because of its presently incomplete
chemical and toxicologic characterization. Two-year dietary
intake of pure chloroneb at 12.5 mg/kg body weight/day
resulted in no observed harmful effect in rats and dogs.
The test substance was first 98% chloroneb, then 90%
administered as a 75% ir 65% wettable powder. Increasing
the intake by ten-fold or more suppressed growth and,
variously, caused adverse effects on liver, kidney, stomach,
or thyroid. At no level of intake did these animals accumulate
significant amounts of chloroneb in body tissues examined,
relative to degree of exposure, nor did they accumulate its
chief known metabolite.
Adequate testing of technical chloroneb for tetratogenic,
carcinogenic and mutagenic potential; for effects on reproduc-
tion; and for mammalian metabolism/phamcokinetics is not
avail able.
Topical Discussions
Topics
Acute Oral Toxicity
Acute Dermal Toxicity
Acute Inhalation Toxicity
Primary Eye Irritation
Primary Dermal Irritation
Skin Sensitization
Subchronic (21-day) Toxicity
Acute Testing
Acute Oral Toxicity
The minimum testing needed on acute oral toxicity is one test
in the laboratory rat on each formulated dust product.
No tests on dust formulations containing chloroneb are
avail able.
Acute Dermal Toxicity
The minimum testing needed on acute dermal toxicity is one
test, preferably in the albino rabbit, on each formulated
dust product.
No acute dermal tests are available on dust formulations
containing chloroneb.
90
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Acute Inhalation Toxicity
An acute inhalation toxicity test is required on a dust
formulation if it causes a respirable vapor, or if 20% or
more of the aerodynamic equivalent is composed of particles
not larger than 10 microns. Chloroneb has a relatively high
vapor pressure and should provide a respirable vapor.
Therefore, a test will be needed on each chloroneb dust
formulation. No tests of acute inhalation toxicity are
available on this formulation type.
Primary Eye Irritation
The minimum testing needed to evaluate eye irritation
potential is one test, in albino rabbits, on each formulated
dust product. If the test substance has a pH of 1-3 or
12-14, however, it will be judged corrosive, and an eye
irritation test is not needed. If the test substance has been
judged dermally corrosive, the test substance will be judged
to be corrosive to the eye and an eye irritation test is not
needed.
No tests are available on granular formulations containing
chloroneb.
Primary Dermal Irritation
The minimum testing needed to evaluate dermal irritation
potential is one test, preferably in the albino rabbit,
on each dust formulated product.
Testing on dust formulations containing chloroneb is not
available.
Skin Sensitization
The minimum requirement for assessing dermal sensitization
is an intradermal test in one mammalian species, preferably
the guinea pig, on each dust formulation of chloroneb. None
is available.
Subchrom'c Testing
Subchronic 21-Day Dermal Toxicity
The minimum requirement to assess subchronic 21-day dermal
toxicity is one study, preferably in the albino rabbit, on
each dust formulation of chloroneb if any of its constituents
is likely to increase skin absorption or to potentiate toxic
and pharmacologic effects. The Agency will evaluate need
for this study on a case-by-case basis.
No 21-day dermal study on a dust formulation of chloroneb is
available.
91
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Bibli ography
-MRID CITATION
00001422 Busey, W.M., Crews, L.M., and Kundzins, W.
1967. 24-Month Dietary Feeding--Rats :
Fungicide 1823: Final Report: Project No.
201-124. (Unpublished study received July 8,
1968, under 8F0657; prepared by Hazleton
Laboratories, Inc., submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:091147-B)
00001421 Busey, W.M., and Kundzins, W. 1967. Two-Year
Dietary Feeding--Dogs: Fungicide 1823:
Final Report: Project No. 201-125. (Unpublished
study received July 8, 1968, under 8F0657;
prepared by Hazleton Laboratories, Inc.,
submitted by E.I. du Pont de Nemours and
Co., Inc., Wilmington, Del.; CDL:091147-A)
00001424 E.I. du Pont de Nemours and Company, Inc.
1967. Chioroneb--Chronic Feeding Studies:
Tissue Analysis--Dogs, Rats. (Unpublished
study received July 8, 1968, under 8F0657;
CDL:091147-D)
GS0007-011 Ferenz, R.L. 1979a. Eye Irritation in
Rabbits. (Unpublished study received
December 13, 1979, 'under 352-386; prepared
by Haskell Laboratory, submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:241500)
GS0007-012 Ferenz, R.L. 1979b. Skin Irritation in
Rabbits. (Unpublished study received
December 13, 1979, under 352-386; prepared
by Haskell Laboratory, submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del. ; CDL:241500)
05001156 Gutenmann, W.H., and Lisk, D.J. 1969.
Metabolic Studies with Chloroneb Fungicide
in a Lactating Cow. J. Agric. Food Chem.
17:1008-1010
GS0007-010 Hinckle, L. 1979. Oral LD50 Test. (Unpublished
study received December 13, 1979, under
352-G1A; prepared by Haskell Laboratory,
submitted by E.I. du Pont de Nemours and
Co., Inc., Wilmington, Del.; CDL:241500
92
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-MRID CITATION
00001445 Hood, D.B. 1965. Fifteen-Exposure Dermal
Study with 1,4-Dichloro-2,5-Dimethoxybenzene:
Report No. 106-65. (Unpublished study
received October 27, 1965, under 352-313;
submitted by E.I. du Pont de Nemours and
Co., Wilmington, Del.; CDL:050831-B)
00001423 Kundzin, T. (1967) Three-Generation Reproduction
Study of Fungicide 1823: Final Report:
Project No. 201-126. (Unpublished study
received jUl 8, 1968 under 8F0657; prepared
by Hazelton Laboratories, Inc., submitted
by E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:091147C)
00004982 Kwon, B.K. 1965. Acute Inhalation Toxicity:
Haskell Laboratory Report No. 31-65.
(Unpublished study received October 27,
1965, under 352-313; submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:050831-F)
05001159 Rhodes, R.C., and Pease, H.L. 1971. Fate of
Chloroneb in Animals. J. Agric. Food Chem.
19:750-753
00004980 Sherman, H. 1964a. Ninety-Day Feeding Study
with 1 ,4-Dichloro-2,5-Dimethoxybenzene
(INK-1823): Report No. 81-64. (Unpublished
study received Octover 27, 1965, under
352-313; submitted by E.I. du Pont de
Nemours and Co., Wilmington, Del.; CDL:05.0831-C)
00004980 Sherman, H. 1964b. Ten-dose subacute Oral
Test: Haskell Laboratory Report No. 23-64.
(Unpublished study received Octoer 27,
1965, under 352-313; submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:050831-D)
00001495 WARF Institute, Inc. 1971. Oral LD50 and
Skin Irritation of 1 ,4-Dichloro-2,5-Dimethoxy-
benzene: WARF No. 1080676. (Unpublished
study received October 18, 1971, under
538-79; submitted by O.M. Scott and Sons
Co., Marysville, Ohio; CDL:050143-A)
93
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VI. RESIDUE CHEMISTRY
Residue Chemistry - Manufacturing-Use Chloroneb
Residue Chemistry Profile
Chloroneb is a fungicide used to protect cotton, bean,
soybean, and sugarbeet seedlings against a variety of
diseases. For this use, the fungicide is applied either
directly to seed or in-furrow at time of planting. Chloroneb
is also used on ornamental turf grass to control blights.
Chloroneb has been shown by a variety of methods to be
systemic in plants. The compound is taken up through the
roots and distributed throughout the plants, concentrating
most heavily in roots, lower stem, and cotyledons. There is
little redistribution of residues in plants during maturation.
Chloroneb is extensively metabolized in plants to 2,5-dichl oro-
4-methoxyphenol , which is present in plant tissues as the
free phenol and as a glucose conjugate. The phenol is
metabolized to a small extent to 2,5-dichlorohydroquinone,
which is, in turn, converted to 2,5-dichloroquinone.
In animals, metabolism of Chloroneb also proceeds via
2,5-dichloro-4-methoxyphenolI. Unidentified conjugates of
the phenol have been found in urine and in milk of cows fed
high dose of Chloroneb.
The gas chromatographic method of Pease is capable of
determining Chloroneb, free 2,5-dichloro-4-methoxyphenol,
and acid labile conjugates of the phenol. The method is
suitable for obtaining data on residues in raw agricultural
commodities and for tolerance enforcement. The method has
been validated for use on snap beans, snap bean foliage,
dried beans, peas, soybeans, cottonseed, sugarbeet roots ,
sugarbeet tops, meat, meat by-products, and milk. Ti:e
sensitivity of the method for most commodities is 0.02
ppm.
Data on crops indicate that at present directed rates of
applications, residues are generally higher in plants grown
from seed treated in-furrow than in plants grown from seed
directly treated with the fungicide. Residues in seeds of
plants grown from Chloroneb treated seed are ordinarily
below detectable levels, however, residues in foliage
of plants grown from treated seed are quite high soon
after emergence, decreasing to low but detectable levels
six weeks after emergence. Residues in mature plants
consist principally of free conjugated 2,5-dichloro-
4-methoxyphenol .
94
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Residues were found in the kidney of a cow maintained on 2 ppm
chl oroneb and in milk of a cow maintained on 50 ppm chloroneb.
The residue consisted of 2,5-dichloro-4-methoxyphenol
probably as a conjugate.
Data Gaps
The following data are required to support the tolerances
for chloroneb.
1) Data on the metabolism of chloroneb in food animals.
Available data are qualitative, whereas quantitative as well
as qualitative data on the disposition of chloroneb in food
animals are required.
2) Data on residues in beans and bean vines (forage),
soybeans and soybean vines (forage), cottonseed and cotton
forage, and sugarbeets (roots and tops). Available data were
not submitted in raw* form and, with the exception of the
data on beans, were obtained on an inadequate number of
samples.
3) Information on the storage of agricultural commodities
between sampling and residue analysis. Data on storage
conditions and on the stability of residues during sample
storage are required. No data are available.
4) Data on residues in fractions of processed cottonseed,
soybeans, and sugarbeets. No data are available. The data
would not be required if residue data requested in raw
agricultural commodities are low enough that residues in
processed commodities would not likely exceed 0.1 ppm, the
tolerance on the raw commodities. The Agency assumes a
maximum concentration factor of 5 in processing cottonseed
and soybeans to oil, and a factor of 20 in processing
sugarbeets to dried pulp. Therefore, fractionation studies
would not be required if residues on cottonseed and soybeans
were less than .02 ppm (.lppm/5), and residues on sugarbeets
were less than .005 ppm (.lppm/20).
5) Data on whether residues are transferred from items
of animal feed to meat and milk. Available data were
obtained on too few animals, and were not submitted in
raw* form.
*
Raw data are data which are uncorrected for reagant
blanks, untreated crop blanks, and recovery fortified
samples.
95
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Topical Discussions
Use Patterns and Restrictions
Chloroneb is a fungicide used alone or in combination
with other fungicides to protect cotton, bean, soybean,
and sugarbeet seedlings against damping off, blights,
and other seedling diseases, especially those caused by
species of Pythi urn, Rhi zoctpni a. and Scleroti urn. The
fungicide is applied directly to seed or applied to soil
as an in-furrow treatment at planting. Chloroneb is also
broadcast or sprayed on ornamental turfgrass, including
golf greens and fairways, to control blights caused by
Pythiurn and Typhula species.
Chloroneb is available as an wettable-use product in wettable
powder, dust, and granular formulations containing 1.015% to
65% chloroneb.
Dust and granular formulations of chloroneb intended for
use on seeds of agricultural crops contain a label recommendation
that the products supplement standard fungicide seed treatments.
The label on a wettable powder formulation intended for the
same use indicates that the product may be used alone or
in combination with standard seed treatments.
For use directly
are applied once
on seeds, dust and wettable powder formulations
at the rates indicated below:
LBS. CHLORONEB PER 100 IBS. OF SEED
DUST
072~
0.2
0.5
WETTABLE POWDER
0.16
0.16a
0.24a,
0.24
0.41b
SEED
BEM
SOYBEAN
COTTON
SUGARBEET
a East of the Rocky Mountains.
b West of the Rocky Mountains.
For use as an in-furrow treatment, formulations are applied once
at the following rates:
SEED
BEAN"
SOYBEAN
COTTON
LBS. CHLORONEB PER ACRE
DUST
TTO~
1.0
1.0-2.0
GRANULES
1.0
1.0
1.0-2.0
WETTABLE POWDER
0.98
0.98
1.3-1.95
96
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For use on turfgrass, granular formulations are broadcast
0.17 - 0.37 Ibs. of chloroneb per thousand square feet
(7.4-16.1 Ibs. per acre). Products are applied one to
three times a year for control of gray snow mold (Typhula
blight), or every five to ten days for control of Pythium
blight. The only wettable powder formulation registered
for use on turfgrass is sprayed at 0.16 Ibs. per three
to five gallons per thousand square feet every five to
seven days to control Pythium blight. For the control
of Typhul a blight, it should be sprayed once at 0.24 to
0.37 Ibs. per three to five gallons per thousand square
feet.
Chloroneb formulations contain a number of label restrictions.
Formulations intended for direct application to seeds
have a label warning against use of treated seed for food,
feed, or oil purposes. Labels on formulations intended for
use on bean and soybean seed prohibit grazing of plants
grown from treated seeds within 45 days of planting. Labels
on formulations intended for use on ornamental turfgrass
contain a restriction on grazing or feeding of clippings
from treated areas to livestock.
With the exception of the use of turfgrass, the above
uses of chloroneb are food uses and are expected to result
in residues in human food and animal feed. The use on
ornamental turfgrass does not constitute a food use,
provided the label restriction stated above is followed.
Uptake, Distribution, and Metabolism in PI ants
Whenever a pesticide is proposed for use on agricultural
crops, the Agency requires data on the fate of the pesticide
in plants. It has been demonstrated by a variety of methods
that chloroneb is systemic in plants. Soybean seeds treated
with chloroneb and subsequently germinated in vermiculite
contained a water extractable residue toxic to Rhizoctonia
solani (Thapliyal and Sinclair 1970, 05001302). In a
similar study, soybean seedlings grown from seed dusted with
8 oz. chloroneb per 100 Ibs. of seed were divided into
roots, hypocotyls, cotyledons and leaves, and water soluble
extracts of the plant parts prepared. Extracts of cotyledons
were inhibitory to R. solani 14 days after planting (Thapliyal
and Sinclair 1971, 05001304). Extracts of chickpea
seedlings grown from chloroneb-treated seed, grown in
chloroneb-treated soil, or treated by root immersion in
chloroneb solution, were toxic to Sclerotium rolfsii.
Fungitoxic residues persisted for nine days in seedlings
started in treated soil following transplantation to chloroneb-
free soil. Root extracts were more toxic than extracts
prepared from shoots (Verma and Vyas 1976, 05001172).
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14
Ring-labeled C-chloroneb has been shown by radioautography
to be taken up in cotton seedlings (Rhodes 19??b, 00002218;
Kirk, Sinclair, and lambremont 1969, 05001181), in soybean
seedlings (Kharbanda 1971, GS0007-013), in snap beans
(Rhodes 1968, 00001430), and in turfgrass (Vargas and
Turgeon 1975, 05001134). Heavy labeling of roots and
lower stems was consistently seen in these studies. Cotyledons
were heavily labeled in cotton (Rhodes 19??b, 00002218) and
bean (Rhodes.1968, 00001430) seedlings grown from seeds
planted in C-chloroneb treated soil. Cotyledons were
much less heavily labeled in a five-day old cotton seedling
14
exposed to a C-chloroneb solution by root immersion
(Kirk, Sinclair, and Lambremont 1969, 05001181). There
was noticeable labeling of true leaves only in the bean
and cotton plants grown from seed planted in treated soil
(Rhodes 19??b, 00002218; Rhodes, 1968, 00001430).
Data obtained by analysis of C-chloroneb treated plants
with liquid scintillation techniques support the radio-
autography data. Five-day old bush bean.(Phaseolus vulgaris
seedlings treated by root immersion in C-chloroneb
solution for 48 hours were labeled throughout the plants
with the highest concentration of label in the roots and
lower stem (Thorn 1973,.05001297). Soybean seedlings grown
from seed dusted with C-chloroneb were most heavily
labeled in the cotyledons with little radioactivity in
roots, hypocotyls and true leaves. There was no difference
in radiolabel distribution between seedlings analyzed
nine and 14 days after planting (Thapliyal and Sinclair
1971, 05001304}. Five to seven-day old soybean seedlings
immersed in a C-chloroneb solution tended to accumulate
radioactivity in the lower stem, with lesser amounts in
the cotyledons and very little radioactivity in the upper
stems and true leaves. Roots were not analyzed (Kharbanda
1971, 6S0007-013). There was little redistribution of
radioactivity to upper parts of maturing soybeans exposed
for one week during the seedling stage to C-chloroneb.
It was also demonstrated in the same study that C-chloroneb
applied to true leaves of soybeans migrated to other parts
of the plant although the pattern of distribution was
highly variable (Kharbanda, 1971, 6S0007-013). In snap
bean (Rhodes, 1968, 00001430, Rhodes, Pease, and Brantley,
1971, 05001158) and cotton (Rhodes. 19??b, 00002218; Rhodes,
ase, and Brantley 1971, 05001158) seedlings grown from
C-chloroneb treated seed, radioactive residues predominated
in roots, lower stems, and cotyledons, with little radioactivity
being found in upper stems (above the cotyledons) and true
leaves. There was no redistribution of radioactivity to
upper portions of either cotton or bean plants during
maturation. The level of radioactivity in roots resulting
98
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from in-furrow seed treatment was considerably higher than
the level resulting from direct application of the labeled
fungicide to seeds in both cotton and beans (Rhodes 19??b,
00002218; Rhodes 1968, 00001430).
Some data on metabolism of chloroneb in plants are available.
Extracts of hypocotyls from soybean seedlings immersed
in C-chloroneb solution contained a labeled compound
that was shown by thin-layer chromatography to be more polar
than chloroneb (Kharbanda 1971, GS0007-013). Snap beans
grown in a greenhouse from seed treated in-furrow with
ring-labeled C-chloroneb at 1 Ib. per 12,000 row feet,
and harvested 12 days after planting, contained four degradation
products of chloroneb (Rhodes 1968b, 00001407; Rhodes,
Pease and Brantley 1971, 050011580. These compounds,
comprising over 80% of the total C-residue, were identified
as chloroneb (50.6% of the labeled material), 2,5-dichloro-4-
methoxyphenol (45.8%), 2,5-dichlorohydroquinone (0.6%), and
2,5-dichloroquinone (0.9%). An additional compound comprising
2.1% of the extractable residue was not identified. Identifica-
tion of compounds was based on comparison of chromatographic
mobility, infrared spectra, and mass spectra with reference
standards (Rhodes 1968b, 00001407; Rhodes, Pease, and
Brantley 1971, 05001158).
Cotton plants grown in a greenhouse from seeds treated with
0.92 Ibs. of ring-labeled C-chloroneb per 12,000 row
feet, and extracted and analyzed in the same manner as
the snap beans described above contained the four degration
products of chloroneb in a pattern remarkably like that seen
in beans (Rhodes, Pease, and Brantley 1971, 05001158). Of
the total C-residue, 84% could be extracted, of which
52.1% was chloroneb, 44.2% was 2,5-dichloro-4-methoxyphenol,
0.7% was 2,5-dichlorohydroquinone, 0.9% was 2,5-dichloro-
quinone, and 2.1% was unidentified (Rhodes, Pease, and
Brantley 1971, 05001158).
The above studies show that the predominant residues
from the use of chloroneb on plants are the parent compound
and free 2,5-dichloro-4-methoxyphenol. A somewhat different
picture is seen in bush beans (P. vulgaris) treated by
root immersion in ring-labeled C-chloroneb solution,
Ethanol extracts of roots, combined hypocotyl and cotyledons,
and combined epicotyl and leaves were analyzed by thin-layer
chromatography and found to contain 35% - 76% chloroneb,
4% - 8% of the free phenol, and 21% - 57% of the glucoside
conjugate of the phenol (Thorn 1973, 05001297). Traces
of 2,5-dichlorohydroquinone were also reported. The identity
of the glucoside was determined by comparison of the chromato-
graphic mobility of the labeled metabolite with synthesized
99
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glucoside in three solvent systems, and by crystallization
to constant specific radioactivity of a mixture of the
labeled metabolite and unlabeled synthetic glucoside (Thorn
1973, 05001297).
The failure to observe the glucoside conjugate in significant
amounts in the snap bean and cotton studies (Rhodes 1968b,
00001407; Rhodes, Pease, and Brantley 1971, 05001158)
may be due to the extraction procedure in which the first
step is a digestion of plant material in 5N phosphoric acid.
The glucoside conjugate, if initially present, would be
expected to hydrolyze during the digestion. In the bush
bean study (Thorn 1973, 05001297), the plant tissues were
extracted with 80% ethanol.
The metabolism of chloroneb in plants is adequately defined
for the currently registered uses of chloroneb. Chloroneb
is taken up by plants through roots and distributed throughout
the plant concentrating primarily in roots, lower stem,
and cotyledons. Chloroneb is extensively metabolized to
2,5-dichloro-4-methoxyphenol which is in turn metabolized to
a small extent to 2,5-dichlorohydroquinone, and 2,5-dichloro-
quinone. Evidence from one study indicates that, in bush
beans, the phenol is readily conjugated with glucose and
that the free phenol is present at very low concentration
in beans.
Metabolism of Chloroneb in Food Animals
When use of a pesticide on agricultural crops results
in residues in items of animal feed, the Agency requires
data on the fate of the pesticide in food animals. Data on
metabolism of chloroneb in food animals are sparse. A
cow maintained for 30 days on a diet containing 2 ppm
chloroneb was found to have 0.05 ppm of 2,5-dichloro-4-methoxy-
phenol in its kidneys (du Pont 1967a, 00001431; Rhodes
and Pease 1971, 05001159). Another cow maintained on a diet
containing 50 ppm of chloroneb had measurable milk levels of
the phenol throughout the feeding period, and levels of 14
ppm in urine seven days after chloroneb feeding began
(du Pont 1967a, 00001431; Rhodes and Pease 1971, 05001159).
The samples in these studies were analyzed* by the method of
Pease (see Analytical Method below) which involves digesting
samples in 5N phosphoric acid. Conjugates of 2,5-dichloro-4-
methoxyphenol would likely be hydrolyzed to the free phenol
during the digestion. However, the milk samples from the
cow maintained on 50 ppm chloroneb were also analyzed by an
alternative method in which samples were extracted with an
organic solvent at neutral pH (Rhodes 19 a, 00002214).
It was found that the phenol could be detected in milk
100
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only after refluxing of the sample with hydrochloric acid,
indicating that the phenol was originally present in the
samples as an acid labile conjugate.
A cow maintained for four days on a diet containing 5
ppm chloroneb had detectable amounts of 2,5-dichl oro-4-
methoxyphenol in acid hydrolyzed urine but not in unhydrolyzed
urine, indicating the presence of conjugated phenol.
The amount of phenol in the urine accounted for 44% of the
ingested dose, however, the remaining dose was unaccounted for.
The formation of the .ihenol from chloroneb was demonstrated
by use of an in vitro metabolizing system using a crude
microsomal preparation from beef liver (Gutenmann and
Lisk 1969, 05001156).
The data on metabolism of chloroneb in food animals are
inadequate. The available data show only that chloroneb
is metabolized to 2,5-dichloro-4-methoxyphenol and that
the phenol may be conjugated in milk and in urine. There
have been no studies to determine the quantitative disposition
of administered chloroneb in food animals. (For metabolism
in laboratory animals see the "Toxicology" chapter.)
Analytical Methods
The Agency requires the submission of, or reference to,
validated analytical methods suitable for obtaining data
on the nature and amount of pesticide residues resulting
from proposed use. One method must be suitable for tolerance
enforcement. The regulatory method for determination of
a pesticide in raw agricultural commodities must be capable
of measuring the total toxic residue derived from the
pesticide. Metabolism data indicate that chloroneb, 2,5-dichl oro-
4-methoxyphenol , and conjugates of the latter compound
comprise the bulk of the residue found in plants and animals
as a result of chloroneb use.
The regulatory method for chloroneb in Vol. II of the
Pesticide Analytical Manual is the method of Pease (Pease
1967, 00001429). In this method a sample of plant or animal
tissue is mixed with 5N phosphoric acid and subjected to 12
hours of simultaneous steam distillation and hexane extraction
by means of a Bleidner apparatus. The hexane extract is
carefully concentrated to a small volume and aliquots are
analyzed by microcoullometric gas chromatography (MCGC) with
temperature programming. Concentrated hexane extracts of
samples with high oil content are cleaned-up prior to
analyses by partition into acetonitrile or by Florisil
columm chromatography with ethyl acetate as column elutant.
Acetonitrile and ethyl acetate extracts are carefully
concentrated to a small volume before analysis by MCGC.
101
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The method determines chloroneb and the phenolic metabolite
separately. The compounds are steam distilled during the
phosphoric acid .digestion procedure, and are determined
during a single MCGC run. Chloroneb and the phenol are well
separated on the gas chromatographic column. Conjugates
of the phenol would be expected to hydrolyze during the 12
hour distillation-extraction step and would be determined as
free phenol.
Recovery studies utilizing the Pease method have been
carried out on snap beans, snap bean foliage, dry green
beans, peas, soybeans, cottonseed, sugarbeet roots, and
sugarbeet tops (Pease 1967, 00001429). The average recovery
of chloroneb from 40 samples fortified at 0.02 to 1.0 ppm
was 95% and individual values varied from 77% to 114%.
Average recovery of the phenol from 40 samples fortified at
0.02 to 3.1 ppm was 88% and values ranged from 71% to 110%
(Pease 1967, 00001429).
Recovery studies have also been carried out in bovine
tissues including muscle, subcutaneous fat, liver, kidney,
whole milk, milk fractions (fat and aqueous), and urine
(du Pont 1967a, 00001431). The overall average recovery of
chloroneb from 19 samples fortified at 0.02 to 0.55 ppm was
89% and values varied between 69% to 109%. Average recovery
of 2,5-dichloro-4-methoxyphenol from 21 samples fortified
with 0.02 to 1.03 ppm was 80% and values ranged from 54% to
110%. Recovery of both compounds from urine tended to be
1 ow.
The sensitivity of the method is 0.02 ppm each for both
chloroneb and the phenol metabolite (1 ppm in urine).
The Pease method is adequate for enforcement provided that
no new toxic metabolites of chloroneb are identified.
Residues j_n_ Plants
Whenever a pesticide is proposed for use on an agricultural
crop, the Agency requires data on the nature and amount
of residue on the crop resulting from the proposed use.
Limited residue data have been obtained with.a variety
of chloroneb formulations and ring-labeled C-chloroneb
formulated as a 75% wettable powder. With one exception
(discussed below) crops treated with unlabeled chloroneb
formulations were analyzed for residues of chloroneb and
2,5-dichloro-4-methoxyphenol by,the method of Pease (Pease
1967, 00001429). Samples with C-residues were analyzed
by combustion techniques and subsequent scintillation
counting.
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Cotton
Cotton plants grown in a greenhouse from seeds treated
with the C-chloroneb formulation at 6.75 oz. chloroneb
per 100 Ibs. of seeds contained 150 ppm of chloroneb
equivalents one week after planting, 0.7 ppm after eight
weeks, and 0.2 ppm at 16 weeks. Seeds from plants sampled
at 16-20 weeks contained no detectable (<0.01) residues
(Rhodes, 19??b, 00002218; Rhodes, Pease and Brantley,
1971, 05001158).
Cotton plants, greenhouse-grown from seeds planted in
soil treated with the C-chloroneb formulation to simulate
a field application rate of 2 Ibs. active per 12,000 row
ft., contained 397 ppm of chlorpneb equivalents one week
after planting and 7 ppm after eight weeks. Seeds contained
0.04 ppm after 22 weeks (Rhodes 19??b, 00002218; Rhodes,
Pease, and Brantley 1971, 05001158).
1 4
Cotton plants from seed field-treated with the C-
chloroneb formulation by in-furrow application of 2 Ibs.
per 12,000 row feet contained 0.23 ppm chloroneb equivalents
in whole plants at maturity and 0.03 ppm in seeds (Rhodes,
19??b, 00002218; Rhodes, Pease, and Brantley, 1971, 05001158).
Residues were not detected (<0.01 ppm) in 11 cottonseed
samples from plants grown from seeds treated by direct
application of a 5% dust containing 0.5 to 1.0 Ibs.
of chloroneb per 100 Ibs. of seeds (du Pont 1967c, 00001412;
du Pont 1965, 00001434.). No residues were detected
in two samples of cottonseed from plants grown from seeds
treated by in-furrow application of a wettable powder
containing 75% chloroneb at 1.5 or 2.25 Ibs. of chloroneb
per acre-row (du Pont 1967c, 0001412; du Pont 1965,
00001434). The 13 seed samples were from nine locations in
four southern states and were obtained 123 to 169 days after
treatment. Samples were analyzed by an earlier version of
the Pease method in which the samples are digested in a
strongly alkaline medium instead of in acid. Consequently,
the earlier method does not determine the phenolic metabolite
of chloroneb (du Pont 1965 00001434).
Additional cottonseed samples were analyzed by the Pease
method. Three samples, two from Mississippi and one from
California, were from plants grown from seeds receiving
0.5 Ibs. of chloroneb (unspecified formulation) per 100 Ibs.
of seed. One sample from Texas was from a plant grown
from seed treated in-furrow at 1.2 Ibs. chloroneb (unspecified
formulation) per acre. Plants were harvested 135 to 157
days after treatment. Residues of chloroneb and its
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metabolite could not be detected (<0.02 ppm), except for
a sample from a plant grown from directly treated seeds
that contained 0.03 ppm chloroneb (du Pont 1967c, 00001412).
There are no ata on residues in cotton foliage from use
of non-radiolabeled chloroneb formulations. There are
no data on cottonseed fractions from processed cottonseed.
Snap beans and dried beans
Residues in snap bean plants grown in a greenhouse from seed
treated with 3 oz. C-chloroneb per 100 Ibs. of seed were
127 ppm one week after planting and 2.6 ppm after five weeks.
Residues in edible pods were 0.04 ppm five weeks after planting
(Rhodes 1968, 00001430; Rhodes, Pease, and Brantley 1971,
05001158).
Snap bean plants grown in a greenhouse from.seeds treated
by simulated in-furrow application of the C-chloroneb
application at 2 Ibs. chloroneb per 12,000 row feet contained
290 ppm of chloroneb equivalents one week after planting and
18 ppm after five weeks. Residues in pods were 0.48 ppm at
four weeks and 1.5 ppm five weeks after planting (Rhodes
1968, 00001430; Rhodes, Pease, and Brantley 1971 05001158).
Bean plants grown in the field from seeds treated by
in-furrow application of the radiolabeled chloroneb formu-
lation at 2 Ibs. chloroneb per 12,000 row feet contained 2.1
ppm residues in whole plants at maturity. Pods contained
0.08 ppm. Residues in whole plants fjfld grown from seeds
treated by direct application of the C-chloroneb formu-
lation at 2.6 oz. per Ibs. of seeds were 0.32 ppm at maturity.
Residues in pods were 0.003 ppm (Rhodes 1968, 00001430,
Rhodes, Pease, and Brantley 1971, 05001158). It should be
noted that edible pods from greenhouse grown bean plants
grown from in-furrow treated seeds contained much higher
residues (0.48, 1.5 ppm) than pods from field grown plants
treated in the same manner (0.08 ppm). The greenhouse
plants were pot grown and their roots were, therefore,
confined to the chloroneb treated soil throughout maturation,
whereas the roots of field treated plants could grow
past the chloroneb treated zone.
In a field study carried out at 13 locations in nine geographi-
cally dispersed states, bean seed were treated with chloroneb
(unspecified formulation) in a planter box at 16-36 oz.
chloroneb per 100 Ibs. of seed; in a seed treater at 4-10
oz. chloroneb per 100 Ibs. of seed, or were sown in soil
treated in-furrow with wettable powder, granular, or dust
formulations of chloroneb at 0.5-6 Ibs. chloroneb per
acre-row. Plants were harvested 48-85 days (snap beans) or
104
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84-117 days (dried beans) after treatment, and edible pods
and vines were analyzed by the method of Pease (Pease, 1967,
00001429). Seventeen pod samples were analyzed, 14 of which
contain no chloroneb above the method sensitivity (0.02
ppm), and the remaining three samples contained 0.02 to 0.04
ppm of chloroneb. Thirteen of the 17 pod samples contained
no detectable metabolite (0.02 ppm) and the other four
samples contained metabolite levels of 0.03, 0.04, 0.09.
and 0.14 ppm. Fifteen of the 17 snap bean vine samples
contained chloroneb at 0.03 ppm or less. The remaining two
samples are reported as "<0.2 ppm". Nine of the vine
samples contained metabolite levels of 0.03 ppm or less.
The remaining eight samples contained levels of the phenol
from 0.11 to 2.0 ppm. In general these latter values were
associated with in-furrow application, although within this
group of eight samples, there was little correlation between
application rate and residue level. Four samples of dried
shelled beans and their vines were analyzed by the Pease
method, the beans containing no detectable chloroneb
or metabolite, the vines containing no detectable chloroneb,
and two of the four vine samples containing no detectable
metabolite. The other two vine samples contained 0.26 and
0.31 ppm of the metabolite (du Pont 1967b, 00001412).
Soybeans
Soybean seeds were treated with chloroneb in a seed treater
at 4 oz. active per 100 Ibs., or were sown in soil treated
with granular or wettable powder formulations of chloroneb
at 1 Ib. active per acre. Plant samples from five locations
in four states were harvested 133 to 179 days after treatment
and beans and vines separately analyzed for residues by
the Pease method. Six samples of beans contained no detectable
(<0.02 ppm) level of either chloroneb or its metabolite,
2,5-dichloro-4-methoxyphenol. A single vine sample contained
no detectable (<0.04 ppm) residue of either chloroneb or
the metabolite (du Pont 1967b, 00001412).
Sugarbeets
Seeds were treated with chloroneb (unspecified formulation)
at 2 to 12 ounces per 100 Ibs. of seed. Six plant samples
from three states were harvested 131 to 309 days after
treatment, and roots and tops were analyzed separately
for chloroneb and its phenol metabolite by the Pease method
(Pease 1967, 00001429). No sample contained detectable
(0.02 ppm) levels of either chloroneb or its metabolite.
There have been no data submitted on processed sugarbeet
fractions.
105
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Adequacy of the data on residues in plants
The residue data are inadequate. There were no raw data
submitted with any study. Raw data are needed by Agency
scientists to evaluate data reliability.
No data on the handling of samples between harvest and
analysis were presented. The only information on this
matter indicates that sugarbeets sampled between 10/13/65
and 10/20/66 (du Pont 1967b, 00001412) were analyzed
between 1/4/67 and 6/2/67 (du Pont 1968a, 00003269). Data
on the storage stability of pesticide residues on crops is
particularly relevant to chloroneb because of its volatility
and the volatility of its phenol metabolite.
For most field grown crops, an insufficient number of
samples were analyzed. Six soybean samples were analyzed
for residues, and only one soybean foliage sample. Six
sugarbeet samples were analyzed for residues in roots and
tops. There were 18 cotton seed samples analyzed; however,
only five of these samples were analyzed by methods capable
of detecting both chloroneb and 2,5-dichloro-4-methoxy-phenol
and only two of these five reflected in-furrow use, the
treatment method resulting in highest residues. There was
one cotton foliage sample analyzed.
There were 23 bean plants analyzed, pods (or dried beans)
and foliage being analyzed separately. Of the 23 bean
plant samples, 12 reflected direct seed treatment and 11
reflected in-furrow treatment. The number of bean plant
samples is considered adequate.
There were no data on fractions of processed soybeans,
cottonseed, or sugarbeets. These data are required whenever
the possibility exists that residues may concentrate in
a particular fraction of a processed commodity.
Residues j_n Animals
When use of a pesticide on agricultural crops results
in residues in items of animal feed, the Agency requires
data on whether residues are transferred to meat, milk,
poultry, and eggs.
Residues in Meat and Milk
There are limited data available on residues in meat and
milk. In one feeding study, three cows were maintained on
diets containing 0, 2, and 50 ppm chloroneb administered in
a 65% wettable powder formulation. The cow maintained on 2
ppm chloroneb was sacrificed after 30 days of feeding, and
106
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the cow fed 50 ppm chloroneb was switched to chloroneb-free
rations after 30 days and sacrificed after an additional seven
days, an unacceptable procedure for a feeding study. Milk
collected during the feeding study, and muscle, fat, liver,
and kidney obtained at sacrifice were analyzed for chloroneb
and 2,5-dichloro-4-methoxyphenol by the method of Pease
(Pease 1967, 00001429). Chloroneb per se was not detected
in any sample (<0.02 ppm). The phenol was present at 0.05
ppm in kidney tissue of the cow fed 2 ppm, however, the
phenol was not detected in tissues of the cow fed 50 ppm
chloroneb and sacrificed after a seven day withdrawal
period. The metabolite was not detected in milk of the
cow at 2 ppm chloroneb, but was present at 0.3 to 0.4 ppm
in milk from the cow fed 50 ppm chloroneb. The metabolite
dropped to undetectable (<0.02 ppm) levels in milk two days
after withdrawal of chloroneb treated rations (Rhodes and
Pease 1971, 05001159; du Pont 1967a, 00001431). Fraction-
ation of the phenol-containing milk revealed that the bulk
of the residue was in the aqueous phase (du Pont 1967a,
00001431).
In another study, a cow was maintained for four days on
a diet containing 5 ppm chloroneb administered as the
pure compound. Milk collected during the study was analyzed
by a gas chromatographic method with e-lectron capture
detection. Neither of the compounds was detected (0.02
ppm)(Gutenmann and Lisk 1969, 05001156). No tissues were
analyzed for residues in the study, and the method may not
have had the capability of detecting conjugates of the
phenol metabolite.
There are no data on residues of chloroneb in poultry and
eggs.
Adequacy of the Data
The data on residues of chloroneb in milk and meat are
not adequate. Raw data were not included and thus cannot
be evaluated by Agency scientists. In addition, an insufficient
number of animals were studied. One cow fed 2 ppm chloroneb
was examined for tissue residues while chloroneb feeding
was in progress (Rhodes and Pease 1971, 05001159; du Pont
1967a, 00001431). Another cow, fed an exaggerated level of
50 ppm chloroneb, was shown to have no detectable (<0.02
ppm) tissue residues of either chloroneb or metabolite.
However, the animal was not sacrificed until seven days after
chloroneb treatment had ceased (Rhodes and Pease 1971,
05001159; du Pont 1967a, 00001431). Thus data on the
two cows cannot be compared. Milk samples from three
cows fed 2, 5, and 50 ppm were analyzed, but the method used
107
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for analysis of milk from the cow fed 5 ppm chloroneb may
not have detected conjugates of the phenol (Gutenmann and
Lisk 1969, 05001156), whereas another study indicates that
a conjugate is the primary residue of chloroneb to be
found in milk (Rhodes 19??a, 00002214).
Unpublished Agency guidelines require that feeding studies
be conducted on a minimum of 4 groups of 3 animals per
group. The groups are fed 0-, 1-, 3-, and 10- fold the
amount of pesticide expected in the diet, were the feed item
in question to contain the tolerance level of pesticide.
Normally the Agency requires that the pesticide fed correspond
to the "aged" residue, however, data show that chloroneb is
metabolized similarly in plants and animals and thus the
parent compound above may be fed.
Residue Chemistry - Formulated Chloroneb
Registration Requirements
There are no residue chemistry data required for the non-food
use of chloroneb.
For future registration of a pesticide product for use on a
food or feed crop not covered by this Standard, the Agency
must be provided with a full range of data including a
validated method for analysis of pesticide residues in or on
the raw agricultural commodity, data on metabolism of the
pesticide in plants and (when appropriate) in animals, and
residue data reflecting the proposed use of the pesticide on
the crop. As discussed in this Standard an analytical
method suitable for obtaining chloroneb residue data and for
tolerance enforcement is available. Registrants are therefore
not required to provide a method.
Required Labeling - Wettable Powder
Labels on wettable powder chloroneb used for direct application
to seed should contain a restriction against the use of
treated seed for food, feed, or oil purposes. Wettable
powder chloroneb intended for use on beans or soybeans
should bear a label restriction against grazing of treated
plants within 45 days of planting. Labels on wettable
powder chloroneb intended for use on ornamental turf grass
should contain a restriction against grazing or feeding of
clippings from treated areas to livestock.
Granular
^^^•MHHMMBBMBBM (
Granular chloroneb intended for use on beans or soybeans
should bear a label restriction against grazing of treated
plants within 45 days of planting. Labels on granular
108
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chloroneb intended for use on ornamental turf grass should
contain a restriction against grazing or feeding of clippings
from treated areas to livestock.
As gaps in the residue chemistry data base are filled, other
label restrictions or warnings may become necessary.
Dust
Labels on dust chloroneb used for direct application
to seed should contain a restriction against the use of
treated seed for food, feed, or oil purposes. Dust chloroneb
intended for use on beans or soybeans should bear a label
restriction against grazing of treated plants within 45 days
of planting.
As gaps in the residue chemistry data base are filled, other
label restrictions or warnings may become necessary.
109
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Bib!iography
-MRID
00001434
00001431
00001412
00003269
05001156
05001181
GS0007-013
00001429
CITATION
E.I. du Pont de Nemours & Company, Incorporated
(1965?) Method for Determining Residues of
1,4-Dich1oro-2,5-Dimethoxybenzene. (Unpublished
study received Jul 7, 1965 under unknown
admin, no-; CDL:120886-A)
E.I. du Pont de Nemours & Company, Incorporated
(1967a) Chloroneb Livestock Feeding Studies:
Milk and Meat. (Unpublished study received
Jul 8, 1968 under 8F0657; CDL:091146-U)
E.I. du Pont de Nemours & Company, Incorported
(1967b) Results of Tests on the Amount of
Residue in Crops Grown in Chloroneb Treated
Soil. (Unpublished study received Jul 8,
1968 under 8F0657; COL :091146-1)
E.I. du Pont de Nemours & Company, Incorporated
(1968) Chloroneb--Pesticide Petition No.
8F0657: Supplemental Information: Answer
to FDA Letter of June 4, 1968. (Unpublished
study received Jul 8, 1968 under 8F0657;
CDL:091146-A)
Gutenmann, W.H., Lisk, D.J. (1969) Metabolic
studies with Chloroneb fungicide in a
lactating cow. Journal of Agricultural
and Food Chemistry 17(5):1008-1010
Kirk, B.T., Sinclair, J.B., Lambremont, E.N.
(1969) Trans!ocation of C14-labeled chloroneb
and DMOC in cotton seedlings. Phytopathology
59(10): 1473-1476
Kharbanda, P.O. (1971) Systemicity of C14-labeled
chloroneb in soybean tissues. Unpublished
Ph.D Dissertation, University of Illinois,
46 pp.
Pease, H.L. (1967) Determination of residues
of Chloroneb and a metabolite by microcoulometric
gas chromatography. Journal of Agricultural and
Food Chemistry 15(5):917-919. Undated
method. (Also In unpublished submission
received Oct 16, 1967 under 8F0657; submitted
by E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:092951-G)
110
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-MRID CITATION
00002214 Rhodes, R.C. (19??a) Determination of
2,5-Dichloro-hydroquinone and 2,5-Dichloroquinone
in Milk. Undated method. (Unpublished
study received Jul 8, 1968 under 8F0657;
submitted by E.I. du Pont de Nemours & Co.,
Inc., Wilmington, Del.; CDL:091146-D )
00002218 Rhodes, R.C. (19??b) Greenhouse Studies with
C-14 Ring-Labeled Chloroneb in Cotton
Plants. (Unpublished study received Jul 8,
1968 under 8F0657; submitted by E.I.
du Pont de Nemours & Co., Inc., Wilmington,
Del.; CDL:091146-S)
00001430 Rhodes, R.C. (1968a) Studies with C-14
Ring-Labeled Chloroneb in Bean Plants.
(Unpublished study received Jul 8, 1968
under 8F0657; submitted by E.I. du Pont de
Nemours & Co., Inc., Wilmington Del.;
CDL:091146-T) (MRID 00001430)
00001407 Rhodes, R.C. (1968b) Chemical Identification
of Metabolites of Chloroneb in Bean Plants.
(Unpublished study received Jul 8, 1968
under 8F0657; submitted by E.I. du Pont
de Nemours & Co., Inc., Wilmington, Del.;
CDL:091146-B)
05001159 Rhodes, R.C., Pease, H.L. (1971) Fate of
chloroneb in animals. Journal of Agricultural
and Food 19(4): 750-753
00001158 Rhodes, R.C., Pease, H.L., Brantley, B.K.
(1971) Fate of C14-labeled chloroneb in
plants and soils. Journal of Agricultural
and Food Chemistry 19(4):745-749
05001302 Thapliyal, P.N., Sinclair, J.B. (1970)
Uptake of three systemic fungicides by
germinating soybean seed. Phytopathology
60(9):1373-1375
05001304 Thapliyal, P.N., Sinclair, J.B. (1971)
Translocation of benomyl, carboxin, and
chloroneb in soybean seedlings. Phytopathology
61(10:1301-1302
111
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-MR ID CITATION
05001297 Thorn, G.D. (1973) Uptake and metabolism of
chloroneb by Phaseolus vulgaris. Pesticide
Biochemistry and Physiology 3(2):137-140
05001134 Vargas, J.M., Turgeon, A.J. (1975) Translocation
of C14 labeled chloroneb in three turfgrass
species. Canadian Journal of Plant Science
55(l):85-88
05001172 Verma, R.K. , Vyas, S.C. (1976) Uptake,
translocation and persistence of five
systemic fungicides in gram seedlings.
Pesticides 10(12):21-24
112
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VII. ECOLOGICAL EFFECTS
Ecological Effects - Manufacturing-Use Chloroneb
Ecological Effects Profile
Currently available data indicate that manufacturing-use
chloroneb is practically non-toxic to most terrestrial
wildlife. Manufacturing-use chloroneb is moderately toxic
to aquatic organisms.
Manufacturing-use chloroneb appears to be relatively non-toxic
to birds. Dietary studies on both the bobwhite quail and
mallard duck yielded LC50 values of greater than 5000 ppm.
An acute oral study for birds is not available.
The available aquatic toxicity data suggest that manufacturing-
use chloroneb is moderately toxic to fish and aquatic
invertebrates. The 48 hour LC5Q for an aquatic invertebrate
(D a p h n i a) was approximately 6 ppm. The 96 hour LC50 for a
coldwater fish (rainbow trout) was 3.7 ppm. The test for a
warmwater fish is not available.
Data Gaps
The following fish and wildlife studies testing the effects
of technical chloroneb are required.
An avian single-dose oral LD,
either the bobwhite quail or'
mallard duck.
b. A 96 hour acute LC5Q to a species
of warmwater fish (preferably the
bluegill sunfish).
Guidelines Section
163.71-1
163.72-1
Considering use patterns and environmental fate information,
a "second tier" study may be required. Section 163.72-4 of
the June 10, 1978 proposed Guidelines lists the requirements
for an embryolarval and/or an aquatic invertebrate life
cycle test. The use information and available half-life
data suggest that chronic levels of the chemical could be
available to the aquatic environment. If the leaching data
indicate chemical movement, one or both of these tests will
be necessary. Whether or not one or both of these tests
will be required will depend on environmental fate and
toxicity data. A determination will be made after the
Agency receives the data.
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Topical Discussions
Corresponding to each of the Topical Discussions listed
below is the number of the section(s) in the 'Proposed
Guidelines' of July 10, 1978. (43 FR No. 132,29696) which
explain(s) the minimum data that the Agency require to
adequately assess chloroneb's Ecological Effects. Where no
section number is listed, a minimum requirement has not been
set for such information.
Guidelines Section
Birds 163.71-1, 163.71-2
Fish 163.72-1
Aquatic Invertebrates 163.72-2
Freshwater Fish
The minimum data required for establishing the acute toxicity
of manufacturing-use chloroneb for fish is a determination
of the 96-hour LCgQ for a coldwater species (preferably
rainbow trout) ana a warmwater species (preferably bluegill
sunfi sh).
Acceptable data are available on the acute toxicity of
technical chloroneb to rainbow trout (Salmo gairdneri).
Zihal (1979) determined the 96-hour LC5Q of 90% technical
chloroneb at 3.7 ppm. This study characterizes chloroneb
as moderately toxic to coldwater fish, and satisfies
the requirement for a coldwater fish study.
Trivits (1979) provides supplemental information for
warmwater fish (bluegill sunfish, Lepomis macrochirus).
This study does not fulfill the guideline requirements
for toxicity studies for warmwater fish. It does, however,
provide sufficient information to characterize chloroneb as
at least moderately toxic to warmwater fish. Because no
studies were available that satisfy the guideline requirements,
a data gap exists for warmwater fish.
Birds
Birds may be exposed to pesticides by feeding on contaminated
plants or insects, by dermal contact and/or inhalation
when close to outdoor sprays and dust. To assess the impact
of a pesticide on birds, the Agency requires certain avian
toxicity tests to support the registration of pesticides.
114
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A determination of the avian acute single-dose oral LD
is required to support the registration of every manufacturing
use product and formulated product for outdoor application.
Acute testing must be performed on one avian species, either
a wild waterfowl or an upland gamebird. (The species tested
shall be the same as one of the two species used for the
avian dietary tests.) Information regarding the acute
toxicity of chloroneb to birds is not available; as such a
data gap exists.
A determination of the subacute dietary LCcg (5-day
dietary exposure) is also required to support the registration
of all manufacturing-use products and all formulated products
intended for outdoor application. These studies should
be conducted using the technical material in the diet of
an upland gamebird and a wild waterfowl.
Acceptable data are available on the effects of chloroneb
in the diet of mallard ducks (Anas piatyrhynchps) and bobwhite
quail (Colinis virginianus). The information f? summarized
in the following table:
TABLE: DIETARY TOXICITY OF CHLORONEB TO BIRDS
8-DAY
SPECIES FORMULATION DIETARY REFERENCE
Mallard duck 90% Technical >5000 ppm Hinkle 1979 (GS00007-001)
Bobwhite quail 90% Technical >5000 ppm Hinkle 1979 (GS00007-002)
These studies characterize chloroneb's dietary toxicity
as practically non-toxic to upland game birds and wild
waterfowl. The dietary study requirements for birds have
been satisfied.
A decision to require chronic toxicity data (reproductive
or simulated and actual field tests), must await further
information.
Aquatic Invertebrates
A determination of the 48-hour EC50 or LC5Q for an
aquatic invertebrate species is required to support the
registration of all manufacturing-use products and for all
formulated products intended for outdoor application.
A 48-hour toxicity test (Goodman 1979) was performed using
90% technical chloroneb on the water flea, Daphnia magna.
The reported 48-hour LCcg was 6.19 ppm. This study
characterizes chloroneb as moderately toxic to freshwater
115
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aquatic invertebrates. The guidelines requirement for
the'acute toxicity to freshwater aquatic invertebrates has
been satisfied.
The decision to require life-cycle or other tests on aquatic
invertebrates will depend on, but not be limited to, a
consideration of chloroneb's use patterns, persistence,
bioaccumulation, mobility and degradation rates. Sufficient
information on the environmental fate of chloroneb is
not available at this time.
Wettable Powder - Ecological Effects Profile
The toxicity of wettable powder chloroneb to wildlife may be
estimated from tests on the manufacturing-use chemical.
Topical Discussions
See the Manufacturing-Use Chloroneb section of this chapter
for the ecological effects requirements to support the
registration of chloroneb formulated products.
The use patterns and formulations currently under consideration
do not indicate the need for acute fish and wildlife tests
using the formulated products. The toxicity of the various
formulations and the subsequent hazard to wildlife can be
estimated by using the toxicity data provided by tests of
the technical chemical.
Ecological Effects Profile - Granular Chloroneb
The toxicity of granular chloroneb to wildlife may be
estimated from tests on the technical chemical.
Topical Discussions
See the Manufacturing-Use Chloroneb section of this chapter
for the ecological effects requirements to support the
registration of chloroneb formulated products.
Fish and Wildlife
The use patterns and formulations currently under considera-
tion do not indicate the need for acute fish and wildlife
tests using the formulated products. The toxicity of the
various formulations and the subsequent hazard to wildlife
can be estimated by using the toxicity data provided by
tests of the technical chemical.
116
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Terrestrial PI ants
The only available study (Scott 1971; 00001496) indicates
that granular chloroneb has no phytotoxic effects on host
grasses at the highest level tested. The no effect level
for bentgrass (4.6, 9, or 12% granular formulation) was
58.5 pounds a.i. per acre. For Kentucky blue grass and
perrenial ryegrass, the no effect level was 9.8 pounds
a.i. per acre for 4.6, 9, or 12% granular formulations.
This type of data is not, at present, required for regis-
trati on.
Ecological Effects -.Dust Chloroneb
The toxicity of dust chl oroneb to wildlife may be
estimated from tests on the technical chemical.
Topical Discussions
See the Manufacturing-Use Chloroneb section of this chapter
for the ecological effects requirements to support the
registration of Chloroneb formulated products.
The use patterns and formulations currently under consideration
do not indicate the need for acute fish and wildlife tests
using the formulated products. The toxicity of the various
formulations and the subsequent hazard to wildlife can be
estimated by using the toxicity data provided by tests of
the technical chemical.
117
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Bibliography
-MRID CITATION
GS0007-005 Goodman, N.C. (1979) 48-Hour LC5Q to
Daphnia magna. (Unpublished study received
Dec. 13, 1979 under 352-386 submitted by
E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:241500)
GS0007-002 Hinkle, S. (1979a) Avian Dietary Toxicity
(LCcn) Study in Bobwhite Quail Project
No. T 201-528. (Unpublished study received
Dec. 13, 1979 'under 352-386; prepared by
Hazleton Laboratories, Inc., submitted by
E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:241500)
GS0007-001 Hinkle, S. (1979b) Avian Dietary Toxicity
(LCcQ) i" Mallard Ducks Project No.
2012527. (Unpublished study received Dec. 13,
1979 under 352-386; prepared by Hazleton
Laboratories, Inc., submitted by E.I. du
Pont de Nemours & Co., Inc., Wilmington,
Del.; CDL:241500)
00001496 O.M. Scott & Sons Company (1971) Summary of
Results for: Granular Vermiculite Chloroneb
Formulations for Turfgrass Disease Control:
Environmental Protection Agency Report.
(Unpublished study received Oct. 18, 1971
under 538-79; CDL:023122-A)
GS0007-004 Trivits, R.L. (1979) 96-Hour LC5Q to
Bluegill Sunfish. (Unpublished study
received Dec. 13, 1979 under 352-
386 submitted by E.I. du Pont de Nemours &
Co., Inc. Wilmington, Del.; CDL:241500)
GS0007-003 Zihal, A.J. (1979) 96-Hour LC5Q to Rainbow
Trout. (Unpublished study received Dec. 13,
1979 under 352-386; submitted by E.I. du
Pont de Nemours & Co., Inc., Wilmington,
Del.; CDL:241500)
118
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OFFICE OF PESTICIDE PROGRAMS
PESTICIDE DOCUMENT MANAGEMENT SYSTEM
CASE BIBLIOGRAPHY
-------
GUIDE TO USE OF THIS BIBLIOGRAPHY
Content of Bibliography. This bibliography contains
citations of all the studies reviewed by EPA in arriving
at the positions and conclusions stated e1se\*here in
this standard. The bibliography is divCi'ded wttp 3
sections: (1) citations that contributed information
useful to the review of the chemical and considered to
be part of the data base supporting registrations under
the standard, (2) citations examined and judged to be
inappropriate for use in developing the standard, and
(3) standard reference material. Primary sources for
studies in this bibliography have been the body of data
submitted to EPA and its predecessor agencies in support
of past regulatory decisions, and the published technical
1iterature.
Units of Entry. The 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 typically
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
bibliographic citation. The Agency has attempted also
to unite basic documents and commentaries upon them,
treating them as a single study.
Identification of Entries. The entries in this bibliography
are sorted by author, date of the document, and title.
Each entry bears, to the left of the citation proper, an
eight-digit numeric identifier. This number is unique
to the citations, and should be 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 be preceded by a nine-character temporary
identifier. This is also to be used whenever a specific
reference is needed.
119
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4. Form of the Entry. In addition to the Master Record
Identi fier (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 submissin. 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, we have 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 data 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. T-his is the third element in the citation.
In some cases it has been necessary for out
bibliographers to create or enhance a document
title. Any such editorial insertions are contained
between square brackets.
d. Trailing Parentheses. For studies submitted to
the Agency in the past, the trailing parentheses
include (in addition to any self-explanatory
text) the following elements describing the
earliest known submission:
(1) Submission Date. Immediately following
the word 'received* appears the date of
the earliest known submission.
(2) Administrative Number. The next element,
immediately following the word 'under1,
is the registration number, experimental
perimt number, petition number, or other
administrative number associated with
the earliest known submission.
120
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(3) Submitter. The third element is the
submitter, following the phrase 'submitted by1
When authorship is defaulted to the
submitter, this element is omitted.
(4) Volume Identification. The final
element in the trailing parentheseis
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
'CDL1, 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 acessin number 123456. the first
study would be 123456-A; the second,
123456-B; the 26, 123456-Z; and the
27th, 123456-AA.
121
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Section 1: Citations Considered to be Part of the Data Base
Supporting Registrations Under the Standard.
Product Chemistry Bibliography
-MRID CITATION
GS0007-015 Alvarez, J.R., inventor; E.I. du Pont de
Nemours and Co., assignee (1968) Process for
Preparing 1,4 dichloro-2,5-dimethosybenzene
US. patent 3,363,005, Jan. 9
00001428 E.I. duPont de Nemours & Company, Incorporated
(1967) Name, Chemical Identity, and Composition:
Chloroneb. (Unpublished study received
Oct. >16, 1967 under 8F0657; CDL:092951-F)
00001444 E.I. duPont de Nemours & Company, Incorporated
(1977) "Demosan" 65W Fungicide: Product
Chemistry. Includes method dated October
15, 1976 and undated method. (Unpublished
study received May 27, 1977 under 352-312;
CDL.-232274-A)
05013181 Haglid, F.R., inventor; E.I. duPont de Nemours
and Co., assignee (1979) Process for
preparing 1,4-dichloro-2,5-dimethoxybenzene,
U.S. patent 4,159,391. Jun 26. 3 p.
Int. CL 2 C 07C 41/001 U.S. C1. 568/649
GS007-009 Scribner, R.M.; Soboczenski, E.J.; inventor;
(1966) Methods for Protecting Plants and
Seeds from Fungi. United States plant
patent 3,265,564. Aug 9
Environmental Fate Bibliography
-MRID CITATION
05001292 Azevedo, J.L., E.P. Santana, and R. Bonatelli, Jr.
1977. Resistance and mitotic instability
to chloroneb and 1,4-oxathiin in Aspergillus
nidulans. Mutation Res. 48(2):163-172
05001308 Georgopoulos, S.G., A. Kappas, and A.C. Hastie.
1976. Induced sectoring in diploid Aspergillus
nidulans as a criterion of fungitoxicity by
interference with hereditary processes.
Phytopath. 66(2):217-220
122
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-MRID CITATION
GS0007-006 Harvey, J. 1979. Stability of [14C]chloroneb
in water at various pH values. (Unpublished
study received Dec. 13, 1979, under 352-GIA;
submitted by E.I. du Pont de Nemours 4 Co., Inc.,
Wilmington, Del. CDL:241500.)
GS0007-007 Harvey, J. 1979. ..Activated sewage sludge
metabolism of [ C]chloroneb. (Unpublished
study received Dec. 13, 1979, under 352-GIA;
submitted by E.I. du Pont de Nemours 4 Co., Inc.,
Wilmington, Del. CDL:241500.)
05001155 Hock, W.K., and H.D. Sisler. 1969. Metabolism
of chloroneb by Rhizoctonia solani and
other fungi. J. Agri. Food Chem. 17(1): 123-128
05001167 Kappas, A. 1978. On the mechanisms of
induced somatic recombination by certain
fungicides in Aspergillus hidulans.
Mutation Res. 51(Z):189-197
00001426 Rhodes, R.C. 1968. Disappearance of C-ring-
labeled chloroneb from soil. (Unpublished
study received July 8, 1968, under 8F0657;
submitted by E.I. du Pont de Nemours 4
Co.^, Inc., Wilmington, Del. CDL:091147-J.)
05001170 Wiese, M.V., and J.M. Vargas, Jr. 1973.
Interconversion of chloroneb and 2,5-dichloro-
4-methoxyphenol by soil microorganisms.
Pesticide Biochem. Physiol. 3(2):214-222.
Toxicology Bibliography
-MRID CITATION
00001422 Busey, W.M., Crews, L.M., and Kundzins, W.
1967. 24-Month Dietary Feeding—Rats:
Fungicide 1823: Final Report: Project No.
201-124. (Unpublished study received July 8,
1968, under 8F0657; prepared by Hazleton
Laboratories, Inc., submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:091147-B)
00001421 Busey, W.M., and Kundzins, W. 1967. Two-Year
Dietary Feeding—Dogs: Fungicide 1823:
Final Report: Project No. 201-125. (Unpublished
study received July 8, 1968, under 8F0657;
prepared by Hazleton Laboratories, Inc.,
submitted by E.I. du Pont de Nemours and
Co., Inc., Wilmington, Del.; CDL:091147-A)
123
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-MRID CITATION
00001424 E.I. du Pont de Nemours and Company, Inc.
1967. Chloroneb—Chronic Feeding Studies:
Tissue Analysis--Dogs, Rats. (Unpublished
study received July 8, 1968, under 8F0657;
CDL:091147-D)
GS0007-011 Ferenz, R.L. 1979a. Eye Irritation in
Rabbits. (Unpublished study received
December 13, 1979, under 352-385; prepared
by Haskell Laboratory, submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:241500)
GS0007-012 Ferenz, R.L. 1979b. Skin Irritation in
Rabbits. (Unpublished study received
December 13, 1979, under 352-386; prepared
by Haskell Laboratory, submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:241500)
05001156 Gutenmann, W.H., and Lisk, D.J. 1969.
Metabolic Studies with Chloroneb Fungicide
in a Lactating Cow. J. Agric. Food Chem.
17:1008-1010
GS0007-010 Hinckle, L. 1979. Oral LD50 Test. (Unpublished
study received December 13, 1979, under
352-G1A; prepared by Haskell Laboratory,
submitted by E.I. du Pont de Nemours and
Co., Inc., Wilmington, Del.; CDL:241500
00001445 Hood, D.B. 1965. Fifteen-Exposure Dermal
Study with 1,4-Dichloro-2,5-Dimethoxybenzene:
Report No. 106-65. (Unpublished study
received October 27, 1965, under 352-313;
submitted by E.I. du Pont de Nemours and
Co., Wilmington, Del.; CDL:050831-B)
00001423 Kundzin, T. (1967) Three-Generation Reproduction
Study of Fungicide 1823: Final Report:
Project No. 201-126. (Unpublished study
received jUl 8, 1968 under 8F0657; prepared
by Hazelton Laboratories, Inc., submitted
by E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:091H7C)
124
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-MR ID
00004982
CITATION
Kwon, B.K. 1965. Acute Inhalation Toxicity:
Haskell Laboratory Report No. 31-65.
(Unpublished study received October 27,
1965, under 352-313; submitted by E.I. du
Pont de Nemours and
Del.; CDL:050831-F)
Co., Inc., Wilmington,
05001159
00004980
Rhodes, R.C., and Pease,
Chloroneb in Animals.
19:750-753
H.L. 1971
J. Ag r i c.
Fate of
Food Chem.
Sherman, H. 1964a. Ninety-Day Feeding Study
with 1 ,4-Dichloro-2,5-Dimethoxybenzene
(INK-1823): Report No. 81-64. (Unpublished
study received Octover 27, 1965, under
352-313; submitted by E.I. du Pont de
Nemours and Co., Wilmington, Del.; CDL:050831-C)
00004980
00001495
Sherman, H. 1964b. Ten-dose subacute Oral
Test: Haskell Laboratory Report No. 23-64.
(Unpublished study received Octoer 27,
1965, under 352-313; submitted by E.I. du
Pont de Nemours and Co., Inc., Wilmington,
Del.; CDL:050831-D)
WARF Institute, Inc. 1971. Oral LD50 and
Skin Irritation of 1,4-Dichloro-2,5-Dimethoxy-
benzene: WARF No. 1080676. (Unpublished
study received October 18, 1971, under
538-79; submitted by O.M. Scott and Sons
Co., Marysville, Ohio; CDL:050143-A)
Residue Chemistry Bibliography
-MRID
00001434
00001431
CITATION
E.I. du Pont de Nemours & Company, Incorporated
(1965?) Method for Determining Residues of
1,4-Dichloro-2,5-Dimethoxybenzene. (Unpublished
study received Jul 7, 1965 under unknown
admin, no-; CDL:120886-A)
E.I. du Pont de Nemours & Company, Incorporated
(1967a) Chloroneb Livestock Feeding Studies:
Milk and Meat. (Unpublished study received
Jul 8, 1968 under 8F0657; CDL:091146-U)
125
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-MRID CITATION
00001412 E.I. du Pont de Nemours & Company, Incorported
(1967b) Results of Tests on the Amount of
Residue in Crops Grown in Chloroneb Treated
Soil. (Unpublished study received Jul 8,
1968 under 8F0657; CDL:091146-1)
00003269 E.I. du Pont de Nemours & Company, Incorporated
(1968) Chioroneb--Pesticide Petition No.
8F0657: Supplemental Information: Answer
to FDA Letter of June 4, 1968. (Unpublished
study received Jul 8, 1968 under 8F0657;
CDL.-091146-A)
05001156 Gutenmann, W.H., Lisk, D.J. (1969) Metabolic
studies with chloroneb fungicide in a
lactating cow. Journal of Agricultural
and Food Chemistry 17(5):1008-1010
05001181 Kirk, B.T., Sinclair, J.B., Lambremont, E.N.
(1969) Translocation of C14-labeled chloroneb
and DMOC in cotton seedlings. Phytopathology
59(10): 1473-1476
GS0007-013 Kharbanda, P.O. (1971) Systemicity of C14-labeled
chloroneb in soybean tissues. Unpublished
Ph.O Dissertation, University of Illinois,
46 pp.
00001429 Pease, H.L. (1967) Determination of residues
of Chloroneb and a metabolite by microcoulometric
gas chromatography. Journal of Agricultural and
Food Chemistry 15(5):917-919. Undated
method. (Also In unpublished submission
received Oct 16, 1967 under 8F0657; submitted
by E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:092951-G)
00002214 Rhodes, R.C. (19??a) Determination of
2,5-Dichloro-hydroquinone and 2,5-Dichloroquinone
in Milk. Undated method. (Unpublished
study received Jul 8, 1968 under 8F0657;
submitted by E.I. du Pont de Nemours & Co.,
Inc., Wilmington, Del.; CDL:091146-D)
*r
00002218 Rhodes, R.C. (19??b) Greenhouse Studies with
•C-14 Ring-Labeled Chloroneb in Cotton
Plants. (Unpublished study received Jul 8,
1968 under 8F0657; submitted by E.I.
du Pont de Nemours & Co., Inc., Wilmington,
Del.; CDL:091146-S)
126
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-MRID CITATION
00001430 Rhodes, R.C. (1968a) Studies with C-14
Ring-Labeled Chloroneb in Bean Plants.
(Unpublished study received Jul 8, 1968
under 8F0657; submitted by E.I. du Pont de
Nemours & Co., Inc., Wilmington Del.;
CDL:091146-T) (MRID 00001430)
00001407 Rhodes, R.C. (1968b) Chemical Identification
of Metabolites of Chloroneb in Bean Plants.
(Unpublished study received Jul 8, 1968
under 8F0657; submitted by E.I. du Pont
de Nemours & Co., Inc., Wilmington, Del.;
CDL:091146-B)
05001159 Rhodes, R.C., Pease, H.L. (1971) Fate of
chloroneb in animals. Journal of Agricultural
and Food 19(4): 750-753
00001158 Rhodes, R.C., Pease, H.L., Brantley, B.K.
(1971) Fate of C14-labeled chloroneb in
plants and soils. Journal of Agricultural
and Food Chemistry 19(4):745-749
05001302 Thapliyal, P.N., Sinclair, J.B. (1970)
Uptake of three systemic fungicides by
germinating soybean seed. Phytopathology
60(9):1373-1375
05001304 Thapliyal, P.N., Sinclair, J.B. (1971)
Translocation of benomyl , carboxin, and
chloroneb in soybean seedlings. Phytopathology
61(10:1301-1302
05001297 Thorn, G.D. (1973) Uptake and metabolism of
chloroneb by Phaseolus vulgaris. Pesticide
Biochemistry and Physiology 3(2):137-140
05001134 Vargas, J.M., Turgeon, A.J. (1975) Translocation
of C14 labeled chloroneb in three turfgrass
species. Canadian Journal of Plant Science
55(l):85-88
05001172 Verma, R.K., Vyas, S.C. (1976) Uptake,
translocation and persistence of five
systemic fungicides in gram seedlings.
Pesticides 10(12):21-24
127
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Ecological Effects Bibliography
-MRID CITATION
GS0007-005 Goodman, N.C. (1979) 48-Hour LC5Q to
Daphnia magna. (Unpublished study received
Dec. 13, 1979 under 352-386 submitted by
E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:241500)
GS0007-002 Hinkle, S. (1979a) Avian Dietary Toxicity
(LC,.Q) Study in Bobwhite Quail Project
No. T 201-528. (Unpublished study received
Dec. 13, 1979 under 352-386; prepared by
Hazleton Laboratories, Inc., submitted by
E.I. du Pont de Nemours & Co., Inc.,
Wilmington, Del.; CDL:241500)
GS0007-001 Hinkle, S. (1979b) Avian Dietary Toxicity
(LC5Q) in Mallard Ducks Project No.
201=527. (Unpublished study received Dec. 13,
1979 under 352-386; prepared by Hazleton
Laboratories, Inc., submitted by E.I. du
Pont de Nemours & Co., Inc., Wilmington,
Del.; CDL:241500)
00001496 O.M. Scott & Sons Company (1971) Summary of
Res'ults for: Granular Vermiculite Chloroneb
Formulations for Turfgrass Disease Control:
Environmental Protection Agency Report.
(Unpublished study received Oct. 18, 1971
under 538-79; CDL:023122-A)
GS0007-004 Trivits, R.L. (1979) 96-Hour LCc« to
Bluegill Sunfish. (Unpublishedustudy
received Dec. 13, 1979 under 352-
386 submitted by E.I. du Pont de Nemours &
Co., Inc. Wilmington, Del.; CDL:241500)
GS0007-003 Zihal, A.J. (1979) 96-Hour LC5Q to Rainbow
Trout. (Unpublished study received Dec. 13,
1979 under 352-386; submitted by E.I. du
Pont de Nemours & Co., Inc., Wilmington,
Del.; CDL:241500)
128
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Section 2:
OFFICE OF PESTICIDE PROGRAMS
PESTICIDE DOCUMENT MAN\GS*!ENT SYSTEM
C\SE BIBLIOGRAPHY
Citations Ekarained and judged to be Citations Inappropriate for Use
in Developing the Standard.
-MRID CITATION
335018584 Aaron, J.J.; Kaleel, E.M.; Winefordner, J.D. (1979) Comparative
study of low-temperature and room-temperature phosphorescence
characteristics of several pesticides. Journal of Agricultural
and Ebod Chemistry 27(6):1233-1237.
305331219 Aetna, H.E.; Waite, B.H. (1975) Control of root rot in bean
(??Phaseolus vulgaris??) with fungicides in El Salvador. Pages
73,?In?Proceedings—American Phy to pathological Society:
Caribbean Division; Dec 4-7, 1975. Val. 2. St. Paul, Minn.:
American Ehytopathologial Society.
335001441 Adaickalam, V.; Prasad, N.N. (1976) Efficacy of certain fungicides
on the control of sesame leaf spot of rice. Annaraalai
University Agricultural Research Annual 6:103-112.
005001445 Agarval, D.K.; Sarbhoy, A.K. (1976) Effect of different fungicides
on the pre-energence rot of soybean caused by?Macrophcmina?
??phaseolina??. Indian Phytopathology 29(1):100.
005001153 Agarwal, D.K.; Sarbhoy, A.K. (1976) Efficacy of different
fungicides (in vitro) to seedling rot of soybean. Indian
Phytopathology 29 (4):458.
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032949-A)
000001473 E.I. du Pont de Nemours & Company, Incorporated (1970?) Evaluation
of Two Rates of Demosan 65W on Arid Del in ted Cottonseed in
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000031476 E.I. du Pont de Nemours & Company, incorporated (1971?) Cottonseed
Treatenant Studies, Delta Pine and Land Co., Scott, Mississippi
1971. (Unpublished study received Apr 3, 1972 under 352-350;
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003001434 E.I. du Pont de Nemours & Company, incorporated (1971?) Evaluation
of Selected 1971 Regional Cottonseed Treatment Samples in Lab-
oratory: Pythium and Fhizoctonia Boosted Soil Plantings, Eecem-
ber, 1971. (Unpublished study received Apr 3, 1972 under
352-360; CEL:003095-Q)
000031474 E.I. du Pont de Nemours & Company, Incorporated (1971?) Evaluation
of Three Rates of " Demosan" Chloroneb on Acid and Regianed
Cottonseed in P/thium and Rhiaocbonia Boosted Soil in Greenhouse
Plantings in 1971. (Unpublished study received Apr 3, 1972
under 352-350; CEL:003395-F)
333001435 E. I. du Pont de Nemours & Company, Incorporated (1971?) Summary of
"Demosan" T Performance in the 1971 Regional Cottonseed Treat-
ment Trials. (Unpublished study received Apr 3, 1972 under
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138
-------
303001492 E.I. du Pont da Nemours & Company, Incorporated (1972?) Performance
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003301442 E.I. du Pont de Nemours & Company, Incorporated (1972) Eata
Supporting the Use of "Demosan" 65W Chloroneb Fungicide at the
Reduced Rata of 6 Ozs. per 100 Ibs. of Cottonseed. CUipub-
lished study received Nov 5, 1972 under 352-312; CEL:C02950-A)
000001451 E.I. du Pont de Nemours & Company, Incorporated (1972) EBta
Supporting Use of Tersan-.(R)? SP-G Turf Fungicide for the Con-
trol of Snow Mold (Typhula) . (Unpublished study received Jan
10, 1972 under 352-359; CEL.-003093-A)
300001452 E. I. du Pont de Nemours & Company, Incorporated (1972) EBta Sup-
porting the Use of Eemosan-i(R)? T Seed Fungicide as a Cottonseed
Treatment. (Unpublished study received Apr 3, 1972 under
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030001440 E.I. du Pont da Namours & Company, Incorporated (1974) Data Sup-
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Rate of 10 Oz. per 100 Ibs. of Cottonseed West of the Rocky
fountains. (Unpublished study received Sep 5, 1974 under 352-
312; CEL:002466-A)
333031453 E.I. du Pont de Namours & Company, Incorporated (1975) Data
Supporting the Use of "Cemosan" T Seed Fungicide on Beans.
(Unpublished study received Feb 10, 1975 under 352-360;
CDL: 221888-A)
GS0007-003 E.I. du Pont de Nemours & Company, Incorporated. (1979) Storage
Stability of Technical Chloroneb November, 1973 to October
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305307871 E.I. du Pont de Nemours and Co., assignee (1954) Werkwijze an
middel ter bescherming van pi anten tegen aantasting door
bodemfungi EMethod and product for the protection of plants
against iriFaction caused by soil fungi | Dutch octrooiaanvrage
5,402,669. Sept 15. 31 p. Int. CL. A~01n, C 07c.
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and greenhouse evaluations of various systemic fungicides for
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