United Slates
Environmental Protection
Agency
Office of
Pesticide* and Toxic Substances
Washington DC 20460
January 1981
&EPA
2, 3-dichloro
- 1, 4-naphthoquinone
(Dichlone)
Pesticide Registration
Standard
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DICHLONE
Pesticide Registration Standard
Bruce Kapner
Diane Beavers
William Boodee
Linda Garczynski
Robert Hoist
Dennis McLane
Jim Stone
Greg Wiedemann
Project Manager (SPRD)
Product Manager (RD)
Chemist (HED)
Writer/Editor (SPRD)
Plant Physiologist (HED)
Wildlife Biologist (HED)
Product Manager (RD)
Plant Pathologist (BFSD)
January 1981
Office of Pesticides and Toxic Substances
Environmental Protection Agency
401 M Street, S.W.
Washington, D.C. 20460
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TABLE OF CONTENTS
Page No.
Chapter I
HOW TO REGISTER UNDER A REGISTRATION STANDARD
Organization of the Standard 1
Purpose of the Standard 1
Requirement to Register Under the Standard 3
"Product Specific" Data and "Generic Data" 3
Data Compensation Requirement under FIFRA 3(c) (1) (D) 5
Obtaining Data to Fill "Data Gaps"; FIFRA 3(c)(2)(B) 6
Amendments to the Standard 7
Chapter II
AGENCY POSITION ON DICHLONE
Regulatory Position for Dichlone 8
Criteria for Registration Under the Standard 8
Product Composition Standards 9
Manufacturing-Use Dichlone . 9
Formulated Dichlone Products 9
Acute Toxicity Standards 9
Manufacturing-Use Dichlone 9
Formulated Dichlone Products 10
Labeling Standards 10
Use Patterns: Manufacturing-Use Dichlone 10
Use Patterns: Formulated Dichlone Products 10
Product Chemistry 10
Physical Hazard - Precautionary Labeling 10
Human Hazard - Precautionary Labeling 11
Ecological Effects 11
Environmental Fate 11
Storage and Disposal. 11
Data Requirements and Data Gaps 11
Tolerance Reassessment 12
Regulatory Rationale 12
Product Composition Standards 12
Acute Toxicity Limits 12
Use Patterns 12
Data Gaps 13
Tables 14
Chapter III
PRODUCT CHEMISTRY
Introduction 26
DISCIPLINARY REVIEW
Chemistry Profile 26
Data Requirements and Data Gaps 27
Required Labeling 27
TOPICAL DISCUSSION
Chemical Identity 28
Manufacturing Process 30
Discussion on Formation of Unintentional Ingredients 31
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TABLE OF CONTENTS (Continued)
Declaration and Certification of Ingredients 31
Product Analytical Methods and Data 31
Physical/Chemical Properties 33
Chapter Bibliography 37
Chapter IV
ENVIRONMENTAL FATE
DISCIPLINARY REVIEW
Environmental Fate Profile 39
Use Profile 40
Data Gaps 40
TOPICAL DISCUSSIONS
Physico-Chemical Transformation 43
Hydrolysis .' 43
Photolysis 43
Metabolism 43
Soil 44
Aquatic 44
Microbiological ,«. 44
Activated Sludge . 47
Mobility 47
Leaching 47
Volatility 47
Absorption/Desorption 47
Water Dispersal. 48
Field Dissipation 48
Terrestrial 48
Aquatic 48
Terrestrial/Aquatic (Forest) 48
Aquatic Impact Uses 49
Accumulation....... 49
Rotational Crops 49
Irrigated Crops 49
Fish 49
Chapter Bibliography. 50
Chapter V
TOXICOLOGY
DISCIPLINARY REVIEW
Toxicology Profile 51
Data Requirements and Data Gaps 51
Required Labeling. 51
TOPICAL DISCUSSION
Acute Testing
Acute Oral Toxicity 53
Acute Dermal Toxicity. 54
Acute Inhalation Toxicity 54
Primary Eye Irritation 55
Primary Dermal Irritation. 55
Dermal Sensitization 55
Acute Delayed Neurotoxiicity 56
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TABLE OF CONTENTS (Continued)
Subchronic Testing
Subchronic Oral Toxicity 56
Subchronic 21-day Dermal Toxicity 56
Subchronic 90-day Dermal Toxicity 57
Subchronic Inhalation Toxicity 57
Subchronic Neurotoxicity 57
Chronic Testing
Chronic Feeding Studies 57
Oncogenicity 58
Teratogenicity 58
Reproduction 58
Mutagenicity 59
Metabolism 59
Clinical Trials 60
Emergency Treatment 60
Chapter Bibliography 61
Chapter VI
RESIDUE CHEMISTRY
DISCIPLINARY REVIEW
Residue Chemistry Profile 62
Data Gaps 63
Required Labeling 63
TOPICAL DISCUSSIONS
Use Patterns 65
Aquatic Uses 65
Agriculture and Ornamental Uses 65
Metabolism 66
Analytical Methodology 66
Residue Data 68
Residue in or on Apples 69
Residue on Peaches 70
Residue in or on Tomatoes 70
Residue on Celery 71
Residue on Beans 71
Residue in or on Cherries 72
Residue in or on Plums and Fresh Prunes 72
Residue in or on Strawberries 73
Residue in Meat and Milk 73
Regulatory Incidents 74
Chapter Bibliobraphy 75
Chapter VII
ECOLOGICAL EFFECTS
DISCIPLINARY REVIEW
Ecological Effects Profile 77
Ecological Effects Hazard Assessment 78
Data Gaps 78
Required Labeling 78
TOPICAL DISCUSSION
Avian Single Dose Oval LD™ 82
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TABLE OF CONTENTS (Continued)
Avian Dietary LC™ 82
Avian Reproduction .... 82
Mammalian Acute Tbxicity. 82
Fish Acute Toxicity 83
Acute Toxicity to Aquatic Invertebrates 83
Effects on Terrestrial Macrophytes ». 85
Effects of Dichlone on Algae 86
Effects of Dichlone on Aquatic Macrophytes 87
Nitrogen Fixation Potential 87
Effects of Dichlone on Amphibians 87
Effects of Dichlone on Beneficial Invertebrates 88
Chapter Bibliography 89
Chapter VIII
BIBLIOGRAPHY
Guide to Use of the Bibliography. 93
Section I (. 95
Section II 102
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LIST OF TABLES
Table Title Page
1-1 Product Chemistry Data Requirements for Manufacturing- 14
Grade Dichlone by Composition Characteristics
1-2 Product Chemistry Data Requirements for End-Use 15
Products by Composition Characteristics
II Environmental Fate Dichlone Generic Data Require- 18
ments by Use Patterns
III-l Ecological Effects Data Requirements for End-Use 20
Dichlone Products by Composition Characteristics
III-2 Ecological Effects Generic Data Requirements for 21
Dichlone by Use Patterns
IV-1 Toxicology Data Requirements for Dichlone Products 23
by Composition Characteristics
IV-2 Toxicology Generic Data Requirements for Dichlone 24
by Use Patterns
1 Dichlone Technical Chemical Characteristics 29
2 Manufacturers and Formulators of Dichlone Products 32
3 Use Patterns 41
4 Registered Application Rates 42
5 Effects of Dichlone on Microbes 46
6 Effects of Dichlone on Aquatic Invertebrates 84
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CHAPTER I
HOW TO REGISTER
UNDER A REGISTRATION STANDARD
Organization of the Standard
Purpose of the Standard
Requirement to Re-register Under the Standard
"Product Specific" Data and "Generic" Data
Data Compensation Requirements under FIFRA 3(c)(l)(D)
Obtaining Data to Fill " Data Gaps"; FIFRA 3(c)(2)(B)
Amendments to the Standard
Organization of the Standard
This first chapter explains the purpose of a Registration Standard and
summarizes the legal principles involved in registering or re-registering
under a Standard. The second chapter sets forth the requirements that must
be met to obtain or retain registration for products covered by this
particular Registration Standard. In the remaining chapters, the Agency
reviews the available data by scientific discipline, discusses the Agency's
concerns with the identified potential hazards, and logically develops the
conditions and requirements that would reduce those hazards to acceptable
levels.
Purpose of the Standard
Section 3 of the Federal Insecticide, Fungicide, and Rodenticide Act
(FIFRA) provides that "no person in any State may distribute, sell, offer
for sale, hold for sale, ship, deliver for shipment, or receive (and having
so received) deliver or offer to* deliver, to any person any pesticide which
is not registered with the Administrator [of EPA]." To approve the
registration of a pesticide, the Administrator must find, pursuant to
Section 3(c)(5) that:
"(A) its composition is such as to warrant the proposed claims for it;
(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 product" basis, evaluating each product-specific application
somewhat independently. In the review of products containing similar
components, there was little opportunity for a retrospective review of the
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full range of pertinent data available in Agency files and in the public
literature. Thus the "product by product" approach was often inefficient
and sometimes resulted in inconsistent or incomplete regulatory judgments.
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. When EPA issued new requirements for registration in
1975 (40 CFR 162) and proposed new guidelines for hazard testing in 1978
(43 FR 29686, July 10, 1978 and 43 FR 37336, August 2, 1978), many products
that had already been registered for years were being sold and used without
the same assurances of hunan and environmental safety as was being required
for new products. Because of this inconsistency, Congress directed EPA to
re-register all previously registered products, so as to bring their
registrations and their data bases into compliance with current
requirements, [See FIFRA Section 3(g)].
Facing the enormous job of re-reviewing and calling-in new data for the
approximately 35,000 current registrations, and realizing the
inefficiencies of the "product by product" approach, the Agency decided
that a new, more effective method of review was needed.
A new review procedure has been developed. Under it, EPA publishes
documents called Registration Standards, each of which discusses a
particular pesticide active ingredient. Each Registration Standard
sutimarizes all the data available to the Agency on a particular active
ingredient and its current uses, and sets forth the Agency's comprehensive
position on the conditions and requirements for registration of all
existing and future products which contain that active ingredient. These
conditions and requirements, all of which must be met to obtain or retain
full registration or reregistration under Section 3(c)(5) of FIFRA, include
the submission of needed scientific data which the Agency does not now
have, compliance with standards of toxicity, composition, labeling, and
packaging, and satisfaction of the data compensation provisions of FIFRA
Section 3(c)(l)(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 sane special regulatory
restriction is needed to ensure against unreasonable adverse effects to man
or the environment. Many such risks of unreasonable adverse effects can be
lessened if expressly-designed label precautions are strictly followed.
Thus the special regulatory restriction for a "restricted use" pesticide is
usually a requirement that it be applied only by, or under the supervision
of, an applicator who has been certified by the State or Federal government
as being competent to use pesticide safely, responsibly, and in accordance
with label directions. A restricted-use pesticide can have other
regulatory restrictions [40 CFR 162.11(c)(5)] instead of, or in addition
to, the certified applicator requirement. These other regulatory
restrictions may include such actions as seasonal or regional -limitations
on use, or a requirement for the monitoring of residue levels after use.
A pesticide classified for "general use," or not classified at all, is
available for use by any individual who is in compliance with State or
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local regulations. The Registration Standard review compares information
about potential adverse effects of specific uses of the pesticide with risk
criteria listed in 40 CFR 162.11(c), and thereby determines whether a
product needs to be classified for "restricted use." If the Standard does
classify a pesticide for "restricted use," this determination is stated in
the second chapter.
Requirement to Reregister Under the Standard
FIFRA Section 3(g), as amended in 1978, directs EPA to reregister all
currently registered products as expeditiously as possible. Congress also
agreed that reregistration 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 reregistration. 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 reregistration 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, lexicology, Residue Chemistry, and Ecological Effects.
These determinations are based primarily on the data Guidelines proposed in
43 FR 29696, July 10, 1978; 43 FR 37336, August 22, 1978; and 45 FR 72948,
Mbvember 3, 1980, 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 sane 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. Ihe
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 are 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
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(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 reregistration of any product, whether it is a manufactur-
ing-use or end-use product, and without regard to its intended use pattern,
must submit or cite enough of this kind of data to allow EPA to evaluate
the product. For such purposes, "product specific" data on any product
other than the applicant's is irrelevant, unless the other product is
closely similar in composition to the applicant's. (Where it has been
found practicable to group similar products for purposes of evaluating,
with a single set of tests, all products in the group, the Standard so
indicates.) "Product specific" data on the efficacy of particular end-use
products is also required where the exact formulation may affect efficacy
and where failure of efficacy could cause public health problems.
All other data needed to evaluate pesticide products concerns the
properties or effects of a particular ingredient of products (normally a
pesticidally active ingredient, but in seme 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 ID-50 of the active ingredient in its technical
or purer grade; see proposed 40 CFR 163.81-1(a), 43 FR 37355].
Other "generic" data are required to evaluate all products which both
contain a particular ingredient and are intended for certain uses (see,
e.g., proposed 40 CFR 163.82-1, 43 FR 37363, which requires subchronic oral
testing of the active ingredient with respect to certain use patterns
only). Where a particular data requirement is use-pattern dependent, it
will apply to each end-use product which is to be labeled for that use
pattern (except where such end-use product is formulated from a registered
manufacturing-use product permitting such formulations) and to each
manufacturing-use product with labeling that allows it to be used to make
end-use products with that use pattern. Thus, for example, a subchronic
oral dosing study is needed to evaluate the safety of any manufacturing-use
product that legally could be used to make an end-use, food-crop
pesticide. But if an end-use product's label specified it was for use only
in ways that involved no food/feed exposure and no repeated human exposure,
the subchronic oral dosing study would not be required to evaluate the
product's safety; and if a manufacturing-use product's label states that
the product is for use only in making end-use products not involving
food/feed use or repeated human exposure, that subchronic oral study would
not be relevant to the evaluation of the manufacturing-use product either.
If a registrant of a currently registered manufacturing-use or end-use
product wishes to avoid the costs of data compensation [under FIFRA Section
3(c)(l)(D)] or data generation [under Section 3(c)(2)(B)] for "generic"
data that is required only with respect to some use patterns, he may elect
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to delete those use patterns from his labeling at the time he reregisters
his product. An applicant for registration of a new product under this
Standard may similarly by request approval for only certain use patterns.
Data Compensation Requirements under FIFRA 3(c)(l)(D)
Under FIFRA Section 3(c)(l)(D), an applicant for registration, reregistra-
tion, or amended registration must offer to pay compensation for certain
existing data the Agency has used in developing the Registration Standard.
Ihe data for which compensation must be offered is all data which
aredescribed 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 registant in support of an application for an
experimental use permit, an amendment adding a new use to a
registration, or for registration, or to support or maintain in
effect an existing registration;
(3) they are the kind of data which are relevant to the Agency's
decision to register or reregister the applicant's product
under the Registration Standard, taking into account the
applicant's product's composition and intended use pattern(s);
(4) the Agency has found the data to be valid and usable in reaching
regulatory conclusions; and
(5) they are not data for which the applicant has been exempted by
FIFRA Section 3(c)(2)(D) from the duty to offer to pay
compensation. (This exemption applies to the "generic" data con-
cerning the safety of an active ingredient of the applicant's
product, not to "product specific" data. The exemption is
available only to applicants whose product is labeled for end-
uses for which the active ingredient in question is present in
the applicant's product because of his use of another
registered product containing that active ingredient which he
purchases frcm another producer.)
An applicant for reregistration 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)(l)(D).
An applicant would never be required to offer to pay for "product
specific" data submitted by another firm. In many, if not in most cases,
data which is specific to another firm's product will not suffice to allow
EPA to evaluate the applicant's product, that is, will not be useful to the
Agency in determining whether the applicant's product is registrable.
There may be cases, however, where because of close similarities between
the composition of two or more products, another firm's data may suffice to
allow EPA to evaluate sane 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.
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Each applicant for registration or reregistration of a manufacturing-
use product, and each applicant for registration or reregistration of an
end-use product, who is not exempted by FIFRA Section 3(c)(2)(D), must
comply with the Section 3(c)(l)(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 reregistration (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 have not been located in the published literature search
that EPA conducted as part of preparing this Standard. Such instances of
missing but required data are referred to in the Standard as "data gaps".
FIFRA Section 3(c)(2)(B), added to FIFRA by the Congress in 1978,
authorizes EPA to require registrants to whom a data requirement applies to
generate (or otherwise produce) data to fill such "gaps" and submit those
data to EPA. EPA must allow a reasonably sufficient period for this to be
accomplished. If a registrant fails to take appropriate and timely steps
to fill the data gaps identified by a section 3(c)(2)(B) order, his
product's registration may be suspended until the data is submitted. A
mechanism is provided whereby two or more registrants may agree to share in
the costs of producing data for which they are both responsible.
The Standard lists, in its summary second chapter, the "generic" data
gaps and notes the classes of products to which these data gaps pertain.
The Standard also points out that to be registrable under the Standard, a
product must be supported by certain required "product specific" -data. In
sane 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 reregistering currently registered products, EPA
will issue Section 3(c)(2)(B) directives requiring the registrants to take
appropriate steps to fill all identified data gaps — whether the data in
question are "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
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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, B.C., or
copies of which may be requested from the Agency. When all the present
"data gaps" have been filled and the submitted data have been reviewed, the
Agency will revise the Registration Standard. '.Thereafter, when the Agency
determines that the internally maintained addenda have significantly
altered the conditions for registration under the Standard, the document
will be updated and re-issued for publication.
While the Registration Standard discusses only the uses and hazards of
products containing the designated active ingredient(s), the Agency is also
concerned with the potential hazards of some inert ingredients and
impurities. Independent of the development of any one Standard, the Agency
has initiated the evaluation of some inert pesticide ingredients. Where
the Agency has 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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Chapter II
Agency Position on Dichlone
Regulatory Position for Dichlone
Dichlone as described in this Standard may be registered for sale,
distribution, reformulation, and use in the United States. The Agency has
considered the limited anount of scientific data obtained from the open
literature as of January 15, 1980, and the data submitted by the
registrants up through the time of publication of this Standard. In view
of this information, 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
have been met or exceeded for dichlone. Products currently registered may
be reregistered subject to the requirements for data submission. New
dichlone 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, dichlone products must meet the following
conditions:
1. The product must meet the composition standards specified below.
2. The product must meet the acute toxicity standards specified below.
3. The product must meet the labeling standards specified below.
4. The applicant must submit all data specified in the section Data
Requirements and Data Gaps.
5. The applicant must offer, when applicable, to pay compensation to the
extent required by 3(c)(l)(D) and 3(c)(2)(D) of the Federal Insecticide,
Fungicide and Kodenticide Act [FIFRA], as amended, 7 U.S.C. 136(c)(l)(D)
and 136(c)(2)(D).
6. The applicant must request that the Agency use all applicable data
cited in the Standard in making the registration decision.
7. The applicant must submit the application package in the required
form as specified in this Standard and the accompanying guidance package.
The following two companies have submitted data in support of dichlone
registration, and have not waived their rights to compensation for these
data: FMC Corporation and Uniroyal.
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Product Composition Standards
Manufacturing- Use Dichlone*
To be covered under this Standard, manufacturing-use dichlone products with
any percentage of active ingredient (a.i.) are acceptable with appropriate
certification of limits. Nevertheless, given current manufacturing-use
product grades and methods of synthesis, the Agency expects that most
technical material will range above 90% a.i.
The Agency identified the possibility of lead contamination during
manufacture of dichlone. Therefore, for dichlone products to be
registered under this Standard, identification and certification of
all impurities in the technical product must be made.
Formulated Dichlone Products**
Ib be covered under this Standard, formulated dichlone 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.
Acute Toxicity Standards
Manufacturing- Use Dichlone
The Agency will consider registration of manufacturing-use dichlone
products which have established Ibxicity Categories I through IV
ratings for each of the following acute effects:
Acute Oral Ibxicity
Acute Dermal Ibxicity
Acute Inhalation Ibxicity
Primary Eye Irritation
Primary Dermal Irritation
*As used in this Standard, "manufacturing-use" means any pesticide product
that is used solely for the manufacturing of end-use pesticide products.
This term includes both technical and formulation intermediate products.
**Formulated dichlone products include: Vfettable Powder, Dust, Flowable
Concentrate, and Solution-Ready-To-Use.
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Formulated Dichlone Products
To be registered for domestic use under this Standard, formulated
dichlone products must have Toxicity Category III or IV ratings for
each of the following acute effects:
Acute Oral Toxicity
Acute Dermal Toxicity
Acute Inhalation Toxicity
Primary Eye Irritation
Primary Dermal Irritation
To be registered for nondomestic use, formulated dichlone products must
have Tbxicity Categories II, III, or IV for acute oral, acute dermal, and
acute inhalation toxicity. For primary eye and skin irritation the product
may have a Toxicity Category I through IV.
Labeling Standards
The formatting requirements are contained in 40 CFR 162.10. The
subsections below explain how each heading will be incorporated.
Use Patterns: Manufacturing-Use Dichlone
To be registered under this Standard, manufacturing-use dichlone must be
formulated into end-use fungicides and herbicides. Manufacturing-use
pesticides may not include end-use directions.
Use Patterns: Formulated Dichlone Products
To be registered under this Standard, formulated dichlone products may be
used only as a fungicide on apples, cherries, peaches, plums and prunes,
strawberries, beans, celery, tomatoes, potatoes, roses and azaleas; and as
a herbicide in aquatic areas. The Agency finds that current dosage rates
and application methods are acceptable under this Standard.
Product Chemistry
All dichlone products must list the active ingredient as 2,3-dichloro-l,4-
naphthoquinone.
Active ingredient:
Dichlone (2,3-dichloro-l,4-naphthoquinone)........ 0-100%
Inert Ingredients................................. 0-100%
Total TOOT
Physical Hazard: Precautionary Labeling
The labeling of manufacturing-use and formulated dichlone products must
bear appropriate warnings in accordance with the nature of the
physical/chemical properties of the product. At the present, there have
been no data submitted to the Agency detailing any physical hazards of
manufacturing-use or formulated dichlone products.
10
-------
Human Hazard: Precautionary Labeling
The required hazard warnings and first aid statements on all manufacturing-
use and formulated dichlone product labels must correspond to the Tbxicity
Category for each acute effect. Refer to 40 CFR 162.10(h)(2)(B) for the
required labeling for each Toxicology Category.
Ecological Effects
All labels for formulated dichlone products intended for use as fungicides
and as algaecides in swimming pools must include the following warning:
"This pesticide is toxic to fish and other aquatic organisms. Do not
contaminate water by cleaning of equipment or disposal of wastes".
For technical and manufacturing-use products, the following must be added:
"This pesticide is toxic to fish and other aquatic organisms. Do not
discharge into lakes, ponds or public water unless in accordance with NPDES
permit. For guidance, contact your Regional Office of the EPA".
All labels for formulated dichlone products intended for use as algaecides
in lakes and ponds must include the following warning: "This pesticide is
toxic to fish and other aquatic organisms. Fish may be killed at the label
application rates. Do not apply to fish bearing waters."
All labels for food crop and ornamental uses must bear a statement similar
to: "This pesticide is toxic to fish."
Environmental Fate
The Agency does not have adequate data on which to base changes to
current environmental fate labeling requirements, and as such,
registrants should retain their current labels.
Storage and Disposal
Appropriate storage and disposal information is required of all
manufacturing-use and formulated dichlone products. For specific
requirements, see 40 CFR 165.
Data Requirements and Data Gaps
All registrants of dichlone products must fulfill the data requirements as
summarized on pages 14 through 25. A full description of the data
requirements can be found in the Proposed Guidelines for the Registration
of pesticides in the United States, 43 FR 29696, July 10, 1978; 43 FR
37336, August 22, 1978; and 45 FR 72948, November 3f 1980.
The Agency has not received acceptable acute toxicity data for any of the
formulated dichlone products. Therefore,.all required acute toxicity tests
are needed for each of the following formulation types: 50% wettable
powder; 2,3,6,and 9% dust; 50% flowable concentrate; 1.5, 4.9, and 5%
flowable concentrate; and 1.5% solution ready to use.
11
-------
Applicants are hereby advised that if the Agency does not receive commit-
ments within the specified time frame from manufacturing-use dichlone
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 they want the
manufacturing-use product to be available.
Tolerance Reassessment
For dichlone, the following tolerances have been established: 3 ppm in or
on apples, beans, celery, cherries, peaches, plums (fresh prunes) and
tomatoes and 15 ppm in or on strawberries. Based on these established
tolerances, the theoretical maximum residue contribution (TMPC) of dichlone
to the human diet is calculated to be 0.4403 mg/day/1.5 kg diet. However,
this TMRC is based on the above crop tolerances and these tolerances can no
longer be supported with the available residue data. A tolerance
reassessment is not possible at this time and will be performed when the
required residue data are supplied and reviewed.
REGULATORY RATIONALE
Product Composition Standards
Ihe Agency will consider for registration the formulated dichlone
products which contain dichlone as the sole active ingredient
if the products meet the acute toxicity standards for domes-
tic use and nondcmestic use if the inert ingredients have been
cleared for food use under 40 CFR 180.1001.
Acute Toxicity Limits
Manufacturing-Use Dichlone
Ihe Agency will consider for registration all manufacturing-use dichlone
products.
Formulated Dichlone Products
Ihe Agency will consider for registration all formulated dichlone products.
Use classification will be determined upon receipt of acute toxicity data.
All formulated products for use on raw agricultural commodities must
contain only those inert ingredients which are cleared under 40 CFR
180.1001.
Use Patterns
To be registered under this Standard, formulated dichlone products may be
used only as a fungicide on apples, cherries, peaches, plums and prunes,
strawberries, beans, celery, tomatoes, potatoes, roses and azaleas; and as
a herbicide in aquatic areas. The Agency finds that current dosage rates
and application methods are acceptable under this Standard.
Manufacturing-use dichlone products may be registered for use only in the
formulation of specific end-use products.
12
-------
Data Gaps
Data on acute toxicity are required for all formulated dichlone products.
Dichlone's food use and the need for tolerance reassessment for those uses
is the basis for dichlone"s chronic toxicology data requirements. Ihe
aquatic use pattern of dichlone requires subchronic testing,
teratogenicity, and mutagenicity data. Ihe aquatic use also necessitates
testing on the environmental fate of dichlone in water, as well as its
chronic effects on wildlife. Product chemistry data pertaining to
manufacturing-use as well as end-use products are needed. Ib support the
establised tolerances, data will have to be submitted on the following:
fate of dichlone residues in plants and animals, residue studies for the
raw agricultural commodities and their by-products reflecting the latest
registered uses and dosage rates, residue processing studies in apple
pomace and tomato pulp, and studies reflecting the persistence of dichlone
residues in water. The Office of Pesticide Programs (OPP) will transfer
scientific information about dichlone to EPA's Office of Drinking Water
(ODW) so that ODW may consider monitoring for dichlone residues in water,
and if necessary, may initiate procedures for regulating those residues
under the Safe Drinking Water Act. Additional hazard data received by OPP
will be conveyed to ODW as required.
13
-------
Table 1-1 Product Chemistry Data Requirements for Manufacturing Grade Dich-lone by Composition Character!sties
Guidelines Section
163.61-3
163.61-4
163.61-5
163.61-6
163.61-7
163.61-8(15
163.61-8(2)
163.61-6(3)
163.61-6(4}
163.61-5(5)
163. 61-8(6)
163.61-?j(7)
163.6i-&(£)
163.G1-F,(9)
163.61-CUQ)
163.6l-8( 11)
16.:. 61 -HI 2)
163.C'-8( 13)
163.61-fc( 14)
163.61-b( 15)
163. 6 l-o ( 16)
165.61-6(17)
163.61-8(18)
Data Requirement
for Manufacturing Products
Product identity and
disclosure of inqredients
Description of
manufacturing process
Discussion on formation of
unintentional inqredients
Declaration and certifica-
tion of ingredient limits
Product analytical methods
and data
Color
Odor
Molting point
Solubil ity
Stability _]
Octana 1 /Water partition
cocf f icient
Physical state
Density or specific gravity
Boi i inq point
Vfipor pressure
PH
Slorago s+abi 1 ity
F lommabi 1 ity
Oxidizing or reducing action
Explos i vonoss
Miscibi 1 ity
Viscosity
Corrosion characteristics
Composition Characteristics
Manufacturing- use
Manufacturing- use
Manufacturing-use
Manufacturing-use
Monuf actur ing-use
Technical
Techn icat
Technical
Techn ical
Tcchn ical
Techn ica 1
Technical & manufacturing use
Technical L monuf ar+ur ing use
Technical & manufacturing- use
Technical & manufacturing use
Technical A manufacturing use
Manuf actur i ng-usf;
Manuf actur i ng-use
Manufacturing use
Manuf actur i ng-use
Manuf actur inq- use
Manufacturing uso
Manu f actur inq-use
Do we
need it?
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
Yes
Yes
Yos
Yes
Yes
Yes
No
No
Yes
Do we
have it?
Yes
No
No
No
No
Yes
No
Yes
Yes
Yes
No
Yes
Yes
No
No
Yes
Yes
No
No
No •
-------
Table 1-2 Product Chemistry-- Data Requirements for End-Use Dichlone Products by Composition Characteristics
Gu idel ines Section
163.61-3
163.61-4
163i61-5
163.61-6
163.61-7
163.61-6(1)
163.61-8(2)
Data Requirement
for End-Use Products
Product identity and
disclosure of ingredients
Description of ]
manufacturing process
Discussion on formation of
unintentional ingredients
Declaration and
cert i f ication of
ingred ient 1 imi ts
Product analytical methods '
and data
Color n
Odor
Composition Characteristics
50£WP
2,3,6,9^0
50? FC
].5%, 4.9$, % FC; \ .5% RTU
50£WP
2,3,6,920
5c;; FC
'\.5%, 4.9%, 5% FCj 1.5£ RTU
5C£WP
2,3,6,9^0
50£FC
].5%j 4.9%, 5% FC; \ .% RTU
50£WP
2,3,6,920
50%- FC
].5%, 4.9%, 5£ FC; 1.5£ RTU
50?;VF
2,3,6,9^0
50^ FC
1.5;;, 4.9^, 5£ FC- \.5'f: RTU
5c;;wp
2,3,6,9^0
50^ FC
1.5.^ 4.9?,, 5% FC; 1.5£ RTU
50^WP
2,3,6,9^0
50? FC
1.5?, 4.9?j 52 FC; 1.5J RTU
Do we
need it?
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Do we
have it?
Yes
Yes
Yes
Yes
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
-------
Table 1-2 Product Chemistry-- Data Requirements for End-Use Dichlone Products by Composition Characteristics (cent.)
O\
Guide! ines Section
163.61-8(7)
161.51-8(6)
163.61-8(9)
163.61-SHO)
163.61-8(11)
163.61-8(12)
163.61-8(13)
Data Requirement
for End-Use Products
Physical state
Density or specific
o,rav i ty
Boi II nq point
Vapor pressure
PH
Storage stability
F 1 ammab i 1 i ty
Composition Characteristics
502WP
2,3,6,9ft)
5Q% FC
1.52, 4.9?;, 5% FC; 1.52 RTU
502wp
2,3,6,920
502 FC
1.52, 4.9?, 52 FC; 1.52 RTU
502WP
2,3,6,920
5G2 FC
1.5?; 4.92, 52 FC; 1.52 RTU
502WP
2,3,6,9^0
502 FC
\,5%, 4.9%j_5% FC; 1.5^ RTU
50^WP
2,3,6,920
502 -FC
1.5$, 4.9?, 52 FC; 1.52 RTU
502WP
2,3,6,9f,D
502 FC
1.52., 4-92, 52 FC; 1.52 RTU
502WP
2,3,6,920
502 FC
1.52, 4.92, 52 FC; 1.52 RTU
Do we
need it?
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
No
YfiS
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Do we
have it?
Yes
Yes
Yes
Yes
No
No •
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
Mo
No
No
No
No
-------
Table 1-2 Product Chemistry-- Data Requirements for End-Use Dichlone Products by Composition Characteristics (cont.)
Guidelines Section
163.61-8(14)
163.61-8(15)
163.61-8(16).
163.61-8(17)
163.61-8(18)
163.61-8(19)
Data Requirement
for End-Use Products
Oxidizing or reducing action
Explosiveness
Miscibi 1 ity
Viscosity
Corrosion characteristics
Dielectric breakdown j
voltage
Composition Character i sties
505SWP
2,3,6,9£D
50£ FC
1.5J, 4.9Jb, 5% FC; 1.5$ RTU
50^WP
2,3,6,9>>D
50$ FC
1.5S, • .9?, 5£ FC; 1.5$ RTU
5C£WP
2,3,6,9£D
50£ FC
1.5$, 4 .92, 5^ FC^ 1.5£ RTU
50 ^WP
2,3,6.95:0
50^ FC
1.52, 4.9£, 5^ FC_i \.5% RTU
50 ^WP
2,3,6,9^0
so ;: FC
1.5?, 4.9£, 5^ FC; 1.5£ RTU
502WP
2,3,6,9^0
50'J FC
1.5J, 4.9$, 5^ FC; 1.52 RTU
Do we
need it?
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
No
Yes
Yes
No
No
Yes
Yes
Yes
Yes
Yes
Yes
No
No
No
No
Do we
have it?
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
No
-------
Table II Environmental Fate— Dlchlone Generic Data Requirements by Use Patterns
Guidel inos Section
1C3.62-7(b)
163.62-7(c)
163.62-8(b)
163.62-8(c)
163.62-8(d)
163.62-8(e)
163.62-8(f)<2)
163.62-8(f)(3)
163.62-8(q)
1 63. 62-9 (b)
163.62-9(c)
Generic Data Requirement
Hydrolysis
Photodegradat ion
Aerobic soi 1 metabol ism
Anaerobic soil metabolism
Anaerobic aquatic metabol ism
Aerobic aquatic metabolism'
Effects of 1
microbes on pesticide
Effects of
pesticide on microbes
Activated sludqe metabolism
Leaching
Volatility
Use Pattern
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
L^kes and Ponds
Food Crops
Ornamental s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
Lnkes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
Lakes end Ponds
Food Crops
Ornamenta Is
Swimming Pools
Lakes and Ponds
Food Crops
Ornamonta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
Lakes and Ponds
Is data required?
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
No
Yos
No
No
No
No
No
Yes
Yes
No
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
Yes
Yes
Yes
Yes
No
No
No
No
Does EPA have Data?
Yes
Yes
Yes
Yes
No
No
No
No
Yes
Yes
No
No
No
No
No
No
No
No
No
Yes
Yes
Yes
Yes
No
No
No
Yes
Yes
Yes
Yes
Must data be submitted?
Yes
Yes
Yes
No
Yes
Yos
L Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yos
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
oo
-------
T=ible II Environmental Fate— Dichlone Generic Data Requirements by Use Patterns (cont.)
Guidelines Section
163.62-9(d)
163.62-9(o)
163.62-10(c)
163.62-10(d)
163.62-10(e)
163.62-10(f )
163.62-11(b)
Generic Data Requirement
Adsorption/desorption
Water dispersal
Terrestrial field
dissipation
Aquatic field 1
dissipation
Terr estr i a 1 /Aquat i c
(forest) ecosystem residue
Aquatic Impact Uses
Combination and tank
mixes
Rotational Crops
Use Pattern
Food Crops
Ornamental s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
Lakes and Ponds
Food Crops
Orncimontcit s
Swimming Pools
Lakes and Pools
Ornamental s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lnkes nnd Ponds
Food Crops
Ornamental s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
L-ikcs and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Is d*+a required?
Yos
Yes
Yos
Yes
Mo
No
Yes
Yes
Yes
Yos
No
No
Yes
Yos
Yos
No
No
No
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yos
Yes
Yes
No
No
Does EPA have Data?
No
No
No
No
No
No
Yes
Yes
No
No
No
No-
No
No
No
No
No
No
No
No
No
Must data be submitted?
Yes
Yes
Yos
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yos
Yes
Yes
Yes
Yes
Yr-s
Yes
Yes
Yes
-------
Table II1-1 Ecological Effects-- Data Requirements for End-Use Dichlone Products by Composition Characteristics
Guidelines Section
163.71-5(1)
163.71-5(2)
163.72-1
163.72-2
163.72-3
163.72-6(n)(1)
163.72-6(a)(2)
Data Requirement
for End-Use Products
Cage or pen field test*
Fui 1 scale field test*
Fish acute LC™
rainbow trout, bluegill
Acute toxic ity to aquatic
invertebrates
Acute toxic ity to estuarine
and marine orqanism
Short term simulated field
test
Long term simulated field
test
Compos i t i on
Characteristics
50?WP
2,3,6,9?D
50? FC
1.5$; 4.9?
50?WP
, 5% FC; 1.5? RTU
2,3,6,9?D
50^ FC '
1.5?, 4.9?
.. 5% FC; 1.5? RTU
50?WP
2,3,6,95:0
50? FC
1.5?, 4.9?
, 5? FC; 1.5? RTU
50?WP
2,3,6,9?D
50? FC
1.5?, 4.9%
, 5? FC; 1.5? RTU
50?WP
2,3,6,9^0
50? FC
1.5?,. 4.92
, 5? FC; 1.5? RTU
50?WP
2,3,6,9?D
50? FC
1.5? 4.9?
50?WP
, 5? FC; 1.5? RTU
2,3,6,9?D
50% FC
1.5, 5?FC,
1.5? RTU
Do we
need it?
No*
No*
No*
No*
No*
No*
No*
No*
Yes
No
No
Yes
Yes
No
No
Yes
No
No
No
No
Yes
No*
No*
Yes*
No*
No*
No*
No*
Do we
have it?
No
No
No
No
No
No
* When additional data is received and evaluated,
those studies may be required.
-------
Fable i I I-2 Ecological Effects— Generic Data Requirements for Dichlone by Usn Patterns
Gui del ines Section
163.62-IKc)
163.62-IHd)
163.62-1 He)
163.71-1
1 63 . 7 1 -2
163.71-3
163.71-4
163.72-1
163.72-2
163.72-3
163.72-4
163.72-5
Gener i c Data Requ i rement
Irrigated Crops
Fish accumulation
Special study - Aquatic
non-crop
Avian Sing le Dose
LD
Avian dietary LCL,. -
mallard - bobwhite quail
Mammalian acute toxic ity
Avian reproduction
a)mallard b)bobwhite quail
Fish acute LC50 -
rainbow trout, blueqill
Acute toxicity to aquatic
invertebrates
Acute toxicity to estuarine
and marine organisms
Embryo larvae and life
cycle studies/fish and
aquatic invertebrates
Aquatic organisms toxicity
and residue studies
Use Pattern
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimmi ng Pool s
Lakes and Ponds
Food Crops
Ornamenta Is
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta Is
Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Is data required?
Yes
Yes
No
No
Yes
Yes
No
Yes
Yes
No
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
No
No
No
Yes
No
No
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
No
No
No
No*
No*
No*
No*
No*
No*
No*
No*
Does EPA Have Data?
No
No
No
No
No
No
No
No
No
No
No
Yes
Yes
Yes
Yes
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Must data be submitted?
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
No
No
No
Yes
No
No
No
No
No
No
No
No
*When additional data is received and evaluated, these studies may be required.
TV)
-------
Table 111-2 Ecological Effects— Generic Data Requirements for Dichlone by Use Patterns (cont.)
Guidelines Section
163.122-1
163.122-1
163.122-2
'63.122-2
163.125-3
Generic Data Requirement
Seed Germination
Veqetative Viqor
Aquatic
Macrophytes
Alqae
Nitogen Fixation
Potential
Use Pattern
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swi mmi nq Poo 1 s
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimminq Pools
Lakes and Ponds
Food Crops
Ornamenta Is
Swimming Pools
Lakes and Ponds
Is data required?
Yes
Yes
No
Yes
Yes
Yes
No
Yes
Yes
Yes
No
Yes
Y?s
Yes
No
Yes
Yes
Yes
Yes
Yes
Does EPA Have Data?
Yes
Yes
Yes
No
No
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Must data be submitted?
Yes
Yes
Yes
Yes
No
No
No
No
No
No
No
No
No
No
-------
Treble IV--!
Toxicology— Data Requirements for Dichlone Products by Composition Characteristics
Gu idol i nes Section
163.61 1
163-81-2
163.61-3
163.81-4
163.81-5
163.81-6
Data Requirement
Acute Oral toxic ity
Acute dermal toxic ity
Acute inhalation toxic ity
Primary eye irritation
Primary dermal irritation
Dermal sensitizat ion
Composition Character i sties
Mnnuf actur inc^-Use
502WP
2,3,6,9£D
502 FC
1.5£, 4.9?, 5 A' FC; 1.52 RTU
M&nuf actur i nq Use
50£WP
2,3,6,920
L_5C£ FC
1.52, 4.92, 52 FC; 1.5? RTU
Manuf actur i ng-Use
502WP
2,3,6,920
50;, FC
1.52 4.92, 52 FC; 1.52 RTU
Manuf actur i nq-Use
502WP
2,3,6,920
507, FC
1.5-X;, 4.9^_5/" FCj^ 1.5$; RTU
Manuf actur i nq-Use
50£WP
2,3,6f9f,D
50 % FC
1.5£, 4.9^j 5? FQi 1.52 RTU
Manuf actur i nq-Usc
50£WP
2,3,6,920
502 FC
1.52 4.92, 52 FC; 1.52 RTU
Do we
need it?
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yns
Yes
Yes
Yes
Yes
Yes
Yes
Do we
have it?
Yes
Ho
No
No
No
No
No
No
No
No
No
No
No
No
No
No
Mo
No
No
No
No
No
No
No
No
No
No
No
No
No
UJ
-------
Table IV-2 Toxicology-- Generic Data Requirements for Dichlone by Use Patterns
Guidelines Section
•163.81-1
163.81-2
163.81-3
163.81-7
163.82-1
163.82-2
163.82-3
163.82-4
163.82-5
163.63-1
Generic Data Requirement
Acute Oral Toxicity
Acute Derma 1 Tox i c i ty
Acute Inhalation
toxlclty 1
Acute de I ayed neuro-
toxiclty
Subchronic oral dosing
Subchronic 21 day dermal
tox 1 c i ty
Subchronic 90 day dermal
tox i c i ty
Subchronic Inhalation
toxiclty
Subchron i c neurotox i c 1 ty_
Chronic feedinq
Use Pattern
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamenta Is
Swimminq Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimminq Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimminq Pools
Lakes and Ponds
Food Crops
Ornamental s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimminq Pools
Lakes and Ponds
Food Crops
Ornamenta 1 s
Swimming Pools
Lakes and Ponds
Food Crops
Ornamental s
L Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Is data required?
Yes
Yes
Yes
No
Yes
Yes
Yes
No
Yes
Yes
Yes
No
No
No
No
No
Yes
Yes
Yes
No
Yes
Yes
No
No
Yes
Yes
Yes
Yes
No
No
No
No
No
No
No
No
Yes
Yes
Yes
No
Does EPA have Data?
Yes
Yes
Yes
No
No
No
No
No
No
Yes
Yes
Yes
No
No
No
No
No
No
Yes
Yes
Yes
Must data be submitted?
No
No
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
No
No
Yes
Yes
Yes
Yes
Yes
Yes
Yes
-------
Table IV-2 Toxicology— Generic Data Requirements for Dlchlono by Use Patterns (cont.)
Guidelines Section
163.83-2
163.83-3
163.83-4
163.84-1
163.85-1
Generic Data Requirement
Oncogen lefty
Teratoqenlclty
Reproduction
Mutagen 1 c 1 ty
Metabo 1 i sm
Use Pattern
Food Crops
Ornamenta 1 s
Swimminq Pools
Lakes and Ponds
Food Crops
Ornaments 1 s
Swimminq Pools
Lakes and Ponds ,
Food Crops
Ornamentals
Swimminq Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Food Crops
Ornamentals
Swimming Pools
Lakes and Ponds
Is data required?
Yes
Yes
Yes
No
Yes
Yos
Yos
No
Yes
Yes
Yes
No
Yes
Yes
Yes
No
Yes
Yes
Yes
No
Does EPA have Data?
Yes
Yes
Yes
No
No
No
Yes
Yes
Yes
No
No
No
No
No
No
Must data be submitted?
Yes
Yes
Yes
Yes
Yes
Yes
• Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
Yes
ro
-------
Chapter III
Product Chemistry Chapter
Introduction
FIFRA 3(c)(2)(A) requires the Agency to establish guidelines for
registering pesticides in the United States. The Agency requires
registrants to provide quantitative data on all active ingredients, and
provide data on manufacturing impurities and added inerts, 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 manufactur-
ing 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, and upper
limits only for sane unintentional ingredients. Subpart D 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 also requires
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., solubility). Data are also required on the properties of the
formulated product to establish labeling cautions (e.g., flammability,
corrosiveness or storage stability). The Agency uses these data to
characterize each pesticide and to determine its environmental and health
hazards.
DISCIPLINARY REVIEW
Chemistry Profile
Data Requirements and Data Gaps
Required Labeling
Chemistry Profile
Technical dichlone contains a minimum of 95 percent of the active
ingredient (2,3-dichloro-l,4-naphthoquinone). Technical dichlone is a
yellow to brownish-yellow crystalline or powdery substance. Dichlone is
relatively stable to light and heat. Its decomposition by light is
accelerated while it is in solution and it can be sublimed at elevated
temperatures. It is practically insoluble in water but very soluble in
various organic solvents like xylene, dioxane, benzene, and chloroform.
Specific gravity is 1.70 at 25 C, melting point range 188 C - 194 C.
Technical dichlone is used for the formulation of end-use products,
accordingly it is a "manufacturing-use product."
Based on the data reviewed, a technical pesticide product containing
dichlone will have an equivalent concentration of active ingredient, the
same identifiable non 2,3-dichloro-l,4-naphthoquinone components, and
26
-------
properties comparable to those described in this
chapter. Data have been provided on the composition of each of the
registered products, and are in the confidential statement of formula filed
in the Registration Division, OPP. Ml the inerts listed in the
confidential statements of formula are cleared for use on food or feed
under Section 180.1001 of 40 CFR. The majority of the products are
registered for agricultural use (food and nonfood uses) and seme are
registered for use as algaecides in swimming pools, ponds and lakes.
Data Requirements and Data Gaps
All registrants of dichlone products must fulfill the data requirements as
summarized on pages 14 through 17. A full description of the data
requirements can be found in the Proposed Guidelines for the Registration
of pesticides in the United States, 43 FR 29696, July 10, 1978.
Required Labeling;
Ingredient Statement: The ingredient statement for the manufacturing-use
product dichlone will list the active ingredient as:
"Dichlone (2,3-dichloro-l,4-naphthoquinone) % min."
Physical Hazard Precautionary Labeling
Ihe labels of the technical and formulated products containing dichlone
should bear appropriate warnings in accordance with the nature of
physical/chemical properties to be submitted with the products at the time
of reregistration.
27
-------
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 usually requires in order to adequately assess a
pesticide's chemistry. Also under each of the topics is a reference to the
section in the 'Proposed Guidelines'.
Category of Test Guideline Number
Chemical Identity 163.61-3
Manufacturing Process 163.61-4
Discussion on Formation of Unintentional Ingredients 163.61-5
Declaration and Certification of Ingredients 163.61-6
Product Analytical Methods and Data 163.61-7
Physical/Chemical Properties 163.61-8
CHEMICAL IDENTITY (163.61-3)
"Dichlone" is the generally accepted common name for 2,3-dichloro-l,4-
naphthoquinone. Dichlone is approved as the official common name for 2,3-
dichloro-l,4-naphthoquinone by the former Interdepartmental Committee on
Pest Control, the British Standards Institution and the International
Organization for Standardization.
The name "dichlone" will be routinely used in this standard.
Registered trade names for dichlone are: Dichlone, Quintar, Miraclear, and
Phygon.
For the complete technical characterization of the compound, see the
"Chemical Data Sheet" for dichlone in Table 1, following page.
28
-------
TABLE 1
Dichlone Technical Chemical Characterization
Chemical name: 2,3-dichloro-l,4-naphthoquinone
Other name(s): Phygon, Quintar
Type: Fungicide
Shaughnessy #: 029601
C.A.S. #: 117-80-6
Chemical Formula: C-,QH402C12
Mol. Wt.: 227.05
Structural Formula:
Major Use: Fungicide on fruit trees and vegetables. Also used as an
algaecide for the treatment of swimming pools, lakes, and ponds.
29
-------
MANUFACTURING-PROCESS (163.61-4)
There are only two chemical companies which market technical dichlone,
i.e.: FMC Corporation, Agricultural Chemical Division and Aceto Chemical
Company, Inc. In 1971, FMC Corporation, in response to a request for
product chemistry data, informed EPA that they do not manufacture dichlone
but that they import the technical dichlone from Japan. The Aceto Chemical
Company also imports its technical dichlone from Japan. No manufacturing
process for the imported "Japanese" dichlone was reported, and no data have
been submitted concerning the purity of the dichlone product.This
constitutes a data gap.
The literature describes various methods of synthesizing dichlone:
1. The chlorination of sludge (a by-product in the production of phthalic
anhydride from naphthalene), with the use of a catalyst and an inert
solvent [Japanese Patent 67-17736; Tsuchida and Tachibana, 1967, MRID
05004864].
2. The chlorination of naphthalene in carbon tetrachloride and the
oxidation of the chlorinated product by nitric acid and, in turn,
chlorination of the oxidation product [U.S. Patent 3,433,812; Buzbee
and Ecke, 1969, MRID 05001647].
3. The chlorination of sodium naphthionate in nitrobenzene [Nakahara et
al., 1965, MRID 05003899].
4. The chlorination of 1,4-naphthoquinone by the use of FeCUELO and
nitrobenzene [U.S. Patent 2,975,196; Sjoestrand, 1961, MRID 05001652].
5. The chlorination of 1,4-naphthoquinone in carbon tetrachloride and N-
methyl-2-pyrolidone [Japanese Patent 76-113859; Watanabe et al., 1976,
MRID 05004895].
6. The chlorination of 1,4-naphthoquinone in an organic solvent and N,N-
dimethylformamide, N,N-dime thy lace tarn ide or a higher n-n-dimethyl
acylamide [British Patent 1,102,849; Chemische Fabrik von Heyden A.G.,
1968, MRID 05002617].
7. The chlorination of naphthylamine salt and oxidation by nitric acid of
the chlorinated product producing 2,3-dichloro- 1,4-naphthoquinone
[Japanese Patent 69-28300; Itoromogawa et al., 1969, MRID 05005690].
8. The chlorination of 1,4-naphthoquinone in an organic solvent (mono
chloro- benzene) and a catalyst comprised of a tri (low grade alkyl)
phosphoric ester or a tris (low grade alkyl halide) phosphoric ester
[Japanese Patent 78-98943; Matsuura et al., 1978, MRID 05009211]
Although each of these procedures is finely defined, no determination was
made as to the presence and identification of manufacturing impurities.
The chemical reaction employed in the manufacture of the active ingredient
may also produce harmful impurities. The presence of manufacturing
impurities is dependent upon the sort of process used.
30
-------
DISCUSSION CN FORMATION OF UNINTENTIONAL INGREDIENTS (163.61-5)
The nature of the impurities found in the manufactured product depends upon
the kind of manufacturing process used. FMC and Aceto have not submitted
to the Agency the manufacturing process used to synthesize dichlone in
Japan. Therefore, no predictions will be made concerning formation
of unintentional impurities found.
DECLARATION AND CERTIFICATION OF INGREDIENTS (163.61-6)
The Registration Standard includes the composition of technical dichlone,
manufacturing-use dichlone and end-use formulations which contain the
active ingredient. This information is needed to define the acceptable
ranges of concentration allowable in registered products, to prescribe
appropriate test material concentrations in hazard evaluation testing and
later to estimate likely exposures to the active ingredient resulting from
the handling or use of the products which contain it.
Technical dichlone (manufacturing-use product)
There are no data on the certification of dichlone produced by Aceto
Chemical Company, or EMC Chemical Company. This constitutes a data gap.
Information, posted by the U.S. Rubber Company in the Technical
Formulations Handbook (United States Rubber Co., 1965, MRID 00001540)
describes the technical dichlone as containing not less than 95 percent
of the active ingredient 2,3-dichloro-l,4-naphthoquinone with the following
specific particle size distribution, i.e.: the mean particle radius will
range from 3.5 to 6.0 microns and particles with a radius of over 10
microns will be not more than 16 percent of the total. According to the
above information, up to 5% of the technical impurities (including
moisture) can be expected.
There are nine chemical companies registered to manufacture or formulate 21
products containing dichlone as a single active ingredient. There are 19
registered formulated products containing dichlone as a single active
ingredient. HDwever, they are not all registered for agricultural use.
See Table 2, on the following page.
This Registration Standard for dichlone thus covers only those technical
products within the above mentioned composition range for percentage of
active ingredient. Accordingly, pesticide producers and formulators who
wish to register a product containing dichlone that does not fall within
this range of composition must petition the Agency to amend the standard.
PRODUCT ANALYTICAL METHODS AND DATA (163.61-7)
In order to ensure that products contain only those percentages of active
ingredient which they properly claim to contain, it is necessary to have
available analytical methods which may be used to determine the concen-
tration of active ingredient in each formulation.
Second, in the commercial production of pesticide chemicals, reactions
between pesticide ingredients, reactions with packaging materials, as well
as degradation during the long period in which some products may be stored
31
-------
Table 2
Manufacturers and Formulators of Dichlone Products
Product Name
Manufacturer/Formulator
EMC Corp., Agri. Chem. Div
Dichlone 50WP Fungicide
Dichlone 3 Dust
Dichlone 2 Dust
Dichlone Technical
Dichlone 90%
Haviland Agri. Chem. Co.
E-Z-Flo Chemical Co.
Hopkins Agri. Chem. Corp.
Dichlone Dust No. 2
Dichlone Dust No. 3
Dichlone Dust No. 6
E-Z-Flo Dichlone 3 Dust
Dichlone Wettable Powder
Fungicide
Hopkins Quintar 5F
Aceto Chem. Co., Inc.
Paragon Swimming Pool Co., Inc.
Modern Pool Products, Inc.
Agway, Inc.
Dichlone Fungicide
Dichlone 50 WP
Miraclear L
Miraclear P
Berkite 13 Algaecide
Berkite 4
Phygon 6D
Agway Phygon 9D
Agway Phygon SOW
Phygon 3D
32
-------
before use, can result in the formation of chanical impurities. Because of
the potential toxicity of impurities, analytical methods must be provided
for their assessment, both to improve the reliability of the Agency's
hazard assessment and to ensure that marketed products conform to the
standards of purity agreed upon by the pesticide producer.
Though methods for the identification and quantification of dichlone and
possible impurities have not been submitted by the registered manufacturers
of dichlone, the literature indicates various Thin Layer Chromatographic,
Colorimetric and Spectrophotometric methods. These TIC, Colorimetric and
Spectrophotometric methods for detecting and measuring dichlone in its
registered formulations are described in Goza (1972, MRID 05001418) and
Kilgore and White (1970, MRID 05001423). A method regarded as satisfactory
for the determination of dichlone and its impurities is depicted in
Kotakemori and Okada (1968, MRID 05004746). In this study an analytical
gas Chromatographic method reported the principal impurity of Japanese
dichlone as 2-chloro-l,4-naphthoquinone ranging from 0.75 to 2.64%. Also,
the presence of minute quantities of phthalic anhydride and other
unidentified compounds was indicated.
The presence of the phthalic anhydride as an impurity suggests that the
analyzed dichlone was manufactured by the sludge chlorination method
(Tsuchida and Tachibana, 1967, MRID 05004864). The nature of the
impurities found in the manufactured product depends upon the kind of
manufacturing process used.
A toxicological feeding study indicates that technical dichlone fed to
animals contained from 30-600 ppm of lead (FRL, 1952, MRID 00001513).
Although the referenced methods are regarded as satisfactory for
identification, there is not enough analytical data (recoveries, background
sensitivity, etc.) to determine whether or not these methods are adequate
for registration purposes which includes regulatory enforcement.
t
The presence of all impurities in dichlone down to 0.1%, as is required by
the proposed Registration Guidelines Sections 163.61-7(a)(2),(3) has
not been reported.
PHYSICAL/CHEMICAL PROPERTIES (163.61-8)
Some physical/chemical properties reported for manufacturing-use
dichlone are:
Color; yellow to yellow-brownish crystals or powder (United States
Rubber Co., 1965, MRID 00001540)
Odor; no information available, this is a data gap
Solubility; (United States Rubber Co., 1965, MRID 00001540) (grams per
100 g. of solution at 25 C) in:
Water 0.1 ppm
Dioxane 6.2 g
Benzene 4.1 g
33
-------
Glacial Acetic Acid 1.1 g
Ethyl Acetate 1.8 g
Acetone 2.3 g
Diethyl Ether 0.37 g
Xylene 5.6 g
o-dichlorobenzene 4.2 g
Ethyl Alcchol 0.38 g
Skelly Solve B less than 1 g
Carbon Tetrachloride less than 1 g
Dibutyl Hithalate less than 1 g
Dimethyl Formamide 4.2 g
Chloroform 2.9 g
n-Heptane 0.06 g
Mineral oil 0.12 g
Toluene 3.5 g
Melting Point Range: 188°C - 194°C (United States Rubber Co., 1965,
MRID 00001540)
Stability;
Dichlone is relatively stable to light and heat. Its decomposition by
light can be accelerated by solution and it can be sublimed at elevated
temperatures. Although it is stable to hydrolysis in neutral or acid
solution, it reacts readily in an alkaline medium. This is evidenced by a
reddish-purple color indicating the formation of 2-hydroxy-3-chloro-l,4
naphthoquinone (United States Rubber Co., 1965, MRID 00001540).
Octanol/water partition coefficient:
No coefficient has been reported for technical dichlone. Ihis is a data
gap.
Physical State;
Technical dichlone is a solid (United States Rubber Co., 1965, MRID
00001540).
34
-------
Density, bulk density or specific gravity;
The specific gravity of technical dichlone is 1.70 at 25°C. The bulk
density of technical dichlone is 4.5 Ibs./gal. average (United States
Rubber Co., 1965, MRID 00001540).
Vapor pressure:
No vapor pressure for technical dichlone is reported. This is a data gap.
pH:
No determinations of pH were reported. Technical dichlone is practically
insoluble in water. Accordingly, no pH measurement is necessary. For the
formulated products, which can be dispersed with water, pH determinations
are needed.
Storage Stability;
No storage stability data for technical dichlone or any of its formulations
have been submitted. Technical dichlone is claimed by the manufacturer to
be indefinitely stable in closed containers (United States Rubber Go.,
1965, MRID 00001540).
Flammability;
Technical dichlone is a nonccmbustible compound (United States Rubber Co.,
1965, MRID 00001540).
Oxidizing or reducing action;
No data are reported on dichlone as a manufacturing-use product or as a
formulated product. Although dichlone is stable to hydrolysis in neutral
or acid solution it readily reacts in an alkaline medium.
Explosiveness;
No data are reported on the manufacturing-use product and formulated
products of dichlone.
Miscibility;
No emulsifiable liquid products with dichlone as a single active ingredient
have been registered, accordingly, no data regarding "miscibility" are
required.
Viscosity;
No viscosity data are reported for any dichlone liquid formulated products.
Corrosion characteristics;
No data on the corrosiveness of dichlone on containers are reported.
35
-------
Dielectric breakdown voltage;
No data on dielectric breakdown voltage are required because dichlone is
not used around electrical power lines and equipment.
Submittal of samples;
Applicants for registration or reregistration will be notified at the time
of application with regard to the submission of samples.
36
-------
05001647
PRODUCT CHEMISTRY BIBLIOGRAPHY
05002617 ,inventor; Chemische Fabrik von Heyen A.G., assignee (1968)
Process for the production of 2,3-dichloro-naphtho-quinone-
(1,4). British patent specification 1,102,849. Feb 14. 3 p.
Int. Cl. C 07C 49/66.
05001645 Buzbee, L.R.; Bcke, G.G., inventors; Kbppers Co., assignee (1968)
Improvements in or relating to the preparation of
1,2,3,4-tetrachlorotetralin. British patent specification
1,128,115. Sep 25. 8 p. Int. Cl. C 07C 25/18.
Buzbee, L.R.; Ecke, G.G., inventors; Koppers Co., assignee (1969)
Preparation of 2,3-dichloro-l,4-naphthoquinone from
naphthalene. U.S. patent 3,433,812. Mar 18. 5 p. U.S. Cl.
260-396: Int. Cl. C 07C 45/02, 49/66.
05002157 Collerson, R.R.; Harrison, D.J.; Radia, D. (1976) The Infrared
Spectra of High Purity Pesticide Samples. Teddington, England:
National Physical Laboratory. (NPL Division of Chemical
Standards report no. 48)
00001513 Food Research Laboratories, Incorporated (1952) lexicological
Studies of Chemical Additives I. Phygon (2,3-Dichloro-l,4-naph-
thoquinone): Laboratory No. 58084. (Unpublished study received
Dec 22, 1952 under unknown admin, no.; prepared for Naugatuck
Chemical Co., Div. of United States Rubber Co., submitted by
Uniroyal Chemical, Bethany, Conn.; CDL:108443-A)
05001418 Goza, S.W. (1972) Infrared analysis of pesticide formulations.
Journal of the Association of Official Analytical Chemists
55(5):913-917-
05001423 Kilgore, W.W.; White, E.R. (1970) Gas chromatographic separations
of mixed chlorinated fungicides. Journal of Chronatographic
Science 8:166-168.
05005690 Koromogawa, N.; Okada, Y.; Aoki, I., inventors; Takeda Chemical
Industries, assignee (1969) [A method of manufacturing
2,3-dichloro-l,4-naphthoquinone] Japanese patent
specification 69-28300. Nov 21. 2 p.
05004746 Kotakemori, M.; Ando, M. (1968) Nafutokinon-rui no
gasukuronatogurafi [Gas chromatography of naphthoquinones]
Nippon Nbgei Kagaku Kaishi. Journal of the Agricultural
Chemical Society of Japan. 42(12):726-730.
05001467 Kotakemori, M.; Okada, K. (1966) Thin-layer chromatography of some
substituted napthoquinones. Agricultural and Biological
Chemistry 30(9):935-936.
05009211 Matsuura, M.; Sakai, K.; Sato, T.; Yamada, Y.; Bando, K.,
inventors; Kawasaki Kasei Kogyo Co., assignee (1978) [Method
for manufacturing 2,3-dichloro-l,4-naphthoquinone] Japanese
kokai 78 98943. Aug 29. 3 p. Int. Cl._2? C 07C 49/735.
37
-------
05003899 Nakahara, T.; Dehara, M.; Hiyama, H. (1965) [A study on the
chlorination of naphthionic acid] Kagaku Tb Kbgyo (Osaka).
05001652 Sjostrand, B.T.L., inventor; Svenska Oljeslageri Aktiebolaget,
assignee (1961) Chlorination of naphthoquinone. U.S. patent
2,975,196. Mar 14. 2 p.
05004894 Tsuchida, I.; lachibana, T., inventors; (1967) [Production method
for 2,3-dichloro-l,4-naphthoquinone] Japanese patent
specification 67-17736. Sep 16. 3 p. Cl. 16 D 414.
00001540 United States Rubber Company (1965?) Technical Formulators Hand-
book: Phygon: Dichlone. (Unpublished study received Aug 31,
1965 under 8729-3; submitted by ECO Sciences, Inc., Bconton,
N.J.; CDL:009475-E)
05004895 Watanabe, H.; Mitsui, N.; Maeda, S.; Kbnishi, S.; Anitani, T.,
inventors; Seitetsu Chemical Industry, assignee (1976)
Japanese kokai 76-113859. Oct 7. 3 p. Int. Cl.=2? C 07c
49/66.
38
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Chapter IV
Environmental Fate Chapter
DISCIPLINARY REVIEW
Environmental Fate Profile
Use Profile
Data Gaps
Environmental Fate Profile
Ihe submitted data were insufficient to fully assess the environmental fate
of dichlone.
A half-life of five days was determined for dichlone (conmercial
formulation) by a hydrolysis study conducted in a 1/30 molar phosphate
buffer at pH 7. Dichlone dissipates more rapidly in a moist (17.5% water,
pH 6.4) than in a dry (1.6% water, pH 6.2) silt loam soil. Dichlone
exhibited a half-life of one day in the moist soil and one of almost three
months in the dry soil. Although the soil study does not differentiate
between hydrolytic and metabolic degradative processes, the hydrolysis and
soil metabolism studies taken together do suggest that hydrolysis and
perhaps metabolism are major degradative processes of dichlone.
Soil nitrification, as measured by changes in total soil nitrate levels,
was not affected by dichlone at recommended application rates. However,
dichlone reportedly inhibited formation of taproot nodules while
stimulating formation of lateral root nodules. Overall nodulation induced
by Rhizobium leguminosarum was about the same in treated and control
plants. At concentrations between 0.5 and 0.9 ug/ml, dichlone inhibited
£_._ coli growth. Light dependent growth of photoautotrophic and
photoheterotrophic cultures of Rhodosprillum rubrum was inhibited by
dichlone at 1 uM. Dichlone at 3 x 10 M completely inhibited oxygen
evolution and chlorophyll production and markedly decreased cell numbers
of the alga Chlorella by 48 hours of exposure. These studies suggest
that dichlone, at recommended application rates, has deleterious effects on
microbial growth among a diverse group of microorganisms (bacteria and
eukaryotic algae) studied and not just on the target organism, blue-green
algae. For fungi, the response to dichlone is quite variable and an
overall no-effect level cannot be established. An EC™ is approximately
300 to 700 ug dichlone /g of spores.
Dichlone (analytical grade) did not leach in a modified silty clay loam
soil, but no predictions can be made for the soils due to a lack of test
data.
Dichlone was not detected in any cropland or noncropland soil samples
taken in 43 and 11 states, respectively, Ohese samples included sites
having received dichlone applications at 2.2 or 1.8 Ib ai/A.
In summary, although there are too few data to form a comprehensive profile
of the fate of dichlone in the environment, the information available
suggest that, under some conditions, dichlone may be rapidly hydrolyzed
and/or metabolized. In addition, dichlone is injurious to a diverse group
of microorganisms.
39
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Use Profile
Dichlone is a fungicide/herbicide registered for the control of 1) various
plant diseases on selected agricultural crops and ornamentals,and 2)
certain blocm producing blue-green algae in swimming pools, recreational
lakes and farm ponds (see Table 3 on the following page).
Dichlone is formulated as a 50% active ingredient wettable powder, 2-9%
active ingredient dusts, 5% and 50% active ingredient flowable
concentrates, and a 1.5% active ingredient ready-to-use formulation.
The wettable powder, dust, and flowable concentrate formulation are
registered for application to fruit1 trees, potatoes, strawberries, celery,
tomatoes, and ornamentals. The ready-to-use, flowable concentrate, and
wettable powder formulations are used for algae control in lakes, ponds and
pools (see Table 4 for application rates, on page 42). Dichlone was
registered at one time for use on cotton as an in-furrow treatment, on turf
for rust control, and as a seed treatment.
Major dichlone use is in New England and the Great Lakes States, although
some use is also reported in the South. Current use is limited dueQto
phytotoxicity problems on leaves and fruit at temperatures above 85 F and
reported skin irritation. Dichlone use on fruit trees is also limited in
part due to alternative fungicides that are less phytotoxic.
In 1978, 143,299 pounds of dichlone (active ingredient) were imported into
the U.S. for formulation. Of that, the majority of active ingredient is
used in fruit production. Use on other crops, lakes, ponds, and pools is
less extensive.
Data Gaps
Ml registrants of dichlone products must fulfill the data requirements as
summarized on pages 18 through 19. A full description of the data
requirements can be found in the Proposed Guidelines for the Registration
of pesticides in the United States, 43 FR 29696, July 10, 1978.
40
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Site
Apples
Cherries
Peaches
Pluns & Prunes
Strawberries
Beans
Celery
Tomatoes
Potatoes
Rose
Azaleas
Aquatic Areas
Table 3
Use Patterns
Pest
Scab
Bitter rot
Black rot (frogeye leaf spot)
Brown rot
Cherry leaf spot
Brown rot
Leaf curl
Coryneum blight (California blight)
Brown rot
Prune russett scab
Botrytis blight (gray mold)
Anthracnose
Early blight,
Late blight
Botrytis blight (gray mold),
Early blight, Late blight,
Phcma stem rot
Late blight
Black spot
Petal blight
Blue-green algae
41
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Table 4
Registered Application Rates
Formulation Site Rate
WP-50%
Dust 2%
Dust 3%
Apples
Peaches
Cherries
Plums & Prunes
Tomatoes
Strawberries
Beans
Celery
Ornamentals
Lakes, Ponds
Pools
Apples
Cherries
Peaches
Plums & Prunes
1/4-1/2 lb/100 gal water
1/2- 1 lb/100 gal water
1/2-3/4 lb/100 gal water
1/2-3/4 lb/100 gal water
3/4- 1 lb/100 gal water
3/8 lb/100 gal water
1-1 1/2 lb/100 gal water
1/4-1/2 lb/100 gal water
1/4 lb/100 gal water
2.2 oz/325,960 gal water
1 oz/50,000 gal water
35-50
or
45-60
Ib/acre (EMC)
Ib/acre (Haviland)
Dust 6%
Dust 9%
Ready-to-
use 1.5%
Flowable
Concentrate 50%
Apples
Cherries
Peaches
Plums & Prunes
Beans
Celery
Tomatoes
Apples
Cherries
Peaches
Apples
Cherries
Peaches
30-50
30-50
30-50
30-40
up to
20-25
15-20
10-15
or
15-20
10-12
10-12
10-12
Ib/acre
Ib/acre
Ib/acre
Ib/acre
37 Ib/acre
Ib/acre
Ib/acre
Ib/acre ( Agway )
Ib/acre (Haviland)
Ib/acre
Ib/acre
Ib/acre
Pools
Apples
Peaches
Cherries
Tomatoes
Celery
Potatoes
Ornamentals
1 gal/60,000 gal water
3.2 oz/lOOgal water
6.4-12.8 oz/100 gal
6.4 oz/100 gal
9.6-12.8 oz/100 gal
6.4 oz/100 gal
6.4 oz/100 gal
3.2-6.4/100 gal
Flowable
Concentrate 5%
Flowable
Concentrate 1.5%
Lakes, Ponds 1-5 gal/1,000,000 gal water
Pools
1 qt/50,000 gal water
42
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TOPICAL DISCUSSIONS
Corresponding to each of the Ibpical 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 usually requires in order to adequately assess a
pesticide's Environmental Fate. Also under each of the topics is a
reference to the section in the 'Proposed Guidelines'.
Category of Test Guideline Number
Physico-chemical Transformation 163.62-7
Metabolism (Soil, Aquatic and
Microbiological) 163.63-8
Mobility 163.62-9
Field Dissipation 163.62-10
Accumulation 163.62-11
PHYSICO-CHEMICAL TRANSFORMATION 163.62-7
Hydrolysis 163.62-7(b)
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.
One study was reviewed and provides preliminary data on the hydrolysis of
dichlone (Burchfield, 1959, MRID 05001486). A half-life of 5 days was
determined for dichlone in an M/30 phosphate buffer at pH 7. This study
does not satisfy the data requirements, therefore this is a data gap.
Photolysis 163.62-7(c)
Photodegradation studies in water are required to support the registration
of all formulated products intended for terrestrial (except green-house and
domestic outdoor), aquatic, terrestrial/aquatic (forest), or aquatic impact
(except indirect pesticide discharges and discharges into wastewater
treatment systems) uses.
Studies in soil are required to support the registration of all formulated
products intended for crop uses and terrestrial/aquatic (forest) uses.
No data on the photolysis of dichlone are available. This constitutes a
data gap.
METABOLISM 163.62-8
Data on metabolism are required to determine the nature and availability of
pesticide residues to rotational crops and to help in the assessment of
disposal of the material and the establishment of reentry time intervals
for farm workers.
43
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Soil 163.62-8(bfc)
Aerobic metabolism studies are required to support the registration of all
formulated products intended for terrestrial uses or terrestrial/aquatic
(forest) uses. Anaerobic soil metabolism studies are required to support
the registration of all formulated products intended for field and
vegetable crop uses.
One soil metabolism study was reviewed and provided preliminary data on the
degradation of dichlone in soil (Burchfied, 1959, MRID 05001486). Lhder
aerobic conditions only 12% of the applied dichlone (1 ppm) remained after
3 days in soil containing 17.5% water, whereas 45% remained after 3 months
in soil containing 1.6% water. The soil studies did not differentiate
between metabolic and hydrolytic degradative processes. This study does
not satisfy the data requirements, therefore this is a data gap.
Aquatic 163.62-8(d,e)
An aerobic aquatic metabolism laboratory study using radioisotopic
techniques is required to support the registration of all formulated
products intended for aquatic uses and aquatic impact uses that result in
direct discharges into the aquatic environment.
An anaerobic aquatic metabolism laboratory study using radioisotopic
analytical techniques is required to support the registration of all
formulated products intended for aquatic, terrestrial/aquatic (forest), and
aquatic impact uses that result in direct discharges into the aquatic
environment.
No data on the aquatic metabolism of dichlone are available. This
constitutes a data gap.
Microbiological 163.62-8(f)
Data on the effects of microbes on pesticide degradation and the effects
of pesticides on microbes are required to support the registration of all
formulated products intended for the following uses: terrestrial noncrop,
tree fruit/nut crop, field/vegetable crop, aquatic food crop and noncrop,
terrestrial/aquatic (forest), and direct discharge aquatic impact.
Microbiological - Effects of Microbes on Pesticides 163.62-8(f)(2)
One study was reviewed; however, no valid data on the effects of microbes
on dichlone are available. This constitutes a data gap.
Microbiological - Effects of Pesticides on Microbes 163.62-8(f)(3)
Eight studies were reviewed and five are considered valid.
Zweig et al. (1968, MRID 05001627), showed that, at a concentration of
3 x 10 M, dichlone completely inhibits oxygen evolution and chlorophyll
production and markedly decreases cell numbers of the alga Chlorella
pyrenoidosa at 48 hours of exposure. Chlorella cultures were completely
nonviable at 65 and 90 hours of exposure.
44
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Saxena et al. (1973, MRID 05001698), investigated the effect of dichlone on
bacterial photosynthesis in Rhodospirillum rubrum (a photosynthetic
nonsulfur bacterium) and postulated that dichlone causes irreversible
damage to some primary photosynthetic reactions in chromatophores. The
light-dependent growth of photoautotrophic and photoheterotrophic cultures
of R._ rubrum was inhibited at 1 uM, whereas heterotrophic growth was
temporarily inhibited by dichlone at levels greater than 3 uM.
Ihe effects of dichlone on nitrogen cycle processes have been studied by
measuring nitrate evolution and by investigating dichlone1s effect on soil
nitrification and on the symbiotic relationship of host plants and nitrogen-
fixing bacteria. Wilson (1954, MRID 05001641) observed that soil
nitrification, as measured by nitrate evolution, was inhibited 38% by
dichlone at 95 ppm. Kecskes and Vincent (1969, MRID 05004330)
demonstrated that dichlone (0.6 gAg) applied to vetch (Vicia sativa )
seeds inhibited the development of taproot nodules and stimulated the
development of lateral root nodules in both soil and sand. Ibtal nodule
formation, however, decreased by 12% compared with that in controls.
Neely et al. (1973, MRID 05001654) reported that dichlone at concentrations
between 0.5 and 0.9 g/ml temporarily inhibited Escherichia coli growth.
Sulfhydryl-containing compounds (cysteine, homocysteine, and reduced
glutathione) prevented the inhibitory effects of dichlone when added with
the dichlone and slightly shortened the growth recovery time lag when added
30 minutes after dichlone treatment. Ihis study contains useful
information on the effects of dichlone on microorganisms, although E. coli
is not a representative soil organism.
A study by Le Tbureau (1957, MRID 05001519) indicated that dichlone at a
concentration of 10 M delayed growth of Verticillium albo-atrum (a
fungus) for over 12 days and inhibited the growth about 70%. In a study
conducted by Miller and McCallan (1955, MRID 05001657), dichlone was shown
to inhibit germination of fungus spores. The chart below shows the dose of
dichlone required to inhibit germination at the 50% level. Ihe dose is in
micrograms of dichlone per gram of spores.
Species EDQ
Neurospora sitophila 560 ug/g spores
Monilinia fructicola 385
Alternaria oleracea 400
Rhizopus nigricans 680
Myrothecium verrucaria no effect at 1400 ug/g spores
Table 5 summarizes the effects of dichlone on selected microbes. These
studies partially fulfill the data requirements by providing information on
the effect of dichlone on nitrification.
45
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Table 5
Effects of Dichlone on Microbes
Range of
dichlone
concentrations
(active
ingredient)
19-95 ppm
Species
unspecified
Observations Reference
Nitrification, as measured by Wilson (1954)
N03 evolution, was inhibited MRID 05001641
at 95 ppm but not at 19 ppm.
0.6 g/kg seed Rhizobium spp.
3.5 x 10~5M Chlorella
pyrenoidosa
-150 uM
0.5 - 0.9
ug/ml
Rhodospirillum
rubrum
Escherichia coli
Vetch taproot nodules were
inhibited; lateral root
nodules were stimulated.
Only 88% of plants formed
nodules (compared with 100%
of controls).
0~ evolution decreased about
50% within 60 minutes. After
48 hours, 02 evolution
decreased to zero. Cell viabi-
lity was destroyed within 65-
90 hours.
Photoautotrophic and photo-
he terotrophic growth were
inhibited at 1 uM or more.
Growth was inhibited; however,
recovery to near normal growth
was observed following inhi-
bition.
Kecskes and
Vincent (1969
MRID 05004330
Zweig et al.
(1968) MRID
05001627
Saxena et al.
(1973) MRID
05001698
Neely et al.
(1973) MRID
05001654
46
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All studies specified in Section 163.62-8(f)(3), except those on
nitrification, are required for dichlone. It is also recommended, per
Section 163.62-3, that sufficient data be acquired on the effects of
dichlone on aquatic nontarget microorganisms (viz., the eukaryotic algae).
This reconniendation is made because the available data suggest that
dichlone may have an adverse impact on these microorganisms; which
constitute the majority of the primary producers in aquatic environments.
Activated Sludge 163.62-8(g)
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 systems.
No data on the activated sludge metabolism of dichlone are available. This
constitutes a data gap.
MOBILITY 163.62-9
Data on mobility are required to determine pesticide residue movement in
the environment.
Leaching 163.62-9(b)
Leaching data are required to support registration of formulated products
intended for terrestrial noncrop, tree fruit/nut crop, field/vegetable
crop, and terrestrial/aquatic (forest) uses.
Hslling et al.(1974, MRED 05001190) found that dichlone was immobile on
soil TLC plates coated with a modified (sieved to <250 urn) Hagerstown silty
clayloam. This study showed Rf values ranging from 0.01 to 0.03 with a
mean R^ of 0.02.
Alone, this study is insufficient to draw any conclusions regarding
dichlone's leaching potential. This constitutes a data gap.
Volatility 163.62-9(c)
Laboratory volatility studies using nonradioisotopic analytical techniques
are required to support the registration of all formulated products
intended for greenhouse use.
Volatility data are only required for pesticides used in greenhouses.
Therefore, data are not required on the volatility of dichlone because
no formulated products of dichlone have yet been proposed for green-
house use.
Adsorption/Desorption 163.62-9(d)
A laboratory study using radioisotopic or nonradioisotopic analytical
techniques is required to support the registration of all formulated
products intended for all terrestrial uses, terrestrial/aquatic (forest)
uses, aquatic uses, and aquatic impact uses (if the pesticides are
discharged directly into the aquatic environment).
47
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No data on the adsorption/desorption of dichlone are available. This
constitutes a data gap.
Water Dispersal 163.62-9(e)
A field study tailored to one or more representative sites is required to
support the registration of all formulated products intended for aquatic
uses and aquatic impact uses (if the pesticides are discharged directly
into aquatic sites).
No data on the water dispersal of dichlone are available. This constitutes
a data gap.
FIELD DISSIPATION 163.62-10
A field dissipation study under actual use conditions is required to
support the registration of all formulated products intended for
terrestrial (except greenhouse) uses, aquatic uses, and terrestrial/aquatic
(forest) uses.
Terrestrial 163.62-10(b)
Terrestrial field dissipation studies using the formulated product are
required to support the registration of each pesticide formulation intended
for all terrestrial (except greenhouse) uses, terrestrial/aquatic (forest)
uses, and aquatic food crop uses.
Two studies were reviewed and one was considered valid. In a monitoring
study conducted by Wiersma et al. (1972, MRID 05004938) dichlone was not
detected in any sample of cropland soils sampled in 43 states, and
noncropland soils sampled in 11 states.
These data alone are insufficient to assess the rate or the impact of the
dissipation of dichlone in the field. This constitutes a data gap.
Aquatic 163.62-10(c)
Aquatic field dissipation studies using the formulated product are required
to support the registration of each pesticide formulation intended for all
aquatic uses, terrestrial/aquatic (forest) uses, and aquatic impact uses
(if the pesticides are discharged directly into the aquatic environment).
No data on the aquatic dissipation of dichlone are available. Ihis
constitutes a data gap.
Terrestrial/Aquatic (Forest) 163.62-10(d)
A special ecosystem residue study is needed to support the registration of
each pesticide formulation intended for terrestrial/aquatic (forest) uses.
No data on the terrestrial/aquatic dissipation of dichlone are required
because the use pattern indicates that introduction into the forest
environment would not occur.
48
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Aquatic Impact Uses 163.62-10(e)
Aquatic impact use studies are required to support the registration of all
formulated products that will be directly or indirectly discharged into the
aquatic environment or are intended for use in wastewater treatment systems.
No data on the aquatic impact of dichlone are available. This
constitutes a data gap.
ACCUMUIATIOSI 163.62-11
Data on accumulation are required to determine accumulation in food chains.
Rotational Crops 163.62-11(b)
Botational crop studies are required to support the registration of all
formulated products intended for field/vegetable and aquatic food crop uses.
No data on the accumulation of dichlone in rotational crops are
available. This constitutes a data gap.
Irrigated Crops 163.62-11(c)
A crop residue study under actual field use conditions is required to
support the registration of all formulated products intended for aquatic
food or aquatic noncrop uses, or for use in holding ponds or effluent and
other discharged sources used to irrigate crops. No data on the
accumulation of dichlone in irrigated crops are available. This
constitutes a data gap.
Fish 163.62-ll(d)
This laboratory study employing radioisotopic or nonradioisotopic
analytical techniques is required to support the registration of all
formulated products intended for terrestrial noncrop, tree fruit/nut crop,
and field/vegetable crop uses; aquatic food crop and noncrop uses;
terrestrial/aquatic (forest) use; and aquatic impact (direct discharge)
uses.
No data on the accumulation of dichlone in fish are available. This
constitutes a data gap.
49
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ENVIRONMENTAL FATE BIBLIOGRAPHY
05001486 Burchfield, H.P. (1959) Comparative stabilities of Dyrene,
l-fluoro-2,4-dinitrobenzene, dichlone, and captan in a silt
loam soil. Contributions from Boyce Thompson Institute
20:205-215.
05001190 Helling, C.S.; Dennison, D.G.; Kaufman, D.D. (1974) Fungicide
movement in soils. Phytopathology 64(8):1091-1100.
05004330 Kecskes, M.; Vincent, J.M. (1969) Nehany fungicid hatasa
a Rhizobium leguminosarum sp. re: II. Fenykamras es uveghazi
vizsgalatok. [The effect of some fungicides on Rhizobium
leguminosarum; II. Light room and glasshouse
investigations] Agrokemia es Talajtan. [Agrochemistry and
Soil Science.] 18(3/4):461-472.
05001654 Neely, W.C.; Smith, R.C.; Cody, R.M.; McDuffie, J.R.; Lansden,
J.A.; Ellis, S.P. (1973) Biological and Photobiological Action
of Pollutants on Aquatic Microorganisms. Auburn, Ala.: Water
Resources Research Institute, AuburnlMiversity. (WRRI Bulletin
9; also available from: NTIS, Springfield, Va.; PB-220 167)
05001540 Powell, D. (1951) Phygon XL for the control of peach blossom
blight. Plant Disease Reporter 35(2):76-77.
05001698 Saxena, J.; Sikka, H.C.; Zweig, G. (1973) Effect of certain
substituted naphthoquinones on growth and respiration
of Rhodospirillum rubrum. Pesticide Biochemistry and
Physiology 3(l):66-72.
05004895 Watanabe, H.; Mitsui, N.; Maeda, S.; Konishi, S.; Amitani, T.,
inventors; Seitetsu Chemical Industry, assignee (1976)
Japanese kokai 76-113859. Oct 7. 3 p. Int. Cl. 2 C 07c
49/66.
05004938 Wiersma, G.B.; Tai, H.; Sand, P.F. (1972) Pesticide residue levels
in soils, FY 1969—National Soils Monitoring Program.
Pesticides Monitoring Journal 6(3):194-228.
50
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Chapter V
Toxicology Chapter
DISCIPLINARY REVIEW
Toxicology Profile
Data Requirements and Data Gaps
Required Labeling
Toxicology Profile
Technical Dichlone
Insufficient data were reported to support an assessment of technical
dichlone's acute toxicity. The low acute oral LD5Qin rats (1.63 gAg)
indicates a potentially low acute oral toxicity in humans. No data were
reported for acute dermal and acute inhalation toxicity.
Insufficient data were available to support an assessment of technical
dichlone's irritation and sensitization potential. An inadequate eye
irritation study conducted on rabbits suggests that technical dichlone is
moderately irritating to the eye. An inadequate dermal sensitization
conducted on guinea pigs suggests no allergic response.
Insufficient data were available for the assessment of subchronic and
chronic toxicity of technical dichlone. The oncogenic, reproduction,
chronic feeding, and mutagenicity studies submitted were inadequate due to
improper testing protocols and/or insufficient data reporting. No data
were available for teratology and animal metabolism.
Dichlone Formulations
No tests were reported for the wettable powder, dust, flowable concentrate,
and ready-to-use formulations to assess the acute oral, dermal,
and inhalational toxicities, primary eye and dermal irritation, and dermal
sensitization.
Data Requirements and Data Gaps
All registrants of dichlone products must fulfill the data requirements as
summarized on pages 23 through 25. A full description of the data
requirements can be found in the Proposed Guidelines for the Registration
of pesticides in the United States, 43 FR 37336, August 22, 1978.
Required Labeling
Acute Oral Toxicity
The acute oral toxicity for technical dichlone in rats is 1.63 gAg* which
corresponds to Toxicity Category III. Precautionary statements for the
acute oral toxicity is: "Harmful if swallowed".
Labels may be changed after submission of acute toxicity data.
51
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Primary Eye Irritation
One test has shown that dichlone is a moderate eye irritant. This test had
sane inadequacies that will necessitate more testing. At this time,
however, a precautionary statement, "Eye Irritant" is required on the
label.
Primary Dermal Irritation
One test has shown that dichlone is a moderate skin irritant. This test
had seme inadequacies that will necessitate more testing. At this time,
however, a precautionary statement, "Skin irritation is possible, especialy
at elevated temperatures" is required on the label.
Dichlone Formulations
No acute oral, dermal, or inhalation toxicity, primary eye or primary skin
irritation, or skin sensitization tests are available. Therefore, no
additional labeling is required at this time.
52
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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 43 FR 37336, August 22,
1978, which explain(s) the minimum data that the Agency usually requires in
order to adequately assess a pesticide's toxicology. Also under each of
the topics is a reference to the section in the 'Proposed Guidelines'.
Acute Testing Guideline Section
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
Dermal 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
Chronic Testing
Chronic Feeding Studies 163.83-1
Oncogenicity 163.83-2
Teratogenicity 163.83-3
Reproduction 163.83-4
Mutagenicity 163.84-(l-4)
Metabolism 163.85-1
ACUTE TESTING
ACUTE ORAL TOXICITY (163.81-1)
The minimum testing needed on acute oral toxicity is one test with the
laboratory rat using the technical chemical and each manufacturing-use and
formulated product.
Technical
The acute oral LD™ of dichlone (Phygon of unspecified purity, as a
suspension in water containing 2% Tween 80) in the rat was 1.63 g/kg in one
test and 1.32 g/kg in a second test conducted in the same laboratory
(FRL,1952a, MRID 00001521). The presence of 30 and 598 ppm of lead in the
samples used, although undesirable, was characteristic of the technical
product in use at that time and would not have materially affected these
acute toxicity measurements. Signs of intoxication included sluggishness,
depression, gastrointestinal irritation, and temporary weight loss. At
autopsy, seme treated animals showed cardiac and pulmonary congestion,
gastric hemorrhage, and intestinal hemorrhage.
53
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This test in rats is adequate to fulfill data requirements for an acute
oral test. Based on these data, dichlone can be placed in toxicity
Category III, corresponding to a low acute oral hazard.
In guinea pigs, the LD5Q for a sample of dichlone (Phygon) contain-
ing 30 ppm of lead was 0.32 gA9- (FRL 1952a, MRID 00001521). Signs of
intoxication included depression and stupor. Based on lethal dose values,
the guinea pig is more sensitive than the rat to large doses of dichlone
(Phygon). Testing in species other than the rat is not required to fulfill
data requirements.
Dichlone Formulations
No tests were reported for the wettable powder, dust, flowable concentrate,
and ready-to-use formulations to assess the acute oral toxicity of
dichlone. Testing is required for all the mentioned formulations.
ACUTE DERMAL TOXICITY (163.81-2)
The minimum testing needed on acute dermal toxicity is one test, on the
rat or albino rabbit, on each technical, manufacturing-use and formulated
product.
Technical
No tests of acute dermal toxicity are available on technical dichlone.
Testing is required.
Dichlone Formulations
No tests were reported for the wettable powder, dust, flowable concentrate,
and ready-to-use formulations to assess the acute dermal toxicity.
Testing is required for all the mentioned formulations.
ACUTE INHALATION TOXICITY (163.81-3)
The minimum testing required on acute inhalation toxicity is one test,
preferably on the rat, for each manufacturing-use product and each
formulated product that is a gas, that produces a respirable vapor, or
that is composed of 20% or more of particles not larger than 10 microns in
diameter.
Technical
No tests were reported on the acute inhalation of technical dichlone.
Testing is required.
Dichlone Formulations
No tests were reported for the wettable powder, dust, flowable concentrate,
and ready-to-use formulations to assess the acute inhalation toxicity.
Testing is required for all the mentioned formulations.
54
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PRIMARY E?E IRRITATION (163.81-4)
Ihe minimum testing needed to evaluate eye irritation potential is one best
on the albino rabbit on each technical, manufacturing-use and formulated
product.
Technical
Application of one drop of 5% suspension of Phygon in physiological saline
to the eyes of five rabbits resulted in moderate irritation of the
conjunctiva and mild irritation of the cornea; these effects were
reversible within two days (FRL, 1952b, MRID 00001522). Although this
study indicates a moderate eye irritation hazard, the test must be repeated
using an adequate number of rabbits to fulfill data requirements.
Dichlone Formulations
No tests were reported for the wettable powder, dust, flowable concentrate,
and ready-to-use formulations to assess the primary eye irritation.
Testing is required for all the mentioned formulations.
PRIMARY DERMAL IRRITATION (163.81-5)
The minimum testing needed to evaluate dermal irritation potential is one
test on a mamnal, preferably on the albino rabbit, for each technical,
manufacturing-use and formulated product.
Technical
Application of a 20% suspension of Phygon to intact and abraded rabbit skin
(for 6 hours/day on days 1-5 and 15-20) resulted in slight dermal
irritation; no irritation was observed 3-4 days after the last application
(FRL, 1952b, MRID 00001522). Although this study indicates only a slight
dermal irritation hazard for dichlone, this test must be repeated using a
measured amount of test substance over a single 24-hour exposure period to
fulfill data requirements. Additional testing is required.
Dichlone Formulations
No tests were reported for the wettable powder, dust, flowable concentrate,
and ready-to-use formulations to assess the primary dermal irritation.
Testing is required for all the listed formulations.
DERMAL SENSITIZATION (163.81-6)
The minimum testing required to assess dermal sensitization is an
intradermal test on one mammalian species, preferably the guinea pig, for
each manufacturing-use and formulated product.
Technical
No evidence of an allergic response was observed following a dermal
sensitization test on a 0.1% suspension of Phygon in six guinea pigs (FRL,
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1952b, MRID 00001522). However, to adequately assess sensitization
potential, this test must be repeated using a larger number of animals.
Additional testing is required.
Formulations
No tests are available for wettable powder formulations, dust formulations,
flowable concentrate formulations and ready-to-use formulations to assess
the dermal sensitization potential. Testing is required for all the
mentioned formulations.
ACUTE DELAYED NEUROTCKICITY (163.81-7)
The minimum data requirements for acute delayed neurotoxicity is one test
for the technical formulation, using the adult hen.
The acute delayed neurotoxicity data are required if the active ingredient,
or any of its metabolites, degradation products, or impurities cause acetyl
cholinesterase depression or are structurally related to a substance that
induces delayed neurotoxicity.
An acute delayed neurotoxicity study is not required on dichlone because it
is not expected to cause acetyl cholinesterase depression nor is it related
to a substance that induces delayed neuropathy.
SUBCHRONIC TESTING
SUBCHRONIC OPAL TOXICITY (163.82-1)
The minimum data requirements for subchronic toxicity are one test for the
technical formulation in two mammalian species, preferably using the rat
and dog.
The subchronic rat and dog studies are required. The rat subchronic
feeding study is required to lay the foundation for the rat two year
feeding study. It provides us with information on possible toxicity within
six months where as the chronic study will take years to provide such data.
Since only one chronic feeding study is required (in rats), there is no
substitute for the second species, a subchronic feeding study on the dog.
In a limited subchronic oral test, rats were given 0, 500, 1,580 or 5,000
pptn of Phygon in the diet for 12 weeks (FRL, 1952c, MRID 00001523). The
test sample contained 30 to 600 ppm of lead. Growth depression, probably
the result of the unpalatability of the diet, was observed throughout the
study at the highest dose (5,000 ppm) and during the first four weeks at
1,580 ppm. No significant changes were observed in clinical chemistry
parameters. Animals were bred during the last month of the study,
necropsies were not performed (except on one animal that died during the
study), and the test sample was contaminated with lead; therefore, this
study cannot be considered an adequate subchronic test.
No adequate tests of dichlone in dogs are available. No reliable
conclusions can be drawn from a study in dogs given 500 or 1,580 ppm of
Phygon in the diet for one year (FRL, 1952d, MRID 00001524) because too few
animals were tested (three dogs per dose), the Phygon samples were
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contaminated with high levels of lead (30 or 600 ppm), and three dogs
became pregnant during the test. Additional subchronic oral testing is
required.
SUBCHRONIC 21-DftY DERMAL TQXICI1Y (163.82-2)
The minimum requirement to assess subchronic 21-day dermal toxicity is one
study in the rabbit on the technical product.
This test is not required for dichlone because data from the subchronic 90-
day dermal toxicity study are required.
SUBCHRONIC 90 DAY DERMAL TQXICITY (163.82-3)
The minimum data requirement for subchronic 90-day dennal toxicity is one
test for the technical formulation, preferably using the albino rabbit.
A subchronic 90-day dermal toxicity test is required on dichlone because
it is unintentionally applied to skin when it is applied as an agricultural
fungicide and as a herbicide for the control of algae in swimming pools.
SUBCHRONIC IMIALATION TOXICITY (163.82-4)
The minimum data requirement for subchronic inhalation toxicity is one test
for the technical formulation, preferably using the albino rabbit.
A subchronic inhalation study will be required if the pesticidal uses
result in repeated exposure at a concentration that is likely to cause a
toxic effect as determnined by the acute inhalation and other testing.
SUBCERONIC NEUROTQXICITY (162.82-5)
The minimum data requirements for subchronic neurotoxicity are one test in
the chicken for the technical formulation or compounds which gave positive
results on the acute neurotoxicity test. The minimum requirement, for
subchronic neurotoxicity is one test for the technical formulation on
compounds which caused irreversible neurological toxicity in a mammalian
species and the test must be performed on that species.
A subchronic neurotoxicity study of dichlone is not required because an
acute neurotoxicity study was not required. At present there is no
evidence to require a mammalian study.
CHRONIC TESTING
CHRONIC FEEDING (163.83-1)
The minimum requirement for chronic feeding study is testing in one
mammalian species, preferably the laboratory rat.
A chronic feeding study is required for dichlone because certain uses
require tolerances.
A 2-year feeding study on the rat was conducted on Fhygon at 0, 500, 1,580,
and 5,000 ppm; the sample tested was contaminated with 600 ppm lead
(FRL,1952c, MRID 00001523). Growth rate was depressed at the highest
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dose. The animals used were part of a reproduction study (discussed in the
section on reproduction in this review), and the total nunber of test
animals was too low; therefore, this cannot be considered an adequate
chronic test. Testing must be repeated in the rat utilizing, if possible,
lead-free test material.
CNCOGENICITY (163.82-2)
The minimum requirement for oncogenicity, is testing in two mammalian
species, preferably the rat and mouse, using the technical formulation.
This study is required for dichlone because certain of its uses require a
tolerance. No oncogenicity tests are available on dichlone that meet
currently accepted protocols. No oncogenic potential was noted in mice
given dichlone orally for 18 months (21 days by gavage at 10 mg/kg/day,
then in feed at 30 ppm) or by a single injection (21.5 mg/kg) (Innes et
al., 1969, MRID 05004401 and Bionetics Research laboratories,1968, MRID
05010016). However, because of the large number of shortcomings in the
design and conduct of these tests, results were inconclusive. Additional
testing is required in the rat and mouse.
TERATOGENICITY (163.83-3)
The minimum requirement for teratogenicity is testing in two mammalian
species using technical formulations.
This study is required for dichlone because certain of its end-uses require
a tolerance.
No teratogenicity studies are available for dichlone. Testing in two
mammalian species is required.
REPRODUCTION (163.83-4)
The minimum requirement for reproduction is testing in one mammalian
species, preferably the laboratory rat, using the technical formulation and
lasting for two generations.
This study is required for dichlone because certain of its uses require a
tolerance.
Technical
Phygon (exact dichlone content unspecified) with lead contamination of 600
ppm was administered in the diet at concentrations of 0, 500, 1,580, or
5,000 ppm to groups of rats (10 male and 10 female rats) from about 25 days
of age (FRL, 1952c, MRID 00001523). There was no indication of impaired
ability to conceive and bear litters in any dose group. However,
throughout all the matings of the FQ generation and the two matings of
the F, and F~ generations, a pattern was established in which the
animals in the high-dose group had lower weights (at birth, at weaning, and
at mating) and produced smaller litters with poorer survival to weaning
than did the control at the two lower dose groups. The interpretation of
these effects is made difficult by the fact that apparent unpalatability of
the high-dose diet led to reduced food consumption. The growth depression
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in the adults might be attributable to this. Ihe fetal effects might also
be attributable indirectly to reduced food consumption because of reduced
maternal ability to provide adequate nutrition.
Ihe group sizes were not sufficiently large, particularly at the high-dose
level, and histopathological examinations were not performed on the FI
adults or on F-^ and F- weanlings. Therefore, this study can only give
supplementary information on the reproductive effects of Phygon.
Additional testing in the laboratory rat is required.
MUTAGENICITY (163.84-1 through-4)
The following studies represent only the minimum requirements for data on
the potential heritable effects of dichlone.
1. A mammalian in-vitro point mutation test.
2. A sensitive sub-mammalian point mutation test. (Bacteria, fungi,
insect).
3. A primary ENA damage test (i.e. sister chronatid exchange or
unscheduled DNA synthesis).
4. A mammalian in-vitro cytogenetics test. If this test suggests a
positive result, a dominant lethal or heritable translocation test
may be required.
After the results of 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's mutagenic testing requirements are not final, the
standards for these tests should be based on the priciples set forth
therein (43 FR 37388, August 22, 1978). Protocols and choices of test
systems should be accompanied by a scientific rationale. Substitutions of
test systems for those listed above will be considered after discussion
with the Agency.
The requirements should be considered an interim guide and not final Agency
policy. However, the Agency does consider the above testing scheme to be
a reasonable minimum requirement.
Mutagenicity testing is required for dichlone because certain of its uses
require a tolerance. A test for gene mutations in Salmonella using
dichlone (Anderson et al., 1972, MRID 05001460) was inadequate because of
several deficiencies in reporting (e.g., criteria for judging results
positive or negative were not stated) and the fact that no metabolic
activation system was used.
METABOLISM IN LABORATORY ANIMALS (163.85-1)
The minimum data requirements for metabolism require testing in the
laboratory rat with analytically pure compound of the active ingredient to
determine absorption, distribution, metabolism and excretion of the
compound.
A metabolism study is required for dichlone because the product requires a
chronic feeding study and an oncogenicity study. Testing is required.
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CLINICAL TRIALS
No clinical studies in humans have been conducted using dichlone.
EMERGENCY TREATMENT
No information on the prevention and treatment of dichlone intoxication is
available. This information is required.
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TOXICOLOGY BIBLIOGRAPHY
05001460 Anderson, K.J.; Leighty, E.G.; Takahashi, M.T. (1972) Evaluation
of herbicides for possible mutagenic properties. Journal of
Agricultural and Food Chemistry 20(3):649-656.
05010016 Bionetics Research Laboratories (1968) Evaluation of Carcinogenic,
Teratogenic, and Mutagenic Activities of Selected Pesticides
and Industrial Chemicals. Vol. I: Carcinogenic Study.
Bethesda, Md.: National Cancer Institute, Division of Cancer
Cause and Prevention. (National Cancer Institute report no.
NCI-DCCP-CG-1973-1-1; available from: NTIS, Springfield, VA;
PB-223 159)
00001521 Food Research Laboratories, Incorporated (1952) Acute Oral Tbxici-
ty: [Phygon]. (Unpublished study received Dec 22, 1952 under
unknown admin, no.; prepared for Naugatuck Chemical Co., Div. of
United States Rubber Co., submitted by Uniroyal Chemical,
Bethany, Conn.; CDL:108443-C)
00001522 Food Research laboratories, Incorporated (1952) Dermal Ibxicity
Studies: [Phygon]. (Unpublished study received Dec 22, 1952
under unknown admin, no.; prepared for Naugatuck Chemical Co.,
Div. of United States Rubber Co., submitted by Uniroyal
Chemical, Bethany, Conn.; CDL:108443-D)
00001524 Food Research Laboratories, Incorporated (1952) Dog Feeding
Studies: [Phygon]. (Unpublished study received Dec 22, 1952
under unknown admin, no.; prepared for Naugatuck Chemical Co.,
Div. of United States Rubber Co., submitted by Uniroyal
Chemical, Bethany, Conn.; CDL:108443-F)
00001523 Food Research laboratories, Incorporated (1952) Rat Feeding
Studies: [Phygon]. (Unpublished study received Dec 22, 1952
under unknown admin, no.; prepared for Naugatuck Chemical Co.,
Div. of United States Rubber Co., submitted by Uniroyal
Chemical, Bethany, Conn.; CDL:108443-E)
05004401 Innes, J.R.M.; Ulland, B.M.; Valerio, M.G.; Petrucelli, L.;
Fishbein, L.; Hart, E.R.; Pallotta, A.J.; Bates, R.R.; Falk,
H.L.; Gart, J.J.; Klein, M.; Mitchell, I.; Peters, J. (1969)
Bioassay of pesticides and industrial chemicals for
tumorigenicity in mice: a preliminary note. Journal of the
National Cancer Institute 42(6):1101-1114.
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Chapter VI
Residue Chemistry Chapter
DISCIPLINARY REVIEW
Residue Chemistry Profile
Generic Data Gaps
Required Labeling
Residue Chemistry Profile
Dichlone is marketed in the USA as a herbicide (plant regulator) and as a
fungicide. The metabolism and/or pathway of degradation of dichlone when
applied to aquatic areas and agricultural crops has not been detailed.
There is seme indication in the literature that dichlone in solution under
ordinary laboratory conditions decreases in concentration with time. When
similar solutions of dichlone were exposed to sunlight, conversion products
were noted. The major conversion product was determined to be 2-chloro-3
phenyl-l,4-naphthoquinone. No metabolism or breakdown patterns of dichlone
were identified in plants and animals. Additional studies should be
submitted exhibiting the nature of the major residues when dichlone is
applied to plants and digested by animals.
Assuming that dichlone per se is the only residue to be determined,
adequate analytical methods are available for analysis in agricultural
conmodities such as apples, beans, celery, cherries, peaches, plums (fresh
prunes), tomatoes and strawberries.
Residue studies show the use of certain application rates of dichlone on
apples, beans, celery, cherries, peaches, plums (fresh prunes), tomatoes
and strawberries. These studies show that the residues of dichlone per se,
resulting from these certain applications, do not exceed the established
pesticide tolerances for the above commodities. However, the residue
studies do not reflect residues which could result from the latest
registered uses including the maximum proposed rates. Accordingly,
additional residue studies have to be submitted to justify the registered
uses and established tolerances.
Because some by-products of treated crops, such as apple pomace, bean
vines, forage and hay and tcmato pulp are fed to cattle, horses, pigs and
other farm animals, residue studies should be submitted reflecting the
extent to which residues of these commodities are fed to food animals.
These include residue studies on cover crops in fruit orchards that are
being grazed by food animals. If the residue studies indicate that food
animals are fed agricultural commodities carrying residues, then animal
feeding studies are needed to reflect the degree of transfer of residues to
the meat and milk of these animals.
There are no records of regulatory incidents involving the enforcement of
dichlone tolerances.
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Generic Data Gaps
Metabolism and degradation studies indicating the nature of the residue in
plants and animals caused by an application or by the feeding of dichlone
have not been reported.
If the final resulting residue is identified as being different from
dichlone per se, analytical methodology is needed to identify and quantify
these residues on treated crops, their by-products and incidental
commodities (cover crops in orchards).
Residue data have to be submitted reflecting dichlone residues as a result
of the maximum registered usage rate, in samples taken on certain dates
after the application, in order to establish a time lapse degradation
pattern for the residues. Residue studies reflecting dormant applications
in combination with other applications to apple and peach trees are
required.
Residue processing studies have to be submitted showing the amount of
dichlone residue in apple pomace and tcmato pulp. If a concentration of
residue in apple pomace and tomato pulp is indicated to the extent that the
residue level exceeds that of the tolerance level established for the raw
agricultural commodity, a Food Additive tolerance for the apple pomace and
the tomato pulp will be required.
Residue studies reflecting the persistence of dichlone residues in water
resulting from the proposed uses are essential in determining whether
appropriate tolerances for potable water, fish, irrigated crops, etc. will
have to be established. The Office of Pesticide Programs (OPP) will
transfer scientific information about dichlone to EPA's Office of Drinking
Water (ODW) so that ODW may consider monitoring for dichlone residues in
water.
Animal feeding studies have to be submitted to establish the extent of
transfer of residues to meat and milk of animals as a result of the maximum
registered uses.
All residue studies should be supported by storage stability studies if
samples were held in storage before analysis. Handling history of the
samples should accompany the residue studies.
Required Labeling
Certain label restrictions will depend on the content of available data to
be submitted. For instance, a lack of residue data on cover crops could be
handled through a label restriction like "do not graze livestock on cover
crops in treated orchards."
Since there are registered uses which direct the application of dichlone to
lakes (recreational areas) and farm ponds, there is a reasonable
expectation that dichlone may be carried over and accunulated in potable
water, fish, irrigated crops and livestock. In the later case, residues
may result in meat and milk.
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Accordingly, to prevent hunan exposure by the drinking of treated water,
the use of treated water for livestock, the taking of fish from treated
water, the use of treated water for irrigational purposes, and the drainage
of treated water into flowing streams, appropriate tolerances instead of
label restrictions may be necessary for the affected ccnmodities.
Ihere is an indication that the presently maximum registered application
rates are different from those in effect when the tolerances were
established. All current and future label use directions should be
consistent with the restrictions specified in the Use Restriction Section
of the Topical Discussions for each crop.
Accordingly, the required labeling will depend on the fulfillment of the
generic data gaps.
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TOPICAL DISCUSSIONS
This Registration Standard for dichlone is concerned with formulations
containing a single active ingredient. Conclusions or implications derived
from data on single active ingredient formulations do not necessarily apply
to multiple active ingredient formulations.
USE PATTERNS
Dichlone is marketed in the USA as a fungicide and a herbicide. As a fungi-
cide, dichlone is applied to various agricultural connodities and ornament-
al plants to control a number of plant diseases. As a herbicide, dichlone
is applied to aquatic environments such as lakes, ponds, and swimming pools
to control blue-green algae.
Dichlone is formulated as a flowable concentrate, a ready-to-use product, a
wettable powder and a dust. The flowable concentrate is formulated with
50%, 5%, 4.9% and 1.5% active ingredient. The ready-to-use product
formulation contains the active ingredient at 1.5%.
The wettable powder is formulated with 50% active ingredient; the dichlone
dust with 9%, 6%, 3% and 2% active ingredient.
When the above formulations are being used, the following should be
observed: "Dichlone is toxic to fish, bees, pets and wildlife. Therefore,
keep out of lakes, streams, or ponds unless they are the specific site
being treated. Do not contaminate water by cleaning of equipment or
disposal of waste. Keep away from domestic animals and foodstuffs. Do not
use in sprays containing lime, calcium arsenate, or dinitro conpounds, oil
or emulsifiable concentrates. Do not apply when runoff is likely to occur,
or within 10 to 14 days of an oil spray. Do not apply prior to or during
periods of excessively high (85 F) temperatures, nor when weather
conditions favor drift of dust from treated crop areas."
Aquatic Uses
When dichlone is applied to aquatic areas for the treatment of blue-green
algae, the following use-limitations are required on the labels:
Lakes and ponds
Flowable concentrate: Use 0.333 gallons of 5% dichlone concentrate per
acre-foot of water (spray) about every three weeks.
Wettable powder: Use 1.1 oz. dichlone/acre - foot of water every two or
three days.
Swimming Pools
Flowable concentrate: Use 1 qt. 1.5% dichlone concentrate/50,000 gallons
of water every week or less.
Wettable powder: Use 0.5 oz. dichlone/50,000 gallons of water every week
to every two weeks.
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Ready-to-use product: Use 0.5 gal. 1.5% dichlone formulation/30,00 gallons
of water every two weeks. :
NOTE: Always apply when water temperature is above 55 F.
Agricultural and Ornamental Uses
When dichlone is used as a fungicide, it is applied to various agricultural
crops and ornamentals for the prevention or treatment of various plant
diseases. The treatment may consist of a single application or a series of
applications with each one being applied at a designated stage of bud,
blossom, fruit and/or leaf development.
Ornamental Use
The recommended rates of application for ornamentals are: On roses use a
multiple foliar spray at 0.125 Ib. a.i./lOO gal. every seven days after
leaves first appear.
On azaleas, use a multiple foliar spray at 0.25 Ib. a.i./lOO gallons every
two days for the treatment of petal blight.
Agricultural Uses
The proposed maximum rates of application of dichlone to agricultural
commodities will be described in the section covering the residues of
dichlone on the agricultural crops.
METABOLISM (in plants and animals)
No information on the fate of dichlone has ever been submitted by
manufacturers or interested parties. An article by White et _al. (1969,
MR1D 05001410) showed that standard solutions of dichlone decreased in
concentration with time under ordinary laboratory conditions. There was a
simultaneous increase in the concentration of degradation and/or conversion
products. The major conversion product was determined to be 2-chloro-3-
phenyl-l,4-naphthoquinone. This same conversion product was noted after a
solution of dichlone was exposed to sunlight.
A study by Owens (1969, MRID 05002878), shows that dichlone, when reacted
(under laboratory conditions) with glutathione, produced an indeterminable
product which was assumed to be a mixture of mono- and di-substituted
products.
This limited information gives some indication of the possible fate of
dichlone. However, for registration purposes, more extensive studies,
preferably some studies using radio-tracer techniques, should be
submitted. Presently, the fate of dichlone residue in plants and animals is
not adequately explained. This is a data gap.
ANALYTICAL METHODOLOGY
Until the path of metabolism and degradation of dichlone residues in plants
and animals can be clarified, it is assumed that the residue of concern is
dichlone per se. Accordingly, the methods at hand for the analysis of
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dichlone will determine dichlone per se (the parent compound). Hie
accepted method for the determinatiorTof dichlone in agricultural crops,
i.e., peaches, apples, strawberries, stringbeans and tomatoes, is published
in the Pesticide Analytical Manual, Volume II. Ihe principles of the above
method are explained in Burchfield (1948, MRID 05001359) and Bornmann
(1957, MRID 05002988). This method was subjected to thorough analytical
research for accuracy and sensitivity. According to this method,
vegetables are stripped with benzene, the extract cleaned up on an
activated Florisil colunn and eluted with 1% acetone in benzene. Any
residues of dichlone which are present will react with dimethylamine to
produce an intense orange color. Ihe dimethylamine reaction product is
then read spectrophotonetrically at 495 millimicrons and compared with
previously established dichlone-standard readings.
Additional work proving the adequacy of the above method is shown in Miller
(1965, MRID 05001416) and lane (1958, MRID 05001408). The first study
reports results on 10 collaborators who fortified peach-, tomato-, and
strawberry samples with dichlone in the 0.5-4.0 ppm range. The method
sensitivity was found to be 0.25 ppm. Recoveries of dichlone residues in
peaches were 78-112%; in tomatoes, 88-110% and in strawberries, 80-105%.
In Lane (1958, MRID 05001408), practically the same method was tried out on
peaches, apples, strawberries, stringbeans and tomatoes. The fortification
levels of dichlone ranged from 0.4 ppm to 1.0 ppm resulting in recoveries
of 85% to 101%, averaging 91% for 18 crops. These data are very consistent
and support the adequacy of the method.
In Zweig (1972, MRID 05001656) the author discusses a gas chromatographic
method for the analysis of dichlone residues in or on agricultural crops.
Since no particulars as to the operation of the method are reported, no
opinion can be offered as to its adequacy with regard to recovery and
sensitivity.
For the analysis of dichlone residues in tobacco a method is presented
in Hoffman (1965, MRID 05001490) by which dichlone can be determined
independently of other chemicals applied, such as maleic hydrazide. One
option is to extract the crop sample with benzene and water, then draw off
the water, concentrate the benzene and cleanup the benzene extract on a
florisil column eluting the column with methylene chloride. Evaporate the
eluate and take up dichlone residues in absolute alcohol and add
triethylamine to develop a blue color. Measure the absorbance of the
colored solution at 650 millimicrons. Recoveries from treated tobaccos
were found in the range of 93-100%. Maleic hydrazide does not form a
colored complex with triethylamine.
Another option is to extract the sample with methylene chloride, filter the
extract and reduce the volume to about 1 ml. Apply the sample to a T.L.C.
plate and develop the plate in 1:1 chloroform: trichloroethylene.
Determine the dichlone residue band under a long-wave ultraviolet light
source with a dichlone reference spot run on the same plate. Scrape off
the band representing the dichlone residue and extract with methylene
chloride by mixing with a stirring rod. Filter and extract two more times
with methylene chloride. Combine the methylene chloride extracts and
reduce volume. Spot an amount representing a known quantity of sample and
also spot standard amounts of dichlone. Develop the plate as before. When
the plate is dry, spray with diethylamine and estimate the amount of
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dichlone by comparing sample spot with standard spots. This latter method
offers a simple technique for the fast screening of samples.
Quantitatively, the spectrophotometric procedure is far better for
determining dichlone residues in tobaccos.
The above detailed spectrophotcmetric method was researched in regard to
the use of dimethylamine, diethylamine and triethylamine in color
development for the reaction with dichlone residues. It was found in a
tryout with cherries that the respective absorbance maxima were 484, 492
and 672 millimicrons. The use of triethylamine with an absorbance maximum
wavelength of 672 millimicrons was less susceptible to interference from
extraneous material.
The analysis of dichlone by the use of micro-coulometric gas chromatography
was researched in Burke (1962, MRID 05002348). The method is discussed as
a rapid pesticide screening procedure. The relative retention ratios of 71
pesticides, one being dichlone as compared with aldrin, are reported.
Various cleanup procedures are discussed relative to the crop being
sampled. The instrumentation used was a Dohrmann micro-coulcmetric gas
chromatograph equipped with an aluminum colunn, 1/4 inch outside diameter
by 6 feet long, packed with 30/60 mesh acid-washed Chronosorb P coated with
20% Dow-Corning high vacuum silicone grease. Helium was the carrier gas at
120 ml/min. Column temperature was 220 C and the injection block
temperature 250 C. The relative retention time of dichlone relative to
that of aldrin is 0.59.
For the analysis of dichlone in water, an extraction procedure is discussed
in Faust (1965, MRID 05003909) consisting of its steam distillation from an
acid aqueous medium, after which chloroform for ultraviolet detection is
enployed. Specifics of this method are discussed in Newell (1954?, MRID
00001515). This method is adequate for the analysis of dichlone from water
samples in the range of 8-250 parts per billion with an average recovery of
86%. Cne of the negative factors affecting the rate of recovery is that
some hydrolysis of the 2,3-dichloro-l,4-naphthoquinone to 2-hydroxy-3-
chloro-l,4-naphthoquinone occurs. Accordingly, a 100% recovery is seldom
achieved. Solutions of 500 and 700 ppb were run but recoveries dropped to
70%.
Additional submissions, (Patrashku, 1971, MRID 05004240; Mills, 1972, MRID
05004950; and Kovacs, 1966, MRID 05003005) discuss a Russian colorimetric
method which has very little practical applicability in the USA because of
the suggested Russian instrumentation. Two submissions contain practical
cleanup procedures that could have been used in the analysis and
identification of dichlone residues in agricultural crops. However, the
availability of recently developed, advanced and more sensitive methods
renders these two procedures obsolete.
RESIDUE DATA
Field residue data for dichlone reflects the registered use in regard to
dosage rate, mode of application, number and timing of treatments,
formulations used and geographical areas represented. No metabolism data
regarding the fate of dichlone residues in or on agricultural crops were
submitted. Accordingly, there is no way of knowing whether or not dichlone
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per se is the final degradation residue to be determined. However, for the
sake of evaluating the residue data submitted, it has to be assumed that
dichlone per se is the final residue to be measured.
The analytical method used to generate the residue data involves the
stripping of the agricultural crop with benzene, filtering of the extract
and concentrating to a smaller volume. An aliquot of the extract is mixed
with aqueous dimethylamine for color development with possible dichlone
residues. The intensity of the color is then measured on a Beckman DU
spectrophotometer. This method was tried out on pole beans, cherries,
plums, prunes and strawberries. Samples were fortified over a range from
0.13 ppm to 1.79 ppm. Recoveries ranged from 83%-109%, averaging 91%.
This method is deemed adequate for the purpose of collecting residue data.
Residues in or on Apples
No storage stability study of dichlone residues on agricultural crops was
submitted. The dichlone residue data at hand do not provide a history of
the analyzed samples concerning the dates of collection, whether the
samples were kept frozen or when the analyses were performed.
The directions for use on apples call for delayed dormant and for foliar
applications up to one day prior to harvest. Two kinds of applications are
offered, i.e., single or multiple dust applications at a maximum rate of
1.5 Ib. a.i./per acre, (1 day PHI indicated); and single or multiple spray
applications at a maximum rate of 4 Ib. a.i./acre/application (1 day PHI
indicated). Seme rates of application are expressed in terms of pounds of
a.i./lOO gallons of water applied to the point of runoff; however, the
maximum amount applied per acre is not indicated. The maximum amount of
dichlone applied per acre is dependent on the number and size of trees per
acre and whether or not the application is made to a dormant tree or a full
covered tree. When applied to the point of runoff, the rate of application
expressed in this manner should correct for the number and size of trees.
The available residue data (United States Rubber, 1956, MRID 00001510),
reflect seven single 1/2 Ib. a.i./lOO gallon spray applications to apple
trees in six different states of USA. (One application reflects a rate of
1 Ib. a.i./lOO gallons). The interval between spray and harvest varies
from zero days to nine days. The maximum dichlone residues on apples
resulting from 1/2 Ib. a.i./lOO gallon is 1.2 ppm at one day, 0.68 ppm at
six days, 0.24 ppm at seven days, 0.1 ppm at eight days and 0.00 ppm at
nine days (sensitivity of the method 0.2 ppm). The one application of 1
Ib. a.i./lOO gallons of water reflects residues of 1.07 ppm at zero day and
no residues (0.00 ppm) at seven weeks (sensitivity of the method 0.2 ppm).
Apple blanks are reported at 0.0 ppm (sensitivity of the method 0.2 ppm).
These residue data are not adequate to support a 3 ppm tolerance for
residues in or on apples because: (1) The residue data reported do not
reflect the maximum proposed dosage rate. (2) The residue data do not
reflect residues resulting from proposed dust applications. (3) The
residue data do not reflect residues resulting from registered multiple
dust or spray application. (4) The data do not reflect the registered
dormant use of apple trees. (5) Although enough geographic areas are
represented, not enough data are presented reflecting the same conditions
in the same geographic area.
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Residue on Peaches
Ihe directions for use on peaches call for dormant and foliar applications
up to seven days before harvest.
Two kinds of applications are offered, i.e., single or multiple dust
applications at a maximum rate of 1.5 Ib. a.i./per acre (3 and 7 day PHI's
indicated) and single or multiple spray applications at a maximum rate of
2.5 Ibs. a.i./acre/application (7 day PHI indicated). There are sane rates
of application which are expressed as pounds of a.i. per 100 gallons of
water.
The available residue data for peaches (United States Rubber, 1956, MRID
00001510) reflect seven single 1/2 Ib. a.i./lOO gallon spray applications
to the foliage of peach trees in five different states of the USA. The
interval between spray and harvest varies from zero to nine days. The
maximum reported residue on peaches is 1.7 ppm in four studies in three
different states at one day after the application; 1.4 ppm six days after
the application and 0.3 ppm eight and nine days after the application.
Crop blanks are reported as 0.0 ppm (sensitivity of the method 0.2 ppm).
These residue data are insufficient for the same reasons as stated in
the above section on residues on apples. These data do not support a
tolerance of 3 ppm for residues in or on peaches.
Residues in or on Tomatoes
Residue data reflecting the use of dichlone on tomatoes are presented in
Naugatuck Chemical (1955?, MRID 00001534). The directions for use call for
foliar applications, applications to the plant bed and transplant dip-
applications. The transplant dip-application is a single application at a
rate of 0.5 Ib. a.i./lOO gallons. The plant bed is treated with multiple
spray applications at a maximum rate of 0.5 Ib./lOO gallons not to exceed
1.25 Ib. a.i./acre/application. The foliar applications can be made by
multiple dust applications at a maximum rate of 0.6 Ib. a.i./acre at
unspecified frequency, or by multiple spray applications at a maximum rate
of 1.25 Ib. a.i./acre. Note: do not exceed 1.25 Ib. a.i./acre application.
The reported results were obtained by a method practically identical to the
one reported in Miller (1965, MRID 05001416) and Lane (1958, MRID
05001408). This method is deemed adequate for the purpose intended.
Dichlone can be used as late as the day of harvest. The residue data
reflect five samples, all representing multiple spray application in one
single location (State of Connecticut).
No sample history is reported. Two samples reflecting multiple spray
applications at a rate of 0.5 Ib. a.i./acre show, at day zero, a residue of
0.92 ppm (three applications) and at seven days after the last application,
0.19 ppm (nine applications). One sample representing four spray
applications at a rate of 0.75 Ib. a.i./acre shows, at day zero, a residue
of 1.25 ppm. One sample reflecting spray applications at 1 Ib. a.i./acre
shows at zero day a residue of 1.43 ppm. One sample reflecting residues
resulting from four spray applications at 1-1/2 Ibs. a.i./acre shows at
day zero a residue of 2.28 ppm. These residue data are not adequate to
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support a 3 ppm tolerance for residues in or on tomatoes because: (1) The
residue data reported do not reflect all maximum registered uses such as
dusts, dips and use on seed beds. (2) Ihe data do not reflect residues
that result from various uses in different geographic areas.
Residues on Celery
The directions for use on celery call for multiple foliar dust applications
at a maximum rate of 0.75 Ib. a.i./acre every 7-10 days. Multiple foliar
spray applications at a maximum rate of 0.50 Ib. a.i./acre (not to exceed
0.75 Ib. a.i./acre/application) are suggested every 5-7 days beginning 7-10
days after plant set.
The residue data at hand (Naugatuck Chemical, 1955?, MRID 00001534) were
collected by the same method as that used for the collection of the tomato
residue data. This method is deemed adequate for the intended purpose.
Ihe reported residue data are from one spray location in Florida. Fully
grown celery was sprayed with dichlone at the rate of 0.25 Ib. a.i./acre
(1/2 Ib. Phygon XL/acre) and was harvested the same day. Ihe celery was
topped but not trimmed. Five samples were analyzed and residues were
reported to range from 0.2-1.5 ppm (average 0.68 ppm for five values).
Ihe residue data are not adequate to support a 3 ppm tolerance for residues
in or on celery because: (1) Ihe residue data reflect half the registered
spray-use of 0.5 Ib. a.i./acre. (2) Ihe residue data do not reflect the
maximum registered dust use of 0.75 a.i./acre/application. (3) Not enough
geographic representation of growing areas are represented. (4) Ihe data
do not reflect possible residues resulting from applications in the same
geographic area. (5) The residue data do not reflect the use of multiple
dust applications to celery at a maximum proposed application rate.
Residues on Beans
Ihe directions for foliar treatment of beans proposed multiple dust
applications at a maximum rate of 1.11 Ib. a.i./acre every seven days
beginning at pre-bloom, but not within seven days of harvest. Foliar
treatment of beans by means of a spray at a maximum registered rate of
1-1/8 Ib. a.i./150 gallons of water/acre every seven days for five
applications, beginning just before bloom, is an alternate registered use.
Do not apply within seven days of harvest.
The analytical method used to determine the residues was the same as that
used previously for apples and peaches. The lower limit of sensitivity
claimed is 0.2 ppm. The recoveries at fortification levels of 0.13 ppm to
0.64 ppm range from 90%-109%. This method is deemed appropriate for the
purpose intended.
The reported data (United States Rubber Company, 19??, MRID
00001529)reflect residue studies on pole beans and string beans in three
locations in the State of Washington. Residue data on green beans were all
obtained after single applications of dust at a maximum rate of 0.9 Ib.
a.i./acre. ND data were presented on spray-treatments. Eight samples from
three locations were analyzed. Seven consisted of "pole" beans and one of
string beans. Maximum residues reported were 0.4 ppm in "pole" beans
harvested five days after treatment with 0.9 Ib. dichlone per acre. All
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other samples, representing rates of 0.6-0.9 Ib. a.i./acre and preharvest
intervals 9-21 days, showed residues of 0.0-0.1 ppm (sensitivity of method
0.2 ppm). All blanks were reported as 0.0 ppm (sensitivity of method
0.2 ppm). The reported residue data are not adequate to support a 3 ppm
tolerance of residues in or on beans because: (1) Ihe residue data do not
reflect the maximum registered use of 1-1/8 Ib. a.i./acre. (2) Ihe
residue data do not reflect multiple dust applications. (3) The residue
data do not reflect the use of multiple spray applications at the maximum
registered rate. (4) Not enough geographic areas were represented. (5)
Not enough data are presented reflecting uses in the same geographic area
at a maximum registered application rate.
Residues in or on Cherries
Ihe directions for use on cherries propose a single delayed dormant
application at the maximum application rate of 1.2 Ib. dichlone dust/acre.
Multiple foliar dust applications are proposed at a maximum application
rate of 1.5 Ib./acre. A preharvest interval of three days is indicated.
Multiple foliar spray applications are proposed at maximum application
rate of 0.50 Ib. a.i./lOO gallons, not to exceed 5 Ib.a.i./acre/application.
Data are reported (United States Rubber Company, 19??, MRID 00001529) on
residues from six samples of cherries from three states (a total of five
locations). All were sprayed (apparently single applications) at 0.25 Ib.
a.i. 100 gallons. Maximum residue found was 0.4 ppm on a sample harvested
seven days after treatment. All other samples showed residues of 0.0
(sensitivity of method 0.2 ppm) -0.2 ppm,representing pre-harvest intervals
of 0, 5 and 7 days. Recoveries from knowns at 0.45-0.90 ppm were 83-106%;
all blanks reported as 0.0 ppm.
The reported residue data are not adequate to support a 3 ppm tolerance for
residues in or on cherries because: (1) Ihe residue data do not reflect
the maximum registered use of 0.5 Ib. a.i./lOO gallon. (2) Ihe residue
data do not reflect the use of multiple dust and multiple spray
applications at the maximum registered rate. (3) Not enough residue data
were reported resulting from the maximum registered use at various days
after the application, establishing a residue decline pattern.
Residue in or on Plums and Fresh Prunes.
Ihe directions for use on plums reflect a single delayed dormant dust
application at the maximum rate of 1.2 Ib. a.i./acre. The directions for
foliar treatment indicate multiple dust applications at a maximum rate of
1.5 Ib. dichlone/acre (three-day PHI indicated). Also, foliar spray
applications are suggested at a maximum rate of 0.375 Ib./lOO gallons, not
to exceed 1.25 Ib. a.i./acre. A three-day PHI is indicated.
The directions for use on prunes suggest a foliar multiple dust application
at a maximum rate of 1.5 Ib. a.i./acre (a three-day PHI is indicated). In
addition, foliar multiple spray applications are registered at a maximum
rate of 0.375 Ib. a.i./lOO gallons of water, not to exceed 1.25 Ib.
a.i./acre. A multiple spray application is suggested at a maximum rate of
0.25 Ib. a.i./acre with a three-day preharvest interval.
Data are reported (United States Rubber Company, 19??, MRID 00001529) on
residues on three samples of plums and two samples of prunes (fresh) from
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four states. All received single applications of sprays at 0.25 Ib.
a.i./lOO gallons. All samples were harvested seven days after spraying.
The maximum residue was 0.6 ppm on a sample of plums fron California;
residues on all other samples were 0.0 (sensitivity of method 0.2 ppm)~0.1
ppm. Recoveries using samples fortified at 0.63 and 0.90 ppm were 86%-
100%. All blanks were reported as 0.0 ppm (sensitivity of method 0.2
ppm).
The reported residue data are not adequate to support a 3 ppm tolerance for
residues in or on plums and fresh prunes because: (1) The residue data do
not reflect the maximum registered spray application a rate of 0.375 Ib.
a.i./lOO gallons. (2) The residue data do not reflect the use of multiple
dust and multiple spray applications at the maximum registered application
rate. (3) No data were reported at various times, starting at zero day,
which would permit the establishment of a residue decline pattern. (4) No
residue data were submitted reflecting the delayed dormant use. Generally,
not enough data is reported to justify the maximum registered uses for
plums and fresh prunes.
Residues in or on Strawberries
Tne directions for use on strawberries suggest a multiple foliar spray
application at the maximum registered rate of 0.375 Ib. a.i./200
gallon/acre every 10-14 days. Eb not apply within three days of harvest.
The residue data reported for strawberries (United States Rubber
Company, 19??, MRID 00001529) reflect the use of dichlone on seven samples
of strawberries from five states. All received single sprays at 0.375-0.5
Ib. a.i./acre. The harvest of the samples was 3-19 days after spraying.
Of two samples frcm different locations receiving 0.5 Ib. a.i./acre
harvested three days after spraying, a maximum residue of 10.5 ppm was
reported. Of two samples from two other locations receiving 0.375-0.5 Ib.
a.i./acre and taken seven days after spraying, the maximum residue was 0.88
ppm. Other samples taken at 6-19 days after spraying had residues of 0.0
(sensitivity of method 0.2 ppm)-0.1 ppm. Recoveries using samples
fortified at 9 ppm were 96-98%; at 1.8 ppm, 86% and at 0.43-0.90 ppm, 92-
93%. All blanks were reported as 0.0 ppm (sensitivity of method 0.2 ppm).
The reported residue data are not adequate to support a 15 ppm tolerance
for residues in or on strawberries because: (1) The residue data do not
reflect a residue decline pattern justifying the 15 ppm tolerance. (2)
Overall, not enough is reported to reflect the level of residues that may
result from the maximum registered use. (3) No sample history is reported
indicating the date of analysis as compared to the time of harvest. (4)
No sample storage report was submitted.
Residues in Meat and Milk
Consideration is given to the possible feeding of treated crops and
by-products to cattle, horses, pigs, and other farm animals. It is a well-
known agricultural practice that apple pomace (wet or dry) is fed to cattle
at ca. 1/3 the daily diet. Tomato pulp (dried) is fed to beef and dairy
animals at 10-25% of the daily diet; to pigs and horses at 10% of the diet
and to finishing lambs at 15-25% of the diet. Bean vines, forage and hay
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can be fed to beef cattle at up to 20% of the diet and to dairy cows at up
to 37% of the diet. No residue studies were reported for the indicated
commodities including cover crops in fruit orchards which may be grazed.
These residue studies are essential in order to determine the extent to
which dichlone residues are fed to food-animals. If these commodities
containing residues are fed to food-animals, then feeding studies with
ruminants and nonruninants should be performed at several dosage levels;
including exaggerated dosages, preferably threefold and tenfold to
determine whether or not residues will transfer to meat and milk. No
feeding study with ruminants and nonruminants have been reported.
REGUIATORy INCIDENTS
No report was made on any regulatory action taken by FDA in regard to the
registered uses of dichlone.
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RESIDUE CHEMISTRY BIBLIOGRAPHY
05002988 Bornmann, J.H. (1957) Report on phygon. Journal of the
Association of Official Agricultural Chemists 40(1):273-274.
05001359 Burchfield, H.P.; McNew, G.L. (1948) The colorimetric
determination of 2,3-dichloro-l,4-naphthoquinone on seed.
Phytopathology 38:665-669.
05002348 Burke, J.; Johnson, L. (1962) Investigations in the use of the
micro-coulometric gas chromatograph for pesticide residue
analysis. Journal of the Association of Official Agricultural
Chemists 45(2):348-354.
05003909 Faust, S.D.; Hunter, N.E. (1965) Chemical methods for the
detection of aquatic herbicides. Journal of the American Water
Works Association 57(8):1028-1037.
05001490 Hoffman, I.; Parups, E.V.; Morley, H.V. (1965) Identification and
determination of dichlone residues in treated tobaccos.
Journal of the Association of Official Agricultural Chemists
48(5):1063-1066.
05003005 Kovacs, M.F., Jr. (1966) Rapid detection of chlorinated pesticide
residues by an improved TIC technique: 3 1/4 X 4" micro slides.
Journal of the Association of Official Analytical Chemists
49(2):365-370.
05001408 Lane, J,R. (1958) Determination of Phygon residues on food crops.
Journal of Agricultural and Food Chemistry 6(10):746-747.
05001416 Miller, G.A. (1965) Dichlone residues on foods. Journal of the
Association of Official Agricultural Chemists 48(4):759-762.
05004950 Mills, P.A.; Bong, B.A.; Kamps, L.R.; Burke, J.A. (1972) Elution
solvent system for Florisil column cleanup in organochlorine
pesticide residue analyses. Journal of the Association of
Official Analytical Chemists 55(1):39-43.
00001534 Naugatuck Chemical (1955?) The Results of Tests on the Amount of
Residue Remaining, Including a Description of the Analytical
Method Used. (Unpublished study received Jun 1, 1955 under 16;
submitted by Naugatuck Chemical, Div. of United States Rubber
Co., Naugatuck, Conn.; CDL.-092299-L)
00001515 Newell, J.E.; Mazaika, R.J.; Cook, W.J. (1954?) The Micro Deter-
mination of Phygon in Water. Undated method. (Unpublished
study received May 10, 1957 under 400-11; prepared by Naugatuck
Chemical, Div. of United States Rubber Co., submitted by
Uniroyal Chemical, Bethany, Conn.; CDL:120159-A)
05002878 Owens, R.G.; Blaak, G. (1960) Chemistry of the reactions of
dichlone and captan with thiols. Contributions from Boyce
Thompson Institute 20(8):475-497.
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05004240 Patrashku, F.I.; Sorokskaya, L.B.; Rekhter, B.A. (1971)
Gpredeleniye figona v rasteniyakh pri pomoshchi tonkosloinoi
khronatografii i fotonetricheskimi metodami. [Determination
ofphygon in plants by thin-layer chronatography and photometric
methods] Pages 181-183, In Trudy Vsesoyuznogo Soveshchaniya
po Issledovaniya Ostatkov Pestitsidov i Profilaktike
Zagrayazneniya Imi Produktov Pitaniya, Kbrmov i Vheshnei
Sredy,Metody Analiza, 2nd; 1970, Tallin(?). [Transactions of
the All-Union Conference on the Residues of Pesticides and
Prophylaxis of Contamination by Them of Foodstuffs, Feeds and
the Environment, Methods of Analysis, 2nd; 1970, Tallin(?).J
Edited by O.M. Tarim.
00001529 United States Rubber Company (19??) The Results of Tests on the
Mount of Residue Remaining, Including a Description of the Ana-
lytical Method Used: [Phygon]. (Unpublished study received Aug
12, 1955? under 188; CDL:090216-A)
00001510 United States Rubber Company (1956) [Phygon-XL Residue on Fruit].
(Unpublished study received Jan 15, 1957 under 400-11; submitted
by Uniroyal Chemical, Bethany, Conn.; CEL:003230-O)
05001410 White, E.R.; Kilgore, W.W.; Mallett, G. (1969) Phygon. Fate of
2,3-dichloro-l,4-napththoquinone in crop extracts. Journal of
Agricultural and Food Chemistry 17(3):585-588.
05001656 Zweig, G.; Sherma, J. (1972) Phygon (dichlone). Pages
584-585, In Analytical Methods for Pesticides and Plant Growth
Regulators. Vol. VI: Gas Chronatographic Analysis. Edited by
G. Zweig and J. Sherma. New York: Academic Press.
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Chapter VII
Ecological Effects Chapter
DISCIPLINARY REVIEW
Ecological Effects Profile
Ecological Effects Hazard Assessment
Data Gaps
Required Labeling
Ecological Effects Profile
A limited amount of information is available on the effects of dichlone on
birds, fish, aquatic invertebrates, aquatic plants, amphibians, and
beneficial invertebrates.
Subacute 8-day avian dietary studies on three species of upland game birds-
bobwhite quail (Colinus virginianus), Japanese quail (Coturnix c.
japonica) and ring-necked pheasant (Phasianus colchicus) - indicate
technical dichlone is practically nontoxic to this group of birds. The
values range from >4640 to >5000 ppm. An eight day dietary study on
mallard ducks resulted in an LC5Q >5000 ppm indicating technical dichlone
also is practically nontoxic to waterfowl.
Acute 96-hour LCcn's are available on both coldwater and warmwater fish.
Rainbow trout (Salmo gairdneri) and bluegill sunfish ( Lepomis
macrochirus had respective LC50 values of .034 ppm and .041 ppm. These
values are sufficient to characterize technical dichlone as being very
highly toxic to cold and warmwater fish. Additional acute studies on carp
(Cyprinus carpio )have confirmed that technical dichlone is very highly
toxic to warmwater fish.
Five species of freshwater aquatic invertebrates - including daphnids
(Daphnia magna) and amphipods (Gammarus fasciatus) have been tested
against technical dichlone. The subacute LCSO's range from 14 ppb to 45
ppb. These data indicate technical dichlone is very highly toxic to
freshwater aquatic invertebrates.
For algae the ix>-effect concentration is dependent upon the species.
Studies have shown a no-effect concentration ranging from 75 ppb (0.253
uM/D to 32 ppm (115.6 uM/1).
Aquatic macrophytes, emerged and submerged, apparently are quite tolerant
of dichlone. Ten species from various families and divisions were
unaffected at 12 ppm dichlone.
For terrestrial plants, the no-effect levels range from 3 lb/100 gal.
diluant for tobacco (senescence retardant), to 59 mg/tcmato seedling, to
2 oz./cwt of sugarbeet seed and 16 ppm for cucumber seed.
During seed treatment of leg ones, the nitogen fixing symbiont, Rhizobium ,
may be affected by a 1 to 2 oz./cwt treatment, however, the legume growth
and yield will not be affected.
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One study on an amphibian, the South African clawed toad (Xenopus
laevis ), examined the effects of dichlone on developing embryos. In this
short-term teratology study, dichlone produced effects at concentrations
greater than 75 ppb and 50% mortality within one day of exposure between
125 ppb and 150 ppb. These data suggest dichlone is very highly toxic to
early life stages of amphibians.
One scientifically sound beneficial insect study was conducted on a
wettable powder formulation containing dichlone. Phygon XI was tested
against the honey bee (Apis mellifera). There is sufficient
information to characterize the product as moderately toxic to bees when
ingested and relatively nontoxic to bees exposed to direct application or
dried residue. When bees were exposed to Phygon XI in orchards at 0.5 Ib.
of formulation/100 gals, the product was not toxic or repellent.
Ecological Effects Hazard Assessment
The Ecological Effects Branch anticipates that some of dichlone's use
patterns are likely to contaminate aquatic sites adjacent to treated fields
as well as vegetation in and around the target site. Aquatic organisms
appear to be sensitive to dichlone. Although environmental fate data are
not available, it is evident that the direct application of the 5% product
at 5 gallons per 1,000,000 gallons of water will produce a concentration of
0.25 ppm. This is about 32 times the acute LC50 (0.034 ppm) for rainbow
trout. This constitutes a hazard to fish, indicating the need for the
following label statement, "Consult your State fish and game agency before
applying this product. Fish may be killed at label application rates".
The Agency will address other aquatic concerns upon receipt of acceptable
envirormental fate data.
Data Gaps
All registrants of dichlone products must fulfill the data requirements as
summarized on pages 20 through 22. A full description of the data
requirements can be found in the Proposed Guidelines for the Registration
of pesticides in the United States, 43 FR 29696, July 10, 1978 and 45 FR
72948, November 3, 1980.
Ecological Effects Labeling Requirements
All manufacturing-use dichlone product labels must include the following
warning:
"This pesticide is toxic to fish and other aquatic organisms. Do not
discharge into lakes, ponds, or public water unless in accordance
with NPDES permit. For guidance, contact your Regional Office of the
EPA."
All labels for formulated dichlone products intented for use as fungicides
and as algaecides in swimming pools must include the following warning:
"This pesticide is toxic to fish and other aquatic organisms. Do not
contaminate water by cleaning of equipment or disposal of wastes."
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All labels for formulated dichlone products intended for use as algaecides
in lakes and ponds must include the following warning:
"This pesticide is toxic to fish and other aquatic organisms. Fish
may be killed at the label application rates. Do not apply to fish
bearing waters."
All labels for food crop and ornamental uses must bear a statement similar
to:
"This pesticide is toxic to fish."
Additional labeling will be deferred until the required data has been
received and evaluated.
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TOPICAL DISCUSSIONS
Corresponding to each of the Ibpical Discussions listed below is the number
of the section(s) in the 'Proposed Guidelines' (43 FR 29696, July, 10, 1978
and 45 FR 72948, November 3, 1980) which explain(s) the data that the
Agency will utilize to adequately assess dichlone's Ecological Effects.
Where no section number is listed, a minimum requirement has not been set
for such information.
Category of Test Guideline Number
Effects on Birds 163.71-1,2,4
Effects on Mammals 163.71-3
Effects on Freshwater Fish 163.72-1
Effects on Aquatic Invertebrates 163.72-2
Effects on Terrestrial Macrophytes 163.122-1
Effects on Algae 163.122-2
Effects on Aquatic Macrophytes 163.122-2
Nitrogent Fixation Potential 163.125-3
Effects on Amphibians
Effects on Beneficial Invertebrates
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the following are the categories of toxicity used in the topical
discussions.
Mammalian
Acute Oral (mg/Kg)
<10 very highly toxic
10-50 highly toxic
51-500 moderately toxic
501-2000 slightly toxic
>2000 practically nontoxic
Avian
Acute Oral (mg/Kg)
10-50
51-500
501-2000
>2000
Dietary (ppm)
<50
50-500
501-1000
1001-5000
>5000
Aquatic Organisms
ppm
0.1-1
>1-10
>10-100
>100
very highly toxic
highly toxic
moderately toxic
slightly toxic
practically nontoxic
very highly toxic
highly toxic
moderately toxic
slightly toxic
practically nontoxic
very highly toxic
highly toxic
moderately toxic
slightly toxic
practically nontoxic
*Category terminology taken from: Brooks, H.L. et al. (1973).
Insecticides, Cooperative Extension Service, Kansas State University,
Manhattan, Kansas.
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AVIAN SINGLE DOSE ORAL LD5Q (163.71-1)
Data on the single-dose oral LD5Q are required to support the
registration of manufacturing-use dichlone and all formulated dichlone
products when intended for outdoor use. Technical dichlone is the
preferred product to be tested. The species tested shall be the same as
one of the two species selected for the avian dietary I£5Q in Section
163.71-2.
There were no studies submitted to the Agency dealing with avian single-
dose oral LD5Q. This constitutes a data gap.
AVIAN DIETARY LC5Q (163.71-2)
A determination of the subacute dietary LC^ is required to support the
registration of all manufacturing-use dichlone and all formulated dichlone
products when they are intended for outdoor use. Technical dichlone is the
preferred test material. The mallard duck, bobwhite quail or ring necked
pheasant are the preferred test species.
The following two studies reporting four test results were reviewed and
found to be adequate for registration.
Species
Mallard
Ring-Necked Pheasant
Bobwhite Quail
Bobwhite Quail
Formulation
95%
95%
95%
98.4%
I£50 (PPM)
>5000
>5000
>5000
>4640
Reference
Hill, 1975
Fink, 1973, MRID 00001549
There is sufficient information to characterize dichlone as slightly to
practically nontoxic to upland game birds and waterfowl.
AVIAN REPRODUCTION (163.71-4)
A reproduction study is required to support the registration of a
formulated dichlone product if any of the following conditions exists: 1)
dichlone is persistent in the environment, 2) dichlone is stored or
accumulated in plant or animal tissue, and 3) the dichlone product is
intended for use where birds may be subjected to repeated or continued
exposure. The test material will be technical dichlone. The bobwhite
quail and mallard duck are the preferred species.
No data on avian reproduction have been submitted to the Agency. This is a
required study because the use of dichlone on agricultural crops would
subject birds to repeated exposure.
MAMMALIAN ACUTE TOXICITY (163.71-3)
These data are not needed for dichlone because the data on laboratory
animals reviewed in the Toxicology Chapter are generally sufficient for an
estimate of toxicity to wild mammals. Based on the data in dichlone's oral
toxicology review, there do not appear to be any unusual hazards to wild
mammals.
82
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FISH ACUTE TOXICITY (163.72-1)
A determination of the 96 hour LC™ is required to support the
registration of manufacturing-use dichlone and of each formulated dichlone
product. The test material required is technical dichlone. In addition, a
formulated product must be tested if its intended use is direct
introduction into the aquatic environment. The rainbow trout and bluegill
sunfish are the preferred species.
Three studies were reviewed and the data are presented below:
Species Formulation LC5Q (ppm) Reference
Rainbow trout
Bluegill sunfish
Fathead minnow
97%
97%
100%
0.034 McCann, 1976a
0.041 McCann, 1976b
0.150 Maloney and Palmer, 1956,
MRID 05003523
There are significant data to characterize dichlone as very highly toxic to
both coldwater and warmwater fishes. There were no tests using the ready-
to-use, wettable powder, or flowable concentrate formulations. This
constitutes a data gap for these formulations.
ACUTE TOXICITY TO AQUATIC INVERTEBRATES (163.72-2)
A determination of the EC™ or I£,-Q for an aquatic invertebrate species
is required to support the registration of manufacturing-use dichlone and
of each formulated dichlone product. The test material will be the
technical material. In addition, a formulated product will be tested if
its intended use is direct introduction into the aquatic environment.
Immature invertebrates (daphnids, amphipods, stoneflies, or mayflies)
should be used whenever possible.
Three studies were reviewed, and the data follows in Table 6 on the follow-
ing page.
83
-------
Species
Daphnia magna
Cypridopsis
vidua
Gammarus
fasciatus
Asellus
brevicaudus
Palaemonetes
kadiakensis
Daphnia magna
Daphnia magna
Table j>
Effects of Dichlone on Aquatic Invertebrates
Formulation LC™ (ppm) Reference
Technical
Technical
•Technical
Technical
Technical
Technical
Unknown
LC5Q
0.025 (48 hr.)
0.12
0.24
0.20
0,45
0.014 (26 hr.)
0.026 (26 hr.)
Sanders (1970)
MRID 05001497
Crosby and Tucker,
1966, MRID 05001465
Frear and Boyd,
1967, MRID 00002875
These tests do not conform to the protocol as stated in the EPA 1978
guidelines. However, collectively, using the data above, there is
sufficient information to characterize dichlone as highly toxic to aquatic
invertebrates. Consequently, no further acute aquatic invertebrate
toxicity studies are required on the technical. No tests were conducted
using the formulations that are used in the aquatic environment.
Therefore, to complete a hazard evaluation, the ready-to-use, flowable
concentrate, and wettable powder formulations must be tested.
84
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TERRESTRIAL MACROPHYTES (163.122-1)
As a wettable powder seed treatment, 2 oz. ai/cwt of seed has no effect on
peas, waxbeans, sugar beets, or cucumbers. As a foliar spray, 3 Ib. ai/100
gal. water or greater than 0.56 kg. ai/ha did not effect tobacco except to
retard senescence. A half a pound ai/100 gal. water does not affect either
tonates or potatoes.
Species
Tobacco
Formulation No Effect or
EC10 Level
Tomato
Potato
Sugar Beets
Oats
Cucumber
Peas
Beans, Wax
ai
>3 lb/100 gal
Reference
Rich and Taylor (1957)
MRID 05001576
wp (50%) >1.12 kg/ha Walker (1966) MRID
Sretards chlorophyll 05001635
senescencet
ai
59 mg/seedling
(0.125%)
50% 0.5 Ib ai/100
(liquid) gal
50% 0.5 Ib ai/100
(Liquid) gal
50% ai 2 oz ai/100 cwt
seed
(antagonism
with DCPA but
not with 2,4-D)
Jacks (1951) MRID
05001433
Bilbruch and Rich (1961)
MRID 05003839
Bilbruch and Rich (1961)
MRID 05003839
Wheatley and Johnson
(1962) MRID 05001489
Nash and Harris (1973)
MRID 05001493
ai
ai
>16ppm
>4 ppm + <0.13 ppm
2,4-D (synergism) Nash and Harris (1973)
MRID 05001493
wp (50%) >2 oz ai/cwt seed
wp (50%) >2 oz ai/cwt seed
wp (50%) >2 oz ai/cwt seed
deZeeuw et al. (1959)
MRID 05001580
deZeeuw et al. (1959)
MRID 05001580
deZeeuw et al. (1959)
MRID 05001500
There is an antagonistic effect with DCPA and a synergistic effect with
2,4-D while neither dichlone nor DCPA or 2,4-D exhibited any effect (up to
0.13 ppm with 2,4-D)
85
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EFFECT OF DICHLONE ON ALGAE (163.122-2)
The no observed effect level of dichlone on algae, when introduced as
the technical material, varies from species to species. As shown below,
the values range from .075 ppm to 32 ppm.
Species
Anacystis nidulans
Calothrix braunii
No Effect Level\
0.075 ppm
(in light)
2.0 ppm
Reference
Whitton (1966) MRID
05002615
Maloney and Palmer, 1956,
MRID 05003523
Cylindrospermum licheniforme 4.0 ppm
Microcystis aeruginosa
Nostoc muscorum
Phormidium tenue
Plectonema nostocorum
Symploca erecta
Ankistrodesmus falcatus
A._ falcatus acicularis
Chlamydomonas communis
C._ paradoxa
Chlorella variegata
Chlorococcum botryoides
C._ humicola
Coccomyxa simplex
Coelastrum proboscideum
Gloeocystis gravillei
Mesotaenium caldariorum
Oocystis lacustris
0._ marsonii
Scendesmus basilensis
Sj._ obliquus
Sphaerella lacustris
Stigeoclonium nanum
Achnanthes linearis
0.25 ppm
0.25 ppm
2.0 ppm
0.25 ppm
1.0 ppm
Achnanthes linearis
Gomphonema parvulum
Nitzschia palea #1
Nitzschia Palea #2
Nitzschia palea #3
#1
#2
32.0
4.0
2.0
1.0
4.0
32.0
8.0
8.0
16.0
2.0
4.0
16.0
32.0
32.0
32.0
0.5
4.0
1.0
1.0
1.0
1.0
0.5
0.5
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
ppm
In a laboratory study using Chlorella pyrenoidosa, dichlone
(3 x 10 M) exhibited a short term growth reduction of 56% while
chlorophyll content and oxygen evolution was reduced 100% (Zweig et al.,
1968, MRID 05001627).
In another laboratory study, Zweig et al. (1972, MRID 05001597) showed that
the EC™ for Chlorella carbon dioxide fixation was 1.05 uM.
86
-------
EFFECT OF DICHLONE ON AQUATIC MICROPHYTES (163.122-2)
Technical dichlone had no apparent phytotoxic effect on 10 aquatic
macrophytes during an outdoor pond test. The no-effect level was found to
be greater than 12 ppm. The common and species names are listed below
(Audia and Preston, 1965, MRID 05002173).
Soft rush
Swamp potato
Water Purslane
Pepperwort
Water Pern
Salvinia
Floating Fern
Water Hyacinth
Water Lettuce
Juncus effusus
Sagittaria sinensis
Ludwigia palustris
Marsilea quadrifolia
Azolla caroliniana
Salvinia rotundifolia
Ceratopteris thaiictroides
Eichornia crassipes
Pistia stratiotes
NITROGEN FIXATION POTENTIAL (162.125-3)
Because soybeans and other legumes, to be econcmicaly feasable in their
growth and production, require a bacteria symbiont (Rhizobium spp.) to
fix atmospheric nitrogen, the sensitivity of this symbiont to dichlone
will be covered in this section.
In pure culture, Rhizobium species show varying sensitivities according to
the resistance or sensitivity of the strain. However, 30 ppm is a minimal
value that was determined on seven species.
As a seed treatment at the time of innoculation with Rhizobium, dichlone
at 1 or 2 oz ai/cwt of legume seed is the no effect level for the growth
and yield of the plant even though the Rhizobium may be physiologically
affected and slow to infect.
+ or - symbiosis
with legume
+(Subterranean Clover)
-(cowpea Rhizobium )
No effect
Level
4 oz/cwt
(50% powder)
Reference
Williams et al. (1960)
MRID 05001377
50 ppm (sensitive)
400 ppm (resistant) Odeyemi (1976) MRID
05001655
2 oz/cwt
(50% powder)
+( R leguminosarum )
-(7 species of Rhizobium ) 30 ppm (w/v)
Ruhloff and Burton (1951)
MRID 05001773
Afifi et al. (1969)
MRID 05002504
EFFECT OF DICHLONE ON AMPHIBIANS
A teratology study was conducted on the embryo of the South African clawed
toad (Xenopus laevis). When 0.15 ppm of technical dichlone was applied
to the embryos, they completely disintegrated within one day (Anderson and
Prahlad,1976, MRID 05005290).
87
-------
There is sufficient information to characterize the toxicity of dichlone as
very highly toxic to the early life stage of amphibians.
EFFECT OF DICHLQNE ON BENEFICIAL INVERTEBRATES
Qie study showed that 0.5 lb/100 gal. water of Phygon XL was not toxic to
honey bees (Apis mellifera) exposed to direct application or dried
residues. HDwever, the material was moderately toxic in a feeding study.
Dichlone was also found not to be repellent to bees in field tests (King,
1959, MRJD 05001322).
There is sufficient information to characterize dichlone as low in toxicity
to honey bees, except when ingested.
88
-------
ECOLOGICAL EFFECTS BIBLIOGRAPHY
05002504
05005290
05002173
05003839
05001465
05001580
00001549
00002875
05001433
GS000801
Afifi, N.M.; Moharram, A.A.; Hamdi, Y.A.; Abd-El-Malek, Y.A.
(1969) Sensitivity of Rhizobium species to certain fungicides.
Archiv fuer Mikrobiolog ie 66(2):121-128.
Anderson, R.J.; Prahlad, K.V. (1976) The deleterious effects of
fungicides and herbicides on Xenopus laevis onbryos. Archives
of Environmental Contamination and Toxicology 4(3):312-323.
Audia, W.V.; Preston, W.H., Jr. (1965) The effects of several
algaecides on aquatic plants. Pages 451-455, In Proceedings of
the Nineteenth Annual Meeting of the Northeastern Weed Control
Conference. Farmingdale, N.Y.: Northeastern Weed Control
Conference.
Bilbruck, J.D.; Rich, A.E. (1961) The effect of various dichlone
treatments on the growth, yeild, and disease incidence of
potatoes and tomatoes in New Hampshire. Plant Disease Reporter
45(2):128-133.
Crosby, D.G.; Tucker, R.K. (1966) Tbxicity of aquatic herbicides
to Daphnia magna. Science 154(3746):289-291.
deZeeuw, D.J.; Guyer, G.E.; Wells, A.L.; Davis, R.A. (1959) The
effects of storage of vegetable seeds treated with fungicides
and insecticides on germination and field stand. Plant Disease
Reporter 43(2):213-220.
Fink, R. (1973) Eight-Day Dietary LC™—Bobwhite Quail—Technical
Dichlone: Final Report: Project NO. 104-102. (Unpublished study
received Get 9, 1973 under 279-833; prepared by Truslow Farms,
Inc., submitted by FMC Corp., Philadelphia, Pa.; CDL:008721-A)
Frear, D.E.H.; Boyd, J.E. (1967) Use of Daphnia magna for the
microbioassay of pesticides: I. Development of standardized
techniques for rearing Daphnia and preparation of dosage-mor-
tality curves for pesticides. Journal of Economic Entomology.
60(5):1228-1236. (Also jn unpublished submission received
May 11, 1977 under 239-2458; submitted by Chevron Chemical Co.,
Richmond, Calif.; CDL:230225-A)
Jacks, H. (1951) Soil disinfection: XI. Control of foot-rot
(Phytophthora cryptogea P.&L.) of tomatoes. New Zealand
Journal of Science and Technology 33A(4):71-75.
Hill, E.F.; Heath, R.G.; Spann, J.W.; Williams,J.D. (1975) Lethal
Dietary Tbxicities of Environmental Pollutants to Birds; Washing-
ton, D.C.; U.S. Fish and Wildlife Service. (Special Scientific
Report—Wildlife, no. 191)
05001322
King, C.C. (1959) The effects of fungicides.
Culture 87:678-681.
Gleanings in Bee
89
-------
05001493
05001655
05003523 Maloney, T.E.; Palmer, C.M. (1956) Toxicity of six chemical
compounds to thirty cultures of algae. Water and Sewage Works
103:509-513.
GS000802 McCann, J.A. (1976a) Biological Report of Analysis, Rainbow Trout
(Salmo gairdnerii) Test No. 1054, Sample No. 143228, EPA
Registration No. 2749-30, Product Name, Dichlone Fungicide;
Producer Name, K. Sakai and Company, Inc. US EPA Beltsville
laboratory
GS000803 McCann, J.A. (1976b) Biological Report of Analysis, Bluegill
(Lepomis macrochirus) Test No. 1036, Sample No. 143228, EPA
Registration No. 2749-30, Product Name, Dichlone Fungicide;
Producer Name, K. Sakai and Company, Inc. US EPA Beltsville
Laboratory
Nash, R.G.; Harris, W.G. (1973) Screening for phytotoxic pesticide
interaction. Journal of Environmental Quality 2(4):493-497.
Cdeyemi, O. (1976) Resistance of Rhizobium to Thiram, Spergon, and
Phygon: Doctoral Thesis. Ithaca, N.Y.: Cornell University.
(Available from: University Microfilms International, Ann
Arbor, Michigan; order no. 77-18,187)
05001576 Rich, S.; Taylor, G.S. (1957) Cottonseed oil formulations of
organic fungicides for tobacco. Plant Disease Reporter
41(5):465-467.
05001773 Ruhloff, M.; Burton, J.C. (1951) Compatibility of rhizobia with
seed protectants. Soil Science 72:283-290.
05001497 Sanders, H.O. (1970) Toxicities of some herbicides to six species
of freshwater crustaceans. Journal of the Water Pollution
Control Federation 42(8):1544-1550.
05001635 Walker, E.K. (1966) Effect of foliar sprays of Phygon XL-50 on
green fixation flue-cured tobacco. Canadian Journal of Plant
Science 46:326-328.
05001489 Wheatley, G.W.; Johnson, R.T. (1962) Germination-emergence of
sugar beet seed as affected by treatment and storage. Journal
of the Merican Society of Sugar Beet Technologists
XI (8):649-655.
05002615 Whitton, B.A. (1968) Effect of light on toxicity of various
substances to Anacystis nidulans. Plant and Cell Physiology
9(l):23-26.
05001377 Williams, W.A.; Harwood, L.H.; Hills, F.J. (1960) Incompatibility
of seed treatment fungicides and seed-applied legume inoculum
observed on field-grown subterranean clover. Agronomy Journal
52 (6):363-365.
90
-------
05001597 Zweig, G.; Carroll, J.; Tamas, I.; Sikka, B.C. (1972) Studies on
effects of certain quinones. II. Photosynthetic incorporation
of 14C02 by Chlorella. Plant Physiology 49(3):385-387.
05001627 Zweig, G.; Hitt, J.E.; McMahon, R. (1968) Effect of certain
quinones, diquat, and diuron on Chlorella pyrenoidosa Chick.
(Bnerson strain). Weed Science 16(l):69-73.
91
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OFFICE OF PESTICIDE PROGRAMS
PESTICIDE DOCUMENT MANAGEMENT SYSTEM
CASE BIBLIOGRAPHY
92
-------
GUIDE TO USE OF THIS BIBLIOGRAPHY
1. Content o£ Bibliography. Tnis bibliography contains
citations of all the studies reviewed by EPA in arriving at
the positions and conclusions stated elsewhere in this
standard. The bibliography is divided into 2 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, and (2)
citations examined and judged to be inappropriate for use in
developing the standard. 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 literature.
2. Units of Entry. The unit of entry in this bibliogrpahy 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 reivew, and can be
described with a conventional bibliographic citation. The
Agency has attempted also to unite basic documents and
coimientaries upon them, treating them as a single study.
3. 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, and eight-digit numeric identifier. This number is
unique to the citations, and should be called the "Master
Record Identifier", "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.
4. Form £f the Entry. In add ition to the Master Record
Identifier (MRID), each entry consists of a bibliographic
citation containing standard elements followed, in the case
of materials submitted to EPA, by a description of the
earliest known submission. The bibliographic conventions
used reflect the standards of the American National
Standards Institute (ANSI), expanded to provide for certain
special needs. Some explanatory notes of specific elements
follow:
a. Author. Whenever the Agency could confidently
identify one, we have chosen to show a personal
author. When no individual was identified, the Agency
93
-------
has shown an identifiable laboratory or testing
facility as author. As a last resort, the Agency has
shown the first known submitter as author.
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.
Title. This is the third element in the citation.
In some cases it has been necessary for our
bibliographers to create or enhance a document title.
Any such editorial insertions are contained between
square brackets.
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 "under", is the
registration number, experimental permit number,
petition number, or other administrative number
associated with the earliest known submission.
(3) Submitter. The third element is the submitter,
following the phrase "submitted by". When author-
ship is defaulted to the submitter, this element
is emitted.
(4) Volume Identification. The final element in the
trailing parentheses identifies the EPA accession
number of the volume in which the original
submission of the study appears. The six-digit
accession number follows the symbol "CDL",
standing for "Company Data Library". This
accession number is in turn followed by an
alphabetic suffix which shows the relative
position of the study within the volume. For
example, within accession number 123456, the first
study would be 123456-A; the second, 123456-B; the
26, 123456-Z; and the 27th, 123456-AA.
94
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Section 1: Citations Considered to be Part of the Data Base Supporting
Registration Under the Standard.
MRID
05002617
05001645
05001647
05002157
00001513
CITATION
PRODUCT CHEMISTRY BIBLIOGRAPHY
05001418
005001423
05005690
05004746
05001467
, inventor; Chemische Fabrik von Heyen A.G., assignee (1%8)
Process for the production of 2,3-dichloro-naphtho-quinone-
(1,4). British patent specification 1,102,849. Feb 14. 3 p.
Int. Cl. C 07C 49/66.
Buzbee, L.R.; Ecke, G.G., inventors; Kbppers Co., assignee (1968)
Improvements in or relating to the preparation of
1,2,3,4-tetrachlorotetralin. British patent specification
1,128,115. Sep 25. 8 p. Int. Cl. C 07C 25/18.
Buzbee, L.R.; Ecke, G.G., inventors; Kbppers Co., assignee (1969)
Preparation of 2,3-dichloro-l,4-naphthoquinone fron
naphthalene. U.S. patent 3,433,812. Mar 18. 5 p. U.S. Cl.
260-396: Int. Cl. C 07C 45/02, 49/66.
Collerson, R.R.; Harrison, D.J.; Radia, D. (1976) The Infrared
Spectra of High Purity Pesticide Samples. Teddington, England:
National Physical Laboratory. (NPL Division of Chemical
Standards report no. 48)
Food Research Laboratories, Incorporated (1952) Toxicological
Studies of Chemical Additives I. Phygon (2,3-Dichloro-l,4-naph-
thoquinone): Laboratory No. 58084. (Unpublished study received
Dec 22, 1952 under unknown admin, no.; prepared for Naugatuck
Chemical Co., Div. of United States Rubber Co., submitted by
Uniroyal Chemical, Bethany, Conn.; CDL:108443-A)
Goza, S.W. (1972) Infrared analysis of pesticide formulations.
Journal of the Association of Official Analytical Chemists
55 (5):913-917.
Kilgore, W.W.; White, E.R. (1970) Gas chromatographic separations
of mixed chlorinated fungicides. Journal of Chromatographic
Science 8:166-168.
Koromogawa, N.; Okada, Y.; Aoki, I., inventors; Takeda Chemical
Industries, assignee (1969) A method of manufacturing
2,3-dichloro-l,4-naphthoquinone Japanese patent
specification 69-28300. Nov 21. 2 p.
Kotakemori, M.; Ando, M. (1968) Nafutokinon-rui no
gasukuronatogurafi. [Gas chronatography of naphthoquinones]
Nippon Nogei Kagaku Kaishi. [Journal of the Agricultural
Chemical Society of Japan.] 42(12):726-730.
Kotakemori, M.; Okada, K. (1966) Thin-layer chromatography of some
substituted napthoquinones. Agricultural and Biological
Chemistry 30(9):935-936.
95
-------
MRID CITATION
05009211 Matsuura, M.; Sakai, K.; Sato, T.; Yamada, Y.; Bando, K.,
inventors; Kawasaki Kasei Kogyo Co., assignee (1978) [Method
for manufacturing 2,3-dichloro-l,4-naphthoquinone] Japanese
kokai 78 98943. Aug 29. 3 p. Int. a.2 C 07C 49/735.
05003899 Nakahara, T.; Dehara, M.; Hiyama, H. (1965) [A study on the
chlorination of naphthionic acid] Kagaku To Kogyo (Osaka).
05001652 Sjostrand, B.T.L., inventor; Svenska Oljeslageri Aktiebolaget,
assignee (1961) Chlorination of naphthoquinone. U.S. patent
2,975,196. Mar 14. 2 p.
05004894 Tsuchida, I.; Tachibana, T., inventors; (1967) [Production method
for 2,3-dichloro-l,4-naphthoquinone] Japanese patent
specification 67-17736. Sep 16. 3 p. Cl. 16 D 414.
00001540 United States Rubber Company (1965?) Technical Formulators Hand-
book: Phygon: Dichlone. (Unpublished study received Aug 31,
1965 under 8729-3; submitted by ECO Sciences, Inc., Boonton,
N.J.; CDL:009475-E)
05004895 Watanabe, H.; Mitsui, N.; Maeda, S.; Konishi, S.; Mitani, T.,
inventors; Seitetsu Chemical Industry, assignee (1976)
Japanese kokai 76-113859. Oct 7. 3 p. Int. C1.2 C 07c
49/66.
ENVIRONMENTAL FATE BIBLIOGRAPHY
05001486 Burchfield, H.P. (1959) Comparative stabilities of Dyrene,
l-fluoro-2,4-dinitrobenzene, dichlone, and captan in a silt
loam soil. Contributions fron Boyce Thompson Institute
20:205-215.
05001190 Helling, C.S.; Dennison, D.G.; Kaufman, D.D. (1974) Fungicide
movement in soils. Phytopathology 64(8):1091-1100.
05004330 Kecskes, M.; Vincent, J.M. (1969) Nehany fungicid hatasa
a Rhizobium leguminosarum sp-re.: II. Fenykamras es uveghazi
vizsgalatok. [The effect of some fungicides on Rhizobium
leguminosarum : II. Light room and glasshouse
investigations] Agrokemia es Talajtan. [Agrochemistry and
Soil Science.] 18(3/4):461-472.
05001654 Neely, W.C.; Smith, R.C.; Cody, R.M.; McDuffie, J.R.; Lansden,
J.A.; Ellis, S.P. (1973) Biological and Photobiological Action
of Pollutants on Aquatic Microorganisms. Auburn, Ala.: Water
Resources Research Institute, AuburnUniversity. (WRRI Bulletin
9; also available from: NTIS, Springfield, Va.; PB-220 167)
05001540 Powell, D. (1951) Phygon XL for the control of peach blossom
blight. Plant Disease Reporter 35(2):76-77.
96
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05001698
05004895
05004938
05001460
05010016
00001521
00001522
00001524
00001523
CITATION
Saxena, J. ; Sikka, H.C.; Zweig, G. (1973) Effect of certain
substituted naphthoquinones on growth and respiration
of Rhodospirillum rubrum . Pesticide Biochemistry and
Physiology 3(1): 66-72.
Watanabe, H. ; Mitsui, N. ; Maeda, S. ; Kbnishi, S. ; Amitani, T.f
inventors; Seitetsu Chemical Industry, assignee (1976)
Japanese kokai 76-113859. Cct 7. 3 p. Int. C1.2 C 07c
49/66.
Wiersma, G.B. ; Tai, H.; Sand, P.P. (1972) Pesticide residue levels
in soils, FY 1969 — National Soils Monitoring Program.
Pesticides Monitoring Journal 6 (3): 194-228.
TOXICOLOGY BIBLIOGRAPHY
Anderson, K.J.; Leighty, E.G.; Takahashi, M.T. (1972) Evaluation
of herbicides for possible mutagenic properties. Journal of
Agricultural and Food Chemistry 20(3) :649-656.
Bionetics Research Laboratories (1968) Evaluation of Carcinogenic,
Teratogenic, and Mutagenic Activities of Selected Pesticides
and Industrial Chemicals. Vol. I: Carcinogenic Study.
Bethesda, Md.: National Cancer Institute, Division of Cancer
Cause and Prevention. (National Cancer Institute report no.
NCI-DCCP-CG-1973-1-1; available from: NTIS, Springfield, VA;
PB-223 159)
Food Research Laboratories, Incorporated (1952) Acute Oral Toxici-
ty: [Pnygon] . (Unpublished study received Dec 22, 1952 under
unknown admin, no.; prepared for Naugatuck Chemical Co., Div. of
United States Rubber Co., submitted by Uniroyal Chemical,
Bethany, Conn.; CDL:108443-C)
Food Research laboratories, Incorporated (1952) Dermal Toxicity
Studies: [Phygon] . (Unpublished study received Dec 22, 1952
under unknown admin, no.; prepared for Naugatuck Chemical Co.,
Div. of United States Rubber Co., submitted by Uniroyal
Chemical, Bethany, Conn.; CDL:108443-D)
Food Research Laboratories, Incorporated (1952) Dog Feeding
Studies: [Phygon] . (Unpublished study received Dec 22, 1952
under unknown admin, no.; prepared for Naugatuck Chemical Co.,
Div. of United States Rubber Co., submitted by Uniroyal
Chemical, Bethany, Conn.; CDL:108443-F)
Food Research Laboratories, Incorporated (1952) Rat Feeding
Studies: [Phygon] . (Unpublished study received Dec 22, 1952
under unknown admin, no.; prepared for Naugatuck Chemical Co.,
Div. of United States Rubber Co., submitted by Uniroyal
Chemical, Bethany, Conn.; CDL:108443-E)
97
-------
MRID CITATION
05004401 Innes, J.R.M.; Ulland, B.M.; Valerio, M.G.; Petrucelli, L.;
Fishbein, L.; Hart, E.R.; Pallotta, A.J.; Bates, R.R.; Falk,
H.L.; Gart, J.J.; Klein, M.; Mitchell, I.; Peters, J. (1969)
Bioassay of pesticides and industrial chemicals for
tumorigenicity in mice: a preliminary note. Journal of the
National Cancer Institute 42(6):1101-1114.
RESIDUE CHEMISTRY BIBLIOGRAPHY
05002988 Borrmann, J.H. (1957) Report on phygon. Journal of the
Association of Official Agricultural Chemists 40(1):273-274.
05001359 Burchfield, H.P.; McNew, G.L. (1948) Ihe colorimetric
determination of 2,3-dichloro-l,4-naphthoquinone on seed.
Phytopathology 38:665-669.
05002348 Burke, J.; Johnson, L. (1962) Investigations in the use of the
micro-coulcmetric gas chronatograph for pesticide residue
analysis. Journal of the Association of Official Agricultural
Chemists 45(2):348-354.
05003909 Faust, S.D.; Hunter, N.E. (1965) Chemical methods for the
detection of aquatic herbicides. Journal of the American Water
Works Association 57(8):1028-1037.
05001490 Hoffman, I.; Parups, E.V.; Morley, H.V. (1965) Identification and
determination of dichlone residues in treated tobaccos.
Journal of the Association of Official Agricultural Chemists
48(5):1063-1066.
05003005 Kovacs, M.F., Jr. (1966) Rapid detection of chlorinated pesticide
residues by an improved TLC technique: 3 1/4 X 4" micro slides.
Journal of the Association of Official Analytical Chemists
49(2):365-370.
05001408 Lane, J.R. (1958) Determination of Phygon residues on food crops.
Journal of Agricultural and Food Chemistry 6(10):746-747.
05001416 Miller, G.A. (1965) Dichlone residues on foods. Journal of the
Association of Official Agricultural Chemists 48(4):759-762.
05004950 Mills, P.A.; Bong, B.A.; Kamps, L.R.; Burke, J.A. (1972) Elution
solvent system for Florisil column cleanup in organochlorine
pesticide residue analyses. Journal of the Association of
Official Analytical Chemists 55(l):39-43.
00001534 Naugatuck Chemical (1955?) l"he Results of Tests on the Amount of
Residue Remaining, Including a Description of the Analytical
Method Used. (Unpublished study received Jun 1, 1955 under 16;
submitted by Naugatuck Chemical, Div. of United States Rubber
Co., Naugatuck, Conn.; CDL:092299-L)
98
-------
MRID CITATION
00001515 Newell, J.E.; Mazaika, R.J.; Cook, W.J. (1954?) The Micro Deter-
mination of Phygon in Water. Undated method. (Unpublished
study received May 10, 1957 under 400-11; prepared by Naugatuck
Chenical, Div. of United States Rubber Co., submitted by
Uniroyal Chemical, Bethany, Conn.; CDL:120159-A)
05002878 Owens, R.G.; Blaak, G. (1960) Chemistry of the reactions of
dichlone and captan with thiols. Contributions from Boyce
Thompson Institute 20(8):475-497.
05004240 Patrashku, F.I.; Sorokskaya, L.B.; Rekhter, B.A. (1971)
Opredeleniye figona v rasteniyakh pri pcmoshchi tonkosloinoi
khromatografii i fotcmetricheskimi metodami. [Determination
ofphygon in plants by thin-layer chromatography and photometric
methods.] Pages 181-183, In Trudy Vsesoyuznogo Soveshchaniya
po Issledovaniya Ostatkov Pestitsidov i Profilaktike
Zagrayazneniya Imi Produktov Pitaniya, Kbrmov i Vheshnei
Sredy,Metody Analiza, 2nd; 1970, Tallin. [Transactions of
the Ail-Union Conference on the Residues of Pesticides and
Prophylaxis of Contamination by Them of Foodstuffs, Feeds and
the Environment, Methods of Analysis, 2nd; 1970, Tallin.]
Edited by O.M. Tamn.
00001529 United States Rubber Company (19??) The Results of Tests on the
Amount of Residue Remaining, Including a Description of the Ana-
lytical Method Used: [Phygon]. (Unpublished study received Aug
12, 1955? under 188; CDL-.090216-A)
00001510 United States Rubber Company (1956) [Phygon-XL Residue on Fruit].
(Unpublished study received Jan 15, 1957 under 400-11; submitted
by Uniroyal Chemical, Bethany, Conn.; CDL:003230-O)
05001410 White, E.R.; Kilgore, W.W.; Mallett, G. (1969) Phygon. Fate of
2,3-dichloro-l,4-napththoquinone in crop extracts. Journal of
Agricultural and Food Chemistry 17(3):585-588.
05001656 Zweig, G.; Sherma, J. (1972) Phygon (dichlone). Pages
584-585, In Analytical Methods for Pesticides and Plant Growth
Regulators. Vol. VI: Gas Chrcmatographic Analysis. Edited by
G. Zweig and J. Sherma. New York: Academic Press.
ECOLOGICAL EFFECTS BIBLIOGRAPHY
05002504 Afifi, N.M.; Moharram, A.A.; Hamdi, Y.A.; Abd-El-Malek, Y.A.
(1969) Sensitivity of Rhizobium species to certain fungicides.
Archiv fuer Mikrobiolog ie 66(2):121-128.
05005290 Anderson, R.J.; Prahlad, K.V. (1976) The deleterious effects of
fungicides and herbicides on Xenopus laevis embryos. Archives
of Environmental Contamination and Toxicology 4(3):312-323.
99
-------
MRID
05002173
05003839
05001465
05001580
00001549
00002875
GS000801
05001433
05001322
05003523
GS000802
CITATION
Audia, W.V.; Preston, W.H., Jr. (1965) The effects of several
algaecides on aquatic plants. Pages 451-455, In Proceedings of
the Nineteenth Annual Meeting of the Northeastern Weed Control
Conference. Farmingdale, N.Y.: Northeastern Weed Control
Conference.
Bilbruck, J.D.; Rich, A.E. (1961) The effect of various dichlone
treatments on the growth, yield, and disease incidence of
potatoes and tomatoes in New Hampshire. Plant Disease Reporter
45(2):128-133.
Crosby, D.G.; Tucker, R.K. (1966) Toxicity of aquatic herbicides
to Daphnia magna. Science 154(3746):289-291.
deZeeuw, D.J.; Guyer, G.E.; Wells, A.L.; Davis, R.A. (1959) The
effects of storage of vegetable seeds treated with fungicides
and insecticides on gemination and field stand. Plant Disease
Reporter 43(2)-.213-220.
Fink, R. (1973) Eight-Day Dietary LC™—Bobwhite Quail—Technical
Dichlone: Final Report: Project No. 104-102. (Unpublished study
received Get 9, 1973 under 279-833; prepared by Truslow Farms,
Inc., submitted by FMC Corp., Philadelphia, Pa.; CDL:008721-A)
Frear, D.E.H.; Boyd, J.E. (1967) Use of Daphnia magna for the
microbioassay of pesticides: I. Development of standardized
techniques for rearing Daphnia and preparation of dosage-mor-
tality curves for pesticides. Journal of Economic Entomology.
60(5):1228-1236. (Also In unpublished submission received
May 11, 1977 under 239-2458; submitted by Chevron Chemical Co.,
Richmond, Calif.; CDL:230225-A)
Hill, E.F.; Heath, R.G.; Spann, J.W.; Williams,J.D. (1975) Lethal
Dietary Toxicities of Environmental Pollutants to Birds; Washing-
ton, D.C.; U.S. Fish and Wildlife Service. (Special Scientific
Report—Wildlife, no. 191)
Jacks, H. (1951) Soil disinfection: XI. Control of foot-rot
( Phytophthora cryptogea P. & L.) of tomatoes. New Zealand
Journal of Science and Technology 33A(4):71-75.
King, C.C. (1959) The effects of fungicides.
Culture 87:678-681.
Gleanings in Bee
Maloney, T.E.; Palmer, C.M. (1956) Toxicity of six chemical
compounds to thirty cultures of algae. Water and Sewage Works
103:509-513.
McCann, J.A. (1976a) Biological Report of Analysis, Rainbow Trout
(Salmo gairdnerii) Test No. 1054, Sample No. 143228, EPA
Registration No. 2749-30, Product Name, Dichlone Fungicide;
Producer Name, K. Sakai and Company, Inc. US EPA Beltsville
laboratory
100
-------
MRID CITATION
GS000803 McCann, J.A. (1976b) Biological Report of Analysis, Bluegill
(Lepomis macrochirus) Test No. 1036, Sample No. 143228, EPA
Registration No. 2749-30, Product Name, Dichlone Fungicide;
Producer Name, K. Sakai and Company, Inc. US EPA Beltsville
Laboratory
05001493 Nash, R.G.; Harris, W.G. (1973) Screening for phytotoxic pesticide
interaction. Journal of Environmental Quality 2(4):493-497.
05001655 Odeyemi, O. (1976) Resistance of Rhizobium to Thiram, Spergon, and
Phygon: Doctoral Thesis. Ithaca, N.Y.: Cornell University.
(Available from: University Microfilms International, Ann
Arbor, Michigan; order no. 77-18,187)
05001576 Rich, S.; Taylor, G.S. (1957) Cottonseed oil formulations of
organic fungicides for tobacco. Plant Disease Reporter
41(5):465-467.
05001773 Ruhloff, M.; Burton, J.C. (1951) Compatibility of rhizobia with
seed protectants. Soil Science 72:283-290.
05001497 Sanders, H.O. (1970) Toxicities of some herbicides to six species
of freshwater crustaceans. Journal of the Water Pollution
Control Federation 42(8):1544-1550.
05001635 Walker, E.K. (1966) Effect of foliar sprays of Phygon XL-50 on
green fixation flue-cured tobacco. Canadian Journal of Plant
Science 46:326-328.
05001489 Wheatley, G.W.; Johnson, R.T. (1962) Germination-emergence of
sugar beet seed as affected by treatment and storage. Journal
of the American Society of Sugar Beet Technologists
XI(8):649-655.
05002615 Whitton, B.A. (1968) Effect of light on toxicity of various
substances to Anacystis nidulans. Plant and Cell Physiology
9(l):23-26.
05001377 Williams, W.A.; Harwood, L.H.; Hills, F.J. (1960) Incompatibility
of seed treatment fungicides and seed-applied legume inoculum
observed on field-grown subterranean clover. Agronomy Journal
52(6):363-365.
05001597 Zweig, G.; Carroll, J.; Tamas, I.; Sikka, H.C. (1972) Studies on
effects of certain quinones. II. Photosynthetic incorporation
of 14C02 by Chlorella. Plant Physiology 49(3):385-387.
05001627 Zweig, G.; Hitt, J.E.; McMahon, R. (1968) Effect of certain
quinones, diquat, and diuron on Chlorella pyrenoidosa Chick_
(Emerson strain). Weed Science 16(1):69-73. ~~
101
-------
Section 2: Citations Examined and Judged to be Citations Inappropriate for Use
in Developing the Standard.
MRID CITATION
05002927 inventor; Svenska Oljeslageri Aktiebolaget, assignee (1960)
Improvements in or relating to the manufacture of halogenated
organic compounds. British patent specification 854,977. ISfov
23. 5 p._.Int. Cl. C 07C.
05006253 Akatsuka, M. (1963) Kinon-rui no kenkyu (dai-ippo)
isonikochinsan-hidoraj ido oyobi 2,3-dikuroro-alpha-nafutokinon
no kishokuteiryo ni tsiute. [Quinones: I. Colorimetric
determinations of isonicotinic acid hydrazide and
2,3-dichloro-alpha-naphthoquinone.] Yakugaku Zasshi. [Journal
of the Pharmaceutical Society of Japan.] 83(3):227-233.
05011978 Alabaster, J.S. (1958) Toxicity of weedkillers, algicides and
fungicides to trout. Pages 84-85, In Proceedings of the 4th
British Weed Control Conference; Brighton. Droitwich, England:
British Weed Control Conference.
05001352 Anderson, B.S. (1974) Infrared analysis of pesticides. Canadian
Journal of Spectroscopy 19(2):37-39.
05003871 Anderson, L.D.; Atkins, E.L., Jr.; Todd, F.E.; McGregor, S.E.
(1962) Toxicity of pesticides to honeybees. Gleanings in Bee
Culture 90(1):152-153.
05005694 Ashino, I., inventor; Andrews (and George) Company, assignee
(1977) Gycmo ho-ozai. [An anti-fouling agent for fish nets.]
Japanese kokai 77-117425. Get 1. 2 p. Int. Cl._2? A OIK
74/00; A 01N 9/02; A OlN 23/00.
05001604 Babu, B.H.; Rao, N.V.S. (1968) Search for physiologically active
compounds: Part XII. Synthesis and fungistatic activity of
5:6- and 5:8-quincline quinones. Pages 31-36, In Proceedings—
Indian Academy of Science, Section A.
Vol. 67. Bangalore, India: Indian Academy of Sciences.
05001646 Baillie, E.G.; Stevens, L.F., inventors; Pittsburgh Plate Glass
Co., assignee (1961) Pesticidal composition. U.S. patent
2,976,206. Mar 21. 3 p.
05004249 Binder, H.; Ruehl, K., inventors; Ruetgerswerke und Teerverwertung
A.-G., assignee (1965) Verfahren zur Herstellung von
2,3-Dichlornaphthochinon-(l,4). [Method for the production of
2,3-d ichloro-1,4-naphthoqu inone.] German (Fed. Rep.)
auslegeschrift 1,194,392. Jun 10. 2 p.
05004231 Blagonravova, L.N. (1969) Vplyv khlororhanichnykh otrutokhimikativ
na aktyvnis1 khlorofilazy deyakikh roslin. [Effect of
chlororganic chemical weed-killers on activity of
chlorophyllase in some plants.] Ukrains'kii Botanichnii
Zhurnal. [Ukrainian Botanical Journal.] 26(4):103-106.
05002922 Blagonravova, L.N.; Nilov, G.I. (1976) Vliyanie pestitsidov na
aktivnost1 peroksidazy khrena. [Effect of pesticides on the
activity of horseradish peroxidase.] Khimiya v Sel'skom
Khozyaistve. [Chemistry in Agriculture.] 14(11):41-42.
05005758 Blagonravova, L.N.; Nilov, G.I.; Avdoshina, E.G. (1972) Vliyanie
khlororganicheskikh pestitsidov na soderzhanie vitamina E v
list'yakh rastenii. [The effect of organochlorine pesticides
on the vitamin E content of plant leaves.] Byulleten1
Gosudarstvennogo Nikitskogo Botanicheskogo Sada. [Bulletin of
the Nikitskii State Botanical Garden.] 3(19):57-59.
102
-------
MRID CITATION
05003807 Blagonravova, L.N.; Shcherbanovskii, L.R. (1974) Vliyanie
naftokhinonov na aktivnost1 in vitro peroksidazy khrena
obyknovennogo. [Influence of naphthoquinones on the in vitro
activity of peroxidase from horseradish.] Prikladnaya
Biokhimiya i Mikrobiologiya. [Applied Biochemistry and
Microbiology.] X(5):666-669.
05005013 Blois, M.S. (1960) Electron Paramagnetic Resonance Studies of
Biological and Biochemical Systems. Stanford, Calif.:
Stanford University. (Appendix A: 13 pages; 7 unpaged figures;
Biophysics Laboratory, Stanford University, report no. 12; also
available from U.S. Department of Commerce, Office of Technical
Services, Washington D.C., report no. 153411)
05005693 Bonino, G.; Ciferri, R.; Morselli, G., inventors; Societa
Elettrica ed Elettrochimica del Caffaro, assignee (1948)
Processo e composti per la conservazione del legname in opera.
Italian brevetto per invenzione industriale 436820. Jun 14. Ip.
05005692 Bonino, G.B.; Ciferri, R., inventors; Societa Elettrica ed
Elettrochimica del Caffaro, assignee (1948) Prodotti
anticrittoganici acuprici a base di sostanze organiche.
Italian brevetto per invenzione industriale 433853. Apr 15. 2p.
05004748 Bregadze, A.G. (1969) [The effect exerted by fungicides effective
against peach mildew on certain physiological indicators of the
plant.] Trudy Instituta Zashchity Rastenii, Tiflis.
XXI:303-310.
05004230 Bregadze, A.G. (1971) [Anatomical changes in peach plants treated
with new fungicides.] Trudy Instituta Zashchity Rastenii,
Tiflis. [Transactions of the Institute of Plant Protection.]
XXIII:286-294.
05001365 Brinkerhoff, L.A.; Fink, G.; Kbrtsen, R.A.; Swift, D. (1954)
Further studies on the effect of chemical seed treatments on
nodulation of legumes. Plant Disease Reporter 38(6):393-400.
05001320 Burchfield, H.P.; Gullstrom, O.K.; McNew, G.L. (1948) Agricultural
dusts: preparation of dusts of uniform particle size by
fractional sedimentation. Analytical Chemistry
20(12):1168-1173.
05001353 Burchfield, H.P.; McNew, G.L. (1950) Mechanism of particle size
effects of fungicides on plant protection. Contributions from
Boyce Thompson Institute 16(3):131-161.
05001354 Burchfield, H.P.; Schuldt, P.H. (1958) Pyridine-alkali reactions
in the analysis of pesticides containing active halogen atoms.
Journal of Agricultural and Food Chemistry 6(2):106-111.
05003514 Burkat, S.E.; Ivanov, B.C.; Romanova, N.V. (1965) Obnaruzhenie i
fotometri cheskoe opredelen ie 2,3-d ikhlor-1,4-naftokhinona.
[2,3-dichloro-l,4-naphthoquinone] Zhurnal Analiticheskoi
Khimii. [Journal of Analytical Chemistry.] 20(2):266-268.
05002156 Buu-Hoi, N.P.; Demerseman, P. (1952) The condensation of
2:3-dichloro-l:4-naphthaquinone with alpha-naphthols. Journal
of the Chemical Society 1952:4699-4700.
05001357 Byrde, R.J.W.; Woodcock, D. (1952) Fungicides and phytotoxicity.
Nature 169(4299):503-504.
05001321 Byrde, R.J.W.; Woodcock, D. (1953) Fungicidal activity and
chemical constitution. II. Compounds related to
2:3-dichloro-l:4-naphthoquinone. Annals of Applied Biology
40(4):675-687.
103
-------
MRID
05002350
05003384
05007015
05001455
05005962
05003589
05001842
05005954
05002007
05001496
05003276
05001651 Dye
05001391
05005421
05001623
05004329
CITATION
Castillo, G.; Ellames,-,G.J.; Csborne, A.G.; Sammes, P.G. (1978)
Use of long-range C-TI coupling constants for structural
assignments of juglone derivatives. Journal of Chemical
Research (S) 2:45.
Chernichenko, I.A. (1967) Spektrofotcmetricheskii metod
opredeleniya 2,3-dikhlor-l, 4-naftokhinona v atmosferncm
vozdukhe. [Spectrophotcmetric determination of
2,3-dichloro-l,4-naphthoquinone in the atmosphere.] Gigiena
Naselennykh Mest. [Hygiene in Populated Places.] :125-128.
Chernichenko, I.A. (1973) Experimentalnoe obosnovanie dopustimogo
urovnia soderzhania dichlornaftohinona v atmosfernom vozduhe.
dichloronaphthoquinone concentration in the air.] Gigiena
Naselennykh Mest. [Hygiene in Populated Places.] (12):78-85.
Cho, D.H.; Parks, L.; Zweig, G. (1966) Photoreduction of quinones
by isolated spinach chloroplasts. Biochimica et Biophysica
Acta 126(2):200-206.
Chugai Seiyaku Kabishiki Kaisha, assignee (1965) Fumigenes
fongicides. [Fungicidal fumigants.] Belgian brevet
d1invention 655,516. Mar 1. 14 p.
Clark, V.M.; Hutchinson, D.W.; Lyons, A.R.; Roschnik, R.K. (1969)
Acylation reactions involving halogenoquinones. Journal of the
Chemical Society: Section C (2):233-238.
Coover, H.W., Jr.; Dickey, J.B., inventors; Eastman Kodak,
assignee (1952) Process for preparing 1,4-naphthoquinone
compounds. U.S. patent 2,585,229. Feb 12. 5p. Cl. 260-396.
Davignon, L.F.; St-Pierre, J.; Charest, G.; Tburangeau, F.J.
(1965) A study of the chronic effects of insecticides in man.
Canadian Medical Association Journal 92(12):597-602.
Davis, H.C.; Hidu, H. (1969) Effects of pesticides on embryonic
development of clams and oysters and on survival and growth of
the larvae. Fishery Bulletin 67(2):393-404.
Degelaen, J.; Arte, E.; Van Eerdewegh, B.; Van Meerssche, M.;
Dereppe, J.M. (1977) Comparative NMR study in nematic phases of
the bicyclic compounds: 1,4-naphthoquinone,
2,3-dichloro-l,4-naphthoquinone and naphthalene. Journal of
Molecular Structure 36(2):263-267.
Dittmer, D.S., ed. (1959) Handbook of Toxicology. Volume V:
Fungicides. Philadelphia, Pa.: W.B. Saunders. (Available
from: University Microfilms International, Ann Arbor, MI)
H.W., inventor; Food Machinery and Chenical Corp., assignee
(1956) Composition for controlling growth of fungi comprising
dichloronaphthaquinone and bentonite sulfur. U.S. patent
2,771,389. Nov 20. 2 p.
Ebine, S. (1961) Formation of naphthol and naphthoquinone
derivatives from 3,4-benzotropolone. Chemistry and Industry
39:513-514.
Eipper, A.W. (1959) Effects of five herbicides on farm pond plants
and fish. New York Fish and Game Journal 6(l):46-56.
Fitzgerald, G.P. (1957) The control of the growth of algae with
CMU. Transactions of the Wisconsin Academy of Sciences, Arts
and Letters 46:281-294.
Fitzgerald, G.P. (1960) Loss of algicidal chemicals in swimming
pools. Applied Microbiology 8:269-274.
104
-------
MRID CITATION
05001650 Fletcher, H.H., inventor; United States Rubber Cb., assignee
(1947) Manufacture of chlorinated quinones. U.S. patent
2,422,229. Jun 17. 2 p.
00001551 FMC Corporation (1970) Name, Chemical Identity and Conposition of
Dichlone. (Unpublished study received Nov 24, 1970 under
1F1072; submitted by FMC Corp., Philadelphia, Pa.;
CDL:093382-C)
00001528 Food Research Laboratories (1955?) Transcript of Histopathological
Report on Dogs in Phygon Feeding Experiment: Laboratory
No. 58084. (Unpublished study received Jun 1, 1955 under 16;
submitted by Naugatuck Chemical, Div. of United States Rubber
Co., Naugatuck, Conn.; CDL:092299-E)
05004250 Fuhlhage, D.W., inventor; Thcmpson-Hayward Chemical Co., assignee
(1969) Verfahren zur Herstellung alpha-halogenierter Ketone
Oder Saeuren. [Procedure for the preparation of
alpha-halogenated ketones or acids.] German (Fed. Rep.)
offenlegungsschrift 1,946,283. Sep 11. 7 p.
05001413 Gaertner, R. (1954) Reactivities of carbonyl-activated angular and
"vinyl" chlorine substituents in adducts from dienes and
chloroquinones. Syntheses of chloronaphthoquinones. Journal
of the American Chemical Society 76:6150-6155.
05001385 Cause, E.M.; Montalvo, D.A.; Rowlands, J.R. (1967) Electron spin
resonance studies of the chloranil-cysteine, dichlone-cysteine
and dichlone-glutathione reactions. Biochimica et Biophysica
Acta 141(1):217-219.
05001516 Gerdemann, J.W. (1951) Effect of seed treatment on forage legunes
in wet and dry soil. Phytopathology 41:610-614.
05001515 Gill, D.L. (1950) Effectiveness of fungicidal sprays and dusts in
azalea petal blight control. Phytopathology 40:333-340.
05001609 Graham, S.O. (1963) Indophenol blue as a chrornogenic agent for
identification of halogenated aromatic hydrocarbons. Science
139:835-836.
05001840 Granados, H.; Snog-Kjaer, A.; Glavind, J.; Dam, H. (1949)
Experimental dental caries. XIV. Further studies on effect of
certain quinones. Pages 669-674, JLn Proceedings—Society for
Experimental Biology and Medicine. Vol. 72. New York:
Academic Press.
00001532 Green, R.J., Jr. (1970) Study of Dichlone Residues on Scotch Spear-
mint 1970. (Unpublished study received Sep 1, 1970 under
1E1125; prepared by Purdue Univ., Dept. of Botany and Plant
Pathology, submitted by Rutgers Univ., New Brunswick, N.J.;
CDL:090900-B)
05001661 Hamed, A.S.; Salem, S.H. (1977) Effect of sane pesticides on the
growth of Rhizobium leguminosarum in liquid culture media.
Pages 103-109, In Proceedings of the Vllth Meeting of the Soil
Biology Section of the Society for Soil Science of the
Hungarian Association of Agricultural Sciences; Sep 2-4, 1975,
Keszthely University of Agriculture, Hungary. Budapest,
Hungary: Akademiai Kiado.
05001666 Hashimoto, T. (1969) Fish-toxicity problems of pesticides in
Japan—the present situation and the policies of the Ministry
of Agriculture and Forestry. PANS 15(3):325-329.
105
-------
MRID CITATION
05001997 Hashimoto, Y.; Fukami, J. (1969) Toxicity of orally and topically
applied pesticide ingredients to carp, Cyprinus carpio Linne.
Botyu-Kagaku. [Scientific Pest Cbntrol.] 34(2):63-66.
05000770 Heath, R.G.; Spann, J.W.; Hill, E.F.; Kreitzer, J.F. (1972)
Comparative Dietary Toxicities of Pesticides to Birds.
Washington, D.C.: U.S. Fish and Wildlife Service. (Special
scientific report: Wildlife, no. 152)
05005070 Herschler, R.J., inventor; Crown Zellerbach, assignee (1973)
Enhanced plant tissue penetration. U.S. patent 3,756,801. Sep
4. 7 p. Int. Cl. A Oln 5/00,9/100; Cl. 71-65.
05001610 Hildebrand, A.A.; Koch, L.W. (1950) Observations on six years'
seed treatment of soybeans in Ontario. Scientific Agriculture
30 (3):112-118.
00003275 Hinstridge, P.A. (1970) Determination of Dichlone Residues on or in
Pears: R-1160. (Unpublished study received Jun 14, 1971 under
1F1072; submitted by FMC Corp., Philadelphia, Pa.; CDL:091849-A)
05002170 Hofer, A.W. (1958) Selective action of fungicides on rhizobium.
Soil Science 86:282-286.
05001466 Ikemoto, I.; Yakushi, K.; Naito, Y.; Kuroda, H.; Sano, M. (1977)
The crystal and molecular structure of an orthorhombic
modification of 2,3-dichloro-l,4-naphthoquinone. Acta
Crystallographica, Section B 33:2076-2079.
05005007 Ivanov, B.C.; Makovskaya, E.I. (1970) K voprosu o vliyanii
dikhlornaftokhinona na organizm zhivotnykh. [Effect of
dichloronaphthoquinone on animals.] Gigiena Primeneniya,
Toksikologiya Pestitsidov i Klinika Otravlenii. [Hygiene of
the Application and Toxicology of Pesticides and Clinical
Aspects of Poisoning.] 8:160-166.
05004995 Iwamoto, H.; Kikuchi, M. (1960) Kogyo seihin no hobai ni kansuru
kenkyu (dai juppo): kakushu kobaizai no kobai ryoku ni tsuite
(sono shi). Kinon-kei kagcbutsu ni tsuite. [Studies on the
prevention of mold growth on industrial manufactures. (Part
10): on the antifungal activity of various fungicides (IV)-
On the quinone compounds.] Hakko Kyokaishi. [Journal of the
Fermentation Association.] 18:352-357.
05001435 Jacks, H.; Graham, G.J. (1955) Seed disinfection: XI. Control of
head smut (Sorosporium reilianum (Kuhn) McAlpine) of maize.
New Zealand Journal of Science and Technology, Series A
37(2):141-145.
05007089 Jegier, Z. (1964) Health hazards in insecticide spraying of crops.
Archives of Environmental Health 8:670-674.
05007502 Johnson, D.W. (1968) Pesticide and fishes—a review of selected
literature. Transactions of the Merican Fisheries Society
97(4):398-424.
05001421 Josien, M.L.; Fuson, N.; Lebas, J.M.; Gregory, T.M. (1953) An
infrared spectroscopic study of the carbonyl stretching
frequency in a group of ortho and para quinones. Journal of
Chemical Physics 21(2):331-340.
05009402 Kanazawa, J.; Masuda, T.; lizuka, H.; Yamada, T.; Suzuki, T.
(1973) Do jo oyobi sakumotsu no zanryunoyakubunsekiho.
[Analytical methods for determining pesticide residues on soil
and crops (5).] Nippon Dojo-Hiryogaku Zasshi. [Journal of the
Science of Soil and Animal Fertilizers, Japan.] 44(12):491-502.
106
-------
MRID
05005570
05001498
05005005
05001425
05001322
05003809
05005691
05001386
05003808
05013361
05001408
05009464
05001519
CITATION
Kato, T. (1962) Rubiakayadorikobachi ni taisuru shinnoyaku no
eikyo ni tsuite no kisoteki kenkyu. [Effects of modern
pesticides on Anicetus beneficus Ishii et Yasumatsu (Hym.
Encyrtidae) , the most effective parasite of Ceroplastes
rubens Maskell.] Kyusku Daigaku Nogakubu Gakugei Zasshi.
Kecskes, M. (1970) Comparative investigations of the action of
fungicides on Rhizobium leguminosarum Frank and its symbiosis
with Vicia sativa. Mededelingen van de Eaculteit
Landbouwwetenschappen, Rijksuniversiteit Gent. [Conraunications
of the Faculty of Agricultural Sciences, State University of
Ghent.] 35 (2): 505-514.
Kecskes, M. ; Vincent, J.M. (1969) Nehany fungicid hatasa
a Rhizobium leguminosarum sp. -re: I. Laboratoriumi
vizsgalatok. [The effect of some fungicides on Rhizobium
leguminosarum sp.: I. laboratory investigations.] Agrokemia
es Talajtan. [Agrochemistry and Soil Science.] 18(1):57-70.
Kecskes, M. ; Vincent, J.M. (1973) Compatibility of fungicide
treatment and rhizobium inoculation of vetch seed. Acta
Agronomica Academiae Scientiarum Hungaricae 22 (1/2): 249-263.
King, C.C. (1959) The effects of fungicides. Gleanings in Bee
Culture 87:678-681.
Kiprianov, A.I.; Stetsenko, A.V. (1953) Vzairoodeistvie
metilenovykh osnovanii azotistykh geterotsiklov s khinonami.
Zhurnal Cbshchei Khimii. [Journal of General Chemistry]
23:1912-1920.
Koromogawa, N. ; Okada, Y. ; Aoki, I., inventors; Takeda Chemical
Industries, assignee (1969) [A method of manufacturing
2,3-dichloro-l,4-naphthoquinone.] Japanese patent
specification 69-28301. Nov 21. 1 p.
Ruhr, R. J. ; Davis, A.C.; Bourke, J.B. (1974) Dissipation of
Gunthion, Sevin, Polyram, Phygon and Systox from apple orchard
soil. Bulletin of Environmental Contamination and Toxicology
11 (3): 22 4-230.
Labunskii, V.V. (1969) Voprosy gigieny truda i toksikologii v
proizvodstve 2,3-dikhlor-l,4-naftokhinona. [Industrial hygiene
and toxicology in the production of
2,3-dichloro-l,4-naphthoquinone.] Vrachebnoe Delo. [Medical
Profession.] (10): 89-92.
labunskiy, V.V. (1970) K sravnitel'noi otsenke toksicheskogo
deistviya al'fa-naftokhinona i nekotorykh ego proizvodnykh.
Farmakologiya i Toksikologiya (Kiev) . [Pharmacology and
Toxicology.] (5): 148-150.
Lane, J.R. (1958) Determination of Phygon residues on food crops.
Journal of Agricultural and Food Chemistry 6(10) : 746-747.
Lane, J.R. (1964) Phygon — also dichlone. Pages 141-150,
In Analytical Methods for Pesticides, Plant Growth
Regulators, and Food Additives. Vol. 3. Edited by G. Zweig.
New York: Academic Press.
Le Tburneau, D. ; McLean, J.G.; Guthrie, J.W. (1957) Effects of
some phenols and quinones on growth in vitro of Verticillium
albo-atrum . Phytopathology 47:602-606.
107
-------
MRID CITATION
05005011 Lisovskaya, E.V.; Zholdakova, Z.I.; Grigor'eva, L.V. (1967)
Experimental' noe obosnovanie predel'no dopustimoi
kontsentratsii 2,3-dikhlor-l,4-riaftokhinona v vode vodoemov.
Prcmyshlennye Zagryazneniya Vodoemov. [Industrial Pollutants
of Reservoirs.] (8):61-71.
05001396 Livingston, R.J. (1977) Review of current literature concerning
the acute and chronic effects of pesticides on aquatic
orgasnistns. CRC Critical Reviews in Environmental Control
7(4):325-351.
05010898 Lord, F.T. (1949) The influence of spray programs on the fauna of
apple orchards in Nova Scotia. III. Mites and their
predators. Canadian Entomologist LXXXI(8):202-214.
05003924 Lozinskii, M.O.; Pupko, L.S.; Dychenko, A.I.; Kukota, S.N. ;
Protopopova, G.V.; Cherepenko, T.I.; Pel'kis, P.S. (1971)
Sintez i insektitsidnaya aktivnost1 zameshchennykh
gamma-bromatsetouksusnogo efira i nitroformal1 degida. [The
synthesis and insecticidal activity of substituted
arylhydrazones of gamma-bromoacetoacetic ester and
nitroformaldehyde.] Fiziologicheski Aktivnye Veshchestva.
05001331 MacNeil, J.D.; Frei, R.W.; Hutzinger, 0. (1973)
Electron-donor-acceptor complexing reagents in the analysis of
pesticides. VI. Influence of structure in detection and
identification. Mikrochimica Acta 5:641-650.
05001838 MacPhee, A.W. (1953) The influence of spray programs on the fauna
of apple orchards in Nova Scotia. V. The predacious
thrips Haplothrips faurei Hood. Canadian Entomologist
LXXXV:33-40.
05001388 MacPhee, A.W.; Sanford, K.H. (1954) The influence of spray
programs on the fauna of apple orchards in Nova Scotia. VII.
Effects on some beneficial arthropods. Canadian Entomologist
LXXXVI:128-135.
05001389 MacPhee, A.W.; Sanford, K.H. (1956) The influence of spray
programs on the fauna of apple orchards in Nova Scotia. X.
Supplement to VII. Effects on some beneficial arthropods.
Canadian Entomologist LXXXVIII(11):631-634.
05010580 MacPhee, A.W.; Sanford, K.H. (1961) The influence of spray
programs on the fauna of apple orchards in Nova Scotia. XII.
Second supplement to VII. Effects on beneficial arthropods.
Canadian Entomologist XCIII:671-673.
05001625 Maloney, T.E.; Palmer, C.M. (1956) Toxicity of six chemical
compounds to thirty cultures of algae. Water and Sewage Works
103(11):509-513.
05006838 Maruyama, K.; Arakawa, S. (1974) The photochemical reaction of
1,4-naphthoquinone derivatives with hydrogen donors. Bulletin
of the Chemical Society of Japan 47(8):1960-1966.
05004247 Matthews, D.N.; Kelly, R.J.; loveless, F.C., inventors; thited
States Rubber Co., assignee (1964) Catalyseurs pour la
polymerisation d'olerines. [Catalysts for polymerization of
olefins.] Belgian brevet d1 invention 652,314. Dec 16. 29 p.
05001517 McCallan, S.E.A.; Miller, L.P.; Magill, M.A. (1955) Chemical names
for active ingredients of fungicides. Phytopathology
45(6):295-302.
108
-------
CITATION
05005035 McCallan, S.E.A.; Miller, L.P.; Weed, R.M. (1954) Comparative
effect of fungicides on oxygen uptake and germination of
spores. Contributions from Boyce Ihcmpson Institute
18(1):39-68.
05001665 McCully, K.A. (1969) Analysis of multiple pesticide
residues—chemical identity and confirmation of results. World
Review of Pest Control 8(1):59-74.
05003100 McKinley, W.P.; Magarvey, S.A. (1960) A quantitative method for
the determination of 2,3-dichloro-l,4-naphthoquinone (Phygon)
residues in cherry extracts. Journal of the Association of
Official Agricultural Chemists 43(4):825-828.
05001430 McLeod, A.G.; Ihcmson, R. (1958) THe effect of several fungicides
on stem rot of tobacco. New Zealand Journal of Agricultural
Research 1(6):866-873.
05004331 Miller, L.P. (1956) Use of radioactive tracers in studying
fungicidal action. Pages 223-233,?In?Conference on
Radioisotopes in Agriculture.
05001657 Miller, L.P.; McCallan, S.E.A. (1955) Seme examples of the use of
radioisotopes in studies of pesticide action. Pages
546-555, Iri International Horticultural Congress, Report, 14th;
Aug 29-Sep 6, 1955, The Hague, Netherlands. Edited by I.J.P.
Nieuwstraten. Wageningen, Netherlands: H. Veenman.
05005695 Miyaki, T.; Onuki, J., inventors; Ninon Paint Company, assignee
(1958) 2,3-Dikuroru-l,4-nafutokinon no haigosuru sentei ho-o
toryo no seizcho. [A method of manufacturing a ship-bottom
anti-fouling paint containing 2,3-dichloro-l,4-naphthoquinone.]
Japanese patent specification 58-3719. May 14. 2 p.
05001342 Nagayoshi, H.; Suzuki, K.; Kashiwa, T. (1975) Systematic
identification and determination of pesticides. Part 9:
classification of 89 pesticides and related compounds by
thin-layer chromatography. A translation of: Noyaku Kensasho
Hokoku. [Bulletin of the Agricultural Chemicals Inspection
Station.] 15:22-30.
05001405 Nath, S.; Baruah, G.D.; Singh, R.S. (1971) Raman and infrared
spectra of 2,3-dichloronaphthoquinone. Indian Journal of Pure
and Applied Physics 9(12):1071-1073.
00001527 Naugatuck Chemical (1955) The Name, Chemical Identity, and Composi-
tion of the Pesticide Chemical: [Phygon]. (Unpublished study
received Jun 1, 1955 under 16; submitted by Naugatuck Chemical,
Div. of United States Rubber Co., Naugatuck, Conn.; CDL:
092299-A)
05001525 Neely, D. (1970) Persistence of foliar protective fungicides.
Phytopathology 60(11):1583-1586.
00001516 Newell, J.E.; Mazaika, R.J.; Cook, W.J. (1958) Ihe microdeter-
mination of 2,3-dichloro-l,4-naphthoquinone (Phygon) in water.
Agricultural and Pood Chemistry 6(9):669-671. (Also In unpub-
lished submission received Sep 19, 1961 under 400-11; submitted
by Uniroyal Chemical, Bethany, Conn.; CEL:124354-A)
109
-------
MRID
05002693
CITATION
Nilov, G.I.; Blagonravova, L.N. (1968) Izmenenie aktivnosti
khlorofillazyi soderzhaniya khlorofilla v list'yakh rasteniy
pod vliyaniemnekotorykh khlororganicheskikh pestitsidov. [The
change of the activity of chlorophyllase and the content of
chlorophyll in plant leaves as affected by sane organochlorine
pesticides.] Pages 21-23, In Doklady Vsesoyuznoi Akaderaii
Sel'skokhozyaistvennykh Nauk. Nauk. [Proceedings of the
Ail-Union Academy of Agricultural Sciences, Vol. 6.] Moscow,
USSR: Vsesoiuznaia Akademiia Sel'skokhoziaistvennykh Nauk
Imeni V. I. Lenina.
05004237 Nilov, G.I.; Blagonravova, L.N. (1970) Fitotoksicheskoe deistvie
nekotorykh khlororganicheskikh pestitsidov na rasteniya. [The
phytotoxic effect of sane chlororganic pesticides on plants.]
Trudy, Gosudarstvennyi Nikitskii Botanicheskii Sad.
05002692 Nilov, G.I.; Blagonravova, L.N.; Kutishcheva, G.A. (1968) Vliyanie
nekotorykh khlororganicheskikh pestitsidov na dinamiku i
metabolizm sakharov v list'yakh masliny. [Effect of seme
organochlorine pesticides on the dynamics and metabolism of
sugars in olive leaves.] Byulleten Gosudarstvennogo Nikitskogo
Botanicheskogo Sada. [Bulletin of the Nikitskii State
Botanical Garden.] l(7):54-59.
00001508 O'Brien, G.E. (1956) Dichlone as a Control for Algae and Submersed
Aquatic Weeds: Agricultural Chemicals: Bethany Information Sheet
#82. Paper presented at the Weed Society of America Meeting;
Jan 5, 1956; New York, N.Y. (Unpublished study received Jan 15,
1957 under 400-11; prepared by United States Rubber Co., submit-
ted by Uniroyal Chemical, Bethany, Conn.; CEL:003230-M)
05001324 Odeyemi, O.; Alexander, M. (1976) Resistance of Rhizobium to
thiram, spergon, and phygon. Pages 171, In Abstracts of the
Annual Meeting of the «Smerican Society for Microbiology.
Edited by R.A. Day.
05001615 Odeyemi, O.; Alexander, M. (1977) Use of
fungicide-resistant Rhizobia for legume inoculation. Soil
Biology and Biochemistry 9(4):247-251.
05004893 Ohuchi, H.; Takagi, K., inventors; Mitsui Chemical Industries,
assignee (1954) [Production method for
2,3-dichloro-l,4-naphthoquinone.] Japanese patent
specification 54-1838. Apr 11. 2 p.
05001841 Oku, H.; Nakanishi, T.; Shiraishi, T.; Ouchi, S. (1973)
Phytoalexin induction by some agricutural [sic. agricultural]
fungicides and phytotoxic metabolites of pathogenic fungi.
Scientific Reports of the Faculty of Agriculture, Okayama
University 42:17-20.
05005006 Oshchepkova, E.P. (1964) Antiseptirovanie tovarnoi drevesnoi
massy. [Use of antiseptics for preservation of comnercial
groundwDod.] Bumazhnaya Promyshlennost. [Paper Industry.]
39(1):17-18.
05001387 Oudbier, A.J.; Bloomer, A.W.; Price, H.A.; Welch, R.L. (1974)
Respiratory route of pesticide exposure as a potential health
hazard. Bulletin of Environmental Contamination and Toxicology
110s
-------
MRID CITATION
05001327 Owens, R.G. (1953) Studies on the nature of fungicidal action.
II. Chemical constitution of benzenoid and quinonoid compounds
in relation to fungitoxicity and inhibition of amino- and
sulfhydryl-dependent enzymes. Contributions from Boyce
Thompson Institute 17:273-282.
05001326 Owens, R.G. (1953) Studies on the nature of fungicidal action. 1.
Inhibition of sulfhydryl-, amino-, iron-, and copper-dependent
enzymes in vitro by fungicides and related compounds.
Contributions from Boyce Thompson Institute 17:221-242.
05001664 Owens, R.G. (1969) Metabolism of fungicides and related compounds.
Annals of the New York Academy of Sciences 160(1):114-132.
05002878 Owens, R.G.; Blaak, G. (1960) Chemistry of the reactions of
dichlone and captan with thiols. Contributions from Boyce
Thompson Institute 20(8):475-497.
05001520 Owens, R.G.; Blaak, G. (1960) Interaction of captan and dichlone
with coenzyme A and other thiols. Phytopathology
50(9):649-650.
05001393 Owens, R.G.; Blaak, G. (1960) Site of action of captan and
dichlone in the pathway between acetate and citrate in fungus
spores. Contributions from Boyce Thompson Institute
20(8):459-474.
05001328 Pal, R.N.; Gopalakrishnan, V. (1968) Preliminary trials on the
toxicity of "Algistat" to fish and algae. Fish Technology
5(2):101-103.
05001575 Palm, E.T.; Young, R.A. (1957) The compatibility of certain
organic fungicides and antibiotics in treatment mixtures as
indicated by stability and phytotoxicity. Plant Disease
Reporter 41(3):151-155.
05003840 Parups, E.V. (1962) The effect of 2,3-dichloro-l,4-naphthoquinone
on maleic hydrazide treated greenhouse-grown tobacco. Tobacco
154(3):23-26.
05003841 Parups, E.V.; White, F.H. (1963) The effect of maleic hydrazide
and 2,3-dichloro-l,4-naphthoquinone on field-grown cigar
tobacco. Tobacco 157(3):29-31.
05003926 Perevoznikov, M.A. (1977) 0 toksichnosti nekotorykh pestitsidov
dlya ryb. [The toxicity of some pesticides to fish.] Izvestiya
Gosudarstvennogo Nauchno-Issledovatel'skogo Instituta Ozernogo
i Rechnogo Rybnogo Khozyaistva. [Bulletin of the State
Scientific Research Institute of Lake and River Fisheries.]
121:95-96.
05001424 Prakash, G.; Ebdnett, E.M. (1978) Discriminant analysis and
structure-activity relationships. I. Naphthoquinones. Journal
of Medicinal Chemistry 21(4):369-374.
05001472 Quinby, J.R.; Stewart, R.B.; Watkins, G.M. (1963) Seed treatment
studies on sorghum in Texas. Agronomy Journal 53(6):550-551.
05013360 Rathaiah, Y. (1973) Etude du faux mildiou du cotonnier
(Ramularia areola Atk.); II. Essais in vitro de divers
fongicides classiques ou systemiques. [Grey mildew of cotton
caused by Ramularia areola Atk.: II. In vitro tests of certain
classical or systemic fungicides.] Coton et Fibres Tropicales
(French Edition) XXVIII(4):523-527.
05002767 Reddish, G.F., ed. (1954) Antiseptics, Disinfectants, Fungicides
and Chemical and Physical Sterilization. Philadelphia, Pa.:
Lea and Febiger.
Ill
-------
MRID CITATION
05001415 Reitz, L.P.; Hansing, E.D.; Davidson, F.E.; Decker, A.E. (1947)
Viability and seed treatment of flax. Journal of the American
Society of Agronomy 39:959-970.
05001599 Riley, H.K.; Daigle, C.J. (1948) Spray tests for azalea petal
blight. Pages 651-653, In Proceedings—American Society for
fibrticultural Science. Vol. 51. St. Joseph, Mich.: American
Society for Borticultural Science.
05001476 Saito, G.; Matsunaga, Y. (1971) The electron-acceptor strengths of
some substituted naphthoquinones. Bulletin of the Chemical
Society of Japan 44(7):1788-1791.
05001483 Sawicki, E.; Stanley, T.W.; McPherson, S. (1961)
Spectrophotonetric determination of 1,4-naphthoquinane and its
2,3-dichloro derivative. Chemist-Analyst 50:103-104.
05001995 Saxena, J.; Sikka, H.; Zweig, G. (1972) Effect of quinone
pesticide (dichlone) on various modifers of growth of
Rhodospirillum rubrum. Pages 7, In Abstracts of the Annual
Meeting of the American Society of Microbiology.
05001996 Saxena, J.; Sikka, B.C.; Schwelitz, F.; Zweig, G. (1973)
Permeability changes in dichlone-treated Chlorella
pyrenoidosa as influenced by pH and temperature. Pages
170, In Abstracts of the Annual Meeting of the American
Societyof Microbiology.
05001508 Saxena, J.; Sikka, B.C.; Zweig, G.; Gordon, G.B. (1974) Structural
and functional changes in mouse fibroblast cells treated with
2,3-dichloro-l,4-naphthoquinone (dichlone). Pesticide
Biochemistry and Physiology 4(2):185-200.
05001598 Schwelitz, F.D.; Sikka, B.C.; Saxena, J.; Zweig, G. (1973)
Ultrastructural changes in isolated spinach chloroplast and
in Chlorella pyrenoidosa chick (Emerson strain) treated with
dichlone. Plant Physiology. Suppl. 51:27.
05001509 Schwelitz, F.D.; Sikka, H.C.; Saxena, J.; Zweig, G. (1974)
Ultrastructural changes in isolated spinach chloroplasts and
in Chlorella pyrenoidosa chick (Emerson strain) treated with
dichlone. Pesticide Biochemistry and Physiology 4(4):379-385.
05005012 Sergeev, G.B.; Batyuk, V.A.; Karunina, L.P.; Zenin, S.V. ;
Kurzanova, V.V. (1970) Gazokhramatograficheskii analiz
produktov okisleniya nekotorykh naftokhinolfosfatov. [Gas
chromatographic analysis of the oxidation products of sane
naphthoquinone phosphates.] Vestnik Moskovskogo Universiteta,
Khimiya. [Journal of Moscow University, Chemistry.]
11(6):674-679.
05004245 Shein, S.M.; Troyanov, I.A.; Mel'nik, Y.P.; Pozdnyakova, E.M.;
Mostoslavskii, M.A., inventors; (1962) Sposob polucheniya
2,3-dikhlornaftokhinona-l,4. [Method for producing
2,3-dichloro-naphthoquinone-l,4.] U.S.S.R. opisanie
izobreteniya k avtorskomu svidetel'stvu 148040. Jun 21. 2 p.
05005422 Sikka, B.C.; Carroll, J.; Zweig, G. (1971) Effect of certain
quinone pesticides on acetate photonetabolism and dark CO?
fixation in Chlorella. Pesticide Biochemistry and Physiology
1(3/4):381-388.
112
-------
MRID CITATION
05001843 Sikka, H.C.; Saxena, J.; Zweig, G. (1973) Effect of dichlone on
the permeability of Chlorella pyrenoidosa. Pages
73, In Abstracts—1973 Meeting of the Weed Science Society of
Anerica; Feb 6-8, 1973, Atlanta, Georgia. Champaign, 111.:
Weed Science Society of America.
05001398 Sikka, B.C.; Schwartzel, E.H.; Saxena, J.; Lynch, R.S.; Zweig, G.
(1975) Action of dichlone on the human eyrthrocyte membrane.
Pages 507-512, In Environmental Quality and Safety.
Supplement: Pesticides. New York: Academic Press.
05001392 Sikka, B.C.; Schwartzel, E.H.; Saxena, J.; Zweig, G. (1974)
Interaction of dichlone with human erythrocytes. I. Changes
in cell permeability. Chemico-Biological Interactions
9(4):261-272.
05002004 Sikka, B.C.; Shimabukuro, R.H.; Zweig, G. (1972) Studies on effect
of certain quinones. I. Electron transport,
photophosphorylation, and CO2 fixation in isolated
chloroplasts. Plant Physiology 49(3):381-384.
05001653 Sjoestrand, B.T.L., inventor; (1960) Manufacture of halogenated
organic compounds. U.S. patent 2,955,117. Get 4. 3 p.
05001513 Sleeth, B. (1946) The effect of fungicidal seed treatments on
guayule seeding emergence. Phytopathology 36:999-1010.
05001491 Smith, C.F.; Jones, I.D.; Calvin, L.D. (1950) Effect of
insecticides on the flavor of peaches—1949. Journal of
Economic Entomology 43(2):179-181.
05001612 Scmers, E. (1962) Mechanisms of toxicity of agricultural
fungicides. Science Progress 50(198):218-234.
05001474 Sproston, T., Jr.; Bassett, E.G. (1954) Paper chrcmatography of
some substituted naphthoquinones. Analytical Chemistry
26(3):552-553.
05003894 Steffen, K.; Peschel, H. (1975) Biochemische Transformation durch
Pilze und antifungale Wirkung von 1,4-Naphthochinonen,
biosynthetischen Zwischenprodukten und chemisch verwandten
Stoffen. [Biochemical transformation by fungi, and antifungal
activity of 1,4-naphthoquinones, of biosynthetic intermediary
products, and of chemically related compounds.] Angewandte
Botanik 49(3/4):155-167.
05001375 Suzuki, K.; Miyashita, K.; Nagayoshi, H.; Kashiwa, T. (1973)
Separation and identification of 20 pesticides in their
mixture. Agricultural and Biological Chemistry
37(8):1959-1962.
05001468 Suzuki, K.; Nagayoshi, H.; Kashiwa, T. (1974) The systematic
separation and identification of pesticides in the second and
third division. Agricultural and Biological Chemistry
38(8):1433-1442.
05004778 Syrowatka, T.; Jurek, A. (1974) Rakotworczosc pestycydow
Higieny. [Annals of the Polish Institute of Hygiene.]
XXV(5):563-576.
113
-------
MRID CITATION
05006344 Takaoka, K. (1967) Karamatsu senkobyo ro yakuzai bojo ni kansuru
kenkyu (Dai-ippo) karanatsusenkcbyokin ni taisuru kakashu
noyakuyosa sakkinzai ro kokinryoku. [Studies on the chemical
control of the shoot blight of larch caused by Guiganardia
laricina (Sawada) Yamamoto et K. Ito. I. Inhibiting effect
of several fungicides on the mycerial growth of Guiganardia
laricina (Sawada) Yamamoto et K. Ito.] Sankyo Kenkyusho
Nempo. [Annual Report of Sankyo Research Laboratories.]
19:118-120.
05001660 Tate, H.D.; O'Brien, G.E. (1956) Dichlone as a control for algae
and submersed aquatics. Pages 30, In Proceedings—13th North
Central Weed Control Conference. Lincoln, Nebr.: North
Central Weed Control Conference.
05004750 Tatsuyama, K. (1967) Noyaku to sesshoku sareta kurorera no iro no
henka—noyakukenkyu ni okeru kurorera no riyo. [Discoloration
of Chlorella cells treated with several pesticides—utilization
of Chlorella cells for the study of pesticides.] Nippon
Shokubutsu Byori Gakkaiho. [Annals of the Phytopathological
Society of Japan.] 33(3):192-195.
05001382 Taylor, R.H. (1953) Grape mold control. Australian Plant Disease
Recorder 5:6.
05001422 Thonas, E.J.; Burke, J.A.; Lawrence, J.H. (1968) Thin-layer
chronatography; relative migration data (RTDE) of chlorinated
pesticides. Journal of Chromatography 35(1):119-121.
05001419 Thompson, J.F.; Mann, J.B.; Apodaca, A.O.; Kantor, E.J. (1975)
Relative retention ratios of ninety-five pesticides and
metabolites on nine gas-liquid chromatographic columns over a
temperature range of 170 to 204 degrees C in tvvo detection
modes. Journal of the Association of Official Analytical
Chemists 58(5):1037-1050.
05001518 Tyler, L.J.; Murphy, R.P.; MacDonald, H.A. (1956) Effect of seed
treatment on seedling stands and on hay yields of forage
legumes and grasses. Phytopathology 46:37-44.
00001526 United States Rubber Company (1955?) The Name, Chemical Identity,
and Composition of the Pesticide Chemical: [Phygon]. (Unpub-
lished study received Feb 11, 1957 under 107; CDL:092387-C)
00001525 United States Rubber Company (1957?) The Name, Chemical Identity,
and Composition of the Pesticide Chemical: [Phygon]. (Unpub-
lished study received Aug 15, 1958 under 188; CDL:092464-D)
00001539 United States Rubber Company (1965?) Phygon Technical (Dichlone):
Agricultural Chemicals(R): Bethany Information Sheet No. 63.
(Unpublished study received Aug 31, 1965 under 8729-3; submitted
by ECO Sciences, Inc., Boonton, N.J.; CDL:009475-D)
05001373 Vaczi, L.; Uri, J. (1954) Studies on the enzyme penicillinase.
Acta Microbiologica Academiae Scientiarum Hungaricae
II(1/2):167-177.
05001374 Vainio, H.; Parkki, M.G. (1975) Deterioration of drug
biotransformation in rat liver by a fungicide dichlone. Acta
Physiologica Scandinavica 95(2):60A-61A.
05004233 Vasilenko, N.M. (1973) Osobennosti gigienicheskogo normirovaniia v
zavisimosti ot kharaktera toksicheskogo deystviya khimicheskikh
veshchestv. [Characteristics of hygienic standardization in
relation to the nature of the toxic effect of chemical
substances.] Gigiena Truda. [Labor Hygiene.] 9:71-74.
114
-------
MRID CITATION
05001329 Vasilenko, N.M.; Labunskii, V.V. (1972) Toxicology of
benzoquinones, naphthoquinones, and their derivatives (review).
A translation of: Gigiena Truda i Professional'nye
Zabolevaniya. [labor Hygiene and Occupational Diseases.]
16(8):29-34.
05005961 Vire, J.C.; Patriarche, G.J. (1978) Determinations coulometriqu.es
de quinones et de chloronaphtoquinones a 1'aide du titane (III)
electrogenere. [Coulometric determinations of quinones and
chloronaphthoquinones using electro-generated titanium (III).]
Analytical Letters 11(4):307-317.
05003810 Vladimirtsev, I.F.; Stromberg, A.G. (1957) Polyarogaficheskoe
issledovanie 2,3-proizvodnykh 1,4-naftokhinona. [Polarographic
study of 2,3-derivatives of 1,4-naphthoquinone.] Zhurnal
Cbshchei Khimii. [Journal of General Chemistry.] 27:1029-1041.
05006881 Walsh, G.E. (1972) Insecticides, herbicides, and polychlorinated
biphenyls in estuaries. Journal of the Washington Academy of
Sciences 62(2):122-139.
05007016 Watanabe, S.; Momo, H.; Kashiwa, T. (1972) Noyaku no
kan'iteirycbunseki e no hakuso-kurcmatogurafu—denshito-meta-ho
no oyo. [Application of densitonetry to simple determination
of pesticides by thin-layer chromatography..] Nogaku Kensasho
Hokoku. [Bulletin of the Agricultural Chemicals Inspection
Station.] (12):19-22.
00001541 Weintraub, R. (1966) Phytotoxicity Studies: [Aqua Biotics Algae De-
stroyer] . (Unpublished study received Jul 21, 1966 under 8709-
1; prepared by Martins Aquarium, submitted by Aquarium Pharma-
ceuticals, Perkasie, Pa.; CDL:009483-A)
05001512 Wolf, F.T. (1966) The effect of some synthetic quinones on the
Hill reaction in spinach chloroplasts. Phytochemistry
5(2):263-265.
05004756 Woodcock, D. (1977) Nonbiological conversions of fungicides.
Pages 209-249, In Antifungal Compounds. Edited by M.R. Siegel
and H.D. Sisler. New York: Marcel Dekker.
00001512 Wurtz, C.B. (1956) Bio-Assay of Phygon-XL. (Unpublished study
received May 8, 1962 under unknown admin, no.; prepared by
Consulting Biologists for Naugatuck Chemical, submitted by
Uhiroyal Chemical, Bethany, Conn.; CDL.-108441-A)
05005246 Yoshida, M.; Cnaka, M.; Fujita, T.; Nakajima, M. (1979) Inhibitory
effects of pesticides on growth and respiration of cultured
cells. Pesticide Biochemistry and Physiology 10(3):313-321.
05002159 Zuman, P. (1962) Quantitative treatments of substituent effects
inpolarography. IV. Linear free energy relationships in
quinoid series. Collection of Czechoslovak Chemical
Communications 27:2035-2057.
05001397 Zutshi, U.; Kaul, B.L. (1975) Studies on the cytogenetic activity
of some conmon fungicides in higher plants. Cytobios
12(45):61-67.
05001409 Zweig, G.; Hitt, J.E.; Cho, D.H. (1969) Mode of action of
dipyridyls and certain quinone herbicides. Journal of
Agricultural and Pood Chemistry 17(2):176-181.
115
-------
MRID CITATION
05012878 Zweig, G.; Sikka, H.; Saxena, J. (1974) Comparative effects of
quinone herbicides on plant and animal cell membranes (abstract
no. 180). Pages 78-78, In Abstracts—1974 Meeting of the Weed
Science Society of Merica; Feb 12-14, 1974, Las Vegas, Nevada.
Champaign, 111.: Weed Science Society of America.
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