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## 1. Table of Contents
1. Executive summary ............................................................................................................. .... 4 2. Introduction .................................................................................................................. ........... 5 3. Use Characterization .......................................................................................................... ..... 6 A. Thiophanate methyl as a Conventional Ac tive Ingredient: Products and Uses ............... 6 B. Carbendazim Use as a Conventional Activ e Ingredient for Tree Injection ..................... 7 C. Carbendazim Industrial Uses as an Active Ingredient (MBC) ......................................... 7 D. Carbendazim Antimicrobial Products .............................................................................. 7 E. Overall Status of Product Labels ...................................................................................... 7 F. Usage.......................................................................................................................... .......... 8 2. Conclusions from Previous Risk Assessments ..................................................................... 10 A. Decisions from Previous Re registration Actions ........................................................... 10 Thiophanate Methyl Assessments......................................................................................... 10 Antimicrobial Assessments - Carbendazim .......................................................................... 13 Carbendazim Assessments .................................................................................................... 13 B. Ecological Risks ............................................................................................................. 14 C. Drinking Water Exposure ............................................................................................... 14 D. Clean Water Act Programs ............................................................................................. 15 3. Environmental Fate and Transport........................................................................................ 15 A. Fate Properties of Residues of Concern ......................................................................... 15 B. Transformation Products ................................................................................................ 22 4. Receptors...................................................................................................................... ......... 24 A. Aquatic Toxicity of Thiophanate methyl ....................................................................... 24 B. Aquatic Toxicity of MBC .............................................................................................. 25 C. Terrestrial Toxicity of Thiophanate methyl ................................................................... 26 D. Terrestrial Toxicity of MBC .......................................................................................... 27 E. Additional Effects .......................................................................................................... 2 8 F. Ecological Incidents .......................................................................................................... . 28 5. Exposure Pathways of Concern ............................................................................................ 29 6. Analysis Plan ................................................................................................................. ....... 30 A. Stressors of Concern....................................................................................................... 31 Ecological Risk Assessment ................................................................................................. 31 Drinking Water ................................................................................................................ ..... 32 B. Measures of Exposure .................................................................................................... 33 C. Measures of Effect ......................................................................................................... 33 D. Endangered Species Assessments .................................................................................. 35 E. Endocrine Disruptor Screening Program ....................................................................... 35 7. Preliminary Identification of Data Gaps ............................................................................... 35 A. Environmental Fate ........................................................................................................ 35 B. Effects ....................................................................................................................... ...... 40 8. References .................................................................................................................... ......... 47

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3 9. Appendices .................................................................................................................... ........ 50 A. SIP and STIR Results ..................................................................................................... 50 B. Structures of Thiophanate Methyl and Degradates ........................................................ 55 C. OPPIN Bibliography of Environmental Fate and Ecological Eff ects Studies Submitted to support the Registrations of Thiophanate Methyl or MBC .................................................. 57 102001 Thiophanate methyl Eco Effects Bibliography ........................................................ 57 128872 Carbedazim (MBC) Eco Effects Bibliography ........................................................ 68 102001 Thiophanate-methyl Fate Chemistry Bibliography ................................................. 73 128872 Carbendazim Fate Chemistry Bibliography ............................................................. 81 D. A CTIVE 

### Registrations For 102001 / 23564- 05-8 / Thiophanate-methyl ........................ 88 E. Active Registrations for 128872 / 10605-21-7 / Carbendazim\ ..................................... 98

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4 

# 1. Executive summary

The Environmental Fate and Effects Division (EFE D) and the Antimicrobial Division (AD)have completed the preliminary problem formulation for the ecological ris k, environmental fate, endangered species, and drinking water assessments to be conducted as pa rt of the registration review of Thiophanate methyl [Dimet hyl((1,2,-phenylene)bis(iminocarbonothioyl))bis (carbamate) and carbendazim (methyl benzimid azol-2-ylcarbamate). In this document, Thiophanate methyl is referred to as “TF” and Carbendazim as “MBC” noting that TM is the active ingredient of many formulated products wh ile MBC is the are active ingredient for only limited conventional and antimicrobial products in addition to being the primary (and fungicidally active) degradate of TM. This problem formulation describes the methods EFED and AD plan to use during the completion of drin king water and ecological risk assessments in support of registration review and provides an ov erview of the environm ental fate, ecological effects, and potential risks associ ated with the use of the two fungi cides, as well as uncertainties unique to their risk assessment. This document also identifies additional studies that would be beneficial to the conduct of an ecological risk assessment.

Major findings are:

(1) Several key studies for environmental fate and transport for the two chemicals appear to be incomplete by current guideline standards and / or need to be supplemented with studies at additional test sites to fully understand the environmental fa te of TM and MBC

a. 835.2120, Hydrolysis . Existing studies for TM and MBC will be re-reviewed. An additional test at 35 C is also required for MBC to provide additional data on the hydrolysis rate. b. 835.4100, Aerobic soil metabolism . Existing studies do not adequately describe the formation and decline of TM metabolites a nd there are insufficient studies with MBC applied. New studies are requested for both TM and MBC in three new test soils.

c. 835.4200 and 835.4300, Aerobic aquatic metabolism and anaerobic aquatic metabolism . Aerobic aquatic and anaerobic aqua tic metabolism. New studies are requested for both TM and MBC in three new test sediment and water systems. d. 835.1230. Batch equilibrium adsorption / desorption . An updated review will be conducted of a previously submitted study (MRID 42351001) which includes batch equilibrium adsorption /desorption studies for TM, MBC, and other metabolites of TM. Pending the outcome of this re view, a new study may be required. (2) Updated environmental chemistry methods (ECM s) for TM and MBC in water and soil is required along with their associated inde pendent laboratory va lidations (ILVs); (3) The database is incomplete for Thiophanate methyl in areas of chronic toxicity. At this time, no additional data are requested as the chronic data for its degradate MBC will be utilized. This is based on the assumption that chronic toxi city of TM is related to long-term exposure to MBC, the major and terminal degradate of TM; (4) Toxicity to aquatic plants are re quested (guideline studies: 850.4400, 850.4500 and 850.4550) for the MBC degradate to assess potentia l impacts to this group. This is based on the expected concentrations of MB C in the aquatic environment;

### `

5 (5) Whole sediment toxicity test for aquatic i nvertebrates are requested (guideline studies: 850.1735 and 850.1740). This is based on K oc 

### values > 1000 for MBC and the expectation that this degradate will reach both fresh and es tuarine/marine habitats from current uses; (6) The environmental fate and transport database is sufficient and complete for most of the antimicrobial uses except where non-guideline leaching studies are required for the following use scenarios:

a. Exterior paint coated surfaces b. Wood protective stains

c. Roof coatings d. Treated textiles



# 2. Introduction

This preliminary problem formulation is in supp ort of the Registration Review of Thiophanate Methyl (TM) and Carbendazim (MBC). In this problem formulation, TM and MBC will be considered as two independent pesticides for prod ucts containing either TM or MBC. Due to the fact that MBC is the major degradation product of TM, MBC will also be considered in the PF for TM.

TM was first registered as a pesticide in th e U.S. in 1973. MBC has been registered as an independent active ingredient since 1968. It is noted, however, that the extent and variety of registered uses for TM is much greater than MBC. Both TM and MBC are in the benzimidazole class of systemic fungicide th at is absorbed by sprouts, l eaves, and roots of plants and translocated within the transpiration system in plant xylem.

TM and MBC inhibit the development of fungal ge rm tubes, the formation of appressoria, and the growth of mycelia. Their fungi toxic action is based on blockage (inhibition) of nuclear division during mitosis and destab ilization of fungal cell structur es. MBC interferes with cell division and DNA biosynthesis in fungi and has been shown to be genetically toxic through inhibition of the spindle a pparatus in cell division.

In the environment, TM is expected to degr ade rapidly to its primary degradate methyl 2- benzimidazolylcarbamate (MBC) 1 

### . EFED assumes that the initial, acute short-term exposure (after application of TM) may e ither the parent TM or MBC (s ince the half-life for conversion from TM to MBC may be from less than one day to several days by various environmental pathways) and that long-term chronic exposure will involve the MBC degradate. Though TM shows only moderate toxicity to most fish and invertebrate species (LC 50 

### values of 1.1-49.5 mg a.i/L (ppm) for acute toxicity to technical), MBC has been observed to be more highly toxic with acute LC 50 

### toxicity values as low as 10 μg a.i/L ( ppb) for fish and observed chronic effects at concentrations as low as 2.1 ppb for fish and 25 p pb for aquatic invertebrates. For species that are much more sensitive on an acute basis to M BC than TM, acute and chronic effects are more likely to occur after TM is converted to MBC

.

1 Note that in many of the source documents cited he re MBC is often referred to as carbendazim.

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6 

# 3. Use Characterization

Summaries of the active product registrations for thiophanate methyl and carbendazim are provided in Appendix D and E, respectively.


## A. Thiophanate methyl as a Co nventional Active Ingredient: Products and Uses Labeled use patterns for TM fungicide on agricu ltural food and feed cr ops are represented by over ninety five active end-use products containi ng up to 85% of the ac tive ingredient TM in product formulations. In addi tion, twelve new products are pe nding. Seventy four of the products are formulated with the single active in gredient TM while twenty nine are multi active mixtures with other fungicides including Chlo rothalonil, Mancozeb, Iprodione, Tebuconazole, Propiconazole, Etridiazole, Flut olanil, Captan, Cymoxanil, an d Pyraclostrobin. Many of the products contain less TM than the other active components which may range up to 72% of the mixture. Preliminary review of current labe ls by EPA has shown some products that permit yearly rates as high as 2.8 lbs a. i/A on food crops divided into 2 to 4 separate applications (EPA Reg. No. 73545-11).

In addition to use on a wide variety of agricult ural food and feed crops, registered uses also include non-food/feed use sites such as golf cour ses, sod farms, greenhouses and nurseries. TM has also registered residential uses on lawns, ornamental trees , shrubs, and plants. Preliminary review of current labels by EPA has shown that residential and commercial turf application rates may range from 2.7 to over 8.1 lbs a.i /application with seasonal limits of 2.7 lbs a.i on golf course fairways to 21.7 lbs a.i on tees and gr eens (EPA Reg. No. 1001-63). In general, 14 day application intervals are recommended.

Treatment equipment for TM products include s aircraft and ground equipment. Ground equipment includes drench, flood and drip irriga tion systems. The products may be applied by soil application, seed treatm ent and foliar application.

TM is applied as preventive and/ or curative fungicide to combat large variety of primary target pests including blight (blossom, gummy stem, stem end, shoot, pod, stem, tip, brown needle and leaf), certain algae , various rot species (brown, black, white, stor age, bulls-eye, charcoal, clove, foot, crown, fruit and jacket), scab (apple scab) mildews ( black pox, flyspeck, powdery ) , sooty blotch, molds (blue, gray and white vari eties), numerous species of spot (target, early leaf, late leaf, liver, brown, frog-eye, cherry leaf , eye Brook’s fruit and downy), as well as web blotch, rust, leaf scorch, smut and fusarium species

.

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7 

## B. Carbendazim Use as a Convention al Active Ingredient for Tree Injection Currently MBC is only registered as a conventional activ e ingredient for use as a tree injection application to ornamental trees. There are three active Section 3 products containing MBC (Imisol TM 

### 7946-21, Abasol TM 

### 7946-20, and Fungisol TM 

### 7946-14). All three products are coformulated with debacarb/2-EEEBC (PC 115001; CAS # 62732-91-6). In addition, Imisol TM 

### is co-formulated with imidacloprid (PC 129099, CAS # 138264-41-3) and Abasol TM 

### is coformulated with avermec tin (PC 122804, CAS # 71751-41-2).

All three MBC-containing products c onsist of 4 or 6 mL (product) ca psules that are injected via a closed micro-injection system consisting of a f eeder tube and compressible injector unit (the “Mauget System”) 2 

### . The maximum number of capsules allo wed per treatment is determined by the size of the tree as measured by the diameter at breast height (DBH ). MBC comprises 0.3% (w/w) of all three products.



## C. Carbendazim Industrial Uses as an Active Ingredient (MBC)

Carbendazim 

### is registered for use as an indus trial microbiocide and broad spectrum fungistat/algaecide to control or inhibit the growth of bacteria, fungi, and algae, respectively, in exterior paints, stains, masonry coatings, coat ings, exterior insulati on and finishing systems (EIFS) coatings, paper coatings, inks, textiles, size-press and other fill er/sealant solutions for non-food grade products, building materials, roof coatings, stucco and joint cements, cement admixtures, concrete admixtures, and gypsum bo ard, plastics (PVC), wood protective stains, solvent based wood protective stains, adhesives, grouts, plasters, sealants, caulks, fillers, architectural products, finishes and special pur pose coatings, plastic mills such as wood composites, piping and gaskets



## D. Carbendazim Antimicrobial Products MBC is included in 12 products from 4 companies when used for fungicidal protection in paints and coatings and is produced by two companies as technical ingredient containing 7.5 % to 99 % of the MBC.



## E. Overall Status of Product Labels

As stated in the previous four sections, there are many labeled use patterns for TM and for MBC. A review of some of the labels shows that most of the information needed for future modeling is present. However, OPP requests registrants to review their respective labels and provide all missing information. The label should include th e following information: the maximum single application rate in lbs a.i/A; the maximum number of applicati ons/year; the minimum application

2 http://www.mauget.com/index.cfm?PageID=12&gen2

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8 intervals; application procedure(s); application ti ming and all of the appli cation restrictions, if any. In case of any of the information is mi ssing, EFED / AD will use the most conservative parameters that may lead to conservative exposure estimates.



## F. Usage

A full use report has not been received from the Biological Economic Analys is Division at this time, but a final report will be available to be utilized for the Re gistration Review risk assessment. Interim reports have been analyzed for this usage assessment.

Thiophanate methyl usage data indicates wide usage on a variet y of agricultural food and feed crops. According to the Screening Level Usag e Analysis (SLUA: Biological and Economic Analysis Division, 3/7/2013), TM is used on over 34 agricultural cr ops with variable percentages of each crop treated. The percent treated may ra nge from less than 2.5% to as high as 50% for strawberry crops. Other crops with 30% or more of the crop treated include apples, green beans, pears, and pistachios.

Current major crop uses and EPA estimated % cr op treated include almonds (5-10%), apples (20-30%), apricots (,2.5%), gree n beans (25-45%), blueberries (5 -25%), cantaloupes (10-25%), celery(5%), cherries (5-10%), cotton (<2.5%), cu cumbers (5-15%), dry beans (5-15%), peas (5- 15%), grapefruit (5-10%), grapes (5-15%), hone ydew melons (10%), on ions (<2.5%), oranges (<2.5%) , peaches (5-15%), peanuts (<2.5%), pears (15-30%), pecans (<2.5%), peppers (<2.5%), pistachios (30-40%), plums (<2.5%), pr unes (<2.5%), potatoes (<2.5%), pumpkins (5- 10%), soybeans (<2.5%), squash (5-10%), st rawberries (20-50%), sugar beets (<10%), tangerines (<2.5%), tomatoes, (5-20%) walnut s (<2.5%), watermelons (15-25%), and wheat (<2.5%). Based on Agency maximum percent cr op use estimates for these crops the annual number of acres could potentially exceed 4,500,000 acres on a nationwide basis using USDA 2007 Agricultural Census estimates for crop acreages.

The U.S. Geological Survey (USGS) pesticide us e map (Figure 2) shows regional scale patterns in use intensity within the United States. The USGS pesticide maps are largely based on state level estimates of pesticide use rates for individual crops and cr op acreage data from the National Agricultural Statistics Service. Usage patterns appear to vary geographically over the last 10 years of evaluation. The maps and details on th eir preparation are prov ided here:

http://water.usgs.gov/nawqa/ pnsp/usage/maps/compound_listing.php http://water.usgs.gov/nawqa/pnsp/usage/maps/about.php

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9

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10 No acreage estimates for TM for non-food uses (golf courses, sod farms, greenhouses and nurseries, residential uses on lawn s, ornamental trees, and shrubs ) have been compiled at this time. This type of estimate is quite difficult to conduct. However, it is assumed that this acreage could potentially be substantial. For example, in attempting to determine modeling procedures for golf courses the Agency consulted the Go lf 20/20 Industry Report for 2002. There were about 15,827 golf courses in the United States as of March 2003. Golf course characteristics information provided by the Golf Course Superintendents Association of America (GCSAA) 3 

### indicates that an 18-hole golf facility averages about 150-20 0 acres of total land, including water bodies, hard structures, and out-of-play areas. A typical urban golf course is only 110-120 acres, and courses in resort areas may be 170-190 acres (G. Lyman, GCSAA; personal communication 11/19/04). Generally, pesticides are not applied to entire golf courses, but rather to some holes and some parts of the course (e.g., tees, greens, and/or fairways). Based on a median estimate of 150 acres/course multiplied by 15,827 total courses and reduced to 50% as potential turf area coverage the total potential acreage could be ove1,000,000 acres nationwide. For commercial sod farms, USDA Census estimates were made in 2007. In 2007, sod farms showed a 6 % increase in acreag e with an 11.4% decrease in the number of farms since 2002. The total nationwide acreage of sod farms was estimated to be 409, 000 acres in 2007. The highest number of such farms was located in southe rn states (1,037 farms-266,000 acres) with Florida, Texas and Georgia being the dominant states.

No usage data is available for the in dustrial use of MBC It is important to note however that such data may be necessary for modeling exposure for these uses (e xample yearly production data for these uses are required for down the drain modeling.



# 2. Conclusions from Previous Risk Assessments

A. Decisions from Previous Reregistration Actions

Thiophanate Methyl Assessments

EFED conducted the following ecological risk assessments for TM on the following actions:

(1) The 2001 EFED RED Chapter and subseq uent 2005 OPP Reregistration Eligibility Document The first EFED RED Chapter was prepar ed on 5/24/2000 and was released in 2001. In this document, use patterns and application methods were assessed including aerial and/or ground applications to major crop groups such as tree crops (apples, almonds, nectarines, cherries, citrus, peaches, pecans, plums, prunes a nd apricots), row crops (lima snap bean and drytype beans), vegetable crops (celery, cucumber, peanuts, potato-white/Irish, pumpkin), small grains (such as wheat), and turf and ornamental uses. In this EFED RED chapter the assumption was made that acute exposure and risk to terrest rial and aquatic organism s are primarily related to parent TM and chronic exposure and risk are primarily related to the MBC degradate. Although TM appears to be stable in aerobic aquatic systems and to resist hydrolysis at pH 7, the chemical reaching the soil system is expected to degrade to its major degradate MBC within few days following application. Rapid degradation to MBC is expected based on the short half-live

3 URL: 

### Golf Course Superintendents Association of America

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11 observed in aerobic soil and anaerob ic aquatic systems via biotic and abiotic processes. MBC, on the other hand, is relatively long lived in aerob ic soil and aerobic aquatic systems and also considered stable to hydrolysis and photolysis (for more details on the fate of TM and MBC, refer to section 5 of this document). No evidence has been presented to refute this assumption that rapid conversion to MBC will occur from TM appl ied to soils or transported to water bodies.

The EFED RED Chapter and EPA final RED documents were revised as follows:

 In June, 2002: A revision of the RED was made in response to registrant label revisions which provided for significant re duction of many of the highest use rates and numbers of permitted yearly applications assessed in the 2001 RED (refer to June 24, 2002 memo from EFED). In this assessment, the maximum ground application use rates were reduced to 1.4 lbs a.i/A for onions with one application per year; and to 5.45 lbs a.i/A for commercial turf uses with one applic ation per year. Additionally, the maximum aerial application rates to potat oes were reduced to 0.93 lbs a. i/A with three applications per year; and to 0.7 lbs a.i/A w ith four application per year for apples and grapes. in October 2005); and

 In October 2005: The last revision of the RED was released containing a number of mitigation measures affecting label rates and crop/non-crop registration sites. This revision promulgated to mitigate human health risks. These changes in application rates also reduced levels of ecological exposure as well. The mitigation measures are summarized in Table 1

.

Table 1. Measures required in the 2005 RED for thi ophanate methyl to mitigate human health risks. (Those which also affect ecologi cal exposure have been put in bold text .)

 Reduce turf application rates in reside ntial/public areas (e.g. parks, athletic fields, lawns) to 2.74 lbs ai/a cre, maximum of 10.88 lbs ai/acre per year, 14 day retreatment interval.

 Reduce golf course turf application ra tes to 8.16 lbs ai/acre/application. 21.8 lbs ai/acre/year, 14 day retrea tment interval for tees and greens.

 Reduce golf course turf application rates to 5.45 lbs ai/acre/year, except in Florida, which has a maximum annual rate of 2.72 lbs ai/acre on fairways.

 Require wettable powder formulations labeled for aerial/chemigation applications to be packaged in water soluble bags.

 Require wettable powder formulations not packag ed in water soluble bags to specifically prohibit aerial/chemigation use.

 Require an enclosed cab for planters/operators while planting potato seed that has been treated with dust

 Require double-layer PPE, chemical-resistant gl oves, and a chemical-resistant apron to be worn when applying dip treatment and mi xing/loading/applying dip treatment.

 Single-layer PPE (Baseline) and chemical-resist ant gloves must be worn when handlers are performing certain tasks (see section IV of the RED). N Single-layer PPE (Baseline) must be worn by handlers during certain task s (see section IV of the RED)

 The Agency has determined that sign ificant risk reducti on would occur by reducing the

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12 maximum allowable rate on cut flowers to 0.5 lb ai/acre, which is currently the typical rate at which TM is applied to cut flowers.

 For post-application reentry, workers will be re quired to observe a 3-day Restricted Entry Intervals (REIs) for almonds and peanuts; 2-day REIs for apples, cherries, peaches, nectarines, apricots, and plum s/prunes; 24-hour REIs for strawberries, blueberries, wheat, celery, cucurbits, soybeans, and green bean s and 12-hour REIs for woody ornamentals.

 The maximum single application rate for orna mentals is 1.8 lb ai/acre for homeowners using spray products.

 Only granular formulations are now available to residents for broadcast lawn treatment. Use of liquid formulations for broadcast turf/lawn use is restricted to commercial pest control operators (PCOs).

 Product labels were revised to specifically prohibit belly grinder and hand application methods. N PCO treatment of backyard fruit trees will be allowed only up to fruit set.

 As a result of ecological mitiga tion activities, application ra tes and applications per year have been reduced as follows: aerial application of grapes and apples 0.7 lb ai/acre and 4 applications per year; aerial application of soybeans 0.7 lb ai/acre and 2 applications per year; ground application of golf course fairways 5.45 lb ai/acre and 1 application per year; aerial application of potatoes 0.93 lb ai/acre and 3 allowable applications per year; and ground application of onions 1.4 lb ai/acre and 1 application per year.

 Reduce the concentration of MBC in paint from 0.5% to 0.35% based on dermal MOEs which exceed the Agency’s level of concern (i.e., MOEs<1,000).

It is noted that in the 2005 RED, label mitig ation measures for MBC products include reduction of the concentration of MBC in paint from 0.5 % to 0.35% based on dermal MOEs which exceed the Agency’s level of concern (i.e., MOEs<1,000);

(2) In June, 2009: Section 3 seed treatment uses on sweet corn, peanuts, vegetables and wheat. (5/30/2006; DP Barcodes 315775 and 323266). It is noted that though thes e crops represent considerable acreage on a nationw ide basis, they are not the major crops on which TM is used with the exception of wheat which has the 4 th 

### highest usage of TM per year in the U.S. (over 51,000 lbs a.i/year for non-seed treated wheat); and

(3) The 2012 Drinking Water Assessment (D335121). Conservative assumptions were made to address the exposure levels fr om drinking water possible on an acute and chronic basis possible from either TM or MBC; total toxi c residue exposure on an acute or sub-chronic basis was calculated based upon whether a hi gher estimate was obtained by assuming TM was the predominate or by assuming MBC wa s the predominate toxic residue. Chronic exposure estimates assumed MBC as the predominate toxic residue.

Hereunder, the major conclusions of the previous risk assessments:

In the 2001 EFED RED Chapter, registered uses of TM did not exceed levels of concern (LOCs) for acute toxicity to birds as the LC 50 level >10,000 PPM was not exceeded at predicted exposure levels. Chronic LOCs for birds, base d on MBC residue estimates, were exceeded by

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13 wide margins for the highest use scenarios (appl es, beans, wheat, onions, ornamentals and turf) on certain types of vegetation using the Mallar d duck MBC NOAEC of 103 ppm. Effected parameters were egg weight and hatc hling body weight at 513 ppm (MRID 42474801).

TM did not exceed mammalian acute levels of con cern at any weight range (15 gm or higher). However, MBC LOCs for chronic risk to 15- 35 gm mammals were exceeded for the highest application rates for multiple application scenarios, particularly turf and ornamental uses. These uses also exceeded chronic LOCs for 1000 gm mammals. However, uses on apples, onions, and beans showed lower RQs which exceeded a chroni c LOC of 1.0 for certain vegetation types and high numbers of applications, but no t for other types of food sources.

For fish and aquatic invertebrates the acute LO Cs based on TM toxicity were not exceeded except for endangered species at highest us e scenarios (apples, beans, wheat, onions, ornamentals and turf). Chroni c effects based on MBC concentrations, are predicted for all modeled uses of TM to fish and aquatic inve rtebrates. This is not unexpected given the difference in acute and chronic toxicity of MBC (measured in μg a.i/L) as compared to TM (measured in mg a.i/L). These trends also hol d true for marine fish and invertebrates.

LOCs for aquatic plants were exceeded for TM using the EC50 of 0.93 ppm for the freshwater diatom, Navicula pelliculosa . Toxicity studies for aquatic pl ants were not required for MBC.

In the 2009 risk assessment, the major concerns were the potent ial acute or chronic effects from ingestion of treated seeds or pl ants containing residue s after seedling development. For aquatic species ingestion of semi-aquatic or aquatic plants that have sy stemically adsorbed TM or MBC residues from soils or uptake of residues in leac hed residues transported to water bodies in runoff was considered.

The general, approaches used in the original EFED RED Chap ter and subsequently in the 2009 new use seed treatment applications will be utiliz ed in the upcoming Registration Review efforts, but a more robust reassessment of the most curre nt labels and crop uses will be undertaken to assess the need for additional modeling exposure scenarios and to determ ine if label changes made in recent years will have a notable potentia l effect on previous conclusions for ecological risk.



## Antimicrobial Assessments - Carbendazim The antimicrobial uses of Carbendazim have not previously been assessed for environmental risks.



## Carbendazim Assessments As noted previously, the only regi stered conventional use of MBC is as a tree injection. Given this application method, it has hi storically been viewed as a “closed system” with minimal likelihood of environmental exposure. Therefore, there are no recent ecol ogical risk assessments or drinking water exposure assessmen ts for this particular chemic al/use pattern. However, in a 2008 Preliminary Problem Formulation (DP Barcode 357028) for debacarb (PC code 115001, also only formulated for use as a tree injecti on and always co-formulated with MBC), EFED acknowledged that the pote ntial exists for debacarb residues to translocate into leaves, fruits, and

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14 seeds, and result in debacarb exposure to terr estrial wildlife. A lthough the debacarb PF acknowledged the leaves/fruits/see ds of treated trees may drop in to adjacent water bodies and lead to exposures to aquatic receptors, the PF conc luded that exposure via this pathway is likely to be “minimal given the limited tree injecti on use pattern.” Analogous considerations are assumed to apply to the MBC formulated for use in tree injection. Therefor e, in comparison with MBC loadings to the terrestrial environment and water bodies that result from conventional crop and landscape applications of TM, loadings that result from MBC tree injection are expected to be minimal. Consequently, the TM ecological ri sk assessments that address MBC are considered to provide the most current unders tanding of MBC ecological risks


## B. Ecological Risks

As stated above, the Agency has conducted multi ple ecological risk assessments on Thiophanate methyl that serve as a basis fo r this scoping document. The primar y risks issues that have been identified for terrestrial, aquatic organisms a nd aquatic plants are related to the more toxic degradate MBC Thiophanate methyl risk quoti ents for aquatic plants have also exceeded concern levels as well. The most recent, comp rehensive assessment of all uses conducted for TM and it’s degradate, MBC, is the revise d EFED RED Chapter (USEPA, 2002). The major ecological conclusions presented in that RED were as summarized in Table 1 for TM and in Table 2 for MBC.

Table 1 Summary of Acute Risk Concerns Identified for Th iophanate methyl in Previous Assessments for Conventional uses (excluding seed treatments 3 

### ) (N.D. =not determined)

Birds Mammals Terr. Plants Terr. Inverts Fish BCF Aquatic Inverts Aquatic Plants Groundwater Contamination Persistence Degradates of Concern No Yes 1 N.D. 2 N.D. No No No Yes Yes No MBC

1 

### Acute risk is only predicted for NC Apples at 12 applications. Other modeled scenarios did not exceed 0.5

2 

### Terrestrial plants were tested to 1.4 lbs ai/A only. No e ffects observed at this level.

Table 2. Summary of Chronic Risk Concerns Identified for Methyl 

### 2-benzimidazolylcarbamate (MBC) as a Degradate from Thiophanate methyl Uses ( N.D. =not determined)

Birds Mammals Terr. Plants Terr. Inverts Fish BCF Aquatic Inverts Aquatic Plants Groundwater Contamination Persistence Degradates of Concern Yes Yes N.D. N.D. Yes No Yes N.D. Yes Yes c N.A.



## C. Drinking Water Exposure

A drinking water exposure assessment (DWA) wa s conducted for thiophanate methyl and its toxic degradate MBC in 2012 using the PRZM/E XAMS aquatic exposure models (DP Barcodes D335121 and D357892; 1/17/12). This DWA evalua ted existing (with higher EDWCs) along

### `

15 with multiple new uses that were requested on co tton, blueberries, bushberri es, caneberries, leafy Brassica greens, turnip greens, tomatoes, ginsen g, citrus, mustard grown for seed, tuberous & corm vegetables seed-piece treatment, tree nuts, mushrooms, and sunflower seed treatment. The separate exposure assessments for parent and MBC fulfilled the need for separate drinking water exposure estimates to be incorporated in the se parate dietary risk assessments by the Health Effects Division. Acute exposure concentrations estimates using conservative (protective) modeling input assumptions ranged up to 83.6 ppb for parent TM and up to 90.8 ppb for MBC (after additional refinements as described in the referenced DWA) . Chronic exposure endpoints for cancer (based upon 30-year average estimated concentrations) for parent TM were up to 4.7 ppb for parent and 31.3 ppb for MBC (after refi nements). Chronic exposure endpoints for noncancer endpoints (based upon 1 in 10 year return frequency annual estimated concentrations) for parent TM were up to 7.3 ppb for parent a nd 47.2 ppb for MBC (after refinements). These EDWCs are separate conservative estimates specific to TM or MBC exposure and are not designed to be additive for a combined exposur e assessment. Previous drinking water exposure estimates from groundwater using the SCI-GROW model to represen t vulnerable drinking water wells were much lower: 0.176 ppb for parent and 8.57 ppb for MBC for both acute and chronic exposure levels (EFED Reregistration Eligibility Document Science Chapter; 5/24/2000). Use of the newer ground-water exposure estimate model w ill be evaluated in the risk assessment to determine if groundwater exposure estimates are increased (based upon previous experience with compounds of similar fate propert ies it is not expected, however, that exposure estimates with PRZM-GW at the Tier 1 level will still not be higher than drinking wa ter exposure estimates from surface water sources.



## D. Clean Water Act Programs

As part of the PF process, OPP and OW have an agreement that States would be able to use the most sensitive aquatic endpoints identified in th e PF for prioritization and possibly to use as benchmark criteria. Thiophanate methyl and MB C have not been iden tified as a cause of imp1airment for any water bodies listed as im paired under section 303(d) of the Clean Water Act. No Total Maximum Daily Load (TMDL) criter ia have been developed for either compound. Aquatic benchmarks have been estab lished for TM and are available at: http://www.epa.gov/oppefed1/ecoris k_ders/aquatic_life_benchmark.htm

There are no aquatic benchmarks established for MBC per se

.



# 3. Environmental Fate and Transport

A. Fate Properties of Residues of Concern

Residues of concern are TM and its major degradate MBC for application to food and nonfood/feed crops and MBC for its labeled plant injection and industrial uses. The physiochemical, fate and transport propert ies for TM are summarized in Table 2 and for MBC in

### `

16 Table 3

. Most of the available studies are quite old and the design, data collection, and reviews of them are not complete by current OPP standards; some environmental fate values are therefore marked “tentative” in Tables 2 and 3. These va lues will be reassessed after updated evaluations are made and, in some cases, new studies are submitted and reviewed by the Agency. Based on the available data, acute exposure may be variab ly predominately parent or MBC but chronic exposure is likely to almost al ways be predominately to MBC. MBC is somewhat less mobile (more likely to be adsorbed to sediment and organic matter) than thiophanate methyl, but is significantly more persistent.

Note that in this section some of the studies cited were used to support yet another active ingredient that was pr eviously registered in the United States (benomyl). Benomyl rapidly degrades in the environment to MBC (often w ithin a few hours and always within a few days) 4



### . MBC is environmentally persistent with half-lives of several months excep t that in aerobic or anaerobic aquatic systems half-lives can be as short as one or two months.

The environmental fate and transport database is sufficient and complete for most of the antimicrobial uses except where non-guideline leaching studies are required for use scenarios like: • Exterior paint coated surfaces • Wood protective stains • Roof coatings • Treated textiles

Table 2. Physicochemical and Fate Prope rties of Thiophanate methyl.

Property Value Reference (MRID# or Citation)

Chemical Name Thiophanate Methyl Product chemistry

Chemical Structure

Chemical Group Benzimidazole Product chemistry

CAS Number 23564-05-8 Product chemistry

4 EFED previously summarized the results of these studi es in the benomyl RED chap ter (date ca. 3/21/2000; DP Barcodes D221855 and D264105.) 

## NHCS.NHCO.OCH 3



## NHCS.NHCO.OCH 3 

## *

### `

17 Table 2. Physicochemical and Fate Prope rties of Thiophanate methyl.

Property Value Reference (MRID# or Citation)

Molecular Weight (g Mole -1 ) 342.4 Tomlin, 1997 (ed.) 5

Molecular Formula C 12 H 14 N 4 O 4 S 2 Tomlin, 1997 (ed.)

Water solubility at 25 ○ C (mg L -1 ) 21.8 Tomlin, 1997 (ed.)

Octanol/water partition coefficient K ow and (log K ow ) 32 (1.5) Tomlin, 1997 (ed.)

Vapor Pressure (Torr) 1.3 E-5 Tomlin, 1997 (ed.)

Henry’s Law Constant (atm cu m 3 mole -1 ) 2.69 E-7 Calculated from VP &solubility

Hydrolysis half-lives pH 5: stable, pH 7: 36 days; pH 9: 0.7 days 6

. Study conducted at 22 o C (45 o C and 65 o C rates may also be available.)
(tentative) Major Degradation products: MBC (AV-1951 also formed, more information may be available after the EFED review is completed) (28.6% @ pH 7) a 400955-07
See also: 00120582 (alt. # 00036690) and
0062540

Aqueous photolysis half-life 2.17 days pH 5 buffer @ 3 to 17 C.Major Degradation product: MBC (49.7%) and DX105 (14.3%), both maxima at 5.5 days. 41482806

Soil photolysis half-lives 2.9-5.5 days Major Degradation product: MBC (21.7%) 41482807 and 42094601

5 The Pesticide Manual, A World Compendium (11th ed ition 1997), Tomlin, Clive D. S., ed., British Crop Protection Council, 20 Bridport Road, Thornton Heath, CR4 7QG, U.K.

6 Here and elsewhere in Table 2 and Table 3 all environmental fate half-lives for thiophanate-methyl and MBC were based on first order rates calculated using linear regressions of log-transformed data. In some cases, in the updated risk assessment if the previous model fits appear to be inadequate, degradation half-lives will be recalculated according to newer EFED guida nce utilizing using nonlinear regression an d SFO, DFOP, or IORE equations. The equations can be found in the document, Standard Operating Procedure for Using the NAFTA Guidance to Calculate Representative Half-life Values and Characterizing Pesticide Degr adation (Bohaty et al., 2012).

### `

18 Table 2. Physicochemical and Fate Prope rties of Thiophanate methyl.

Property Value Reference (MRID# or Citation)

Aerobic soil metabolism half-life (days) <1 in each of 3 test soils 2 Maximum, final MBC concentration: 71.8%, 35.7% @ 365 days; Exter sandy loam. 71.4%, 22.0% @ 365 days; clay loam. 82.7%, 1.0% @ 365 days; (other) sandy loam.
DX-105 reached a maximum of 8 to 11% in the 3 test soils. Test soils: clay loam soil (pH 7.2), 2 sandy loam soils (pH 5.7 and 7.5). Access. 00106085

Aerobic aquatic half-life (water/ sediment system) (days) Default value is stable for modeling when data requirement is still outstanding.
All values listed below are tentative. Results classified as supplemental: TM half-life = 1.8 days in river water:sediment and 3.2 days in pond system. river water:sediment system
MBC maxima:81.6% of the applied in the river system (8 days posttreatment) 75.1% in the pond system ( at 16 days) MBC appeared to decline over the course of the studies, especially the p ond water system (300-day study) 45621401

Anaerobic aquatic half-life (water/ sediment system) (days) 1 @ 21 o C Major Degradation product:
MBC- Maximum 54% in sediment
Maximum 28.6% in water 4006 1501 92186019 40061500 133502

435965-01

Soil Water Partition Coefficient (K oc , L Kg -1 ) 188.6, 136.6, 225.0, 858.8, 358.5, and 117.7 in six test soils. (Avg. = 318) 7 42351001

Terrestrial Field half-lives < 1 day 1 day 4.2 days Major Degradation product: MBC (6.1 to 10.0 %) 419301-01

419301-02

434337-01

7 Thiophanate-methyl, DX-105, and FH-432 had Kads ranging from 0.27 to 14.1. Thiophanate-methyl, DX-105, and FH-432 desorbed relatively easily fro m soil and are therefore expected to be mobile. However Kads values of MBC (Kads 0.45 to 88.2) were nearly equal to the Kdes values (Kdes 0.33 to 161) indicating that MBC is not readily desorbed from the soil.

### `

19 Table 2. Physicochemical and Fate Prope rties of Thiophanate methyl.

Property Value Reference (MRID# or Citation)

Table 3. Physicochemical and Fate Properties of Carbendazim (MBC) 1



### .

Property Value Reference (MRID# or Citation)

MBC Chemical Name Methyl 2-benzimidzolylcarbamate or Carbendazim (MBC) Product chemistry

Chemical Structure

Chemical Group Benzimidazole Product chemistry

CAS Number 17804-35-2 Product chemistry

Molecular Weight 191.18 g Mole -1 Tomlin, 1997 (ed.)

Molecular Formula C 9 H 9 N 3 O 2 Tomlin, 1997 (ed.)

Water solubility at 25 ○ C (mg L -1 ) 8 Tomlin, 1997 (ed.)
Access. No. 00151418

Vapor pressure (Torr) 7.5 E-10 Tomlin, 1997 (ed.) Octanol/water partition coefficient K ow and (log K ow ) 33 (1.52) Tomlin, 1997 (ed.) Henry’s Law Constant (atm cu m 3 mole

1 ) 2.36 E-11 Calculated from VP &solubility Hydrolysis half-life Stab le at pH 5 and 7, but subject to hydrolysis at pH 9 3 Study temperature: 25 0 C. ( tentative data ) MBC apparently was stable at pH 5, 7, and 9 in a benomyl study, but was not the major degradate formed at pH 9 (Access. #151418) 43129614. See also Benomyl study Acc. Nos. 00151418 (same as
00259471 a and Acc.# 00154696

Aqueous photolysis half-life Stable (99% remaining at 32 days.) (study with benomyl applied) Acc.#00151419
Other published b

### `

20 Table 3. Physicochemical and Fate Pr operties of Carbendazim (MBC) 1



### .

Property Value Reference (MRID# or Citation)

Soil photolysis half-lives Stable (derived from benomyl study where MBC formed and constituted 99% of the applied material at study end (3 2 days post-treatment.) Acc. #00151420 (benomyl study)

See also Acc. # 00120626 b
(submitted published study for MBC, no review located.)

Aerobic soil metabolism half-life (days) 320 in Keyport silt loam as measured in study with benomyl applied (benomyl half-life was 0.8 days 41255801 (Benomyl , supplmtl. For MBC). Addit. data on 3 soils (TM applied) may be avail. in Acc. #00106085. Aerobic aquatic half-life (water/ sediment system) (days) Tentative
23 and 61 (90 th %ile Upper C.I. of mean = 100) In a study with benomyl applied, MBC degraded with an estimated half-life of 61 days in a clay loam/water system at pH 7.3 incubated aerobically for 30 days (MRID# 41291501).
Results of MRID 4562001 were determined to be unacceptable. 41291501

45620001

Anaerobic aquatic metabolism half-life (days) 743 (Benomyl applied, but rapidly converted to MBC) 31, but unclear if study was ultimately accepted. 41137701

45620001 Soil water partition coefficient (K oc , L Kg

1 ) Tentative: 1,885 (Average of 6 soils) Individual Freundlich adsorption values: 3.77 (l/n =0.77) in sandy loam 4.74 (l/n=0.712 ) in loam 0.45 (l/n=0.827) in sand, 88.2 (l/n=0.609) in clay loam 4.47 ( l/n=0.752) in loam 5.71 (l/n=0.747) in loamy sand Acc. No. 00151422
See also Helweg (1977). d

Terrestrial Field half-lives 22 days 94 days 33.9 days 419301-01
419301-02
434337-01

### `

21 Table 3. Physicochemical and Fate Pr operties of Carbendazim (MBC) 1



### .

Property Value Reference (MRID# or Citation)

a In MRID 43129614 (in review) there apparently was hydrolysis of MBC at pH 9 (the registrant calculated a logarithmic-linear hal f-life of 65 days). In Acc.# 00151418, a study with benomyl applied. At pH 5, the half-life of benomyl was 3.5 hr., major degradate was MBC. At pH 7, the half-life of benomyl was 1.5 hr., the major degradates were MBC (approx. 75% of total radioactivity) and (STB or 3-butyl-2,4-dioxo[1,2-a]s-triazino benzimidazole) at 25% of total radioactivity. At pH 9, the half-life of benomyl was less than 1 hr., the major degradate was (STB) reaching 80 - 90% of total radioactivity and not subject to further hydrolysis over the 30 days study. When formed, MBC ap peared to be stable to hydrolysis over the 30-day study period. Similar results are reported in a published study: M. Anastassiadesa and W. Schwack. 1998. Journal of Chromatography A 825: 45–54.

b Fleeker, J.R. and Lacy, H.M. 1977. Photolysis of Meth yl 2-Benzimidazolecarbamate. J . Agric. Food Chem., - 25:51-55.

c Helweg, A. (1977) Degradation and adsorption of carbendazim and 2-aminobenzimidazole in soil. Pestic. Sci. 8:71-78. (Also In unpublished submission received Sep 27, 1979 under 4581-340; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:099006-G)

d Helweg, A. (1977) Degradation and adsorption of carbendazim and 2-aminobenzimidazole in soil. Pestic. Sci. 8:71-78. (Also In unpublished submission received Sep 27, 1979 under 4581-340; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:099006-G)



### MBC appears to be less soluble than its parent TM and is not expected to be affected by volatility (VP= 7.5 E-5) from dry/wet soil or wa ter (HLC= 2.1 E-11). Tentative results indicate that TM may be stable to hydrolysis and photol ysis at pH 5 and increasingly subject to hydrolysis at higher pH (Table 2) whereas MBC app ears to be stable to h ydrolysis at pH 5 and 7 but subject to hydrolysis at pH 9, but less so than TM (tentative data, s ee Table 3). Photolysis appears to be another mechanism of TM degradation when it is expos ed to sunlight (half-lives of 2 to 6 days in water and soil) but MBC is not photodegraded (and is a major photolytic product of TM).

Under most environmental conditions, parent TM is expected to degrade rather quickly into the major metabolite MBC which appears to be of gr eater persistence. Therefore, MBC has a more important influence on long-term environmenta l concentrations (i.e ., chronic exposure is predominately to MBC). Additionally, MBC appears to be slightly mobile compared to its mobile parent (average K oc 

### = 318 L Kg -1 

### for parent compared to 1,885 Kg -1 

### for MBC). MBC is more likely to be adsorbed to soil/sediment a nd organic matter and less mobile than its parent TM. In general, fate properties of TM and MBC demonstrate that under most environmental conditions thiophanate methyl de grades almost completely to MBC within a few days after application (additional studies ar e being requested to clarify u nder which conditions parent TM is more persistent, but the available data do s how that it is more resi stant to hydrolysis under acidic conditions)

. MBC is environmentally persistent with half-lives of several months excep t that in aerobic or anaerobic aquatic systems half-lives can be as short as one or two months. However, persistent in aquatic systems may be hi ghly variable (i.e., 743 t 1/2 

### in an accepted study, apparently much shorter in another study, but those data cannot be used as the study was deemed unacceptable).

### `

22 Additional data are being requested to clarify the fate of both TM and MBC in soil and aquatic systems.



## B. Transformation Products

MBC is expected to remain the degradate of concern for the ecological risk assessment both because of its persistence and high toxicity. St ructures and full chemical names for degradates commonly detected in environmental fate studies are provided in “Structures of Thiophanate Methyl and Degradates”. However, only MBC is, to the extent that is determined to date from available studies, consistently a major degradate detected in environmental fate studies at high concentrations (e.g., it reached a maximum con centration >70% of applied in aerobic soil metabolism studies). MBC is generally highly persis tent (half-lives of a few months or longer) under aerobic conditions in soil and water, but is (apparently ) less persistent under anaerobic conditions (Table 2).

While MBC is the major degradate both in te rms of exposure potentially and toxicological activity, other degradates formed as secondary minor products (usually, but not always, reported at concentrations below 10% of applied parent th iophanate methyl in envi ronmental fate studies). However, as it is not clear whether all available st udies or data have been fully incorporated in previous reviews, EFED will obtain copies of these studies and determine whether significant additional insights into the environmental transf ormation of thiophanate methyl and MBC can be extracted for the reregistration risk assessment. In soil and water thiopha nate methyl typically degrades to 2(N-methoxycarbonyl thioureido) phenylene]thiour ea (aka. AV-1951) via hydrolysis of the one side chain to dimethyl[1,2-(4- hydroxyphenylene) bis (imonocarbonothioyl)] bis (carbamate) (aka. 4-OH-TM) through oxidation of the phenyl ring. AV-1951 is transformed to methyl benzimidazol 2-yl carbamate (carbendazim/MB C) via closure of the side change to form a benzimidazole ring. Carbendazim is then par tially hydrolyzed to form 2-aminobenzimidazole (aka. 2-AB). Finally, 4-OH-TM, carbendazim, and 2-AB are further degraded into bound compounds and CO 2 

### . Structures of each of these transf ormation products are provided in Table 13.

One caveat with regard to the c onclusions regarding the residues of concern in this preliminary assessment is that the amount of unidentified bou nd residues formed in some environmental fate studies was quite high. For example, at the cl ose of a 12-month anaerobic aquatic metabolism study (MRID 40061501) unextracted residues reached 83.7% of the applied radioactivity from the thiophanate methyl a pplication (the cumulative 14 

### CO 2 

### was 4.0% of applied); new studies are being required.

Based on the available data, MBC is expected to remain the degradate of concern for the ecological risk assessment both because of its pers istence and high toxicit y. Structures and full chemical names for degradates commonly detected in environmental fate studies are provided in “Structures of Thiophanate Met hyl and Degradates”. Updated re views of these studies and additional studies in some cases will be requested to determine whether significant additional insights into the environmental transformation of thiophanate methyl and MBC can be extracted for the reregistration risk assessment. The re quested new studies should better address issues

### `

23 such as: (1.) the identity of unextracted residues, (2.) whether TM and MBC might be significantly more persistent in acidic soil and wa ter environments and (3.) a fuller accounting of degradation products of MBC and the MBC decline rate.

### `

24 

# 4. Receptors

. 

## A. Aquatic Toxicity of Thiophanate methyl

Current test results indicate that TM displays only moderate to slight toxicity to aquatic invertebrates and fish with toxicity values well above 1 mg ai/L ( Table 3 ) The most sensitive aquatic animal species tested was the mysid, Americamysis bahia , with an LC 50 

### of 1.1 mg ai/L. The macrophyte, Lemna gibba , was tested and showed an EC 50 

### at 4.7 mg ai/L afte r 7 days with an NOAEC of 0.43 mg ai/L for frond pr oduction. For nonvascular plants , the most sensitive species tested was the freshwater diatom , Navicula pelliculosa , with a 96-h EC 50 

### of 0.93 mg ai/L for cell density. The other 4 tested algal species displayed EC 50 

### levels greater than the highest concentrations tested when acetone was utilized as a solvent (0.095 to 4.3 mg ai/L).

Table 4. Summary of the Most Sensitive E ndpoints from Aquatic Toxicity Studies for TM Taxonomic

Group Study Type Surrogate Species Toxicity Value In PPM Acute Toxicity Classification Source

Freshwater fish 1 Acute Rainbow Trout ( Oncorhynchus mykiss ) LC 50 = 11 mg ai/L Slightly toxic 42887001

Chronic(Early LifeStage) Rainbow Trout No data --

Freshwater invertebrates Acute Water Flea ( Daphnia magna ) EC 50 = 5.4 mg ai/L Moderately toxic 42298101

Chronic Water Flea No data --

Estuarine/marine fish Acute Sheepshead Minnow ( Cyprinodon variegatus ) LC 50 = 49.5 mg ai/L Slightly toxic 42123503

Estuarine/marine mollusc Acute Eastern Oyster ( Crassostrea virginica ) EC 50 = 2.2 mg ai/L Endpoint: shell growth Moderately toxic 42094602

Estuarine/marine
crustacean Acute Mysid, Americamysis bahia LC 50 =1.1 mg ai/L Moderately toxic 42123502

Aquatic plants and algae Vascular Duckweed ( Lemna gibba ) NOAEC=4.7 mg ai/L EC 50 > 4.7 mg ai/L -- 42123505

### `

25 Taxonomic

Group Study Type Surrogate Species Toxicity Value In PPM Acute Toxicity Classification Source

Nonvascular Freshwater diatom, Navicula pelliculosa NOAEC = 0.43 mg/L EC 50 =0.93 mg/L -- 42229802

1 Freshwater fish may be surrogate s for aquatic-phase amphibians.



## B. Aquatic Toxicity of MBC

The MBC degradate (Carbendazim) is significant ly more toxic to aquatic organisms when compared to TM. Acute LC 50 

### values for fish range between 10 and 1120 μg ai/L and acute EC 50 

### /LC 50 

### values for aquatic invertebrates range between 98 to 350 μg ai/L ( Table 4 ). MBC is also chronically toxic to aquati c organisms at much lower con centrations than the TM with NOAEC values ranging from 13 μg ai/L for Daphnia magna to 0.99 μg ai/L for the Channel catfish. No aquatic plant data has been received for MBC.

Table 5. Summary of the Most Sensitive E ndpoints from Aquatic Toxicity Studies for MBC 3
Taxonomic

Group Study Type Surrogate Species Toxicity Value In PPB of active ingredient Acute Toxicity Classification Source

Freshwater fish 1 Acute Channel catfish, Ictalurus punctatus LC 50 = 10 ug ai/L Very highly toxic 40098001

21 Day Acute Rainbow trout Oncorhynchus mykiss LOAEC – survival= 54 ug ai/L with NOAEC of 26 ug ai/L 42882301

Chronic (Early Life Stage) Channel catfish, Ictalurus punctatus NOAEC = 0.99 ug ai/L LOAEC = 2.1 ug ai/L Egg production __ 43872801

Estuarine/marine fish Acute Sheepshead Minnow ( Cyprinodon variegatus ) LC 50 >1160 ug ai/L > Moderately toxic 40975001

Freshwater invertebrates Acute Water Flea EC 50 = 110 ug ai/L Highly toxic 43205502

Chronic Water Flea NOAEC = 3.1 ug ai /L LOAEC = 6.6 ug ai/L -- 42529401

Estuarine/marine mollusc Acute Eastern Oyster ( Crassostrea virginica ) EC 50 >1160 ug ai/L Endpoint: shell growth > Moderately toxic 40975002

### `

26 Taxonomic

Group Study Type Surrogate Species Toxicity Value In PPB of active ingredient Acute Toxicity Classification Source

Estuarine/marine
crustacean Acute
Mysid, Americamysis bahia LC 50 =98 ug ai/L Very Highly toxic 40964701

Chronic NOAEC=24.8 ug ai/L LOAEC = 50.4 ug ai/L Endpoints affected: egg production, growth, survival 42723701 MBC test In Benomyldata set1 Freshwater fish may be surrogate s for aquatic-phase amphibians.

2 Toxicity endpoints presented, i.e. , NOAEC or EC 50 , are the only ones available from the study.

3 MBC is also registered as the active i ngredient Carbendazim under PC Code 128872

4 MBC data available for this algal sp ecies in open literature. EC50 reporte d to be 0.64 ppm (Canton, J.H. 1976)



## C. Terrestrial Toxicity of Thiophanate methyl

For terrestrial receptors, TM is classified as practically non-toxic on an acute exposure basis to the laboratory rat based on an oral LD 50 

### of >5000 mg ai/kg bw ( Table 5 ). TM is also practically non-toxic to birds on an acute dietary basis (LD 50 

### > 4,586 mg/kg-diet. In four avian reproduction studies no reproductive effects to birds were observed at 103 PPM or more in the diet for mallard duck or bobwhite quail. Howe ver, in the mallard study egg size and hatchling body weight were affected at 511 PPM.

TM is classified as practi cally non-toxic on an acute c ontact basis to honeybees ( Apis mellifera ) with a 48-h LD 50 

### of > 100 ug ai/bee.

Table 6. Summary of the Most Sensitive Endpoin ts from Terrestrial Toxicity Studies for TM Taxonomic

Group Study Type Surrogate Species Toxicity Value (all units in terms of

measured active ingredient) Acute Toxicity Classification Source

Birds 1 Acute Bobwhite quail, Colinus virginianus LD 50 > 4640 mg/kgbw Practically non-toxic 00083012

Sub-acute dietary Mallard duck, Anas platyrhynchos LC 50 > 4586 ppm Slightly to practically non-toxic 41930104

Chronic Mallard duck, Anas platyrhynchos NOAEC =103 ppm LOAEC = 511 ppm Egg wt and hatchling body wt -- 42474801

Mammals Acute Oral Laboratory rat ( Rattus norvegicus ) LD 50 >5000 mg/kgbw with technical Practically non-toxic 41644301

### `

27 Taxonomic

Group Study Type Surrogate Species Toxicity Value (all units in terms of

measured active ingredient) Acute Toxicity Classification Source

Acute Inhalation Laboratory rat LC 50 > 1.7 mg/L 41482804

Chronic Laboratory rat ( Rattus norvegicus ) NOAEL = 195 mg/kg/day LOAEL = 630 mg/kg/day Endpoint: reduced pup weight -- 42899101-105 43624401

Insects Acute
contact Honey bee ( Apis mellifera L. ) LD 50 > 100 μg ai/bee Practically non-toxic 40053209

Terrestrial plants Seedling Emergence Soybean NOAEL <1.4 lb ai/A EC 25 >1.4 lb ai/A Endpoint: -- 44404101

Onion NOAEL = 1.4 lb/A EC 25 >1.4 lb/A Endpoint: shoot dry weight -- 44404101

1 Birds represent surrogates for terrest rial-phase amphibians and reptiles.



## D. Terrestrial Toxicity of MBC

MBC is classified as practica lly non-toxic to birds on an acute exposure basis with oral LD 50 

### values > 2100 mg ai/kg bw ( Table 6 ). Dietary LC 50 

### values for birds are also in excess of 4200 ppm in feed. No chronic avian studies have been submitted for MBC, but a study with Benomyl and measured concentrations of MBC in the diet was submitted . In this avian reproduction study conducted with Benomyl (MRID 44103002) MBC was m easured in the diet and the resulting LOAEC was determined to be 720 ppm with a NOAE C of 322 ppm. Endpoints affected included viable embryos, normal hatchlings of eggs set, and 14 day survival of young.

The LD 50 

### for honey bee, A. mellifera , was > 50 ug ai/bee (practically non-toxic).

Table 7. Summary of the Most Sensitive Endpo ints from Terrestrial Toxicity Studies for MBC Taxonomic

Group Study Type Surrogate Species Toxicity Value (all units in terms of

measured active ingredient) Acute Toxicity Classification Source

Birds Acute Bobwhite quail, Colinus virginianus LD 50 > 4200 mg/kg-bw Practically non- toxic 43129605

Sub-acute dietary Mallard duck, Anas platyrhynchos LC 50 > 4467 ppm Slightly to practically non- toxic 43205501

### `

28 Taxonomic

Group Study Type Surrogate Species Toxicity Value (all units in terms of

measured active ingredient) Acute Toxicity Classification Source

Chronic Bobwhite quail, Colinus virginianus NOAEC=322 ppm LOAEC = 720 ppm Viable embryos, normal hatchlings, 14 day survivors -- 44103002- based on measured MBC in diet for Benomyl
test

Mammals Acute Laboratory Rat Rattus norvegicus LD50 >10000 mg/Kg Acc. 256025 (cited in 2005 RED)

Chronic Rabbit NOEAL= 20 mg/Kg/day LOAEL = 40 mg/Kg/day fetal wt. decrease 45051001 00260571 (cited in 2005 RED)

Insects Acute
contact Honey bee ( Apis mellifera L. ) LD 50 > 50 μg ai/bee Practically non-toxic 00154695

Terrestrial plants Seedling Emergence Dicot – EC 25 = Endpoint: No data

Monocot – NOAEC EC 25 = Endpoint: No data



## E. Additional Effects

Open literature studies with 5 species of earthworms in British apple orchards receiving five Benomyl spray applications at 0.28 kg/ha or five TM spray applications at 0.78 kg/ha resulted in observation of drastic population reductions over a 1-3 year period (Stringer, A. and C. Lyons. 1973). A later study to determine the contact toxicity of Thia bendazole, TM, and Benomyl showed that Lumbricus terrestris immersed for 1 minute in a 0.5% suspension of these chemicals were killed in 14 days (MRID 00154694. Wright, M.A. and A. Stringer, 1973.). This concentr ation was intended to mimic what might be expected from soil drench treatments used in orchards. La ter studies conducted by the University of Arkansas on 10 different turf fungicides also showed that exposure to Eisenia fetida from these three fungicides were also found to cause significant mortality (Roark, JK.H. a nd J.J. Dale, 1979.). Further investigation into potential risks to soil invertebrates will be unde rtaken in the Registration Review process.



## F. Ecological Incidents

The ecological incident information system (EIIS ) is an OPP database that houses ecological incidents that have been reported to the Agency. When available, EIIS includes date and location of an incident, type and magnitude of effects obs erved in various species, use(s) of pesticides

### `

29 known or suspected of contributing to the incident, and results of a ny chemical residue analysis or other analyses conducted during incident investig ation. EIIS incidents are categorized according to the certainty that the incide nt resulted from pesticide exposu re. The Avian Monitoring System (AIMS) is a database administered by the Amer ican Bird Conservancy th at contains publicly available data on reported avian in cidents involving pest icides. Many of the incidents listed in this database are also in the EIIS.

EFEDs Incident Database had 3 incidents in wh ich Thiophanate was appl ied and 1 incident in which Carbendazim (MBC) was applied. . None of these incidents invo lved single chemical applications or spills. The in cidents involved runoff to a pond fr om golf course use (Deltamethrin and Imidacloprid also were both used) and a chem ical warehouse fire in which many chemicals were washed into an adjacent stream. No certa inty was assigned to TM or MBC as the causative agent as more toxic chemicals were also involve d. A single honeybee inci dent is listed for TM, but Captan and Imidan were also used on the ap ple orchard adjoining the farm where the bee kill occurred. The Carbendazim incident in Australia involved formation of fish with multiple heads in a hatchery and a river near Macadamia nut plantations. Though Carbendazim was detected and applied at the plantations some triazines were also used. The investigation was carried out by Australian officials, but a causative ag ent was not determined with certainty. 

# 5. Exposure Pathways of Concern

Thiophanate methyl may be applied for convent ional uses as a foliar spray by aerial or ground application equipment. For this reason both sp ray drift and runoff may be considered primary routes of exposure. TM is a systemic fungicide and therefore residues are expected to collect in plant tissues in leaf, root and stem areas of targ et crops. Degradation to the more persistent MBC degradate in or on plants, soils or water receiving runoff or drift can be expected within days. Degradation to MBC in water is a more rapid pro cess than in soils or on foliar surfaces. Major pathways for exposure to non-target organisms are summarized below:

Terrestrial Organisms - Direct exposure to residues duri ng application either dermally or via inhalation of spray droplets - Exposure to applied residues on foliar surfaces from dermal contact - Systemic adsorption by plants of residues through roots or folia r surfaces or from seed uses - Dietary exposure through feed ing on vegetation or insects th at have been exposed during application of TM either directly or via off target spray dr ift or from injec tion usage of MBC - Dietary exposure through i ngestion of treated seeds - Ingestion of residues through drinking water sour ces such as puddles, irri gation ditches, canals, contaminated irrigation water or dew with in or adjacent to the application site.

Aquatic or Semi Aquatic Organisms - Exposure via water which has received direct spray drift - Dermal exposure from spray drif t into littoral areas (semi aquatic plants, amphibians and semi aquatic insects, and reptiles) near application sites - Exposure to residues resulting from runoff origin ating on treated areas. Degradates, such as MBC, may be the more prevalent constituents of this runoff.

### `

30 - Dietary ingestion of aquatic or semi aquatic plant tissues that ha ve systemically adsorbed TM or MBC residues.

Drinking water and inhalation e xposure pathways were screen ed using the SIP (Screening Imbibition Program) and STIR (Screening Tool for Inhalation Risk) screening methods and were found to be exposure pathways of low concern (no LOC exceedances are expected). SIP and STIR are described in detail at: http://www.epa.gov/oppefe d1/models/terrestrial/index.htm

. Based on an initial SIP run exposure through drin king water alone is a potential chronic concern for birds if the avian NOAEL is assumed to be 150 ppm. However, it should be noted that LOAEL were > 150 ppm with no true NOAEL established.

Based on the initial STIR run i nhalation is not expected to be a significant exposure route.

Given the specificity of the MBC tree injection use pattern, the only viable transport mechanism consists of translocation/uptake to foliage, frui t, seeds and pollen in tr eated trees. Although there is the potential for MBC residues in leaves, fruits, and seeds to drop into adjacent water bodies, exposures to aquatic receptors via this pathway are expected to be minimal given the limited tree injection use pattern. Pathways for exposure to non-target terres trial organisms are:

‐ Dietary exposure through f eeding on treated vegetation (mammals, birds, terrestrial insects)

Antimicrobial Uses

For the screening-level risk asse ssment, OPP presumes that Carbe ndazim poses potential risks to organisms in the aquatic environment if the activ e ingredient and/or any major degradates leach from treated exterior surfaces and are transpor ted to impounded water bodies (e. g., ponds, lakes, reservoirs) or flowing waterways (e . g., streams, rivers). Active ingr edient and/or degradates also may reach the aquatic environment via down-the- drain discharge from use on textiles. Aquatic organisms likely to be exposed include fish, i nvertebrates, and aquatic plants. For aquatic animals, the major route of exposure is considered to be uptake via the respiratory surface (gills) or the integument from surface wa ter residues. Based on the low K ow 

### , bioaccumulation in aquatic organisms is unlikely. For aquatic plants, the majo r route of exposure is c onsidered to be uptake from surface water.



# 6. Analysis Plan

The major stressors of concern for this Problem Formulation are Thiophanate methyl and it’s more toxic and persistent degrad ate, MBC (also registered as th e active ingredient, Carbendazim)

Estimates of residue levels on terrestrial surf aces for both chemicals will be produced through use of TREX modeling and actual foliar surface dissipation da ta for both TM and MBC when available. The more conservative scenario will be selected for use in the characterization of risk to terrestrial organisms. Mon itoring data from previously regi stered uses of Benomyl (MBC is

### `

31 the major degradate) as well as current Thiophanate methyl or Carbendazim (MBC) uses will be considered in characterizing expected levels of exposure for terrestrial organisms. In addition, SIPS and STIR models will be employed to char acterize the likelihood and levels of exposure from inhalation or drinking water when current application methods are employed.

Estimates of surface and groundwat er monitoring exposure levels will be modeled for both TM and MBC using the latest PRZM EXAMS modeling fo r scenarios determined to be of the highest concern. Groundwater exposure potential will be modeled using the latest version of the SCIGROW and PRZM GW models. Nationwide monitoring programs will also be consulted for data regarding MBC or TM detec tions in surface or groundwater.

MBC/Carbendazim – conventional uses

As a conservative screening approach, consistent with the problem formulation for debacarb (DP Barcode 357028), the analysis would assume th e entire application /injection would be translocated to plant foliage/pol len and then assume that mammals/birds/terrestrial invertebrates consumed 100% of their diet on contaminated food items. In order to refine this exposure estimate, estimates of the uptake, translocation and degradation of MBC in situ would be helpful. Any available information on above usage (total us age and the distribution of use) will also be used to characterize the analysis.

MBC/Carbendazim – Industrial uses

For Carbendazim application to exte rior structures and use in text iles, estimated acute and chronic exposure concentrations in surface water will be compared to acute and chronic ecotoxicity endpoints to determine potential ri sks to listed and nonlisted speci es for each receptor group (fish, aquatic invertebrates, and aquatic plants).



## A. Stressors of Concern

Ecological Risk Assessment

The stressors of ecological concern for terrestrial organisms are TM and its main degradate MBC. Submitted studies indicate that both the parent and the MBC degradate show low toxicity to birds on an oral or acute dietary basis No chroni c avian studies have been submitted for MBC, but avian reproduction studies with Thiophanate methyl showed advers e effects at dietary concentrations 511 ppm for malla rd duck (reduced egg and hatchl ing body weights). An avian reproduction study with Benomyl and measured MBC concentrations produced adverse effects to reproduction at 720 ppm of MBC in the diet. Base d on expected concentrations of TM and MBC (particularly with turf and sod uses) there is chro nic concern from these st ressors for birds feeding on exposed vegetation.

Thiophanate methyl is relative ly non-toxic on an acute basis to mammals with a dietary LD 50 

### values of >5000 mg ai/Kg of bodyweight. The 14 day dermal LD50 value was also observed to be > 5000 mg/kg. The chronic NOAEL for the rat was observed to be 195 ppm for Thiophanate

### `

32 methyl. There is chronic concern from thes e stressors for small mammals feeding on exposed vegetation.

Thiophanate methyl has been tested with terrestrial crop plants at an application rate of 1.21 lbs ai/Acre with 25% effects to cucumber and soybean at 0.8 and 1.0 lbs ai/acre test concentrations. Other tested species were not affect ed by TM at 1.21 lbs ai/acre. Terrestrial plant testing data for the MBC degradate has not been submitted or reviewed by the Agency at this time.

Thiophanate methyl and its MBC de gradate were found to have low acute contact toxicity to the honey bee ( Apis mellifera ) with LD 50 levels 

### > 100 ug ai/bee and > 50 ug ai/bee, respectively. In open literature studies surveys of ryegrass/clover pastures following benomyl and carbendazim applications showed signifi cant reductions in earthworm popu lations when compared to untreated areas (Keogh 1975). This trend was also noted for seve ral earthworm species in apple orchards following benomyl and thiophanate methyl applications (Stringer, A. 1974)

The major stressor of concern for aquatic organisms is MBC, which displays very high toxicity to aquatic invertebrates and fish a nd is predicted to be available in aquatic habitat due to rapid degradation of the parent and the relative stabilit y of MBC. Submitted data indicate that MBC is acutely toxic to fish and aquatic invertebrates at concentration levels ranging from 12 ppb for freshwater fish to 98 ppb for mari ne invertebrate. Chronic toxici ty is indicated for freshwater invertebrates at 6.6 ppb and for a freshwater fish at 3.2 ppb. Toxicity data for the Thiophanate methyl is generally observed to be an orde r of magnitude less t oxic than MBC with EC 50 

### of 26.8 ppm for the aquatic invertebrate, Daphnia magna and 8.1 ppm for rainbow trout. It should be noted that testing with channel ca tfish, by FWS labs in the 1980’s, s howed this species to be more sensitive to both Thiophanate 70WP and MBC with LC 50 

### levels of 30 ppb and 10 ppb, respectively. The marine mollusk (eastern oyster) was affected at lower levels than marine crustacea with an EC 50 

### of 2200 ppb for thiophanate methyl and 1140 ppb for the MBC degradate. The most sensitive aquatic plant for Thiophanate methyl showed an EC 50 

### 0f 930 ppb, but 4 other tested species were le ss affected with EC 50 

### values of > 1000 ppb observed. No aquatic plant data for the MBC degradate has been submitted or reviewed by the Agency at this time.



## Drinking Water

The drinking water assessments conducted to suppor t the registration review human health risk assessments of thiophanate methyl will incor porate model estimates of thiophanate methyl residues of concern, which arise from MBC and pare nt converted to MBC, a nd, to the extent it is formed, the secondary metabolite 2-A,B (A. Parmar, 06/24/09, D360625 as cited in DP Barcode: D397646, “Carbendazim: Dietary Exposure an d Risk Assessments for the Fungicide Carbendazim (MBC), Including Potential Residues in Orange Juice”, 1/17/2012). However, 2- A,B is not formed significantly in environmenta l waters. The thiophanate methyl / MBC residues of concern will be reevaluated pending receipt and review of environmental fate data that were unavailable at the time of writing of this Problem Formulation for reregistration. Analysis will include assessment of MBC alone (assuming all e xposure as this moiety ) as well because of significant chronic exposure concerns for human health risk analysis.

### `

33 

## B. Measures of Exposure

EFED will use standard available m odels to evaluate potential expos ures to aquatic and terrestrial organisms as described at http://www.epa.gov/pesticid es/science/models_db.htm. In addition, E-FAST and any additional available exposure mode ls may be used to assess use in drains, drain lines, irrigation supply systems, waste water systems, sewage systems, sewer lines, and storm sewers. E-FAST is described in detail at http://www.epa.gov/oppt/exposure/pubs/efast.htm.

Based on results of aquatic toxic ity studies on the aquatic degradat e MBC, this degradate will be included with Thiophanate methyl in the residue s of concern modeled fo r aquatic exposure. Because Thiophanate methyl and the MBC have sim ilar toxicity to terrestrial organisms, a total toxic residues approach will be used for te rrestrial modeling, though chronic exposure to MBC will be explored in more detail as the terres trial half-life values are longer and thus more persistent for this chemical.

For Carbendazim applications to exterior su rfaces, estimated environmental concentrations (EECs) will be modeled to provide estimates of acute and chronic exposure in the aquatic environment. The EECs are determined for a 1-ha, 1-m deep farm pond, based on the amount of Carbendazim leached from treated surfaces and the number and size of treated structures per unit of area. Estimates of aquatic e xposure levels of the current indoor uses of Carbendazim will be produced through the use of Down-the Drain and PDP modules of Exposure and Fate Assessment Screening Tool (EFAST), version 2.0

i. Available Monitoring Data

The Agency is aware of monitoring conducted by federal and state agenci es and this route of exposure will be considered in the assessment to the extent that data on Thiophanate methyl and MBC are available. Limited detections of MBC in surface waters were reported in the USGS NAWQA monitoring program.



## C. Measures of Effect

Toxicity data presented in Section 3 of this pr oblem formulation will be used to calculate risk quotients. Any additional information submitted by th e registrant or found in the open literature prior to conduct of the risk assessment will also be considered. The open literature studies are identified using EPA’s ECOTOXicol ogy database (ECOTOX) (USEPA, 2007 c ), which employs a literature search engine for locat ing chemical toxicity data for a quatic life, terrestrial plants, and wildlife. The evaluation of both sources of data can also pr ovide insight into the direct and indirect effects of pesticides on biotic communities from loss of species that are sensitive to the chemicals and from changes in structure and functional characteristics of the affected communities.

### `

34 Environmental fate studies ar e listed by MRID (or Accession number, the predecessor to the MRID document accounting system) for each guidelin e requirement. Several studies could not be unambiguously identified for this review (primarily those studies providing MBC fate data) and are identified as needing further review below (the associated documents could not be retrieved in time to be reviewed for this Problem Formulation).

### `

35 

## D. Endangered Species Assessments

Consistent with the Agency’s responsibility under the Endangered Species Act (ESA), the Agency will evaluate risks to federally listed th reatened and/or endangere d (listed) species from registered uses of pesticides in registration re view. The process for evaluating potential risks to listed species is further described at http://www.epa.gov/oppfead1/enda nger/litstatus/riskasses.htm

.



## E. Endocrine Disruptor Screening Program

Neither Thiophanate methyl nor Carbendazim (M BC) were included in the first group of 67 chemicals issued an order to conduct Tier 1 EDSP testing. For additional information the EDSP program, visit http://www.epa.gov/endo/. 

# 7. Preliminary Identification of Data Gaps

A. Environmental Fate

Environmental fate studies ar e listed by MRID (or Accession number, the predecessor to the MRID document accounting system) for each guideline requirement. Most of the available studies are quite old and the reviews of them are not co mplete by current OPP sta ndards; the status of these studies has often been updated to “in review”. Many original submissions from registrants were not available at the time of EFED’s evaluation and some may have to be reclassified after they are made available (for example, some studies with benomyl applied may have been previously classified as M BC studies.).The following data are required (listed by OCSPP Guideline number):

835.2120, Hydrolysis . Existing studies for TM and MBC will be re-reviewed. An additional test at 35 C is also required for MBC to provide addi tional data on the hydrol ysis rate (persistent pesticides even with slight mobility are likely to be found in groundwat er at relatively high concentrations unless subject to hydrolysis as predicted with the PRZM-GW model).

e. 835.4100, Aerobic soil metabolism . Existing studies do not adequa tely describe the formation and decline of TM metabolites and there are in sufficient studies with MBC applied. New studies are requested for both TM and MBC in three new test soils, at least one of which has a pH<6 one a pH <6.3 and the other a pH > 7.5 (both TM an d MBC are hypothesized to be more stable in acidic soils). 835.4200, Aerobic aquatic metabolism . New studies are requested for both TM and MBC in three new test systems, at least one of which has a pH<6 one a pH <6.3 and the other a pH > 7.5 (both TM and MBC are hypothesized to be more stable in acidic systems).

### `

36 1 835.4300, Anaerobic aquatic metabolism . New studies are requested for both TM and MBC in three new test systems, at least one of which has a pH<6 one a pH <6.3 and the other a pH > 7.5 (both TM and MBC are hypothesized to be more stable in acidic systems).

835.1230. Batch equilibrium adsorption / desorption . An updated review will be conducted of a previously submitted study (MRID 42351001) which includes batch equilibrium adsorption /desorption studies for TM, MBC, and other me tabolites of TM. Pending the outcome of this review, a new study may be required.

Table 8. Submitted Environmental Fate Da ta for thiophanate methyl and MBC. 

### (MBC data are in shaded rows, TM in unshaded rows.

OCSPP Guideline Data Requirement Chem Submitted Studies (MRID or Access. #) Study Classificat ions Are more data needed? Justification and/or Assump tions EPA will Make in Absence of Data - Some Example texts are include

835.2120 Hydrolysis TM 40095507

92186016 In Review

NA TBD An updated review is needed of this 1986 study to provide more detail on the decline of TM and formation of MBC and degradates. This is a “Phase 3 summary” of 40095507(submitted 1990).
TM 00036690

or 00120582

------- Unknown --- 1973 “alkaline hydrolysis” study probably superseded by 40095507 (1986 study). If additional data are available from this study the status will be changed to “in review” until a DER is completed.

TM 00039706 Unknown. --- 1980 “half-life in wa ter” study – study type will be ascertained and reviewed if deemed necessary to complete fate data requirements. TM 00062540 Unknown --- 1972 study of hydrolysis at pH 10; probably superseded by 40095507.
835.2120 Hydrolysis MBC 43129614 In Review Yes 1992 European study – no review located. TM RED indicates there is an acceptable study for MBC Hydrolysis but lists only MRID 40095507 – a TM hydrolysis rate study.
` `00154696 Unknown --- 1984 Hydrolysis study, will be reviewed if necessary to supplement MRID 43129614 review.
MBC ? 00259471

or 00151418 NA --- This is a 1985 benomyl hydrolysis study. Since benomyl hydrolyzes quickly to MBC will be reviewed if needed for supplemental information on MBC hydrolysis. 835.2240 Aqueous photolysis TM 41482806 Acceptable No
TM 92186017 ---
TM 00036697 (same as 00039707), 00120625 Older studies, review not located. Risk assessment will rely on the acceptable results from 441482806..

TM 00120585 Unknown Published study that could supply additional data: Buchenauer et a. (1973) Pestic. Sci. 4:343-348.

### `

37 OCSPP Guideline Data Requirement Chem Submitted Studies (MRID or Access. #) Study Classificat ions Are more data needed? Justification and/or Assump tions EPA will Make in Absence of Data - Some Example texts are include

835.2240 Aqueous photolysis MBC 00151419 (benomyl, supplm. For MBC) In review --- Benomyl hydrolysis study (Powley, 1985), may contain useful supplemental information on MBC hydrolytic stability. See al so Access. No. 00097586 – reported dated 1971 which may also contain a benomyl hydrolysis study.
43129615 Unknown 1993 MBC “photostability” study; preliminary review will be conducted to see if supplemental information can be extracted from this study.
MBC 120626? Not Reviewed N/A Possibly supplemental. See footnote 8

835.2410 Soil photolysis TM 41482807 Acceptable No MR ID 42094601 provides additional information for 41482807. TM 42094601 Acceptable
835.2410 Soil photolysis MBC 00151420 Acceptable No Benomyl study – rapid and complete hydrolysis to MBC and used as surrogate data to meet MBC 835.2410 requirement.
835.4100 Aerobic soil metabolism TM+ MBC 00106085 Acceptable No Most recent study with TM (1982). Degradation in 3 test soils. Due to the rapid transformation to MBC (half-life <1 day in all 3 soils) study may meet requirements for MBC as well.
835.4100 Aerobic soil metabolism MBC 41255801(( Benomyl study) Acceptable No Study was classified acce ptable to support the registration of benomyl. Benomyl quickly converted to MBC and a MBC half-life was calculated.
835.4200 Anaerobic soil metabolism 154699 40158401 N/A No This study was determined to be acceptable, however, this study type is no longer required.

835.4300 Aerobic aquatic metabolism TM 45621401 Supplemen tal No 2001 study classified as supplemental (water aerobic, sediment anaerobic). Older study exists under Access. # 00165361
835.4300 Aerobic aquatic metabolism MBC 45620001 Unaccepta ble No Degradation of MBC in 2 systems

MBC 41291501 Acceptable This is a study with benomyl applied, determined to provide adequate information (benomyl was rapidly converted to MBC on the day of application in the study and the decline rate of MBC was calculated from this study.) See: EFED Benomyl RED Chapter, DP Barcode D264105.
835.4400 Anaerobic aquatic metabolism TM 40061501 Acceptable

835.4400 Anaerobic aquatic metabolism MBC 41137701 Acceptable This is a study with benomyl applied, determined to provide adequate information (benomyl was rapidly converted to MBC in the study and the decline rate of MBC was calculated from this study.)

8 Study type not confirmed, published article that was submitted b registrant: Helweg, A. (1977) Degradation and adsorption of carbendazim and 2-aminobenzimidazole in soil. Pestic. Sci. 8:71-78. (Also In unpublished submission received Sep 27, 1979 under 4581-340; submitted by Agchem Div., Pennwalt Co rp., Philadelphia, PA; CDL:099006- G)

### `

38 OCSPP Guideline Data Requirement Chem Submitted Studies (MRID or Access. #) Study Classificat ions Are more data needed? Justification and/or Assump tions EPA will Make in Absence of Data - Some Example texts are include

835.1230 Adsorption/ Desorption TM 42351001 Acceptable No

835.1230 Adsorption/ Desorption MBC 00151421+ 00151422 Acceptable No 00151421-22 are reported in the TM RED as meeting data requirements; these studies were to support benomyl registration but include experiments with MBC and 2-A,B. MBC 42351001 Acceptable No Study also included experiments to determine ads. /desorption properties of TM degradates MBC, DX105, and FH-432. 835.1410 Volatility – laboratory TM 40053210 42380101 Waived No MRID 42380101 was reviewed and determined to be supplemental but the requirement was later waived. TM 41482802 N/A No Supporting study reporting vapor pressure
835.1410 MBC None Waived No Waived in RED (2005).
835.6100 Terrestrial field dissipation (TFT) TM 43433701+ 43545801 Acceptable

TFT TM 41930101 Acceptable

TFT TM 41930102 Acceptable

TFT MBC 43941301 In review Benomyl applied. EFED RED Chapter says benomyl half-life was 86 days, need to confirm whether they meant to say that MBC half-life was 86 days.
TFT MBC 00146415 Acceptable 835.6100 Analytical method in soil TM 00035222 00036685 00053447 00053453 00077286 No review located.

835.6100 Analytical method in soil MBC 44295403 44295402 No review located. Yes Submitted to support benomyl registration, includes method for MBC in soil and an Independent Laboratory Validation.
835.6100/ 835.6200 Analytical method in water TM 00056043 00097927 00062539 No review located. Yes

835.6100/ 835.6200 Analytical method in water MBC None N/A. Yes

835.6200 Aquatic field dissipation TM None Waived No

835.6200 Aquatic field dissipation MBC None Waived No

MBC 41274801 In review Listed in EFED RED Chapter as fulfilling requirements; benomyl EFED RED chapter explains that this soil column l eaching in rice paddy soil adequately met requirements for 835.6200 However, TM and MBC do not currently have rice or other aquatic uses registered.

### `

39 OCSPP Guideline Data Requirement Chem Submitted Studies (MRID or Access. #) Study Classificat ions Are more data needed? Justification and/or Assump tions EPA will Make in Absence of Data - Some Example texts are include

165-4 (850.1730) Fish bioconcentration TM 133504 62545 120570 Waived EFED RED Chapter mentions waiver of the 165-4 (now 850.1730) study for MBC but not for TM. However, no study is required for TM which converts to the more persistent and more tightly bound MBC degradate.
165-4 (850.1730) Fish bioconcentration MBC 260573 Waived

### `

40 

## B. Effects For the major degradate MBC (Carbendazim), acute and chronic toxicity data are available for mammals, freshwater fish, and freshwater invertebra tes. Toxicity data is also available for terrestrial plants and for vascul ar and non-vascular aquatic plants for Thiophanate methyl, but not for the MBC degradate. In general, the data set is adequate for assessment of the TM parent with the exception that terrestrial plan t testing should be conducted at a higher rate to reflect current labels. No avian chronic data is available for the MBC degradate and expected MBC EECs exceed the NOAEL observed and test ed in the Thiophanate avia n reproduction study with the Mallard duck.

Table 9. Submitted Aquatic Ecological Effects Data for Thiophanate methyl

OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are further data needed to conduct risk assessment? Comments

850.1010 Freshwater invertebrate acute toxicity 40095505 supplemental No 00069601 supplemental 42298101 acceptable

00069602 00120662 supplemental

40995506 supplemental With Topsin 70WP

N.G. Crayfish acute 00097506 00106092 supplemental

850.1025 850.1035 850.1045 850.1055 Saltwater invertebrate acute toxicity 42123502 suppleme ntal No The only acceptable data are with a product. However, further testing is not required 00069603 acceptable 00083016 supplemental Mollusc study 42094602 supplemental No Minimal shell growth not attained in controls. However we have acceptable estuarine mollusc data on the MBC degradate

00120660 invalid

850.1075 Freshwater fish acute toxicity 00097506 00108092 acceptable No Adequate acute toxicity data has been generated for fish 42887001 acceptable

00083015- Rainbow
trout acceptable

### `

41 OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are further data needed to conduct risk assessment? Comments

00083015 Bluegill acceptable

42123501 acceptable

00081598 00041990 acceptable

TN 0635 supplemental 00041990 No relevant Summary of 00081598

00050516 supplemental

00055944 00088453 00062534 Invalid

00065065 invalid Open literature-no raw data

41560901 invalid

850.1075 Saltwater fish acute toxicity 42123503 acceptable No

850.1300 Freshwater invertebrate life cycle No data No No Chronic data for the MBC degradate is available

850.1350 Saltwater invertebrates life cycle No data No No Chronic data for the MBC degradate is available

850.1400 Freshwater fish early-life stage No data No No Chronic data for the MBC degradate is available for two species

850.1400 Saltwater fish early-life stage No data No No surrogate chronic data with MBC has been submitted for a marine species 850.1500 Fish life cycle No data -- 850.4400 Aquatic plant Toxicity Test using Lemna
spp. 42123505 acceptable No --

850.4500 850.4550 Algal toxicity Cyanobacteria 42229802 acceptable No 42229801 acceptable No 42229803 acceptable No 42298102 acceptable No

### `

42 OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are further data needed to conduct risk assessment? Comments

850-1735 Sediment Toxicity Test with Aquatic Invertebrate No data No This requirement should be fulfilled by chronic exposure testing with the MBC degradate



### Table 10. Submitted Terrestrial Ecologi cal Effects Data for Thiophanate methyl

OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are data needed for risk assessment? Comments

850.2100 Avian oral toxicity 00083012 acceptable No 00121596 acceptable

00042894 00056033 00098146 00120567 Invalid Japanese quail – same study- multiple MRIDs

850.2200 Avian dietary toxicity 00069600 acceptable No 00083013 acceptable 00083014 acceptable 41930104 acceptable 41930103 Supplemental LC50 > 3882 PPM (mean measured concentration)

850.2300 Avian reproduction 42474801 acceptable No Egg size and body weight of Mallard offspring effected (42474801) at 500 PPM with NOAEL at 103 ppm 00120658 acceptable

00120659 acceptable

42930701 acceptable

42475201 Invalid

Nonguideline Avian inhalation No data No

Acute oral mammal-rat 41644301 Valid 96.55 % technical

Acute oralmammalmouse 00057655 Valid

850.3020 Honey bee
acute contact 40053209 acceptable No --

### `

43 OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are data needed for risk assessment? Comments

toxicity 00080286 No-Insufficient data

850.3030 Honey bee residue on foliage 00163178 No letter summarizing research

OECD 213 Honey bee acute Oral Toxicity No Data Yes Exposure of honey bees to TM via oral routes is expected based on magnitude of residue studies

OECD 237 Honey bee Larval Toxicity Test No Data Yes Exposure of honey bees to TM via oral routes is expected based on magnitude of residue studies 850.3040 Field testing for pollinators No data No --

850.4100 Seedling Emergence and Seedling Growth 42123504 44237401 44404101 Acceptable for up to 1.4 lbs ai/Acre rate Yes Data is acceptable to for application rates < 1.4 lbs ai/Acre; Data are needed for higher applications

850.4150 Vegetative Vigor 42123504 44237401 44404101 Acceptable for up to 1.4 lbs ai/Acre rate Yes Data is acceptable to for application rates < 1.4 lbs ai/Acre; Data are needed for higher applications

Table 11. 

### Aquatic Ecological Effects Data for the MBC 1 

### Degradate (Carbendazim; PC Code 128872)

OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are data needed for risk assessment? Current Additional Data Need

850.1010 Freshwater invertebrate 43205502 supplemental No

00154467 acceptable

42414201 MBC data submitted for Benomylcontract draft- acceptable00154693 Open litsupplemental Benomyl, Thiophanate and MBC toxicity to 4 FW organisms

850.1075 Freshwater fish acute toxicity 00154690 supplemental No Conducted with 50WP formulation

00154691 unacceptable

00165115

### `

44 OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are data needed for risk assessment? Current Additional Data Need

43129606 supplemental

43129607 acceptable

40098001 supplemental USFWS 10 study results with LC50 range from 7.4 to 650 ppb. Different age ranges. 00154692 supplemental Summary report for MBC tests conducted by USFWS

850.1300 Freshwater invertebrate life cycle 40987901 Hutton, 1986 acceptable No MBC study conducted for Benomyl

42529401 acceptable No MBC st udy conducted for Benomyl

850.1400 Fish Early Life stage 43011801 acceptable No MBC st udy conducted for Benomyl

43872801 In review

850.1025 850.1035 850.1045 850.1055 Estuarine/Marine Invertebrate
acute 40964701 with Mysid acceptable No

Acute Marine Mollusc 40975002 Eastern oyster acceptable No

850.1075 Estuarine Marine fish acute 40975001 Sheepshead minnow Core No

850.1350 Estuarine/Marine Invertebrate chronic 42723701

see benomyl acceptable No MBC study conducted for Benomyl with Mysid

850.4400 Aquatic plant growth: Tier II vascular plants 43913601 supplemental Yes This test is with a Flusilazole/Carbendazim mixture product

850.4500 850.4550 Aquatic nonvascular plants No data No data Yes

1 

### MBC=Methyl-2-benzimidazolecarbamate is the majo r degradate of Benomyl and Thiophanate methyl

### `

45 Table 12. Terrestrial Effects Data for the MBC Degradate (Carbendazim; PC Code 128872)

OCSPP Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are data needed for risk assessment? Comments for Clarification or on Additional Data Needs

850.2100 Avian oral toxicity 43129604 acceptable No 00154667 acceptable 850.2200 Avian dietary toxicity 00154688 acceptable No - 00154689 acceptable 43129605 acceptable 43205501 supplemental 40% mortality at 4467 ppm 00165113 IBT study submitted with Carbendazim 00165114 IBT study submitted with Carbendazim

850.2300 Avian reproduction 44103001 acceptable No Acceptabl e reproduction studies for Benomyl measured MBC concentration levels in the diet-adverse effects observed at 720 ppm in Mallard ducks 44103002 acceptable

Nonguideline Avian inhalation No data No

850.3020 Honey bee
acute contact toxicity 00154695 acceptable No LD50 >50 ug ai/bee

OECD 213 Honey bee acute Oral Toxicity No Data Yes Exposure of honey bees to MBC via oral routes is expected based on magnitude of residue studies

OECD 237 Honey bee Larval Toxicity Test No Data Yes Exposure of honey bees to MBC via oral routes is expected based on magnitude of residue studies 850.3030 Honey bee residue on foliage No data No --

850.3040 Field testing for pollinators No data No --

850.4100 Seedling Emergence and Seedling Growth No data No Data requir ement addressed with TM

850.4150 Vegetative Vigor No Data Data requirement addressed with TM

Earthworm Toxicity 154694 Supplemental No
47807011 Supplemental With Ecolan a mixture of Trifluralin and Carbendazim

### `

46 Guideline Number: 

### 850.4100 and 850.4150 - Requested in Previous RED Study Title: 

### Terrestrial Plant Seedling Emergence and Vegetative Vigor at highest labeled rate for crop use of Thiophanate methyl

Rationale for Requiring the Data 

### Tier I tests were conducted using tec hnical TM: MRID 44104101 and 42123504 for seedling emergence and vegetative vigor, respectively. The maximum dosag e tested was 1.4 lbs ai per acre. These data are not useful for risk a ssessment purposed because the maximum label rate exceeds the maximum rate tested. Tier 1 seedlin g emergence and vegetative vigor tests are needed at the maximum application rate for TM. Pending results of Tier 1 tests, Tier 2 tests may be required (e.g., if effects are statistically si gnificant and/or greater than 25% relative to controls). Practical Utility of the Data 

### These data will enable risk assessment of TM app lications to terrestrial plants. Absence such data, risk to terrestrial plants at higher appli cation rates may have to be presumed, which will greatly increase concerns with listed species determinations.

MBC data Requested to Alleviate Uncertaint ies regarding MBC Degradate Toxicity and Risk from Uses of Thiophanate methyl

Guideline Number: 850.4400, 850.4500 and 850.4550 Study Title: Aquatic Plant Acute Toxicity testing with MBC Rationale for Requiring the Data Based on expected concentrations of MBC in th e aquatic environment 850. 4400, 850.4500 and 850.4550 toxicity to aquatic plants are required to assess potentia l impacts to this group. No data on MBC toxicity to aquatic plants was submitted. Given that MBC is s ubstantially more toxic than TM to aquatic animals, data are needed to assess risk to aquatic plants.

Practical Utility of the Data 

### MBC is expected to be present in aquatic envi ronments and has been shown to be toxic to aquatic plants in open literature studies . Wit hout acceptable studies risk to plants from this degradate of TM cannot be assessed with certainty.

### `

47 Guideline Number: OECD 213 Study Title: Honey bee Adult Acute Oral Toxicity Testing with TM and MBC degradate Rationale for Requiring the Data 

### Thiophanate methyl and it’s degr adate MBC are systemic fungicides which may be transported into foliar tissues and pollen of exposed plants a nd thus be secondarily ingested by pollinators. Although on an acute contact basis, TM and MBC are practically non -toxic to adult honey bees, their toxicity on an acute oral basis is not known. Past experience indicates contact toxicity is not a reliable indicator of oral toxicity in bees. Available information from magnitude of residue studies indicates both TM and MBC will be present in and/or on plant tissues. Practical Utility of the Data 

### These data are needed in order to assess poten tial risks of TM and MBC residues in pollen and nectar to bees.

Guideline Number: OECD 237 Study Title: Honey bee Larval Toxicity Test, Single Exposure with TM and MBC degradate Rationale for Requiring the Data 

### Thiophanate methyl and it’s degr adate MBC are systemic fungicides which may be transported into pollen of exposed plants and thus be tran sported back to the hive and ingested by honeybee larvae. No data are available to evaluate the t oxicity of TM and MBC to honey bee larvae. Past experience indicates that adult cont act toxicity is not a reliable indi cator of pesticide toxicity to larvae. Practical Utility of the Data 

### These data are needed in order to assess poten tial risks of TM and MBC residues in pollen and nectar to larval bees.

Guideline Number: Non-Guideline Study Title: Whole sediment Chronic toxi city test for aquatic invertebrates Rationale for Requiring the Data 

### Based on current proposed uses of TM the MBC de gradate is expected to reach in the benthic aquatic environment and partition to sedime nts based on Koc values > 1000 for MBC, persistence in aerobic soil of >10 days. Eval uation of estimated concentrations of MBC degradate in pore water relative to chronic toxicity to freshwater invertebrates suggests potential risks to benthic invertebrates. Sediment toxicity tests evalua te exposure not only through pore water, but also through ingestion of sediment particles and food. Whole sediment chronic toxicity test for aquatic invert ebrates are therefore requested per 40 CFR Part 158 requirements. Practical Utility of the Data 

### Receipt of this information will enable risk asse ssment to benthic invertebrates to be evaluated for the MBC degradate from all relevant routes of exposure and for species that are present in the sediments.



# 8. References

### `

48 See also Appendix C for a list of studies submitted to the Agency to meet Environmental Fate or Ecological Effects data requirements for Th iophanate methyl and Carbendazim (MBC).

Bohaty, R.F.H.; W. Eckel, K. White, and D. Young. 2012 (USEPA). Standard Operating Procedure for Using the NAFTA Guidance to Calculate Representative Half-life Values and Characterizing Pesticide Degrada tion (November 30, 2012). Available at: http://www.epa.gov/oppefed1/ecorisk_ders/deg radation_kinetics/f tt_sop_using_nafta_gui dance.pdf

Jones, R.D. et al., 2000. Guidance for use of the Index Reservoir and Percent Crop Area Factor in Drinking Water Assessments (March 21, 2000). Office of Pesticide Programs, Environmental Fate and E ffects Division, U.S. Envir onmental Protection Agency. Arlington, VA.

USEPA. 1999. Guidance for Use of the Inde x Reservoir in Drinking Water Exposure Assessments. Arlington, VA.

USEPA. 2000. Drinking Water Screening Level Assessment. Part A: Applying a Percent Crop Area Adjustment to Tier II Surface Water M odel Estimates for Pesticide Drinking Water Exposure Assessments. FQPA Science Po licy Document .Public Comment Draft September 1, 2000. Federal Register: Oc tober 11, 2000 (volume 65, number 197). Electronic copy available at http://w ww.epa.gov/pesticides/trac/science/ .

U.S. EPA. 2003b. Use of Regional Percent Cr op Area Factors in Re fined Drinking Water Assessments. US EPA Office of Pesticide Programs (OPP), Environmental Fate and Effects Division (EFED), Water Quality Technical Team (WQTT). Arlington, VA

USEPA, 2003c. SCI-GROW 2.3: Windows Versi on of SCI-GROW. September 30, 2003. Office of Pesticide Programs, Environmental Fate and Effects Division, U.S. Environmental Protection Agency. Arlington, VA.

USEPA. 2004. Overview of the Ecological Risk Assessm ent Process in the Office of Pesticide Programs . United States Environmental Protec tion Agency (USEPA). Environmental Fate and Effects Division. Office of Pesticide Programs. Available at http://www.epa.gov/espp/consultation/ecorisk-overview.pdf

.

USEPA. 2007 a . Ecological Incident Information System. http://www.epa.gov/espp/consultation/ecorisk-overview.pdf

USEPA. 2007 b . ECOTOXicology Database. Office of Research and Development National Health and Environmental Effects Research Laboratory’s (NHEERL’s) Mid-Continent Ecology Division (MED). http://cfpub.epa.gov/ecotox/

### `

49 USEPA. 2009 c . Guidance for Selecting Input Parameters in Modeling the E nvironmental Fate and Transport of Pesticides. Version 2.1. U. S. Environmental Protection Agency, Office of Pesticide Programs, Environmental Fate and Effects Division, Oct. 22, 2009. Online at: http://www.epa.gov/oppefed1/models/w ater/input_parameter_guidance.htm

USEPA 2013. Usage/Use Report Package in Sup port of Registration Review Carbendazim (128872). U.S. Environmental Protection Ag ency, Office of Chemical Safety and Pollution Prevention, Biological and Econom ic Analysis Division. November 25, 2013.

USEPA. 2013. Screening Level Usage Analysis. U.S. Environmental Protection Agency, Office of Chemical Safety and Pollution Preventi on, Biological and Economic Analysis Division. May 7, 2013.

Toxicity References

References cited in this document, but not cont ained in the citations included in Appendix C.

Canton, J.H. 1976. The Toxicity of Benomyl, Thi ophanate-methyl, and BCM to Four Freshwater Organisms. Bull. Of Environmental C ontamination and Toxicology, Vol. 16, No. 2

Roark, J.H. and J.L. Dale, 1979. The Effect of Turf Fungicides on Earthworms. Arkansas Academy of Science proceedings, Vol. XXXIII, 1979.

Stringer, A. and Clive H. Lyons, 1974. The E ffect of Benomyl and Thiophanate-methyl on Earthworm Populations in Apple Orchar ds. Pesticide Science, 1974, 5. 189-196

### `

50 

# 9. Appendices

A. SIP and STIR Results

STIR Model INPUT/OUTPUT


# Welcome to the EFED Physical Chemistry, Application Methods, and Model Parameters



# Screening Tool for Inhalation Risk Pesticid

e Applicati on Rate (lb ai/acre) 2.8



### This tool is designed to provide the risk assessor with a rapid method for determining the potential Pesticid

e Applicati on Rate (mg/cm 2 ) 3.14E02



### significance of the inhalation exposure route to birds and mammals in a risk assessment. Saturate d Air Vapor Concent ration (mg/m 3 ) 0.23954 3644 This is the theoretical maximum pure product air concentration at a temperature of 25oC and pressure 1atm Height of Direct Spray Column (m) 1 Note: Assumes 3.3 m for aerial and 1m for ground



# Input Duration of Direct Spray Inhalatio n (min) 0.5 Note: Assumes 1.5 minutes for aerial and 30 seconds for ground

Application and Chemical Information Air Column Concent ration After Spray (mg/cm 3 ) 0.00031 3838

Enter Chemical Name Thioph anate methyl *Fractio n of Spray 0.9 Modify the fraction of spray inhaled here to account for the droplet

### `

51 Inhaled distribution specified on the label

Enter Chemical Use Fungici de Is the Application a Spray? (enter y or n) y

If Spray What Type (enter ground or air) ground Avian Calcula tions

Enter Chemical Molecular Weight (g/mole) 342.4 Animal Wt from Oral Study (kg) 0.178

Enter Chemical Vapor Pressure (mmHg) 1.30E05 Bird Wt Assume d (kg) 0.02

Enter Application Rate (lb a.i./acre) 2.8 Vapor Inhalatio n Dose(mg/kgbw) 0.03011 193

Inhalatio n Rate (cm 3 /hr) 2514.10 8068 Note: Uses USEPA (1993) approach, resting rate multiplied by 3

Toxicity Properties Estimat ed Avian Inhalatio n LD 50 (mg/kg) 35910.9 2612

Bird Adjuste d Avian Inhalatio n LD 50 (mg/kg) #VALUE !

Enter Lowest Bird Oral LD 50 (mg/kg bw) 4640 Spray Droplet inhalatio n Dose(mg/kgbw) 0.29588 3798 Enter Mineau Scaling Factor 1.50. Enter Tested Bird Weight (kg) 0.178

Mammal Mamma lian Calcula tions

Enter Lowest Rat Oral LD 50 (mg/kg bw) 5000 Animal Wt from Inhalatio n Study 0.35 Note: Most inhalation toxicity "six pack" studies use the rat whose default weight is

### `

52 (kg) 0.35 kg

Enter Lowest Rat Inhalation LC 50 (mg/L) 5000 Mammal Wt Assume d (kg) 0.015

Duration of Rat Inhalation Study (hrs) 4 Inhalatio n Rate 2370.19 8518 Note: Uses USEPA (1993) approach, resting rate multiplied by 3

Enter Rat Weight (kg) 0.35 Vapor Inhalatio n Dose(mg/kgbw) 0.03785 1066 Mammal ian Inhalatio n LD 50 (mg/kg) 135439. 9153 Note: Converted from an LC50 to an LD50 based on the weight of the test animal, the default is a 0.35 kg rat



# Output Adjuste d Mammal ian LD 50 (mg/kg) 297673. 9771 Note: Mammalian LD50 adjusted from 350g rat to 15 g mammal



### Results Avian (0.020 kg ) Spray Droplet Inhalatio n Dose(mg/kgbw) 0.37192 9565 Maximum Vapor Concentration in Air at Saturation (mg/m 3 ) 2.40E01 Maximum 1-hour Vapor Inhalation Dose (mg/kg) 3.01E02 ground Adjusted Inhalation LD 50 #VALU E! air Ratio of Vapor Dose to Adjusted Inhalation LD 50 #VALU E! #VALUE ! yMaximum Posttreatment Spray Inhalation Dose (mg/kg) 2.96E01 n Ratio of Droplet Inhalation Dose to Adjusted Inhalation LD 50 #VALU E! #VALUE !



### Results Mammalian (0.015 kg ) Maximum Vapor 2.40E-

### `

53 Concentration in Air at Saturation (mg/m 3 ) 01

Maximum 1-hour Vapor Inhalation Dose (mg/kg) 3.79E02 Adjusted Inhalation LD 50 2.98E+ 05

Ratio of Vapor Dose to Adjusted Inhalation LD 50 1.27E07 Exposur e not Likely Significa ntMaximum Posttreatment Spray Inhalation Dose (mg/kg) 3.72E01

Ratio of Droplet Inhalation Dose to Adjusted Inhalation LD 50 1.25E06 Exposur e not Likely Significa nt



### SIPS 1.0 INPUT/OUTPUT

Table 1. Inputs Parameter Value Chemical name Thiophanate methyl Solubility (in water at 25 o C; mg/L) 8

Mammalian LD 50 (mg/kg-bw) 5000 Mammalian test species laboratory rat Body weight (g) of "other" mammalian species

Mammalian NOAEL (mg/kg-bw) 5000 Mammalian test species laboratory rat Body weight (g) of "other" mammalian species

Avian LD 50 (mg/kg-bw) 4640 Avian test species northern bobwhite quail Body weight (g) of "other" avian species Mineau scaling factor 1.15

Mallard NOAEC (mg/kg-diet) 103 Bobwhite quail NOAEC (mg/kg-diet) 150 NOAEC (mg/kg-diet) for other bird species Body weight (g) of other avian species NOAEC (mg/kg-diet) for 2nd other bird species Body weight (g) of 2nd other avian species

### `

54 Table 2. Mammalian Results Parameter Acute Chronic Upper bound exposure (mg/kg-bw) 1.3760 1.3760 Adjusted toxicity value (mg/kg-bw) 3845.8028 3845.8028 Ratio of exposure to toxicity 0.0004 0.0004

Conclusion* Drinking water exposure alone is NOT a potential

concern for mammals Drinking water exposure alone is NOT a potential

concern for mammals

Table 3. Avian Results Parameter Acute Chronic Upper bound exposure (mg/kg-bw) 6.4800 6.4800 Adjusted toxicity value (mg/kg-bw) 3342.7930 5.1101 Ratio of exposure to acute toxicity 0.0019 1.2681

Conclusion* Drinking water exposure alone is NOT a potential concern for birds Exposure through drinking water alone is a

potential concern for birds

*Conclusion is for drinking water exposure alone. This does not combine all routes of exposure. Therefore, when aggregated with other routes ( i.e ., diet, inhalation, dermal), pesticide exposur e through drinking water may contribute to a total exposure that has potential for effects to non-target animals.

### `

55 

## B. Structures of Thiophanate Methyl and Degradates

Table 13. Structures and properties of thiopha nate methyl and its degradates.



## Thiophanate Methyl (parent)

IUPAC Name: Dimethyl 4,4'- o -phenylenebis(3-thioallphanate) CAS name: Dimethyl((1,2,-phenylene)bis(im inocarbonothioyl))bis(carbamate) CAS #: 23564-05-8 SMILES: S=C(N)N(C(=O)OC)c1 ccccc1N(C(=O)OC)C(N)=S Molecular Formula: C12H14N4O4S2 Average mass: 342.394012 Da Synonyms: Carbamic acid, [1,2-phenylenebis(imi nocarbonthioyl)]bis-dimethyl ester. Bis(3-(methoxycaronyl)- 2-thioreido)benzene. Dimethyl 1,2-phenylenebis (carbamothioylcarbamate). Methyl thiophanate. Topsin M, Cercobin M, Thiophanate M, Banrot, Fungo, TD-1771, NF-44, Enovit Methyl, Duosan, Systec. 

# NHCS.NHCO.OCH 3



# NHCS.NHCO.OCH 3 

# *

Carbendazim (HOE 017411)

IUPAC Name: methyl benzimidazol-2-ylcarbamate



# N

N NH OMe

O H * OCH3 C

AV-1951

IUPAC Name: 2(N-methoxy carbonyl thio ureido) phenylenelthiourea

### `

56 

## NHCNHCOCH 3



## NHCNH 2 

## S O

S

2-AB

IUPAC Name: 2-Aminobenzimidazole



## N H N NH 2 

## C

4-OH-TM

IUPAC Name: Dimethyl[1,2-(4-hydroxyphenyl ene)bis(imonocarbonothioyl)]bis (carbamate)



## NHCNHCOCH 3



## NHCNHCOCH 3 

## O H S O

S O

DX105:

methyl N-[2-(N'-methoxycarbony1thiour eido)pheny1-aminocarbony1]carbamate 1-(3-methoxycarbony1-2-thioureido)-2-(3-methoxycarbony1ureido) benzene OR Methyl-N-[2-(N’-methoxycarbonyl-thiour eido)phenylaminocarbonyl]carbamate

### `

57 FH-432:

dimethyl-4,4'-o-phenylenebis-al1ophanate

or carbamic acid, N,N'-[1,2-phenylenebis(i minocarbonyl)]bis-, dimethyl ester SMILES: O=C(Nc1ccccc1NC(=O)NC(=O)OC)NC(=O)OC Molecular Formula: C12H14N4O6 Average mass: 310.262787 Da



## C. OPPIN Bibliography of Environmental Fate and Ecological Effects Studies Submitted to support the Registrations of Thiophanate Methyl or MBC

102001 Thiophanate methyl Eco Effects Bibliography

### `

58 

## (c hecked 06-10-2013.)

Avian Single Dose Oral Toxicity

MRID DER-PDF Image Citation Reference

42894 or 56033 2004902 2004962 W.A. Cleary Corporation (19??) Oral Toxicity to Japanese Quails. (Unpublished study received Mar 4, 1971 under unknown admin. no.; CDL:104612-C or CDL:132787-B)

55934 2004846 Pg.3-4 Accession No.127270 Hashimoto, Y.; Noguchi, T.; Makita, T.; et al. (1970) Toxicological Evaluation of Thiophanate-methyl (I ) Acute and Sub-acute Toxicity of Thiophanate-methyl. (Unpublished study received Feb 17, 1972 under unknown admin. no.; prepared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Agchem Div., King of Prussia, Pa.; CDL:127270-L)

83012 2004878 2004946 Fink, R.; Beavers, J.B.; Brown, R. (1977) Final Report: Acute Oral LD50-- Bobwhite Quail: Project No. 110-118. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Wildlife Inter- national, Ltd. and Washington College, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:232169-B)

98146 2004928 W.A. Cleary Corporation (19??) Oral Toxicity to Japanese Quails: ?Thiophanate-methyl|. (Unpublished study received Mar 16, 1971 under 1001-51; CDL:101533-B)
120567 2004902 W.A. Cleary Corp. (19??) Oral Toxicity to Japanese Quails. (Unpublished study received Mar 16, 1971 under 1001-50; CDL:022098-C)

121596 2004910 Fink, R.; Beavers, J.; Brown, R. (1977) Acute Oral LD50--Mallard Duck: Topsin M Technical: Project No. 110-119. Final rept. (Unpublished study received May 12, 1978 under 4581-322; pre- pared by Wildlife International Ltd. and Washington College, submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:233882-B) ID= NAOTHIO1 on the DER

48146 2004858 ICI United States, Incorporated (1975?) PP588 2E: Toxicology. Summary of studies 226444-C through 226444-J. (Unpublished study received on unknown date under unknown admin. no.; CDL: 226444-B)
92186003 Summary of MRID 00083012 Shellenberger, T. (1990) Pennwalt Corporation Phase 3 Summary of MRID 00083012. Topsin M - Acute Oral LD50 Test - Bobwhite Quail: Project No. 110- 118. Prepared by WILDLIFE INTERNATIONAL, LTD. 11 p. 92186004 Summary of MRID 00121596 Shellenberger, T. (1990) Pennwalt Corporation Phase 3 Summary of MRID 00121596. Topsin M-Acute Oral LD50 Test - Mallard Duck: Project No. 110-119. Prepared by Wildlife International, LTD. 11 p.



### Avian Dietary Toxicity

MRID DER-PDF Image Citation Reference

### `

59 69600 2004920 2004964 Fink, R.; Beavers, J.B.; Brown, R. (1977) Final Report: Eight-day Dietary LC50--Bobwhite Quail: Project No. 110-116. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Wildlife International, Ltd. and Washington College, submitted by Penn- walt Corp., Philadelphia, Pa.; CDL:232169-D)

83013 2004966 Fink, R. (1975) Final Report: Eight-day Dietary LCI50^--Bobwhite Quail: Project No. 110-107. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Truslow Farms, Inc., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:232169-C)

83014 2004907 2004940 Fink, R. (1975) Final Report: Eight-day Dietary LCI50^--Mallard Ducks: Project No. 110-108. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Truslow Farms, Inc., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:232169-E)

41930103 2057707- contract draft Pedersen, C.; Helsten, B. (1991 ) Thiophanate-Methyl: 8-Day Acute Dietary LC50 in Mallard Ducklings: Final Report: Lab Project Number BLAL 90-DC-150. Unpublished study pre pared by Bio-Life Assoc., Ltd. 53 p.

41930104 2080562 2080562- contract draft Pedersen,C.; Helsten, B. (1991) Thiophanate-Methyl: 8-Day Acute Dietary LC50 Study in Mallard Ducklings: Final Report: Lab Pro- ject Number: BLAL 90-DC 150-A. Unpublis hed study prepared by Bio-Life Assoc., Ltd. 58 p.
92186005 Summary of MRID 00069600 Shellenberger, T. (1990) Pennwalt Corporation Phase 3 Summary of MRID 00069600. Eight-day Dietary LC 50 of Topsin M Technical to Bobwhite Quail: Project No. 110-116. Prepared by Wildlife International, Ltd. 12 p.



### Avian Reproduction

MRID Citation Reference

108872 2004948 Cannon Laboratories, Inc. (19??) Avian Reproduction: No. 777-40.(Unpublished study received Jul 26, 1977 under 4581-322; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL: 236529-A)
120658 2004929 Krize, J. (1978) Reproducti on Study of Topsin M Technical 94% (N.B. 77-126-4) in Bobwhite Quail: Laboratory No. 7E-7561. (Unpublished study received May 12, 1978 under 4581-322; pre- pared by Cannon Laboratories, Inc., submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:233882-C)
120659 2004949 Krize, J. (1978) Reproducti on Study of Topsin M Technical 94% (N.B.- -77-126-4) in Mallard Ducks: Laboratory No. 7E-7562. (Unpublished study received May 12, 1978 under 4581-322; pre- pared by Cannon Laboratories, Inc., submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:233882-D)

42474801 2078055 2082513- contract draft Pedersen, C.; Lesar, C. (1992) Thiophanate-methyl: Toxicity and Reproduction Study in Mallard Ducks: Lab Project Number: 89 DR 36. Unpublished study prepared by Bio-Life Associates, Ltd. 399 p.

### `

60 42475201 2078056 2004957=

memo Pedersen, C.; Fletcher, D.; Lesar, C. (1992) Thiophanate-methyl: Toxicity and Reproduction Study in Bobwhite Quail: Lab Project Number: 89 QR 40. Unpublished study prepared by Bio-Life Associates, Ltd. 443 p.

42930701 2004916 2004975=

memo Pedersen, C.; Solatycki, A. (1993) Thiophanate-methyl: Toxicity and Reproduction Study in Bobwhite Quail: Lab Project Number: 106-014- 07. Unpublished study prepared by Bio-life Associates, Ltd. 443 p.



### Acute Toxicity to Freshwater Fish

MRID DER-PDF Image Citation Reference

50516 or 57655 or 80283 2004898 2004922 Noguchi, T.; Hashimoto, Y.; Makita, T.; et al. (1970) Toxicological Evaluation of Thiophanate-methyl: (I) Acute and Sub-acute Tox- icity of Thiophanate-methyl. (Unpublished study received Sep 5, 1972 under 2G1249; prepared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:091777-K)
81598 2004926 Krize, J.W. (1978) 96-hour Static LC50 in Bluegill Sunfish: Laboratory No. 8E-3306. (Unpublished st udy received Sep 27, 1979 un- der 4581-340; prepared by Cannon Laboratories, Inc., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:099011-R)

83015 Or 39709 2004927 2004961 Kuc, W.J. (1977) The Acute Toxicity of Topsin^(R)I M Fungicide 70% W.P. to the Bluegill Sunfish,~Lep omis macrochirus~Rafinesque and Rainbow Trout,~Salmo gairdneri~Richardson: UCES Project # 11506- 41-02. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Union Carbide Corp., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:232169-F)

97506 or 106092 2007909 2007910 2004950= lab audit Bailey, H.C. (1981) Acute Toxicity of Topsin^(R)I M Fungicide to Channel Catfish (Ictalurus punct atus) and Louisiana Red Crayfish (Procambarus clarkii): SRI Project LSC-1514. Final rept. (Unpublished study received Mar 22, 1982 under 4581-322; prepared by SRI International, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:070726-A)
41560901 2004911 Nishibe, T.; Saika, O.; Kosaka, S.; et al. (1983) Thiophanate- Methyl: Acute Toxicity Study in Rainbow Trout: Lab Project Numb- er 0073. Unpublished study prepared by Niss o Institute for Life Science, Biomedical Research Dept. 14 p.
42123501 2004952 Bettencourt, M. (1991) Thiophanate-methyl--Acute Toxicity to Bluegill Sunfish (Lepomis macrochirus) Under Flow-through Condi- tions: Lab Project Number: 91-8-3871: 12442.0191.6109.105. Un- published study prepared by Springborn Laboratories, Inc. 66 p.
42887001 2004955 Bettencourt, M. (1993) Thiophanate-Methyl--Acute Toxicity to Rainbow Trout (Oncorhynchus mykiss) Under Flow-Through Conditions: Lab Project Number: 93-4-4738: 12681.1292.6101.108. Unpublished study prepared by Springborn Laboratories, Inc. 67 p.

41990 2004926 Pg.3 Jacobson, S.O.; Terrell, Y. (1980) Topsin^(R)I M Fungicide Technical--Cannon's Bluegill Sunfish Toxicity Study 8E-3306. (Unpublished study received Jul 11, 1980 under 4581-322; pre- pared in

### `

61 cooperation with Cannon Laboratories, Inc., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:099310-F)

55944 2004942 invalid Mixon, W.W. (1971) Fish Toxicity--Topsin M and E. (Unpublished study received Feb 17, 1972 under unknown admin. no.; submitted by Pennwalt Corp., Agchem Div., King of Prussia, Pa.; CDL: 127270-AA)

88453 or 62534 2004908 Invalid 2004963 Mixon, W.W. (1971) Letter sent to Agchem File dated Oct 12, 1971: Fish toxicity of Topsin M--origi nating in food. (Unpublished study received Feb 9, 1973 under 4581-288; submitted by Penn- walt Corp., Philadelphia, Pa.; CDL:007463-O)



### 65065 2004924 invalid Yoshida, K.; Nishiuchi, Y. (1972) Toxicity of Pesticides to Some Water Organisms. (Translated from: Bull. Agr. Chem. Inspect. Stn. no. 12:122-128 (Japan); unpublished study)

Acute Toxicity to Freshwater Invertebrates

MRID DER-PDF Image Citation Reference

69601 2004905 Roberts, S.; Parke, G.S.E. (1977) 96-hour Static LC50 in~Daphnia~ ?~magna~: Laboratory No. 7E-611 5. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Cannon Laboratories, Inc., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL: 232169-G)

69602 2004925 70% WP formulation test Roberts, S.; Parke, G.S.E. (1977) 96-hour Static LC50 in~Daphnia~ ?~magna~: Laboratory No. 7E-611 6. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Cannon Laboratories, Inc., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL: 232169-H)

97506 2007909 2004950=lab audit Bailey, H.C. (1981) Acute Toxicity of Topsin^(R)I M Fungicide to Channel Catfish (Ictalurus punct atus) and Louisiana Red Crayfish (Procambarus clarkii): SRI Project LSC-1514. Final rept. (Unpublished study received Mar 22, 1982 under 4581-322; prepared by SRI International, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:070726-A)

106092 2004926 2007910 Bailey, H. (1981) Acute Toxicity of Topsin M Fungicide to Channel Catfish ... and Louisiana Red Crayfish ...: SRI Project LSC- 1514. Final rept. (Unpublished study rece ived Jul 21, 1982 under 4581-322; prepared by SRI International, subm itted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:070993-D)
120662 2004925 Roberts, S.; Parke, G. (1977) Static 96-hour Toxicity Study of Topsin WP 70% in Daphnids: Laboratory No. 7E-6116. (Unpublished study received Apr 29, 1977 under 4581-322; prepared by Cannon Laboratories, Inc., submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:235913-A)

40095505 2004951 2004970 Nishibe, T. (1986) Thiophanate-methyl: Acute Toxicity Study in Daphnids: Laboratory Project ID. NISSO TXR 0215. Unpublished study prepared by Nippon Soda Co., Ltd. 23 p. Daphnia carinata
40095506 DER not Nishibe, T. (1986) Thioph anate-methyl Formulation--Topsin M 70%

### `

62 located 70% WP formulation test WP: Acute Toxicity Study in Daphnids: Laboratory Project ID. NISSO TXR 0216. Unpublished study prep ared by Nippon Soda Co., Ltd. 23 p.

42298101 2004934 2004915=

memo Putt, A. (1992) Thiophanate-methyl --Acute Toxicity to Daphnids (Daphnia magna) Under Flow-through Conditions: Final Report: Lab Project Number: 92-4-4217: 12681.1191.6100.115. Unpub- lished study prepared by Springborn Labs., Inc. 68 p.
92186006 Summary of MRID 40095505 Saika, O. (1990) Pennwalt Corp oration Phase 3 Summary of MRID 40095505. Thiophanate-methyl - Acute Toxicity Study in Daphnids: Project No. TXR-215. Prepared by Nippon Soda Co. Ltd. 10 p.



### Acute Toxicity to Estu arine/Marine Organisms

MRID DER-PDF Image Citation Reference

69603 2004945 Vilkas, A.G. (1977) ?96-hour LC50 of Topsin M 70% WP to~Palaemo~- ?~netes pugio~|: UCES Project # 11506-41-02. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Union Carbide Corp., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:232169-J)
83016 2004947 Vilkas, A.G. (1977) The Acute Toxicity of Topsin M 70% WP to theFiddler Crab,~Uca pugilator~: UCES Project # 11506-41-02. (Unpublished study received Nov 8, 1977 under 4581-322; prepared by Union Carbide Corp., submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:232169-I)
120660 2004969 Roberts, S.; Parke, G.; Charle s, S. (1977) Static 96-hour Toxicity Study of Topsin M 70% W.P. in Straight-hinge Oyster Larvae: Laboratory No. 7E-7943. (Unpublished study received May 12, 1978 under 4581-322; prepared by Cannon L aboratories, Inc., submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:233882-E)

42094602 2004971 2004912=

memo 2004932=

memos Dionne, E. (1991) Thiophanate-methyl: Acute Toxicity to Eastern Oyster (Crassostrea virginica) Under Flow-Through Conditions: Lab Project Number: 91-7-3816: 12442.0191.6107.504. Unpublished study prepared by Springborn Labs, Inc. 66 p.

42123502 2004972 Bettencourt, M. (1991) Thiopha nate-methyl--Acute Toxicity to Mysid Shrimp (Mysidopsis bahia) Under Flow-through Conditions: FinalReport: Lab Project Number: 91-7-3845: 12442.0191.6110.515. Unpublished study prepared by Springborn Labs., Inc. 67 p.
42123503 2004913 Bettencourt, M. (1991) Thiophanate-methyl--Acute Toxicity to Sheepshead Minnow (Cyprindon variegatus) Under Flow-through Conditions: Final Report: Lab Project Number: 91-8-3872: 12442.0191.6111.505. Unpublished study prepared by Springborn Labs., Inc. 68 p.



### Fish Early Life Stage/Aquatic In vertebrate Life Cycle Study

### `

63 MRID DER-PDF Image Citation Reference

55934 2004846 Pg.3-4 Accession No.127270 Hashimoto, Y.; Noguchi, T.; Makita, T.; et al. (1970) Toxicological Evaluation of Thiophanate-methyl (I) Acute and Sub-acute Toxicity of Thiophanate-methyl. (Unpublished study received Feb 17, 1972 under unknown admin. no.; prepared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Agchem Div., King of Prussia, Pa.; CDL:127270-L)



### Seed Germination/Seedline Emergence and Vegetable Vigor Tier I

MRID DER-PDF Image Citation Reference

42123504 2004933 Hoberg, J. (1991) Thiopha nate-methyl-Determination of Effects on Seed Germination, Seedling Emerge nce and Vegetative Vigor of Ten Plant Species: Final Report: Lab Project Number: 91-7-3854: 12442.1190.6100.610. Unpublished study prepared by Springborn Labs., Inc. 154 p.
44237401 Supplemental Report Hoberg, J. (1997) Thiophanate-methyl--Determination of the Effects on Seed Germination, Seedling Emergence, and Vegetative Vigor of ten Plant Species: Supplemental Report: Lab Project Number: 91-7- 3854: 12442.1190.6100.610. Unpublished study prepared by Springborn Labs, Inc. 50 p.

44404101 2004936 Supplemental Report 2004956 pg3 Teixeira, D. (1997) Thiophanate-meth yl--Determination of Effects on Seed Germination and Seedling Emergence of Two Plant Species: Final Report (Supplement): Lab Project Number: 12442.0597.6247.610: 97-7-7033. Un published study prepared by Springborn Labs, Inc. 101 p.



### Seed germination/seedling emergence and vegetative vigor Tier II

MRID DER-PDF Image Citation Reference

42123504 2004933 2004935-

memo 2004956-

memo Hoberg, J. (1991) Thiophanate-methyl-Determination of Effects on Seed Germination, Seedling Emerge nce and Vegetative Vigor of Ten Plant Species: Final Report: Lab Project Number: 91-7-3854: 12442.1190.6100.610. Unpublished study prepared by Springborn Labs., Inc. 154 p.

44237401 Supplement al Report Hoberg, J. (1997) Thiophanate-methyl--Determination of the Effects on Seed Germination, Seedling Emergence, and Vegetative Vigor of ten Plant Species: Supplemental Report: Lab Project Number: 91-7- 3854: 12442.1190.6100.610. Unpublished study prepared by Springborn Labs, Inc. 50 p.

### `

64 44404101 2004936 Supplement al Report 2004956-

memo Teixeira, D. (1997) Thiophanate-meth yl--Determination of Effects on Seed Germination and Seedling Emergence of Two Plant Species: Final Report (Supplement): Lab Project Number: 12442.0597.6247.610: 97-7-7033. Un published study prepared by Springborn Labs, Inc. 101 p.



### Aquatic plant growth Tier I

MRID DER-PDF Image Citation Reference

42123505 2004953 Hoberg, J. (1991) Thiophanate-methyl--Toxicity to the Duckweed Lemna gibba G3: Final Report: Lab Project Number: 91-8-3878: 12442.1190.6101.410. Unpublished study prepared by Springborn Labs., Inc. 57 p.
42229801 2004973 Hoberg, J. (1992) Thiophanate-Methyl--Toxicity to the Freshwater Green Alga, Selenastrum capricornutum: Final Report: Lab Project Number: 91-9-3915: 12442.1190.6102.430. Unpub- lished study prepared by Springborn Laboratories, Inc. 68 p.
42229803 2004974 Hoberg, J. (1992) Thiophanate-methyl--Toxicity to the Marine Diatom, Skeletonema costatum: Lab Pr oject Number: 91-10-3939: 12442.1190.6102.450. Unpublished study prepared by Springborn Labs, Inc. 72
p.



### Aquatic plant growth Tier II

MRID DERPDF Image Citation Reference

42123505- repeated 2004953 2004935 Pg. 2 Hoberg, J. (1991) Thiophanate-methyl--Toxicity to the Duckweed Lemna gibba G3: Final Report: Lab Project Number: 91-8-3878: 12442.1190.6101.410. Unpublished study prepared by Springborn Labs., Inc. 57 p.
42229801 2004973 Hoberg, J. (1992) Thiophanate-Methyl--Toxicity to the Freshwater Green Alga, Selenastrum capricornutum: Final Report: Lab Project Number: 91- 9-3915: 12442.1190.6102.430. Unpub - lished study prepared by Springborn Laboratories, Inc. 68 p.
42229802 2004914 Hoberg, J. (1992) Thiophanate-Me thyl--Toxicity to the Freshwater Diatom Navicula Pelliculosa: Final Report: Lab Project Number: 91-10-3965: 12442. 1190. 6102. 440. Unpublished study prepared by Springborn Laboratories, Inc. 71 p.
42229803 2004974 Hoberg, J. (1992) Thiophanate-methyl--Toxicity to the Marine Diatom, Skeletonema costatum: Lab Project Number: 91-10-3939: 12442.1190.6102.450. Unpublished study prepared by Springborn Labs, Inc. 72 p.

42298102 2004954 2004915 Hoberg, J. (1992) Thiophanate-methyl--Toxicity to the Freshwater BlueGreen Alga Anabaena Flos-Aquae: Final Report: Lab Project Number:

### `

65 = memo 91-10-3963: 12442.1190.6102.420. Unpub- lished study prepared by Springborn Labs., Inc. 67 p.



### Honey bee acute contact

MRID DERPDF Image Citation Reference

40053209 2004931 Yamada, T.; Matsuda, M. (1986) Thiophanate-methyl - Honey Bee AcuteContact LD50: Study No. NISSO IE-6703M. Unpublished study prepared by Nippon Soda Co., Ltd., Biological Laboratory. 11 p.

92186015 Summary of MRID 40053209 Soeda, Y. (1990) Pennwalt Corporation Phase 3 Summary of MRID 40053209. Thiophanate-methyl - Honey Bee Acute Contact LD50: Project IE - 6703M. Prepared by Nippon Soda Co. LTD. 9 p.
80286 2004965 Pennwalt Corporation (1971) ?Toxicity Study of Topsin on Bees|. (Compilation; unpublished study received on unknown date under 4581- 287; CDL:051129-P)



### Honey bee residue on foliage

MRID DER-PDF Image Citation Reference

163178 Letter Johansen, C. (1971) Letter sent to Homer dated Sep 24, 1971: [Toxicity to honey bees of Topsin M insecticide treatments on cherries]. 3 p.



### Laboratory Mammal Toxicity

MRID DER-PDF Image Citation Reference

N/A 2078058 OFFICE OF PESTICIDE PROG RAMS HEALTH EFFECTS DIVISION

I TOX ONELINERS report Oct. 2000



### Non-Guideline Study to be considered

MRID DER-PDF Image Citation Reference

1823 Mallinckrodt, Incorporated (1975?) Foliage Plants: Phytotoxicity. (Unpublished study received Feb 4, 1975 under 372-46; CDL: 006409- F)

1824 Mallinckrodt, Incorporated (1975?) Co ntainer & Bedgrown Herbaceous Plants: Phytotoxicity. (Unpublis hed study received Feb 4, 1975 under 372-46; CDL:006409-J)

### `

66 1825 Mallinckrodt, Incorporated (1975? ) Container & Bedgrown Woody Plants: Phytotoxicity. (Unpublis hed study received Feb 4, 1975 under 372-46; CDL:006409-N)

36692 Summary Pennwalt Corporation (1972) Summary of Metabolism of Topsin M in Animals, Plants and Soil (As Presented in the Original Applica- tion of February 1972). (Unpublished study received Nov 18, 1974 under 5F1573; CDL:096461-N)

36694 Open Lit Mercer, R.T. (1971) Some studies on the systemic activity of the Thiophanate fungicides in plants. Pesticide Science 2(?/Sep- Oct):214- 218. (Also~In~unpublished submission received Nov 18, 1974 under 5F1573; submitted by Pennwalt Corp., Agchem Div., King of Prussia, Pa.; CDL:096461-Q)

57658 DER not located Pennwalt Corporation (19??) Acut e Toxicity on Metabolites of Thiophanate-methyl in Plants. (Unpublished study received Sep 5, 1972 under 2G1249; CDL:091777-S)

62533 Letter Mixon, W.W. (1972) Letter sent to J.L. Sandeno dated May 22, 1972: Algicidal properties of Topsin M. (Unpublished study received 1973 under 4581-EX-14; submitted by Pennwalt Corp., Philadel- phia, Pa.; CDL:210059-W)

62534 Letter 2004963 Mixon, W.W. (1971) Letter sent to Agchem File dated Oct 12, 1971: Fish toxicity of Topsin M--origi nating in food. (Unpublished study received 1973 under 4581-EX-14; CDL:210059-X)

42498801 Amend Wright, M. (1992) Amendment 1 to Executive Summary Final Report: ?Carbon 14|-Thiophanate Methyl Nature of the Residue in Laying Hens MRID No. 42472102: Lab Project Number: 38948: XBL 91021. Unpublished study prepared by ABC Labs, Inc. and XenoBiotic Labs, Inc. 20 p.

48033008 Open Lit Kojima, H.; Katsura, E.; Takeuchi, S.; et al. (2004) Screening for Estrogen and Androgen Receptor Acti vities in 200 Pesticides by In Vitro Reporter Gene Assays Using Chinese Hamster Ovary Cells. Environmental Health Perspectives 112(5): 524-531.

48033010 Open Lit Nishihara, T.; Nishikawa, J.; Kanayama, T.; et al. (2000) Estrogenic Activities of 517 Chemicals by Yeas t Two-Hybrid Assay. Journal of Health Science 46(4): 282-298.

ACC 070998 2004901 

### Residue Monitoring: water, soil and crayfish (Rice 

# - 0.7 lbs a.i./A)

57660 80286 2004903 Smith, R.G. (1971) Letter sent to Obren Keckemet dated Oct 11, 1971: Pencap and Topsin toxicity. (Unpubl ished study received Sep 5, 1972 under 2G1249; submitted by Pennwalt Corp., Philadel- phia, Pa.; CDL:091777-U)
62545 2004904 Pennwalt Corporation (1972) Re sidues of Topsin M in Fish Tissue. (Unpublished study received 1973 under 4581-EX-14; CDL: 210059- AO)

81597 2004906- registrant summary Pennwalt Corporation (1978) Fish and Wildlife Safety. Summary of study 099011-R. (Unpublished study received Sep 27, 1979 under 4581-340; CDL:099011-Q)

### `

67 N/A 2004921 Eco Data Summary table
62514 2004923 Summary of fish data already reviewed
2004935 1993 Memo on multiple studies
39705 2004941 Summary of multiple studies by registrant
62516 2004943 Summary of multiple studies by registrant
69599 2004944 Summary of multiple studies by registrant
106091 2004968 Summary of multiple studies by registrant

### `

68 

## 128872 Carbedazim (MBC) Eco Effects Bibliography

Revisited 07/25/13 Note: MBC is a major degradate of thiophanate methyl and benomyl

Avian Single Dose Oral Toxicity

MRID DER-PDF Image Citation Reference

154667 2048625 2048626= contract draft 2048649-memo Beavers, J. (1985) An Acute Oral Toxicity Study in the Bobwhite with H-15,607: Final Report: Project No. 112-163. Unpublished study prepared by Wildlife International Ltd. 15 p.

43129604 2048641 Grimes, J.; Hoxter, K.; J aber, M. (1990) Methyl Benzimidazole Carbamate (LX1132-01): An Acute Oral Toxicity Study with the Bobwhite: Lab Project Number: 190-155. Unpublished study prepared by Wildlife International Ltd. 33 p.



### Avian Dietary Toxicity

MRID DER-PDF Image Citation Reference

154688 2048627 Fink, R. (1974) Eight-day Dietar y LC50 - Bobwhite Quail H-9129: Re- port No.665-74: Final Re port: Project No. 112-103. Unpublished study prepared by Truslow Farms Incorporated. 8 p.
154689 2048628 Fink, R. (1975) Eight-day Dietary LC50 - Mallard Ducks H-9129: Re- port No. 108-75: Final Report: Project No. 112-104. Unpublished study prepared by Truslow Farms Incorporated. 10 p.

165113 DER not located IBT study Fletcher, D. (1973) Report to E. I. du Pont de Nemours and Co.: 8- Day Dietary LC50 Study with H-7310; MR-1747 in Mallard Ducklings IBT No. 651-03198. Unpublished study prepared by Industrial Bio-Test Laboratories, Inc. 14 p.

165114 DER not located IBT study Fletcher, D. (1973) Report to E. I. du Pont de Nemours and Co. 8- Day Dietary LC50 Study with H-7310; MR-1747 in Bobwhite Quail: IBT No. 651-03203. Unpublished stud y prepared by Industrial BioTest Laboratories, Inc. 14 p.
43129605 2048642 |Grimes, J.; Hoxter, K.; J aber, M. (1990) Methyl Benzimidazole Carbamate (LX1132-01): A Dietary LC50 Study with the Bobwhite: Lab Project Number: 190-154. Unpublished study prepared by Wildlife International Ltd. 33 p.
43205501 2048645 Ebert, E.; Leist, K. (1987) 8-Day Dietary LC50 Test in the Mallard Duck (Anas platyrhynchos) with BCM Technical: Lab Project Number: 87.0707: A36805. Unpublished study prepared by Hoechst Aktiengesellschaft. 31 p.

### `

69 Acute Toxicity to Freshwater Fish

MRID DER-PDF Image Citation Reference

154690 2048629 Heinemann, J. (1971) Acute Static Fish Toxicity Study - Freshwater H-6881 (MR-581): Report No. 150-71: Final Report: Project No. 201-255. Unpublished study prepared by Hazleton Laboratories. 12 p.
154691 2048630 Wetzel, J. (1984) 96-Hour LC50 to Bluegill Sunfish: Report No. 401- 84: MR No. 4581-206. Unpublished study prepared by E. I. du Pont de Nemours & Co., Inc. 6 p.

165115 DER not loca ted Sleight, B. (1972) Bioassay R eport ... Acute Toxicity of MR-1566,H-7310 to Bluegill (Lepomis macrochirus) and Rainbow Trout (Salmo gairdneri): HLO 455-72: MR-1566-1. Unpublished study prepared by Bionomics, Inc. 8 p.
43129606 2048643 Bowman, J. (1989) Acute Flow-Through Toxicity of LX1132-01 (Methyl Benzimidazole Carbamat e) to Rainbow Trout (Salmo gairdneri): Lab Project Number: 38100. Unpublished study prepared by Analytical Bio-Chemistry Lab. Inc. 126 p.
43129607 2048644 Bowman, J. (1989) Acute Flow-Through Toxicity of LX1132-01 (Methyl Benzimidazole Carbamate) to Bluegill (Lepomis macrochirus): Lab Project Number: 38099. Unpublished study prepared by Analytical Bio-Chemistry Lab., Inc. 114 p.
40098001 2048637 EFED Review of Mayer and Ellersieck Data for Catfish, Rainbow trout and Fathead minnow



### Acute Toxicity to Freshwater Invertebrates

MRID DER-PDF Image Citation Reference

154467 2048623 2048624 Hall, C. (1985) Static Acute 48- hour EC50 of Carbendazim (INE965- 231) and Carbendiam-HCL (INU-810-11) to Daphnia magna: Report No. 156-85. Unpublished study prepared by DuPont Haskell Labor- atory. 10 p.
154693 2048631 Canton, J. (1976) The toxi city of Benomyl, Thiophanate-methyl, and BCM to four freshwater organisms. Bulletin of Environmental Contamination & Toxicology 16(2):214-218.

42414201 2048640 2048639= study report Baer, K. (1992) Static, Acut e, 48-hour EC50 of DPX-E965-299 (Carbendazim, MBC) to Daphnia Magna: Lab Project Number: 4581-929: 185-92. Unpu blished study prepared by E.I. du Pont de Nemours and Co. 25 p.
43205502 2048646 Fischer, R. (1988) The effect of Carbendazim--Substance, Technical (Identification Code: HOE 017411 of ZD99 0010) to Daphnia magna (Waterflea) in a Static-Acute Toxicity Test (Method

### `

70 OECD): Lab Project Number: OEK88/091E: A39285. Unpublished study prepared by Hoechs t Aktiengesellschaft. 41 p.



### Acute Toxicity to Estu arine/Marine Organisms

MRID DER-PDF Image Citation Reference

40964701 2048634 2048653- memo Boeri, R. (1988) Static Acute Toxi city of Carbendazim Technical tothe Mysid, Mysidopsis bahia: Enseco Marblehead Laboratory Project DP1688. Unpublished study prepared by Enseco Inc. 22 p.
40975001 2048635 Boeri, R. (1988) Static Acut e Toxicity of Carbendazim Technical to the Sheepshead Minnow, Cyprinodon variegatus: Proj. ID DP1588. Unpublished study prepared by Enseco Inc. 21 p.
40975002 2048636 Boeri, R. (1988) Flow Through Acute Toxicity of Carbendazim Techni- cal to the Eastern Oyster, Crassostrea virginica: Proj. ID DP2688. Unpublished study prepared by Enseco Inc. 22 p.



### Fish Early Life Stage/Aquatic In vertebrate Life Cycle Study

MRID DER-PDF Image Citation Reference

42529401 2048640 Baer, K. (1992) Chronic Toxicity of DPX-E965-299 (Carbendazim, MBC) to Daphnia Magna: Lab Project Number: 4581-929: 599-92. Unpublished study prepared by E.I. du Pont de Nemours and Co. 422 p.

42723701 benomyl 2016984 Ward, T.; Boeri, R. (1992) Life-cycle Toxicity of DPX-E965-299 (Carbendazim, MBC) to the Mysid, Mysidopsis bahia: Lab Project Number: 4581-929: 806-92: 97-DU. Unpublished study prepared by T.R. Wilbury Labs, Inc. 299 p.
43011801 2016995 Baer, K. (1993) Early Life-Stage Toxicity Test on DPX-E965-299 (Carbendazim, MBC) with Rainbow Trout (Oncorhynchus mykiss): Lab Project Number: 596/93: 9598/001. Unpublished study prepared by E. I. du Pont de Nemours and Co. Haskell Lab. for Toxicology. 665 p.
43872801 2017018 Rhodes, J.; Hurshman, B.; Leak, T. (1995) Early Life-Stage Toxicity of Benomyl (As Car bendazim, DPX-E965-299) to the Channel Catfish (Ictalurus punctatus) Under Flow-Through Conditions: Amended Report No. 1: Lab Project Number: 236-95: 45352: HLO 236-95. Unpublished study prepared by ABC Labs, Inc. 780 p.
Not given 2048638 Hutton, D.G. 1986 Chronic toxicity to Daphnia of carbamic acid, 1H-benzimidazol-2-yl, methyl ester

### `

71 Aquatic plant growth

MRID DER-PDF Image Citation Reference

43913601 2017020 in 099100 folder Flusilazole + Carbendazim Thompson, S. (1995) DPX-N7872-236: Influence on Growth and Reproduction of Selenastrum capricornutum: Lab Project Number: 112A-137: AMR 3343-95. Unpublished study prepared by Wildlife International Ltd. and DuPont's Haskell Lab for Toxicology and Industrial Medicine. 49 p. Check PC Code 128835



### Honey bee acute contact

MRID DER-PDF Image Citation Reference

154695 2048633 Meade, A. (1984) Acute Cont act LD50 Study in Honey Bees (Apis me- llifera L.) with INE965-212: Project No. ABM-84-5. Unpublished study prepared by E. I. du Pont de Nemours & Co. 6 p.



### Non-Guideline Study Selections to be considered

MRID DER-PDF Image Citation Reference

57658 Pennwalt Corporation (19??) Ac ute Toxicity on Metabolites of Thiophanate-methyl in Plants. (Unpublished study received Sep 5, 1972 under 2G1249; CDL:091777-S)

37195 Open lit Clemons, G.P.; Sisler, H.D. ( 1969) Formation of fungitoxic derivative from Benlate. Phytopathology 59(?/May):705-706. (Also~In~ unpublished submission received Jan 23, 1970 under 0G0936; sub- mitted by E.I. du Pont de Nemours & Co., Inc., Wilmington, Del.; CDL:091599-N)
154692 2048637 Columbia National Fishery Research Laboratory (1984) Summary of Acute Toxicity: Methyl 2-benzimidazolecarbamate. Unpublished study. 4 p.
154694 Open lit- check Benomyl Stringer, A.; Wright, M. (1973) The effect of Benomyl and related compounds on Lumbricus terrestris and other earthworms. Pestic. Sci. 4:165-170.

42687002 DER not located- HED? Reynolds, V.; Sarrif, A. (1993) A Review of the Genetic Toxicity Studies on Benomyl and Carbendazim: Lab Project Number: HLR 1-93. Unpublished study prepared by DuPont's Haskell Laboratory for Toxicology and Industrial Medicine. 69 p.

47807011 DER not located Elancolan= Trifluralin + Carbendazim Hanisch, A. (1994) Effects of Elancolan Regarding Reproduction and Development of Eisenia fetida: Laboratory Test: Final Report. Project Number: RE402, RE402800/DOC. Unpublished study prepared by Institut fuer Pflanzenschutz. 29 p.

### `

72 48033008 Open lit Kojima, H.; Katsura, E.; Takeuchi, S.; et al. (2004) Screening for Estrogen and Androgen Receptor Acti vities in 200 Pesticides by In Vitro Reporter Gene Assays Using Chinese Hamster Ovary Cells. Environmental Health Perspectives 112(5): 524-531.

48033010 Open Lit Nishihara, T.; Nishikawa, J.; Kanayama, T.; et al. (2000) Estrogenic Activities of 517 Chemicals by Yeast Two-Hybrid Assay. Journal of Health Science 46(4): 282-298.
154694 2048632 Stringer, A.; Wright, M. (1973) The effect of Benomyl and related compounds on Lumbricus terrestris and other earthworms. Pestic. Sci. 4:165-170.
97616 compilation E.I. du Pont de Nemour s & Company, Incorporated (1972) Residue Studies--Fish: Benomyl: Methyl 2-Benzimidazolecarbamate (MBC): 2-Aminobenzimidazole (2-AB). (Compilation; unpublished study received Jan 18, 1972 under 352-354; CDL:131800-A)

### `

73 

## 102001 Thiophanate-methyl Fate Chemistry Bibliography

Revised 05/17/12 161-1 Hydrolysis

MRID DER-PDF Image Citation Reference

36690 or 120582 DER not located Kosaka, S. (1973) Alkaline Hydrolysis of Thiophanate-methyl and the Hydrolyzed Products. (Unpublished study received Nov 18, 1974 under 5F1573; prepared by Nippon Soda Co., Ltd., submitted by Pennwalt Corp., Agchem Div., King of Pr ussia, Pa.; CDL:096461-L)

40095507 2004820 2007739 Nomura, O. (1986) Thiophanate-meth yl: Hydrolysis [Study]: Laboratory Project ID. EC-67. Unpublished study prepared by Nippon Soda Co., Ltd. 44 p.

92186016 2004820 – registrant summary Soeda, Y. (1990) Pennwalt Corporation Phase 3 Summary of MRID 40095507. Thiophanate-methyl - Hydrolysis: Project EC-67. Prepared by Nippon Soda Co. LTD. 12 p.

39706 2063503- draft Pennwalt Corporation (1980) Thiopha nate-methyl--Half-Life Study in Water: Project No. WT-9-80. (Unpublished study received Jul 11, 1980 under 4581-322; CDL:099510-G)
62540 2063511 Pennwalt Corporation (1972) De gradation of Topsin M in Water at pH 10 and Not Kept in Sunlight. (Unpublished study received 1973 under 4581-EX-14; CDL:210059-AH)

40053210 DER not located Soeda, Y.; Shiotani, H. (1986) Thiophanate-methyl - Volatility [from Water]: Study No. NISSO EC-61. Unpublished study prepared by Soda Co., Ltd., Environmental Toxicology Laboratory. 9 p.



### 161-2 Photodegradation-water

MRID DER-PDF Image Citation Reference

41482806 2004840 Soeda, Y.; Shiotani, H. (1 987) Thiophanate-methyl Photodegradation in Water: Lab Study No.: NISSO EC-74. Unpublished study pre- pared by Nippon Soda Co., Ltd., Environmental Toxicology Laboratory. 35 p.

92186017 2004840 Registrant Summary Soeda, Y. (1990) Pennwalt Corporation Phase 3 Summary of MRID 41482806. Thiophanate-methyl - Phot odegradation in water: Project EC-74. Prepared by Nippon Soda Co. Ltd. 14 p.

36697 2063503 Pennwalt Corporation (1972) Photod ecomposition of Topsin M in Water. (Unpublished study received Nov 18, 1974 under 5F1573; CDL:096461-T)

39707 2063503 Pennwalt Corporation (1972) Photod ecomposition of Topsin M in Water. (Unpublished study received Jul 11, 1980 under 4581-322; CDL:099510-H)

120585 Open lit Buchenauer, H.; Edgington, L.; Grossman, F. (1973) Photochemical transformation of thiophanate-methyl and thiophanate to alkyl

### `

74 benzimidazol-Z-yl carbamates. Pestic. Sci. 4:343-348. (Also In unpublished submission received Jan 15, 1975 under 4581-EX-17; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:094717-B)

120625 Summary Agchem (1978) Photodegradation of 14C Thiophanate-Methyl in Water and Soils. (Compilation; unpublished study received Sep 27, 1979 under 4581-340; CDL:099006-F)



### 161-3 Photodegradation-soil

MRID DER-PDF Image Citation Reference

35223 or 49663 or 73577 Fate summary 2063518 Pennwalt Corporation (19??) ?Degra dation of Topsin M under UV Light on Glass and on Soil|. (Unpublished study received Sep 4, 1972 under 2G1249; CDL:091775-C)

35226 Fate summary 2063518 Noguchi, T.; Kosaka, S.; Soeda, Y.; et al. (1971) ?Studies on the Biotransformation of Thiophanate-methyl in Animal, Plant and Soil|. (Unpublished study received Sep 4, 1972 under 2G1249; prepared by Nippon Soda Co., Ltd., submitted by Pennwalt Corp., Agchem Div., King of Prussia, Pa.; CDL:091775-F)

72939 Fate summary 2063518 Pennwalt Corporation (1972) Photodec omposition of Topsin M in Five Soils. (Unpublished study received Feb 9, 1973 under 4581-EX- 14; CDL:127285-E)
39703 2063501 Pennwalt Corporation (1 980) Thiophanate-methyl-- Soil Photodegradation: Project No. WT-10-80. (Unpublished study received Jul 11, 1980 under 4581-322; CDL:099510-C)

53448 or 62527 Fate summary 2063518 Pennwalt Corporation (19??) Degr adation of Topsin M on Soil Exposed to UV Light. (Unpublished study rece ived Feb 17, 1972 under unknown admin. no.; CDL:127269-E)
62522 Nippon Soda Company, Limited (19??) Studies on the Stability of Thiophanates under Non-biological Conditions. (Unpublished study received 1973 under 4581-EX-14; submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:210059-J)
62528 2063507 Soeda, Y.; Kosaka, S.; Noguchi, T. (1971?) Fate of Thiophanate- methyl Fungicide and Its Metabolites on Plant Leaves and Glass Plates. (Unpublished study received 1973 under 4581-EX-14; pre- pared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:210059-Q)

66570 DER not located Nippon Soda Company, Limited (19??) ph Dependance of Stability of Thiophanates. (Unpublished study received on unknown date under 4581-278; submitted by Pennwalt Corp., Philadelphia, Pa.; CDL: 227184-D)
88446 2004967 Pennwalt Corporation (1972) ?The Fate of Topsin E and Topsin M in Soil|. Summary of studies 007463-D through 007463-K, 007463-M through 007463-R, 007453-V, 007463-X, 007463-AA and 007463-AC through 007463-AF. (Unpublished study, including letter dated Dec 6, 1972 from J.L. Sandeno to E.J. Bowles, received Feb 9, 1973 under

### `

75 4581-288; CDL:007463-C)

88447 62524 2063505 Noguchi, T.; Kosaka, S.; Ohkuma, K.; et al. (1971) Studies on the Biotransformation of Thiophanate-methyl in Animal, Plant and Soil (Part II). (unpublished study received Feb 9, 1973 under 4581-288; prepared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:007463-F)
88448 2063509 Pennwalt Corporation (1971) ?Degradation of Topsin E and Topsin M on Soil Exposed to UV Light|. (Compilati on; unpublished study received Feb 9, 1973 under 4581-288; CDL:007463-H)

97264 DER not located compilation W.A. Cleary Corporation (1970) ?Thiophanates: Chemical Study|. (Compilation; unpublished study received on unknown date under 1001- 50; CDL:022093-B)

97923 DER not located Pennwalt Corporation (19??) Studies on the Stability of Thiophan- ates under Non-biological Conditions. (Unpu blished study re- ceived Feb 9, 1973 under 4581-288; CDL:007463-D)
117873 2063517 Pennwalt Corp. (1973) Results of Tests on the Amount of ?Topsin M| Residue Remaining, Including a Description of the Analytical Method Used. (Compilation; unpublished st udy received Sep 7, 1972 under 2G1249; CDL:091779-I)

120563 Results of Tests Agchem (1973) Results of Tests on the Amount of Residue Remaining, Including a Description of the Analytical Method Used: ?Topsin M|. (Compilation; unpublished study received Feb 9, 1973 under 4581-287; CDL:007461-A)

120617 DER not located Agchem (1973) ?Chemical Study of Topsin M|. (Compilation; unpublished study received 1973 under 5F1573; CDL:098424-A)

120647 DER not located Agchem Div., Penwalt Corp. (1972) ?Environmental Study: Topsin Formulations|. Unpublished compilation. 426 p.
41482807 2004880 Soeda, Y.; Shiotani, H. (1987) Thiophanate-methyl Photodegradation on Soil: Lab Study No.: NISSO EC-75. Unpublished study prepared by Nippon Soda Co., Ltd., Environmental Toxicology Laboratory. 24 p.

92186018 2004880 Summary of MRID 41482807 Soeda, Y. (1990) Pennwalt Corporation Phase 3 Summary of MRID41482807. Thiophanate-methyl - Photodegradation on Soil: Project EC75. Prepared by Nippon Soda Co. LTD. 14 p.

62537 2063499 Pennwalt Corporation (1972) Degradation and Photodecomposition of Topsin M in Five Soils. (Unpublished study received 1973 under 4581- EX-14; CDL:210059-AC)

42094601 Response to MRID 41482807 Shiotani, H. (1991) Thiophanate-methyl: Photodegradation on Soil : Comments to EPA Phase 4 Response to MRID 41482807 : Lab Project Number: EC-336. Unpublished study pre pared by Nippon Soda Co., Ltd. 13 p.



### 162-1 Aerobic soil metabolism

MRID DER-PDF Image Citation Reference

### `

76 35226 2063505 Noguchi, T.; Kosaka, S.; Soeda, Y.; et al. (1971) ?Studies on the Biotransformation of Thiophanate-methyl in Animal, Plant and Soil|. (Unpublished study received Sep 4, 1972 under 2G1249; prepared by Nippon Soda Co., Ltd., submitted by Pennwalt Corp., Agchem Div., King of Prussia, Pa.; CDL:091775-F)

39704 2063502 Pennwalt Corporation (1980) Anaerobic Soil Metabolism Using Thiophanate-methyl: Project No. WT-7-78. Includes method entitled: A simple apparatus and quantitative method for determining the persistence of pesticides in soil. (Unpublished study including published data, received Jul 11, 1980 under 4581-322; CDL: 099510-D)
62525 2063506 Kosaka, S.; Soeda, Y.; Hagiwara, S.; et al. (1972) Influences of Thiophanate-methyl to Soil Microorganisms and Fate of the Chemi- cal in Soil. (Unpublished study received 1973 under 4581-EX-14; prepared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:210059-N)

106085 2004779 2007730 2063511 Agchem (1982) Aerobic Soil Metabolism Using Thiophanate-methyl: Project No. WT-7-78. (Unpublished study received Jul 21, 1982 under 4581-322; CDL:070992-B)
62537 2063699 Pennwalt Corporation (1972) Degradation and Photodecomposition of Topsin M in Five Soils. (Unpublished study received 1973 under 4581- EX-14; CDL:210059-AC)



### 162-2 Anaerobic soil metabolism

MRID Citation Reference



### 162-3 Anaerobic aquatic metab.

MRID DER-PDF Image Citation Reference

40061501 2007731 2004860 Dykeman, R. (1986) Thiophanate-methyl - Anaerobic Aquatic Metabolism: Amended Final Report: Laboratory Project Identification WT-1- 82. Unpublished study prepared by Pennwalt Corp., Agchem Div. 127 p.

92186019 2004660 Summary Wright, J. (1990) Pennwalt Corporation Phase 3 Summary of MRID 40061501. Thiophanate-Methyl Anaerobic Aquatic Metabolism: Project WT-1-82. Prepared by Pennwalt Corporation. 16 p.
40061500 Pennwalt Corp. (1987) Anaerobic Aquatic Metabolism: Thiophanate Methyl. Compilation of 1 study.

133502 2007731 Pg. 3 Agchem (1983) Anaerobic Aquatic Metabolism of Thionphanatemethyl: Project No. WT-1-82. (Unpublished study received Dec 15, 1983 under 4581-322; CDL:251979-C)

### `

77 162-4 Aerobic aquatic metab.

MRID DER-PDF Image Citation Reference

165361 DER not located Pennwalt Corp. (1982) Aerobic Aquatic Metabolism of Thiophanatemethyl: Project No. WT-8-82. Unpublished study. 23 p.
45621401 2003609 Volkl, S. (2001) (Carbon 14)-Thiophanate-Methyl: Route and Rate of Degradation in Aerobic Aquatic Systems: Lab Project Number: 735063. Unpublished study prepared by RCC Ltd. 168 p. {OPPTS 835.3180}
45620001 2003607 Ritter, A. 1988. Degradation of carbendazim (HOE 01741 1) in two aerobic aquatic systems. Unpublished study performed by RCC Umweltchemie AG, Switzerland; sponsored by Ho echst Aktiengesell schaft, Frankfurt, Germany; and submitted by Cerexagri, Inc., King of Prussia, PA. RCC Project No.: 088132. Experiment initiation July 23, 1987, and completion December 24, 1987 (p. 7). Final report issued March 2 1, 1988.



### 163-1 Leach/adsorp/desorption

MRID DER-PDF Image Citation Reference

36695 or 62541 or 2063508 - draft Pennwalt Corporation (1972) Vertical Movement of Topsin M. (Unpublished study received Nov 18, 1974 under 5F1573; CDL:096461-S)

39702 2063500 draft Pennwalt Corporation (1978) Adsorption and Desorption of 14C Thiophanate-methyl in Soils: Project No. WT-4-78. (Unpublished study received Jul 11, 1980 under 4581-322; CDL:099510-B)

49662 120563 2063613 Pennwalt Corporation (1973) Residues in Soil--Topsin M and Top- sin E. (Unpublished study received Feb 9, 1973 under 4581-EX- 14; CDL:127285-C)

53449 121072 2063516 Noguchi, T.; Kosaka, S.; Soeda, Y.; et al. (1970) Studies on the Biotransformation of Thiophanate-methyl in Animal and Plant ( Part I). (Unpublished study received Feb 17, 1972 under un- known admin. no.; prepared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:127269-G)

53450 62524 or 88447 2063505 Noguchi, T.; Kosaka, S.; Ohkuma, K.; et al. (1971) Studies on the Biotransformation of Thiophanate-methyl in Animal, Plant and Soil (Part II). (Unpublished study received Feb 17, 1972 under unknown admin. no.; prepared by Nippon Soda Co., Ltd., Japan, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:127269-H)

62530 DER not located Pennwalt Corporation (1971) Soil- -Vertical Movement--Topsin M. (Unpublished study received 1973 under 4581-EX-14; CDL:210059-S)

88450 2063510- draft Pennwalt Corporation (1971) ?Vertical Movement of Topsin E and Topsin M in Soil|. (Compilation; unpublished study received Feb 9, 1973 under 4581-288; CDL:007463-J)

### `

78 120563 Results of Tests Agchem (1973) Results of Tests on the Amount of Residue Remaining, Including a Descripti on of the Analytical Method Used: ?Topsin M|. (Compilation; unpublished study received Feb 9, 1973 under 4581-287; CDL:007461-A)

120623 DER not located Agchem (1978) A 14C Thiophanate-methyl Soil Binding Study (Applicable to Adsorption/Desorption). (Unpublished study received Sep 27, 1979 under 4581-340; CDL:099006-C)

120627 120688 2063515 Nisso Institute for Life Science (1972) Fate of Thiophanate-methyl in Soil. (Unpublished study received Sep 27, 1979 under 4581- 340; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:099006-H)
120630 2063514 Agchem (1972) Vertical Movement--Topsin M Fungicide 70% W.P.: Woodburn Silty Clay Loam. (Unpublished study received Sep 27, 1979 under 4581-340; CDL:099006-K)

120633 DER not located Agchem (1978) Adsorption and Desorption of 14C Thiophanatemethyl in Soils: Project No. WT-4-78. (Unpublished study received Sep 27, 1979 under 4581-340; CDL:099006-N)
120647 Compilation Agchem Div., Penwalt Corp. (1972) ?Environmental Study: Topsin For- mulations|. Unpublished compilation. 426 p.
120655 MBC study Van Wambeke, E.; Van Assc he, C. (1975?) The Importance of Some Factors Involved with the Persistence of Carbendazim (MBC) in Soil

. (Unpublished study received Nov 8, 1977 under 4581-322; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:232170-B)

41482808 DER not located Soeda, Y.; Shiotani, H. (1987) Thiophanate-methyl: Soil ColumnLeaching: Lab Study No.: NISSO EC-90. Unpublished study prepared by Nippon Soda Co., Ltd., Environmental Toxicology Laboratory. 32 p.
41560902 2004821 Soeda, Y.; Shiotani, H. (1987) Thiophanate-Methyl: Batch Equilibrium (Adsorption/Desorption): Lab Project Number: NISSO EC-89. Unpublished study prepared by Nippon Soda Co., Ltd.; Environmental Toxicology Lab. 36 p.
42351001 2004881 Shiotani, H. (1992) Thiophanate-methyl--Batch Equilibrum(Adsorption/Desorption on Soild): Lab Project Number: NISSO EC362. Unpublished study prepared by Nippon Soda Co., Ltd., Envir. Tox. Lab. 106 p.



### 163-2 Volatility - lab

MRID DERPDF Image Citation Reference

42380101 2004822 Shiotani, H. (1992) Thiophanate- methyl--Laboratory Volatility from Soil: Lab Project Number: NISSO EC-381: 163-2. Unpub- lished study prepared by Environ. Tox. Lab, NIPPON SODA., Ltd. 57 p.



### 164-1 Terrestrial field dissipation

### `

79 MRID DER-PDF Image Citation Reference

37935 DER not located Miller, H.J. (1973) Topsin Persistence in Soil--Greenhouse Test-- Wyndmoor. (Unpublished study received Nov 18, 1974 under 5F1573; submitted by Pennwalt Corp., Agchem Div., King of Prus- sia, Pa.; CDL:096461-P)

39708 DER notlocatedMBC study Landskov, A.O.; Lindaberry, H.L. (1972) ?Calculations of Residues of Topsin M and MBC in Run-off Water|. (Unpublished study re- ceived Jul 11, 1980 under 4581-322; submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:099510-I)

49661 DER not located Pennwalt Corporation (1973) Residues in Grass--Topsin M and Top- sin E. (Unpublished study received Feb 9, 1973 under 4581-EX- 14; CDL:127285-B)

49662 DER not located Pennwalt Corporation (1973) Residues in Soil--Topsin M and Top- sin E. (Unpublished study received Feb 9, 1973 under 4581-EX- 14; CDL:127285-C)

53439 DER not located Pennwalt Corporation (1972) Moveme nt of Pencap M Out of Treated Areas. (Compilation; unpublished study received Jan 8, 1974 under 4581-EX-16; CDL:127286-D)

61203 DER not located Lindaberry, H.L.; Landskov, A.O. ( 1972) ?Residues of Penncap-M in soil|. (Unpublished study received Sep 29, 1980 under 4581-292; submitted by Pennwalt Corp., Philadelphia, Pa.; CDL:243398-E)

62543 DER not located Pennwalt Corporation (1971) Residues of Topsin M versus Benlate-- Soil. (Unpublished study received 1973 under 4581-EX-14; CDL: 210059-AM)

62544 DER not located Lindaberry, H.L. (1972) Residues of Topsin M and MBC in Run-Off Water. (Unpublished study received 1973 under 4581-EX-14; CDL: 210059- AN)

72378 DER not located Pennwalt Corporation (1972) ?Soil and Water Run Off Tests for Pencap M versus Methyl Parathion E.C.|. (Compilation; unpub- lished study received Dec 4, 1980 under 4581-292; CDL:244308-E)
102320 compilation Pennwalt Corp. (1972) ?Run-off Studies on Pencap M and Topsin M|. (Compilation; unpublished study received on unknown date under 3F1361; CDL:093631-L)

106086 2063512 Agchem (1981) Topsin M Fungicide--Field Dissipation: Project No. WT-1- 81. (Unpublished study received Jul 21, 1982 under 4581-322; CDL:070992-C)

106087 DER not located Agchem (1981) Residues in Water, Soil, and Crayfish: ?Topsin M|. (Unpublished study received Jul 21, 1982 under 4581-322; CDL: 070992- D)

106094 DER not located Agchem (1981) ?Residues of Topsin M in Soil and Other Subjects|. (Compilation; unpublished study received Jul 21, 1982 under 4581-322;

### `

80 CDL:070998-C)

117873 Results of Tests Pennwalt Corp. (1973) Results of Te sts on the Amount of ?Topsin M| Residue Remaining, Including a Description of the Analytical Method Used. (Compilation; unpublished st udy received Sep 7, 1972 under 2G1249; CDL:091779-I)

120563 Results of Tests Agchem (1973) Results of Tests on the Amount of Residue Remaining, Including a Description of the Analytical Method Used: ?Topsin M|. (Compilation; unpublished study received Feb 9, 1973 under 4581-287; CDL:007461-A)

120569 DER not located Caldwell, R. (1972) Thiophanate (Met hyl, Ethyl) Persistence Study. (Unpublished study received Sep 7, 1971 under 1001-50; prepared by Univ. of Florida, Agricultural Resear ch Center, submitted by W.A. Cleary Corp., Somerset, NJ; CDL:022101-A)

120580 The Results of Tests Agchem (1974) The Results of Tests on the Amount of Residue Remaining, Including a Description of the Analytical Methods Used: ?Topsin M|. (Compilation; unpublished study received Nov 18, 1974 under 5F1573; CDL:094316-A)
120583 Letter Miller, H. (1973) Letter sent to O. Keckemet dated Apr 27, 1973: Topsin persistence in soil--greenhouse test --Wyndmoor. (Unpub- lished study received Sep 1, 1973 under 2G1249; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:094577-C)
120586 Open Lit Fleeker, J.; Lacy, H.; Schu ltz, I.; et al. (1974) Persistence and metabolism of thiophanate-mythyl in soil. J. Agr. Food Chem. 22(4):592- 595. (Also In unpublished submission received Jan 15, 1975 under 4581- EX-17; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:094717-C)

120628 120688 2063515 Nisso Institute for Life Science (1972) Field Studies on Per- sistence and Fate of Thiophanate-methyl in Soil. (Unpublished study received Sep 27, 1979 under 4581-340; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:099006-I)

120632 DER not located Kosaka, S.; Fujino, A.; Tanoue, T. (1974) Uptake by Radish and Fate of Thiophanate-methyl in Soil. (Unpub lished study re- ceived Sep 27, 1979 under 4581-340; prepared by Nippon Soda Co., Ltd., Japan, submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:099006-M)

120637 DER not located W.A. Cleary Corp. (1972) ?Topsin Residues in Soil and Grass|. (Compilation; unpublished study received Feb 7, 1973 under 1001-50; CDL:120356-A)
41930101 2004842 Dykeman, R. (1991) Field Dissipation Study for Thiophanate-Methyl Applied to an Apple Orchard: Final Report: Lab Project Number: WT-86- C-25:6012-188: 87-001. Unpublished study prepared by Hazleton Labs America in coop. with ACDS Corp. 469 p.
41930102 2004862 Dykeman, R. (1991) Field Dissipation Study for Thiophanate-Methyl Applied to a Dry Bean Crop: Final Report: Lab Project Number: WT 86- C-27: 6012-186: 87029. Unpublished study prepared by Hazle- ton Labs America in coop. with Hulst Re search Farm Services. 439 p.
43433701 2004882 Wright, J. (1994) Terrestrial Dissipation of Topsin-M Applied to a Lettuce Crop: Lab Project Number: BR-92-30: ML92-0299-ATO: 92.135.

### `

81 Unpublished study prepared by Plant Sciences, Inc. and Morse Labs, Inc. 827 p.
43545801 Supplemen tal Report

see 43433701 Wright, J. (1995) Terrestrial Dissipation of Topsin-M Applied to a LettuceCrop: Supplemental Report: Lab Project Numbers: BR-92-30: ABR149570-E: 132853. Unpublished study prepared by Plant Sciences, Inc.; Morse Labs, Inc. 8 p.

88451 DER not located Pennwalt Corporation (1973) Residues of Topsin M and Topsin E in Grass and Soil (Turf Field Plots). (Unpublished study received Feb 9, 1973 under 4581-288; CDL:007463-K)
88452 See below Pennwalt Corporation (1972) Run-off Water Residues--Topsin M. (Unpublished study received Feb 9, 1973 under 4581-288; CDL: 007463- M)

62532 120563 2063513 Pennwalt Corporation (1972) Run- Off Water Residues--Topsin M. (Unpublished study received 1973 under 4581-EX-14; CDL:210059-V)

46788 DER not located Pennwalt Corporation ( 1971) Run-Off Water Residues--Topsin M. (Unpublished study received Feb 17, 1972 under unknown admin. no.; CDL:127269-F)



### 165-5 Fish Bioaccumulation

MRID DER-PDF Image Citation Reference

133504 DER not located Agchem (1983) Bluegill Bioaccumulation Study--Thiophanate-methyl: Project No. WT-10-82. (Unpublished study received Dec 15, 1983 under 4581-322; CDL:251979-E)

62545 DER not located Pennwalt Corporation (1972) Residues of Topsin M in Fish Tissue. (Unpublished study received 1973 under 4581-EX-14; CDL: 210059- AO)

120570 DER not located W.A. Cleary Corp. (1972) Residues of Topsin M in Fish Tissue. (Unpublished study received Sep 7, 1971 under 1001-50; CDL: 022101-B)



### ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^



## 128872 Carbendazim Fate Chemistry Bibliography

Revisited 07/25/13 Note to reviewer- Many benomyl studies foun d in this folder (parent chemical)- also a degradate of thiophanate methyl and benomyl. Some DERs were found in benomyl fate folder (099101)

161-1 Hydrolysis

MRID DER- Citation Reference

### `

82 PDF Image

154696 2052719 pg. 1 Priester, T. (1984) Hydrolysis of Carbendazim [2-Carbon-14]: Docu- ment No. AMR-265-84. Unpublished study prepared by E. I. du Pont de Nemours & Co. 23 p.

43129614 DER not located Mullee, D. (1992) BCM Technical Grade (HOE 17411) Hydrolysis: Lab Project Number: 121/172. Unpublished study prepared by Safepharm Labs. Ltd. 23 p.

Acc 259471 2052710 Wheeler, J. 1985. Hydrolysis of [phenyl-14c(u)]benomyl. Document No. AMR 419-85. E.I. du Pont de Nemours and Company, Inc., Wilmington, DE. Acc. No. 259471. Reference 1 .



### 161-2 Photodegradation-water

MRID DER-PDF Image Citation Reference

154697 2052719 pg. 19 Morales, R. (1984) The Effect of Light on 2-[Carbon-14] Benomyl Aqueous Solutions. Unpublished study. 16 p.

42686801 Contract draft – Surfadone LP-100 Saxena, A.; Marengo, J.; Marsh, S. (1991) Photodegradation of (inert ingredient) in a Buffered Aqueous Solution under Artificial Sunlight: Final Report: Lab Project Number: SC 900134: W-7. Unpublished study prepared by Battelle Memorial Institute. 115 p.

43129615 DER not located Mullee, D. (1993) Photostability (BCM Technical): Lab Project Number: 121/182. Unpublished study prepared by Safepharm Lab. Ltd. 17 p.
Open lit 2052719- pg 13 F l e e k e r , J. R. and Lacy, H. M . , " P h o t o l y s i s of Methyl 2-Benzimidazolecarbamate," J . Agr. Food Chem., -2 5 , 51 ( 1 9 7 7 ) .



### 161-3 Photodegradation-soil

MRID DER-PDF Image Citation Reference

120626 2052719 pg. 1 Helweg, A. (1977) Degradation and adsorption of carbendazim and 2- aminobenzimidazole in soil. Pestic. Sci. 8:71-78. (Also In unpublished submission received Sep 27, 1979 under 4581-340; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:099006-G)

No MRID 2052719 pg. 16 G a r d i n e r , J. A., "Laborat ory Exposure of Methyl-1-(Butylc a r b amo y l ) -2-14~-~enzimidazolecarbamatet o Mo i s t u r e , Non-S t e r i l e S o i l and UV Light," undated.



### Photo Stability

MRID DER-PDF Citation Reference

### `

83 Image

Not provided 2052719 pg 15 G a r d i n e r , J. A., " S t a b i l i t y of Methyl-1-( Butylcarbamoy1)- 2-Benzimidazolecarbamate i n S u n l i g h t , " undated



### .



### 162-1 Aerobic soil metabolism

MRID DERPDF Image Citation Reference

4125580 1 2052714 2052718- summary Marsh, B.H., and M.F. Arthur. 1989. Aerobic metabolism o f [phenyl(U)- 14 Clbenornyl i n Keyport s i l t loam. Laboratory Project ID: B a t t e l l e Project No. N-0518-8200; du Pont Report No. AMR-1112-88. Unpublished study performed by B a t t e l l e Memorial I n s t i t u t e , Columbus, OH, and submitted by E.I. du Pont de Nemo urs and Company, Inc., Wilmington, DE.



### 162-2 Anaerobic soil metabolism

MRID DERPDF Image Citation Reference

154699 40158401 2052719 Pg. 38 2052718

- summary Han, J. (1984) Anaerobic Soil Met abolism of 2-[Carbon-14]-Benomyl and Methyl 2-[Carbon-14]-Benzimidazol ecarbamate. Unpublished study prepared by E. I. du Pont de Nemours & Co., Inc. 16 p.

41137701 2052713 2052718

- summary Arthur, M.F., B.H. Marsh, L.C. F adel, and T.C. Zwick. 1989. Anaerobic aquatic metabol ism o f [phenyl (u) -14c] benomyl i n West Jefferson, Ohio, pond water and sediment. Laboratory Project ID: B a t t e l l e Project No. N0799- 8800; du Pont Report No. AMR-770-87. Unpublished study performed by B a t t e l l e Columbus D i v i s i o n , Columbus, OH, and submitted by E. I. du Pont deNemours and Company, Inc., Wilmington, DE.



### 162-4 Aerobic aquatic metab.

MRID DER-PDF Image Citation Reference

45620001 Contract draft available Ritter, A. (1988) Degradation of Carbendazim (HOE 017411) in Two Aerobic Aquatic Systems: Lab Project Number: 088132: A37801: HOE 017411. Unpublished study prepared by RCC Umweltchemie AG. 90 p. {OPPTS 835.3180}

### `

84 41291501 2052716 Arthur, M.F., K.L. Schweitzer, L.C. Fadel, B.H. Marsh, and S.S. Marsh. 1989. Aerobic aquatic metabol i sm o f [phenyl (u) -14c] benomyl i n Greenvi 11 e,M i s s i s s i p p i , water and sediment. Laboratory ProjectID: B a t t e l l e Project No. N-0966-730; du Pont Report No. AMR1452-89. Unpublished study performed by B a t t e l l e Columbus D i v i s i o n , Columbus, OH, and submitted by E.I. du Pont de Nemo urs and Company, Inc., Wilmington, DE.



### 162-4 Anaerobic aquatic metab.

MRID Citation Reference

41137701 2052718 Arthur, M.F., B.H. Marsh, L.C. F adel, and T.C. Zwick.1989. Anaerobic aquatic metabol i sm o f [phenyl (u) -14c] benomyl i n WestJefferson, Ohio, pond water and sediment. Laboratory Project ID: B a t t e l l e Project No. N0799-8800; du Pont Report No. AMR-770-87. Unpublished study performed by B a t t e l l e Columbus D i v i s i o n , Columbus, OH, and submitted by E.I. du Pont de Nemours and Company, Inc., Wilmington, DE



### .



### 163-1 Leach/adsorp/desorption

MRID DER-PDF Image Citation Reference

120626 2052719 pg. 2 Helweg, A. (1977) Degradation and adsorption of carbendazim and 2- aminobenzimidazole in soil. Pestic. Sci. 8:71-78. (Also In unpublished submission received Sep 27, 1979 under 4581-340; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:099006-G)
120631 Open Lit Aharonson, N.; Kafkafi, U. (1975) Adsorption, mobility, and persistence of thiabendazole and methyl 2-benzimidazolecarbamate in soils. J. Agric. Food Chem. 23(4):720-724. (Also In unpub- lished submission received Sep 27, 1979 under 4581-340; sub- mitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL: 099006-L)

Not provided 2052719 open lit Aharonson, N. and K a f k a f i , U., "Adsorption and Benzimidazole F u n g i c i d e s o n Mo n tmo r i l l o n i t e a n d ~ a o i i n i t eC l a y , " J. Agr .Food Chem.,

- 23, 4 3 4 ( 1 9 7 5 ) .

120655 2052719 pg. 43 Van Wambeke, E.; Van Assche, C. (1975?) The Importance of Some Factors Involved with the Persistence of Carbendazim (MBC) in Soil. (Unpublished study received Nov 8, 1977 under 4581-322; submitted by Agchem Div., Pennwalt Corp., Philadelphia, PA; CDL:232170-B)

No MRID 2052719 pg. 47 Rhodes, R. C. and Long, J. D . , "Run-off and Leaching S t u d i e s w i t h Me t h y l 2-14~-~enzimidazolecarbamate o n S o i l , " u n d a t e d .

154702 2052719 pg. 50 Rhodes, R.; Long, J. (1974) Run-off and mobility studies on Benomyl in soils and turf. Bulletin of Environmental Contamination & Toxicology 12(4):385-393.

154703 2052719 Aharonson, N.; Kafkafi, U. (1975) Adsorption of Benzimidazole

### `

85 pg. 2 fungicide on montmorillonite and kao linite clay surfaces. J. Agric. Food Chem. 23(3):434-437.

154704 2052719 pg. 55 Janutolo, D.; Stipes, R. (1978) Benz imidazole fungitoxicants in Virginia soils: movement, disappearance, and effect on micro- organisms: Bulletin 113: Virginia Polytechni c Institute and State University. Blackburg, VA: VA Water Resources Research Centre. 65 P.

43129616 DER not located Lindner, W. (1991) Assessm ent of Leaching Rates for 2- Methoxycarbonylamino-Benzimidazole Fungicide from Paint Films: Lab Project Number: RABCM2-7/91. Unpublished study prepared by Riedel-De Haen Aktiengesellschaft. 13 p.

41274801 2052715 2052717 Ryan D. 1989. Soil column leachi ng of [phenyl(~)-'4~]benomyiln a rice paddy soil. Completed on October 9, 1989. Performed and submitted by E.I. du Pont de Nemo urs and Company, Wilmington, DE.



### 164-1 Terrestrial field dissipation

MRID DER-PDF Image Citation Reference

41648901 2016976 Found w/PC # 099101 McNally, M. (1990) Field Soil Dissipation of Formulated Carbendazim and Benlate 50 DF Fungicide: Lab Project Number: AMR-1216-88. Unpublished study prepared by E.I. du Pont de Nemours and Co. 104 p.

42059102 2017299 Found w/PC # 099101 McNally, M. (1991) Field Soil Dissipation of Formulated Carbendazim and Benlate 50 DF Fungicide: Lab Project Number: AMR 1216-88: ML89.0116.DUP. Unpublished study prepared by E. I. du Pont de Nemours and Co. 44 p.

42060201 2017299 Found w/PC # 099101 McNally, M. (1991) Field Soil Dissipation of Formulated Carbendazim and Benlate 50 DF Fungicide: Lab Project Number: AMR 1216-88: ML89-0116-DUP. Unpublished study prepared by E. I. du Pont de Nemours and Co., and Morse Labs, Inc. 44 p.

42686701 2016982 Found w/PC # 099101 McNally, M. (1993) Field Soil Dissipation of Formulated Carbendazim and Benlate 50 DF Fungicide--Supplement No. 2: Lab Project Number: AMR 1216-88: ML89-0116-DUP. Unpublished study prepared by DuPont. 173 p.

44295403 2017144 Found w/PC # 099101 Xu, B. (1996) Independent Laboratory Validation of a Proposed Enforcement Analytical Method for Benomyl Metabolites, Carbendazim, and 2-Aminobenzimidazole in Soils by Capillary Electrophoresis: Final Report: Lab Project Number: 008-06: AMR 3650-95: AMR 2953-94. Unpublished study prepared by Centre Analytical Laboratories, Inc. 75 p.
Open lit 2052719 Baude, F. J,, Pease H. L. and Halt, R. F., " Fate of Benomyl on Field Soil and Turf," J. Agr. Food Chem.,-22, 413, (1974) Multiple states



### 164-5 Long term soil dissipation

MRID DER-PDF Image Citation Reference

### `

86 154700 2052179 Pg. 44 Sinha, A.; Agnihotri, V.; Singh, K. (1980) Persistence of Carbendazim in soil and its effect on Rhizos phere fungi of sugarbeet seedlings. Indian Phytopath 33(1):21-25.

154704 2052719 pg. 2 Janutolo, D.; Stipes, R. (1978) Benzimidazole fungitoxicants inVirginia soils: movement, disappearance, and effect on microorganisms: Bulletin 113: Virginia Polytechnic Institute and State University. Blackburg, VA: VA Water Resources Research Centre. 65 P.

42059102 42060201 2017299 Found w/PC # 099101 Folder # F000923 McNally, M. (1991) Field Soil Dissipation of Formulated Carbendazim and Benlate 50 DF Fungicide: Lab Project Number: AMR 1216-88: ML89.0116.DUP. Unpublished study prepared by E. I. du Pont de Nemours and Co. 44 p.

42060201 2017299 Found w/PC # 099101 Folder # F000923 McNally, M. (1991) Field Soil Dissipation of Formulated Carbendazim and Benlate 50 DF Fungicide: Lab Project Number: AMR 1216-88: ML89-0116-DUP. Unpublished study prepared by E. I. du Pont de Nemours and Co., and Morse Labs, Inc. 44 p.

42686701 2016982 Found w/PC # 099101 Folder # F000923 McNally, M. (1993) Field Soil Dissipation of Formulated Carbendazim and Benlate 50 DF Fungicide--Supplement No. 2: Lab Project Number: AMR 1216-88: ML89-0116-DUP. Unpublished study prepared by DuPont. 173 p.



### 165-1 Confined rotational crop

MRID DER-PDF Image Citation Reference

40496806 2052721 Rhodes, B. (1984) Greenh ouse Crop Rotation Study with ?2-?Carbon 14|| Carbendazim: Laboratory Projec t ID: AMR-495-86. Unpublish- ed study prepared by E.I. du Pont de Nemours and Co., Inc. 35 p.



### 165-4 Bioaccumulation in fish

MRID DER-PDF Image Citation Reference

154468 ACC 260573 2052711 2052712 2052720 Hutton, D. (1985) Laboratory Studies of [2-Carbon-14] CarbendazimBioconcentration in Bluegill Sunfish: Report No. 428-84. Unpublished study prepared by DuPont Haskell Laboratory. 47 p.

2052719 pg 75 H a z l e t o n L a b o r a t o r i e s , " T i s s u e Residue Study - B l u e g i l l S u n f i s h H-7122," Dec. 2 , 1971, Submitted to Du Pont.



### Non-Guideline Study Selections

MRID Citation Reference

### `

87 154701 2052719 pg. 2 Ramakrishna, C.; Gowda, T.; Sethunathan, N. (1979) Effect of Beno- myl and its hydrolysis products, MBC and Ab , on nitrification in a flooded soil. Bull. Environm. Contam. Toxicol. 21:328-333.

42812301 Letter Sharp, J. (1993) Letter Sent to O ffice of Pesticide Programs dated June 16, 1993: Effects of Harvesan Fungici de (DPX-7872-1 23): a combination of flusilazole and carbendazim on soil microflora. Prepared by Du Pont Agric. Products. 1 p.

42982601 DER not located Danneberg, G. (1993) Study of t he Effects of DPX-N7872-123 on theActivity of the Microflora of Soil: Final Report: Lab Project Number: BE-S11-92-01-DEH-02. Unpublished study prepared by Battelle Europe. 27 p.

40896 Tolerance study Reuter, J. (1975) Distribution and Identification of Residues in Apple Fruit with 14C Topsin M. (Unpublished study received Jan 15, 1975 under 4581-EX-17; prepared in cooperation wi th Mal- linckrodt, submitted by Pennwalt Corp., Philadelphia, Pa.; CDL: 094719-E)

Not provided 2052719 pg 22 

### P r i n c e , J. 

### L . , 

## " D e t e r m i n a t i o n o f Residues of Carbendazim i n Crops and S o i l , " Du Pont Document N o . 

### AMR-260-84, undated

44295402 ECM Method Adams, G. (1995) Residue Procedur e for the Analysis of Benomyl, Carbendazim (MBC), and 2-Aminobenzimidazole (2AB) in Soils by Capillary Electrophoresis: Lab Project Number: AMR 2953-94. Unpublished study prepared by Du Pont Agricultural Products and McKenzie Laboratories, Inc. 35 p.

2052723 2052724 

### Fate Database Oneliner Reports 1990 and 1994

### `

88 

## D. A CTIVE 

## Registrations Fo r 102001 / 23564-05-8 / Thiophanate-methyl

Registration # Registration Name 

### /status Rate Company Name 

### /# % of Active

228-626



### 06/30/11 NUFARM T-METHYL SPC 4.5 F FUNGICIDE/ Active - Conditionally Registered (06-Jul-2004)

, Turf & Ornamental use 7-20 oz /100 gal/A NUFARM AMERICAS, INC./ 228 46.2

228-628



### 12/21/09 NUFARM T-METHYL SPC 50 WSB FUNGICIDE/ Active - Conditionally Registered (12-Oct-2004)

, 

### Turf and Ornamental use 8-16 oz/ 100gal/A

6-16/1000 sq ft NUFARM AMERICAS, INC./ 228 50

228-631



### 04/23/2010 NUFARM T-METHYL SPC GRANULAR FUNGICIDE/ Active - Conditionally Registered (10-May-2006) 

### Turf and Ornamental use NUFARM AMERICAS, INC./ 228 2.08

228-652



### 12/03/12 NUFARM T-METHYL 4.5 F FUNGICIDE/ Active - Registered (22- Mar-2007) 

### Many Crop Uses + conifers 0.7-1.4 lbs ai/A NUFARM AMERICAS, INC./ 228 46.2

228-655



### 06/24/11 NUFARM T-METHYL 70 WSB FUNGICIDE/ Active - Conditionally Registered (07-May-2007) 

### Many Crop Uses + conifers 0.7-1.4 lb ai/A Max 2.8 lb ai/yr NUFARM AMERICAS, INC. 70

264-990 

### 01/30/10 TOPS 30 FLOWABLE FUNGICIDE/ Active - Conditionally Registered (08- Mar-2005)

, 

### Seed Treatment BAYER CROPSCIENCE LP/264 30

538-88 

### 06/21/11 SYSTEMIC FUNGICIDE/ Active - Conditionally Registered (19-Feb-1974)

, Concurrent - Under Reregistration (10- Feb-2005) 

### Lawn and Turf use only 2.72 lbs ai/app up to 21.77 lbs ai/yr – 14 day interval- turf SCOTTS COMPANY/538, 2.3

538-133 PROTURF FERTILIZER PLUS DSB FUNGICIDE / Active - Conditionally Registered (27-Apr-1979)

, Concurrent - Under Reregistration (10-Feb-2005) 538 SCOTTS COMPANY/538, 1.75

538-EIT ANDERSON'SSYSTEMIC FUNGICIDE/ Pending - Under Review (09-Jan-2001) 538 SCOTTS COMPANY/ 538, 2.3

869-EUE GREEN LIGHT FUNG AWAY III SYSTEMIC LAWN FUNGICIDE/ Pending - Under Review (31-Jan-2002) GREEN LIGHT COMPANY/869 2.08

### `

89 1001-63 3336 WP TURF AND ORNAMENTAL FUNGICIDE/ Active - Conditionally Registered (26-Sep-1988)

, Concurrent - Under Reregistration (10- Feb-2005) CLEARY CHEMICALS, LLC/1001 50

1001-69



### 09/09/13 3336 F/ Active - Conditionally Registered (24-Oct-1995) , Ornamental, 

### Lawn and Turf use only 2.68 gal//A per year - golf course w 14 D interval CLEARY CHEMICALS, LLC/1001 41.25

1001-70 3336 G/ Active - Conditionally Registered (24-Oct-1995)

, Concurrent - Under Reregistration (10- Feb-2005) 1001 CLEARY CHEMICALS, LLC/1001 2.08

1001-78 3336 PLUS SYSTEMIC FUNGICIDE/ Active - Conditionally Registered (05- Aug-2004)

, Concurrent - Under Reregistration (10- Feb-2005) 1001 CLEARY CHEMICALS, LLC/1001 19.4

1001-80 PREMIUM SYSTEMIC FUNGICIDE/ Active - Conditionally Registered (28- Jan-2008) 1001 CLEARY CHEMICALS, LLC/1001 44.62

1001-81 3336(R) 70EG/ Active - Conditionally Registered (18-Sep-2008) 1001 CLEARY CHEMICALS, LLC/1001 70

1001-89 3336 EG/ Active - Conditionally Registered (20-Jun-2013) 1001 CLEARY CHEMICALS, LLC/1001 50

1381-222 THIOPHANATE-METHYL 45% F FUNGICIDE/ Active - Registered (15- Nov-2007) WINFIELD SOLUTIONS, LLC/1381 46.2

1381-228 THIOPHANATE-METHYL 50% WSB FUNGICIDE/ Active - Registered (28- Sep-2007) 1381 WINFIELD SOLUTIONS, LLC/1381 50

8033-118 TOPSIN M TECHNICAL/ Active - Conditionally Registered (16-Jan-1973)

, Concurrent - Under Reregistration (10- Feb-2005) NIPPON SODA CO., LTD./ 8033 97

8033-119 FANATE 70WSB/ Active - Conditionally Registered (25-Jul-2001)

, Concurrent - Under Reregistration (10- Feb-2005) 8033 NIPPON SODA CO., LTD./ 8033 70

8033-120 TOPSIN M 70WP/ Active - Conditionally Registered (23-Aug-2000)

, Concurrent - Under Reregistration (10- Feb-2005) 8033 NIPPON SODA CO., LTD./ 8033 70

### `

90 8033-121 TOPSIN M 5D FUNGICIDE/ Active - Conditionally Registered (06-Jan-1983)

, Concurrent - Under Reregistration (10- Feb-2005) 8033 NIPPON SODA CO., LTD./ 8033 5

8033-122 TOPSIN 4.5 FL / Active - Conditionally Registered (03-Nov-1983)

, Concurrent - Under Reregistration (10- Feb-2005) 8033 NIPPON SODA CO., LTD./ 8033 45

8033-123 TOPSIN M 5G FUNGICIDE/ Active - Conditionally Registered (22-Mar-1990)

, Concurrent - Under Reregistration (10- Feb-2005) 8033 NIPPON SODA CO., LTD./ 8033 5

8033-124 TOPSIN M 85 WDG/ Active - Conditionally Registered (22-Mar-1990)

, Concurrent - Under Reregistration (10- Feb-2005) 8033 NIPPON SODA CO., LTD./ 8033 85

8033-125 TOPSIN M WSB/ Active - Conditionally Registered (22-Dec-1993)

, Concurrent - Under Reregistration (10- Feb-2005) 8033 NIPPON SODA CO., LTD./ 8033 70

8033-126 TOPSIN M 70WDG/ Active - Conditionally Registered (10-Jun-2005) 8033 NIPPON SODA CO., LTD./ 8033 70

8033-128 FANATE II 4.5F/ Active - Registered (06-Aug-2009) 8033 NIPPON SODA CO., LTD./ 8033 46.2

8033-REO THIOPHANATE METHYL 4.1 SC FUNGICIDE/ Pending - Under Review (27-Jun-2013) 8033 NIPPON SODA CO., LTD./ 8033 41.3

8033-RGN THIOPHANATE METHYL 4.1 SC T&O FUNGICIDE/ Pending - Under Review (27-Jun-2013) 8033 NIPPON SODA CO., LTD./ 8033 41.3

10163-EUI THIOPHANATE-METHYL 70-W/ Pending - Under Review (15-Sep-1999) GOWAN COMPANY/10163 70

10163-249 THIOPHANATE METHYL 80 WDG/ Active - Conditionally Registered (07- Nov-2000)

, Concurrent - Under Reregistration (10-Feb-2005) 10163 GOWAN COMPANY/10163 80

10163-262 THIOPHANATE METHYL 70-W AGRICULTURAL FUNGICIDE/ Active - Conditionally Registered (30- Oct-2001)

, Concurrent - Under Reregistration (10- Feb-2005) 10163 GOWAN COMPANY/10163 70

10163-291 THIOPHANATE-METHYL TECHNICAL 98.4/ Active - Conditionally Registered (14-Dec-2006) 10163 GOWAN COMPANY/10163 98.4

### `

91 10163-292 THIOPHANATE-METHYL TECHNICAL/ Active - Conditionally Registered (17-Jun-1999)

, Concurrent - Under Reregistration (10-Feb-2005) 10163 GOWAN COMPANY/10163 95.1

34704-921 THIOFAN 8 METHYL 4.5 FUNGICIDE/ Active - Registered (28- Mar-2006) LOVELAND PRODUCTS, INC. 34704 46.2

34704-932 THIO-M 50 WSB FUNGICIDE/ Active - Conditionally Registered (05-Jul-2006) 34704 LOVELAND PRODUCTS, INC. 34704 50

34704-1007 LPI THIO-M 70 WSB/ Active - Registered (05-Jun-2008) 34704 LOVELAND PRODUCTS, INC. 34704 70

34704-1008 LPI THIO-M AG 4.5F/ Active - Registered (05-Jun-2008) 34704 LOVELAND PRODUCTS, INC. 34704 46.2

35935-59 ET-003/ Active - Conditionally Registered (21-Mar-2006) NUFARM LIMITED/35935 98

48234-12 SYSTEC 1998 FL/ Active - Conditionally Registered (06-Mar-1995)

, Concurrent - Under Reregistration (10- Feb-2005) REGAL CHEMICAL CO./ 48234 46.2

48234-13 SYSTEC 1998 WDG/ Active - Conditionally Registered (06-Mar-1995)

, Concurrent - Under Reregistration (10- Feb-2005) 48234 REGAL CHEMICAL CO./ 48234 85

51036-GIR THIOPHANATE METHYL 2G/ Pending - Under Review (09-Jul-2001) BASF SPARKS LLC/51036 2

51036-GIE THIOPHANATE METHYL 1G/ Pending - Under Review (09-Jul-2001) 51036 BASF SPARKS LLC/51036 1.04

51274-1 COLORSTAR PLUS/ Active - Conditionally Registered (07-Jan-2011) NELSON PLANT FOOD/51274 .2

53883-RNR T-METHYL 2.08G/ Pending - Under Review (16-Dec-2002) CONTROL SOLUTIONS, INC./ 53883 2.08

53883-RNE T-METHYL 4.5L/ Pending - Under Review (16-Dec-2002) 53883 CONTROL SOLUTIONS, INC./ 53883 46.2

53883-RRR T-METHYL 1.04G/ Pending - Under Review (16-Dec-2002) 53883 CONTROL SOLUTIONS, INC./ 53883 1.04

53883-183 T-METHYL G-PR O GRANULAR/ Active - Conditionally Registered (10- Jan-2006) 53883 CONTROL SOLUTIONS, INC./ 53883 2.08

### `

92 53883-321 QUALI-PRO TM 85 WDG/ Active - Registered (19-Nov-2012) 53883 CONTROL SOLUTIONS, INC./ 53883 85

55146-127 ST-METHYL 540 FS/ Active - Registered (15-Jan-2013) NUFARM AMERICAS, INC./ 55146 46.2

58185-30 FUNGO 50 WSB WETTABLE POWDER TURF & ORNAMENTAL SYSTEMIC FUNGICIDE/ Active - Conditionally Registered (27-Jan-1994)

, Concurrent - Under Reregistration (10- Feb-2005) EVERRIS NA, INC./ 58185 50

58185-33 DOMAIN FL/ Active - Conditionally Registered (22-Feb-1996)

, Concurrent - Under Reregistration (10-Feb-2005) 58185 EVERRIS NA, INC./ 58185 46.2

59807-5 OHP 4.5 L FUNGICIDE/ Active - Registered (20-Sep-2007) OHP, INC./ 59807 46.2

59807-6 OHP 50 WP FUNGICIDE/ Active - Registered (17-Sep-2007) 59807 OHP, INC./ 59807 50

66222-134 THIOPHANATE METHYL 4.5 F/ Active - Conditionally Registered (20- Sep-2001)

, Concurrent - Under Reregistration (10-Feb-2005) MAKHTESHIM AGAN OF NORTH AMERICA, INC./ 66222 46.2

66222-145 NATIONS AG II THIOPHANATE METHYL 85 WDG/ Active - Conditionally Registered (14-Nov-2001)

, Concurrent - Under Reregistration (10- Feb-2005) 66222 MAKHTESHIM AGAN OF NORTH AMERICA, INC./ 66222 85

66330-292 THIOPHANATE METHYL 70W/ Active - Conditionally Registered (14- Jun-2001)

, Concurrent - Under Reregistration (10-Feb-2005) ARYSTA LIFESCIENCE NORTH AMERICA, LLC /66330 70

66330-293 THIOPHANATE METHYL 4.5L/ Active - Conditionally Registered (06- Aug-2001)

, Concurrent - Under Reregistration (10-Feb-2005) 66330 ARYSTA LIFESCIENCE NORTH AMERICA, LLC/66330 46.2

66330-294 Active - Conditionally Registered (10- Oct-2001)

, Concurrent - Under Reregistration (10-Feb-2005) 66330 ARYSTA LIFESCIENCE NORTH AMERICA, LLC /66330 50

66330-301 THIOPHANATE METHYL 70W WSB/ Active - Conditionally Registered (06- Sep-2001)

, Concurrent - Under 66330 ARYSTA LIFESCIENCE NORTH 70

### `

93 Reregistration (10-Feb-2005) AMERICA, LLC /66330

66330-304 THIOPHANATE METHYL 98% TECH/ Active - Conditionally Registered (19-Jul-2001)

, Concurrent - Under Reregistration (12-Jan-2006) 66330 ARYSTA LIFESCIENCE NORTH AMERICA, LLC /66330 98.3

66330-327 THIOPHANATE METHYL 85EG / Active - Registered (01-May-2002)

, Concurrent - Under Reregistration (10- Feb-2005) 66330 ARYSTA LIFESCIENCE NORTH AMERICA, LLC /66330 85

66330-335 THIOPHANATE METHYL 4.5F AG/ Active - Conditionally Registered (11- Aug-2004)

, Concurrent - Under Reregistration (10-Feb-2005) 66330 ARYSTA LIFESCIENCE NORTH AMERICA, LLC /66330 46.2

70506-250 T-BIRD 85 WDG/ Active - Conditionally Registered (20-Apr-2006) UNITED PHOSPHORUS, INC/70506 85

70506-251 T-BIRD 4.5L/ Active - Conditionally Registered (20-Apr-2006) 70506 UNITED PHOSPHORUS, INC/70506 46.2

70506-304 ANDERSONS GOLF PRODUCTS FUNGO FLO/ Active - Conditionally Registered (09-Aug-2004)

, Concurrent - Under Reregistration (10-Feb-2005) 70506 UNITED PHOSPHORUS, INC/70506 45

72112-1 TRANSOM 50 WSB/ Active - Conditionally Registered (13-Jan-2006) PROKOZ, INC./ 72112 50

72112-2 TRANSOM 4.5 F/ Active - Conditionally Registered (13-Jan-2006) 72112 PROKOZ, INC./ 72112 46.2

83070-1 TEE-OFF 4.5F/ Active - Conditionally Registered (30-Nov-2006) ADVAN LLC/83070 46.2

83558-21 THIOPHANATE-METHYL TECHNICAL/ Active - Conditionally Registered (12-Feb-2001)

, Concurrent - Under Reregistration (10-Feb-2005) CELSIUS PROPERTY B.V., AMSTERDAM (NL)/ 83558 99

84229-3 THIOPHANATE-METHYL 85% WDG/ Active - Conditionally Registered (07-Aug-2008) TIDE INTERNATIONAL, USA, INC./ 84229 85

84930-34 ARC-TFAN 4.5FL FUNGICIDE/ Active - Registered (28-Apr-2011) ARCANA, LLC/84930 45

85724-1 AKOTOP 85 WG/ Active - Registered (10-Mar-2009) AAKO B.V./ 85724 85

### `

94 86363-10 THIOFAN8 4.0/ Active - Registered (30-Jun-2011) KAIZEN TECHNOLOGIES, LLC/86363 41.25

89167-22 AX TFM 4.5FL FUNGICIDE/ Active - Registered (14-Jan-2013) AXION AG PRODUCTS, LLC/89167 45

89442-14 THIOPHANATE METHYL 4.5F SELECT/ Active - Conditionally Registered (16-Jul-2013) PRIME SOURCE, LLC/89442 46.2



## Mixture Products- multi actives

228-630 NUFARM TM+IP SPC FUNGICIDE + Iprodione/ Active - Conditionally Registered (07-Nov-2005) NUFARM AMERICAS, INC./ 228 19.65 19.65

228-638 NUFARM TM + CTN SPC 66.6 WDG FUNGICIDE With Chlorothalonil / Active - Conditionally Registered (07- Dec-2006) 228 NUFARM AMERICAS, INC./ 228 16.66/5 0

228-639 TM + CTN E-PRO 90 WDG FUNGICIDE with Chlorothalonil/ Active - Conditionally Registered (07- Dec-2006) 228 NUFARM AMERICAS, INC./ 228 18/72

264-958 TOPS MZ POTATO SEED-PIECE TREATMENT FUNGICIDE with Mancozeb/ Active - Conditionally Registered (05-Oct-1995)

, Concurrent - Under Reregistration (31-Jul-2007) BAYER CROPSCIENCE LP/264 2.5/6

264-973 EVOLVE POTATO SEED PIECE TREATMENT FUNGICIDE with Mancozeb and Cymoxanil/ Active - Conditionally Registered (05-Oct-1995)

, Concurrent - Under Reregistration (31- Jul-2007) 264 BAYER CROPSCIENCE LP/264 2.5/6/1

264-998 FOUR WAY PEANUT SEED TREATMENT FUNGICIDE With Metalaxyl, Trifloxystrobin, and Captan/ Active - Conditionally Registered (10-Jun-2005)

, Concurrent - RUP (10-Jun-2005) 264 BAYER CROPSCIENCE LP/264 13.6/8/ 2/ 49

432-1414 26/36 FUNGICIDE With Iprodione / Active - Conditionally Registered (01-Mar-2005) BAYER ENVIRONMENTA L SCIENCE/432 19.65/ 19.65

432-1440 SYSSTAR WDG With Flutolanil / Active - Conditionally Registered (09-Nov-2000)

, Concurrent - Under Reregistration (07- 432 BAYER ENVIRONMENTA L SCIENCE/432 28.58/ 51.42

### `

95 Apr-2010)

432-RUUR Systar With Flutolanil / Pending - Under Review (14-May-1999) 432 BAYER ENVIRONMENTA L SCIENCE/432 1/1.8

1001-90 RACHET FUNGICIDE with Tebuconazole / Active - Registered (20-May-2013) CLEARY CHEMICALS, LLC/1001 36.3/ 7.1

7969-268 ACRONIS FUNGICIDE SEED TREATMENT with Pyraclostrobin / Active - Conditionally Registered (29- Oct-2009) BASF CORPORATION/7 969 37.92/ 4.22

1001-72 SPECTRO 90 WDG with Chlorothalonil / Active - Conditionally Reregistered (09-Mar-2000)

, Concurrent - Under Reregistration (10- Feb-2005) CLEARY CHEMICALS, LLC/1001 18/72

8033-127 TEBUCONAZOLE/TOPSIN PREMIX/ Active - Conditionally Registered (31- Jan-2008) NIPPON SODA CO., LTD./ 8033 37.5/7. 5

9198-228 ANDERSONS GOLF PRODUCTS FERTILIZER PLUS FUNGICIDE VIII with Iprodione / Active - Conditionally Registered (09-May-2005) THE ANDERSONS LAWN FERTILIZER DIVISION, INC./ 9198 2.05/1. 02

9198-229 ANDERSONS GOLF PRODUCTS FLUID FUNGICIDE with Iprodione/ Active - Conditionally Registered (31- May-2006) 9198 THE ANDERSONS LAWN FERTILIZER DIVISION, INC./ 9198 19.65/ 19.65

34704-IUL PCC 1215 FUNGICIDE DUST with Mancozeb / Pending - Under Review (04-Jan-2002) LOVELAND PRODUCTS, INC./ 34704 2.5/6

34704-1064 PROTOCOL with Propiconazole / Active - Conditionally Registered (12- Apr-2012) 34704 LOVELAND PRODUCTS, INC./ 34704 23.7/7. 1

48234-7 CONSYST WDG with Chlorothalonil/ Active - Conditionally Registered (22-Nov-1993)

, Concurrent - Under Reregistration (10-Feb-2005) REGAL CHEMICAL CO./ 48234 16.66/5 0

53883-309 QUALI-PRO ENCLAVE 5.3F With Chlorothalonil, Iprodione, and Tebuconazole / Active - Registered (16-Nov-2012) CONTROL SOLUTIONS, INC./ 53883 9.4/24. 7/ 9.4/2.8

53883-323 QUALI-PRO TMI 20/20 with 53883 CONTROL 19.65/

### `

96 Iprodione / Active - Registered (25-Jan2013) SOLUTIONS, INC./ 53883 19.65

58185-10 BANROT BROAD SPECTRUM FUNGICIDE 40% WETTABLE POWDER with Etridiazole/ Active - Conditionally Registered (17-Jul-1987)

, Concurrent - Under Reregistration (10- Feb-2005) EVERRIS NA, INC./ 58185 25/15

58185-23 BANROT 8 G FUNGICIDE with Etridiazole / Active - Conditionally Registered (17-Jul-1987)

, Concurrent - Under Reregistration (10- Feb-2005) 58185 EVERRIS NA, INC./ 58185 5/3

58185-31 DUOSAN WSB WETTABLE POWDER TURF AND ORNAMENTAL FUNGICIDE with Mancozeb / Active - Conditionally Registered (04-Aug-1993)

, Concurrent - Under Reregistration (31- Jul-2007) 58185 EVERRIS NA, INC. 15.6/64

58185-32 DUOSAN BROAD SPECTRUM CONTACT ORNAMENTAL FUNGICIDE with Mancozeb/ Active- Conditionally Registered (04-Aug1993)

, Concurrent - Under Reregistration (31-Jul-2007) 58185 EVERRIS NA, INC./ 58185 15.6/64

66330-311 I PRODIONE /THIOPHANATE METHYL COMBO/ Active - Conditionally Registered (30-Jun-2004)

, Concurrent - Under Reregistration (10- Feb-2005) ARYSTA LIFESCIENCE NORTH AMERICA, LLC /66330 19.65/ 19.65

70506-254 PEREGRINE with Chlorothalonil / Active - Registered (19-Sep-2006) UNITED PHOSPHORUS, INC/70506 16.66/5 0

70506-261 DOVETAIL with Iprodione/ Active - Registered (25-Apr-2007) 70506 UNITED PHOSPHORUS, INC/70506 19.65/ 19.65

83070-2 TEE-1 UP WDG FUNGICIDE with Chlorothalonil/ Active - Registered (11-Jun-2007) ADVAN LLC/83070 16.66/5 0

89167-26 AX TFM-TEB LIQUID FLOWABLE FUNGICIDE with Tebuconazole/ Active - Registered (06-Feb-2013) AXION AG PRODUCTS, LLC/89167 37.5/7. 5



### Section 18 registrations

Section 18’s, CA, TOPSIN M WSB 8033 NIPPON SODA CO., LTD. 70

### `

97 WA, WI, MN, VA, DE, NY, ID, OR, GA

### `

98 

## E. Active Registrations for 128872 / 10605-21-7 / Carbendazim\

Registration # Registration Name Company # Company Name % of Active Ingredient



### Industrial Use Products

365-80 MERGAL BCM Active - Conditionally Registered (17-Mar-2000) 365 TROY CHEMICAL COMPANY LIMITED 99

365-81 BCM TECHNICAL Active - Conditionally Registered (17-Mar-2000)

, Concurrent - Under Reregistration (04-Jan-2005) 365 TROY CHEMICAL COMPANY LIMITED 99

707-303 ROCIMA 63 INDUSTRIAL MICROBICIDE with Diuron and Octhilinone Active - Conditionally Registered (02-Oct-2003)

, 707 ROHM & HAAS CO 7.5/20/2.7

707-304 ROCIMA 65 INDUSTRIAL MICROBICIDE Active - Conditionally Registered (05- Nov-2003) with 128996 and 128101 707 ROHM & HAAS CO 9/3.5/5

5383-102 MERGAL S 90 Active Registered (25-Jun-1996)

, with Octhilinone and 128996 5383 TROY CHEMICAL CORP 9.9/4.5/4.9

5383-108 POLYPHASE 662 with 107801 Troysan and Irgarol Active - Conditionally Registered (29-Aug-2001) 5383 TROY CHEMICAL CORP 12/4/4

5383-109 POLYPHASE 663 with Diuron and Troysan KK Active - Conditionally Registered (13-Sep-2001)

, Concurrent - Under Reregistration (28-Oct-2005) 5383 TROY CHEMICAL CORP 9/15/3

5383-110 POLYPHASE 678 with Troysan KK Active - Conditionally Registered (01-May-2002) 5383 TROY CHEMICAL CORP 15/5

5383-133 TROY EX 2085 with Troysan KK Active - Registered (31-Jan-2008) 5383 TROY CHEMICAL CORP 15/5

### `

99 5383-134 TROY EX-2108 Active - Conditionally Registered (27- Jul-2007) 5383 TROY CHEMICAL CORP 20

39967-71 PREVENTOL A 14-D with Diuron and OcthilinoneActive - registered (30-Jul2008)

, Reregistration (12- May-2010) 39967 LANXESS CORPORATION 10/22/3

74075-2 INTACE FUNGICIDE B-350 Active - Conditionally Registered (06-Jan-2005) 74075 INTACE 43.54



### Tree Injection uses

7946-14 Tree Injection

uses FUNGISOL with 2-EEEBC Active - Conditionally Registered (08-Sep-1993)

, Reregistration (16-Jul-2010) 7946 J. J. MAUGET CO. 0.3/1.7

7946-20 Tree Injection

uses ABASOL (TM) with 2- EEEBC and Abamectin Active - Conditionally Registered (30-Dec-1996)

, Reregistration (16-Jul-2010) 7946 J. J. MAUGET CO. 0.3/1.7/0.46

7946-21 Tree Injection

uses IMISOL with 2-EEEBC and Imidacloprid Active - Conditionally Registered (28-Nov-1997)

, Reregistration (16-Jul-2010) 7946 J. J. MAUGET CO. 0.3/1.7/5