UNITED STATES ENVIRONMENTAL PROTECTION AGENCY 

WASHINGTON, D.C. 20460 

OFFICE OF CHEMICAL SAFETY AND 

POLLUTION PREVENTION 

MEMORANDUM 

Date: 03/02/2016 

Subject: Bensulide. Summary of Analytical Chemistry and Residue Data in Support of 

Registration Review. 

From: 

Through: 

To: 

PC Code: 009801 DP Barcode: D429307 

Decision No.: 507866 Registration No.: 10163-200 

Petition No.: NA Regulatory Action: Registration Review 

Risk Assessment Type: Single Chemical Case No.: 2035 

TXR No.: NA CAS No.: 741-58-2 

MRID No.: NA 40 CFR: 180.241 

Ideliz Negr6n-Encarnaci6n, Ph.D., Chemist,· RAB V ~ "-

Health Effects Division (HED; 7509P) ~ 7 

Danette 

Thomas 

Drew

Bloem

, Senior 

, C~~ 

Chemis~D, RAB V (7509~ 

Elizabeth Holman, Physical Scientist ~ ~ 

ChemSAC Designated Reviewers (HED; 7509P) 

Margaret Hathaway I Kevin Costello 

Pesticide Re-evaluation Division (7508P) 

Summary of Submitted Residue Chemistry Studies 

OCSPP 860 MRIDNumber Title 

Series 

Guideline 

860.1520 44435501 Magnitude of the Residue ofBensulide in Tomato Processed Commodities. 

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Table of Contents 

1.0 Executive Summary ............................................................................................................ 3

2.0 Regulatory Recommendations ............................................................................................ 3

2.1 Data Deficiencies/Data Needs .......................................................................................... 3

2.2 Tolerance Considerations ................................................................................................. 4

2.2.1 Enforcement Analytical Method ............................................................................... 4

2.2.2 Recommended Tolerances ........................................................................................ 4

2.2.3 International Harmonization ..................................................................................... 5

3.0 Introduction ......................................................................................................................... 5

3.1 Chemical Identity ............................................................................................................. 6

3.2 Physical/Chemical Characteristics ................................................................................... 6

3.3 Pesticide Use Pattern/Directions for Use (860.1200) ....................................................... 7

4.0 Metabolite/Degradate Residue Profile ................................................................................ 7

4.1 Nature of the Residue ....................................................................................................... 7

4.2 Residues of Concern Summary and Rationale ................................................................. 8

5.0 Residue Profile .................................................................................................................... 8

5.1 Residue Analytical Methods (860.1340) .......................................................................... 8

5.1.1 Tolerance Enforcement and Data Collection Methods ............................................. 8

5.1.2 Multi-Residue Methods (860.1360) .......................................................................... 8

5.1.4 Submittal of Analytical Reference Standards (860.1650) ........................................ 9

5.2 Storage Stability (860.1380) ............................................................................................ 9

5.3 Residue Data .................................................................................................................. 10

5.3.1 Crop Field Trials (860.1500) .................................................................................. 10

5.3.2 Field Rotational Crops (860.1900) ......................................................................... 11

5.3.3 Processed Food and Feed (860.1520) ..................................................................... 11

5.3.4 Meat, Milk, Poultry and Eggs (860.1480) .............................................................. 12

5.3.5. Food Handling (860.1460) ...................................................................................... 12

5.3.6 Water, Fish, and Irrigated Crops (860.1400) .......................................................... 12

5.4 Food Residue Profile ...................................................................................................... 12

Appendix A. International Residue Limits Table ........................................................................ 14

Appendix B. Comparison of Residue Levels of Bensulide and its Oxon .................................... 15

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1.0 Executive Summary 

Bensulide [S-(O,O-diisopropyl phosphorodithioate) ester of N-(2-mercaptoethyl)benzenesulfonamide] is an herbicide registered in the U.S. for food/feed uses on bulb onion, garlic, 

shallots, peppers (bell/nonbell), tomatillo, leafy vegetable except brassica (crop group (CG) 4), 

leafy brassica vegetable (CG 5), and cucurbit vegetable (CG 9), and a regional registration for 

use on carrots. The registrant as also previously indicated interest in maintaining tolerances 

in/on tomato for import purposes. Tolerances ranging from 0.10 to 0.15 ppm are established in 

the 40 CFR § 180.241 for residues of bensulide including its oxygen analog in/on these raw 

agricultural commodities. No tolerances have been established for any processed food/feed 

commodities or any animal commodities. The emulsifiable concentrate (EC) end-use product 

Prefar 4-E (EPA Reg. No. 10163-200) is the only bensulide formulation class registered for use 

on food/feed crops in the U.S. This formulation is typically applied to the soil preplant 

(incorporated) or preemergence (banded or broadcast) using ground equipment. 

The residue database for bensulide is complete with the exception of crop field trials with nonbell pepper (domestic) and tomato (import). Adequate methods are available for the enforcement 

of tolerances for bensulide and its oxygen analog in/on plant commodities. The tolerance 

expressions in the code of federal regulations (CFR) needs to be modified according to the 

interim guidance on writing tolerance expressions (S. Knizner, 05/27/2009), and the tolerance for 

fruiting vegetables CG 8 needs to be removed while a tolerance for tomatillo and bell pepper 

may be established. A tolerance for tomato may be included pending registrant feedback with 

regards to data previously requested to support use on imported tomatoes. 

2.0 Regulatory Recommendations 

There are no residue chemistry considerations that would preclude granting reregistration for 

bensulide on all crops with the exception of non-bell peppers. The specific label modifications 

are discussed in section 2.3. 

2.1 Data Deficiencies/Data Needs 

Three geographically representative field trials on non-bell peppers are required. Pending the 

submission of these data, the instructions for application to non-bell peppers should be removed 

from the label. This data deficiency was identified in the bensulide’s residue chemistry chapter 

in support of the Registration Eligibility Decision (RED; C. Eiden, D238417, 10/06/1997) and 

the registration review scoping document (T. Goodlow, D347549, 06/10/2008). 

Twelve crop field trials for bensulide on tomato grown in Mexico were required in the bensulide 

residue chemistry chapter in support of the Registration Eligibility Decision (RED; C. Eiden, 

D238417, 10/06/1997). The label from Mexico was submitted and describes a similar use 

pattern with the one registered in the US. The registrant expressed their intent to submit a 

proposal to address this data gap (conference call on 11/16/2015, coordinated by Margaret 

Hathaway). Pending the submission of these data, the twelve crop field trials are still required. 

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2.2 Tolerance Considerations 

2.2.1 Enforcement Analytical Method 

Adequate methods are available for tolerance enforcement for plant commodities. The Pesticide 

Analytical Manual (PAM) Vol. II lists Gas Chromatography (GC) Method I, using either 

phosphorus-sensitive thermionic detection or flame photometric detection, for the determination 

of bensulide and bensulide oxygen analog in plant commodities. Thin layer chromatography 

(TLC) Method A is available for confirmation. Moreover, the PAM (Volume I, Appendix I) 

indicates that bensulide is recovered using Multiresidue Methods Sections 302 (Luke Method; 

Protocol D), 304 (Mills Method; Protocol E, fatty foods) and 303 (Mills, Onley, Gaither Method; 

Protocol E, non-fatty foods). No information regarding the recovery of bensulide oxygen analog 

using Multiresidue Methods is included in the PESTDATA database. 

2.2.2 Recommended Tolerances 

HED recommends modifying the tolerance expression and crop groups included in the CFR for 

bensulide. The tolerance expressions in the 40 CFR § 180.241 (a) and (c) need to be modified to 

include both, coverage and compliance statements for enforcement purposes, as recommended in 

the Interim Guidance on Writing Tolerance Expressions (S. Knizner, 05/27/2009). The 

recommended tolerance expressions are: 

(a) General. “Tolerances are established for residues of the herbicide bensulide, including its 

metabolites and degradates, in or on the commodities in the following table. Compliance with the 

tolerance levels specified in the table below is to be determined by measuring only bensulide, S-

(O,O-diisopropyl phosphorodithioate) ester of N-(2-mercaptoethyl) benzenesulfonamide, and its 

oxygen analog, S-(O,O-diisopropyl phosphorothioate) of N-(2-mercaptoethyl) 

benzenesulfonamide, in or on the commodity.” 

(c) Tolerance with regional registration. “Tolerances with regional registration, as defined in 

§180.1(l), are established for residues of the herbicide bensulide, including its metabolites and 

degradates, in or on the commodities in the following table. Compliance with the tolerance levels 

specified in the table below is to be determined by measuring only bensulide, S-(O,O-diisopropyl 

phosphorodithioate) ester of N-(2-mercaptoethyl) benzenesulfonamide, and its oxygen analog, S-

(O,O-diisopropyl phosphorothioate) of N-(2-mercaptoethyl) benzenesulfonamide, in or on the 

commodity.” 

Since non-bell pepper field trial data are not available, HED concludes that the fruiting vegetable 

crop group 8 tolerance should be deleted and bell pepper and tomatillo tolerances established in 

support of domestic registrations. Additional data is required to support a tolerance for tomato 

imported from Mexico. The establishment of a tolerance for tomato may be recommended if this 

data (or a waiver request) is received from the registrant and considered adequate to support this 

use. Tolerances included in the 40 CFR 180.241 need to be modified as specified in the table 

below. 

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Table 2.2.2. Tolerance Summary for Bensulide. 

Commodity Established 

Tolerance (ppm) 

HED-Recommended 

Tolerance (ppm) 

Comments 

(correct commodity definition) 

Vegetable, fruiting, group 8 0.10 Remove 

Pepper, bell None 0.10 

Tomatillo None 0.10 

Tomato, subgroup 8-10A* None 0.10 

*May be established pending review of required data in support of import use. 

2.2.3 International Harmonization 

There is no Codex, Mexican or Canadian maximum residue limits established for bensulide. 

Therefore, harmonization is not germane to this assessment. 

2.3 Label Recommendations 

The following recommendations are based on the review of the label of bensulide’s end use 

product Prefar 4-E (EPA Reg. No. 10163-200, 12/13/2013): 

 The current label of Prefar 4-E includes instructions for use on non-bell peppers such as 

chili peppers, cooking peppers, pimentos and sweet peppers. A magnitude of residue 

study for bensulide in/on non-bell peppers has been required in the RED and scoping 

document. Alternatively, it was indicated that the registrant could restrict use to bell 

peppers. Since these data have not been received, HED recommends that the label of the 

bensulide products containing instructions for use on bell and non-bell peppers is 

modified to restrict the use to only bell peppers. Moreover, reference to the fruiting 

vegetables crop group needs to be removed. 

 The maximum seasonal application rate for cucurbit vegetables, tomatillo and bell 

peppers needs to be specified in the label of Prefar 4-E. A maximum seasonal application 

rate of 6 lbs ai/A is adequate for crops under these crop groups. 

3.0 Introduction 

Bensulide [S-(O,O-diisopropyl phosphorodithioate) ester of N-(2-mercaptoethyl)benzenesulfonamide] is a herbicide registered for food/feed uses on brassica leafy vegetables, carrots, 

peppers (bell/nonbell), tomatillo, cucurbits, leafy vegetables, and bulb onions. Bensulide’s mode 

of action is through the inhibition of cell division in the roots and shoots of plants. The 

emulsifiable concentrate (EC) end-use product is the only bensulide formulation class registered 

for use on food/feed crops. These formulations are typically applied to the soil preplant 

(incorporated) or preemergence (banded or broadcast) using ground equipment. 

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3.1 Chemical Identity 

Table 3.1. Bensulide and Bensulide Oxon Nomenclature. 

Compound Chemical Structure 

Common name Bensulide 

IUPAC name O,O-diisopropyl-S-2-phenylsulfonylaminoethylphosphorodithioate 

CAS name S-(O,O-diisopropyl phosphorodithioate) ester of N-(2-mercaptoethyl) 

benzenesulfonamide 

CAS # 741-58-2 

Compound Chemical Structure 

Common name Bensulide Oxon 

IUPAC name O,O-diisopropyl-S-2-phenylsulfonylaminoethylphosphorothioate 

CAS name S-(O,O-diisopropyl phosphorothioate) of N-(2-mercaptoethyl) 

benzenesulfonamide 

CAS # 20243-81-6 

3.2 Physical/Chemical Characteristics 

Bensulide (5.6 mg/L) is moderately soluble in water; however, it is less soluble than its oxon 

(461 mg/L, EPISuite v. 4.10). Both compounds have low volatility and the oxon has a lower 

octanol/water partition coefficient. 

Table 3.2. Physicochemical Properties of Bensulide and Bensulide Oxon 

Parameter Value Reference 

Bensulide 

Molecular weight (g/mole) 397.54 MRID 45761801 

Melting point (°C) 36 MRID 41532001 

Water solubility ( mg/L at 25°C) 5.6 MRID 41532001 

Vapor pressure at 25°C (mmHg) 8.2 x 10-7 MRID 41532001 

Dissociation constant (pKa) Not Applicable 

Octanol/water partition coefficient Log(KOW) 4.20 H. Zhong, D428601, 

09/14/2015 (values 

modeled with EPI Suite, v 

4.10) 

Bensulide oxon 

Molecular weight (g/mole) 381.44 H. Zhong, D428601, 

09/14/2015 (values 

modeled with EPI Suite, v 

Melting point (°C) 89.97 

Water solubility ( mg/L at 25°C) 461.24 

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Table 3.2. Physicochemical Properties of Bensulide and Bensulide Oxon 

Parameter Value Reference 

Vapor pressure at 25°C (mmHg) 2.48 10-8 4.10) 

Dissociation constant (pKa) Not Applicable 

Octanol/water partition coefficient Log(KOW) 2.35 

3.3 Pesticide Use Pattern/Directions for Use (860.1200) 

Prefar 4 E (EPA Reg. No. 10163-200) is the only bensulide end-use product registered in the 

U.S. for food uses; it is registered for application to bulb onion, garlic, shallots, peppers 

(bell/nonbell), tomatillo, leafy vegetable except brassica (CG 4), leafy brassica vegetables (CG 

5), cucurbit vegetables (CG 9), and regional use on carrots grown in Texas. Maximum single 

application rates range from 5 to 6 lbs ai/A. 

Conclusions: Since magnitude of the residue data have not been submitted for non-bell peppers, 

HED concludes that they should be removed from the label. For clarity, the label needs to be 

modified to remove reference to the fruiting vegetable crop group and specify application to bell 

peppers and tomatillo. In addition, the maximum seasonal application rate is not specified for 

cucurbit vegetables, tomatillo, or bell peppers. A maximum seasonal application rate of 6 lbs 

ai/A is adequate for crops in these crop groups. 

4.0 Metabolite/Degradate Residue Profile 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997

4.1 Nature of the Residue 

Plants: The reregistration requirements for plant metabolism are fulfilled. Acceptable studies 

depicting the qualitative nature of the residue in carrots, lettuce, and tomatoes have been 

submitted and evaluated. HED has determined that the bensulide residues of concern are those 

that are currently regulated, bensulide and bensulide oxygen analog. 

Livestock: Data pertaining to the nature of the residue in animals are not required. The only 

livestock feed item associated with registered bensulide uses is carrot culls which is fed to dairy 

cattle and may consist of up to 10% of the diet. Currently, product labels include a restriction 

against the feeding of treated carrots to livestock. Although the Agency normally does not 

support this type of feeding restriction, in the 1997 chemistry chapter for the RED it was 

determined that this restriction can be allowed because use of bensulide on carrots is limited to 

TX and low residues are present on carrots. If additional uses of bensulide that may result in 

residues in feedstuff are proposed in the future, livestock metabolism studies will be required. 

Confined Rotational Crops: The reregistration requirements for accumulation in rotational 

crops are fulfilled. An adequate confined rotational crop study has been submitted and 

evaluated. The nature of the residue in rotational crops appeared to be similar to the nature of 

the residue in primary crops. No limited field trials or tolerances for inadvertent residues of 

bensulide were required, provided that a 120-day plantback interval is established for rotational 

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crops. Limited field rotational crop trials would be required to support plantback intervals of less 

than 120 days. Currently, product labels specify a plantback interval of 120 days for all crops 

not included on the label. 

4.2 Residues of Concern Summary and Rationale 

The nature of the residues in plants is adequately established based on carrot, lettuce and tomato 

metabolism studies. The residues of concern for risk assessment in plants and drinking water and 

tolerance enforcement in plants consists of bensulide and its oxon (C. Eiden, D238417, 

10/06/1997). 

Table 4.3. Summary of Metabolites and Degradates to be included in the Risk Assessment and 

Tolerance Expression

Matrix Residues included in Risk 

Assessment 

Residues included in 

Tolerance Expression 

Plants Primary Crop Bensulide and its Oxon Bensulide and its Oxon 

Rotational Crop NS1 NS1

Livestock 

Ruminant 

NR1

 NR1

Poultry 

Drinking Water Bensulide and its Oxon Not Applicable 

1 NS = Not specified. It was indicated that the nature of the residue seems to be similar to that on primary crops (C. 

Eiden, D218575, 04/02/1997). Following the 120-day plant-back interval (PBI), residues in rotational crops do not 

need to be considered for risk assessment and tolerance enforcement. 2

 NR = Not required to support the established uses of bensulide. Livestock metabolism studies may be required if 

new uses are sought. 

5.0 Residue Profile 

5.1 Residue Analytical Methods (860.1340) 

5.1.1 Tolerance Enforcement and Data Collection Methods 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997

Adequate methods are available for data collection and tolerance enforcement for plant 

commodities. The PAM Vol. II lists GC Method I, using either phosphorus-sensitive thermionic 

detection or flame photometric detection, for the determination of bensulide and bensulide 

oxygen analog in plant commodities. Moreover, TLC Method A is available for confirmation. 

Method I uses benzene as a solvent. Methods used for data collection were modifications of 

Method I with the substitution of toluene for benzene. 

5.1.2 Multi-Residue Methods (860.1360) 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997

The PAM (Volume I, Appendix I) indicates that bensulide is completely recovered (>80%) using 

Multiresidue Methods Sections 302 (Luke Method; Protocol D) and 304 (Mills Method; Protocol 

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E, fatty foods) and partially recovered (70%) using Section 303 (Mills, Onley, Gaither Method; 

Protocol E, non-fatty foods). No information regarding the recovery of bensulide oxygen analog 

using Multiresidue Methods is included in the PESTDATA database. 

5.1.3 Data Acquisition Methods 

Tomato Processing Study: 4435501.der.doc

The samples used in the tomato processing study were analyzed for bensulide and bensulide 

oxon by EN-CAS Analytical Laboratories using the analytical method #CSJ-009-02, entitled 

Analytical Method for the Determination of Bensulide and Bensulide Oxon in Various Crops by 

Gas Chromatography, issued 6/01/94, included in Gowan Study #94005-GOWN, RAC 

Residues - Bell Peppers as the reference method with minor EN-CAS modifications as needed. 

The method was validated for analysis of whole tomatoes. Method validation recoveries for 

bensulide ranged from 88 to 92% (mean= 90% ± 1.5, n = 6). Method validation recoveries for 

bensulide oxon ranged from 86 to I 06% (mean= 96% ± 7.6, n = 6). One unfortified control and 

two control samples fortified at different levels of bensulide and bensulide oxon and duplicate 

subsamples of the two samples from the treated plot were analyzed for each set. Bensulide 

procedural recoveries ranged from 94 to 101% (mean= 97% ± 3.0, n = 4). Bensulide oxon 

procedural recoveries ranged from 76 to 81% (mean= 78% ± 2.4, n = 4). 

Conclusions: An adequate data acquisition method was used to analyze the samples of bensulide 

on tomato. The method is supported by adequate method validation and concurrent recoveries 

for bensulide and its oxygen analog. 

5.1.4 Submittal of Analytical Reference Standards (860.1650) 

Reference standards for bensulide (expiration date 04/30/2018) and its oxygen analog (expiration 

date 07/23/2017) are currently available in the standard repository (personal communication with 

Gregory Verdin, 09/29/2015). These standards need to be supplied before their expiration date. 

5.2 Storage Stability (860.1380) 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997

A storage stability study evaluated in the RED indicated some degree of instability of residues of 

bensulide per se in/on broccoli, cabbage, cucumber and leaf lettuce under frozen storage 

conditions. Residues of bensulide per se were demonstrated to be stable for up to 6 months in/on 

cabbage and cucumber, and for less than 3 months in/on broccoli and leaf lettuce. Residues of 

bensulide per se declined by 55-61% in/on broccoli after 12 months and by 51-53% in cabbage, 

43-46% in/on cucumber, and 57-59% in/on leaf lettuce after 36 months. Based on the storage 

intervals employed in the submitted residue studies and the stability data submitted, HED 

believes that residues of bensulide oxon were stable during the given storage periods prior to 

analysis. 

The Agency considered the results of the available storage stability data during tolerance 

reassessment, and concluded that in order to account for potential residue losses during storage 

prior to analysis, the tolerance for bensulide residues should be increased from 0.10 ppm (based 

on non-detectable levels of bensulide per se (0.05 ppm) plus bensulide oxon (0.05 ppm)) to 0.15 

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ppm (based on twice the limit of detection for bensulide per se (0.10 ppm) plus the limit of 

detection for bensulide oxon (0.05 ppm)) for the following commodities or crop groups: 

curcurbits, leafy vegetables, Brassica (Cole) leafy vegetables group. Residues of bensulide and 

bensulide oxon were stable in carrots (data translated from potatoes), onions, and bell peppers 

during the periods of storage prior to analysis. Therefore, tolerances for these commodities are 

based on field trial data that has not been corrected for residue losses during storage. 

For the tomato processing study, frozen samples were received at EN-CAS from the field test 

sites on 8/20/97. Samples were transferred to a laboratory freezer for storage where they 

remained frozen until homogenization and subsampling. Freezer storage temperatures were 

monitored on a daily basis and were maintained approximately at or below 14 ° F. Complete 

temperature monitoring data are available upon request. Sample storage time from sampling in 

the field to extraction for analysis at the analytical laboratory was 8 days. 

Conclusions. Adequate storage stability data are available to support the established uses of 

bensulide. The established tolerances have been modified to consider potential loss that may 

have occurred during storage of the field trial samples. Because the storage time from sampling 

of the tomato samples in the field to analysis was 8 days, the samples of the processing study are 

supported by adequate storage stability data. 

5.3 Residue Data 

5.3.1 Crop Field Trials (860.1500) 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997

Adequate data are available to support the currently registered uses on bulb onion (garlic and 

shallot), tomatillo, bell-peppers, leafy vegetable except brassica (CG 4), leafy brassica vegetable 

(CG 5), and cucurbit vegetable (CG 9), and carrots grown in Texas. 

Non-bell Peppers 

Representative commodities for the fruiting vegetables crop group 8 include tomato, bell pepper, 

and a cultivar of a non-bell pepper. A magnitude of residue study for bensulide in/on non-bell 

peppers has been required in the RED and scoping document. Three geographically 

representative field trials on non-bell peppers were required. These data have not been submitted. 

Alternatively, it was indicated that the registrant could restrict use to bell peppers only. 

Currently, the bensulide end-use product label (e.g. Prefar 4-E; EPA Reg. No. 10163-200, 

12/13/2013) includes instructions for use on non-bell peppers such as chili peppers, cooking 

peppers, pimentos and sweet peppers. In the absence of the required non-bell pepper data, the 

label should be amended to remove the non-bell pepper cultivars and restrict the use to bell 

peppers only. 

Tomato 

The established domestic use on tomatillo is covered by the tolerance for tomato (40 CFR § 

180.1). Therefore, the tomato domestic field trial data does support the tomatillo use. In the 

residue chemistry chapter for the RED it was stated that the registrant had previously proposed to 

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retain the tolerance for fruiting vegetables crop group 8 (i.e. includes tomato) for import 

purposes. To support the import tolerance, HED requested English translations of the labels 

from all countries where bensulide can be applied to tomato, 12 tomato field trials conducted in 

Mexico, and a tomato processing study. The Mexican labels were provided by the registrant 

(Prefar 480-E, Mexican label received on 11/16/2015) and a tomato processing study is available 

(MRID 44435501, currently under review). Crop field trial data conducted in Mexico has not 

been submitted. However, the Mexican label specifies a single application rate of 6 lbs ai/A to 

tomato. HED notes that domestic tomato field trial data are available which employed a single 

preplant incorporated or preemergence broadcast application of the 4 lb/gal EC formulation at 

4.0 lb ai/A (8 trials), 5.0 lb ai/A (5 trials), 6.0 lb ai/A (5 trials), 8.0 lb ai/A (1 trial), or 10 lb ai/A 

(1 trial) followed by harvest of tomatoes at maturity in 15 trials, green tomatoes in 4 trials in CA 

(5 lbs ai/A), and the entire tomato plant in 1 trial (overall, PHIs ranged from 65 to 165 days); 

residues of bensulide and its oxygen analog were less than the LOQ (<0.05 ppm each) in/on 

samples (C. Eiden, D238521, 10/07/1997). The registrant indicated their intent to submit a 

proposal or waiver for the previously requested crop field trials (11/30/2015, meeting 

coordinated by Margaret Hathaway). Provided that the US crop field trials were conducted in 

locations with similar climate and conditions to those in Mexico, and that the final review of the 

label indicates that the application scenarios in the US and Mexico are similar, HED may 

conclude that these field trial data are sufficient to waive the previously requested 12 Mexican 

tomato field trials and support a tolerance of 0.10 ppm in/on imported tomato. Otherwise, the 

petitioner should submit the previously requested 12 Mexican tomato field trials conducted at the 

maximum rate for the importing countries. 

Conclusion: Magnitude of residue studies are required to support uses on non-bell peppers. In 

the absence of this study it is recommended that this use is eliminated from the label. Crop field 

trial data (or an acceptable waiver request) needs to be submitted to establish a tolerance for 

tomato imported from Mexico. 

5.3.2 Field Rotational Crops (860.1900) 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997

Based on the confined rotational study, no limited field trials or tolerances for inadvertent 

residues of bensulide were required, provided that a 120-day plantback interval is established for 

rotational crops. Limited field rotational crop trials would be required to support plantback 

intervals of less than 120 days. Currently, product label specify a plantback interval of 120 days 

for all crops not included on the label. 

5.3.3 Processed Food and Feed (860.1520) 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997 

Tomato Processing Study: 44435501.der.doc

Tomato processing studies were required in the RED to support domestic uses or residues in/on 

imported tomatoes. Currently, the only crop under the tomato subgroup that is registered for 

domestic uses is tomatillo which is used mainly as seasoning, in chili sauce, salsas, and meats. 

Moreover, a tomato processing study was required to support uses on tomato to be imported. 

A tomato processing study was provided by the registrant (MRID 44435501). This study was 

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conducted in tomatoes following one ground application with Prefar® Herbicide whose active 

ingredient is bensulide. A field trial was established at in California. Since tomatoes grown in 

California represent greater than 68% of the U.S. production, testing in this area ensured 

adequate representation. Two plots were established at the test site. One plot was untreated and 

provided control samples. Another plot was treated with an exaggerated application rate of the 

test substance. Bensulide was applied to the treated plot one time as a preplant incorporated 

application. The application was made at an exaggerated rate (5X) of 29.8 lb active ingredient 

(a.i.)/A in 29 gallons per acre (GPA) of carrier using a tractor-mounted ground sprayer. Whole 

fruit was collected at normal commercial maturity 99 days after the application (DAA) and 

shipped frozen overnight with dry ice to the analytical laboratory. These samples were analyzed 

immediately. Since residues in the RAC samples were <0.1 ppm, processing of the tomatoes was 

not required. 

Conclusions: Tolerances for tomato processed commodities are not required since the tolerance 

for the RAC covers residues in processed commodities. 

5.3.4 Meat, Milk, Poultry and Eggs (860.1480) 

Residue Chemistry Chapter for the RED: C. Eiden, D238417, 10/06/1997

Feeding studies for bensulide in/on livestock are not required. The only livestock feed item 

associated with registered bensulide uses is carrot culls which is fed to dairy cattle and may 

consist of up to 10% of the diet. Currently, product labels include a restriction against the 

feeding of treated carrots to livestock. In the 1997 chemistry chapter for the RED it was 

determined that this restriction can be allowed because use of bensulide on carrots is limited to 

Texas and low residues are present on carrots. If additional uses of bensulide are required in the 

future, livestock feeding studies may be required. 

5.3.5. Food Handling (860.1460) 

Bensulide is presently not registered for use in food-handling establishments; therefore, no 

residue chemistry data are required under this guideline topic. 

5.3.6 Water, Fish, and Irrigated Crops (860.1400) 

Bensulide is presently not registered for direct use on water and aquatic food and feed crops; 

therefore, no residue chemistry data are required under this guideline topic. 

5.4 Food Residue Profile 

The nature of the residues in plants is adequately established based on carrot, lettuce and tomato 

metabolism studies. Tolerances are established in the 40 CFR § 180.241 for the use of bensulide 

on bulb onion, leafy vegetable except brassica (CG 4), leafy brassica vegetables (CG 5), fruiting 

vegetable (CG 8), and cucurbit vegetables (CG 9), and a regional registration for use on carrots. 

Uses on garlic and shallots are in the label as well which is covered by the tolerance for bulb 

onion, refer to the 40 CFR § 180.1. The established tolerances are based on measurement of 

bensulide and its oxygen analog and range from 0.10 to 0.15 ppm. The 0.10 ppm tolerances are 

based on combined levels of bensulide and its oxon at the LOQ of 0.05 ppm. However, in order 

Page 12 of 20
Bensulide Summary of Analytical Chemistry and Residue Data Barcode D429307 

Page 13 of 15 

to account for potential residue losses during storage prior to analysis, the tolerance for bensulide 

residues on brassica vegetables (CG 5), cucurbit vegetables (CG 9) and leafy vegetables (CG 4) 

is 0.15 ppm (based on twice the limit of quantitation for bensulide per se (0.10 ppm) plus the 

limit of quantification for bensulide oxon (0.05 ppm)). 

Metabolism studies conducted with lettuce, carrot and tomato show that parent bensulide was at 

quantifiable levels only in carrot, while the oxygen analog was quantified in lettuce and carrot, 

refer to Appendix B. Levels of the oxon were higher than those of parent bensulide only in 

lettuce, which suggest that the oxon may predominate. Moreover, PDP data for lettuce (years 

2010 and 2011) shows that bensulide was detected in 6 of 1487 samples whereas bensulide oxon 

was detected in 49 of those 1487 samples. Generally, the concentration of the oxon in/on lettuce 

is higher than that of parent bensulide. PDP data for carrots do not show quantifiable residues of 

bensulide or its oxon while data for tomato do not shows residues of bensulide’s oxygen analog. 

 

Page 13 of 20
Bensulide Summary of Analytical Chemistry and Residue Data Barcode D429307 

Page 14 of 15 

Appendix A. International Residue Limits Table

Bensulide (PC Code 009801) 

Summary of U.S. and International Tolerances and Maximum Residue Limits 

Residue Definition:

U.S. Canada Mexico2 Codex

40 CFR 180.241:

(a) General. (1) -(O,O-diisopropyl 

phosphorodithioate) of N-(2-mercaptoethyl) 

benzenesulfonamide including its oxygen analog 

S-(O,O-diisopropyl phosphorothioate) of N-(2-

mercaptoethyl) benzenesulfonamide

None None 

Commodity1 Tolerance (ppm) /Maximum Residue Limit (mg/kg)

U.S. Canada Mexico2 Codex

Onion, bulb 0.10 

Vegetable, brassica, leafy group 5 0.15

Vegetable, cucurbits group 9 0.15

Vegetable, fruiting group 8 0.10

Vegetable, leafy except brassica 

group 4

0.15

 

Completed: M. Negussie; 09/21/15

1

 Includes only commodities of interest for this action. 

2 Mexico adopts U.S. tolerances and/or Codex MRLs for its export purposes. 

(c) Tolerances with regional registrations. Tolerances with regional registration, as defined in §180.1(l), 

are established for the residues of S-(O,O-diisopropyl phosphorodithioate) of N-(2-mercaptoethyl) 

benzenesulfonamide including its oxygen analog S-(O,O-diisopropyl phosphorothioate) of N-(2-

mercaptoethyl) benzenesulfonamide in or on the following food commodities: 

Commodity Parts per million 

Carrot, roots 0.10 

 

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Bensulide Summary of Analytical Chemistry and Residue Data Barcode D429307 

Page 15 of 15 

Appendix B. Comparison of Residue Levels of Bensulide and its Oxon 

Table B.1 summarizes residue data for commodities that do not have PDP data available for both 

parent bensulide and its oxon. The purpose is to provide information to address the dietary 

exposure and risk assessment. In addition, PDP data for lettuce (in which bensulide and its oxon 

were measured) were included. 

Table B.1. Summary of Residue Levels for Bensulide and its Oxon 

Matrix (Reference) Use Pattern / 

PDP Sample ID 

Bensulide Bensulide 

Oxon 

Factor 

(Oxon/Parent) 

Tomato Metabolism 

(D179576, 04/21/1993) 

8.6 lbs ai/A pre-plant 

112-153 day PHI 

ND 

(86% TRR 

iden/char) 

ND 

(86% TRR 

iden/char) 

NA 

Lettuce Metabolism 

(D1855889, 03/29/1993) 

8.6 lbs ai/A soil preplant 

67 day PHI 

ND 

(86% TRR 

extracted) 

2% TRR 

(86% TRR 

extracted) 

NA 

Carrot Metabolism 

(D177460, 06/02/1992) 

8.6 lbs ai/A soil preplant 

126 day PHI 

30% TRR 

(94% TRR 

extracted) 

2.8% TRR 

(94% TRR 

extracted) 

0.09x 

Squash Field Data 

(D218256, 01/24/1996) 

9 lbs ai/A pre-plant ND1 ND1 NA 

Cucumber Field Data 

(D218256, 01/24/1996) 

9 lbs ai/A pre-plant ND1 ND1 NA 

Bulb Onion 

(D206633, 11/29/1994) 

9 lbs a.i./A pre-plant or 

pre-emergence 

Harvest at Maturity 

ND1

 ND1 NA 

Bell Peppers 

(D238521, 10/07/1997) 

5-9 lbs ai/A pre-plant or 

pre-emergence 

109-129 day PHIs 

ND1

 ND1 NA 

Lettuce PDP Results 

(years 2010-2011) 

2010-6721 0.005 0.01 2.0 

2010-6845 0.004 0.005 1.3 

2010-7044 0.014 0.12 8.6 

2010-7052 0.005 0.008 1.6 

2010-7265 0.014 0.023 1.6 

2011-6295 0.012 0.003 0.3 1

 The LOQ is reported to be 0.05 ppm. 

Lettuce: The metabolism study with lettuce showed detection of the oxon but not of the parent 

bensulide which suggest that the oxon may predominate. PDP data for lettuce (years 2010 and 

2011) shows that bensulide (LOD ≤ 0.014 ppm) was detected in 6 of 1487 samples whereas 

bensulide oxon (LOD ≤ 0.002 ppm) was detected in 49 of those 1487 samples. The samples in 

which both were detected were included in the table above in order to estimate the ratio of the 

concentration of the oxon with respect to parent bensulide. These factors range from 0.3 to 8.6. 

This data suggest a factor of 9x for oxon residues with respect to bensulide. 

Other Crops (Non-Leafy): The metabolism study with tomato and carrot and the crop field trial 

data do not suggest that parent bensulide or the oxon may be present at significant 

concentrations. PDP data with summer squash, carrot and tomato was generated for bensulide 

and its oxon. Only two sample of tomato showed bensulide being detected; however, there were 

not detects of the oxon. This suggest that both residues of concern would be at low 

concentrations and that the oxon do not seem to predominate in these crops. 

Page 15 of 20
Bensulide [PC Code 00980 I ]/Gowan Company 

B.7.7 

B.7.7.1 

B.7.7.2 

B.7.7.3 

B.7.7.3.1 

Document ID: 

Report: 

Guidelines: 

Effects of Industrial Processing and/or Household Preparation 

(Annex HA 6.5; Annex IHA 8.5) 

Nature of the Residue 

(Annex HA 6.5.1; Annex IHA 8.5.1) -Not a data requirement in North America 

Distribution of the Residue in Peel/Pulp 

(Annex HA 6.5.2; Annex IHA 8.5.2) 

To be included if available. 

Magnitude of Residues on Set of Representative Processes 

(Annex HA 6.5.3; Annex IHA 8.5.3) 

Tomato 

MRID No. 44435501 

Carringer, S. (1997) Magnitude of the Residue of Bensulide in Tomato 

Processed Commodities. Study Numbers: AA970609 and 97-0003. 

Unpublished study prepared by Gowan Company. 162 p. 

EPA OCSPP Harmonized Test Guideline 860.1520 Processed Food/Feed 

(August 1996) 

PMRA Regulatory Directive DIR98-02 -Residue Chemistry Guidelines, 

Section 10 - Processed Food/Feed 

OECD Guideline 508 Magnitude of the Pesticide Residues in Processed 

Commodities (October 2008) 

GLP Compliance: No deviations from regulatory requirements were reported which would 

have an impact on the validity of the study. 

Acceptability: The study is considered scientifically acceptable. The acceptability of this 

study for regulatory purposes is addressed in the forthcoming U.S. EPA 

Residue Chemistry Summary Document, DP#~.,?· 

Evaluator: Ideliz Negr6n-Encamaci6n, Ph.D., Chemist ~---

Note: This Data Evaluation Record (DER) was originally prepared under contract by Versar, Inc. (6850 Versar Center, 

Springfield, VA 22151 ; submitted 12/04/2015). The DER has been reviewed by HED and revised to reflect current Office of 

Pesticide Programs (OPP) policies. 

EXECUTIVE SUMMARY 

In response to the Residue Chemistry Chapter of the Bensulide Reregistration Eligibility 

Decision (RED; DP# 238417, C. Eiden, 9/11/97), Gowan Company has submitted a processing 

study with bensulide on tomato. In one trial conducted in CA during the 1997 growing season, a 

4 lb ai/gal emulsifiable concentrate (EC) formulation of bensulide (Prefar® Herbicide) was 

applied to tomatoes as a single preplant incorporated application at 29.8 lb ai/A (designated 5x 

by the petitioner) the day before planting. The application was made using ground equipment in 

a spray volume of29 gal/A. No adjuvant was used. Tomatoes (RAC) were harvested at 

EPA MRID #: 44435501 Page I of5 

Page 16 of 20
Bensulide [PC Code 009801]/Gowan Company 

EPA MRID #: 44435501 Page 2 of 5 

maturity 98 days after planting (DAP) at a 99-day preharvest interval (PHI). No processing was 

conducted with the study. 

Samples were stored frozen at the test facility, during shipping, and at the analytical laboratory 

until analysis. The storage interval between harvest and analysis was 8 days. Samples were 

analyzed on the day of extraction. No storage stability data are needed to support the study. 

Samples were analyzed for residues of bensulide and bensulide oxon using a gas 

chromatography method with flame photometric detection (GC/FPD), Method #CSI-009-02, 

with minor modifications. Acceptable method validation and concurrent recoveries were 

reported for samples of tomato fortified with bensulide and bensulide oxon each at 0.05-5.0 ppm, 

thus validating the method. The limit of quantitation (LOQ; determined as the lowest level of 

method validation, LLMV) was 0.05 ppm for each analyte. The fortification levels used in 

concurrent method recovery were adequate to bracket expected residue levels. Concurrent 

recoveries were corrected for apparent residues in controls; residues in treated samples were not 

corrected for residues in controls. 

Following a single preplant incorporated application of a 4 lb ai/gal EC formulation of bensulide 

at an exaggerated rate of 29.8 lb ai/A, residues of bensulide and bensulide oxon were each below 

the LOQ (<0.05 ppm) in/on all samples of tomato. Because residues were below the LOQ in/on 

all samples following exaggerated-rate (reportedly ~5x) application, no processing was 

conducted. 

The maximum theoretical processing factors for tomato are 1.4x and 5.5x for puree and paste 

(based on loss of water; OCSPP 860.1520, Table 2) and 1.4x for juice (based on separation into 

components; OCSPP 860.1520, Table 3). 

I. MATERIALS AND METHODS 

A. MATERIALS 

Table B.7.7.3.1-1. Nomenclature for Bensulide. 

Common name Bensulide 

Identity S-(O,O-diisopropyl phosphorodithioate) ester of N-(2-

mercaptoethyl)benzenesulfonamide 

CAS no. 741-58-2 

Company experimental name Not applicable 

Other synonyms (if applicable) Not Applicable 

Common name Bensulide oxon 

Identity S-(O,O-diisopropyl phosphorothioate) ester of N-(2-

mercaptoethyl)benzenesulfonamide 

CAS no. 20243-81-6 

Company experimental name Not applicable 

Other synonyms (if applicable) Bensulide oxygen analog 

Page 17 of 20
Bensulide [PC Code 009801]/Gowan Company 

EPA MRID #: 44435501 Page 3 of 5 

Table B.7.7.3.1-1. Nomenclature for Bensulide. 

B. Study Design 

1. Test Procedure 

One trial was conducted on tomato in CA during the 1997 growing season reflecting a single 

preplant incorporated application of a 4 lb ai/gal EC formulation of bensulide at an exaggerated 

rate. 

Location and detailed use pattern for the trial is provided in Table B.7.7.3.1-2. 

Table B.7.7.3.1-2. Study Use Pattern. 

Location: City, State; 

Year 

(Trial ID) 

End-use 

Product1

Method of Application/ 

Timing of Application

Volume

(gal/A)

Rate per 

Application

(lb ai/A) 

Retreatment 

Interval 

(days) 

Total 

Rate 

(lb ai/A) 

Surfactant/ 

Adjuvant

Porterville, CA; 1997 

(AA970609.CA) 

4 lb ai/gal 

EC 

1. Preplant incorporated; 1 

day before planting. 

29.6 29.8 -- 29.8 None 

1 4 lb ai/gal emulsifiable concentrate (EC) formulation (Prefar® Herbicide). 

The registrant indicated that tomatoes were initially stunted, presumably due to the exaggerated 

rate of the test substance application; however, tomatoes had recovered by harvest and were in 

excellent condition. Irrigation was used as necessary. No unusual weather conditions were 

reported to have adversely affected crop production or yield during the study. 

Sample Handling and Preparation 

Single control and duplicate treated samples (>5.0 lb) of tomatoes were collected 98 DAP at a 

PHI of 99 days. Samples were placed in frozen storage (-7 to 16 °F) at the test site within 1 hour 

of collection and were shipped frozen within 5 days of harvest via overnight delivery on dry ice 

to the analytical laboratory, EN-CAS Analytical Laboratories (Winston-Salem, NC). Samples 

were stored frozen (≤14 °F) at the analytical laboratory until analysis. Samples were prepared 

for analysis by homogenizing in the presence of dry ice. 

Sample Processing 

No processing was conducted.

2. Description of Analytical Procedures 

Samples were analyzed for residues of bensulide and bensulide oxon using GC/FPD Method 

#CSI-009-02, with minor modifications including replacing nitrogen-phosphorus detection with 

flame photometric detection. 

Page 18 of 20
Bensulide [PC Code 009801]/Gowan Company 

EPA MRID #: 44435501 Page 4 of 5 

Briefly, samples were extracted with toluene and centrifuged. The supernatant was filtered 

through sodium sulfate, then evaporated to dryness by rotary evaporation and reconstituted in 

hexane. The hexane solution was partitioned three times with acetonitrile (ACN), and the ACN 

phases were combined and mixed with water, saturated NaCl solution, and 2% citral in toluene. 

The resulting citral/toluene layer was back-washed twice with water/NaCl then filtered through 

sodium sulfate for analysis by GC/FPD. 

The LOQ (determined as the LLMV) was 0.05 ppm for each analyte. The limit of detection 

(LOD) was not reported. 

II. RESULTS AND DISCUSSION 

Method performance was evaluated during method validation and by use of concurrent recovery. 

For method validation and concurrent recovery, samples of tomato were fortified with bensulide 

and bensulide oxon, each at 0.05 and 5.0 ppm for method validation and at 0.05 and 1.0 ppm for 

concurrent recoveries. Recoveries were within the acceptable range of 70-120%; therefore, the 

method was considered valid for the analysis of bensulide residues in/on tomato matrices (Table 

B.7.7.3.1-3). The fortification levels bracketed the measured residues. Concurrent recoveries 

were corrected for apparent residues in controls. 

Based on representative calibration curves, the detector response was linear for tomato matrices 

(coefficients of determination for bensulide and bensulide oxon were: r2 ≥0.9982 and r2

≥0.9974 within the range of 0.100-2.0 ng standard injected). Representative chromatograms of 

control samples, fortified samples, and treated samples were provided. The control 

chromatograms generally had no peaks of interest above the chromatographic background. The 

fortified sample chromatograms contained only the analyte of interest, and peaks were 

symmetrical and well defined. Apparent residues in controls were below the LOQ (<0.05 ppm) 

for both analytes in/on all matrices. The reported residue values were not corrected for apparent 

residues in controls. 

Table B.7.7.3.1-3. Summary of Method Validation and Procedural/Concurrent Recoveries of Bensulide and 

Bensulide Oxon from Tomato Matrices.

Matrix Analyte Fortification 

Level (ppm) 

Sample size 

(n) 

Recoveries1

(%) 

Mean ± Std. Dev.

(%) 

Method Validation 

Tomato Bensulide 0.05-5.0 6 88-92 90 ± 1.5 

Bensulide oxon 0.05-5.0 6 86-106 96 ± 7.9 

Concurrent Recoveries 

Tomato Bensulide 0.05-1.0 4 94-101 97 ± 3.0 

Bensulide oxon 0.05-1.0 4 76-81 78 ± 2.4 1 Concurrent recoveries were corrected for apparent residues in controls. 

Sample storage conditions and durations are summarized in Table B.7.7.3.1-4. Tomato samples 

were stored for 8 days between harvest and extraction for analysis. Samples were analyzed on 

the day of extraction. No storage stability data are needed to support the study. 

Page 19 of 20
Bensulide [PC Code 009801]/Gowan Company 

EPA MRID #: 44435501 Page 5 of 5 

Table B.7.7.3.1-4. Summary of Storage Conditions1. 

Matrix Analyte Storage Temperature Actual Storage Duration Interval of Demonstrated Storage Stability

Tomato\ Bensulide and 

bensulide oxon

≤16 °F 8 days None needed. 

1 Interval from harvest/processing to extraction. Samples were analyzed on the day of extraction. 

Residues found in samples and processing factors are given in Table B.7.7.3.1-5. Following a 

single preplant incorporated application of a 4 lb ai/gal EC formulation of bensulide at an 

exaggerated rate of 29.8 lb ai/A, residues of bensulide and bensulide oxon were each below the 

LOQ (<0.05 ppm) in/on all samples of tomato. Because residues were below the LOQ in/on all 

samples following exaggerated-rate (reportedly ~5x) application, no processing was conducted. 

Table B.7.7.3.1-5. Residue Data from Tomato Processing Study with Bensulide. 

Commodity Analyte Residues (ppm) 

[Average]1

Processing Factor Median Processing Factor

Tomato (RAC) Bensulide <0.05, <0.05 [<0.05] -- 

Bensulide oxon <0.05, <0.05 [<0.05] -- 1 The LOQ was 0.05 ppm for each analyte; the LOD was not reported. All values are the result of duplicate analyses and 

duplicate injections. 

III. CONCLUSIONS 

The tomato processing study is considered scientifically acceptable. Following a single preplant 

incorporated application of a 4 lb ai/gal EC formulation of bensulide at an exaggerated rate of 

29.8 lb ai/A, residues of bensulide and bensulide oxon were each below the LOQ (<0.05 ppm) 

in/on all samples of tomato. Because residues were below the LOQ in/on all samples following 

exaggerated-rate (reportedly ~5x) application, no processing was conducted. 

The maximum theoretical processing factors for tomato are 1.4x and 5.5x for puree and paste 

(based on loss of water; OCSPP 860.1520, Table 2) and 1.4x for juice (based on separation into 

components; OCSPP 860.1520, Table 3). 

An acceptable method was used for residue quantitation; no storage stability data are required to 

support sample storage durations and conditions. 

REFERENCES

Residue Chemistry Chapter of the Bensulide Reregistration Eligibility Decision, DP# 238417, C. 

Eiden, 9/11/97. 

Page 20 of 20