Test Material: Propyzamide (Pronamide, RH-23315)

MRID: 48599207

Title: Method Validation Study for the Determination of Residues of Propyzamide and its Metabolites in Surface Water, Ground Water and Drinking Water by Liquid Chromatography with Tandem Mass Spectrometry

MRID: 48690302

Title: Independent Laboratory Validation of Enforcement Method for theDetermination of Propyzamide and its RH-24644, RH-24655, RH24580, RH-26059, and UK1 Metabolites in Water (surface water, ground water and drinking water) by Li quid Chromatography with Tandem Mass Spectrometry

EPA PC Code: 101701

OCSPP Guideline: 850.6100

For CDM Smith

Primary Reviewer: Lynne Binari Signature:

Date: 8/11/14

Secondary Reviewer: Lisa Muto Si g nature:

Date: 8/11/14

QC/QA Manager: Joan Gaidos Signature:

Date: 8/11/14Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 2 of 12 Analytical method for propyzamide and it s transformation products RH-24644, RH-24655, RH-24580, RH-26059 and UK1 in water

Reports: ECM: EPA MRID No.: 48599207. Grote nhuis, A. and Q. Li. 2011. Method Validation Study for the Determination of Residues of Propyzamide and its Metabolites in Surface Water, Grou nd Water and Drinking Water by Liquid Chromatography with Tandem Mass Spectrometry. Dow AgroSciences Study No.: 110587. Report prepared, sponsored, and submitted by Dow AgroSciences LLC, Indianapolis, Indi ana; 81 pages. Final report issued September 6, 2011. ILV: EPA MRID No. 48690302. Robaugh, D. 2011. Independent Laboratory Validation of Enforcement Method for the Determination of Propyzamide and its RH-24644, RH-24655, RH-24580, RH-26059, and UK1 Metabolites in Water (surface water, ground water and drinking water) by Liquid Chromatography with Tandem Mass Spectrometry. Pyxant Labs Study No.: 2340. Dow AgroSciences Study No.: 110676. Report prepared by Pyxant Labs Inc., Colorado Springs, Colorado, sponsored and submitted by Dow AgroSciences LLC, Indianapolis, Indi ana; 226 pages. Final report issued September 12, 2011.
Document No.: MRIDs 48599207 & 48690302
Guideline: 850.6100
Statements: ECM: The study was conducted in accordance with USEPA FIFRA Good Laboratory Practice (GLP) standards, with the exception that GLP characterizations of test substa nces RH-24655 and RH-26059 occurred during the course of the st udy rather than prior to experiment initiation (p. 3 of MRID 48599207). Signed and dated No Data Confidentiality, GLP, and Quality Assurance statements were provided (pp. 2-4). A statement of the authenticity of the study report was included with the quality assurance statement (p. 4). ILV: The study was conducted in accordance with USEPA FIFRA GLP standards (p. 3 of MRID 48690302). Signed and dated No Data Confidentiality, GLP, and Quality Assurance statements were provided (pp. 2-4). A statement of the authenticity of the study report was included with the quality assurance statement (p. 4).
Classification: This analytical method is classified as supplemental. For all analytes, performance data to validate the method at 10x LOQ were not reported. Sufficient results to validate the c onfirmatory method were not provided. Recommended modifications to the ECM were not implemented in an amended final ECM report. ILV performance data for 0.05 μg/L (LOQ) fortified UK1 (RH-23801) in ground water did not meet OCSPP Guideline 850.6100 criteria. The waters used in the ILV were not characterized.
PC Code: 101701
Reviewer: Karen Milians, Chemist Signature: Date:Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 3 of 12 Executive Summary

This analytical method, Dow AgroSciences St udy No. 110587, is designedfor the quantitative determination of propyzamide and its tr ansformation products RH-24644, RH-24655, RH-24580, RH-26059, and UK1 (RH-23801) in water using LC/M S/MS. For all analytes, performance data to validate the method at 10x LOQ were not reported. The LOQ is less than the lowest toxicological level of concern in water. The ILV validated the quantitation ion method after two trials, with the exception of 0.05 μg/L (LOQ) UK1 fortified ground water (RSD 22%). Sufficient results to validate the confirmatory method were not provided. Modi fications to improve precision and repeatability of the method were ma de to the ECM by the independent laboratory; however, the recommended modifications were not implemented in an amended final ECM report. The waters used in th e ILV were not characterized.

Table 1. Analytical Method Summary

Analyte(s) by Pesticide MRID
EPA Review Matrix Method Date (dd/mm/yyyy) Registrant Analysis Limit of Quantitation (LOQ) Environmental Chemistry

Method Independent Laboratory Validation Propyzamide

48599207 48690302 Water 06/09/2011 Dow AgroSciences LLC LC/MS/MS 0.05 μg/L

RH-24644 0.05 μg/L

RH-24655 0.05 μg/L

RH-24580 0.05 μg/L

RH-26059 0.05 μg/L

UK1 (RH-23801) 0.05 μg/L

I. Principle of the Method

Water (4.0 mL) was combined with acetonitrile ( 1.0 mL), vortexed for a few seconds to mix, then centrifuged (2,000 rpm, 10 minutes; p. 20 of MRID 48599207). An aliquot (1.0 mL) was transferred to an autosampler vial and analyzed by LC/MS/MS.

Samples were analyzed for propyzamide (RH-23315) and its products RH-24644, RH-24655, RH-24580, RH-26059 and UK1 by HPLC (Zorbax SB-C8, 4.6 mm x 75 mm, 3.5 μm column) using a mobile phase of (A) ace tonitrile with 0.1% formic acid and (B) water with 0.1% formic acid [percent A:B at 0 min. 10:90, 3-5 min. 100:0, 5:15-7 min. 10:90) with MS/MS-ESI (electrospray ionization) detection and multiple reaction monitoring (MRM); positive ion mode for propyzamide, RH-24644, RH-24655, RH-24580 a nd UK1, and negative ion mode for RH26059 (pp. 11, 15-18 of MRID 48599207). Injection volume was 30 μL. Analytes were identified using two ion transitions; one for qua ntitation (Q) and one for confirmation (C; p. 21 of MRID 48599207). Ion transitions monitored were as follows: m/z 256 → 190 (Q) and m/z 258 → 192 (C) for propyzamide, m/z 256 → 173 (Q) and m/z 258 → 109 (C) for RH-24644, m/z 258 → 190 (Q) and m/z 258 → 173 (C) for RH-24655, m/z 274 → 173 (Q) and m/z 274 → 109 (C) for RH-24580, m/z 288 → 188 (Q) and m/z 290 → 190 (C) for RH-26059, and m/z 222 → 156 (Q) and m/z 222 → 139 (C) for UK1.Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 4 of 12 In the ILV, the autosampler temperature was reduced from ambient to ca . 15°C due to possible stability issues with the analytes (p. 34; Appendix B, p. 218 of MRID 48690302); no other modifications were reported. However, the ILV considered, in addition to autosampler temperature, the use of syringes and glass pipettes to fortify sa mples (analytes may adhere to plastic) and daily preparation of the mixed calibration standards to be critical method steps (p. 34 of MRID 48690302).

The LOQ and LOD for all analytes were the same in the ECM and ILV at 0.05 μg/L (0.05 ng/mL) and 0.015 μg/L (0.015 ng/mL), respectiv ely (p. 24 of MRID 48599207; p. 33 of MRID 48690302).

II. Recovery Findings

ECM (MRID 48599207): Mean recoveries and relative standard devi ations (RSDs) were within guideline requirements (mean 70-120%; RSD ≤ 20%) for analysis of propyzamide, RH-24580, RH-24644, RH-24655, RH-26059 and UK1 in ground wate r, surface water and drinking water at fortification levels of 0.05 μg/L (LOQ) a nd 1.0 μg/L (20x LOQ; Tables 20-22, pp. 48-50). Recoveries from samples fortified at 0.015 μg /L (LOD) ranged (matrices combined) from 83- 112% for propyzamide, 87-119% for RH- 24580, 74-103% for RH-24644, 90-104% for RH24655, 87-99% for RH-26059, and 87-106% for UK1 (D ER Attachment 2). Performance data (recovery results) from confirmation ion anal yses were not reported. Confirmation ratio differences [comparison of the confirmation ra tio (confirmation ion peak area/quantitation ion peak area) of the recovery sample with the av erage confirmation ratio of the standards, p. 22]

were ≤ 20% for all analytes at both fortification le vels in the three water matrices, with the exception of one 0.05 μg/L RH-24655 fortified surface water sample (Tables 2-19, pp. 30-47). The water matrices were well characterized (p. 19).

ILV (MRID 48690302): Mean recoveries and relative standard deviations (RSDs) were within guideline requirements (mean 70-120%; RSD ≤ 20%) for analysis of propyzamide, RH-24580, RH-24644, RH-24655, RH-26059 and UK1 in ground wate r, surface water and drinking water at fortification levels of 0.05 μg/L (LOQ) and 1.0 μg /L (20x LOQ), with the exception of 0.05 μg/L (LOQ) UK1 fortified ground water (RSD 22%; Tables 19-36, pp. 55-72). Performance data (recovery results) from confirmation ion analyses were not reported. The water matrices were not characterized, but were reported as obtained from Dow AgroSciences (p. 23). The method for quantitation ion analyses was validated, with modi fications, after two trials , with the exception of 0.05 μg/L (LOQ) UK1 fortified ground water (pp. 31-33).Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 5 of 12 Table 2. Initial Validation Method Recoveries for Propyzamide and Its Transformation Products in Water

Analyte Fortification Level (μg/L) Number of Tests Recovery Range (%) Mean Recovery (%) Standard Deviation (%) Relative Standard Deviation (%) Ground (Well) Water

Propyzamide (RH-23315) 0.015 (LOD) 2 94, 101 * * * 0.05 (LOQ) 6 85-116 99 13.3 13.5
1.0 6 96-115 103 7.5 7.3

RH-24580 0.015 (LOD) 2 105, 117 * * * 0.05 (LOQ) 6 95-111 102 5.4 5.3
1.0 6 100-108 103 2.8 2.7

RH-24644 0.015 (LOD) 2 91, 93 * * * 0.05 (LOQ) 6 81-115 96 14.5 15.1
1.0 6 96-120 107 8.4 7.8

RH-24655 0.015 (LOD) 2 92, 100 * * * 0.05 (LOQ) 6 96-105 101 2.9 2.9
1.0 6 98-104 101 2.1 2.1

RH-26059 0.015 (LOD) 2 96, 99 * * * 0.05 (LOQ) 6 92-96 93 1.6 1.7
1.0 6 97-99 98 0.8 0.8

UK1 (RH-23801) 0.015 (LOD) 2 99, 103 * * * 0.05 (LOQ) 6 95-111 100 5.7 5.7
1.0 6 99-107 103 3.1 3.0 Surface (Pond) Water

Propyzamide (RH-23315) 0.015 (LOD) 2 83, 112 * * * 0.05 (LOQ) 6 92-118 100 9.0 9.0
1.0 6 98-118 107 7.8 7.3

RH-24580 0.015 (LOD) 2 103, 119 * * * 0.05 (LOQ) 6 84-112 100 9.7 9.7
1.0 6 97-104 101 2.4 2.4

RH-24644 0.015 (LOD) 2 77, 99 * * * 0.05 (LOQ) 6 91-114 98 8.2 8.4
1.0 6 101-122 108 8.9 8.2

RH-24655 0.015 (LOD) 2 96, 104 * * * 0.05 (LOQ) 6 88-103 95 5.1 5.3
1.0 6 95-102 97 2.1 2.2

RH-26059 0.015 (LOD) 2 92, 99 * * * 0.05 (LOQ) 6 91-95 93 1.8 1.9
1.0 6 93-98 96 1.6 1.7

UK1 (RH-23801) 0.015 (LOD) 2 89, 106 * * * 0.05 (LOQ) 6 100-104 102 1.3 1.3
1.0 6 96-101 98 1.7 1.7 Drinking (Tap) Water

Propyzamide (RH-23315) 0.015 (LOD) 2 86, 104 * * * 0.05 (LOQ) 6 87-104 97 7.7 7.9
1.0 6 95-120 111 10.1 9.1

RH-24580 0.015 (LOD) 2 87, 93 * * * 0.05 (LOQ) 6 95-108 102 5.1 5.0Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 6 of 12 Analyte Fortification Level (μg/L) Number of Tests Recovery Range (%) Mean Recovery (%) Standard Deviation (%) Relative Standard Deviation (%)
1.0 6 98-108 102 3.7 3.6

RH-24644 0.015 (LOD) 2 74, 103 * * * 0.05 (LOQ) 6 79-100 93 8.8 9.5
1.0 6 100-120 113 10.2 9.1

RH-24655 0.015 (LOD) 2 90, 102 * * * 0.05 (LOQ) 6 91-104 96 4.6 4.8
1.0 6 96-106 101 3.7 3.7

RH-26059 0.015 (LOD) 2 87, 97 * * * 0.05 (LOQ) 6 92-97 95 2.1 2.2
1.0 6 98-102 100 1.5 1.5

UK1 (RH-23801) 0.015 (LOD) 2 87, 92 * * * 0.05 (LOQ) 6 91-115 104 9.7 9.3
1.0 6 99-102 100 1.2 1.2 Data (quantitation ion results) were obtained from Tables 20-22, pp. 48-50 of MRID 48599207 and DER Attachment 2 (LOD recovery results). Confirmation ion recovery results were not reported. * Not calculated, n = 2.

Table 3. Independent Validation Method Recoveries for Propyzamide and Its Transformation Products in Water 1

Analyte Fortification Level (μg/L) Number of Tests Recovery Range (%) Mean Recovery (%) Standard Deviation (%) Relative Standard Deviation (%)
Ground Water Propyzamide (RH-23315) 0.05 (LOQ) 5 78-117 99 15 16

1.0 5 73-107 89 12 14

RH-24580 0.05 (LOQ) 5 91-131 112 15 13
1.0 5 92-102 97 4.2 4.4

RH-24644 0.05 (LOQ) 5 89-98 93 3.7 4.0
1.0 5 96-100 98 1.8 1.8

RH-24655 0.05 (LOQ) 5 88-112 101 9.0 8.9
1.0 5 85-105 97 7.5 7.7

RH-26059 0.05 (LOQ) 5 103-111 107 3.2 3.0
1.0 5 103-105 104 0.84 0.80

UK1 (RH-23801) 0.05 (LOQ) 5 55-103 85 19 22
1.0 5 82-107 95 11 12
Surface Water Propyzamide (RH-23315) 0.05 (LOQ) 5 86-98 88 6.5 7.4

1.0 5 98-108 102 4.8 4.7

RH-24580 0.05 (LOQ) 5 96-114 107 7.6 7.2
1.0 5 95-100 98 2.3 2.3

RH-24644 0.05 (LOQ) 5 99-105 103 2.4 2.3
1.0 5 90-98 95 3.2 3.4

RH-24655 0.05 (LOQ) 5 93-101 96 3.3 3.4
1.0 5 94-103 97 3.5 3.6

RH-26059 0.05 (LOQ) 5 112-116 114 1.6 1.4
1.0 5 100-107 104 2.9 2.8Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 7 of 12 Analyte Fortification Level (μg/L) Number of Tests Recovery Range (%) Mean Recovery (%) Standard Deviation (%) Relative Standard Deviation (%)

UK1 (RH-23801) 0.05 (LOQ) 5 105-124 112 7.4 6.6
1.0 5 93-105 99 4.2 4.3 Drinking Water Propyzamide (RH-23315) 0.05 (LOQ) 5 80-102 93 9.3 10
1.0 5 95-103 100 3.3 3.3

RH-24580 0.05 (LOQ) 5 96-119 110 8.6 7.8
1.0 5 102-110 107 3.6 3.3

RH-24644 0.05 (LOQ) 5 93-100 97 2.9 3.0
1.0 5 91-101 97 4.7 4.8

RH-24655 0.05 (LOQ) 5 84-107 97 9.0 9.3
1.0 5 99-104 102 2.0 2.0

RH-26059 0.05 (LOQ) 5 102-110 105 3.4 3.3
1.0 5 103-108 105 2.3 2..2

UK1 (RH-23801) 0.05 (LOQ) 5 104-119 108 6.4 5.9
1.0 5 93-100 96 3.0 3.1 Data (quantitation ion results) were obtained from Tables 19-36, pp. 55-72 of MRID 48690302. Confirmation ion recovery results were not reported. 1 Water matrices were not characterized ; all three control matrices were obtained from Dow AgroSciences (p. 23 of

MRID 48690302).

III. Method Characteristics

In the ECM and ILV, the LOQ and LOD values for propyzamide, RH-24580, RH-24644, RH24655, RH-26059 and UK1 in water were 0.05 μg/L and 0.015 μg/L, respectively (p. 24 of MRID 48599207; p. 25 of MRID 48690302). Follo wing the method of Keith, L. H., et al . (see section V. References below), the LOD and LOQ for determination of propyzamide and its transformation products in water were calculated using the standard deviation from the 0.05 μg/L recovery results (p. 24 of MRID 48599207). The LOD was calculated as three times the standard deviation (3 s ), and the LOQ was calculated as ten times the standard deviation (10 s ) of the recovery results (Table 23, p. 51 of MRID 48599207). The calculated values support the LOQ and LOD established for the study.Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 8 of 12 Table 4. Method Characteristics Propyzamide RH-24580 RH-24644 RH-24655 RH-26059 UK1 Limit of Quantitation (LOQ) 0.05 μg/L 0.05 μg/L 0.05 μg/L 0.05 μg/L 0.05 μg/L 0.05 μg/L

Limit of Detection (LOD) 0.015 μg/L 0.015 μg/L 0.015 μg/L 0.015 μg/L 0.015 μg/L 0.015 μg/L

Linearity (Power fit calibration curve r and concentration range) 1 Surface Water

r = 0.9991 (0.015-2.0

μg/L) r = 0.9968 (0.015-2.0

μg/L) r = 0.9978 (0.015-2.0

μg/L) r = 0.9984 (0.015-2.0

μg/L) r = 0.9999 (0.05-2.0

μg/L) r = 0.9927 (0.015-2.0

μg/L)
Ground Water
r = 0.9963 (0.015-2.0

μg/L) r = 0.9936 (0.015-2.0

μg/L) r = 0.9986 (0.015-2.0

μg/L) r = 0.9955 (0.015-2.0

μg/L) r = 0.9999 (0.015-2.0

μg/L) r = 0.9995 (0.015-2.0

μg/L) Drinking Water
r = 0.9999 (0.05-2.0

μg/L) r = 0.9937 (0.015-2.0

μg/L) r = 0.9996 (0.015-2.0

μg/L) r = 0.9974 (0.015-2.0

μg/L) r = 0.9999 (0.015-2.0

μg/L) r = 0.9982 (0.015-2.0

μg/L) Repeatable

Yes Yes Yes Yes Yes Yes, except at LOQ in ground water (RSD 22%) Reproducible
Yes Yes Yes Yes Yes Yes, except in ground water (RSD 22%) Specific Could not be determined; recovery results from confirmation ion analyses were not provided. Data were obtained from p. 25; Figures 1-18, pp. 91-108 of MRID 48690302. 1 Reviewer-calculated r 2 values for the provided ILV calibration curv es (matrices combined) were 0.9926-0.999 for

propyzamide, 0.9873-0.9936 for RH-24580, 0.9955-0.9991 for RH-24644, 0.9909-0.9968 for RH-24655, 0.9998 (n = 3) for RH-26059, and 0.9855-0.9989 for UK1 (DER Attachment 2). The study authors reported calculated r 2 values (quantitation ion analyses) of 0.9991, 0.9985, 0.99 98, 0.9997, 0.9998, 0.9998 for propyzamide, RH-24644, RH-24655, RH-24580, RH-26059 and UK1, respectively (p. 23 of MRID 48599207). Reported ECM r 2 values could not be verified by reviewer because complete calibration data were not reported (Figures 7-13, pp. 58-62 of MRID 48599207).

IV. Method Deficiencies and Reviewer’s Comments

1. For both the ECM and ILV, performance data at 10x LOQ were not reported to validate the method. A validation sample set should consist of, at a minimum, a reagent blank, two unspiked matrix control samples, five ma trix control samples spike at the LOQ, and five matrix control samples spiked at 10x LOQ for each analyte and matrix.

2. For the ILV, the following fortifications us ing the quantitation i on method did not meet OCSPP Guideline 850.6100 criteria for precisi on and accuracy (mean recoveries for replicates at each spiking level between 70% and 120% and relative standard deviations (RSD) ≤ 20%): 0.05 μg/L (LOQ) fortified UK1 in ground water (RSD 22%; Table 30, p. 66 of MRID 48690302).

3. For both the ECM and ILV, insufficient perf ormance data (no recovery results) were provided to validate the confirmation ion anal yses. For the ECM, only confirmation ratioPropyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 9 of 12 difference results, i.e. comparison of the confirmati on ratio (confirmation ion peak area/quantitation ion peak ar ea) of the recovery sample with the average confirmation ratio of the calibration standards, were reported (pp. 21-22; Tables 2-19, pp. 30-47 of MRID 48599207). Chromatograms from confirmati on ion analyses of 0.05 μg/L (LOQ) and 1.0 μg/L (20x LOQ) fortified samples were provided; however, the respective calibration curves to allow calculation of r ecoveries were not provided (Figures 15-16, pp. 65-68; Figures 18-19, pp. 71-74; Figur es 21-22, pp. 77-80 of MRID 48599207).

For the ILV, no results (recovery results or chromatograms) from confirmation ion analyses were reported.

4. The ILV implemented several modifications to the ECM to improve precision and repeatability of the method (p. 34; A ppendix B, pp. 217-218 of MRID 48690302). The autosampler temperature was reduced from ambient to ca . 15°C due to possible stability issues with the analytes. Additionally, the IL V considered the use of syringes and glass pipettes to fortify samples (analytes may adhe re to plastic) and daily preparation of the mixed calibration standards to be critical me thod steps. The modifications recommended by the independent laboratory were not impl emented in an amended final ECM report.

5. The waters used in the ILV were not characte rized. The water matrices were reported as obtained from Dow AgroScie nces (p. 23 of MRID 48690302).

6. In the ECM, the stability of the analytes prep ared in acetonitrile a nd stored at -20°C was investigated (pp. 24-25 of MRID 48599207) . Quantitation ion analyses found propyzamide (RH-23315, 96.4% recovered) a nd RH-24580 (100.2%) were stable up to 57 days, RH-24644 (96.2%), RH-24655 (96.4% ) and RH-26059 (110.2%) up to 56 days and UK1 (97.8%) up to 41 days. Recoveries fr om confirmation ion analyses were also determined, but not reported.

In addition, stability of the sample extrac ts was investigated (p. 25 of MRID 48599207). Following initial analyses, the samples were st ored at 4°C for 3-6 days, then re-analyzed. Quantitation ion analyses determined mean recoveries for all analytes ranged from 91- 107% with RSDs of 1.3-7.0%. Prop yzamide (RH-23315), RH-24644, RH-24655, RH24580 and UK1 were found to be stable up to 3 days and RH-26059 up to 6 days after sample preparation.

7. It was reported for the ILV that one batch of thirty-eight samples required approximately four person hours over one calendar day to co mplete the preparati on (p. 34 of MRID 48690302). Instrument analysis of water samp les was three hours. Data manipulation required an additional one to two person hour s. Initial solution preparation required approximately three person hours.Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 10 of 12 V. References

Keith, L. H.; Crummett, W.; Deegan, J., Jr.; Libby, R. A.; Taylor, J. K.; Wentler, G. Anal. Chem. 1983, 55 , 2210-2218 (p. 27 of MRID 48599207).

U.S. Environmental Protection Agency. 2012. Ecological Effects Test Guidelines, OCSPP 850.6100, Environmental Chemistry Methods an d Associated Independent Laboratory Validation. Office of Chemical Safety a nd Pollution Prevention, Washington, DC. EPA 712-C-001.

40 CFR Part 136. Appendix B. Definition and Pro cedure for the Determination of the Method Detection Limit-Revision 1.11, pp. 317-319.Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 11 of 12 Attachment 1: Chemical Names and Structures

Propyzamide (Kerb, pronamide, RH-23315, RH-3315, RH-315)

IUPAC Name: 3,5-Dichloro-N-(1,1-dimethylprop-2-ynyl)benzamide
CAS Name: 3,5-Dichloro-N-(1,1-dimethyl-2-propynyl)-benzamide
CAS Number: 23950-58-5 SMILES String: CC(C)(NC(=O)c1cc(Cl)cc(Cl)c1)C#C (EPI Suite, v3.12 SMILES).

RH-24644 (RH-4644)

IUPAC Name: 3,5-Dichloro-N-(1,1,2-trimethylprop-2-enyl)benzamide
CAS Name: 2-(3,5-Dichlorophenyl)-4,4-dime thyl-5-methylene oxozoline
CAS Number: 29918-40-9 SMILES String: Not reported.

RH-24655

IUPAC Name: 3,5-Dichloro-N-(1,1-dimethylpropenyl)benzamide
CAS Name: Not reported.
CAS Number: Not reported. SMILES String: Not reported.Propyzamide (PC 101701) MRIDs 48599207 (ECM)/ 48690302 (ILV)

Page 12 of 12 RH-24580 (RH-4580)

IUPAC Name: 3,5-Dichloro-N-(1,1-dimethyl-2-oxopropyl)benzamide
CAS Name: N-(1,1-Dimethyl acetonyl )-3,5-dichloro-benzamide
CAS Number: 29918-41-0 SMILES String: Not reported.

RH-26059

IUPAC Name: 3-[(3,5-Dichlorobenzoyl)am ino]-3-methylbutanoic acid
CAS Name: Not reported.
CAS Number: Not reported. SMILES String: Not reported.

RH-23801 (UK1, 3-chloro kerb)

IUPAC Name: 3-Chloro-N-(1,1-dimethylpropynyl)benzamide
CAS Name: Not reported.
CAS Number: Not reported. SMILES String: Not reported.