Test Material: Propyzamide (Pronamide, RH-23315)

MRID: 49300802

Title: Method Validation Study for the Determination of Residues of Propyzamide and its Relevant Metabolites in Soil by Liquid Chromatography with Tandem Mass Spectrometry

MRID: 49300801

Title: Propyzamide - Independent Laboratory Validation of an Analytical Method for the Determination of Residues of Propyzamide and its Relevant Metabolites in Soil by Li quid Chromatography with Tandem Mass Spectrometry

EPA PC Code: 101701

OCSPP Guideline: 850.6100

For CDM Smith

Primary Reviewer: Lisa Muto Signature:

Date: 11/17/14

Secondary Reviewer: Lynne Binari Si g nature:

Date: 11/17/14

QC/QA Manager: Joan Gaidos Signature:

Date: 11/17/14Propyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 2 of 10 Analytical method for propyzamide and it s transformation products RH-24580 and RH24644 in soil

Reports: ECM: EPA MRID No.: 49300802. Hill, R.C., Q. Li and V. Dixit. 2013. Method Validation Study for the Determination of Residues of Propyzamide and its Relevant Metabolites in Soil by Liquid Chromatography with Tandem Mass Spectrometry. Dow AgroSciences Study No.: 110586. Report prepared, sponsored, and submitted by Dow AgroSciences LLC, Indianapolis, Indiana; 101 pages. Final report issued May 22, 2013. ILV: EPA MRID No. 49300801. Ge mrot, F. 2013. Propyzamide - Independent Laboratory Validation of an Analytical Method for the Determination of Residues of Propyzamid e and its Relevant Metabolites in Soil by Liquid Chromatography with Tandem Mass Spectrometry. EAS Study No.: S13-03290. Dow AgroSciences Study No.: 130751. Report prepared by Eurofina Agroscience Services Chem SAS, Vergèze, France, sponsored and submitted by Dow AgroScie nces LLC, Indianapolis, Indiana; 96 pages. Final report issued November 15, 2013.
Document No.: MRIDs 49300802 & 49300801
Guideline: 850.6100
Statements: ECM: The study was conducted in acco rdance with USEPA FIFRA Good Laboratory Practice (GLP) standard s (p. 3 of MRID 49300802). 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 st atement (p. 4). A signature page was also included (p. 5). ILV: The study was conducted in acco rdance with OECD GLP standards (2007; p. 3 of MRID 49300801). The test fa cility was compliant with French GLP (Appendix D, p. 96). 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 wa s not included; a signature page was included (p. 5).
Classification: This analytical method is classified as supplemental. The study sponsor did not specify that the soil used in the ILV was either an equivalent, or more difficult, analytical sample condition as that used in the ECM. For all analytes in the ECM, performance data to validate the method at 10×LOQ were not reported. Sample recoveries were corrected in the ECM. In the ECM, no chromatograms were provided for three of the four soil matrices. Linearity data was not provided for one of the four soils in the ECM.
PC Code: 101701
Reviewer: Karen Milians, Ph.D., Chemist Signature: Date:

Executive SummaryPropyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 3 of 10 This analytical method, Dow AgroSciences St udy No. 110586, is designedfor the quantitative determination of propyzamide and its transf ormation products RH-24644 and RH-24580 in soil
at 0.005 μ g/g using LC/MS/MS. For all analytes in th e ECM, sample recoveries were corrected and performance data to validate the method at 10×LOQ were not reported. The LOQ is less than the lowest toxicological level of concern in so il. The ILV validated th e method after one trial with no modifications or difficulties; sa mples fortified at 10×LOQ were included. The study sponsor did not specify that the soil used in the ILV (loamy sand soil) was either an equivalent, or more difficult, analytical sample condition as that used in the ECM (clay, loam, and silt loam soils).

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

49300802 49300801 Soil 22/05/2013 Dow AgroSciences LLC LC/MS/MS 0.005 μg/g RH-24644

RH-24580

I. Principle of the Method

Samples (5.0 ± 0.05 g) of soil were extracted twice with aceton itrile:water (80:20, v:v; 25 mL then 20 mL) by spinning via vortex for 10 seconds then shaking via recipr ocating shaker for 30 minutes at ca . 180 excursions/minute (p. 11; Appe ndix 1, p. 98 of MRID 49300802). Soil and extract were separated by centrifugation (5 mi nutes at 2000 rpm) and decanting. The volume of the combined extracts was adjusted to 50 mL using acetonitrile:water (80:20, v:v). After centrifugation (5 minutes at 4000 rpm), the combined extract was further diluted to a 5x dilution using acetonitrile:wat er (80:20, v:v) prior to analysis.

Samples were analyzed for propyzamide (R H-23315) and its products RH-24644 and RH-24580 by HPLC (Zorbax SB-C8, 4.6 mm x 75 mm, 3.5 μm column) using a mobile phase of (A) water with 0.1% formic acid and (B) ace tonitrile with 0.1% formic ac id [percent A:B at 0.01 min. 75:25, 3.00-5.00 min. 10:90, 5:15-8.00 min. 75:25) with MS/MS-ESI (electrospray ionization; positive mode) detection and multiple reacti on monitoring (MRM; p. 11; Appendix 1, pp. 100- 101 of MRID 49300802). Injection volume was 10 μL. Analytes were iden tified using two ion transitions; one for quantitation (Q) and one for confirmation (C; p. 21 of MRID 48599207). Ion transitions monitored were as follows: m/z 256.0 → 190.0 (Q) and m/z 258.0 → 192.0 (C) for propyzamide, m/z 274.1 → 145.1 (Q) and m/z 274.1 → 109.0 (C) for RH-24580 and m/z 256.0 → 145.0 (Q) and m/z 256.0 → 109.0 (C) for RH-24644.

In the ILV, the method was performed exact ly as written (pp. 19-20 of MRID 49300801). Approximate retention times for the analytes were reported as ca . 3.9 minutes for propyzamide,

ca . 3.7 minutes for RH-24580 and ca . 4.7 minutes for RH-24644. The ILV study author noted the typing errors in the ECM which caused the ex traction solvent and storage temperature to be “not in line with the validated method” (p. 26). The reviewer noted these typing errors as well.Propyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 4 of 10 The LOQ for all analytes was the same in the ECM and ILV at 0.005 μg/g (p. 18 of MRID 49300802; Table 1, p. 30 of MRID 49300801). The LOD for all analytes was 0.0015 μg/g in the ECM and ILV.

II. Recovery Findings

ECM (MRID 49300802): Mean recoveries and relative standard devi ations (RSDs) were within guidelines (mean 70-120%; RSD ≤ 20%) for analysis of propyzamide, RH-24580 and RH-24644 in four soils (clay, loam and tw o silt loam) at fortification levels of 0.005 μg/g (LOQ) and 0.5 μg/g (100×LOQ; corrected recoveries; Tables 3-14, pp. 24-37). Performance data (recovery results) from quantitation and confirmation ion an alyses were comparable; recovery data was corrected for residues found in the control sample s. Recoveries from samples fortified at 0.0015 μg/g (LOD) ranged (matrices/quantification and confirmation ions combined) from 67-93% for propyzamide, 53-93% for RH-24580 and 67-87% fo r RH-24644 (DER Attachment 2). The soil matrices were well characterized (Table 2, p. 23).

ILV (MRID 49300801): Mean recoveries and relative standard deviations (RSDs) were within guidelines (mean 70-120%; RSD ≤ 20%) for analysis of propyzamide, RH-24580 and RH-24644 in loamy sand soil at fortification levels of 0.005 mg/kg (LOQ) and 0.050 mg/kg (10×LOQ; quantitation and confirmation ion analyses; Table 7, p. 36). Perfor mance data (recovery results) from quantitation and confirmation ion analyses were comparable. Recoveries from samples fortified at 0.0015 mg/kg (LOD) ranged (quantific ation and confirmation ions combined) from 107-117% for propyzamide, 42-81% for RH-24580 and 108-112% for RH-24644 (DER Attachment 2). The soil matrix was well character ized (soil origin was not reported; p. 16). The method was validated in the first trial (p. 25).

Table 2. Initial Validation Method Recoveries for Propyzamide and Its Transformation Products in Soil 1Propyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 5 of 10 Analyte Fortification Level (μg/g) Number of Tests Recovery Range (%) Mean Recovery (%) Standard Deviation (%) Relative Standard Deviation (%) Clay (United Kingdom; Soil 001) Quantitation ion Propyzamide (RH-23315) 0.005 (LOQ) 6 83-89 86 2.0 2.3
0.5 6 81-92 87 4.4 5.1

RH-24580 0.005 (LOQ) 6 84-93 87 3.7 4.3

0.5 6 85-92 88 2.6 3.0

RH-24644 0.005 (LOQ) 6 80-87 84 2.9 3.5
0.5 6 84-90 87 2.9 3.4
Confirmation ion Propyzamide (RH-23315) 0.005 (LOQ) 6 78-97 88 7.6 8.7
0.5 6 83-90 87 3.4 3.9

RH-24580 0.005 (LOQ) 6 83-94 88 4.3 4.9

0.5 6 81-91 88 3.7 4.2

RH-24644 0.005 (LOQ) 6 84-88 86 2.0 2.4
0.5 6 81-89 86 3.1 3.6 Loam (United King dom; Soil 002) Quantitation ion Propyzamide (RH-23315) 0.005 (LOQ) 6 81-96 86 6.2 7.1

0.5 6 86-90 88 1.5 1.7

RH-24580 0.005 (LOQ) 6 80-98 88 6.8 7.7
0.5 6 86-93 90 2.3 2.5

RH-24644 0.005 (LOQ) 6 81-88 85 2.5 2.9
0.5 6 81-89 85 3.2 3.8
Confirmation ion Propyzamide (RH-23315) 0.005 (LOQ) 6 78-90 85 4.8 5.6
0.5 6 80-90 86 4.2 4.9

RH-24580 0.005 (LOQ) 6 78-87 83 3.5 4.2
0.5 6 85-91 89 2.1 2.3

RH-24644 0.005 (LOQ) 6 85-90 87 2.1 2.4
0.5 6 84-90 87 2.0 2.3 Silt loam (Germany; Soil 003) Quantitation ion Propyzamide (RH-23315) 0.005 (LOQ) 6 85-91 89 2.2 2.4
0.5 6 79-87 84 3.3 3.9

RH-24580 0.005 (LOQ) 6 85-95 89 3.6 4.0
0.5 6 85-92 88 3.0 3.4

RH-24644 0.005 (LOQ) 6 81-90 86 4.3 4.9

0.5 6 80-86 83 2.2 2.6
Confirmation ion Propyzamide (RH-23315) 0.005 (LOQ) 6 74-90 84 5.5 6.6

0.5 6 81-90 87 3.4 3.9

RH-24580 0.005 (LOQ) 6 83-96 89 5.7 6.4
0.5 6 82-91 87 3.7 4.2

RH-24644 0.005 (LOQ) 6 83-91 87 3.4 4.0
0.5 6 80-89 84 3.3 3.9 Silt loam (United Kingdom; Soil 004) Quantitation ion Propyzamide 0.005 (LOQ) 6 84-99 87 5.9 6.8Propyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 6 of 10 Analyte Fortification Level (μg/g) Number of Tests Recovery Range (%) Mean Recovery (%) Standard Deviation (%) Relative Standard Deviation (%) (RH-23315) 0.5 6 84-93 89 3.3 3.7

RH-24580 0.005 (LOQ) 6 87-102 95 7.2 7.6

0.5 6 89-99 93 3.9 4.2

RH-24644 0.005 (LOQ) 6 80-97 90 6.5 7.2
0.5 6 84-94 88 4.5 5.1
Confirmation ion Propyzamide (RH-23315) 0.005 (LOQ) 6 83-99 90 5.8 6.5
0.5 6 89-94 91 2.1 2.4

RH-24580 0.005 (LOQ) 6 84-90 87 2.4 2.7

0.5 6 88-96 92 3.5 3.8

RH-24644 0.005 (LOQ) 6 87-92 89 2.2 2.5
0.5 6 83-90 87 3.0 3.4 Data (corrected recovery results) were obtained from Tables 3-14, pp. 24-37 of MRID 49300802. 1 Soil matrices were fully characteri zed (USDA texture classification; Table 2, p. 23 of MRID 49300802). 2 Ion transitions monitored were as follows: m/z 256.0 → 190.0 (Q) and m/z 258.0 → 192.0 (C) for propyzamide, m/z 274.1 → 145.1 (Q) and m/z 274.1 → 109.0 (C) for RH-24580 and m/z 256.0 → 145.0 (Q) and m/z 256.0 → 109.0 (C) for RH-24644.

Table 3. Independent Validation Method Recoveries for Propyzamide and Its Transformation Products in Loamy Sand Soil 1

Analyte Fortification Level (mg/kg) Number of Tests Recovery Range (%) Mean Recovery (%) Standard Deviation (%) Relative Standard Deviation (%)

Quantitation ion Propyzamide (RH-23315) 0.005 (LOQ) 5 89-104 97 7 7
0.050 5 88-102 98 6 6

RH-24580 0.005 (LOQ) 5 81-99 87 8 9
0.050 5 88-97 95 4 4

RH-24644 0.005 (LOQ) 5 102-121 109 7 7
0.050 5 100-113 106 5 5
Confirmation ion Propyzamide (RH-23315) 0.005 (LOQ) 5 91-104 97 5 5

0.050 5 90-104 98 5 5

RH-24580 0.005 (LOQ) 5 88-106 97 7 7
0.050 5 92-104 88 5 5

RH-24644 0.005 (LOQ) 5 110-115 113 3 2
0.050 5 101-114 109 5 5 Data (results) were obtained from Table 7, p. 36 of MRID 49300801 and DER Attachment 2 (standard deviations). 1 Soil matrix was fully characterized (USDA texture clas sification; soil origin not reported; p. 16 of MRID

49300801). 2 Ion transitions monitored were as follows: m/z 256.0 → 190.0 (Q) and m/z 258.0 → 192.0 (C) for propyzamide, m/z 274.1 → 145.1 (Q) and m/z 274.1 → 109.0 (C) for RH-24580 and m/z 256.0 → 145.0 (Q) and m/z 256.0 → 109.0 (C) for RH-24644.Propyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 7 of 10 III. Method Characteristics

In the ECM and ILV, the LOQ and LOD values for propyzamide, RH-24580 and RH-24644 in soil were 0.005 μg/g and 0.0015 μg/g, respectiv ely (p. 18 of MRID 49300802; p. 14; Table 1, p. 30 of MRID 49300801). Following 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 soil were calculated using the standard deviati on from the 0.005 μg/g recovery results (p. 18 of MRID 49300802). 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. The calculated values support the LOQ a nd LOD established for the method.

Table 4. Method Characteristics Propyzamide RH-24580 RH-24644 Limit of Quantitation (LOQ) 0.05 μg/g Limit of Detection (LOD) 0.015 μg/g

Linearity (Least squares calibration curve r and concentration range) 1,2 Clay r = 0.998 (Q) r = 1.000 (C) (0.03-20 ng/mL) r = 0.999 (Q) r = 0.999 (C) (0.03-20 ng/mL) r = 0.994 (Q) r = 0.997 (C) (0.03-20 ng/mL)

Loam r = 0.999 (Q) r = 0.999 (C) (0.03-20 ng/mL) r = 0.998 (Q) r = 0.999 (C) (0.03-20 ng/mL) r = 0.996 (Q) r = 0.998 (C) (0.03-20 ng/mL) Silt loam (-003) r = 0.998 (Q) r = 0.999 (C) (0.03-20 ng/mL) r = 0.999 (Q) r = 0.999 (C) (0.03-20 ng/mL) r = 0.998 (Q) r = 0.999 (C) (0.03-20 ng/mL) Silt loam (-004)

Not reported Repeatable Yes Reproducible Yes (only loamy sand soil was tested in ILV) Specific Yes Data were obtained from p. 18; Tables 3-14, pp. 24-37; Tables 28-32, pp. 51-52 of MRID 49300802 and Table 7, p. 36 of MRID 49300801. 1 Reviewer-calculated r 2 values (matrices/ions combined) for the provided ECM r values were 0.9960-1.000 for

propyzamide, 0.9960-0.9980 for RH-24580 and 0.9880 -0.9980 for RH-24644 (DER Attachment 2). Reviewercalculated r 2 values for the provided ECM calibration curves (matrices/ions combined) were 0.9988-0.9999 for propyzamide, 0.9993-0.9999 for RH-24580 and 0.9942-0.9981 for RH-24644. The ILV study author reported calculated r 2 values (ions combined) of 0.9991 for propyzamide, 0.9997-0.9968 for RH-24580 and 0.9982-0.9991 for RH-24644 (Figures 1-6, pp. 33-43 of MRID 49300801). Reviewer-calculated r 2 values for the provided ILV calibration curves (ions combined) were 0.9988-0.9999 for propyzamide, 0.9993-0.9999 for RH-24580 and 0.9942-0.9981 for RH-24644 (DER Attachment 2). 2 The concentration range 0.03 to 20 ng/mL was equivalent to sample concentrations of 0.0015 to 1.00 mg/kg (pp.

23, 26 of MRID 49300801). Linearity is satisfactory when r 2 ≥ 0.995.Propyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 8 of 10 IV. Method Deficiencies and Reviewer’s Comments

1. The study sponsor did not specif y that the soil used in the ILV (loamy sand soil, organic carbon 1.87 ± 0.20%; p. 16 of MRID 49300801) was either an equivalent, or more difficult, analytical sample c ondition as that used in the EC M (clay, loam, and silt loam soils, total organic carbon 2.1-4.4% ; Table 2, p. 23 of MRID 49300802). 2. In the ECM, no performance data was provi ded for 10×LOQ to validate the method. A validation sample set should consist of, at a minimum, a reagent blank, two unspiked matrix control samples, five matrix control samples spike at the LOQ, and five matrix control samples spiked at 10x LOQ for each analyte and matrix.

3. In the ECM, sample recoveri es were corrected for residue s found in the control samples (Tables 3-14, pp. 24-37 of MRID 49300802). Th ere was no indication that recoveries were corrected in the ILV (pp. 23- 24; Tables 1-6, pp. of MRID 49300801).

4. In the ECM, no chromatograms were provided for three of the four soil matrices. Only those of clay soil (Soil S01) were included; this set of chromatograms was complete, except for a reagent blank.

5. In the ECM, a calibration curve and data were not provided for one of the four soils, the Silt Loam Soil -004; however, calibration data was provided for the stability (Soil S01 clay only) and matrix effect studies (T ables 22-27, pp. 45-50 of MRID 49300802). Least squares calibration curve r values for both auxiliary studies were reported as 0.997-0.999 for propyzamide, 0.997-1.000 for RH-24580 and 0.995-0.999 for RH-24644 (ions combined; Tables 28-32, pp. 51-52).

6. A significant typographical erro r in the ECM was noted by the reviewer and the ILV study author (p. 11; Appendix 1, p. 98 of MRID 49300802). The extraction solvent [acetonitrile:water (80:20, v:v)] was err oneously reported as “acetonitrile:1.0N HCl (80:20, v:v)” on p. 11 of the study report. The correct extraction solv ent was reported in Appendix 1. The ILV study author noted the t yping errors in the ECM which caused the extraction solvent and storage temperature to be “not in line with the validated method” (p. 26 of MRID 49300801). This was not a modification of the ECM report.

7. In the ILV, the reviewer noted that the LOD for the method was reported as 0.003 mg/kg on p. 18; however, due to data in the Tables and Figures section, the reviewer reported that the LOD of the ILV was the same as the ECM, 0.0015 μ g/g (p. 18; Tables 1-6, pp. 30-35; Figures 13-14, pp. 50-51; Figures 25- 26, pp. 62-63; Figures 37-38, pp. 74-75 of MRID 49300801).

8. A reagent blank chromatogram was not included in the ECM or ILV.

9. The soil matrices were well characterized in the ECM and ILV (Table 2, p. 23 of MRID 49300802; p. 16 of MRID 49300801). Soil sources were specified in the ECM, but not in the ILV.Propyzamide (PC 101701) MRIDs 49300802 (ECM)/ 49300801 (ILV)

Page 9 of 10 10. In the ECM, the stability of the analytes prep ared in acetonitrile a nd stored at -20°C was investigated (p. 19 of MRID 49300802). It wa s determined that propyzamide (RH-23315) and RH-24580 were stable for up to 57 days, and RH-24644 was stable for up to 56 days.

In addition, stability of the sample extracts was investigated (p. 19; Tables 15-20, pp. 38- 43 of MRID 49300802). Quantitation and conf irmation ion analyses found RH-23315 (85-93% recovered), RH-24580 (85-91%) and RH -24644 (84-88%) were stable in all soil extracts for 4 days at ca . 4°C (matrices combined; LOQ and 10×LOQ combined, n = 3 for each; mean recoveries reported).

In the ILV, stability of the sample extract s was also investigated (pp. 25-26; Table 9, p. 37 of MRID 49300801). Quantitation ion anal yses found RH-23315 (85% recovered), RH-24580 (91%) and RH-24644 (104%) were stable in the sample extracts for 7 days at 4°C (LOQ, n = 5 for each; mean recoveries reported; confirmation ion not monitored).

11. In the ECM, matrix effects were determined for each analyte/ion/matrix combination compared to neat solvent (p. 20; Tabl e 21, p. 44 of MRID 49300802). Matrix effects were most notable for the clay soil; however, the results showed that the matrix effects were within ±20% and not significant. The ch romatograms of control samples of the clay soil (Soil S01) showed small peaks at the retention times of the analytes, but these interferences were below the limit of detection, typically 10-20% of the LOQ at most (Tables 3-8, pp. 24-35; Figures 11 -12, pp. 77-84 of MRID 49300802).

In the ILV, matrix effects were determined to be insignificant, as well (<20%; p. 25; Table 8, p. 36 of MRID 49300801). Chromatogr ams of the control samples showed no interferences (Figures 11-12, pp. 48-49; Figures 23-24, pp. 60-61; Figures 35-36, pp. 72- 73 of MRID 49300801).

12. It was reported for the ILV that one set of fourteen samples required approximately five person hours to complete the preparati on and extraction ( p. 26 of MRID 49300801). Subsequent LC/MS analysis and evaluation required ca . 4 hours. The ILV study author reported that there was no communication with the method developers during the study; the only communication which occurred was the clarification of the extraction solvent prior to experime nt initiation.

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. 21 of MRID 49300802).

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 49300802 (ECM)/ 49300801 (ILV)

Page 10 of 10 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-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 3,5-Dichloro-N-(1,1-dimethyl-2-oxo-n- propyl)benzamide (Table 1, p. 22)
CAS Number: 29918-41-0 SMILES String: Not reported.