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# Submission Report

Submission Information Submission ID : 25427700 Submission Name : Revised test plan and robust summaries for C4 AR Number : 

## Chemical Information CAS Number : 170373-17-8 Ninth Collective Index Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylSupporting Chemicals : (163515-14-8) dimethenamid



## Submitter Information Submitter's Name : EXPONENT, INC. Address : 1800 Diagonal Road, Suite 500 City : Alexandria State : VA ZIP/Postal Code : 22314 Country : US Type of Submitter : Company 

## Technical Point of Contact Information Technical Point of Contact : Jane P. Staveley Title : Senior Managing Scientist Phone Number : 919-228-6480 Fax Number : E-Mail Address : jstaveley@exponent.com 

## Additional Technical Point of Contact Information Technical Point of Contact : Title : Phone Number : Fax Number : E-Mail Address : 

## Sponsor Information Sponsor's Name : BASF Corp Address : 1609 Biddle Ave City : Wyandotte State : MI ZIP/Postal Code : 48192 Country : US 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintPhone Number : 734-324-6212 Fax Number : E-Mail Address : ralph.parod@basf.com Type of Sponsor : Company 

## Technical Point of Contact Information Technical Point of Contact : Ralph Parod Title : Senior Toxicologist Phone Number : Fax Number : E-Mail Address : 

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## Melting Point
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Melting Point Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4

- dimethyl- CAS# 170373-17-8 Sponsored Chemical Result Type:
Test Substance Result Type: Estimated 

### Results - Melting Point Melting Indicator:
Melting Point Value/Range (Temperature): circa 72.7 °C

Results Remarks: MPBPVP (v1.43) Program Results:

=============================== Experimental Database Structure Match: no data SMILES : s1cc(c(c1C)NC(COC)C)C CHEM : MOL FOR: C10 H17 N1 O1 S1 MOL WT : 199.31 ------------------------ SUMMARY MPBVP v1.43 ------ --

------------ Boiling Point: 277.88 deg C (Adapted Stein and Brow n Method) Melting Point: 120.86 deg C (Adapted Joback Method) Melting Point: 48.59 deg C (Gold and Ogle Method) Mean Melt Pt : 84.73 deg C (Joback; Gold,Ogle Methods) Selected MP: 72.68 deg C (Weighted Value) 

### Study/Method - Melting Point Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: Method/Guideline and Test Condition Remarks: The melting temperature was estimated by MPBPWIN v1.43 found in EPIWIN v4.00. Measured data for water solubility (472.5 mg/L) was entered. For all other parameters, the default values in EPIWIN were used. GLP: Not Applicable
Study Reference: EPISuite v4.00, US Environmental Protection Agency,2000-2008 

### Reliability/Data Quality - Melting Point Reliability: 2 - Valid With Restrictions 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintReliability Remarks: Scientifically acceptable method of calculation. 

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## Melting Point
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Melting Point Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: dimethenamid-P CAS No. 163515-14-8 Batch No.: Lot RS-1289-111596 Purity 99.4% Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Melting Point Melting Indicator:
Melting Point Value/Range (Temperature): <= -50 °C

Results Remarks: Solidification point below -50 deg C. 

### Study/Method - Melting Point Key Study Sponsor Indicator: Year Study Performed: 1999
Method/Guideline Followed: OECD 102
Method/Guideline and Test Condition Remarks: The test was performed according to OECD Test Guideline 102 and EEC A1. The test substance was cooled in a Perkin Elmer Pyr is 1 Differential Scanning Calorimeter (DSC) from 20 t o -50 deg C at 5 deg C/minute. During the run, the he at flow of the sample relative to a reference material was measured. GLP: Yes
Study Reference: Kroehl, T. 1999. Physical Properties of Dimethenami dP (PAI). BASF Aktiengesellschaft, Ecology and Environmental Analytics, BASF RegDoc #99/10167. 

### Reliability/Data Quality - Melting Point Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted melting point determination guidelines. 

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## Boiling Point
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Boiling Point Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: dimethenamid-P CAS No. 163515-14-8 Batch No.: Lot RS-1289-111596 Purity 99.4% Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Boiling Point Boiling Indicator:
Boiling Point Value/Range (Temperature): >= 280 °C

Results Remarks: There is no boiling point detected until 280 deg C 

### Study/Method - Boiling Point Key Study Sponsor Indicator: Key
Year Study Performed: 1999
Method/Guideline Followed: OECD 103
Method/Guideline and Test Condition Remarks: The test was performed according to OECD Guideline 103 and EEC A2.1.4.5. The test was performed using a Mettler FP80/FP81HT apparatus. A sample of test substance was heated in a capillary inside a heated metal block. A light beam was directed through the sample onto a photocell. T he principle of this method is that, when the boiling point is reached, bubbles rising in the capillary give a decrease in the intensity of light received by the photocell. The photocell gives a stop signal to a digital indicator reading out the temperature measured by a resistance thermometer located in the block. GLP: Yes
Study Reference: Kroehl, T. 1999. Physical Properties of Dimethenami dP (PAI). BASF Aktiengesellschaft, Ecology and Environmental Analytics, BASF RegDoc #99/10167. 

### Reliability/Data Quality - Boiling Point Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted boiling temperature determination guidelines. 

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## Boiling Point
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Boiling Point Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[((1S)-2-methoxy-1-methylethyl)-2,4-dimethylmethylethyl)]-2,4-dimethylCAS# 170373-17-8
Sponsored Chemical Result Type:
Test Substance Result Type: Estimated 

### Results - Boiling Point Boiling Indicator:
Boiling Point Value/Range (Temperature): circa 277.8 °C

Results Remarks: MPBPVP (v1.43) Program Results:

=============================== Experimental Database Structure Match: no data SMILES : s1cc(c(c1C)NC(COC)C)C CHEM : MOL FOR: C10 H17 N1 O1 S1 MOL WT : 199.31 ------------------------ SUMMARY MPBVP v1.43 ------ --

------------ Boiling Point: 277.88 deg C (Adapted Stein and Brow n Method) Melting Point: 120.86 deg C (Adapted Joback Method) Melting Point: 48.59 deg C (Gold and Ogle Method) Mean Melt Pt : 84.73 deg C (Joback; Gold,Ogle Methods) Selected MP: 72.68 deg C (Weighted Value) 

### Study/Method - Boiling Point Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: Method/Guideline and Test Condition Remarks: The boiling temperature was estimated by MPBPWIN v1.43 found in EPIWIN v4.00. Measured data for wate r solubility (472.5 mg/L) was entered. For all other input parameters, the default values in EPIWIN were used. GLP: Not Applicable
Study Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008 

### Reliability/Data Quality - Boiling Point 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintReliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Boiling Point
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Boiling Point Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: The test substance in this study is a technical gra de material of an active ingredient known as S-dimethenamid or SAN 1289 also known as (S)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methox y1-methylethyl)acetamide - CAS No.: 163515-14-8 - Purity: 94.6% (determined by HPLC) Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Boiling Point Boiling Indicator:
Boiling Point Value/Range (Temperature): = 122.6 °C @ Pressure: 0.093 hPa

Results Remarks: 

### Study/Method - Boiling Point Key Study Sponsor Indicator: Year Study Performed: 1997
Method/Guideline Followed: Other
Method/Guideline and Test Condition Remarks: The boiling point was determined following US EPA Subdivision D, No.63-6, ASTM D1120, D850 & D86, and OECD 103 dynamics method. The boiling point is defined as the temperature at which the vapor pressure of a liquid becomes equal to external pressure. To determine this, test substance (60 mL) was heated under vacuum and with stirring in a 100 mL round bottom flask, attached to a West type condenser. After a reflux rate of 1-2 drops per second was achieved and stabilized for 5 minutes, three temperature and pressure readings were recorded ove r a period of five minutes, and the average determined. GLP: Yes
Study Reference: Chen, H. 1997. Boiling Point of SAN 1289 H, Technical. SANDOZ Agro, Inc., Des Plaines, Illinois , unpublished. BASF RegDoc #97/5194. 

### Reliability/Data Quality - Boiling Point 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintReliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted boiling point determination guidelines. 

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## Boiling Point
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Boiling Point Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: Racemic C4, CAS# 87676-01-1, 3-Thiophenamine, N-(2-methoxy-1-methylethyl)-2,4-dimethylSponsored Chemical Result Type:
Test Substance Result Type: Estimated 

### Results - Boiling Point Boiling Indicator:
Boiling Point Value/Range (Temperature): circa 260.3 °C @ Pressure: 1013 hPa

Results Remarks: 

### Study/Method - Boiling Point Key Study Sponsor Indicator: Year Study Performed: 1989
Method/Guideline Followed: Method/Guideline and Test Condition Remarks: The atmospheric pressure, 760 mmHg was entered into the equation describing the vapor pressure at different temperatures: Ln(X)=16.2376-34211.99/(K - 94.8) This equation was developed in a vapor pressure stu dy done over the temperature range 80.47 - 190.37 deg C. Since the highest temperature tested in the vapor pressure study was 190.37 deg C and the estimated boiling temperature was 260.3 deg C, the result was extrapolated. GLP: No
Study Reference: Wilson, LC, vapor pressure measurements, Report fro m Wiltec Res. Co. letter report,1989.03.09 

### Reliability/Data Quality - Boiling Point Reliability: 4 - Not Assignable
Reliability Remarks: 1. The vapor pressure study which this calculated boiling temperature is based upon lacks methodological details. 2. The estimate was derived through extrapolation outside of the tested temperature range. 

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## Vapor Pressure
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Vapor Pressure Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: Racemic C4, CAS# 87676-01-1, 3-Thiophenamine, N-(2-methoxy-1-methylethyl)-2,4-dimethylSponsored Chemical Result Type:
Test Substance Result Type: Estimated 

### Results - Vapor Pressure Vapor Pressure Value/Range (Pressure): circa 0.015 hPa @ Temperature: 25 °C

Results Remarks: 

### Study/Method - Vapor Pressure Key Study Sponsor Indicator: Year Study Performed: 1989
Method/Guideline Followed: Method/Guideline and Test Condition Remarks: In this study the vapor pressure was determined at 12 temperatures over the range 80.5-190.4 deg C. The equation of the best-fit line was: lnP(mmHg) = 16.2376 - 4211.99/(Temp (K) - 94.8) Using this equation, the vapor pressure at 25 deg C (298.15 K) was extrapolated (2.718 was used as the natural logarithm in the calculation). The extrapolated vapor pressure in mmHg was multiplied by 1.33 to obtain the vapor pressure in hPa. GLP: No
Study Reference: Wilson, LC, vapor pressure measurements, Report fro m Wiltec Res. Co. letter report,1989.03.09 

### Reliability/Data Quality - Vapor Pressure Reliability: 4 - Not Assignable
Reliability Remarks: 1. The extrapolated vapor pressure at 25 deg C is significantly outside of the tested temperature ran ge and should be used cautiously. 2. No methodology presented. 

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## Vapor Pressure
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Vapor Pressure Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: The test substance in this study was a reference (high purity) grade material of an isomeric active ingredient in a manufacturing-use product. This ingredient is known as S-dimethenamid or SAN 1289 H also known as (S)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methox y1-methylethyl)acetamide - CAS No. 163515-14-8 Lot No.: RS-1289-082495 Purity: 98.6% (determined by HPLC and GC) Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Vapor Pressure Vapor Pressure Value/Range (Pressure): = 2.51E-5 hPa @ Temperature: 25 °C

Results Remarks: There was no flow-rate dependence of the results, indicating that the inert carrier gas was saturated with the test substance during the study. Thus, the final values of vapor pressure were determined by averaging all three values at all three flow rates. Mean extraction efficiencies ranged from 91.5% to 103% for 4 spiked samples. The measured vapor pressure of SAN 1289H was: At 25 deg C: 3.47 x 10^-5 hPa (+/- 1.29 x 10^-5) At 20 deg C: 2.51 x 10^-5 hPa (+/- 0.39 x 10^-5) These values are essentially equivalent as shown by the overlap of the ranges described by the standard deviations. The vapor pressures were reported in Pa (1 hPa = 10 0 Pa) 

### Study/Method - Vapor Pressure Key Study Sponsor Indicator: Year Study Performed: 1996
Method/Guideline Followed: Other
Method/Guideline and Test Condition Remarks: The test was performed according to US EPA Subdivision D, No. 63-9, as well as EEC A.4 gas saturation method. The vapor pressure was measured at two temperatures by the ga s saturation method. The procedure included measureme nt of the vapor pressure of a reference substance (dimethyl phthalate) and 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintdetermination of the efficiency of the extraction a nd analytical procedures used to recover trapped material. The trapping system consisted of two cryogenic traps in a series. Three nominal carrier gas flow rates were used and flow rates recorded frequently during the course of the study. Studies were done at 20 and 25 deg C. For each data point, the apparent flow rate, atmospheric pressure, ambient temperature, and temperature of the thermostated chamber were recorded. Analyses of the concentratio n of test substance were performed by HPLC. GLP: Yes
Study Reference: Chen, H., Laster, W. 1996. Vapor pressure of SAN 1289 H. SANDOZ Agro, Inc., Des Plaines, Illinois, unpublished. BASF RegDoc #96/5418. 

### Reliability/Data Quality - Vapor Pressure Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted vapor pressure determination guidelines. 

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## Vapor Pressure
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Vapor Pressure Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethylCAS# 170373-17-8 Sponsored Chemical Result Type:
Test Substance Result Type: Estimated 

### Results - Vapor Pressure Vapor Pressure Value/Range (Pressure): circa 0.00296 hPa @ Temperature: 25 °C

Results Remarks: MPBPVP (v1.43) Program Results:

=============================== Experimental Database Structure Match: no data SMILES : s1cc(c(c1C)NC(COC)C)C CHEM : MOL FOR: C10 H17 N1 O1 S1 MOL WT : 199.31 ------------------------ SUMMARY MPBVP v1.43 ------ --

------------ Boiling Point: 277.88 deg C (Adapted Stein and Brow n Method) Melting Point: 120.86 deg C (Adapted Joback Method) Melting Point: 48.59 deg C (Gold and Ogle Method) Mean Melt Pt : 84.73 deg C (Joback; Gold,Ogle Methods) Selected MP: 72.68 deg C (Weighted Value) Vapor Pressure Estimations (25 deg C): (Using BP: 277.88 deg C (estimated)) (Using MP: 72.68 deg C (estimated)) VP: 0.00202 mm Hg (Antoine Method) : 0.27 Pa (Antoine Method) VP: 0.00222 mm Hg (Modified Grain Method) : 0.296 Pa (Modified Grain Method) VP: 0.00388 mm Hg (Mackay Method) : 0.517 Pa (Mackay Method) Selected VP: 0.00222 mm Hg (Modified Grain Method) : 0.296 Pa (Modified Grain Method)Subcooled liquid VP: 0.00627 mm Hg (25 deg C, ModGrain method) : 0.835 Pa (25 deg C, Mod-Grain method) 

### Study/Method - Vapor Pressure Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: Method/Guideline and Test Condition Remarks: The vapor pressure was estimated by MPBPWIN v1.43 found in EPIWIN v4.00. Measured data for water solubility (472.5 mg/L) was entered. For all other 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintinput parameters, the default values in EPIWIN were used. GLP: Not Applicable
Study Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008 

### Reliability/Data Quality - Vapor Pressure Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Partition Coefficient
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Partition Coefficient Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: - CAS No.: 163515-14-8 - CAS Name: (S)-2-Chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methox y1-methylethyl)-acetamide- Common Name(s): dimethenamid-p (formerly Sdimethenamid) - BASF internal name: BAS 656 H (Formerly SAN 1289 H) - Batch No.: Lot No. RS-1289-111596 - Purity: 99.73% (GC); 99.45% (HPLC) (Radiolabeled chemical purity of 96.0%) Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured


### Results - Partition Coefficient Partition Coefficient Value/Range (Log K ow ): = 1.89 @ Temperature: 24 °C

Results Remarks: Temperature was consistently measured at 23.8 deg C

. The mean Pow from each test condition was 83.6, 57. 8 and 91.3. The mean log Pow from each test condition was 1.93, 1.7 7, and 1.96. The mean Pow and mean log Pow are 77.6 (+/- 17.0) a nd 1.89 (+/- 0.10) respectively. The overall recovery of dimethenamid-P was 100.14 + /- 1.55%. The effect of pH was not investigated since there i s no dissociation in water. 

### Study/Method - Partition Coefficient Key Study Sponsor Indicator: Year Study Performed: 1998
Method/Guideline Followed: OPPTS 830.7550
Method/Guideline and Test Condition Remarks: The test was performed according to US EPA OPPTS 830.7550, Partition Coefficient (n-Octanol/Water) Shake Flask Method, August, 1996, as well as OECD 107 and EEC A.8 shake flask method. The octanol-water partition coefficient was determined at 24 deg C. under three different test conditions (2. 5, 5 and 10 mL of 14C dimethenamid P n-octanol dosing solution). Each test condition was duplicated. A saturated water solution (20 mL ) was used in each case. The amounts of test substance in the octanol and water phases was calculated using the 14C liquid scintillation counts. GLP: Yes 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintStudy Reference: Lam, W.W. 1988. Determination of the n-Octanol/Wate r Partition Coefficient for Dimethenamid-p. BASF Corporation Agricultural Products Group, Research Triangle Park, NC, unpublished. BASF RegDoc #98/5071. 

### Reliability/Data Quality - Partition Coefficient Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted guidelines. 

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## Partition Coefficient
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Partition Coefficient Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethylCAS# 170373-17-8 Sponsored Chemical Result Type:
Test Substance Result Type: Estimated


### Results - Partition Coefficient Partition Coefficient Value/Range (Log K ow ): circa 2.68

Results Remarks: KOWWIN Program (v1.67) Results:

=============================== Log Kow(version 1.67 estimate): 2.68 SMILES : s1cc(c(c1C)NC(COC)C)C CHEM : MOL FOR: C10 H17 N1 O1 S1 MOL WT : 199.31 -------+-----+------------------------------------- -- -----+---------+-------- TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE -------+-----+------------------------------------- -- -----+---------+-------- Frag | 4 | -CH3 [aliphatic carbon] | 0.5473 | 2.1892 Frag | 1 | -CH2- [aliphatic carbon] | 0.4911 | 0.4911 Frag | 1 | -CH [aliphatic carbon] | 0.3614 | 0.3614 Frag | 1 | -O- [oxygen, aliphatic attach] |-1.2566 | -1.2566 Frag | 4 | Aromatic Carbon | 0.2940 | 1.1760 Frag | 1 | -N [aliphatic N, one aromatic attach] |-0.9170 | -0.9170 Frag | 1 | Aromatic Sulfur | 0.4082 | 0.4082 Const | | Equation Constant | | 0.2290 -------+-----+------------------------------------- -- -----+---------+-------- Log Kow = 2.6813 

### Study/Method - Partition Coefficient Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintMethod/Guideline and Test Condition Remarks: The partition coefficient was estimated by KOWWIN v1.67 found in EPIWIN v4.00. Measured data for wate r solubility (472.5 mg/L) were entered. For all other input parameters, the default values in EPIWIN were used. GLP: Not Applicable
Study Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008 

### Reliability/Data Quality - Partition Coefficient Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Water Solubility
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Water Solubility Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: - Name: S-dimethenamid or SAN 1289 H - CAS# 163515-14-8 - ID code: RS-1289-082495 - Purity: 98.6% Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Water Solubility Water Solubility Indicator: Water Solubility Value/Range (Solubility): = 1449 mg/L @ Temperature: 25 °C

pH Value: Value/Lower Range: circa 5.9 Upper Range: 6.4
pKa - Protein Kinase:
pH Value at Saturation:
Results Remarks: The calculated mean solubilities and standard deviations at each of three flow rates (0.4, 0.2, and 0.1 mL/minute) were 1455 +/ - 30 mg/L, 1450 +/- 7 mg/L, and 1451 +/- 14 mg/L, respectively. The mean solubility in water was 1449 +/- 17 mg/L a t 25 deg C and pH value of 6.16 +/- 0.28 There is no dissociation in water, therefore pH dependence on solubility is not applicable. 

### Study/Method - Water Solubility Key Study Sponsor Indicator: Year Study Performed: 1996
Method/Guideline Followed: OECD 105
Method/Guideline and Test Condition Remarks: The test was performed according to US EPA Subdivision D, No. 63-8, OECD 105, EEC A.6 column elution method. Solubility was determined by measuring the concentrations of test substance in clear saturated aqueous solutions generated from contact with excess test substance. Excess test substance was loaded onto a support and added to a generator column. Deionized distilled water was then continuously recirculated through the column until equilibrium was establishe d. 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintAliquots were periodically withdrawn for analysis by HPLC. Equilibrium was established by obtaining reproducible concentrations over a period of three consecutive days. Concentrations of triplicate aliquots at each of three flow rates, all less than 0.5 ml/minute, were used to calculate the reported solubility. GLP: Yes
Study Reference: Laster, W. 1996. Solubility of SAN 1289 H in Water. SANDOZ Agro, Inc., Des Plaines, Illinois, unpublished. BASF RegDoc #96/5411. 

### Reliability/Data Quality - Water Solubility Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted guidelines. 

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## Water Solubility
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Water Solubility Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl; Also known as 2,4-dimethyl-N-(1-methyl2methoxy) ethyl-3-aminothiophene, or C4; Lot 8336B01C4 and Purity of 98.44%. Sponsored Chemical Result Type: Measured

Test Substance Result Type: Measured 

### Results - Water Solubility Water Solubility Indicator: Water Solubility Value/Range (Solubility): = 472.51 mg/L @ Temperature: 22 °C

pH Value: Value/Lower Range: = 10.06
pKa - Protein Kinase:
pH Value at Saturation:
Results Remarks: The preliminary water solubility result was 475.07 mg/L or 0.0476% at 22°C. The water solubility determined in the Flask Method was based upon an average of three measurements: 24 hr: 493.40 mg/L 36 hr: 448.97 mg/L 48 hr: 475.17 mg/L density of H2O at 22oC = 0.9978 g/mL Average Conc. (mg/L) = 472.51 Average Conc. (%) = 0.0474 The 24 hr sample prep pH = 10.06 

### Study/Method - Water Solubility Key Study Sponsor Indicator: Key
Year Study Performed: 2009
Method/Guideline Followed: OECD 105
Method/Guideline and Test Condition Remarks: The water solubility for 2,4-dimethyl-N-(1-methyl2methoxy) ethyl 3-aminothiophene (C4) was determine d using OECD Guideline for the Testing of Chemicals #105 using the Flask Method. A series of three measurements of C4 were taken. The test was conducted by accurately weighing 100 m g of C4 into each of three 100 mL volumetric flasks that were diluted to volume with deionized water. Each flask was placed on a magnetic stir. After 24 hours stirring, one flask was filtered for separating the undissolved C4, the 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintfiltrate was extracted into dichloromethane, concentrated to 1 mL, diluted, and assayed using GC

FID analytical method ATM-3017. The other two flasks were treated similarly and tested at intervals of 3 6 and 48 hours. All measurements were made at ambient temperature. The water solubility was calculated with average response factor of C4 of known concentrations using an external standard calculation. If the concentrations measured in at least the last two flasks do not differ by more tha n 15%, the test is satisfactory. GLP: No
Study Reference: Rachamalla, LR. 2009. Determination of water solubility of 2,4-dimethyl-N-(1-methyl-2methoxy) ethyl-3-aminothiophene (C4) by OECD guideline for the testing of chemicals #105 flask method. BASF DOC ID 2008/7019372. BASF Corporation, 14385 West Port Arthur Road, Beaumont, TX 77705. 

### Reliability/Data Quality - Water Solubility Reliability: 1 - Valid Without Restrictions
Reliability Remarks: Study was performed according to an accepted test guideline. 

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## Photodegradation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Photodegradation Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethylCAS# 170373-17-8 Sponsored Chemical Result Type:
Test Substance Result Type: Estimated 

### Results - Photodegradation Photodegradation Result Description: Indirect Photolysis
Photodegradation Value/Range:
Half Life: = 1.057 Hours

Rate Constant: = .0000000001213895 cm3/(molecule*sec)

Photo Medium: Air
Temperature:

Sensitizer: Hydroxy Radicals

Sensitizer Concentration and Units: 1500000 molecules/cm3

Light Source:
Light Source Spectrum: UV/VIS Absorption Spectrum: Quantum Yield:

Breakdown Products Description:
Results Remarks: AOP Program (v1.92) Results:

=========================== SMILES : s1cc(c(c1C)NC(COC)C)C CHEM : MOL FOR: C10 H17 N1 O1 S1 MOL WT : 199.31 ------------------- SUMMARY (AOP v1.92): HYDROXYL RADICALS (25 deg C) -------- Hydrogen Abstraction = 71.4237 E-12 cm3/molecule-sec Reaction with N, S and -OH = 0.0000 E-12 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintcm3/molecule-sec Addition to Triple Bonds = 0.0000 E-12 cm3/molecule-sec Addition to Olefinic Bonds = 0.0000 E-12 cm3/molecule-sec **Addition to Aromatic Rings = 49.9658 E-12 cm3/molecule-sec Addition to Fused Rings = 0.0000 E-12 cm3/molecule-sec OVERALL OH Rate Constant = 121.3895 E-12 cm3/molecu le
-sec HALF-LIFE = 0.088 Days (12-hr day; 1.5E6 OH/cm3) HALF-LIFE = 1.057 Hrs ........................ ** Designates Estimation(s ) Using ASSUMED Value(s) ------------------- SUMMARY (AOP v1.91): OZONE REACTION (25 deg C) ----------- ****** NO OZONE REACTION ESTIMATION ****** (ONLY Olefins and Acetylenes are Estimated) Experimental Database: NO Structure Matches Fraction sorbed to airborne particulates (phi): 0.000208 (Junge-Pankow, Mackay avg) 0.00401 (Koa method) Note: the sorbed fraction may be resistant to atmospheric oxidation 

### Study/Method - Photodegradation Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: Deviations from Method/Guideline: Method/Guideline Description: Photodegradation was estimated by AOPWIN v1.92 foun d in EPIWIN v4.00. Measured data for water solubility (472.5 mg/L) were entered. For all other input parameters, the default values in EPIWIN were used. Method/Guideline and Test Condition Remarks: GLP: Not Applicable
Study Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008 

### Reliability/Data Quality - Photodegradation Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Photodegradation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Photodegradation Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: dimethenamid, CAS No. 163515-14-8

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Estimated 

### Results - Photodegradation Photodegradation Result Description: Indirect Photolysis
Photodegradation Value/Range:
Half Life: = 2.452 Hours

Rate Constant: = .0000000000052336 cm3/(molecule*sec)

Photo Medium: Air
Temperature:

Sensitizer: Hydroxy Radicals

Sensitizer Concentration and Units: 1500000 molecules/cm3

Light Source:
Light Source Spectrum: UV/VIS Absorption Spectrum: Quantum Yield:

Breakdown Products Description:
Results Remarks: AOP Program (v1.92) Results:

=========================== SMILES : s1c(c(N(C(C)COC)C(=O)CCL)c(c1)C)C CHEM : MOL FOR: C12 H18 CL1 N1 O2 S1 MOL WT : 275.80 ------------------- SUMMARY (AOP v1.92): HYDROXYL RADICALS (25 deg C) -------- Hydrogen Abstraction = 36.3819 E-12 cm3/molecule-sec Reaction with N, S and -OH = 0.0000 E-12 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintcm3/molecule-sec Addition to Triple Bonds = 0.0000 E-12 cm3/molecule-sec Addition to Olefinic Bonds = 0.0000 E-12 cm3/molecule-sec **Addition to Aromatic Rings = 15.9541 E-12 cm3/molecule-sec Addition to Fused Rings = 0.0000 E-12 cm3/molecule-sec OVERALL OH Rate Constant = 52.3360 E-12 cm3/molecul e -sec HALF-LIFE = 0.204 Days (12-hr day; 1.5E6 OH/cm3) HALF-LIFE = 2.452 Hrs ........................ ** Designates Estimation(s ) Using ASSUMED Value(s) ------------------- SUMMARY (AOP v1.91): OZONE REACTION (25 deg C) ----------- ****** NO OZONE REACTION ESTIMATION ****** (ONLY Olefins and Acetylenes are Estimated) Experimental Database: NO Structure Matches Fraction sorbed to airborne particulates (phi): 0.0641 (Junge-Pankow, Mackay avg) 0.000455 (Koa method) Note: the sorbed fraction may be resistant to atmospheric oxidation 

### Study/Method - Photodegradation Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: Deviations from Method/Guideline: Method/Guideline Description: Photodegradation was estimated by AOPWIN v1.92 foun d in EPIWIN v4.00. Experimentally determined water solubility, vapor pressure, partition coefficient, and boiling temperature were manually entered, all other parameters were the default values found in EPIWIN. Method/Guideline and Test Condition Remarks: GLP:
Study Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008. 

### Reliability/Data Quality - Photodegradation Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Photodegradation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Photodegradation Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: [14C]-S-dimethenamid was obtained by isolation of t he individual enantiomers from 14C-SAN 582 H - CAS No.: 163515-14-8 - Purity: [14C]-S-Dimethenamid, enantiomeric purity : Z 98%, specific activity: 50.56 mCi/mmol Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Photodegradation Photodegradation Result Description: Photodegradation Value/Range:
Half Life:

Rate Constant:

Photo Medium: Water
Temperature:

Sensitizer:

Sensitizer Concentration and Units: Light Source: Xenon Lamp
Light Source Spectrum: >= 290 nm
UV/VIS Absorption Spectrum: Quantum Yield:

Breakdown Products Description:
Results Remarks: In the irradiated samples, the material balance ranged from 99.6 to 103% TAR (total applied radioactivity) in the dimethenamid study and 98 to 102% in the dimethenamid-P study. For the dark control samples, the material balance of radioactivity averaged 102% TAR for dimethenamid-P and 99.8% TAR for the racemic compound. 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintDimethenamid and dimethenamid-P were gradually photodegraded following the first order kinetics wi th rates of 0.042/day and 0.051/day respectively. The half-lives, under continuous irradiation, were 16.4 days for dimethenamid and 13.7 days for dimethenami dP. No degradation was observed in the dark controls throughout the study periods. The material balance ranged from 98 to 102% of the applied 14C material. DT50 = 14-16 days Since the simulated sunlight in each study was 1.47 and 1.88 times greater, respectively, than the spri ng noon sunlight at 40 deg N latitude, these half-live s represent: Dimethenamid: 1.47 x 16.4 = 24.1 days Dimethenamid-P: 1.88 x 13.7 = 25.7 days 

### Study/Method - Photodegradation Key Study Sponsor Indicator: Year Study Performed: 1997
Method/Guideline Followed: Other

Deviations from Method/Guideline: Method/Guideline Description: TEST SYSTEM Two separate studies were conducted to determine th e photolysis of the racemic dimethenamid (Sabat, 1992 ) and dimethenamid-P (Guirguis, 1997) in aqueous solutions. In both studies, photolysis of radiolabeled test substance in aqueous solutions (1 00 mg/L) was determined in pH 7 buffer under a xenon lamp with wavelengths < 290 nm filtered out, approximating the spectrum of natural sunlight. Irradiation was continuous at 8.55 x 10^2 W/m^2 (or 3.1 x 10^6 W-hour/m^2) in the dimethenamid study an d 1.1 x 10^3 W/m^2 (or 4.0 x 10^6 W-hour/m^2) in the dimethenamid-P study (1.47 and 1.88 times the sprin g noon sunlight at 40 deg N latitude, respectively). Samples were collected at 0, 1, 5, 11, 15 and 19 da ys after treatment for the dimethenamid study and 0, 2 , 5, 8, 12 and 16 days after treatment for the dimethenamid-P study. Dark controls were analyzed at each interval in the dimethenamid-P study, but only at the final period in the dimethenamid study. Each irradiated and dark control sample was partitioned with ethyl acetate a nd the ethyl acetate layer was analyzed by TLC. Method/Guideline and Test Condition Remarks: Other aqueous systems photodegradation studies available: Sen, P.K. 1994. SAN 582 H: Quantum Yield Determination. SANDOZ Agro, Inc., Des Plaines, Illinois 60018, unpublished. BAS F RegDoc #94/10636. In a GLP study performed according to US EPA, Subdivision N, 161-2, dimethenamid was found to hav e a DT50 of 5.97 in spring at 40 deg N latitude when it was photolyzed with monochromatic light at waveleng th of 313 nm. Scharf, J. 1999. Photolytical Halflife of dimethenamid in the top layer of aqueous systems. BASF AG, Ecology and Environmental Analytics, Limburgerhof, Germany, unpublished. BASF RegDoc #99/10073. A non-GLP study performed according to Council Directive 94/37/EC (July 22, 1994) calculated DT50 estimates for dimethenamid in the range of 0.2 -5.9 days in aqueous systems. These values were determin ed using the quantum yield and a program (Quantum.301) 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintwhich used algorithms for the direct phototransformation of chemicals in water. GLP: Yes
Study Reference: Guirguis, A.S. 1997. S-dimethenamid: Photodegradati on study in an aqueous solution. SANDOZ Agro, Inc., De s Plaines, Illinois, unpublished. BASF RegDoc #97/519 5 Sabat, M. 1992. SAN 582 H: Photodegradation Study i n Aqueous Solution. SANDOZ Agro,Inc., Des Plaines, Illinois, unpublished. BASF RegDoc #92/12388. 

### Reliability/Data Quality - Photodegradation Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted direct photodegradation determination guidelines. 

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## Stability in Water
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Stability In Water Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: dimethenamid-P and dimethenamid

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Stability In Water Stability in Water Result Description: Stability in Water Value/Range: circa 31 Days @ 25 °C
pH Value: Value or Lower Range: = 5 Upper Range: 9
Hydrolysis Indicator: No
Preliminary Test:

Effect : Half-Life @ pH Value

Breakdown Products Description:
Results Remarks: Both dimethenamid and dimethenamid-P were hydrolytically stable in pH 5.0, 7.0 and 9.0 buffer solutions at 25 deg C (+/- 1 deg C) for a period of 31 days. 

### Study/Method - Stability In Water Key Study Sponsor Indicator: Year Study Performed: 1997
Method/Guideline Followed: Other 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintDeviations from Method/Guideline: Method/Guideline Description: The test was performed according to US EPA Subdivision N, No. 161-1 (fulfills EEC C.7). In separate studies, buffer solutions at pH 5, 7 an d 9 were fortified with 14C-dimethenamid or 14C-dimethenamid P to a concentration of 100 mg/kg and incubated at 25 +/- 1 deg C for 30 or 31 days. Samples were collected at day 0, 1, 7, 14, 21 and 30 or 31. Each sample was partitioned with ethyl acetate or ethyl ether, and the organic layer characterized by TLC. Method/Guideline and Test Condition Remarks: abiotic

GLP: Yes
Study Reference: Guirguis, A.S., 1997. Hydrolysis of s-dimethenamid. SANDOZ Agro, Inc., Des Plaines, IL, unpublished. BA SF Reg. Doc. #97/5184 

### Reliability/Data Quality - Stability In Water Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted guidelines. 

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## Transport Between Environmental Compartments Fugacity/Dist
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Transport Between Environmental Compar tments Fugacity/Dist Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: dimethenamid

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Estimated 

### Results - Transport Between Environmental Compartments Fugacity/Dist Fugacity/Distribution Result Description: Multimedia (Fugacity) Modeling

Test Results: Level III Fugacity Model (Full-Output):

======================================= Chem Name : Molecular Wt: 275.8 Henry's LC : 8.2e-008 atm-m3/mole (Henry database) Vapor Press : 1.89e-005 mm Hg (user-entered) Log Kow : 1.89 (user-entered) Soil Koc : 141 (KOCWIN MCI method) Mass Amount Half-Life Emissions (percent) (hr) (kg/hr) Air 0.125 4.91 1000 Water 18.9 1.44e+003 1000 Soil 80.8 2.88e+003 1000 Sediment 0.173 1.3e+004 0 Fugacity Reaction Advection Reaction Advection (atm) (kg/hr) (kg/hr) (percent) (percent) Air 4.76e-012 796 56.3 26.5 1.88 Water 1.27e-012 412 856 13.7 28.5 Soil 1.64e-011 880 0 29.3 0 Sediment 1.33e-012 0.419 0.157 0.014 0.00523 Persistence Time: 1.51e+003 hr Reaction Time: 2.17e+003 hr Advection Time: 4.96e+003 hr Percent Reacted: 69.6 Percent Advected: 30.4 Half-Lives (hr), (based upon Biowin (Ultimate) and Aopwin): Air: 4.906 Water: 1440 Soil: 2880 Sediment: 1.296e+004 Biowin estimate: 2.204 (months ) Advection Times (hr): Air: 100 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintWater: 1000 Sediment: 5e+004 Transport Table: Emissions (kg/h) Halflife (hr) Mass Distribution (percent) Loss by

Reaction (percent) Loss by

Advection (percent) Air 1000 4.91 0.125 26.5 1.88 Water 1000 1440 18.9 13.7 28.5 Soil 1000 2880 80.8 29.3 0 Sediment 13000 0.173 0.014 0.00523 Temperature:

Level of Multi-media Model: III
Model Input (Water Solubility): 1449 mg/L
Model Input (Vapor Pressure): .0000189 mm Hg
Model Input (log K ow ): 1.89
Model Input (Melting Point): Henry's Law Constant: Model Concentration -- Air:
Model Concentration -- Water: Model Concentration -- Soil:
Model Concentration -- Sediment:
Results Remarks: 

### Study/Method - Transport Between Environmental Compartments Fugacity/Dist Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: Deviations from Method/Guideline: Method/Guideline Description: The fugacity was determined using EQC Level III mod el as found in EPIWIN v4.00. Degradation in air, water , soil and sediment was determined from the BIOWIN (ultimate) and the AOPWIN program. Direct photolysi s was not considered in this model. Experimentally determined values for the boiling temperature, vapo r pressure, the octanol-water partition coefficient, and water solubility were manually entered. All other i nput parameters used were the default values found in EPIWIN. Method/Guideline and 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintTest Condition Remarks: GLP: Not Applicable
Study Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008. 

### Reliability/Data Quality - Transport Between Environment al

Compartments Fugacity/Dist Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Transport Between Environmental Compartments Fugacity/Dist
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Transport Between Environmental Compar tments Fugacity/Dist Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethylCAS# 170373-17-8

Sponsored Chemical Result Type:
Test Substance Result Type: Estimated 

### Results - Transport Between Environmental Compartments Fugacity/Dist Fugacity/Distribution Result Description: Multimedia (Fugacity) Modeling

Test Results: Level III Fugacity Model (Full-Output):

======================================= Chem Name : Molecular Wt: 199.31 Henry's LC : 5.71e-008 atm-m3/mole (Henrywin progra m) Vapor Press : 0.00222 mm Hg (Mpbpwin program) Liquid VP : 0.00658 mm Hg (super-cooled) Melting Pt : 72.7 deg C (Mpbpwin program) Log Kow : 2.68 (Kowwin program) Soil Koc : 158 (KOCWIN MCI method) Mass Amount Half-Life Emissions (percent) (hr) (kg/hr) Air 0.0853 2.11 1000 Water 21.1 900 1000 Soil 78.6 1.8e+003 1000 Sediment 0.202 8.1e+003 0 Fugacity Reaction Advection Reaction Advection (atm) (kg/hr) (kg/hr) (percent) (percent) Air 3.25e-012 870 26.5 29 0.885 Water 9.4e-013 505 656 16.8 21.9 Soil 9.53e-012 942 0 31.4 0 Sediment 9.43e-013 0.539 0.126 0.018 0.0042 Persistence Time: 1.04e+003 hr Reaction Time: 1.34e+003 hr Advection Time: 4.55e+003 hr Percent Reacted: 77.2 Percent Advected: 22.8 Half-Lives (hr), (based upon Biowin (Ultimate) and Aopwin): Air: 2.115 Water: 900 Soil: 1800 Sediment: 8100 Biowin estimate: 2.465 (weeks-months) Advection Times (hr): 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintAir: 100 Water: 1000 Sediment: 5e+004 Transport Table: Emissions (kg/h) Half

-life (hr) Mass Distribution (percent) Loss by

Reaction (percent) Loss by

Advection (percent) Air 1000 2.11 0.085336 29 0.885 Water 1000 900 21.1 16.8 21.9 Soil 1000 1800 78.6 31.4 0 Sediment 8100 0.202 0.018 0.0042 Temperature:

Level of Multi-media Model: III
Model Input (Water Solubility): 472.5 mg/L
Model Input (Vapor Pressure): Model Input (log K ow ): Model Input (Melting Point): Henry's Law Constant: Model Concentration - - Air:
Model Concentration - - Water: Model Concentration - - Soil:
Model Concentration - - Sediment:
Results Remarks: 

### Study/Method - Transport Between Environmental Compartments Fugacity/Dist Key Study Sponsor Indicator: Year Study Performed: 2011
Method/Guideline Followed: Deviations from Method/Guideline: Method/Guideline Description: Fugacity was determined using EQC Level III model a s found in EPIWIN v4.00. Equal emission to air, water , and soil were assumed. Measured data for water solubility was entered. All other input parameters used in the calculation weret the default values fo und in EPIWIN. Method/Guideline and Test Condition Remarks: GLP: Not Applicable 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintStudy Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008 

### Reliability/Data Quality - Transport Between Environme ntal

Compartments Fugacity/Dist Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Biodegradation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Biodegradation Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: dimethenamid, radiolabled, CAS No. 163515-14-8

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Biodegradation Biodegradability Indicator:
Effect : Concentration Value Time

in Days Biodegradation

Value Biodegradation

Value Range

Half Life:

Rate Constant:

Temperature:

Incubation Condition: Aerobic

Inoculum Type:

Inoculum Concentration:
Inoculum Remarks:

Pre-Exposure Indicator: Pre-Exposure Remarks:
Theoretical Carbon DiOxide: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintTheoretical Oxygen Demand: Chemical Oxygen Demand:
Control Substance Remarks:
Breakdown Products Description:
Results Remarks: Recovery of radioactivity in the river and pond systems varied between 97 and 102% TAR. In both systems, the proportion of radioactivity in the wat er decreased below 32% TAR and 105 days after treatmen t, whereas radioactivity in the sediment increased to above 67% TAR at 105 days. Similar results were observed in the non-sterile samples and the sterile controls. In addition, the amount of bound residues increased to approximately 52% TAR in both systems. Volatile radioactivity (14CO2) accounted for 2.7% T AR at 105 days. Degradation of dimethenamid followed first-order kinetics and DT50 values were calculated by the method of Timme and Frehse. For the water phase, DT50 values were 20 and 28 day s for the river and pond systems, respectively. The DT50 values for the whole system were 23 days (rive r) and 33 days (pond). 

### Study/Method - Biodegradation Key Study Sponsor Indicator: Year Study Performed: 1994
Method/Guideline Followed: Deviations from Method/Guideline: Method/Guideline Description: Water and sediment were taken from two different systems, the Rhine River and a pond. The properties of the sediment and water were determined at the beginning and end of the study. The study was done in glass metabolism flasks containing 200 g sediment a nd 530 mL water to which 256 ug radiolabeled dimethenamid was added. The system was continuously ventilated, and the effluent air passed through a trapping system for CO2 and organic compounds. The samples were incubated at 20 deg C in the dark and the water gently stirred from the top without disturbing the sediment. Two flasks of each system were taken for analysis a t day 0, 0.25, 1, 2, 7, 14, 28, 56, and 105. Sterile samples were collected and analyzed only at day 105. At each sampling, the water layer was removed and partitioned with ethyl acetate. The sediment was extracted with acetonitrile/water. The bound residues were characterized to determine the proportions of fulvi c and humic acids, and fulvin. Extractable residues were characterized by TLC and HPLC. Method/Guideline and Test Condition Remarks: GLP: Yes 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintStudy Reference: Wyss-Benz, M., Vokel, W., 1994. [3-14C-thienyl] dimethenamid degradation and metabolism in aerobic aquatic systems, RCC, Researc h and Consulting Company AG, Switzerland, unpublished, BASF RegDoc.#94/10641. 

### Reliability/Data Quality - Biodegradation Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study conducted according to acceptable guideline 

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## Biodegradation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Biodegradation Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4 -dimethyl-; Reg. No. 364802 (Process intermediate o f BAS 656-PH, DMTA-P); Batch ID: B1112B01C4, CAS No: 170373-17-8; Purity 97.4 corr. area %.
Sponsored Chemical Result Type: Measured

Test Substance Result Type: Measured 

### Results - Biodegradation Biodegradability Indicator: No Degradation Observed

Effect : Concentration Value Time

in Days Biodegradation

Value Biodegradation

Value Range 28 = 1.8 % Degradation

Half Life:

Rate Constant:

Temperature: 22 °C

Incubation Condition: Aerobic

Inoculum Type: Activated Sludge

Inoculum Concentration: 4 mg/L

Inoculum Remarks: Municipal activated sludge from the wastewater treatment plan of Mannheim, Germany was collected from the aeration tank of the plant. A suitable aliquot of the suspension was sieved by a finely woven mesh with a mesh size of about 1 mm. To reduc e the content of inorganic carbon in the blank contro l, the activated sludge was aerated with carbon dioxid e free air for about 48 hours at 22 +/- 2 deg C. At the day of exposure the aeration was stopped and th e sludge was allowed to settle. The supernatant was discarded and the residue of the sludge suspension 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintwas filled up with tap water. The sludge of the suspension was adjusted to a concentration of 800 mg/L of dry weight. Aliquots of 0.5 mL were added to the test vessels to obtain a sludge concentration o f 4 mg/L dry substance in the test assays. Pre-Exposure Indicator: Pre-Exposure Remarks:
Theoretical Carbon DiOxide: Theoretical Oxygen Demand: Chemical Oxygen Demand:
Control Substance Remarks: Aniline was the control substance

Breakdown Products Description:
Results Remarks: The extent of biodegradation is expressed as a percentage of formed Total Inorganic Carbon (TIC) o f the Total Organic Carbon (TOC) based on the amount of the test compound added initially. The biodegradation degree (% TIC/TOC): 1.8% +/- 1% after an exposure period of 28 days (mean value of five test assays, limit of confidence 95%). Reg. No. 364802 (Process-intermediate of BAS 656-PH , DMTA-P) was, in this test, poorly biodegradable. Assessment in accordance to criteria of the OECD Te st Guideline: The test substance was not readily biodegradable under the conditions of this test. Degradation degree of the reference substance was > 60% TIC/TOC after 14 days. It was 75% (mean value). Degradation degree in the inhibtion control was > 2 5% TIC/TOC after 28 days. It was 45% (mean value). 

### Study/Method - Biodegradation Key Study Sponsor Indicator: Key
Year Study Performed: 2009
Method/Guideline Followed: OECD 310

Deviations from Method/Guideline: No
Method/Guideline Description: OECD 310, Ready Biodegradability - CO2 in sealed vessels (Headspace Test). The CO2-headspace test is an aquatic batch test method to determine the aerobic biodegradability of a test substance in closed bottles by analysis of the evolved carbon dioxide (CO2). The test compound, as the sole source of carbon and energy, is added to mineral salts medium inoculated with a mixed population of micro organisms and incubated in sealed vessels with a headspace of air. Biodegradation (mineralization to carbon dioxide) is determined by measuring the net increas e in Total Inorganic Carbon (TIC) levels over time compared with blanks without test compound. The tes t generally runs for 28 days. The extent of biodegradation is expressed as a percentage of form ed 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintTIC of the total organic carbon (TOC) based on the amount of the test compound added initially. Method/Guideline and Test Condition Remarks: The test guideline recommends a test concentration of the test substance of 2-40 mg/L Total Organic Carbo n (TOC). Generally a test concentration of 20 mg/L TO C is used. The selected test concentration of 20 mg/L TOC corresponds to approximately 33 mg/L test substance. It is anticipated that the selected test concentration causes no toxic effects to the microorganisms. The selected test concentration was tested in an additional inhibition control test ass ay and no toxic effects to the microorganisms were observed. The CO2-Headspace test was performed in 160 mL incubation bottles filled up to a volume of 100 mL. The oxygen available in the headspace of the bottles is used for the aerobic mineralization processes. The amount of oxygen allows the complete biodegradation. The aqueous phase, a mineral medium with municipal inoculum, contains the test compound , directly added by a suitable syringe. The bottles were closed with butyl rubber septa gas tight and shaken by an orbital shaker with a speed of about 1 50 r/min and incubated at a temperature of 22 +/- 2 de g C. The pH value of the mineral medium was checked and adjusted to the required range of 7.4 +/- 0.2. The following test assays were prepared: 23 blank control assays; 25 test substance assays; 23 inhibition control test assays; 11 reference substance assays; 5 assays for abiotic control. At each sampling day (days 4, 7, 14, 19, 22, 26, an d 28), 3 bottles of each test assays were sacrificed. (At the end of the exposure, 5 bottles for the test substance treatment were assayed). 1 mL 7M sodium hydroxide solution was injected with a syringe through the septum in each test bottle. The bottles were shaken for about one hour. The CO2 in the headspace, evolved by biologial processes, is dissolved in the alkaline solution. The bottles wer e opened and the amount of Total Inorganic Carbon (TI C) was determined with a carbon analyzer. The measured TIC-values were compared with the added amount of T OC and expressed as biodegradation degree and plotted by a biodegradation curve. GLP: Yes
Study Reference: Schwarz, H. 2009. Report Reg. No. 364802 (Process intermediate of BAS 656-PH, DMTA-P), Determination of the Biodegradability in the CO2-Headspace Test. BAS F DocID 2009/1050251. Experimental Toxicology and Ecology BASF SE 67056 Ludwigshafen, Germany; Projec t No. 27G0934/083656. 

### Reliability/Data Quality - Biodegradation Reliability: 1 - Valid Without Restrictions
Reliability Remarks: Well-documented study conducted according to accept ed guidelines and under GLP. 

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## Biodegradation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Biodegradation Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: - Name: 14C-dimethenamid-P and 14C-dimethenamid - CAS No.: 163515-14-8

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Results - Biodegradation Biodegradability Indicator:
Effect : Concentration Value Time

in Days Biodegradation

Value Biodegradation

Value Range

Half Life:

Rate Constant:

Temperature:

Incubation Condition: Aerobic

Inoculum Type: Soil

Inoculum Concentration:
Inoculum Remarks:

Pre-Exposure Indicator: Pre-Exposure Remarks:
Theoretical Carbon DiOxide: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintTheoretical Oxygen Demand: Chemical Oxygen Demand:
Control Substance Remarks:
Breakdown Products Description:
Results Remarks: In the study by Wendt (1997), half-life (as determined by the % recovery of radioactivity) was approx. 6.7 days (as interpolate d graphically by the reviewer) for dimethenamid-P and 7 days for dimethenamid. The material balance for the dimethenamid-P incubations ranged from 92.9 to 101.5% TAR (total applied radioactivity), and that for dimethenamid ranged from 93.8 to 101.7% TAR. The degradation of both dimethenamid and dimethenamid-P coincided with the formation of up t o seven polar metabolites, none of which exceeded 9% TAR. After t he 182 day incubation period, 14CO2 accounted for 28-29% TAR f or both treatments. Up to 9% TAR was associated with fulvic acid. The humic acid fraction contained up to 25% of the TAR, and 10% TAR was not extractable at the end of the study. In the study by Kruger and Bade (1990), the half-li fe (as determined by the % recovery of radioactivity) was approx. 35 days (as determined by the reviewer)

. The material balance ranged from 82.1 to 108.3% TAR and averaged 92.1% TAR. Volatile breakdown products were mainly in the form of 14CO2 (17.7% TAR at day 365). The mineralization of CO2 increased with time showing that dimethenamid is completely degraded in soil. 

### Study/Method - Biodegradation Key Study Sponsor Indicator: Year Study Performed:

Method/Guideline Followed: Deviations from Method/Guideline: Method/Guideline Description: An aerobic soil metabolism study (Wendt, 1997) was performed according to US EPA Subdivision N, 162-1. The aerobic soil metabolism of 14C-dimethenamid-P and 14C-dimethenam id were compared in Elliot clay loam soil from the U.S

.. Fresh moist soil was screened through a 2 mm sieve prior to test substance application. The concentrations of both test substances were 1.595 mg/kg moist soil (1.994 mg/kg dry soil). Incubation conditions were: aerobic by continuous flow of air, temperature maintained at 23 +/- 1 deg C, and soil moisture at 75% of field capacity. Volatiles were trapped by continuously washing the effluent gas with 1 N NaOH and ethylene glycol. Soil was extracted with 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintmethanol, then methanol: 0.1N HCl. The extracts were pooled, concentrated, and characterized by TLC and HPLC. Bound residues were characterized by extracti on with 0.1N NaOH to separate the fulvic acid, humic acid, and humin fractions. Soil characteristics: - Soil designation: Elliot Clay Loam - Textural class (USDA): Clay loam - Origin: Champaign County, IL (USA) - Particle size distribution 0.063 - 2 mm 24% 0.002 - 0.063 mm 44% <0.002 mm 32% - Organic C% 2.4 - CEC (meg/100 g; cation exchange capacity) 15.6 - PH (CaCl2) 6.4 - FC (g H2O/100 g dry soil; field capacity, determined at 0.33 bar) 33.37 Another aerobic soil metabolism study was performed by Kruger and Bade(1990). This study was also conducted according to US EPA Subdivision N: 162-1. Methods were similar to the study by Wendt (1997), except in this case Kenyon loam soil was used and t he aliquots of treated soil were incubated for interva ls up to one year. Method/Guideline and Test Condition Remarks: A ready biodegradability test was not performed wit h dimethenamid since it was assumed to be not readily biodegradable. This assumption is supported by the results of BIOWIN v.410 (EPIWIN v3.20) which predict that ready biodegradation will not occur, that the time frame for primary biodegradation is days to weeks, and th e time frame for ultimate biodegradation is months. GLP: Yes
Study Reference: Kruger, J.P., Bade, T.R., 1990. Aerobic soil metabolism of SAN 582H, SANDOZ Agro Inc.,Des Plaine s, IL, unpublished, BASF RegDoc.#90/11105 Wendt, D.R. 1997. Comparative aerobic soil metaboli sm of SAN 1289 H and SAN 582 H. Sandoz Agro, Inc., Des Plaines, Illinois 60018, unpublished. BASF RegDoc #97/5257. 

### Reliability/Data Quality - Biodegradation Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to acceptable guidelines. 

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## Biodegradation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Biodegradation Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: dimethenamid, CAS No. 163515-14-8

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Estimated 

### Results - Biodegradation Biodegradability Indicator:
Effect : Concentration Value Time

in Days Biodegradation

Value Biodegradation

Value Range

Half Life:

Rate Constant:

Temperature:

Incubation Condition: Aerobic

Inoculum Type:

Inoculum Concentration:
Inoculum Remarks:

Pre-Exposure Indicator: Pre-Exposure Remarks:
Theoretical Carbon DiOxide: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintTheoretical Oxygen Demand: Chemical Oxygen Demand:
Control Substance Remarks:
Breakdown Products Description:
Results Remarks: Linear and Non-Linear models in BIOWIN v4.10 predic t that dimethenamid does not biodegrade fast. The primary degradation timeframe is predicted to be days to weeks and the ultimate biodegradation timeframe is predicted to be months. 

### Study/Method - Biodegradation Key Study Sponsor Indicator: Year Study Performed:

Method/Guideline Followed: Deviations from Method/Guideline: Method/Guideline Description: Biodegradation was estimated by BIOWIN v4.10 found in EPIWIN v4.00. Experimentally determined water solubility, vapor pressure, partition coefficient, and boiling temperature were manually entered. All other input parameters were the default values found in EPIWIN. Method/Guideline and Test Condition Remarks: GLP: Not Applicable
Study Reference: EPISuite v4.00, US Environmental Protection Agency, 2000-2008. 

### Reliability/Data Quality - Biodegradation Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation. 

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## Acute Toxicity to Aquatic Vertebrates

CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Vertebrates Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Identity: dimethenamid-P technical (SAN 1289 H) Lot: #6663-50-1 Purity: 91.1%

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Method - Acute Toxicity To Aquatic Vertebrates Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 72-1

Other Method/Guideline: Deviations from Method/Guideline: Species: Oncorhynchus mykiss

GLP: Yes
Analytical Monitoring: Yes
Test Type: Flow-through

Test Vessel:
Water Media Type: Freshwater

Test Concentrations: Measured

Nominal and Measured Concentrations: Test concentrations: Control, Solvent Control, 1.4, 2.3, 3.7, 6.5 and 11 mg ai/L (measured as total dimethenamid)
The concentration control analysis yielded mean mea sured concentrations between 103 and 110% of nominal concentrations; hen ce, results confirm nominal values. Exposure Period: 96 Hours

Vehicle Used:

Vehicle Name: 

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and Units: Alkalinity:
Dissolved Oxygen: 8.8-9.6 mg/L
pH Value: Value/Lower Range: = 8.2 Upper Range: 8.3
Test Temperature and Units: Value/Lower Range: 11 Upper Range: 13 °C

Photo (Light/Dark): 16/8
Salinity:

TOC:

Water Hardness: 124 mg/L
Method/Guideline Test Conditions Remarks: The study was performed according to US EPA Subdivi sion E, Guideline 72-1. Test Species Species: Oncorchynchus mykiss, rainbow trout Age: ca. 4 months old Body weight: ca. 1.9 g Body length: ca. 5.1 cm Test design Type: continuous flow-through Duration: 96 hours Fish per test concentration: 20 (instantaneous load ing 1.3 g fish/L water) Test concentrations: Control, Solvent Control, 1.4, 2.3, 3.7, 6.5 and 11 mg ai/L (measured as total dimethenamid) Analytics: GC with electron capture detection Statistics: binomial method Limit Test: No 

### Test Results - Acute Toxicity To Aquatic Vertebrates NOEC Exposure Duration: 96 Hours

NOEC: = 3.7 mg/L
LOEC Exposure Duration:
LOEC:
NOELR Exposure Duration:
NOELR:
LOELR Exposure Duration:
LOELR:

LC/EC Mean Value : Exposure Duration Exposure

Units LC/EC % Value Description Mean

Value or Lower Upper

Mean Value Units Effect

Observed Basis for

Concentration 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintMean Value 96 Hours LC 50 % = 6.3 mg/L

Results Remarks: Analytical Measurements The concentration control analysis yielded mean mea sured concentrations between 103 and 110% of nominal concentrations; hen ce, results confirm nominal values. Biological Results The TS caused no mortality or other signs of toxici ty in the rainbow trout up to 3.7 mg ai/L during the test. After 96 h of expos ure, mortality in the 6.5 and 11 mg ai/L was 55 and 100%, respectively. 

### Reliability/Data Quality - Acute Toxicity To Aquatic Ver tebrates Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to an accepted test g uideline for fish acute toxicity testing. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity To Aquatic Vertebrates Reference: Graves, W., Swigert, J., 1996. SAN 1289 H Technical : A 96-hour flow-through acute toxicity test with rainbow trout (Oncorchynchus myk iss). Wildlife International, Ltd., Easton, Maryland, USA, unpublished. BASF RegDoc #96 /5417. 

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## Acute Toxicity to Aquatic Vertebrates

CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Vertebrates Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Identity: dimethenamid-P technical (SAN 1289 H) Lot: #6663-50-1 Purity: 91.1%

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Method - Acute Toxicity To Aquatic Vertebrates Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 72-1

Other Method/Guideline: Deviations from Method/Guideline: Species: Lepomis macrochirus

GLP: Yes
Analytical Monitoring: Yes
Test Type: Flow-through

Test Vessel:
Water Media Type: Freshwater

Test Concentrations: Measured

Nominal and Measured Concentrations: Concentrations: Control, Solvent Control, 2.4, 4.1, 7.5, 12 and 20 mg ai/L (measured) The concentration control analysis yielded mean mea sured concentrations between 95 and 104% of nominal concentrations; henc e, results confirm nominal values. Exposure Period: 96 Hours

Vehicle Used:

Vehicle Name: 

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and Units: Alkalinity:
Dissolved Oxygen: 7.6-8.3 mg/L
pH Value: Value/Lower Range: = 8.2 Upper Range: 8.4
Test Temperature and Units: Value/Lower Range: 22 Upper Range: 22.5 °C

Photo (Light/Dark): 16/8
Salinity:

TOC:

Water Hardness: 136 mg/L
Method/Guideline Test Conditions Remarks: The study was performed according to US EPA Subdivi sion E, Guideline 72-1. Test Species Species: Lepomis macrochirus, bluegill sunfish Body length: ca. 2.3 cm Body weight: ca. 0.29 g Test design Type: continuous flow-through Duration: 96 hours Fish per test concentration: 20 (instantaneous load ing 1.9 g fish/L water) Concentrations: Control, Solvent Control, 2.4, 4.1, 7.5, 12 and 20 mg ai/L (measured) Analytics: GC with electron capture detection Statistics: binomial method Limit Test: No 

### Test Results - Acute Toxicity To Aquatic Vertebrates NOEC Exposure Duration: 96 Hours

NOEC: = 4.1 mg/L
LOEC Exposure Duration:
LOEC:
NOELR Exposure Duration:
NOELR:
LOELR Exposure Duration:
LOELR:

LC/EC Mean Value : Exposure Duration Exposure

Units LC/EC % Value Description Mean

Value or Lower Mean Value Upper

Mean Value Units Effect

Observed Basis for

Concentration 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint96 Hours LC 50 % = 10 mg/L

Results Remarks: Analytical Measurements The concentration control analysis yielded mean mea sured concentrations between 95 and 104% of nominal concentrations; henc e, results confirm nominal values. Biological Results The TS caused mortality to the fish only at concent rations of 12 mg ai/L and higher. Symptoms such as lethargy and discolora tion were observed at 7.5 mg ai/L (72 and 96 h), 12 mg ai/L (24 h and later) and 20 mg ai/L (24 h until death). 

### Reliability/Data Quality - Acute Toxicity To Aquatic Ver tebrates Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to an accepted test g uideline for fish acute toxicity testing. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity To Aquatic Vertebrates Reference: Graves, W., Swigert, J., 1996. SAN 1289 H Technical : A 96-hour flow-through acute toxicity test with the bluegill (Lepomis macrochiru s). Wildlife International, Ltd., Easton, Maryland, USA, unpublished. BASF RegD oc #96/5414. 

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## Acute Toxicity to Aquatic Vertebrates

CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Vertebrates Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1- methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: Sponsored Chemical Result Type: Test Substance Result Type: Estimated 

### Method - Acute Toxicity To Aquatic Vertebrates Year Study Performed: 2011
Method/Guideline Followed:
Other Method/Guideline: Deviations from Method/Guideline: Species:

GLP: Not Applicable
Analytical Monitoring: Test Type:

Test Vessel:
Water Media Type:

Test Concentrations:
Nominal and Measured Concentrations: Exposure Period:

Vehicle Used:

Vehicle Name:

Vehicle Amount and Units: Alkalinity: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintDissolved Oxygen:

pH Value:

Test Temperature and Units:
Photo (Light/Dark): Salinity:

TOC:

Water Hardness:

Method/Guideline Test Conditions Remarks: The acute toxicity to fish was estimated using ECOS AR v1.00 in EPIWIN v4.00. Measured data for water solubility entered. For all other input parameters, the defaul t values in EPIWIN were used. Limit Test: 

### Test Results - Acute Toxicity To Aquatic Vertebrates NOEC Exposure Duration:
NOEC:
LOEC Exposure Duration:
LOEC:
NOELR Exposure Duration:
NOELR:
LOELR Exposure Duration:
LOELR:

LC/EC Mean Value : Exposure Duration Exposure

Units LC/EC % Value Description Mean

Value or Lower Mean Value Upper

Mean Value Units Effect

Observed Basis for

Concentration

96 Hours LC 50 % circa 12 mg/L 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintResults Remarks: ECOSAR Program (v1.00) Results:

============================== SMILES : s1cc(c(c1C)NC(COC)C)C CHEM : CAS Num: ChemID1: ChemID2: ChemID3: MOL FOR: C10 H17 N1 O1 S1 MOL WT : 199.31 Log Kow: 2.68 (KowWin estimate) Melt Pt: Wat Sol: 472.5 mg/L (measured)
ECOSAR v1.00 Class(es) Found

------------------------------ Thiophenes Predicted ECOSAR Class Organism Du ration End Pt mg/L (ppm)

=========================== ================== == ====== ====== ========== Thiophenes : Fish 96 -hr LC50 12.032 Thiophenes : Daphnid 48 -hr LC50 8.677 Thiophenes : Green Algae 96 -hr EC50 16.779 Thiophenes : Fish ChV 0.725 ! Thiophenes : Daphnid ChV 0.825 ! Thiophenes : Green Algae ChV 12.151

=========================== ================== == ====== ====== ========== Neutral Organic SAR : Fish 96 -hr LC50 40.712 (Baseline Toxicity) : Daphnid 48 -hr LC50 25.509 : Green Algae 96-hr EC50 14.544 : Fish ChV 3.807 : Daphnid ChV 2.658 : Green Algae ChV 5.961 Note: * = asterisk designates: Chemical may not be soluble enough to measure this predicted effect. Note: ! = exclamation designates: The toxicity val ue was determined from a predicted SAR using established acute-to-chronic ratios and ECOSAR regression techniques which are documented in the s upporting Technical Reference Manual. When possible, this toxicity valu e should be considered in a weight of evidence approach. Thiophenes:

---------- For Fish and Daphnid Acute Toxicity Values: If the log Kow of the chemical is greater than 5.0, or if the compound is solid an d the LC50 exceeds the water solubility by 10X, no effects at saturation a re predicted for these endpoints. For Green Algae Acute Toxicity Values: If the log K ow of the chemical is greater than 6.4, or if the compound is solid and t he EC50 exceeds the water solubility by 10X, no effects at saturation are pre dicted for these endpoints. For All Chronic Toxicity Values: If the log Kow of the chemical is greater than 8.0, or if the compound is solid and the ChV e xceeds the water solubility by 10X, no effects at saturation are predicted for these endpoints.

ECOSAR v1.00 SAR Limitations:

---------------------------- Maximum LogKow: 5.0 (LC50) Maximum LogKow: 6.4 (EC50) Maximum LogKow: 8.0 (ChV) Maximum Mol Wt: 1000 Baseline Toxicity SAR Limitations:

--------------------------------- Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50) Maximum LogKow: 6.4 (Green Algae EC50) Maximum LogKow: 8.0 (ChV) Maximum Mol Wt: 1000 

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### Reliability/Data Quality - Acute Toxicity To Aquatic Ver tebrates

Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation
Key Study Sponsor Indicator: 

### Reference - Acute Toxicity To Aquatic Vertebrates Reference: EPI Suite v4.00, U.S. Environmental Protection Agen cy, 2000 - 2008. 

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## Acute Toxicity to Aquatic Invertebrates

CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Invertebrat es Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Identity: dimethenamid-P technical (SAN 1289 H) Lot: #6663-50-1 Purity: 91.1%

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Method - Acute Toxicity To Aquatic Invertebrates Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 72-2

Other Method/Guideline: Deviations from Method/Guideline: Species/In Vitro System: Daphnia magna

GLP: Yes
Analytical Monitoring: Yes
Test Type: Flow-through

Test Vessel:
Water Media Type: Freshwater

Test Concentrations: Measured

Nominal and Measured Concentrations: Concentrations: Control, Solvent control (dimethylf ormamide, DMF), 3.4, 5.2, 9.0, 14 and 26 mg ai/L (measured)
The measured test concentrations ranged from 104-11 8% of nominal at test initiation and from 81-108% at the end of the test. Exposure Period: 48 Hours

Vehicle Used: Yes

Vehicle Name: Other 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintOther Vehicle

Name: dimethylformamide

Vehicle Amount and Units: Alkalinity: 184 mg/L CaCO3
Dissolved Oxygen: 8.1-9.3 mg/L
pH Value: Value/Lower Range: = 8.1 Upper Range: 8.3
Test Temperature and Units: Value/Lower Range: 19.8 Upper Range: 20 °C

Photo (Light/Dark): 16/8
Salinity:

TOC:

Water Hardness: 136 mg/L
Method/Guideline Test Conditions Remarks: The study was performed according to US EPA FIFRA S ubdivision E,Guideline 72-2. Test Species Species: Daphnia magna, water flea Age: less than 24 h at test initiation Housing: parent daphnids are housed individually Culture conditions in accordance with test conditio ns Test design: Type: flow-through Number of replicates: 2 Number of daphnids per replicate: 10 Concentrations: Control, Solvent control (dimethylf ormamide, DMF), 3.4, 5.2, 9.0, 14 and 26 mg ai/L (measured) Examinations: assessment of immobility (and other e ffects) after 24 and 48 h Analytics: analytical verification of TS concentrat ions was conducted in each replicate of each concentration at test initiation and termin ation using gas chromatography with Nitrogen-Phosphorus Detection (NPD) Statistics: standard procedures, probit analysis Limit Test: No 

### Test Results - Acute Toxicity To Aquatic Invertebrate s NOEC Exposure Duration: 48 Hours

NOEC: = 3.4 mg/L
LOEC Exposure Duration:
LOEC:
NOELR Exposure Duration:
NOELR:
LOELR Exposure Duration: 

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LC/EC Mean Value : Exposure Duration Exposure

Units LC/EC % Value Description Mean

Value or Lower Mean Value Upper

Mean Value Units Effect

Observed Basis for

Concentration

48 Hours EC 0 % = 5.4 mg/L
48 Hours EC 50 % = 12 mg/L

Results Remarks: Analytical measurements The measured test concentrations ranged from 104-11 8% of nominal at test initiation and from 81-108% at the end of the test. The following results are based on mean measured concentrations. Biological results Mortality/immobility was observed at test concentra tions greater than or equal to 9.0 mg ai/L. After 48 h 90% of the daphnid s at 14 mg ai/L and 100% of the daphnids at 25 mg ai/L were immobile or dead. A t test termination, one daphnid at 5.2 mg ai/L appeared lethargic and one d aphnid in the 9.0 mg ai/L group was immobile and one was lethargic. The 48 h EC50 was calculated using probit analysis.

Conclusion: In a 48 h flow-through acute toxicity study with Da phnia magna the EC50 of dimethenamid -P was 12 mg ai/L, the no mortality/im mobility concentration (EC0) was 5.4 mg ai/L, and the NOEC was 3.4 mg ai/L. Resu lts are based on mean measured concentrations. 

### Reliability/Data Quality - Acute Toxicity To Aquatic In vertebrates Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to an accepted test g uideline for aquatic invertebrate toxicity testing. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity To Aquatic Invertebrates Reference: Graves, W., Smith, G., 1996. SAN 1289 H Technical: A 48-hour flow-through acute toxicity test with the cladoceran (Daphnia magna). Wildlife International, Ltd., Easton, Maryland, USA, unpublished, unpublished. BA SF RegDoc #96/5415. 

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## Acute Toxicity to Aquatic Invertebrates

CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Invertebrat es Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1- methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: Sponsored Chemical Result Type: Test Substance Result Type: Estimated 

### Method - Acute Toxicity To Aquatic Invertebrates Year Study Performed: 2011
Method/Guideline Followed:
Other Method/Guideline: Deviations from Method/Guideline: Species/In Vitro System:
GLP: Not Applicable
Analytical Monitoring: Test Type:

Test Vessel:
Water Media Type:

Test Concentrations:
Nominal and Measured Concentrations: Exposure Period:

Vehicle Used:

Vehicle Name:

Vehicle Amount and Units: Alkalinity: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintDissolved Oxygen:

pH Value:

Test Temperature and Units:
Photo (Light/Dark): Salinity:

TOC:

Water Hardness:

Method/Guideline Test Conditions Remarks: The acute toxicity to daphnids was estimatedn using ECOSAR v1.00 in EPIWIN v4.00. Measured value for water solubility entered. For al l other input parameters, the default values in EPIWIN were used. Limit Test: 

### Test Results - Acute Toxicity To Aquatic Invertebrate s NOEC Exposure Duration:
NOEC:
LOEC Exposure Duration:
LOEC:
NOELR Exposure Duration:
NOELR:
LOELR Exposure Duration:
LOELR:

LC/EC Mean Value : Exposure Duration Exposure

Units LC/EC % Value Description Mean

Value or Lower Mean Value Upper

Mean Value Units Effect

Observed Basis for

Concentration

48 Hours LC 50 % circa 8.7 mg/L 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintResults Remarks: ECOSAR Program (v1.00) Results:

============================== SMILES : s1cc(c(c1C)NC(COC)C)C CHEM : CAS Num: ChemID1: ChemID2: ChemID3: MOL FOR: C10 H17 N1 O1 S1 MOL WT : 199.31 Log Kow: 2.68 (KowWin estimate) Melt Pt: Wat Sol: 472.5 mg/L (measured)
ECOSAR v1.00 Class(es) Found

------------------------------ Thiophenes Predicted ECOSAR Class Organism Du ration End Pt mg/L (ppm)

=========================== ================== == ====== ====== ========== Thiophenes : Fish 96 -hr LC50 12.032 Thiophenes : Daphnid 48 -hr LC50 8.677 Thiophenes : Green Algae 96 -hr EC50 16.779 Thiophenes : Fish ChV 0.725 ! Thiophenes : Daphnid ChV 0.825 ! Thiophenes : Green Algae ChV 12.151

=========================== ================== == ====== ====== ========== Neutral Organic SAR : Fish 96 -hr LC50 40.712 (Baseline Toxicity) : Daphnid 48 -hr LC50 25.509 : Green Algae 96-hr EC50 14.544 : Fish ChV 3.807 : Daphnid ChV 2.658 : Green Algae ChV 5.961 Note: * = asterisk designates: Chemical may not be soluble enough to measure this predicted effect. Note: ! = exclamation designates: The toxicity val ue was determined from a predicted SAR using established acute-to-chronic ratios and ECOSAR regression techniques which are documented in the s upporting Technical Reference Manual. When possible, this toxicity valu e should be considered in a weight of evidence approach. Thiophenes:

---------- For Fish and Daphnid Acute Toxicity Values: If the log Kow of the chemical is greater than 5.0, or if the compound is solid an d the LC50 exceeds the water solubility by 10X, no effects at saturation a re predicted for these endpoints. For Green Algae Acute Toxicity Values: If the log K ow of the chemical is greater than 6.4, or if the compound is solid and t he EC50 exceeds the water solubility by 10X, no effects at saturation are pre dicted for these endpoints. For All Chronic Toxicity Values: If the log Kow of the chemical is greater than 8.0, or if the compound is solid and the ChV e xceeds the water solubility by 10X, no effects at saturation are predicted for these endpoints.

ECOSAR v1.00 SAR Limitations:

---------------------------- Maximum LogKow: 5.0 (LC50) Maximum LogKow: 6.4 (EC50) Maximum LogKow: 8.0 (ChV) Maximum Mol Wt: 1000 Baseline Toxicity SAR Limitations:

--------------------------------- Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50) Maximum LogKow: 6.4 (Green Algae EC50) Maximum LogKow: 8.0 (ChV) Maximum Mol Wt: 1000 

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### Reliability/Data Quality - Acute Toxicity To Aquatic In vertebrates

Reliability: 2 - Valid With Restrictions
Reliability Remarks: Scientifically acceptable method of calculation.
Key Study Sponsor Indicator: 

### Reference - Acute Toxicity To Aquatic Invertebrates Reference: EPI Suite v4.00, U.S. Environmental Protection Agen cy, 2000 - 2008. 

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## Acute Toxicity to Aquatic Plants
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Plants Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Identity: SAN 1289 H technical (dimethenamid-P tech nical) Lot: #6663-50-1 Purity: 91.1%

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Method - Acute Toxicity To Aquatic Plants Year Study Performed: 1997
Method/Guideline Followed: Other

Other Method/Guideline: EPA OPP 122-2 and 123-2

Deviations from Method/Guideline: Species: Other
Other Species: Lemna gibba (duckweed)

GLP: Yes
Analytical Monitoring: Yes
Test Type: Static

Test Vessel:
Water Media Type:

Test Concentrations: Measured

Nominal and Measured Concentrations: Nominal concentrations: control, 0.0010, 0.0030, 0. 0089, 0.027 and 0.081 mg/L Measured concentrations: 0.0012, 0.0032, 0.0073, 0. 026 and 0.074 mg/L
Exposure Period: 14 Days

Vehicle Used:

Vehicle Name: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintVehicle Amount and Units: Alkalinity:
Dissolved Oxygen:
pH Value: Value/Lower Range: = 4.9 Upper Range: 5.6
Test Temperature and Units: Value/Lower Range: 23 Upper Range: 25 °C

Photo (Light/Dark): continuous light(ca. 4500-5400 lux)
Salinity:

TOC:

Water Hardness:

Method/Guideline Test Conditions Remarks: The test was performed according to US EPA FIFRA Su bdivision E, Guideline 122-2 and 123-2. Test species Species: Lemna gibba G3 Source: University of California at Los Angeles, Lo s Angeles, CA, USA Cultures: maintained in-house at approx. 25 deg C a nd 4500-5500 lux; transferred 6 days prior to test initiation Test design Type: static renewal Duration: 14 days Renewals: days 3, 6, 9 and 12 Nominal concentrations: control, 0.0010, 0.0030, 0. 0089, 0.027 and 0.081 mg/L Measured concentrations: 0.0012, 0.0032, 0.0073, 0. 026 and 0.074 mg/L Nutrient Solution: Hoagland's medium Temperature: 24 +/- 1 deg C pH of fresh solutions: 4.9-5.3 pH of old solutions: 5.0-5.6 Light: continuous (ca. 4500-5400 lux) Test vessels: 270 mL crystallizing dishes filled wi th 100 mL nutrient solution Analytics: measured concentrations were determined in fresh solutions from day 0 in samples from bulk treatment solutions and in sam ples from aged media from day 3. Measurement was conducted using GC with nitrogen -phosphorus detection (GCNPD).Frond counts were made on days 3, 6, 9, 12 and 14. At test termination (day 14),the dry weight of fronds in each test vessel wa s determined. Statistics: William's Test, Shapiro-Wilks' Test, Ba rtlett's Test; linear regression and standard procedures Limit Test: No 

### Test Results - Acute Toxicity To Aquatic Plants NOEC Exposure Duration:
NOEC:
LOEC Exposure Duration:
LOEC: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintNOELR Exposure Duration:
NOELR:
LOELR Exposure Duration:
LOELR:

Effect : Exposure Duration Exposure

Units Type % Value Description Mean

Value or Lower Mean Value Upper

Mean Value Units Basis

for Effect Basis for Concentration

14 Days EC 50 % = 0.0089 mg/L Other

Results Remarks: Analytical measurements The measured test concentrations ranged from 82-120 % of nominal test concentrations. Measured concentrations at test sol ution renewal (days 3, 6, 9 and 12) decreased significantly and ranged from 15- 36% of nominal concentrations. The biological results are based on initial measured concentrations. Biological results At test termination, the control averaged 841 frond s per replicate. Frond production in the treatment levels (0.0012, 0.0032, 0.0073, 0.026 and 0.074 mg/L) averaged 799, 907, 772, 86 and 35 fronds per replicate, respectively. A significant reduction in frond density was observed in the 0.026 and 0.074 mg/L treatment levels when compared to the control. Base d on frond density, the 14- day EC50 was 0.016 mg/L (95% confidence limits 0.00 55 - 0.048 mg/L). At test termination, frond biomass averaged 0.2224 g in the control and 0.1984, 0.1833, 0.1592, 0.0229 and 0.0149 in the tr eatment levels (0.0012, 0.0032, 0.0073, 0.026 and 0.074 mg/L), respectively . The biomass in all treatment levels except the lowest was significantl y reduced relative to the control. Based upon biomass, the 14-day EC50 was 0. 0089 mg/L (95% confidence limits 0.0025 - 0.032 mg/L).

Conclusion: In a 14-day static renewal test with Lemna gibba, d imethenamid-P caused significant reductions in frond production at conce ntrations greater than or equal to 0.026 mg/L. The EC50 was calculated to be 0.016 mg/L and the EC25 was 0.0082 mg/L, based on initial measured concentratio ns. 

### Reliability/Data Quality - Acute Toxicity To Aquatic Plan ts Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to an accepted test g uideline for aquatic plant toxicity testing. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity To Aquatic Plants 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintReference: Hoberg, J, 1997b. SAN 1289 H Technical: Toxicity to duckweed, Lemna gibba. Springborn Laboratoties, Inc., Wareham, Massachuset ts, USA, unpublished. BASF RegDoc #97/10742. 

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## Acute Toxicity to Aquatic Plants

CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Plants Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Identity: dimethenamid-P technical (SAN 1289 H) Lot: #6663-50-1 Purity: 91.1%

Sponsored Chemical Result Type: See Test Plan and Category Analysis

Test Substance Result Type: Measured 

### Method - Acute Toxicity To Aquatic Plants Year Study Performed: 1997
Method/Guideline Followed: Other

Other Method/Guideline: EPA OPP 122-2 and 123-2

Deviations from Method/Guideline: Species: Selenastrum capricornutum

GLP: Yes
Analytical Monitoring: Yes
Test Type: Static

Test Vessel:
Water Media Type:

Test Concentrations: Measured

Nominal and Measured Concentrations: Nominal concentrations: Control, 0.0016, 0.0030, 0. 0063, 0.013, 0.025 and 0.050 mg ai/L
Measured concentrations (mean values between test i nitiation and test termination):Control, 0.0013, 0.0021, 0.0054, 0.009 6, 0.021 and 0.044 mg ai/L Exposure Period: 5 Days

Vehicle Used:

Vehicle Name: 

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and Units: Alkalinity:
Dissolved Oxygen:
pH Value: Value/Lower Range: = 7.3 Upper Range: 7.6
Test Temperature and Units: Value/Lower Range: 25 °C

Photo (Light/Dark): continuous white fluorescent lamps
Salinity:

TOC:

Water Hardness:

Method/Guideline Test Conditions Remarks: The test was performed according to US EPA FIFRA Su bdivision E, Guideline 122-2 and 123-2. Test species Species: Pseudokirchneriella subcapitata strain 164 8 (syn. Selenastrum capricornutum; syn. Ankistrodesmus bibraianus) Source: obtained from University of Texas at Austin , Austin, TX, USA Cultures maintained in-house Initial cell densities 3 x 10^3 cells/mL
Test design Type: static system Duration: 5 days Six concentrations tested, each with 3 replicates p lus a control with 3 replicates Assessments of growth: daily Nominal concentrations: Control, 0.0016, 0.0030, 0. 0063, 0.013, 0.025 and 0.050 mg ai/L Measured concentrations (mean values between test i nitiation and test termination): Control, 0.0013, 0.0021, 0.0054, 0.00 96, 0.021 and 0.044 mg ai/L Analytics: analytical verification of TS concentrat ions was conducted in each concentration at test initiation and terminati on using GC Statistics: standard procedures, William's Test, Sh apiro-Wilks' Test, Bartlett's Test Algal Assay Procedure (AAP) medium according to AST M Temperature: 25 deg C pH at test initiation: 7.3-7.6 Light: continuous white fluorescent lamps (ca. 4000 -4500 lux) Test vessels: replicate, glass, sterile, 250 mL Erl enmeyer flasks Shaking: continuous at 100 rpm Limit Test: No 

### Test Results - Acute Toxicity To Aquatic Plants NOEC Exposure Duration:
NOEC:
LOEC Exposure Duration:
LOEC:
NOELR Exposure Duration: 

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LOELR Exposure Duration:
LOELR:

Effect : Exposure Duration Exposure

Units Type % Value Description Mean

Value or Lower Mean Value Upper

Mean Value Units Basis

for Effect Basis for

Concentration

5 Days EC 50 % = 0.017 mg/L Cell Number

Results Remarks: Mean measured test concentrations during the course of the test ranged from 72- 88% of nominal test concentrations. Biological resu lts are based on mean measured concentrations. Biological Results At test termination, cells exposed to the 0.0013, 0 .0021, 0.0054, 0.0096 and 0.021 mg/L treatment levels and the control did not exhibit morphological changes. However, bloated cells were observed at the highest treatment level tested, 0.044 mg/L. A significant reduction in cell density occurred in the 0.0054, 0.0096, 0.021, and 0.044 mg/L treatment levels. At the lowest two test concentrations (0.0013 and 0.021 mg/L) growth was more or less ide ntical to the control. Conc., mg/L Inhibition, % 0.0013 25 0.0021 2.3 0.0054 18 0.0096 31 0.021 73 0.044 99 After an 8-day recovery period at a concentration o f 0.0030 mg/L, cells from the 0.044 mg/L exhibited signs of recovery. Th is indicates that dimethenamid-P has an algistatic, rather than algic idal, effect at a mean measured concentration of 0.044 mg/L. EC50 (5-day) = 0.017 mg/L (based on cell density) EC25 (5-day) = 0.011 mg/L Conclusion: In a 5-day algae test with S.capricornu tum the EC50 of dimethenamid-P was found to be 0.017 mg ai/L, the EC25 was 0.011 m g ai/L (measured). The growth of cells after transfer to fresh medium (dilution to 0 .0030 mg ai/L) indicated that dimethenamid-P has an algistatic, rather than algic idal, effect at a mean measured concentration of 0.044 mg ai/L.
Remarks: In similar studies, also conducted under U S EPA FIFRA Subdivision J, Guidelines 122-2 and 123-2, the toxicity to blue-gr een algae (Anabaena flosaquae)and the freshwater diatom (Navicula pelliculo sa) was determined. For A.flosaquae, the 5-day EC50 was 0.38 mg a.i./L and the 5- day EC25 was 0.11 mg a.i./L (based on mean measured concentrations). For N. pel liculosa, the 5-day EC50 was 0.34 mg a.i./L and the 5-day EC25 was 0.12 mg a.i./ L (based on mean measured concentrations). 

### Reliability/Data Quality - Acute Toxicity To Aquatic Plan ts Reliability: 1 - Valid Without Restrictions 

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Remarks: GLP study performed according to an accepted test g uideline for algal toxicity testing. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity To Aquatic Plants Reference: Hoberg, J., 1997a. SAN 1289 H Technical: Toxicity t o the freshwater green alga, Selenastrum capricornutum. Springborn Laboratories, Inc., Wareham, Massachusetts, USA, unpublished. BASF RegDoc #97/5170. 

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## Acute Toxicity to Aquatic Plants

CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity To Aquatic Plants Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1- methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl-; Reg. No. 364802 Process-intermediate of BAS 656-PH, DMTA-P); Batch ID: B1112B01C4; CAS# 170373-17-8; Purity 98.3 coor. are a-%.

Sponsored Chemical Result Type: Measured

Test Substance Result Type: Measured 

### Method - Acute Toxicity To Aquatic Plants Year Study Performed: 2010
Method/Guideline Followed: OECD 201

Other Method/Guideline: Deviations from Method/Guideline: No
Species: Pseudokirchnerella subcapitata

GLP: No
Analytical Monitoring: Yes
Test Type: Static

Test Vessel: Open
Water Media Type:

Test Concentrations: Both

Nominal and Measured Concentrations: Nominal Concentrations of: 0 (control), 10, 22, 46, 100, 220 mg/L
Mean measured concentrations of: 0, 9.0, 20.3, 45.1 , 98.2, and 209.5 mg/L Exposure Period: 72 Hours

Vehicle Used: No

Vehicle Name:

Vehicle Amount and Units: 

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Dissolved Oxygen:
pH Value: Value/Lower Range: = 7.9 Upper Range: 8.5
Test Temperature and Units: Value/Lower Range: 22.9 Upper Range: 23.3 °C

Photo (Light/Dark): continuous light
Salinity:

TOC:

Water Hardness:

Method/Guideline Test Conditions Remarks: The study was conducted according to the following test guidelines: (1) Commission Regulation (EC) No 440/2008, Part C.3 an d (2) OECD 201 (March 2006). The exposure period was 72 hours. Algae used in the test were from a stock algal cult ure which is maintained continuously at the test facility. The algae are ob tained at regular intervals from SAG (collection of algal cultures at Universit y of Gottingen, Germany) and are kept in liquid culture. The test species/strain is Pseudokirchneriella subcapitata KORSHIKOV (SAG 61.81). The test medium was prepared per OECD Guideline 201 . The pH of the medium was 8.1. The results of preliminary tests were used to estab lish the test concentrations for the test. Test medium was prepared according to OEC D Guideline 201. The pH value of the test medium was 8.1. Three replicates for each test substance concentration were prepared; 6 replicates for the control; 1 additiona l replicate per test group for initial concentration control analysis only; and 1 additional uninoculated (without algae) replicate per test group for background fluo rescence correction and to determine the influence of the test design on test substance stability. The test substance is a mixture that is partially s oluble in water. Therefore, the test solutions were prepared following general guidance provided in OECD 23 in order to achieve a water accommodate fraction (WAF) of the test substance. Each test solution was prepared separately (differential load ing) by directly adding test substance to test medium. The beakers were covered and the test solutions were stirred gently on a magnetic stir plate for approxi mately 1 day at 20 +/- 2 deg C. All test solutions were visibly clear and no undiss olved test substance was observed. The algal inoculum was from a 4-day old stock cultu re in exponential growth. An initial cell density of 5,000 cells/mL was attained by adding the inoculum culture (50,000 cells/mL) to each test solution at a ratio of 1:100. Test vessels were Erlenmeyer flasks (nominal volume 250 mL) plugged with gas permeable silicone sponge caps, test volume of 100 mL, initial cell density 0.5x10^4 cells/mL, test temperature 22.9-23.3 deg C , shaking rate was continuous at approximately 85 rpm and route of exposure was stat ic exposure via the test medium. Universal white light, average 5277 lux (+/- 15%) a t a wavelength of 400 - 700 nm was provided continously. Test vessels were rearran ged daily to minimize the potential effect of slight variations in illuminati on. An analytical method by determination of total orga nic carbon for the measurement of test substance in test water was dev eloped by BASF and used to verify the nominal test concentrations. Sampling was performed at the start of the exposure (0 h) from the inoculated replicate 7 of each concentration and the control. At the end of the exposure (72 h) samples of the inoculated replicates of the test concentrations and control group were taken. The replicates were combi ned before sampling. Since 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintalgal cells would interfere with the TOC determinat ion, the samples were centrifuged for about 15 minutes at about 4500 rpm to remove the algae. Additionally, samples were collected from the unino culated replicate 0 of each test concentration and the control at the end of th e exposure. Fluorescence was measured in each replicate (except replicate 7) at 0, 24, 48, and 72 h. At the end of the exposure period, the co rrelation between fluorescence and cell density was evaluated using d irect microscoping counting. The yield and growth rate over the exposure period was calculated for each replicate flask of each test group and percent inhibition of the mean yield and growth rate determined by comparison to the control. ECx values were calculated via interpolation from the concentration- response relationship. SAS statistical software was used for the statistical evaluation of the data . The Dunnett's test (one-sided) was carried out at a 95% confidence level for deter mination of the LOEC. Algal morphology was examined microscopically on th e inoculum culture and on a pooled sample from each test concentration at test termination. Limit Test: No


### Test Results - Acute Toxicity To Aquatic Plants NOEC Exposure Duration: 72 Hours

NOEC: = 10 mg/L Nominal
LOEC Exposure Duration: 72 Hours

LOEC: = 22 mg/L Nominal
NOELR Exposure Duration:
NOELR:
LOELR Exposure Duration:
LOELR:

Effect : Exposure Duration Exposure

Units Type % Value Description Mean

Value or Lower Mean Value Upper

Mean Value Units Basis

for Effect Basis for

Concentration

72 Hours EC 10 % = 22 mg/L Biomass Nominal
72 Hours EC 50 % = 58.9 mg/L Biomass Nominal
72 Hours EC 10 % = 46.5 mg/L Growth Rate Nominal
72 Hours EC 50 % = 97 mg/L Growth Rate Nominal

Results Remarks: The following observations were recorded after 72 hours for each of the nominal test groups: 0 mg/L = no remarkable observations 10 mg/L = no remarkable observations 22 mg/L = no remarkable observations 46 mg/L = no remarkable observations 100 mg/L = low cell density 220 mg/L = no algal cells were observed 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintThe limit of quantification of the analytical metho d (TOC) was 0.2 - 4.8 mg/L. The recovery efficiency was 103 - 105%. Measured co ncentrations ranged from 91.0 to 102.7% of nominal at 0 hours. At 72 hours, measured concentrations in the inoculated replicates ranged from 89.0 to 93.9% of nominal, an d in the uninoculated replicates ranged from 88.0 to 101.3% of nominal. Since the analytically determined concentrations of the test substance in the test solutions were within +/- 20% of the nominal c oncentrations, the effect concentrations can be expressed relative to the nom inal concentration for the evaluation of the test substance. Based upon yield (cell density at test termination minus cell density at test initiation), percent inhibition was - 14.1, 10.0, 30.5, 91.8, and 99.8 in the 10, 22, 46, 100 and 220 mg/L test concentrations, respectiv ely. Based upon growth rate, percent inhibition was -0.4 16, 2.16, 9.46, 51.6, and 95.9% in the 10, 22, 46, 100 and 220 mg/L test conc entrations, respectively. Toxicity response variables for algal yield based o n nominal concentrations are the following: EC10 = 22.0 mg/L EC50 = 58.9 mg/L EC90 = 97.7 mg/L NOEC = 10 mg/L LOEC = 22 mg/L
(Note: the table of test results lists these values as based upon biomass) Toxicity response variables for algal growth rate b ased on nominal concentrations are the following: EC10 = 46.5 mg/L EC50 = 97.0 mg/L EC90 = 198 mg/L NOEC = 22 mg/L LOEC = 46 mg/L
The test conformed to all validity criteria in OECD 201. The validity criteria were met as follows: The cell multiplication factor in the untreated con trol was 142-fold after 72 hours (counted cell density: 71x10^4 cells/mL). The mean coefficient of variation for section-by-se ction growth rates for each test day in the control cultures was 4.18%. The coefficient of variation of average specific gr owth rates during the whole test period in replicate control cultures was 2.89%

. The test is valid according to the guidelines. No d eviations from test guidelines or other incidents occurred during the c ourse of the reported test which may have influenced the results.



### Reliability/Data Quality - Acute Toxicity To Aquatic Pl ants Reliability: 1 - Valid Without Restrictions
Reliability Remarks: Well-documented study conducted according to accept able methods and under GLP.
Key Study Sponsor Indicator: Key 

### Reference - Acute Toxicity To Aquatic Plants Reference: Salinas, E. 2011. Report: Reg. No. 364802 (Process- intermediate of BAS 656-PH, DMTA -P) growth inhibition study in unicellular gre en algae Pseudokirchneriella subcapitata KORSHIKOV. BASF DocID 2010/1079231. Exp erimental Toxicology and Ecology BASF SE 67056 Ludwigshafen, Germany, Projec t No: 60E0934/083697. 

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## Acute Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was T01184 (SAN 582-Stufe C -4 "Via Keto-Enol"). This test substance was the racemic C4 , CAS No. 87676-07-1, 3-thiophenamine,N-(2-methoxy-1-meth ylethyl)-2,4-dimethylSponsored Chemical Result Type: Measured


### Method - Acute Toxicity Route of Administration: Oral
Type of Exposure: Gavage
Species: Rat

Mammalian Strain: Wistar

Gender: Male

Number of Animals per Dose: 3

Dose: 519 and 2077 mg/kg (actual dose of undiluted TS)
Year Study Performed: 1988
Method/Guideline Followed: OECD 401

GLP: No Data
Method/Guideline and Test Condition Remarks: The test was performed according to OECD 401 from F ebruary 1987. TEST ANIMALS: - Species: rat - Strain: Wistar, Charles River WIGA, BRD - Sex: male - Age: 5-6 weeks - Body weight: 190-220 g - Feed: Kliba Nr.24-343-4 TEST ADMINISTRATION: - Preliminary test: none - Route of exposure: oral gavage - Exposure volume: 10 mL/kg - Doses: 519 and 2077 mg/kg (actual dose of undilut ed TS) - Number of animals per sex per dose: 3 - Vehicle: PAGA (1mL/100g) EXAMINATIONS: - Animals were observed for mortality and clinical signs during a 14 day observation period 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintThe identity of the vehicle solvent (PAGA) is uncle ar. 

### Test Results - Acute Toxicity Concentration (LC/LD) : LC/LD % Value Description Value/Lower

Concentration Upper

Concentration Units
LD 50 % = 1038 mg/kg -bw

Number of Deaths ( Male ): Number of Deaths ( Female ): Number of Deaths ( Total ):
Results Remarks: MORTALITY: - The acute oral LD50 was 1038 mg/kg bw - At 519 mg/kg bw: no treatment-related deaths - At 2077 mg/kg bw: 3/3 animals died (latency of de ath 26- 38 hours postexposure) CLINICAL SIGNS: 2077 mg/kg: - Weak: 3/3 between 13-58 minutes, 3/3 from 1-24 h - Atonic: 3/3 between 13-58 minutes, 3/3 from 1-24 h - Palsied: 3/3 at 24 hours, 0/3 from 1-24 h - Salivation: 3/3 between 13-58 minutes, 0/3 from 1 -24 h - Prone position: 1/3 at 24 hours - Decreased motor activity: 1/3 at 3 and 4 hours, 3 /3 at 24 hours - Dizzy: 3/3 at 24 h - Ataxia: 1/3 at 13-58 minutes, 1/3 at 3 h, 2/3 at 4 h, 3/3 at 24 h - Lacrimation: 1/3 at 24 h - Ruffled hair: 2/3 at 4 h, 3/3 at 24 h - Dozy: 3/3 at 24 h - Slowed breathing: 3/3 between 13-58 minutes, 2/3 at 1, 3, and 4 h, 3/3 at 24 h - Strained breathing: 3/3 between 13-58 minutes, 1/ 3 at 1 h, 2/3 at 2, 3, and 4 h, 3/3 at 24 h - Reddened penis, paws, and ears (strong blood flow ): 3/3 at 3, 4 h - Swelling: 1/3 at 24 h - Diarrhea: 2/3 at 1 h, 3/3 at 2, 3, and 4 h INTERNAL EXAMINATIONS: - Grossly enlarged stomach in 2/3 deaths (stretched with fluid and feed) - Stomach lining: reddened (2/3 animals) - Colon contents were very hard 519 mg/kg: - Weak: 1/3 within 13-58 minutes, 3/3 at 1 h therea fter - Atonic: 1/3 within 13-58 minutes, 3/3 at 1, 2, 3, 4, 24, and 48 h(disappeared at 72 h) - Palsied: No data - Salivation: 3/3 at 13-58 minutes, 1, 2, and 3 h (disappeared at 4 h) - Prone position: No data - Decreased motor activity: 2/3 at 2, 3, 4, and 24 hours (disappearance at 48) - Dizzy: 1/3 at 2, 3, and 4 h (disappeared at 24 h) 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint- Ataxia: 1/3 at 13-58 minutes, 1/3 at 3 h, 2/3 at 4 h, 3/3 at 24 h - Lacrimation: No data - Ruffled hair: 1/3 at 3 h, 2/3 at 4 h, 3/3 at 24 h , 1/3 at 48 h, 0/3 at 72 h - Dozy: 2/3 at 1, 2, 3, and 4 h (disappeared at 24 h) - Slowed breathing: 2/3 at 2, 3, and 4 h, 3/3 at 24 h, 1/3 at 48 h, 0/3 at 72 h - Strained breathing: 2/3 at 2, 3, and 4 h, 3/3 at 24 h, 1/3 at 48 h, 0/3 at 72h -Reddened ears: 2/3 at 4 h - Reddened paws: 1/3 at 4 h - Swelling: none - Diarrhea: No data Conclusion: 

### Reliability/Data Quality - Acute Toxicity Reliability: 2 - Valid With Restrictions
Reliability Remarks: This study was performed in accordance with OECD 40 1 (Feb. 1987) with acceptable deviations. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity Reference: Hamburger, F. 1988. T01184 (SAN 582H-Stufe 4 C-4 "V ia KetoEnol") Acute Oral LD50 Toxicity Study in Male Rats. Sandoz, Ltd. Agro Division Department of Toxicology, Basel, Switzerland. Study No.: 6949/88. 17 Nov 1988. 

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## Acute Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Acute Toxicity Route of Administration: Inhalation
Type of Exposure: Aerosol
Species: Rat

Mammalian Strain: Sprague-Dawley

Gender: Both M/F

Number of Animals per Dose: 10

Concentration: The average measured concentration was 2.2 mg/L.
Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 81-3

GLP: Yes
Method/Guideline and Test Condition Remarks: The study was performed according to U.S. EPA FIFRA , Subdivision F, Paragraph 81-3. Five male and five female rats were exposed nose-on ly to the undiluted TS as a liquid aerosol for four hours. The target atmo sphere concentration was > 2.0 mg/L. Actual chamber concentrations were determined every hour during th e exposure using a gas chromatographic method. Partic le size was also determined every hour following treatment. The animals were observed for 14 days after the exposur e. Body weights were determined prior to the beginning of t he test and on days 7 and 14 after exposure. All animals we re sacrificed at day 15 and a gross necropsy was perfo rmed. 

### Test Results - Acute Toxicity Concentration (LC/LD) : LC/LD % Value Description Value/Lower

Concentration Upper

Concentration Units 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintLC 50 % > 2.2 mg/L

Number of Deaths ( Male ): Number of Deaths ( Female ): Number of Deaths ( Total ): 0

Results Remarks: The average measured concentration was 2.2 mg/L. Th e mass median aerodynamic diameter (MMAD) was determined to be 3. 4 um with a geometric standard deviation (GSD) of 2.0 um. Approximately 4% of the aerosol was less than or equal to 1.0 um, approxima tely 59% less than or equal to 4.0 um and approximately 94% was less than or equal to 10.0 um. All animals survived through the observation period

. Labored breathing was noted in the last two hours o f the exposure for two of the ten animals. Signs exhibite d upon removal from the chamber and during the first two h ours after exposure included secretory (lacrimation, chromodacryorrhea, red and clear nasal discharge an d dried red facial material) and respiratory (labored breat hing and moist rales) responses. Similar signs were obse rved after day two. Body weights increased normally and no abnormalities were noted at necropsy. Conclusion: The 4-hour inhalation LC50 for dimethenamid-P in ma le and female Sprague-Dawley rats was determined to be gre ater than 2.2 mg/L. 

### Reliability/Data Quality - Acute Toxicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted acute inh alation toxicity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity Reference: Hoffman, G. 1996. An acute (4-hour) inhalation toxi city of SAN 1289 H technical in the rat via nose-only expos ure. Huntington Life Sciences, East Millstone, New Jerse y, USA, unpublished. BASF RegDoc #96/5397. 

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## Acute Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Acute Toxicity Route of Administration: Oral
Type of Exposure:
Species: Rat

Mammalian Strain: Sprague-Dawley

Gender: Both M/F

Number of Animals per Dose: 10

Dose: 350, 400 and 500 mg/kg bw.
Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 81-1

GLP: Yes
Method/Guideline and Test Condition Remarks: The study was conducted according to U.S. EPA FIFRA , Subdivision F, Paragraph 81-1. Groups of ten rats (5/sex/dose) were given undilute d oral doses of the TS in a single oral dose at 350, 400 or 500 mg/kg bw. The dosing volumes were 0.29, 0.34 or 0.42 mL/kg for lo w, medium, and high doses. The animals were observed f or 14 days after the exposure. Body weights were determin ed pretest, on the day of dosing, and weekly thereafte r. All animals received a gross necropsy at study terminat ion. 

### Test Results - Acute Toxicity Concentration (LC/LD) : LC/LD % Value Description Value/Lower

Concentration Upper

Concentration Units
LD 50 % = 466 mg/kg -bw 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintNumber of Deaths ( Male ): Number of Deaths ( Female ): Number of Deaths ( Total ):
Results Remarks: One male rat died in the 400 mg/kg bw dosage group. All 500 mg/kg bw males died. Two females in the 500 mg/kg b w dosage group died. Male LD50: 429 mg/kg bw Female LD50: 531 mg/kg bw Combined LD50: 466 mg/kg bw

Clinical observations observed in all animals on th e day of dosing consisted of lacrimation and excessive saliv ation. All high-dose animals exhibited decreased activity. Signs seen on the day after dosing included: yellow ano-g enital staining, black and/or brown staining on the snout, oral area, buccal area and/or extremities, lethargy, dec reased food consumption, and decreased fecal volume or no stool. All surviving animals were free of clinical signs b y day 5 after dosing. Overall, the animals gained body weig ht as expected for their age. Treatment-related effects o n gross pathology were observed only in animals which died and consisted of red thymic region, fluid in thoracic c avity, red lungs, black mucosa or brown fluid in the stoma ch and red testes. Conclusion: The oral LD50 values for dimethenamid-P in Sprague- Dawley rats were determined to be 429 mg/kg bw for males, 531 mg/kg bw in females and 466 mg/kg bw for the combin ed
sexes. 

### Reliability/Data Quality - Acute Toxicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted acute ora l toxicity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity Reference: Blaszcak, D. 1996. Acute oral toxicity with SAN 128 9 H technical in rats. Huntington Life Sciences, East Millstone, New Jersey, USA, unpublished. BASF RegDo c #96/11087. 

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## Acute Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1% Sponsored Chemical Result Type: Measured


### Method - Acute Toxicity Route of Administration: Dermal
Type of Exposure: Occlusive
Species: Rabbit

Mammalian Strain: New Zealand White

Gender: Both M/F

Number of Animals per Dose: 10

Dose: 2000 mg/kg bw
Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 81-2

GLP: Yes
Method/Guideline and Test Condition Remarks: The study was performed according to U.S. EPA FIFRA , Subdivision F, Paragraph 81-2. Undiluted TS was applied to the clipped epidermis ( dorsal trunk surface) of ten rabbits (5/sex) at 2000 mg/kg bw. The site was covered with gauze and impervious plastic during the 24 h e xposure. Following the exposure, the wrappings were removed and the test site was wiped free of excess material with 0. 9% saline. The exposure surface was approx. 12 x 14 cm which is at least 10% of the body area. The animals were observed for 14 days after dosing. Body weights were determi ned on the day before testing, on the day of dosing and on days 8 and 15 after dosing. A gross necropsy was performed on all animals. 

### Test Results - Acute Toxicity Concentration (LC/LD) : LC/LD % Value Description Value/Lower

Concentration Upper

Concentration Units 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintLD 50 % > 2000 mg/kg -bw

Number of Deaths ( Male ): Number of Deaths ( Female ): Number of Deaths ( Total ): 0

Results Remarks: No mortality or clinical observations. Four of the ten animals exhibited slight body weight loss by day 8, but gained weight thereafter. The remaining six animals exhibited bod y weight gains or no weight change during the study. There w ere no internal findings at necropsy. Three of the ten ani mals exhibited a red subcutaneous discoloration/foci at the dose site. Conclusion: The dermal LD50 for dimethenamid-P in rabbits was determined to be greater than 2000 mg/kg bw for mal es and females. 

### Reliability/Data Quality - Acute Toxicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted acute der mal toxicity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity Reference: Blaszcak, D. 1996. Acute dermal toxicity with SAN 1 289 H technical in rabbits. Huntington Life Sciences, Eas t Millstone, New Jersey, USA, unpublished. BASF RegDo c #96/5395. 

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## Acute Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Acute Toxicity Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was T01184 (SAN 582-Stufe C -4 "Via Keto-Enol"), 98.7% a.i. This test substance was th e racemic C4, CAS No. 87676-07-1, 3-thiophenamine,N-( 2-methoxy-1-methylethyl)-2,4-dimethylSponsored Chemical Result Type: Measured


### Method - Acute Toxicity Route of Administration: Dermal
Type of Exposure: Semi-Occlusive
Species: Rat

Mammalian Strain: Wistar

Gender: Both M/F

Number of Animals per Dose: 10

Dose: 4153 mg/kg bw
Year Study Performed: 1988
Method/Guideline Followed: OECD 402

GLP: Yes
Method/Guideline and Test Condition Remarks: The study was performed according to OECD Test Guid eline 402 from February 1987 and EPA Guideline 81/2 and c onducted under Good Laboratory Practices.

TEST ANIMALS: - Species: rat - Strain: Wistar:Crl:(W1)BR, a Han/Wistar rat - Age: 8-14 weeks old - Male body weight: 295-320 g - Female body weight: 225-240 g - Feed: KLIBA N0. 24-343-4, provided ad libitum bef ore and after dosing - Water: provided ad libitum - Identified with cage card - Housed individually in Macrolon cages with steril ized wood chips - All animals were healthy at the beginning of the test ENVIRONMENTAL CONDITIONS: - Photoperiod: 12 hours light:dark - Temperature: 23 +/- 2 deg C 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint- Relative air humidity: 30-70% - Air changes: 15 air changes/hour TEST METHODS: DOSING: - The animals were acclimated for a period of 7 day s prior to dosing - The animals' backs were clipped free of hair and the TS was evenly applied to a skin area of 16 cm^2 (corre sponding to approximately 10% of the body surface) - The dose was 4153 mg/kg bw - The test site was covered with 8-layer porous gau ze - The duration of the exposure was 24 h - At the end of the 24 hour exposure, the dressings were removed, excess compound wiped off and the skin was gently washed with water OBSERVATIONS: - On the day of application animals were observed f or mortality during the first 4 hours, and hourly for up to 7 hours - Daily observations of mortality were performed fo r the following 13 days -The nature, severity, approximate time of onset an d duration of symptoms were observed at the onset of the test and after 1, 2, 3, 4 and 24 hour postapplication and also daily for the remaining 13 days - Bodyweights were recorded on days 1, 2, 3, 8 and 15 NECROSPY: - All surviving animals were euthanized with CO2, necropsied, and examined for gross abnormalities - No data on whether a control site was also employ ed - The test site was shaved on the day of dosing, no t 24 h prior 

### Test Results - Acute Toxicity Concentration (LC/LD) : LC/LD % Value Description Value/Lower

Concentration Upper

Concentration Units
LD 50 % > 4153 mg/kg -bw

Number of Deaths ( Male ): 0

Number of Deaths ( Female ): 0

Number of Deaths ( Total ): 0

Results Remarks: - No mortality or dose-related signs of toxicity we re observed - After a slight weight loss during the first days postapplication, all animals gained weight during the 14 day observation period - Necrospy revealed no treatment-related gross abnormalities - No irritation of the treated skin area was observ ed - The acute dermal toxicity is > 4153 mg/kg bw

Conclusion: 

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### Reliability/Data Quality - Acute Toxicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to an accepted test g uideline with acceptable deviations. Key Study Sponsor Indicator: 

### Reference - Acute Toxicity Reference: Hamburger, F. 1988. T01184 (SAN 582-Stufe C-4 "Via KetoEnol") Acute dermal toxicity study in male and fema le rats. Sandoz, Ltd. Agro Division Department of Toxicology , Basel, Switzerland. Study No.: 6963/88. 15 Dec 1988. 

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## Repeated-Dose Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Repeated-Dose Toxicity Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1- methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: - The test substance (TS) was T01184 (SAN 582-Stufe C-4 "Via KetoEnol") - Purity: 95.3% - Assigned study no.: 11167 - Storage: at room temperature - Physical characteristics: dark brown liquid Sponsored Chemical Result Type: Measured


### Method - Repeated-Dose Toxicity Route of Administration: Oral
Type of Exposure: In Food
Species: Rat

Mammalian Strain: Other

Other Strain:

Gender: Both M/F

Number of Animals per Dose: 16

Dose: 350, 750 and 1000 ppm.
Year Study Performed: 1994
Method/Guideline Followed:
GLP: Yes
Exposure Period: 4 Weeks
Frequency of Treatment: continuous (ad libitum)
Post-Exposure Period: Method/Guideline and Test Condition Remarks: This study was conducted as a pilot study to determ ine acceptable doses in a subsequent neurotoxicity test. TEST ANIMALS: - Species: rat - Strain: Charles River:CD VAF/Plus - Age: 5 weeks - Feed: Ground diet (Certified Rodent Chow #5002), provided ad 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintlibitum - Water: available ad libitum - Housing: individually in stainless steel wire-mes h cages - Each rat was identified by cage, group, sex and n umbered metallic ear tag ENVIRONMENTAL CONDITIONS: - Photoperiod: 12 hour light/dark - Temperature: 71 +/- 1 deg F - Relative humidity: 50 +/- 8.4% TEST METHODS TEST SUBSTANCE ANALYSIS: - Homogeneity: Prior to the initiation of the study , ten stratified test article:diet mixture samples were c ollected from diets as they were dispensed from the blender (sample 1 from the botto m of the test diet and sample 10 from the top) - Stability: A composite sample was collected from each diet mixture. Samples were dispensed into glass containers and st ored under normal laboratory conditions for 3, 5, and 10 days. Sample s were analyzed in duplicate. Additional stability analysis was perfor med on a sample which was frozen and removed from the freezer after 7 day s, then stored at room temperature for an additional 3 days. PRESTEST: - The rats were observed daily during a 10 day accl imation period for any clinical signs of disease and all rats were given a detailed physical examination - For the first 3 days of the acclimation period, a nimals were housed 3 per cage to acclimate to automatic watering system - After this time, animals were individually housed - The animals were randomly assigned to one of thre e dose groups DOSING: - The original doses were 1000, 2500, and 4000 ppm; however, diet consumption markedly decreased during the first 4 d ays of the study. These initial doses were selected based on d ata from previous studies. This initial dose was given for t he first 4 days of the study and then replaced with basal diet on s tudy day 8, doses were changed to: 0(control), 350, 750 and 100 0 ppm. - Number of animals per sex per group: 16 - Duration of exposure: 4 weeks OBSERVATIONS: - Mortality: at least twice daily throughout the st udy - Clinical signs: the rats were observed for signs of overt toxicity at the times of the morbidity/mortality checks; detailed o bservations of appearance and condition, behavior and activity, ex cretory functions, respiration, orifices, eyes and palpable masses were made at least once weekly - Body weights: determined pretest and at least onc e weekly throughout the dosing period - Feed consumption: individual feed consumption was measured at least 3 times weekly and calculated on a weekly bas is STATISTICS: - Body weights and food consumption values were ana lyzed using ANOVA and Bartlett's test for homogeneity of varian ce - Treatment groups were compared to the control gro up, by sex, using the appropriate t-statistic (for equal or unequal varia nce) as described by Steel and Torrie - Dunnett's multiple comparison tables or pairwise comparisons with a Bonferroni correction were used to determine the significance of differences 

### Test Results - Repeated-Dose Toxicity 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintConcentration (LOAEL/ LOAEC/ NOAEL/ NOAEC) : LOAEL/ LOAEC/ NOAEL/ NOAEC Population Value Description Value/Lower

Concentration Upper

Concentration Units

Results Remarks: MORTALITY: - All animals survived the exposure RECURRING OBSERVATIONS: - During the first four days of the study all anima ls had decreased defecation (at the original higher doses) - Following the reduction in dosage levels, inciden ces of decreased defecation were reduced CLINICAL SIGNS: - Decreased defecation was observed throughout the study particularly in the 750 and 1000 ppm groups - Seven males and 10 females in the 750 ppm group a nd 13 males and 8 females in the 1000 ppm group were cold to the to uch one or more weeks during the study - Ptosis was observed in both the male and female g roups BODY WEIGHTS: - Body weights increased throughout the study, exce pt on days 9 and 10, when the treated male groups showed slightl y decreased weights - Male animals resumed weight gain beginning on day 11 - Treated females showed weight decreases on study day 9 - The 750 and 1000 ppm females had decreased body w eight gains through day 13 - Weight decreases through this period can be attri buted to the animals' return and acclimation to treated diets - All treated groups had statistically significant weight decreases of 20% or more when compared to the control groups FOOD AND COMPOUND CONSUMPTION: - Comparable to the control group - Average food consumption (mg/kg/day): Males 350: 28.262 750: 56.654 1000: 70.528 Females 350: 30.468 750: 61.324 1000: 73.595 TEST SUBSTANCE ANALYSES: - Homogeneity: All diet mixtures were shown to be h omogenous and accurately prepared. - Stability: Analytical results suggest that the TS was stable in the feed under the 7 days frozen/3 days at room temperature regimen at the 350 to 1000 ppm levels. No significant loss of arti cle was observed at the 2500 and 4000 ppm levels after 5 da ys of room temperature storage. Conclusion: Based on the results of this study, 1000 ppm is rec ommended as the highest dose for a subchronic neurotoxicity study i n rats. 

### Reliability/Data Quality - Repeated-Dose Toxicity Reliability: 2 - Valid With Restrictions 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintReliability Remarks: No pathological examinations were performed which r educe the value of the findings. This study was performed as a dose finding study for subsequent neurotoxicity studies. Key Study Sponsor Indicator: 

### Reference - Repeated-Dose Toxicity Reference: Schaefer, G.J. 1994. 4 Week Oral Toxicity Study in Rats - Pilot. International Research and Development Corporation, Mattawan, MI. Study No.: 658-006. January 27, 1994. BASF RegDoc# 94/11935. 

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## Repeated-Dose Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Repeated-Dose Toxicity Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1- methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was SAN 582 H C-4 Intermedi ate. The test substance was the racemic C4, CAS No. 876-76-07-1, 3- thiophenamine,N-(2-methoxy-1-methylethyl)-2,4-dimet hylSponsored Chemical Result Type: Measured


### Method - Repeated-Dose Toxicity Route of Administration: Oral
Type of Exposure: In Food
Species: Rat

Mammalian Strain: Other

Other Strain:

Gender: Both M/F

Number of Animals per Dose: 32

Dose: 100, 300, 1000 ppm(Males: ca. 6.2, 18.2, 57.7 mg/kg bw/day; Females: ca. 7.4, 20.7, 66.0 mg/kg bw/day) Year Study Performed: 1994
Method/Guideline Followed:
GLP: Yes
Exposure Period: 13 Weeks
Frequency of Treatment: continuous (ad libitum)
Post-Exposure Period: Method/Guideline and Test Condition Remarks: TEST SUBSTANCE ANALYSES: - Test samples of treated diet were assessed for ho mogeneity and stability - Positive control preparations were tested to veri fy stability in the diet for up to one week - Periodic analyses of each test diet prepared were collected for each of the first 4 weeks and monthly for the remai nder of the study and were analyzed in duplicate for test artic le concentration EXPERIMENTAL DESIGN 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintTest Animals & Environmental Conditions: - The animals were housed individually for the enti rety of the study (except day 1 of acclimation in which they we re housed 3 per cage) - Age at randomization: 41 days - Body weight at randomization: males 138-162 g; fe males 116-134 g - The acclimation period was a minimum of 7 days - During acclimation, the animals were observed for any clinical signs of disease - The animals were provided with basal laboratory d iet of Certified Rodent Chow #5002 (replaced 3 times/study week) and tap water ad libitum - Temperature: 70-73 deg F (71 +/- 0.9 deg F) - Humidity: 46-70% (57 +/- 8.4%) - Photoperiod: fluorescent lighting provided 12 hou rs per day Exposure: - The animals were randomly assigned to the positiv e control, vehicle control, and the three concentration groups - The positive control was 16 mg/kg/day acrylamide - Animals were randomly selected for neurobehaviora l examination and neuropathology, which were conducted over a 4-5 day period; the animals were divided into approx. equal squads of male and female rats from each group - For each dose and controls 16 males and 16 female s were exposed to the TS - Exposure concentrations: 100, 300, 1000 ppm (sele cted on the basis of available data from IRDC Study Number 658-006, "4-W eek Oral Toxicity Study in Rats-Pilot") - The positive control was administered by intragas tric intubation (5 times/week for 13 weeks) IN-LIFE EXAMINATIONS Mortality: - At least twice daily throughout the study Clinical Signs: - Twice daily for signs of overt toxicity at the ti mes of the moribundity/mortality checks - Detailed examinations were conducted once each we ek beginning with treatment, particular attention was given to d etect behavioral and/or neurological abnormalities Weekly Body Weights: - Recorded weekly from randomization until euthanas ia for all animals Food & Compound Consumption: - Recorded weekly from randomization until euthanas ia for all animals - Compound consumption was calculated on the corres ponding food consumption weeks Functional Observational Battery (FOB): - Performed on six animals selected for neuropathol ogy and five additional animals randomly selected from the toxicity animals for each sex in each group were evaluated using FOB - FOB testing was performed approx. 7 days prior to dosing, and during study weeks 4, 8 and 13 - Home Cage Measurements: posture, involuntary moto r movements, palebral closure, measurements during handling, eas e of removal and handling reactivity, lacrimation and salivation, pa lebral closure, piloerection, exophthalmus - Open Field Measurements: rearing, urination and d efecation, involuntary motor movements, gait and gait score, mobility score, arousal, vocalizations, respiration, stereotype and bizarre behaviors - Sensorimotor Measurements: approach response, tou ch response, click response, tail-pinch response, pupil response, air- righting reflex, thermal response, hind foot splay, grip strength, 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint- Physiological Measurements: body weight and recta l body temperature Motor Activity Evaluations: - The activity and emotionality of each rat were as sessed in a Digiscan Activity Monitor - Animals were monitored for 6 consecutive 5-minute intervals, allowing for examination of exploratory and acclimation activity levels Ophthalmoscopic Examinations: - Conducted on each animal by a veterinary ophthalm ologist once during the pretest and at study termination (90 days); rat s with ophthalmoscopic pathology were removed from the randomization popul ation Disposition of Animals: - Animals selected for neuropathological examinatio ns were anesthetized by i.p. injection of sodium phenobarbital at study termination, perfused, and selected neural tissues were preserved in phosphate buffered fixative - Following week 13, animals not selected for neuro pathological examination were euthanized by CO2 asphyxiation and necropsied; each rat was examined for external abnormalities, includ ing palpable masses, and the thoracic and abdominal cavities and organs were examined for grossly evident morphological changes - Tissues were saved in buffer for histopathologica l examination Clinical Pathology: - Conducted on 11/sex/group at pretest and survivin g animals at study termination - Hematological, biochemical, and urological parame ters were assessed Anatomic Pathology - Neuropathology animals: Macroscopic - Six animals per sex were selected from the 11 ani mals per sex designated as behavior test animals and were select ed for examination Microscopic - Both sciatic nerves were collected and fixed for microscopic examination Anatomic Pathology - Toxicity Test Animals: Macroscopic - Complete postmortem examination performed in all toxicity test animals - All survivors were sacrificed by CO2 asphyxiation and examined for external abnormalities including palpable masse s - Any internal masses were recorded - Representative samples of organs were collected a nd preserved Organ Weights - Absolute organ weights from all surviving toxicit y test animals were recorded along with postmortem body weights an d appropriate weight ratios (relative to body and brain weight) c alculated Microscopic - A full complement of organs and tissues were exam ined microscopically for the vehicle control and high-dose groups euthan ized at study termination and on all toxicity test animals from a ll groups euthanized during the course of the study - In addition, the following tissues were examined microscopically for all toxicity test animals in the low and mid dose group s: liver, kidney (2), and lung (2) - The observed lesions were graded as trace, mild, moderate, or
severe STATISTICAL ANALYSES: - All statistical analyses compared the treatment g roups with the vehicle 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintcontrol with levels of significance at p = 0.05 and p = 0.01 

### Test Results - Repeated-Dose Toxicity Concentration (LOAEL/ LOAEC/ NOAEL/ NOAEC) : LOAEL/ LOAEC/ NOAEL/ NOAEC Population Value Description Value/Lower

Concentration Upper

Concentration Units

NOAEL Male circa 18.2 mg/kg bw/day NOAEL Female circa 20.7 mg/kg bw/day

Results Remarks: PREPARED TEST AND CONTROL ARTICLE ANALYSES Prepared diet homogeneity: - The 100 and 300 ppm formulations prepared on June 30, 1993 were shown to be homogenous and accurately prepared, the calculated mean concentrations found at 100 and 300 ppm levels were 93 to 100% of the respective target concentrations - The 1000 ppm dietary mixture prepared on June 30, 1993 was not unequivocally shown to be homogenous Prepared diet stability: - The TS was stable under selected storage conditio ns Periodic Analyses of Prepared Diets: - Dosage formulations prepared for study weeks 1-4, 8 and 12 contained 85% to 106% of the target concentrations IN-LIFE EXAMINATIONS Mortality: - One male in the 300 ppm group was euthanized on d ay 37 which had
an abscess in the mouth (likely cause of morbidity) - One female in the 300 ppm group was euthanized on day 8, a reported right-protruding eye with severe acute panophthalmi tis was the likely cause of morbidity - One female in the 1000 ppm group was euthanized o n day 10 with the cause of morbidity unknown - There were no treatment-related gross or microsco pic abnormalities in these rats - It was concluded that the cause of morbidity in t hese three rats was not treatment-related Clinical Signs: - No treatment-related findings Weekly Body Weights: - Statistically significant (p<=0.01) reductions in mean body weight (week 1-13) and inhibitions in body weight gain (weeks 0- 13) were noted for males and females in the 1000 ppm group when co mpared with the vehicle control; these effects were determined to b e treatmentrelated - Positive control animals showed body weight reduc tions and inhibited body weight gain during the study - Non-treatment-related but statistically significa nt body weight reductions were noted sporadically for females in the 100 (p<= 0.05) and 300 (p<=0.01) ppm groups - Non-treatment-related but statistically significa nt weight gain inhibitions were noted sporadically for females in the 100 (p<= 0.05) and 300 (p<=0.05 during weeks 1-2, p <0.01 for all other si gnificant periods) ppm groups 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintFood & Compound Consumption: - Treatment-related, statistically (p<=0.01 and p<= 0.05 in males; p<=0.01 in females) and/or biologically significant reducti ons in food consumption were noted during study weeks 1-13 for males and fe males in the 300 and 1000 ppm groups when compared with that of male s and females in the vehicle control group - Similar reductions were noted in the positive con trol group males - Statistically-significant (p<=0.01 and p<=0.05) b ut non-treatment -related reductions (considered to be a function of normal b iological variability due to their sporadic nature and the lack of a similar effect in the 100 ppm males) in food consumption were observed in 100 ppm females when compared with the vehicle control group Note: Compound consumption in mg/kg bw/day was esti mated by the study authors by calculating the mean of the weekly (weeks 1-13) mean compound consumption values for males and females. FUNCTIONAL OBSERVATIONAL BATTERY (FOB) Home cage measurements: - No statistically significant or biologically rele vant findings Measurements during handling: - No statistically significant or biologically rele vant findings Open field measurements: - No statistically significant or biologically rele vant findings - Sporadic bizarre behaviors were noted Sensorimotor measurements: - A statistically significant reduction in hind foo t splay for 1000 ppm females compared to control at week 4; this difference was considered to be a function of normal biological variability - The hind foot splay values for the positive contr ol groups were increased at all FOB testing intervals when compared with the vehicle control group Grip strength: - No statistically or biologically relevant finding s Physiological measurements: - No statistically or biologically relevant changes in body temperature MOTOR ACTIVITY EVALUATIONS - No pertinent findings resulting from evaluation o f motor activity data which were determined to have biological significance OPHTHALMOSCOPIC EXAMINATIONS - No treatment-related ophthalmoscopic abnormalitie s were detected CLINICAL PATHOLOGY - Hematology: no treatment-related effects - Biochemistry: small but statistically significant (p<=0.01) increases in cholesterol were noted in both males and females in the 1000 ppm group; for males in the 300 ppm group a small but s tatistically significant(p<=0.01) decrease in albumin was observ ed at the pretest interval - Urinalysis: no treatment-related effects ANATOMIC PATHOLOGY - Neuropathology animals: no treatment-related effe cts Toxicity Test Animals: - Macroscopic: no treatment-related effects - Microscopic: no treatment-related microscopic cha nges, all microscopic changes were considered to be of spontaneous origin having no toxicological significance Organ weights: - A dose-related reduction in the group terminal bo dy weight was seen in both males and females of all treated group s compared to the vehicle control (statistically significant in t he 1000 ppm group) - In 1000 ppm males, the group mean relative weight s of brain (p<=0.05) and testis (p<=0.01) for the males were i ncreased - In females, the group mean relative weights of br ain (1000 ppm, p<=0.01), kidney (100 ppm, p<=0.05; 300 and 1000 pp m, p<=0.01), liver (1000 ppm, p<=0.01) and ovary (100 and 1000 p pm, p<=0.05)
were 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintincreased - All of these higher relative weights were conside red to be a reflection of the lower body weight and not due to any primary TS changes in those organs based on the fact that there was no si gnificant absolute weight difference for these organs and the re were no TS related gross or microscopic changes in these organ s) Conclusion: The NOAEL of the TS when administered orally via th e diet to Charles River Crl:CD VAF/Plus rats was considered to be 300 ppm for systemic toxicity (based on body weight and food co nsumption reductions and body weight gain inhibitions in both sexes at 1000 ppm) and greater than 1000 ppm for neurotoxicity (d ue to the lack of findings at any level evaluated). For systemic t oxicity, the NOAEL is ca. 18.2 mg/kg bw/day for males and 20.7 m g/kg bw/day for females. 

### Reliability/Data Quality - Repeated-Dose Toxicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: Well-documented study conducted according to accept able methods and under GLP. Key Study Sponsor Indicator: 

### Reference - Repeated-Dose Toxicity Reference: Schaefer, G.J. 1994. 13 Week Combined Subchronic Or al Toxicity and Neurotoxicity Study in Rats. International Research and Development Corporation, Mattawan, MI. Study No.: 658-005. Subm itted to: Sandoz Agro, Inc. May 6, 1994. BASF RegDoc# 94/11896. 

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## Repeated-Dose Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Repeated-Dose Toxicity Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Repeated-Dose Toxicity Route of Administration: Oral
Type of Exposure: In Food
Species: Rat

Mammalian Strain: Sprague-Dawley

Gender: Both M/F

Number of Animals per Dose: 10

Dose: 0, 500, 1500, 3000 ppm (ca. 39, 118 and 239 mg/kg b w)
Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 82-1

GLP: Yes
Exposure Period: 90 Days
Frequency of Treatment: Post-Exposure Period: Method/Guideline and Test Condition Remarks: The study was performed according to U.S. EPA FIFRA , Subdivision F, Paragraph 82-1. - The TS was administered to 10 male and female Spr ague-Dawley CD rats at dietary concentrations of 0, 500, 1500, and 3000 ppm over a period of 90 days - Analyses for stability and homogeneity of the tes t substance in the diet as well as for correct concentration were performed - Test substance intake was 39, 118 and 239 mg/kg b w for the 500, 1500 and 3000 ppm groups, respectively - Body weight and food consumption were determined weekly - The animals' state of health was checked twice da ily, moreover, comprehensive clinical examinations of the animals were performed 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintonce a week - Clinical chemistry and hematological examinations of the animals were carried out at the end of the administration p eriod - Ophthalmological examinations were carried out in all animals before the start and at the end of the administrati on period - At the end of the treatment period all animals we re sacrificed, subjected to complete gross examinations - The following organs were weighed for all animals at the scheduled sacrifice interval: adrenal glands, brain, kidneys, testes with epididymides, liver, ovaries and spleen - The following tissues were examined histopatholog ically in the control and 3000 ppm dose group: adrenal glands, aorta (thoraci c), brain (medulla/pons, cerebrum and cerebellum), esophagus, heart, intestine, cecum, colon, duodenum, ileum, jejunum, rectum, kidneys, liver, lungs (with mainstem bronchi), lymp h nodes (mesenteric, mediastinal), nerve (sciatic), pancrea s, pituitary gland, salivary gland (submandibular), spleen, stom ach, thymic region, thyroid/parathyroid glands, urinary bladder , gross lesions, testes with epididymides, ovaries and uter us (body/horns with cervix) - In addition, the kidneys, lungs, and liver were e xamined for all animals in the 500 and 1500 ppm groups - After fixation, animal tissues were routinely pro cessed, embedded in paraffin, cut at 4-7 microns, mounted o n glass slides, stained with hematoxylin and eosin and examined by light microscopy 

### Test Results - Repeated - Dose Toxicity Concentration (LOAEL/ LOAEC/ NOAEL/ NOAEC) : LOAEL/ LOAEC/ NOAEL/ NOAEC Population Value Description Value/Lower

Concentration Upper

Concentration Units

NOAEL = 500 ppm

Results Remarks: Stability analyses demonstrated that the TS was sta ble in the diet for the period of time presented to the animals and that the TS was homogeneously distributed in the feed. Concentr ation verification analyses confirmed the theoretical die tary concentrations.

CLINICAL SIGNS & MORTALITY - No mortalities occurred during the study, and the re were no clinical signs which were considered to be treatment-related. OPHTHALMOSCOPIC FINDINGS - No treatment-related effects were observed. BODY WEIGHT & FOOD CONSUMPTION - Mean body weight gain was statistically decreased (p<=0.01) in 3000 ppm males and the females treated with 1500 an d 3000 ppm - Mean body weights of 3000 ppm males were statisti cally lower (p<=0.05) than those of the control animals during weeks 3 an d 5 of the study - The mean body weight of the 1500 ppm females was statistically lower (p<=0.05) than that of the control animals during w eek 1 of the 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintstudy - At study termination, the mean body weight values of the mid and high dose males were 5% and 7% lower than that of the co ntrol animals, for the mid and high dose females, the mean body weight values were 4% and 5% lower than that of the control animals - No treatment-related effects were observed regard ing food consumption

STATISTICALLY SIGNIFICANT MEAN WEEKLY BODY WEIGHT GAIN VALUES - Males

------------------------------------- Control 500ppm 1500ppm 3000ppm Week 0 77.1 76.7 71.8* 76.7 Week 1 53.6 55.7 49.7 42.8**

STATISTICALLY SIGNIFICANT MEAN CUMULATIVE BODY WEIGHT GAIN VALUES - Males

----------------------------------------- Control 500ppm 1500ppm 3000ppm Week 1 53.6 55.7 49.7 42.8** Week 2 109.3 111.8 102.8 80.4* Week 3 159.7 163.1 145.8 127.6* Week 4 195.3 199.2 178.8 166.6* Week 5 228.9 232.1 212.7 195.4* Week 6 257.1 263.9 239.3 232.2*

STATISTICALLY SIGNIFICANT MEAN WEEKLY BODY WEIGHT GAIN VALUES - Females

------------------------------------------ Control 500ppm 1500ppm 3000ppm Week 1 24.5 21.9 14.4** 15.4**

STATISTICALLY SIGNIFICANT MEAN CUMULATIVE BODY WEIGHT GAIN VALUES - Females

----------------------------------------- Control 500ppm 1500ppm 3000ppm Week 1 24.5 21.9 14.4** 15.4** Week 9 124.6 118.0 105.3* 106.2*

------------------------------------ * P<=0.05 **P<=0.01

HEMATOLOGY - An increase in clotting time as measured by activ ated partial thromboplastin time was noted. URINALYSIS - The mean activated partial thromboplastin (APTT) was statistically significantly (p<= 0.01) higher than that of the co ntrol; however, this was not considered to be biologically significant - No additional statistically significant effects o n the urinalysis parameters investigated. CLINICAL CHEMISTRY - Serum gamma-glutamyltransferase was increased in both sexes at the high dose and in males at 1500 ppm. - Cholesterol was also increased in both sexes at t he high dose (p<=0.01) - The mean serum alkaline phosphatase values for th e males treated with 1500 ppm and 3000 ppm were significantly (p<=0 .05) lower than 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintthose of the control animals - Mean gamma-glutamyl transferase values were signi ficantly increased in comparison to the control values in the males treat ed with 1500 ppm (p<=0.05) and with 3000 ppm (p<=0.01)

STATISTICALLY SIGNIFICANT MEAN CLINICAL CHEMISTRY VALUES - Males

--------------------------------------- Control 500ppm 1500ppm 3000ppm Aspartate Aminostransferase (SGOT) 84 72* 72* 61** Alkaline Phosphatase 120 104 87** 85** Cholesterol 65 73 80 96** Albumin 4.4 4.5 4.6* 4.7** Gamma-Glutamyl Transferase 1 0 3* 5**

STATISTICALLY SIGNIFICANT MEAN CLINICAL CHEMISTRY VALUES - Females

--------------------------------------- Control 500ppm 1500ppm 3000ppm Creatinine 0.4 0.4 0.4* 0.4 Total Protein 7.2 7.5 7.6 7.9* Globulin (calculated) 2.0 2.1 2.2 2.4** Total Bilirubin 0.2 0.1 0.1* 0.1*

------------------------------------ * P<=0.05 **P<=0.01

ORGAN WEIGHTS - Absolute liver weights were significantly (p<=0.0 1) increased in both sexes at the high dose - Statistically significant increases in liver/body weight and liver/brain ratios of males in all dose groups - Relative liver weights were increased by 11, 21 a nd 36% in males in the low, mid and high doses, respectively. - Absolute and relative liver weights of the 3000 p pm females were significantly (p<=0.01) elevated - The liver/body weight ratio of the 1500 ppm femal es also statistically elevated (p<=0.01) - Relative liver weight was increased in high dose females by 25%. - The absolute and relative liver weights of 500 pp m females were generally comparable to the controls - The test substance had no effect on adrenal, brai n, kidney and spleen weights - The group mean absolute weight, organ to body wei ght ratios and organ to brain weight ratios of all the examined re productive organs were unaffected in all dose groups

STATISTICALLY SIGNIFICANT TERMINAL ORGAN AND BODY WEIGHTS, ORGAN/BODY WEIGHT AND ORGAN/BRAIN WEIGHT RATIOS - Males

------------------------------------------------- Control 500ppm 1500ppm 3000ppm Kidney - Organ weight / total body weight (x1000) 8.41 8.52 8.90 9.78** Liver - Weight (g) 15.237 17.124 17.654 19.303** Liver - Organ weight / total body weight (x1000) 2.92 3.25** 3.53** 3.97** Liver - Organ weight / brain weight 6.75 7.79* 8.14** 8.54**

STATISTICALLY SIGNIFICANT TERMINAL ORGAN AND BODY 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintWEIGHTS, ORGAN/BODY WEIGHT AND ORGAN/BRAIN WEIGHT RATIOS - Females

------------------------------------------------- Control 500ppm 1500ppm 3000ppm Liver - Weight (g) 8.830 8.743 9.417 10.395** Liver - Organ weight / total body weight (x1000) 3.13 3.18 3.51** 3.91** Liver - Organ weight / brain weight 4.26 4.29 4.66 5.03**

------------------------------------ * P<=0.05 **P<=0.01

HISTOPATHOLOGICAL FINDINGS - No treatment-related macroscopic changes were obs erved - Histologically the only treatment-related finding was hepatocellular hypertrophy in both sexes (periportal in males and centrilobular in females) at 3000 ppm and 1500 ppm and in females only at 500 ppm - Swelling of hepatocellular cells and subsequent l iver weight increase generally indicates an adaptive response of the liv er to handling the chemical and not frank toxicity - The reproductive organs examined were unaffected by treatment with the test substance Definite signs of toxicity were observed at the hig h dose of 3000 ppm including decreased body weight gains, increased se rum gammaglutamyltransferase and increased cholesterol. Lesser effects on body weight gain and gamma-glutamyltransferase were also observed at the mid dose of 1500 ppm. The only changes noted at 500 ppm were a decrease in aspartate aminotransferase, a sl ight increase in relative liver weight (males only) and hepatocel lular hypertrophy in females. The decrease in aspartate a minotransferase is of questionable toxicological significance. Abso lute liver weights were not affected at 500 ppm and the relati ve liver weight was increased only slightly in males. The hepatocel lular hypertrophy was only minimal or slight. Enlarged li vers coupled with enlarged hepatocytes is generally interpreted as a physiological response to the chemical and does not represent frank toxicity. The slight physiological changes at 500 ppm are not considered an adverse effect and, therefore, 50 0 ppm is considered a no observed adverse effect level (NOAE L). Conclusion: The NOAEL was found to be 500 ppm (ca. 39 mg/kg bw) for male and female Sprague-Dawley CD rats. 

### Reliability/Data Quality - Repeated-Dose Toxicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted subchroni c toxicity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Repeated-Dose Toxicity Reference: Blanset, D. 1996. A subchronic (3-month) toxicity s tudy of SAN 1289 H in the rat via dietary administration. Hunti ngdon Life Sciences, East Millstone, New Jersey, USA, unpublis hed. BASF RegDoc #96/5420. 

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## Genetic Toxicity in vivo
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Genetic Toxicity in vivo Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 96.3% Sponsored Chemical Result Type: See Test Plan and Category Analysis 

### Method - Genetic Toxicity in vivo Type of Study: Bone Marrow Chromosomal Aberration
Type of Test: Micronucleus assay

Route of Administration: Intraperitoneal
Type of Exposure:
Species: Mouse

Strain: ICR

Gender: Both M/F

Dose: 103, 205, and 410 mg/kg bw in a volume of 20 mL/kg bw Year Study Performed: 1996
Method/Guideline Followed: OECD 474

GLP: Yes

Duration of Treatment/ Exposure Period and Units: Frequency of Treatment: 1X
Positive, Negative, and Solvent Control Substance(s): The negative control group received the vehicle onl y (corn oil). Cyclophosphamide was used as the positi ve control. Number of Animals per Sex and Dose Group: 15

Method/Guideline and Test Condition Remarks: The study was performed according to OECD 474 "Mammalian Erythrocyte Micronucleus Test" and EEC 79/831, B12. The TS was tested for clastogenicity and the abilit y to have a spindle 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintposition effect in ICR mice using a micronucleus test. The TS was dissolved in corn oil and was administered in a single i.p. dose to 15 male and female mice per group at doses of 103, 205, and 410 mg/kg bw in a volume of 20 mL/kg bw. The doses were selected based on a preliminary toxicity study wher e mortality was observed at doses of 600 mg/kg bw and above. The negative control group received the vehicle only. Cyclophosphamide was used as the positive control. Five animals per sex per group were sacrificed at 2 4, 48, and 72 h after administration of the TS and the bone marrow of two femora was prepared. The positive controls were sacrificed 24 h after administration. After stainin g of the preparations, 1000 polychromatic erythrocyte s were evaluated per animal. Verification of the TS concentrations were determin ed analytically. 

### Test Results - Genetic Toxicity in vivo Systemic Toxicity:

Genotoxic Effect: Negative

Results Remarks: The target concentrations were verified analyticall y. No mortality occurred at any dose level. The administration of the TS led to clinical symptoms in animals at 205 and 410 mg/k g bw. These symptoms included lethargy, hyperactivity and aggressiveness. There were no clinical signs of toxicity in the vehicle control, the low dose or th e positive control groups. No inhibition of erythropoiesis as determined from the ratio of polychromatic to normochromatic erythrocytes was detected. The administration of the TS did not lead to an increase in the number of polychromatic erythrocytes containing micronuclei i n any of the dose groups at any time period measured after treatment. The administration of the positive control resulted in the expected increase in micronuclei, demonstrating the sensitivity of the assay. Conclusion: Under the conditions of this test, the TS does not have a chromosome damaging (clastogenic) effect in vivo. 

### Reliability/Data Quality - Genetic Toxicity in vivo Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted clastogenicity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Genetic Toxicity in vivo Reference: Putman, D., et al. 1996. Micronucleus cytogenetic assay in mice: SAN 1289 H technical MICROBIOLOGICAL Associates, Rockville, Maryland, USA, unpublished. BASF RegDoc #96/5401. 

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## Genetic Toxicity in vitro
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

- 

### Test Substance - Genetic Toxicity in vitro Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was T0 1184 (SAN 582, step C4 "Via Keto-Enol"). The test substance was the racemic C4, CAS No. 87676-01-1, 3-thiophenamine,N-(2-methoxy-1-methylet hyl)-2,4-dimethylSponsored Chemical Result Type: Measured


### Method - Genetic Toxicity in vitro Type of Study: Bacterial reverse mutation assay

Concentrations: 200, 300, 600, 1000, 2000, 3000 ug/plate
Year Study Performed: 1988
Method/Guideline Followed: OECD 471

GLP: No
Postive, Negative, and Solvent Control Substance (s): Negative controls: - DMSO with and without metabolic activation Positive controls: With metabolic activation: - 2-aminoanthracene 3 ug/plate (TA1535 and TA98) - 2-aminoanthracene 10 ug/plate (TA100 and TA97) - Benzo(a)pyrene 3 ug/plate (TA98) Without metabolic activation: - 9-aminoacridine 100 ug/plate (TA97) - MMNG 3 ug/plate (TA1535 and TA100) - 2-Nitrofluorine 2 ug/plate (TA98) - Mitomycin C 0.5 ug/plate (TA102) Method/Guideline and Test Condition Remarks: METHODOLOGY: - The study is similar to OECD Test Guideline 471 CONTROLS: - Every plate received 0.1 mL of the solvent Negative controls: - DMSO with and without metabolic activation Positive controls: With metabolic activation: - 2-aminoanthracene 3 ug/plate (TA1535 and TA98) - 2-aminoanthracene 10 ug/plate (TA100 and TA97) - Benzo(a)pyrene 3 ug/plate (TA98) Without metabolic activation: - 9-aminoacridine 100 ug/plate (TA97) - MMNG 3 ug/plate (TA1535 and TA100) - 2-Nitrofluorine 2 ug/plate (TA98) - Mitomycin C 0.5 ug/plate (TA102) Beginning of test substance administration: - The TS and all control substances were mixed with the top agar components and were directly plated without pr eincubation (standard method) BACTERIAL STRAINS: TA97, TA98, TA100, TA102, TA1535 - The strain-selections were made according to Mut. Res. 113, 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint(1983), 173-215. - The organisms were received from Prof. B.N. Ames - They were activated, controlled, and identified a ccording to standard operating procedures RAT LIVER HOMOGENATE: - A 9000g supernatant from the liver of Aroclor 125 4 induced male rats - The homogenate was frozen in aliquots of 2 mL, it was stored at -70 to -80 deg C until use - The S9 contained per mL: supernatant from liver h omogenate (0.1 mL), NADP (4 umol), glucose-6-phosphate (5 umo l), Na/K phosphate buffer pH 7.4 (100 umol), MgCl2 (8 umol), KCl (33 umol) PLATE TEST: - The agar mixture was poured into plates and allow ed to harden - Two or three plates were used for each concentrat ion of the TS, for the positive control and for the solvent - The plates were then incubated at 37 deg C for 90 h and then checked for the presence of the light background lawn - The number of revertants on each plate were count ed ANALYSIS: - Colonies were counted after a 90 hour incubation period with a ARTEK 880 counting instrument - The examination was without randomization and the analysis was without standard methods 

### Test Results - Genetic Toxicity in vitro Details on Cytogenetic Assay:
Statistics:

Effect : Species Other Species Strain Other

Strain Metabolic Activation Genotoxic

Effect Conclusion

Results Remarks: SOLUBILITY: - Stable in DMSO up to 30000 ug/mL (3000 ug/plate) - The solutions of the TS were added to the tester plates within one hour after preparation TOXICITY: - The two highest concentrations, 2000 and 3000 ug/ plate, were partially bacteriotoxic MUTAGENICITY: - The positive controls showed the expected mutagen icity pattern - Treatment of 1000 ug/plate without metabolic acti vation increased the number of TA1535 revertants 1.60 times that of the control without metabolic activation - The data are shown below for TA1535 (without meta bolic activation): Conc. A B C Mean X/control 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint0.00 48 36 45 43 1 300 51 52 55 53 1.23 1000 71 76 60 69 1.60 3000 b b b - - b = bacteriotoxic - Addition of S9 completely suppressed the inductio n of mutants of strain TA 1535 - Treatment with the TS had no mutagenic effect on any of the other tester strains up to the bacteriotoxic dose r ange Conclusion: The TS is a weak, per se active mutagen for Salmone lla typhimurium under the test conditions used. 

### Reliability/Data Quality - Genetic Toxicity in vitro Reliability: 1 - Valid Without Restrictions
Reliability Remarks: The test was performed according to Sandoz Pharma D ivision SOP, which is in accordance with OECD Test Guidelin e 471 "Bacterial Reverse Mutation Test" with no significa nt deviations. Key Study Sponsor Indicator: 

### Reference - Genetic Toxicity in vitro Reference: Suter, W. 1988b. T01184 San 582H C-4 Intermediate ( Via KetoEnol) Mutagenicity Evaluation Using Salmonella typh imurium. Sandoz, Ltd. Pharma Division Research and Development. Study No.: Mut. Bact. 30/88_2. 11 Nov 1988. 

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## Genetic Toxicity in vitro
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

- 

### Test Substance - Genetic Toxicity in vitro Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P (analytical grade reference st andard) CAS#: 163515-14-8 Batch No.: RS-1289-111596 Purity 99.4% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Genetic Toxicity in vitro Type of Study: Bacterial reverse mutation assay

Concentrations: 4 to 5000 ug/plate
Year Study Performed: 1997
Method/Guideline Followed:
GLP: Yes
Postive, Negative, and Solvent Control Substance (s): For control purposes and to demonstrate the sensiti vity of the test system, a negative control and positive controls both with and without S9 mix were tested. Method/Guideline and Test Condition Remarks: The study was performed according to OECD Test Guid elines 471 and 472 and EC 92/69 B14 and B13. S. typhimurium strains TA100, TA1535, TA1537, TA98, and E.coli strain WP2 uvrA were used The test system strains were exposed to the TS diss olved in DMSO at doses ranging from 4 to 5000 ug/plate. The study consisted of a standard plate test and preincubatio n test both with and without metabolic activation (Aroclor indu ced rat liver S9 mix). Three plates were used per dose for each strain. 

### Test Results - Genetic Toxicity in vitro Details on Cytogenetic Assay:
Statistics:

Effect : Species Other Species Strain Other

Strain Metabolic Activation Genotoxic

Effect Conclusion



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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintResults Remarks: A bacteriotoxic effect was observed depending on th e strain and test conditions at doses greater than or equal to 2500 ug/plate in the standard plate test and at doses greater than o r equal to 500 ug/plate in the preincubation test. The mean number of rever tant colonies was not increased in any strain either with or without S9 activation. Expected increases in revertant colonie s were obtained with the positive controls. Another Ames test was performed by the same investi gators using dimethenamid technical, 91.1%. This test also reported a negative result.
Engelhardt, G., and Hoffman, H. 1997. Salmonella typhimurium/Escherichia coli reverse mutation assay with sdimethenamid. BASF Aktiengesellschaft, Ludwigshafen, Germany, unpublished. BASF RegDoc #97/10622. Conclusion: According to the results of the study, analytical g rade pure dimethenamid-P is not mutagenic in the Ames reverse mutation assay. 

### Reliability/Data Quality - Genetic Toxicity in vitro Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted in vitro reverse mutation testing guidelines. Key Study Sponsor Indicator: 

### Reference - Genetic Toxicity in vitro Reference: Engelhardt, G., and Hoffman, H. 1997. Salmonella typhimurium/Escherichia coli reverse mutation assay (standard plate test and preincubation test) with s-dimethena mid. BASF Aktiengesellschaft, Ludwigshafen, Germany, unpublis hed. BASF RegDoc #97/10621. 

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## Genetic Toxicity in vitro
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

- 

### Test Substance - Genetic Toxicity in vitro Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was T0 1184 (SAN 582, step C4 "Via Keto-Enol"). The test substance was the racemic C4, CAS No. 87676-01-1, 3-thiophenamine,N-(2-methoxy-1-methylet hyl)-2,4-dimethylSponsored Chemical Result Type: Measured


### Method - Genetic Toxicity in vitro Type of Study: Bacterial reverse mutation assay

Concentrations: 500, 1000, 1500, 2000, 2500 and 3000 ug/plate
Year Study Performed: 1988
Method/Guideline Followed: OECD 471

GLP: No
Postive, Negative, and Solvent Control Substance (s): Negative controls: - DMSO with and without metabolic activation Positive controls: With metabolic activation: - 9-aminoacridine 3 ug/plate Without metabolic activation: - MMNG 3 ug/plate Method/Guideline and Test Condition Remarks: METHODOLOGY: - The study is similar to OECD Test Guideline 471 CONTROLS: - Every plate received 0.1 mL of the solvent Negative controls: - DMSO with and without metabolic activation Positive controls: With metabolic activation: - 9-aminoacridine 3 ug/plate Without metabolic activation: - MMNG 3 ug/plate Beginning of test substance administration: - The TS and all control substances were mixed with the top agar components and were directly plated without pr eincubation (standard method) BACTERIAL STRAIN: TA1535 - The strain-selections were made according to Mut. Res. 113, (1983), 173-215. - The organisms were received from Prof. B.N. Ames - They were activated, controlled, and identified a ccording to standard operating procedures RAT LIVER HOMOGENATE: - A 9000g supernatant from the liver of Aroclor 125 4 induced male rats - The homogenate was frozen in aliquots of 2 mL, it was stored at -70 to -80 deg C until use - The S9 contained per mL: supernatant from liver h omogenate 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint(0.1 mL), NADP (4 umol), glucose-6-phosphate (5 umo l), Na/K phosphate buffer pH 7.4 (100 umol), MgCl2 (8 umol), KCl (33 umol) PLATE TEST: - The agar mixture was poured into plates and allow ed to harden - The TS was plated at 25, 250 and 2500 ug/plate - Two or three plates were used for each concentrat ion of the TS, for the positive control and for the solvent - The plates were then incubated at 37 deg C for 90 h and then checked for the presence of the light background la wn - The number of revertants on each plate were count ed ANALYSIS: - Colonies were counted after a 90 hour incubation period with a ARTEK 880 counting instrument - The examination was without randomization and the analysis was without standard methods 

### Test Results - Genetic Toxicity in vitro Details on Cytogenetic Assay:
Statistics:

Effect : Species Other Species Strain Other

Strain Metabolic Activation Genotoxic

Effect Conclusion

Results Remarks: SOLUBILITY: - Stable in DMSO up to 30000 ug/mL (3000 ug/plate) - The solutions of the TS were added to the tester plates within one hour after preparation TOXICITY: - 2500 ug/plate was partially bacteriotoxic, 3000 u g/plate was bacteriotoxic MUTAGENICITY: - The positive controls showed the expected mutagen icity pattern - Treatment of 2000 ug/plate without metabolic acti vation increased the number of TA1535 revertants 2.53 time s that of the control without metabolic activation; higher concentrations were bacteriotoxic - The number of revertants increased in a dose-depe ndent manner until the bacteriotoxic concentrations - The data are shown below for TA1535 (without meta bolic activation): Conc. A B C Mean X/control 0 41 34 40 38 1 500 57 62 68 62 1.63 1000 70 80 88 79 2.08 1500 85 85 110 93 2.45 2000 95 91 103 96 2.53 2500 76* 86 97 86 2.26 3000 b b 71* 71 1.87 b = bacteriotoxic * = reduced background lawn of growth 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint- Treatment with the TS had no mutagenic effect on any of the other tester strains up to the bacteriotoxic dose r ange Conclusion: The TS is a weak, per se active mutagen for Salmone lla typhimurium under the test conditions used. 

### Reliability/Data Quality - Genetic Toxicity in vitro Reliability: 1 - Valid Without Restrictions
Reliability Remarks: The test was performed according to Sandoz Pharma D ivision SOP, which is in accordance with OECD Test Guidelin e 471 "Bacterial Reverse Mutation Test" with no significa nt deviations. Key Study Sponsor Indicator: 

### Reference - Genetic Toxicity in vitro Reference: Suter, W. 1988c. T01184 San 582H C-4 Intermediate ( Via KetoEnol) Mutagenicity Evaluation Using Salmonella typh imurium. Sandoz, Ltd. Pharma Division Research and Development. Study No.: Mut. Bact. 30/88_3. 11 Nov 1988. 

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## Genetic Toxicity in vitro
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

- 

### Test Substance - Genetic Toxicity in vitro Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Genetic Toxicity in vitro Type of Study: Mammalian cell gene mutation assay

Concentrations: 100 - 400 ug/mL without S9-mix and from 100 - 450 u g/mL with S9 mix Year Study Performed: 1996
Method/Guideline Followed: OECD 476

GLP: Yes
Postive, Negative, and Solvent Control Substance (s): A vehicle negative control was used as well as appr opriate positive controls to demonstrate the sensitivity of the test system both with and without metabolic activation.
Method/Guideline and Test Condition Remarks: The study was performed according to OECD Test Guid eline 476 "In Vitro Mammalian Cell Gene Mutation Test." The TS was tested for its ability to induce gene mu tations at the HPRT locus in the CHO-K1-BH4 cell line in vitro . The dose levels used were selected based on results from a p reliminary toxicity assay. The cells were treated for 5 hours. The concentrations of the TS dissolved in DMSO were fro m 100 - 400 ug/mL without S9-mix and from 100 - 450 ug/mL with S9 mix. A vehicle negative control was used as well as approp riate positive controls to demonstrate the sensitivity of the test system both with and without metabolic activation. 

### Test Results - Genetic Toxicity in vitro Details on Cytogenetic Assay:
Statistics:

Effect : Species Other Species Strain Other

Strain Metabolic Activation Genotoxic

Effect Conclusion



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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintResults Remarks: The treatment medium was cloudy, but without visibl e precipitation of the TS at concentrations greater than or equal to 400 u g/mL. Toxicity (i.e. the cloning efficiency was reduced) occurred at the hig her concentrations tested. Positive controls gave expected results. With the t est material, no biologically significant increases in the mutant frequency were observed either with or without meta bolic activation. Conclusion: It is concluded that the TS is not mutagenic in the CHO/HGPRT test. 

### Reliability/Data Quality - Genetic Toxicity in vitro Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted gene mutation testi ng guidelines. Key Study Sponsor Indicator: 

### Reference - Genetic Toxicity in vitro Reference: San, R., Clark, J. 1996. CHO/HGPRT mutation assay: SAN 1289 H technical. MICROBIOLOGICAL Associates, Rockville, M aryland, USA, unpublished. BASF RegDoc #96/5404. 

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## Genetic Toxicity in vitro
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

- 

### Test Substance - Genetic Toxicity in vitro Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was T0 1184 (SAN 582, step C4 "Via Keto-Enol"). The test substance was the racemic C4, CAS No. 87676-01-1, 3-thiophenamine,N-(2-methoxy-1-methylet hyl)-2,4-dimethylSponsored Chemical Result Type: Measured


### Method - Genetic Toxicity in vitro Type of Study: Bacterial reverse mutation assay

Concentrations: 25, 250 and 2500 ug/plate
Year Study Performed: 1988
Method/Guideline Followed: OECD 471

GLP: No
Postive, Negative, and Solvent Control Substance (s): Negative controls: - DMSO with and without metabolic activation Positive controls: With metabolic activation: - 2-aminoanthracene 3 ug/plate (TA1535 and TA98) - 2-aminoanthracene 10 ug/plate (TA100 and TA97) - Benzo(a)pyrene 3 ug/plate (TA98) Without metabolic activation: - 9-aminoacridine 100 ug/plate (TA97) - MMNG 3 ug/plate (TA1535 and TA100) - 2-Nitrofluorine 2 ug/plate (TA98) - Mitomycin C 0.5 ug/plate (TA102) Method/Guideline and Test Condition Remarks: METHODOLOGY: - The study is similar to OECD Test Guideline 471 CONTROLS: - Every plate received 0.1 mL of the solvent Negative controls: - DMSO with and without metabolic activation Positive controls: With metabolic activation: - 2-aminoanthracene 3 ug/plate (TA1535 and TA98) - 2-aminoanthracene 10 ug/plate (TA100 and TA97) - Benzo(a)pyrene 3 ug/plate (TA98) Without metabolic activation: - 9-aminoacridine 100 ug/plate (TA97) - MMNG 3 ug/plate (TA1535 and TA100) - 2-Nitrofluorine 2 ug/plate (TA98) - Mitomycin C 0.5 ug/plate (TA102) Beginning of test substance administration: - The TS and all control substances were mixed with the top agar components and were directly plated without pr eincubation (standard method) BACTERIAL STRAINS: TA97, TA98, TA100, TA102, TA1535 - The strain-selections were made according to Mut. Res. 113, 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint(1983), 173-215. - The organisms were received from Prof. B.N. Ames - They were activated, controlled, and identified a ccording to standard operating procedures RAT LIVER HOMOGENATE: - A 9000g supernatant from the liver of Aroclor 125 4 induced male rats - The homogenate was frozen in aliquots of 2 mL, it was stored at -70 to -80 deg C until use - The S9 contained per mL: supernatant from liver h omogenate (0.1 mL), NADP (4 umol), glucose-6-phosphate (5 umo l), Na/K phosphate buffer pH 7.4 (100 umol), MgCl2 (8 umol), KCl (33 umol) PLATE TEST: - The agar mixture was poured into plates and allow ed to harden - The TS was plated at 25, 250 and 2500 ug/plate - Two or three plates were used for each concentrat ion of the TS, for the positive control and for the solvent - The plates were then incubated at 37 deg C for 90 h and then checked for the presence of the light background la wn - The number of revertants on each plate were count ed ANALYSIS: - Colonies were counted after a 90 hour incubation period with a ARTEK 880 counting instrument - The examination was without randomization and the analysis was without standard methods 

### Test Results - Genetic Toxicity in vitro Details on Cytogenetic Assay:
Statistics:

Effect : Species Other Species Strain Other

Strain Metabolic Activation Genotoxic

Effect Conclusion

Results Remarks: SOLUBILITY: - Stable in DMSO - The solutions of the TS were added to the tester plates within one hour after preparation TOXICITY: - Not toxic at any concentration MUTAGENICITY: - The positive controls showed the expected mutagen icity pattern - Treatment of 2500 ug/plate without metabolic acti vation increased the number of TA1535 revertants 2.30 time s that of the control without metabolic activation - The number of revertants increased in a dose-depe ndent
manner - The data are shown below for TA1535 (without meta bolic activation): Conc. A B Mean X/control 0.00 42 52 47 1 25.0 61 53 57 1.21 250 60 50 55 1.17 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint2500 105 111 108 2.30 - Addition of S9 completely suppressed the inductio n of mutants of strain TA 1535 - Treatment with the TS had no mutagenic effect on any of the other tester strains up to the bacteriotoxic dose r ange Conclusion: The TS is a weak, per se active mutagen for Salmone lla typhimurium under the test conditions used. 

### Reliability/Data Quality - Genetic Toxicity in vitro Reliability: 1 - Valid Without Restrictions
Reliability Remarks: The test was performed according to Sandoz Pharma D ivision SOP, which is in accordance with OECD Test Guideline 471 "Bact erial Reverse Mutation Test" with no significant deviations. Key Study Sponsor Indicator: 

### Reference - Genetic Toxicity in vitro Reference: Suter, W. 1988a. T01184 San 582H C-4 Intermediate ( Via KetoEnol) Mutagenicity Evaluation Using Salmonella typh imurium. Sandoz, Ltd. Pharma Division Research and Development. Study No.: Mut. Bact. 30/88_1. 11 Nov 1988. 

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## Reproductive Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Reproductive Toxicity Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1- methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was SAN 582 H C-4 Intermedi ate. The test substance was the racemic C4, CAS No. 87676-01-1, 3

- thiophenamine,N-(2-methoxy-1-methylethyl)-2,4-dimet hylSponsored Chemical Result Type: Measured


### Method - Reproductive Toxicity Route of Administration: Oral
Type of Exposure: In Food
Species: Rat

Mammalian Strain: Other

Other Strain:

Gender: Both M/F

Number of Animals per Dose: 32

Dose: 100, 300 and 1000 ppm (Males: ca. 6.2, 18.2, 57.7 m g/kg bw/day; Females: ca. 7.4, 20.7, 66.0 mg/kg bw/day) Year Study Performed: 1994
Method/Guideline Followed:
GLP: Yes
Exposure Period: 13 Weeks
Frequency of Treatment: continuous (ad libitum)
Post-Exposure Period: Method/Guideline and Test Condition Remarks: TEST SUBSTANCE ANALYSES: - Test samples of treated diet were assessed for ho mogeneity and stability - Positive control preparations were tested to veri fy stability in the diet for up to one week - Periodic analyses of each test diet prepared were collected for each of the first 4 weeks and monthly for the remainder of the study and were analyzed in duplicate for test article concent ration 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintEXPERIMENTAL DESIGN Test Animals & Environmental Conditions: - The animals were housed individually for the enti rety of the study (except day 1 of acclimation in which they we re housed 3 per cage) - Age at randomization: 41 days - Body weight at randomization: males 138-162 g; fe males 116-134 g - The acclimation period was a minimum of 7 days - During acclimation, the animals were observed for any clinical signs of disease - The animals were provided with basal laboratory d iet of Certified Rodent Chow #5002 (replaced 3 times/study week) and tap wa ter ad libitum - Temperature: 70-73 deg F (71 +/- 0.9 deg F) - Humidity: 46-70% (57 +/- 8.4%) - Photoperiod: fluorescent lighting provided 12 hou rs per day Exposure: - The animals were randomly assigned to the positiv e control, vehicle control, and the three concentration groups - The positive control was 16 mg/kg/day acrylamide - Animals were randomly selected for neurobehaviora l examination and neuropathology, which were conducted over a 4-5 day period; the animals were divided into approx. equal squads of male and female rats from each group - For each dose and controls 16 males and 16 female s were exposed to the TS - Exposure concentrations: 100, 300, 1000 ppm (sele cted on the basis of available data from IRDC Study Number 658-006, "4-W eek Oral Toxicity Study in Rats-Pilot") - The positive control was administered by intragas tric intubation (5 times/week for 13 weeks) IN-LIFE EXAMINATIONS Mortality: - At least twice daily throughout the study Clinical Signs: - Twice daily for signs of overt toxicity at the ti mes of the moribundity/mortality checks - Detailed examinations were conducted once each we ek beginning with treatment, particular attention was given to detect behavioral and/or neurological abnormalities Weekly Body Weights: - Recorded weekly from randomization until euthanas ia for all animals Food & Compound Consumption: - Recorded weekly from randomization until euthanas ia for all animals - Compound consumption was calculated on the corres ponding food consumption weeks Disposition of Animals: - Following week 13, animals not selected for neuro pathological examination were euthanized by CO2 asphyxiation and necropsied; each rat was examined for external abnormalities, includ ing palpable masses, and the thoracic and abdominal cavities and organs were examined for grossly evident morphological changes - Tissues were saved in buffer for histopathologica l examination Clinical Pathology: - Conducted on 11/sex/group at pretest and survivin g animals at study termination - Hematological, biochemical, and urological parame ters were 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintassessed Anatomic Pathology - Toxicity Test Animals: Macroscopic - Complete postmortem examination performed in all toxicity test animals - All survivors were sacrificed by CO2 asphyxiation and examined for external abnormalities including palpable masses - Any internal masses were recorded - Representative samples of the following reproduct ive organs were collected and preserved for examination: ovaries (2 ), testis with epididymides (2), mammary gland (females only), pro state gland and seminal vesicle (2), uterus (both horns), the uteru s and cervix, and the vagina Organ Weights - Absolute organ weights from all surviving toxicit y test animals
were recorded along with postmortem body weights and app ropriate weight ratios (relative to body and brain weight) calculat ed - Of the organs with reproductive function, only th e ovaries and the testes were weighed Microscopic - A full complement of organs and tissues were exam ined microscopically for the vehicle control and high-dose groups euthan ized at study termination and on all toxicity test animals from a ll groups euthanized during the course of the study. - Representative samples of the following reproduct ive organs were collected and preserved for examination: ovaries (2 ), testis with epididymides (2), mammary gland (females only), pro state gland and seminal vesicle (2), uterus (both horns), the uteru s and cervix, and the vagina - In addition, the following tissues were examined microscopically for all toxicity test animals in the low and mid dose group s: liver, kidney (2), and lung (2) - The observed lesions were graded as trace, mild, moderate, or
severe STATISTICAL ANALYSES: - All statistical analyses compared the treatment g roups with the vehicle control with levels of significance at p = 0.05 and p = 0.01 Pre-Mating Exposure / Males: Pre-Mating Exposure / Females: 

### Test Results - Reproductive Toxicity Concentration (LOAEL/ LOAEC/ NOAEL/ NOAEC) : LOAEL/ LOAEC/ Population Value Description Value/Lower

Concentration Upper

Concentration Units



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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintNOAEL/ NOAEC NOAEL Female

(Maternal) = 66 mg/kg bw NOAEL Male

(Paternal) = 57 mg/kg bw

Results: Results for Organ Weights and Pathology are summari zed below: ANATOMIC PATHOLOGY - Macroscopic: no treatment-related effects on any examined reproductive tissue or non-reproductive tissue - Organ weights: a dose-related reduction in the gr oup terminal body weight was seen in both males and females of all tr eated groups compared to the vehicle control (statistically significant i n the 1000 ppm group), consequently the group mean relative weights of bra in (p< 0.05) and testis (p< 0.01) for the males and the brain 1000 ppm, p< 0.01), kidney (100 ppm, p< 0.05; 300 and 1000 ppm, p< 0.01), liver (10 00 ppm, p< 0.01) and ovary (100 and 1000 ppm, p< 0.05) for the females w ere higher in the 1000 ppm group (all of these higher relative weights wer e considered to be a reflection of the lower body weight and not due to any primary TS changes in those organs based on the fact that there was no significant absolute weight difference for these organs and there were n o TS related gross or microscopic changes in these organs) - Microscopic: no treatment-related microscopic cha nges on reproductive or non-reproductive tissues, all microscopic change s were considered to be of spontaneous origin having no toxicological signi ficance Results Remarks: This study is a sub-chronic toxicity/neurotoxicity study that was not performed specifically to assess toxicity to fe rtility. Data from examinations of reproductive organs and tissues are summarized h ere. The entry for Repeat Dose Toxicity contains the fol lowing information: Prepared test and control article analyses; Mortali ty; Clinical Signs; Weekly Body Weights; Food & Compound Consumption; Function al Observational Battery; Motor Activity Evaluations; Opthalmoscopic Evaluations; and Clinical Pathology. Conclusion: No effects were observed on reproductive organs or tissues up to and including the highest dose tested (ca. 57.7 mg/ kg bw/day for males and 66.0 mg/kg bw/day for females) 

### Reliability/Data Quality - Reproductive Toxicity Reliability: 2 - Valid With Restrictions 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintReliability Remarks: This is a well-documented study conducted according to acceptable methods and under GLP. The purpose of this study wa s not to examine toxic effects to fertility. However, reproductive o rgans were examined for lesions so the study is relevant. Key Study Sponsor Indicator: 

### Reference - Reproductive Toxicity Reference: Schaefer, G.J. 1994. 13 Week Combined Subchronic Or al Toxicity and Neurotoxicity Study in Rats. International Research and Development Corporation, Mattawan, MI. Study No.:658-005. Submi tted to: Sandoz Agro, Inc. May 6, 1994. BASF RegDoc# 94/11896. 

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## Reproductive Toxicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Reproductive Toxicity Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 8710 Purity 92.6% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Reproductive Toxicity Route of Administration: Oral
Type of Exposure: In Food
Species: Rat

Mammalian Strain: Wistar

Gender: Both M/F

Number of Animals per Dose: 50

Dose: 0, 100, 500, and 2000 ppm
Year Study Performed: 1989
Method/Guideline Followed: OECD 416

GLP: Yes
Exposure Period:
Frequency of Treatment: continuous
Post-Exposure Period: Method/Guideline and Test Condition Remarks: The study was performed according to OECD 416 "Two- Generation Reproduction Toxicity." The TS was administered in the diet to groups of 25 male and 25 female sexually immature Wistar rats (F0 parental g eneration) at the following doses: 0, 100, 500, and 2000 ppm. After 70 days of treatment, F0 animals were mated to produce the F1 generation. Groups of 25 male and 25 females were selected from the F1 pups as the F1 pa rental generation and were dosed with 0, 100, 500, or 2000 ppm post weaning for 101 days. This breeding program was rep eated to produce the F2 generation. The study was terminated with the 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintsacrifice of the F2 weanlings and F1 adult animals. Test diets containing the TS were offered continuously through out the study. The stability and homogenous distribution of the TS in the diet
were evaluated prior to study start. Analyses to confirm correct concentrations were performed periodically during the study. Food consumption of the F0 and F1 parents was deter mined weekly up to the mating period. After mating, female food consum ption was determined on days 0, 7, 14 and 21 of gestation and on days 1, 4, 7 and 14 post partum. In general, body weights of F0 and F1 parents were determined once weekly until the mating period. During gestation an d lactation F0/F1 females were weighed on days 0, 7, 14 and 21 of gestation and on days 1, 4, 7, 14 and 21 after birth. The F1 and F2 pups were weighed on the day of or day after birth and o n days 4, 7, 14 and 21 post partum.
The parents' and the pups' state of health was chec ked at least once each day, and parental animals were examined for their m ating and reproductive performances. Pups were sexed and evaluated as to h ealth, and pup viability was recorded. All pups were examined macr oscopically at necropsy. All F0 and F1 parental animals were assessed by gro ss pathology (including liver weight determination) and subjecte d to a histopathological examination, special attention being paid to the organs of the reproductive system. The mean TS intake during premating (F0 and F1 pare ntal animals) is shown in the following table. Dietary dose Test Substance Intake level (ppm) (mg/kg bw) 100 10 500 50 2000 150 Pre-Mating Exposure / Males: Pre-Mating Exposure / Females: 

### Test Results - Reproductive Toxicity Concentration (LOAEL/ LOAEC/ NOAEL/ NOAEC) : LOAEL/ LOAEC/ NOAEL/ NOAEC Population Value Description Value/Lower

Concentration Upper

Concentration Units

NOAEL Male

(Paternal) = 2000 ppm

NOAEL Female

(Maternal) = 2000 ppm

Results: The stability and homogeneity of the TS in the diet and target dietary concentrations were confirmed by analysis. F0 and F1 Parents: There were no effects due to treatment on any repro ductive 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintparameter. Clinical examinations - Food consumption was decreased at 2000 ppm in bot h F0 and F1 - Mean body weights were decreased by 6% in F0 male s and 8% in F1 males - Body weight gain was decreased by 12% in F0 males and 8% in F1 males Clinical pathology - The absolute liver weight was increased by 11% an d 19% in F0 males and females respectively and by 10% and 21% in F1 males and females respectively - The relative liver weight was increased by 17% an d 23% in F0 males and females respectively and by 20% and 21% in F1 males and females respectively Clear signs of general, systemic toxicity occurred in both parental generations at 2000 ppm. Toxicity was char acterized by decreased food consumption and increased liver weight in both sexe s and impaired body weight gain in males. At 500 ppm there was a v ery slight increase in liver weight (F0 males 4%, females 10%; F1 males 3%, females 4%). An increase in liver is most likely an adaptive response to the liver handling of the chemical and does not represent frank toxicity. Therefore, the slight inc rease in liver weight at 500 ppm is not considered an adverse effe ct. F1 and F2 Pups: There were no effects on pup survival. At 2000 ppm, pup body weight gains were reduced during lactation period f or both the F1 and F2 generations. There was no effect on pup body weights at 500 or 100 ppm. Results Remarks: In a 90-day oral subchronic study in rats, there we re no changes in the absolute or relative weights of ovaries or testes ( with epididymides) in rats examined at terminal sacrifice. In addition, no gro ss or microscopic lesions were noted in these reproductive organs. The highest dose tested was 3000 ppm in the diet (239 m g/kg bw/day). Blanset, D. 1996. A subchronic (3-month) toxicity s tudy of SAN 1289 H in the rat via dietary administration. Hunti ngdon Life Sciences, East Millstone, New Jersey, USA, unpublis hed. BASF RegDoc #96/5420. Conclusion: There were no adverse effects on reproductive param eters of the parental animals at any dose level. Clear signs of general, systemic toxicity occurred in both parental generations at 2000 ppm. The only treatment-related effect on pups was a decreased pu p weight gain during lactation at 2000 ppm. Therefore, the NOAEL for reproductive function is 2000 ppm (ca. 150 mg/kg bw /day). The NOAEL for parental systemic toxicity and developmen tal toxicity is 500 ppm (ca. 50 mg/kg bw/day). 

### Reliability/Data Quality - Reproductive Toxicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted reproduct ive toxicity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Reproductive Toxicity Reference: Sutter, P., et al. 1989. SAN 582 H: Two-generation reproduction study in the rat. RCC, Research & Consulting Compan y AG, Switzerland, unpublished. BASF RegDoc #90/11140. 

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## Developmental Toxicity/Teratogenicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Developmental Toxicity/Teratogenicity Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 8605 Purity 92% Sponsored Chemical Result Type: See Test Plan and Category Analysis



### Method - Developmental Toxicity/Teratogenicity Route of Administration: Oral
Type of Exposure: Gavage
Species: Rabbit

Mammalian Strain: New Zealand White

Gender: Female

Number of Animals per Dose: 20

Dose: 37.5, 75, and 150 mg/kg bw
Year Study Performed: 1988
Method/Guideline Followed: OECD 414

GLP: Yes
Exposure Period: 12 Days
Frequency of Treatment: daily, days 6-18 post insemination
Post-Exposure Period: Method/Guideline and Test Condition Remarks: The study was performed according to OECD 414 "Tera togenicity." The test substance was tested for its prenatal toxi city in New Zealand white rabbits. The TS was combined with equal amounts of HiSil and suspended in aqueous 0.5% carboxymethylcellulose. T wenty pregnant female rabbits/group were administered the TS by st omach tube at doses of 37.5, 75, and 150 mg/kg bw on days 6-18 po st insemination (p.i.). A dose volume of 10 mL/kg bw was used. The control group, consisting of 20 does, was dosed with an amount of HiSil in carboxymethylcellulose equal to that given in the h igh dose group. Analytical verification of the stability and homoge neity of 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintdimethenamid in carboxymethylcellulose were determined and verifica tion of test concentrations was performed three times during the current study. Food consumption and body weights of the animals we re recorded regularly throughout the study period. The state of health of the animals was checked at least once each day. All females were sacrificed on day 29 p.i.. The num ber of corpora lutea were determined and the number and distribution of implantation sites were classified. The fetuses were dissected from the ute rus, sexed, weighed and further investigated for any external, soft tis sue and skeletal findings. 

### Test Results - Developmental Toxicity/Teratogenicity Concentration (LOAEL/ LOAEC/ NOAEL/ NOAEC) : LOAEL/ LOAEC/ NOAEL/ NOAEC Population Value Description Value/Lower

Concentration Upper

Concentration Units

NOAEL Female

(Maternal) = 37.5 mg/kg bw LOAEC Fetal = 75 mg/kg bw

Results Remarks: Analytical determinations demonstrated that the TS concentrations were acceptably close to the target levels. In the 150 mg/kg bw dose, two animals aborted and t his was considered a treatment-related effect. Clinical signs considered related to treatment were localized alopecia at the high dose and reduce d feces at the mid and high doses. Food consumption was reduced by 24% in high dose an imals. During the treatment period, a body weight loss occurred in hi gh dose animals and body weight gain was reduced by 22% at the mid dose. There were no gross pathological findings which wer e related to treatment. There were no treatment-related effects in implanta tion, live litter size, fetal sex ratio or fetal body weight. Likewise, there were no effects on external, soft tissue or skeleta l variations or malformations. Conclusion: The TS produced clear signs of maternal toxicity at 150 mg/kg bw
as evidenced by reduced food consumption, a body weigh t loss and clinical signs. Maternal toxicity, though less severe, was a lso observed at the mid dose including a reduced body weight gain and clini cal signs. Two animals aborted at the high dose, but especially in rabbits, a low incidence of abortions at the high dose must be see n in connection with clear maternal toxicity. For this prenatal toxicity study in New Zealand Whi te rabbits, the NOAEL for maternal toxicity was 37.5 mg/kg bw, and the developmental toxicity NOAEL was 75 mg/kg bw. 

### Reliability/Data Quality - Developmental Toxicity/Teratogenicity Reliability: 1 - Valid Without Restrictions 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintReliability Remarks: GLP study performed according to accepted teratogen icity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Developmental Toxicity/Teratogenicity Reference: Hoberman, A. 1988. Developmental toxicity (embryo/f etal toxicity and teratogenic potential) study of SAN 582 H admin istered orally (stomach tube) to New Zealand white rabbits. ARGUS Research Laboratories, Horsham, Pennsylvania, USA, unpublish ed. BASF RegDoc #88/11376. 

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## Developmental Toxicity/Teratogenicity
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Developmental Toxicity/Teratogenicity Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P, SAN 1289-H Technical CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1%, S-dimethenamid; 96.3 total dimethenam id Sponsored Chemical Result Type: See Test Plan and Category Analysis



### Method - Developmental Toxicity/Teratogenicity Route of Administration: Oral
Type of Exposure: Gavage
Species: Rat

Mammalian Strain: Sprague-Dawley

Gender: Female

Number of Animals per Dose: 25

Dose: 25, 150, and 300 mg/kg bw
Year Study Performed: 1996
Method/Guideline Followed: Other

GLP: Yes
Exposure Period: 9 Days
Frequency of Treatment: daily, days 6-15 post coitum
Post-Exposure Period: Method/Guideline and Test Condition Remarks: The study was performed according to U.S. EPA FIFRA , Subdivision F, Paragraph 83-3. The TS was administered to 25 pregnant female rats per group by stomach tube at dosages of 25, 150, and 300 mg/kg b w on post coitum (p.c.) days 6-15. The TS was suspended in 0.5% aque ous carboxymethylcellulose after first adhering the TS to HiSil 233 as the carrier. A standard dose volume of 10 mL/kg bw was used. The control group, consisting of 25 dams, was dosed wit h the vehicle only. Analytical verification of stability and homogeneit y of the TS in 0.5% carboxymethylcellulose were determined prior to the study start. 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintVerification of test concentrations was performed t wice during the study. Food consumption and body weights of the animals we re recorded regularly throughout the study period. The state of health of the animals was checked twice each day. On p.c. day 20, all females were sacrificed and ass essed by gross pathology (including weight determination of the li ver). The number of corpora lutea were determined and the number and distribution of implantation sites was classified. The fetuses were removed from the uterus, sexed, weighed and investigated for any external findings. Approximately one half of the fetuses wer e examined for soft tissue findings and one half were examined for skeletal findings. 

### Test Results - Developmental Toxicity/Teratogenicity Concentration (LOAEL/ LOAEC/ NOAEL/ NOAEC) : LOAEL/ LOAEC/ NOAEL/ NOAEC Population Value Description Value/Lower

Concentration Upper

Concentration Units

NOAEL Female

(Maternal) = 25 mg/kg bw/day NOAEL Fetal = 25 mg/kg bw/day

Results Remarks: Analytical determinations demonstrated that TS conc entrations were acceptably close to the target level. - No mortalities, abortions, or premature deliverie s occurred during the study. - The 300 mg/kg group had increased incidences of e xcess lacrimation, piloerection, excess salivation, decreased motor ac tivity, orange substance on fur, swollen ocular membrane, ptosis, dark pink skin, urinestained abdominal fur and coldness to touch. - There were no signs of clinical toxicity related to treatment observed in mid or low dose animals. BODY WEIGHT & FOOD CONSUMPTION - A statistically significant reduction in feed con sumption occurred at all dose levels during the treatment pe riod; however, absolute food consumption was considered inappropriate to evaluat e treatmentrelated effects due to the random variability of maternal b ody weight gain in the 25 mg/kg bw/day group. - The relative feed consumption (body weight is con sidered) was only statistically reduced at 25 mg/kg bw/day on p.c. da ys 6-9 and only slightly reduced on p.c. days 9-12 and 12-16 (this effect was not considered toxicologically relevant). - Absolute and relative feed consumption values wer e significantly reduced (p<=0.05 and p<=0.01) in the 150 and 300 mg /kg bw/day dosage groups for the entire gestation period after dosage was be gun (GDs 6-20) and in the 300 mg/kg bw/day group for the entire ge station period (GDs 0- 20). - Relative feed consumption was significantly incre ased (p <=0.05) in the 150 and 300 mg/kg bw/day dosage groups on GDs 16-20 (rebound phenomena) - Significant weight loss (p <=0.01) in the 300 mg/ kg bw/day dosage 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintgroup occurred on GDs 6-9 as compared with the cont rol group values - At 300 mg/kg bw/day, group mean body weights and weight gains
were statistically reduced during the entire dosing peri od (gestation days 6 through 15) compared with the control group - Body weight gains were reduced in the 25 and 150 mg/kg bw/day dosage groups when compared to control values on GD s 6-9 (the reduction in the 25 mg/kg bw/day group is most like ly associated with the reduction in feed consumption (p<0.05,0.01 ) during days 6- 9, 12-16 and 6-16) - There were statistically significant reductions i n body weights and weight gains in the 150 mg/kg bw/day dose (body weights on days 9 and 12; body weight gains, days 6-16) - For the 25 mg/kg bw/day group, there were no stat istically significant decreases in body weight at any weighin g interval during the study; however, the group means were numerically lower tha n the control - A significant (p<0.01) reduction in the 25 mg/kg bw/day group occurred when compared to the control during the dosing peri od, this is probably associated with the reduction in feed consumption ( p<0.05,0.01) during days 6-9, 12-16 and 6-16. ORGAN WEIGHTS - Relative liver weights were increased (p <=0.01) at 300 mg/kg bw/day (8%); there were no necropsy observations considere d related to treatment. - Dose-dependent but not statistically significant tendencies for increased absolute liver weight (approx. 4.0%) and reduced te rminal body weight in the 300 mg/kg bw/day. REPRODUCTIVE PARAMETERS - There were no treatment-related effects on pre- o r postimplantation loss, the number of resorptions or number of viable fetus es, or on the sex distribution of fetuses. FETAL BODY WEIGHTS - Mean fetal weight was slightly (non-statistically ) reduced at 300 and 150 mg/kg bw/day (3 and 2%, respectively); these were considered biologically important as they were associated with the increase d incidences of reversible delays in ossification in these groups SKELETAL & VISCERAL ABNORMALITIES - No treatment-related findings occurred in relatio n to external, soft tissue or skeletal malformations. - Distended ureters were seen in seven high dose fe tuses in three litters compared to three control group fetuses in two litt ers. Because the litter incidence did not differ significantly from control , this increase was not considered treatment-related. - At 300 and 150 mg/kg bw/day there was a statistic ally significant increase in the incidence of two retarded ossifications, ste rnal centra and pelvic pubis. Further evaluation of the delayed ossificati ons indicated that these differences were spurious, primarily due to unusual ly low control values, and not related to treatment. The report states tha t these variations are generally considered to be reversible delays in dev elopment associated with reduced fetal body weights and resolving with continued growth - The total numbers of fetuses with any identified alterations were 13(3.5%), 12(3.2%), 20(6.4%, p<=0.05), and 31(7.7%, p<=0.01) and the average percentages of fetuses with any alterat ions were 3.4, 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrint3.2, 4.5 and 7.5% in the vehicle control, 25, 150 a nd 300 mg/kg bw/day dosage groups, respectively. Conclusion: Administration of the TS to pregnant Sprague-Dawley rats during organogenesis produced distinct signs of maternal t oxicity at the high dose of 300 mg/kg bw as evidenced by initial b ody weight loss, subsequent reduced maternal body weight gain, clini cal observations and increased liver weight. A reduced maternal body weight gain also occurred at 150 mg/kg bw. Slight fetal weight decreases were observed at 150 and 300 mg/kg bw. The only differen ces noted from control at 25 mg/kg bw were a slight and transient decrease in maternal body weight gain and food consumption duri ng the first three days of treatment. These differences were not considered to be of toxicological significance. For this study, the NOAEL for maternal toxicity is 25 mg/kg bw/day, based on a decrease in body weight/gain and feed consumption at 150 mg/kg bw/day (these effects plus clinical signs at 300 mg /kg bw/day). The NOAEL for developmental toxicity is also 25 mg/kg b w/day, based on an increased incidence in incomplete ossification o f the second sternal centra and/or pelvic pubis at 150 and 300 m g/kg bw/day. These variations were considered to possibly relate to a delay in fetal maturity related to maternal effects at the 2 higher doses (slightly smaller fetuses and decreases in maternal body weight and maternal body weight gains). 

### Reliability/Data Quality - Developmental Toxicity/Teratogenicity Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed according to accepted developme ntal toxicity testing guidelines. Key Study Sponsor Indicator: 

### Reference - Developmental Toxicity/Teratogenicity Reference: York, R. 1996. Oral (gavage) developmental toxicity study of SAN 1289 H in rats. ARGUS Research Laboratories, Horsha m, Pennsylvania, USA, unpublished. BASF RegDoc #97/5274. 

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## Pharmacokinetics and Metabolism
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Pharmacokinetics And Metabolism Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: [3-Thienyl-14C] Dimethenamid, racemic. The radiochemical purity was > 99% and the specific activity was 157 ìCi/mg. Sponsored Chemical Result Type: See Test Plan and Category Analysis



### Method - Pharmacokinetics And Metabolism Route of Administration: Other

Other Route of Administration: oral gavage or intravaneous injection
Species: Rat

Mammalian Strain:

Gender: Both M/F
Number of Animals per Dose:
Dose: Group 1: Oral dose of 10 mg/kg bw Group 2: IV dose of 10 mg/kg bw Group 3: Oral dose of 1000 mg/kg bw Group 4: Oral dose of unlabeled TS for 14 days at 1 0 mg/kg bw followed with a 14C oral dose of 10 mg/kg bw Group 5: Rats were bile duct cannulated and receive d an oral dose of 10 mg/kg bw Year Study Performed: 1992
Method/Guideline Followed: Other

GLP: Yes
Exposure Period: 168 Hours
Frequency of Treatment: Body Fluids Sampled:
Tissues Sampled:

Excretion Routes: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintMethod/Guideline and Test Condition Remarks: The TS was administered to five groups: Group 1: Oral dose of 10 mg/kg bw Group 2: IV dose of 10 mg/kg bw Group 3: Oral dose of 1000 mg/kg bw Group 4: Oral dose of unlabeled TS for 14 days at 1 0 mg/kg bw followed with a 14C oral dose of 10 mg/kg bw Group 5: Rats were bile duct cannulated and receive d an oral dose of 10 mg/kg bw Groups 1-4 had 6 rats/sex/dose while group 5 consisted of 3 rats/sex/dose. Excreta from each group and bile from group 5 were collected periodically until sacrifice at 168 hours. Additional rat experiments, set up to collect blood and tissue samples at 1, 4, 24, 72 and 168 hours, were set up with 2 dose groups (3/sex/group) exposed to either 10 or 1000 mg/kg bw. 

### Test Results - Pharmacokinetics And Metabolism Metabolites Excreted:

Metabolites in Tissues: Metabolites in Body Fluids:
Results Remarks: The TS was well-absorbed by oral administration: adding the radioactivity in the carcass the total oral absorption was 94.5% and 92.8% in males and females, respectively. The TS was mainly excreted i n the bile (75-82%) with 2-4% in the feces and 8-12% in the urine. Excretion via the bile was very rapid; i n 7 hours 45-64% of the oral dose was excreted in the bile. By 168 hours after treatment, an average of 9 0% of the administered dose was eliminated by all routes. There were some differences in the excretion patter n between the dose levels, with urinary excretion increasing from the low dose (35-47% of the dose) t o the high dose (62-63% of the dose) and fecal excretion decreasing from the low dose (48-58%) to the high dose (26-30%). These data indicate that biliary excretion might be saturated for the high dose group resulting in more radioactivity eliminat ed via the kidney. The blood radioactivity level decreased slowly over the experimental period of 168 hours and was primarily associated with red blood cells. The maximum blood radioactivity (0.05 and 0.1 ìg test material/g blood for males and females, respectivel y) was reached at about 72 hours after a single oral l ow -dose administration. For the high oral dose, the maximum blood radioactivity was also reached at 72 hours, but did not significantly decrease between 7 2- 168 hours. Overall, tissue radioactivities were comparable between the sexes and residue levels decreased steadily over time and were small by 168 hours.

There is excellent evidence that the metabolic profile of dimethenamid-P would be the same in rat as the racemic dimethenamid. Toxicology studies conducted with dimethenamid-P resulted in similar conclusions and end-points as the racemic dimethenamid. 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintConclusion: There was no significant difference in absorption, distribution, elimination, and metabolism of dimethenamid between the sexes or between exposure routes. There was also no significant difference percent absorption between t he low dose and the high dose, or between single and multiple doses. These data showed that dimethenamid and its metabolites had no tendency to bioaccumulat e in animal systems. 

### Reliability/Data Quality - Pharmacokinetics And Metabolis m Reliability: 1 - Valid Without Restrictions
Reliability Remarks: The study was performed according to GLP and standa rd test guidelines. Key Study Sponsor Indicator: 

### Reference - Pharmacokinetics And Metabolism Reference: Vollmin, S. 1992. Absorption, distribution, metabolism and excretion of (14C) SAN 582 in rat after single and multiple doses (addendum to: SAN 5 82 H metabolism in rat; BASF RegDoc# 89/11026). SANDOZ Agro, Ltd., Basle, CH. BASF RegDoc# 92/12428. 

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## Skin Irritation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Skin Irritation Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Skin Irritation Species: Rabbit

Mammalian Strain: New Zealand White
Type of Coverage: Semi-Occlusive
Preparation of Test Site:
Gender:
Number of Animals per Dose: 6
Amount/Concentration Applied: Approximately 0.5 mL of undiluted TS
Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 81-5

GLP: Yes
Exposure Period: 4 Hours
Total Volume applied and Units: 0.5 ml
Control Group Type:

Vehicle Used:

Vehicle Name:

Vehicle Amount and Units: Post-Exposure Period:
Grading Scale: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintMethod/Guideline and Test Condition Remarks: The study was performed according to U.S. EPA FIFRA , Subdivision F, Paragraph 81-5. Approximately 0.5 mL of undiluted TS was tested for skin irritation potential in 6 New Zealand White rabbits. The test site was covered with a 6 cm2 gauze patch and secured with a semiocclusive dressing. The duration of the test wa s 4 hours, at the end of the exposure the test site w as washed with 0.9% saline. Skin irritation was scored at 30 min, 24, 48, and 72 h after removal of the TS

. 

### Test Results - Skin Irritation Grade:
Primary Irritation Index:
Lesions:
Erythema:

Edema:

Results Remarks: Three animals exhibited slight erythema with no ede ma and two animals exhibited very slight (barely perceptible) erythema with no edema. These animals were free of all dermal irritation by 72 h after removal of the TS. SKIN IRRITATION VALUES (ERYTHEMA / EDEMA) Animal# Time After Patch Removal Mean Scores 30 24h 48h 72h 1 0/0 1/0 1/0 0/0 0.5 2 1/0 1/0 1/0 0/0 0.8 3 1/0 2/0 2/0 0/0 1.3 4 0/0 0/0 0/0 0/0 0.0 5 1/0 2/0 1/0 0/0 1.0 6 1/0 2/0 1/0 0/0 1.0 Interpretation of Results: Not Irritating

Conclusion: According to EU criteria, the TS was not a skin irritant on the New Zealand White rabbit following a 4 h exposure to intact skin. 

### Reliability/Data Quality - Skin Irritation Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted skin irritation/corrosion testing guidelines. Key Study Sponsor Indicator: 

### Reference - Skin Irritation Reference: Blaszcak, D. 1996. Primary dermal irritation study with SAN 1289 H technical in rabbits. Huntingdon Li fe Sciences, East Millstone, New Jersey, USA unpublished. BASF RefDoc #96/5406. 

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## Skin Irritation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Skin Irritation Test Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: The test substance (TS) was T01184 (SAN 582-Stufe C -4 "Via Keto-Enol). The test substance was the racemic C4, CAS No. 87676-01-1, 3-thiophenamine,N-(2-methox y1-methylethyl)-2,4-dimethylSponsored Chemical Result Type: Measured


### Method - Skin Irritation Species: Other
Other Species: Rat

Mammalian Strain: Other

Other Strain: Wistar:Crl:(W1)BR, a Han/Wistar rat
Type of Coverage: Semi-Occlusive
Preparation of Test Site: Shaved

Gender: Both M/F
Number of Animals per Dose: Amount/Concentration Applied: 4153 mg/kg bw
Year Study Performed: 1988
Method/Guideline Followed: Other

GLP: No
Exposure Period: 24 Hours
Total Volume applied and Units: 4 ml
Control Group Type:

Vehicle Used:

Vehicle Name:

Vehicle Amount and Units: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintPost-Exposure Period: 14 Days
Grading Scale:

Method/Guideline and Test Condition Remarks: The study was performed according to OECD Test Guideline 402 from February 1987 and EPA Guidelines 81/2 and Good Laboratory Practices. Study period: Nov. 29, 1988 - Dec. 13, 1988 TEST ANIMALS: - Species: rat - Strain: Wistar:Crl:(W1)BR, a Han/Wistar rat - Age: 8-14 weeks old - Male body weight: 295-320 g - Female body weight: 225-240 g - Feed: KLIBA N0. 24-343-4, provided ad libitum before and after dosing - Water: provided ad libitum - Identified with cage card - Housed individually in Macrolon cages with sterilized wood chips - All animals were healthy at the beginning of the test TEST METHODS: DOSING: - The animals were acclimated for a period of 7 day s prior to dosing - The animals' backs were clipped free of hair and the TS was evenly applied to a skin area of 16 cm^2 (corresponding to approximately 10% of the body surface) - The dose was 4153 mg/kg bw - The test site was covered with 8-layer gauze - The duration of the exposure was 24 h - At the end of the 24 hour exposure, the dressings were removed, excess compound wiped off and the ski n was gently washed with water OBSERVATIONS: - On the day of application animals were observed f or mortality during the first 4 hours, and hourly for up to 7 hours - Daily observations of mortality were performed daily for the following 13 days -The nature, severity, approximate time of onset an d duration of symptoms were observed at the onset of the test and after 1, 2, 3, 4 and 24 hour postapplication and also daily for the remaining 13 days - Bodyweights were recorded on days 1, 2, 3, 8 and 15 NECROSPY: - All surviving animals were euthanized with CO2, necropsied, and examined for gross abnormalities 

### Test Results - Skin Irritation Grade:
Primary Irritation Index:
Lesions:
Erythema:

Edema:

Results Remarks: This is a dermal acute toxicity study. No irritatio n was observed at the tested dose of 4153 mg/kg. 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintInterpretation of Results: Not Irritating

Conclusion: No irritation of the treated skin area was observed



### Reliability/Data Quality - Skin Irritation Reliability: 4 - Not Assignable
Reliability Remarks: This is a secondary finding from a acute dermal toxicity test. Key Study Sponsor Indicator: 

### Reference - Skin Irritation Reference: 

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## Eye Irritation
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Eye Irritation Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1%
Sponsored Chemical Result Type: See Test Plan and Category Analysis 

### Method - Eye Irritation Species: Rabbit

Mammalian Strain: New Zealand White

Gender:
Number of Animals per Dose: 6
Amount/Concentration Applied: 0.1 mL of undiluted TS
Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 81-4

GLP: Yes
Exposure Period: 72 Hours
Total Volume applied and Units: 0.1 ml
Control Group Type:

Vehicle Used:

Vehicle Name:

Vehicle Amount and Units: Post-Exposure Period:
Grading Scale:

Tool: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintMethod/Guideline and Test Condition Remarks: The study was performed according to U.S. EPA FIFRA , Subdivision F, Paragraph 81-4. The TS was tested for eye irritation in 6 New Zeala nd White rabbits. A volume of 0.1 mL of undiluted TS w as applied once to one eye of each rabbit; the test si te was not washed out. Readings of the eyes were carri ed out 1, 24, 48, and 72 h after the application of th e TS. 

### Test Results - Eye Irritation Overall Grading Score:

Overall Irritation Score: Primary Irritation Index:
Lesions:

Cornea:

Iris:
Conjunctivae (Chemosis): Conjunctivae (Redness):
Results Remarks: All six rabbits exhibited slight conjunctival redne ss and/or chemosis and moderate to severe conjunctival discharge at 1 h after exposure. The discharge and chemosis were not observed at 24 h after treatment. Four animals were free of conjunctival redness by 24 h and the remaining two animals were free by 48 h. There were no corneal or iridial effects observed.

MEAN EYE IRRITATION SCORES Animal Corneal Iris Conjunctival Conjunctiva Number Opacity Redness Swelling 1 0 0 0 0 2 0 0 0 0 3 0 0 0.33 0 4 0 0 0.33 0 5 0 0 0 0 6 0 0 0 0 Interpretation of Results: Not Irritating

Conclusion: The TS is not considered an eye irritant by EU criteria. 

### Reliability/Data Quality - Eye Irritation Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted eye irritation/corrosion testing guidelines. Key Study Sponsor Indicator: 

### Reference - Eye Irritation Reference: Blaszcak, D. 1996. Primary eye irritation study wit h SAN 1289 H technical in rabbits. Huntingdon Life 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintSciences, East Milstone, New Jersey, USA unpublished. BASF RegDoc #96/5396. 

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## Skin Sensitization
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethyl

### Test Substance - Skin Sensitization Test Substance: (163515-14-8) dimethenamid

Test Substance Purity/Composition and Other Test Substance Comments: Name: dimethenamid-P CAS#: 163515-14-8 Batch No.: 6663-50-1 Purity 91.1% Sponsored Chemical Result Type: See Test Plan and Category Analysis


### Method - Skin Sensitization Test Type: In Vivo
Study Type: Buehler Test
Species: Guinea pig

Mammalian Strain: Dunkin-Hartley

Route of Induction: Epicutaneous, Occlusive
Route of Challenage Exposure: Dermal

Gender: Both M/F
Number of Animals per Dose: 20

Concentration: 0.3 mL of the undiluted TS
Year Study Performed: 1996
Method/Guideline Followed: EPA OPP 81-6

GLP: Yes
Exposure Period: 6 Hours
Induction Frequency of Treatment: once per week for three weeks
Challenge Exposure Period: 6 Hours
Challenge Frequency of Treatment: ONCE
Total Volume applied and Units: Control Group Type: 

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2/14/2012 http://iaspub.epa.gov/hpvis/ServSubmissionPrintVehicle Used:

Vehicle Name:

Vehicle Amount and Units:
Positive Control Substance: The sensitivity of the test method was tested sever al times a year with a positive control agent, dinitrochlorobenzene. Post-Exposure Period:
Negative Control Substance: Method/Guideline and Test Condition Remarks: The study was performed according to U.S. EPA FIFRA , Subdivision F, Paragraph 81-6. The TS was evaluated for its skin sensitizing potential using the Buehler test. For induction, 20 Dunkin-Hartley guinea pigs (10/sex) received three cutaneous applications of the TS for 6 hours under occlusive dressing. Treatments were once per week f or three weeks with 0.3 mL of the undiluted TS. Ten untreated animals were used in a control group. A cutaneous challenge application of 0.5 mL of undiluted TS preparation was carried out 14 days after the third induction on a non-treated area usi ng the same procedure as that for induction. The contr ol animals were also treated during the challenge phra se to differentiate dermal irritation scores from sensitization reactions. Readings for dermal change s were performed 24 and 48 hours after patch removal. The sensitivity of the test method was tested sever al times a year with a positive control agent, dinitrochlorobenzene. 

### Test Results - Skin Sensitization Measurement Period and Units:
Percent Sensitized Test Substance:
Percent Sensitized Positive Control:
Percent Sensitized Negative Control:
Sensitization Score:

Results Remarks: Irritation increased in incidence and severity duri ng the induction phase. At challenge, 17/20 test animals exhibited dermal responses compared to 0/10 in the controls. Results of Buehler Sensitization Test Challenge Control Group: 0/10 Test Group: 17/20 x/y: total number of animals with positive reaction s at 24 and/or 48 h/number of animals tested Interpretation of Results: Sensitizing

Conclusion: The TS is considered to be a skin sensitizer in the Buehler test. 

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### Reliability/Data Quality - Skin Sensitization Reliability: 1 - Valid Without Restrictions
Reliability Remarks: GLP study performed to accepted skin sensitization testing guidelines. Key Study Sponsor Indicator: 

### Reference - Skin Sensitization Reference: Blaszcak, D. 1996. Closed-patch repeated insult dermal sensitization study with SAN 1289 H technica l in guinea pigs. Huntingdon Life Sciences, East Millstone, New Jersey, USA unpublished. BASF RefDoc #96/11088. 

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## Use Information
CAS Number : 170373-17-8
Sponsored Chemical Name : 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2 ,4-dimethylTest Substance: (170373-17-8) 3-Thiophenamine, N-[(1S)-2-methoxy-1-methylethyl]-2,4-dimethylTest Substance Purity/Composition and Other Test Substance Comments: Reference:
Description:

Use Pattern: C4 is a site-limited closed-system intermediate use d in the manufacture of the herbicide dimethenamid. I t is produced at only one site in the U.S. The production volume is between 5 and 15 million pound s per year; hence C4 is an HPV chemical. Processing occurs in closed systems with no routine exposure possible except for QC sampling. Samples are handle d in laboratory settings according to a chemical hygiene plan and using engineering controls such as fume hoods. C4 is a relatively non-volatile liquid, so the probability of inhalation exposure is quite low and air monitoring is not warranted. Dermal exposures that might be associated with sampling th e materials (and waste streams) during the manufacturing process are prevented through worker training regarding proper health and safety procedures, the use of proper personal protective equipment (PPE), and engineering controls. The vast majority of C4 is converted to the desired product and the inventory of C4 on site at any one time is small, i.e., less than 250,000 pounds in a single storage tank. Any small amount of C4 that might end up in the final product is regulated by t he active ingredient registration. All organic and aqueous waste streams from the processes that use C 4 are incinerated or disposed of via an on-site deep well. Potential environmental exposures are limited to spills onsite, which are handled in accordance with recognized emergency response and safety procedures to minimize potential exposures. The use of secondary containment at the manufacturing site further limits potential environmental release. In summary, C4 poses a minimal exposure threat to workers or the environment.



### http://iaspub.epa.gov/hpvis/ServSubmissionPrint Last updated on Tuesday, February 14, 2012 

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