Dimethenamid

Dimethenamid[1][2]
Names
	IUPAC name (RS)-2-Chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide
	Other names Frontier Herbicide; Dimethenamid-P ((S)-isomer)
Identifiers
CAS Number	87674-68-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:81789 ;
ChemSpider	82842 ;
ECHA InfoCard	100.121.887
KEGG	C18499 ;
PubChem CID	91744;
RTECS number	AB5444200;
UNII	8504Z6C4XZ ;
CompTox Dashboard (EPA)	DTXSID4032376 ;
	InChI InChI=1S/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3 Key: JLYFCTQDENRSOL-UHFFFAOYSA-N ; InChI=1/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3 Key: JLYFCTQDENRSOL-UHFFFAOYAR;
	SMILES CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C; ClCC(=O)N(c1c(scc1C)C)C(COC)C;
Properties
Chemical formula	C12H18ClNO2S
Molar mass	275.79 g/mol
Appearance	Tan to brown liquid
Density	1.141 g/cm3
Hazards
Main hazards	Xn (harmful)
Safety data sheet	MSDS from BASF
R-phrases (outdated)	R22
Flash point	151 °C (304 °F; 424 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Dimethenamid is a widely used herbicide. In 2001, about 7 million pounds of dimethenamid were used in the United States.[3] Dimethenamid is registered for control of annual grasses, certain annual broadleaf weeds and sedges in field corn, seed corn, popcorn and soybeans. Supplemental labeling also allows use on sweet corn, grain sorghum, dry beans and peanuts. In registering dimethinamide (SAN 582H/Frontier), EPA concluded that the primary means of dissipation of dimethenamid applied to the soil surface is photolysis, whereas below the surface loss was due largely to microbial metabolism. The herbicide was found to undergo anaerobic microbial degradation under denitrifying, iron-reducing, sulfate-reducing, or methanogenic conditions.[4] In that study, more than half of the herbicide carbon (based on 14C-labeling) added was found to be incorporated irreversibly into soil-bound residue.

References

Dimethenamid at Sigma-Aldrich
Material Safety Data Sheet from BASF
2000-2001 Pesticide Market Estimates Archived 2009-02-07 at the Wayback Machine, U.S. Environmental Protection Agency
Crawford, J.J.; Sims, G. K.; Simmons, F. W.; Wax, L. M.; Freedman, D. L. (2002). "Dissipation of the herbicide (14C) Dimethenamid under anaerobic aquatic conditions in flooded soil microcosms". J. Agric. Food Chem. 50 (6): 61483–1491. doi:10.1021/jf010612i. PMID 11879025.

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[1] Dimethenamid at Sigma-Aldrich

[2] Material Safety Data Sheet from BASF

[3] 2000-2001 Pesticide Market Estimates Archived 2009-02-07 at the Wayback Machine, U.S. Environmental Protection Agency

[4] Crawford, J.J.; Sims, G. K.; Simmons, F. W.; Wax, L. M.; Freedman, D. L. (2002). "Dissipation of the herbicide (14C) Dimethenamid under anaerobic aquatic conditions in flooded soil microcosms". J. Agric. Food Chem. 50 (6): 61483–1491. doi:10.1021/jf010612i. PMID 11879025.