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
EC Number	618-045-5;
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
	Occupational safety and health (OHS/OSH):
Main hazards	Xn (harmful)
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H332, H410, H411
Precautionary statements	P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P321, P330, P333+P313, P363, P391, P501
Flash point	151 °C (304 °F; 424 K)
Safety data sheet (SDS)	MSDS from BASF
	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 belonging to the chloroacetamide class (group 15). Group 15 herbicides inhibit synthesis of certain long-chain fatty acids, thus reducing plant growth.^[3] In 2001, about 7 million pounds (3,200 t) of dimethenamid were used in the United States.^[4] 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.^[5] 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^{[permanent dead link]} from BASF
^ Lamberth, C. (2016). Chloroacetamide Herbicides. In Bioactive Carboxylic Compound Classes (eds C. Lamberth and J. Dinges). https://doi.org/10.1002/9783527693931.ch21
^ 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.

[1] Dimethenamid at Sigma-Aldrich

[2] Material Safety Data Sheet^{[permanent dead link]} from BASF

[3] Lamberth, C. (2016). Chloroacetamide Herbicides. In Bioactive Carboxylic Compound Classes (eds C. Lamberth and J. Dinges). https://doi.org/10.1002/9783527693931.ch21

[4] 2000-2001 Pesticide Market Estimates Archived 2009-02-07 at the Wayback Machine, U.S. Environmental Protection Agency

[5] 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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