Chemistry:Dimethenamid
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| Names | |
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| IUPAC name
(RS)-2-Chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide
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| Other names
Frontier Herbicide
Dimethenamid-P ((S)-isomer) | |
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| Properties | |
| 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 |
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| GHS Signal word | Warning |
| H302, H317, H332, H410, H411 | |
| P261, P264, P270, P271, P272, P273, P280, P301+312, P302+352, P304+312, P304+340, P312, P321, P330, P333+313, P363, P391, P501 | |
| 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   ?)
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| 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 reducing availability of ipids, proteins, and lignin for the 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[yes|permanent dead link|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 , 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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