Dimethenamid

From WikiProjectMed
Jump to navigation Jump to search
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.121.887 Edit this at Wikidata
EC Number
  • 618-045-5
KEGG
RTECS number
  • AB5444200
UNII
  • 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 checkY
    Key: JLYFCTQDENRSOL-UHFFFAOYSA-N checkY
  • 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
  • CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C
  • ClCC(=O)N(c1c(scc1C)C)C(COC)C
Properties
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:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H317, H332, H410, H411
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).
☒N verify (what is checkY☒N ?)

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

  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.
Retrieved from "https://mdwiki.org/wiki/Dimethenamid"