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Dimethenamid





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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.

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

3D model (JSmol)

  • Interactive image
  • ChEBI
    ChemSpider
    ECHA InfoCard 100.121.887 Edit this at Wikidata
    EC Number
    • 618-045-5
    KEGG

    PubChem CID

    RTECS number
    • AB5444200
    UNII

    CompTox Dashboard (EPA)

    • 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

    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

    GHS07: Exclamation markGHS09: Environmental hazard

    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).

    ☒N verify (what is checkY☒N ?)

    Infobox references

    References

    edit
  • ^ 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.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Dimethenamid&oldid=1227328761"
     



    Last edited on 5 June 2024, at 02:20  





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    This page was last edited on 5 June 2024, at 02:20 (UTC).

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