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| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 432074581 | verifiedrevid = 432074581
| Reference=<ref> at ]</ref><ref> from ]</ref> | Reference=<ref> at ]</ref><ref>{{Dead link|date=November 2019 |bot=InternetArchiveBot |fix-attempted=yes }} from ]</ref>
| ImageFile=Dimethenamid.png | ImageFile=Dimethenamid.png
| ImageSize=180px | ImageSize=180px
| IUPACName=(''RS'')-2-Chloro-''N''-(2,4-dimethyl-3-thienyl)-''N''-(2-methoxy-1-methylethyl)acetamide | IUPACName=(''RS'')-2-Chloro-''N''-(2,4-dimethyl-3-thienyl)-''N''-(2-methoxy-1-methylethyl)acetamide
| OtherNames=Frontier Herbicide<br>Dimethenamid-P ((''S'')-isomer)<ref> at AlanWood.net</ref> | OtherNames=Frontier Herbicide<br>Dimethenamid-P ((''S'')-isomer)
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 82842 | ChemSpiderID = 82842
| EINECS = 618-045-5
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 81789 | ChEBI = 81789
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| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|??}}
| CASNo=87674-68-8 | CASNo=87674-68-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8504Z6C4XZ
| PubChem=91744 | PubChem=91744
| SMILES=CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C | SMILES=CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C
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| FlashPtC = 151 | FlashPtC = 151
| AutoignitionPtC = | AutoignitionPtC =
| RPhrases = {{R22}} | GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|317|332|410|411}}
| PPhrases = {{P-phrases|261|264|270|271|272|273|280|301+312|302+352|304+312|304+340|312|321|330|333+313|363|391|501}}
}} }}
}} }}


'''Dimethenamid''' is a widely used ]. In 2001, about 7 million pounds of dimethenamid were used in the United States.<ref> {{webarchive|url=https://web.archive.org/web/20090207095013/http://www.epa.gov/oppbead1/pestsales/01pestsales/usage2001_2.htm |date=2009-02-07 }}, ]</ref> 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, '''Dimethenamid''' is a widely used ] belonging to the chloroacetamide class (group 15). Group 15 herbicides inhibit synthesis of certain long-chain fatty acids, thus reducing plant growth.<ref>Lamberth, C. (2016). Chloroacetamide Herbicides. In Bioactive Carboxylic Compound Classes (eds C. Lamberth and J. Dinges). https://doi.org/10.1002/9783527693931.ch21</ref> In 2001, about {{convert|7|e6lb|t}} of dimethenamid were used in the United States.<ref> {{webarchive|url=https://web.archive.org/web/20090207095013/http://www.epa.gov/oppbead1/pestsales/01pestsales/usage2001_2.htm |date=2009-02-07 }}, ]</ref> 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 ], 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.<ref>{{cite journal|last=Crawford|first=J.J. |author2=Sims, G. K. |author3=Simmons, F. W. |author4=Wax, L. M. |author5=Freedman, D. L. |title=Dissipation of the herbicide (14C) Dimethenamid under anaerobic aquatic conditions in flooded soil microcosms |journal=] |year=2002|volume=50|issue=6|pages=61483–1491 |doi=10.1021/jf010612i|pmid=11879025 }}</ref> In that study, more than half of the herbicide carbon (based on <sup>14</sup>C-labeling) added was found to be incorporated irreversibly into soil-bound residue.
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.<ref>{{cite journal|last=Crawford|first=J.J. |author2=Sims, G. K. |author3=Simmons, F. W. |author4=Wax, L. M. |author5=Freedman, D. L. |title=Dissipation of the herbicide (14C) Dimethenamid under anaerobic aquatic conditions in flooded soil microcosms |url=http://pubs.acs.org/doi/abs/10.1021/jf010612i |journal=] |year=2002|volume=50|issue=6|pages=61483–1491 |accessdate=2015-01-18 |doi=10.1021/jf010612i}}</ref> 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== ==References==
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{{organic-compound-stub}}

Latest revision as of 02:20, 5 June 2024

Dimethenamid
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)
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
  • InChI=1S/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3Key: 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,5-6H2,1-4H3Key: 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/cm
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. In 2001, about 7 million pounds (3,200 t) of dimethenamid were used in the United States. 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. In that study, more than half of the herbicide carbon (based on C-labeling) added was found to be incorporated irreversibly into soil-bound residue.

References

  1. Dimethenamid at Sigma-Aldrich
  2. Material Safety Data Sheet 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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