| Revision as of 11:59, 1 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit | Latest revision as of 02:20, 5 June 2024 edit undoMfernflower (talk | contribs)Extended confirmed users7,847 editsNo edit summaryTags: Mobile edit Mobile web edit Advanced mobile edit | ||
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| {{chembox | {{chembox | ||
| | Verifiedfields = changed | |||
| ⚫ | |Reference=<ref> at ]</ref><ref> from ]</ref> | ||
| | verifiedrevid = 432074581 | |||
| ⚫ | |ImageFile=Dimethenamid.png | ||
| ⚫ | | Reference=<ref> at ]</ref><ref>{{Dead link|date=November 2019 |bot=InternetArchiveBot |fix-attempted=yes }} from ]</ref> | ||
| ⚫ | |ImageSize=180px | ||
| ⚫ | | ImageFile=Dimethenamid.png | ||
| ⚫ | |IUPACName=(''RS'')-2-Chloro-''N''-(2,4-dimethyl-3-thienyl)-''N''-(2-methoxy-1-methylethyl)acetamide | ||
| ⚫ | | ImageSize=180px | ||
| ⚫ | |OtherNames=Frontier Herbicide<br>Dimethenamid-P ((''S'')-isomer) |
||
| ⚫ | | IUPACName=(''RS'')-2-Chloro-''N''-(2,4-dimethyl-3-thienyl)-''N''-(2-methoxy-1-methylethyl)acetamide | ||
| ⚫ | | OtherNames=Frontier Herbicide<br>Dimethenamid-P ((''S'')-isomer) | ||
| |Section1={{Chembox Identifiers | |Section1={{Chembox Identifiers | ||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| | |
| ChemSpiderID = 82842 | ||
| | EINECS = 618-045-5 | |||
| | ChEBI_Ref = {{ebicite|changed|EBI}} | |||
| | ChEBI = 81789 | |||
| | 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 | | 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 | ||
| | InChIKey = JLYFCTQDENRSOL-UHFFFAOYAR | | InChIKey = JLYFCTQDENRSOL-UHFFFAOYAR | ||
| | SMILES1 = ClCC(=O)N(c1c(scc1C)C)C(COC)C | | SMILES1 = ClCC(=O)N(c1c(scc1C)C)C(COC)C | ||
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| | StdInChI = 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 | | StdInChI = 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 | ||
| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
| | StdInChIKey = JLYFCTQDENRSOL-UHFFFAOYSA-N | | StdInChIKey = JLYFCTQDENRSOL-UHFFFAOYSA-N | ||
| | CASNo_Ref = {{cascite|correct|??}} | |||
| | CASNo=87674-68-8 | | CASNo=87674-68-8 | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | |||
| ⚫ | | |
||
| | UNII = 8504Z6C4XZ | |||
| ⚫ | | |
||
| ⚫ | | PubChem=91744 | ||
| ⚫ | | |
||
| ⚫ | | SMILES=CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C | ||
| ⚫ | | RTECS = AB5444200 | ||
| | KEGG_Ref = {{keggcite|correct|kegg}} | |||
| | KEGG = C18499 | |||
| }} | }} | ||
| |Section2={{Chembox Properties | |Section2={{Chembox Properties | ||
| | |
| Formula=C<sub>12</sub>H<sub>18</sub>ClNO<sub>2</sub>S | ||
| | |
| MolarMass=275.79 g/mol | ||
| | |
| Appearance=Tan to brown liquid | ||
| | |
| Density=1.141 g/cm<sup>3</sup> | ||
| | |
| MeltingPt= | ||
| | |
| BoilingPt= | ||
| | |
| Solubility= | ||
| }} | }} | ||
| |Section3={{Chembox Hazards | |Section3={{Chembox Hazards | ||
| | |
| ExternalSDS = from ] | ||
| | |
| MainHazards='''Xn''' (harmful) | ||
| | FlashPtC = 151 | |||
| | FlashPt=151 °C | |||
| | AutoignitionPtC = | |||
| | Autoignition= | |||
| | |
| 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 ] 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. | |||
| '''Dimethenamid''' is a widely used ]. In 2001, about 7 million pounds of dimethenamid were used in the United States.<ref>, ]</ref> | |||
| ==References== | ==References== | ||
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Latest revision as of 02:20, 5 June 2024
 | |
| 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 
|
| EC Number |
|
| KEGG | |
| PubChem CID | |
| RTECS number |
|
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| 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 |  
|
| 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
| |
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
- Dimethenamid at Sigma-Aldrich
- Material Safety Data Sheet 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.