Butamifos
{{Chembox
| ImageFile = Butamifos Structural Formula.svg
| ImageSize = 200px
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| Section1 = {{Chembox Identifiers
| CASNo = 36335-67-8
| EINECS = 609-231-7
| PubChem = 37419
| ChemSpiderID = 34329
| UNII = KHP91X76U4
| KEGG = C11022
| SMILES = CCC(C)NP(=S)(OCC)OC1=C(C=CC(=C1)C)[N+](=O)[O-]
| StdInChI=1S/C13H21N2O4PS/c1-5-11(4)14-20(21,18-6-2)19-13-9-10(3)7-8-12(13)15(16)17/h7-9,11H,5-6H2,1-4H3,(H,14,21)
| StdInChIKey = OEYOMNZEMCPTKN-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=13 | H=21 | N=2 | O=4 | P=1 | S=1
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| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|410}}
| PPhrases = {{P-phrases|264|270|273|301+317|330|391|501}}
| MainHazards =
| FlashPt =
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Butamifos is an herbicide that is used to control weeds.{{citation|surname1=Toshiyuki Katagi|periodical=Journal of Agricultural and Food Chemistry|title=Photochemistry of organophosphorus herbicide butamifos|volume=41|issue=3|at=pp. 496–501|issn=0021-8561|date=March 1993|language=German|doi=10.1021/jf00027a028
}}
Production
The production of butamifos is based on N-[chloro(ethoxy)phosphinothioyl]butan-2-amine and 5-methyl-2-nitrophenol and is described in the following reaction sequence:{{citation|surname1=Thomas A. Unger|periodical=Pesticide Synthesis Handbook|title=Butamifos|publisher=Elsevier|at=p. 376|isbn=978-0-8155-1401-5|date=1996|language=German|doi=10.1016/b978-081551401-5.50299-9|url={{GBurl|-9cHDi8OOO4C|page=376}}
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Properties
Butamifos is a chiral molecule. The technical product uses a mixture of the (R)- and (S)-isomers.{{PPDB|1682|Name=Butamifos|Abruf=2022-07-19}}
In a study, the level of pesticide contamination in soil and water of an agriculturally intensive area in Nepal was investigated. Endosulfan, Iprobefos, monocrotophos, mevinphos, and butamifos were detected in water samples, while cypermethrin, dichlorvos, and cyfluthrin were detected in soil samples. The increased concentration of butamifos in water may be due to higher water solubility and lower affinity for adsorption in soil.{{citation|surname1=Kafle, B. K., Pokhrel, B., Shrestha, S., Raut, R., Dahal, B. M.|periodical=International Journal of Geology, Earth & Environmental Sciences|title=Determination of pesticide residues in water and soil samples from Ansikhola watershed, Kavre, Nepal|volume=5|issue=2|at=pp. 119-127|date=2015|language=German|url=https://www.researchgate.net/publication/281430111
}}
Use
= Application and mode of action =
Butamifos is used on beans, turf and various vegetables. The active ingredient is a non-systemic, selective herbicide. Its effect is based on inhibition of microtubule formation. It also acts as an acetylcholinesterase inhibitor, making it moderately toxic to mammals.{{citation|surname1=Paranjape, Kalyani.|title=The pesticide encyclopedia|publisher=CABI|publication-place=Wallingford, Oxfordshire UK|at=p. 74|isbn=978-1-78064-014-3|date=2014|language=German|url={{GBurl|cnDHBgAAQBAJ|page=74}}}}
= Trade name =
= Registration =
No plant protection products containing butamifos are registered in the European Union or Switzerland.{{Cite web |title=European Commission Directorate-General for Health and Food Safety |url=https://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/active-substances/?event=as.details&as_id=682 }}