Butamifos

Butamifos is an herbicide that is used to control weeds.^[2]

Butamifos

Identifiers
CAS Number	36335-67-8
3D model (JSmol)	Interactive image
ChemSpider	34329
ECHA InfoCard	100.126.299
EC Number	609-231-7
KEGG	C11022
PubChem CID	37419
UNII	KHP91X76U4
CompTox Dashboard (EPA)	DTXSID5058068
InChI InChI=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) Key: OEYOMNZEMCPTKN-UHFFFAOYSA-N
SMILES CCC(C)NP(=S)(OCC)OC1=C(C=CC(=C1)C)[N+](=O)[O-]
Properties
Chemical formula	C13H21N2O4PS
Molar mass	332.35 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H302, H410
Precautionary statements	P264, P270, P273, P301+P317, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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:^[3]

Synthesis of butamifos

Properties

Butamifos is a chiral molecule. The technical product uses a mixture of the (R)- and (S)-isomers.^[4]

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.^[5]

Use

Application and mode of action

Butamifos is used on beans, turf and various vegetables.^[3] 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.^[4][6]

Trade name

A crop protection product containing the active ingredient butamifos is marketed under the trade name Cremart.^[3]

Registration

No plant protection products containing butamifos are registered in the European Union or Switzerland.^[7]