Phosphonamidothionate derivatives and their use as pesticides
AssigneeAsahi Kasei Kogyo Kabushiki Kaisha
InventorsHiromichi Yoshikawa, Teruyuki Misumi
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Abstract
A novel phosphonamidothionate derivative represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the disclosure. The present novel compound has excellent properties with respect to not only pesticidal activity but also maintenance of the pesticidal activity over a prolonged period of time after application. The present novel compound can be prepared by a new unique process in which the direct phosphorylation of a carbamate compound is involved.
Claims12
A phosphonamidothionate derivative represented by the formula ##STR46## wherein R.sup.1 and R.sup.2 each independently represent a straight-chain alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms and R.sup.3 represents a phenyl group unsubstituted or substituted with a chlorine atom, a methyl group, a nitro group, a methylthio group or a nitrile group, an alkyl group having 1 to 4 carbon atoms or a 5-methyl-2-isoxazolyl group.
A process for preparing a phosphonamidothionate derivative represented by the formula ##STR47## wherein R.sup.1 and R.sup.2 each independently represent a straight-chain alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms and R.sup.3 represents a phenyl group unsubstituted or substituted with a chlorine atom, a methyl group, a nitro group, a methylthio group or a nitrile group, an alkyl group having 1 to 4 carbon atoms or a 5-methyl-2-isoxazolyl group, which comprises the steps of
- (1) reacting a carbamic acid ester derivative represented by the formula ##STR48## wherein R.sup.1 and R.sup.2 each independently represent a straight-chain alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms,
- with methylphosphonothioic dichloride in dioxane in the presence of an amine, to thereby obtain a methylphosphonothioyl chloride derivative represented by the formula ##STR49## wherein R.sup.1 and R.sup.2 are as defined above, and (2) subsequently reacting the methylphosphonothioyl chloride derivative of formula (III) with a compound represented by the formula
- HO--R.sup.3 (IV)
- wherein R.sup.3 represents a phenyl group unsubstituted or substituted with a chlorine atom, a methyl group, a nitro group, a methylthio group or a nitrile group, an alkyl group having 1 to 4 carbon atoms or a 5-methyl2-isoxazolyl group,
- in tetrahydrofuran in the presence of an amine.
A pesticidal composition comprising as an active ingredient a pesticidally effective amount of a phosphonamidothionate derivative represented by the formula ##STR50## wherein R.sup.1 and R.sup.2 each independently represent a straight-chain alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms and R.sup.3 represents a phenyl group unsubstituted or substituted with a chlorine atom, a methyl group, a nitro group, a group having 1 to 4 carbon atoms or a 5-methyl-2-isoxazolyl group, and a sanitary or agriculturally and horticulturally acceptable carrier or diluent.
A method for combatting sanitary insect pests or agricultural and horticultural insect pests, which comprises applying to the insect pests or a habitat thereof a pesticidally effective amount of a phosphonamidothionate derivative represented by the formula ##STR51## wherein R.sup.1 and R.sup.2 each independently represent a straight-chain alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms and R.sup.3 represents a phenyl group unsubstituted or substituted with a chlorine atom, a methyl group, a nitro group, a methylthio group or a nitrile group, an alkyl group having 1 to 4 carbon atoms or a 5-methyl-2-isoxazolyl group.
Dependencies are inferred from the claim text.