Sumitomo Chemical Company, Limited

Takeda Pharmaceutical Company Limited

Takayuki Okabe

Kunio Mukai

Haruyasu Yamamoto

Masachika Hirano

Kiyoshi Kasamatsu

Yusuke Murakawa

Shiro Ishii

A dithiolphosphoric acid ester of the formula, ##STR1## wherein R is methyl or ethyl group, and when R is methyl group, A is iso-butyl, sec-butyl or tert-butyl group and B is methyl, ethyl or n-propyl group, when R is ethyl group and A is sec-butyl or tert-butyl group, B is methyl group, and when R is ethyl group and A is iso-butyl group, B is methyl, ethyl or n-propyl group, which is useful as a soil pesticidal composition for pests in soil.

Dithiolphosphoric acid esters

A trithiophosphoric acid ester of the formula: ##STR1## wherein R is lower alkyl group, and R.sub.1 and R.sub.2 are different from each other, R.sub.1 is C.sub.1 -C.sub.4 alkyl group and R.sub.2 is isobutyl, sec-butyl or tert-butyl group, which is useful as a soil pesticidal composition for pests in soil.

Trithiophosphoric acid ester as a soil pesticide

A trithiophosphoric acid ester of the formula; ##STR1## wherein R.sub.1 is methyl or ethyl group, which is useful as a soil pesticidal composition for pests in soil.

A dithiolphosphoric acid ester of the formula, ##STR1## wherein A is sec-butyl or tert-butyl group, and B is iso-propyl, n-butyl, iso-butyl, sec-butyl or tert-butyl group, which is useful as a soil pesticidal composition for pests in soil.

Dithiolphosphoric acid ester as a soil pesticide

Phosphoro-thioates or dithioates of the formula (I), ##STR1## wherein R is a C.sub.1 -C.sub.3 alkyl group, R.sub.1 is a C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.4 alkylamino or allylamino group, R.sub.2 is a halogen atom, a C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a hydrogen or halogen atom or a C.sub.1 -C.sub.3 alkyl group, R.sub.4 is a C.sub.1 -C.sub.3 alkyl group, and X is an oxygen or sulfur atom, provided that when R.sub.1 is a C.sub.1 -C.sub.4 alkylamino or allylamino group, X is an oxygen atom, a process for producing phosphoro-thioates or dithioates of the formula (I) characterized by condensing a pyrimidine of the formula (II), ##STR2## wherein Y is a halogen atom, and R.sub.2, R.sub.3 and R.sub.4 are as defined above, with a thio- or dithio-phosphate of the formula, ##STR3## wherein M is an alkali metal atom or an ammonium group, and R, R.sub.1 and X are as defined above, an insecticide, acaricide and nematocide characterized by containing phosphoro-thioates or dithioates of the formula (I) as an active ingredient, and pyrimidines, novel intermediate compounds, of the formula (II) wherein R.sub.2 is a C.sub.1 -C.sub.4 alkoxy group or a halogen atom, R.sub.3 is a hydrogen or halogen atom or a C.sub.1 -C.sub.3 alkyl group, and R.sub.4 is a C.sub.2 -C.sub.3 alkyl group.

Organo-phosphoric esters and their production and use

Organophosphorus esters of the formula (I), ##STR1## wherein R is a C.sub.1 -C.sub.2 alkyl group, R.sub.1 is a C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.4 alkylamino, phenyl or phenoxy group, R.sub.2 and R.sub.3, which may be the same or different, are each a C.sub.1 -C.sub.5 alkyl or methoxy C.sub.2 -C.sub.3 alkyl group and X is an oxygen or sulfur atom, a method for producing organophosphorus esters of the formula (I) characterized by condensation reaction of s-triazines of the formula, ##STR2## wherein M is a potassium or sodium atom and R.sub.2 and R.sub.3 are as defined above, with a halogenated compound of the formula, ##STR3## wherein Y is a halogen atom and R, R.sub.1 and X are as defined above, and an insecticide, acaricide and/or nematocide characterized by containing organophosphorus esters of the formula (I) as an active ingredient.

Triazinyl-organophosphorus esters

Pyrimidin-4-yl-phosphorothionates of the formula (I), ##STR1## wherein R is a C.sub.1 -C.sub.2 alkyl group, R.sub.1 is a C.sub.1 -C.sub.2 alkoxyl or C.sub.1 -C.sub.4 alkylamino group, R.sub.2 and R.sub.3, which may be the same or different, are each a halogen atom, a C.sub.1 -C.sub.3 alkoxyl or methylmercapto group, and X is an oxygen or sulfur atom; a process for producing pyrimidin-4-yl-phosphorothionates of the formula (I) characterized by condensing a 4-hydroxypyrimidine of the formula (II), ##STR2## wherein R.sub.2 and R.sub.3, which may be the same or different, are each a halogen atom, a C.sub.1 -C.sub.3 alkoxyl or methylmercapto group, with a halogen compound of the formula, ##STR3## wherein R is a C.sub.1 -C.sub.2 alkyl, R.sub.1 is a C.sub.1 -C.sub.2 alkoxyl or C.sub.1 -C.sub.4 alkylamino group, Y is a halogen atom and X is an oxygen or sulfur atom; an insecticide, acaricide and nematocide characterized by containing pyrimidin-4-yl-phosphorothionates of the formula (I) as an active ingredient; 4-hydroxypyrimidines of the formula (II) wherein R.sub.2 and R.sub.3, which may be the same or different, are each a halogen atom, a C.sub.2 -C.sub.3 alkoxyl or methylmercapto group; and a process for producing 4-hydroxypyrimidines of the formula (II) wherein R.sub.2 and R.sub.3, which may be the same or different, are each a halogen atom, a C.sub.2 -C.sub.3 alkoxyl or methylmercapto group, characterized by reacting an acetamidine hydrochloride of the formula, ##STR4## wherein R.sub.4 is a halogen atom, a C.sub.2 -C.sub.3 alkoxyl or methylmercapto group, with a .beta.-ketoester of the formula, ##STR5## wherein R.sub.5 is a halogen atom, a C.sub.2 -C.sub.3 alkoxyl or methylmercapto group, and R.sub.6 is a C.sub.1 -C.sub.2 alkyl group.

Growing community of inventors

Nishinomiya, Japan

Takayuki Okabe