Sumitomo Chemical Company, Limited

Kunio Mukai

Masachika Hirano

Takeo Satomi

Mitsuru Sasaki

Naganori Hino

Tadashi Ooishi

Takayuki Okabe

Toshiro Kato

Yoshimi Yamada

Keimei Fujimoto

Akihiko Mine

Kohshi Tateishi

Ryo Yoshida

Hisami Takeda

Toshiaki Ozaki

Yositosi Okuno

Sigeo Yamamoto

Katsuji Nodera

Akio Kimura

Hiroshi Taya

Taizo Ogawa

Hiroshi Tsuchiya

Shunichi Hashimoto

Kiyoshi Kasamatsu

Isao Ohno

Yukio Ishiguri

Haruyasu Yamamoto

Katsutoshi Tanaka

Yoshio Fujita

Koshi Tateishi

Takaji Yamamoto

Kouichi Ishibe

Hideo Sakamoto

Rokuo Koyanagi

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 soil disinfectant composition for preventing and controlling diseases caused by pathogenic fungi living in soil, which comprises an effective amount of at least one of phenylphosphinic acid and its salts as an active ingredient, and at least one inert carrier or diluent.

Soil disinfectant

A fungicidal composition which comprises as an active ingredient a fungicidally effective amount of a compound of the formula: ##STR1## wherein X is a hydroxyl group or a hydroxyamino group, or its salt and an inert carrier or diluent.

Fungicidal composition comprising alpha-substituted ethylphosphinic

Soil disinfectants and method of use

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.

Pyrimidin-4-yl-phosphorus esters and insecticidal, acaricidal or

Nematocidal O-ethyl S-alkyl S-isopropyl phosphorodithiolates.

O-Ethyl S-alkyl S-isopropyl phosphoro-dithiolate, and their use as

Pesticidal compositions containing, as active ingredient, a compound of the formula ##STR1## wherein R.sub.1 is lower alkyl, lower alkenyl, lower alkynyl or a radical of the formula ##STR2## IN WHICH X is lower alkyl, halogen or hydrogen and n is zero or an integer of 1 to 5,

Amido phosphorothiolate pesticide

Phosphorothiolates represented by the formula, ##STR1## wherein R is an alkyl; A is an alkyl, haloalkyl, alkenyl, alkinyl, alkylthioalkyl, phenylthioalkyl, phthalimidoalkyl or phenylalkyl; X is hydrogen, a halogen or an alkyl; and n is an integer of 1 to 5, are obtained by (1) reacting sodium or potassium hydrosulfide with a compound represented by the formula, ##STR2## WHEREIN R, X and n have the same significances as mentioned above, to prepare a thiophosphate represented by the formula, ##STR3## wherein R, X and n have the same significances as mentioned above; and M is an alkali metal, and then (2) reacting said thiophosphate with a halide represented by the formula,

Phosphorothiolate pesticidal composition

The present invention relates to new herbicidal phosphorothioate (phosphorodithioate) derivatives and to preparation thereof.

Amide phosphorothiolate herbicides

Process for preparing 5-methyl-2-nitrophenol of high purity by sulfonating tri-m-cresyl phosphate, nitrating the sulfonated tri-m-cresyl phosphate, hydrolyzing the nitrated, sulfonated tri-m-cresyl phosphate to obtain a mixture of nitro-m-cresols, steam-distilling the mixture, and repeatedly washing the distillate with a dilute aqueous alkaline solution.

Preparation of 5-methyl-2-nitrophenol

Phosphorothiolates represented by the formula, ##STR1## wherein R is an alkyl; A is an alkyl, haloalkyl, alkenyl, alkinyl, alkylthioalkyl, phenylthioalkyl, phthalimidoalkyl or phenylalkyl; X is hydrogen, a halogen or an alkyl; and n is an integer of 1 to 5, are obtained by (1) reacting sodium or potassium hydrosulfide with a compound represented by the formula, ##STR2## WHEREIN R, X, and n have the same significances as mentioned above, to prepare a thiophosphate represented by the formula, ##STR3## wherein R, X and n have the same significances as mentioned above; and M is an alkali metal, and then (2) reacting said thiophosphate with a halide represented by the formula,

Phosphorothiolates

Compounds of the formula ##STR1## WHERE R.sub.1 is lower alkenyl, optionally substituted by chlorine or bromine, or R.sub.1 is alkoxyalkyl; R.sub.2 and R.sub.3 are lower alkyl; R.sub.4 is lower alkyl, lower alkoxy or halogen; and n is zero or an integer of 1-5, which are useful as herbicides, insecticides, acaricides and nematocides.

The present invention relates to compounds of the formula: ##STR1## wherein R.sub.1 is lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, unsubstituted aralkyl, lower alkyl or halogen-substituted aralkyl or halogen-substituted alkenyl; R.sub.2 is lower alkyl; Y is hydrogen or methyl and X is lower alkyl; n is an integer of 1 to 5, and a method of producing these compounds. These compounds are eminently suited for killing weeds, injurious insects, nematodes and acaricides.

Growing community of inventors

Nishinomiya, Japan

Kunio Mukai