Sumitomo Chemical Company, Limited

Masachika Hirano

Nobushige Itaya

Nobuo Ohno

Takashi Matsuo

Toshio Mizutani

Yoshitoshi Okuno

Isao Ohno

Kunio Mukai

Hisami Takeda

Keimei Fujimoto

Takeo Satomi

Noritada Matsuo

Kazunori Tsushima

Naganori Hino

Shigeyoshi Kitamura

Tadashi Ohsumi

Toshio Nishioka

Kiyoshi Kasamatsu

Yukio Suzuki

Akihiko Mine

Takayuki Okabe

Ryo Yoshida

Toshihiko Yano

Sumio Nishida

Kohichi Aketa

Takeshi Okuno

Osamu Magara

Kohshi Tateishi

Yuzuru Sanemitsu

Takashi Kato

Toshiro Kato

Mitsuru Sasaki

Masato Mizutani

Makoto Hatakoshi

Osamu Kirino

Yositosi Okuno

Katsuji Nodera

Minoru Ueda

Yoo Tanabe

Shigehiro Ooba

Norbushige Itaya

Koichi Aketa

Koshi Tateishi

Hideo Sakamoto

An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.

Novel ether compound, a process for manufacturing the same, a

This invention relates to a novel compound represented by the following general formula (I), its production, and an insecticidal and acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.

6-pyridyl- and 6-phenyl-3-phenyl-1-hexenes and -1-hexynes, composition

Ether compounds of the general formula, ##STR1## wherein W represents CH group or nitrogen atom, and (1) when W is the CH group, R.sub.1 represents hydrogen atom, fluorine atom, chlorine atom, bromine atom or methyl group, R.sub.2 represents hydrogen atom or fluorine atom, R.sub.3 and R.sub.4 are same or different and represent hydrogen atom, a halogen atom, a C.sub.1-4 alkyl, a C.sub.1-4 alkoxyl, difluoromethoxy or 2,2,2-trifluoroethoxy group, or represent, taken together, methylenedioxy group, A represents oxygen atom, methylene group or imino group, and when the A represents oxygen atom or methylene group, X and Y represent, taken together, ethylene group or 1,1-difluoroethylene group and when the A represents imino group, both X and Y represent methyl group or represent, taken together, ethylene group or 1,1-difluoroethylene group, and

Certain phenoxy-benzyloxy ether derivatives and an insecticidal and/or

Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.

Optically active phenyl acetates

An insecticidal composition comprising, as an active ingredient, an optically active .alpha.-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate and an inert carrier having a strong insecticidal activity without any appreciable toxicity to plants as well as to mammals.

Insecticidal composition containing optically active

The present invention relates to insecticidal compositions of low toxicity to fishes and mammals characterized by containing m-(p-bromophenoxy)-.alpha.-cyanolbenzyl trans- or trans-rich-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate of the formula (I), ##STR1## and at least one of the organo-phosphoric esters of the formula (II), ##STR2## wherein R.sub.1 and R.sub.2 are each a C.sub.1 -C.sub.3 alkyl group, X.sub.1, X.sub.2 and X.sub.3 are each an oxygen or sulfur atom, Y.sub.1 and Y.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 lower alkyl, methylmercapto, cyano or nitro group or a halogen atom, Z is a carbon or nitrogen atom and n is 0 or 1, in a ratio of 1 to 1-100 (part by weight) of the former to the latter, and insecticides obtained by mixing said compositions with a carrier or a diluent and if necessary an additive. The term 'trans-rich' shows the ratio of trans/cis is not less than 75/25.

Insecticidal and/or acaricidal composition exhibiting low toxicity to

Amide phosphorothiolate derivatives of the formula, ##STR1## wherein X is an oxygen or sulfur atom, Y is an oxygen or sulfur atom or imino group, R.sub.1 and R.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a C.sub.1 -C.sub.4 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a hydrogen atom, a methyl group or chlorine atom and n is 1 or 2, a process for producing said derivatives characterized by reacting the salt of thiophosphoric ester represented by the formula, ##STR2## wherein X, Y, R.sub.1 and R.sub.2 are as defined above and M is a sodium or potassium atom or ammonium group, with a haloacetamide derivative of the formula, ##STR3## wherein R.sub.3, R.sub.4, R.sub.5, Z and n are as defined above and W is a halogen atom, and a combined insecticide, acaricide, nematocide and/or fungicide containing said derivatives as an active ingredient.

Amide phosphorothiolate derivatives and their use as pesticides

The present invention relates to cyclopropanecarboxylates of the formula (I), ##STR1## wherein R and X may be same or different, each is a chlorine or bromine atom, and their production and use as an insecticide and/or acaricide.

Cyclopropanecarboxylates and a low fish toxic insecticide and/or

The present invention relates to insecticidal compositions of low toxicity to fishes and mammals characterized by containing m-(p-bromophenoxy)-.alpha.-cyanobenzyl trans- or trans-rich-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate of the formula (I), ##STR1## and a carbamic ester of the formula (III), ##STR2## wherein R is a group of the formula, ##STR3## in which X is a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxyl group and n is 1 or 2, in a ratio of 1 to 1-100 (part by weight) of the former to the latter, and insecticides obtained by mixing said compositions with a carrier or a diluent and if necessary an additive. The term 'trans-rich' shows the ratio of trans/cis is not less than 75/25.

Carboxylic acid esters of the formula (I), ##STR1## wherein X is a hydrogen atom, or a C.sub.1 -C.sub.3 alkyl or a C.sub.1 -C.sub.3 alkoxyl group or a halogen atom linked to the meta or para position and R.sub.1 is a group of the formula (II) or (III), ##STR2## wherein R.sub.2 is a hydrogen atom or a methyl group, and when R.sub.2 is a methyl group R.sub.3 is also a methyl group, and when R.sub.2 is a hydrogen atom R.sub.3 is a group of the formula, ##STR3## (wherein R.sub.5 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, vinyl or a C.sub.1 -C.sub.3 alkoxymethyl group, R.sub.6 is a hydrogen or halogen atom or a methyl group, or, taken together, R.sub.5 and R.sub.6 may form a tetramethylene group by connecting together at ends thereof), R.sub.4 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or 3,4-methylenedioxy group, n is 1 or 2 and Y is a isopropyl or cyclopropyl group. These carboxylic acid esters are produced by reacting the reactive derivatives of a carboxylic acid represented by the formula, ##STR4## wherein R.sub.1 is a group of the formula (II) or (III), ##STR5## wherein R.sub.2, R.sub.3, R.sub.4, n and Y are as defined above, and Z is a halogen atom, with an alcohol of the formula (IV), ##STR6## wherein X is as defined above, in the presence of an acid-binding agent. These carboxylic acid esters are useful as insecticides and acaricides.

Benzyl pyrrolyl methyl carboxylate insecticides and acaricides

A carboxylate of the formula, ##STR1## wherein R.sub.1 is an allyl or propargyl group, R.sub.2 is a group of ##STR2## in which R.sub.3 is a hydrogen atom or a methyl group, and when R.sub.3 is a hydrogen atom, R.sub.4 is a group of ##STR3## (in which R.sub.7 is a chlorine, bromine or fluorine atom, or a methyl, vinyl, methoxycarbonyl or methoxymethyl group, R.sub.8 is a hydrogen, chlorine, bromine or fluorine atom or a methyl group), and when R.sub.3 is a methyl group, R.sub.4 is a methyl group, R.sub.5 is an isopropyl or cyclopropyl group, R.sub.6 is an alkyl group having 1 to 3 carbon atoms or alkoxy group having 1 to 3 carbon atoms, or a chlorine, bromine or fluorine atom, n is 1 or 2, and --(R.sub.6).sub.n may include a 3,4-methylenedioxy group, and its use as an insecticide and/or acaricide.

Insecticidal and acaricidal 3,5-dioxo-2,3,4,5-triazine compounds

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

A method for preparing an optically active .alpha.-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)-isovalerate, which consists substantially of or is rich in (S)-.alpha.-cyano-3-phenoxybenzyl (S)-2-(4-substituted-phenyl)isovalerate.

Method for preparing an optically active .alpha.-cyano-3-phenoxybenzyl

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.

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Ibaraki, Japan

Masachika Hirano