Otsuka Kagaku Kabushiki Kaisha

Otsuka Kagaku Yakuhin Kabushiki Kaisha

Otsuka Chemical Co., Ltd.

Hisashi Takao

Norio Osaki

Norio Yasudomi

Yasuo Shimizu

Takeshi Goto

Tetsuya Imai

Tadateru Murata

Yoshifumi Nakacho

Yoshinori Endo

Akira Tanaka

Tsunehiko Masatomi

Isao Tada

Takashi Soeda

Nobuyoshi Asai

Kenji Kase

Rokuro Harima

Mitsuyasu Kawata

Shoji Asano

Kazutoshi Kikkawa

Shuya Shimada

Takeshi Misawa

Sadahiko Iida

Pyridazinone derivatives, and insecticidal and miticidal composition

Disclosed is a phosphoric acid ester derivative represented by the general formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each lower alkyl, X.sup.1 and X.sup.2 are the same or different and are each a hydrogen atom or halogen atom, and Y is an oxygen atom or sulfur atom. The phosphoric acid ester derivatives of the present invention are usable as insecticides and miticides having excellent residual activity and low toxicity to warm blooded animals.

Pesticidal

This invention provides an imidazole derivative represented by the formula ##STR1## wherein R is lower alkyl, lower alkoxyalkyl, lower alkoxycarbonylmethyl or cyanomethyl, and X.sup.1 and X.sup.2 are each a hydrogen atom or halogen atom, process for preparing the derivative, and a fungicidal compositions comprising the derivative for use in agriculture and horticulture.

Fungicidal imidazole derivatives

A pyran derivative represented by a general formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, cycloalkyl or phenyl, R.sub.2 is alkyl having 8 to 20 carbon atoms, R.sub.3 is hydrogen, halogen, ##STR2## or --CH.sub.2 N A, R.sub.4 and R.sub.5 being each lower alkyl or cycloalkyl, A being --CH.sub.2 13 , oxygen or nitrogen atom, N A forms five or six-member ring (the ring may have no substitutent or have at least one substituent selected from lower alkyl, lower alkoxy and halogen atom), or an acid salt thereof, are useful as agricultural miticides.

Pyran derivatives

This invention provides an imidazol-1-yl-carboxylic acid ester derivative represented by the formula ##STR1## wherein R.sup.1 is lower alkyl, cycloalkyl or R.sup.3 (CH.sub.3).sub.2 C--(wherein R.sup.3 is halogenomethyl, acyloxymethyl or alkoxycarbonyl), R.sup.2 is a hydrogen atom, lower alkyl or cycloalkyl, X is a hydrogen atom, halogen atom, lower alkyl, cycloalkyl, lower alkenyl, lower alkoxyl, lower alkenyloxy, lower alkynyloxy, lower alkylthio, haloalkyl, haloalkenyl, substituted or unsubstituted phenyl, substituted or unsubstiuted benzyl, substituted or unsubstituted phenoxy, nitro, cyano, --COR.sup.4 l (wherein R.sup.4 is lower alkoxyl, lower alkenyloxy, benzyloxy, lower alkylamino or anilino)or ##STR2## (wherein R.sup.5 and R.sup.6 are each lower alkyl, acyl, sulfonyl or lower alkoxycarbonyl), n is an integer of from 1 to 3, Y and Z are the same or different and are each an oxygen atom or sulfur atom, a is 0 or 1, and b is 1 or 2, process for preparing the derivative, and a fungicidal composition comprising the derivative as an active component.

Fungicidal imidazol-1-yl-carboxylic acid ester derivatives

A pyran derivative represented by a general formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, cycloalkyl or phenyl, R.sub.2 is alkyl having 8 to 20 carbon atoms, R.sub.3 is hydrogen, halogen, ##STR2## R.sub.4 and R.sub.5 being each lower alkyl or cycloalkyl, A being --CH.sub.2 --, oxygen or nitrogen atom, ##STR3## forms five or six-member ring (the ring may have no substituent or have at least one substituent selected from lower alkyl, lower alkoxy and halogen atom), or an acid salt thereof, are useful as agricultural miticides.

Disclosed are novel phosphoric ester derivatives of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 each represents a lower alkyl group; R.sup.3 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a lower alkylthio group; X.sup.1 and X.sup.2 are the same or different and each represents a hydrogen atom or a halogen atom; and Y represents an oxygen atom or a sulfur atom, and insecticidal and miticidal compositions containing said derivatives.

Phosphoric ester derivatives and insecticidal and miticidal compositions

.gamma.-Pyrone phosphoric ester derivative represented by the general formula below is useful as an effective component of an insecticidal or miticidal composition for agricultural and horticultural uses. ##STR1## wherein R.sup.1 is hydrogen, lower alkyl group, lower alkenyl group, cycloalkyl group or phenyl group, R.sup.2 is hydrogen or lower alkyl group unsubstituted or substituted with halogen atom, A is --SR.sup.3 or --NR.sup.4 R.sup.5, B is OR.sup.6, R.sup.3 being lower alkyl group, cycloalkyl group or phenyl group, R.sup.4 being hydrogen or lower alkyl group, R.sup.5 being lower alkyl group, lower alkenyl group, cycloalkyl group, phenyl group or benzyl group, R.sup.4 and R.sup.5 may link to form piperidino or morpholino group, R.sup.6 being lower alkyl group, cycloalkyl group or phenyl group, Y is oxygen or sulfur atom.

.gamma.-Pyrone phosphoric ester derivatives and insecticidal and

A sulfenyl carbamate derivative represented by the formula ##STR1## wherein Ar represents ##STR2## R.sup.1 represents --X--COO--R.sup.3 or --Y--CN in which X and Y is each an alkylene group having 1 to 6 carbon atoms and R.sup.3 is an alkyl group having 1 to 8 carbon atoms; R.sup.2 represents --CH.sub.2 --.sub.n O--R.sup.4 in which R.sup.4 is an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group or a benzyl group; and n is an integer or 2 to 5.

Sulfenyl carbamate derivatives and insecticidal compositions containing

A process for purifying an aminosulfenylcarbamate derivative represented by the formula (I) ##STR1## wherein Ar is ##STR2## and R.sup.1 and R.sup.2 are the same or different and are each C.sub.1-8 alkyl, C.sub.3-6 cycloalkyl, benzyl which is unsubstituted or substituted with halogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxy, phenyl which is unsubstituted or substituted with halogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxy, --X--COOR.sup.3 or --Y--CN (in which X and Y are each straight-chain or branched-chain alkylene and R.sup.3 is C.sub.1-8 alkyl or C.sub.3-6 cycloalkyl), R.sup.1 and R.sup.2, when taken together, represent a 5- or 6-membered heterocyclic ring which may contain a sulphur or oxygen atom, the process comprising bringing a solution of the unreacted carbamate-containing aminosulfenylcarbamate derivative of the formula (I) in a water-insoluble organic solvent into contact with an aqueous alkali solution or a mixture of alkali, water and a water-soluble organic solvent. The aminosulfenylcarbamate derivatives are known insecticides.

Process for purifying aminosulfenylcarbamate derivatives

A novel S-methyl N-[{N-methyl-N-(N,N-disubstituted aminosulfenyl)carbamoyl}oxy]thioacetamidate derivative represented by the formula (I): ##STR1## which has insecticidal, miticidal or nematocidal activity comparable to or higher than known methomyl but which is quite low in toxicity to warm-blooded animals as compared to methomyl, is disclosed. An insecticidal, miticidal or nematocidal composition containing the same, and a process for preparing the same are also disclosed. A method for controlling noxious insects, mites or nematodes by using the same is further disclosed.

Carbamate derivatives, insecticidal, miticidal or nematocidal

This invention relates to carbamate derivatives represented by the formula (I): ##STR1## a process for preparing the derivatives and insecticides containing the derivatives.

Carbamate derivatives and insecticidal, miticidal or nematocidal

A pyran derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.4 are each the same or different alkyl having 1 to 6 carbon atoms, R.sub.2 and R.sub.3, when attached to a nitrogen atom, forms a saturated hetrocyclic ring which has as a hetero atom a nitrogen atom is addition to the nitrogen atom attached to R.sub.2 and R.sub.3, or oxygen atom, and an acid addition salt thereof. The compounds have antibacterial and insecticidal action.

Heterocyclic containing 5-oxo pyrans

2,2'-BIS(3,4-Epoxy-5-oxotetrahydropyran)ethers represented by the formula ##STR1## wherein R is hydrogen atom or straight-chain or branched-chain alkyl having 1 to 6 carbon atoms; a process for preparing the same.

Growing community of inventors

Tokushima, Japan

Hisashi Takao