Sumitomo Chemical Company, Limited

Yoshio Hisada

Toshiro Kato

Chiyozo Takayama

Akira Fujinami

Shigeo Yamamoto

Nobuyuki Kameda

Yoshinori Nakayama

Shuichiro Asao

Kunihiko Furuzawa

Akio Manabe

Kiyoto Maeda

Yuji Funaki

Hideo Agui

Kazuo Izumi

N-acylimidazole represented by the formula: ##STR1## wherein R is a lower alkyl group, and X, Y and Z are, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group, a halogenated lower alkyl group, a lower alkoxy group, a lower alkylthio group, a cyano group or a nitro group, or two of X, Y and Z, taken together, may form a methylenedioxy group, which is useful for controlling plant diseases.

Fungicidal N-acylimidazoles

N-acylimidazole compounds represented by the formula: ##STR1## wherein X is halogen atom, or alkyl, alkoxy, lower alkylthio, halogen-substituted alkyl, phenyl, phenoxy, cyano, phenyl lower alkoxy or nitro group, R.sub.1 and R.sub.2, which may be the same or different, are hydrogen or halogen atom, or alkyl, lower alkenyl, lower alkoxy, trifluoromethyl, lower cycloalkyl lower alkyl or lower alkoxy lower alkyl group, or R.sub.1 and R.sub.2, taken together, may form lower alkylene or halogen-substituted lower alkylene group, m is 0 or 1, n is 0, 1 or 2, and when n is 2, (X).sub.2 groups may form methylenedioxy group, which compounds are useful for controlling plant-disease, regulating plant growth and controlling weeds.

Fungicidal N-(phenyl-lower alkanoyl-)-imidazole derivatives,

An imidazolidinedione compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, Y is an oxygen atom or a sulfur atom, and R.sub.1 and R.sub.2 are each a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkylthio group, an ar(C.sub.1 -C.sub.4)alkylthio group, a C.sub.1 -C.sub.4 alkoxy(C.sub.2 -C.sub.4)alkoxy group, a phenyl group, a phenoxy group, a C.sub.1 -C.sub.4 alkylthiophenoxy group, a C.sub.1 -C.sub.8 alkylamino group, a C.sub.2 -C.sub.8 alkenylamino group or a cyano(C.sub.1 -C.sub.4)alkylamino group, which is useful as an agricultural chemical such as insecticides, acaricides, nematocides and/or fungicides with high safety to mammalian animals and human beings.

Imidazolidinedione compounds, and their production and use

1-Branched-alkylcarbonyl-3-(3,5-dihalophenyl)imidazolidine-2,4-diones of the formula: ##STR1## wherein X is a chlorine or bromine atom and R is a C.sub.3 -C.sub.5 branched alkyl group, which show high fungicidal activities without any material toxicity to mammals and plants and which can be produced by reacting the corresponding 1-unsubstituted compound with a branched alkanecarboxylic acid or a reactive derivative thereof.

1-Branched-alkylcarbonyl-3-(3,5-dihalophenyl)imidazolidine-2,4-diones

1-Cycloalkylcarbonyl-3-(3,5-dihalophenyl)imidazolidine-2,4-diones of the formula: ##STR1## wherein X is a chlorine or bromine atom, R.sub.1 is a C.sub.3 -C.sub.6 cycloalkyl, tetramethylcyclopropyl, 2,2-dimethyl-3-isobutenylcyclopropyl or 2,2-dimethyl-3-dichlorovinylcyclopropyl group and R.sub.2 and R.sub.3 are individually a hydrogen atom or a methyl group, which show high fungicidal activities without any material toxicity to mammals and plants and which can be produced by reacting the corresponding 1-unsubstituted compound with a cycloalkanecarboxylic acid or a reactive derivative thereof.

Fungicidal

N-(3,5-Dihalophenyl)-.alpha.-spirocycloalkanesuccinimides of the formula: ##STR1## wherein X is a chlorine or bromine atom and R is a C.sub.3 -C.sub.6 alkylene group, which show high fungicidal activities without any material toxicity to mammals and plants and which can be produced by reacting the corresponding .alpha.-spirocycloalkanesuccinic acid or its anhydride with 3,5-dichloroaniline or 3,5-dibromoaniline.

N-(3,5-dihalophenyl)-.alpha.-spirocycloalkanesuccinimides, and their

A method for preventing and eradicating bacterial infectious plant disease which comprises applying to plants a composition containing, as an active ingredient, at least one 4(1H)-oxo-3-quinolinecarboxylic acid derivative represented by the general formula (I): ##STR1## wherein A represents --OCH.sub.2 O--(at the 6 and 7 position) or ##STR2## (at the 5 and 6 position), wherein R.sub.4 represents a hydrogen atom or a lower alkyl group; R.sub.1 represents a hydrogen atom, a lower alkyl group, an amino group, an ammonium group or an alkali metal atom; R.sub.2 represents a lower alkyl group, a halogenated lower alkyl group, a hydroxyalkyl group, an alkenyl group, or an alkoxyl group; and R.sub.3 represents a hydrogen atom or a lower alkyl group.

Systemic antimicrobial quinolines for plant disease

3-(3',5'-Dihalophenyl)-1-sulfenylimidazolidine-2,4-diones of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, Y.sub.1, Y.sub.2 and Y.sub.3 are each a chlorine atom or a fluorine atom and R.sub.1 and R.sub.2 are individually a hydrogen atom or a methyl group, which show high microbicidal activities against various fungi without any material toxicity to mammals and plants and can be produced by reacting the corresponding 1-unsubstituted compound with a sulfenyl halide.

N'-Sulfenyl-N'-dihalophenylimidazolidinediones

Novel N-(3,5-dihalophenyl)cyclopropanedicarboximides of the formula: ##STR1## wherein X and Y are each a chlorine atom or a bromine atom and R.sub.1, R.sub.2 and R.sub.3 are individually a hydrogen atom or a methyl group, which show high microbicidal activities against various fungi and bacteria without any material toxicity to mammals and plants and which can be produced by reacting the corresponding cyclopropanedicarboxylic acid or its anhydride with a 3,5-dihaloaniline.

Halogenated N-(3,5-dihalophenyl)cyclopropanedicarboximides

3-(3' -Dihalophenyl)-1-sulfonylimidazolidine-2,4-5'-diones of the formula: ##STR1## wherein X is a halogen atom, R.sub.1 is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.4 alkenyl group or a halogenated C.sub.1 -C.sub.4 alkyl group having 1 to 3 halogen atoms, and R.sub.2 and R.sub.3 are individually a hydrogen atom or a methyl group, which show high microbicidal activities against various fungi and bacteria without any material toxicity to mammals and which plants and can be produced by reacting the corresponding 1-unsubstituted compound with a sulfonyl halide.

Growing community of inventors

Kawanishi, Japan

Yoshio Hisada