Ishihara Sangyo Kaisha, Ltd.

Rikuo Nasu

Kanichi Fujikawa

Ryuzo Nishiyama

Nobuyuki Sakashita

Isao Yokomichi

Toshio Nakajima

Ryohei Takahashi

Tadaaki Toki

Itaru Shigehara

Terumasa Komyoji

Motohiko Hamaguchi

Hideshi Yoshimura

Kazumi Suzuki

Keiichiro Ito

Takahiro Haga

Fumio Kimura

Shigeyuki Nishimura

Takao Awazu

Kuniaki Nagatani

Junichi Kawashima

Isamu Katsuyama

Hayato Ariyoshi

Toshihiko Yamamoto, Deceased

By Hikotaro Yamamoto, Legal Representative

Toshihiko Yamamoto

Taku Shimura

Tekeshi Ohshima

Takeshi Oshima

A method for halogenating an aromatic compound, which comprises reacting the aromatic compound of the formula (I): ##STR1## wherein X is a hydroxyl group, an amino group or an acylamino group, each of Z.sub.1 and Z.sub.2 is a hydrogen atom or a halogen atom, one of R and Y is a hydrogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and Q is a nitrogen atom or --C(T).dbd. (wherein T is a hydrogen atom, a halogen atom, a nitro group, a cyano group or a trifluoromethyl group), with a halogenating agent to obtain a 3-halogenoaromatic compound of the formula (II): ##STR2## wherein one of R' and Y' is a halogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and X, Z.sub.1, Z.sub.2 and Q are as defined above.

Method for halogenating an aromatic compound

A process for producing 3,5-difluoroaniline, which comprises reacting a benzonitrile compound of the formula (I): ##STR1## wherein each of X.sub.1, X.sub.2 and X.sub.3 is hydrogen, chlorine, bromine or a cyano group, provided that at least one of X.sub.1 to X.sub.3 is a cyano group, with a mineral acid for hydrolysis and decarboxylation to obtain an aniline compound of the formula (II): ##STR2## wherein each of X.sub.4, X.sub.5 and X.sub.6 is hydrogen, chlorine or bromine, provided that at least one of X.sub.4 to X.sub.6 is hydrogen, and in the case of a compound of the formula (II) wherein X.sub.4, X.sub.5 and X.sub.6 are not simultaneously hydrogen, reacting such a compound with hydrogen in a presence of a catalyst for reduction to obtain 3,5 -difluoroaniline.

Process for producing 3,5-difluoraniline

A method for producing a dichloromethylpyridine of the formula (II): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which are independent of one another, is a hydrogen atom, a halogen atom, an alkoxy group or a phenoxy group which may be substituted, provided that R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are not simultaneously hydrogen atoms, which comprises reacting a trichloromethylpyridine of the formula (I): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with a reducing agent, wherein:

Method for producing dichloromethylpyridines

Novel imidazole compounds are disclosed, which are represented by the following general formula: ##STR1## wherein: R.sub.1 represents a cyano group or a --CSNHR.sub.5 group, wherein R.sub.5 represents a hydrogen atom, a C.sub.1-4 alkyl group, or a --COR.sub.6 group, wherein R.sub.6 represents a C.sub.1-4 alkyl group, a halogenated C.sub.1-4 alkyl group, or a phenyl group;

Imidazole compounds and biocidal composition comprising the same for

A biocidal composition containing, as active ingredients, at least one imidazole compound represented by formula (I): ##STR1## wherein R.sup.1 represents a phenyl group, a halogen-substituted phenyl group, an alkyl group, or a halogen-substituted alkyl group; and R.sup.2 represents a halogen atom, and at least one other specific compound. The combination of the compound represented by formula (I) and other specific compound can produce an unexpected effect in amount required and biocidal spectrum.

Biocidal composition

5,6-Dichloro-.beta.-trifluoromethylpyridine or 2,5,6-trichloro-.beta.-trifluoromethylpyridine is produced by reacting 6-chloro-.beta.-trifluoromethylpyridine or 2,6-dichloro-.beta.-trifluoromethylpyridine with chlorine gas to chlorinate the 5-position of pyridine nucleus thereof:

Process for producing 5-chloro-.beta.-trifluoromethylpyridines

4-(Pyridyl-2-oxy)phenoxyalkanecarboxylic acid derivative is produced by reacting 2-phenoxypyridine derivative with 4-hydroxyphenoxyalkanecarboxylic acid derivative. The products which are effective as an active ingredient of a herbicide can be obtained at high yield by an interphenoxylation.

Process for producing 4-(pyridyl-2-oxy)-phenoxyalkanecarboxylic acid or

2-Chloro-5-trichloromethyl pyridine is produced by reacting .beta.-picoline with chlorine in a gaseous phase at 300.degree. to 500.degree. C. in the presence of an inert diluent of nitrogen, a halogenated methane, a halogenated ethane a halogenated ethylene or a mixture thereof. 2-Chloro-5-trichloromethyl pyridine is useful as an intermediate for medicines, agricultural chemicals, dyes especially herbicides.

Process for producing 2-chloro-5-trichloromethyl pyridine

Phenoxypropane compounds represented by the general formula (I): ##STR1## wherein X is a 4-halophenoxy group, a 2,4-dihalophenoxy group, a 4-trifluoromethylphenoxy group, a 2-halo-4-trifluoromethylphenoxy group, a 5-halopyridyl-2-oxy group or a 3,5-dihalopyridyl-2-oxy group; and Y is a halogen atom, a hydroxy group, a (C.sub.1 -C.sub.4)-alkoxy group in which the alkyl moiety thereof may be substituted with a hydroxy group(s), a (C.sub.1 -C.sub.4)alkylcarbonyloxy group or a phenylcarbonyloxy group in which the phenyl moiety thereof may be substituted with a halogen atoms(s), useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.

Herbicidal compound, herbicidal composition containing the same, and

A sulfonanilide compounds having the formula (I): ##STR1## wherein X.sub.1 is hydrogen atom, a halogen atom, methyl group or trifluoromethyl group, X.sub.2 is hydrogen atom or a halogen atom, R.sub.1 is a (C.sub.1 -C.sub.4) alkyl group or a halo(C.sub.1 -C.sub.4) alkyl group, R.sub.2 is hydrogen atom, a (C.sub.1 -C.sub.4) alkyl group, trifluoromethyl group or nitro group, R.sub.3 is hydrogen atom, --SO.sub.2 R.sub.1 group (R.sub.1 is the same as defined above), a (C.sub.2 -C.sub.4) acyl group, a (C.sub.2 -C.sub.4) acylmethyl group, a (C.sub.1 -C.sub.4) alkyl group, a (C.sub.1 -C.sub.4) alkoxy (C.sub.1 -C.sub.4) alkyl group or a (C.sub.3 -C.sub.4) alkenyl group, R.sub.4 is hydrogen atom or a halogen atom, and n is an integer of 0 to 2; and a salt thereof, which is useful as a herbicidal component.

Pyridine-2-thio, -2-sulfinyl, and -2-sulfonyl sulfonanilide compounds

N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR1## wherein X.sub.1 represents a halogen atom or methyl group; X.sub.2 represents hydrogen or halogen atom; X.sub.3 and X.sub.4 respectively represent hydrogen or halogen atom; X.sub.5 represents hydrogen or halogen atom; and X.sub.6 represents a halogen atom or nitro or trifluoromethyl group are novel compounds. The compositions containing the compound as the active ingredient are effective as the insecticide for extinction of injurious insects with high safety in agricultural, forestry and hygienic applications.

N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof

N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR1## wherein X.sub.1 represents a halogen atom; X.sub.2 represents hydrogen or halogen atom; X.sub.3 and X.sub.4 respectively represent hydrogen or chlorine atom; X.sub.5 represents hydrogen or halogen atom; and X.sub.6 represents a halogen atom or nitro or trifluoromethyl group are novel compounds. The compositions containing the compound as the active ingredient are effective as the insecticide for extinction of injurious insects with high safety in agricultural, forestry and hygienic applications.

Phenoxy malonic acids and derivatives thereof represented by the general formula (I): ##STR1## wherein X is a 4-trifluoromethylphenoxy group or a 3,5-dichloropyridyl-2-oxy group; and R is a hydroxy group, an --O-- cation group or a (C.sub.1 - C.sub.4)alkoxy group, useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.

3,5-Dichloropyridyl-2-oxy-phenoxy malonic acids and derivatives and

Phenoxy valeric acids and derivatives thereof represented by the general formula (I): ##STR1## wherein X is a hydrogen atom or a chlorine atom; and R is a hydroxy group, an --O-cation group, a (C.sub.1 - C.sub.4)alkoxy group, a (C.sub.1 - C.sub.4)alkylthio group, a benzyloxy group, or an amino group which may be substituted with a (C.sub.1 - C.sub.4)alkyl group(s), a phenyl group or a pyridine-2-yl group, useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.

Herbicidal compound, herbicidal composition containing the same and

Phenoxypropane compounds represented by the general formula (I): ##STR1## wherein X is a 4-halophenoxy group, a 2,4-dihalophenoxy group, a 4-trifluoromethylphenoxy group, a 2-halo-4-trifluoromethylphenoxy group, a 5-halopyridyl-2-oxy group or a 3,5-dihalopyridyl-2-oxy group; and Y is a halogen atom, a hydroxy group, a (C.sub.1 -C.sub.4)alkoxy group in which the alkyl moiety thereof may be substituted with a hydroxy group(s), a (C.sub.1 -C.sub.4)alkylcarbonyloxy group or a phenylcarbonyloxy group in which the phenyl moiety thereof may be substituted with a halogen atom(s), useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.

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Kusatsu, Japan

Rikuo Nasu