Sankyo Company, Limited

Teruomi Jojima

Hideo Takeshiba

Yukiyoshi Takahi

Takao Kinoto

Toshiaki Yanai

Katsuhiko Kawakubo

Takashi Matsui

Hideakira Tsuji

Toyokuni Honma

Shinjiro Yamamoto

Masahiro Shindo

Teiji Omino

Compounds of formula (I): ##STR1## [in which: A represents a group of formula --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --;

Pyridazinone derivatives, their preparation and their use in

Compounds of formula (I): ##STR1## (in which R.sup.1 and R.sup.3 are hydrogen or halogen: R.sup.2 is hydrogen, alkyl, alkoxy or halogen; R.sup.4 is hydrogen and R.sup.5 is hydroxy or alkoxy; or R.sup.4 is hydroxy and R.sup.5 is hydrogen; except that R.sup.1, R.sup.2 and R.sup.3 may not all simultaneously be hydrogen) are valuable agricultural fungicides.

Pyridazinone derivatives and their use as agricultural fungicides

Compounds of formula (I): ##STR1## [wherein R.sup.1 and R.sup.3 represent hydrogen or halogen atoms, R.sup.2 represents a hydrogen or halogen atom or a lower alkyl or alkoxy group (provided R.sup.1, R.sup.2 and R.sup.3 are not simultaneously hydrogen), represents a single or double carbon-carbon bond and, where it is a single bond, R.sup.4 represents a group of formula --SR.sup.5 (wherein R.sup.5 represents an optionally substituted alkyl, phenyl, aralkyl or pyridyl group or a lower alkenyl group) and, where it is a double bond, R.sup.4 represents hydrogen] can be prepared by reacting a compound of formula (II): ##STR2## with a compound of formula R.sup.6 H [where R.sup.6 represents a group --SR.sup.5, a group --SR.sup.7 (where R.sup.7 represents a group of formula ##STR3## and Y represents oxygen or sulphur, R.sup.8 and R.sup.9 represent lower alkoxy groups and R.sup.10 represents a lower alkoxy, lower alkyl or phenyl group), a methoxy group or a halogen atom] to give a compound of formula (IV): ##STR4## or, where R.sup.6 represents a methoxy group, a methyl ester thereof; reacting this compound with hydrazine to give a compound of formula (V): ##STR5## and, if necessary, treating the compound of formula (V) with an acid or a base to produce the compound of formula (VI). All of the compounds of formula (I) are valuable antifungal agents and compounds of formula (V) where R.sup.6 represents a group of formula --SR.sup.5 are novel compounds.

Process for producing antifungal oyridazinone derivatives

Pyrazole derivatives of formula (I): ##STR1## (R.sup.1 is methyl, halogen or nitro; n is 2 or 3; R.sup.2 is hydrogen, C.sub.1-4 alkyl, C.sub.3-4 alkenyl or aralkyl; R.sup.3 is C.sub.1-4 alkyl, C.sub.3-4 alkenyl or phenyl; A is C.sub.1-5 alkylene) are of use as herbicides.

Herbicidal 5-aminoalkoxy-4-benzoyl-1,3-dimethyl-pyrazole derivatives

6-(3- And/or 5-halophenyl)pyridazines having an N-substituted carbamoyloxy, carbamoylthio, thiocarbamoyloxy or thiocarbamoylthio group at the 3- position on they pyridazine system and 6-(3- and/or 5-halophenyl)-3-pyridazone derivatives having a substituted or unsubstituted hydrocarbyloxycarbonyl substituent at the 2-position of the pyridazine ring have good fungicidal activity, making them useful as agricultural fungicides suitable for application to seeds, plants and agricultural land, and can be prepared by reacting the corresponding 6-substituted pyridazone or pyridazinethione with the corresponding carbamoyl halide or halocarbonate.

Pyridazine derivatives and their use as agricultural fungicides

New organic phosphorus compounds having the formula ##STR1## wherein R.sub.1 represents an alkyl group of 1-4 carbon atoms, R.sub.2 represents an alkoxy group of 1-4 carbon atoms or phenyl group and R.sub.3 represents hydrogen atom, an alkyl group of 1-4 carbon atoms, phenyl group or the group of the formula -X-R.sub.4 in which R.sub.4 represents an alkyl group of 1-6 carbon atoms or a benzyl group which may be substituted with a halogen atom in the phenyl moiety and X represents oxygen atom or sulfur atom. The present compounds are prepared by reacting a phosphoric or phosphonic acid halide having the formula ##STR2## wherein R.sub.1 and R.sub.2 are as defined above and Y represents a halogen atom with a pyridazinone derivative having the formula ##STR3## wherein R.sub.3 is as defined above. The present compounds show a superior insecticidal activity against various harmful insects, e.g., rice stem borers, planthoppers, mites, aphids, flies, mosquitoes and the like and thus they are useful as an insecticide or acaricide.

Organic pyridazyl phosphorothioates and their use as insecticides

Agricultural fungicidal compositions containing as an active ingredient one or more of 6-(substitutedphenyl)-3(2H)-pyridazinone compounds, salts thereof and 6-(substituted-phenyl)-4,5-dihydro-3(2H)-pyridazinone compounds, as well as new pyridazinone compounds having fungicidal activities.

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Hiromachi, Japan

Teruomi Jojima