Sumitomo Chemical Company, Limited

Masayuki Enomoto

Eiki Nagano

Ryo Sato

Masaharu Sakaki

Toru Haga

Susumu Takemura

Kouichi Morita

Satoru Kizawa

Junya Takahashi

Masayo Sugano

Tomoyuki Kusaba

Rei Matsunaga

Masahiro Tamaki

Hisayuki Hoshi

Toru Uekawa

Minoru Takano

Yuzuru Sanemitsu

Kazuo Saito

Masaharu Sakai

Shinsuke Shojima

Mitsunori Hiratsuka

Yoshitomo Tohyama

Kazuo Saitoh

Novel pyrimidin-4-one derivatives of formula &lsqb;1&rsqb; are provided, which are useful as active ingredients of herbicides, wherein R,is hydrogen or alkyl; R,is alkyl optionally substituted with halogen; R,is alkyl optionally substituted with halogen, alkenyl, or alkynyl; and Q is substituted phenyl. Also provided are intermediates for their production and processes for producing these intermediates.

Pyrimidin-4-one derivatives, their use, intermediates for their production, and processes for producing these intermediates

The present invention provides novel pyridazin-3-one derivatives of general formula (1): ##STR1## wherein R.sup.1 is haloalkyl; R.sup.2 and R.sup.3 are independently hydrogen, alkl, haloalkyl, or alkoxyalkyl; X is hydrogen or halogen; Y is halogen, nitro, cyano, or trihalomethyl; Z.sup.1 is oxygen, sulfur, CH.sub.2, or NH; R.sup.4 is hydrogen, halogen, or alkyl; and R.sup.5 is cycoalkyl, formyl, benzyl, alkyl with an epoxy group, or other substituents as defined in the description, and herbicides containing them as active ingredients.

Pyridazin-3-one derivatives and their use

Pyrimidin-4-one derivatives, their intermediates for their production

Novel compounds of the formula �1! are disclosed, wherein X is hydrogen, fluorine or chlorine; Y is fluorine, chlorine or bromine; R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.2 and Q are various groups. Also disclosed are herbicidal compositions containing these compounds as active ingredients and methods for controlling unfavorable weeds by application of these compounds.

Epoxyphenol derivatives and herbicides containing them as active

There are disclosed novel pyrimidone derivatives of the formula I: ##STR1## wherein X is hydrogen, chlorine, methyl or ethyl, R.sup.2 is hydrogen or methyl, and Q is ##STR2## A is fluorine, chlorine or bromine; and R.sup.1 is alkyl, alkenyl, alkynyl, alkoxyalkyl or haloalkyl. Also disclosed are a herbicidal composition containing a herbicidally effective amount of the compound (I) as an active ingredient and a method for exterminating undesired weeds by applying a herbicidally effective amount of the compound (I) to an area where the undesired weeds grow or will grow.

Pyrimidone derivatives and their use

There is disclosed an iminothiazoline derivative of the general formula: ##STR1## wherein R.sub.1 is (halo)alkyl, (halo)alkenyl, (halo)alkynyl or the like; R.sub.2 is (halo)alkyl, optionally substituted aryl, formyl, cyano or the like; R.sub.3 is hydrogen, (halo)alkyl or the like; and Q is a group of the particular general formula. Also disclosed are a herbicide containing a herbicidally effective amount of the iminothiazoline derivative and a method for controlling unfavorable weeds, which includes applying a herbicidally effective amount of the iminothiazoline derivative to an area where the unfavorable weeds grow or will grow.

Iminothiazoline derivatives and herbicides containing them as active

A benzimidazole derivative having the formula, ##STR1## wherein R is cyano or thiocarbamoyl; Q is lower alkyl or a group represented by the formula NQ.sup.1 Q.sup.2, in which Q.sup.1 and Q.sup.2 are independently lower alkyl, lower alkyl substituted with phenyl, lower alkenyl or lower alkynyl, or they form a lower alkylene ring when taken together at their ends which ring may include a hereto atom; X is hydrogen or halogen; and Z is a group which consists of (a) one oxygen atom or two non-adjacent oxygen atom, (b) --CF.sub.2 -- group and (c) any one of a single bond, --CF.sub.2 --, --CFH--, CFCl-- and --CH.sub.2 -- groups and forms a five-membered or six membered ring together with two adjacent carbon atoms of the benzene ring; is obtained by reacting a corresponding 2-cyanobenzimidazole compound and a sulfamoyl chloride derivative. The benzimidazole derivative is incorporated into agricultural and horticultural fungicides as an active ingredient.

Benzimidazole derivatives, agricultural and horticultural fungicides

There is disclosed a compound of the formula: ##STR1## wherein X is hydrogen or halogen; Y is halogen; Z is oxygen or sulfur; R.sup.1 is hydrogen or alkyl; and R.sup.2 is a group of the formula: ##STR2## wherein R.sup.3 and R.sup.4 are the same or different, and each is hydrogen, alkyl, cycloalkyl or benzyl, or the ends of R.sup.3 and R.sup.4 are connected together to be alkylene; or R.sup.2 is a group of the formula: ##STR3## wherein R.sup.5 and R.sup.6 are the same or different, and each is hydrogen or alkyl, or the ends of R.sup.5 and R.sup.6 are connected together to be alkylene, with the proviso that R.sup.2 is a group of the formula: ##STR4## when Z is oxygen, which is useful as a herbicide.

Tetrahydrophthalimide derivatives and their use as herbicides

A benzimidazole derivative having the formula, ##STR1## wherein R is cyano or thiocarbamoyl; Q is lower alkyl or a group represented by the formula NQ.sup.1 Q.sup.2, in which Q.sup.1 and Q.sup.2 are independently lower alkyl, lower alkyl substituted with phenyl, lower alkenyl or lower alkynyl, or they form a lower alkylene ring when taken together at their ends which ring may include a hetero atom; X is hydrogen or halogen; and Z is a group which consists of (a) one oxygen atom or two non-adjacent oxygen atom, (b) --CF.sub.2 --group and (c) any one of a single bond, --CF.sub.2 --, --CFH--, CFCl-- and --CH.sub.2 --groups and forms a five-membered or six membered ring together with two adjacent carbon atoms of the benzene ring; is obtained by reacting a corresponding 2-cyanobenzimidazole compound and a sulfamoyl chloride derivative. The benzimidazole derivative is incorporated into agricultural and horticultural fungicides as an active ingredient.

Benzimidazole derivatives agricultural and horticultural fungicides

A compound of the formula: ##STR1## wherein R.sup.1 is a trifluoromethyl group or a pentafluoroethyl group, R.sup.2 is a methyl group or an amino group, R.sup.3 is a C.sub.1 -C.sub.7 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo (C.sub.1 -C.sub.6) alkyl group, a halo (C.sub.3 -C.sub.6) alkenyl group or a C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.3)alkyl group and Y is an oxygen atom or a sulfur atom, which is useful as a herbicide.

Uracil derivatives and their herbicidal use

A compound of the formula: ##STR1## wherein X is an oxygen atom or a sulfur atom, Y is a hydrogen atom or a fluorine atom, Z is a methylene group or a group of the formula: N--R.sub.5 (in which R.sub.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group), R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group, a halo(C.sub.3 -C.sub.7)alkenyl group, a cyano(C.sub.1 -C.sub.6)alkyl group, a C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group, R.sub.2 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; R.sub.3 and R.sub.4 are, the same or different, each is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; n is an integer of 0 or 1, which is useful as a herbicide.

N-phenylimides, and their production and use

A compound of the formula: ##STR1## wherein R.sup.1 is a trifluoromethyl group or a pentafluoroethyl group, R.sup.2 is a hydrogen atom or a methyl group, R.sup.3 is a C.sub.1 -C.sub.7 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.1 -C.sub.6)alkyl group, a halo(C.sub.3 -C.sub.6)alkenyl group or a C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.3)alkyl group and X is a hydrogen atom or a fluorine atom, which is useful as a herbicide.

N-aminouracil derivatives, and their production and use

A benzimidazole derivative having the formula, ##STR1## wherein R is cyano or thiocarbamoyl; Q is lower alkyl or a group represented by the formula NQ.sup.1 Q.sup.2, in which Q.sup.1 and Q.sup.2 are independently lower alkyl, lower alkyl substituted with phenyl, lower alkenyl or lower alkynyl, or they form a lower alkylene ring when taken together at their ends which ring may include a hetero atom; X is hydrogen or halogen; and Z is a group which consists of (a) one oxygen atom or two non-adjacent oxygen atom, (b) --CF.sub.2 -- group and (c) any one of a single bond, --CF.sub.2 --, --CFH--, CFCl-- and --CH.sub.2 -- groups and forms a five-membered or six membered ring together with two adjacent carbon atoms of the benzene ring; is obtained by reacting a corresponding 2-cyanobenzimidazole compound and a sulfamoyl chloride derivative. The benzimidazole derivative is incorporated into agricultural and horticultural fungicides as an active ingredient.

There are disclosed novel benzofuran derivatives of the formula: ##STR1## Also disclosed are a herbicidal composition containing the above benzofuran derivative as an active ingredient and a method for exterminating undesired weeds by the application of a herbicidally effective amount of the above benzofuran derivative to an area where the undesired weeds grow or will grow.

Growing community of inventors

Takarazuka, Japan

Masayuki Enomoto