Sumitomo Chemical Company, Limited

Ryo Yoshida

Katsuzo Kamoshita

Eiki Nagano

Hiroshi Matsumoto

Shunichi Hashimoto

Seizo Sumida

Ichiki Takemoto

Naganori Hino

Hiroyuki Konishi

Kouichi Morita

Toru Haga

Hideyuki Shibata

Yuzuru Sanemitsu

Shinichi Kawamura

Tatsuhiro Hamada

Yoshihiro Mano

Ryo Sato

Koji Nakayama

Nobuaki Mito

Junichi Sato

Takeo Satomi

Masayuki Fukushima

Masachika Hirano

Hiroshi Noguchi

Junya Takahashi

Kunio Mukai

Hiromichi Oshio

Haruhiko Katoh

Hirofumi Oshita

Yoshiaki Kosuge

Kamoshita Katsuzo

Takemoto Ichiki

Soji Otsuki

Kozo Tsuji

Mitsuru Sasaki

Yoshinori Nakayama

Fumio Horide

Shuichiro Asao

Yoshiro Mano

Shunich Hashimoto

Eiyoshi Itooka

Hideo Sakamoto

A compound of the formula (VIII): ##STR1## wherein R.sup.1 represents a halo-(C.sub.1 to C.sub.6)-alkoxy group at the ortho or meta position; and W.sup.2 represents a methanesulfonyl group, a methylthio group or ##STR2## wherein R.sup.44 is a (C.sub.1 to C.sub.3)-alkoxy group.

5-substituted-2,4-diphenylpyrimidine derivatives, their production and

A compound is disclosed having the formula: ##STR1## wherein R.sup.1 represents a halo-(C.sub.1 to C.sub.6)-alkoxy group at the ortho or meta position, R.sup.2 and R.sup.3, which may be either the same or different, each represents a hydrogen atom, a halogen atom, a (C.sub.1 to C.sub.2)-alkyl group, a halo-(C.sub.1 to C.sub.2)-alkyl group, a (C.sub.1 to C.sub.2)-alkoxy group, a nitro group, a (C.sub.1 to C.sub.2)-alkylthio group, a halo-(C.sub.1 to C.sub.2)-alkylthio group or a halo-((C.sub.1 to C.sub.2)-alkoxy group, provided that both of R.sup.2 and R.sup.3, if each representing a substituent other than a hydrogen atom, are not at the ortho position for the pyrimidine ring at the same time, and W.sup.1 represents a methanesulfonyl group, or a methylthio group; provided that when W.sup.1 is a methylthio group, R.sup.1, R.sup.2 and R.sup.3 are R.sup.11, R.sup.22 and R.sup.33 wherein R.sup.11 represents a halo-(C.sub.1 to C.sub.6)-alkoxy group at the ortho or meta position, R.sup.22 and R.sup.33, which may be either the same or different, each represents a hydrogen atom, a halogen atom, a (C.sub.1 to C.sub.2)-alkyl group, a halo-(C.sub.1 to C.sub.2)-alkyl group, a (C.sub.1 to C.sub.2)-alkoxy group, or a halo-(C.sub.1 to C.sub.2)-alkoxy group, and both of R.sup.22 and R.sup.33, if each representing a substituent other than a hydrogen atom, are not at the ortho position for the pyrimidine ring at the same time.

5-substituted-2,4-diphenylpyrimidine derivatives

A compound of the formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, or a halogen atom, a (C.sub.1 to C.sub.3)-alkyl group, a halo-(C.sub.1 to C.sub.3)-alkyl group, a (C.sub.1 to C.sub.6)-alkoxy group, a (C.sub.2 to C.sub.6)-alkynyloxy group, a (C.sub.2 to C.sub.6)-alkenyloxy group, a halo-(C.sub.2 to C.sub.6)-alkynyloxy group, a halo-(C.sub.2 to C.sub.6)-alkenyloxy group, a (C.sub.1 to C.sub.2)-alkylthio group, a halo-(C.sub.1 to C.sub.6)-alkoxy group, a halo-(C.sub.1 to C.sub.2)-alkylthio group, a phenoxy group, a (C.sub.1 to C.sub.3)-alkylcarboxy group, a halo-(C.sub.1 to C.sub.3)-alkylcarboxy group, a (C.sub.1 to C.sub.2)-alkoxy-(C.sub.1 to C.sub.2)-alkoxy group, a halo-(C.sub.1 to C.sub.2)-alkoxy-halo-(C.sub.2 to C.sub.3)-alkoxy group, a (C.sub.1 to C.sub.3)-alkylsulfonyloxy group, a halo-(C.sub.1 to C.sub.3)-alkylsulfonyloxy group, a cyano group, a (C.sub.1 to C.sub.3)-alkoxycarbonyl group or an aminomethyl group, at the ortho or meta position; R.sup.2 and R.sup. 3, which may be either the same or different, each represents a hydrogen atom, a halogen atom, a (C.sub.1 to C.sub.2)-alkyl group, a halo-(C.sub.1 to C.sub.2)-alkyl group, a (C.sub.1 to C.sub.2)-alkoxy group, a nitro group, a (C.sub.1 to C.sub.2)-alkylthio group, a halo-(C.sub.1 to C.sub.2)-alkylthio group or a halo-(C.sub.1 to C.sub.2)-alkoxy group; and R.sup.4 represents a (C.sub.1 to C.sub.2)-alkyl group, provided that both R.sup.1 and R.sup.2 are not a hydrogen atom at the same time and that both of R.sup.2 and R.sup.3, if each representing a substituent other than a hydrogen atom, are not at the ortho position for the pyrimidine ring at the same time. The compound is used as herbicides.

5-substituted-2,4-diphenylpyrimidine derivatives and their use

A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.1 -C.sub.8 alkyl group except isopropyl, which is useful as a herbicide.

Tetrahydrophthalimides, and their production and use as herbicides

A herbicidal composition which comprises a herbicidally effective amount of the combinations of (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6 ,7-tetrahydro-1H-isoindole-1,3(2H)-dione and (b) at least one of (2-amino-4-methylphosphinobutyryl)alanylalanine and its salt (bialaphos) and DL-homoalanin-4-yl(methyl)phosphinic acid and its salt (glufosinate), and an inert carrier or diluent. The composition exerts synergistic herbicidal activity.

Herbicidal composition

A herbicidal composition which comprises as an active ingredient a herbicidally effective amount of the combination of (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6 ,7-tetrahydro-1H-isoindole-1,3(2H)-dione and (b) a compound of the formula: ##STR1## wherein R.sub.1 is any one of the formulas: ##STR2## wherein R.sub.2 is a C.sub.1 -C.sub.4 alkyl group, and an inert carrier or diluent. The composition shows a synergistic herbicidal potency.

A herbicidal composition which comprises as the active ingredients (a) 2-(4-chloro- fluoro-5-n-pentyloxycarbonylmethoxyphenyl)-4,5,6,7-tetrahydro-2H-isoindole - 1,3-dione and (b) at least one of methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenoneoxime-O-acetate (PPG-1013), 1-(carboethoxy)ethyl 5-[2-chloro-4-trifluoromethyl)phenyl]-2-nitrobenzoate (lactofen) and 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinol inecarboxylic acid (imazaquin), and an inert carrier or diluent. Said composition exerts an enhanced herbicidal potency.

Herbicidal composition with lactofon

A herbicidal composition which comprises as the active ingredients (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and (b) at least one of 2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1- one (sethoxydim) and methyl 4-hydroxy-6,6-dimenthyl-2-oxo-3-[1-[(2-propenyloxy)imino]butyl]-3-cyclohex ene-1-carboxylate (alloxydim), and an inert carrier or diluent.

A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, which is useful as a herbicide.

Alkoxy-nitrobenzene and alkoxy-aminobenzene compounds useful in the

Tetrahydrophthalimides, and their production and use

A herbicidal composition which comprises as an active ingredient a herbicidally effective amount of the combination of (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6 ,7-tetrahydro-1H-isoindole-1,3(2H-dione and (b) a compound of the formula: ##STR1## wherein R.sub.1 is any one of the formulas: ##STR2## wherein R.sub.2 is a C.sub.1 -C.sub.4 alkyl group, and an inert carrier or diluent. The composition shows a synergistic herbicidal potency.

A tetrahydrophthalimide compound of the formula: ##STR1## wherein R is methyl or n-pentyl, which is useful as a post emergent herbicide for soybean field.

Tetrahydrophthalimide compounds, and their production and use

A herbicidal composition which comprises as the active ingredients (a) 2-(4-chloro-2-fluoro-5-n-pentyloxy-carbonylmethoxyphenyl)-4,5,6,7-tetrahyd ro- -2H-isoindole-1,3-dione and (b) at least one of methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenoneoxime-O-acetate (PPG-1013), 1-(carboethoxy)ethyl 5-[2-chloro-4-trifluoromethyl)phenyl]-2-nitrobenzoate (lactofen) and 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinol inecarboxylic acid (imazaquin), and an inert carrier or diluent. Said composition exerts an enhanced herbicidal potency.

A compound of the formula: ##STR1## wherein R is a C.sub.2 -C.sub.3 alkyl group, a C.sub.3 -C.sub.4 alkenyl group, or a C.sub.3 -C.sub.4 alkynyl group, and X is a chlorine or bromine atom, is disclosed. These compounds are useful as intermediates in the production of herbicidal 3-chlorotetrahydroindazoles.

2-fluoro-4-halo-5-marcapto-phenyl-hydrazines

A herbicidal composition which comprises as the active ingredients (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and (b) 2-[[(E)-3-chloroallyloxyimino]propyl]-5-(2-ethylthiopropyl)-3-hydroxycyclo hex-2-enone (clethodim), and an inert carrier or diluent.

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Kawanishi, Japan

Ryo Yoshida