Stauffer Chemical Company

Zeneca Limited

Ici Americas, Inc.

Imperial Chemical Industries Limited

Zeneca Litmited

David L Lee

Charles G Carter

Frank X Woolard

William J Michaely

Francis H Walker

David Cartwright

John M Cox

Glynn Mitchell

John E Barton

Hsiao-Ling M Chin

David B Kanne

Raymond A Felix

Nhan H Nguyen

Gary W Kraatz

Donald R James

John M Shribbs

Nigel John Barnes

John E D Barton

Herbicidal compounds

A compound of formula (I): ##STR1## or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X.sup.1 and X.sup.2 are independently oxygen or sulphur, R.sup.1 is an optionally substituted heterocyclic or cycloalkyl group, and Y is an optionally substituted C.sub.2 -C.sub.4 alkylene group which is optionally interposed by an oxygen atom, a group ##STR2## a group ##STR3## or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R.sup.b is alkyl or alkoxy; provided that when X, X.sup.1 and X.sup.2 are oxygen, R.sup.1 is not pyridyl or pyrimidinyl. Processes for the preparation of these compounds and herbicidal compositions containing them are also described and claimed.

This invention relates to processes for the preparation of aryl-.beta.-diketones and aryl-pyrimidine ketones. In addition, this invention relates to the preparation of aryl-.beta.-triketones and dimethyl aminomethylene .beta.-diketones, which are useful as crop protection intermediates.

Processes for the preparation of aryl-.beta.-diketones, arylpyrimidine

This invention relates to 4-benzoylisoxazoles of formula (I) ##STR1## as well as herbicide compositions containing them and their use as herbicides.

Herbicidal 4-benzoylisoxazoles derivatives

Herbicidal 3-substituted pyridine compounds and derivatives thereof of the formula: ##STR1## wherein Ar is a substituted or unsubstituted 5- or 6-membered heteroaryl group having 1, 2 or 3 ring nitrogen atoms with the remainder of the ring atoms being carbon; a substituted or unsubstituted 5-membered heteroaryl group having a ring heteroatom of oxygen or sulfur with the remainder of the ring atoms being carbon; or a substituted or unsubstituted 5-membered heteroaryl group having one ring nitrogen atom and either an oxygen or sulfur ring heteroatom with the remainder of the ring atoms being carbon. Herbicidal compositions containing such 3-substituted pyridine compounds and derivatives thereof and methods of controlling undesirable vegetation employing these compounds and derivatives are also disclosed. The compounds in which XR is hydroxyl are also useful as intermediates for producing the disclosed 3-substituted pyridine derivatives.

3-substituted pyridine compounds and derivatives thereof

A compound of formula (I): ##STR1## or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X.sup.1 and X.sup.2 are independently oxygen or sulphur, R.sup.1 is an optionally substituted heterocyclic or cycloalkyl group, and Y is an optionally substituted C.sub.2 -C.sub.4 alkylene group which is optionally interposed, by an oxygen atom, a group ##STR2## a group ##STR3## or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R.sup.b is alkyl or alkoxy; provided that when X, X.sup.1 and X.sup.2 are oxygen, R.sup.1 is not pyridyl or pyrimidinyl. Processes for the preparation of these compounds and herbicidal compositions containing them are also described and claimed.

Herbicidal 4-cycloalkyl-5-substituted pyrimidine compounds of the formula ##STR1## are described. Herbicidal compositions containing such substituted-pyrimidinyl compounds and methods of controlling undesirable vegetation employing these compounds are also disclosed. The compounds in which XR, is hydroxyl are also useful as intermediates for producing the disclosed substituted-pyrimidinyl derivatives.

4-cycloalkyl-5-substituted pyrimidine compounds useful as crop

Herbicidal compositions containing 4-benzoylisoxazole compounds and antidotal compounds therefor to reduce injury to various crops, particularly corn, from the phytotoxic effects of 4-benzoylisoxazole herbicides when used alone or in combination with additional pesticidally active ingredients. Methods for reducing phytotoxicity or injury to crop plants, particularly corn crops, due to 4-benzoylisoxazole herbicides are also described.

Herbicidal compositions of 4-benzoylisoxazole and antidotes therefor

A compound of formula (I): ##STR1## or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X.sup.1 and X.sup.2 are independently oxygen or sulphur, R.sup.1 is an optionally substituted heterocyclic or cycloalkyl group, and Y is an optionally substituted C.sub.2 -C.sub.4 alkylene group which is optionally interposed by an oxygen atom, a group ##STR2## or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R.sup.b is alkyl or alkoxy; provided that when X, X.sup.1 and X.sup.2 are oxygen, R.sup.1 is not pyridyl or pyrimidinyl. Processes for the preparation of these compounds and herbicidal compositions containing them are also described and claimed.

A compound of formula (I): ##STR1## or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X.sup.1 and X.sup.2 are independently oxygen or sulphur, R.sup.1 is an optionally substituted heterocyclic or cycloalkyl group, and Y is an optionally substituted C.sub.2 -C.sub.4 alkylene group which is optionally interposed by an oxygen atom, a group ##STR2## or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R.sup.b is alkyl or alkoxy; provided that when X, X.sup.1 and X.sup.2 are oxygen R.sup.1 is not pyridyl or pyrimidinyl. Processes for the preparation of these compounds and herbicidal compositions containing them are also described and claimed.

Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexandediones. The intermediate benzoic acids of this invention have the following structural formula ##STR1## wherein R.sup.6 is chlorine, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or hydroxy; n is the integer 0 or 2; and R.sup.7 is C.sub.1 -C.sub.4 alkyl.

Trisubstituted benzoic acid intermediates

Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR2## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; R.sup.1 and R.sup.2 together are alkylene having 3 to 6 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.7 is hydrogen or 3-C.sub.1 -C.sub.4 alkoxy; and R.sup.8 is (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) OCF.sub.3 ; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined, their use as herbicides and herbicidal compositions containing the compounds.

Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones

Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexanediones. The intermediate benzoic acids of this invention have the following structural formula ##STR1## wherein R.sup.6 is chlorine, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or hydroxy; n is the integer 0 or 2; and R.sup.7 is C.sub.1 -C.sub.4 alkyl.

Growing community of inventors

Martinez, CA, United States of America

David L Lee