Stauffer Chemical Company

Zeneca Limited

Ici Americas, Inc.

Other

Imperial Chemical Industries Limited

Raymond A Felix

Frank X Woolard

Eugene G Teach

David L Lee

Donald R James

Hsiao-Ling M Chin

Joanna K Hsu

David B Kanne

Jeffery T Springer

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 substituted N-benzotriazoles of the formula ##STR1## in which: R.sup.1, R.sup.2, R.sup.3,R.sup.4, R.sup.5,R.sup.6, R.sup.7, X are as defined in the specification. The compounds exhibit herbicidal activity.

N-benzotriazoles

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

Substituted N-benzotriazoles of the general formula ##STR1## exhibit herbicidal activity. Herbicidal compositions and related methods of using the substituted N-benzotriazoles are also disclosed.

This invention relates to a process for producing a compound of the formula ##STR1## comprising reacting a compound having the formula ##STR2## with cyanogen chloride or cyanogen bromide.

2-(substituted imino)-1,3,4-dihydrothiadiazoles

Compounds having the formula ##STR1## in which: R.sub.1 is hydrogen or fluoro;

Arylpyridone herbicides

Compounds having the formula ##STR1## wherein R is an aromatic or aliphatic group; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, C.sub.1-4 alkyl or phenyl; X is halogen; and Y is halogen or an aromatic group; are prepared in a regioselective manner by treating a compound having the formula ##STR2## with a catalytic amount of a palladium(O) or a palladium(II) transition metal catalyst.

Process for the preparation of N-allylamides from O-allylimidates

A 2-iminophenyl thiazolidine having the formula ##STR1## wherein R is hydrogen or methyl; R.sub.1 is halo, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, perhalomethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthhio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, C.sub.1 -C.sub.4 alkyloxyiminomethyl, benzyloxyiminomethyl, 1-(C.sub.1 -C.sub.4 alkyl)-oxyiminoethyl or 1-benzyloxyiminoethyl; R.sub.2 is hydrogen or halo; R.sub.3 and R.sub.4 are independently hydrogen, halo, nitro, cyano, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkoxy, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; and X is hydrogen or halogen. Also disclosed is a process for making the compounds and a method of use which comprises applying the compound or composition to the locus where control is desired.

Iminophenylthiazolidines, process of preparation and method of use

Novel herbicides are 3-(substituted) phenyl-2-(substituted imino)-1,3,4-dihydrothiadiazoles. Also disclosed are intermediates for such compounds, and processes for producing the herbicidal compounds and their intermediates.

Novel 2-(substituted imino)-1,3,4-dihydrothladiazoles

An iminooxazolidine having the formula ##STR1## wherein X and Y are the same or different and are selected from the group consisting of cyano, halogen, acyl, alkyl, alkylthio, haloalkyl, trihalomethylthio, alkylsulfenyl, alkoxy, carboalkoxy and trihalomethyl wherein the alkyl groups have from 1 to 5 carbon atoms;

Iminooxazolidines and herbicidal method of use

A process of the preparation of iminooxazolidines which comprises (a) reacting a urea alcohol of the formula ##STR1## X, Y, n and R are as defined, with a dehydrating agent to form an intermediate salt compound of the formula ##STR2## wherein X, Y, n and R are as previously defined and X.degree. is halogen or other salt forming anion and (b) reacting said salt compound with a base to form a compound of the formula ##STR3##

Process for preparation of iminooxazolidines

A process for the preparation of cyclic urea compounds in which a substituted anilino alkanone is reacted with an arylsubstituted isocyanate to form an intermediate imidazoline compound, and said imidazoline compound is hydrogenated in the presence of suitable catalyst to form an imidazolidine of the formula ##STR1## wherein X, X', Y and Y' are the same or different and are selected from the group consisting of trifluoromethyl, chloro, bromo, fluoro, hydrogen, cyano, nitro, alkyl, thioalkyl, halothioalkyl, alkoxy and sulfonylalkyl wherein the alkyl groups have from 1 to 4 carbon atoms; and R is selected from the group consisting of hydrogen and alkyl having from 1 to about 4 carbon atoms. Also included are intermediate anilino alkanones and the process of making them.

Cyclic ureas

Compounds having the formula ##STR1## in which R is hydrogen, cyano or --COOR.sub.2 ; R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; and Z is ##STR2## in which A is halogen, B is halogen or hydrogen and Y is nitrogen or --CH--, are herbicides.

Herbicidal phosphonomethyl amides

A substituted oxazolidone compound having the formula ##STR1## wherein Ar.sup.1 and Ar.sup.2 are the same or different and are aromatic or a substituted aromatic group wherein the substituent is selected from chlorine, bromine, chloride or trifluoromethyl, and R is lower alkyl having from 1 to 6 carbon atoms.

Oxazolidone herbicides and methods of use

Herbicidally active thiolcarbamates are employed in combination with certain allyl amine salts of thiocarbamic acid compounds having the formula ##STR1## wherein R.sub.4 and R.sub.5 are independently selected from the group consisting of allyl, alkyl substituted allyl, and lower alkyl groups having from about 1 to about 6 carbon atoms;

Growing community of inventors

Richmond, CA, United States of America

Raymond A Felix