Stauffer Chemical Company

Imperial Chemical Industries Limited

Harry Tilles

Francis H Walker

Eugene G Teach

Donald R James

Michael D Broadhurst

Lawrence L Buren

Paul E Hoch

Barney J Randolph

Novel herbicides have the formula ##STR1## in which R is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylcarbamoyl, C.sub.1 -C.sub.4 mono- or dialkylamino, phenoxy or nitro;

Arylphosphonoamidate herbicides

Novel S-benzyl thiolcarbamates are disclosed, having the formula ##STR1## in which R.sup.1 is selected from the group consisting of hydrogen and methoxy,

S-benzyl thiolcarbamates and their use in controlling weeds in rice

Herbicidal active sulfoxide and sulfone compounds and their method of use as described herein. The compounds have the following generic formula: ##STR1## wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and lower haloalkyl; R.sub.1 and R.sub.2 taken together form an alkylene group having 5 or 6 carbon atoms, alkyl substituted alkylene group or ##STR2##

Herbicidal active sulfoxide and sulfone compounds

Herbicidal active sulfoxide compounds

Thiocarbamates are prepared by a process comprising reacting an aqueous solution of a thiocarbamate salt with an organic halide in the presence of a catalytic amount of a quaternary ammonium salt having the formula

Thiocarbamate preparation utilizing quaternary ammonium salt catalysts

A mixture of cis and trans isomers of S-isopropyl-1-(5-ethyl-2-methylpiperidinecarbothioate) has been found to have improved herbicidal properties in contrast to the trans isomer alone. Preferably the mixture contains at least about 20%, most preferably between about 60 and about 65%, of the cis isomer. The S-isopropyl-1-(5-ethyl-2-methylpiperidinecarbothioate) having a desired amount of cis isomer can be produced by a two-step process comprising hydrogenation of 2-methyl-5-ethyl pyridine using a catalyst comprising rhodium supported on activated carbon to produce 2-methyl-5-ethyl piperidine and reacting the piperidine with isopropyl chlorothiolformate.

Herbicidal effect of a mixture of cis and trans isomers of

Process for increasing the cis content of a mixture of cis and trans

Novel compounds having the formula ##STR1## in which X is hydrogen, mono- or dihalo or 2-methyl; Y is oxygen or sulfur; R is alkyl, lower alkenyl, chloro-lower alkenyl, carbomethoxymethyl or methyl-thiomethyl; and R.sub.1 is lower alkyl, lower alkenyl or p-chlorobenzyl, provided that if X is 4-chloro, R is other than methyl-thiomethyl. The novel compounds of this type possess aphicidal activity. Also disclosed is a novel process for making O-(substituted)benzyl thiocarbamate intermediates for these compounds.

Process for preparation of O-(substituted)benzyl thiocarbamates

Novel compounds having the formula ##STR1## in which X is hydrogen, mono- or dihalo or 2-methyl; Y is oxygen or sulfur; R is alkyl, lower alkenyl, chloro-lower alkenyl, carbomethoxymethyl or methyl-thiomethyl; and R.sub.1 is lower alkyl, lower alkenyl or p-chlorobenzyl, provided that if X is 4-chloro, R is other than methyl-thiomethyl. The novel compounds of this type possess aphicidal activity Also disclosed is a novel process for making O-(substituted)benzyl thiocarbamate intermediates for these compounds.

S-alkyl carbonimidothioates and their use as aphicides

Intermediate compounds useful for manufacturing herbicidal active sulfoxide and sulfone compounds are described herein. The compounds have the following generic formula: ##EQU1## wherein R is selected from the group consisting of lower alkyl and haloalkyl; R.sub.1 and R.sub.2 taken together can form a heterocyclic ring structure having from 2 to 10 carbon atoms or alkyl substituted heterocyclic ring structure. The heterocyclic ring can be provided with cross-bonding.

Growing community of inventors

El Cerrito, CA, United States of America

Harry Tilles