Shell Oil Comapny

E.i. Dupont De Nemours and Company

Willy D Kollmeyer

Steven A Roman

James E Powell

Samuel B Soloway

Charles H Tieman

George B Payne

Kurt H Pilgram

Kurt G Sundelin

Thomas L Brown

Paul E Porter

Earl K Jackson

Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;

Oxabicycloalkane herbicides

Compounds of the formulas I, II, or III ##STR1## wherein R is an alkyl group containing 2 to 6 carbon atoms optionally substituted by one or more halogen atoms, a cycloalkyl group containing 3 to 6 ring carbon atoms optionally substituted by one of more alkyl groups containing 1 or 2 carbon atoms, an aryl or aralkyl group containing 6 to 10 carbon atoms optionally ring-substituted by one or more halogen atoms or alkyl groups containing 1 or 2 carbon atoms or an alkoxycarbonyl alkyl group in which the alkyl portions contain from 1 to 6 carbon atoms, are useful as insecticides, particularly against the species of the Order Lepidoptera.

Insecticidal 2,6-difluorobenzoyl derivatives of

Oxacycloalkane-alpha-(thio)carboxylic acid derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or optionally-substituted alkyl; n is 0 or 1; X is O or S and Y is NR.sup.4 R.sup.5 or when X is O then Y is also OH or OR.sup.3 in which R.sup.3, R.sup.4 and R.sup.5 is H or an optionally-substituted hydrocarbyl group; and W is an optionally-substituted unsaturated, cycloalkyl, secondary alkyl, aromatic or heterocyclic group, are useful as plant growth regulators, herbicides, intermediates and the like.

Oxacycloalkane-alpha-(thio)carboxylic acid derivatives and use as plant

Intermediates for oxabicycloalkane herbicides

Certain substituted, 7-oxabicyclo[2.2.1]heptan-2-ols and -2-ones as

Novel compounds of the formula ##STR1## wherein R.sup.1 is (halo)alkyl or optionally substituted phenyl; R.sup.2 is H, or alkyl; R.sup.3 and R.sup.4 each is alkyl; and X and Y each is O or S, are useful as insecticides and miticides.

Beta-imidazolyl-alpha-(trifluoromethyl)ethenyl phosphates and

Certain substituted 3-cyclohexene-1-ol are intermediates to herbicides and plant growth.

The present invention is directed to novel compounds of formulas I or II ##STR1## wherein R is an optionally substituted unsaturated group containing up to 4 carbon atoms, a cycloalkyl group containing 3 to 10 carbon atoms, a secondary alkyl group containing 3 to 10 carbon atoms, an aromatic group containing up to 14 carbon atoms or a heterocyclic group containing up to 14 carbon atoms; in formula I, m is 0, 1 or 2; n is 1, 2 or 3; R.sup.1 and R.sup.2 each independently is a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or a hydroxyalkyl or an alkoxymethyl group in which the alkyl portion contains 1 to 6 carbon atoms; X is CH.sub.2 when m is 0, 1 or 2; or X is oxygen when m is 1 or 2; or in formula II, n is 1, 2 or 3; m is 0 or 1; and R.sup.1 and R.sup.2 each independently is a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or a hydroxyalkyl or an alkoxymethyl group in which the alkyl portion contains 1 to 6 carbon atoms. The compounds of formulas I and II are useful as plant growth regulators or herbicides.

Oxaspiro alkane and alkene ether herbicides

Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or alkyl; n is 0 or 1 and R is an unsaturated moiety, are useful as herbicides and plant growth regulators.

2-Cyano-tetrahydrofuran-5-methanols

Herbicidal cyano-tetrahydrofuranylmethyl ether and

Certain spiro ether derivatives are useful as herbicides.

Spiro ether herbicides

3-Azabicyclo(3.1.0)hexane-2-carbonitrile, a precursor for preparing 3-azabicyclo(3.1.0)hexane-2-carboxylic acid, a plant male gametocide, is prepared by (a) treating 3-azabicyclo(3.1.0)hexane with a chlorinating agent to form 3-chloro-3-azabicyclo(3.1.0)hexane; (b) treating a solution of that compound with a strong inorganic base and a lower alkanol, to give a solution of the corresponding 3-azabicyclo(3.1.0.)hex-2-ene; (c) treating the solution with an alkali metal bisulfite to form the 2-bisulfite adduct of 3-azabicyclo(3.1.0)hex-2-ene; (d) treating the reaction mixture containing the adduct with an alkali metal cyanide to form 3-azabicyclo(3.1.0)hexane-2-carbonitrile.

Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile

3-Azabicyclo(3.1.0)hexane, a precursor for preparing 3-azabicyclo(3.1.0)hexane-2-carboxylic acid, a plant gametocide, is prepared by (a) treating cis-1,2-cyclopropanedicarboxylic acid with benzylamine, to form 3-(benzyl)-3-azabicyclo(3.1.0)hexane-2,4-dione, (b) selectively reducing the dione to 3-(benzyl)-3-azabicyclo(3.1.0)hexane, and (c) hydrogenolysis of that compound to 3-azabicyclo(3.1.0)hexane.

3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione

A method of regulating and/or modifying the growth of plants by applying to the plant locus, certain beta-substituted ethanesulfinic acids, and oxygen esters thereof, is described as well as plant growth regulant formulations containing them. Some of the compounds described for use in the method of the invention are novel.

Plant growth regulators

Insecticidal 2-substituted-2-(acetoxyethyl) esters of (1-methyl-2-imidazolidinylidene)nitroacetic acid.

Growing community of inventors

Modesto, CA, United States of America

Willy D Kollmeyer