Shell Oil Comapny

Robert J Searle

Royston H Davis

Janet A Day

Roger E Woodall

Michael J Bull

Barry R Devlin

Clive B Boyce

Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.3 each is hydrogen or R.sup.1 and R.sup.3 together form a second carbon-to-nitrogen bond, R.sup.2 is hydrogen or cyano, R.sup.4 is alkyl and Ar is one of certain aromatic moieties. The compounds can be used as abscission agents for the loosening of fruit and/or leaves on plants.

Compounds for the loosening of fruit and/or leaves on plants

2-cyano-2-carboxy-3-azabicyclo[3.1.0]hexane, hydrates, esters, and salts thereof, useful as pollen-suppressants.

2-Cyano-2-carboxy-3-azabicyclo[3.1.0]hexane, hydrates, esters, and salts

3-Azabicyclo(3.1.0)hexane-2-carboxylic acid, a plant gametocide, is prepared by effecting reaction between cis 2-aminomethylcyclopropyl-1,1-dimethyl acetal and a cyanide in the presence of a liquid lower-alkanecarboxylic acid; treating the resulting N-alkanoyl-3-azabicyclo(2.1.0)hexane-2-carbonitrile with a strong acid; treating the resulting 3-alkanoyl-3-azabicyclo(3.1.0)hexane-2-carboxylic acid with strong acid to form the desired 3-azabicyclo(3.1.0)hexane-2-carboxylic acid.

Process for preparing 3-azabicyclo(3.1.0)hexane-2-carboxylic acid

3-azabicyclo(3.1.0)hexane-2-carboxylic acid, a plant gametocide, is prepared by effecting reaction between cis 2-aminomethylcyclopropyl-1,1-dimethyl acetal and a cyanide in the presence of a liquid lower-alkanecarboxylic acid; treating the resulting N-alkanoyl-3-azabicyclo(2.1.0)hexane-2-carbonitrile with a strong acid; treating the resulting 3-alkanoyl-3-azabicyclo(3.1.0)hexane-2-carboxylic acid with strong acid to form the desired 3-azabicyclo(3.1.0)hexane-2-carboxylic acid.

2-Aminomethylcyclopropyl-1,1-dialkylacetals

Esters of 2-carboxy-3-azabicyclo(3.1.0)hex-2-ene, useful as intermediates to the cis-racemate of methanoproline, and as inhibitors of pollen formation in cereal grains.

Esters of 2-carboxy-3-azabicyclo-(3.1.0)hex-2-ene

Certain esters of alpha-substituted-phenoxybenzyl alcohols of the formula ##STR1## wherein A represents certain optionally substituted aralkyl, alkyl or cyclopropyl groups at least one of X and Y is sulfur and the other independently represents oxygen or sulfur and R represents certain alkyl, alkenyl, alkynyl, aralkyl, alkaryl or aryl groups, hydrogen or a salt-forming cation, are useful as pesticides.

Phenoxybenzyl ester pesticides

Certain dispirocyclopropane carboxylates are useful as pesticides.

Dispirocyclopropane carboxylate pesticides

Compounds of the formula ##STR1## wherein R is alkenyl, aralkyl or alkyl; X is H, CN, thioamide, or alkynyl; and Y is phenoxyphenyl or phthalimido, are useful as pesticides.

2-Substituted isovaleric acid ester pesticides

Certain carboxylic acid esters in which the alcohol portion contains an alpha-thioamide group are useful as pesticides.

Thioamide pesticides

Pesticidal benzyl ethers of the formula: ##STR1## wherein each symbol has a meaning defined in the specification.

Benzyl ethers

Alpha-cyano-phenoxybenzyl-isovalerates

Cyclopropane derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2 are alkyl; R.sub.3 is hydrogen, alkynyl or cyano; R.sub.4 is optionally substituted phenyl and n is an integer of 2 to 5 are useful as pesticides.

Growing community of inventors

Sittingbourne, United Kingdom

Robert J Searle