Shell Oil Comapny

E.i. Dupont De Nemours and Company

Steven A Roman

Samuel B Soloway

Willy D Kollmeyer

James E Powell

Charles H Tieman

George B Payne

Kurt G Sundelin

Charles A Horne, Jr

Stephen A Salvo

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

Intermediates for oxabicycloalkane herbicides

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

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

Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.

Cyclopropanecarboxylate pesticides and their preparation

Certain 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines are useful as pesticides.

Use of pyrroloquinazolinediamines as pesticides

(1R,cis)-Oxyimino-substituted cyclopropanecarboxylic acids are prepared via a (1R,4R,5S)-2-acetoxy-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexane intermediate.

Preparation of (1R,cis)-oxyimino-substituted cyclopropanecarboxylic acids

(1R,cis)-Oxyimino-substituted cyclopropanecarboxylic acids are prepared via a (1R,4R,5S)-4-acetoxy-6,6-dimethyl-2-oxo-3-oxabicyclo [3.1.0]hexane intermediate.

Preparation of (1R, cis)-oxyimino-substituted cyclo-propanecarboxylic

Novel pyrethroid intermediates ##STR1## wherein R.sup.1 and R.sup.2 each is alkyl are prepared by treating 2,2-dimethyl-3-(2-oxopropyl)cyclopropylacetaldehyde with a trialkylsilyldialkylamine. The above compounds can be treated with ozone to form 2,3-dimethyl-3-(2-oxopropyl)cyclopropanecarbaldehyde.

Ketoenamine pyrethroid intermediates

Novel pyrethroid intermediates ##STR1## wherein R.sup.1 and R.sup.2 each is alkyl are prepared by treating 2,2-dimethyl-3-(2-oxopropyl)cyclopropylacetaldehyde with a trialkylsilyldialkylamine. The above compounds can be treated with ozone to form 2,2-dimethyl-3-(2-oxopropyl)cyclopropanecarbaldehyde.

(1R,cis)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein R.sup.1 is C.sub.3-6 alkyl and R is .alpha.-cyano-3-phenoxybenzyl or 3-phenoxybenzyl, are highly active pesticides.

Oxyimino-substituted (1R,cis)cyclopropanecarboxylate pesticides

(1R,cis)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein X is chlorine, bromine or OR in which

Oxyimino-substituted (1R, cis)-cyclopropanecarboxylate pesticides

New cyclopropane compounds have the formula ##STR1## wherein X is chlorine, bromine or OR in which

Oxyimino-substituted cyclopropanecarboxylate

Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.

Cyclopropanecarboxylate pesticides preparation

(1R, Trans)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein X is chlorine, bromine or OR in which

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Oakdale, CA, United States of America

Steven A Roman