Imidazolidinones, and imidazolidinethiones, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents

A method for the control of undesirable monocotyledonous and dicotyledonous plant species comprising:

• applying to the foliage of said plants or to soil containing seeds or other propagating organs thereof, a herbicidally effective amount of a compound having the structure:
• ##STR225## wherein R is hydrogen;
• C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.4 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.3)alkylammonium;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen, or C.sub.1 -C.sub.3 alkoxycarbonyl or with two C.sub.1 -C.sub.4 alkoxy groups or two halogen atoms;
• C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
• C.sub.3 -C.sub.10 alkynyl or,
• a cation of alkali metals or organic-ammonium;
• R.sub.1 and R.sub.2 each represent C.sub.1 -C.sub.3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R.sub.1 and R.sub.2 is 2 to 5;
• and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with methyl;
• A is nitrogen or --CR.sub.3 ;
• W is oxygen or sulfur;
• X is hydrogen, halogen or methyl;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, NR.sub.4 R.sub.5, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy,
• CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ;
• R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl;
• And, when taken together, Y and Z may form a ring in which YZ is represented by
• (1) the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 2, 3 and 4, provided that when A is --CR.sub.3, then X is hydrogen;
• or
• (2) by the structure:
• ##STR226## where, when A is CR.sub.3, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alkoxy, or X is hydrogen;
• and when A is nitrogen, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, OCF.sub.3, OCHF.sub.2, OCF.sub.2 CHF.sub.2, C.sub.1 -C.sub.4 alkylamino, dialkyl(C.sub.1 -C.sub.4)amino, chlorophenoxy, methylphenyl, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, R.sub.7 or R.sub.8, may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• or
• (3) by the structures:
• ##STR227## where B is oxygen or sulfur;
• R.sub.9 and R.sub.10 each represent hydrogen, halogen, phenyl, or C.sub.1 -C.sub.4 alkyl;
• R.sub.11 and R.sub.12 each represent hydrogen, C.sub.1 -C.sub.4 alkyl and phenyl;
• and when R.sub.1 and R.sub.2 are not the same, the optical or cis- or trans-isomer thereof or except when R is a salt-forming cation, the acid addition salts thereof.

A method for the selective control of undesirable monocotyledonous and dicotyledonous plant species in the presence of graminaceous crops, leguminous crops or sunflowers, comprising:

• applying to the locus in which the crops are planted or growing, an effective amount of a compound having the structure:
• ##STR234## wherein R is hydrogen;
• C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.4 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.3)alkylammonium;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen, or C.sub.1 -C.sub.3 alkoxycarbonyl or with two C.sub.1 -C.sub.4 alkoxy groups or two halogen atoms;
• C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
• C.sub.3 -C.sub.10 alkynyl or,
• a cation of alkali metals or organicammonium;
• R.sub.1 and R.sub.2 each represent C.sub.1 -C.sub.3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R.sub.1 and R.sub.2 is 2 to 5;
• and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with methyl;
• A is nitrogen or --CR.sub.3 ;
• W is oxygen or sulfur;
• X is hydrogen, halogen or methyl;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, NR.sub.4 R.sub.5, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ;
• R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl;
• and, when taken together, Y and Z may form a ring in which YZ is represented by
• (1) the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4, provided that when A is --CR.sub.3, then X is hydrogen;
• or
• (2) by the structure:
• ##STR235## where, when A is CR.sub.3, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.3 alkoxy, and X is hydrogen;
• and when A is nitrogen, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyltho, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, OCF.sub.3, OCHF.sub.2, OCF.sub.2 CHF.sub.2, C.sub.1 -C.sub.4 alkylamino, dialkyl(C.sub.1 -C.sub.4)amino, chlorophenyl, methylphenyl, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, R.sub.7 or R.sub.8, may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• or
• (3) by the structures:
• ##STR236## where B is oxygen or sulfur;
• R.sub.9 and R.sub.10 each represent hydrogen, halogen, phenyl, or C.sub.1 -C.sub.4 alkyl;
• R.sub.11 and R.sub.12 each represent hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl;
• and when R.sub.1 and R.sub.2 are not the same, the optical or cis- or trans-isomers thereof or except when R is a salt-forming cation, the acid addition salts thereof.

A method for regulating the growth of graminaceous crops, leguminous crops or sunflowers, comprising:

• applying to the foliage of the crops or to the soil in which there have been planted, a plant growth regulating amount of a compound having the structure:
• ##STR237## wherein R is hydrogen;
• C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.4 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzoyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.3)alkylammonium;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen, or C.sub.1 -C.sub.3 alkoxycarbonyl or with two C.sub.1 -C.sub.4 alkoxy groups or two halogen atoms;
• C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
• C.sub.3 -C.sub.10 alkynyl or,
• a cation of alkali metals and organicammonium;
• R.sub.1 and R.sub.2 each represent C.sub.1 -C.sub.3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R.sub.1 and R.sub.2 is 2 to 5;
• and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with methyl;
• A is nitrogen or --CR.sub.3 ;
• W is oxygen or sulfur;
• X is hdyrogen, halogen or methyl;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, NR.sub.4 R.sub.5, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ;
• R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl;
• and, when taken together, Y and Z may form a ring in which YZ is represented by
• (1) the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4, provided that when A is --CR.sub.3, then X is hydrogen;
• or
• (2) by the structure:
• ##STR238## where, when A is CR.sub.3, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.3 alkoxy, and X is hydrogen;
• and when A is nitrogen, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, OCF.sub.3, OCHF.sub.2, OCF.sub.2 CHF.sub.2, C.sub.1 -C.sub.4 alkylamino, dialkyl(C.sub.1 -C.sub.4)amino, chlorophenyl, methylphenyl, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, R.sub.7 or R.sub.8, may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• or
• (3) by the structures:
• ##STR239## where B is oxygen or sulfur;
• R.sub.9 and R.sub.10 each represent hydrogen, halogen, phenyl, or C.sub.1 -C.sub.4 alkyl;
• R.sub.11 and R.sub.12 each represent hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl.

A herbicidal composition comprising an inert diluent and a herbicidally effective amount of a compound having the structure:

• ##STR240## wherein R is hydrogen;
• C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.4 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.3)alkylammonium;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen, or C.sub.1 -C.sub.3 alkoxycarbonyl or with two C.sub.1 -C.sub.4 alkoxy groups or two halogen atoms;
• C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
• C.sub.3 -C.sub.10 alkynyl or,
• a cation of alkali metals and organic-ammonium;
• R.sub.1 and R.sub.2 each represent C.sub.1 -C.sub.3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R.sub.1 and R.sub.2 is 2 to 5;
• and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with methyl;
• A is nitrogen or --CR.sub.3 ;
• W is oxygen or sulfur;
• X is hydrogen, halogen or methyl;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, NR.sub.4 R.sub.5, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ;
• R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl;
• and, when taken together, Y and Z may form a ring in which YZ is represented by
• (1) the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4, provided that when A is --CR.sub.3, then X is hydrogen;
• or
• (2) by the structure:
• ##STR241## where, when A is CR.sub.3, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alkoxy, and X is hydrogen;
• and when A is nitrogen, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, OCF.sub.3, OCHF.sub.2, OCF.sub.2 CHF.sub.2, C.sub.1 -C.sub.4 alkylamino, dialkyl(C.sub.1 -C.sub.4)amino, chlorophenyl, methylphenyl, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, R.sub.7 or R.sub.8, may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• or
• (3) by the structures:
• ##STR242## where B is oxygen or sulfur;
• R.sub.9 and R.sub.10 each represent hydrogen, halogen, phenyl, or C.sub.1 -C.sub.4 alkyl;
• R.sub.11 and R.sub.12 each represent hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl;
• and when R.sub.1 and R.sub.2 are not the same, the optical or cis- or trans-isomers thereof or except when R is a salt-forming cation, the acid addition salts thereof.

A process for the production of the compound of the formula ##STR243## wherein R may be hydrogen, but preferably is

• C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.4 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.3)alkylammonium;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen, or C.sub.1 -C.sub.3 alkoxycarbonyl or with two C.sub.1 -C.sub.4 alkoxy groups or two halogen atoms;
• C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
• or
• C.sub.3 -C.sub.10 alkynyl;
• R.sub.1 and R.sub.2 each represent C.sub.1 -C.sub.3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R.sub.1 and R.sub.2 is 2 to 5;
• and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with methyl;
• A is nitrogen of --CR.sub.3 ;
• W is oxygen or sulfur;
• X is hydrogen, halogen or methyl;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, NR.sub.4 R.sub.5, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• R.sub.3 is hydrogen, chlorine, bromine, iodine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ;
• R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl;
• and, when taken together, Y and Z may form a ring in which YZ is represented by
• (1) the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4, provided that when A is --CR.sub.3, then X is hydrogen;
• or
• (2) by the structures:
• ##STR244## where B is oxygen or sulfur;
• R.sub.9 and R.sub.10 each represent hydrogen, halogen, phenyl, or C.sub.1 -C.sub.4 alkyl;
• R.sub.11 and R.sub.12 each represent hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl;
• and when R.sub.1 and R.sub.2 are not the same, the optical or cis- or trans-isomers thereof characterized by reducing a compound of the formula ##STR245##

A process for the production of a compound of the formula:

• ##STR247## wherein R is preferably methyl but may be
• C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.4 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.3)alkylammonium;
• C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups:
• C.sub.1 -C.sub.3 alkoxy, phenyl, halogen, or C.sub.1 -C.sub.3 alkoxycarbonyl or with two C.sub.1 -C.sub.4 alkoxy groups or two halogen atoms;
• C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
• or
• C.sub.3 -C.sub.10 alkynyl;
• R.sub.1 and R.sub.2 each represent C.sub.1 -C.sub.3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R.sub.1 and R.sub.2 is 2 to 5;
• and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with methyl;
• A is nitrogen or --CR.sub.3 ;
• W is oxygen or sulfur;
• X is hydrogen, halogen or methyl;
• Y and Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, NR.sub.4 R.sub.5, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
• R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ;
• R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.5 is C.sub.1 -C.sub.4 alkyl;
• and, when taken together, Y and Z may form a ring in which YZ is represented by
• (1) the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4, provided that when A is --CR.sub.3, then X is hydrogen;
• or
• (2) by the structure:
• ##STR248## where, when A is CR.sub.3, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alkoxy, and X is hydrogen;
• and when A is nitrogen, L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, C.sub.1 -C.sub.4 alkylamino, dialkyl(C.sub.1 -C.sub.4)amino, OCF.sub.3, OCHF.sub.2, OCF.sub.2 CHF.sub.2, chlorophenyl, methylphenyl, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, with the proviso that only one of L, M, R.sub.7 or R.sub.8, may represent a substituent other than hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• or
• (3) by the structures:
• ##STR249## where B is oxygen or sulfur;
• R.sub.9 and R.sub.10 each represent hydrogen, halogen, phenyl, or C.sub.1 -C.sub.4 alkyl;
• R.sub.11 and R.sub.12 each represent hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl;
• and when R.sub.1 and R.sub.2 are not the same, the optical or cis- or trans-isomers thereof characterized by reacting a compound of the formula ##STR250## with a compound of the formula ##STR251## where R, A, R.sub.1, R.sub.2, W, X, Y and Z are as defined, above, with the provisos that (1) when A is --CR.sub.3, W is S;
• and (2) when taken together, Y and Z may form a ring in which YZ are represented by (a) the structure:
• --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4, in which instance R.sub.3 and X are each hydrogen;
• or (b) ##STR252## where L, M, R.sub.7 and R.sub.8 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and R.sub.3 and X are each hydrogen characterized by reacting the compounds in the presence of a strong organic acid.