EP0133310B1 — Imidazolidinones, and imidazolidinethiones, proce…

Claim 1

Independent Claim 669 words

A compound having the structure: wherein R is hydrogen; C 1 ―C 12 alkyl optionally substituted with one of the following groups: C 1 ―C 4 alkoxy, halogen, hydroxyl, C 3 -C 6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C 1 ―C 4 alkylphenyl, C 1 ―C 4 alkoxyphenyl, nitrophenyl, carboxyl, C 1 ―C 3 alkoxycarbonyl, cyano or tri(C 11 ―C 3 ) alkylammonium; C 3 ―C 12 alkenyl optionaly substituted with one of the following groups: C,-C 3 alkoxy, phenyl, halogen, or C 1 ―C 3 alkoxycarbonyl or with two C 1 ―C 4 alkoxy groups or two halogen atoms; C 3 ―C 6 cycloalkyl optionally substituted with one ot two C 1 ―C 3 alkyl groups; C 3 ―C 0 alkynyl; or, a cation; R 1 and R 2 each represent C 1 ―C 3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R 1 and R 2 is 2 of 5; or when R 1 and R 2 are taken together with the carbon to which they are attached, they may form a C 3 ―C 6 cycloalkyl group ring optionally substituted with methyl; A is nitrogen or CR 3 ; W is oxygen or sulfur; X is hydrogen, halogen or methyl; Y and Z are each hydrogen, halogen, C 1 ―C 6 alkyl, C 1 ―C 4 hydroxyalkyl, C 1 ―C 6 alkoxy, C 1 ―C 4 alkylthio, phenoxy, C 1 ―C 4 haloalkyl, OCF 2 CHF 2 , OCF 3 , OCHF 2 , nitro, cyano, NR 4 R S , C 3 ―C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 ―C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C 1 ―C 4 alkyl, C 1 ―C 4 alkoxy or halogen; R 3 is hydrogen, halogen, C 1 ―C 4 alkyl, C 1 ―C 4 alkoxy, CF 3 , N0 2 , OCF 3 , OCHF 2 or OCF 2 CHF 2 ; R 4 is hydrogen or C 1 ―C 4 alkyl; R 5 is C 1 ―C 4 alkyl; or when taken together, Y and Z form part of a ring in which YZ is represented by (1) the structure ―(CH 2 ) n ―, where n is an integer of 2, 3 and 4, provided that when A is CR 3 , then X is hydrogen; or (2) by the stucture where, when A is CR 3 , L, M, R 7 abd R 8 each represent hydrogen, halogen, C 1 ―C 4 alkyl or C 1 ―C 3 alkoxy, and X is hydrogen; and when A is nitrogen, L, M, R 7 and R 8 each represent hydrogen, halogen, C 1 ―C 4 alkyl, C 1 ―C 4 alkoxy, C 1 ―C 4 alkylthio, C 1 ―C 4 alkylsulfonyl, C 1 ―C 4 haloalkyl, N0 2 , CN, phenyl, phenoxy, amino, C 1 ―C 4 alkylamino, dialkyl(C 1 ―C 4 )amino, OCF 3 , OCHF 2 , OCF 2 CHF 2 , chlorophenyl, methylphenyl, C 3 ―C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 ―C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF 3 , NO 2 or CH 3 group, with the proviso that only one of L, M, R 7 or R 8 , may represent a substituent other than hydrogen, halogen, C 1 ―C 4 alkyl or C 1 ―C 4 alkoxy; or (3) by the structures: where B is oxygen or sulfur; R 9 and R 10 each represent hydrogen, halogen, phenyl, or C 1 ―C 4 alkyl; R 11 and R 12 each represent hydrogen, C 1 ―C 4 alkyl or phenyl; and when R 1 and R 2 are not the same, the optical or cis- or trans-isomers thereof; and except when R is a cation, the acid addition salts thereof.

Claim 2

Dependent Claim 669 words

A compound having the structure: wherein R is hydrogen; C 1 ―C 12 alkyl optionally substituted with one of the following groups: C 1 ―C 4 alkoxy, halogen, hydroxyl, C 3 -C 6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C 1 ―C 4 alkylphenyl, C 1 ―C 4 alkoxyphenyl, nitrophenyl, carboxyl, C 1 ―C 3 alkoxycarbonyl, cyano or tri(C 11 ―C 3 ) alkylammonium; C 3 ―C 12 alkenyl optionaly substituted with one of the following groups: C,-C 3 alkoxy, phenyl, halogen, or C 1 ―C 3 alkoxycarbonyl or with two C 1 ―C 4 alkoxy groups or two halogen atoms; C 3 ―C 6 cycloalkyl optionally substituted with one ot two C 1 ―C 3 alkyl groups; C 3 ―C 0 alkynyl; or, a cation; R 1 and R 2 each represent C 1 ―C 3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R 1 and R 2 is 2 of 5; or when R 1 and R 2 are taken together with the carbon to which they are attached, they may form a C 3 ―C 6 cycloalkyl group ring optionally substituted with methyl; A is nitrogen or CR 3 ; W is oxygen or sulfur; X is hydrogen, halogen or methyl; Y and Z are each hydrogen, halogen, C 1 ―C 6 alkyl, C 1 ―C 4 hydroxyalkyl, C 1 ―C 6 alkoxy, C 1 ―C 4 alkylthio, phenoxy, C 1 ―C 4 haloalkyl, OCF 2 CHF 2 , OCF 3 , OCHF 2 , nitro, cyano, NR 4 R S , C 3 ―C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 ―C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C 1 ―C 4 alkyl, C 1 ―C 4 alkoxy or halogen; R 3 is hydrogen, halogen, C 1 ―C 4 alkyl, C 1 ―C 4 alkoxy, CF 3 , N0 2 , OCF 3 , OCHF 2 or OCF 2 CHF 2 ; R 4 is hydrogen or C 1 ―C 4 alkyl; R 5 is C 1 ―C 4 alkyl; or when taken together, Y and Z form part of a ring in which YZ is represented by (1) the structure ―(CH 2 ) n ―, where n is an integer of 2, 3 and 4, provided that when A is CR 3 , then X is hydrogen; or (2) by the stucture where, when A is CR 3 , L, M, R 7 abd R 8 each represent hydrogen, halogen, C 1 ―C 4 alkyl or C 1 ―C 3 alkoxy, and X is hydrogen; and when A is nitrogen, L, M, R 7 and R 8 each represent hydrogen, halogen, C 1 ―C 4 alkyl, C 1 ―C 4 alkoxy, C 1 ―C 4 alkylthio, C 1 ―C 4 alkylsulfonyl, C 1 ―C 4 haloalkyl, N0 2 , CN, phenyl, phenoxy, amino, C 1 ―C 4 alkylamino, dialkyl(C 1 ―C 4 )amino, OCF 3 , OCHF 2 , OCF 2 CHF 2 , chlorophenyl, methylphenyl, C 3 ―C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 ―C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF 3 , NO 2 or CH 3 group, with the proviso that only one of L, M, R 7 or R 8 , may represent a substituent other than hydrogen, halogen, C 1 ―C 4 alkyl or C 1 ―C 4 alkoxy; or (3) by the structures: where B is oxygen or sulfur; R 9 and R 10 each represent hydrogen, halogen, phenyl, or C 1 ―C 4 alkyl; R 11 and R 12 each represent hydrogen, C 1 ―C 4 alkyl or phenyl; and when R 1 and R 2 are not the same, the optical or cis- or trans-isomers thereof; and except when R is a cation, the acid addition salts thereof.

Claim 3

Dependent Claim 265 words

A compound according to Claim 1 having the structure: wherein R, R 1 , R 2 , R 3 , X and W are as defined in Claim 1 above, excepting that when R is a cation, it is a cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; Y and Z each, independently, represent hydrogen, halogen, C 1 ―C 6 alkyl, C 1 ―C 6 alkoxy, C 1 ―C 4 alkylthio, phenoxy, nitro, C 1 ―C 4 haloalkyl, OCF 2 CHF 2 , OCF 3 OCHF 2 , CN, NR 4 R 5 , C 3 ―C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 ―C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C 1 ―C 4 alkyl, C 1 ―C 4 alkoxy or halogen; R 4 is hydrogen or C 1 ―C 4 alkyl; R 5 is C 1 ―C 4 alkyl; or when taken together, Y and Z form part of a ring in which YZ are represented by the structure: ―(CH 2 ) n ―, where n is an integer of 2, 3 or 4 and X is hydrogen, or by the structure: where L, M, R 7 and R 8 each represent hydrogen, halogen, C,-C 4 alkyl or C 1 ―C 3 alkoxy; and when R 1 and R 2 are not the same, the optical or cis- or trans-isomers thereof; and except when R is a cation, the acid addition salts thereof.

Claim 4

Dependent Claim 237 words

A compound according to Claim 1, having the structure: wherein R, R 1 , R 2 , W and X are as defined in Claim 1 above, excepting that when R is a cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; Y and Z each, independently, represent hydrogen, halogen, C 1 ―C 6 alkyl, C 1 -C 6 alkoxy, CN, N0 2 , OCF 3 , OCHF 2 , OCF 2 CHF 2 , phenoxy, C 1 -C 4 haloalkyl, C 1 -C 4 alkylthio, C 1 -C 4 hydroxyalkyl, NR 4 R 5 , C 3 -C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 -C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; R 4 is hydrogen or C 1 -C 4 alkyl; R s is C 1 -C 4 alkyl; or when taken together Y and Z form part of a ring in which YZ are represented by the structure: -(CH 2 ) n -, where n is an integer of 2, 3 or 4; and when R 1 and R 2 are not the same, the optical and cis- or trans-isomers thereof; and except when R is a cation, the acid addition salts thereof.

Claim 5

Dependent Claim 225 words

A compound according to Claim 1, having the structure: wherein R, R 1 , R 2 , W and X are as defined above in Claim 1, excepting that when R is a cation, it is a cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; and L, M, R 7 and R represent hydrogen, halogen, C 1 -C 4 alkyl, C,-C 4 alkoxy, C,-C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, N0 2 , CN, phenyl, phenoxy, amino, OCF 3 , OCHF 2 , OCF 2 CHF 2 , C 1 -C 4 alkylamino, dialkyl(C l -C 4 )amino, chlorophenyl, methylphenyl, C 3 -C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 -C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenoxy substituted with one Cl, CF 3 , N0 2 or CH 3 group, with the proviso that only one of L, M, R 7 or R 8 , may represent a substituent other than hydrogen, halogen, C l -C 4 alkyl or C 1 -C 4 alkoxy; and when R 1 and R 2 are not the same, the optical and cis-or trans-isomers thereof; and except when R is a cation, the acid addition salts thereof.

Claim 6

Dependent Claim 126 words

A compound according to Claim 1, having a structure: wherein R, R 1 , R 2 , W and B are as defined above in Claim 1, excepting that when R is a cation, it is a cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead silver, nickel, ammonium, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium; R 9 and R 10 each represent hydrogen, halogen, C 1 -C 4 alkyl or phenyl; and R 11 and R 12 each represent hydrogen, C 1 -C 4 alkyl or phenyl; and when R 1 and R 2 are not the same, the optical or cis- or trans-isomers thereof; and except when R is a cation, the acid addition salts thereof.

Claim 7

Dependent Claim 111 words

A compound according to Claim 1, having a structure: wherein R, R 1 , R 2 , W and Bare as defined above in Claim 1, excepting that when R is a cation, it is a cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead silver, nickel, ammonium or organic ammonium; Rg and R 10 each represent hydrogen, halogen, C 1 -C 4 alkyl or phenyl; R 11 and R, 2 each represent hydrogen, C 1 -C 4 alkyl or phenyl; and when R, and R 2 are not the same, the optical isomers thereof; and except when R is a cation, the acid addition salts thereof.

Claim 8

Dependent Claim 42 words

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 as defined in Claim 1.

Claim 9

Dependent Claim 44 words

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 as defined in Claim 1.

Claim 10

Dependent Claim 20 words

A herbicidal composition comprising an inert diluent and a herbicidally effective amount of a compound as defined in Claim 1.

Claim 11

Dependent Claim 500 words

A process for the production of the compound of the formula wherein R may be hydrogen, but preferably is C 1 -C 12 alkyl optionally substituted with one of the following groups: C 1 -C 4 alkoxy, halogen, hydroxyl, C 3 -C 6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkoxyphenyl, nitrophenyl, carboxyl, C 1 -C 3 alkoxycarbonyl, cyano or tri(C 1 -C 3 ) alkylammonium; C 3 -C 12 alkenyl optionally substituted with one of the following groups: C 1 -C 3 alkoxy, phenyl, halogen, or C 1 -C 3 alkoxycarbonyl or with two C 1 -C 4 alkoxy groups or two halogen atoms; C 3 -C 6 cycloalkyl optionally substituted with one or two C 1 -C 3 alkyl groups; C 3 -C 10 alkynyl; R 1 and R 2 each represent C 1 -C 3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R 1 and R 2 is 2 of 5; or when R 1 and R 2 are taken together with the carbon to which they are attached, they may form a C 3 -C 6 cycloalkyl ring optionally substituted with methyl; A is nitrogen or CR 3 ; W is oxygen or sulfur; X is hydrogen, halogen or methyl; Y and Z are each hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 haloalkyl, OCF 2 CHF 2 , OCF 3 , OCHF 2 , nitro, cyano, NR 4 R 5 , C 3 -C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 -C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; R 3 is hydrogen, chlorine, bromine, iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, CF3, NO 2 , OCF 3 , OCHF 2 or OCF 2 CHF 2 ; R 4 is hydrogen or C 1 -C 4 alkyl; R s is C 1 -C 4 alkyl; or when taken together, Y and Z form part of a ring in which YZ is represented by (1) the structure-(CH 2 ) n -, where n is an integer of 2, 3 and 4, provided that when A is CR 3 , then X is hydrogen; or (2) by the structures: where B is oxygen or sulfur; Rg and R 10 each represent hydrogen, halogen, phenyl, or C 1 -C 4 alkyl; R 11 and R 12 each represent hydrogen, C 1 -C 4 alkyl or phenyl; and when R 1 and R 2 are not the same, the optical or cis- or trans-isomers thereof, characterized by reducing a compound of the formula wherein R, R 1 , R 2 , A, X, Y and Z are as defined above.

Claim 12

Dependent Claim 500 words

A process for the production of the compound of the formula wherein R may be hydrogen, but preferably is C 1 -C 12 alkyl optionally substituted with one of the following groups: C 1 -C 4 alkoxy, halogen, hydroxyl, C 3 -C 6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkoxyphenyl, nitrophenyl, carboxyl, C 1 -C 3 alkoxycarbonyl, cyano or tri(C 1 -C 3 ) alkylammonium; C 3 -C 12 alkenyl optionally substituted with one of the following groups: C 1 -C 3 alkoxy, phenyl, halogen, or C 1 -C 3 alkoxycarbonyl or with two C 1 -C 4 alkoxy groups or two halogen atoms; C 3 -C 6 cycloalkyl optionally substituted with one or two C 1 -C 3 alkyl groups; C 3 -C 10 alkynyl; R 1 and R 2 each represent C 1 -C 3 alkyl or cyclopropyl, with the proviso that the sum of the number of carbon atoms in R 1 and R 2 is 2 of 5; or when R 1 and R 2 are taken together with the carbon to which they are attached, they may form a C 3 -C 6 cycloalkyl ring optionally substituted with methyl; A is nitrogen or CR 3 ; W is oxygen or sulfur; X is hydrogen, halogen or methyl; Y and Z are each hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 haloalkyl, OCF 2 CHF 2 , OCF 3 , OCHF 2 , nitro, cyano, NR 4 R 5 , C 3 -C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, C 3 -C 8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; R 3 is hydrogen, chlorine, bromine, iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, CF3, NO 2 , OCF 3 , OCHF 2 or OCF 2 CHF 2 ; R 4 is hydrogen or C 1 -C 4 alkyl; R s is C 1 -C 4 alkyl; or when taken together, Y and Z form part of a ring in which YZ is represented by (1) the structure-(CH 2 ) n -, where n is an integer of 2, 3 and 4, provided that when A is CR 3 , then X is hydrogen; or (2) by the structures: where B is oxygen or sulfur; Rg and R 10 each represent hydrogen, halogen, phenyl, or C 1 -C 4 alkyl; R 11 and R 12 each represent hydrogen, C 1 -C 4 alkyl or phenyl; and when R 1 and R 2 are not the same, the optical or cis- or trans-isomers thereof, characterized by reducing a compound of the formula wherein R, R 1 , R 2 , A, X, Y and Z are as defined above.

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

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