3-(5-carboxy-4-substituted-phenyl)-(thio)uracil-esters and salts

Claim 2

Compounds of the formula ##STR21## wherein R 1 signifies hydrogen, C 1-4 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl, C 2-6 -alkoxyalkyl, formyl, C 2-6 -alkanoyl or C 2-6 -alkoxycarbonyl, R 2 signifies hydrogen, C 1-6 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl or C 2-6 -alkoxyalkyl, R 3 signifies halogen or nitro, R 4 signifies hydrogen or halogen, R 5 signifies hydrogen, halogen, C 1-4 -alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C 1-5 -alkoxy)methyl, (C 1-5 -alkylthio)methyl, cyano, nitro or thiocyanato, R 6 signifies hydrogen, C 1-4 -alkyl or C 1-4 -fluoroalkyl, or R 5 and R 6 together signify tri- or tetramethylene in which one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C 1-3 -alkyl, and X signifies oxygen or sulphur, with the provisos that (i) R 6 is C 1-4 -alkyl or C 1-4 -fluoroalkyl when R 5 is fluorine and (ii) R 6 is hydrogen or C 1-4 -alkyl and X is oxygen when R 5 is cyano, as well as the alkali metal, alkaline earth metal, ammonium and organic base salts of those compounds of formula I in which R 1 and/or R 2 signifies hydrogen.

Claim 3

Compounds of the formula ##STR22## wherein R 1 ' signifies C 1-4 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl, C 2-6 -alkoxyalkyl, formyl, C 2-6 -alkanoyl or C 2-6 -alkoxycarbohyl, R 2 ' signifies C 1-6 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl or C 2-6 -alkoxyalkyl, R 3 signifies halogen or nitro, R 4 signifies hydrogen or halogen, R 5 signifies hydrogen, halogen, C 1-4 -alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C 1-5 -alkoxy)methyl, (C 1-5 -alkylthio)methyl, cyano, nitro or thiocyanato, R 6 signifies hydrogen, C 1-4 -alkyl or C 1-4 -fluoroalkyl, or R 5 and R 6 together signify tri- or tetramethylene in which one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C 1-2 -alkyl, and X signifies oxygen or sulphur, with the provisos that (i) R 6 is C 1-4 -alkyl or C 1-4 -fluoroalkyl when R 5 is fluorine and (ii) R 6 is hydrogen or C 1-4 -alkyl and X is oxygen when R 5 is cyano.

Claim 4

Compounds of the formula ##STR22## wherein R 1 ' signifies C 1-4 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl, C 2-6 -alkoxyalkyl, formyl, C 2-6 -alkanoyl or C 2-6 -alkoxycarbohyl, R 2 ' signifies C 1-6 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl or C 2-6 -alkoxyalkyl, R 3 signifies halogen or nitro, R 4 signifies hydrogen or halogen, R 5 signifies hydrogen, halogen, C 1-4 -alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C 1-5 -alkoxy)methyl, (C 1-5 -alkylthio)methyl, cyano, nitro or thiocyanato, R 6 signifies hydrogen, C 1-4 -alkyl or C 1-4 -fluoroalkyl, or R 5 and R 6 together signify tri- or tetramethylene in which one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C 1-2 -alkyl, and X signifies oxygen or sulphur, with the provisos that (i) R 6 is C 1-4 -alkyl or C 1-4 -fluoroalkyl when R 5 is fluorine and (ii) R 6 is hydrogen or C 1-4 -alkyl and X is oxygen when R 5 is cyano.

Claim 5

Compounds according to claim 2, wherein R 1' signifies methyl.

Claim 6

Compounds according to claim 2, wherein R 2' signifies C 1-6 -alkyl or C 2-6 -alkoxyalkyl.

Claim 7

Compounds according to claim 2, wherein R 3 signifies chlorine or bromine.

Claim 8

Compounds according to claim 2, wherein R 4 signifies fluorine.

Claim 9

Compounds according to claim 2, wherein R 5 signifies hydrogen, chlorine, bromine, methyl or ethyl.

Claim 10

Compounds according to claim 2, wherein R 5 signifies fluorine.

Claim 11

Compounds according to claim 2, wherein R 6 signifies methyl, ethyl or trifluoromethyl.

Claim 12

Compounds according to claim 2, wherein R 5 and R 6 together signify tri- or tetramethylene.

Claim 13

A compound according to claim 2, selected from: Isopropyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-[1,4,5,6,7,8-hexahydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1-(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[5-bromo-3,6-dihydro-3,4-dimethyl-2,6-dioxo-1-(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-iodo-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-hydroxymethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-ethyl3-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-bromo-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-nitro-2,6-dioxo-1(2H)-pyrimidinyl]benzoate, 2-methoxy-1-methylethyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate and tert.-butyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate.

Claim 14

A compound according to claim 2, selected from: Isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-fluoro-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-4-propyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate and isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-5-fluoro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate.

Claim 15

A compound according to claim 1, selected from: Ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-[1,4,5,6,7,8-hexahydro-2,4-dioxo-3(2H)-quinazolinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-bromo-4-fluoro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-{1,2,5,7-tetrahydro-2,4-dioxo-thieno[3,4-d]pyrimidin-3(4H)-yl}-benzoate, Isopropyl 2-chloro-5-[1,4,5,6,7,8-hexahydro-2,4-dioxo-3(2H)-quinazolinyl]-benzoate.

Claim 16

A compound according to claim 2, selected from: isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-ethyl-5-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, ethyl 2-chloro-5-[1,4,5,6,7,8-hexahydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl]-benzoate, ethyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-ethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, ethyl 2-chloro-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate ethyl 2-chloro-5-[3,6-dihydro-3,4,5-trimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4,5-trimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-{1,2,5,7-tetrahydro-1-methyl-2,4-dioxo-thieno[3,4-d]pyrimidin-3(4H)-yl}-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,5-dimethyl-4-ethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[5-cyano-3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2,4-dichloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-bromo-4-chloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-acetyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-{1,2,4,5,6,7-hexahydro-1-methoxycarbonyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl}-benzoate, isopropyl 2-chloro-4-fluoro-5-[5-chloro-3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[5-bromo-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, tert.butyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-5-[1,4,5,6,7,8-hexahydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl]-benzoate, 2-propenyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, 2-propynyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate and methyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate.

Claim 17

A compound according to claim 2, selected from: Isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-5-fluoro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-5-fluoro-4-fluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-5-fluoro-4-fluoromethyl-3-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-propyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[5-chloro-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate and isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-methoxymethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate.

Claim 18

A weed control composition, characterized in that it contains an effective amount of at least one compound of the formula ##STR23## wherein R 1' signifies hydrogen, C 1-4 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl, C 2-6 -alkoxyalkyl, formyl, C 2-6 -alkanoyl or C 2-6 -alkoxycarbonyl, R 2' signifies hydrogen, C 1-6 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl or C 2-6 -alkoxyalkyl, R 3 signifies halogen or nitro, R 4 signifies hydrogen or halogen, R 5 signifies hydrogen, halogen, C 1-4 alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C 1-5 alkoxy)methyl, (C 1-5 -alkylthio)methyl, cyano, nitro or thiocyanato, R 6 signifies hydrogen, C 1-4 -alkyl or C 1-4 -fluoroalkyl, or R 5 and R 6 together signify tri- or tetramethylene in whcih one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C 1-3 -alkyl, and X signifies oxygen or sulphur, with the provisos that (i) R 6 is C 1-4 -alkyl or C 1-4 -fluoroalkyl when R 5 is fluorine and (ii) R 6 is hydrogen or C 1-4 -alkyl and X is oxygen when R 5 is cyano as well as formulation adjuvants.

Claim 19

A weed control composition, characterized in that it contains an effective amount of at least one compound of the formula ##STR23## wherein R 1' signifies hydrogen, C 1-4 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl, C 2-6 -alkoxyalkyl, formyl, C 2-6 -alkanoyl or C 2-6 -alkoxycarbonyl, R 2' signifies hydrogen, C 1-6 -alkyl, C 2-4 -alkenyl, C 2-4 -alkynyl or C 2-6 -alkoxyalkyl, R 3 signifies halogen or nitro, R 4 signifies hydrogen or halogen, R 5 signifies hydrogen, halogen, C 1-4 alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C 1-5 alkoxy)methyl, (C 1-5 -alkylthio)methyl, cyano, nitro or thiocyanato, R 6 signifies hydrogen, C 1-4 -alkyl or C 1-4 -fluoroalkyl, or R 5 and R 6 together signify tri- or tetramethylene in whcih one methylene can be replaced by oxygen or sulphur and which is optionally substituted with C 1-3 -alkyl, and X signifies oxygen or sulphur, with the provisos that (i) R 6 is C 1-4 -alkyl or C 1-4 -fluoroalkyl when R 5 is fluorine and (ii) R 6 is hydrogen or C 1-4 -alkyl and X is oxygen when R 5 is cyano as well as formulation adjuvants.

Claim 20

A weed control composition according to claim 16, characterized in that it contains an effective amount of at least one compound selected from the group: Isopropyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-[1,4,5,6,7,8-hexahydro-1-methyl-2,4-dioxo-3(2H)-quinazolinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[5-bromo-3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-iodo-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-hydroxymethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-ethyl-3-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-bromo-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-nitro-2,6-dioxo-1(2H)-pyrimidinyl]benzoate, 2-methoxy-1-methylethyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate and tert.butyl 2-chloro-4-fluoro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate as well as formulation adjuvants.

Claim 21

A weed control composition according to claim 16, characterized in that it contains an effective amount of at least one compound selected from the group: Isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-fluoro-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-4-propyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate and isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-5-fluoro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate as well as formulation adjuvants.

Claim 22

A method for the control of weeds, characterized by treating the locus to be protected against weeds and/or the weeds with an effective amount of a composition in accordance with claim 16.

Claim 23

A method for the control of weeds, characterized by treating the locus to be protected against weeds and/or the weeds with an effective amount of a composition in accordance with claim 17.

Claim 24

A method for the control of weeds, characterized by treating the locus to be protected against weeds and/or the weeds with an effective amount of a composition in accordance with claim 18.