Patent EA-000842-B1 (EA)
Title: Stable herbicidal compositions containing metal chelates of herbicidal dione compositions
Inventor: SCHER HERBERT BENSON
IPC: A01N35/06
Filed: 1997-02-03
Abstract: 1. A chemically stable herbicidal composition comprising, in a liquid medium, a di- or trivalent transition metal chelate of an herbicidal dione of the formula (I):   wherein R<1> represents a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms; a cycloalkyl group containing from three to six carbon atoms optionally substituted by one or more R<3> groups or one or more groups selected from halogen, -CO2R<4>; -SR<5> and -OR<5>; a cycloalkenyl group containing five or six carbon atoms optionally substituted by one or more R<3> groups or one or more halogen atoms or a group -CO2R<4>; or a group of the formula -(CH2)p-phenyl-(R<6>)q; R<2> represents cyano; -COR<7>; -CO2R<7>; or -S(O)mR<8>; or R<1> and R<2> together with the carbon atoms to which they are attached form a five- or six-membered 1,3-cycloalkanedione group, which 1,3-cycloalkanedione group is optionally substituted with from one to six substituents independently selected from halogen, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)cycloalkyl, cyano, nitro, (C1-C6) haloalkoxy, -CO2R<9>, -S(O)mR<10>, -NR<11>R<12>, -C(O)R<13>, -SO2NR<11>R<12>, phenyl and phenyl substituted with one or more halo or C1-C4 alkyl groups, wherein two substituents on the same carbon atom of the 1,3-cycloalkanedione group taken together can form an alkylene group having 2 to 6 carbon atoms; R<3> represents a straight-or branched chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms; or a cycloalkyl group containing from three to six carbon atoms; R<4> represents a straight- or branched-chain alkyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms; or a cycloalkyl group containing from three to six carbon atoms; R<5> represents a straight- or branched-chain alkyl group containing up to three carbon atoms; R<6> represents a halogen atom or a group selected from -R<4>, nitro, cyano, -CO2R<4>, -NR<61>R<62> and -OR<4>; R<61> represents hydrogen, a straight- or branched-chain alkyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms, or a cycloalkyl group containing from three to six carbon atoms; R<62> represents a straight- or branched-chain alkyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms, a cycloalkyl group containing from three to six carbon atoms, or a group selected from COR<4>, -CO2R<4> and -CONR<4>R<61>; wherein R<4> and R<61> are part of a group -CONR<4>R<61>, they may, together with the nitrogen to which they are attached, form a five- or six-membered ring optionally having one additional heteroatom in the ring which is oxygen or nitrogen e.g., pyrrolidine, morpholine, pyrrole, piperidine and piperazine, wherein the ring is optionally substituted by one or more alkyl groups containing up to three carbon atoms; and when R<61> and R<62> are part of a group -NR<61>R<62> they may, together with the nitrogen to which they are attached, form a five- or sixmembered ring optionally having one additional heteroatom in the ring which is oxygen or nitrogen e.g., pyrrolidine, morpholine, pyrrole, piperidine and piperazine, wherein the ring is optionally substituted by one or more alkyl groups containing up to three carbon atoms; R<7> represents hydrogen or straight- or branched-chain alkyl group containing up to six carbon atoms; R<8> represents (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl (C3-C8)cycloalkyl optionally substituted with halogen, cyano or (C1-C4)alkyl; or phenyl optionally substituted with one to three of the same or different halogen, nitro, cyano, (C1-C4)haloalkyl, (C1-C4) alkyl, (C1-C4)alkoxy or -S(O)mR<8>; R<9> represents (C1-C4)alkyl; R<10> represents (C1-C4)alkyl, (C1-C4)alkyl substituted with halogen or cyano, phenyl or benzyl; R<12> and R<12> independently represents hydrogen or (C1-C4)alkoxy; R<13> represents (C1-C4)alkyl or (C1-C4)alkoxy; X represents a halogen atom; a straight- or branched-chain alkyl or alkoxy group containing up to six carbon atoms which is optionally substituted by one or more groups -OR<15> or one or more halogen atoms; or a group selected from nitro, cyano, -CO2R<16>, -S(O)mR<15>, O(CH2)rOR<15>, -COR<16>, -OSO2R<18> , -NR<16>R<17>, -SO2NR<16>R<17>, -CONR<16>R<17> and -CSNR<16>R<17>; R<15> represents a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms; R<16> and R<17> each independently represents a hydrogen atom or a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms; R<18> represents a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms; or a cycloalkyl group containing from three to six carbon atoms; each Z independently represents halo, nitro, cyano, S(O)mR<2>, OS(O)mR<2>, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, carboxy, (C1-C6)alkylcarbonyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkylcarbonyl, amino, (C1-C6)alkylamino, (C1-C6)dialkylamino having independently the stated number of carbon atoms in each alkyl group, (C1-C6)alkylcarbonylamino (C1-C6) alkoxycarbonyiamino, (C1-C6)alkylaminocarbonylamino, (C1-C6)dialkylaminocarbonylamino having independently the stated number of carbon atoms in each alkyl group, (C1-C6)alkoxycarbonyloxy, (C1-C6)alkylaminocarbonyloxy, (C1-C6)dialkylaminocarbonyloxy, phenylcarbonyl, substituted phenylcarbonyl, phenylcarbonyloxy, substituted phenylcarbonyloxy, phenylcarbonylamino, substituted phenylcarbonylamino phenoxy or substituted phenoxy; m is zero, one or two; n is zero or an integer from one to four; p is zero or one; q is zero or an integer from one to five; and r is one, two or three. 2. A chemically stable herbicidal composition according to claim 1, wherein said liquid medium is a member selected from the group consisting of water, organic solvents and liquid herbicides. 3. A chemically stable herbicidal composition according to claim 1, wherein the transition metal is selected from the group consisting of Cu<+2>, Co<+2>, Zn<+2> and Ni<+2>. 4. A chemically stable herbicidal composition according to claim 1 having a pH of between about 2 and about 7. 5. A chemically stable herbicidal composition according to claim 1, wherein the molar ratio of the compound of formula (I) to the transition metal is between about 2:1 and 2:5. 6. A chemically stable herbicidal composition according to claim 1, further comprising at least one co-herbicide. 7. A chemically stable herbicidal composition according to claim 6, wherein said coherbicide is selected from the group consisting of acetanilides, tralkoxydim, bromoxynil and its esters, thiafluamide, MCPA and its esters, 2,4-D and its esters, and fluroxypyr meptyl. 8. A chemically stable herbicidal composition according to claim 6, wherein said liquid medium is a co-herbicide. 9. A chemically stable herbicidal composition according to claim 6, wherein said liquid medium is water. 10. A chemically stable herbicidal composition according to claim 6, wherein said liquid medium comprises a microencapsulated co-herbicide dispersed in water. 11. A chemically stable herbicidal composition according to claim 1, wherein the herbicidal dione is of the formula:   wherein X, Z and n have the same meanings as in claim 1; each Q independently represents C1-C4 alkyl or CO2R<a> wherein R<a> is C1-C4 alkyl; and z is 0 or an integer from 1 to 6. 12. A chemically stable herbicidal composition according to claim 11, wherein z is zero; X is chloro, bromo, nitro, cyano, C1-C4 alkyl, -CF3, -S(O)mR<15> or -OR<15>; and n is one or two; and each Z is independently chloro, bromo, nitro, cyano, C1-C4 alkyl, -CF3, -OR<15>, -OS(O)mR<2> or -S(O)mR<2>. 13. A chemically stable herbicidal composition according to claim 11, wherein the herbicidal dione is a member selected from the group consisting of 2-(2'-nitro-4'-methylsulfonyl-berizoyl)-1,3-cyclohexanedione, 2-(2'-nitro-4'- methylsulfonyloxybenzoyl)-1,3- cyclohexanedione and 2-(2'-chloro-4'-methylsulfonylbenzoyl)-1,3-cyclohexanedione. 14. A chemically stable herbicidal composition according to claim 1, wherein the herbicidal dione is of the formula:   wherein R<50> is a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms which may be the same or different; or a cycloalkyl group containing from three to six carbon atoms which is optionally substituted by one or more groups selected from R<55> and one or more halogen atoms which may be the same or different; one of R<51> and R<53> is -S(O)tR<56> and the other of R<51> and R<53> is a halogen atom; a straight- or branched-chain alkyl group containing up to six carbon atoms which is substituted by -OR<55>; -R<55>; nitro; cyano; -SR<55>; -OR<55>; -O(CH2)sOR<55>; or -CO2R<55>; and when R<51> is S(O)tR<56>, R<53> may be hydrogen; R<52> and R<54>, which may be the same or different, each is a halogen atom; a hydrogen atom; a straight- or branched-chain alkyl group containing up to six carbon atoms which is substituted by -OR<55>; -R<55>; nitro; cyano; -OR<55>; -O(CH2)sOR55; or -CO2R<55>; R<55> and R<56>, which may be the same or different, each is a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms which may be the same or different; s is an integer from l to 3; and t is zero, 1 or 2. 15. A chemically stable herbicidal composition according to claim 14, wherein R<50> is a cycloalkyl group. 16. A chemically stable herbicidal composition according to claim 14, wherein the herbicidal dione is a member selected from the group consisting of 2-cyano-1-[2-chlor