TH899A - Diazole and Triazole - Google Patents

Abstract

The process for preparing diazole and triazole urea, compounds that have shown potential for use in agriculture, particularly as herbicides.

Claims (36)

1. Compounds with the following chemical formulas: (chemical formula) where R is 1H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl (AlKynyl), SR4, OR, CH2OR6, CH2CH2OR6, N(CH3)2, CF3, CF2CF3]Cl, NHCH3, N(CH3)2]CH(OCH302 or (chemical formula) R2 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, CH2OCH3, CH2CH, OCH3, CH2SCH3, CH2CH2SCH3 or C1-C4 alkyl which is replaced by F1-3 atoms; R3 is H or CH3; R4 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, CH2CO2R6 or CH(CH3)CO2R6; R5 is C1-C4 alkyl, C3-C4 alkyneyl, C3-C4 alkynyl, CH2CO2R6, CH(CH3)CO2R6 or CH2CF3; R6 is C1-C4 alkyl; W is O or S; Z is (chemical formula); R7 is H, C1-C4 alkyl, C1-C4 alkoxy, F, C(O)NR21K22, Cl, Br, No2, CF3, CO2R9, SO2NR10R11, C(O)SR10, SO2N(OCH3)CH3, QSO2R12, S(O)nR13, CH2CO2R20, CH(CH3)CO2R20, CH2S(O)nR13, CH(H3)S(O)nR13, C3-C4 alkyneyl. R8 is H, F, Cl, Br, CF3, NO2, C1-C3 alkyl or C1-C3 alkyl; R9 is C1-C6 alkyl, CH2CH2, OCH3, CH2, CH2, OCHCH3, CH2, CH2 CH2, OCH2, CH3, C3-C6 alkynyl, C3-C6 alkynyl or C1-C3 alkyl which is replaced by 3 Cl or F1 atoms; R10 and R11 are independent, i.e. C1-C3 alkyl; R1 is C1-C4 alkyl, CH2 CH2OCH3, CH2, CH2CH2, OCH3 or C1-C4 alkyl which is replaced by 3 F, Cl or Br atoms. With 1-5 atoms of F, Cl, or Br; n is 0, 1, or 2; Q is or NCH3; R14 is H, CH3, OCH3, F, Cl, Br, NO2, SO2NR10R11, SO2N(OCH3)CH3, OSO2R12, or S(O)nR13; R15 is H, Cl, Br, CH3, OCH3, or NO2; R16 is H, C1-C4-alkyl, C1-C4-alcolyte, F, Cl, Br, CH3, SO2NR10R11, SO2N(OCH3)CH3, or S(O)nR13; R17 is H, F, Cl, Br, CH3, OCH3, or OCH3, w' is 0 or S; R18 is H, C1-C4-alkyl, C1-C4-alcolyte. R10 is, F, Cl, Br, NO2, SO2NR10R11, SO2N(OCH3)CH3 or S(O)nR13; R19 is, Cl, NO2, CF3, CO2R9, SO2N(OCH3)CH3, SO2NR10R11, QSO2R12, S(O)nR13 or C1-C3 alkoxy which is replaced by Cl or F'1-5 atoms; R20 is C1-C4 alkyl, CH2CH2, OCH3, CH2, CH2Cl or CH2CH=CH2; R21 is C1-C3 alkyl or OH5; R22 is C1-C3 alkyl; and R21 and R22 may be combined into (chemical formulas) with the requirement that (1) the total number of carbon atoms of R10 and R11 must be less than or equal to (2) The total number of carbon atoms of R1 and R2 must be less than or equal to 6; (3) When w' is O, then R18' is H, Cl, Br, CH3 or CO2R20; (4) When w' is O, then R18 is H, Cl, B or CH3, then z is (chemical formula); (5) When w is s, then R3 is H; (6) When R7 is H, then R8 is H; and (7) R14 and R15 must not be NO2. 2. Compounds with the following chemical formulas: R' is H, CH3, or C2H5; R1' is CH3, C2H5, SCH3, OCH3, or OCH2H5; R2' is CH3, C2H5, or OCH3; Z' is (chemical formula) R7 is C1-C4 alkyl, C1-C4 alkoxy, F, Cl, Br, NO2, CF3, CO2R9, SO2NR10R11, C(O)NR21R22, SO2N(OCH3)CH3, QSO2R12, S(O)nR13C(O)SR10, CH2CO2R20, CH(CH3)CO2R20, CH2S(O)nR13, CH(CH3)S(O)nR13, C3-C4 alkyloxy. R8 is H, F, Cl, Br, CF3, NO2, C1-C3 alkyl or C1-C3 alkyl, which is replaced by OCH3 or OCH2-H5, or C1-C3 alkoxy, which is replaced by a) Cl, Br or F1-5 atoms or b) OCH3 or OCH2H5; R9 is H, F, Cl, Br, CF3, NO2, C1-C3 alkyl or C1-C3 alkyl; R9 is C1-C6 alkyl, CH2CH2, OCH3, CH2, CH2, OCHCH3, CH2, CH2 CH2, OCH2, CH3, C3-C6 alkenyl, C3-C6 alkyl or C1-C3 alkyl, which is replaced by cl or F1-3 atoms; R10 and R11 are independent, i.e., C1-C3 alkyl; R12 is C1-C4-alkyl, CH2. R13 is a C1-C4 alkyl alkyl atom; R14 is H, CH3, OCH3, F, Cl, Br, NO2, SO2NR10R11, SO2N(OCH3)CH3, OSO2R12 or S(O)nR13; R16 is H, C1-C4 alkyl, C1-C4 alkoxy, F, Cl, Br, NO2, SO2NR10R11, SO2N(OCH3)CH3 or S(O)nR13; R18 is H, C1-C4 alkyl, C1-C4 alkoxy, F, Cl, Br, NO2, SO2NR10R11, SO2N(OCH3)CH3 or S(O)nR13; R2 O is C1-C4 alkyl, CH2CH2, OCH3, CH2, CH2Cl or CH2CH=CH2; Q is 0 or NCH3; R21 is C1-C3 alkyl or OH5; R22 is C1-C3 alkyl; and R21 and R22 may be combined to form (chemical formula) with the following requirements: (1) the total number of carbon atoms of R10 and R11 must be less than or equal to 4; and (2) R1' and R2' must not be H simultaneously; and salts of these substances that are suitable for agricultural use. 3. The compound of claim 1, where w is 0 and R3 is H. 4. The compounds of claim 3, where z is (chemical formula) w' is s; R19CO2CH3,SO2N(CH3)2 or SO2CH3; and R15 and R17 are H. 5. The compound of claim 4, which z is (chemical formula). 6. The compounds of claim 5, where R1 is C1-C2 alkyl, SR4, OR5, CH2OCH3, N(CH3)2 or Cl; R2 is C1-C2 alkyl, CH2CF, CH2CH=CH2 or CH2C=CH; and R4 and R5 are independent, i.e. CH3C2H5. 7. The compound of claim 6, where z is (chemical formula), R7 is something other than H; and R8 is H, F, Cl, Br, CF3, CH3O or CH3. 8. Compounds of claim 7 where R7 is Cl, NO2, CO2R9, SO2NR10R11, OSO2R12; R8 is H; R9 is C1-C3 alkyl, CH2CH=CH2, CH2CH2OCH3 or CH2CH2Cl; R10 and R11 are independent, i.e. C1-C2 alkyl; and R12 and R13 are independent, i.e. C1-C3 alkyl. 9. The compounds of claim 8, where R9, R10, R11, R12, R13 are CH3. 10. The compound of claim 2 in which R' is CH3 or C2H5. 11. The compound of claim 10 which (chemical formula) R8 is H, F, Cl, Br, CF3, CH3 or OCH3. 12. Compounds of claim 11 where R7 is Cl, NO2, CO2R9, SO2NR10R11, OSO2R12 or SO2R13; R8 is H; R9 is C1-C3 alkyl, CH2CH=CH2, CH2CH2OCH3 or CH2CH2Cl; R10 and R11 are independent, i.e. C1-C2 alkyl; and R12 and R13 are independent, i.e. C1-C3 alkyl. 13. The compounds of claim 12, where R9, R10, R11, R12, and R13 are CH3. 14. The compound of claim 1, which is 2-[[(5-methylthio-1-methyl1H1,2,4-triazole-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 15. The compound of claim 1, which is 2-[[(5-ethylthio-1-methyl1H1,2,4-triazole-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 16. The compound of claim 1, which is 2-[[(5-ethyl-1-methyl1H1,2,4-triazole-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 17. The compound of claim 1, which is 2-[[(5-methoxy-1-methyl1H1,2,4-triazole-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 18. The compound of claim 1, which is N-[(5-methoxy-1-methyl1H1,2,4-triazole-3-yl)aminocarbonyl]aminosulfonyl]-2-chlorobenzenesulfonamide. 19. The compound of claim 1, which is N-[(5-methoxy-1-methyl1H1,2,4-triazole-3-yl)aminocarbonyl]aminosulfonyl]N',N'-dimethyl-1,2-benzene disulfonamide. 20. The compound of claim 2, which is 2-[[(4,5-dimethyl-1H-imidazole-2-yl)aminocarbonyl]aminosulfonyl]benzoic, methyl ester. 21. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 1 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 22. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 2 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 23. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 3 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 24. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 4 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 25. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 5 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 26. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 6 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 27. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 7 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 28. A suitable mixture for controlling unwanted plant growth containing the compounds of Patent 8 in effective quantities and at least one of the following: a surface reactivator, a solid or liquid diluent. 29. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 1 in quantities that produce an effect at the desired control point. 30. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 2 in quantities that produce an effect at the desired control point. 31. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 3 in quantities that produce an effect at the desired control point. 32. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 4 in quantities that produce an effect at the desired control point. 33. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 5 in quantities that produce an effect at the desired control point. 34. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 6 in quantities that produce an effect at the desired control point. 35. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 7 in quantities that produce an effect at the desired control point. 36. Method of use for controlling unwanted plant growth, which involves applying the compounds of claim 8 in quantities that produce an effect at the desired control point (Clause 36, page 9, Figure).