Claims
- 1. A compound represented by the formula (I) or its salt: wherein X and Y are independent of each other and represent hydrogen, halogen, cyano, nitro, (C1-4)alkyl, (C1-4)haloalkyl, or (C1-4)haloalkoxy;Z is oxygen or sulfur; Q is A is oxygen, sulfur, or imino; R1 is hydrogen, (C1-4)alkyl, or (C1-4)haloalkyl, and can be independent of each other; R2 and R3 are independent of each other and are selected from the group consisting of hydrogen, halogen, cyano, nitro, (C1-4)alkyl, (C1-4)haloalkyl, (C2-6)alkenyl, (C2-6)haloalkenyl and amino which may be optionally substituted with (C1-4)alkyl or (C1-4)haloalkyl; Ar is a substituted or unsubstituted carbocyclic aromatic ring.
- 2. The compound or its salt according to claim 1 whereinAr is a substituted or unsubstituted carbocyclic aromatic ring which can be fused with another substituted or unsubstituted five or six membered carbocyclic or heterocyclic aromatic ring, in which the carbocyclic or heterocyclic aromatic ring may be substituted with up to seven substituents independently selected from the group consisting of halogen, (C1-6)alkyl, halo(C1-6)alkyl, (C1-6)alkoxy, halo(C1-6)alkoxy, (C1-6)alkylthio, (C1-6)alkylsulfonyl, (C1-6)alkylsulfinyl, (C1-6)dialkylaminocarbonyl, cyano, nitro, amino, hydroxy, (C1-6)alkylsulfonylamino, (C1-6)alkoxycarbonyl(C1-6)alkoxy, (C1-6)alkoxycarbonyl-halo(C1-6)alkyl, (C2-6)alkenyloxycarbonyl(C1-6)alkoxy(C1-6)alkyl, (C1-6)alkylcarbonylamino, bisbenzoylamino, aminoacetyl, aminotrifluoroacetyl, and amino(C1-6)allylsulfonate.
- 3. The compound or its salt according to claim 1 whereinX and Y are independently hydrogen or halogen; Z is oxygen or sulfur; R1 is (C1-4)alkyl; R2 is (C1-4)haloalkyl; R3 is hydrogen; Ar is phenyl, pyridyl, pyrimidyl, pyridazinyl, triazolyl, thiazolyl or isothiazolyl, or phenyl, pyridyl, pyrimidyl, pyridazinyl, triazolyl, thiazolyl or isothiazolyl substituted with upto five substituents independently selected from the group consisting of halogen, (C1-6)alkyl, (C1-6)haloalkyl, (C1-6)alkoxy, (C1-6)haloalkoxy, (C1-6)alkylthio, (C1-6)alkylsulfonyl, (C1-6)alkylsulfinyl, di(C1-6)alkylaminocarbonyl, cyano, nitro, amino, hydroxy, (C1-6)alkylsulfonylamino, (C1-6)alkoxycarbonyl(C1-6)alkoxy, (C1-6)alkoxycarbonyl-halo(C1-6)alkyl, (C2-6)alkenyloxycarbonyl(C1-6)alkoxy(C1-6)alkyl, (C1-6)alkoxycarbonylamino, bisbenzoylamino, aminoacetyl, aminotrifluoroacetyl, and amino(C1-6)alkylsulfonate.
- 4. The compound or its salt according to claim 1 whereinX is fluorine; Y is chlorine; R1 is methyl; R2 is trifluromethyl; Ar is phenyl, 2-iodo-phenyl, 2-trifluoromethoxyphenyl, 2-nitrophenyl, 4-nitrophenyl, 4-aminophenyl, 4-hydroxyphenyl, 4-methylsulfonylaminophenyl, 4-(1-ethoxycarbonylethoxy)phenyl, 2-cyanophenyl, 2-cyano-3-fluorophenyl, 2-cyano-4-fluorophenyl, 2-amino-4(1-ethoxy-carbonylethoxy)-phenyl, 2-cyano-4-nitrophenyl, 4-amino-2-cyanophenyl, 4-nitro-2-trifluoromethylphenyl, 4-amino-2-trifluoromethylphenyl, 4-acetylamino-2-trifluoro-methylphenyl, 4-(1-ethoxycarbonylethoxy)-2-nitrophenyl, or 5-chloro-4-(1-ethoxycarbonyl-ethoxy)-2-nitrophenyl.
- 5. A process for producing a compound represented by the formula (I) in claim 1 or its salt, which comprises reacting a compound represented by the formula (II): wherein X, Y, Z, and Q are as defined in claim 1;with a compound of the formula: Ar-Hal, wherein Hal is a halogen atom and Ar is as defined in claim 1, in the presence of a base.
- 6. A process for producing a compound or its salt represented by the formula (I) in said claim 1, wherein Q is Q1, which comprises reacting a compound represented by formula (III): wherein X, Y, Z, and Ar are as defined in claim 1;with a compound of the formula (IV): wherein R1and R2 are as defined in claim 1 and R4 represents a C1-4 alkyl group, in the presence of a base.
- 7. A process for producing a compound or its salt represented by the formula (I) in claim 1, wherein Q is Q1, which comprises reacting a compound represented by formula (V): wherein X, Y, Z, and Ar are as defined as in claim 1 and R5 represents a C1-4alkyl or phenyl group;with a compound of the formula (IV): wherein R1 and R2 are as defined in claim 1 and R4 represents a C1-4 alkyl group, in the presence of a base.
- 8. A process for producing a compound or its salt represented by the formula (I) in claim 1, wherein Q is Q1, which comprises reacting a compound represented by formula (VI): wherein R1 is as defined in claim 1;with a compound of the formula (VII): wherein X, Y, Z, and Ar are as defined in claim 1 and L represents a leaving group, in the presence of a base.
- 9. A process for producing a compound or its salt represented by the formula (IX): wherein X, Y, Z, R1, R2, R3 and Ar are as defined in claim 1, which comprises reacting a compound represented by formula (VIII): wherein X, Y, Z, R1, R2, R3 and Ar are as defined in claim 1; with a thionating agent in the presence of a base.
- 10. A process for producing a compound or its salt represented by the formula (I) in claim 1, wherein R1 is alkyl, haloalkyl, or amino, and Q is Q1, which comprises reacting a compound represented by formula (VIII′) with an alkylating agent or an aminating reagent: wherein X, Y, Z, R2, R3, A, and Ar are as defined in claim 1 and R1 is hydrogen.
- 11. A process for producing a compound or its salt represented by the formula I in claim 1, which comprises reacting a haloaryl compound of formula (XII): wherein Hal represents a halogen atom and X, Y and Q are as defined in claim 1;with an aryl hydroxyl compound or thiohydroxy compound, or its salt.
- 12. A process for producing a compound or its salt represented by the formula (II): wherein X, Y, Z, and Q are as defined in claim 1, which comprises reacting a compound of formula (XIII): wherein R6 represents a C1-4 alkyl or a heteroaryl group and X, Y, Z, and Q are as defined in claim 1;with a hydrolytic reagent.
- 13. A herbicidal composition, characterized in that it contains at least one compound according to claim 1.
- 14. A herbicidal composition which comprises an effective amount of a compound of claim 1 and an agricultural adjuvant.
- 15. A method for controlling weeds, which comprises applying to the locus to be protected a herbicidally effective amount of a compound of claim 1.
- 16. A method for controlling weeds in a corn field which comprises applying a herbicidally effective amount of a compound of claim 1 to the corn field.
- 17. A method for controlling weeds in a soybean field which comprises applying a herbicidally effective amount of a compound of claim 1 to the soybean field.
- 18. A method for controlling weeds, which comprises applying to the locus to be protected a herbicidally effective amount of a compound of claim 1 in combination with another herbicide.
- 19. A method for controlling weeds of claim 15 wherein the compound of claim 1 is applied to soil as a preemergent herbicide.
- 20. A method for controlling weeds of claim 15 wherein the compound of claim 1 is applied to plant foliage.
- 21. A method for controlling weeds of claim 15 wherein the another herbicide is an acetanilide, or sulfonylurea.
- 22. A method to desiccate a plant which comprises applying to the plant a compound of claim 1.
- 23. A method to desiccate a plant of claim 22 wherein the plant to which the compound is applied is a potato plant or a cotton plant.
Parent Case Info
This is a Continuation-in-Part of application Ser. No. 09/970,220 filed Oct. 1, 2001; the disclosure of which is incorporated herein by reference.
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
09/970220 |
Oct 2001 |
US |
Child |
10/001816 |
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US |