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US 6,617,282 B2Granted
Processes for preparing 3-phenyl-2,4(1H, 3H)-pyrimidinediones
AssigneeIshihara Sangyo Kaisha, Ltd.
InventorsMark Read, Masamitsu Tsukamoto, Sandeep Gupta
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Abstract
A process for producing 3-phenyl-2,4(1H,3H)-pyrimidinediones having the general formula I and their salts which comprises reacting the isocyanates represented by the general formula (II) and the substituted hydrazono esters represented by the general formula (III) in the presence of a base. These compounds are useful as herbicides, defoliants and desiccants.
Claims8
A process for producing 3-phenyl-2,4(1H,3H)-pyrimidinediones having the general formula (I) and their salts
- wherein
- A1 is hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cyloalkynyl, cycloalkylalkyl, each being optionally substituted,
- A2 is hydrogen, —Q1—A3 wherein Q1 is O, S, SO, or SO2;
- A3 is hydrogen or A4 (A4 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cyloalkynyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclicalkyl, each being optionally substituted), —Q1—CQ2—A3 wherein Q2 is O or S, —Q1—CQ2—Q2—A3, —Q1—CQ2—N(A3)2, —CQ2—A3, —CQ2—Q2—A3, —CQ2—N(A3)2, —N(A3)2, —N(Q1—A3)2, —N(CQ2—A3)2, —N(Q1—A3)(CQ2—A3), —N(CQ2—Q2—A3)2, —N(A3)—CQ2—N(A3)2, or —SO2—N(A3)2, each A3 group of (A3)2 being independently same or different,
- any two of (A1)l and (A2)m groups being optionally combined through a saturated or unsaturated carbon, —CQ2—, and/or hetero O, N, S, SO, or SO2 linkage to form a cyclic ring having up to 12 membered ring, each being optionally substituted,
- l is an integer of 1 to 5, m is an integer of 1 to 3, l+m is an integer of 2 to 5,
- R1 is A4, —Q1—A3, —Q1—CQ2—A3, —Q1—CQ2—Q2—A3, —Q1—CQ2—N(A3)2, —CQ2—A3, —CQ2—Q2—A3, —CQ2—N(A3)2, —N(A3)2, —N(Q1—A3)2, —N(CQ2—A3)2, —N(Q1—A3)(CQ2—A3), —N(CQ2—Q2—A3)2, —N(A3)—CQ2—N(A3)2, or —SO2—N(A3)2, each A3 group of (A3)2 being independently same or different,
- R2 is hydrogen or R1,
- R1 and R2 groups being optionally combined together with N of N(R1)(R2) through a saturated or unsaturated carbon, —CQ2—, and/or hetero O, N, S, SO, or SO2 linkage to form a cyclic ring having up to 12 membered ring, each being optionally substituted,
- which comprises reacting an isocyanate represented by the general formula (II)
- wherein A1, A2, l and m are as defined above, and a substituted hydrazono ester represented by the general formula (III)
- wherein R5 is A4, R1 and R2 are as defined above, with the presence of a Grignard reagent.
9 more elements
A compound or its salt represented by the formula (I-c)
- wherein
- X, Y are hydrogen, halogen, cyano, nitro, alkyl, alkoxy, cycloalkyl, cycloalkylalkyl or thiocarbamoyl,
- Z is O, S, SO, SO2 or NR wherein R is alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl,
- Ar is pyridyl, pyrimidyl, triazolyl, thiazolyl, isothiazolyl, or phenyl, or pyridyl, pyrimidyl, triazolyl, thiazolyl, isothiazolyl, or phenyl substituted with up to five substituents independently selected the from group consisting of bromo, chloro, fluoro, iodo, (C1-C4)alkyl, halo(C1-4)alkyl C1-4)alkoxy, (C1-4)alkylthio, halo(C1-4)alkoxy, (C1-4)alkylsulfonyl, (C1-C3)alkylsulfinyl, di(C1-4)alkylaminocarbonyl, cyano, nitro, (C1-4)alkylsulfonylamino, (C1-4)alkoxycarbony(C1-4)alkoxy, and (C1-4)alkoxycarbonylamino,
- R3 is A4, —Q1—A3, —Q1—CQ2—A3, —Q1—CQ2—Q2—A3, —Q1—CQ2—N(A3)2, —CQ2—A3, —CQ2—Q2—A3, —CQ2—N(A3)2, —N(A3)2, —N(Q1—A3)2, —N(CQ2—A3)2, —N(Q1—A3)(CQ2—A3), —N(CQ2—Q2—A3)2, —N(A3)—CQ2—N(A3)2, or —SO2—N(A3)2, each A3 of (A3)2 being independently same or different,
- R4 is hydrogen or R3,
- R3 and R4 groups being optionally combined together with C of ═C(R3)(R4) to form a cyclopentylidene.
4 more elements
Dependencies are inferred from the claim text.