Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-02-10
2000-08-08
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514269, 544123, 544319, A61K 31535, A01N 4354, C07D41300, C07D23902
Patent
active
061002577
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase under 35 U.S.C. .sctn.371 of prior PCT International Application No. PCT/JP 96/02169 which has an International filing date of Aug. 1, 1996 which designated the United States of America, the entire contents of which are hereby incorporated by reference.
TECHNICAL FIELD
The present invention relates to pyrimidin-4-one derivatives, their use, intermediates for their production, and processes for producing these intermediates.
BACKGROUND ART
GB-A-2 130 214 discloses some pyrimidin-4-one derivatives having herbicidal activity.
DE-A-38 16 994 discloses some 2-haloalkyl-4-hydroxy pyrimidine derivatives.
Chemical Abstracts 51:9629g (1957) discloses 6-ethyl-5-(4-chlorophenyl)-2-dichloromethyl-3H-pyrimidin-4-one.
Chemical Abstracts 88:152546n (1978) discloses some 2-methyl-pyrimidin-4-one derivatives.
EP-A-0 168 262 discloses that some 2-alkyl-pyrimidin-4-one derivatives are useful in the treatment of heart diseases, hypertension, cerebrovascular diseases and thrombosis.
EP-A-0 544 166 discloses some 2-methyl4(3H)-pyrimidone compounds.
EP-A-0 568 041 discloses that some 3-phenyl-6-trifluoromethylpyrimidin-4-one derivatives have herbicidal activity.
EP-A-0 561 319 discloses that some pyrimidin-2,6-dione compounds have herbicidal activity.
EP-A-0 617 033 discloses that some pyrimidin-2,5-dione compounds have herbicidal activity.
DISCLOSURE OF INVENTION
The present inventors have intensively studied to find a compound having excellent herbicidal activity. As a result, they have found that pyrimidin-4-one derivatives represented by formula [1] as depicted below have excellent herbicidal activity, thereby completing the present invention.
Thus the present invention provides a compound of the formula: ##STR1## wherein R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sup.2 is C.sub.1 -C.sub.3 alkyl optionally substituted with one or more halogen atoms; R.sup.3 is C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogen atoms, C.sub.3 -C.sub.6 alkenyl, or C.sub.3 -C.sub.6 alkynyl; and Q is substituted phenyl (hereinafter referred to as the present compound(s)); and a herbicide containing it as an active ingredient.
The present invention also provides a process for producing compound [1], which comprises reacting a compound of the formula: ##STR2## wherein Q, R.sup.1, and R.sup.2 are as defined above, with a compound of the formula: trifluoromethanesulfonyloxy, or p-toluenesulfonyloxy; and R.sup.3 is as defined above.
The present invention further provides a compound of the formula: ##STR3## wherein Q and R.sup.1 are as defined above; R.sup.21 is C.sub.1 -C.sub.3 alkyl substituted with one or more halogen atoms, which is useful as an intermediate for the production of some of the present compounds; and a process for producing a compound of the formula: ##STR4## wherein Q, R.sup.1 , and R.sup.2 are as defined above, which comprises reacting a compound of the formula: ##STR5## wherein R.sup.19 and R.sup.20 are independently C.sub.1 -C.sub.3 alkyl, and Q and R.sup.1 are as defined above, with a compound of the formula: ##STR6## wherein R.sup.2 is as defined above.
The compound [2] may be present as a compound of the formula: ##STR7## which is a tautomer thereof.
Examples of Q in the present invention include [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula: ##STR8## wherein X is hydrogen or halogen;
Y is halogen, nitro, cyano, or trifluoromethyl;
Z.sup.1 is oxygen, sulfur, NH, or methylene;
Z.sup.2 is oxygen or sulfur;
n is 0 or 1;
B is hydrogen, halogen, nitro, cyano, chlorosulfo, --OR.sup.10, --SR.sup.10, --SO.sub.2 --OR.sup.10, --N(R.sup.10)R.sup.11, --SO.sub.2 N(R.sup.11)R.sup.12, --NR.sup.11 (COR.sup.13), --NR.sup.11 (SO.sub.2 R.sup.14), --N(SO.sub.2 R.sup.14)--(SO.sub.2 R.sup.15), --N(SO.sub.2 R.sup.14)(COR.sup.13), --NHCOOR.sup.13, --COOR.sup.13, --CON(R.sup.11)R.sup.12, --CSN--(R.sup.11)R.sup.12, --COR.sup.16, --CR.sup.17 .dbd.CR.sup.18 CHO, --CR.sup.17 .dbd.CR.sup.18 COOR.sup.13, CR.sup.17 .dbd.CR.sup.18 CON--(R.sup.11)R.sup.12, --CH.sub.2 CHWCOOR.sup.13
REFERENCES:
patent: 5726124 (1998-03-01), Tice et al.
Enomoto Masayuki
Hoshi Hisayuki
Sanemitsu Yuzuru
Shah Mukund J.
Sumitomo Chemical Company Ltd.
Truong Tamthom N.
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