Pyrazin-2-one derivatives, their use, and intermediates for thei

Details Pyrazin-2-one derivatives, their use, and intermediates for thei Pyrazin-2-one derivatives, their use, and intermediates for thei

1998-03-20

2000-01-18

Shah, Mukund J.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544 52, 544105, 544354, 544405, 544408, 504225, 504235, A01N 4360, C07D24118, C07D40304, C07D40504, C07D41304

Patent

active

060157747

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to pyrazin-2-one derivatives, their use, and intermediates for their production.


DISCLOSURE OF INVENTION

The present inventors have intensively studied to find a compound having excellent herbicidal activity. As a result, they have found that pyrazin-2-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: ##STR2## wherein R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sup.2 is C.sub.1 -C.sub.3 haloalkyl; 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 optionally 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: ##STR3## 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: ##STR4## wherein Q, R.sup.1, and R.sup.2 are as defined above, which is useful as an intermediate for the production of the present compounds.
Compound [2] may also be present in the form of a compound, which is its tautomer, as depicted below: ##STR5## wherein Q, R.sup.1, and R.sup.2 are as defined above.
In the present invention, the substituent Q may be, for example, [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula: ##STR6## wherein X is hydrogen or halogen; Y is halogen, nitro, cyano, or trifluoromethyl; --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), --NR.sup.11 (COOR.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.10, --CR.sup.17 .dbd.CR.sup.18 CON(R.sup.11)R.sup.12, --CH.sub.2 CHWCOOR.sup.13, or --CH.sub.2 CHWCON(R.sup.11)R.sup.12 ; C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.8 alkoxyalkoxyalkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkoxy}carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, --CH.sub.2 CON(R.sup.11)R.sup.12, --CH.sub.2 COON(R.sup.11)R.sup.12, --CH(C.sub.1 -C.sub.4 alkyl)CON(R.sup.11)R.sup.12, --CH(C.sub.1 -C.sub.4 alkyl)COON(R.sup.11)R.sup.12, C.sub.2 -C.sub.8 alkylthioalkyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylsulfonyl, (C.sub.1 -C.sub.8 alkyl)carbonyl, (C.sub.1 -C.sub.8 alkoxy)carbonyl, or hydroxy C.sub.1 -C.sub.6 alkyl; cyano, carboxyl, hydroxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, or (C.sub.1 -C.sub.6 alkyl)carbonyl; C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.10 alkoxyalkoxyalkyl, (C.sub.1 -C.sub.5 alkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, carboxyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.8 alkoxy)carbonyl, (C.sub.1 -C.sub.6 haloalkoxy)carbonyl, (C.sub.3 -C.sub.10 cycloalkoxy)carbonyl, (C.sub.3 -C.sub.8 alkenyloxy)carbonyl, (C.sub.3 -C.sub.8 alkynyloxy)carbonyl, aminocarbonyl, (C.sub.1 -C.sub.6 alkyl)aminocarbonyl, di(C.sub.1 -C.sub.6 alkyl)aminocarbonyl, (C.sub.1 -C.sub.6 alkyl)aminocarb

REFERENCES:
patent: 3501472 (1970-03-01), Wilcox et al.
patent: 5643855 (1997-07-01), Kilama et al.
Chemical Abstracts vol. 115, Aug. 5, 1991, No. 5, 115:48626d "Electrochemical and spectrophotometric studies of 2-hydroxy-3-(p-hydroxy-henyl)-6-methylpyrazine".

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