Pyridazin-3-one derivatives, their use, and intermediates for th

Details Pyridazin-3-one derivatives, their use, and intermediates for th Pyridazin-3-one derivatives, their use, and intermediates for th

1998-01-30

2000-07-18

Bernhardt, Emily

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504225, 504221, 544114, 544238, 544239, 544105, 544 585, A01N 4358, C07D23714, C07D40304, C07D40504, C07D41304

Patent

active

060907533

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to pyridazin-3-one derivatives, their use as herbicides, and intermediates for their production.


BACKGROUND ART

EP-A-0029123 discloses a process for the preparation of substituted anilines and novel substituted anilines. In particular, it teaches that certain substituted anilines obtained by this process are useful as important starting materials for the preparation of novel substituted pyridazin-3-one derivatives having herbicidal activity in postemergence application. These pyridazin-3-one derivatives are, however, different from those of the present invention in that they have a substituted phenoxyphenyl group as an essential structural element at position 2 of the pyridazinone ring and further have quite distinct substituents on the pyridazinone ring.


DISCLOSURE OF INVENTION

The present inventors have intensively studied to find a compound having excellent herbicidal activity. As a result, they have found that pyridazin-3-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 C.sub.1 -C.sub.3 haloalkyl; R.sup.2 and R.sup.3 are the same or different and are hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, or C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula: ##STR2## wherein X is hydrogen or halogen; Y is halogen, nitro, cyano, or trifluoromethyl; SO.sub.2 --OR.sup.10, N(R.sup.11)R.sup.12, 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.10, CON(R.sup.11)R.sup.12, CSN(R.sup.11)R.sup.12, COR.sup.16, CR.sup.17 .dbd.CR.sup.18 COR.sup.16, 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 CH--WCOOR.sup.13, CH.sub.2 CHWCON(R.sup.11)R.sup.12, CR.sup.17 .dbd.NOR.sup.33, CR.sup.17 .dbd.NN(R.sup.11)R.sup.12, CR.sup.17 (Z.sup.2 --R.sup.34).sub.2, OCO.sub.2 R.sup.19, or OCOR.sup.19 ; C.sub.3 -C.sub.8 cycloalkylalkyl, 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, 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; hydroxy 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)aminocarbonyloxy C.sub.1 -C.sub.6 alkyl, or di(C.sub.1 -C.sub.6 alkyl)aminocarbonyloxy C.sub.1 -C.sub.6 alkyl; haloalkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C

REFERENCES:
patent: 4360672 (1982-11-01), Parg et al.

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