Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1992-10-27
1994-01-11
Fan, Jane T.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504225, 504235, 504209, 504247, 546278, 546167, 540598, 544131, 544360, A01N 4340, C07D40104
Patent
active
052781348
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel 3-(aminooxoacetyl)-2-(2-imidazolin-2-yl)pyridine and their salts, having a herbicidal activity.
BACKGROUND ART
The imidazolinone herbicides, a potent class, have publicly known and until recently, British patent No. 2,174,395 discloses the compounds having the following formula (A). ##STR1## Wherein:
R.sup.1 is C.sub.1 -C.sub.4 alkyl;
R.sup.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl;
B is CO.sub.2 R.sup.3, CONHR.sup.6, CHO, CH.sub.2 OH, COCH.sub.3, COC.sub.6 H.sub.5, CN, CH.sub.3, CH.dbd.NOH, CH.sub.2 COOH, CONHOH, CHROH, CH.sub.2 CH.sub.2 COOH, ##STR2## (wherein, R.sup.3 is hydrogen, dialkylimino, substituted alkyl, alkenyl or cation, R.sup.6 is hydrogen, hydroxy or alkenyl) A is hydrogen, COR.sup.4, SO.sub.2 R.sup.5, etc.
The above patent introduces many a herbicidal compounds, but they have recognized a disadvantage in that except for soybean, such compounds failed to exert an effective selectivity of herbicidal activity as herbicide.
Also, such imidazolinone compounds are specified in the following patents, say, German Patent No. 2,833,274, U.S. Pat. Nos. 4,824,466/4,851,021/4,824,474, European Patent No. 41,623/298,029/322,616.
However, the current situation is that the undesirable vegetation should be controlled so as to improve the growth of useful crops such as corn, rice, cotton, wheat, and soybean. The failure to check the weed growth in such useful crops may bring about significant losses to farmers and to consumer as well. Thus, the continuous research to develop more effective products should be required for a good harvest.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to novel compounds demonstrating a herbicidal activity and to agriculturally suitable compositions thereof, and a method of their uses as general and/or selective preemergent and/or postemergent herbicides or plant growth regulants.
More specifically, said compounds demonstrating a herbicidal activity are 3-(aminooxoacetyl)-2-(2-imidazolin-2-yl)pyridine having a following stucture of general formula(I). ##STR3## wherein,
R.sup.1 is C.sub.1 -C.sub.4 alkyl;
R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.5 cycloalkyl or C.sub.1 -C.sub.4 alkyl optionally substituted with 1-4 fluorine;
R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl optionally substituted with substituents contained in the following group I, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl;
R.sup.4 is the same as R.sup.3 ; or phenyl, benzyl, pyridyl, furanyl, thiophenyl, benzofuranyl, dihydrobenzofuranyl, benzothiophenyl, dihydrobenzothiophenyl, indolyl, indolinyl, optionally substituted with 0-3 same or different substituents selected from the substituents contained in group II ; and when taken together, connecting R.sup.3 and R.sup.4, a 3-7 membered ring may be formed, which may contain 0-3 double bonds or 0-3 O, N, SOn(n=0-2);
W is O or S;
X is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxyalkyl, or halogen;
Y, Z are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxyalkyl, C.sub.1 -C.sub.6 alkylthio, phenoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkylamino, C.sub.1 -C.sub.6 alkylsulfonyl or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; and when taken together, a 5-6 membered ring may be formed in which may contain O,N,S, double bonds or--(CH.sub.2).sub.n --, (n=0-4);
A is hydrogen or --COR.sup.5 (where R.sup.5 is hydrogen, methyl or CH.sub.2 Cl); when A is hydrogen, tautomeric isomer may exist;
Group I contains hydroxy, alkoxy, haloalkoxy, cyano, --CO.sub.2 R.sup.6 (where R.sup.6 is hydrogen, alkyl, alkenyl, or alkynyl), alkylthio, alkylsulfonyl, phenylthio, phenylsulfonyl, haloalkylthio, alkenoxy, alkoxy, --NR.sup.6 R.sup.7 (where R.sup.6, R.sup.7 are each hydrogen, alkyl, alkenyl or alkynyl or R.sup.6, R.sup.7 may form a ring), phenyl, or phenoxy;
Group II contains group I substituents, halogen,
REFERENCES:
patent: 4824474 (1989-04-01), Numata et al.
patent: 4851092 (1989-07-01), Maresch
Chang Hae S.
Hwang In T.
Jeon Dong J.
Kim Dae W.
Ryu Jae W.
Fan Jane T.
Korea Research Institute of Chemical Technology
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