Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-07-15
1998-11-10
Lambkin, Deborah C.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504244, 504310, 504313, 504314, 568327, 568374, 558426, 558428, 560 53, 560119, 546314, A01N 3104, A01N 4336, C07C 49115, C07D21170
Patent
active
058344047
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/02249 filed Nov. 07, 1995.
FIELD OF THE INVENTION
The present invention is related to novel bicycloheptanedione derivatives and a herbicide.
BACKGROUND ART
Substituted bicycloheptanedione derivatives similar to the compounds according to the present invention and herbicides comprising such derivative are disclosed in Japanese Patent Laid-opened No. Hei 3-255047.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to provide a herbicide which can be advantageously manufactured in an industrial scale, assures firm herbicidal efficacy with a lower dose and high safeness, and possesses a better selectivity in the herbicidal activity between crops and weeds.
The present invention is directed to substituted bicycloheptanedion e ##STR2## wherein R represents C.sub.1 -C.sub.4 alkyl, R.sup.1 represents hydrogen, C.sub.1 -C.sub.10 alkyl in either straight or branched chain, C.sub.2 -C.sub.4 alkenyl, aralkyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl, hydroxy C.sub.1 -C.sub.4 alkyl, --A--C.sub.3 -C.sub.4 alkyl, --A--C.sub.3 -C.sub.6 cycloalkyl, --A--C(O)r, --A--CH.sub.2 CN or phenyl, A represents a single bond or C.sub.1 -C.sub.4 alkylene, r represents hydrogen, C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 alkoxy or phenyl, substituted pyridyl, ##STR3## wherein R and R.sup.1 are as described above and R.sup.10 is C.sub.1 -C.sub.4 alkyl, aralkyl or acetyl. -C.sub.10 alkyl in either straight or branched chain represented by R.sup.1, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl and so on can be given.
As examples of the C.sub.2 -C.sub.4 alkenyl, vinyl, allyl, crotyl and the like can be given.
As examples of the C.sub.2 -C.sub.4 alkylnyl, ethynyl, propargyl and the like can be given.
As examples of the aralkyl, benzyl, .alpha.-methylbenzyl, .alpha., .alpha.-dimethylbenzyl, 2-phenylethyl, of those which benzene ring may be substituted with any of lower alkyls, halogen atoms, lower alkoxy, nitro, etc., and the like can be given.
As examples of the C.sub.2 -C.sub.4 haloalkynyl, iodopropargyl and the like can be given.
As examples of the C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, methoxymethyl, methoxyethyl, methoxypropyl, methoxyisopropyl, ethoxymethyl, ethoxyethyL, ethoxypropyl, propoxymethyl, propoxyethyl, propoxypropyl, butoxymethyl, butoxyethyl, isopropoxymethyl, isobutoxymethyl, butoxyethyl, t-butoxymethyl, butoxyethyl and the like can be given.
As examples of the C.sub.1 -C.sub.4 haloalkyl, trifluoromethyl, trifluoroethyl, trichloromethyl, pentafluoroethyl, tribromomethyl and the like can be given.
As examples of the C.sub.2 -C.sub.4 haloalkenyl, chlorovinyl, 3-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 1-chloroallyl, 3-chlorocrotonyl and the like can be given.
As examples of the hydroxy C.sub.1 -C.sub.4 alkyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxyisopropyl and the like can be given.
And, A of --A--C.sub.3 -C.sub.6 cycloalkyl, --A--C(O)r and --A--CH.sub.2 CN described above is a single bond or C.sub.1 -C.sub.4 alkylene, such as methylene, ethylene and trimethylene, and wherein r represents hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or phenyl. Further, as examples of the C.sub.3 -C.sub.6 cycloalkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like can be given.
As example of the substituent to phenyl and pyridyl represented by R.sup.2 propyl, isopropyl, butyl, isobutyl and t-butyl, C.sub.2 -C.sub.4 alkenyl, such as vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl and 3-butenyl, C.sub.2 -C.sub.4 alkynyl, such as ethynyl and propargyl, C.sub.1 -C.sub.4 haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, bromomethyl, dibromomethyl, chloroethyl, fluoroethyl, dichloroethyl, difluoroethyl, trifluoroethyl, tetrafluoromethyl, perfluoroethyl, chloropropyl, fluoropropyl, perfluoropropy
REFERENCES:
patent: 5006158 (1991-04-01), Carter et al.
patent: 5092919 (1992-03-01), Nguyen
patent: 5094685 (1992-03-01), Baba et al.
patent: 5114461 (1992-05-01), Geach et al.
patent: 5228898 (1993-07-01), Ueda et al.
Adachi Hiroyuki
Kawana Takashi
Sagae Takahiro
Takahashi Akihiro
Tomida Kazuyuki
Lambkin Deborah C.
Nippon Soda Co. Ltd.
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