Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1994-11-21
1996-03-19
Daus, Donald G.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544263, 549446, C07D48704, A01N 4390
Patent
active
055004075
DESCRIPTION:
BRIEF SUMMARY
"This is a Section 371 filing of PCT/EP94/00778 filed Mar. 14, 1994, published as WO 94/21640".
The present invention relates to novel herbicidally active triazolopyrimidines, to their preparation, to compositions containing said compounds as active ingredients, and to the use thereof for controlling weeds, especially in crops of cultivated plants or for inhibiting plant growth.
Herbicidally active triazolopyrimidines are known and disclosed, inter alia, in WO 90/12012 and U.S. Pat. No. 4,209,621.
Novel triazolopyrimidines having herbicidal and growth-regulating properties have now been found.
Accordingly, the invention relates to compounds of formula I ##STR2##
wherein
R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; and
R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio,
C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C .sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkylthio, halogen, amino, C.sub.1 -C.sub.4 alkylamino or C.sub.1 -C.sub.4 dialkylamino.
Halogen substituents in the above definitions will be taken to mean fluoro or iodo, and preferably chloro and bromo.
The alkyl groups occurring in the definitions of the substituents may be straight-chain or branched and are typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl. Methyl and ethyl are preferred. Such structural units may also occur in the following substituents.
Haloalkyl will conveniently be alkyl groups that carry one or more, preferably one to five, identical or different halogen substituents, said halogen substituents being bromo or iodo and, preferably, fluoro and chloro. Illustrative examples of such groups are difluoromethyl, chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, 2,2,2-trifluoroethyl and 1,1,2,2-tetrafluoroethyl.
Alkoxy is typically methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy. Methoxy and ethoxy are preferred.
Haloalkoxy is exemplified by difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy or 1,1,2,2-tetrafluoroethoxy.
Alkylthio is typically methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio. Methylthio is preferred.
Haloalkylthio will typically be difluoromethylthio, trifluoromethylthio, 2,2,2-trifluoroethylthio or 1,1,2,2-tetrafluoroethylthio. Difluoromethylthio and trifluoromethylthio are preferred.
Alkoxyalkoxy will typically be methoxymethoxy, methoxyethoxy, ethoxymethoxy, ethoxyethoxy and propoxymethoxy. Methoxymethoxy is preferred.
Alkoxyalkyl is typically methoxymethyl, methoxyethyl, ethoxymethyl or ethoxyethyl. Methoxymethyl is preferred.
Alkylamino is typically methylamino, ethylamino, n-propylamino or isopropylamino. Methylamino is preferred.
Dialkylamino is exemplified by dimethylamino, methylethylamino, diethylamino or n-propylmethylamino. Dimethylamino is preferred.
In preferred compounds of formula I, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. Among this group of compounds, those compounds are particularly preferred in which R.sub.1 is hydrogen, methyl or ethyl.
Preferred compounds of formula I are also those wherein R.sub.1 is methyl and R.sub.2 is as defined for formula I. Among this group of compounds, those compounds are especially preferred in which R.sub.2 is trifluoromethyl or C.sub.1 -C.sub.4 haloalkoxy.
Further preferred compounds of formula I are those wherein R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, halogen, amino, C.sub.1 -C.sub.4 alkylamino or C.sub.1 -C.sub.4 dialkylamino.
Among this group of compounds, those compounds of formula I are particularly preferred wherein R.sub.2 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, chloro, bromo, amino, methylamino or dimethylamino. Among this g
REFERENCES:
Hauser et al., Alkaline Cleavage of Unsymmetrical .beta.-Diketones, J. Am. Chem. Soc. vol. 70, pp. 4023-4026 (1948).
.beta.-Diketones from Methyl Alkyl Ketones, Organic Synthesis, vol. 51, pp. 90-93 (1971).
Treibs et al., Synthesen mit Acetessigsavres tert.-butylester, Chem. Ber., No. 87, pp. 1163-1166 (1954) plus English Abstract (1954).
Abdulla et al., An Efficient Conversion of Ketones to .alpha.,.beta.-Unsaturated Ketones, J. Org. Chem., vol. 43, No. 21, pp. 4248-4250 (1978).
English Translations of Lopyrev et al., Ahurnal Obshchei Khimii, vol. 53, No. 7, p. 1684 (1983).
Hauser et al., The Acylation of Ketones to form .beta.-Diketones or .beta.-Keto Aldehydes, Organic Reactions, vol. VIII, pp. 59-63 (1954).
Temple, Jr., The Chemistry of Heterocyclic Compounds, vol. 37, cover page and table of contents (1981).
Ciba-Geigy Corporation
Daus Donald G.
Mathias Marla J.
Teoli, Jr. William A.
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