Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-07-28
1997-03-18
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544218, 544219, A01N 4366, A01N 4356, C07D40312
Patent
active
056123388
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a compound of formula I ##STR2## wherein R.sub.1 is hydrogen or methyl, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.5 alkanoyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, CN, NO.sub.2, or wherein two of these substituents are adjacent to each other and together are a methylenedioxy or difluoromethylenedioxy radical, at least one of these three substituents is N, and
The compounds of the invention have fungicidal properties and are suitable fungicides especially for use in agriculture and horticulture.
The invention further relates to a process for the preparation of the novel compounds, to fungicidal compositions that contain such compounds as active ingredients, as well as to the use of such compounds and compositions for controlling phytopathogenic fungi.
In the narrower sense, the invention relates to a compound of formula I, wherein R.sub.1, R.sub.2, K, L, M and Y have the given meanings and R.sub.3, R.sub.4, R.sub.5 are each independently of one another hydrogen, halogen, C.sub.1 C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, CN, NO.sub.2, or wherein two of these substituents are adjacent to each other and together are a methylenedioxy or difluoromethylenedioxy radical.
In formula I above and throughout this specification, alkyl, haloalkyl, haloalkoxy or alkoxy groups, depending on the number of carbon atoms, are straight-chain or branched. Alkyl is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl. The C.sub.2 -C.sub.5 alkoxycarbonyl substituent is comprised of a C.sub.1 -C.sub.4 alkoxy group and a carbonyl group.
Halogen by itself or as moiety of an alkyl or alkoxy group is fluoro, chloro, bromo or iodo.
If the compounds of formula I contain asymmetrical carbon atoms, then the compounds are obtained in optically active form. Solely owing to the presence of the aliphatic double bond the compounds are obtained at all events in the [E] or [Z] form. Atropisomerism can also occur. All the possible isomeric forms as well as mixtures thereof, for example racemic mixtures and any form of [E/Z] mixtures, are embraced by formula I.
An important group of compounds falling within the scope of formula I embraces those compounds wherein one of the substituents K, L or M is nitrogen and the others are both CH, wherein R.sub.2 is hydrogen or halogen, and the substituents R.sub.1, R.sub.3, R.sub.4, R.sub.5 and Y have the given meanings (subgroup IA), and, among these, preferably those compounds wherein K is nitrogen, L and M are CH and R.sub.1 is methyl (subgroup Ia).
A further important group of compounds falling within the scope of formula I embraces those compounds wherein two of the substituents K, L and M are nitrogen, and the third substituent is CH, and the remaining substituents have the given meanings (subgroup IB) and, among these, preferably those compounds wherein K is CH and L and M are nitrogen, R.sub.1 is methyl, R.sub.4 is hydrogen and R.sub.2, R.sub.3, R.sub.5 and Y have the given meanings (subgroup IBB).
Within this last mentioned group of pyrimidine derivatives IBB, those compounds are preferred wherein R.sub.2 is hydrogen or halogen, Y is oxygen and R.sub.3 and R.sub.5 are each independently of the other hydrogen, halogen, methyl, ethyl, methoxy, ethoxy, CF.sub.3, OCF.sub.3, OCHF.sub.2, NO.sub.2 or CN, or both adjacent to each other are a methylenedioxy or difluoromethylenedioxy radical (subgroup Ib).
A further group of compounds falling within the scope of formula I embraces 1,3,5-triazinyl derivatives, i.e. those compounds wherein the substituents K, L and M are nitrogen, and Y and R.sub.1 to R.sub.5 have the given meanings (subgroup IC), preferably those compounds wherein R.sub.1 is methyl, R.sub.4 is hydrogen, Y is oxygen and R.sub.2, R.sub.3 and R.sub.5 have the given meanings (subgroup ICC).
Within this last mentioned group ICC, those compounds are preferred wherein R.sub.2 is fluoro, chloro, bromo, OCH.sub.3
REFERENCES:
patent: 5055477 (1991-10-01), Oda et al.
Patent Abstracts of Japan, 15, No. 271 (C-0848) JP 309 3774 (1991).
Ciba-Geigy Corporation
McC. Roberts Edward
Morris Patricia L.
LandOfFree
Pyrazolyl acrylic acid derivatives, intermediates thereto, and i does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Pyrazolyl acrylic acid derivatives, intermediates thereto, and i, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Pyrazolyl acrylic acid derivatives, intermediates thereto, and i will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1706518