Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Silicon containing doai
Patent
1997-12-04
1999-11-16
Geist, Gary
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Silicon containing doai
556437, 556438, 556441, 556426, 556465, 556449, 556415, 556417, 556446, A01N 5510
Patent
active
059858532
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new derivatives of .beta.-methoxy acrylic acid, their preparation process and their use as pesticides.
A subject of the invention is the compounds of formula (I): ##STR3## in which: R.sub.1, R.sub.2 and R.sub.3, identical or different, represent a linear, branched or cyclic alkyl radical, an alkenyl or alkynyl radical, containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, an aryl radical optionally substituted by one or more halogen atoms, one or more hydroxyl radicals, one or more linear or branched alkyl radicals, optionally substituted by one or more halogen atoms, one or more O-alkyl or S-alkyl radicals optionally substituted by one or more halogen atoms, O-alkyl, O-alkenyl, O-alkynyl, S-alkyl, S-alkenyl or S-alkynyl radical, optionally substituted by one or more halogen atoms and containing up to 11 carbon atoms, an aryl radical containing up to 14 carbon atoms, a C.tbd.N, NO.sub.2, NH.sub.2, ##STR4## CO.sub.2 alk.sub.3 radical, alk.sub.1, alk.sub.2 and alk.sub.3, identical to or different from each other, representing an alkyl radical containing up to 8 carbon atoms, exception of hydrogen.
The geometry of the double bond of the .beta.-methoxy acrylic part can be Z, E or an E+Z mixture.
In the definition of the various substituents: isobutyl, sec-butyl, terbutyl radical, linear or branched pentyl, hexyl, heptyl or octyl, cyclopentyl radical, propynyl, butenyl or butynyl radical, piperidinyl, piperazinyl or morpholinyl radical,
A more particular subject of the invention is the compounds of formula (I) in which the geometry of the exo double bond (enol ether) is Z.
A particular subject of the invention is the compounds of formula (I) in which R.sub.1, R.sub.2 and R.sub.3 each represent an alkyl radical containing up to 4 carbon atoms and in particular those in which R.sub.1, R.sub.2 and R.sub.3 each represent a methyl or ethyl radical, as well as those in which R.sub.4 represents a halogen atom, as well as those in which R.sub.4 represents an alkyl radical containing up to 4 carbon atoms.
Among the preferred compounds of the invention, there can be mentioned more particularly those whose preparation is given hereafter in the experimental part and quite especially the compounds of Examples 1, 4 and 5.
Also a subject of the invention is a preparation process for the compounds of formula (I) characterized in that a compound of formula (II): ##STR5## in which Hal represents a halogen atom, X and R.sub.4 retain their previous meaning, is subjected to the action of a compound of formula (III): ##STR6## in which R.sub.1, R.sub.2 and R.sub.3 retain their previous meaning, in order to obtain the corresponding compound of formula (I).
In a preferred implementation of the process of the invention, the reaction between the compound of formula (II) and the compound of formula (III) is carried out in an aprotic dipolar solvent such as acetonitrile or dimethyl formamide, in the presence of a tertiary amine such as triethylamine, and in the presence of palladium, for example in the presence of bis(triphenylphosphine) palladium (II) chloride, or metallic palladium on a charcoal support, of a tertiary phosphine such as triphenylphosphine and a copper-based catalyst such as cuprous iodide,
The compounds of formula (II) are new products and are in themselves a subject of the present invention.
The compounds of formula (II) can be prepared according to the reaction diagram: ##STR7##
The starting product of formula (A) can be prepared according to the following process: ##STR8##
The compounds of formula (II) can also be prepared according to the following reaction diagram: ##STR9##
The experimental part set out hereafter gives examples of the preparation of the compounds of formula (II).
The compounds of formula (I) have useful properties which allow their use for combating parasites. It can be for combating parasites of vegetation whether they be parasites of the soil or of the parts above ground, parasites of premises and parasites of animals.
The compounds o
Laugraud, deceased Sylvain
Laugraud, legal representative by Bruno
Laugraud, legal representative by Philippe
Laugraud, legal representative by Rolande
Laugtaud, legal representative by Pierre
Geist Gary
Hoechst Marion Roussel
Vollano Jean F
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