Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1995-12-01
1998-05-19
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504242, 504243, 544302, 544314, 544318, 544319, 544334, C07D23902, A01N 4354
Patent
active
057535949
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to 3-halo-3-hetarylcarboxylic acid derivatives of the general formula I ##STR2## in which R is a formyl group, a group CO.sub.2 H or a radical which can be hydrolyzed to COOH, and the remaining substituents have the following meanings: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; R.sup.3 forms a 3- to 4-membered alkylene or alkenylene chain in which in each case one methylene group is replaced by oxygen; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, or R.sup.3 is linked to R.sup.13 as mentioned above to form a 5- or 6-membered ring; to three nitrogen atoms and/or one sulfur or oxygen atom and which can have attached to it one or more of the following radicals: halogen, nitro, cyano, hydroxyl, mercapto, amino, 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, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl or phenyl; C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -alkylthioalkyl or phenyl;
Similar carboxylic acid derivatives, amongst others also 3-halo derivatives, are described in the literature, for example in EP-A 347 811, EP-A 400 741, EP-A 409 368, EP-A 481 512, EP-A 517 215 and in the earlier German Application P 41 42 570 (EP-A-548 710), but none of them have a hetaryl radical attached to them in the 3-position.
The biological action and selectivity of the known compounds is not always satisfactory.
It was an object of the invention to provide compounds with an improved selectivity to crop plants and/or better herbicidal or bioregulatory action.
We have found that this object is achieved by the 3-halo-3-hetarylcarboxylic acid derivatives defined at the outset, which have outstanding herbicidal and plant-growth-regulating properties.
The compounds according to the invention are synthesized starting from the epoxides IV, which are obtained from the aldehydes or ketones II or the olefins III in a generally known manner, for example as described by J. March, Advanced Organic Chemistry, 2nd ed., 1983, p. 862 and p. 750: ##STR3##
3-Halo-3-hetarylcarboxylic acid derivatives of the formula VI can be prepared by reacting the epoxides of the formula IV (for example where R=COOR.sup.9) with halogen derivatives MZ of the formula V where Z has the meaning given in claim 1 and M is hydrogen, an alkali metal cation or the equivalent of an alkaline earth metal cation: ##STR4##
The reaction can also be carried out in the presence of a diluent. All solvents which are inert to the reagents used may be used for this purpose.
Examples of such solvents or diluents are water, aliphatic, alicyclic and aromatic hydrocarbons, all of which may be chlorinated, such as, for example, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride and trichloroethylene, ethers, such as, for example, diisopropyl ether, dibutyl ether, propylene oxide, dioxane and tetrahydrofuran, ketones, such as, for example, acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, nitriles, such as, for example, acetonitrile and propionitrile, alcohols, such as, for example, methanol, ethanol, isopropanol, butanol and ethylene glycol, esters, such as, for example, ethyl acetate and amyl acetate, acid amides, such as, for example, dimethylformamide and dimethylacetamide, sulfoxides and sulfones, such as, for example, dimethyl sulfoxide and sulfolane, and bases, such as, for example, pyridine.
The reaction is preferably carried out at from 0.degree. C. to the boiling point of the solvent or solvent mixture.
The presence of a reaction catalyst may be advantageous. Suitable catalysts are organic acids and inorganic acids, and also Lewis acids. Examples are, inter alia, sulfuric acid, hy
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Baumann Ernst
Bratz Matthias
Gerber Matthias
Harreus Albrecht
Rademacher Wilhelm
BASF - Aktiengesellschaft
Qazi Sabiha N.
Shah Mukund J.
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