Isoxazolylbenzoyl derivatives

Details Isoxazolylbenzoyl derivatives Isoxazolylbenzoyl derivatives

1997-08-22

1998-11-10

Lambkin, Deborah C.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504269, 548240, 548206, A01N 4380, C07D26106, C07D27502

Patent

active

058344020

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP96/00592 Feb. 13, 1996.
The present invention relates to novel herbicidally active isoxazolylbenzoyl derivatives, to processes for the preparation of the isoxazolylbenzoyl derivatives, to compositions comprising them, and to the use of these derivatives or of the compositions comprising them for controlling weeds.
The literature discloses herbicidally active isoxazolylbenzoyl derivatives, for example EP 609797.
European Patent Application EP-A-0 418 175 discloses 4-benzoyl-isoxazole derivatives which have herbicidal properties. The benzoyl group is not substituted by a heterocyclic group.
However, the herbicidal properties of the known compounds and the tolerance by crop plants are less than fully satisfactory.
It is an object of the present invention to find novel isoxazolylbenzoyl derivatives which have improved properties.
There have now been found novel isoxazolylbenzoyl derivatives of the formula I ##STR2## where the substituents have the following meanings: L and M are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C.sub.1 -C.sub.4 -alkoxy, or are halogen, cyano, nitro, a group --(Y).sub.n --S(O).sub.m R.sup.7 or a group --(Y).sub.n --CO--R.sup.8, has one to three heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen and which is unsubstituted or substituted by halogen, cyano, nitro, a group --CO--R.sup.8, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.8 -cycloalkyl, 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 -halo-alkylthio, di-C.sub.1 -C.sub.4 -alkylamino, phenyl which is unsubstituted or substituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, or an oxo group which may also exist as a hydroxyl group in the tautomeric form, or which forms a bicyclic system together with a fused phenyl ring which is unsubstituted or substituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, a fused carbocycle or a fused second heterocycle which is unsubstituted or substituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkyl, R.sup.10, -C.sub.4 -alkoxy or NR.sup.9 R.sup.10, ##STR3## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or --CO.sub.2 R.sup.3, -cycloalkyl, which can be unsubstituted or substituted by one or more halogen atoms or by C.sub.1 -C.sub.4 -alkyl and -C.sub.4 -acyl, or a chlorine atom;
Compounds of the formula I where R.sup.1 is H are obtained by acylating the al., JOC 43, 2087 (1978)! with a benzoic acid derivative of the formula III (T=Cl) to give an ester of the formula B1, converting this ester by reacting it with p-toluene-sulfonic acid in toluene to give a 1,3-diketone of the formula C1, thereupon either converting the 1,3-diketone C1 with triethyl orthoformate into an enol ether D1 or with dimethylformamide dimethyl acetal into an enamine D2, and reacting D1 or D2 with hydroxylamine to give the isoxazolylbenzoyl derivative of the formula I.a. The reaction sequence is compiled in the equation which follows: ##STR4##
Benzoic acid derivatives of the formula III can be prepared as follows:
Benzoyl halides such as, for example, benzoyl chlorides of the formula III (T=Cl) are prepared in a manner known per se by reacting the benzoic acids of the formula III (T=OH) with thionyl chloride.
The benzoic acids of the formula III (T=OH) can be prepared in a known manner from the corresponding esters of the formula III (T=C.sub.1 -C.sub.4 -alkoxy) by acidic or alkaline hydrolysis.
The intermediates of the formula III can be synthesized for example in accordance with equations 2 and 3 via the routes described hereinbelow. ##STR5## T is C.sub.1 -C.sub.4 -alkoxy, x is Cl, Br, I, --OS(O).sub.2 CF.sub.3, --OS(O).sub

REFERENCES:
patent: 5480857 (1996-01-01), Cramp et al.
patent: 5489570 (1996-02-01), Geach et al.
patent: 5656573 (1997-08-01), Roberts et al.
patent: 5658858 (1997-08-01), Bailey et al.

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