Herbicidally active pyrazol-4-ylbenzoyl compounds

Details Herbicidally active pyrazol-4-ylbenzoyl compounds Herbicidally active pyrazol-4-ylbenzoyl compounds

1997-07-30

1998-12-08

Higel, Floyd D.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

564234, 564242, 564244, 564261, 564263, 564265, 564266, 564270, 564271, 564274, 564283, 564288, 564289, 564290, 564291, 564294, 564295, 544 53, 544318, 544335, 546174, 546330, 548128, 548131, 548136, 548141, 548143, 548204, 548214, 548236, 548247, 5482674, 5483701, 548550, 548551, 5483641, 5483647, 5483657, 549 38, 549 39, 549 77, 549450, 549451, 558405, A01N 4376, A01N 4380, C07D26110, C07D26330, C07D27722, C07D30738, C07D52100

Patent

active

058469079

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP96/00635 filed Feb. 14, 1996.
The present invention relates to novel herbicidally active pyrazolylbenzoyl compounds, to processes for the preparation of the pyrazolylbenzoyl compounds, to compositions comprising them, and to the use of these compounds or compositions comprising them for controlling weeds.
Herbicidally active pyrazolylbenzoyl compounds have been disclosed in the literature, for example in EP 352543.
However, the herbicidal properties of the known compounds and their tolerance by crop plants are not entirely satisfactory.
It was an object of the present invention to find novel pyrazolylbenzoyl compounds with improved properties.
We have found that this object is achieved by novel pyrazolylbenzoyl compounds of the formula I ##STR2## where the substituents are as follows: L, 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 hetero atoms selected from the group consisting of oxygen, sulfur and 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 -haloalkylthio, di-C.sub.1 -C.sub.4 -alkylamino, by 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 by an oxo group which may also be present 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 or with a fused carbocycle or with 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 C.sub.1 -C.sub.4 -alkyl, and alkylphenylsulfonyl and
Compounds of the formula I are obtained by acylating 5-hydroxypyrazoles of the formula IIa with a benzoyl derivative of the formula III (T=C1) and subjecting the pyrazole ester formed to a rearrangement reaction to give the compounds of the formula Ic. ##STR4##
In the abovementioned formulae, T is halogen and L, M and Z are as described at the outset.
The first step of the reaction sequence, namely the acylation, is carried out in a generally known manner, for example by adding a benzoyl derivative of the formula III (T=C1) to the solution or suspension of a 5-hydroxypyrazole IIa in the presence of an auxiliary base. The reactants and the auxiliary base are expediently employed in approximately equimolar amounts. A slight excess of the auxiliary base, for example 1.2 to 1.5 mol equivalents, based on II, may be advantageous in some cases.
Suitable auxiliary bases are for example tertiary alkylamines, pyridine or alkali metal carbonates, while methylene chloride, diethyl ether, toluene or ethyl acetate can be used as solvents. During the addition of the acid chloride, the reaction mixture is advantageously cooled to 0.degree.-10.degree. C., and the mixture is then stirred at a higher temperature, for example at 25.degree.-50.degree. C., until the reaction has ended.
Work-up is carried out in the customary manner, for example the reaction mixture is poured into water and extracted using methylene chloride. After the organic phase has been dried and the solvent removed, the crude 5-hydroxypyrazole ester can be employed in the rearrangement reaction without further purification. Preparation examples for benzoic esters of 5-hydroxypyrazoles ca

REFERENCES:
King, "Medicinal Chemistry: Principles and Practice", pp. 206 to 209 (1994) .

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