Herbicidally active phenyldiketone compounds

Details Herbicidally active phenyldiketone compounds Herbicidally active phenyldiketone compounds

1997-07-30

1998-12-08

Higel, Floyd D.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504234, 504242, 504261, 504263, 504244, 504265, 504266, 504270, 504271, 504274, 504283, 504288, 504289, 504290, 504294, 504295, 504291, 504309, 544 53, 544318, 544335, 546174, 546330, 548128, 548131, 548136, 548141, 548143, 548204, 548214, 548236, 548247, 5482674, 548550, 548551, 5483701, 549 38, 549 39, 549 77, 549450, 549451, 558405, A01N 4380, A01N 4376, C07D26110, C07D26330, C07D27722, C07D30738, C07D52100

Patent

active

058469060

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP96/00624 filed Feb. 14, 1996 published as WO96/26193 Aug. 29, 1996.
The present invention relates to novel phenyldiketone compounds which are herbicidally active, to processes for the preparation of the phenyldiketone compounds, to compositions comprising them, and to the use of these compounds or the compositions comprising them for controlling weeds.
The literature discloses herbicidally active phenyldiketone compounds, for example EP 625505.
However, the herbicidal properties of the known compounds and their tolerance by crop plants are only moderately satisfactory.
It was an object of the invention to find novel phenyldiketone derivatives which have improved properties.
We have found that this object is achieved by novel phenyldiketone compounds of the formula I ##STR2## in which 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 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 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 -haloalkylthio, di-C.sub.1 -C.sub.4 -alkylamino or 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 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.6 -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, tert-butyl;
The phenyldiketone derivatives can exist in the following tautomeric forms: ##STR3##
Compounds of the formula I are obtained by acylating the magnesium enolate A2 of a cyanoketone of the formula A1 ##STR4## with a benzoic acid derivative of the formula III (T=C1) to give the enolized compound Ic. ##STR5##
In the abovementioned formulae, L, M and Z have the meanings mentioned at the outset, and T is halogen.
The first step of the reaction sequence is carried out in such a way that a methanolic solution of a cyanoketone of the formula A1 is treated with magnesium and a small amount of CCl.sub.4, and this is allowed to react until the magnesium enolate is obtained. Analogous C-acylations of cyanoketones are described, for example, in EP-A 496 630 and EP-A 496 631.
After the methanol has been removed, the magnesium enolate obtained, of the formula A2, is dissolved in toluene or acetonitrile, acetonitrile being preferred, and then an amount of the acid chloride of the formula III which is equivalent to A1 is added dropwise in the form of a solution in acetonitrile. After the mixture has been stirred at 25.degree. C. to 50.degree. C. for 1-16 hours, the reaction is complete. For working-up, the mixture is concentrated in vacuo, the residue which remains is taken up in a solvent, such as ethyl acetate or methylene chloride, and washed using 10 percent strength HCl in order to destroy the magnesium salt. After the organic phase has been washed with water, it is dried using a desiccant, such as sodium sulfate, and concentrated. The product is precipitated from the residue which remains by trituration with a hydrocarbon, such as petroleum ether, cyclohexane or n-pentane.
The cyanoketones of the for

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