Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1999-09-01
2000-07-04
Stockton, Laura L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
548210, A01N 4380, C07D27506
Patent
active
060838809
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to saccharin-5-carbonylcyclohexane-1,3,5-trione derivatives of the formula I ##STR2## where: L is C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 -alkoxy; -C.sub.6 -alkenyl, C.sub.3 -C.sub.5 -alkynyl, benzyl or phenyl, the phenyl rings in each case being unsubstituted or mono- or polysubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.3 -alkoxy or halogen; chlorine, cyano, nitro or trifluoromethyl;
The invention further relates to herbicidal compositions comprising compounds I and to methods for controlling undesirable vegetation using the saccharin derivatives I.
Herbicidally active saccharincarbonylcyclohexanedione derivatives are known from WO 96/05182.
EP-A 252 298 describes herbicidal benzoyl-1,3,5-cyclohexanetriones, but these compounds do not have a saccharin structure.
It is further known to use saccharin derivatives as fungicides, for example from JP Publication 72/00419 and 73/35457, and in pharmacy, for example from EP-A 594 257.
However, the herbicidal properties of these prior art compounds and their tolerance by crop plants are not entirely satisfactory.
It is an object of the present invention to provide novel saccharin derivatives having improved properties.
We have found that this object is achieved by the saccharin-5-carbonylcyclohexane-1,3,5-trione derivatives of the general formula I defined at the outset.
Compounds of the formula I are obtained according to scheme 1 by acylating cyclohexane-1,3,5-triones of the formula II with a saccharin-5-carbonyl chloride of the formula III and rearranging the resulting enol ester of the formula IV in the presence of a catalyst to give the active compound of the formula I. ##STR3##
In scheme 1 above, the substituents R.sup.1 to R.sup.4, L, M and Z are each as defined at the outset.
The first step of the reaction sequence in scheme 1 is carried out by adding the acyl chloride III to a solution or suspension of the cyclohexane-1,3,5-trione II in the presence of an auxiliary base. The reactants and the auxiliary base are preferably employed in equimolar amounts, but a slight excess of from 1.2 to 1.5 mole equivalents of the auxiliary base may be advantageous. Suitable solvents are methylene chloride, tetrahydrofuran, ethyl acetate, toluene or, preferably, acetonitrile. Suitable auxiliary bases are alkali metal carbonates, pyridine or tertiary alkylamines, preferably triethylamine. During the addition of the acyl chloride, the reaction mixture is preferably cooled to from 0 to 10.degree. C., and thereafter, the mixture is stirred at from 20 to 70.degree. C., in particular from 25 to 40.degree. C., until the reaction has ended.
The enol ester IV can be isolated prior to the rearrangement, but the reaction is preferably carried out by admixing the reaction mixture with from two to four, preferably 2.5, equivalents of triethylamine and subsequently, at 25.degree. C., adding from 2 to 10, in particular 3, mol % of a cyano compound such as acetone cyanohydrin or preferably trimethylsilyl cyanide and then stirring the reaction mixture at from 20 to 40.degree. C., preferably at 25.degree. C., until no more enol ester IV is present. Examples of the cyanide-catalyzed rearrangement of enol esters of cyclohexane-1,3,5-triones are given in EP-A 252 298.
Work-up is carried out by acidifying the reaction mixture with 5% strength hydrochloric acid or sulfuric acid and subsequent extraction with a solvent such as ethyl acetate or methylene chloride. The extract is dried over sodium sulfate or magnesium sulfate, the solvent is distilled off under reduced pressure and the crude product is, if required, purified. The reaction product is purified for example by chromatography (silica gel, cyclohexane/ethyl acetate) or recrystallization (methanol/water or glacial acetic acid/water). A further purification method is the extraction of a solution of the crude product in ethyl acetate with an aqueous alkali metal carbonate solution, in which the end product passes over into the aqueous phase. Acidification of the aqueous solution and reextraction af
REFERENCES:
patent: 5744425 (1998-04-01), Plath et al.
JP 7200419--Abstract, 1972.
JP 7335457--Abstract, 1974.
Spitzer, Monatshefter der Chem. 11, 104 (1890).
Riedl et al., Liebigs Ann. Chem. 585, 209 (1954).
Murin et al., Chem. Ber. 92, 2033 (1959).
Deyn Wolfgang von
Engel Stefan
Hill Regina Luise
Kardorff Uwe
Misslitz Ulf
BASF - Aktiengesellschaft
Stockton Laura L.
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