Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-02-03
1998-04-28
Richter, Johann
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
548210, C07D27506, A01N 4380
Patent
active
057444250
DESCRIPTION:
BRIEF SUMMARY
This application is 371 of PCT/EP95/02973 filed Jul. 27, 1995.
The present application relates to saccharin derivatives of the formula I ##STR2## where the substituents have the following meanings: L and M are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, chlorine, cyano, methylsulfonyl, nitro or trifluoromethyl; C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.5 -alkynyl, C.sub.1 -C.sub.4 -acyl, benzyl or phenyl, the phenyl rings in each case being unsubstituted or substituted by halogen or C.sub.1 -C.sub.4 -alkyl; ##STR3## where either R.sup.1 to R.sup.6 are hydrogen or methyl, or, if R.sup.1, R.sup.2, R.sup.3, R.sup.5 and R.sup.6 are hydrogen, R.sup.4 is 2-ethylthiopropyl, tetra-hydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl or 1-methylthiocyclopropyl, R.sup.2 and R.sup.3 form a three-membered ring such that a 2-linked ##STR4## and agriculturally customary salts of the compounds I.
The invention further relates to herbicidal compositions containing the compounds I, and methods of controlling undesired plant growth using the saccharin derivatives I. Moreover, the present invention also encompasses intermediates for preparing the final products I according to the invention and preparation processes for the products I, starting from the novel intermediates of the formulae IV and V ##STR5## where the remaining radicals L, M and Z have the abovementioned meanings.
Saccharin derivatives having herbicidal action cannot be inferred from the prior art. However, unsubstituted saccharin (o-sulfo-benzimide, i.e. L, M, Q and Z in formula I=H) has been known as a synthetic sweetener for a long time. 4-Hydroxysaccharin is further known as a sweetener (German Offenlegungsschrift 3 607 343). The use of saccharin derivatives in pest control is also known, e.g. JP publication 72/00419, 73/35457 (fungicides) and in pharmacy, e.g. EP-A 594 257 and literature references mentioned therein.
Herbicidally active 2-aroylcyclohexanediones are a subject of the earlier German Application P 44 03 670. Among other things, linkage with saccharin and N-alkylsaccharin is mentioned without giving a preparation route for these compounds.
Heterocyclic compounds having a sulfonamide-containing ring have been disclosed as herbicides, a typical representative which can be mentioned here being bentazone ##STR6##
It is an object of the present invention to make available novel herbicides having a basic structure which was hitherto unknown for this indication.
We have found that this object is achieved by the compounds I and the intermediates IV and V defined at the outset. The intermediates IV and their preparation are the subject of the parallel German Application DE-A 44 27 996.
Compounds of the formula I are obtained by acylating compounds of the formula II or III with an acid chloride of the formula V and rearranging to give saccharin derivatives of the formula I.1: ##STR7##
In the abovementioned formulae, L and M have the meaning given at the outset and Z is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.5 -alkynyl, C.sub.1 -C.sub.4 -acyl or benzyl or phenyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.4 -alkyl.
The first step of the reaction sequence, the acylation, is carried out in a generally known manner, e.g. by addition of an acid chloride of the formula V to the solution or suspension of a cyclohexane-1,3-dione II or III in the presence of an auxiliary base. The reactants and the auxiliary base are in this case expediently employed in equimolar amounts. A small excess, e.g. from 1.2 to 1.5 mol equivalents, based on II or III, of the auxiliary base can be advantageous in certain circumstances.
Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. The solvents used can be e.g. methylene chloride, diethyl ether, toluene or ethyl acetate.
During the addition of the acid chloride, the reaction mixture is preferably cooled to from 0.degree. to 10.degree. C., then stirred
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Deyn Wolfgang von
Engel Stefan
Gerber Matthias
Kardorff Uwe
Kast Jurgen
BASF - Aktiengesellschaft
Crosslutz Laura
Richter Johann
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