Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1999-06-23
2000-08-22
O'Sullivan, Peter
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504196, 549216, 549217, 549396, A01N 4316, A01N 5716
Patent
active
061072540
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The present invention relates to novel 5-(dioxabicyclohept-6-yl)cyclohexenone oxime ethers of the formula I ##STR2## where R.sup.1 is hydrogen, the equivalent of an agriculturally useful cation, C.sub.1 -C.sub.10 -alkylcarbonyl, C.sub.1 -C.sub.10 -alkylsulfonyl, C.sub.1 -C.sub.10 -alkylphosphonyl, benzoyl, benzenesulfonyl or benzenephosphonyl, where the last three radicals may additionally carry 1 to 5 halogen atoms; -C.sub.4 -alkyl; -C.sub.6 -alkynylene chain which may carry an exo-methylene substituent (.dbd.CH.sub.2) and/or in each case one to three additional substituents selected from the group consisting of C.sub.1 -C.sub.3 -alkyl substituents and halogen atoms, which may carry one to three C.sub.1 -C.sub.3 -alkyl substituents and which contains, in addition to methylene or methine units, one of the following bridge members: oxygen, sulfur, --SO--, --SO.sub.2 -- or --N(R.sup.i)--, where R.sup.i is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl; unsubstituted, partially or fully halogenated and may carry, if it is not fully halogenated, one to three substituents selected from the group consisting of nitro, cyano, formyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -alkynyloxy and --NR.sup.5 R.sup.6, where -C.sub.6 -alkynyl and -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -acyl or benzoyl, which may carry one to three additional substituents selected from the group consisting of nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkylthio.
The invention additionally relates to the compounds I as active substances, plants.
Herbicidally active cyclohexenone oxime ethers having a tetrahydropyran-4-yl radical in position 5 of the cyclohexenone ring are known from the literature (EP-A 142 741, DE-A 38 38 309 and EP-A 456 112).
EP-A 230 235 describes herbicidally active 5-(3, 7-dioxabicyclo[4.1.0]hept-1-yl)cyclohexenone oximes which differ from the compounds according to the invention in that the bicycle is linked in position 1 instead of position 6.
The herbicidal properties of the prior art compounds with regard to their activity and in particular with regard to their selectivity against grass weeds in grass-like crops are not always entirely satisfactory.
It is an object of the present invention to provide novel herbicidally active cyclohexenone oximes. It is a further object to provide novel growth-regulating compounds.
We have found that this object is achieved by the novel 5-(dioxabicyclohept-6-yl)cyclohexenone oxime ethers I defined at the outset. Furthermore, we have found herbicidal and growth-regulating compositions comprising the compounds I, processes for preparing the compounds I and intermediates of the formula II required for their preparation, a method for controlling undesirable vegetation using the compounds I and the use of the compounds I as herbicides and growth regulators.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomer or diastereomer mixtures. The invention provides the pure enantiomers or diastereomers and also the mixtures thereof.
The moieties mentioned in the definition of the radicals R.sup.1 to R.sup.6 and Z or as substituents of alkyl, alkenyl, alkynyl and phenyl are collective terms for individual listings of the individual group members. The radicals alkyl, alkylthio, alkoxy, alkylcarbonyl, alkylsulfonyl, alkylphosphonyl, alkenyl, alkenyloxy, alkynyl and alkynyloxy can be straight-chain or branched. The unsubstituted alkylene, alkenylene and alkynylene chains are straight-chain. Halogenated substituents preferably have attached to them one to three identical or different halogen atoms. The term halogen represents in each case bromine, iodine, and in particular fluorine or ch
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Kardorff Uwe
Maywald Volker
Misslitz Ulf
Rheinheimer Joachim
Walter Helmut
BASF - Aktiengesellschaft
O'Sullivan Peter
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