Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-08-14
1999-12-21
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504244, 504247, 504262, 504263, 504265, 504266, 504270, 504272, 504273, 504275, 504280, 504283, 504239, 504294, 544332, 546153, 546290, 546340, 548132, 548136, 548182, 548203, 548214, 548225, 548235, 548260, 5482658, 5482694, 5483411, 5483771, 5483791, 5483794, 548563, 548571, 549 79, 549497, 549498, C07D30754, C07D30746, C07D33324, C07D33322, A01N 4308, A01N 4310, A01N 4328
Patent
active
060049030
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel benzoyl derivatives having a herbicidal action, processes for the preparation of the benzoyl derivatives, agents which contain them and the use of these derivatives or agents containing them for weed control.
Herbicidal 2-aroylcyclohexanediones are disclosed in the literature, for example in EP 90262, EP 135191, EP 186118, EP 186119, EP 186120, EP 319075, WO 9005712, JO 3052862 and JO 3120202.
However, the herbicidal properties of the known compounds and the tolerance by crops are satisfactory only to a limited extent.
It is an object of the present invention to provide novel 2-aroylcyclohexanediones having improved properties.
We have found that this object is achieved by novel benzoyl derivatives of the formula I ##STR3## where L and M are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl or C.sub.1 -C.sub.4 -alkoxy, where these groups may be unsubstituted or substituted by one to five halogen atoms or C.sub.1 -C.sub.4 -alkoxy, or are each 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, radical containing one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, 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 unsubstituted or halogen-, cyano-, nitro-, C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -haloalkyl-substitated phenyl or by an oxo group which may also be present in tautomeric form as a hydroxyl group, or which forms a bicyclic system with a fused-on phenyl ring substituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, a fused-on carbocyclic structure or a fused-on second heterocyclic structure 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, NR.sup.9 R.sup.10, -C.sub.4 -alkoxy, or NR.sup.9 R.sup.10, formula II, ##STR4## where R.sup.1, R.sup.2, R.sup.4 and R.sup.6 are each hydrogen or C.sub.1 -C.sub.4 -alkyl, -cycloalkyl, where these groups may carry from one to three of the following substituents: halogen, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -alkoxy, tetrahydrothiopyran-3-yl six-membered carbocyclic ring,
Benzoyl derivatives of the formula Ia ##STR5## where L is 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, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano and M is 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, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano and Q and Z have the abovementioned meanings, are preferred.
Other preferred benzoyl derivatives are those of the formula Ib ##STR6## where L and M are each 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, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano and Q and Z have the meanings stated in claim 1.
Compounds of the formula Ic are obtained by reacting compounds of the formula II with a benzoic acid derivative of the formula III and subjecting the product to a rearrangement reaction to give benzoyl derivatives of the formula Ic: ##STR7##
In the abovementioned formulae, T is halogen and L, M and Z have the abovementioned meanings.
The first
Deyn Wolfgang von
Engel Stefan
Harreus Albrecht
Hill Regina Luise
Kardorff Uwe
BASF - Aktiengesellschaft
Rao Deepak R.
Shah Mukund J.
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