Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-08-17
2000-01-11
Owens, Amelia
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
549 15, A01N 4324, C07D32708, C07D33908
Patent
active
060136073
DESCRIPTION:
BRIEF SUMMARY
The present invention-relates to novel hetaroyl derivatives having herbicidal activity, processes for preparing the hetaroyl derivatives, compositions which contain them and the use of these derivatives or compositions containing them for controlling weeds.
The literature discloses herbicidally active 2-hetaroylcylohexadiones, for example in WO 948988, WO 9404524 and EP 283261.
The herbicidal properties of the known compounds and the tolerability to crop plants can only be satisfactory, however, to a limited extent.
It is an object of the present invention to find novel 2-hetaroylcyclohexanediones having improved properties.
We have found that this object is achieved by the hetaroyl derivatives of the formula I ##STR2## where the substituents have the following meanings: L and M 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; halogen, cyano, nitro; C.sub.2 -C.sub.6 -alkynyl, C1-C.sub.4 -alkoxy [sic], 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; halogen; groups: C.sub.1 -C.sub.4 -alkyl, hydrogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyloxycarbonyl; 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; halogen; groups: C.sub.1 -C.sub.4 -alkyl, hydrogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyloxycarbonyl; R.sup.3 and R.sup.2 can form a bond; 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; halogen; groups: C.sub.1 -C.sub.4 -alkyl, hydrogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyloxycarbonyl; R.sup.3 and R.sup.2 can form a bond; 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; halogen; groups: C.sub.1 -C.sub.4 -alkyl, hydrogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyloxycarbonyl; ##STR3## where the substituents have the following meanings: R.sup.5, R.sup.6 and R.sup.10 hydrogen, C.sub.1 -C.sub.4 -alkyl; being possible for these groups, if desired, to carry one to three of the following substituents: halogen, C.sub.1 -C.sub.4 -thioalkyl or C.sub.1 -C.sub.4 -alkoxy; or tetrahydropyran-3-yl, tetrahydropyran-4-yl; or carbocyclic ring;
Compounds of the formula I are obtained by reacting compounds of the formula II with a benzoic acid derivative of the formula III and rearranging them to give hetaroyl derivatives of the formula I. ##STR4##
In the above scheme 1, T in the formulae mentioned has the meaning halogen or OH and L, M, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n have the meanings given above.
The first step of the reaction sequence, the acylation, is carried out in a generally known manner, eg. by addition of an acid chloride of the formula III (T.dbd.Cl) or of a carboxylic acid III T(.dbd.OH) activated, for example, with DCC (dicyclocarbodiimides or similar agents known from the literature, eg. triphenylphosphine/DEAD=diethyl azodicarboxylate, 2-pyridine disulfide/triphenylphosphine to the solution or suspension of a cyclohexanedione II, if appropriate 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, eg. from 1.2 to 1.5 mol equivalents, based on II, of the auxiliary base can be advantageous
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Deyn Wolfgang von
Engel Stefan
Hill Regina Luise
Kardorff Uwe
Misslitz Ulf
BASF - Aktiengesellschaft
Owens Amelia
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