Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-08-24
1999-07-20
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
504282, C07D40906, C07D41106
Patent
active
059257679
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel herbicidally active pyrazol-4-yl-hetaroyl derivatives, to processes for the preparation of the pyrazol-4-yl-hetaroyl derivatives, to compositions comprising them, and to the use of these derivatives or of the compositions comprising them for controlling weeds.
Herbicidally active pyrazolylaroyl derivatives are disclosed in the literature, for example in WO 9504054, WO 9401431 and EP 629623 and EP 344774.
However, the herbicidal properties of the known compounds and their compatibility with crop plants are only moderately satisfactory.
It is an object of the present invention to provide novel pyrazol-4-yl-hetaroyl derivatives which have improved properties.
We have found that this object is achieved by pyrazol-4-yl-hetaroyl derivatives of the formula I ##STR2## where the substituents have the following meanings: L and M are 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, 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; 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; 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.2 and R.sup.3 may form a linkage; 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; 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 may form a linkage; 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; 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 R.sup.5 is C.sub.1 -C.sub.4 -alkyl, and alkylphenylsulfonyl,
Compounds of the formula I 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 hetaroyl derivatives of the formula I. ##STR4##
In the above Scheme 1, T in the abovementioned formulae has the meanings halogen or OH, and L, M, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 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 adding an acid chloride of the formula III (T=Cl) or a carboxylic acid III (T=OH) which has been activated for the literature, eg. triphenylphosphine/DEAD=diethyl azodicarboxylate, 2-pyridine disulfide/triphenylphosphine to the solution or suspension of a cyclohexnedione II in the presence or absence of an auxiliary base. The reactants and the auxiliary base are expediently employed in equimolar amounts. A slight excess, eg. 1.2 to 1.5 mole equivalents, of the auxiliary base, based on II, may be advantageous in certain cases.
Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Examples of solvents which can be used are methylene chloride, dioxane, diethyl ether, toluene, acetonitrile or ethyl acetate.
The reaction mixture is
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Deyn Wolfgang von
Engel Stefan
Gotz Norbert
Hill Regina Luise
Kardorff Uwe
BASF - Aktiengesellschaft
Ramsuer Robert W.
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