Substituted 2-phenylpyridines as herbicides

Details Substituted 2-phenylpyridines as herbicides Substituted 2-phenylpyridines as herbicides

1998-03-13

2000-01-04

Huang, Evelyn Mei

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

546330, 546334, 546335, 546337, 546342, 546345, 546346, A01N 4340, C07D21361

Patent

active

060109807

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel substituted 2-phenylpyridines of the formula I ##STR2## where the variables have the following meanings: n is 0 or 1; --CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7) R.sub.8, --O-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6, --O-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7)R.sup.8, --S-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6 or --S-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7)R.sub.8, where -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.3 -C.sub.4 -alkynyl, -alkyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl-C.sub.1 -C.sub.4 -alkyl and =hydrogen.
The invention furthermore relates to defoliation of plants, defoliation of plants which comprise the compounds I as active ingredients, and/or defoliation of plants using the compounds I, compositions and compositions for the desiccation and/or defoliation of plants using the compounds I, and
Herbicidally active substituted 2-phenylpyridines have already been disclosed in WO 95/02580, WO 95/02590 and the earlier German Applications DE-A 19 500 760, DE-A 19 500 758, DE-A 19 500 911 and DE-A 19 528 943.
WO 95/02580 describes a multiplicity of herbicidally active 2-phenylpyridines. However, this publication does not describe the compounds of the formula I and their especially advantageous properties.
Regarding the harmful plants, the herbicidal action of the known compounds is, however, not always fully satisfactory.
It is an object of the present invention to provide novel herbicidally active compounds which allow better targeted control of undesirable plants than has been possible to date. It is also an object of the present invention to provide novel compounds which act as desiccants/defoliants.
We have found that these objects are achieved by the herbicidally active substituted 2-phenylpyridines of the formula I defined at the outset, and by novel intermediates IIb for their preparation.
We have also found herbicidal compositions which comprise the compounds I and which have very good herbicidal action. We have furthermore found processes for the preparation of these compositions and methods of controlling undesirable vegetation using the compounds I.
We have furthermore found that the compounds I are also suitable for the defoliation/desiccation of parts of plants, suitable crop plants being cotton, potatoes, oil seed rape, sunflowers, soya beans or field beans, in particular cotton and potatoes. Thus, we have found compositions for the desiccation and/or defoliation of plants, processes for the preparation of these compositions and methods for the desiccation and/or defoliation of plants using the compounds I.
Depending on their substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they are present as enantiomer or diastereomer mixtures. The invention relates to the pure enantiomers or diastereomers and to their mixtures.
The substituted 2-phenylpyridines I where R.sup.6 =hydrogen can be present in the form of their agriculturally useful salts, the nature of the salt generally not being important. Suitable salts are generally salts of those bases where the herbicidal action is not adversely affected in comparison with the free compound I.
Especially useful salts are salts of the alkali metals, preferably sodium and potassium salts, of the alkaline earth metals, preferably calcium and magnesium salts, of the transition metals, preferably zinc and iron salts, and ammonium salts where the ammonium ion can have attached to it, if desired, one to four C.sub.1 -C.sub.4 -alkyl, hydroxy-C.sub.1 -C.sub.4 -alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl(2-hydroxyethyl)ammonium salts, furthermore phosphonium salts, sulfonium salts such as preferably tri(C.sub.1 -C.sub.4 -alkyl)sulfonium salts, and sulfoxonium salts

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