Substituted 2-phenyl pyridines, their manufacture and use as...

Details Substituted 2-phenyl pyridines, their manufacture and use as... Substituted 2-phenyl pyridines, their manufacture and use as...

1999-11-17

2002-07-16

Aulakh, Charanjit S. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S295000, C546S288000, C546S339000, C546S341000, C546S342000, C546S345000, C504S116100, C504S167000, C504S254000

Reexamination Certificate

active

06420314

ABSTRACT:

This application is a 371 of PCT/EP98/02878 filed May 15, 1998, now WO 98/54137 Dec. 3, 1998.
The present invention relates to novel substituted 2-phenylpyridines of the formula I
in which the substituents and the index m have the following meanings:
m is 0 or 1;
is halogen, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulfinyl, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylthio or cyano;
R
2
is fluorine or trifluoromethyl;
R
3
is hydrogen or halogen;
R
4
is halogen or cyano;
R
5
is CO
2
R
6
, OR
7
, SR
7
, C(R
8
)═N—O—R
7
or C(R
8
)═C(R
8
)—CO—O—R
6
, where
R
6
is hydrogen, an unsubstituted or halogen-substituted C
1
-C
8
-alkyl-, C
3
-C
6
-alkenyl- or C
3
-C
6
-alkynyl radical; C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkenyloxycarbonyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkynyloxycarbonyl-C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl;
R
7
may have the meaning of R
6
or may be CH
2
—CO
2
[C
1
-C
4
-alkylene)]—CO
2
R
9
or CH[C
1
-C
4
-alkyl]CO
2
—[C
1
-C
4
-alkylene]—CO
2
R
9
;
R
8
is hydrogen, halogen or C
1
-C
4
-alkyl and
R
9
is hydrogen or C
1
-C
4
-alkyl,
and the agriculturally useful salts of the compounds I.
Furthermore, the invention relates to
a process for preparing the compounds I and
intermediates of the formula II,
herbicides and compositions for the desiccation and/or defoliation of plants which comprise the compounds I as active substances,
methods for controlling undesirable vegetation and for the desiccation and/or defoliation of plants using the compounds I.
Substituted 2-phenyl-3-chloropyridines having herbicidal activity are already known from WO 95/02580, WO 95/02590 and WO 97/11059.
However, the herbicidal activity of the prior art compounds with respect to harmful plants is not always entirely satisfactory.
It is an object of the present invention to provide novel herbicidally active compounds which allow better selective control of undesirable plants. It is a further object to provide novel compounds which have desiccant/defoliant action.
We have found that these objects are achieved by the substituted 2-phenylpyridines of the formula I defined at the outset having herbicidal activity, and by the novel intermediates II for their preparation.
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 relates to the pure enantiomers or diastereomers and also to mixtures thereof.
The substituted 2-phenylpyridines I where R
6
, R
7
and R
9
=hydrogen may be present in the form of their agriculturally useful salts, the kind of salts usually not being important. Suitable in general are the salts of those bases whose herbicidal activity is not impaired in comparison to the free compound I.
Suitable salts are in particular those of the alkali metals, preferably sodium salts and potassium salts, of the alkaline earth metals, preferably calcium salts and magnesium salts, those of the transition metals, preferably zinc salts and iron salts, and ammonium salts where the ammonium ion, if desired, may carry one to four C
1
-C
4
-alkyl or hydroxy-C
1
-C
4
-alkyl substituents and/or one 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
1
-C
4
-alkyl)sulfonium salts and sulfoxonium salts such as preferably tri-(C
1
-C
4
-alkyl)sulfoxonium salts.
The terms alkyl, alkylene haloalkyl, alkoxy, carboxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkenyl and alkynyl used in the definition of the substituents R
1
, R
6
, R
7
, R
8
and R
9
are—like the term halogen—collective terms for individual enumerations of the individual group members. All alkyl moieties may be straight-chain or branched. The haloalkyl radical preferably carries one to five identical or different halogen atoms.
Specific meanings are, for example:
halogen: fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine;
C
1
-C
4
-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C
1
-C
6
-alkyl: C
1
-C
4
-alkyl as mentioned above, and n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
C
1
-C
8
-alkyl: C
1
-C
6
-alkyl as mentioned above, and, inter alia, n-heptyl, n-octyl;
C
3
-C
4
-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl and 2-methylprop-2-en-1-yl;
C
3
-C
6
-alkenyl: C
3
-C
4
-alkenyl as mentioned above, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl, preferably ethenyl and prop-2-en-1-yl;
C
3
-C
4
-alkynyl: prop-1-in-1-yl, prop-2-in-3-yl, n-but-1-in-1-yl, n-but-1-in-4-yl, n-but-2-in-1-yl;
C
3
-C
6
-alkynyl: C
3
-C
4
-alkynyl as mentioned above, and n-pent-1-in-1-yl, n-pent-1-in-3-yl, n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n-pent-2-in-5-yl, 3-methylbut-1-in-1-yl, 3-methylbut-1-in-3-yl, 3-methylbut-1-in-4-yl, n-hex-1-in-1-yl, n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl, n-hex-1-in-6-yl, n-hex-2-in-1-yl, n-hex-2-in-4-yl, n-hex-2-in-5-yl, n-hex-2-in-6-yl, n-hex-3-in-1-yl, n-hex-3-in-2-yl, 3-methylpent-1-in-1-yl, 3-methylpent-1-in-3-yl, 3-methylpent-1-in-4-yl, 3-methylpent-1-in-5-yl, 4-methylpent-1-in-1-yl, 4-methylpent-2-in-4-yl and 4-methylpent-2-in-5-yl, preferably prop-2-in-1-yl, 1-methylprop-2-in-1-yl;
C
1
-C
3
-fluoroalkyl: C
1
-C
3
-alkyl as mentioned above where in each case 1-5 hydrogen atoms are replaced by fluorine, e.g. fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl, preference is given to difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl and 3,3,3-trifluoropropyl, particular preference is given to trifluoromethyl;
C
1
-C
4
-haloalkyl: C
1
-C
4
-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine

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