Substituted 2-phenylpyridine as herbicide

Details Substituted 2-phenylpyridine as herbicide Substituted 2-phenylpyridine as herbicide

1999-02-17

2002-09-10

Rotman, Alan L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S244000, C504S255000, C546S290000, C546S293000, C546S294000, C546S345000

Reexamination Certificate

active

06448205

ABSTRACT:

The present invention relates to novel substituted 2-phenyl-pyridines of the formula I
in which the variables have the following meanings:
n is zero or 1;
R
1
is mercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylaminosulfonyl or di(C
1
-C
6
-alkyl)aminosulfonyl;
R
2
,R
3
independently of one another are hydrogen or halogen;
R
4
is cyano, hydroxyl, halogen, C
1
-C
6
-alkoxy or phenylmethoxy, it being possible for the phenyl ring to be unsubstituted or to have attached to it one to three substituents, in each case selected from the group consisting of hydroxyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, hydroxycarbonyl, (C
1
-C
6
-alkoxy)carbonyl and (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkoxy;
R
5
is hydrogen, nitro, cyano, hydroxylamino, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, —COCl, —CO—OR
6
, —CO—N(R
7
)R
8
, —CO—O—(C
1
-C
4
-alkylene)—CO—R
6
—, —CO—O—(C
1
-C
4
-alkylene)—CO—N(R
7
)R
8
, —X
1
—(C
1
-C
4
-alkylene)—CO—R
6
, —X
1
—(C
1
-C
4
-alkylene)—CO—OR
6
, —X
1
—(C
1
-C
4
-alkylene)—CO—O—(C
1
-C
4
-alkylene)—CO—OR
6
, —X
1
—(C
1
-C
4
-alkylene)—CO—N(R
7
)R
8
, —X
1
—R
9
, —CH═C(R
10
)—CO—OR
6
, —CH═C(R
10
)—CO—O—(C
1
-C
4
-alkylene)—CO—OR
6
, —CH═C(R
10
)—CO—N(R
7
)R
8
, formyl, —CO—R
6
,
 —C(R
8
)═N—OR
15
, —X
1
—(C
1
-C
4
-alkylene)—C(R
8
)═N—OR
15
, —CH═C(R
10
)—C(R
8
)═N—OR
15
, —CH(C
1
-C
6
-alkoxy)
2
, —N(R
16
)R
17
, —N(R
16
)—SO
2
—(C
1
-C
6
-alkyl), —N(R
16
)—CO—(C
1
-C
6
-alkyl), chlorosulfonyl, hydroxysulfonyl or —SO
2
—N(R
18
)R
19
;
R
6
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl or 3-oxetanyl;
R
7
is hydrogen or C
1
-C
6
-alkyl;
R
8
is hydrogen, hydroxyl, C
1
-C
6
-alkyl, hydroxycarbonyl-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, phenyl-C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy or C
3
-C
6
-alkynyloxy or
R
7
and R
8
together are a tetra- or pentamethylene chain which can have attached to it a (C
1
-C
6
-alkoxy)carbonyl radical;
R
9
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl or C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl;
R
10
is hydrogen, halogen or C
1
-C
6
-alkyl;
R
11
-R
14
independently of one another are hydrogen, C
1
-C
6
-alkyl or (C
1
-C
6
-alkoxy)carbonyl;
R
15
is hydrogen, C
1
-C
6
-alkyl, phenyl-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
16
is hydrogen or C
1
-C
6
-alkyl;
R
17
is hydrogen, C
1
-C
6
-alkyl, hydroxycarbonyl-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy;
R
18
is hydrogen or C
1
-C
6
-alkyl;
R
19
is hydrogen, C
1
-C
6
-alkyl, hydroxycarbonyl-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy or
R
18
and R
19
together are a tetra- or pentamethylene chain which can have attached to it a (C
1
-C
6
-alkoxy)carbonyl radical;
X
1
-X
3
independently of one another are oxygen or sulfur, and to the agriculturally useful salts of the compounds I where R
6
=hydrogen.
Moreover, the invention relates to
the use of the compounds I as herbicides or for the desiccation/defoliation of plants,
herbicidal compositions and compositions for the desiccation and/or defoliation of plants which comprise the compounds I as active substances,
methods of controlling undesirable vegetation and for the desiccation and/or defoliation of plants using the compounds I,
processes for the preparation of the compounds I and of herbicidal compositions and compositions for the desiccation and/or defoliation of plants which make use of the compounds I, and to
intermediates of the formulae IIa, V and VI.
WO 95/02580 describes a large number of herbicidally active 2-phenylpyridines. The general formula in this publication also embraces some of the present compounds I where R
1
=C
1
-C
4
-alkylthio.
WO 94/05153 relates to herbicidally active benzene compounds which can also have attached to them, inter alia, a pyridine ring which is substituted by halogen and methylthio. However, the specific substitution pattern of the present 2-phenylpyridines cannot be found in this publication.
DE-A 19 500 760, DE-A 19 500 758 and DE-A 19 500 911 already describe certain substituted 2-phenylpyridines of the type of the compounds I where mercapto, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulfinyl or C
1
-C
4
-alkylsulfonyl occupy the 5-position of the pyridine ring as herbicidal and desiccant/defoliant active ingredients.
However, the herbicidal activity of the known compounds is not always entirely satisfactory with regard to the harmful plants.
It is an object of the present invention to provide novel herbicidally active compounds with which undesirable plants can be controlled better, in a targeted fashion, than was possible to date. It was also an object to provide novel compounds which have a desiccant/defoliant action.
We have found that this object is achieved by the substituted 2-phenylpyridines of the formula I defined at the outset which have a herbicidal action, and by novel intermediates V and VI for their preparation.
We have furthermore found herbicidal compositions which comprise the compounds I and which have a very good herbicidal activity. Moreover, we have found processes for the preparation of these compositions and methods for controlling undesirable vegetation using the compounds I.
Moreover, we have found that the compounds I are also suitable for the defoliation/desiccation of parts of plants, suitable plants being crop plants such as cotton, potatoes, oilseed rape, sunflowers, soya beans or field beans, in particular cotton and potatoes. Accordingly, 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 the substitution pattern, the compounds of the formula I can have one or more chiral centers, in which case they are present as enantiomer or diastereomer mixtures. The invention relates not only to the pure enantiomers or diastereomers, but also to mixtures of these.
The substituted 2-phenylpyridines I where R
6
=hydrogen can exist in the form of their agriculturally useful salts, the nature of the salt generally being of no importance. In general, suitable salts are salts of those bases where the herbicidal activity is not adversely affected in comparison with the free compound I.
Especially suitable salts are those of the alkali metals, preferably sodium and potassium salts, the alkaline earth metals, preferably calcium and magnesium salts, those of the transition metals, preferably zinc and iron salts, and also ammonium salts where the ammonium ion can, if desired, have attached to it one to four C
1
-C
4
-alkyl, hydroxy-C
1
-C
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
1
-C
4
-alkyl)sulfonium salts, and sulfoxonium salts such as, preferably, tri(C
1
-C
4
-alkyl)sulfoxonium salts.
The organic moieties mentioned for the substituents R
1
and R
4
to R
19
or as radicals on a phenyl ring or on tetra- or pentamethylene are collective terms for individual enumerations of the individual group members. All carbon chains, ie. all alkyl, haloalkyl, phenylalkyl, alkylene, alkoxy, haloalkoxy, phenylalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, hydroxycarbonylalkyl, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, alkenyloxy and alkynyloxy moieties can be straight-chain or branched. Halogenated substituents preferably have attached to them one to five identical or different halogen atoms.
The meaning halogen is in each case f

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