Substituted 2-phenylpyridines as herbicides

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

2001-07-05

2002-08-13

Fan, Jane (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S295000, C546S280400, C546S280100

Reexamination Certificate

active

06432880

ABSTRACT:

This application is a 371 of PCT/EP00/00095 filed Jan. 8, 2000 now WO 00/42015 filed Jul. 20, 2000.
The present invention relates to novel substituted 2-phenyl-5 pyridines of the formula I
where:
n is zero or 1;
R
1
is aminosulfonyl, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl or C
1
-C
6
-haloalkylsulfonyl;
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, where the phenyl ring may be unsubstituted or may carry from 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—OR
6
, —CO—O—(C
1
-C
4
-alkylene)—CO—N(R
7
)R
8
, —X
1
—(C
1
-C
4
-alkylene)—CO—OR
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
, —CN(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 or C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl;
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;
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;
X
1
-X
3
independently of one another are oxygen or sulfur;
and 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 ingredients,
methods for controlling undesirable vegetation and for the desiccation and/or defoliation of plants using the compounds I,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation and/or defoliation of plants using the compounds I and also
intermediates of the formula IIa.
WO 96/21646 and WO 96/21647 have already described certain substituted 2-phenylpyridines of the type of the compounds I having, inter alia, C
1
-C
4
-alkylsulfinyl or C
1
-C
4
-alkylsulfonyl in the 5-position of the pyridine ring for use as herbicides and desiccants/defoliants.
Furthermore, 2-phenylpyridines having herbicidal and/or desiccant/defoliant activity, which differ from the present compounds I in that R
1
is directly attached to the pyridine ring, form part of the subject matter of WO 98/07700.
However, the herbicidal activity of the prior art compounds is, with a view to the harmful plants, not always entirely satisfactory.
It is an object of the present invention, therefore, to provide novel herbicidally active compounds which allow better selective control of undesirable plants than known compounds. It is a further object to provide novel compounds which have a desiccant/defoliant action.
We have found that these objects are achieved by the herbicidal substituted 2-phenylpyridines of the formula I defined at the outset and by novel intermediates IIa for their preparation.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Furthermore, we have found that the compounds I are also suitable for the desiccation/defoliation of parts of plants, suitable plants being crop plants such as cotton, potatoes, oilseed rape, sunflower, soybean or field beans, in particular cotton and potatoes. In this regard, we have found compositions for the desiccation and/or defoliation of plants, processes for preparing 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 contain one or more chiral centers, in which case they exist in the form of enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and mixtures thereof.
The substituted 2-phenylpyridines I where R
6
=hydrogen may be present in the form of their agriculturally useful salt, the type of salt being generally immaterial. In general, the salts of such bases are suitable where the herbicidal activity is not adversely affected in comparison to the free compound I.
Suitable salts are, in particular, 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 may, if desired, carry one to four C
1
-C
4
-alkyl, 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 organic molecular moieties mentioned for the substituents R
1
and R
4
to R
19
or as radicals on a phenyl ring are collective terms for individual listings of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, phenylalkyl, alkylene, alkoxy, haloalkoxy, phenylalkoxy, alkylsulfinyl, alkylsulfonyl, hydroxycarbonylalkyl, alkenyl, alkynyl, alkenyloxy and alkynyloxy moieties can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.
The term halogen represents in each case fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
Examples of other meanings are:
C
1
-C
6
-alkyl: C
1
-C
4
-alkyl such as CH
3
, C
2
H
5
, CH
2
-C
2
H
5
, CH(CH
3
)
2
, n-butyl, CH(CH
3
)—C
2
H
5
, CH
2
—CH(CH
3
)
2
and C(CH
3
)
3
, or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethyipropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylp ropyl, 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 or 1-ethyl-2-methylpropyl, in particular CH
3
, C
2
H
5
, CH
2
—C
2
H
5
, CH(CH
3
)
2
, n-butyl, C(CH
3
)
3
, n-pentyl or n-hexyl;
C
1

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