Substituted 2-(benzoaryl)pyridines

Details Substituted 2-(benzoaryl)pyridines Substituted 2-(benzoaryl)pyridines

2000-01-11

2002-05-07

Rotman, Alan L. (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S244000, C504S252000, C504S253000, C546S270100, C546S271700

Reexamination Certificate

active

06383986

ABSTRACT:

The present invention relates to novel substituted 2-(benzaryl)pyridines of the formula I
where:
n is zero or 1;
R
1
is hydrogen, cyano, nitro, amino, hydroxyl, mercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, C
1
-C
6
-alkylaminosulfonyl or di(C
1
-C
6
-alkyl)aminosulfonyl;
R
2
and R
3
independently of one another are each hydrogen or halogen;
R
4
is cyano, hydroxyl, halogen, C
1
-C
6
-alkoxy or benzyloxy, where the phenyl ring may be unsubstituted or may carry 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;
X is the —Y—C(ZR
5
)═N— moiety of a hetaryl ring, where the nitrogen may be attached to &agr; or &bgr; and
Y is oxygen, sulfur or —N(R
6
)—;
Z is a chemical bond, oxygen, sulfur, —S(O)—, —SO
2
— or —N(R
7
)—;
R
5
, R
6
and R
7
independently of one another are each hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, cyano-C
1
-C
4
-alkyl, hydroxy-C
1
-C
4
-alkyl, C
3
-C
6
-alkenyl, cyano-C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, cyano-C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkoxy-C
1
-C
4
-alkyl, C
3
-C
4
-alkenyloxy-C
1
-C
4
-alkyl, C
3
-C
4
-alkynyloxy-C
1
-C
4
-alkyl, C
3
-C
8
-cycloalkyloxy-C
1
-C
4
-alkyl, amino-C
1
-C
4
-alkyl, C
1
-C
4
-alkylamino-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkyl)amino-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkylthio-C
1
-C
4
-alkyl, C
3
-C
4
-alkenylthio-C
1
-C
4
-alkyl, C
3
-C
4
-alkynylthio-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfinyl-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkylsulfinyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkenylsulfinyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkynylsulfinyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkylsulfonyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkenylsulfonyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkynylsulfonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl, hydroxycarbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkylthio)carbonyl-C
1
-C
4
-alkyl, aminocarbonyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylaminocarbonyl-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkyl)aminocarbonyl-C
1
-C
4
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C
1
-C
4
-alkyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member, and where each cycloalkyl, phenyl and heterocyclyl ring may be unsubstituted or may carry one to four substituents, in each case selected from the group consisting of cyano, nitro, amino, hydroxyl, carboxy, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, (C
1
-C
4
-alkoxy)carbonyl, (C
1
-C
4
-alkyl)carbonyl, (C
1
-C
4
-haloalkyl)carbonyl, (C
1
-C
4
-alkyl)carbonyloxy, (C
1
-C
4
-haloalkyl)carbonyloxy and di(C
1
-C
4
-alkyl)amino, or, if Z is a chemical bond, R
5
is also hydrogen, cyano, mercapto, amino, halogen, —CH
2
—CH(halogen)-R
8
, —CH═CH—R
8
or —CH═C(halogen)-R
8
, where R
8
is hydroxycarbonyl, (C
1
-C
4
-alkoxy)carbonyl, (C
1
-C
4
-alkylthio)carbonyl, aminocarbonyl, C
1
-C
4
-alkylaminocarbonyl or di(C
1
-C
4
-alkyl)aminocarbonyl,
or R
5
and R
7
together are a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain which may in each case be unsubstituted or may carry one to four C
1
-C
4
-alkyl groups or one or two (C
1
-C
4
-alkoxy)carbonyl groups,
and the agriculturally useful salts of these compounds I.
The invention further relates to
the use of the compounds I as herbicides and/or the desiccation/defoliation of plants,
herbicides and compositions for the desiccation and/or defoliation of plants which comprise the compounds I as active substances,
processes for preparing the compounds I and herbicides and compositions for the desiccation/defoliation of plants using the compounds I,
Methods for controlling undesirable vegetation and for the desiccation/defoliation of plants using the compounds I, and
novel intermediates of the formulae Va/Vb, VIa/VIb and VIIIa/VIIIb, from which the compounds I are obtainable.
WO 96/11917 describes certain benzoxazoles and benzthiazoles and EP-A 616 807 describes certain benzimidazoles having various pharmaceutical activities whose general formulae—if the substituents are chosen appropriately—formally also include some of the present compounds I.
It is an object of the present invention to provide novel herbicidal 2-arylpyridines 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 this object is achieved by the present substituted 2-(benzaryl)pyridines of the formula I.
Furthermore, we have found herbicides which comprise the compounds I and have a 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. 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. E/Z isomers may also be possible for compounds I having at least one olefinic radical. The invention relates to the pure enantiomers or diastereomers and also to mixtures thereof.
The organic moieties mentioned in the definition of the substituents R
1
, R
4
to R
8
or as radicals on cycloalkyl, phenyl or heterocyclic rings or on the chain R
5
-R
7
are—like the term halogen—collective terms for individual listings of the individual group members. All carbon chains, i.e. all the alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, hydroxycarbonylalkyl, aminocarbonylalkyl, cycloalkylalkyl, phenylalkyl, heterocyclylalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl and cyanoalkynyl moieties, can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogens. The term halogen represents in each case fluorine, chlorine, bromine or iodine.
Other examples of meanings are:
C
1
-C
4
-alkyl: CH
3
, C
2
H
5
, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and C(CH
3
)
3
;
C
1
-C
4
-haloalkyl: a C
1
-C
4
-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, ie. for example CH
2
Cl, dichloromethyl, trichloromethyl, CH
2
F, CHF
2
, CF
3
, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C
2
F
5
, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH
2
—C
2
F
5
, CF
2
—C
2
F
5
, 1-fluoromethyl-2-fluoroethyl, 1-chloromethyl-2-chloroethyl, 1-bromomethyl-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or n-

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