Substituted (4-brompyrazole-3-yl) benzazoles

Details Substituted (4-brompyrazole-3-yl) benzazoles Substituted (4-brompyrazole-3-yl) benzazoles

2000-10-25

2002-11-19

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S270000, C504S280000, C548S217000, C548S166000, C548S377100

Reexamination Certificate

active

06482774

ABSTRACT:

The present invention relates to novel substituted (4-bromopyrazol-3-yl)benzazoles of the formula I
where:
R
1
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
2
is cyano, 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
-alkylsulfinyl, C
1
-C
4
-haloalkylsulfinyl, C
1
-C
4
-alkylsulfonyl or C
1
-C
4
-haloalkylsulfonyl;
R
4
is hydrogen or halogen;
R
5
is hydrogen, halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
Z is a group —N═C(XR
6
)—O— or —N═C(XR
6
)—S— which may be attached to &agr; via the nitrogen, oxygen or sulfur;
X is a chemical bond, oxygen, sulfur, —S(O)—, —SO
2
—, —NH— or —N(R
7
)—;
R
6
, R
7
independently of one another are each 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
-alkyl sulfinyl-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
-alkenyl sulfonyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkynylsulfonyl-C
1
-C
4
-alkyl, hydroxycarbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, which may carry a cyano or (C
1
-C
4
-alkoxy)carbonyl group, (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, di(C
1
-C
4
-alkyl)-phosphonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)imino-C
1
-C
4
-alkyl, (C
3
-C
4
-alkenyloxy)imino-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 from one to four substituents, in each case selected from the group consisting of cyano, nitro, amino, hydroxyl, carboxyl, 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;
if x is a chemical bond, oxygen, sulfur, —NH— or —N(R
7
)—, R
6
may also be (C
1
-C
4
-alkyl)carbonyl, (C
1
-C
4
-haloalkyl)carbonyl, (C
1
-C
4
-alkoxy)carbonyl, C
1
-C
4
-alkylsulfonyl or C
1
-C
4
-haloalkylsulfonyl;
if X is a chemical bond, R
6
may furthermore be 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, di(C
1
-C
4
-alkyl)aminocarbonyl or di(C
1
-C
4
-alkyl)phosphonyl;
or R
6
and R
7
together are a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain which may in each case be unsubstituted or may carry from 1 to 4 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.
Furthermore, the invention relates to
the use of the compounds I as herbicides and/or for the desiccation and/or defoliation of plants,
herbicidal compositions and compositions for the desiccation and/or defoliation of plants which comprise the compounds I as active ingredients,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I,
methods for controlling undesirable vegetation and for the desiccation and/or defoliation of plants using the compounds I, and also
novel intermediates of the formulae Va and Vb.
The present (4-bromopyrazol-3-yl)benzazoles I are covered by the general formula of active compounds which form part of the subject matter of the earlier application DE-A 19 652 240.
It is an object of the present invention to provide novel herbicidally active pyrazole compounds which allow better selective control of undesirable plants than the compounds of the prior art. 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 present substituted (4-bromopyrazol-3-yl)benzazoles of the formula I.
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, oil seed rape, sunflower, soybean or field beans, in particular cotton. Thus, 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. For compounds I having at least one olefinic radical, E/Z isomers may also be possible. The invention provides both the pure enantiomers or diastereomers and also mixtures thereof.
The organic moieties mentioned in the definition of the substituents R
1
, R
2
and R
5
to R
8
or as radicals on cycloalkyl, phenyl or heterocyclic rings are—like the term halogen—collective terms for individual listings of the individual group members. All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, oxyalkyl, aminoalkyl, oxycarbonylalkyl, aminocarbonylalkyl, phosphonylalkyl, oxyaminoalkyl, phenylalkyl, heterocyclylalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl and cyanoalkynyl moieties, can be straight-chain or branched. Halogenated substituents preferably carry from 1 to 5 identical or different halogen atoms. 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, CH(CH
3
)
2
, n-butyl, 1-methylpropyl, 2-methylpropyl or 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, i.e., for example, CH
2
F, CHF
2
, CF
3
, CH
2
Cl, CH(Cl)
2
, C(Cl)
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 nonafluorobutyl;
C
1
-C
6
-alkyl: C
1
-C
4
-alkyl as mentioned above, and also, for example, n-pentyl, 1-methy

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