Substituted pyrazol-3-ylbenzazoles, their use as herbicides...

Details Substituted pyrazol-3-ylbenzazoles, their use as herbicides... Substituted pyrazol-3-ylbenzazoles, their use as herbicides...

1999-06-16

2001-05-15

Higel, Floyd D. (Department: 1613)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C504S243000, C504S246000, C504S262000, C504S263000, C504S265000, C504S266000, C548S120000, C548S152000, C548S159000, C548S162000, C548S161000, C548S164000, C548S222000, C548S173000

Reexamination Certificate

active

06232470

ABSTRACT:

The present invention relates to novel substituted pyrazol-3-ylbenzazoles 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
3
is hydrogen, halogen, cyano, nitro, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
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 —NC═C(XR
6
)—O— or —N═C(XR
6
)—S— which may be bonded to &agr; via the nitrogen, oxygen or sulfur;
X is a chemical bond, oxygen, sulfur, —S(O)—, —SO
2
—, —NH— or —NC
1
(R
7
)—;
R
6
and 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
-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
-alkyl-sulfonyl-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, 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 carry one to four substituents selected in each case 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 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 compounds I as herbicides and/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 compounds,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I, and
methods for controlling undesirable vegetation and for the desiccation/defoliation of plants using the compounds I.
Certain aryl pyrazoles, where, in addition to phenyl, various benzoheterocyclyl radicals are also mentioned in principle as aryl radicals, are already described as herbicides in patent applications WO 92/02509, WO 92/06962, WO 86/01255, WO 96/15115, WO 96/15116 and WO 96/40643.
Furthermore, the general formula of WO 96/01254 embraces, when the substituents are chosen appropriately, inter alia compounds of the formula II
who are also said to have herbicidal activity.
It is an object of the present invention to provide novel herbicidally active pyrazole 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 present substituted pyrazol-3-ylbenzazoles of the formula I.
Furthermore, we have found herbicidal compositions 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. 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
to R
3
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, ie. all the 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 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, CH(CH
3
)
2
, 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
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-b

Affiliated with

Also associated with

Rating

Substituted pyrazol-3-ylbenzazoles, their use as herbicides... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Substituted pyrazol-3-ylbenzazoles, their use as herbicides..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted pyrazol-3-ylbenzazoles, their use as herbicides... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2447707