Substituted 3-phenylpyrazoles

Details Substituted 3-phenylpyrazoles Substituted 3-phenylpyrazoles

1999-02-01

2001-03-06

Higel, Floyd D. (Department: 1613)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C504S139000, C548S337100

Reexamination Certificate

active

06197973

ABSTRACT:

The present invention relates to novel substituted 3-phenylpyrazoles of the formula I
in which the variables have the following meanings:
R
1
is 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, cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
4
is hydrogen or halogen;
R
5
is cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
6
, R
7
independently of one another are C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, hydroxy-C
1
-C
4
-alkyl, cyano-C
1
-C
4
-alkyl, 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
-haloalkyl-sulfinyl-C
1
-C
4
-alkyl, C
3
-C
4
o-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
3
-C
6
-alkenyl, cyano-C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkyl, C
3
-C
6
-alkynyl, cyano-C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, (C
1
-C
4
-alkyl)-carbonyl, (C
1
-C
4
-haloalkyl)carbonyl, (C
1
-C
4
-alkoxy)carbonyl, aminocarbonyl, (C
1
-C
4
-alkyl)aminocarbonyl, di(C
1
-C
4
-alkyl)aminocarbonyl, (C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl)carbonyl, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, (C
1
-C
4
-alkyl)carbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-haloalkyl)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
8
-cycloalkyl)carbonyl-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, hydroxycarbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl which can have a (C
1
-C
4
-alkoxy)imino group attached to it, (C
1
-C
4
-haloalkoxy) 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
-alkylamino)carbonyl-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkylamino)carbonyl-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 or 3- to 7-membered heterocyclyl or heterocyclyl-C
1
-C
4
-alkyl, it being possible, if desired, for all cycloalkyl rings and heterocycles to contain a carbonyl or thiocarbonyl ring member, and it being possible for each cycloalkyl, phenyl or heterocyclyl ring to be unsubstituted or to have attached to it 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;
X is a chemical bond, a 1,2-ethynediyl group or a group *—CH
2
—CH(R
8
)— or *—CH═C(R
8
)— which is bonded to the phenyl ring via the bond characterized with an asterisk, where R
8
is hydrogen, cyano, nitro, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
Y is oxygen or sulfur;
and to the agriculturally useful salts of the compounds I.
Furthermore, the invention relates to
the use of these compounds I as herbicides,
herbicidal compositions which comprise the compounds I as active substances,
processes for the preparation of the compounds I and of herbicidal compositions using the compounds I, and
methods of controlling undesirable vegetation using the compounds I.
Herbicidally active 3-phenylpyrazoles have already been described in EP-A 443 059, WO 92/06 962, JP-A 03/151 367, WO 92/02 509, WO 96/15 115, WO 95/32 188, WO 95/33 728, WO 96/01 254, WO 96/02518 and WO 96 40 643.
However, the herbicidal properties of the known herbicides are 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 than was possible to date.
We have found that this object is achieved by the present substituted 3-phenylpyrazoles of the formula I and by their herbicidal activity.
We have furthermore found herbicidal compositions which comprise the compounds I and have a very good herbicidal activity. Moreover, we have found processes for the preparation of these compositions and methods of controlling undesirable vegetation 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 are present as enantiomer or diastereomer mixtures. Depending on the meaning of X, E/Z isomers are also possible. The invention relates both to the pure enantiomers or diastereomers and to mixtures of these.
Suitable amongst the agriculturally useful salts are mainly salts of those cations or the acid addition salts of those acids whose cations, or anions, respectively, do not adversely affect the herbicidal activity of the compounds I. Thus, especially suitable cations are the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion which, if desired, can have attached to it one to four C
1
-C
4
-alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)sulfonium and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)sulfoxonium.
Anions of useful acid addition salts are principally chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic moieties mentioned for the substituents R
1
to R
3
and R
5
to R
8
or as radicals on cycloalkyl, phenyl or heterocyclyl rings are collective terms for individual enumerations of the individual group members. All carbon chains, ie. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyanoalkyl, hydroxyalkyl, hydroxycarbonylalkyl, aminoalkyl, aminocarbonylalkyl, phenylalkyl, heterocyclylalkyl, alkylcarbonyl, haloalkylcarbonyl, alkylcarbonyloxy, haloalkylcarbonyloxy, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylamino, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylsulfinyl, alkynylsulfinyl, alkenylsulfonyl, and alkynylsulfonyl moieties may be straight-chained or branched. Halogenated substituents preferably have attached to them one to five identical or different halogen atoms.
The meaning of halogen is in each case fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
Other examples are:
C
1
-C
4
-alkyl: CH
3
, C
2
H
5
, n-propyl, CH(CH
3
)
2
, n-butyl, 1-methyl-propyl, CH
2
—CH(CH
3
)
2
or C(CH
3
)
2
or C(CH
3
)
3
, in particular CH
3
or C
2
H
5
;
C
1
-C
6
-alkyl: C
1
-C
4
-alkyl as mentioned above, or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,

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