2-pyrazolyl oxyphenyl acetic acid derivatives, agents containing

Details 2-pyrazolyl oxyphenyl acetic acid derivatives, agents containing 2-pyrazolyl oxyphenyl acetic acid derivatives, agents containing

1998-06-25

2000-06-13

Higel, Floyd D.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5483671, 514407, C07D23122, C07D23120, C07D23112, A01N 4356

Patent

active

060751495

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to compounds of the formula I ##STR2## and to salts thereof where the variables having the following meanings: n is 0, 1, 2, 3 or 4, it being possible for the radicals R.sup.1 to be different when n is greater than 1; which can additionally have attached to it one or, independently of one another, two substituents selected from the group consisting of: chlorine, bromine, methyl and trifluoromethyl; -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; halogen atoms and, if desired, together with the halogen atoms, one or, independently of one another, two or three of the following substituents: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and C.sub.1 -C.sub.4 -alkylthio; two adjacent carbon atoms of the phenyl radical and which, in turn, can have attached to it one to four halogen atoms and, if appropriate, together with the halogen atoms, one or, independently of one another, two of the following substituents: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and C.sub.1 -C.sub.4 -alkylthio; aromatic ring which is bonded directly or via a group (--CR.sup.3 R.sup.4 --) and which, besides carbon atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and one oxygen or sulfur atom or one oxygen or sulfur atom as ring members, where -C.sub.4 -alkyl, or, together with the carbon atom to which they are bonded: a group (--C(.dbd.O)--) or (--C(.dbd.NOR.sup.5)--), where, in turn,
The invention furthermore relates to compositions for controlling harmful fungi and animal pests which comprise the compounds I or salts thereof, and to the use of the compounds I and the salts thereof, and of the compositions comprising them, for this purpose.
2-Hetaryloxyphenylacetic acid derivatives which have a fungicidal and, in some cases insecticidal, action have been disclosed in the following publications: EP-A 178 824, EP-A 256 667, EP-A 398 692, EP-A 477 631, EP-A 513 580, WO-A 94/10159 and EP-A 623 604.
The prior-art compounds of this type are as yet unsatisfactory with a view to the ranges of action and application rates.
It is an object of the present invention to remedy this with the aid of the present invention.
We have found that this object is achieved via the compounds I and their salts defined at the outset.
There have furthermore been found compositions for controlling harmful fungi and animal pests which comprise the compounds I or their salts, and the use of the compounds I and their salts and of the compositions comprising them for this purpose.
The compounds I are obtainable by known processes following various routes. In principle, it is irrelevant when synthesizing them whether the group "O-Het-R.sup.2 " or the group "Q" is constructed first.
The compounds I are obtainable via the compounds Z which, in turn, are accessible by reacting compounds of the formula II with hydroxy heterocycles of the formula III. ##STR3##
In this formula as fluorine, chlorine, bromine or the nitro group; group L and which can additionally be converted into the group Q of the compounds I--as described below--for example: nitro, --CO--CO--OR', --CO--CO--NHR', --CO--OR' or --CO--CH.sub.3 (R'=C.sub.1 -C.sub.4 -alkyl).
This reaction is normally carried out at from 0 to 120, preferably from 20 to 60.degree. C.
Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone and methyl ethyl ketone, or else dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one and 1,3-dimethyltetrahydro-2(1H)-pyrimidinone; dimethyl sulfoxide, dimethylacetamide and dimethylformamide are especially preferred.
Mixtures o

REFERENCES:
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patent: 5374644 (1994-12-01), Clough et al.
patent: 5416068 (1995-05-01), Grammenos et al.
patent: 5523280 (1996-06-01), Chene et al.
patent: 5776965 (1998-07-01), Kim et al.

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