Ortho-substituted 2-methoxyiminophenyl-N-methylacetamides

Details Ortho-substituted 2-methoxyiminophenyl-N-methylacetamides Ortho-substituted 2-methoxyiminophenyl-N-methylacetamides

1995-08-21

2000-02-29

Morris, Patricia L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5483667, C07D23120, C07D23118

Patent

active

06031110&

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to compounds of the general formula ##STR2## where the index and the substituents have the following meanings: n is 0, 1, 2, 3 or 4, it being possible for the radicals R.sup.1 to be different if n is greater than 1; also carry one or two radicals from the group consisting of Cl, CH.sub.3, CF.sub.3 and OCH.sub.3 ; -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; five halogen atoms or one to three of the following radicals: halogen, 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; to two adjacent C atoms of the phenyl radical and which for its part can carry one to four halogen atoms or one or two of the following radicals: nitro, cyano, halogen, 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; which, in addition to carbon atoms, can contain one to three of the following hetero atoms as ring members: oxygen, sulfur and nitrogen; in addition to carbon atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or an oxygen or sulfur atom as ring members.
The invention further relates to processes for preparing these compounds, compositions containing them and their use for the control of fungi and pests.
Substituted 2-alkoxyiminophenylacetamides are known (EP-A 398 692, EP-A 477 631, JP-A 4 182 461, WO 92/13 830 and GB 22 53 624). The compounds have fungicidal and partly also insecticidal action (EP-A 477 631). Their action, however, is unsatisfactory.
It has surprisingly been found that the compounds of the general formula I according to the invention have a greatly improved activity and plant tolerability.
In addition, processes for preparing these compounds, compositions containing them and their use for the control of fungi and pests have been found.
The compounds of the formula I are prepared in analogy to various methods known per se from the literature. In the synthesis of the compounds I, the sequence in which the groups R.sup.2 --Y--XCH.sub.2 -- or group [sic] --C(.dbd.NOCH.sub.3)--CO--NHCH.sub.3 are synthesized from the corresponding precursors is in general insignificant.
These groups are particularly preferably obtained by the processes described below, the group which is not involved in the reaction in each case being shown in the following reaction schemes in a simplified manner for better clarity: --C(.dbd.NOCH.sub.3)--CO--NHCH.sub.3 or its precursor as R.sup.#.
The compounds of the general formulae I and II are obtained by reaction of IA or IIA with hydroxy- or mercapto-substituted five-membered ring heteroaromatic systems III in inert solvents in the presence of a base. ##STR3##
This reaction is customarily carried out at from 0.degree. C. to 80.degree. C., preferably 20.degree. C. to 60.degree. C. Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, ketones such as acetone and methyl ethyl ketone, as well as dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one and 1,3-dimethyltetrahydro-2(1H)-pyrimidinine [sic], particularly preferably dichloromethane, acetone and dimethylformamide.
Mixtures of the solvents mentioned can also be used.
Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassi

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