Iminooxybenzylcrotonate esters, their preparation and their use

Details Iminooxybenzylcrotonate esters, their preparation and their use Iminooxybenzylcrotonate esters, their preparation and their use

1997-05-22

1999-07-13

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514255, 514256, 514344, 514357, 544180, 544182, 544217, 544218, 544219, 544224, 544239, 544242, 544319, 544335, 544336, 544406, 544408, 544409, 546290, 546298, 546301, 546328, 546334, C07D23926, C07D23934, A01N 4340, A01N 4354

Patent

active

059227109

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to iminooxybenzylcrotonate esters of the formula I ##STR2## where the index and the substituents have the following meanings: n is 0, 1, 2, 3 or 4, it being possible for the substituents R to be different if n is greater than 1; or to two adjacent ring atoms, which contains three to four members from the group consisting of 3 or 4 carbon atoms, 2 or 3 carbon atoms and 1 or 2 nitrogen, oxygen and/or sulfur atoms, it being possible for this bridge, together with the ring to which it is bonded, to form a partially unsaturated or aromatic radical; alkylthio, haloalkylthio or cycloalkyl; which is substituted by customary groups,
2-Phenylcrotonic acids having fungicidal activity are disclosed in the literature (EP-A 280 185; EP-A 463 488; DE-A 41 16 090).
It is an object of the present invention to provide active compounds having improved activity.
We have found that this object is achieved by the compounds I defined at the beginning. Processes for their preparation, compositions containing them and methods for their use, in particular for controlling animal pests and harmful fungi, have additionally been found.
The compounds I are obtainable by various methods. They are particularly advantageously obtained by reacting a benzyl derivative of the formula II with an oxime of the formula III or its salt. ##STR3##
L.sup.1 in the formula II is a leaving group, ie. a nucleophilically replaceable group such as halogen (eg. chlorine, bromine or iodine), or an alkyl- or arylsulfonate (methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or 4-methylphenylsulfonate).
The oximes III can also be used in the form of their salts, eg. with inorganic acids, such as hydrochlorides, hydrobromides, hydrosulfates and hydrophosphonates.
The reaction of the compounds II and III is customarily carried out at from 0.degree. C. to 80.degree. C., preferably 20.degree. C. to 60.degree. C., in an inert solvent in the presence of a base.
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, nitrites such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol, ketones such as acetone and methyl ethyl ketone, and also dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one and 1,2-dimethyltetrahydro-2(1H)-pyrimidine, preferably methylene chloride, acetone, toluene, tert-butyl methyl ether 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 (eg. lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide), alkali metal and alkaline earth metal oxides (eg. lithium oxide, sodium oxide, calcium oxide and magnesium oxide), alkali metal and alkaline earth metal hydrides (eg. lithium hydride, sodium hydride, potassium hydride and calcium hydride), alkali metal amides (eg. lithium amide, sodium amide and potassium amide), alkali metal and alkaline earth metal carbonates (eg. lithium carbonate and calcium carbonate) and also alkali metal hydrogen carbonates (eg. sodium hydrogen carbonate), organometallic compounds, in particular alkali metal alkyls (eg. such as methyllithium, butyllithium and phenyllithium), alkylmagnesium halides (eg. methylmagnesium chloride) and also alkali metal and alkaline earth metal alkoxides (eg. sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium), additionally organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine. Pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and also bicyclic amines. Sodium hydroxide, potassium carbonate and potassium tert-butoxide are particularly prefe

REFERENCES:
patent: 4937372 (1990-06-01), Wenderoth et al.
patent: 5221762 (1993-06-01), Wingert et al.
patent: 5298527 (1994-03-01), Grammenos et al.
patent: 5387607 (1995-02-01), Brand et al.
patent: 5563168 (1996-10-01), Brand et al.

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