Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-11-20
1999-08-10
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514340, 514384, 514538, 514727, 514730, 5483661, 5483681, 5483704, 5483707, 5483711, 560 39, 560 61, 564253, 568715, 568807, 5462761, A01N 4356, C07D23120, C07D23122
Patent
active
059359862
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to compounds of the general formula I ##STR3## in which 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 differ if n is greater than 1; alkynyloxy or substituted bridge which is bonded to two adjacent ring atoms and which three to four members selected from the group consisting of 3 or 4 carbon atoms, 1, 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; ##STR4## the bond marked with .circle-solid. being the bond to the oxygen and the indices and the substituents having the following meanings: which, besides carbon atoms, can contain one to three of the following hetero atoms as ring members: oxygen, sulfur and nitrogen; or atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and one or two oxygen or sulfur atoms or one oxygen or one sulfur atom as ring members; m is greater than 1; -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -alkoxycarbonyl; o is greater than 1; which, besides carbon atoms, can contain one to three of the following hetero atoms as ring members: oxygen, sulfur and nitrogen; or besides carbon atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and one or two oxygen or sulfur atoms or one oxygen or one sulfur atom as ring members; alkynyloxy; which, besides carbon atoms, can contain one to three of the following hetero atoms as ring members: oxygen, sulfur and nitrogen; and which can be bonded to the skeleton either directly or via an oxygen or sulfur atom; or atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and one or two oxygen or sulfur atoms or one oxygen or one sulfur atom as ring members.
The invention furthermore relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling animal and fungal pests.
The literature describes hetaryloxybenzylalkoxyacrylic esters having a fungicidal and, in some cases, also insecticidal, acaricidal and nematicidal action in general form (EP-A 278 595; EP-A 254 426; EP-A 358 692; WO-A 94/19,331, WO-A 94/00,436).
It was an object of the present invention to provide compounds with an improved activity.
Accordingly, we have found that this object is achieved by the compounds I defined at the outset. Furthermore, processes for the preparation of these compounds, compositions comprising them, and their use for controlling animal and fungal pests have been found.
The compounds I are accessible via a variety of methods which are known per se from the literature cited.
For example, the compounds I are obtained by reacting the benzyl derivative II with a hydroxyazole of the formula III in the presence of a base. ##STR5## L in formula II is a nucleophilically exchangeable group, for example halogen, eg. chlorine, bromine and iodine, or an alkyl- or arylsulfonate, eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate and 4-methylphenylsulfonate.
The reaction is conventionally carried out at from 0.degree. C. to 100.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 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, alcohols, such as methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol, ketones, such as acetone and methyl ethyl ketone, and also ethyl acetate, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone, dimethylacetamide, 1,3-dimethylimidazolidin-2-one and 1,2-dimethyltetrahydro-2(1H)-pyrimidine, preferably methylene chloride, acetone, N-methylpyrrolidone and dimethylformamide. Mixtures of th
Ammermann Eberhard
Harries Volker
Kirstgen Reinhard
Konig Hartmann
Lorenz Gisela
BASF - Aktiengesellschaft
Oswecki Jane C.
Ramsuer Robert W.
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