Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-12-15
1999-05-18
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5482658, 5482674, A01N43/653
Patent
active
059050870
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to iminooxybenzyl compounds of the formuls I ##STR2## where the index and the substituents have the following meanings: R.sup.1 is C(CO.sub.2 R.sup.a).dbd.CHR.sup.b, C(CO.sub.2 R.sup.a).dbd.CHOR.sup.b, C(CO.sub.2 R.sup.a).dbd.NOR.sup.b or C(CONR.sup.a R.sup.c).dbd.NOR.sup.b ; differ from each other if n is greater than 1; alkynyloxy or substituted bridge which is bonded to two adjacent ring atoms and which can contain three to four members 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 un-saturated or aromatic radical; alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio or cycloalkyl; alkenylthio, alkynyl, alkynyloxy or alkynylthio; which can contain, as ring members, one to three of the following hetero atoms: oxygen, sulfur and nitrogen, in addition to carbon atoms, and which can be bonded to the skeleton directly or via an oxygen or sulfur atom; or can contain, as ring members, one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or an oxygen or a sulfur atom, in addition to carbon atoms, which can contain, as ring members, one to three of the following hetero atoms: oxygen, sulfur and nitrogen, in addition to carbon atoms; or can contain, as ring members, one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or one or two oxygen or sulfur atoms, in addition to carbon atoms.
The invention furthermore relates to processes for the preparation of these compounds, to compositions comprising them, and to the use of these compositions for controlling animal and fungal pests.
The literature discloses fungicidally active hetaryliminooxybenzyl compounds in general form (EP-A 370 629; EP-A 414 153; EP-A 460 575; EP-A 463 488; EP-A 472 300; EP-A 569 384; WO-A 90/07,493).
In contrast, it is an object of the present invention to provide compounds with an improved activity.
We have found that this object is achieved by the compounds I defined at the outset. Moreover, we have found processes for the preparation of these compounds, compositions comprising them, and the use of these compositions for controlling animal and fungal pests.
The compounds I can be prepared by various routes. The compounds I are particularly advantageously obtained by reacting a benzyl compound of the formula II with an oxime of the formula III or a salt thereof. ##STR3##
In the formula II, L.sup.1 is a leaving group, i.e. a nucleophilically exchangeable group, such as halogen (e.g. chlorine, bromine and iodine), or an alkyl- or arylsulfonate (e.g. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate and 4-methylsulfonate).
The oximes III can also be used in the form of their salts, for example with inorganic acids, such as hydrochlorides, hydrobromides, hydrogen sulfates and hydrogen phosphonates.
The compounds II and III are usually reacted 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, 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 dimethyl sulfoxide, dimethyl-formamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one and 1,2-dimethyltetrahydro-2(1H)-pyrimidine, preferably methylene chloride, acetone, toluene, tert-butyl methyl ether and dimethyl-formamide. Mixtures of these can also be used.
Suitable bases are, generally, inorganic compounds, such as alkali metal hydroxides and alkaline earth metal hydroxides (e.g. lith
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Ammermann Eberhard
Lorenz Gisela
Muller Bernd
Rohl Franz
Sauter Hubert
BASF - Aktiengesellschaft
Oswecki Jane C.
Richter Johann
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