Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1998-06-25
2000-05-16
McKane, Joseph
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
514567, 514538, 514620, 558391, 560 22, 562440, 564164, 564265, A01N 3702, A01N 3712, C07C25503, C07C25132
Patent
active
060638133
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to cyanoiminooxime ethers of the formula I ##STR2## where the variables have the following meanings: X is NOCH.sub.3, CHOCH.sub.3 or CHCH.sub.3 ; or C.sub.1 -C.sub.4 -alkoxy; when m is 2; alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or hetaryl,
Furthermore, the invention relates to processes and intermediates for the preparation of these compounds, to compositions comprising them, and to the use of the compounds I for controlling animal pests and harmful fungi.
Cyanoiminooxime ethers of the formula I which are fungicidally and insecticidally active have been disclosed in the following publications: WO-A 95/18789 and WO-A 93/16986. However, the active ingredients disclosed in these publications are not yet satisfactory with regard to their activity.
It is an object of the present invention to provide novel compounds with an improved activity against harmful fungi and pests.
We have found that this object is achieved by the cyanoiminooxime ethers I defined at the outset. Furthermore, we have found processes and intermediates for their preparation, compositions comprising them for controlling animal pests and harmful fungi, and the use of the compounds I for this purpose.
The compounds I are obtainable by various routes following processes known per se.
In principle, it is irrelevant when synthesizing the compounds I whether the group --C(X)--CO--YR.sup.1 or the group --CH.sub.2 ON.dbd.C(R.sup.3)--C(R.sup.4)=N--CN is constructed first.
The construction of the group --C(X)--CO--YR.sup.1 has been disclosed, for example, in the following publications: EP-A 422 597, EP-A 463 488, EP-A 370 629, EP-A 460 575, EP-A 472 300, WO-A 90/07493, WO-A 92/13830, WO-A 92/18487, DE Appl. P 44 20 416.7.
In the descriptions of syntheses below, "Houben-Weyl" means: Houben-Weyl, Methoden der Organischen Chemie [methods in Organic Chemistry], Georg Thieme verlag, Stuttgart. (R.sup.3)--C(R.sup.4).dbd.N--CN, a procedure is generally followed in which a benzyl derivative of the formula II is reacted with a hydroxyimine of the formula III. ##STR3##
L.sup.1 in formula II is a nucleophilically exchangeable leaving group, e.g. halogen or a sulfonate group, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. sodium hydride, potassium hydroxide, potassium carbonate or triethylamine, following methods known from the literature (cf. Houben-Weyl, 4th Edition, Vol. E 14b, p. 370 et seq. and Vol. 10/1, p. 1189 et seq.). carbonylhydroxyimino derivative IV with bis(trimethylsilyl)carbodiimide. ##STR4##
The reaction is carried out in a manner known per se in an inert organic solvent, preferably with fluoride or cyanide catalysis or in the presence of Lewis acids such as titanium tetrachloride (Liebigs Ann. Chem. 1986, page 142 et seq.; Angew. Chemie 96, 1984, page 437 et seq.).
Occasionally, it may be advantageous prior to the reaction to provide the oxime function of IV by generally known methods with a protective group, e.g. an acyl group (alkylcarbonyl group) or a sulfonyl group, which can be reeliminated at a later point in time. This protective-group technology can also be applied to nucleophilic centers in the radical R.sup.4.
The carbonylhydroxyimino derivatives IV which have not already been disclosed can be prepared by methods known per se (cf. Org. Synth. 16, 1936, page 46; Bull. Chem. Soc. Jap. 44, 1971, page 219 et seq.; DE-A-27 22 416; Gazz. Chim. Ital. 61, 1931, page 943 et seq.; Chem. Ber 106, 1973 page 1688 et seq.). the benzyl derivative II with the carbonylhydroxyimino derivative IV to give a corresponding benzyl oxime of the formula V and subsequently to react V with bis(trimethylsilyl)carbodiimide to give I. ##STR5##
The reaction of IV with II is carried out by a method similar to the synthesis described below for 1.1. The reaction of V with bis(trimethylsilyl)carbodiimide is carried out by a method similar to the synthesis described below under 1.2. III with a
Ammermann Eberhard
Bayer Herbert
Grammenos Wassilios
Grote Thomas
Harries Volker
BASF - Aktiengesellschaft
McKane Joseph
Sackey Ebenezer
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