Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1998-07-29
2000-03-28
O'Sullivan, Peter
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
560 35, 564134, 564139, 564142, 564149, 564150, 514255, 514274, 514357, 514365, 514379, 514438, 514459, 514522, 514538, 514539, 544335, 544336, 546335, 548204, 548236, 549 72, 549426, 558391, A01N 3324, A01N 3734, A01N 4340, A01N 4310
Patent
active
060432829
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to azinooxime ethers of the formula I ##STR2## where the variables have the following meanings: or C.sub.1 -C.sub.4 -alkoxy; if m is 2; unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl,
The invention additionally relates to processes and intermediates for preparing these compounds and to compositions comprising them for controlling animal pests and harmful fungi.
Phenylacetic acid derivatives of type I having fungicidal and insecticidal action are disclosed in the following publication: WO-A 95/18789. The active compounds published there, however, are unsatisfactory with respect to their action.
It is an object of the present invention to provide novel compounds of this type having improved action against harmful fungi and pests.
We have found that this object is achieved by the azinooxime ethers I defined at the outset. We have additionally found processes and intermediates for their preparation and compositions comprising them for controlling animal pests and harmful fungi and their use for this purpose.
The compounds I are obtainable in various ways by processes known per se.
In principle, it is unimportant in the synthesis of 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).dbd.N--N.dbd.C(R.sup.5)R.sup.6 is synthesized first.
The synthesis of the group --C(X)--CO--YR.sup.1 is 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. ON.dbd.C(R.sup.3)--C(R.sup.4).dbd.N--N.dbd.C(R.sup.5)R.sup.6 a procedure is generally used in which a benzyl derivative of the formula II is reacted with a hydroxyimine of the formula III. ##STR3## L.sup.1 in the formula II is a nucleophilically replaceable leaving group, eg. halogen or a sulfonate group, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate. solvent in the presence of a base, eg. sodium hydride, potassium hydroxide, potassium carbonate or triethylamine, according to the methods described in Houben-Weyl, 4th Edition, Vol. E 14b, p. 370 et seq. and Vol. 10/1, p. 1189 et seq. hydrazone V with a carbonyl compound of the formula VI. ##STR4## The reaction is carried out, if appropriate with acid catalysis, in a manner known per se in an inert organic solvent (cf. Bull. Soc. Chim. Fr. 713 (1968); Houben-Weyl, 4th Edition, Vol. X/2, page 104 et seq.). J. Med. Chem. 21 (1978), 623; J. Chem. Soc. 101 (1912), 2238; J. Org. Chem. 25 (1960), 313). consists in reacting a carbonylhydroxyimino derivative IV with a hydrazone of the formula VII, as described in 1.2. ##STR5## 2. Alternatively, the compounds I can also be obtained by first reacting the benzyl derivative II with the carbonylhydroxyimino derivative IV to give a corresponding benzyloxime of the formula VIII, and then reacting VIII with a compound VII (see above) to give I. ##STR6## The reaction of IV with II is carried out similarly to the synthesis such as is described in 1.1. The reaction of VIII with VII is carried out similarly to the synthesis which is described in 1.2. compound of the formula VIII first with hydrazine hydrate to give the hydrazone of the formula IX and then reacting this with a carbonyl compound of the formula VI. ##STR7## The reactions are carried out similarly to the synthesis which is described in 1.2. benzyl derivative of the formula II with a hydroxyimine of the formula V. ##STR8## L.sup.1 in the formula II is a nucleophilically replaceable leaving group, eg. halogen or a sulfonate group, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate. in 1.1. III as in EP-A 493 711 using a lactone X into the corresponding benzoic acid XI and converting XI via the corresponding halides XII into the cyanocarboxylic acids XIII, which are converted by way of the Pinner reaction (Angew. Chem. 94, 1 (1982)) into the .alpha.-ketoesters XIV and, if desired, reacted further to give the .a
Ammermann Eberhard
Bayer Herbert
Grammenos Wassilios
Grote Thomas
Harries Volker
BASF - Aktiengesellschaft
O'Sullivan Peter
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