C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/280, 260/305
C07D 233/61 (2006.01) C07D 403/02 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1120035
ABSTRACT OF THE DISCLOSURE 1-Aryl-2-(1H-imidazol-1-yl)-ethanone oxime others are known to exist as a mixture of isomers corresponding to the formulas: Image Image (It) and (Ic) transm- isomer cis- isomer To prepare such an isomer in a stereospecifically pure form, the stereoisomer of the corresponding ethanone oxima is first converted into an alkali salt in a polar solvent, such as acetone or dimethylformamide, and the converted to the desired ether by reaction it at a temperature not higher than 40°C with a halogen compound capable of forming the desired ether. Isolation of the ether product is obtained by precipitating it as an acid addition salt upon addition of a suitable organic or mineral acid, e/g/. aqueous acetic, hydrochloric, sulfuric or, most preferably, nitric acid. A stereospecific ethanone oxime in either its trans- or cis- isomer form corresponding to the formula: Image Image or (It) (Ic) transm- isomer cis- isomer -1- can be stereospecifically synthesized from the corresponding 2-halogen ethanone having the formula A-CO-CH2-Hal (IV) which, in making the cis oxime (IIc), is first converted with imidazole or a suitably substituted derivative thereof and subsequently oximated by reaction with hydroxylamine at an elevated temperature; or which, in preparing the trans oxime (IIc), is first oximated by reaction with hydroxyl- amine under mild conditions and subsequently converted in the cold with imidazole or a suitably substituted derivative thereof. She products are effective fungicides or bacteri- cides and consequently useful as chemotherapeutic agents in combatting undesirable lower plant organisms in the fields of human as well as veterinary medicine and also as fungi- cides in agriculture and horticulture. -2-
328168
Mixich Georg
Thiele Kurt
Macrae & Co.
Siegfried Aktiengesellschaft
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