Document Type and Number:
Japanese Patent JPS5070342
Kind Code:
A
Abstract:
1465568 Racemic or optically active derivatives of cyclopropane carboxylic acid ROUSSEL UCLAF 22 Oct 1974 [22 Oct 1973] 45653/74 Headings C2C and C2P The invention relates to racemic or optically active derivatives of cyclopropane carboxylic acid of cis or trans structure of Formula I in which R represents either a R 1 group which is either hydrogen, or an alkali metal atom, or an alkyl radical containing from 1 to 6 carbon atoms, substituted if necessary, or a R 2 group which is either a benzyl radical, substituted, if necessary, by one or more substituents selected from an alkyl, an alkenyl, an alkadienyl, a methylenedioxy, a benzyl radical and a halogen atom, or a cyclohexene dicarboximide methyl radical having a double bond at any position in the hexagonal nucleus and, if necessary, substituted on the said hexagonal nucleus by one or more halogen atoms, one or more methyl radicals or one or more acetoxy radicals, or a radical of formula in which Y 1 and Y 2 , the same or different, represent hydrogen, an alkyl, alkenyl or alkadienyl radical and Y 3 represents hydrogen, an alkyl, alkenyl, alkadienyl, alkynyl, or aryl radical or a heterocyclic radical, all these radicals being capable, if necessary, of being substituted, or a 1-oxo 2-Z 3-methyl 2-cyclopentene 4-yl residue of formula in which Z represents an alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, or cycloalkenyl radical or a heterocyclic radical. The compounds have insecticidal properties. Compounds of the general Formula I in which R is H are prepared by reacting 2,2-dimethyl 3- formyl cyclopropane 1-carboxylic acid, the configuration of which at the 1- and 3-positions is the same as that desired in the product, with a phosphonate or phosphorane containing a 1- ethyl propane-2-one 1-yl chain in the presence of a strong base. Suitable phosphonates include, for example, O,O-dialkyl alpha-ethyl acetonyl phosphonate and a suitable phosphorane is, for example, an alpha-ethyl acetonyl triaryl phosphorane, e.g. alpha-ethyl acetonyl triphenyl phosphorane. Compounds of the general Formula I in which R is other than H or an alkali metal atom are prepared by reacting a compound of Formula I wherein R represents hydrogen or an alkali metal (or a functional derivative thereof) with a compound of formula XOH (or a functional derivative thereof) wherein X represents a group R 2 or an optionally substituted alkyl group. When R represents hydrogen then this acid may, if desired, be used in the form of, for example, its acid chloride, anhydride, mixed anhydride or a salt. The alcohol of formula XOH may, for example, be used in the form of a halide derivative of formula X-Hal or an alkali metal derivative. Alpha-ethyl-acetonyltriphenylphosphorane is prepared by reacting propyltriphenyl phosphonium iodide with ethyl thioacetate. Dipropyl alphaethyl acetonylphosphonate is produced by reacting tripropyl phosphonate and ethyl acetate.
Application Number:
JP12108874A
Publication Date:
June 11, 1975
Filing Date:
October 22, 1974
Export Citation:
International Classes:
A01N53/02; A01N53/04; A01N53/10; C07C62/38; C07C51/00; C07C67/00; C07C69/757; C07D209/48; C07D307/45; C07F9/535; (IPC1-7): A01N9/24; C07C61/04; C07C69/74; C07D307/20