3-(1,2-Propadienyl)-cyclopropane-carboxylates
AssigneeRoussel Uclaf
InventorsJean Tessier, Jean-Pierre Demoute, Joseph Cadiergue
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Abstract
Novel 3-(1,2-propadienyl)-cyclopropane-carboxylates of the formula ##STR1## wherein R is alcohol used in pyrethrinoid synthesis, X and Y are both hydrogen or individually halogen or X is hydrogen or halogen and Y is alkyl of 1 to 18 carbon atoms or halogen or X is hydrogen or halogen or alkyl of 1 to 18 carbon atoms and Y is --COOR' or --CN or ##STR2## R' is alkyl of 1 to 18 carbon atoms, R.sub.2 and R.sub.3 are individually hydrogen or alkyl of 1 to 18 carbon atoms or R.sub.2 and R.sub.3 together with the nitrogen atom form a heterocycle having pesticidal properties.
Claims28
A 3-(1,2-propadienyl)-cyclopropane-carboxylate of the formula ##STR35## wherein R is selected from the group consisting of (1) alkyl of 1 to 18 carbon atoms, (2) benzyl optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkadienyl of 4 to 8 carbon atoms, methylenedioxy and halogens, ##STR36## wherein R.sub.1 is selected from the group consisting of hydrogen and methyl and R.sub.2 ' is selected from the group consisting of --C.tbd.CH and 5-benzyl-3-furyl-methyl, ##STR37## wherein a is selected from the group consisting of hydrogen and methyl and R.sub.3 ' is an aliphatic group of 2 to 6 carbon atoms containing at least one carbon-carbon unsaturation, ##STR38## wherein a and R.sub.3 ' have the above definition and R.sub.1 ' and R.sub.2 " are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, phenyl, cyano and alkoxy carbonyl of 2 to 5 carbon atoms, ##STR39## wherein B is selected from the group consisting of --CH.sub.2 --, ##STR40## --O-- and --S--, R.sub.4 is selected from the group consisting of hydrogen, C.tbd.N, --CH.sub.3, --CONH.sub.2, --CSNH.sub.2 and --C.tbd.CH, n is an integer from 0, 1 or 2 and R.sub.5 is selected from the group consisting of halogen and --CH.sub.3 ##STR41## wherein R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are selected from the group consisting of hydrogen, chlorine and methyl and S/I symbolizes an aromatic ring or dihydro, tetrahydro or hexahydro ring, (9) (succinimido or maleimido) --CH.sub.2 -- ##STR42## wherein R.sub.10 is selected from the group consisting of hydrogen and --CN, R.sub.12 is selected from the group consisting of --CH.sub.2 -- and --O-- and R.sub.11 is selected from the group consisting of thiazolyl and thiadiazolyl with the bond to ##STR43## being in any one of the positions, R.sub.12 being bonded to R.sub.11 by the carbon atom included between a sulfur atom and a nitrogen atom, ##STR44## wherein R.sub.13 is selected from the group consisting of hydrogen and --CN, ##STR45## wherein R.sub.13 has the above definition ##STR46## wherein R.sub.14 is selected from the group consisting of hydrogen, methyl, ethynyl and --CN and R.sub.15 and R.sub.16 are individually selected from the group consisting of hydrogen, bromine and fluorine and ##STR47## wherein R.sub.14 has the above definition, p is 0, 1 or 2, each R.sub.17 is selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, --CF.sub.3, 3,4-methylenedioxy, chlorine, bromine and fluorine, B' is selected from the group consisting of --O-- and --S--, X and Y are both hydrogen or individually halogen or X is hydrogen or halogen and Y is alkyl of 1 to 18 carbon atoms or halogen.
Dependencies are inferred from the claim text.