Roussel Uclaf

Other

Laurent Taliani

Jacques Perronnet

Jean Tessier

Jean-Pierre Demoute

Jean Buendia

Michel Vivat

Jean-Louis Brayer

Andre Teche

Marc D Benoit

Pierre Girault

Andre Poittevin

Gilles Mourioux

A compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl and alkynyl of up to 8 carbon atoms, optionally substituted cycloalkyl or cycloalkenyl of up to 8 carbon atoms, optionally substituted aryl of 6 to 18 carbon atoms, optionally substituted aralkyl of 7 to 24 carbon atoms, optionally substituted benzoyl and optionally substituted heterocycle, the optional substituents being at least one member of the group consisting of halogen, phenoxy, thiazolyl, alkyl and alkoxy of 1 to 6 carbon atoms and haloalkyl, Alk.sub.1 and Alk.sub.2 are individually optionally substituted alkyl of 1 to 8 carbon atoms, X is --O-- or --S-- and R' is hydrogen or halogen in any position on the phenyl and the geometry of the double bond is E or Z or a mixture of E and Z and having useful pesticidal properties.

Insecticidal benzofuran derivatives

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of Ar-O- and aryl, polyaryl and condensed polyaryl unsubstituted or substituted and heterocycle unsubstituted or substituted, Ar is aryl of 6 to 14 carbon atoms unsubstituted or substituted, heteroaryl unsubstituted or substituted and heterocyclic unsubstituted or substituted, W is selected from the group comsisting of --(CH.sub.2).sub.n.sbsb.1 --or --(CH.sub.2).sub.n.sbsb.2 --NY--(CH.sub.2).sub.n.sbsb.3, n.sub.1, n.sub.2 and n.sub.3 are individually integers from 2 to 6, Y is selected from the group consisting of hydrogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 12 carbon atoms and aralkyl of 7 to 14 carbon atoms unsubstituted or substituted, --COOAlk and --COR.sub.2, Alk is alkyl of 1 to 12 carbon atoms, R.sub.2 is selected from the group consisting of alkyl of 1 to 12 carbon atoms, alkenyl and alkynyl of 2 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms unsubstituted or substituted and heterocyclic unsubstituted or substituted, Z is selected from the group consisting of hydrogen, ##STR2## R.sub.2 is alkyl of 1 to 12 carbon atoms or aralkyl of 7 to 18 carbon atoms, Alk' is alkyl of 1 to 12 carbon atoms, ArAlk is aralkyl of 7 to 18 carbon atoms, R.sub.2 ' is R.sub.2, R.sub.3 and R.sub.3 ' are selected from the group consisting of aryl substituted or unsubstituted, heteroaryl substituted or unsubstituted, heterocyclic unsubstituted or substituted and R.sub.1 with the proviso that Z is not hydrogen when W is --(CH.sub.2).sub.3 --and R.sub.1 is 2,4-dichlorophenoxy and their non-toxic, pharmaceutically acceptable acid addition salts having fungicidal activity.

Acylated amine compounds which are useful fungicigal agents

Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.1 is selected from the group consisting of ##STR4## X', X, Y, Y' and Y' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 8 carbon atoms and aryl of 6 to 14 carbon atoms, the dotted line indicating an optional double bond, r' is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CF.sub.3, --COOAlk and alkoxy of 1 to 8 carbon atoms and Alk has the above definition, R' and R'' are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 6 to 18 carbon atoms, --CF.sub.3, --COOAlk' and alkoxy of 1 to 8 carbon atoms and Alk' is alkyl of 1 to 8 carbon atoms having pesticidal properties and novel intermediates.

Novel pyrrole derivatives

Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.1 is selected from the group consisting of ##STR4## X', X, Y, Y' and Y' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 8 carbon atoms and aryl of 6 to 14 carbon atoms, the dotted line indicating an optional double bond, r' is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CF.sub.3, --COOAlk and alkoxy of 1 to 8 carbon atoms and Alk has the above definition, R' and R'' are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 6 to 18 carbon atoms, --CF.sub.3 ' --COOAlk' and alkoxy of 1 to 8 carbon atoms and Alk' is alkyl of 1 to 8 carbon atoms having pesticidal properties and novel intermediates.

Novel .beta.-lactones of 2-hydroxy-cyclopentane-carboxylic acids of the formula ##STR1## 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 --CH.sub.2 --O--CH.sub.2 --CH.sub.3 and --X--Ar, X is selected from the group consisting of --O-- and --CH.sub.2 --, Ar is an optionally substituted member selected from the group consisting of thienyl, thiazolyl, phenyl and thiadiazolyl, the optional substituents being at least one member selected from the group consisting of halogen and --CF.sub.3 and the wavy lines indicate that the groups may be in the .alpha.,.beta. or .beta.,.alpha.-positions or mixtures thereof having hypotensive activity and their preparation.

.beta.-Lactones of 2-hydroxy-cyclopentane-carboxylic acids

Novel .beta.-lactones of 2-hydroxy-cyclopentane-carboxylic acids of the formula ##STR1## 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 --CH.sub.2 --O--CH.sub.2 --CH.sub.3 and --X--Ar, X is selected from the group consisting of --O-- and --CH.sub.2 --, Ar is an optionally substituted member selected from the group consisting of thienyl, thiazolyl, phenyl and thiadiazolyl, the optional substituents being at least one member selected from the group consisting of halogen and --CF.sub.3 and thw wavy lines indicate that the groups may be in the .alpha., .beta. or .beta., .alpha.-positions or mixtures thereof having hypotensive activity and their preparation.

Novel 3-(phosphoryloxy) or (phosphonyloxy)-thiophenes of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and ##STR2## wherein R' and R' are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 is selected from the group consisting of cyano, alkoxy carbonyl of 2 to 4 carbon atoms and ##STR3## wherein Z is selected from the group consisting of phenyl and alkyl of 1 to 4 carbon atoms, R.sub.3 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, phenyl, morpholino, piperidinyl and alkoxy carbonyl of 2 to 4 carbon atoms and X is selected from the group consisting of oxygen and sulfur having pesticidal properties and their preparation.

3-(Phosphoryloxy) and (phosphonyloxy)-thiophenes

Novel 3-(phosphoryloxy) and (phosphonyloxy)-thiophenes

Novel thiadiazoles of the formula ##STR1## wherein R is alkyl of 1 to 3 carbon atoms, W is selected from the group consisting of oxygen and sulfur, X is selected from the group consisting of --O--, --S-- and ##STR2## R' is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, n is 1, 2, 3 or 4 and R' is selected from the group consisting of hydrogen, --CN, alkoxy of 1 to 3 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, phenyl optionally substituted with one member of the group consisting of halogen, alkyl of 1 to 3 carbon atoms and alkoxy of 1 to 3 carbon atoms or substituted with two members of the group consisting of halogen, alkyl of 1 to 3 carbon atoms and alkoxy of 1 to 3 carbon atoms, having insecticidal and nematocidal activity.

Novel thiadiazoles

Novel thiadiazoles of the formula ##STR1## wherein R is selected from the group consisting of alkoxy of 1 to 8 carbon atoms, cycloalkyloxy of 3 to 7 carbon atoms, alkylthio of 1 to 8 carbon atoms optionally substituted with carbalkoxy of 2 to 5 carbon atoms, alkenylthio of 2 to 4 carbon atoms, ##STR2## and benzyloxy, benzylthio, benzyl and phenyl, all aryl being optionally substituted with 1 to 2 members of the group consisting of chlorine, bromine, alkyl of 1 to 3 carbon atoms and alkoxy of 1 to 3 carbon atoms, Z and Z.sub.1 are alkyl of 1 to 4 carbon atoms and R.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms optionally substituted with a member of the group consisting of chlorine, bromine and alkyloxy of 1 to 4 carbon atoms, phenyl optionally substituted with 1 to 2 members of the group consisting of bromine, chlorine, alkyl of 1 to 3 carbon atoms and alkoxy of 1 to 3 carbon atoms, alkenyl of 2 to 4 carbon atoms optionally substituted with at least one member of the group consisting of chlorine and alkoxy of 1 to 3 carbon atoms, ##STR3## and carbalkoxy of 2 to 6 carbon atoms and X is selected from the group consisting of alkyl of 1 to 4 carbon atoms and alkenyl of 2 to 4 carbon atoms, both optionally substituted with at least one chlorine having herbicidal properties and novel intermediates.

Certain 2-carbamoyl-1,2,4-thiadiazole-3-one herbicides

Novel 4-phosphoryloxy-5-cyano-thiazoles of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms and benzyl optionally substituted with 1 to 2 members of the group consisting of halogen,methyl and methoxy, R.sub.1 is selected from the group consisting of alkyl and alkoxy of 1 to 3 carbon atoms, R.sub.2 is alkyl of 1 to 3 carbon atoms and X and Z are individually selected from the group consisting of oxygen and sulfur having particularly insecticidal properties but also acaricidal and nematocidal properties.

Novel phosphoryloxy-thiazoles

Novel thiazole derivatives of the formula ##EQU1## wherein A is alkylene of 3 to 5 carbon atoms optionally substituted with a member of the group consisting of =0 and ##EQU2## wherein R' is alkyl of 1 to 5 carbon atoms and R is alkyl of 2 to 3 carbon atoms having insecticidal and/or acaricidal properties and their preparation.

Novel thiazole derivatives as insecticides and acaricides

Novel 3-phosphoryloxy-isothiazoles of the formula ##SPC1## Wherein R is selected from the group consisting of alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms and ##EQU1## R' and R' being individually SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND ALKYL OF 1 TO 3 CARBON ATOMS, R.sub.1 is alkyl of 1 to 3 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 12 carbon atoms, cyano, carbalkoxy of 2 to 4 carbon atoms and NHR'', and R'' is selected from the group consisting of hydrogen and aryl of 6 to 10 carbon atoms, R.sub.3 is selected from the group consisting of cyano, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, carbamoyl, carbalkoxy of 2 to 4 carbon atoms and ##EQU2## A and B are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X is selected from the group consisting of oxygen and sulfur which have excellent insecticidal properties.

Certain isothiazolol esters of phosphorus acids

Novel compounds of the formula ##EQU1## wherein X is selected from the group consisting of oxygen and sulfur, X.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cyano and ##EQU2## Y.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and amino, n is 0, 1 or 2, X.sub.2 is selected from the group consisting of hydrogen, chlorine, bromine, alkyl of 1 to 6 carbon atoms, cyano and ##EQU3## R is alkyl of 1 to 6 carbon atoms, R.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and ##EQU4## and R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms with the proviso that X.sub.1 is other than alkyl when X.sub.2 is alkyl or hydrogen, having insecticidal, nematocidal and acaricidal properties.

Novel thiazole derivatives

Thiazole derivatives of the formula ##SPC1## Wherein A is alkylene of 3 to 5 carbon atoms optionally substituted with a member of the group consisting of =0 and ##EQU1## wherein R' is alkyl of 1 to 5 carbon atoms and R is alkyl of 2 to 3 carbon atoms having insecticidal and/or acaricidal properties and their preparation.

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Les Pavillons Sous Bois, France

Laurent Taliani