Roussel Uclaf

Jacques Perronnet

Laurent Taliani

Pierre Girault

Andre Teche

Claude Bonne

Jean-Pierre Demoute

Andre Poittevin

Novel crotonamides of the formula ##STR1## wherein R is selected from the group consisting of adamantyl, bornyl, 5',6'-dihydroendo-5'-dicyclopentadienyl and saturated and unsaturated cycloalkyl of 3 to 8 carbon atoms optionally substituted with a member of the group consisting of alkyl of 1 to 6 carbon atoms, hydroxy, chlorine and alkoxycarbonyl of 1 to 6 alkyl carbon atoms and R.sub.1 is alkyl of 1 to 3 carbon atoms having pre- and post-emergence herbicidal properties.

Novel crotonamides

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 ureas of the formula ##STR1## wherein A and B are chlorine or A is chlorine or hydrogen and B is --CF.sub.3, R and R.sub.1 are individually alkyl of 1 to 3 carbon atoms and R.sub.2 is alkyl of 1 to 6 carbon atoms optionally substituted with a halogen having herbicidal properties, particularly useful in cultivated grass crops and their preparation and use.

Novel ureas

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

Antiandrogenic compositions comprising an effective amount of at least one compound of the formula ##STR1## wherein X and Y are individually selected from the group consisting of hydrogen, halogen, --CF.sub.3, --NO.sub.3 and alkylthio of 1 to 4 carbon atoms and R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, phenyl, benzyl and hydroxymethyl and an inert pharmaceutical carrier and a method of inducing antiandrogenic activity in warm-blooded animals as well as novel oxadiazines of formula I with the proviso that when R is other than benzyl or hydroxymethyl at least one of X and Y is alkylthio of 1 to 4 carbon atoms.

3-Oxo-5,6-dihydro-1,2,4-oxadiazines useful as antiandrogenic agents

Imidazolidines of the formula ##STR1## wherein X is selected from the group consisting of oxygen and amine which inhibit the effects of androgens on peripheric receptors without interfering with normal hypophysial functions.

1-(3'-Trifluoromethyl-4'-nitrophenyl)-4,4-dimethyl imidazolidines

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 crotonanilides of the formula ##STR1## wherein R' is selected from the group consisting of ##STR2## R and R.sub.1 are alkyl of 1 to 6 carbon atoms and R.sub.2 is selected from the group consisting of hydrogen, methyl and methoxy having pre- and post-emergence herbicidal activity.

3-Methoxy crotonanilides as herbicides

Novel crotonanilides of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## X is selected from the group consisting of alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 7 carbon atoms, Z is alkyl of 1 to 6 carbon atoms, X.sub.1 is alkoxyalkyl of 2 to 12 carbon atoms, X.sub.2 is alkyl of 1 to 3 carbon atoms, X.sub.3 is selected from the group consisting of alkyl or alkoxy of 1 to 3 carbon atoms and R.sub.1 and R.sub.2 are individually alkyl of 1 to 3 carbon atoms having pre- and post-emergence herbicidal activity.

Crotonanilides

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 crotonanilides of the formula ##STR1## wherein Z is selected from the group consisting of --O-- and --S--, R is selected from the group consisting of alkyl of 1 to 6 carbon atoms and optionally substituted phenyl, X and Y are individually selected from the group consisting of hydrogen, halogen, lower alkyl of 1 to 6 carbon atoms optionally substituted with at least one halogen, alkoxy of 1 to 3 carbon atoms, alkylthio and alkylsulfinyl of 1 to 6 carbon atoms, acyl of an organic carboxylic acid of 1 to 6 carbon atoms, --NO.sub.2 and --CF.sub.3, R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, alkoxycarbonyl with 1 to 6 alkyl carbon atoms, nitro and alkylthio, alkylsulfinyl and alkylsulfonyl of 1 to 3 alkyl carbon atoms and R.sub.2 is alkyl of 1 to 6 carbon atoms, said compounds existing in the form of their E or Z isomers or mixtures thereof and having herbicidal properties.

Novel crotonanilides

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.

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Paris, France

Jacques Perronnet