Chevron Research Company

Gulf Research & Development Company

Joseph E Moore

David C Chan

Robert K Griffith

Yuh-Lin Yang

N-cyanoalkyl-N-haloalkylthio alkyl-, aryl- and aralkyl-carboxamides of the general formula: ##STR1## wherein R is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, lower alkenyl of 2 to 6 carbon atoms or lower alkynyl of 2 to 6 carbon atoms, all optionally substituted with 1 to 4 halogen atoms; lower alkoxyalkylene; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 16 carbon atoms; or substituted aryl or substituted aralkyl both substituted with 1 to 3 substituents independently selected from phenyl, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, halogen, nitro, cyano, ##STR2## wherein R.sup.4 is hydrogen or lower alkyl of 1 to 6 carbon atoms, ##STR3## wherein R.sup.5 and R.sup.6 are independently hydrogen or lower alkyl of 1 to 6 carbon atoms; R.sup.1 and R.sup.2 are independently hydrogen, or lower alkyl of 1 to 6 carbon atoms; and R.sup.3 is alkyl of 1 to 3 carbon atoms substituted with 3 to 6 halogen atoms or trihalovinyl are fungicidal.

N-cyanoalkyl-N-haloalkylthio carboxamides as fungicides

Compounds of the formula: ##STR1## wherein R is aryl of 6 to 12 carbon atoms or aralkyl of 7 to 14 carbon atoms either optionally substituted with 1 to 3 substituents independently selected from lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, lower alkylsulfinyl of 1 to 6 carbon atoms, lower alkylsulfonyl of 1 to 6 carbon atoms, halogen, trihalomethyl, nitro, cyano or carboxyl; alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, lower alkenyl of 2 to 6 carbon atoms, or lower alkynyl of 2 to 6 carbon atoms, all optionally substituted with 1 to 3 halogen atoms; lower alkoxyalkylene; lower alkylene carbalkoxy; lower alkylthioalkylene; lower alkylsulfinylalkylene; or lower alkylsulfonylalkylene; R.sup.1 and R.sup.2 are independently hydrogen, lower alkyl of 1 to 6 carbon atoms, aryl of 6 to 12 carbon atoms, or thienyl, or taken together form an alkylene bridge to give a cycloalkyl group of 3 to 10 carbon atoms; and R.sup.3 is alkyl of 1 to 3 carbon atoms substituted with 3 to 6 halogen atoms or trihalovinyl are fungicidal.

Fungicidal N-cyanoalkyl-N-haloalkylthio sulfonamides

Compounds of the formula: ##STR1## wherein R is aryl of 6 to 12 carbon atoms, substituted aryl substituted with 1 to 3 substituents independently selected from halogen lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, lower alkylthio of 1 to 4 carbon atoms, nitro, cyano or S(O).sub.n R.sup.4 wherein n is 1 or 2 and R.sup.4 is lower alkyl of 1 to 4 carbon atoms; lower alkylamino of 1 to 6 carbon atoms; the group ##STR2## where R.sup.5 and R.sup.6 are independently hydrogen, lower alkyl of 1 to 6 carbon atoms, aryl or substituted aryl; or alkyl of 1 to 10 carbon atoms, lower cycloalkyl of 3 to 8 carbon atoms, lower alkenyl of 2 to 6 carbon atoms, lower alkynyl of 2 to 6 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms, or alkylthioalkyl of 2 to 8 carbon atoms, all optionally substituted with 1 to 3 halogen atoms; R.sup.1 and R.sup.2 are independently hydrogen, or lower alkyl of 1 to 6 carbon atoms; and R.sup.3 is lower alkyl of 1 to 3 carbon atoms substituted with 3 to 6 halogen atoms or trihalovinyl, are fungicidal.

1-substituted-3-polyhaloalkylthio hydantoin fungicides

Fungicidal oxadithiadiazapentalenes of the formula ##STR1## wherein R and R' are independently hydroxy or lower alkyl; R.sup.1 is hydrogen or lower alkyl; R.sup.2 and R.sup.3 are each, independent of the other, hydrogen, halogen, alkenyl, hydroxy, hydroxyalkenyl, alkoxy, alkoxyalkyl, alkoxyalkenyl, alkylthio, or haloalkyl having from 1 to 3 carbon atoms and from 1 to 4 halogen atoms or R.sup.2 and R.sup.3 together are alkylidiene, alkoxyalkenyl or together with the carbon atom to which they are joined form a cycloalkyl group; and R.sup.4 and R.sup.5 are each independent of the other hydrogen, alkyl, alkoxy, halogen, haloalkyl, nitro, cyano, or dialkylamino. The compounds can be prepared by reacting sulfur chloride with the appropriate substituted N-cyanoalkylenecarboxyamide corresponding to the substituent desired at the 2-position of the compounds. The compounds are useful for controlling plant fungus; especially Grape Downy Mildew fungus and Tomato Late Blight fungus.

Fungicidal 2-substituted-3-oxa-3a

Herbicidal and fungicidal oxadithiadiazapentalenes of the formula ##STR1## wherein X is halo and R is alkyl, haloalkyl, halovinyl, cycloalkyl, thiocayanatoalkyl, aryl, aryloxy, arylthiomethyl, aryloxymethyl, benzylthiomethyl, benzyloxymethyl or heterocyclic are prepared by reacting a sulfur halide and an N-cyanomethylcarboxamide of the formula ##STR2## wherein R is as defined above.

Fungidal and herbicidal 2-substituted-3-oxa-3a.lambda..sup.4,

4-HALO-5-ARYL-1,2,3-DITHIAZOLE, USEFUL AS FUNGICIDES, OVICIDES, INSECTICIDES AND HERBICIDES, ARE PREPARED BY REACTING A N-aryl cyanothioformamide and a sulfur dihalide in the presence of a catalytic amount of a formamide compound or quaternary ammonium salt.

Method for control of fungi using 4-halo-5-aryl-1,2,3,-dithiazoles

Certain 4-halo-5-aryl-1,2,3-dithiazole compounds and their preparation

Compounds of the formula ##STR1## wherein R, R.sup.1 and R.sup.2 are hydrogen, halogen, hydroxy, alkyl or alkenyl optionally substituted with halogen atoms and R.sup.3 is a haloalkyl, haloalkenyl or aryl group, possess morphogenetic hormonal mimetic insecticidal activity.

Insecticidal hydrocarbyl sulfenylmercapto pyrimidines

N-substituted-thio N-alkyl carbamoyl chlorides are prepared by reacting an N-arylthio- or N-aliphaticthio-N-alkylamine with phosgene. The N-arylthio- or N-aliphaticthio-N-alkyl carbamoyl chlorides are useful intermediates for the preparation of pesticides.

Carbamoyl chlorides

Bis-phenylhydrazone sulfides of the formula ##EQU1## wherein R.sup.1 and R.sup.2 individually are hydrogen or alkyl, Ar is phenyl or substituted phenyl, and n is 1, 2 or 3, have morphogenetic hormonal mimetic insecticidal activity.

Insecticidal bis-phenylhydrazone sulfides

Phenylhydrazone sulfides of the formula: ##EQU1## wherein R.sup.1 and R.sup.2 individually are hydrogen or alkyl, R.sup.3 is alkyl, haloalkyl or phenyl substituted with up to 3 halogens, to 5 halogens, Ar is phenyl substituted with up to 5 halogens, and n is 1, 2 or 3, have morphogenetic hormonal mimetic insecticidal activity.

Growing community of inventors

Richmond, CA, United States of America

Joseph E Moore