Chevron Research Company

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Chevron Research

Laroy H Edwards

James D Cleveland

Compounds of the formula: ##STR1## wherein X is independently halogen, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, nitro, lower alkylsulfinyl of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, amino or trifluoromethyl; n is 0, 1, 2 or 3; R is hydrogen, alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 8 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 of the same or different halogen atoms; or aryl of 6 to 12 carbon atoms; or substituted aryl substituted with 1 to 3 substituents independently selected from lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, and the group --S(O).sub.k R.sup.2 where k is 0, 1 or 2 and R.sup.2 is lower alkyl of 1 to 4 carbon atoms, nitro, cyano or halogen; and R.sup.1 is lower alkyl of 1 to 6 carbon atoms, lower cycloalkyl of 3 to 8 carbon atoms or aryl of 6 to 12 carbon atoms, provided that R and R.sup.1 are not both cyclohexyl, are fungicidal and in some cases insecticidal.

2-thio-organotin-4(3H)-quinazolinone

Compounds of the formula: ##STR1## wherein R is aryl or 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, --S(O).sub.n R.sup.2 wherein n is 1 or 2 and R.sup.2 is lower alkyl of 1 to 4 carbon atoms; or alkyl, cycloalkyl, lower alkenyl or lower alkynyl, all optionally substituted with 1 to 3 halogen atoms; and R.sup.1 is lower alkyl, trialkylsilylmethylene, aryldialkylsilylmethylene, aryl; aralkyl, or substituted aryl or aralkyl are fungicidal.

1-iodopropargyl-3,4-disubstituted-.DELTA..sup.2 -1,2,4-triazolidin-5-one

Compounds of the formula: ##STR1## wherein X is independently halogen, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, nitro, the group R.sup.1 --S(O).sub.m -- wherein R.sup.1 is lower alkyl of 1 to 6 carbon atoms and m is 0, 1 or 2, amino, or trifluoromethyl; n is 0, 1, 2 or 3; and R is alkyl of 1 to 10 carbon atoms; cycloalkyl of 3 to 8 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 of the same or different halogen atoms, or aryl of 6 to 12 carbon atoms or substituted aryl substituted with 1 to 3 groups independently selected from lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, lower alkylthio of 1 to 4 carbon atoms, oxidized alkylthio, nitro, cyano, or halogen are fungicidal.

4-quinazalone fungicides

Compounds of the formula: ##STR1## wherein R is aryl of 6 to 10 carbon atoms; substituted aryl substituted with 1 to 5 substituents selected from halogen, nitro, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, trihalomethyl, or ##STR2## wherein R.sup.2 is lower alkyl of 1 to 4 carbon atoms; alkyl of 1 to 8 carbon atoms; cycloalkyl of 3 to 8 carbon atoms; 1-alkylcycloalkyl of 4 to 9 carbon atoms; 1-alkylthio-1,1-dialkylmethyl of 4 to 7 carbon atoms; 1-alkoxy-1,1-dialkylmethyl of 4 to 7 carbon atoms; furyl; thienyl; or pyridyl; and R.sup.1 is lower alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, aryl of 6 to 10 carbon atoms, substituted aryl of 6 to 10 carbon atoms substituted with 1 to 5 lower alkyl groups of 1 to 6 carbon atoms or aralkyl of 7 to 12 carbon atoms are fungicidal.

Fungicidal 5-oxo-4-trisubstituted tin-1,3,4-oxadiazolines

Compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently lower alkyl having from 1 to 4 carbon atoms; and R.sup.3 is lower alkyl having from 1 to 6 carbon atoms, lower cycloalkyl having from 3 to 6 carbon atoms optionally substituted with methyl or ethyl, lower alkoxyalkyl having up to a total of 8 carbon atoms or lower alkylthioalkyl having up to a total of 8 carbon atoms are insecticidal.

Insecticidal 5-thiocarbamoyl-1,3,4-oxadiazoles

Compounds of the formula: ##STR1## wherein X is oxygen or sulfur; R.sup.1 and R.sup.2 are independently lower alkyl having from 1 to 4 carbon atoms; and R.sup.3 is lower alkyl having from 1 to 6 carbon atoms, lower cycloalkyl having from 3 to 6 carbon atoms optionally substituted with methyl or ethyl, lower alkoxyalkyl having up to a total of 8 carbon atoms or lower alkylthioalkyl having up to a total of 8 carbon atoms are insecticidal.

Insecticidal N-carbamoyl-oxadiazolidin-5-ones and thiones

Compounds of the formula ##STR1## wherein R is hydrogen, lower alkyl or lower alkoxy, R.sup.1 and R.sup.2 are independently lower alkyl and Y is either oxygen or sulfur possess insecticidal activity.

Insecticidal 2-oxo-3-dialkoxyphosphoro-5-cyclopropyl-1,3,4-oxadiazoline

2-Thiohaloalkenyl-4-dialkoxyphosphino-thioyloxy-6-alkyl-1,3-pyrimidines represented by the formula: ##STR1## wherein R and R.sup.1 are independently lower alkyl; R.sup.2 is hydrogen, lower alkyl or lower alkoxy; X, Y and Z are independently halogen or hydrogen with at least one of X, Y and Z being halogen; possess fungicidal and insecticidal activity.

Fungicidal and insecticidal

N-tetrachloroethylthio-substituted halomethanesulfonamides of the formula ##STR1## wherein R is alkyl, cycloalkyl, acyl, X is fluoro, chloro, bromo or iodo and R' is tetrachloroethyl, are useful as algicides.

N-Tetrachloro-ethylthio-substituted halomethanesulfonamides as aquatic

N-trichlorovinylthio-substituted halomethanesulfonamides of the formula ##STR1## wherein R is alkyl, cycloalkyl, aryl, X is fluoro, chloro, bromo or iodo and R' is trichlorovinyl, are fungicides and algicides.

N-Alkyl or aryl-N-(trichlorovinylthio)-halomethane sulfonamides

Compounds of the formula ##STR1## wherein X is halo or C.sub.1 -C.sub.4 alkyl, n=1, 2 or 3 and R and R' are hydrogen or C.sub.1 -C.sub.6 alkyl have herbicidal and plant-growth regulating activity.

Herbicidal and plant-growth-regulating 2-phenoxyalkyl-oxadiazoles

Novel sulfonamides of the formula ##STR1## wherein R.sup.1 is alkyl, cycloalkyl or aryl; R.sup.2 is haloalkyl or halovinyl; and X is hydrogen or halogen and at least one X is halogen, are useful for the prevention or cure of fungal infections.

Fungicidal N-(haloaliphaticthio)halovinylsulfonamides

Thiadiazin-5-one compounds of the formula ##STR1## wherein R.sup.1 is alkyl and R.sup.2 is alkyl, alkenyl, cycloalkyl or aryl are prepared by reacting a thiosemicarbazide and an alkyl alpha-halothioacetate. Addition of a dialkylhalothiophosphate to the thiadiazin-5-one compounds produces useful thiadiazine insecticides.

Process for production of

Thiadiazine compounds of the formula (I) ##STR1## wherein R.sup.1 is alkyl, R.sup.2 is alkyl, cycloalkyl, alkenyl or aryl, R.sup.3 is alkyl and R.sup.4 is alkyl, are useful as insecticides. The thiadiazine compounds are prepared by the addition of a dialkylhalothiophosphate to a tetrahydro-6H-1,3,4-thiadiazin-5-one.

Insecticidal

Compounds of the formula ##STR1## wherein R.sup.1 is alkyl, alkenyl, cycloalkyl or aryl; R.sup.2 is alkyl, haloalkyl, alkenyl or aryl; and R.sup.3, R.sup.4 and R.sup.5 individually are alkyl or aryl, possess pesticidal activity.

Growing community of inventors

Napa, CA, United States of America

Laroy H Edwards