Chevron Research Company

Chevron Research

David C Chan

William L Schinski

Irene C Huang

Joseph E Moore

Stephen D Ziman

Richard N Reynolds, Jr

Arthur A Whipp

Yuh-Lin Yang

Robert K Griffith

3-(N-acyl-N-arylamino)-gamma-butyrolactones and thiobutyrolactones have fungicidal activity.

Fungicidal 3-(N-acyl-N-arylamino)-gamma-butyrolactones and

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 Ar is aryl, R.sup.1 is halomethyl, R.sup.2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkyl, alkylthio, alkenylthio, alkynylthio, aryl or NR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 individually are hydrogen, alkyl, alkenyl or alkynyl, R.sup.3 is hydrogen or alkyl, n is 1 or 2, Y is O, S or NR wherein R is hydrogen, alkyl, alkenyl or alkynyl, have been found to be useful herbicides. The compounds are prepared by acylation of the corresponding N-heterocyclealkylene-N-arylamine.

Herbicidal N-oxadiazolylmethyl-, N-thiadiazolylmethyl-, and

3-(N-butyryl or valeryl-N-arylamino)-gamma-butyrolactones and their thio analogs. These compounds are useful as fungicides.

Fungicidal 3-(N-acyl-N-arylamino) lactones

Compounds of the formula: ##STR1## wherein X is oxygen or sulfur; Z is oxygen or sulfur; R is pyridyl optionally substituted with 1 to 3 substituents independently selected from halogen, lower alkyl or lower alkoxy optionally substituted with 1 to 3 of the same or different halogen atoms or nitro; R.sup.1 is lower alkyl; and R.sup.2 is a 5- or 6-membered heterocyclic ring containing 1 to 3 ring nitrogens and the remainder of the ring atoms carbon atoms, a quinoline ring or a phenyl ring, all optionally substituted with 1 to 3 substituents independently selected from halogen, trihalomethyl, lower alkyl or lower alkoxy are fungicidal.

Fungicidal N-pyridyloxyalkyl amides

Compounds of the formula: ##STR1## wherein X is oxygen or sulfur;

Fungicidal N-pyridyloxy alkyl amines

Salts, esters, amides, hydrazides and hydroxyamides of 4-methyl-4-[3'-(4'-trifluoromethylphenoxy)-phenoxy]crotonic acid are herbicidal against broad leaf plants.

Herbicidal

N-[1-(2'-substituted-alkyl)-amidomethyl and carboalkoxymethyl]-substituted-N-acylanilines have fungicidal activity.

1-(2'-Haloalkyl)-amidomethyl-substituted acetanilide fungicides

N-(2-[4-(4-trifluoromethylphenoxy)-phenoxy]propyl)-N-methylformamide. The base compound is prepared via formylation of the corresponding amine intermediate. The compounds are useful as fungicides, herbicides and plant-growth regulators and especially as cotton defoliants or desiccants.

Diphenoxy ether formamide plant-growth regulator

3-(N-acyl-N-arylamino) and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and thiobutyrolactones have fungicidal activity.

Fungicidal 3-(N-acyl-N-arylamino)-and

Compounds of the formula ##STR1## wheren X.sup.1 is halo or trihalomethyl, X.sup.2 is hydrogen or halo, R.sup.1 is nitro or --OR.sup.3, R.sup.2 is hydrogen or --OR.sup.4, R.sup.3 ##STR2## R.sup.4 is ##STR3## and R is hydroxy, alkoxy, alkenoxy, alkynoxy, thiol, alkythio, alkenylthio, amino, mono- or di-substituted amino or OM, wherein M is a monovalent cation; R' and R' are hydrogen, alkyl, alkenyl, alkynyl or phenyl; and Y is oxygen, sulfur, or substituted or unsubstituted nitrogen, have herbicidal activity.

Herbicidal 3-butyrolactones

Fungicidal 3-(N-acyl-N-arylamino)- and

Compounds represented by the formula ##STR1## wherein R and R.sup.1 are independently hydrogen or lower alkyl; R.sup.2 is lower alkenyl, lower alkynyl or --CH.sub.2 X wherein X is halogen, hydroxyl, lower alkoxy, lower alkylthio or a furanyl ring; and Z is hydroxyl, lower alkoxy or --NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 are independently hydrogen or lower alkyl possess fungicidal activity. Moreover, some of the compounds of this invention also possess herbicidal activity.

Fungicidal N-1-substituted cyclopropyl-N-acyl-2,6-dialkylaniline

Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is phenyl or substituted phenyl; R.sup.1 is halomethyl; R.sup.2 and R.sup.3 are each independently hydrogen, alkyl, phenyl, benzyl, substituted phenyl or benzyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl or thiocyanoalkyl; R.sup.4 is hydrogen or alkyl; n is 0 or 1; m is 0 or 1; R is hydrogen, alkyl, alkenyl, alkynyl, alkylthioalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, phenyl, benzyl, substituted phenyl or benzyl, or R is acyl of the formula ##STR2## wherein R.sup.5 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, acetonyl, or the group --NR'R' wherein R' and R' are independently hydrogen, alkyl or phenyl; with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring or a heterocyclic ring; or R and R.sup.2 may be joined together to form a heterocyclic ring; or R and R.sup.3 may be joined together to form a heterocyclic ring.

N-Haloacetylphenylamino carbonyl cyclic intermediates

3-(N-arylamino)-gamma-butyrolactones, butyrolactams and thiobutyrolactones are intermediates for compounds having fungicidal activity.

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Petaluma, CA, United States of America

David C Chan