Uniroyal Chemical Company, Inc.

Uniroyal Inc.

Uniroyal Chemical Ltd./ltee

Uniroyal Chemical Limited

Other

Richard C Moore

Mark A Dekeyser

Anupama Mishra

Winchester L Hubbard

Rupert A Covey

Richard J Strunk

Benjamin J Pierce

Richard R Regis

Paul T McDonald

Howard L Plant

Patricia J Forbes

Kevin J Donovan

A class of compounds useful for providing long-term control of pests, such as insects, nematodes and acarids, having the structural formula: ##STR1## where R is lower alkyl, phenyl, substituted phenyl, naphthyl or substituted napthyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.2 is C.sub.1 -C.sub.6 alkyl or phenyl; R.sup.3 is C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkylthio; R.sup.4 is C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylamino or C.sub.1 -C.sub.6 dialkylamino; and X is oxygen or sulfur.

Oxime phosphate pesticidal compounds, compositions and methods

Compounds of the formula: ##STR1## wherein R is alkyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, haloalkyl, phenyl, naphthyl, alkenyl, substituted phenyl, benzyl or substituted benzyl; R.sup.1 is hydrogen, alkyl or phenyl; R.sup.2 is alkyl, alkoxy, alkylthio, alkylamino or dialkylamino; R.sup.3 is alkyl; and X and X.sup.1 are each independently sulfur or oxygen; exhibit insecticidal, acaricidal and nematicidal activity. Also disclosed are compositions comprising such compounds as well as methods of controlling insects, acarids and nematodes.

Phosphorous substituted tetrazolinones and insecticidal use thereof

Organophosphorus-substituted oxadiazines are disclosed which exhibit insecticidal, acaricidal and nematicidal activity, as well as compositions including such compounds, and methods for controlling insects, acarids or nematodes employing such compounds and/or compositions. Also disclosed are novel intermediates useful in the preparation of such compounds.

Oxadiazinyl organophosphorus pesticides

A new class of 2-(tetrahydro-2-theinyl)phenyl esters of phosphorothioic acid is disclosed. This class of compounds is an effective pesticide and finds particular application as an insecticide. A class of pesticidal compositions employing these compounds in combination with a carrier therefor is also set forth.

2-(tetrahydro-2-thienyl)phenyl esters of phosphorothioic acid

A compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.6 cycloalkyl; X is hydrogen or methyl;

2-(tetrahydro-2-thienyl)phenols and carbamate derivatives

##STR1## where X is oxygen or sulfur; X.sup.1 is oxygen, sulfur, NH or NR.sup.3 ; C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.13 alkoxyalkyl, C.sub.7 -C.sub.9 aralkyl, C.sub.5 -.sub.6 cycloalkyl, C.sub.3 -C.sub.12 alkenyl, naphthyl, phenyl, phenyl substituted with at least one member selected from the group consisting of: halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, methylenedioxy, NR.sup.4 R.sup.5 (wherein R.sup.4 and R.sup.5 are the same or different and are hydrogen or C.sub.1 -C.sub.6 alkyl), C.sub.2 -C.sub.5 alkoxycarbonyl, carboxy, phenoxy, nitro, cyano, trihalomethyl, trihalomethoxy, C.sub.1 -C.sub.6 alkylthio, and C.sub.1 -C.sub.6 fluoroalkylthio; or benzyl substuted with at least one member selected from the group consisting of: halogen C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, methylenedioxy, C.sub.2 -C.sub.5 alkoxycarbonyl, phenoxy, nitro, cyano, trihalomethyl, trihalomethoxy, C.sub.1 -C.sub.6 alkylthio and C.sub.1 -C.sub.6 fluoroalkylthio; and R.sup.1, and R.sup.3 may be the same or different and are C.sub.1 -C.sub.4 alkyl and R.sub.2 may be C.sub.1 -C.sub.4 alkyl, alkoxy, alkylthio and alkyl amino is disclosed. The application is also directed to a pesticidal composition comprising the above-recited compound and a carrier.

Phosphorus substituted tetrazolinones and pesticidal use

Thiomethyl-substituted organosilane compounds demonstrate unexpected insecticidal and acaricidal control. Also disclosed are compositions comprising such compounds, a method of controlling pests employing such compounds, and a process of manufacturing such compounds.

Thiomethyl-substituted organosilane compounds and their use as pesticides

A compound having the formula ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl, cyclopropyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.4 -C.sub.8 diakylaminoalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.2 -C.sub.4 alkylsulfinylalkyl, C.sub.2 -C.sub.4 alkylsulfonylalkyl, phenyl, C.sub.7 -C.sub.9 aralkyl, C.sub.7 -C.sub.9 alkaryl, furyl, thienyl or pyridyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.3, R.sup.4 and R.sup.5 are the same or different and are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 and R.sup.7 are the same or different and are hydrogen, C.sub.1 -C.sub.4 alkyl, allyl, benzyl or tolyl with the proviso that both R.sup.6 and R.sup.7 are not hydrogen; and n is O, 1 or 2 and methods of making same are disclosed. This compound is useful as a pesticide. Intermediates useful in synthesizing this pesticidally effective compound are also taught. These intermediate compounds have the structural formulas ##STR2## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 and n have the same meanings as the pesticidally effective compound recited above; and Q is a leaving group. Methods of making these intermediate compounds are described.

Substituted oxime carbamates

A compound having the structural formula ##STR1## where R.sup.1 and R.sup.2 are the same or different and are hydrogen; however, both R.sup.1 and R.sup.2 cannot be hydrogen if R.sup.3 and R.sup.4 are both hydrogen or if one of R.sup.3 and R.sup.4 is hydrogen and the other nitro; in addition R.sup.1 and R.sup.2 may be the same or different and may be fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.9 aralkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.7 -C.sub.9 aralkoxy, phenoxy, provided that if both R.sup.3 and R.sup.4 are hydrogen, then R.sup.1 and R.sup.2 cannot be 3-phenoxy and hydrogen; also R.sup.1 and R.sup.2 may be the same or different and may be phenylthio, phenylsulfonyl, alkali metal carboxylate, C.sub.2 -C.sub.5 alkoxycarbonyl, phenoxycarbonyl or --NR.sup.5 R.sup.6 ; R.sup.3 and R.sup.4 are the same or different and are C.sub.1 -C.sub.4 alkylsulfonyl, nitro; provided that if the other of R.sup.3 and R.sup.4 is hydrogen then R.sup.1 and R.sup.2 cannot both be hydrogen, also R.sup.3 and R.sup.4 may be the same or different and may be --OCX.sub.n H.sub.3-n or any of the meanings given for R.sup.1 and R.sup.2 with the proviso that if R.sup.3 and R.sup.4 are together hydrogen or bromine then if R.sup.1 and R.sup.2 are both hydrogen the bromine cannot be 4-bromo; R.sup.5 and R.sup.6 are the same or different and are hydrogen or C.sub.1 -C.sub.2 alkyl with the proviso that when R.sup.5 and R.sup.6 are both hydrogen then R.sup.1, R.sup.2 and R.sup.3 cannot all be hydrogen; X is fluorine, chlorine or bromine; and n is 1, 2 or 3 is disclosed. The compounds of this invention are effective as a nematocidal and/or a miticidal agent. A process for forming these compounds is also set forth.

Substituted oxadiazinone miticidal compositions and use

2-(tetrahydro-2-thienyl)phenols and carbamate derivatives thereof

A compound having the structural formula ##STR1## where R.sup.1 and R.sup.2 are the same or different and are hydrogen; however, both R.sup.1 and R.sup.2 cannot be hydrogen if R.sup.3 and R.sup.4 are both hydrogen or if one of R.sup.3 and R.sup.4 is hydrogen and the other nitro; in addition R.sup.1 and R.sup.2 may be the same or different and may be fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.9 aralkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.7 -C.sub.9 aralkoxy, phenoxy, provided that if both R.sup.3 and R.sup.4 are hydrogen, then R.sup.1 and R.sup.2 cannot be 3-phenoxy and hydrogen; also R.sup.1 and R.sup.2 may be the same or different and may be phenylthio, phenylsulfonyl, alkali metal carboxylate, C.sub.2 -C.sub.5 alkoxycarbonyl, phenoxycarbonyl or --NR.sup.5 R.sup.6 ; R.sup.3 and R.sup.4 are the same or different and are C.sub.1 -C.sub.4 alkylsulfonyl, nitro; provided that if the other of R.sup.3 and R.sup.4 is hydrogen then R.sup.1 and R.sup.2 cannot both be hydrogen, also R.sup.3 and R.sup.4 may be the same or different and may be --OCX.sub.n H.sub.3-n or any of the meanings given for R.sup.1 and R.sup.2 with the proviso that if R.sup.3 and R.sup.4 are together hydrogen and bromine then if R.sup.1 and R.sup.2 are both hydrogen the bromine cannot be 4-bromo; R.sup.5 and R.sup.6 are the same or different and are hydrogen or C.sub.1 -C.sub.2 alkyl with the proviso that when R.sup.5 and R.sup.6 are both hydrogen then R.sup.1, R.sup.2 and R.sup.3 cannot all be hydrogen; X is fluorine, chlorine or bromine; and n is 1, 2 or 3 is disclosed. The compounds of this invention are effective as a nematocidal and/or a miticidal agent. A process for forming these compounds is also set forth.

Substituted oxadiazinones

A compound of the formula ##STR1## wherein R is allyl, halocyclopropyl, C.sub.3 -C.sub.5 alkoxycarbonylmethyl, C.sub.7 -C.sub.9 aralkyl, styryl, phenyl, naphthyl, furanyl, pyridyl, thienyl, phenyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, trihalomethyl, C.sub.1 -C.sub.4 alkoxy, trihalomethoxy, trihalomethylthio, C.sub.1 -C.sub.4 alkylthio, phenyl, phenoxy, cyano or nitro or C.sub.7 -C.sub.9 aralkyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, trihalomethyl, C.sub.1 -C.sub.4 alkoxy, trihalomethoxy, trihalomethylthio, C.sub.1 -C.sub.4 alkylthio, phenyl, phenoxy, cyano or nitro; R.sup.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.7 -C.sub.9 aralkyl, phenyl, C.sub.7 -C.sub.9 aralkyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, trihalomethyl, C.sub.1 -C.sub.4 alkoxy, trihalomethoxy, trihalomethylthio, C.sub.1 -C.sub.4 alkylthio, phenyl, phenoxy, cyano or nitro or phenyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, trihalomethyl, C.sub.1 -C.sub.4 alkoxy, trihalomethoxy, trihalomethylthio, C.sub.1 -C.sub.4 alkylthio, phenyl, phenoxy, cyano or nitro, however, if R is substituted phenyl or substituted C.sub.7 -C.sub.9 aralkyl, then R.sup.1 cannot be hydrogen; R.sup.2 is C.sub.1 -C.sub.4 alkyl, however, if R or R.sup.1 is 4-chlorophenyl, R.sup.2 cannot be isopropyl; and X, Y and Z are the same or different and are oxygen or sulfur, is disclosed. A method is provided for protection against pests by employing a pesticidally effective amount of the compound above. A composition comprising the compound above and an inert carrier therefor, for pesticidal use, is also taught. The disclosure also recites a compound of the formula ##STR2## where R and R.sup.1 have the meanings of the first mentioned compound. The compound, effective as an intermediate in the synthesis of the above compound, is produced by the reaction of a compound of the formula ##STR3## where R has the meanings given above with a compound of the formula

Certain 2-(pyridyl or

A compound having the formula ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl, cyclopropyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.4 -C.sub.8 dialkylaminoalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.2 -C.sub.4 alkylsulfinylalkyl, C.sub.2 -C.sub.4 alkylsulfonylalkyl, phenyl, C.sub.7 -C.sub.9 aralkyl, C.sub.7 -C.sub.9 alkaryl, furyl, thienyl or pyridyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.3, R.sup.4 and R.sup.5 are the same or different and are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 and R.sup.7 are the same or different and are hydrogen, C.sub.1 -C.sub.4 alkyl, allyl, benzyl or tolyl with the proviso that both R.sup.6 and R.sup.7 are not hydrogen; and n is 0, 1 or 2 and methods of making same are disclosed. This compound is useful as a pesticide. Intermediates useful in synthesizing this pesticidally effective compound are also taught. These intermediate compounds have the structural formulas ##STR2## where R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the same meanings as the pesticidally effective compound recited above; and Q is a leaving group. Methods of making these intermediate compounds are described.

An organophosphorus compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.4 alkyl; R.sup.1 is hydrogen or methyl; or R and R.sup.1 together are a diradical having the formula --SC(Y).dbd.Z--, where Y is halogen, hydrogen or C.sub.1 -C.sub.2 alkyl; and Z is nitrogen, CH, C(CH.sub.3) or C(C.sub.2 H.sub.5) with the proviso that if Y is hydrogen, Z cannot be CH; R.sup.2 is hydrogen, chlorine or bromine; R.sup.3 is methyl or ethyl; R.sup.4 is methoxy, ethoxy, --SCH.sub.3 or --SC.sub.2 H.sub.5 ; and X is oxygen or sulfur and their hydrochlorides is disclosed. These compounds are useful as insecticides or nematocides. In another aspect of this invention a method of controlling rice planthoppers is provided. In this method an insecticidally effective amount of a compound having the formula given above where R is C.sub.1 -C.sub.4 alkyl or benzyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; or R and R.sup.1 together are a diradical selected from the group consisting of --CH.dbd.CH--CH.dbd.CH--, --CH.dbd.CCl--CH.dbd.CH--, --CH.dbd.C(CH.sub.3)--CH.dbd.CH-- and --SC(Y).dbd.Z--, where Y is halogen, hydrogen or C.sub.1 -C.sub.2 alkyl; and Z is nitrogen, CH, C(CH.sub.3) or C(C.sub.2 H.sub.5); R.sup.2 is hydrogen or bromine; R.sup.3 is methyl or ethyl; R.sup.4 is methoxy, ethoxy or propylthio, with the proviso that if R.sup.2 is bromine, R.sup.4 is propylthio, and X is oxygen or sulfur is applied to the loci where rice planthoppers reside.

Substituted pyrimidinyl organophosphorus insecticides

A method is disclosed for combating the soil insect, corn rootworm which comprises contacting the corn rootworm with an effective amount of N-methyl 2-(1-methylethyl)phenylcarbamate.

Growing community of inventors

Wallingford, CT, United States of America

Richard C Moore