Fmc Corporation

Kanagawa Chemical Laboratory, Ltd.

Ernest L Plummer

David E Seelye

John F Engel

Kiyoshi Kondo

Richard B Phillips

John A Dixson

Blaik P Halling

John M Tymonko

Hiromichi Kono

Kirk A Simmons

Marjorie J Plummer

Anthony J Martinez

Raymond M Palmere

Ronald Eugene Montgomery

The present application discloses herbicidal substituted-phenyl-1,2,4-Triazol-5(1H)-thiones and -ones, herbicidal compositions containing these compounds, methods of preparing them, and methods for controlling undesired plant growth by preemergence and/or postemergence application of the herbicidal compositions to the locus where control is desired. The herbicidal compounds are compounds of the formula ##STR1## wherein: Ar is selected from ##STR2## R is selected from haloalkyl; R.sup.1 is selected from alkyl;

Herbicidal substituted phenyl-1,2,4-triazol-5(1H)-thiones

The present application discloses herbicidal substituted-phenyl-1,2,4-Triazole-5(1H)-thiones and -ones, herbicidal compositions containing these compounds, methods of preparing them, and methods for controlling undesired plant growth by preemrgence and/or postemergence application of the herbicidal compositions to the locus where control is desired. The herbicidal compounds are compounds of the formula ##STR1## wherein Ar is selected from ##STR2## R is selected from haloalkyl; R.sup.1 is selected from alkyl;

Herbicidal substituted-phenyl-1,2,4-triazol-5(1H)-thiones and -ones

N-[(Alpha-perhaloalkylbenzyloxy)pyridyl]-N'-benzoylurea compounds of the following structural formula are useful insecticides: ##STR1## in which R.sub.A is selected from the group consisting of -hydrogen, -halogen, -lower alkyl, -lower alkoxy, -benzyl, and -benzyloxy;

N-[(alpha-perhaloalkylbenzyloxy)pyridyl]N'-benzoylurea insecticides

N-[(Alpha-perhaloalkylbenzyloxy)pyridyl]-N'-benzoylurea compounds of the following structural formula are useful insecticides: ##STR1## in which R.sub.A is selected from the group consisting of -hydrogen, -halogen, -lower alkyl, -lower alkoxy, -benzyl, and -benzyloxy; R.sub.B is selected from -hydrogen and -halogen; R.sub.C and R.sub.D are both -hydrogen or together constitute a --COCO-- bridge; R.sub..alpha. is a perhaloalkyl substituent; R.sub.3 is selected from the group consisting of -hydrogen, -halogen and -phenylthio; R.sub.4 is selected from the group consisting of -hydrogen, -halogen, -lower alkyl, -lower alkoxy, -lower alkoxyalkyl, -lower haloalkoxy, -lower alkylthio, -lower alkylsulfonyl, and -diallylamino; or R.sub.3 and R.sub.4 at adjacent ring positions constitute a --OCH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, or --CF.sub.2 CF.sub.2 O-- bridge; and R.sub.5 is -hydrogen or -lower alkyl.

N-[(alpha-perhaloalkylbenzyloxy)pyridyl]-N'-benzoylurea insecticides

A 2,2'-bridged[1,1'-biphenyl]-3-ylmethyl compound of the following formula is an intermediate to insecticidal esters. ##STR1## wherein n is 1-4 and Y is a leaving group readily displaced by carboxylate anions.

[1,1'-biphenyl]compounds having a 2,2'-(alkyl)bridge and a

Benzofurans of the formula ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetamido, R.sup.2 is at least one of halo, cyano, alkyl(C.sub.1 -C.sub.8), cycloalkyl(C.sub.3 -C.sub.8), hydroxy, alkoxy(C.sub.1 -C.sub.8), acyl(C.sub.1 -C.sub.8), acyloxy(C.sub.1 -C.sub.8), alkoxy(C.sub.1 -C.sub.8)carbonyl, alkoxy(C.sub.1 -C.sub.8)carbonylalkyl(C.sub.1 -C.sub.8), phenyl, phenyloxy, trifluoromethyl or dialkyl(C.sub.1 -C.sub.8)amino, m is 0-3, and at least one of the carbon atoms of the benzene ring of said benzofuran is substituted. The compounds are intermediates in the preparation of pyrazoline insecticides.

Tetrafluoro-2,3-dihydrobenzofurans

A method for controlling soil-borne insects such as southern corn rootworm is disclosed and exemplified in which the pyrethroid 2,4,6-trifluorophenylmethyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylat e is applied to the soil for initial and residual insect control.

Method for control of soil-borne insects

Compounds of the formula ##STR1## wherein Z is ##STR2## compositions containing the compounds, and their utility as dietary and foliar insecticides are disclosed and exemplified.

N-(4-(2-aryltetrafluoroethoxy)-3-methoxyphenyl)-N'-benzoylurea insect

Tetrafluorobenzofurans of the formula ##STR1## are prepared by contacting, at elevated temperature in an aprotic solvent, an ether of the formula ##STR2## with a catalytic mixture of metallic cooper and a polydentate or other ligand, wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetylimido, R.sup.2 is at least one of hydrogen, halo, cyano, alkyl, hydroxy, alkoxy, acyl, acyloxy, alkoxycarbonyl, alkoxycarbonylalkyl, phenyl, phenyloxy, trifluoromethyl or dialkylamino. The products are intermediates in the preparation of pyrazoline insecticides.

Process of preparation of tetrafluoro 2,3-dihydrobenzofurans

Fluoropyridinylmethyl cyclopropanecarboxylate insecticides

Substituted [1,1'-biphenyl]-3-ylmethyl compounds carrying leaving groups are intermediates to insecticidal esters.

Intermediates to insecticidal [1,1'-biphenyl]-3-ylmethyl esters

Insecticidal compounds of the formula ##STR1## in which A and B are both halogen or hydrogen, or one of A and B is hydrogen, and the other of A and B is halogen; Z and W are independently O or S; the substituted benzofuranyl or benzothienyl group is attached at position 5 or 6; R is halogen; m is 0 to 3; R' is F or CF.sub.3 ; methods for their preparation and formulation, insecticidal compositions, and their use to control insects are disclosed.

Insecticidal urea substituted 2,3-dihydro- benzofuran and benzothiophene

Insecticidal compounds of the formula: ##STR1## in which A is chloro and B is hydrogen or A and B are both fluoro, X is oxygen or sulfur and one of R.sup.1 and R.sup.2 is or includes an optionally substituted 5-membered heteroaryl ring, their method for preparation and formulation, insecticidal compositions thereof, and their use to control insects, are disclosed and exemplified.

Insecticidal heteroaryl substituted phenyl benzoylureas

2-(Alpha-perhaloalkylbenzyloxy)pyridyl compounds of the following structural formula are intermediates to N-[(alpha-perhaloalkylbenzyloxy)pyridyl]-N'-benzoylurea insecticides: ##STR1## in which R.sub..alpha. is a perhaloalkyl substituent;

2-(alpha-perhaloalkylbenzyloxy)pyridyl insecticide intermediates

Certain benzocycloalkaneheteroaromaticmethyl, e.g., benzocycloalkanethiophenemethyl, esters and insecticidal compositions containing these esters are useful for the control of a broad range of insects and acarids.

Growing community of inventors

Yardley, PA, United States of America

Ernest L Plummer