Abstract: It has now been found that certain novel bis(substituted phenyl)-1 {[4-(saturated heterocyclyl-substituted)phenyl-methyl](4-piperidyl)}methane derivatives have provided unexpected insecticidal activity. These compounds are represented by formula (I); where R through R15, m, n, s, A, B, D and W are defined herein. In addition, compositions comprising an insecticidally effective amount of at least one compound of formula (I), and optionally, an effective amount of at least one of a second compound, with at least one insecticidally compatible carrier are also disclosed; along with methods of controlling insects comprising applying said compositions to a locus where insects are present or are expected to be present.

Abstract: An improved process is described for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans. This improved process is focused on steps to produce key intermediates, namely compounds of Formula (I): where R3, R4, R5, R6 and x are defined herein.

Abstract: An improved process is described for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans. This improved process is focused on steps to produce key intermediates, namely disubstitutedphenolylalkyl substituted dihydrobenzofurans of formula I: where R3, R4, R5, R6 and x are defined herein.

Abstract: A process is described for preparing 1-aryltriazolinones of formula I useful in the production of commercial herbicides: by (i) carbonylating an amidrazone of formula (A) with one or more carbonylating agent, or by (ii) condensing a hydrazonoyl derivative of formula (A) with one or more ring-forming agent, wherein formula (A) is where W, X, Y, Z, and R1 are fully described herein. Preferred are those where W is halogen or —NHR where R is hydrogen or haloalkyl; X and Y are independently selected from hydrogen, chloro, or fluoro; Z is hydrogen, bromo, iodo, nitro, amino, or methylsulfonylamino; and R1 is methyl. Certain compounds of formula (A) are novel compositions of matter. The process as described herein has utility in providing compounds of formula I in unexpectedly high yield and purity.

Abstract: A process is described for preparing 1-aryltriazolinones of formula I useful in the production of commercial herbicides: 1

Abstract: A process is described for preparing 1-aryltriazolinones of formula I useful in the production of commercial herbicides: by (i) carbonylating an amidrazone of formula (A) with one or more carbonylating agent, or by (ii) condensing a hydrazonoyl derivative of formula (A) with one or more ring-forming agent, wherein formula (A) is where W, X, Y, Z, and R1 are fully described herein. Preferred are those where W is halogen or —NHR where R is hydrogen or haloalkyl; X and Y are independently selected from hydrogen, chloro, or fluoro; Z is hydrogen, bromo, iodo, nitro, amino, or methylsulfonylamino; and R1 is methyl. Certain compounds of formula (A) are novel compositions of matter. The process as described herein has utility in providing compounds of formula I in unexpectedly high yield and purity.

Abstract: A process is described for preparing 1-aryltriazolinones of formula I useful in the production of commercial herbicides: 1

Abstract: A process is described for preparing 1-aryltriazolinones of formula I useful in the production of commercial herbicides: by (i) carbonylating an amidrazone of formula (A) with one or more carbonylating agent, or by (ii) condensing a hydrazonoyl derivative of formula (A) with one or more ring-forming agent, wherein formula (A) is where W, X, Y, Z, and R1 are fully described herein. Preferred are those where W is halogen or —NHR where R is hydrogen or haloalkyl; X and Y are independently selected from hydrogen, chloro, or fluoro; Z is hydrogen, bromo, iodo, nitro, amino, or methylsulfonylamino; and R1 is methyl. Certain compounds of formula (A) are novel compositions of matter. The process as described herein has utility in providing compounds of formula I in unexpectedly high yield and purity.

Abstract: A process for preparing an alkyl &agr;-2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl &agr;-acetyl-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2,4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.

Abstract: A process for preparing an alkyl &agr;-2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl &agr;-acetyl-5-[4-(difluoromethyl)4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2, 4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.

Abstract: A process for preparing an alkyl .alpha.-2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4 -triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl .alpha.-acetyl-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-t riazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2, 4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo- 1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.

Abstract: A process is disclosed in which the 4-position of the 1-(2-fluorophenyl) group attached to a 4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, an intermediate in the route to prepare the herbicide ethyl .alpha.-2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2 ,4-triazol-1-yl]-4-fluorobenzenepropanoate, is chlorinated in good yield. The process involves adding chlorine gas in three separate steps, with by-product hydrogen chloride being removed at the end of each chlorine addition step.

Abstract: Dioxetanes which couple with organic and biological molecules of the formula: ##STR1## wherein X is a leaving group which is removed by an `activating agent to produce light, wherein A is a coupling substituent, Ar is a substituent selected from the group consisting of phenyl and naphthyl to provide a label are described. R.sub.1 is an optional linker substituent and can have between 1 and 30 carbon atoms with some of the carbon atoms being oxygen, sulfur, nitrogen or phosphorus. Ar as phenyl is preferred. The dioxetane coupled molecules are useful in assays of all types where luminescence can be used as an indicator.

Abstract: Dioxetanes which couple with organic and biological molecules of the formula: ##STR1## wherein X is a leaving group which is removed by an activating agent other than an enzyme which is removed by an activating agent to produce light, wherein A is a coupling substituent, Ar is a substituent selected from the group consisting of phenyl and naphthyl to provide a label are described. R.sub.1 is an optional linker substituent and can have between 1 and 30 carbon atoms with some of the carbon atoms being oxygen, sulfur, nitrogen or phosphorus. Ar as phenyl is preferred. The dioxetane coupled molecules are useful in assays of all types where luminescence can be used as an indicator.

Abstract: An improved process for the difluoromethylation of a 1-(optionally substituted)phenyl-1H-1,2,4-triazol-5-one at the 4-position of the triazole ring with chlorodifluoromethane significantly reduces the cycle time required for the reaction. The improvement comprises reacting the triazolinone with potassium carbonate in a glyme solvent, heating one molar equivalent of a sodium or potassium salt of the triazolinone with 0.1 to 1 molar equivalent of potassium carbonate and 1.5 to 1.8 molar equivalents of chlorodifluoromethane in a glyme solvent, the concentration the triazolinone in the glyme being in the range of 5 to 15 percent weight/volume, at a temperature in the range of 165.degree. to 200.degree. C. for 5 to 30 minutes, with a 10 to 15 percent molar excess of chlorodifluoromethane, either at atmospheric pressure under an inert atmosphere or in a sealed autoclave, and recovering the difluoromethylated triazolinone.

Abstract: A method for preparing an alkoxyethylidene-substituted aryl hydrazine having the formula ##STR1## and thereafter cyclizing the same with a cyanate salt under mildly acidic conditions in the presence of an organic solvent, optionally in the presence of a cyclization-aiding amount of water, to form an aryl triazolinone of the formula ##STR2## wherein X is independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro, hydroxy, --NHSO.sub.2 R.sup.1, --NR.sup.1 SO.sub.2 R.sup.1, or --N(SO.sub.2 R.sup.1).sub.2, where R.sup.1 is lower alkyl; R is lower alkyl, and each R is the same; and n is an integer of from 1-3, which triazolinones am useful as intermediates for preparing herbicides.

Abstract: A method for preparing an alkoxyethylidene-substituted aryl hydrazine having the formula ##STR1## and thereafter cyclizing the same with a cyanate salt under mildly acidic conditions in the presence of an organic solvent, optionally in the presence of a cyclization-aiding amount of water, to form an aryl triazolinone of the formula ##STR2## wherein X is independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro, hydroxy, --NHSO.sub.2 R.sup.1, --NR.sup.1 SO.sub.2 R.sup.1, or --N(SO.sub.2 R.sup.1).sub.2, where R.sup.1 is lower alkyl; R is lower alkyl, and each R is the same; and n is an integer of from 1-3, which triazolinones are useful as intermediates for preparing herbicides.