Metabolites of the prototype insecticide (2E,4E)-N-isobutyl-6-phenylhexa-2,4-dienamide. 1. Synthesis, chromatography, spectroscopy, and biological activity

Horsham, Mark A.; Class, Thomas J.; Johnston, John J.; Casida, John E.

doi:10.1021/jf00087a046

Cited by 6 publications

(17 citation statements)

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“…Several analytical methods were used for com-Knowledge of molecular sites sensitive to metabolism parison of the authentic standards (Horsham et al, 1989) Casida, 1966) insecticides. Several analytical methods were used for com-Knowledge of molecular sites sensitive to metabolism parison of the authentic standards (Horsham et al, 1989) Casida, 1966) insecticides.…”

Section: More Than 20 Insecticidal Isobutylamides [N-(2-mentioning

confidence: 99%

“…Several analytical methods were used for com-Knowledge of molecular sites sensitive to metabolism parison of the authentic standards (Horsham et al, 1989) Casida, 1966) insecticides. The parent isobutylamide and compounds syn-was used as the carrier gas at 40 cm/s (Horsham et al, 1989). Protograde) to methanol Over a period of 50 min followed by type insecticide 3 (referred to in this paper as the parent 100% methanol for an additional 30 min with a constant flow rate isobutylamide) was selected for study for three reasons: of 0.8 mL/min a t 25 "C (Horsham et al, 1989).…”

Section: More Than 20 Insecticidal Isobutylamides [N-(2-mentioning

confidence: 99%

“…R, and MS characteristics are reported by Horsham et al (1989). GC-mass spectrometry (GC-MS) involved the Hewlett-Packard 5985B GC-MS system with a fused silica capillary column (SPB5, 0.25-pm film thickness, 0.32 mm X 15 m; Supelco) with a sequential temperature program of 90 "C for 3 min, 25 "C/min to 160 "C, 160 "C for 1 min, and 2 "C/min to 240 "C and helium as the carrier gas (30 cm/s) for separation.…”

Section: More Than 20 Insecticidal Isobutylamides [N-(2-mentioning

confidence: 99%

“…Each of the metabolite standards is of lower toxicity than the parent isobutylamide to mice and to PB-pretreated houseflies (Horsham et al, 1989). The principal products are the amide and the carboxylic acid whereas some 6-hydroxy and p-hydroxy isobutylamides are also detected.…”

mentioning

confidence: 95%

“…The hydroxamic acid should be present in largest amount from the unsubstituted amide substrate in the mouse microsomal oxygenase system containing PSCP as an amidase inhibitor to minimize its subsequent hydrolysis to the carboxylic acid. On the other hand, the hydroxamic acid is readily analyzed by GC-MS (CI) as its major dimethyl derivative (R, 11.3 min; Horsham et al, 1989). The standard HPLC system used for other metabolites gave very low sensitivity and a broad early peak with the standard hydroxamic acid [perhaps due to its strong chelating properties; see Corbett and Chipko (1979)j.…”

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Metabolites of the prototype insecticide (2E,4E)-N-isobutyl-6-phenylhexa-2,4-dienamide. 2. Formation in mouse and rat liver microsomal systems, rat hepatocytes, and houseflies

Johnston¹,

Horsham²,

Class³

et al. 1989

J. Agric. Food Chem.

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Elliott, M.; Farnham, A. W.; Janes, N. F.; Johnson, D. M.; Pulman, D. A. Synthesis and Insecticidal Activity of Lipophilic Amides. Part 2 Effect of Heteroatom Replacements and of Introducing Methyl Groups in the Pentadiene System. Pestic. Sci. 198713, Jacobson, M. The Unsaturated Isobutylamides. In Naturally Occurring Insecticides; Jacobson, M., Crosby, D. G., Eds.; Dekker: New York, 1971; pp 137-176. Johnston, J. J.; Horsham, M. A.; Class, T. J.; Casida, J. E. Metabolites of the Prototype Insecticide (2E,4E)-N-Isobutyl-6phenylhexa-2,4-dienamide9 2. Formation in Mouse and Rat Liver Microsomal Systems, Rat Hepatocytes, and Houseflies. J . Agric. Food Chem. 1989, following paper in this issue. Jones, E. R. H.; Skattebol, L.; Whiting, M. C. Researches on Acetylenic Compounds. Part LIV. The Preparation and Synthetical Applications of Ethynylmagnesium Bromide. J. Chem. SOC. 1956,4765-4768. King, F. D.; Pike, S.; Walton, D. R. M. Silylhydroxylamines as Reagents for High-yield RCOCl -RNCO Conversions. J. Chem. Soc., Chem. Commun. 1978,351-352. Levin, J. I.; Turos, E.; Weinreb, S. M. An Alternative Procedure for the Aluminum-Mediated Conversion of Esters to Amides. Synth. Commun. 1982, 12, 989-993. McOmie, J. F. W.; Watts, M. L.; West, D. E. Demethylation of Aryl Methyl Ethers by Boron Tribromide. Tetrahedron 1968, Mestres, R.; Palomo, C. A New Reagent for Activating Carboxy Groups; Preparation and Reactions of Phenyl N-Phenylphosphoramidochloridate. Synthesis 1982, 288-291. Miyakado, M.; Nakayama, I.; Yoshioka, H.; Nakatani, N. The Piperaceae Amides I Structure of Pipercide, a New Insecticidal

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“…Several analytical methods were used for com-Knowledge of molecular sites sensitive to metabolism parison of the authentic standards (Horsham et al, 1989) Casida, 1966) insecticides. Several analytical methods were used for com-Knowledge of molecular sites sensitive to metabolism parison of the authentic standards (Horsham et al, 1989) Casida, 1966) insecticides.…”

Section: More Than 20 Insecticidal Isobutylamides [N-(2-mentioning

confidence: 99%

“…Several analytical methods were used for com-Knowledge of molecular sites sensitive to metabolism parison of the authentic standards (Horsham et al, 1989) Casida, 1966) insecticides. The parent isobutylamide and compounds syn-was used as the carrier gas at 40 cm/s (Horsham et al, 1989). Protograde) to methanol Over a period of 50 min followed by type insecticide 3 (referred to in this paper as the parent 100% methanol for an additional 30 min with a constant flow rate isobutylamide) was selected for study for three reasons: of 0.8 mL/min a t 25 "C (Horsham et al, 1989).…”

Section: More Than 20 Insecticidal Isobutylamides [N-(2-mentioning

confidence: 99%

Section: More Than 20 Insecticidal Isobutylamides [N-(2-mentioning

confidence: 99%

mentioning

confidence: 95%

mentioning

confidence: 99%

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Metabolites of the prototype insecticide (2E,4E)-N-isobutyl-6-phenylhexa-2,4-dienamide. 2. Formation in mouse and rat liver microsomal systems, rat hepatocytes, and houseflies

Johnston¹,

Horsham²,

Class³

et al. 1989

J. Agric. Food Chem.

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Hydrozirconation of Alkynes

Milligan,

Hammill,

Crocker

et al. 2023

Organic Reactions

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Since the first preparation of organozirconocenes from alkenes and alkynes in 1972, hydrozirconation has become one of the most commonly used stoichiometric methods to convert readily available starting materials into reactive but stable organometallic intermediates. A broad range of subsequent transformations may be employed to convert organozirconocenes in situ into high‐value functionalized products, often with the strategic formation of one (or several) new carbon–carbon bonds. This chapter focuses on the hydrozirconation of terminal and internal alkynes, and the subsequent synthetic transformations of the resulting alkenylzirconocenes. Zirconocene hydrochloride, Cp 2 Zr(H)Cl, is most frequently employed for the hydrozirconation step and can be used as a reagent or prepared in situ. Subsequent reactions of alkenylzirconocenes include additions to inorganic electrophiles such as halogens, as well as in situ ligand transfers to other metals, such as palladium and zinc, that further expand the range of accessible bond formations. The initial discussion focuses on the mechanism and stereochemical considerations, and on the steric and electronic factors that determine the regiochemistry of the either kinetically or thermodynamically controlled hydrozirconation. The “Scope and Limitations” section presents information on functional group compatibilities and is organized by the type of synthetic transformation of alkenylzirconocenes. Representative applications of the hydrozirconation of alkynes are showcased in syntheses of natural products, comparisons to alternative methods for the hydrometallation of alkynes. The goal of this chapter is to demonstrate the significance of hydrozirconation in organic synthesis, including the utility of the stoichiometric zirconium organometallics obtained from alkyne substrates, and to provide inspiration for the future development of new synthetic methods and strategies.

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Regio- and stereoselective synthesis of Z-vinylic tellurides from propargylic alcohols: a route to chiral Z-enynes

et al. 2005

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Metabolites of the prototype insecticide (2E,4E)-N-isobutyl-6-phenylhexa-2,4-dienamide. 1. Synthesis, chromatography, spectroscopy, and biological activity

Cited by 6 publications

References 19 publications

Metabolites of the prototype insecticide (2E,4E)-N-isobutyl-6-phenylhexa-2,4-dienamide. 2. Formation in mouse and rat liver microsomal systems, rat hepatocytes, and houseflies

Metabolites of the prototype insecticide (2E,4E)-N-isobutyl-6-phenylhexa-2,4-dienamide. 2. Formation in mouse and rat liver microsomal systems, rat hepatocytes, and houseflies

Hydrozirconation of Alkynes

Regio- and stereoselective synthesis of Z-vinylic tellurides from propargylic alcohols: a route to chiral Z-enynes

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