Methylene group modifications of the N-(isothiazol-5- yl)phenylacetamides. Synthesis and insecticidal activity

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 8, 1999, Pages 3381-3388

  Samaritoni, Jack G ^a   Babcock, Jon M ^a   Schlenz, Michelle L ^a   Johnson, George W ^a  

^a Discovery Research   (United States)

Author keywords

E nolether; Insect control; Isothiazolylatropamide; Isothiazolylglyoxylamide; Isothiazolylphenylacetamide; Oxime; Synthesis

Indexed keywords

ACETAMIDE DERIVATIVE; ENAMINE; ETHER DERIVATIVE; FUNCTIONAL GROUP; INSECTICIDE; ISOTHIAZOLE DERIVATIVE; N,N DIMETHYLFORMAMIDE; OXIME DERIVATIVE; THIAZOLE DERIVATIVE;

AGRICULTURE; ANIMAL; APHID; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONTROLLED STUDY; INSECT; INSECT CONTROL; LEPIDOPTERA; MASS SPECTROMETRY; MOTH; NEMATODE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETAMIDES; ANIMALS; APHIDS; INSECTICIDES; INSECTS; MOLECULAR STRUCTURE; MOTHS; SPODOPTERA; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

ANIMALIA; APHIDIDAE; INSECTA; LEPIDOPTERA; MELOIDOGYNE JAVANICA; OXY; TRIFLUORO;

EID: 0032868476     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990095s     Document Type: Article

References (13)

1. Abraham, R. J.; Loftus, P. Proton and Carbon-13 NMR Spectroscopy; Heyden: London, 1978; pp 23-24.
2. Dahmani, Z.; Rahmouni, M.; Brugidou, R.; Bazureau, J. P.; Hamelin, J. A New Route to α-Hetero β-Enamino Esters using a Mild and Convenient Solvent-Free Process Assisted by Focused Microwave Irradiation. Tetrahedron Lett. 1998, 39, 8453-8456.
3. Gatta, F.; Misiti, D. Sodium Periodate Oxidation of Tetrahydro-β-carboline Derivatives. J. Heterocycl. Chem. 1989, 26, 537-539.
4. Hackler, R. E.; Johnson, G. W.; Samaritoni, J. G. N-(5-Isothiazolyl)amide Pesticides. WO 95/31448, 1995.
5. Harris, C. E.; Chrisman, W.; Bickford, S. A.; Lee, L. Y.; Torreblanca, A. E.; Singaram, B. Enamine Oxidations. 2. Selective Oxidative Cleavage of β,β-Disubstituted Enamines Using Alumina Supported Permanganate. Synthesis of One-Carbon Dehomologated Carbonyl Compounds from Enamines. Tetrahedron Lett. 1997, 38, 981-984.
6. Okada, I.; Okui, S.; Takahashi, Y.; Fukuchi, T. Synthesis and Acaricidal Activity of Pyrazole-5-carboxamide Derivatives. J. Pestic. Sci. 1991, 16, 623-629.
7. Rao, A. V. R.; Chakraborty, T. K.; Reddy, K. L. Studies Directed Towards the Synthesis of Immunosuppressive Agent FK-506: Construction of the Tricarbonyl Moiety. Tetrahedron Lett. 1990, 31, 1439-1442.
8. Ruminsky, P. G. Preparation of Fluorobutenamine Derivatives as Pesticides. WO 92/15555, 1992.
9. Samaritoni, J. G.; Arndt, I.; Bruce, T.; Dripps, J. E.; Gifford, J.; Hatton, C. J.; Hendrix, W. H.; Schoonover, J. R.; Johnson, G. W.; Hegde, V. B.; Thornburgn, S. N-Alkyl-N-(5-Isothiazolyl)- and N-(Alkyl-Isothiazolin-5-ylidene)phenylacetamides. Synthesis and Biological Activity. J. Agric. Food Chem. 1997, 45, 1920-1930.
10. Takagi, K.; Aotsuka, T.; Morita, H. Synthesis of Pyrimidino-[4,5-b][1,5]benzodiazepin-2-ones and Pyrimidino[1,6-α]-benzimidazol-1-ones from 4-Ethoxycarbonylamino-1H-1,5-benzodiazepine-3-carbonitrile via 4-(2-Aminoanilino)pyrimidin-2(1H)-one-5-carbonitriles. J. Heterocycl. Chem. 1986, 23, 1443-1449.
11. Vetelino, M. G.; Coe, J. W. A Mild Method for the Conversion of Activated Aryl Methyl Groups to Carboxaldehydes Via the Uncatalyzed Periodate Cleavage of Enamines. Tetrahedron Lett. 1994, 35, 219-222.
12. Wasserman, H. H.; Han, W. T. Vicinal Tricarbonyl Products from Singlet Oxygen Reactions. Application to the Synthesis of Carbacephams. Tetrahedron Lett. 1984, 25, 3743-3746.
13. Wasserman, H. H.; Ives, J. L. Reaction of Singlet Oxygen with Enamino Carbonyl Systems. A General Method for the Synthesis of α-Keto Derivatives of Lactones, Esters, Amides, Lactams, and Ketones. J. Org. Chem. 1985, 50, 3573-3580.