Projuvenoids: Synthesis and Biological Evaluation of Sulfenylated, Sulfinylated, and Sulfonylated Carbamates

Archives of Insect Biochemistry and Physiology

Volumn 32, Issue 3-4, 1996, Pages 659-669

  Ujváry, István ^a   Matolcsy, György ^a   Bélai, Iván ^a   Szurdoki, Ferenc ^a,c   Bauer, Krisztina ^a   Varjas, László ^a   Kramer, Karl J ^b  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Fenoxycarb; Juvenile hormone analogs; Proinsecticides; Sulfenylcarbamates; Sulfinylcarbamates

Indexed keywords

ALEYRODIDAE; BEMISIA TABACI; IPOMOEA BATATAS; PIERIS BRASSICAE; SITOPHILUS ORYZAE; SOLANUM TUBEROSUM;

CARBAMIC ACID DERIVATIVE; FENOXYCARB; INSECTICIDE; JUVENILE HORMONE; PRODRUG; SULFUR;

ANIMAL; ARTICLE; BEETLE; BIOASSAY; BUTTERFLY; CHEMICAL STRUCTURE; CHEMISTRY; INSECT; MOLECULAR MIMICRY; SYNTHESIS;

ANIMALS; BEETLES; BIOLOGICAL ASSAY; BUTTERFLIES; CARBAMATES; INSECTICIDES; INSECTS; JUVENILE HORMONES; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PHENYLCARBAMATES; PRODRUGS; SULFUR;

EID: 0029715226     PISSN: 07394462     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-6327(1996)32:3/4<659::aid-arch37>3.0.co;2-9     Document Type: Article

References (28)

1. Brown MS (1972): N-Substituted arylcarbamoyl sulfides. U.S. Patent 3 679 733.
2. Brown MS, Kohn GK (1974): N-Chlorothio carbamates. U.S. Patent 3 843 689.
3. Chiu YC, Black AL, Fukuto TR (1975): Thiolysis as an activation process in N-sulfenylated derivatives of methylcarbamate esters. Pestic Biochem Physiol 5:359-366.
4. Collins C, Kennedy JM, Fahmy MAH, Miller TA (1980): Mode of action of sulfenylated carbamates: Rapid conversion of N,N′-thiodicarbamates to parent carbamate measured by neurophysiological bioassay. Pestic Biochem Physiol 13:158-163.
5. Dorn S, Frischknecht ML, Martinez V, Zurflüh R, Fischer U (1981): A novel non-neurotoxic insecticide with a broad activity spectrum. Z Pflanzenkr Pflanzenschutz 88:269-275.
6. Drabek J, Neumann R (1985): Proinsecticides. In Hutson DH, Roberts TR (eds): Progress in Pesticide Biochemistry and Toxicology, vol. 5. New York: John Wiley & Sons, pp 35-86.
7. Fahmy MA, Fukuto TR (1983): Rationale and chemistry of proinsecticidal methylcarbamates. In Miyamoto J, Kearney PC (eds): Pesticide Chemistry: Human Welfare and the Environment, vol. 1. Oxford: Pergamon Press, pp 193-200.
8. Fahmy MAH, Chiu YC, Fukuto TR (1974): Selective toxicity of N-substituted biscarbamoyl sulfides. J Agric Food Chem 22:59-62.
9. Fahmy MAH, Mallipudi NM, Fukuto TR (1978): Selective toxicity of N,N′-thiodicarbamates. J Agric Food Chem 26:550-557.
10. Fischer U, Schneider F, Zurflüh R (1978): Pesticidal carbamic acid esters. Eur Pat Appl 4,334.
11. Fukuto TR (1983): Structure-activity relationships in derivatives of anticholinesterase insecticides. In Miyamoto J, Kearney PC (eds): Pesticide Chemistry: Human Welfare and the Environment, vol. 1. Oxford: Pergamon Press, pp 203-212.
12. Henrick CA (1982): Juvenile hormone analogs: Structure-activity relationships. In Coats JR (ed): Insecticide Mode of Action. New York: Academic Press, pp 315-402.
13. Henrick CA (1991): Juvenoids and anti-juvenile hormone agents: Past and present. In Hrdý I (ed): Insect Chemical Ecology. The Hague: SPB Academic Publishing, pp 429-452.
14. Kinoshita Y, Fukuto TR (1980): Insecticidal properties of N-sulfonyl derivatives of propoxur and carbofuran. J Agric Food Chem 28:1325-1327.
15. Kramer KJ, Beeman RW, Hendricks LH (1981): Activity of Ro13-5223 and Ro13-7744 against stored-product insects. J Econ Entomol 74:678-680.
16. McDermott SD, Spillane WJ (1984): Synthesis and reactions of sulfamides. A review. Org Prep Proc Int 16:49-77.
17. Nakayama A, Iwamura H, Fujita T (1984): Quantitative structure-activity relationship of insect juvenile hormone mimetic compounds. J Med Chem 27:1493-1502.
18. Okot-Kotber BM, Ujváry I, Mollaaghababa R, Szurdoki F, Matolcsy G, Presrwich GD (1991): Physiological influence of fenoxycarb pro-insecticides and soldier head extracts of various termite species on soldier differentiation in Reticulitermes flavipes (Isoptera). Sociobiology 19:77-90.
19. Prestwich GD (1990): Proinsecticides: Metabolically activated toxicants. In Hodgson E, Kuhr RJ (eds): Safer Insecticides: Development and Use. New York: Marcel Dekker Inc. pp 281-335.
20. Satoh GT, Plapp FW Jr (1993): Use of juvenoid insect growth regulators for management of cotton aphid and sweet potato whitefly populations. In Proceedings of the Beltwide Cotton Conference, vol. 2. Memphis, TN: National Cotton Council, pp. 751-757.
21. Sláma K (1981): Juvenoids in retrospect and juvenogens in prospect. In Sehnal F, Zabza A, Menn JJ, Cymborowski B (eds): Regulation of Insect Development and Behavior. Wroclaw: Wroclaw Technical University Press, pp 853-868.
22. Sláma K, Romanuk M (1976): Juvenogens, biochemically activated juvenoid complexes. Insect Biochem 6:579-586.
23. Tomlin C (ed) (1994): The Pesticide Manual. 10th Ed. Farnham: The British Crop Protection Council.
24. Ujváry I, Matolcsy G, Varjas L (1992): Novel sulphur-containing compounds with juvenile hormone activity. In Otto D, Weber B (eds): Insecticides: Mechanism of Action and Resistance. Andover: Intercept, pp 147-154.
25. Umetsu N, (1992): Design of proinsecticides. In Draber W, Fujita T (eds): Rational Approach to Structure, Activity, and Ecotoxicology of Agrochemicals. Boca Raton, FL: CRC Press, pp 251-274.
26. Varjas L (1985): Changes of juvenoid-sensitivity in larvae of the large white butterfly, Pieris brassicae L., reared at four different photoperiods. Acta Phytopathol Acad Sci Hung 20:327-335.
27. Wallace GC, Zebra EN (1989): In-vitro evidence for activative thiolysis and self-synergism of sulfenyl dicarbamate derivatives of 3,4-methylenedioxyphenyl N-methylcarbamate. Pestic Sci 27:233-241.
28. Wimmer Z, Romanuk M, Sláma K (1988): Synthesis and application of juvenile hormone analogues. In Sehnal F, Zabza A, Delinger DL (eds): Endocrinological Frontiers in Physiological Insect Ecology. Wroclaw: Wroclaw Technical University Press, pp 733-736.