Insect Juvenile Hormone Activity of Alkyl (2E,4E)-3,7,11-Trimethyl-2,4-dodecadienoates. Variations in the Ester Function and in the Carbon Chain

Journal of Agricultural and Food Chemistry

Volumn 24, Issue 2, 1976, Pages 207-218

  Henrick, Clive A ^a   Willy, W Edward ^a   Staal, Gerardus B ^a  

^a Zoecon Research and Development   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

JUVENILE HORMONE; UNSATURATED FATTY ACID;

AEDES; ANIMAL; APHID; ARTICLE; BIOASSAY; DRUG EFFECT; HOUSE FLY; INSECT; LARVA; LEPIDOPTERA; METAMORPHOSIS; MOTH; SPECIES DIFFERENCE; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; TENEBRIO;

AEDES; ANIMAL; APHIDS; BIOLOGICAL ASSAY; FATTY ACIDS, UNSATURATED; HOUSEFLIES; INSECTS; JUVENILE HORMONES; LARVA; LEPIDOPTERA; METAMORPHOSIS, BIOLOGICAL; MOTHS; PUPA; SPECIES SPECIFICITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TENEBRIO;

EID: 0016930430     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf60204a018     Document Type: Article

References (139)

1. Amos, T. G., Williams, P., Du Guesclin, P. B., Schwarz, M., J. Econ. Entomol. 67, 474 (1974)
2. Anderson, R. J., Corbin, V. L., Cotterell, G., Cox, G. R., Henrick, C. A., Schaub, F., Siddall, J. B., J. Am. Chem. Soc. 97, 1197 (1975).
3. Anderson, R. J., Henrick, C. A., Siddall, J. B., Zurflüh, R., J. Am. Chem. Soc. 94, 5379 (1972).
4. Bell, E. W., Gast, L. E., Cowan, J. C., Friedrich, J. P., Bowers, W. S., J. Agric. Food Chem. 21, 925 (1973)
5. Benskin, J., Perron, J. M., Can. Entomol. 105, 619 (1973).
6. Bowers, W. S., Science 164, 323 (1969).
7. Bowers, W. S., U.S. Patent 3563982 (Feb 16, 1971a).
8. Bowers, W. S., Mitt. Schweiz. Entomol. Ges. 44, 115 (1971b).
9. Brown, H. C., Geoghegan, Jr., P., J. Am. Chem. Soc. 89, 1522 (1967).
10. Brown, H. C., Rei, M-H., J. Am. Chem. Soc. 91, 5646 (1969).
11. Burden, R. S., Crombie, L, J. Chem. Soc. C, 2477 (1969)
12. Chang, H.-L.W., Tetrahedron Lett., 1989 (1972).
13. Chodnekar, M. S., Pfiffner, A., Rigassi, N., Schwieter, U., Suchy, M., U.S. Patent 3879429 (April 22, 1975).
14. Corey, E. J., Gilman, N. W., Ganem, B. E., J. Am. Chem. Soc. 90, 5616 (1968)
15. Corey, E. J., Katzenellenbogen, J. A., Roman, S. A., Gilman, N. W., Tetrahedron Lett., 1821 (1971).
16. Cruickshank, P. A., U.S. Patent 3453362 (July 1, 1969).
17. Cruickshank, P. A., Mitt. Schweiz. Entomol. Ges. 44, 97 (1971).
18. Cruickshank, P. A., Palmere, R. M., Nature (London) 233, 488 (1971).
19. Gumming, J. E., McKague, B., Can. Entomol. 105, 509 (1973).
20. Daoud, D. S., Sehnal, F., Bull. Entomol. Res. 64, 643 (1974)
21. Dart, M. C., Henbest, H. B., J. Chem. Soc., 3563 (1960)
22. Fetizon, M., Jurion, M., J. Chem. Soc., Chem. Commun., 382 (1972)
23. Franke, A., Traber, W., U.S. Patent 3824274 (July 16, 1974)
24. Gelbic, I., Sehnal, F., Bull. Entomol. Res. 63, 7 (1973).
25. Hamlen, R. A., J. Econ. Entomol. 68, 223 (1975)
26. Harris, R. L., Chamberlain, W. F., Frazar, E. D., J. Econ. Entomol. 67, 384 (1974).
27. Hartzell, S. L., Sullivan, D. F., Rathke, M. W., Tetrahedron Lett., 1403 (1974)
28. Henrick, C. A., Belgian Patent 778241 (Jan 19,1972)
29. Henrick, C. A., U.S. Patent 3752843 (Aug 14, 1973).
30. Henrick, C. A., U.S. Patent 3793353 (Feb 19, 1974a).
31. Henrick, C. A., U.S. Patent 3816484 (June 11, 1974b)
32. Henrick, C. A., U.S. Patent 3824290 (July 16, 1974c)
33. Henrick, C. A., U.S. Patent 3833635 (Sept 3, 1974d).
34. Henrick, C. A., U.S. Patent 3845089 (Oct 29, 1974e).
35. Henrick, C. A., Anderson, R. J., Cox, G. R., Staal, G. B., Ludvik, G. F., Zoecon Corporation, Palo Alto, Calif., unpublished results, 1976
36. Henrick, C. A., Schaub, F., Siddall, J. B., J. Am. Chem. Soc. 94, 5374 (1972)
37. Henrick, C. A., Siddall, J. B., Belgian Patent 778242 (Jan 19, 1972).
38. Henrick, C. A., Siddall, J. B., U.S. Patent 3712922 (Jan 23, 1973a)
39. Henrick, C. A., Siddall, J. B., U.S. Patent 3737450 (June 5, 1973b).
40. Henrick, C. A., Siddall, J. B., U.S. Patent 3755411 (Aug 28, 1973c).
41. Henrick, C. A., Siddall, J. B., U.S. Patent 3803185 (April 9, 1974a).
42. Henrick, C. A., Siddall, J. B., U.S. Patent 3826804 (July 30, 1974b)
43. Henrick, C. A., Siddall, J. B., U.S. Patent 3882154 (May 6, 1975a).
44. Henrick, C. A., Siddall, J. B., U.S. Patent 3882156 (May 6, 1975b).
45. Henrick, C. A., Siddall, J. B., U.S. Patent 3904662 (Sept 9, 1975c)
46. Henrick, C. A., Siddall, J. B., U.S. Patent 3912815 (Oct 14, 1975c)
47. Henrick, C. A., Siddall, J. B., Staal, G. B., Zoecon Corporation, Palo Alto, Calif., unpublished results, 1970.
48. Henrick, C. A., Staal, G. B., Siddall, J. B., J. Agric. Food Chem. 21, 354 (1973)
49. Henrick, C. A., Willy, W. E., Baum, J. W., Baer, T. A., Garcia, B. A., Mastre, T. A., Chang, S. M., J. Org. Chem. 40, 1 (1975a).
50. Henrick, C. A., Willy, W. E., Garcia, B. A., Staal, G. B., J. Agric. Food Chem. 23, 396 (1975b).
51. Henrick, C. A., Willy, W. E., McKean, D. R., Baggiolini, E., Siddall, J. B., J. Org. Chem. 40, 8 (1975c).
52. Isler, O., Ruegg, R., Chopard-dit-Jean, L., Wagner, H., Bernhard, K., Helo. Chim. Acta 39, 897 (1956).
53. Jakob, W. L., Mosq. News 32, 592 (1972)
54. Jakob, W. L., J. Econ. Entomol. 66, 819 (1973)
55. Jarolim, V., Hejno, K., Sehnal, F., Sorm, F., Life Sci. 8, 831 (1969)
56. Johnson, W. S., Werthemann, L., Bartlett, W. R., Brocksom, T. J., Li, T., Faulkner, D. J., Peterson, M. R., J. Am. Chem. Soc. 92, 741 (1970).
57. Jorgenson, M. J., Org. React. 18, 1 (1970)
58. Kennedy, J. P., J. Org. Chem. 35, 532 (1970)
59. Kennedy, J. P., Desai, N. V., Sivaram, S., J. Am. Chem. Soc. 95, 6386 (1973).
60. Kiguchi, K., Ohtaki, T., Akai, H., Mori, K., Appl. Entomol. Zool. 9, 29 (1974).
61. Krimen, L. I., Org. Syn. 50, 1 (1970).
62. Kuhr, R. J., Cleere, J. S., J. Econ. Entomol. 66, 1019 (1973)
63. Landor, S. R., Punja, N., J. Chem. Soc. C, 2495 (1967)
64. Lotzbeyer, J., Bodendorf, K., Chem. Ber. 100, 2620 (1967)
65. Menn, J. J., Beroza, M., Ed., “Insect Juvenile Hormones”, Academic Press, New York, N.Y., 1972.
66. Menn, J. J., Palios, F. M., Environ. Lett. 8, 71 (1975).
67. Metwally, M. M., Sehnal, F., Biol. Bull. 144, 368 (1973).
68. Miller, R. W., Uebel, E. C., J. Econ. Entomol. 67, 69 (1974).
69. Mitsui, T., Nobusawa, C., Fukami, J., Mori, K., Fukunaga, K., Appl. Entomol. Zool. 8, 27 (1973)
70. Morgan, P. B., LaBrecque, G. C., Weidhaas, D. E., Benton, A., Can. Entomol. 107, 413 (1975).
71. Mori, K., Mitt. Schweiz. Entomol. Ges. 44, 17 (1971).
72. Mori, K., Agric. Biol. Chem. 36, 442 (1972).
73. Mori, K., Takigawa, T., Manabe, Y., Tominaga, M., Matsui, M., Kiguchi, K., Akai, H., Ohtaki, T., Agr. Biol. Chem. 39, 259 (1975).
74. Mori, K., Tominaga, M., Watanabe, Y., Matsui, M., Agric. Biol. Chem. 38, 1541 (1974)
75. Mulla, M. S., Norland, R. L., Ikeshoji, T., Kramer, W. L., J. Econ. Entomol. 67, 165 (1974)
76. Nassar, S. G., Staal, G. B., Armanious, N. I., J. Econ. Entomol. 66, 847 (1973)
77. Nemec, V., Jarolim, V., Hejno, K, Sorm, F., Life Sci. 9, 821 (1970).
78. Newman, M. S., Beal, P. F., J. Am. Chem. Soc. 72, 5163 (1950).
79. Nihmura, M., Aomori, S., Ozawa, Y., Mori, K., Matsui, M., Appl. Entomol. Zool. 9, 34 (1974).
80. Nilles, G. P., Zabik, M. J., Connin, R. V., Schuetz, R. D., J. Agric. Food Chem. 21, 342 (1973)
81. O'Donnell, G. W., Sutherland, M. D., Aust. J. Chem. 19, 525 (1966).
82. Ohtaki, T., Kiguchi, K., Akai, H., Mori, K., Appl. Entomol. Zool. 7, 161 (1972).
83. Overberger, C. G., Kaye, H., J. Am. Chem. Soc. 89, 5640 (1967).
84. Ozawa, Y., Mori, K., Matsui, M., Agric. Biol. Chem. 37, 2373 (1973)
85. Palios, F. M., Menn, J. J., Letchworth, P. E., Miaullis, J. B., Nature (London) 232, 486 (1971).
86. Parikh, J. R., Doering, W., von, E., J. Am. Chem. Soc. 89, 5505 (1967).
87. Pattenden, G., Weedon, B. C. L., J. Chem. Soc. C, 1997 (1968).
88. Plapp, F. W., Jr., Vinson, S. R., Pestic. Biochem. Physiol. 3, 131 (1973)
89. Pommer, H., Arend, W., U.S. Patent 2831884 (April 22, 1958)
90. Free, D. J., Can. Entomol. 106, 1019 (1974)
91. Quistad, G. B., Staiger, L. E., Schooley, D. A., J. Agric. Food Chem. 22, 582 (1974)
92. Quistad, G. B., Staiger, L. E., Schooley, D. A., J. Agric. Food Chem. 23, 299 (1975).
93. Rad wan, W., Sehnal, F., Experienta 30, 615 (1974).
94. Ramirez, H., Dershowitz, S., J. Org. Chem. 22, 41 (1957).
95. Roberts, J. D., Chambers, V. C., J. Am. Chem. Soc. 73, 3176 (1951)
96. Romanuk, M., Slama, K., Sorm, F., U.S. Patent 3634470 (Jan 11, 1972a)
97. Romanuk, M., Sorm, F., Slama, K., U.S. Patent 3707491 (Dec 26, 1972b).
98. Ruzicka, Z., Sehnal, F., Cairo, V. G., Z. Angew. Entomol. 76, 430 (1974).
99. Sarmiento, R., McGovern, T. P., Beroza, M., Mills, G. D., Jr., Redfern, R. E., Science 179, 1342 (1973).
100. Sato, K., Mizuno, S., Hirayama, M., J. Org. Chem. 32, 177 (1967).
101. Schaefer, C. H., Wilder, W. H., J. Econ. Entomol. 65, 1066 (1972).
102. Schaefer, C. H., Wilder, W. H., J. Econ. Entomol. 66, 913 (1973).
103. Scheurer, R., Ruzette, M. A., Z. Angew. Entomol. 77, 218 (1974).
104. Schooley, D. A., Bergot, B. J., Dunham, L. L., Siddall, J. B., J. Agric. Food Chem. 23, 293 (1975a)
105. Schooley, D. A., Creswell, K. M., Staiger, L. E., Quistad, G. B., J. Agric. Food Chem. 23, 369 (1975b).
106. Schwarz, M., Braun, B. H., Law, M. W., Sonnet, P. E., Wakabayashi, N., Waters, R. M., Jacobson, M., Ann. Entomol. Soc. Am. 62, 668 (1969).
107. Schwarz, M., Miller, R. W., Wright, J. E., Chamberlain, W. F., Hopkins, D. E., J. Econ. Entomol. 67, 598 (1974a).
108. Schwarz, M., Sonnet, P. E., Wakabayashi, N., Science 167, 191 (1970).
109. Schwarz, M., Sonnet, P. E., Wakabayashi, N., U.S. Patent 3852310 (Dec 3, 1974b)
110. Schwieter, U., Planta, C. V., Ruegg, R., Isler, O., Helo. Chim. Acta 45, 541 (1962).
111. Seebach, D., Corey, E. J., J. Org. Chem. 40, 231 (1975).
112. Siddall, J. B., German Offenlegungsschift 2162532 (July 13, 1972a)
113. Siddall, J. B., U.S. Patent 3651104 (Mar 21, 1972b).
114. Siddall, J. B., U.S. Patent 3709914 (Jan 9, 1973).
115. Siddall, J. B., Caíame, J. P., U.S. Patent 3712880 (Jan 23, 1973).
116. Siddall, J. B., Caíame, J. P., U.S. Patent 3819667 (June 25, 1974)
117. Sisido, K., Kondo, K., Nozaki, H., Tuda, M., Udo, Y., J. Am. Chem. Soc. 82, 2286 (1960).
118. Skorianetz, W., Giger, H., Ohloff, G., Helo. Chim. Acta 54, 1797 (1971).
119. Slama, K., Hejno, K., Jarolim, V., Sorm, F., Biol. Bull. 139, 222 (1970).
120. Slama, K., Romanuk, M., Sorm, F., J. Insect Physiol. 18, 19 (1972).
121. Slama, K., Romanuk, M., Sorm, F., “Insect Hormones and Bioanalogues”, Springer-Verlag New York, New York, N.Y., 1974, p 137.
122. Sorm, F., Mitt. Schweiz. Entomol. Ges. 44, 7 (1971).
123. Staal, G. B., Annu. Rev. Entomol. 20, 417 (1975)
124. Staal, G. B., Nassar, S., Martin, J. W., J. Econ. Entomol. 66, 851 (1973)
125. Stevens, W., Van Es, A., Reel. Trav. Chim. Pays-Bas 83, 1287 (1964).
126. Strong, R. G., Diekman, J., J. Econ. Entomol. 66, 1167 (1973).
127. Taguchi, H., Shimoji, K., Yamamoto, H., Nozaki, H., Bull. Chem. Soc. Jpn. 47, 2529 (1974).
128. Takigawa, T., Mori, K., Matsui, M., Agric. Biol. Chem. 39, 249 (1975).
129. Tar bell, D. S., Mallatt, R. C., Wilson, J. W., J. Am. Chem. Soc. 64, 2229 (1942).
130. van der Tempel, P. J., Huisman, H. O., Tetrahedron 22, 293 (1966).
131. Wakabayashi, N., J. Med. Chem. 12, 191 (1969).
132. Wakabayashi, N., Sonnet, P. E., Law, M. W., J. Med. Chem. 12, 911 (1969)
133. Walker, W. F., Bowers, W. S., J. Agric. Food Chem. 21, 145 (1973)
134. Watson, S. C., Eastham, J. F., J. Organometal. Chem. 9, 165 (1967).
135. Wigglesworth, V. B., Nature (London) 221, 190 (1969a).
136. Wigglesworth, V. B., J. Insect Physiol. 15, 73 (1969b).
137. Wotiz, J. H., Buco, S. N., J. Org. Chem. 20, 210 (1955)
138. Wright, J. E., Bowman, M. C., J. Econ. Entomol. 66, 707 (1973).
139. Wright, J. E., Spates, G. E., J. Agric. Food Chem. 19, 289 (1971)