Development of (4-alkoxyphenoxy)- and (4-alkylphenoxy)alkanaldoxime O-ethers as potent insect juvenile hormone mimics and their structure-activity relationships

Quantitative structure‐activity analysis of larvicidal 1‐(substituted benzoyl)‐2‐benzoyl‐1‐tert‐butylhydrazines against Chilo suppressalis

“…As a preliminary, we examined the effect of the synergist, PB, for dibenzoylhydrazines. The activities for the 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 6.99 (fO.11) ( n = 2) 690 ($0.23) ( n = 4) 680 (f0.02) (n = 2) 5.82 (f0.16) ( n = 2) 6.03 ( n = 1) <5.00 (0%) ( n = 1) 614 ($0.06) (n = 2) <4.00 (0%) (n = 1) <4.00 (0%) (n = 1) <5.00 (45%) (n = 1) 631 (f0.12) (n = 2) 6.45 (fO06) ( n = 3) 6.49 ( f 0 1 5 ) ( n = 2) 6.5 8 (n = 1) 6.02 ( f 0 0 2 ) ( n = 2) 5.38 ( f 0 0 3 ) ( n = 2) 4.68 (f0.06) (n = 2) 6.10 (f0-30) (n = 4) 5.89 (kO.23) (n = 2) 6.44 ( n = 1) 655 (kO.11) ( n = 2) 5.94 (n = 1) 5.51 ($0.16) (n = 2) 5.58…”

Development of N,O-disubstituted hydroxylamines and N,N-disubstituted amines as insect juvenile hormone mimetics and the role of the nitrogenous function for activity

“…This led us to develop a new class of highly active JH mimics, 0-alkyl-N-[(4phenoxyphenoxy) and (4-benzylphenoxy)alkyl]hydroxylamines. The optimization of the structure gave Oisopropyl-lV-[3-[4-(3-methylphenoxy)phenoxy]propyl]hy-0021-8561 /90/1438-0514$02.50/0 droxylamine (9); the activity against C. pipiens was as high as that of our previous propionaldoxime (Niwa et al, 1988; Hayashi et al, 1989) and propyl ether (Niwa et al, 1989) types of compounds. Again in this series of compounds, those with a nitrogen atom at the 6-position were found to be more potent than the corresponding 5oxygen compounds.…”

“…The set of compounds in Table I was prepared by simply reducing the corresponding oximes (Niwa et al, 1988) with sodium cyanoborohydride. Since the optimum molecular length for JH-mimetic activity has been suggested to be about 21A by quantitative structure-activity relationship analysis of terpenoid compounds (Nakayama et al, 1984) and proved valid through a number of developmental works (Nakayama et al, 1985;Niwa et al, 1988Niwa et al, , 1989Hayashi et al, 1989), we confined compounds to be prepared here to those that satisfy this condition, that is phenoxyphenoxy and benzylphenoxy compounds with a side chain made up with seven atoms.…”

“…In our developmental studies on a series of insect juvenile hormone (JH) mimetic compounds, (4-phenoxyphenoxy)-and (4-benzylphenoxy)alkanaldoximes (Niwa et al, 1988), (4-alkoxyphenoxy)-and (4-alkylphenoxy)alkanaldoximes (Hayashi et al, 1989), and (4-phenoxyphenoxy)-and (4-benzylphenoxy)alkyl alkyl ethers (Niwa et al, 1989), we found that the positions of the oxime and ether functions in a molecule are important for high activity. The positional effect has been clearly specified in the ether series of compounds to be at the 5-position from the common phenoxy oxygen atom; the activity against Culex pipiens of (phenoxyphenoxy)-and (benzylphenoxy)propyl propyl ethers was more than 10 times higher than that of the corresponding ethyl butyl and butyl ethyl ethers.…”

3D-QSAR studies on the biological activity of juvenile hormone mimetic compounds for Culex pipiens Larvae

“…The significant roles of JH and JH mimics in interrupting the normal development of insects (Hayashi et al, 1991) stimulated scientists to consider these compounds as potential insect control agents (Henrick et al, 1973;De Kort and Granger, 1981;Hayashi et al, 1989;Keeley et al, 1989;Wigglesworth, 1936Wigglesworth, , 1970Wimmer and Romaòuk, 1981). Biochemical effects of juvenoids are complex and vary from one analog to another since they function as JH agonists or antagonists or both (Kiss et al, 1976).…”