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Molecules 2017, 22(7), 1058; doi:10.3390/molecules22071058

Influence of Pyranose and Spacer Arm Structures on Phloem Mobility and Insecticidal Activity of New Tralopyril Derivatives

1
Institute of Entomology, Guizhou University, Guiyang 550025, Guizhou, China
2
Guizhou Provincial Key Laboratory for Agricultural Pest Management of the Mountainous Region, Guizhou University, Guiyang 550025, Guizhou, China
3
Guizhou Tea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang 550006, Guizhou, China
4
Guizhou Institute of Plant Protection, Guizhou Academy of Agricultural Sciences, Guiyang 550006, Guizhou, China
*
Author to whom correspondence should be addressed.
Received: 22 May 2017 / Revised: 20 June 2017 / Accepted: 20 June 2017 / Published: 25 June 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

Six new conjugates were designed and synthesized by introducing glucose, methyl glucuronate or glucuronic acid moieties on tralopyril. Phytotoxicity and phloem mobility results demonstrated that the introduction of glucose, methyl glucuronate or glucuronic acid moieties can simultaneously solve the tough phytotoxicity problem and phloem mobility transformation of tralopyril. Conjugates 12 and 18 containing the glucuronic acid moiety exhibited higher phloem mobility than conjugates 9, 11, 15 and 17. Conjugates 15, 17 and 18 with methoxymethyl groups on the tralopyril pyrrole nitrogen atom showed activity against Plutella xylostella, while conjugates 9, 11 and 12 with a methene group on the pyrrole N showed no activity. Cabbage roots were incubated in a buffered solution containing conjugates 15, 17 and 18 at 4 mM for 72 h. Only 18 showed systemic insecticidal activity with 100% mortalityagainst P. xylostella, while 15 and 17 showed lower activity andchlorfenapyr showed no activity. The glucuronic acid promoiety imparted more phloem mobility to tralopyril than glucose and methyl glucuronate. The methoxymethyl group bond on the tralopyril skeleton was the key factor in determining the insecticidal activity of the conjugates. A promising systemic proinsecticide containing glucuronic acid and tralopyril moieties was proposed. View Full-Text
Keywords: glucuronic acid; glucose; tralopyril; chlorfenapyr; phloem mobility glucuronic acid; glucose; tralopyril; chlorfenapyr; phloem mobility
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MDPI and ACS Style

Chen, Y.; Lei, Z.W.; Zhang, Y.; Yang, W.; Liu, H.F.; Zhou, Y.F.; Yang, M.F. Influence of Pyranose and Spacer Arm Structures on Phloem Mobility and Insecticidal Activity of New Tralopyril Derivatives. Molecules 2017, 22, 1058.

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