Photodegradation of Novel Nitromethylene Neonicotinoids with Tetrahydropyridine-Fixed Cis Configuration in Aqueous Solution

Abstract

Photodegradation of 1-((6-chloropyridin-3-yl)methyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol (IPPA152001) and 1-((6-chloropyridin-3-yl)methyl)-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine (IPPA152004) was studied in distilled water; high-pressure mercury lamp and xenon lamp were used as light sources. The photolytic rate constants of the two compounds and their half-lives were calculated. Compared with imidacloprid, the order of photodegradation rate of three compounds was as follows: imidacloprid > IPPA152001 > or = IPPA152004. Mercury lamp light intensity was measured with chemical actinometers. The quantum yields for photodegradation of IPPA152001 and IPPA152004 in distilled water were also calculated. Photodegradation products of IPPA152004 were preliminarily identified on the basis of the spectral data of GC-MS, LC-TOF-ESI, and LC-MS-MS in positive mode. The photodegradation pathways of IPPA152004 were proposed according to the structures of photoproducts.

Diastereoselective Metabolism of a Novel Cis-Nitromethylene Neonicotinoid Paichongding in Aerobic Soils

“…The fragmentation pattern for M5 was similar to the photodegradation product 8-carbonyl-derivative as reported by Zhao et al 30 Therefore, M5 was tentatively identified as 1-((6-chloropyridin-3-yl)methyl)-7-methyl-5-propoxy-8-carbonyl-hexahydro-imidazo[1,2-a]pyridine.…”

“…For instance, M1 was found as a product of IPP in aqueous solution after irradiation with a mercury and xenon lamp. 30 In addition, M1 was shown to have activity against insect pests. 37 Similarly, metabolites of imidacloprid derived from treated plants were observed to be highly toxic to aphids.…”

Impact of the novel neonicotinoid insecticide Paichongding on bacterial communities in yellow loam and Huangshi soils

“…Paichongding (IPP, 1-((6-chloropydidin-3-yl) methyl)-7-methyl-8-nitro-5propoxy-1,2,3,5,6,7-hexahydroimidazo[1, 2-α-]-pyridine) is a novel nitromethylene neonicotinoid recently developed by the East China University of Science and Technology in China (Zhao et al 2010;Fu et al 2013a, b;Li et al 2013;Wang et al 2013;Zhang et al 2013;Cai et al 2015b). IPP is different from the traditional neonicotinoids as it is the antagonist of the postsynaptic nicotinic acetylcholine receptors (nAChRs) of insects.…”

“…Several reports have mainly focused on its photodegradation in aqueous solution, translocation in Youdonger (Brassica campestris subsp. Chinensis, Chinese cabbage), IPP metabolism, extractable and bound residue, and transformation in soils (Zhao et al 2010;Fu et al 2013a, b;Li et al 2013;Wang et al 2013;Zhang et al 2013;Cai et al 2015b, c). The effect of IPP on soil microbial communities in aerobic soils has not been reported until now.…”

Organische Chemie 2010

“…Ecust stellte IPPA152004 (98) vor, das gegen imidaclopridresistente Reiszikaden wirkt. Das Produkt soll unter dem Namen Paichongding in China vermarktet werden 130. In den letzten Jahren verschwanden einige ältere Produkte zur Bodenbehandlung vom Markt.…”