Design,Synthesis, and Insecticidal Activities of Novel meta-Diamide Compounds Containing Ethyl Acetate and Their Derivatives

In this study, a series of meta-diamide compounds containing ethyl acetate group and their derivatives were designed and synthesized. Their insecticidal activities against Plutella xylostella, Spodoptera frugiperda and Alfalfa sprouts were evaluated. Preliminary bioassays showed that some of the title compounds exhibited excellent insecticidal activities. Especially compound ethyl N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-N-(4-cyanobenzoyl)glycinate and ethyl N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-N-(6-fluoronicotinoyl)glycinate showed 100 % mortality at 0.1 mg/L against Plutella xylostella and Spodoptera frugiperda, same to broflanilide. Their LC₅₀ against Plutella xylostella is 0.286 mg/L and 0.0218 mg/L, respectively. Moreover, compound ethyl N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-N-(6-fluoronicotinoyl)glycinate displayed faster control efficacy than broflanilide at 0.1 mg/L. The results indicated that meta-diamide compounds containing ethyl acetate group could be developed as novel and promising insecticides.     

溴虫氟苯双酰胺对草地贪夜蛾的亚致死效应

为明确溴虫氟苯双酰胺对草地贪夜蛾Spodoptera frugiperda的亚致死效应,采用点滴法测定溴虫氟苯双酰胺对草地贪夜蛾3龄幼虫的室内毒力及亚致死剂量溴虫氟苯双酰胺(LD₁₅和LD₃₀)对草地贪夜蛾生物学特性的影响,同时测定了亚致死剂量(LD₁₅、LD₃₀)和半致死剂量(LD₅₀)溴虫氟苯双酰胺对草地贪夜蛾3龄幼虫体内解毒酶(GST、EST、MFO)、保护酶(SOD、POD、CAT)活性的影响。结果表明,溴虫氟苯双酰胺对草地贪夜蛾3龄幼虫具有良好的触杀活性,LD₅₀值为0.50μg/g。亚致死剂量(LD₁₅和LD₃₀)溴虫氟苯双酰胺处理草地贪夜蛾3龄幼虫后,幼虫存活率显著下降,较对照分别下降了6.7%和32.88%;LD₃₀处理的成虫畸形率(8.33%)较对照(1.75%)显著升高,产卵前期(3.31 d)较对照(2.88 d)显著延长。溴虫氟苯双酰胺3个不同剂量(LD_15...     

Baseline susceptibility of Helicoverpa armigera,Plutella xylostella,and Spodoptera frugiperda to the meta-diamide insecticide broflanilide

Broflanilide is a novel meta-diamide insecticide that acts as a γ-aminobutyric acid-gated chloride channel allosteric modulator. With its unique mode of action, broflanilide has no known cross-resistance with existing insecticides and is expected to be an effective tool for the management of insecticide resistance. Establishing the baseline susceptibility to this insecticide is an essential step for developing and implementing effective resistance management strategies. Here we evaluated the baseline susceptibility to broflanilide for 3 cosmopolitan lepidopteran pest species, Helicoverpa armigera, Plutella xylostella, and Spodoptera frugiperda. Broflanilide exhibited high activity against populations sampled in the major distribution range of these pests in China, with median lethal concentrations (LC₅₀) ranging between 0.209 and 0.684, 0.076 and 0.336, and 0.075 and 0.219 mg/L for H. armigera, P. xylostella, and S. frugiperda, respectively. Among-population variability in susceptibility to broflanilide was moderate for H. armigera (3.3-fold), P. xylostella (4.4-fold), and S. frugiperda (2.9-fold). The recommended diagnostic concentrations for H. armigera, P. xylostella, and S. frugiperda were 8, 4, and 2 mg/L, respectively. Little or no cross-resistance to broflanilide was detected in 3 diamide-resistant strains of P. xylostella and 1 spinosyns-resistant strain of S. frugiperda. Our results provide critical information for the development of effective resistance management programs to sustain efficacy of broflanilide against these key lepidopteran pests.