山东省不同地区棉蚜对新烟碱类杀虫剂的抗药性检测及酶抑制剂的增效作用研究

为明确山东省棉蚜对新烟碱类杀虫剂的抗性水平,采用毛细管微量点滴法测定了泰安、聊城和东营3个田间种群及1个敏感种群对吡虫啉、烯啶虫胺、啶虫脒、噻虫嗪、噻虫啉、噻虫胺6种新烟碱类杀虫剂的敏感性,同时测定了磷酸三苯酯(TPP)、顺丁烯二酸二乙酯(DEM)和增效醚(PBO)3种酶抑制剂的增效作用。结果表明:泰安棉蚜种群对烯啶虫胺的抗性倍数为16.95,处于中等抗性水平,对吡虫啉和啶虫脒的抗性倍数分别为5.69和9.57,已产生低水平抗性,对噻虫胺、噻虫嗪和噻虫啉的抗性倍数均小于3.0,仍较敏感;聊城棉蚜种群对吡虫啉、啶虫脒和噻虫嗪的抗性倍数分别为28.51、25.88和18.16,属中等抗性水平,对噻虫啉和噻虫胺的抗性倍数分别为6.01和6.37,已产生低水平抗性,对烯啶虫胺仍处于敏感阶段;东营棉蚜种群对吡虫啉、啶虫脒和噻虫胺的抗性倍数分别为37.95、21.52和12.95,已产生中等水平抗性,对噻虫啉、烯啶虫胺和噻虫嗪的抗性倍数分别为7.07、6.38和4.75,处于低水平抗性阶段。多功能氧化酶抑制剂PBO和羧酸酯酶抑制剂TPP对6种供试新烟碱类杀虫剂的增效作用明显,谷胱甘肽-S-转移酶抑制剂DEM对这6种药剂也具有一定的增效作用。研究表明,山东省泰安等3地区棉蚜种群对6种新烟碱类杀虫剂均产生了不同程度的抗药性,多功能氧化酶和羧酸酯酶可能在棉蚜对该类杀虫剂的抗性中起主要作用,谷胱甘肽-S-转移酶可能也具有一定的作用。     

先正达/拜耳建言欧盟新烟碱类杀虫剂计划

为推动破解欧盟有关新烟碱类杀虫剂对蜜蜂健康"理论风险"僵局,先正达和拜耳提出一份行动计划建议。此举是在欧盟委员会就其一项有关2年内禁止在某些作物上使用噻虫胺、吡虫啉和噻虫嗪等新烟碱类杀虫剂     

长翅型与短翅型褐飞虱对杀虫剂的敏感性比较

采用稻苗浸渍法测定了长、短翅型褐飞虱对烯啶虫胺、环氧虫啶、呋虫胺、噻虫嗪、噻虫胺、吡虫啉、毒死蜱、敌敌畏、噻嗪酮、异丙威、吡蚜酮和醚菊酯的敏感性，并对其体内解毒酶活力进行了比较分析。结果表明:长翅型与短翅型褐飞虱若虫对新烟碱类杀虫剂呋虫胺、噻虫嗪、噻虫胺和吡虫啉的敏感性存在显著差异，长翅型比短翅型更敏感；相反，对于有机磷类杀虫剂毒死蜱，短翅型褐飞虱则更敏感；2种生物型对烯啶虫胺、环氧虫啶、敌敌畏、噻嗪酮、异丙威、吡蚜酮和醚菊酯的敏感性无显著差异。解毒酶相对比活力测定结果表明，长翅型褐飞虱若虫酯酶比活力显著高于短翅型，细胞色素P450单加氧酶比活力显著低于短翅型，而谷胱甘肽S-转移酶比活力无显著性差异。本研究结果可为褐飞虱的有效防控提供科学参考。     

巴西重新评价烟碱类农药

巴西生态管理部门启动蜜蜂高风险农药的再评价项目,环境局(IBAMA)将从拜耳的吡虫啉入手,开展噻虫嗪、噻虫啉、啶虫脒等烟碱类杀虫剂的再评价,相关细节已在当月政府公告中公布。在巴西吡虫啉较其它三种烟碱类产品销量     

7种杀虫剂对北京地区烟粉虱成虫毒力的比较研究

本试验比较测定了7种杀虫剂对北京地区烟粉虱成虫的毒力,以期为北京地区高毒农药淘汰提供参考。结果表明:氟虫腈对烟粉虱成虫的毒力最强,其LC50值为2.98(g/mL;新烟碱类杀虫剂啶虫脒、吡虫啉对烟粉虱成虫的生物活性较好,LC50值分别为8.04(g/mL、7.49(g/mL,噻虫嗪对烟粉虱成虫毒力相对较差,LC50值仅为95.03(g/mL;烟粉虱成虫对马拉硫磷、异丙威和噻嗪酮3种杀虫剂不敏感。在北京地区,采用噻虫嗪、马拉硫磷、异丙威和噻嗪酮等杀虫剂,不能有效防治烟粉虱的成虫;氟虫腈、吡虫啉和啶虫脒可以用来防治烟粉虱成虫。     

新疆北疆马铃薯甲虫成虫对新烟碱类杀虫剂的敏感性变化

采用点滴法于2009和2010年监测了新疆维吾尔自治区北疆马铃薯甲虫Leptinotarsa decemlineata 9个田间种群成虫对新烟碱类杀虫剂吡虫啉、啶虫脒、噻虫嗪和噻虫啉的敏感性变化,发现其对吡虫啉和噻虫嗪的敏感性逐年降低。2009年监测的6个种群中有3个对啶虫脒和噻虫嗪低抗(抗性倍数5.0~10.0);2010年监测的6个种群全部对噻虫嗪产生了抗性,其中中抗(抗性倍数10.1~40.0)和低抗种群各3个。噻虫嗪与高效氯氟氰菊酯可能存在交互抗性。     

并非所有新烟碱类杀虫剂都对蜜蜂有害

正英国邓迪大学和圣安德鲁斯大学的相关研究表明,评估新烟碱类杀虫剂对蜜蜂的风险时,需要对特定的化合物及靶标生物进行独立分析,不可一概而论。研究发现,不同新烟碱类杀虫剂对熊蜂构成的威胁存在差异。有别于化学作用与之相近的吡虫啉和噻虫嗪,噻虫胺并未表现出对蜜蜂种群的不良影响。然而自2013年起,这3种新烟碱类杀虫剂均已被欧盟大量禁用。     

我国一项研究或证实3种新烟碱类杀虫剂对蜜蜂存在高风险

<正>近期一项由湖南农业大学植物保护学院、农业部农药检定所、湖南省植物保护研究所、北京依科世福科技有限公司等单位共同完成的研究结果表明,吡虫啉、噻虫嗪和噻虫胺等3种新烟碱类杀虫剂对蜜蜂均存在高风险。研究人员采用饲喂管法和点滴法,分别测定了吡虫啉、噻虫嗪、噻虫胺、啶虫脒4种原药及其制剂对意大利蜜蜂成年工蜂的急性毒性,     

新烟碱类杀虫剂种子包衣防治麦蚜的可行性评价

为评价不同新烟碱类杀虫剂处理种子防治小麦蚜虫的应用潜力,采用种子包衣法分别在室内及田间比较了吡虫啉、噻虫嗪、啶虫脒、烯啶虫胺、噻虫啉防治小麦蚜虫的效果及安全性,并测定了吡虫啉和噻虫嗪的持效、对天敌和小麦产量的影响及其在小麦籽粒中的最终残留量。结果表明,在2.4、3.6和4.8 g/kg种子剂量下,啶虫脒明显降低小麦出苗率,而其它药剂均无显著影响;至抽穗前烯啶虫胺、啶虫脒和噻虫啉对麦蚜的防效低,吡虫啉和噻虫嗪则均有较高防效,在58.17%以上,而在小麦抽穗扬花期防效下降,为33.57%~60.46%。吡虫啉和噻虫嗪对叶部麦蚜防效均相应高于穗部。与喷雾处理相比,吡虫啉、噻虫嗪各剂量种子包衣对瓢虫和蚜茧蜂等天敌昆虫影响小,在3.6、4.8 g/kg种子剂量下,小麦千粒重和产量无显著差异,且在小麦籽粒中的残留量低。表明吡虫啉和噻虫嗪种子包衣防治麦蚜的应用潜力大。     

有机磷类杀虫剂代谢机制研究进展

文章对有机磷类杀虫剂代谢机制的研究进展以及昆虫对此类杀虫剂的相关代谢抗性机制进行了总结,阐述了有机磷杀虫剂的生物代谢途径及相关代谢酶系。在生物体中,有机磷类杀虫剂主要发生氧化代谢、水解代谢和轭合代谢等反应。其氧化代谢主要在细胞色素P450酶系(P450s)的催化作用下进行,其中,最重要的氧化反应是硫代有机磷酸酯类杀虫剂氧化脱硫形成生物毒性更高的有机磷氧化物的反应,以及氧化脱芳(烷)基化的反应;有机磷杀虫剂及其氧化产物在生物体内还可发生水解代谢反应,在对氧磷酶PON1等磷酸三酯酶的催化作用下,水解生成低毒性或者无毒的代谢物;有机磷杀虫剂的轭合代谢主要是在谷胱甘肽硫转移酶(GSTs)的催化下进行的。昆虫对有机磷类杀虫剂的代谢抗性与昆虫中参与此类杀虫剂代谢的解毒酶的改变密切相关,其中,与有机磷类杀虫剂代谢相关的P450s基因的过量表达和酶活性增强、丝氨酸水解酯酶的过量表达及基因突变、GSTs基因的过量表达等,均可导致铜绿蝇Lucilia cuprina、桃蚜Myzus persicae等昆虫对二嗪磷和马拉硫磷等有机磷类杀虫剂的代谢抗性。明确有机磷类杀虫剂的结构特点、代谢途径以及昆虫对此类杀虫剂的代谢抗性机制,对掌握有机磷类杀虫剂的毒理学机制,安全有效地使用此类杀虫剂,有效治理害虫对有机磷类杀虫剂的抗药性,以及开发生物选择性好的新型有机磷类杀虫剂,均具有重要意义。     

Spinosad resistance in female Musca domestica L. from a field-derived population

BACKGROUND: Bait-formulated spinosad is currently being introduced for housefly (Musca domestica L.) control around the world. Spinosad resistance was evaluated in a multiresistant field population and strains derived from this by selection with insecticides. Constitutive and spinosad-induced expression levels of three cytochrome P450 genes, CYP6A1, CYP6D1 and CYP6D3, previously reported to be involved in insecticide resistance, were examined. RESULTS: In 2004 a baseline for spinosad toxicity of Danish houseflies where all field populations were considered to be susceptible was established. In the present study, females of a multiresistant field population 791a were, however, 27-fold spinosad resistant at LC₅₀, whereas 791a male houseflies were susceptible. Strain 791a was selected with spinosad, thiamethoxam, fipronil and imidacloprid, resulting in four strains with individual characteristics. Selection of 791a with spinosad did not alter spinosad resistance in either males or females, but counterselected against resistance to the insecticides thiamethoxam and imidacloprid targeting nicotinic acetylcholine receptors. A synergist study with piperonyl butoxide, as well as gene expression studies of CYP6A1, CYP6D1 and CYP6D3, indicated a partial involvement of cytochrome P450 genes in spinosad resistance. CONCLUSION: This study reports female-linked spinosad resistance in Danish houseflies. Negative cross-resistance was observed between spinosad and neonicotinoids in one multiresistant housefly strain. Spinosad resistance involved alterations of cytochrome P450 gene expression. Copyright © 2011 Society of Chemical Industry     

Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants

Neonicotinoid insecticides are compounds acting agonistically on insect nicotinic acetylcholine receptors (nAChR). They are especially active on hemipteran pest species such as aphids, whiteflies, and planthoppers, but also commercialized to control many coleopteran and some lepidopteran pest species. The most prominent member of this class of insecticides is imidacloprid. All neonicotinoid insecticides bind with high affinity (I₅₀-values around 1 nM) to [³H]imidacloprid binding sites on insect nAChRs. One notable ommission is the neonicotinoid thiamethoxam, showing binding affinities up to 10,000-fold less potent than the others, using housefly head membrane preparations. Electrophysiological whole cell voltage clamp studies using neurons isolated from Heliothis virescens ventral nerve cord showed no response to thiamethoxam when applied at concentrations of 0.3 mM, although the symptomology of poisoning in orally and topically treated noctuid larvae suggested strong neurotoxicity. Other neonicotinoids, such as clothianidin, exhibited high activity as agonists on isolated neurons at concentrations as low as 30 nM. There was no obvious correlation between biological efficacy of thiamethoxam against aphids and lepidopterans and receptor affinity in electrophysiological and binding assays. Pharmacokinetic studies using an LC-MS/MS approach to analyze haemolymph samples taken from lepidopteran larvae revealed that thiamethoxam orally applied to 5th instar Spodoptera frugiperda larvae was rapidly metabolized to clothianidin, an open-chain neonicotinoid. Clothianidin shows high affinity to nAChRs in both binding assays and whole cell voltage clamp studies. When applied to cotton plants, thiamethoxam was also quickly metabolized, with clothianidin being the predominant neonicotinoid in planta briefly after application, as indicated by LC-MS/MS analyses. Interestingly, the N-desmethylated derivative of thiamethoxam, N-desmethyl thiamethoxam, was not significantly produced in either lepidopteran larvae or in cotton plants, although it was often mentioned as a possible metabolite, being nearly as active as imidacloprid. In conclusion, our investigations show that thiamethoxam is likely to be a neonicotinoid precursor for clothianidin.     

Homology modelling of Drosophila cytochrome P450 enzymes associated with insecticide resistance

BACKGROUND: Overexpression of the cytochrome P450 gene Cyp6g1 confers resistance against DDT and a broad range of other insecticides in Drosophila melanogaster Meig. In the absence of crystal structures of CYP6G1 or complexes with its substrates, structural studies rely on homology modelling and ligand docking to understand P450–substrate interactions. RESULTS: Homology models are presented for CYP6G1, a P450 associated with resistance to DDT and neonicotinoids, and two other enzymes associated with insecticide resistance in D. melanogaster, CYP12D1 and CYP6A2. The models are based on a template of the X‐ray structure of the phylogenetically related human CYP3A4, which is known for its broad substrate specificity. The model of CYP6G1 has a much smaller active site cavity than the template. The cavity is also ‘V’‐shaped and is lined with hydrophobic residues, showing high shape and chemical complementarity with the molecular characteristics of DDT. Comparison of the DDT–CYP6G1 complex and a non‐resistant CYP6A2 homology model implies that tight‐fit recognition of this insecticide is important in CYP6G1. The active site can accommodate differently shaped substrates ranging from imidacloprid to malathion but not the pyrethroids permethrin and cyfluthrin. CONCLUSION: The CYP6G1, CYP12D1 and CYP6A2 homology models can provide a structural insight into insecticide resistance in flies overexpressing P450 enzymes with broad substrate specificities. Copyright © 2010 Society of Chemical Industry     

Metabolic interactions of agrochemicals in humans

Agrochemicals and other xenobiotics are metabolized by xenobiotic-metabolizing enzymes (XMEs) to products that may be more or less toxic than the parent chemical. In this regard, phase-I XMEs such as cytochrome P450s (CYPs) are of primary importance. Interactions at the level of metabolism may take place via either inhibition or induction of XMEs. Such interactions have often been investigated, in vitro, in experimental animals, using subcellular fractions such as liver microsomes, but seldom in humans or at the level of individual XME isoforms. The authors have been investigating the metabolism of a number of agrochemicals by human liver microsomes and recombinant CYP isoforms and have recently embarked on studies of the induction of XMEs in human hepatocytes. The insecticides chlorpyrifos, carbaryl, carbofuran and fipronil, as well as the repellant DEET, are all extensively metabolized by human liver microsomes and, although a number of CYP isoforms may be involved, CYP2B6 and CYP3A4 are usually the most important. Permethrin is hydrolyzed by esterase(s) present in both human liver microsomes and cytosol. A number of metabolic interactions have been observed. Chlorpyrifos and other phosphorothioates are potent inhibitors of the CYP-dependent metabolism of both endogenous substrates, such as testosterone and estradiol, and exogenous substrates, such as carbaryl, presumably as a result of the interaction of highly reactive sulfur, released during the oxidative desulfuration reaction, with the heme iron of CYP. The hydrolysis of permethrin in human liver can be inhibited by chlorpyrifos oxon and by carbaryl. Fipronil can inhibit testosterone metabolism by CYP3A4 and is an effective inducer of CYP isoforms in human hepatocytes.     

Comparative analysis of neonicotinoid binding to insect membranes: I. A structure-activity study of the mode of [3H]imidacloprid displacement in Myzus persicae and Aphis craccivora

Neonicotinoids bind selectively to insect nicotinic acetylcholine receptors with nanomolar affinity to act as potent insecticides. While the members of the neonicotinoid class have many structural features in common, it is not known whether they also share the same mode of binding to the target receptor. Previous competition studies with [3H]imidacloprid, the first commercialised neonicotinoid, indicated that thiamethoxam, representing a novel structural sub-class, may bind in a different way from that of other neonicotinoids. In the present work we analysed the mode of [3H]imidacloprid displacement by established neonicotinoids and newly synthesized analogues in the aphids Myzus persicae Sulzer and Aphis craccivora Koch. We found two classes of neonicotinoids with distinct modes of interference with [3H]imidacloprid, described as direct competitive inhibition and non-competitive inhibition, respectively. Competitive neonicotinoids were acetamiprid, nitenpyram, thiacloprid, clothianidin and nithiazine, whereas thiamethoxam and the N-methyl analogues of imidacloprid and clothianidin showed non-competitive inhibition. The chloropyridine or chlorothiazole heterocycles, the polar pharmacophore parts, such as nitroimino, cyanoimino and nitromethylene, and the cyclic or acyclic structure of the pharmacophore were not relevant for the mode of inhibition. Consensus structural features of the neonicotinoids were defined for the two mechanisms of interaction with [3H]imidacloprid binding. Furthermore, two sub-classes of non-competitive inhibitors can be discriminated on the basis of their Hill coefficients for imidacloprid displacement. We conclude from the present data that the direct competitors share the binding site with imidacloprid, whereas non-competitive compounds, like thiamethoxam, bind to a different site or in a different mode.     

Effect of distribution and concentration of topically applied neonicotinoid insecticides in buffalograss,Buchloe dactyloides,leaf tissues on the differential mortality of Blissus occiduus under field conditions

BACKGROUND: Neonicotinoid insecticides are generally efficacious against many turfgrass pests, including several important phloem‐feeding insects. However, inconsistencies in control of western chinch bugs, Blissus occiduus, have been documented in field efficacy studies. This research investigated the efficacy of three neonicotinoid insecticides (clothianidin, imidacloprid and thiamethoxam) against B. occiduus in buffalograss under field conditions and detected statistically significant differences in B. occiduus numbers among treatments. A subsequent study documented the relative quantity and degradation rate of these insecticides in buffalograss systemic leaf tissues, using HPLC. RESULTS: Neonicotinoid insecticides initially provided significant reductions in B. occiduus numbers, but mortality diminished over the course of the field studies. Furthermore, while all three neonicotinoids were present in the assayed buffalograss leaf tissues, imidacloprid concentrations were significantly higher than those of clothianidin and thiamethoxam. Over the course of the 28 day study, thiamethoxam concentrations declined 700‐fold, whereas imidacloprid and clothianidin declined only 70‐fold and 60‐fold respectively. CONCLUSIONS: Field studies continued to verify inconsistencies in B. occiduus control with neonicotinoid insecticides. This is the first study to document the relative concentrations of topically applied neonicotinoid insecticides in buffalograss systemic leaf tissues. Copyright © 2012 Society of Chemical Industry     

寄生蜂细胞色素P450基因家族进化分析

寄生蜂是重要的天敌昆虫，被广泛应用于生物防治，但在实际生产应用中面临诸多问题，如环境适应性和耐药性问题。细胞色素P450是真核生物中广泛存在的超基因家族酶系，参与农药、植物次生代谢物及环境有害物质等的代谢，同时也参与昆虫体内多种内源性化合物的合成与代谢。本文通过对植食性榕小蜂和9种寄生蜂基因组数据的生物信息学分析，共获得615个P450基因，分析表明不同寄生蜂P450基因家族的差异主要发生在CYP3和CYP4簇，而CYP2和Mito簇相对保守；相较于外寄生蜂，内寄生蜂的P450超基因家族有明显的收缩现象；此外，发现了2个在寄生蜂中1：1：1高度保守的P450基因，CYP18和CYP314，以及茧蜂特有的CYP304基因和内寄生蜂特有的CYP28基因。本研究从基因组水平系统地分析了寄生蜂P450超基因家族的进化，为寄生蜂的遗传改良和规模化饲养等提供理论基础。     

Cytochrome P450 monooxygenase-mediated neonicotinoid resistance in the house fly Musca domestica L

Neonicotinoids play an essential role in the control of house flies Musca domestica. The development of neonicotinoid resistance was found in two field populations. 766b was 130- and 140-fold resistant to imidacloprid and 17- and 28-fold resistant to thiamethoxam in males and females, respectively. 791a was 22- and 20-fold resistant to imidacloprid and 9- and 23-fold resistant to thiamethoxam in males and females, respectively. Imidacloprid selection of 791a increased imidacloprid resistance to 75- and 150-fold in males and females, respectively, whereas selection with thiamethoxam had minimum impact. Neonicotinoid resistance was in all cases suppressed by PBO. The cytochrome P450 genes CYP6A1, CYP6D1 and CYP6D3 were constitutively over-expressed in resistant strains and CYP6D1 and CYP6D3 differentially expressed between sexes. The highest level of CYP6A1 expression was observed in both gender of the imidacloprid-selected strain after neonicotinoid exposure. CYP6D1 expression was increased after neonicotinoid exposure in resistant males. CYP6D3 expression was induced in both sexes upon neonicotinoid exposure but significantly higher in females.     

Comparative analysis of neonicotinoid binding to insect membranes: II. An unusual high affinity site for [3H]thiamethoxam in Myzus persicae and Aphis craccivora

Neonicotinoids represent a class of insect-selective ligands of nicotinic acetylcholine receptors. Imidacloprid, the first commercially used neonicotinoid insecticide, has been studied on neuronal preparations from many insects to date. Here we report first intrinsic binding data of thiamethoxam, using membranes from Myzus persicae Sulzer and Aphis craccivora Koch. In both aphids, specific binding of [3H]thiamethoxam was sensitive to temperature, while the absolute level of non-specific binding was not affected. In M persicae, binding capacity (Bmax) for [3H]thiamethoxam was ca 450 fmol mg(-1) of protein at 22 degrees C and ca 700 fmol mg(-1) of protein at 2 degrees C. The negative effect of increased temperature was reversible and hence not due to some destructive process. The affinity for [3H]thiamethoxam was less affected by temperature: Kd was ca 11 nM at 2 degrees C and ca 15 nM at 22 degrees C. The membranes also lost binding sites for [3H]thiamethoxam during prolonged storage at room temperature, and upon freezing and thawing. In A craccivora, [3H]thiamethoxam was bound with a capacity of ca 1000 fmol mg(-1) protein and an affinity of ca 90 nM, as measured at 2 degrees C. Overall, the in vitro temperature sensitivity of [3H]thiamethoxam binding was in obvious contrast to the behaviour of [3H]imidacloprid studied in parallel. Moreover, the binding of [3H]thiamethoxam was inhibited by imidacloprid in a non-competitive mode, as shown with M persicae. In our view, these differences demonstrate that thiamethoxam and imidacloprid, which represent different structural sub-classes of neonicotinoids, do not share the same binding site or mode. This holds also for other neonicotinoids, as we report in a companion article.     

Differential metabolism of sulfoximine and neonicotinoid insecticides by Drosophila melanogaster monooxygenase CYP6G1

Sulfoxaflor [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-λ⁴-sulfanylidene] cyanamide] is in development as the first product from the new sulfoximine class of insect control agents. Highly effective against a variety of sap-feeding pest insects, available data indicate no cross-resistance to sulfoxaflor in pest insect strains that exhibit high levels of resistance to neonicotinoids and other insecticides. In vitro studies of the cytochrome P450 monooxygenase CYP6G1 from Drosophila melanogaster, expressed in a Drosophila cell line, show very high levels of metabolism for a variety of neonicotinoids, but not for sulfoxaflor and its chloropyridine-analog. A sulfoxaflor analog with nitrogen in place of the carbon in the bridge between the pyridine and sulfoximine moiety shows a modest degree of metabolism. In silico homology modeling of the CYP6G1 with the sulfoximines and neonicotinoids suggests that steric effects may limit interactions of the sulfoximines with the reactive heme-oxo complex. A distinct relationship was identified for the summed Hückel charges and the degree of metabolism observed. These observations help explain the lack of sulfoxaflor metabolism by CYP6G1, and in turn provide a basis for the lack of cross-resistance to sulfoxaflor in insecticide resistant strains of pest insects.