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PubMed2004

Evaluation and validation of a commercially available enzyme-linked immunosorbent assay for the neonicotinoid insecticide imidacloprid in agricultural samples.

The performance of a commercially available microtiter plate ELISA kit for the determination of the neonicotinoid insecticide imidacloprid was evaluated for sensitivity, selectivity, influence of organic solvent used for extraction procedure, matrix interference originated from agricultural sample, accuracy, and method comparison with conventional HPLC analysis. The limit of detection for the kit (0.1 or 0.5 ng/mL) was determined. The working range (1-39 ng/mL) experimentally calculated on the basis of a criterion, which is determined as the range from I(20) to I(80), was comparable to that established by the manufacturer (1-50 ng/mL). The linearity of the standard curve based on the kit-assembled standard solutions agreed with the one based on the self-made standard solutions. Specificity studies indicate that the imidacloprid monoclonal antibody can readily distinguish the target compound from other structurally related neonicotinoid analogues and some metabolites, with the exception of clothianidin, the cross-reactivity of which was approximately 12%. To extract imidacloprid from an agricultural sample (apple) as simply and rapidly as possible, some extraction methods were examined. Consequently, the extraction method with hand-shaking for 5 min was the best among the examined methods. For the analysis of imidacloprid in apple samples, it was extracted directly with methanol and the extracts were diluted 10-fold (100-fold in the well) with water prior to ELISA analysis. No significant matrix interference was observed with the dilution factor. Recoveries of imidacloprid from fortified apple samples ranged from 87.7 to 112.0%. The results obtained with the ELISA kit correlated well with those by the reference method (conventional HPLC analysis) for apple samples (r > 0.998). These findings strongly indicate that the ELISA kit may be employed routinely for an on-site imidacloprid residue analysis of apple samples.

Antibodies, Monoclonal↗

PubMed2006

Neonicotinoid insecticides display partial and super agonist actions on native insect nicotinic acetylcholine receptors.

Nicotinic acetylcholine receptors (nAChRs) are present in high density in insect nervous tissue and are targeted by neonicotinoid insecticides. Improved understanding of the actions of these insecticides will assist in the development of new compounds. Here, we have used whole-cell patch-clamp recording of cholinergic neurons cultured from the central nervous system of 3rd instar Drosophila larvae to examine the actions of acetylcholine (ACh) and nicotine, as well as the neonicotinoids imidacloprid, clothianidin and P-CH-clothianidin on native nAChRs of these neurons. Dose-response data yield an EC(50) value for ACh of 19 microm. Both nicotine and imidacloprid act as low efficacy agonists at native nAChRs, evoking maximal current amplitudes 10-14% of those observed for ACh. Conversely, clothianidin and P-CH-clothianidin evoke maximal current amplitudes up to 56% greater than those evoked by 100 microm ACh in the same neurons. This is the first demonstration of 'super' agonist actions of an insecticide on native insect nAChRs. Cell-attached recordings indicate that super agonism results from more frequent openings at the largest (63.5 pS) conductance state observed.

Acetylcholine↗

PubMed2006

Role in the selectivity of neonicotinoids of insect-specific basic residues in loop D of the nicotinic acetylcholine receptor agonist binding site.

The insecticide imidacloprid and structurally related neonicotinoids act selectively on insect nicotinic acetylcholine receptors (nAChRs). To investigate the mechanism of neonicotinoid selectivity, we have examined the effects of mutations to basic amino acid residues in loop D of the nAChR acetylcholine (ACh) binding site on the interactions with imidacloprid. The receptors investigated are the recombinant chicken alpha4beta2 nAChR and Drosophila melanogaster Dalpha2/chicken beta2 hybrid nAChR expressed in Xenopus laevis oocytes. Although mutations of Thr77 in loop D of the beta2 subunit resulted in a barely detectable effect on the imidacloprid concentration-response curve for the alpha4beta2 nAChR, T77R;E79V double mutations shifted the curve dramatically to higher affinity binding of imidacloprid. Likewise, T77K;E79R and T77N;E79R double mutations in the Dalpha2beta2 nAChR also resulted in a shift to a higher affinity for imidacloprid, which exceeded that observed for a single mutation of Thr77 to basic residues. By contrast, these double mutations scarcely influenced the ACh concentration-response curve, suggesting selective interactions with imidacloprid of the newly introduced basic residues. Computational, homology models of the agonist binding domain of the wild-type and mutant alpha4beta2 and Dalpha2beta2 nAChRs with imidacloprid bound were generated based on the crystal structures of acetylcholine binding proteins of Lymnaea stagnalis and Aplysia californica. The models indicate that the nitro group of imidacloprid interacts directly with the introduced basic residues at position 77, whereas those at position 79 either prevent or permit such interactions depending on their electrostatic properties, thereby explaining the observed functional changes resulting from site-directed mutagenesis.

Acetylcholine↗

PubMed2005

Prodrug-oriented molecular design of neonicotinoids: preparation of imidacloprid-related 5,5-dimethoxy-1,3-diazacyclohexane derivatives and their insecticidal activity.

Prodrug-oriented molecular design was attempted for the potent acyclic neonicotinoid insecticide, clothianidin (1-(2-chloro-5-thiazolylmethyl)-3-methyl-2-nitroguanidine). Molecules bearing a CH2COCH2 bridge linking the 1,3-NH ends of clothianidin or their acetals would possibly be hydrolyzed, regenerating the mother compounds. This strategy was used to prepare seven acetals of clothianidin-based molecules that combined 2-chloro-5-thiazolylmethyl, 6-chloro-3-pyridylmethyl or 3-tetrahydrofurfuryl with a nitroimine, cyanoimine or nitromethylene group. The key intermediate, 1,3-diamino-2,2-dimethoxypropane, was prepared from the dihydroxyacetone dimer in four steps. A selected acetal showed a characteristic nerve-impulse pattern for neonicotinoids on an excised American cockroach ganglion, although the neuroblocking activity was fairly low. Some acetals were highly insecticidal against the pea aphid at 0.8-20 ppm 7 days after a spray treatment, this being in a contrast to their far weaker activity by injection into American cockroaches. The biological results suggest that the intrinsic insecticidal activities of the acetals are weak, but would exhibit enhanced activity if hydrolyzed in an external environment.

Acetals↗

PubMed2004

Effects of neonicotinoid insecticides on the bionomics of twospotted spider mite (Acari: Tetranychidae).

Previous reports indicate that applications of imidacloprid, a neonicotinoid insecticide, can lead to population buildups of twospotted spider mite, Tetranychus urticae Koch, in the field. Moreover, laboratory studies showed enhanced fecundity of T. urticae after an imidacloprid treatment. In this study, experiments were conducted in the greenhouse to investigate the potential effects of imidacloprid and several other neonicotinoid insecticides on fecundity, egg viability, preimaginal survivorship, and sex ratio of T. urticae (German strain WI) on French beans, Phaseolus vulgaris L. Four insecticides, i.e., imidacloprid (Confidor 200SL), thiacloprid (Calypso 480 SC), acetamiprid (Mospilan 70 WP), and thiamethoxam (Actara 25 WG), were tested at field-relevant (100, 120, 125, and 95 ppm) and sublethal doses (10, 12, 12.5, and 9.5 ppm), respectively. Both spray and drench applications were tested. At field-relevant doses, fecundity of T. urticae decreased and was lower in the treatments compared with the untreated control, whereas preimaginal survivorship and proportion of female offspring (i.e., sex ratio) were lower compared with the control. At sublethal doses, no significant differences were found among the treatments. Data on egg viability, preimaginal survivorship, and sex ratio at sublethal doses followed the same trends as at field-relevant doses. In an additional experiment, the metabolism of imidacloprid into monohydroxy-imidacloprid, olefine, guanidine, and 6-chloronicotinic acid was compared with the oviposition pattern of T. urticae. These findings are discussed with regard to previous laboratory and field observations of imidacloprid-induced fertility increases in T. urticae.

Animals↗

PubMed2004

Dinotefuran: a potential neonicotinoid insecticide against resistant mosquitoes.

Because pyrethroid, organophosphate, and carbamate resistance is more and more developed in mosquitoes of medical importance, there is an urgent need for alternative insecticides for vector control. Dinotefuran, a new neonicotinoid insecticide commercialized by Mitsui Chemicals (Tokyo, Japan), could be a useful candidate in public health because it shows low mammalian toxicity and great insecticidal activity against a broad range of pests. In this study, the intrinsic toxicity of dinotefuran was evaluated by larval bioassay and topical application against different mosquito strains of Anopheles gambiae Giles, Culex quinquefasciatus Say, and Aedes aegypti L. having none, one, or several resistance mechanisms, respectively, to insecticides. The results showed that dinotefuran was less toxic than most of the commonly used insecticides (e.g., deltamethrin, carbosulfan, and temephos) against the susceptible mosquitoes tested (between 6- and 100-fold at the LD50 level). However, the toxicity of dinotefuran was not strongly affected by the presence of common resistance mechanism, i.e., kdr mutation and insensitive acetylcholinesterase (resistance ratio [RR] from 1.3 to 2.3). More interestingly, the carbamate-resistant strain of Cx. quinquefasciatus was significantly more affected by dinotefuran than the susceptible strain (RR = 0.70), probably because the insensitive acetylcholinesterase is less efficient to degrade nicotinic substrates than normal acetylcholinesterase. Despite the relatively low toxicity of dinotefuran against susceptible mosquitoes, the absence of cross-resistance with common insecticides (pyrethroids, carbamates, and organophosphates) makes neonicotinoids potential candidates for disease vector control, especially in area where mosquitoes are resistant to insecticides.

Aedes↗

PubMed2000

Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors.

The favorable selective toxicity of neonicotinoid insecticides (represented here by imidacloprid, thiacloprid, and a nitromethylene analogue) for insects versus mammals is not shared by three of their N-unsubstituted imine derivatives or by nicotine or epibatidine. The same selectivity pattern is evident at the receptor level, i.e., the insect nicotinic acetylcholine receptor (nAChR) versus mammalian nAChR subtypes (alpha1, alpha3, alpha4, and alpha7) assayed independently. The insect-selective compounds are not protonated with a nitroimine, cyanoimine, or nitromethylene group and the mammalian-selective compounds are ionized at physiological pH. We propose that the negatively charged tip of the nitro or cyano group (not a partial positive charge at imidazolidine N-1 as suggested earlier) interacts with a putative cationic subsite of the insect nAChR. This contrasts with the mammalian nAChRs where the iminium cation (+C-NH2 <--> C =+NH2) of the neonicotinoid imine derivatives or ammonium nitrogen of nicotine or epibatidine interacts with the anionic subsite.

Animals↗

PubMed2001

DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid.

Mutagenesis can be used as a means of predicting likely mechanisms of resistance to novel classes of insecticides. We used chemical mutagenesis in Drosophila to screen for mutants that had become resistant to imidacloprid, a neonicotinoid insecticide. Here we report the isolation of two new dominant imidacloprid-resistant mutants. By recombinational mapping we show that these map to the same location as Rst(2)DDT. Furthermore, we show that pre-existing Rst(2)DDT alleles in turn confer cross-resistance to imidacloprid. In order to localize the Rst(2)DDT gene more precisely, we mapped resistance to both DDT and imidacloprid with respect to P-element markers whose genomic location is known. By screening for recombinants between these P-elements and resistance we localized the gene between 48D5-6 and 48F3-6 on the polytene chromosome map. The genomic sequence in this interval shows a cluster of cytochrome P450 genes, one of which, Cyp6g1, is over-expressed in all resistant strains examined. We are now testing the hypothesis that resistance to both compounds is associated with over-expression of this P450 gene.

Animals↗

PubMed2006

The actions of the neonicotinoid imidacloprid on cholinergic neurons of Drosophila melanogaster.

The neonicotinoid insecticide imidacloprid is an agonist on insect nicotinic acetylcholine receptors (nAChRs). We utilised fura-2-based calcium imaging to investigate the actions of imidacloprid on cultured GFP-tagged cholinergic neurons from the third instar larvae of the genetic model organism Drosophila melanogaster. We demonstrate dose-dependent increases in intracellular calcium ([Ca2+]i) in cholinergic neurons upon application of imidacloprid (10 nM-100 muM) that are blocked by nAChR antagonists mecamylamine (10 microM) and alpha-bungarotoxin (alpha-BTX, 1 microM). When compared to other (untagged) neurons, cholinergic neurons respond to lower concentrations of imidacloprid (10-100 nM) and exhibit larger amplitude responses to higher (1-100 microM) concentrations of imidacloprid. Although imidacloprid acts via nAChRs, increases in [Ca2+]i also involve voltage-gated calcium channels (VGCCs) in both groups of neurons. Thus, we demonstrate that cholinergic neurons express nAChRs that are highly sensitive to imidacloprid, and demonstrate a role for VGCCs in amplifying imidacloprid-induced increases in [Ca2+]i.

Acetylcholine↗

PubMed2006

Application of solid-phase extraction and liquid chromatography-mass spectrometry to the determination of neonicotinoid pesticide residues in fruit and vegetables.

A rapid and simple method for simultaneous analysis of four neonicotinoid insecticides including acetamiprid, imidacloprid, thiacloprid and thiamethoxam in fruit and vegetable matrices has been developed. For instance, ready-to-use cartridges filled with a macroporous diatomaceous material were used to extract in a single step insecticide residues with dichloromethane from aqueous-acetone extracts of fruits and vegetables. The eluate was evaporated, the residue redissolved with methanol and then analyzed by liquid chromatography-mass spectrometry in the electrospray ionization (ESI) positive mode. Average recoveries of the four pesticides were between 74.5 and 105% at both spiking levels 0.1 and 1.0 mg kg(-1) in peach, pear, courgette, celery and apricot. Relative standard deviations (RSDs) were less than 10% for all of the recovery tests. The calculated limits of quantitation (LOQs) (0.1-0.5 mg kg(-1)) were equal or lower then the maximum residue limits (MRLs) established by European legislation (0.1-0.5 mg kg(-1)). The proposed method is fast, easy to perform and could be utilized for monitoring of pesticides residues.

Chemical Fractionation↗

PubMed2005

Insect-vertebrate chimeric nicotinic acetylcholine receptors identify a region, loop B to the N-terminus of the Drosophila Dalpha2 subunit, which contributes to neonicotinoid sensitivity.

A chimera based on the chicken alpha4 nicotinic acetylcholine receptor (nAChR) subunit containing an insert from loop B to the N-terminus of the Drosophila melanogaster Dalpha2 (=SAD) subunit was constructed and co-expressed with the chicken beta2 nAChR subunit in Xenopus laevis oocytes. The actions of the neonicotinoid insecticide imidacloprid were examined. Replacement of the region loop B to the N-terminus of the alpha4 subunit by the corresponding region of the Dalpha2 subunit had little effect on the concentration-response curve for imidacloprid. However, replacement of Glu219 by proline in the YXCC motif in loop C of the chimeric alpha4 subunit resulted in a marked displacement to the left of the concentration-response curve for imidacloprid not seen when an equivalent mutation was made in the alpha4beta2 nAChR. The results suggest that the region loop B to the N-terminus in the Dalpha2 subunit contributes to the high imidacloprid sensitivity of the hybrid Dalpha2beta2 nAChR.

Amino Acid Motifs↗

PubMed2001

Acute poisoning with the neonicotinoid insecticide imidacloprid in N-methyl pyrrolidone.

BACKGROUND: Imidacloprid [1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine, CAS 138261-41-3] belongs to a relatively new class of insecticidal chemistry, the chloronicotinyl neonicotinoid compounds. Animal studies indicate relatively low toxicity to mammals because they have resistant nicotinic receptor subtypes compared to insects, as well as protection of the central nervous system by the blood brain barrier. Despite wide usage, human exposure experience resulting in toxicity is quite limited. CASE REPORT: Here, we report a case of acute ingestion of an insecticide formulation containing 9.7% imidacloprid, <2 % surfactant, and the balance as solvent, N-methyl pyrrolidone. Clinical manifestation included drowsiness, disorientation, dizziness, oral and gastroesophageal erosions, hemorrhagic gastritis, productive cough, fever, leukocytosis, and hyperglycemia. The patient recovered without complication with supportive treatment and was discharged 4 days after ingestion. Follow-up barium upper gastrointestinal examination 1 month later was normal. Because moderate to high dose imidacloprid in animals causes central nervous system activation similar to nicotine, including tremors, impaired pupillary function, and hypothermia, it is unclear whether imidacloprid had a causal role in the patient's initial drowsiness and dizziness. It is more likely that the formulation ingredients, particularly N-methyl pyrrolidone, caused most of the clinical symptoms including minor central nervous system depression, gastrointestinal irritation, and hyperglycemia.

Blood Cell Count↗

PubMed2001

Comparison of neonicotinoid insecticides for use with biodegradable and wooden spheres for control of key Rhagoletis species (Diptera: Tephritidae).

Field-based studies and laboratory bioassays were conducted with apple maggot, Rhagoletis pomonella (Walsh), and blueberry maggot, Rhgoletis mendax Curran, flies to investigate the performance and duration of activity of insecticide-treated biodegradable and wooden spheres for control of Rhagoletis species. Four neonicotinoid insecticide treatments including imidacloprid, thiamethoxam, and thiocloprid at 2% (AI) were evaluated with biodegradable spheres. In 1999, significantly more apple maggot flies were found killed by imidacloprid-treated spheres compared with thiamethoxam-treated spheres during early and late season. In 2000, spheres treated with either of two formulations of imidacloprid killed significantly more apple maggot flies compared with thiamethoxam, thiocloprid, and untreated spheres. In blueberries, there were no significant differences between the numbers of blueberry maggot flies killed by both imidacloprid-treated or thiamethoxam-treated spheres in 1999. However, during the 2000 blueberry field season, both formulations of imidacloprid were significantly more effective in killing blueberry maggot flies compared with spheres treated with thiamethoxam, thiocloprid and untreated controls. Overall, spheres treated with thiocloprid were ineffective and did not kill significantly more apple maggot or blueberry maggot flies compared with the controls. Laboratory bioassays showed that the effectiveness of field-exposed spheres treated with imidacloprid at 4 and d 8% (AI) and thiamethoxam at 4% (AI) in killing apple maggot flies was not significantly reduced over a 12-wk aging period. Additionally, wooden spheres aged outdoors for 12 wk with and without mold maintained residual activity in laboratory tests, whereas biodegradable spheres of equal aging, with and without mold lost their effectiveness in killing apple maggot flies. In other studies, we confirmed that the addition of an external feeding stimulant (sucrose) significantly increases the effectiveness of both biodegradable and wooden spheres treated with imidacloprid at 2% (AI).

Animals↗

PubMed2006

Susceptibility of the adult eye gnat Liohippelates collusor (Diptera: Chloropidae) to neonicotinoids and spinosad insecticides.

Imidacloprid, thiamethoxam (first and second generation neonicotinoid insecticides), and spinosad (a naturally derived biorational insecticide) were evaluated in the laboratory against adult eye gnats, Liohippelates collusor (Townsend), using two modes of exposure. Ingestion experiments revealed that toxicity was the highest for thiamethoxam (Platinum soluble concentrate) followed by technical thiamethoxam, imidacloprid (Admire 2 flowable concentrate), and spinosad (Success* soluble concentrate). When incorporated into 5% sucrose solutions, eye gnat mortality was significantly increased compared to the same concentrations of aqueous insecticide solutions. Contact toxicity experiments revealed that thiamethoxam formulation (Platinum) was the most toxic, followed by technical thiamethoxam, imidacloprid, and spinosad. Increasing the duration of exposure time from 15 min to 30 min significantly increased adult eye gnat mortality, but no further mortality occurred by extending exposure from 30 min to 60 min. Our results suggest that Platinum has good ingestion and contact activity against adult eye gnats. Admire and Success have appreciable ingestion toxicity but low contact activity against adult eye gnats.

Animals↗

PubMed2003

Dihydropiperazine neonicotinoid compounds. Synthesis and insecticidal activity.

Syntheses of various isomeric dihydropiperazines can be approached successfully by taking advantage of the regioselective monothionation of their respective diones. Preparation of the precursor unsymmetrical N-substituted piperazinediones from readily available diamines is key to this selectivity. The dihydropiperazine ring system, as exemplified in 1-[(6-chloropyridin-3-yl)methyl]-4-methyl-3-oxopiperazin-2-ylidenecyanamide (4) and 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-methyl-3-oxopiperazin-2-ylidenecyanamide (25), has been shown to be a suitable bioisosteric replacement for the imidazolidine ring system contained in neonicotinoid compounds. However, placement of the cyanoimino electron-withdrawing group further removed from the pyridine ring, as in 4-[(6-chloropyridin-3-yl)methyl]-3-oxopiperazin-2-ylidenecyanamide (3a), or relocation of the carbonyl group, as in 1-[(6-chloropyridin-3-yl)methyl]-4-methyl-5-oxopiperazin-2-ylidenecyanamide (5), results in significantly decreased bioisosterism. The dihydropiperazine ring system of 4 and 25 also lends a degree of rigidity to the molecule that is not offered by the inactive acyclic counterpart 2-[(6-chloropyridin-3-yl)-methyl-(methyl)amino]-2-(cyanoimino)-N,N-dimethylacetamide (6). A pharmacophore model is proposed that qualitatively explains the results on the basis of good overlap of the key pharmacophore elements of 4 and imidacloprid (1); the less active regioisomers of 4 (3a, 5, and 6) feature a smaller degree of overlap.

Anabasine↗

PubMed2003

Determination of neonicotinoid pesticide residues in vegetables and fruits with solid phase extraction and liquid chromatography mass spectrometry.

A rapid and simple extraction method for the simultaneous analysis of five neonicotinoid insecticides has been developed. Twelve different fruit and vegetable matrixes were extracted with methanol and cleaned up using a graphitized carbon solid phase extraction cartridge loading with a 20% methanol solution. The concentrated eluate after methanol elution was then analyzed for pesticide residues by liquid chromatography/mass spectrometry in the APCI positive mode. The five pesticides including nitenpyram, thiamethoxam, imidacloprid, acetamiprid, and thiacloprid were recovered at 70-95% at spike levels of 0.1 and 1 mg/kg in bell pepper, cucumber, eggplant, grape, grapefruit, Japanese radish, peach, pear, potato, rice, and tomato. Relative standard deviations were less than 10% for all of the recovery tests. The proposed method is fast, easy to perform, and could be utilized for regular monitoring of pesticide residues.

Chromatography, Gas↗

PubMed2005

Neonicotinoid nitroguanidine insecticide metabolites: synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives.

Four neonicotinoid nitroguanidine insecticides (imidacloprid, thiamethoxam, clothianidin, and dinotefuran) acting as nicotinic agonists account for 10-15% of worldwide insecticide sales. General methods are needed for synthesis of their guanidine and aminoguanidine metabolites so they may be used as analytical standards and for evaluation of nicotinic receptor potency. The guanidines are obtained by treating the parent nitroguanidines with Fe powder in aqueous C2H5OH containing NH4Cl and isolated by silica chromatography. The aminoguanidines are prepared as mixtures with the guanidines on reaction of the parent nitroguanidines and Zn powder in glacial acetic acid. The imidacloprid aminoguanidine is isolated as the acetone imine or trifluoroacetamide and the clothianidin and dinotefuran aminoguanidines as the acetone imines using silica chromatography. Deprotection under acidic conditions then leads to the aminoguanidine.HCl salts. Because of stability considerations, a pH partitioning method is used to separate thiamethoxam aminoguanidine and guanidine. An alternate procedure to the aminoguanidine of imidacloprid (but not thiamethoxam, clothianidin, or dinotefuran) is reaction with hydrazine hydrate and NH4Cl in anhydrous C2H5OH. Ambiguities in further biological reactions are clarified by synthesizing authentic standards of three purported metabolites formed via the imidacloprid aminoguanidine: the 1,2,4-triazol-3-one derivative with ethyl chloroformate or ethyl pyrocarbonate, the acetaldehyde imine with acetaldehyde, and the 3-methyl-1,2,4-triazin-4-one derivative with ethyl pyruvate in refluxing toluene. The purported triazolone metabolite is reassigned as the aminoguanidine acetaldehyde imine probably formed as an artifact from acetaldehyde present in the ethyl acetate used for metabolite extraction. Potency at the Drosophila nicotinic receptor is greatly decreased on converting a nitroguanidine to a guanidine or aminoguanidine. In sharp contrast, potency at the vertebrate alpha4beta2 nicotinic receptor is generally increased on conversion from the nitroguanidine to aminoguanidine and particularly guanidine derivatives.

Amination↗

PubMed2001

Insecticidal and neural activities of candidate photoaffinity probes for neonicotinoid binding sites.

Photoreactive derivatives of imidacloprid and its nitromethylene analogue were synthesized as candidate photoaffinity probes for identifying the amino acid residues of nicotinic acetylcholine receptors (nAChRs) that interact with the neonicotinoid insecticides. When the candidate probes were injected into American cockroaches, the nerve cord neural activity initially increased, then ceased and death of the insect followed. Both the nerve cord and toxicity were enhanced by changing the photoreactive substituent from the para position to the meta position on the spacer benzyl moiety. When tested on a Drosophila SAD/chicken beta2 hybrid, recombinant nAChR expressed in Xenopus oocytes, the nitromethylene candidate probes showed agonist activity similar to that previously observed for imidacloprid.

Anabasine↗