52314-67-7Relevant articles and documents
Development of pyrethroid substrates for esterases associated with pyrethroid resistance in the tobacco budworm, Heliothis virescens (F.)
Huang, Huazhang,Ottea, James A.
, p. 6539 - 6545 (2004)
Assays to detect esterases associated with resistance to organophosphorus and pyrethroid insecticides in larvae of H. virescens were developed and evaluated. Cross-resistance to a variety of insecticides was measured in strains resulting from selection with either profenofos (OP-R) or cypermethrin (PYR-R), and resistance in both strains appeared to have a metabolic component. Esters were synthesized that coupled 3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate, the acid moiety of some pyrethroid insecticides, with groups (e.g., p-nitrophenyl-) that could be detected spectrophotometrically following hydrolysis of the resulting esters. Activities toward these pyrethroid esters were significantly higher in both resistant strains than those in a susceptible reference strain. In addition, all pyrethroid esters significantly increased the toxicity of cypermethrin in bioassays with larvae from both PYR-R and OP-R strains. The biological and biochemical activities of these compounds are compared with those with more conventional esterase substrates and insecticide synergists, and the utility of pyrethroid esters as components of rapid assays for detecting esterases associated with insecticide resistance is discussed.
A spectrophotometric assay for pyrethroid-cleaving enzymes in human serum
Butte, Werner,Kemper, Kerstin
, p. 49 - 53 (1999)
A direct continuous spectrophotometric assay to measure pyrethroid-cleaving enzymes in human serum was developed using cis- and trans-α-naphthyl-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate (cis- and trans-naphthyl-Cl2CA). These substrates show a structure very similar to the pyrethroids most often used (e.g. permethrin, cyfluthrin). The method is based on an increase in absorbance at 321 nm which occurs with the hydrolysis of the α-naphthyl esters to α-naphthol. The assay was optimised regarding type of buffer, pH and substrate concentrations, it was linear for at least 10 min at 37°C. These esterases were completely inhibited by bis-(4-nitrophenylphosphate), a specific carboxyesterase inhibitor. They displayed a great individual variability in human serum, activities were between less than 40 and 1000 U/l for cis-naphthyl-Cl2CA, between less than 40 and 2000 U/l for trans-naphthyl-Cl2CA, respectively. However, a correlation of enzyme activity to sex or age could not be observed. Furthermore, the activity of pyrethroid-cleaving esterases did not correspond to the activities of acylesterase, arylesterase, acetylcholinesterase or butyrylcholinesterase. Copyright (C) 1999 Elsevier Science Ireland Ltd.
Preparation method of cyanogen chrysanthemum ester insecticide
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Paragraph 0021; 0025, (2017/08/25)
The invention discloses a preparation method of a Clocythrin pesticide. The method comprises the following steps: a) mixing chrysanthemic acid and chrysanthemyl chloride and placing the mixture into a reaction vessel, adding triethylamine and introducing phosgene, slowly heating to 55-110 DEG C and fully reacting for 1-4 h so as to generate Chrysanthemoyl chloride; and b) dissolving sodium cyanide in an aqueous-phase Triton micellar solution, adding a catalyst and heating to 40 DEG C, slowly and dropwise adding mixed liquor of Chrysanthemoyl chloride and m-Phenoxybenzaldehyde, keeping the temperature and reacting for 1-4 h, cooling to 10 DEG C, adding a few amount of water and crystal seed, fully stirring and precipitating solids, and washing the precipitated solids with alkali, washing, filtering and drying so as to obtain a final product Clocythrin. The solvent in the invention can be recycled, use of the catalyst and water is reduced, and discharge of toxic wastewater and exhaust gas is minimized. The post-processing procedure is simple, and extraction and solvent distillation are not required. The final product can be obtained through simple centrifugation, washing and filtration. Discharge of solid wastes is decreased.
Synthesis of new chiral and nonchiral pyrido [3,2-e],[1,3,4] oxadiazine derivatives
Shet,Shelar,Manvi
body text, p. 149 - 156 (2011/01/03)
A chiral series of 6,7-dichloro-3-[3-(2,2-dihalovinyl)-2,2-dimethylcyclopropyl] -1H-pyrido [3,2-e],[1,3,4] oxadiazines (a-f) and a nonchiral series of 3-substituted, 6,7-dichloro-1H-pyrido [3,2-e][1,3,4] oxadiazines (a-g) have been synthesized. The synthesized compounds were characterized by IR, 1H-NR, HPLC and mass spectral data.
Synthesis and evaluation of a new series of substituted acyl(thio)urea and thiadiazolo [2,3-a] pyrimidine derivatives as potent inhibitors of influenza virus neuraminidase
Sun, Chuanwen,Zhang, Xiaodong,Huang, Hai,Zhou, Pei
, p. 8574 - 8581 (2008/02/07)
A series of substituted acyl(thio)urea and 2H-1,2,4-thiadiazolo [2,3-a] pyrimidine derivatives were prepared and both of their cell culture and enzymatic activity toward influenza virus were tested. Their in vitro neuraminidase inhibitory activities were in good agreement with the corresponding activities in cultured cells and they were evaluated as potent neuraminidase inhibitors. Of the analogues that demonstrated IC50s 0.1 μM, 16 and 60 were further investigated as candidates with the most potential for future development. The molecular docking work of the representative compound was described to provide more insight into their mechanism of action and further rationalize the observations of this new series herein, which represents a novel class of highly potent and selective inhibitors of influenza virus.
Synthesis and biological activity of N′-(substituted pyrimidin-2-yl)-N-dichlorochrysanthemoyl thioureas and their fused heterocyclic compounds
Xue, Sijia,Guo, Yanling,Li, Jingzhi,Ke, Shaoyong,Duan, Liping
, p. 262 - 264 (2007/10/03)
Five N′-(substituted pyrimidin-2-yl)-N-dichlorochrysanthemoyl thioureas (5a-5e) were synthesized from corresponding dichlorochrysanthemic acid in three steps. And two dichlorochrysanthemoylimino-2H-1,2,4-thiadiazolo[2,3-a] pyrimidines were prepared by oxidizing cyclization of 5a, 5b. The structures of these novel target compounds were confirmed by IR, 1H NMR and elemental analyses. The preliminary biological activity tests indicated that some target compounds had better insecticidal activity, fungicidal activity and so on mulriple efficacies.
Parallel synthesis and herbicidal activity of pyrethroid library
Xiao, Yuansheng,Liang, Xinmiao,Wu, Fan,Wan, Boshun
, p. 251 - 253 (2007/10/03)
A pyridine-containing pyrethroid library of 255 compounds was conveniently constructed using parallel synthesis. The library was screened by high through-put screening (HTS), and further study was focused on the compounds with initial bioactivities. The results suggest that some compounds could be potential herbicides.
Hapten and antibody production for a sensitive immunoassay determining a human urinary metabolite of the pyrethroid insecticide permethrin
Ahn, Ki Chang,Watanabe, Takaho,Gee, Shirley J.,Hammock, Bruce D.
, p. 4583 - 4594 (2007/10/03)
Permethrin is the most popular synthetic pyrethroid insecticide in agriculture and public health. For the development of the enzyme-linked immunosorbent assay (ELISA) to evaluate human exposure to permethrin, the glycine conjugate (DCCA-glycine) of a major metabolite, cis/trans-3-(2,2- dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid (DCCA), of permethrin was established as the target analyte. Four different types of the cis- and trans-isomers of immunizing haptens were synthesized as follows: N-(cis/trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carbonyl)glycine (hapten 3), N-(cis/trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1- carbonyl)-4-amino-L-phenyl-alanine (hapten 5), N-(N-(cis/trans-3-(2,2- dichlorovinyl)-2,2-dimethylcyclopropane-1-carbonyl)glycine)-amino-6-(2, 4-dinitrophenyl)aminohexanoic acid (hapten 9), and N-(cis/trans-3-(2,2- dichlorovinyl)-2,2-dimethylcyclopropane-1-carbonyl)glycine-4-oxobutanoic acid (hapten 24). Sixteen polyclonal antibodies produced against each cis- or trans-hapten-thyroglobulin conjugate as immunogens were screened against numerous hapten-bovine serum albumin conjugates as coating antigens. Six ELISAs with both a heterologous hapten structure and a heterologous hapten configuration (cis/trans or trans/cis) between antibody and coating antigen showed a high sensitivity for the target analyte. The IC50 was 1.3, 2.1, and 2.2 μg/L for the trans-target analyte and 0.4, 2.3, and 2.8 μg/L for the cis-target analyte. The immunizing haptens, except for hapten 5, provided the target specific antibodies. Molecular modeling of the haptens supported the selection of reasonable immunizing haptens that best mimicked the target analyte. Hapten 5 was suitable as a coating antigen rather than as an immunogen since it had a different geometry. Very low cross-reactivities were measured to permethrin, its free metabolite (DCCA), PBA-glycine conjugate, and glycine. The ELISA will be optimized for the detection of total cis/trans-DCCA-glycine in human urine samples.
Syntheses of 4-methoxymethylbenzyl permethrinates containing fluorine and their insecticidal activity
Zou, Xinzhuo,Qiu, Zongxing
, p. 173 - 179 (2007/10/03)
In order to investigate the relationship between the position of fluorine atom and insecticidal activity about 4-methoxymethylbenzyl permethrinates containing fluorine, 2 and 3-fluoro-4-methoxymethylbenzyl (±)-cis-permethrinate were synthesized. Their insecticidal activities were tested and the fluorine effect of title compounds was discussed.
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin
Lee, Hu-Jang,Shan, Guomin,Watanabe, Takaho,Stoutamire, Donald W.,Gee, Shirley J.,Hammock, Bruce D.
, p. 5526 - 5532 (2007/10/03)
A competitive enzyme-linked immunosorbent assay (ELISA) for the detection of deltamethrin was developed. Two haptens, cyano[3-(4-aminophenoxy)phenyl]methyl 1 R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate and 3-[(±)-cyano[1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropan ecarbonyloxy]methyl] phenoxyacetic acid, were synthesized and conjugated with thyroglobulin as immunogens. Four antisera were generated and screened against six different coating antigens. The assay that was the most sensitive for deltamethrin was optimized and characterized. The /50 for deltamethrin was 17.5 ± 3.6 μg/L, and the lower detection limit was 1.1 ± 0.5 μg/L. This ELISA assay had relatively low cross-reactivities with other major pyrethroids, such as permethrin, phenothrin, bioresmethrin, cyfluthrin, and cypermethrin. Methanol was found to be the best organic cosolvent for this ELISA, with optimal sensitivity observed at a concentration of 40% (v/v). The assay parameters were unchanged at pH values between 5.0 and 8.0, whereas higher ionic strengths strongly suppressed the absorbances. To increase the sensitivity of the overall method, a C18 sorbent-based solid-phase extraction was used for river water samples. River water samples fortified with deltamethrin were analyzed according to this method. Good recoveries and correlation with spike levels were observed.
