- Synthesis and biological activities of 3-(2-chloro-3,3,3-trifluoroprop-1- enyl)-2,2-dimethyl-N-substituted phenylcyclopropanecarboxamide
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Some amide compounds containing pyrethroids are synthesized. Their structures were confirmed by 1H NMR, MS and elemental analysis. The bioassay results indicated that they showed moderate fungicidal activity.
- Wang, Min-Jun,Sun, Na-Bo,Jin, Jian-Zhong,Zhang, Jian-Fen,Xu, Hui-Ying
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- Novel bifenthrin derivatives, and preparation method and application thereof
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The invention discloses novel bifenthrin derivatives, and a preparation method and application thereof. The novel bifenthrin derivatives have a structural formula as shown in a formula (I) which is described in the specification. In the formula (I), when R1 is H, R2 is a Cl or CF3 substituent group, and R3 is H or a substituted or unsubstituted non-heterocyclic or heterocyclic aryl group; when R1is a Cl substituted group, R 2 is H or a Cl or CF3 substituent group, and R3 is H or a substituted or unsubstituted non-heterocyclic or heterocyclic aryl group; the non-heterocyclic aryl group is a phenyl, naphthyl, anthryl, phenanthryl or pyrenyl group; and the heterocyclic aryl group is a five-to-nine-membered monocyclic or polycyclic heterocyclic aryl group with one or more O or S heteroatoms.According to the invention, a series of the novel bifenthrin derivatives are synthesized mainly by modifying and transforming ortho-position and terminal-position benzene rings on the intermediate benzene rings of bifenthrin; and the novel bifenthrin derivatives have excellent insecticidal and mosquito-killing effect on both larvae and adult mosquitoes, are significantly reduced in toxicity and improved in metabolic stability, and shows good application prospects.
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Paragraph 0092-0103
(2019/08/30)
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- NOVEL CRYSTALLINE FORM OF TEFLUTHRIN, PROCESS FOR ITS PREPARATION AND USE THEREOF
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Provided are the crystalline form of tefluthrin of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods and using the crystal to prepare stable agrochemical formulation. Also provided is the use of various solvents towards the crystalline form preparation conditions.
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Paragraph 0072-0073
(2019/01/05)
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- Preparation method of cyanogen chrysanthemum ester insecticide
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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.
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Paragraph 0029; 0033
(2017/08/25)
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- Design, synthesis, crystal structure and insecticidal evaluation of novel arylpyrazole derivatives containing cyhalothroyl thiourea moiety
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On the basis of the commercial insecticide Fipronil, a series of novel arylpyrazole derivatives containing the cyhalothroyl thiourea moiety were designed and synthesized via the key intermediate 5-amino-3-cyano-1- (substituted phenyl) pyrazole. The structures of target compoundswere characterized by 1H NMR, FT-IR, elemental analysis and single crystal X-ray diffraction analysis. Their insecticidal activities against Culex pipiens and Musca domesticawere evaluated. The results of bioassays indicated that title compounds exhibited satisfactory insecticidal activities. Among those, Compound 7t ((E)-3-(2-chloro- 3, 3, 3-trifluoroprop-1-en-1-yl)-N- ((3-cyano-1-(2, 6- dichloro-4-(trifluoromethyl) phenyl)-1H-pyrazol-5-yl) carbamothioyl)- 2, 2-dimethyl cyclopropane carboxamide) exhibited the best insecticidal activities because of its lowest KT50 values,which are superior to the commercial insecticide Dextral tetramethrin and similar to Prallethrin. The type and position of substituent on the benzene ring played important roles on the biological activities of target compounds.
- Han, Zhen-Yu,Wu, Wen-Yuan,Chen, Fu-Li,Guan, Xi-Lin,Fu, Xiao-Huan,Jiang, Peng,Wan, Rong
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p. 911 - 918
(2017/08/15)
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- Bifenthrin semi-antigen, and quick-detection apparatus and preparation method thereof
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The invention provides a bifenthrin semi-antigen, and a quick-detection apparatus and a preparation method thereof. The bifenthrin semi-antigen is represented as the formula (I). The bifenthrin semi-antigen is used for detecting bifenthrin metabolite, has
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Paragraph 0055; 0057
(2016/10/10)
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- Synthesis and biological activities of 3-1-(3-(2-Chloro-3,3,3-trifluoro- prop-1-enyl)-2,2-dimethylcyclopropanecarbonyl)-3-substituted phenyl thiourea
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Some thiourea compounds containing pyrethroids are synthesized. Their structures were confirmed by 1H-NMR, MS and elemental analysis. The bioassay results indicated that they showed moderate insecticidal and fungicidal activity.
- Sun, Na-Bo,Lei, Chao,Jin, Jian-Zhong,Zhang, Jian-Fen
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p. 1359 - 1363
(2014/01/06)
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- Synthesis and characterization of novel N-acyl cyclic urea derivatives
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A series of novel N-acyl cyclic urea derivatives (3a-3l) have been synthesized by the reactions of 1-((6-chloropyridin-3-yl)methyl)imidazolidin-2- one (1) with various acyl chlorides in the yields of 35-95%. Subsequently, N-acyl cyclic urea derivatives co
- Yang, Tingting,Gao, Guohua
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experimental part
p. 304 - 316
(2012/06/29)
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- 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
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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.
- Sun, Chuanwen,Zhang, Xiaodong,Huang, Hai,Zhou, Pei
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p. 8574 - 8581
(2008/02/07)
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- PROCESS FOR PRPARING GAMMA-CYHALOTHRIN
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A process for the preparation of gamma-cyhalothrin comprising steps of a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride and b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride with the (S)-cyanohydrin of 3-phenoxy benzaldehyde (III).
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- PRODUCTION PROCESS OF GAMMA-CYHALOTHRIN
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A process for the preparation of gamma-cyahlothrin comprising a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride; b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride with 3-phenoxy benzaldehyde in the presence of a source of cyanide to form a diastereoisomeric mixture of cyhalothrin isomers and c) epimerising the diastereoisomeric mixture under conditions in which the least soluble diastereoisomer crystallises from solution.
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- Process for the preparation of enantiomerically pure pyrethroid insecticides
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A process for producing compounds of formula (VIIa) and (VIIb) wherein X is a leaving group; Y and Y1 are idependently Cl or Br; and Z is Cl, Br or a haloalkyl group which process comprises a) reacting a compound of formula (VII) wherein X, Y, Y1 and Z are as defined for compounds (VIIa) and (VIIb) with a substantially optically pure chiral amine in a solvent to form a diastereoisomeric salt; b) separating the diastereomeric salt of each enantiomer; c) converting the diastercomeric salt of each anantiomer separately to compounds of formulae (VIIa) and (VIIb) respectively by acid or base hydrolysis, the use of the compounds in making pyrethroid insecticides and novel intermediates.
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- PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY PURE PYRETHROID INSECTICIDES
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A process for producing compounds of formula (VIIa) and (VIIb) wherein X is a leaving group; Y and Y are idependently Cl or Br; and Z is Cl, Br or a haloalkyl group which process comprises a) reacting a compound of formula (VII) wherein X, Y, Y and
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- Development of Immunoassays for Type II Synthetic Pyrethroids. 1. Hapten Design and Application to Heterologous and Homologous Assays
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Immunoassays differing in selectivities for pyrethroid insecticides have been developed for the detection of type II pyrethroids, including deltamethrin, cypermethrin, and λ-cyhalothrin. Two approaches were employed in hapten synthesis to raise antibodies with different cross-reactions: (1) use of three spacer attachment points to offset different parts of molecules from the points of attachment and (2) use of linkers with and without bulky groups in the enzyme conjugate to reduce antibody affinities for the spacer arm in the immunoassay. The first approach resulted in the preparation of three series of haptens with a spacer attached (1) at the aromatic moiety of pyrethroid, (2) through the middle of the molecule, and (3) at the cyclopropane moiety. Haptens based on the derivatives of the pyrethroid metabolites were also prepared. The second approach involved the use of a linker with a bulky (cyclohexane ring) functionality for preparation of an enzyme conjugate. While most combinations of antibody and conjugate could be used in immunoassays for detection of deltamethrin in the 10-100 μg/L range, in most cases the limits of detection of the assays (for total isomers of a particular target pyrethroid) were lowered 10-50 fold by treatment of the pyrethroid standards with dilute alkali to produce a different isomer mix. Fifteen antisera prepared using 8 haptens were each screened with 14 peroxidase conjugates, and 26 antibody/conjugate combinations were selected for further study on the basis of the assay sensitivity, dynamic behavior, and specificity for deltamethrin, cypermethrin, and cyhalothrin. These immunoassays provided 50% inhibition of antibody binding (IC50) values between 1.5 and 4.2 μg/L of isomerized total deltamethrin and limits of detection of 0.2-0.7 μg/L. The most sensitive immunoassay for total deltamethrin was obtained using cypermethric acid-KLH as the immunogen and a conjugate based on a derivative of cypermethrin coupled through the middle of the molecule to peroxidase. These provided an IC50 of 2 μg/L and a limit of detection of 0.2 μg/L of isomerized total deltamethrin. However, no particular hapten design produced antisera of clearly superior sensitivity or specificity for deltamethrin. Differing cross-reactions with the closely related pyrethroids, deltamethrin, cypermethrin, and cyhalothrin, were obtained, and for several antibodies the cross-reaction as well as the limits of detection could be altered by varying the conjugate combinations. Each of the 12 antibody/enzyme conjugate combinations that sensitively detected deltamethrin were very stereospecific, detecting the αS, 1R cis, (DM1), and αR, 1R cis (DM2) isomers only; the assay sensitivity was greater for the latter isomer.
- Lee, Nanju,McAdam, David P.,Skerritt, John H.
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p. 520 - 534
(2007/10/03)
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- New Chiral Agents for Resolution of Racemic cis-Permethric and cis-Z-cyhalothric Acids
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Resolution of racemic pyrethroid acids (cis-permethric and cis-Z-cyhalothric) using stable optically active amines derived from natural monoterpene (+)-3-carene and preparation of optically active esters of the pyrethroid acids are described.
- Popov, Sergey A.,Tkachev, Alexey V.
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p. 1013 - 1018
(2007/10/03)
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- 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives
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Disclosed are novel compounds of the formula STR1 wherein R1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R2 is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substituted-vinylcyclopropanecarbonyl group. The compounds wherein R2 is other than hydrogen are insecticides.
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- 4-Phenyl-2-indanyl esters of 1R,cis-3-(2-halo-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid
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Insecticidal 4-phenyl-2-indanyl 1R,cis-3-(2-halo-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates having a racemic or optically active indanyl moiety, methods of preparation and use, and efficacy data against representative insect species are disclosed and exemplified.
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- Insecticidal (2,6-dimethyl-3-substituted phenyl)methyl cyclopropanecarboxylates
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(2,6-Dimethyl-3-substituted phenyl)methyl cyclopropanecarboxylates and insecticidal compositions containing these esters are useful for the control of a broad range of insects and acarids.
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- (+)-4-Substituted-2-indanols
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Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R2 is other than hydrogen are insecticides.
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- Process for producing (+)-4-substituted-2-indanols
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Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R2 is other than hydrogen are insecticides.
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- 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives
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Disclosed are novel compounds of the formula STR1 wherein R1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R2 is hydrogen, a tetramethylcylopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2-dichlorocyclopropanecarbonyl group, or a substituted-vinyl-cyclopropanecarbonyl group. The compounds wherein R2 is other than hydrogen are insecticides.
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- 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives
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Disclosed are novel compounds of the formula STR1 wherein R1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R2 is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substituted-vinylcyclopropanecarbonyl group. The compounds wherein R2 is other than hydrogen are insecticides.
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- 1R,Cis-3-(2-halo-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid derivatives
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1R,cis-trifluoromethylethenylcyclopropanecarbonyl compounds of the formula STR1 in which X is halogen and R is halogen, hydroxy, lower alkoxy or an optionally substituted 1,1'-biphenyl-3-methyloxy group, their method of preparation and utility as insecticides and intermediates therefore are described and exemplified.
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- Insecticidal perhaloalkylvinylcyclopropanecarboxylates
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Perhaloalkylvinylcyclopropanecarboxylates having the general formula STR1 are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR1 where R1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
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- (+)-4-Substituted-2-indanol insecticidal ester derivatives
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Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R2 is other than hydrogen are insecticides.
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- 4-Substituted-2-indanols
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Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, and R2 is hydrogen. The compounds are intermediates of cyclopropanecarboxylate and related insecticides.
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- Insecticidal pyrethroid enantiomer pair
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An insecticidal enantiomer pair consisting essentially of a substantially equimolar mixture of S-4-phenyl-2-indanyl 1R, cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate and R-4-phenyl-2-indanyl 1S,cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate, its preparation by liquid chromatography, and its utility as an insecticide are described and exemplified.
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- 4-Substituted-2-indanol insecticidal ester derivatives
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Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, and R2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group. The compounds wherein R2 is other than hydrogen are insecticides.
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- Arthropodicidal 2,2-dimethyl-3-(2-perfluoroalkyl-2-perhaloalkyl-vinyl)-cyclopropanecarboxylic acid esters
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2,2-Dimethyl-3-(2'-perfluoroalkyl-2'-perhaloalkyl-vinyl)-cyclopropane of the formula STR1 in which R is --COOR2, --COOH, --CO--Halogen, --CN or --CO--CH3, R1 is fluorine or CF3, R3 is fluorine, chlori
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- Halogenated esters
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A compound of formula: STR1 wherein one of R1 and R2 represents a group of formula: where W represents an atom of hydrogen, fluorine or chlorine and m has the value one or two, and the other of R1 and R2 represents an atom of fluorine, chlorine or bromine or a group of formula: STR2 where each of X, Y and Z independently represents an atom of hydrogen, fluorine or chlorine, and R3 represents an atom of hydrogen, or the cyano or ethynyl group. The compounds are useful against insect or acarine pests.
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- Insecticidal benzylfurylmethyl perhaloalkylvinylcyclopropanecarboxylates
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Perhaloalkylvinylcyclopropanecarboxylates having the general formula STR1 are disclosed wherein one of Y and Z is a perhaloalkyl group and the other is hydrogen, halogen, or lower alkyl. Compounds in which R is hydroxy, halogen or lower alkoxy are interme
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