150824-47-8

Basic information

• Product Name: Nitenpyram
• Synonyms: -N-((6-Chloropyridin-3-yl);-N-ethyl-N'-methyl-2-nitroethene-1,1-diamine;NITENPYRAM PESTANAL, 100 MG;1,1-Ethenediamine, N-(6-chloro-3-pyridinyl)methyl-N-ethyl-N-methyl-2-nitro-, (1E)-;(E)-N-[(6-Chloropyridin-3-yl)methyl]-N-ethyl-N'-methyl-2-nitroethene-1,1-diamine;Nitenpyram;Nitendyram;Bestyuard
• CAS NO: 150824-47-8
• Molecular Formula: C11H15ClN4O2
• Molecular Weight: 270.72
• Product Categories: NA - NIPesticides;Alpha sort;Insecticides;N;Nicotinoids;N-PAlphabetic;Pesticides&Metabolites;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 150824-47-8.mol

Chemical Properties

• Melting Point: 83-84°
• Boiling Point: 417.2 °C at 760 mmHg
• Flash Point: >70 °C
• Appearance: Powder
• Density: 1.254 g/cm³
• Storage Temp.: 0-6°C
• PKA: 2.46±0.70(Predicted)
• BRN: 8489488
• CAS DataBase Reference: Nitenpyram(CAS DataBase Reference)
• NIST Chemistry Reference: Nitenpyram(150824-47-8)
• EPA Substance Registry System: Nitenpyram(150824-47-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: KH8589450
• Hazardous Substances Data: 150824-47-8(Hazardous Substances Data)

Usage

Uses

Used in Veterinary Medicine:
Nitenpyram is used as an ectoparasiticide for the treatment and prevention of flea infestations in animals. It is an orally administered flea adulticide, which means it is given to the animal in a way that targets adult fleas, helping to control and prevent further infestations.
Used in Pest Control Industry:
In the pest control industry, Nitenpyram is utilized as an insecticide to manage flea populations. Its effectiveness in controlling these ectoparasites makes it a preferred choice for both residential and commercial applications, contributing to a healthier environment for humans and animals alike.

Veterinary Drugs and Treatments

Nitenpyram is indicated as a flea adulticide in dogs and cats. It does not kill ticks, flea eggs, larvae or immature fleas. Nitenpyram may be effective for treating fly larvae (maggots) of various species.

Upstream product

• 120739-77-7 N-(6-chloro-pyridin-3-yl)methyl-N-ethylamine 
• 6061-04-7 1,1-dichloro-2-nitro ethylene 
• 74-89-5 methylamine 
• 120740-46-7 N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2-nitroethenamine 
• 102721-76-6 2-methylamino-2-methylthio-1-nitroethene 
• 1234618-74-6 C₁₀H₁₁Cl₂N₃O₂ 
• 70258-18-3 2-chloro-5-(chloromethyl)pyridine 
• 75-04-7 ethylamine 

Downstream Products

• 1443753-97-6 methyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-4-(3-fluorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-05-9 propyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-4-(3-fluorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443753-98-7 methyl 2-amino-6-[(6-chloro-3-pyridyl)methylethylamino]-4-(4-fluorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-06-0 propyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-4-(4-fluorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443753-99-8 methyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-4-(2,4-dichlorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-10-6 propyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-4-(2,4-dichlorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-00-4 methyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-4-(3,4-dichlorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-11-7 propyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-4-(3,4-dichlorophenyl)-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-01-5 methyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-1,4-dihydro-1-methyl-4-(4-methylphenyl)-5-nitro-3-pyridinecarboxylate 
• 1443754-15-1 propyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-1,4-dihydro-1-methyl-4-(4-methylphenyl)-5-nitro-3-pyridinecarboxylate 
• 1443754-02-6 methyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-1,4-dihydro-4-(2-methoxyphenyl)-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-13-9 propyl 2-amino-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-1,4-dihydro-4-(2-methoxyphenyl)-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1394005-27-6 ethyl 2-amino-4-(4-chlorophenyl)-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 
• 1443754-09-3 propyl 2-amino-4-(4-chlorophenyl)-6-[(6-chloro-3-pyridinylmethyl)ethylamino]-1,4-dihydro-1-methyl-5-nitro-3-pyridinecarboxylate 

Relevant articles and documents

Novel nitenpyram analogues with tetrahydropyridone-fixed cis-configuration: Synthesis, insecticidal activities, and molecular docking studies

To make further researches on the diversity of nitenpyram analogues with a cis-nitromethylene configuration, a series of cis-nitenpyram analogues (3a-q) with tetrahydropyridone-fixed cis-configuration were designed and synthesized. Preliminary bioassays showed that most of the designed nitenpyram analogues exhibited good insecticidal activity at 100 mg/L against Nilaparvata lugens and Myzus persicae, while analogues 3n afforded the best in vitro activity. Modeling the ligand-receptor complexes by molecular docking study revealed the analogues 3 with various substituents on phenyl show their different binding affinities to the insect nAChR, which also explained the structure-activity relationships observed in vitro. The Japan Institute of Heterocyclic Chemistry.

Preparation method of nitenpyram

The invention discloses a preparation method of nitenpyram. The method comprises the steps: carrying out a catalytic reaction in a low-grade chlorinated hydrocarbon solvent by taking N-ethyl-2-chloro-5-pyridinemethylamine and 1,1-dichloro-2-nitroethylene as starting raw materials and anion exchange resin as an acid binding catalyst, ending the reaction, and carrying out filtration to remove the anion exchange resin to obtain a solution of an intermediate compound (II); introducing methylamine gases to the solution of the intermediate compound (II), ending the reaction, and carrying out filtration; and concentrating a filtrate, and separating out a crystal to obtain a target compound (I). The invention provides the preparation method of a synthesis process of nitenpyram, the preparation method is few in reaction steps, simple in process as well as green and environment-friendly in process, and nitenpyram is high in yield and quality. Compared with an existing technical process, the preparation method is simple and convenient in process operation, low in operation cost, free of wastewater discharge, capable of realizing recycle of the catalyst, green and environment-friendly in process, high in product quality and yield, low in cost, very suitable for industrial production and extremely high in industrial application value.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

Nitrogenous heterocyclic compound and use thereof

The invention relates to a nitrogenous heterocyclic compound with a novel structure and use thereof. The nitrogenous heterocyclic compound is a compound represented by a formula I (shown in the description) or a salt thereof acceptable in pesticide science. The nitrogenous heterocyclic compound provided by the invention can serve as a pesticide. Compared with the existing pesticides, the pesticide provided by the invention has the advantages that the chemical stability is better, and meanwhile, the killing activity to resistant insects is better.

Improved preparation method of nitenpyram

The invention relates to an improved preparation method of nitenpyram. The method comprises steps as follows: firstly, 1,1-dichloroethylene has a reaction with a nitration agent comprising hydrochloric acid and sodium nitrate to generate 1,1,1-trichlorine-2-nitroethane, and the 1,1,1-trichlorine-2-nitroethane has an elimination reaction with NaHCO3 to generate a 1,1-dichlorine-2-nitroethylene intermediate; secondly, 2-chlorine-5-chloromethylpyridine has a reaction with ethylamine, and an ethylamine intermediate is prepared; thirdly, the ethylamine intermediate has a reaction with 1,1-dichlorine-2-nitroethylene intermediate and monomethylamine, and the final product nitenpyram is generated. NaNO3 is used to replace traditional nitric acid to serve as a target phase transfer catalyst, the reaction selectivity is improved, the yield is higher, and the operation is safer.

Design, synthesis, insecticidal evaluation and molecular docking studies of cis-nitenpyram analogues bearing diglycine esters

Based on the strategies of receptor structure-guided neonicotinoid design, a series of novel cis-nitenpyram analogues bearing diglycine esters were designed and synthesized. Preliminary bioassays indicated that the insecticidal spectra of the target compounds were expanded compared with our previous work, while all the target compounds presented excellent insecticidal activities against Nilaparvata lugens and Aphis medicagini at 100 mg/L. Among these analogues, 6b showed 100% mortality against Nilaparvata lugens (LC50 = 0.163 mg/L) and 90% against Aphis medicagini at 4 mg/L. SARs suggested that the insecticidal potency of our designed cis-nitenpyram analogues was dual-controlled by the size and species of the ester groups. The molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode compared with the previously designed compounds. Introduction of the peptide bond gave rise to more significant hydrogen bonds between the nitenpyram analogues bonding with the amino acid residues of insect nAChRs. The docking results explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these cis-nitenpyram analogues.

Cis-nitenpyram analogues containing 1,4-dihydropyridine: Synthesis, insecticidal activities, and molecular docking studies

A novel series of cis-nitenpyram analogues (2a-2p) were designed and prepared by introducing the 1,4-dihydropyridine, with their cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most compounds exhibited good insecticidal activities at 20 mg/L against Aphis medicagini, and analogues 2a and 2d afforded the best activity, and both of them had 100% mortality at 4 mg/L. In addition, molecular docking studies were also performed to model the ligand-receptor complexes, and the results explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides. Copyright

Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration

On the basis of the structure of heterocyclic-fused cis configuration derivatives and chain-opening neonicotinoids, two series of novel chain-opening tetrahydropyridine analogues were designed and synthesized. The preliminary bioassay tests were determined on cowpea aphid (Aphis craccivora) and armyworm (Pseudaletia separata Walker). The results showed that some of the target compounds exhibited repellent effects, whereas others showed good insecticidal activities.

Synthesis, insecticidal activity, crystal structure, and molecular docking studies of nitenpyram analogues with an ω-hydroxyalkyl ester arm anchored on the tetrahydropyrimidine ring

On the basis of the research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a new series of nitenpyram analogues with an ω-hydroxyalkyl ester arm anchored on the tetrahydropyrimidine ring was designed and synthesized to further enhance the strength of the hydrogen-bonding action they display in binding with the nAChR. The structures of the target compounds were characterized by 1H NMR, IR, and elemental analysis, and the cis configuration was confirmed by X-ray diffraction. Preliminary bioassays indicated that all of the nitenpyram analogues exhibited good insecticidal activity against Nilaparvata lugens and Myzus persicae at 100 mg/L, whereas analogues 4d and 6a afforded the best in vitro activity that had ≥95% mortality at 4 mg/L; the LC50 values of the analogues 4d and 6a were 0.170 and 0.154 mg/L, respectively. Structure-activity relationship (SAR) studies suggested that their insecticidal potency was also dual-controlled by the flexibility and size of the molecule. In addition, molecular docking simulations revealed that analogues 4d and 6a displayed stronger hydrogen-bonding action in binding with the nAChR, which explained the SARs observed in vitro and implied that the designed nitenpyram analogues are both practical and feasible.

Synthesis, insecticidal activity, and molecular docking studies of nitenpyram analogues with a flexible ester arm anchored on tetrahydropyrimidine ring

To make further researches on the structure-activity relationships (SARs) of our previous synthesized neonicotinoid compounds, a new series of nitenpyam analogues with flexible ester arm were synthesized. Preliminary bioassays indicated that all of our newly designed nitenpyam analogues exhibited good insecticidal activity at 100 mg/L, while analogues 4c and 4d afforded the best in vitro activity, and both of them had 100% mortality at 20 mg/L. The SAR studies suggested that their insecticidal potency was dual-controlled by the length of the ester arm and the size of the ester group. In addition, the molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode, which explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these novel nitenpyam analogues.