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Imidacloprid

Imidacloprid structure

CAS No:
138261-41-3
Formula:
C9H10ClN5O2
Chemical Name:
Imidacloprid
Synonyms:
2-Imidazolidinimine,1-[(6-chloro-3-pyridinyl)methyl]-N-nitro-,(2E)-;(2E)-1-[(6-Chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine;BAY-NTN 33893;Merit;Imidacloprid;NTN 33893;1-[(6-Chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine;Gaucho;Confidor 200SL;Confidor;Admire;Provado;Merit (insecticide);Confidor SL;CP 1;NTN 33893-240FS;Advantage Flea Adulticide;1-[(6-Chloro-3-pyridinyl)methyl]-4,5-dihydro-N-nitro-1H-imidazol-2-amine;Premise;Meritgreen;Hachikusan;1-(2-Chloro-5-pyridylmethyl)-2-(N-nitroimino)imidazolidine;Baimieshi;Prescribe;Trimax;Trimax (pesticide);Pro-Agro;Imicide;Admire 2F;Premis;Premise (insecticide);Gaucho Grande;Genesis;Marathon II;Preventol TM;Grubex;Bayer Advanced Season-Long Grub control;AGST 03001;Genesis (pesticide);Rinfidor;Comodor;Admire Pro;Quick-Bayt;Marathon;Marathon (insecticide);Trimax Pro;NUP 06024;Nuprid;NUP 06023;Alias 2F;AEF 106464;Couraze;Mallet 2F;Pasada;Confidate;Alias;NUQ 05054;Widow;Macho Max;Torrent;Advise;CoreTect;1-(6-Chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine;AE-F 106464-00GR01B0;Couraze Max;Senator;Confidor 240 O-TEQ;Confidor 200 O-TEQ;Timbertreat N 98;Senator (neonicotinoid);Jade;Gaucho 600FS;Kohinor;Confidor 70WG;Biunik 200SL;Provado 2F;Tanrec;Lada;Lada (insecticide);Kumiai Admire;Enforce (pesticide);Enforce;Yashijing;Confidor 100SL;Confidor 350SC;Acceleron IX 409;Merit 2F;Biotlin;Merit 75WP;936094-08-5;937701-26-3;1223531-53-0;1258963-04-0;1395144-24-7
Categories:
Agrochemicals > Insecticides

Description

Imidacloprid is a white solid crystal or powder under ambient conditions and have a low volatility (U.S. EPA, 2010; HSDB, 2006, 2012b).ChEBI: The E-isomer of imidacloprid.

Solid

Imidacloprid Basic Attributes

Molecular Weight：

255.66100

Exact Mass：

255.66

EC Number：

604-069-3

UNII：

3BN7M937V8

HScode：

2933399026

Characteristics

PSA：

89.04000

XLogP3：

1.47780

Density：

1.59 g/cm3

Melting Point：

144 °C

Boiling Point：

442.3ºC at 760mmHg

Flash Point：

221.3ºC

Refractive Index：

1.713

Water Solubility：

H2O: 0.061 g/100mL at 20 ºC

Storage Conditions：

0-6ºC

Vapor Pressure：

5.47E-07mmHg at 25°C

Toxicity：

Acute toxicity of imidacloprid was examined via the oral route in rats and mice, and via the inhalation and dermal routes in rats. Mice appeared to be more sensitive to the acute oral toxicity of imidacloprid than rats. In mice, the median oral lethal doses (LD50) ranged between 131-168 mg/kg (Category II oral toxicant).Other symptoms included decreased motility and lethargy. The same clinical signs were observed in rats following a 4-hour exposure to imidacloprid via the inhalation route.

Collision Cross Section：

158.48 Å² [M-H]-

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2588

wgk germany：

hazard class code：

R11

safety instructions：

S26; S36; S22

RTECS Number：

NJ0560000

Marks：

N; Xn; F

Storage features：

Separated from food and feedstuffs.

Stability/Shelf Life：

Stable to hydrolysis at pH 5-11.

Precautionary statement(s)：

P210-P280-P305 + P351 + P338

Hazard Statements：

H225-H302-H312-H319-H332

GHS Classification：

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P301+P312, P307+P311, P321, P330, P405, and P501|P260, P264, P270, P301+P312, P307+P311, P314, P321, P330, P405, and P501

Imidacloprid Use and Manufacturing

Uses

Nitroguanidine insecticide.Imidacloprid is the active ingredient in AdvantageTM used to control fleas in dogs and cats (HSDB, 2006). Clothianidin is the major metabolite of thiamethoxam and both compounds are registered for use as insecticides. Widespread use increased greatly in the 1990s as alternatives to organophosphosphorus and carbamate insecticides because of their much lower mammalian toxicity and resistance developed to other pesticides. Imidacloprid has become the most widespread insecticide used in the world. A neonicotinoid; the active ingredient in certain neuro-active insecticides. Reports show that when exposed to neonicotinid pesticides honeybees have probelms returnign home after foraging and bumble bee colonies grow poorly and produce fewer queens.The four neonicotinoids are acetamiprid (l),imidacloprid (2), nitenpyram (3) and thiamethoxam (4) (IS0 draft proposal name). They are potent broad spectrum insecticides possessing contact, stomach and systemic activity. The structures are given below and consist of substituted aromatic heterocyclic rings: 6-chloropyridinyl for acetamiprid, imidacloprid and nitenpyram and 3-chlorothiazole for thiamethoxam. Each compound has a methylene bridge, to a cyclic nitroguanidine moiety in imidacloprid and thiamethoxam, to a cyanoamidine in acetamiprid or to a diaminonitroethylene group in nitenpyram. The terminal group for all compounds is a strong electron-withdrawing substituent on an ethene or imino group.

Use Classification：

Insecticides|Pesticides -> Insecticides -> Nicotinoid insecticides -> Nitroguanidine insecticides

Agrochemical：

Imidacloprid has known environmental transformation products that include Imidacloprid-desnitro and Imidacloprid-urea.

Computed Properties

Molecular Weight:255.66
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:255.0523023
Monoisotopic Mass:255.0523023
Topological Polar Surface Area:86.3
Heavy Atom Count:17
Complexity:319
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzylamine

Acrylonitrile

Ethyl acetate

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