Imidacloprid /high quality CAS NO.138261-41-3

Product Name: Imidacloprid

Synonyms: 1-[(6-CHLORO-3-PYRIDINYL)METHYL]-N-NITRO-2-IMIDAZOLIDINIMINE;1-((6-Chloro-3-pyridinyl)methyl)-N-nitro-imidazolidinimine;((6-chloro-3-pyridinyl)methyl)-n-nitro-2-imidazolidinimine;AMIRE;ACIDOR;ADMIRE(R);IMIDACLOPRID PESTANAL;IMIDACLOPRID, 500MG, NEAT

CAS: 138261-41-3

MF: C9H10ClN5O2

MW: 255.66

EINECS: 200-835-2

Product Categories: -;INSECTICIDE;Endocrine Disruptors (Draft)Analytical Standards;IPesticides;Nicotinoids;Alpha sort;Alphabetic;Endocrine Disruptors (Draft)Pesticides&Metabolites;EPA;H-MAnalytical Standards;Insecticides;Method Specific;Agro-Products;Heterocycles;NULL;Agriculture

Mol File: 138261-41-3.mol

Imidacloprid Structure

Imidacloprid Chemical Properties

Melting point 144°C

Boiling point 93.5°C (rough estimate)

density 1.54

vapor pressure 2 x 10-7

refractive index 1.5790 (estimate)

Fp 2 °C

storage temp. 0-6°C

form neat

Water Solubility 0.061 g/100mL at 20 ºC

CAS DataBase Reference 138261-41-3(CAS DataBase Reference)

EPA Substance Registry System 1H-Imidazol-2-amine, 1-[(6-chloro-3-pyridinyl)methyl]- 4,5-dihydro-N-nitro-(138261-41-3)

Safety Information

Hazard Codes N,Xn,F

Risk Statements 11-20/21/22-36-22-20/22

Safety Statements 26-36-22-36/37-16-46-44

RIDADR UN 2588

WGK Germany 2

RTECS NJ0560000

HazardClass 6.1(b)

PackingGroup III

HS Code 29333990

Hazardous Substances Data 138261-41-3(Hazardous Substances Data)

MSDS Information

Provider Language

1-((6-Chloro-3-pyridinyl)methyl)-N-nitro-imidazolidinimine English

Imidacloprid Usage And Synthesis

Chemical Properties White Solid

Uses 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.

Uses 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.

These insecticides are used for foliar and soil application but imidacloprid also has a very high usage as a seed treatment. They have low rates of application: for example thiamethoxam is typically applied to foliage at rates of only 2.5-50 g ha-1. The neonicotinoids are polar, nonvolatile solids with high water solubilities and they are non-ionised at pH values typically found in the environment. The insecticides are not readily hydrolysed. Their polar nature makes them potentially mobile in soil but this is mitigated by their low rates of application and, for acetamiprid and nitenpyram, short persistence. hnidacloprid and thiamethoxam are sufficiently persistent to be used as soil treaments. All the insecticides are efficiently translocated in plants and are effective systemic agents against sucking pests.

Definition ChEBI: The E-isomer of imidacloprid.

Metabolic pathway The photolytic degradation of imidacloprid in different conditions yields diversified degradation products as indicated in the pathways. Photolysis in water gives 6- chloronicotinaldehyde, N-methylnicotinic acid amide, 1- (6-chloro-3-pyridinyl)methyl-2-imidazolinone and 6-chloro-3-pyridylmethylethylenediamine which are identified as main degradates together with a complex mixture of degradation products. On the surface of the tomato plant, four of the 14 metabolites are identified. In tobacco smoke, five degradates are detected, and in field soils, four metabolites are identified from the treated sugarbeet. As for the mammalian metabolites, the pathways are drawn tentatively by the author (see Klein145).

Degradation The hydrolysis of imidacloprid was investigated to US EPA guidelines. [14C]Imidaclopridw as added to sterile aqueous buffer solutions at pH 5,7 and 9 and incubated at 25 °C in the dark for up to 30 days. Analysis was by HPLC and TLC methods. No products of hydrolysis were found at pH 5 or 7. Some imidacloprid (7%) degraded at pH 9 (DT50 355 days) and two products were detected. The major product was not identified but may have resulted from a small transformation of the imidazole ring. The minor product was the cyclic urea (2) as shown in Scheme 1.

The photodegradation of imidacloprid in aqueous buffer at pH 7 was investigated to US EPA guidelines. The UV spectrum of imidacloprid has a maximum at 269 nm. Solutions were irradiated with a xenon lamp (8.9-9.5 μW cm-2) for up to 2 hours at 23-24.5 °C. Samples were analysed by TLC, HPLC and MS. Control samples were protected from irradiation. The DT50 for photolysis of imidacloprid was 57 minutes. No volatile products were produced but a large number of photoproducts were formed. A further study was done using a high initial concentration of imidacloprid so that photoproducts could be identified. Nine products were identified as shown in Scheme 1. The five major products were the cyclic guanidine derivative (3), the cyclic urea (2), an olefinic cyclic guanidine (4) and the fused ring products (5) and (6). These products together accounted for 48% of the applied radiocarbon after 2 hours of irradiation, when 23% of the applied imidacloprid remained. The proposed routes of aqueous photolysis were via loss of the nitro group followed by oxidation and piecemeal degradation of the imidazoline ring affording the minor products 7,8,9,10 and 11 as shown in Scheme 1(PSD, 1993).

Imidacloprid Preparation Products And Raw materials

Raw materials Ethyl acetate-->Chlorine-->Acrylonitrile-->Ethylenediamine-->Benzylamine-->Propionaldehyde-->Nitroguanidine-->Alkylimidazole

Preparation Products Imidacloprid+Validamycin+Monosultap,W.P.-->Imidacloprid+Buprofenzin,W.P.

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