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CAS No.: | 66230-04-4 |
---|---|
Name: | Esfenvalerate |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C25H22ClNO3 |
Molecular Weight: | 419.908 |
Synonyms: | Sumidan;a-Sum;Benzeneaceticacid, 4-chloro-a-(1-methylethyl)-, cyano(3-phenoxyphenyl)methyl ester,[S-(R*,R*)]-;(S)-a-Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)isovalerate;(S,S)-Fenvalerate;1S,1'S-Fenvalerate;Asana;Asana XL;Aa;Fenvalerate a;OMS 3023;S 1844;S 5602Aa;Sumi-Gold;Sumi-alfa;Sumi-alpha;Sumicidin Aa; |
Density: | 1.21 g/cm3 |
Melting Point: | 59 °C |
Boiling Point: | 538.9 °C at 760 mmHg |
Flash Point: | 279.7 °C |
Solubility: | 0.002 mg l-1 (25 °C) |
Appearance: | White crystalline solid |
Hazard Symbols: | T, N |
Risk Codes: | 23/25-43-50/53 |
Safety: | 24-36/37/39-45-60-61 |
Transport Information: | UN 2811 |
PSA: | 59.32000 |
LogP: | 6.67998 |
sodium cyanide
S-(+)-2-(4-chlorophenyl)isovaleryl chloride
3-Phenoxybenzaldehyde
esfenvalerate
Conditions | Yield |
---|---|
With N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide In water; 1,2-dichloro-ethane at 0 - 5℃; for 2.25h; | 36% |
α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate
A
(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
B
esfenvalerate
Conditions | Yield |
---|---|
With ammonia In methanol at -19 - 17℃; for 17 - 260h; Purification / work up; Resolution of racemate; | A n/a B 23% |
Stage #1: α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate In n-heptane; toluene for 2h; Heating / reflux; Resolution of racemate; Stage #2: In methanol at -16 - 0℃; for 65 - 240h; Purification / work up; | |
iron rust In methanol at -5 - 12℃; for 30h; Purification / work up; Resolution of racemate; |
S-(+)-2-(4-chlorophenyl)isovaleryl chloride
(S)-m-phenoxybenzaldehyde cyanohydrin
esfenvalerate
Conditions | Yield |
---|---|
With pyridine |
S-(+)-2-(4-chlorophenyl)isovaleryl chloride
(S)-m-phenoxybenzaldehyde cyanohydrin
A
esfenvalerate
B
[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane a) 0 deg C 1 h, b) r.t., overnight; Yield given. Title compound not separated from byproducts; |
2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
S-(+)-2-(4-chlorophenyl)isovaleryl chloride
A
esfenvalerate
B
[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 0.5h; Acylation; | A 495 mg B 645 mg |
2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride
(S)-m-phenoxybenzaldehyde cyanohydrin
A
(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
B
esfenvalerate
Conditions | Yield |
---|---|
With pyridine In hexane; acetate buffer at 0℃; pH=4.5; Title compound not separated from byproducts; |
(S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate
esfenvalerate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Pseudomonas cepacia lipase gelozyme; AcOH; 1-butanol / hexane / 3 h / 20 °C / Enzymatic reaction 2: pyridine / acetate buffer; hexane / 0 °C / pH 4.5 View Scheme |
2-(4-chlorophenyl)-3-methylbutyric acid
esfenvalerate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: via (S)-(-)-α-methylbenzylamine salt 2: SOCl2; DMF / CHCl3 / 1 h / 60 °C 3: 495 mg / pyridine / CH2Cl2 / 0.5 h View Scheme |
S-isopropyl-4-chlorophenylacetic acid
esfenvalerate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: SOCl2; DMF / CHCl3 / 1 h / 60 °C 2: 495 mg / pyridine / CH2Cl2 / 0.5 h View Scheme |
3-Phenoxybenzaldehyde
esfenvalerate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl / tetrahydrofuran; H2O / 0.5 h / 20 °C 2: 495 mg / pyridine / CH2Cl2 / 0.5 h View Scheme | |
Multi-step reaction with 3 steps 2: Candida cylindracea lipase / H2O / 23 h / 30 °C / pH 5 3: pyridine View Scheme | |
Multi-step reaction with 3 steps 2: 49 percent / Arthrobacter lipase / H2O / 23 h / 40 °C / further lipases and immobilized Arthrobacter lipase; effect of pH, temperature and (S)/(R) mixture of the acetate 3: pyridine View Scheme |
The IUPAC name of Fenvalerate alpha is [(S)-cyano-(3-phenoxyphenyl)methyl](2S)-2-(4-chlorophenyl)-3-methylbutanoate. With the CAS registry number 66230-04-4, it is also named as Esfenvalerate; Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-, (S)-cyano(3-phenoxyphenyl)methyl ester, (alphaS)-. The product's categories are insecticide; EQ - EZMethod specific; pesticides;Alpha sort; endocrine disruptors (draft) alphabetic; EPA; oeko-tex standard 100; pesticides& metabolites; pyrethroids. It is white crystalline solid which is soluble in acetone, acetonitrile, chloroform, ethyl acetate, dimethyl formamide, dimethyl sulfoxide, xylene and other organic solvents. Fenvalerate alpha is a kind of pesticide which is highly toxic. It will produce toxic nitrogen oxide and chloride gas when buring. In addition, the storage environment should be ventilate, low-temperature and dry.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 6.68; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.68; (4)ACD/LogD (pH 7.4): 6.68; (5)ACD/BCF (pH 5.5): 69665.47; (6)ACD/BCF (pH 7.4): 69665.47; (7)ACD/KOC (pH 5.5): 101909.01; (8)ACD/KOC (pH 7.4): 101909.01; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.586; (13)Molar Refractivity: 116.44 cm3; (14)Molar Volume: 346.7 cm3; (15)Polarizability: 46.16×10-24 cm3; (16)Surface Tension: 47.3 dyne/cm; (17)Enthalpy of Vaporization: 81.62 kJ/mol; (18)Vapour Pressure: 1.11E-11 mmHg at 25°C; (19)Rotatable Bond Count: 8; (20)Exact Mass: 419.128821; (21)MonoIsotopic Mass: 419.128821; (22)Topological Polar Surface Area: 59.3; (23)Heavy Atom Count: 30; (24)Complexity: 586.
Uses of Fenvalerate alpha: It is used for control of a wide range of insect pests on cotton, maize, groundnuts, soya beans, sugar cane, sunflowers, sorghum, fruit trees, vegetables, ornamentals, and noncrop land.
When you are using this chemical, please be cautious about it as the following:
It is toxic by inhalation and if swallowed and may cause sensitization by skin contact, so people should avoid contact with skin.. It is also very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) This material and its container must be disposed of as hazardous waste and avoid release to the environment.
People can use the following data to convert to the molecule structure.
1. SMILES: Clc1ccc(cc1)[C@@H](C(=O)O[C@H](C#N)c3cccc(Oc2ccccc2)c3)C(C)C;
2. InChI: InChI=1/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m1/s1.
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 2gm/kg (2000mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C27, 1991. | |
rat | LD50 | oral | 325mg/kg (325mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C287, 1991. | |
rat | LD50 | skin | > 5gm/kg (5000mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C287, 1991. |