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Chlorpyrifos
- Iupac Name：diethoxy-sulfanylidene-(3,5,6-trichloropyridin-2-yl)oxy-λ5-phosphane
- CAS No.: 2921-88-2
- Molecular Weight：350.58
- Modify Date.: 2022-11-29 10:03
- Introduction: Chlorpyrifos is a kind of crystalline organophosphate insecticide, acaricide and miticide used primarily for the control of foliage and soil-borne insect pests in many kinds of food and feed crops. Chlorpyrifos is widely used around the world to control pest insects in agricultural, residential and commercial settings. Its largest usage amount is consumed in corn. It can also be used on other crops or vegetables including soybeans, fruit and nut trees, cranberries, broccoli, and cauliflower. The non-agricultural applications include golf courses, turf, green houses, and no-structural wood treatment. It can also be used as a mosquito adulticide, and used in roach and anti bait stations in child resistant packaging. Its mechanism of action is through suppressing the nervous system of insects via inhibiting acetylcholinesterase.
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1. Names and Identifiers
- 1.1 Name
- Chlorpyrifos
- 1.2 Synonyms
0,0-Diethyl-O-[3,5,6-trichloro-2-pyridyl]phosphorothioate Brodan chlopyrifos chloropyrifos Chlorpyrifos,Chlorpyriphos Chlorpyriphos chlorpyriphos-ethyl Clorpyrifos CUGAT DOWCO DURSBAN EINECS 220-864-4 Empire Equity Eradex MFCD00041800 O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) phosphorothioate O,O-diethyl O-(3,5,6-trichloropyridin-2-yl) phosphorothioate O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate Pyrine suSCon Zidil
- 1.3 CAS No.
- 2921-88-2
- 1.4 CID
- 2730
- 1.5 EINECS(EC#)
- 220-864-4
- 1.6 Molecular Formula
- C9H11Cl3NO3PS (isomer)
- 1.7 Inchi
- InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3
- 1.8 InChkey
- SBPBAQFWLVIOKP-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CCOP(=S)(OCC)OC1=NC(=C(C=C1Cl)Cl)Cl
- 1.10 Isomers Smiles
- CCOP(=S)(OCC)OC1=NC(=C(C=C1Cl)Cl)Cl
2. Properties
- 2.1 Density
- 1.398
- 2.1 Melting point
- 42-44℃
- 2.1 Boiling point
- 200℃
- 2.1 Refractive index
- 1.56
- 2.1 Flash Point
- 181.1°C
- 2.2 Precise Quality
- 348.92600
- 2.2 PSA
- 82.48000
- 2.2 logP
- 5.36870
- 2.2 Solubility
- Insoluble. 0.00013 g/100 mL
- 2.3 VaporDensity
- 12.09
- 2.4 Appearance
- Chlorpyrifos is a white crystalline or irregularly flaked solid. It has a very faint mercaptan-type odor. It is not soluble in water. It can cause slight irritation to the eye and skin.
- 2.5 Carcinogenicity
- Some recent studies havereported associations between chlorpyrifos exposure andincreased risk for cancer for farm workers participating inthe Agricultural Health Study. Specifically, increased risk forglioma and rectal cancer has been associated with chlorpyrifosexposure . Chlorpyrifos was also one pesticideassociated with trends toward higher incidence of lungcancer through 2001 . For all cancers though, follow-up periods are short and exposures are based on recall soresults may be unreliable.
- 2.6 Chemical Properties
- Chlorpyrifos (diethyl 3,5,6-trichloro-2-pyridyl phosphorothionate) is a white crystal-like solid with a strong odor. It does not mix well with water, so it is usually mixed with oily liquids before it is applied to crops or animals (ATSDR, 1997).
- 2.7 Physical Properties
- Chlorpyrifos is a white crystalline or irregularly flaked solid. Chlorpyrifos has a very faint mercaptan-type odor. Chlorpyrifos is not soluble in water. Chlorpyrifos can cause slight irritation to the eye and skin.
- 2.8 Corrosivity
- Corrosive to copper and brass
- 2.9 Decomposition
- Decomposition temperature: approx 160 °C
- 2.10 HenrysLawConstant
- 2.93e-06 atm-m3/mole
- 2.11 Odor
- Mild mercaptan odor
- 2.12 pKa
- -5.28±0.10(Predicted)
- 2.13 Water Solubility
- H2O: Insoluble . 0.00013 g/100 mL
- 2.14 Stability
- Stable. Incompatible with strong oxidizing agents.
- 2.15 StorageTemp
- APPROX 4°C
3. Use and Manufacturing
- 3.1 Agricultural Uses
- Insecticide, Nematicide: A U.S. EPA restricted Use Pesticide (RUP).Chlorpyrifos is one of the most widely used insecticidesin the U.S., both around the home and in agriculture. Abroad-spectrum insecticide, originally used primarilyto kill mosquitoes but no longer registered for that use.Chlorpyrifos is effective in controlling cutworms, cornrootworms, cockroaches, grubs, flea beetles, flies, termites,fire ants, and lice. It is used as an insecticide on grain,cotton, field, fruit, nut and vegetable crops, as well as onlawns and ornamental plants. It is also registered for direct use on sheep and turkeys, for horse site treatment, dogkennels, domestic dwellings, farm buildings, storage bins,and commercial establishments. Chlorpyrifos acts on pestsprimarily as a contact poison, with some action as a stomach poison. It is available as granules, wettable powder, dustable powder and emulsifiable concentrate. Top crop usesin California include cotton, alfalfa, almonds, and oranges.
- 3.2 Definition
- ChEBI: An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.
- 3.3 Potential Exposure
- A potential danger to those involved in the manufacture, formulation, and application of this insecticide.
- 3.4 Shipping
- UN2783 Organo phosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3018 Organophosphorus pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- 3.5 Usage
- Chlorpyrifos is a broad-spectrum organophosphate insecticide sold under the trade names of Dursban, Empire 20, Equity, and Whitmire PT 270. First registered in 1965 to control foliage- and soil-borne insect pests on a variety of food and feed crops, it is one of the most widely used and one of the major insecticides used residentially (U.S. EPA, 2000).
4. Safety and Handling
- 4.1 Symbol
- GHS02;GHS07;GHS09;
- 4.1 Hazard Codes
- T; N
- 4.1 Signal Word
- DANGER
- 4.1 Risk Statements
- R25;R50/53
- 4.1 Safety Statements
- S1/2;S45;S60;S61
- 4.1 Packing Group
- III
- 4.1 Fire Hazard
- Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
- 4.2 Hazard Class
- 6.1(b)
- 4.2 Hazard Declaration
- H225; H315; H410
- 4.2 RIDADR
- UN 2783
- 4.2 Safety Profile
- Poison by ingestion, intraperitoneal, skin contact, and inhalation routes. Human systemic effects by ingestion: paresthesia, muscle weakness, coma. Experimental reproductive effects: developmental toxicity. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, NOx POx and SOx
- 4.3 Caution Statement
- P273-P301 + P310 + P330-P391-P501
- 4.3 WGK Germany
- 3
- 4.3 RTECS
- TF6300000
- 4.3 Safety
-
Hazard Symbols:?
T;
N?
Risk Codes: R25;R50/53
R25 :Toxic if swallowed.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.??
Safety Description: S1/2;S45;S60;S61
S1/2:Keep locked up and out of the reach of children.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
- 4.4 Specification
-
?Chlorpyrifos , its cas register number is 2921-88-2. It also can be called O,O-Diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate ; Phosphorothioic acid O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester ; Chlorpyrifos-ethyl ; Chlorpyritos ; Clorpyrifos ; Dursban HF ; Eradex ; Lorsban 4E-SG ; Pyrinex ; Super I.Q.A.P.T. ; Trichlorpyrphos ; and Dowco 179 .
- 4.5 Toxicity
- Oral-rat LD50: 82 mg/kg; Oral-Mouse LD50: 60 mg/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 3
Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Danger |
| Hazard statement(s) | H301 Toxic if swallowed H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P273 Avoid release to the environment. |
| Response | P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P391 Collect spillage. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
2921-88-2Total: 1 Synthesis Route
9. Other Information
- 9.0 Storage features
- The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
10. Computational chemical data
- Molecular Weight: 350.58g/mol
- Molecular Formula: C9H11Cl3NO3PS
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 348.926284
- Monoisotopic Mass: 348.926284
- Complexity: 303
- Rotatable Bond Count: 6
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 5
- Topological Polar Surface Area: 72.7
- Heavy Atom Count: 18
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccByMAJGAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgIAACAACAKhkiIyhJIIERCgACBiRACCgCAhJWAAmmAkT5gIJuLBkpPEMAhkwBHIyAaQEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
I’ve got to say, I did not know what chlorpyrifos [1] was and therefore had to look it up. Here it is: I can easily see an organothiophosphate with two sets of moieties within its molecule that give rise to different intermolecular forces: apolar or hardly polar regions (pyridine ring, ethyl chain...
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