基本情報
- 標準SMILES
COP(=S)(OC)Oc1ccc([N+](=O)[O-])c(Cl)c1- InChIKey
NZNRRXXETLSZRO-UHFFFAOYSA-N- 分子式
- C8H9ClNO5PS
- 平均分子量
- 297.65 g/mol
- 単同位体質量
- 296.9627583
名称と識別子
- 優先名称
- Chlorthion
- IUPAC
- (3-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-lambda5-phosphane
- 現地名
- チオりん酸O,O-ジメチルO-(3-クロロ-4-ニトロフェニル)
- 英語名
- CHLORTHION
- 分子式
- C8H9ClNO5PS
- 分子量
- 297.65
名称と別名
名称をさらに表示
データベース識別子
- CAS
500-28-7- PubChem CID
- 10372
- DTXSID
DTXSID9041784- ChEMBL
CHEMBL160606- ChEBI
CHEBI:167184- UNII
- 3NTK55T19G
- EC Number
- 207-902-5
- Nikkaji
- J152.065B
物性
構造計算による物性
- XLogP
- 3.5
- 極性表面積
- 106 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 6
- 回転可能結合数
- 4
- 重原子数
- 17
- 形式電荷
- 0
- 複雑度
- 318
実験および物理化学的性質
Solubility
Miscible in benzene, alcohol, ether
MISCIBLE IN AROMATIC SOLVENTS
SOL 1:25,000 IN WATER; READILY MISCIBLE IN TOLUENE & OIL
In water @ 20 °C, 40 mg/l; readily sol in common organic solvents with the exception of mineral oils
In water, 40 mg/l at 20 °C
Boiling Point
136 °C @ 0.23 mm Hg
YELLOW OIL; BP: 125 °C @ 0.1 MM HG /COMMERCIAL PRODUCT/
BP: 136 °C @ 0.3 mbar; 112 °C @ 0.05 mbar
Vapor Pressure
0.000004 [mmHg]
4X10-6 mm Hg @ 20 °C
Kovats Retention Index
1945;1964;1991;1982.4;1956.9
1980.9
物理化学的性質
- 融点
- 21 ° · 21°
- 沸点
- 0.1 · bp0.1 125°
- 比重(密度)
- 420 · d420 1.437
- 屈折率
- 20 · nD20 1.5661
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- Chloroform (Slightly), Methanol (Slightly)
- 外見
- 液体
- 水溶解度
- 40 mg/L · 40mg/L(20℃)
- BRN
- 2292513 · 2292513
- Henry's Law Constant
- 2.5 · 2.5×102 mol/(m3Pa) at 25℃, HSDB (2015)
- 主な用途
- 農業環境
- InChI
- 1S/C8H9ClNO5PS/c1-13-16(17,14-2)15-6-3-4-8(10(11)12)7(9)5-6/h3-5H,1-2H3
- InChIKey
- NZNRRXXETLSZRO-UHFFFAOYSA-N
- SMILES
- COP(=S)(OC)Oc1ccc(c(Cl)c1)[N+]([O-])=O
- EPAの化学物質情報
- Chlorthion (500-28-7)
安全と法規制
GHS分類
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral];H312: Harmful in contact with skin [Warning Acute toxicity, dermal];H332: Harmful if inhaled [Warning Acute toxicity, inhalation];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
Warning
危険有害性情報
Hazards Summary
A cholinesterase inhibitor; [HSDB] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
Hazard Classes and Categories
Acute Tox. 4 (97.6%);Acute Tox. 4 (100%);Acute Tox. 4 (100%);Aquatic Acute 1 (100%);Aquatic Chronic 1 (100%)
Acute toxicity - category 4;Acute toxicity - category 4;Acute toxicity - category 4;Hazardous to the aquatic environment (acute) - category 1;Hazardous to the aquatic environment (chronic) - category 1
Acute Tox. 4 *;Acute Tox. 4 *;Acute Tox. 4 *;Aquatic Acute 1;Aquatic Chronic 1
安全と保護具
Exposure Control and Personal Protection
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
Storage Conditions
...MUST BE STORED IN ITS SEALED ORIGINAL CONTAINERS, IN WELL-AIRED, FRESH & DRY STOREHOUSES OR IN SHADED & POSSIBLY WELL-AIRED PLACES. IT IS RECOMMENDED THAT THE PRODUCT'S TEMP...NOT EXCEED 25-30 °C, & KEEP...AWAY FROM SOURCES OF HEAT, FREE FLAMES OR SPARK-GENERATING EQUIPMENT. CONTAINERS MUST BE STACKED IN SUCH A WAY AS TO PERMIT FREE CIRCULATION OF AIR...AT BOTTOM & INSIDE OF PILES. STORAGE AREAS MUST BE LOCATED AT SUITABLE DISTANCE FROM INHABITED BUILDINGS, ANIMAL SHELTERS, & FOOD STORES; MOREOVER, THEY MUST BE INACCESSIBLE TO UNAUTHORIZED PERSONS, CHILDREN, & DOMESTIC ANIMALS. /PROTHOATE/
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
ANY MATERIAL SPILLED ON SKIN SHOULD BE IMMEDIATELY REMOVED WITH SOAP & WATER. WHEN SPRAYING & DUSTING...CONTAMINATED CLOTHING SHOULD BE CHANGED FREQUENTLY. /ORGANOPHOSPHORUS PESTICIDES/
CONTAINERS ... SHOULD BE CLEANED WITH A SUSPENSION OF BLEACHING POWDER IN WATER OR WITH OTHER ALKALINE SOLN AFTER SOAKING FOR 24 HR AND THEN BE RINSED WITH HOT WATER. /ORGANOPHOSPHORUS PESTICIDES/
THE STRICT OBSERVANCE OF HYGIENE RULES- NO SMOKING AND NO FOOD INTAKE DURING WORK, THOROUGH WASHING WITH SOAP AFTER WORK, CHANGING PROTECTIVE CLOTHING BEFORE GOING HOME- IS OF THE UTMOST IMPORTANCE. /ORGANOPHOSPHORUS PESTICIDES/
THE PROTECTIVE CLOTHING SHOULD BE KEPT IN SEPARATE PLACES WHERE IT CANNOT BE CONTAMINATED WITH TOXIC CHEMICALS. IT SHOULD BE FORBIDDEN TO KEEP THIS CLOTHING IN LIVING QUARTERS. PROTECTIVE CLOTHING MUST BE WASHED AT LEAST ONCE A WEEK AND EACH TIME IT IS CONTAMINATED WITH PESTICIDES. BEFORE WASHING THE CLOTHING SHOULD BE SOAKED FOR SEVERAL HOURS IN A CALCIUM CARBONATE SOLUTION. /PESTICIDES/
Personal Protective Equipment (PPE)
USE OF RUBBER GLOVES, GOGGLES, RESPIRATOR &...PROTECTIVE CLOTHING. /ORGANOPHOSPHORUS PESTICIDES/
WORKERS HANDLING AND APPLYING ORGANOPHOSPHORUS PESTICIDES ... MUST BE GIVEN PERSONAL PROTECTIVE EQUIPMENT COMPRISING OVERALLS MADE OF A TIGHT FABRIC OR POLYVINYL CHLORIDE, GLOVES AND RUBBER BOOTS. THEY MUST WEAR A RESPIRATOR WITH AN ACTIVATED-CARBON GAS FILTER CARTRIDGE AFFORDING PROTECTION FOR A DETERMINED NUMBER OF WORKING HOURS. THE EYES SHOULD BE PROTECTED BY GOGGLES. ... /ORGANOPHOSPHORUS PESTICIDES/
毒性情報
Environmental Fate
.../SOME ORGANOPHOSPHORUS INSECTICIDES/...BREAK DOWN INTO TOXIC COMPONENTS & ACCUM, PROBABLY AS RESULT OF AGING, WEATHERING, PLANT ALTERATION OR OTHER DEGRADATION. /ORGANOPHOSPHORUS INSECTICIDES/
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1800(SRC), determined from a log Kow of 3.45(2) and a regression-derived equation(3), indicates that chlorthion is expected to have low mobility in soil(SRC). Volatilization of chlorthion from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4X10-6 mm Hg(4), and water solubility, 40 mg/l(5). Chlorthion is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4X10-6 mm Hg(4).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1800(SRC), determined from a log Kow of 3.45(2) and a regression-derived equation(3), indicates that chlorthion is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4X10-6 mm Hg(7), and water solubility, 40 mg/l(4). According to a classification scheme(5), a measured BCF of 29(6), suggests the potential for bioconcentration in aquatic organisms is low.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorthion, which has a vapor pressure of 4X10-6 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorthion is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7 hrs(SRC), calculated from its rate constant of 5.9X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase chlorthion may be removed from the air by wet and dry deposition(SRC).
Medical Surveillance
Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. /SRP: Protect from exposure those individuals with/ organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/
Soil Adsorption/Mobility
The Koc of chlorthion is estimated as 1800(SRC), using a log Kow of 3.45(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chlorthion is expected to have low mobility in soil.
Human Toxicity Excerpts
A CHOLINESTERASE INHIBITOR. SYMPTOMS SIMILAR TO PARATHION.
SYMPTOMATOLOGY: 1. NAUSEA...VOMITING, ABDOMINAL CRAMPS, DIARRHEA, EXCESSIVE SALIVATION... 2. HEADACHE, GIDDINESS, VERTIGO & WEAKNESS. 3. RHINORRHEA & SENSATION OF TIGHTNESS IN CHEST ARE COMMON IN INHALATION EXPOSURE. 4. BLURRING OR DIMNESS OF VISION, MIOSIS... TEARING, CILIARY MUSCLE SPASM, LOSS OF ACCOMMODATION & OCULAR PAIN... MYDRIASIS...SOMETIMES SEEN...PROBABLY DUE TO SYMPATHO-ADRENAL DISCHARGE. 5. LOSS OF MUSCLE COORDINATION, SLURRING OF SPEECH, FASCICULATIONS & TWITCHING OF MUSCLES (PARTICULARLY OF TONGUE & EYELIDS), & GENERALIZED PROFOUND WEAKNESS. 6. MENTAL CONFUSION, DISORIENTATION & DROWSINESS. /PARATHION/
SYMPTOMATOLOGY: 7. DIFFICULTY IN BREATHING, EXCESSIVE SECRETION OF SALIVA & OF RESP TRACT MUCUS, ORONASAL FROTHING, CYANOSIS, PULMONARY RALES & RHONCHI & HYPERTENSION, (PRESUMABLY DUE TO ASPHYXIA). 8. RANDOM JERKY MOVEMENTS, INCONTINENCE, CONVULSIONS, & COMA. 9. DEATH PRIMARILY DUE TO RESP ARREST ARISING FROM FAILURE OF RESP CENTER, PARALYSIS OF RESP MUSCLES, INTENSE BRONCHOCONSTRICTION OR ALL THREE. /PARATHION/
TOXICITY IS LOW, IN SPITE OF HIGH ANTICHOLINESTERASE POTENCY (A DISTINCTION ASCRIBED TO SLOW TISSUE ABSORPTION).
Toxic by inhalation & ingestion.
Volatilization from Water/Soil
The Henry's Law constant for chlorthion is estimated as 4.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4X10-6 mm Hg(1), and water solubility, 40 mg/l(2). This Henry's Law constant indicates that chlorthion is expected to be essentially nonvolatile from water surfaces(3). Chlorthion's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces will not occur(SRC). Chlorthion is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4X10-6 mm Hg(1).
Non-Human Toxicity Excerpts
...CHLORTHION HAS RELATIVELY HIGH PERCUTANEOUS TOXICITY FOR DOGS. SINGLE DIPPING IN 0.5% 'EMULSIFIABLE SOLN'...WAS FATAL IN SOME CASES; REPEATED IMMERSION @ 4-DAY INTERVALS...ATTENDED BY SYMPTOMS OF TOXICITY. DOGS SUBJECTED TO TWO DIPPINGS IN 2% SOLN DIED 36 HR AFTER SECOND IMMERSION.
LETHAL ORAL DOSE IN MOST SUSCEPTIBLE ANIMAL...BABY CALF, WAS 50 MG/KG (23 MG/LB). CALVES WERE UNAFFECTED BY 25 MG/KG & ADULT CATTLE BY 50 MG/KG. SUBACUTE TOXICITY STUDIES INDICATE THAT DAILY IP DOSES OF 100 MG/KG (45 MG/LB) FOR APPROX 60 DAYS ARE REQUIRED TO REACH LD50 FOR RATS. DAILY ADMIN OF 50 MG/KG (23 MG/LB) BY SAME ROUTE WAS WITHOUT EFFECT.
LETHAL AMOUNTS OF ORGANOPHOSPHATES CAUSE DEATH BY A COMBINATION OF EFFECTS OF MUSCARINIC, NICOTINIC, & CENTRAL CHOLINERGIC OVERSTIMULATION &/OR RECEPTOR PARALYSIS. THUS HYPOTENSION, BRADYCARDIA, BRONCHOCONSTRICTION & BRONCHIAL FLUID ACCUM, INABILITY OF TONICALLY RIGID (OR FLACCID-PARALYTIC) RESP MUSCLES TO WORK PROPERLY, CYANOSIS & CENTRAL RESP DEPRESSION ARE MANIFESTED. ANIMAL DIES OF ASPHYXIA. FROM THIS IT WOULD SEEM THAT ORGANOPHOSPHATES SHOULD BE CLASSIFIED UNDER POISONS CAUSING...SIGNS OF RESP INSUFFICIENCY. ... IN PRACTICE, HOWEVER, THE OUTSTANDING CLINICAL SIGNS SEEN IN HERD OUTBREAKS & IN AMBULATORY ANIMALS ARE GENERALLY THOSE OF BEHAVIORAL, MOTOR, & MUSCLE STIMULATION. /ORGANOPHOSPHATE PESTICIDES/
SIGNS OF MUSCARINIC CHOLINERGIC OVERSTIMULATION INCLUDE PROFUSE SALIVATION; LACRIMATION; SEROUS OR SEROMUCOUS NASAL DISCHARGE; INCREASED RESPIRATORY SOUNDS...COLIC, & DIARRHEA...PUPIL CONSTRICTION, SWEATING, COUGHING; VOMITING...FREQUENT URINATION. ... CENTRAL NERVOUS SIGNS...INCLUDE...ANXIETY, RESTLESSNESS, & HYPERACTIVITY... /ORGANOPHOSPHATE PESTICIDES/
For more Non-Human Toxicity Excerpts (Complete) data for CHLOROTHION (6 total), please visit the HSDB record page.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of chlorthion with photochemically-produced hydroxyl radicals has been estimated as 5.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours (SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chlorthion was found to undergo hydrolysis at 20, 30, 40, 50, and 60 °C with a half-life of 138, 36, 10, 3, and 1 days, respectively(2). Stability also decreases with extremes of pH(2).
Environmental Fate/Exposure Summary
Chlorthion's production and former use as an insecticide may have resulted in its direct release to the environment. If released to air, a vapor pressure of 4X10-6 mm Hg at 20 °C indicates chlorthion will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorthion will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 7 hrs. Particulate-phase chlorthion will be removed from the atmosphere by wet and dry deposition. If released to soil, chlorthion is expected to have low mobility based upon an estimated Koc of 1800. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole. Chlorthion will not volatilize from dry soil surfaces based upon its vapor pressure. Chlorthion hydrolysis half-lives range from 138 to 1 days at temperatures from 10 to 60 °C. If released into water, chlorthion is expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. A BCF of 29 suggests bioconcentration in aquatic organisms is low. Chlorthion hydrolysis half-lives range from 138 to 1 days at temperatures from 10 to 60 °C. Occupational exposure to chlorthion may have occured through dermal contact with this compound at workplaces where chlorthion was produced or used. (SRC)
安全データ
- wgk
- 3
- rtecs
- TE8050000
- ridadr
- UN2811 6.1/PG 3
- 毒性
- LD50 in male, female rats (mg/kg): 880, 980 orally (Gaines)
- risk_code
- 20/21/22-50/53
- hazard_code
- Xn,N
- safety_code
- 13-60-61
- Hazard Classifications
- Acute Tox. 3 OralAcute Tox. 4 DermalAcute Tox. 4 InhalationAquatic Acute 1Aquatic Chronic 1
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 有毒物質データの
- 500-28-7(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
/It is/ rapidly hydrolyzed to dimethyl thiophosphate & 3-chloro-4-nitrophenol. To a limited extent, there is oxidation to the phosphate & hydrolysis to phosphoric acid & 3-chloronitrophenol.
3-CHLORO-4-NITROPHENYL DIMETHYL PHOSPHOROTHIOATE YIELDS 3-CHLORO-4-NITROPHENOL IN RAT, RABBIT, & IN FLY; IT YIELDS 3-CHLORO-4-NITROPHENYL DIMETHYL PHOSPHATE IN RAT, RABBIT, & FLY: NAKATSUGAWA T, TOLMAN NM, & DAHM PA; BIOCHEM PHARMAC 17: 1517 (1968). /FROM TABLE/
...INVESTIGATORS EXAMINED METABOLISM OF...CHLORTHION...IN RAT & COCKROACH. BY MEANS OF ION EXCHANGE CHROMATOGRAPHY, SUBSTANTIAL AMT OF DEALKYLATED ORGANOPHOSPHORUS COMPD WERE FOUND IN URINE OF RATS AFTER ORAL ADMIN.
用途と製造
Uses
Used as insecticide to control various agricultural and household pests; Also used to protect livestock and as veterinary anthelmintic; [HSDB]
No longer registered as a pesticide for use in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
For Chlorthion (USEPA/OPP PC code 034501) there are 0 labels match./SRP: Not registered for current use in the U.S./
Insecticide /SRP: Former use/
U.S. Production
(1972) LESS THAN 4.54X10+5 GRAMS
(1975) LESS THAN 4.54X10+5 GRAMS
Methods of Manufacturing
REACTION OF 4-NITRO-3-CHLOROPHENOL WITH O,O-DIMETHYL CHLOROTHIONOPHOSPHATE IN THE PRESENCE OF POTASSIUM CARBONATE & COPPER POWDER
Prepn: Schrader, Angew Chem 66, 265 (1954); US patent 2,701,259 (1955 to Bayer).
General Manufacturing Information
CHLORTHION CONTROLS WIDE RANGE OF AGRICULTURAL & HOUSEHOLD INSECTS, INCL HOUSEFLIES, MOSQUITOES, & ROACHES. CHLORTHION IS NO LONGER IN COMMON USAGE.
SOME OF THE LESS DANGEROUS /ORGANOPHOSPHORUS COMPOUNDS/...HAVE FOUND FAVOR AS SYSTEMIC INSECTICIDES FOR USE IN ANIMALS, PARTICULARLY AGAINST WARBLE-FLY INFESTATION IN CATTLE, & AS ANTHELMINTICS: THESE INCLUDE CHLORTHION, TRICHLORPHON, DIAZINON, & FENCHLORPHOS.
Not listed
Material believed to be no longer manufactured, or marketed for crop protection use.
応用分野
使用Insecticide.
上流・下流製品情報
上流原料
サプライヤー14 社
関連反応
関連ノート
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