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부토네이트

Butonate

HCID 31343
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
126-22-7
표준 SMILES
CCCC(=O)OC(C(Cl)(Cl)Cl)P(=O)(OC)OC
InChIKey
BKAQXYNWONVOAX-UHFFFAOYSA-N
분자식
C8H14Cl3O5P
평균 분자량
327.5 g/mol
단동위원소 질량
325.964444

개요

Butonate is a fatty acid ester and a butyrate ester.

이름 및 식별자

우선 이름
Butonate
IUPAC
(2,2,2-trichloro-1-dimethoxyphosphorylethyl) butanoate
현지명
부토네이트
영어명
butonate
분자식
C8H14Cl3O5P
분자량
327.527

이름 및 동의어

BUTONATE126-22-7TribufonButilchlorofosButonatoFekama AT 50Pedix PE 50ENT-20852ButonatButonatumNSC-17872Butanoic acid, 2,2,2-trichloro-1-(dimethoxyphosphinyl)ethyl ester
이름 더 보기
부토네이트T-113F-139NSC17872TRIBUPHONNSC 17872Butanoic acid esterBKAQXYNWONVOAX-UHFFFAOYSA-N
DTXSID5041697ENT 20,852Trichlorfon butanoic acid ester2,2,2-Trichloro-1-(dimethoxyphosphinyl)ethyl butanoateF 139O,O-Dimethyl (2,2,2-trichloro-1-n-butyryloxyethyl)phosphonate39M9R3Q494Dimethyl 1-butyryloxy-2,2,2-trichloroethylphosphonate

데이터베이스 식별자

CAS
126-22-7
PubChem CID
31343
DTXSID
DTXSID5041697
ChEMBL
CHEMBL1570266
ChEBI
CHEBI:82106
UNII
39M9R3Q494
EC Number
204-778-4
Nikkaji
J5.551D

물성

구조 계산 물성

XLogP
2.2
극성 표면적
61.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
5
회전 가능 결합 수
7
무거운 원자 수
17
형식 전하
0
복잡도
296

실험 및 물리화학적 성질

PesticidesPesticides -> Organophosphate Insecticides
OdorSlight ester odor
Density1.3742
Color/FormColorless, somewhat oily liquid
Solubility · 2건

Miscible with most organic solvents

DEODORIZED KEROSENE DISSOLVES 2-3%

Boiling Point129 °C at 0.5 mm HG
DecompositionWhen heated to decomposition it emits highly toxic fumes of /phosphorus oxides and hydrogen chloride/.
Vapor Pressure0.000112 [mmHg]
Refractive IndexIndex of refraction = 1.4707
Physical DescriptionColorless liquid; [HSDB]
Stability/Shelf Life · 2건

Stable to light but decomposes above 150 °C

Stable in neutral or acid aqueous solution; unstable in aqueous alkali.

Other Experimental Properties · 2건

Low smell & staining properties /Technical/

Wt/gal 11.5 lb

물리화학적 성질

끓는 점
0.5 · bp0.5 129°
밀도
1.39 · 1.390±0.06 g/cm3(Predicted)
Henry's Law Constant
3.3 · 3.3×104 mol/(m3Pa) at 25℃, HSDB (2015)
EPA
Butonate (126-22-7)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

유해성 정보

Hazards Summary · 1건

A cholinesterase inhibitor; [Hawley] No visible evidence of toxicity besides inhibition of cholinesterase activity in animal feeding studies; Not mutagenic; [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]

Special ReportsToxicology Review: Residue Reviews 46: 1 (1973)
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Standard Transportation Number49 216 74; Organophosphorus pesticide (compounds & preparations), liquid (poison b) (insecticides, nec, other than agricultural)
Shipment Methods and Regulations · 3건

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 5건

IMO 6.1; Organophosphorous pesticides, liquid, toxic; Organophosphorus pesticides, liquid,toxic,flammable, flashpoint not less than23 °C; Organophosphorous pesticides, solid, toxic

UN 2783; Organophosphorus pesticides, solid, toxic

UN 2784; Organophosphorus pesticides, liquid, flammable, toxic, flashpoint less than 23 °C

UN 3017; Organophosphorus pesticides,liquid, toxic, flammable, flashpoint not less than 23 °C

For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for BUTONATE (6 total), please visit the HSDB record page.

안전 및 보호

Exposure Control and Personal Protection · 1건

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]

Fire Fighting Procedures · 1건

Do not extinguish fire unless flow can be stopped; use water in flooding quantities as fog; solid streams of water may be ineffective; cool all affected containers with flooding quantities of water; apply water from as far a distance as possible; use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides/

Storage Conditions · 1건

...Must be stored in its sealed original containers, in well-aired, fresh and dry storehouses or in shaded and possibly well-aired places. It is recommended that the product's temperature... not exceed 25-30 °C, and 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 and inside of piles. Storage areas must be located at suitable distance from inhabited buildings, animal shelters, and food stores; moreover, they must be inaccessible to unauthorized persons, children, and domestic animals.

Disposal Methods · 1건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive MeasuresAvoid breathing vapors; keep upwind; avoid bodily contact with the material; wash away any material which may have contacted the body with copious amounts of water, or soap and water. /Organophosphorus pesticides/
Personal Protective Equipment (PPE)Wear self-contained breathing apparatus; wear full protective clothing. /Organophosphorus pesticides/

독성 정보

Ecotoxicity Values... The LC50 is 5-20 mg/l for some fishes, 5 mg/l for guppies, and > 1,000 mg/l for Daphnia and bacteria.
Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a structure estimation method(2), indicates that butonate is expected to have low mobility in soil(SRC). Volatilization of butonate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Butonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-4 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a structure estimation method(2), indicates that butonate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.0X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 4.1(SRC), from an estimated log Kow of 1.7(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). When butonate (1.5 kg/ha) was applied to a forest as the preparation Fekama A25, the butonate concentration in a creek in that forest was 1000 ug/L immediately after application, 0.1 ug/L after 6 hours, and 0.02 to 0.05 ug/L after 72 hours(8). At 150 to 250 hours post butonate application, the butonate degradation products trichlorfon and dichlorvos were present in the water at 2 to 3 and 0.06 to 0.08 ug/L, respectively(8). Eutrophic carp ponds containing plankton were treated with 400-1000 ug butonate. The half-life range of butonate in the pond water was found to be 46.5 to 108.7 hours(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butonate, which has an estimated vapor pressure of 1.1X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butonate 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 4.3 days(SRC), calculated from its rate constant of 7.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butonate may be removed from the air by wet or dry deposition(SRC). Butonate is susceptible to direct photolysis by sunlight and the photolysis products of an aqueous solution of butonate exposed to UV light were found to be vinyl butonate, chlorophos, DDVP, and HCl(4).

Adverse EffectsOther Poison - Organophosphate
Milk ConcentrationsSpraying 45 mg butonate/cow after morning milking gave residues of 0.03-0.1 mg/kg in milk from evening milking and equal residues of butonate metabolite, trichlorfon.
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of butonate can be estimated to be 1,100(SRC). According to a classification scheme(2), this estimated Koc value suggests that butonate is expected to have low mobility in soil.

Human Toxicity Excerpts · 2건

/SIGNS AND SYMPTOMS/ 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. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. ... 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction, or all three. /Parathion/.

/OTHER TOXICITY INFORMATION/ Its relatively low mammalian toxicity is attributed to rapid hydrolysis of the butyl and phosphate ester groupings.

Artificial Pollution SourcesButonate's former production and use as an insecticide(1) may have resulted in its direct release to the environment(SRC).
Environmental Bioconcentration · 1건

An estimated BCF of 4.1 was calculated for butonate(SRC), using an estimated log Kow of 1.7(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant for butonate is estimated as 3.0X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that butonate is expected to be essentially nonvolatile from water surfaces(2). Butonate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Butonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5건

/LABORATORY ANIMALS: Acute Exposure/ The alkylating properties of trichlorphone and butonate towards N-7 of guanine of nucleic acids was studied in-vivo in mice. Male mice were given 160 milligrams per kilogram (mg/kg) trichlorphone or 5 or 10 mg/kg butonate intraperitoneally. Both compounds were labeled with carbon-14 in the OCH3 positions. Animals were killed and nucleic acids were isolated from different organs. The nucleic acids and urine from the animals were analyzed for 7-methylguanine labeled with carbon-14. The excretion rate was determined by killing animals at intervals up to 24 hours. The amounts of 7-methylguanine excreted in urine were used to compare the methylating capacity of butonate and trichlorphone with known data for dichlorvos. Maximum amounts of radiocarbon in 7-methylguanine were found in lungs, kidneys and testicles, as well as in livers. These amounts were found shortly after killing and rapidly decreased with time. The excretion rate of 7-methylguanine was very rapid. For butonate the half life in liver was about 2 hours. In the whole body the half life of trichlorphone was less than 24 hours. Based on the excretion of 7-methylguanine in urine, the methylating capacity towards N-7 of guanine in nucleic acids was represented by a ratio of about 100:10:25 for dichlorvos, butonate and trichlorphone, respectively. The authors conclude that the methylating capacity of butonate is lower than that of trichlorphone as shown in-vivo, and is in agreement with the steric factors, the lipid/water partition and the rate of breakdown in the body.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... No effect was observed on rats fed at 0.25% in diet except for reduction in cholinesterase activity; loss of weight at 1%.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Toxicity was studied following intragastric butonate at 25, 50, and 100 mg/kg in horses. Toxic signs were evidenced by various combinations of depression, colic, muscular fasciculation, dyspnea, circling motions, incoordination, prostration, sweating, rigidity, nystagmus, relaxation of the tail and penis, coma, excretion of liquid feces, and depression of blood cholinesterase activity. There were no visible symptoms of toxicity after dietary admin of butonate 10, 25, and 50 mg/kg to horses.

/GENOTOXICITY/ [Mutation research 87:211 (1981).] Mutagenicity: DNA repair-deficient bacterial tests: negative.

/GENOTOXICITY/ Mechanism of genotoxic activity of butonate was investigated using the Ames test. Butonate was not mutagenic.

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of butonate with photochemically-produced hydroxyl radicals has been estimated as 7.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 4.7X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 4.7 years, 170 days, and 17 days at pH values of 7, 8, and 9, respectively(2). In a aqueous environment hydrolysis study, butonate was found to hydrolyze to the hydroxy deriviative chlorophos in acid media (pH 1.9 to 5) and dehydrochlorination occurred in alkaline media (pH 7.4 to 9.4) to produce vinyl butonate(3). Butonate is susceptible to direct photolysis by sunlight and the photolysis products of an aqueous solution of butonate exposed to UV light were found to be vinyl butonate, chlorophos, DDVP, and HCl(4).

Probable Routes of Human Exposure · 2건

Occupational exposure and general population exposure should be low or non-existent since butonate is no longer produced or used in the United States. In the past, butonate was applied directly to the environment as an insecticide and exposure to this compound was primarily in the workplace where butonate was produced or used. (SRC)

... Toxic by inhalation, skin absorption, and/or ingestion. /Organophosphorus pesticide/

안전 데이터

유해 물질 데이터
126-22-7(Hazardous Substances Data)

화학 및 산업

약리 정보

Mechanism of ActionParathion and its relatives are known to inhibit enzyme cholinesterase in all parts of the body by phosphorylating the active site. Toxic signs and symptoms are regarded as indirect consequences of this enzyme inactivation. /Parathion/
Biological Half-Life · 4건

The half-life of butonate in fruits and vegetables is 0.5-1.5 days.

It's half-life in blood stream of cattle is only about 3-4 min.

T/2 on apples and plums was 1.5 days; on cherries, 0.5 days.

/LABORATORY ANIMALS: Acute Exposure/ Male mice were given ... 10 mg/kg butonate intraperitoneally. Tthe half life in liver was about 2 hours. ...

Metabolism/Metabolites · 5건

In plants, butonate was metabolized by deacylation via trichlorphon and demethyltrichlorphon with dichlorvos as minor metabolite and by demethylation via demethylbutonate.

In the liver and blood of warm blooded animals, butonate was degraded primarily by hydrolysis of P-C bond with formation of dimethylphosphate. Small amount of the desmethylbutonate also formed in blood in vitro. Butonate was also hydrolyzed by fish. In insects, the organic acid was removed by esterase action and trichlorofon (Dipterex) was formed, which in turn was metabolized to DDVP.

In aq nonbiological media, butonate was degraded at pH less than 5.5 to trichlorphon, demethyltrichlorphon, and demethylbutonate, at pH greater than 5.5 preferably to vinylbutonate, demethylbutonate, and demethylvinylbutonate with traces of trichlorphon.

The effects of Phosphorus containing insecticides and their metabolites on blood cholinesterase activity were measured by determining the change in pH during hydrolysis of acetylcholine. Naled, dichlorvos, and trichlorfon were stronger inhibitors than butonate.

For more Metabolism/Metabolites (Complete) data for BUTONATE (6 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 1건

... The MAC is 2 mg/cu m. The half-life of butonate in fruits and vegetables is 0.5-1.5 days. The necessary waiting period after treatment is 3-7 days for general-purpose crops, and 10 days for crops to be used in baby food and dietetic preparations.

용도 및 제조

Uses · 6건

Used as insecticide and veterinary anthelmintic (schistosoma and nematodes) and ectoparasiticide; [HSDB]

No longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For butonate (USEPA/OPP Pesticide Code: 35701) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

MEDICATION (VET)

Insecticide

Methods of Manufacturing · 2건

Prepared by reacting Dipterex with N-butyric anhydride: Arthur, Casida, J Agr Food Chem 6, 360 (1958); from alpha-chloro-beta, beta, beta-trichloroethyl butyrate and dimethyl phosphite: Casida, Arthur, US patent 2,911,435 (1959) to Wisconsin Alumni Res Found).

/It is/ made by acylation of trichlorfon ...

Formulations/Preparations · 5건

T 113

TRIBUFON

ENT-20852

PEDIX-BUTONATE

For more Formulations/Preparations (Complete) data for BUTONATE (7 total), please visit the HSDB record page.

General Manufacturing Information · 3건

...It is compatible with non-alkaline pesticides.

Gels for control of equine endoparasites contain butonate, a thickening agent, acid scavenger, and others.

Anthelmintic for horses (Vet) /SRP66: Former use/

응용 분야

용도Insecticide.

공급사9 곳

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Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]
南通众合化工新材料有限公司0513-85666561 15950816326 · [email protected]

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