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  1. 홈
  2. /화합물

에테폰

Ethephon

HCID 27982
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
16672-87-0
표준 SMILES
O=P(O)(O)CCCl
InChIKey
UDPGUMQDCGORJQ-UHFFFAOYSA-N
분자식
C2H6ClO3P
평균 분자량
144.49 g/mol
단동위원소 질량
143.9743087

개요

(2-chloroethyl)phosphonic acid is a phosphonic acid compound having a 2-chloroethyl substituent attached to the P-atom. It has a role as a plant growth regulator.

이름 및 식별자

우선 이름
Ethephon
IUPAC
2-chloroethylphosphonic acid
현지명
에테폰
영어명
Ethephon
분자식
C2H6ClO3P
분자량
144.49

이름 및 동의어

ETHEPHON16672-87-02-Chloroethylphosphonic acid(2-Chloroethyl)phosphonic acidEthrelBromeflorCamposanCerone2-CepaEtheverseFlordimexKamposan
이름 더 보기
에테폰에테폰(ETHEPHON)CEPAEtephonPrepEthephoneetheponChloroethylchlorethephon
EthefonTomathrelCephaEthelFlorel2-Chloroethanephosphonic acidChloroethylphosphonic acidRoll-Fruct

데이터베이스 식별자

CAS
16672-87-0
PubChem CID
27982
DTXSID
DTXSID7024085
ChEMBL
CHEMBL1895474
ChEBI
CHEBI:52741
UNII
XU5R5VQ87S
EC Number
240-718-3
Nikkaji
J1.864C

물성

구조 계산 물성

XLogP
-1
극성 표면적
57.5 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
2
무거운 원자 수
7
형식 전하
0
복잡도
86.9

실험 및 물리화학적 성질

SpringerMaterials PropertiesFusion temperature
Pesticides · 6건

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Plant Growth Regulators

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Ethephon) -> USDA PDB

LogPlog Kow = -0.22
Density1.2 g/cu cm
Color/Form · 3건

Needles from benzene

White waxy solid

White crystalline powder

Solubility · 5건

Freely soluble in ethylene glycol, propylene glycol; practically insoluble in petroleum ether

VERY SLIGHTLY SOL IN AROMATIC SOLVENTS; VERY SOL IN ALCOHOL

Soluble in short-chain alcohols; sparingly soluble in nonpolar organic solvents; insoluble in kerosene and diesel oil.

Readily soluble in methanol, ethanol, isopropanol, acetone, diethyl ether and other polar organic solvents. Sparingly soluble in non-polar organic solvents such as benzene and toluene. Insoluble in kerosene and diesel oil.

For more Solubility (Complete) data for ETHEPHON (6 total), please visit the HSDB record page.

Boiling Point

안전 및 규제

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

GHS 분류

GHS Classification · 6건

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Danger

H302+H332 (14.4%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 4건

Commission Regulation (EC) No 1490/2002

Ethephon is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

06/85/EC, 2004/129/EC, Reg. (EU) 2015/415, Reg. (EU) 2018/917, Reg. (EU) 2019/707, Reg. (EU) 2020/869, Reg. (EU) 2021/745, Reg. (EU) 2022/708, Reg. (EU) 2023/2591, Reg. (EU) 2023/918, Reg. (EU) No 540/2011

Chlorethephon: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Phosphonic acid, (2-chloroethyl)-: Environment tier I assessment
Fire PotentialNONFLAMMABLE
Hazards Summary · 1건

May cause irritation; [HSDB] May cause burns; [eChemPortal: ESIS] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; A cholinesterase inhibitor; May be absorbed through skin; [MSDSonline]

FIFRA Requirements

화학 및 산업

약리 정보

Mechanism of Action · 3건

Plant growth regulator with systemic properties. Penetrates into the plant tissues, and is decomposed to ethylene, which affects the growth processes.

Studies have established the variety of target sites in pests and nontarget organisms at which the metabolically activated organophosphorus pesticides act. The high potency and specificity of the organophosphorus pesticides have made these cmpd useful chemical probes to further the knowledge of their mode of action and their metabolism. Many organophosphorus pesticides have been classified as phosphorylating agents. Some enzymes inhibited by organophosphorus cmpd have included acetylcholinesterase, kynurenine formamidase, neuropathy-target esterase, carboxyesterases, and other unknown esterases. Bioactive phosphorylating agents have been designed that are sufficiently stable to reach the organism, yet are reactive at the target site. The majority of organophosphorus bioactivations have been initiated by oxidation at sulfur or nitrogen connected to phosphorus, but some bioactivations involve oxidation at carbon or heteroatom centers distant from phosphorus. The phosphorus center is not the toxic site of some organophosphorus cmpd. The toxic effects of phosphinyliminodithiolanes, phosphorothionates, and ethephon are mediated through other reactive moieties.

Butyrylcholinesterase (BChE) is inhibited by the plant growth regulator (2-chloroethyl)phosphonic acid (ethephon) as observed 25 years ago both in vitro and in vivo in rats and mice and more recently in subchronic studies at low doses with human subjects. The proposed mechanism is phosphorylation of the BChE active site at S198 by ethephon dianion. The present study tests this hypothesis directly using [(33)P]ethephon and recombinant BChE (rBChE) with single amino acid substitutions and further evaluates if BChE is the most sensitive esterase target in vitro and with mice in vivo. [(33)P]Ethephon labels purified rBChE but not enzymatically inactive diethylphosphoryl-rBChE (derivatized at S198 by preincubation with chlorpyrifos oxon) or several other esterases and proteins. Amino acid substitutions that greatly reduce rBChE sensitivity to ethephon are G117H and G117K in the oxyanion hole (which may interfere with hydrogen bonding between glycine-N-H and ethephon dianion) and A328F, A328W, and A328Y (perhaps by impeding access to the active site gorge). Other substitutions that do not affect sensitivity are D70N, D70K, D70G, and E197Q which are not directly involved in the catalytic triad. The effect of pH and buffer composition on inhibition supports the hypothesis that ethephon dianion is the actual phosphorylating agent without activation by divalent cations. Human plasma BChE in vitro and mouse plasma BChE in vitro and in vivo are more sensitive to ethephon than any other esterases detected by butyrylthiocholine or 1-naphthyl acetate hydrolysis in native-PAGE. All mouse liver esterases observed are less sensitive than plasma BChE to ethephon in vitro and in vivo. More than a dozen other esterases examined are 10-100-fold less sensitive than BChE to ethephon. Thus, BChE inhibition continues to be the most sensitive marker of ethephon exposure.

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
265 °C (decomposes)
DecompositionHazardous Decomposition Products: Carbon monoxide, carbon dioxide, and hydrogen chloride. Reaction to alkaline materials causes evolution of ethylene gas. /Boll Buster/
Melting Point74-75 °C
Vapor Pressure · 2건

0.0000001 [mmHg]

< 7.5X10-8 mm Hg at 20 °C

Physical DescriptionVery hygroscopic solid; [Merck Index] Light beige powder; [MSDSonline]
Stability/Shelf Life · 3건

Aqueous soln are stable below pH 3.5. Above pH 3.5 hydrolysis begins with the release of free ethylene.

Stable at pH less than or equal to 3, decomposing to liberate ethylene at higher pH values.

Sensitive to UV irradiation.

물리화학적 성질

녹는점
70 · 70-72 °C(lit.)
끓는 점
265 °C · 265°C(lit.)
밀도
1.2 · 1.2000
저장 조건
2 · 2-8°C
수용성
Completely soluble in water
용해도
30 mg/ml,DMSO: · DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 25 mg/ml,PBS (pH 7.2): 10 mg/ml
산도 계수 (pKa)
1.88 · 1.88±0.10(Predicted)
물리적 상태
가루
색상
흰색에서 베이지색
Merck
14 · 14,3732
BRN
1751208 · 1751208
Henry's Law Constant
6.9 · 6.9×107 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
흡습성
주요 응용
농업환경
InChI
1S/C2H6ClO3P/c3-1-2-7(4,5)6/h1-2H2,(H2,4,5,6)
InChIKey
UDPGUMQDCGORJQ-UHFFFAOYSA-N
SMILES
OP(O)(=O)CCCl
LogP
-0.22 · -0.220
NIST
Phosphonic acid, (2-chloroethyl)-(16672-87-0)
EPA
Ethephon (16672-87-0)

화학적 성질

Ethephon is a white to tan powder. Commercial product is a white, waxy solid. Commercial products may be available as aqueous solutions or soluble concentrates.

· 5건

Tolerances are established for residues of the plant regulator ethephon [(2-chloroethyl) phosphonic acid] in or on food commodities as follows:[Table#4077]

A tolerance with regional registration, as defined in 180.1(m), of 0.1 ppm is established for residues of the plant regulator ethephon [(2-chloroethyl)phosphonic acid] in or on the food commodity sugarcane.

EPA has evaluated the dietary and residential risks from the supported registered uses of ethephon and has determined that there is a reasonable certainty that no harm to any population subgroup will result from exposure to ethephon. The acute dietary exposure estimates (food + water) for the U.S. population and all population subgroups are <100% of the acute Population Adjusted Dose (aPAD) and are below the Agency's level of concern at the 99.9th percentile of exposure. The highest estimated exposure was to children 1-2 years old at 77% of the aPAD. The chronic dietary exposure estimates (food + water) for the U.S. population are below the Agency's level of concern for the general U.S. population and all population subgroups. The highest estimated average chronic exposure occurred in children 1-2 years of age (16% of the cPAD). This assessment is considered conservative since field trial and tolerance level residues, and screening level water estimates were included in the dietary assessment. Therefore, the tolerances for ethephon established at 40 CFR part 180.300 are now considered reassessed under Section 408 (q) of FFDCA.

Based on the reviews of the generic data for the active ingredient ethephon, the Agency has sufficient information on the health effects of ethephon and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that products containing ethephon for all uses are eligible for reregistration. The Agency has determined that ethephon products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Ethephon is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0382; Pesticide type: Herbicide (growth regulator); Registration Standard Date: 09/01/88; Case Status: RED Approved 12/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Ethephon; Data Call-in (DCI) Date(s): 04/27/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Toxic Combustion ProductsHazardous Combustion Products: Carbon monoxide, carbon dioxide, and hydrogen chloride. /Boll Buster/
Hazard Classes and Categories · 5건

Acute Tox. 4 (67.7%)

Acute toxicity - category 3

Acute toxicity (Dermal) - Category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 3

Skin, Eye, and Respiratory IrritationsMay be irritating to exposed skin and eyes, or if inhaled.
Hazardous Reactivities and Incompatibilities · 2건

Incompatibility: Oxidizing agents ans alkaline materials. Corrosive to iron, mild steel, aluminum, and copper. /Boll Buster/

Incompatible with alkaline materials and with solutions containing metal ions, eg iron, zinc, copper, and manganese-containing fungicides.

안전 및 보호

Fire Fighting Procedures · 2건

Extinguishing Media: Considered non-combustible. Use medium appropriate to surrounding fire. Foam, dry chemical, carbon dioxide, water, or fog. /Boll Buster/

Special Fire Fighting Procedures: Wear protective clothing and self contained breathing apparatus. Do not breathe smoke, gases or vapors. keep non-essential personnel away from the immediate fire area, and out of any fall-out or run-off areas. /Boll Buster/

Storage Conditions · 1건

Keep out of reach of children and animals. Store in original containers only. Store in a cool, dry place. Carefully open containers. After partial use, replace lids and close tightly. Do not put concentrate or dilute material into food or drink containers. Do not contaminate water, food, or feed by storage or disposal. /Boll Buster/

Cleanup Methods · 4건

Small spill or leak: Avoid bodily contact. Confine spill by diking with suitable absorbent material and recover as much free lquid as possible. If spilled on the ground, the affected soil whould be removed to a depth of one or two inches and placed in an appropriate container for proper disposal in accordance with all Federal, State and Local regulations. /Boll Buster/

Large spill or leak: Follow basic procedure as outlined in small spill or leak steps above. Follow this by washing with a strong soap and water solution. Absorb any excess liquid and add to the drums of waste collected. Repeat if necessary. If spilled on the ground, the affected soil should be removed to a depth of one or two inches and placed in an appropriate container for proper disposal. Dispose in accordance with Federal, State, and Local regulations. /Boll Buster/

Do not allow any spill materials to enter waterways. /Boll Buster/

Large spills should be dammed-off and pumped into containers; soak up remainder with absorbent material and dispose of in accordance with local regulations.

Disposal Methods · 5건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Pesticide wastes are acutely hazardous. Improper disposal of excess pesticides, spray mixture, or rinsate is a violation of Federal law. If these wastes cannot be disposed of by use according to label instruction, contact your Stat Pesticide or Environmental Control Agency or the Hazardous Waste representative at the nearest EPA Regional Office for guidance. /Boll Buster/

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Must be disposed of by special means, e.g., suitable incineration, in accordance with local regulations.

Recommendable methods: Incineration. Peer-review: Large amt should be incinerated in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

Preventive Measures · 5건

Use Boll Buster only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /Boll Buster/

Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 48 hr. The REI is 72 hr in areas where average rainfall is less than 25 inches per year. /Boll Buster/

Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 48 hr. The REI is 72 hr in areas where average rainfall is less than 25 inches per year. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated such as plants, soil, or water, is coveralls over long sleeved shirt and long pants, chemical resistant gloves such as any water proof gloves, chemical resistant footwear plus socks, and protective eyewear. for overhead exposure, chemical resistant headgear is required. notify workers of the application by warning them orally and posting warning signs at entrances to treated areas. /Boll Buster/

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

For more Preventive Measures (Complete) data for ETHEPHON (10 total), please visit the HSDB record page.

Allowable Tolerances · 3건

Tolerances are established for residues of the plant regulator ethephon [(2-chloroethyl) phosphonic acid] in or on food commodities as follows: [Table#4076]

A tolerance with regional registration, as defined in 180.1(m), of 0.1 ppm is established for residues of the plant regulator ethephon [(2-chloroethyl)phosphonic acid] in or on the food commodity sugarcane.

Based on the information available, the existing maximum residue level (MRLs) for ethephon in walnuts, blueberries, pineapples, barley grain, rye grain and wheat grain are based on revoked CXLs (Codex MRLs) and need to be reconsidered. EFSA identified revised MRL proposals for all these commodities, except for blueberries for which no additional data is available, and proposed a revised list of MRLs.

Personal Protective Equipment (PPE) · 3건

Personal Protective Equipment (PPE): Applicators and other handlers must wear: Coveralls over short sleeved shirts and short pants, chemical resistant gloves made of any waterproof material (such as Nitrile, Butyl, Neoprene and/or Barrier Laminate), chemical resistant footwear plus socks, protective eyewear, chemical resistant headgear for overhead exposure adn chemical resistant apron when cleaning equipment or mixing and loading. /Boll Buster/

Wear a NIOSH approved pesticide respirator with organic vapor cartridge and pesticide prefilter. /Boll Buster/

GLOVES & EYE SHIELDS ARE ADVISED.

Other Standards Regulations and GuidelinesTHE MAXIMUM PERMISSIBLE AQUEOUS CONCN OF ETHEPHON WAS DETERIMINED IN LARGE BODIES OF WATER. BASED ON TOXICITY DATA THE MAX PERMISSIBLE CONCN OF ETHEPHON IN WATER RESERVOIRS WAS 3 MG/L.

독성 정보

Treatment · 1건

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 5건

PRETREATMENT OF WILD GARLIC (ALLIUM VINEALE L) SHOOTS WITH LOW CONCN OF 2-CHLOROETHYLPHOSPHONIC ACID (CEPA) INCR BASIPETAL TRANSLOCATION OF FOLIAR-APPLIED DICAMBA. ... ETHYLENE FROM CEPA ALTERED METABOLIC "SINK SOURCE" RELATIONSHIPS & PERMITTED INCR BASIPETAL TRANSPORT.

CUT FLOWERINGSTEMS OF TULIPA CULTIVARS WERE TREATED WITH SILVER THIOSULFATE AT 0.01 TO 2.0 MM FOR 10 MIN TO 24 HR. SILVER THIOSULFATE TREATMENT COMPLETELY ABOLISHED INHIBITION OF STEM ELONGATION CAUSED BY TREATMENT WITH ETHEPHON.

DIP TREATMENTS WERE GIVEN TO DORMANT POTATO TUBERS WITH MIXT OF ETHREL & GIBBERELLIC ACID. COMBINATION OF THESE WAS MORE EFFECTIVE FOR SPROUT INDUCTION THAN EITHER APPLIED ALONE. OPTIMUM PROPORTION OF GIBBERELLIN TO ETHREL IS 60-40.

A range of pesticides is widely used in pest management and the chances of exposure to multiple organophosphorus compounds simultaneously are high, especially from dietary and other sources. Although health hazards of individual organophosphorus insecticides have been relatively well characterized, there is lesser information on the interactive toxicity of multiple organophosphorus insecticides. The aim of this study is to elicit the possible interactions in case combined exposure of an organophosphorus pesticide chlorpyrifos and a plant growth regulator ethephon which are used worldwide. The ileum segments of 3 months old Wistar Albino male rats were used in isolated organ bath containing Tyrode solution. Ethephon and chlorpyrifos were incubated (10(-7) M concentration) separately or in combination with each other to ileum and their effects on acetylcholine-induced contractions were studied. The data obtained from this study show that, single and combined exposure to the agents caused agonistic interactions with regard to potency of acetylcholine whereas they caused a decrease on E(max) value of acetylcholine. These findings suggest that exposure to these agents which have direct and indirect cholinergic effects, may cause developing clinical responses with small doses and earlier but the extent of toxicity will be lower.

Health effects of subacute treatment of combinations of gibberellic acid and ethephon (2-chloroethylphosphonic acid) were investigated. Mice was used as an experimental model. Ten groups of male ICR (CD-1) mice were treated with oral doses of 25, 50 and 100 mg of either gibberellic acid (GA3), ethephon (2-chloroethylphosphonic acid) alone or in combination / kg body weight for 11 weeks. A significant dose dependent reduction in weight gain and low dry matter intakes were recorded in animals treated with the combination of both chemicals. Treated groups showed statistically significant increases in mean liver, kidney and spleen weights. Hemoglobin (Hb) and total erythrocyte count (TEC) decreased while total leukocyte count (TLC) was raised in all treated groups. Gibberellic acid (alone) treated animals showed the highest activity of liver aspartate aminotransferase (AST) while no significant variations were recorded among other groups. No significant differences were recorded in the activity of hepatic alanine aminotransferase (ALT). A highly significant variation was recorded among the three treatments in serum urea level. No significant difference was noted among the three treatments in serum creatinine. All treatments caused significant dose dependent increases in creatinine than that of the control group. A highly significant dose dependent variation occurred in acetyl choline esterase (AChE) activity among treated groups. Groups treated with ethephon alone showed the greatest inhibition in brain AChE.

Target OrgansNervous
Health Effects · 1건

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Hepatotoxicity · 1건

Ethephon is one of the most common plant growth regulators, and it used on fruits, vegetables, and cereals for promoting pre- and post-harvest ripening. Adult rats received ethephon at a dose of 200 mg/kg/day by gavage for 14 days. The orderly arrangement of hepatocytes was disrupted and was replaced by blood-filled sinusoids, and the hepatocytes appeared to be degenerated. The authors noted that the observations are probably indicative of degenerative changes associated with ethephon, and concluded that it has hepatotoxic potential.

Ecotoxicity Values · 5건

LC50; Species: Anas platyrhynchos (Mallard Duck) age 17 days; diet >5000 ppm for 8 days

LD50; Species: Chicken; oral 2740 mg/kg (95% confidence interval: 1522-4932 mg/kg)

LC50; Species: Anas platyrhynchos (Mallard Duck) diet >10000 ppm for 8 days

LD50; Species: Anas platyrhynchos (Mallard duck) age 20 weeks; oral via capsule 1998 mg/kg (95% confidence interval: 1748-2283 mg/kg)

For more Ecotoxicity Values (Complete) data for ETHEPHON (29 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1) experimental Koc values ranging from 608 to 8547(2) indicate that ethephon is expected to have low to slight mobility in most soil types but also suggest that it could be immobile in a few soil types(SRC). Ethephon is a diprotic acid and has a pKa1 of 2.5 and pKa2 of 7.2(3), indicating that this compound will exist entirely in the anion form in the environment. Anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize(SRC). Ethephon applied to field sites in Southern California, North Carolina, and Washington (2-6 lb/gallon soluble concentrate (SC)/L), at 1.6-2 lb active ingredient per acre, dissipated with half-lives of 7-25 days(1). Ethephon is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.5X10-8 mm Hg at 20 °C(3). Aerobic degradation of ethephon results in the formation of ethylene gas and soil bound 2-hydroxy ethyl phosphonic acid. Ethephon has a half-life of 7.5 days in sandy loam soil with only 4.7 percent remaining after 30 days(2).

AQUATIC FATE: Based on a classification scheme(1) experimental Koc values ranging from 608 to 8547(2) indicate that ethephon is expected to adsorb to suspended solids and sediment(SRC). A pKa1 of 2.5 and pKa2 of 7.2(3) indicates ethenone will exist entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3.2(SRC), from its log Kow of -0.22(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Anerobic degradation of ethephon results in formation of ethylene and soil bound 2-hydroxy ethyl phosphonic acid. Ethephon has a half-life of 5.3 days in flooded silt loam sediment and in a sediment/pond water system only 1.8 percent of ethephon remained after 30 days incubation(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethephon, which has an estimated vapor pressure of 7.5X10-8 mm Hg at 20 deg(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase ethephon may be removed from the air by wet or dry deposition(SRC). Ethephon does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOther Poison - Organophosphate
Milk ConcentrationsWHEN...FED TO LACTATING COW IN DIET @ 5 PPM, SOME OF DOSE WAS EXCRETED UNCHANGED IN URINE (9.8%), BUT NONE WAS PRESENT IN MILK OR FECES.
Toxicity Summary · 2건

Ethephon (2-chloroethylphosphonic acid) is a generally used plant growth regulator. The data on its toxic effects, especially in humans, are very limited. An 8-year retrospective study using data from the Ramathibodi Poison Center database (2013-2020) included 252 patients. Almost all patients were exposed through ingestion, mainly in unintentional circumstances. The clinical presentations included local effects, gastrointestinal, neurological, and respiratory symptoms. While most patients had either no or only minor clinical effects, six patients experienced moderate/severe effects, and two patients died. The cholinergic toxic syndrome was not frequently observed.

Ethephon is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Ecotoxicity Excerpts · 2건

/AQUATIC SPECIES/ Rainbow trout and Bluegill sunfish appeared relatively tolerant.

/PLANTS/ Phytotoxic when used at extremely high rates.

Signs and Symptoms · 1건

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

규제 정보

FIFRA Requirements · 5건

Tolerances are established for residues of the plant regulator ethephon [(2-chloroethyl) phosphonic acid] in or on food commodities as follows:[Table#4077]

A tolerance with regional registration, as defined in 180.1(m), of 0.1 ppm is established for residues of the plant regulator ethephon [(2-chloroethyl)phosphonic acid] in or on the food commodity sugarcane.

EPA has evaluated the dietary and residential risks from the supported registered uses of ethephon and has determined that there is a reasonable certainty that no harm to any population subgroup will result from exposure to ethephon. The acute dietary exposure estimates (food + water) for the U.S. population and all population subgroups are <100% of the acute Population Adjusted Dose (aPAD) and are below the Agency's level of concern at the 99.9th percentile of exposure. The highest estimated exposure was to children 1-2 years old at 77% of the aPAD. The chronic dietary exposure estimates (food + water) for the U.S. population are below the Agency's level of concern for the general U.S. population and all population subgroups. The highest estimated average chronic exposure occurred in children 1-2 years of age (16% of the cPAD). This assessment is considered conservative since field trial and tolerance level residues, and screening level water estimates were included in the dietary assessment. Therefore, the tolerances for ethephon established at 40 CFR part 180.300 are now considered reassessed under Section 408 (q) of FFDCA.

Based on the reviews of the generic data for the active ingredient ethephon, the Agency has sufficient information on the health effects of ethephon and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that products containing ethephon for all uses are eligible for reregistration. The Agency has determined that ethephon products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Ethephon is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0382; Pesticide type: Herbicide (growth regulator); Registration Standard Date: 09/01/88; Case Status: RED Approved 12/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Ethephon; Data Call-in (DCI) Date(s): 04/27/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

안전 데이터

wgk
2
rtecs
SZ7100000
ridadr
UN 2928 6.1/PG 2
독성
LD50 orally in mice: 2850 mg/kg (Hennighausen)
HS 번호
29319090
risk_code
20/21-34-52/53
hazard_code
C
safety_code
26-28-36/37/39-45-61-28A
포장분류
II
위험 등급
6.1
기존화학 물질
KE-05680
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Corr. 1C
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터
16672-87-0(Hazardous Substances Data)
Metabolism/Metabolites · 6건

AFTER EXPOSURE OF PLANTS TO CEPA, ETHYLENE WAS EVOLVED. PHOSPHATE & CHLORIDE WERE ALSO DETECTED.

IN LEAF & STEM TISSUE OF HEVEA BRASILIENSIS, 2-CEPA WAS CONVERTED INTO 13 & 20 COMPD, RESPECTIVELY. ONE OF COMPD OBTAINED FROM STEM & LEAF WAS IDENTIFIED ... AS 2-HYDROXYETHYL-PHOSPHONIC ACID. THIS COMPD ALSO FORMED ... WHEN ... INCUBATED FOR SEVERAL DAYS IN BUFFER SOLN @ ROOM TEMP.

In rye, ethephon was metabolized to ethylene and CO2.

In suspension cultures of Hevea brasiliensis, ethephon was metabolized to a number of compounds. One chromatographed similarly to 2-hydroxy-ethylphosphonic acid.

For more Metabolism/Metabolites (Complete) data for ETHEPHON (12 total), please visit the HSDB record page.

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Absorption, Distribution and Excretion · 2건

WHEN...FED TO LACTATING COW IN DIET @ 5 PPM, SOME OF DOSE WAS EXCRETED UNCHANGED IN URINE (9.8%), BUT NONE WAS PRESENT IN MILK OR FECES.

WITHIN 12 HR AFTER APPLICATION OF CEPA TO LEAF SURFACES OF APPLE & CHERRY TREES, ETHYLENE WAS DETECTED. CEPA IN LEAVES, HULL, SHELL & KERNEL OF WALNUTS WAS ALSO METABOLIZED.

용도 및 제조

Uses · 6건

Used as plant growth regulator to promote ripening in fruits, nuts, and other crops and to stimulate latex flow in rubber; [HSDB] Used primarily on cotton; [Reference #1]

Farming (Pesticides) [Category: Industry]

For ethephon (USEPA/OPP Pesticide Code: 099801) ACTIVE products with label matches. /SRP: Registered for 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./

A plant-growth regulator that increases rate of ripening of plants by promoting release of ethylene, stimulates rubber latex formation; ripening of sugarcane; flowering agent for pineapple; color enhancer.

In cotton, it is used as a boll opener and defoliant prior to harvesting.

Ethephon is used to promote fruit ripening, abscission, flower induction, breaking of apical dominance (inhibition of the growth of lateral buds by the terminal bud of a shoot), and other plant responses.

U.S. Production · 2건

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Consumption PatternsOn average about 4.1 million pounds of ethephon are used annually on 1.7 million acres. The crops with highest percent crop treated are tart cherries (61%), grapes (40%), processed tomatoes (15%), and cotton (10%).
Methods of Manufacturing · 2건

CLEAVAGE OF THE BIS(2-CHLOROETHYL) ESTER OF 2-CHLOROETHYL PHOSPHONIC ACID

Ethephon is made from tris(2-chloroethyl) phosphite by rearrangement to bis(2-chloroethyl)2-chloroethyl phosphonate followed by hydrolysis

Formulations/Preparations · 5건

Aqueous solutions, liquid concentrate.

Premix Partners: AMADS, chlormequat chloride; cyclanilide; mepiquat chloride.

Emulsifiable concentrate; suspension concentrate (flowable concentrate); soluble concentrate.

First Pick Cotton Harvest Aid/Defoliant (Nufarm Americas Inc): Ethephon 18.3%; Sulfuric acid, monourea adduct 58.6%.

For more Formulations/Preparations (Complete) data for ETHEPHON (44 total), please visit the HSDB record page.

Use Classification · 2건

Plant growth regulators

Environmental transformation -> Pesticides (parent, predecessor)

General Manufacturing Information · 3건

The WHO Recommended Classification of Pesticides by Hazard identifies ethephon (technical grade) as Class III: slightly hazardous; Main Use: plant growth regulator.

ETHEPHON SPRAY ON TOMATO TRANSPLANTS (LYCOPERSICON ESCULENTUM) 12 DAYS PRIOR TO PULLING RESULTED IN PARTIAL PROTECTION OF THE PLANTS FROM FROST INJURY AFTER TRANSPLANTING.

... Ethephon is an organophosphonate as opposed to an organophosphate. It is structurally different from and exhibits different physical/chemical properties than traditional organophosphate compounds. The toxicological profile of ethephon also differs from that of the organophosphate compounds.

응용 분야 · 1건

용도2-Chloroethyl)phosphonic acid (Ethephon) is the most widely used plant growth regulator. Ethephon is often used on wheat, coffee, tobacco, cotton, and rice in order to help the plant's fruit reach mat urity more quickly. The toxicity of Ethephon is actually very low, and any Ethephon used on the plant is converted very quickly to ethylene.

상·하류 제품 정보

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추가 설명

정의ChEBI: A phosphonic acid compound having a 2-chloroethyl substituent attached to the P-atom.