S,S,S-트리부틸 삼티오인산

Tribufos

HCID 5125CAS 78-48-8

기본 정보

표준 SMILES
CCCCSP(=O)(SCCCC)SCCCC
InChIKey
ZOKXUAHZSKEQSS-UHFFFAOYSA-N
분자식
C12H27OPS3
평균 분자량
314.5 g/mol
단동위원소 질량
314.09616511

개요

Tribufos is a colorless to pale yellow liquid with a skunk-like odor; it is used only as a defoliant (a chemical that removes leaves) for cotton plants. Removing the leaves keeps certain pests that may be found on the leaves from damaging the cotton before it is picked.

이름 및 식별자

우선 이름
Tribufos
IUPAC
1-bis(butylsulfanyl)phosphorylsulfanylbutane
현지명
S,S,S-트리부틸 삼티오인산
영어명
1,2,4-Tributylphosphorotrithioate
분자식
C12H27OPS3
분자량
314.51

이름 및 동의어

Tribufos78-48-8ButifosDEF defoliantButiphosS,S,S-TRIBUTYL PHOSPHOROTRITHIOATEMerphos oxideButyl phosphorotrithioateTBTPDe-GreenTribuphosS,S,S-Tributyl trithiophosphate
이름 더 보기
S,S,S-트리부틸삼티오인산S,S,S-트리부틸삼티오인산트리뷰포스S,S,S-트리부틸 삼티오인산S,S,S-트리부틸포스포로트리티오산1,2,4-트리부틸포스포로트리티오에이트DEFDEF 6DEF(R)DEGREEN
Phosphorotrithioic acid, S,S,S-tributyl esterFossfallOrtho phosphate defoliantFosfallButyl phosphorotrithioate ((BuS)3PO)DTXSID1024174TributylphosphorotrithioateB-1,776

데이터베이스 식별자

CAS
78-48-8
PubChem CID
5125
DTXSID
DTXSID1024174
ChEMBL
CHEMBL1901047
ChEBI
CHEBI:38737
UNII
53075G8GRF
EC Number
201-120-8
Nikkaji
J2.827D

물성

구조 계산 물성

XLogP
3.2
극성 표면적
93 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
12
무거운 원자 수
17

실험 및 물리화학적 성질

Pesticides · 6건

Pesticide -> EPA IRIS

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (DEF (Tribufos)) -> USDA PDB

Pesticide

LogP · 2건

log Kow = 5.7

3.23

OdorMercaptan-like odor
Density1.057 at 20 °C
Color/FormColorless to pale yellow liquid
Solubility · 2건

Soluble in aliphatic, aromatic, and chlorinated hydrocarbons and alcohols. Completely miscible in dichloromethane, n-hexane, 2-propanol, and toluene.

In water, 2.3 mg/L at 20 °C

물리화학적 성질

녹는점
-25 ° · <-25°
끓는 점
0.3 · bp0.3 150°; bp4 166.5°
밀도
204 · d204 1.0552
굴절률
20 · nD20 1.534
저장 조건
0 · 0-6°C
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
화학적 성질 · 1건

Tribufos is a colorless to yellow liquid. Tribufos is relatively stable to acids and heat and is hydrolyzed slowly under alkaline conditions. Tribufos has a mercaptan or skunk-like odor. Tribufos has a mercaptan or skunk-like odor. Practically insoluble in water (2.3×10-4 g/ 100 mL); completely miscible in dichloromethane, n-hexane, 2-propanol, toluene.

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H301 (80.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P273, P280, P301+P316, P301+P317, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 88 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

유해성 정보

Regulatory Information · 5건

Hazard Traits - Carcinogenicity; Neurotoxicity

Phosphorotrithioic acid, S,S,S-tributyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorotrithioic acid, S,S,S-tributyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

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

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Phosphorotrithioic acid, S,S,S-tributyl ester: Human health tier I assessment
DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards Summary · 2건

Tribufos is a colorless to pale yellow liquid with a skunk-like odor; it is used only as a defoliant (a chemical that removes leaves) for cotton plants. Removing the leaves keeps certain pests that may be found on the leaves from damaging the cotton before it is picked.

Delayed neuropathy has been reported in at least one agricultural worker; Causes moderate skin and minimal eye irritation in rabbits; Anemia observed in females during one year feeding at nominal doses (NOEL for anemia in females = 0.4 mg/kg); Effects in two year feeding study with rats include bilateral retinal and optic nerve atrophy, cataract, corneal opacity, and signs of anemia, but no adverse effects observed for oncogenicity or neurotoxicity; Reproductive toxicity observed at doses maternally toxic; No evidence of teratogenicity in two animal studies; Evidence for delayed neurotoxicity in hens exposed to single dermal dose of 250-1000 mg/kg; No evidence of mutagenicity; [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]

안전 및 보호

Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
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]

Storage Conditions · 1건

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

Cleanup Methods · 2건

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

독성 정보

Toxicological InformationCDC-ATSDR Toxicological Profile
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 · 4건

DEF at doses which had little effect on brain acetylcholinesterase, inhibited mouse and rat tissue carboxylesterases and potentiated acute toxic action of organophosphorus insecticides.

Effect of diazinon (0.002%) against female Lucilia cuprina was potentiated by prior treatment with 1% s,s,s-tributyl phosphorotrithioate.

DEF acted as synergist when used with endrin and methomyl against the Egyptian cotton leafworm Spodoptera littorals.

DEF synergized diflubenzuron and Bay Sir 8514 3319- and 45-fold, respectively, in Platynota stultana, but was not synergistic in Spodoptera exiqua.

Target Organs · 2건

Gastrointestinal (Stomach and Intestines, part of the digestive system), Hematological (Blood Forming), Neurological (Nervous System)

Nervous

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.

Ecotoxicity Values · 5건

LC50 Grammarus fasciatus /(Scud)/ 100 ug/L/96 hr at 21 °C (95% confidence interval, 68 to 150 ug/L/96 hr). Static conditions without aeration.

LC50 Pteronarcys 2100 ug/L/96 hr at 15 °C (95% confidence interval, 1500 to 2900 ug/L/96 hr). Static conditions without aeration.

LC50 /Oncorhynchus mykiss/ (Rainbow trout) 660 ug/L/96 hr at 13 °C (95% confidence interval, 560 to 750 ug/L/96 hr). Static conditions without aeration.

LC50 Oncorhynchus mykiss (Rainbow trout, weight 0.91 g) 1700 ppb/96 hr (95% confidence limit: 1300-2300 ppb); flow-through /96.2% AI formulated product/

For more Ecotoxicity Values (Complete) data for TRIBUFOS (19 total), please visit the HSDB record page.

규제 정보

FIFRA Requirements · 3건

Tolerances are established for residues of the defoliant tribuphos (S,S,S-tributylphosphorotrithioate) in or on food commodities as follows: Cattle, fat (negligible residue); cattle, meat byproducts (negligible residue); cattle, meat (negligible residue); cotton, undelinted seed; goat, fat (negligible residue); goat, meat byproducts (negligible residue); goat, meat (negligible residue); milk (negligible residue); sheep, fat (negligible residue); sheep, meat byproducts (negligible residue); and sheep, meat (negligible residue).

The Agency has determined that Tribufos is eligible for reregistration provided that: (i) current data gaps and additional data needs are addressed; (ii) the risk mitigation measures outlined in this document are adopted, and label amendments are made to reflect these measures; and (iii) the cumulative risk assessment for the organophosphates support a final reregistration eligibility decision.

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. S,S,S-tributyl phosphorotrithioate is found on List B. Case No: 2145; Pesticide type: herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): S,S,S-tributyl phosphorotrithioate; Data Call-in (DCI) Date(s): 02/04/91, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

안전 데이터

tsca
TSCA listed
rtecs
TG5425000
ridadr
UN 2811
독성
LD50 in male, female rats (mg/kg): 233, 150 orally; 360, 168 dermally (Gaines)
risk_code
24/25-50/53
hazard_code
T,N

화학 및 산업

약리 정보

Metabolism/Metabolites · 4건

/In animals/ metabolism proceeds by hydrolysis followed by methylation and successive oxidation of butylmercaptan, yielding the main metabolite (3-hydroxy)-butylmethylsulfone.

The data presented here indicate that rodents metabolize and excrete delayed neurotoxic organophosphorus esters with great efficiency. By contrast, the adult chicken seems to have difficulty carrying out these processes. The cat is intermediate between rodents and chickens. Although further studies are needed, these results suggest that the hen model may exaggerate the effect of neurotoxic organophosphorus esters. Extrapolation of findings from the chicken may thus overestimate the risk or hazard of organophosphorus esters to humans. This may explain why no human case of O-ethyl-O-nitrophenyl phenylphosphonothioate induced delayed neurotoxicity has been reported despite the fact that it has been in use for over a quarter of a century. Other neurotoxicity data from our laboratory seem to support the suggestion that the cat may be a better model to extrapolate neurotoxicity results to humans. The data presented in this review suggest that the phrmacokinetics and metabolism of organophosphorus esters may play a prominent role in species and age sensitivities for organophosphorus-induced delayed neurotoxicity. Animals that are sensitive to delayed neurotoxicity have a higher accumulation rate, coupled with slower elimination of the neurotoxic agent. These studies, however, do not rule out the possibility that the target tissue of organophosphorus delayed neurotoxicity itself is species or age specific.

The metabolism and residue levels of the defoliant S,S,S-tributyl-phosphorotrithioate (78488) (DEF) were investigated in urine, selected tissue, and milk from a French-Alpine-goat. ... The main route of excretion for the DEF metabolites was the urinary tract, accounting for 52% of the total dose. Fecal excretion accounted for 13% of the total dose. ... The total radioactive residue in fat and milk was composed 31% and 5% respectively of DEF. Less than 1% of the total radioactive residue was contained in the DEF found in the liver, kidney and muscle. The tissue, milk, and urine contained 3-hydroxybutylmethyl-sulfone, a major metabolite. Two minor components of the urine were S,S-dibutyl-phosphorodithioate and S-butyl-phosphorothioate.

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 Classification · 3건

Herbicides that remove leaves from trees and growing plants. They may be either organic or inorganic. Several of the more persistent types have been used in military operations and many are toxic. (From Hawley&apos;s Condensed Chemical Dictionary, 11th ed)

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Chemicals that, while not possessing inherent pesticidal activity, nonetheless promote or enhance the effectiveness of other pesticides when combined.

Absorption, Distribution and ExcretionTribufos is rapidly absorbed and metabolised /in animals/; 96% of the administered radioactivity was excreted within 72 hours.

용도 및 제조

Uses · 6건

Used as cotton defoliant (for machine harvesting), synergist for insecticides, insecticide, herbicide, and growth regulator; [HSDB] Used in the US strictly for defoliating cotton prior to machine harvesting; General use pesticide; [Reference #1]

Farming (Pesticides) [Category: Industry]

For S,S,S-tributyl phosphorotrithioate (USEPA/OPP Pesticide Code:074801) 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./

Cotton defoliant.

Defoliant /from Table/

... Insecticide, herbicide, growth regulator

U.S. Production · 4건

2022: 81,032 lb

(1975) 2.95X10+9 GRAMS (CONSUMPTION)

(1998) 10 thousand-500 thousand pounds

(2002) 10 thousand-500 thousand pounds

Consumption Patterns99% AS A DEFOLIANT ON COTTON; 1% AS A DEFOLIANT ON OTHER FIELD CROPS (1971)
Methods of Manufacturing · 2건

It is made from butanethiol and phosphorus oxychloride in the presence of a base.

Reaction of butyl mercaptan with phosphorus oxychloride in the presence of a base

Formulations/Preparations · 5건

Spray concentrate (700 g active ingredient/L).

Selected products: DEF 6, Folex. Discontinued products: Def, De-Green, E-Z-off D.

There are two technical products of tribufos presently registered. One technical (98.0% ai, liquid) is registered to Bayer (EPA Reg. No. 3125-96) and one to Micro Flo Company (98.1% ai with an EPA Reg. No. 51036-324). There are three liquid end-use products: one registered to Bayer (EPA Reg. No. 3125-282 - 71.5% ai); one registered to Aventis Crop Science (EPA Reg. No. 264-498 - 70.5% ai); and one registered to Micro Flo (EPA Reg. No. 51036-320 -70.5% ai). There was also one Special Local Need (SLN) product registered in Texas, (SLN No. TX810045) which Bayer requested cancellation on July 24, 2000.

Emulsifiable concentrate

For more Formulations/Preparations (Complete) data for TRIBUFOS (8 total), please visit the HSDB record page.

Use ClassificationDEFOLIANTS
응용 분야 · 3건

개요DEF is a cholinesterase-inhibiting organophosphorus pesticide compound used as a cotton defoliant that was registered in 1960.DEF is a colorless to pale-yellow transparent liquid with a skunk-like odor.It is completely miscible with n-hexane, dichloromethane, toluene, and 2-propanol and has an octanol–water partition coefficient of 3.31×105 at 25°C. DEF toxicity is primarily attributed to inhibition of various esterases, including acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), neuropathic target esterase (NTE), and carboxylesterase, resulting in increased accumulation of endogenous acetylcholine (ACh) in cholinergic nerve terminals and related effector organs.

용도1,2,4-Tributylphosphorotrithioate is a defoliant for cotton.

일반 설명Colorless to pale yellow liquid with mercaptan-like odor. Insoluble in water; soluble in aliphatic, aromatic, and chlorinated hydrocarbons.. Used as a growth regulator.

공급사32 곳

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]

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