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다이아지논

다이아지논
다이아지논 구조식 이미지
카스 번호:
333-41-5
한글명:
다이아지논
동의어(한글):
O-디에틸-O-포스포르티오에이트,다이아지논;다이아지논;디아지논
상품명:
Diazinon
동의어(영문):
g301;Anti;Dicid;dyzol;G 301;pt265;AG-500;Antlak;Dazzel;Exodin
CBNumber:
CB7702086
분자식:
C12H21N2O3PS
포뮬러 무게:
304.35
MOL 파일:
333-41-5.mol

다이아지논 속성

녹는점
>120°C (dec.)
끓는 점
306°C
밀도
1.117
증기압
1.2 x 10-2 Pa (25 °C)
굴절률
nD20 1.4978-1.4981
인화점
104.4 °C
저장 조건
APPROX 4°C
물리적 상태
neat
수용성
Slightly soluble. 0.004 g/100 mL
Merck
13,3019
BRN
273790
노출 한도
OSHA PEL: TWA 0.1 mg/m3; ACGIH TLV: TWA 0.1 mg/m3.
CAS 데이터베이스
333-41-5(CAS DataBase Reference)
NIST
Diazinone(333-41-5)
EPA
Phosphorothioic acid, O,O-diethyl O-[6-methyl-2-(1-methylethyl)- 4-pyrimidinyl] ester(333-41-5)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn;N,N,Xn,F
위험 카페고리 넘버 22-50/53-36-20/21/22-11-51/53
안전지침서 24/25-60-61-36-26-16-36/37
유엔번호(UN No.) UN 2783/2810
WGK 독일 3
RTECS 번호 TF3325000
위험 등급 6.1(b)
포장분류 III
HS 번호 29335990
유해 물질 데이터 333-41-5(Hazardous Substances Data)
독성 LD50 in male, female rats (mg/kg): 250, 285 orally (Gaines)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H312 피부와 접촉하면 유해함 급성 독성 물질 - 경피 구분 4 경고 P280,P302+P352, P312, P322, P363,P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H332 흡입하면 유해함 급성 독성 물질 흡입 구분 4 경고 P261, P271, P304+P340, P312
H350 암을 일으킬 수 있음 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 1A, 1B 위험
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 P273, P391, P501
H411 장기적 영향에 의해 수생생물에 유독함 수생 환경유해성 물질 - 만성 구분 2
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.

다이아지논 C화학적 특성, 용도, 생산

개요

Diazinon is a non-systemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon functions as the inhibitor of acetylcholinesterase (AChE), which breaks down the neurotransmitter acetylcholine (ACh) into [choline] and an acetate group. The inhibition of the AChE causes an abnormal accumulation of ACh in the synaptic cleft. However, recent studies have shown that diazinon and other kinds of organophosphate can cause neural toxicity through causing oxidative stress in the neural cells.

화학적 성질

Diazinon is available as a colorless or dark brown liquid. It is sparingly soluble in water but very soluble in petroleum ether, alcohol, and benzene. Diazinon is used for the control of a variety of agricultural and household pests. These include pests in soil, on ornamental plants, fruit, vegetable, crops pests, and household pests like fl ies, fl eas, and cockroaches. Diazinon undergoes decomposition on heating above 120°C and produces toxic fumes, such as nitrogen oxides, phosphorous oxides, and sulfur oxides. It reacts with strong acids and alkalis with the possible formation of highly toxic tetra ethyl thiopyrophosphates. Diazinon is classifi ed as an RUP. Depending on the type of formulation, diazinon is classifi ed as toxicity class II, meaning moderately toxic, or toxicity class III, meaning slightly toxic.

화학적 성질

Diazinon is a combustible, colorless, oily liquid. Faint amine odor. Technical grade is pale to dark brown. Commercial formulations may use carrier solvents which can change the physical properties listed here.

용도

Insecticide.

용도

insecticide, cholinesterase inhibitor

용도

A cholinesterase inhibitor; a nonsystemic organophosphate insecticide.

용도

Nonsystemic contact insecticide used against flies, aphids and spider mites in soil, fruit, vegetables and ornamentals.

용도

Diazinon is used to control a wide range of sucking and chewing insects and mites in a very wide range of crops and is also used as a veterinary ectoparasiticide.

정의

ChEBI: A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.

일반 설명

Diazinon is available in the form of a colourless or dark brown liquid. It is sparingly soluble in water but very soluble in petroleum ether, alcohol, and benzene. Diazinon is used for the control of a variety of agriculture and household pests. These include pests in soil, on ornamental plants, fruit, vegetable, and crops and household pests like flies, fleas, and cockroaches. Diazinon undergoes decomposition on heating above 120°C and produces toxic fumes such as nitrogen oxides, phosphorus oxides, and sulphur oxides. It reacts with strong acids and alkalis with possible formation of highly toxic tetra ethyl thiopyrophosphates. Diazinon is classified as a RUP. Depending on the type of formulation, diazinon is classified as toxicity class II, meaning moderately toxic, or toxicity class III, meaning slightly toxic.

공기와 물의 반응

The neat compound is susceptible to oxidation and should be protected from prolonged exposure to air . Insoluble in water.

건강위험

LIQUID: POISONOUS IF SWALLOWED. Irritating to skin and eyes.

건강위험

Humans are exposed to diazinon during manufacture and professional applications. Diazinon causes poisoning with symptoms such as headache, dizziness, nausea, weakness, feelings of anxiety, vomiting, pupillary constriction, convulsions, respiratory distress or labored breathing, unconsciousness, muscle cramp, excessive salivation, respiratory failure, and coma.

건강위험

Cholinesterase inhibitor; moderately toxic byingestion and skin absorption; ingestion ofapproximately large quantities of 10–15 gcan produce cholinergic effects in adulthuman; poisoning symptoms include headache, dizziness, weakness, blurred vision,pinpoint pupils, salivation, muscle spasms,vomiting abdominal pain, and respiratorydepression; LD50 values in experimentalanimals show wide variation.
LD50 oral (rat): within the range 100–300mg/kg
LD50 oral (guinea pig): 250 mg/kg.

화재위험

Not flammable. POISONOUS GASES ARE PRODUCED WHEN HEATED. Oxides of sulfur and of phosphorus are generated in fires.

농업용

Insecticide, Acaricide: Diazinon is the most widely used pesticide by homeowners on lawns, and is one of the most widely used pesticide ingredients for application around the home and in gardens. It is used to control insects and grub worms. It is a nonsystemic organophosphate insecticide used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Bait is used to control scavenger yellow jackets in the western U.S. It is used on home gardens and farms to control a wide variety of sucking and leaf-eating insects. It is used on rice, fruit trees, sugarcane, corn, tobacco, potatoes and on horticultural plants, and is also an ingredient in pest strips. Diazinon has veterinary uses against fleas and ticks. It is available in dust, granules, seed dressings, wettable powder, and emulsifiable solution formulations. In 1988, there were 500 different products containing diazinon on the market, and used in such products as agricultural sprays and granules, animal ear tags, household sprays and dust and veterinary products. Not approved for use in EU countries. A U.S. EPA restricted Use Pesticide (RUP). The U.S. EPA initiated a program to phase out all non-agricultural uses of diazinon commencing in March, 2001. Many commercial outdoor uses of diazinon have been canceled or restricted to licensed pesticide applicators because of its known toxicity to birds and aquatic life. Diazinon is highly toxic to bees and very highly toxic to birds, fish and aquatic invertebrates. Diazinon was canceled for use on golf courses and sod farms in 1988 because of its high risk to birds

상품명

AG-500®; AI3-19507®; ALFA-TOX®[C]; ANTIGAL®; ANTLAK®; BASUDIN®; BAZUDEN®; CASWELL No. 342®; DACUTOX®; DASSITOX®; DAZZEL®; DIAGRAN®; DIANON®; DIATERR-FOS®; DIAZAJET®; DIAZATOL®; DIAZIDE®; DIAZINON AG 500 WBC®; DIAZINONE®; DIAZITOL®; DIAZOL®; DICID®; DIMPYLATE®; DIPOFENE®; DIZIKTOL®; DIZINON®[C]; DRAWIZON®; DYMET®; DYZOL®); D.Z.N.®; EXODIN®; FEZUDIN®; FLYTROL®; G 301®; G-24480®; GALESAN®; GARDENTOX®; GEIGY 24480®; KAYAZINON®; KAYAZOL®; NEOCIDOL® (OIL); NEOCIDOL®; NIPSAN®; NUCIDOL®; OLEODIAZINON®; ROOT GUARD; SAROLEX®[C]; SPECTRACIDE®; SROLEX®; SUZON®

Safety Profile

Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Mildly toxic by inhalation. Human systemic effects by ingestion: changes in motor activity, muscle weakness, and sweating. Experimental teratogenic and reproductive effects. A skin and severe eye irritant. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, POx, and SOx.

잠재적 노출

roducers, formulators and applicators of this nonsystemic pesticide and acaricide. Diazinon is used in the United States on a wide variety of agricultural crops, ornamentals, domestic animals; lawns and gardens; and household pests.

환경귀착

Biological. Sethunathan and Yoshida (1973a) isolated a Flavobacterium sp. (ATCC 27551) from rice paddy water that metabolized diazinon as the sole carbon source. Diazinon was readily hydrolyzed to 2-isopropyl-4-methyl-6-hydroxypyrimidine under aerobic conditions but less rapidly under anaerobic conditions. This bacterium as well as enrichment cultures isolated from a diazinon-treated rice field mineralized the hydrolysis product to carbon dioxide (Sethunathan and Pathak, 1971; Sethunathan and Yoshida, 1973). Rosenberg and Alexander (1979) demonstrated that two strains of Pseudomonas grew on diazinon and produced diethyl phosphorothioate as the major end product. The rate of microbial degradation increased in the presence of an enzyme (parathion hydrolase), produced by a mixed culture of Pseudomonas sp. (Honeycutt et al., 1984).
Soil. Hydrolyzes in soil to 2-isopropyl-4-methyl-2-hydroxypyrimidine, diethylphosphorothioic acid, carbon dioxide (Getzin, 1967; Lichtenstein et al., 1968; Sethunathan and Yoshida, 1969; Sethunathan and Pathak, 1972; Bartsch, 1974; Wolfe et al., 1976; Somasundaram and Coats, 1991) and tetraethylpyrophosphate (Paris and Lewis, 1973). The half-life of diazinon in soil was observed to be inversely proportional to temperature and soil moisture content (Getzin, 1968). Seven months after diazinon was applied on a sandy loam (2 kg/ha), only 1% of the total applied amount remained and 10% was detected in a peat loam (Suett, 1971).
The reported half-life in soil is 32 days (Jury et al., 1987). Reported half-lives in soil following incubation of 10 ppm diazinon in sterile sand loam, sterile organic soil, nonsterile sandy loam and nonsterile organic soil are 12.5, 6.5, <1 and 2 weeks, respectively (Miles et al., 1979). The reported half-life of diazinon in sterile soil at pH 4.7 was 43.8 days (Sethunathan and MacRae, 1969). Major metabolites identified were diethyl thiophosphoric acid, 2-isopropyl-4-methyl-6-hydroxypyrimidine and carbon dioxide (Konrad et al., 1967). When soil is sterilized, the persistence of diazinon increased more so than changes in soil moisture, soil type or rate of application (Bro-Rasmussen et al., 1968). The halflives for diazinon in flooded soil incubated in the laboratory ranged from 4 to 17 days with an average half-life of 10 days (Sethunathan and MacRae, 1969; Sethunathan and Yoshida, 1969; Laanio et al., 1972). The mineralization half-life for diazinon in soil was 5.1 years (Sethunathan and MacRae, 1969; Sethunathan and Yoshida, 1969).
The half-lives of diazinon in a sandy loam, clay loam and an organic amended soil under nonsterile conditions were 66–1,496, 49–1,121 and 14–194 days, respectively, while under sterile conditions the half-lives were 57–1,634, 46–1,550 and 14–226 days, respectively (Schoen and Winterlin, 1987).
In a silt loam and sandy loam, reported Rf values were 0.86 and 0.88, respectively (Sharma et al., 1986).
Surface Water. In estuarine water, the half-life of diazinon ranged from 8.2 to 10.2 days (Lacorte et al., 1995).
Groundwater. According to the U.S. EPA (1986) diazinon has a high potential to leach to groundwater.
Plant. Diazinon was rapidly absorbed by and translocated in rice plants. Metabolites identified in both rice plants and a paddy soil were 2-isopropyl-4-methyl-6-hydroxypyrimidine (hydrolysis product), 2-(1¢-hydroxy-1¢-methyl)ethyl-4-methyl-6-hydroxypyrimidine and other polar compounds (Laanio et al., 1972). Oxidizes in plants to diazoxon (Ralls et al., 1966; Laanio et al., 1972; Wolfe et al., 1976) although 2-isopropyl-4-methyl- 6-pyrimidin-6-ol was identified in bean plants (Kansouh and Hopkins, 1968) and as a hydrolysis product in soil (Somasundaram et al., 1991) and water (Suffet et al., 1967). Five days after spraying, pyrimidine ring-labeled 14C-diazinon was oxidized to oxodiazinon which was then hydrolyzed to 2-isopropyl-4-methylpyrimidin-6-ol which in turn, was further metabolized to carbon dioxide (Ralls et al., 1966). Diazinon was transformed in field-sprayed kale plants to form hydroxydiazinon {O,O-diethyl-O-[2-(2¢-hydroxy-2¢-propyl)- 4-methyl-6-pyrimidinyl] phosphorothioate} which was not previously reported (Pardue et al., 1970).

신진 대사 경로

The main route of diazinon metabolism in soil, plants and animals is through cleavage of the P-O-pyrimidine group to yield 2-isopropyl-4- methyl-6-hydroxypyrimidine. As with most other phosphorothioates, loss of the pyrimidinyl function in mammalian metabolism probably occurs either through oxidative desulfuration of the thiono group, catalysed by microsomal mixed function oxidases, to give diazoxon followed by hydrolysis catalysed by an A-esterase, or via an oxidative mechanism catalysed by a mixed function oxidase acting directly on diazinon. In the first case the second product is diethyl phosphate and in the second, diethyl phosphorothioate (Yang et al., 1971). Further metabolism then leads to hydroxylation of the methyl and isopropyl groups on the pyrimidine ring. This oxidative metabolism may the act on the pyrimidinol, diazoxon or diazinon itself, the last of which seems to be important in mammalian and avian liver and gives rise to metabolites which still have anticholinesterase or latent anticholinesterase activity.

운송 방법

UN2783 Organophosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Degradation

Diazinon(1) is stable at neutral pH but is slowly hydrolysed in alkaline solutions and rapidly at acidic pH values (PM). Hydrolysis products were identified as the pyrimidinol (2) and diethyl phosphorothioate (3) (PSD, 1991).
When diazinon was dissolved in a water/soil suspension and irradiated with UV light, Mansour et al. (1997) demonstrated that one of the products was iso-diazinon (4) formed via a thiono-thiolo rearrangement (see Scheme 1).

비 호환성

Reaction with nitrosating agents (e.g., nitrites, nitrous gases, nitrous acid) capable of releasing carci- nogenic nitrosamines. Hydrolyzes slowly in water and dilute acid. Reacts with strong acids and alkalis with possible forma- tion of highly toxic tetraethyl thiopyrophosphates. Incompatible with copper-containing compounds. Contact with oxidizers may cause the release of phosphorous oxides. Contact with strong reducing agents, such as hydrides; may cause the formation of flammable and toxic phosphine gas.

폐기물 처리

Diazinon is hydrolyzed in acid media about 12 times as rapidly as parathion, and at about the same rate as parathion in alkaline media. In excess water this compound yields diethylthiophosphoric acid and 2-isopropyl-4-methyl-6-hydroxypyrimidine. With insufficient water, highly toxic tetraethyl monothiopyropho- sphate is formed. Therefore, incineration would be a prefer- able ultimate disposal method with caustic scrubbing of the incinerator effluent . In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by follow- ing package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

주의 사항

Workers should avoid eye contact with diazinon, wear chemical safety glasses or goggles, protective clothing or equipment, wear waterproof boots, long-sleeved shirts, long pants, and a hat. Workers should avoid contamination of food and feed, wash thoroughly after handling and before eating or smoking. In fact, occupational workers should avoid eating, drinking, or smoking in areas of work with the chemical.

참고 문헌

Uner, N, et al. "Effects of diazinon on acetylcholinesterase activity and lipid peroxidation in the brain of Oreochromis niloticus." Environmental Toxicology & Pharmacology 21.3(2006):241.
Shishido, Takashi, K. Usui, and J. I. Fukami. "Oxidative metabolism of diazinon by microsomes from rat liver and cockroach fat body." Pesticide Biochemistry & Physiology 2.1(1972):27-38.
Giordano, G, et al. "Organophosphorus insecticides chlorpyrifos and diazinon and oxidative stress in neuronal cells in a genetic model of glutathione deficiency." Toxicology & Applied Pharmacology 219.2-3(2007):181.

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