りん酸ジメチル(E)-1-(N,N-ジメチルカルバモイル)-1-プロペン-2-イル 化学特性,用途語,生産方法
用途
農薬(殺虫剤)
農薬用途
殺虫剤、ダニ駆除剤
説明
It is a yellowish liquid, bp 130 ?C/0.1 mmHg, vp 9.3 mPa
(20 ?C). It ismiscible with water and most organic solvents
except kerosene. Log Kow = ?0.5. Dicrotophos is rather
stable to heat and slowly hydrolyzed in acidic media and
more rapidly in alkaline media; DT
50 (20 ?C) at pH 5, 7,
and 9 are 88, 72, and 28 d, respectively.
化学的特性
Dicrotophos is an amber liquid with a mild
ester odor.
使用
Dicrotophos is used to control sucking, chewing and boring
insects and mites in a wide range of crops. It is also used as an animal
ectoparasiticide.
製造方法
Dicrotophos is synthesized by the Perkow reaction
from trimethyl phosphite and N,N-dimethyl-α-
chloroacetoacetamide, consisting mainly of the (E)-form.
一般的な説明
A yellow to brown liquid with a mild ester odor. Used to control sucking, boring, and chewing pests on rice, cotton, coffee, apples, and other crops. Effective on ornamentals, trees, and shrubs for aphids, leaf hoppers, and scale insects.
空気と水の反応
Water soluble.
反応プロフィール
Organophosphates, such as DICROTOPHOS, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. DICROTOPHOS is incompatible with the following: Metals [Note: Corrosive to cast iron, mild steel, brass & stainless steel.] .
健康ハザード
DICROTOPHOS is extremely toxic. Probable human oral lethal dose is 5 to 50 mg/kg, 7 drops to one teaspoonful for a 70 kg (150 lb.) person. Closely related in toxicity to azodrin.
火災危険
(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) DICROTOPHOS may burn but does not ignite readily. Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Rapidly hydrolyzes in acid or alkali. Keep away from heat and open flame.
农业用途
Insecticide, Acaricide: EPA restricted Use Pesticide (RUP). Not approved
for use in EU countries. Dicrotophos was introduced in
1956 as a contact systemic pesticide with a wide range of
applications. Today, dicrotophos is currently used mainly
as an insecticide for apples and other fruit crops, and for
cotton pests, mostly in the Mississippi Valley. It is acutely
toxic to birds, especially those that follow their migratory
corridors and feed in the farmlands that have been treated
with this pesticide. Internationally, dicrotophos is used on
rice, coffee and citrus. One of the major degradates of dicrotophos
is monocrotophos. All uses of monocrotophos
have been voluntarily cancelled in the United States due to
its extreme toxicity to humans and wildlife
製品名
BIDIRL®; BIDRIN®; BIDRIN-R®[C];
BIDRIN®[C]; C-709®; C-709®; CARBICRIN®;
CARBICRON®; CARBOMICRON®; CIBA 709®;
DIAPADRIN®; DICRON®; DIDRIN®; EKTAFOS®;
EKTOFOS®;
安全性プロファイル
Poison by ingestion,
inhalation, skin contact, subcutaneous,
intravenous, and intraperitoneal routes.
Mutation data reported. Used to control the
coffee borer and certain economically
important pests of cotton. When heated to decomposition it emits very toxic fumes of
NOx and POx. See also ESTERS.
職業ばく露
A potential danger to those involved
in the manufacture, formulation and application of this
organophosphate. Used to control the coffee borer and certain economically important pests of cotton
発がん性
When rats were fed dicrotophos
in their diets at concentrations of 0, 1, 10, or 100 ppm for
2 years, there were no detectable effects at the 1 ppm
concentration . Plasma cholinesterase was inhibited
at 1 ppm . At 10 and 100 ppm, decreased body weights
and reduced cholinesterase (erythrocyte, plasma, and brain
not specified) activities occurred. Dogs given dicrotophos in
their diets at 0, 0.16, 1.6, or 16 ppm for 2 years showed some instances of slightly excessive salivation . At 16 ppm,
both plasma and RBC cholinesterase activity was decreased.
環境運命予測
Soil. The dimethylamino group is converted to an N-oxide then to -CH2OH and aldehyde groups which further degrade via demethylation and hydrolysis (Hartley and Kidd, 1987). Dicrotophos is rapidly degraded under aerobic and anaerobic conditions forming N,N-dimethylacetoacetamide and 3-hydroxy-N,N-dimethylbutyramide as the major metabolites. Other metabolites included carbon dioxide and unextractable residues. The half-life of dicrotophos in a Hanford sandy loam soil was 3 days (Lee et al., 1989).
Biological. Identified metabolites of dieldrin from solution cultures containing Pseudomonas sp. in soils include aldrin and dihydroxydihydroaldrin. Other unidentified byproducts included a ketone, an aldehyde and an acid (Matsumura et al., 1968; Kearney and Kaufman, 1976). A pure culture of the marine alga, namely Dunaliella sp., degraded dieldrin to photodieldrin and an unknown metabolite at yields of 8.5 and 3.2%, respectively.
Chemical/Physical. Dicrotophos emits toxic fumes of phosphorus and nitrogen oxides when heated to decomposition (Sax and Lewis, 1987; Lewis, 1990).
Dicrotophos is hydrolyzed in sodium hydroxide solutions forming dimethylamine. The hydrolysis half-lives at 38°C and pH values of 1.1 and 9.1 are 100 and 50 days, respectively (Sittig, 1985). Lee et al. (1989) reported that the hydrolysis half-lives of di
代謝経路
The metabolic fate of dicrotophos mirrors very closely that of its
close congener, monocrotophos. Technical dicrotophos contains 82%
of the E-isomer and 6% of the Z-isomer, the balance being various
impurities. Most studies on the metabolic fate of this compound have
used a purified material containing >99% E-isomer. Dicrotophos is a
systemic vinyl phosphate insecticide with a high water solubility and
low log Kow.
The main routes of metabolic degradation are demethylation to des-
O-methyldicrotophos and hydrolysis to dimethyl phosphate and N,N-dimethylacetoacetamide.
In animals and plants, hydroxylation of the
N-methyl group followed by N-demethylation are also important from a
toxicological point of view, since these metabolic steps yield highly
active idubitors of acetylcholinesterase. In the case of dicrotophos,
N-demethylation affords monocrotophos as one of the products of
metabolism.
代謝
The main degradation routes are O-demethylation to
des-O-methyldicrotophos and hydrolysis to dimethyl phosphate
and N,N-dimethylacetoacetamide. Oxidative Ndemethylation
also occurs.
輸送方法
UN3018 Organophosphorus pesticides, liquid,
toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
不和合性
Attacks some metals: Corrosive to cast
iron, mild steel; brass, and stainless steel l304. Decomposes
after prolonged storage, but is stable when stored in glass
or polyethylene containers with temperatures to 40C.
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
廃棄物の処理
Dicrotophos decomposes after
7 days @ 90C and 31 days @ 75°C. Hydrolysis is 50%
complete in aqueous solutions @ 38C after 50 days at pH
9.1 (100 days are required at pH 1.1). Alkaline hydrolysis
(NaOH) yields (CH3)2NH. Incineration is also recommended as a disposal method. In accordance with
40CFR165, follow recommendations for the disposal of
pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting
your local or federal environmental control agency, or by
contacting your regional EPA office
りん酸ジメチル(E)-1-(N,N-ジメチルカルバモイル)-1-プロペン-2-イル 上流と下流の製品情報
原材料
準備製品