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77182-82-2

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77182-82-2 Usage

Organophosphorus herbicides

Glufosinate-ammonium, also known as glufosinate, is a non-selective foliar application of organic phosphorus herbicide, in 1979 first developed by the Federal Republic of Germany Hoechst (Hoechst) chemical synthesis company. Weeding mechanism of Glufosinate-ammonium is absorbed by the blade, having a part suction effect, can be transferred from the base of the blade to the ends, transferred less to other parts of the plant, is harmless for not unearthed shoots and seeds. Plants Glufosinate-ammonium metabolism is disordered in a short period after drug application, a strong cytotoxic agent Glufosinate-ammonium ion is accumulated in plants; poisoned the plant to die. While also severely inhibited photosynthesis, injured plants was yellowish white after lose of the green, after 2 to 5 days, turned yellow and died. After contacted with the soil, lost activity, it should only for spray of stem and leaf at postemergence. Applications: Glufosinate-ammonium is mainly used for destuctive weeding of orchards, vineyards, potato fields, nurseries, forests, pastures, ornamental shrubs and free arable, prevention and weeding of annual and perennial weeds such as foxtail, wild oats, crabgrass , barnyard grass, green foxtail, bluegrass, quackgrass, bermudagrass, bentgrass, reeds, fescue, etc. Also prevention and weeding of broadleaf weeds such as quinoa, amaranth, smartweed, chestnut, black nightshade, chickweed, purslane, cleavers, sonchus, thistle, field bindweed, dandelion, also have some effect on sedges and ferns. When broadleaf weeds in the beginning of growing season and grass weeds in tillering period, dosage of 0.7 to 1.2 kg/hectare was sprayed on weed populations, period of weed control is 4 to 6 weeks, administration again if necessary, can significantly extend the validity period. Potato field should be used in the pre-emergence, it can also be sprayed before harvest, killing and weeding ground stubble, so as to harvest. Prevention and weeding of ferns, dosage of per hectare is 1.5 to 2 kg. Usually alone, sometimes it can also be mixed with simajine, diuron or methylchloro phenoxyacetic acid, and so on. Figure 1 The chemical structural formula of Glufosinate-ammonium. The above information is edited by the lookchem of Liu Yujie.

Toxicity

Male rats acute oral LD50 is 2000 mg/kg, female rats is 1620 mg/kg; male mice acute oral LD50 is 431 mg/kg, female mice is 416 mg/kg; dog acute oral LD50 is 200~400 mg/kg. Male rats acute percutaneous LD50 is > 2000 mg/kg, female rats is 4000 mg/kg. No teratogenic and carcinogenic effects. Rainbow trout LC50 is 320mg/L (96h).

Chemical properties

Low solubility in common organic solvents, solubility in water is large. At pH 5-9, hydrolysis, half-life of soil is <10d. Light stability.

Uses

Different sources of media describe the Uses of 77182-82-2 differently. You can refer to the following data:
1. Organophosphorus herbicides, glutamine synthetase inhibitors, non-selective contact herbicide. There are certain suction effect, can be used for weeding of orchards, vineyards and non-cultivated land, can also be used for prevention and weeding of annual and perennial dicotyledonous weeds and sedges in potato field, such as rat tail foxtail, crabgrass, barnyardgrass, foxtail, wild wheat, wild corn, cocksfoot, fescue, deschampsia flexuosa, hair grass, ryegrass, reed, bluegrass, wild oat, brome, cleavers, henbit, lamium, solanum nigrum, chickweed, quackgrass, bentgrass, calamagrostis grass, field forget-grass, bermuda grass, amaranthus. Depending on crops and weeds, the amount of use varies, the usage amount of per hectare is 1~2 kg or more , such as prevention and weeding of raspberry crops and fern in forests and alpine pastures. Usage amount is 1.5~20kg/hm2.
2. Postemergent herbicide; desiccant.

Production methods

The O, O-diethyl methyl phosphonate reacted with dibromoethane reaction, heated at 80 ℃ for 2 h to get BrCH2CH2P (O) (OC2H5) CH3, and then reacted with (C2H5O2C) 2CNa (NHCOCH3) at 85 ℃to get ( C2H5O2C) 2C (NHCOCH3) CH2CH2P (O) (OC2H5) CH3, which was refluxed with hydrochloric acid, the resulting compound reacted with 28% Glufosinate-ammonium hydroxide for 8 h at 60~70 ℃ to obtain Glufosinate-ammonium. In addition, synthesis of Glufosinate-ammonium included high-pressure catalytic synthesis method, low-temperature of targeting synthesis, using Strecker reaction and Mitchell addition process ,and so on. See "Pesticides" issue 9, 2002.

Acute toxicity

Oral-rat LD50: 1620 mg/kg; Oral-mouse LD50: 416 mg/kg.

Flammability hazard characteristics

Combustible; combustion produces toxic fumes of nitrogen oxides and sulfur oxides.

Storage characteristics

Treasury is ventilation, low-temperature and dry

Description

Glufosinate ammonium is a broad-spectrum contact killing herbicide with the chemical formula c5h15n2o4p and the amount of chemical formula 198.16. It has the characteristics of wide herbicidal spectrum, low toxicity, high activity and good environmental compatibility.

Chemical Properties

solid

Flammability and Explosibility

Notclassified

Agricultural Uses

Herbicide: Glufosinate-ammonium is a naturally occurring broad-spectrum contact herbicide that is used to control a wide range of weeds after the crop emerges or for total vegetation control on non-crop lands. It is used on crops that have been genetically engineered. Glufosinate herbicides are also used to desiccate crops before harvest.

Trade name

BASTA?; DERRINGER?; FINALE?; HOE 00661?; HOE 03986?; HOE 39866?; IGNITE?; LIBERTY?; RELY?; REMOVE?; RUBOUT?; TOTAL?

Safety Profile

A poison by ingestion,subcutaneous, and intraperitoneal routes. Low toxicity byskin contact. Human systemic effects by ingestion: bloodpressure lowering, change in motor activity, coma,cyanosis. When heated to decomposition it emits toxicvapors of NO

Check Digit Verification of cas no

The CAS Registry Mumber 77182-82-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,7,1,8 and 2 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 77182-82:
(7*7)+(6*7)+(5*1)+(4*8)+(3*2)+(2*8)+(1*2)=152
152 % 10 = 2
So 77182-82-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H12NO4P.H3N/c1-11(9,10)3-2-4(6)5(7)8;/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10);1H3

77182-82-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name glufosinate-ammonium

1.2 Other means of identification

Product number -
Other names 2-amino-4-(hydroxymethylphosphinyl)butanoic acid monoammonium salt

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:77182-82-2 SDS

77182-82-2Synthetic route

glufosinate ammonium hydrochloride
59542-49-3

glufosinate ammonium hydrochloride

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With L-serin; ammonia In water at 110℃; pH=8; pH-value; Reagent/catalyst;98%
With ammonium hydroxide; ammonia In water at 70℃; pH=6 - 7;94.9%
With ammonia In methanol; water at 20℃; pH=1; Solvent; Reagent/catalyst;87 g
4-(hydroxymethylphosphinyl)-2-oxobutanoic acid
79778-02-2

4-(hydroxymethylphosphinyl)-2-oxobutanoic acid

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
Stage #1: 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid With ruthenium-carbon composite; ammonia In methanol at 25 - 30℃; under 1500.15 Torr; for 10h; Sealed tube;
Stage #2: With hydrogen at 50℃; under 4500.45 Torr; Temperature; Pressure;
97.8%
Stage #1: 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid With ammonia at 20℃; under 3000.3 Torr; for 1h; Autoclave;
Stage #2: With hydrogen at 50℃; under 30003 Torr; for 6h; Reagent/catalyst; Temperature; Pressure; Autoclave;
95%
Stage #1: 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid With 5%-palladium/activated carbon; ammonia In methanol at 25℃; under 1500.15 Torr; for 4h;
Stage #2: With hydrogen In methanol at 90℃; under 11251.1 Torr; for 6h;
2-amino-4-(methylethoxyphosphoryl)butyronitrile

2-amino-4-(methylethoxyphosphoryl)butyronitrile

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
Stage #1: 2-amino-4-(methylethoxyphosphoryl)butyronitrile With hydrogenchloride In water at 104 - 110℃; for 3.5h; Large scale;
Stage #2: With ammonium hydroxide at 45℃; for 1.5h; pH=7.5; pH-value; Large scale;
97.04%
DL-homoalanin-4-yl(methyl)phosphinic acid
51276-47-2

DL-homoalanin-4-yl(methyl)phosphinic acid

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With ammonia In methanol; water at 20℃; for 1h; Solvent;96%
With ammonia In ethanol; water at 20℃; for 1h; Solvent; Green chemistry;96%
With ammonium carbonate In ethanol at 20℃; for 0.5h; Product distribution / selectivity;
C10H18NO4P

C10H18NO4P

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With hydrogenchloride In water at 10℃; for 2h; Reflux;92.7%
With hydrogenchloride In water at 10℃; for 2h; Reflux;91.2%
glufosinate hydrochloride

glufosinate hydrochloride

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With ammonium hydroxide In methanol; water pH=9;92.5%
C10H18NO4P

C10H18NO4P

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With hydrogenchloride In water at 10℃; for 2h; Reflux;90.5%
With hydrogenchloride In water at 10℃; for 2h; Reflux;8.5 g
C13H24NO4P

C13H24NO4P

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With hydrogenchloride In water at 10℃; for 2h; Reflux;90.4%
C9H16NO4P

C9H16NO4P

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With hydrogenchloride In water at 10℃; for 2h; Reflux;90%
sodium cyanide
773837-37-9

sodium cyanide

3-oxopropylmethylphosphinic acid
121795-01-5

3-oxopropylmethylphosphinic acid

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With ammonium hydroxide; ammonium chloride at 20 - 40℃; for 4h; Reagent/catalyst;81.4%
C10H20NO6P

C10H20NO6P

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
Stage #1: C10H20NO6P With hydrogenchloride for 8h; Reflux;
Stage #2: With ammonium hydroxide for 6h; pH=9; Reflux;
80.96%
(3-cyano-3-hydroxypropyl)(methyl)phosphinic acid

(3-cyano-3-hydroxypropyl)(methyl)phosphinic acid

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
With water; ammonium carbonate at 150℃; for 6h; Reagent/catalyst;45.2 g
1-4-((ethoxy)(methyl)phosphoryl)butene
221319-78-4

1-4-((ethoxy)(methyl)phosphoryl)butene

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: copper dichloride; oxygen; palladium dichloride / water; acetonitrile / 6 h / 45 °C / 3750.38 Torr / Sealed tube
2.1: potassium permanganate; potassium hydroxide / water / 3.5 h / 0 - 50 °C
3.1: ammonia; ruthenium-carbon composite / methanol / 10 h / 25 - 30 °C / 1500.15 Torr / Sealed tube
3.2: 50 °C / 4500.45 Torr
View Scheme
3-[n-butoxy(methyl)phosphoryl]-1-cyanopropyl acetate
172529-93-0

3-[n-butoxy(methyl)phosphoryl]-1-cyanopropyl acetate

ammonium glufosinate
77182-82-2

ammonium glufosinate

Conditions
ConditionsYield
Stage #1: 3-[n-butoxy(methyl)phosphoryl]-1-cyanopropyl acetate With ammonia at 33 - 35℃; under 2625.26 Torr; for 1.6h; Autoclave; Inert atmosphere;
Stage #2: With hydrogenchloride; water for 7h; Temperature; Cooling; Reflux;
ammonium glufosinate
77182-82-2

ammonium glufosinate

Glufosinate-P-ammonium

Glufosinate-P-ammonium

Conditions
ConditionsYield
Stage #1: ammonium glufosinate With nickel(II) chloride hexahydrate; potassium hydroxide In methanol at 60℃;
Stage #2: With hydrogenchloride In water at 100℃; for 3h; Reagent/catalyst; Solvent;
98%

77182-82-2Relevant articles and documents

Synthesis method of glufosinate-ammonium

-

Paragraph 0038-0082, (2021/07/01)

The invention relates to the field of pesticides, in particular to a synthesis method of glufosinate-ammonium. The synthesis method of glufosinate-ammonium comprises the following steps: reacting a mixed aqueous solution of a hydantoin derivative, volatile alkali and a catalyst under 1.0-2.5 MPa, and after the reaction is finished, carrying out post-treatment to obtain glufosinate-ammonium, wherein the catalyst is a guanidine compound. The synthesis method of glufosinate-ammonium provided by the invention jumps out of the thought of separating glufosinate-ammonium from inorganic salt in the prior art, creatively adopts the mutual cooperation of volatile alkali and the catalyst (guanidine compound), and hydrolyzes the hydantoin derivative under the specific pressure of 1.0-2.5 MPa, so that the hydantoin compound is thoroughly hydrolyzed, the yield of glufosinate-ammonium is improved, meanwhile, the reaction time is shortened, acid-base neutralization is not needed after the reaction is finished, inorganic salt is not generated, generation of the inorganic salt in the glufosinate-ammonium preparation process is fundamentally eradicated, three wastes are not generated, the yield of glufosinate-ammonium is high, and industrial popularization is easy.

Process for preparing phosphorus-containing alpha-aminonitriles

-

Paragraph 0096-0099, (2020/06/08)

The present invention relates primarily to processes for preparing particular phosphorus-containing α-aminonitriles of the formulae (Ia) and (Ib) defined hereinafter from corresponding phosphorus-containing cyanohydrin esters and to the use thereof for preparation of glufosinate or of glufosinate salts. The present invention further relates to a process for preparing glufosinate or glufosinate salts.

Method for synthesizing glufosinate ammonium salt

-

Paragraph 0103; 0115-0116; 0123; 0135-0137; 0149-0150, (2019/11/13)

The invention discloses a method for synthesizing a glufosinate ammonium salt. The method comprises the following steps that (1) methyldiethoxyphosphine and n-butanol are used as raw materials to produce an intermediate I by hydrolysis and transesterification; (2) the intermediate I is subjected to a free radical addition reaction with acrolein cyanohydrin acetate to form an intermediate II; (3) the intermediate II is subjected to an aminolysis reaction with ammonia gas to form a mixture of an intermediate III and an intermediate IV; (4) the intermediate III and the intermediate IV are subjected to acid hydrolysis with hydrochloric acid to form an intermediate V; and (5) the intermediate V is neutralized, purified and crystallized to obtain the glufosinate ammonium salt. The method does not need to use toxic raw materials, avoids the large-scale use of ammonia water and ammonium chloride, not only greatly reduces the safety hazard, but also reduces the quantity of by-products and the amount of waste water generated, and the environmental protection risk is greatly reduced; and the purification process is simple, the product content and the yield coefficient are obviously increased,and the method is suitable for industrial scale production.

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