CAS number：1071-83-6
molecular formula：C3H8NO5P
molecular weight：169.07
EINECS number：213-997-4

English synonyms

TOTAL;TILLER;GLYPHOSATE 62 % IPA SALT;Rounduuuuup(Monsanto);KERNEL(R);landmaster;ENVISION(R);tumbleweed

Related categories

Pesticide raw materials; chemical biology; feed additives; organic raw materials; plant hormones and nucleic acids; pesticide residues, veterinary drugs and fertilizers; agricultural herbicide raw materials; amino acid derivatives; herbicides; pesticides; other herbicides; phosphorus compounds; intermediates ;pesticide intermediates;medical raw materials;chemical pesticides;biochemical reagents-phytohormones and nucleic acids;agricultural raw materials;organic chemical raw materials;chemical industry;glyphosate;plant drugs;raw materials;agricultural and veterinary raw materials;Agro-Chemicals;HERBICIDE; 2005/70/EU; GPesticides&Metabolites; Organophosphorous Method Specific; Alphabetic; Endocrine Disruptors (Draft) Analytical Standards; EPA; European Community: ISO and DIN; Herbicides; Method Specific; Insecticides; chemical materials; agricultural raw materials; organic intermediates; agrochemicals; agricultural raw materials-herbicides; pesticide intermediates; reference substances

Introduction

Glyphosate is an organophosphate herbicide. It is a non-selective systemic conduction herbicide for stem and leaf treatment, developed by Monsanto in the early 1970s, and it is generally made into isopropylamine salt or sodium salt when it is usually used. Its isopropylamine salt is the active ingredient of the well-known herbicide trademark "Roundup". Glyphosate is a high-efficiency, low-toxicity, broad-spectrum herbicide with systemic conduction. This product dissolves the wax layer on the surface of the leaves, branches and stems of weeds, and the drug effect quickly enters the plant conduction system to cause the weeds to dry up and die. It can effectively control annual and biennial grasses, sedges and broad-leaved weeds, and has a good control effect on perennial weeds such as thatch, Cyperus cyperi and Bermudagrass. It is widely used in orchards, mulberry gardens, tea gardens, rubber chemical weeding in orchards, grassland renewal, forest fire escapes, railways, highway wasteland and no-till land.

Chemical properties

The pure product is a white solid. m.p.230°C (decomposition). Hardly soluble in common organic solvents; at 25°C, the solubility in water is 1.2%. It is usually made into glyphosate amine salt, such as isopropylamine salt, dimethylamine salt, etc. It can also be made into sodium salt. Glyphosate salts are soluble in water. 

Use

●  A systemic broad-spectrum herbicide. It mainly inhibits enolpyruvyl shikimelin phosphate synthase in plants, thereby inhibiting the conversion of shikimelin to phenylalanine, tyrosine and tryptophan, interfering with protein synthesis and causing plant death.
It was originally used in rubber gardens to control thatch and other weeds, which can make rubber trees tap rubber one year earlier, and old rubber trees will give birth. It is now being gradually promoted in forestry, orchards, mulberry gardens, tea gardens, rice and wheat, rice and rapeseed rotations, etc. Various weeds are sensitive to glyphosate in different degrees, so the dosage is also different. For annual weeds such as barnyardgrass, green foxtail, kangarinia, goosegrass, crabgrass, and pigtail, the dosage is 6-10.5 g/100m2 based on the active ingredients. The dosage of psyllium chinensis, chrysanthemum, commelina, etc. is 11.4-15g/100m2 in terms of active ingredients. 18-30g/100m2 is needed for Imperata Imperata, Bone Grass, Reed, etc. Generally, 3-4.5kg of water is needed, and the stems and leaves of weeds are uniformly and directional sprayed.

●  A non-selective, short-lived post-emergence herbicide for the control of perennial deep-rooted weeds, annual and biennial grasses, sedges and broadleaf weeds

●  It is mainly used for weeding in orchards, tea gardens, mulberry fields and other cash crop gardens

●  Used in orchards, tea gardens, mulberry fields, no-tillage land, and roadside weed control

●  It is a non-selective, non-residual herbicide, very effective against perennial root weeds, widely used in rubber, mulberry, tea, orchards and sugarcane fields

●  It is a systemic conduction broad-spectrum herbicide, suitable for weeding in orchards, tea gardens, mulberry gardens, rubber and forest trees

●  Glyphosate is an organophosphorus herbicide. Its herbicidal properties were discovered by D.D. Baird in the United States in 1971. By the 1980s, it had become an important herbicide in the world. Widely used in agriculture, forestry, animal husbandry, industrial transportation, etc., including forests, rubber plantations, farmland, tea mulberry, orchards, sugarcane fields, border defense roads, forest fire protection belts, and non-agricultural farming such as railways, airports, warehouses, oil depots, and power stations. of weeding. Glyphosate breaks down quickly in the soil and has no shelf life. Calibration of instruments and devices; evaluation methods; working standards; quality assurance/quality control; other.

Production method

●  dialkyl phosphite method
Glycine, dialkyl phosphite, and paraformaldehyde are used as raw materials through addition, condensation, and hydrolysis. The product purity is 95%, the total yield is 80%, and the cost is low.
Chloromethylphosphonic acid method
Preparation of chloromethylphosphonic acid Phosphorus trichloride and paraformaldehyde were reacted at 200-250°C (corresponding pressure 2.5-3.0MPa) for 3-5 hours to obtain chloromethylphosphonic acid dichloride. According to literature reports, the ratio is phosphorus trichloride: polyoxymethylene (1.2-1.5): 1 (mol). The yield is 67% without a catalyst, and the yield can be increased to 80% to 89% with Lewis acid as a catalyst. Domestic research has not yet reached the literature level.
Hydrolysis available chloromethylphosphonic acid.
Cl2P(O)CH2Cl+H2O→(HO)2P(O)CH2Cl+HCl
Synthesis of glyphosate Equimolar chloromethylphosphonic acid and glycine, in aqueous sodium hydroxide solution (pH>10), reflux for 10-20 hours, and then acidify with hydrochloric acid to obtain glyphosate.
If acidified to pH 4, it is monosodium salt; pH 8.5 is disodium salt. If the glyphosate solution is added with equimolar dimethylamine, the solution of glyphosate dimethylamine salt is formed.
iminodiacetic acid method
Preparation of iminodiacetic acid: Chloroacetic acid is reacted with ammonia water in the presence of calcium hydroxide, acidified, and then neutralized with sodium hydroxide. The yield is 85%.
Or use hydrocyanic acid as raw material, react with formaldehyde and ammonia, and the yield is 90%.
Preparation of Diglyphosate: Diglyphosate was prepared by heating iminodiacetic acid, formaldehyde and phosphorous acid in the presence of sulfuric acid with a yield of 90%.
Synthesis of glyphosate: Mix diglyphosate with water, and react with excess hydrogen peroxide in the presence of equimolar sulfuric acid to prepare glyphosate with a yield of 90% to 95%.
There are many ways to oxidize diglyphosate. In addition to hydrogen peroxide, concentrated sulfuric acid, noble metal (palladium, rhodium, etc.) oxides can also be used, and activated carbon air oxidation or electrolysis can also be used. For example, put 10 parts of bisglyphosate, 170 parts of water and 0.6 parts of 5% palladium-activated carbon catalyst in an autoclave, pass oxygen to 2.07×105Pa, and react at 90-100°C. Yield 96%, purity 97%.

●  There are two production methods from the main categories, namely, the production method using iminodiacetic acid (IDA) as the raw material and the production method using glycine-dialkyl phosphite as the raw material. Among them, the glycine-dialkyl phosphite method The production capacity of the device is the largest, and the production enterprises are the most. The production capacity accounts for about 80% of the total glyphosate production in the country, reaching 70,000 tons; the production capacity of the IDA method device is nearly 30,000 tons. There are 4 methods for subdivision: 1) Self-made (using chloroacetic acid method) IDA, the production process of diglyphosate using concentrated sulfuric acid oxidation to glyphosate has been developed since the 1980s, but due to the strong acid wastewater of calcium chloride The amount is large, the yield is low (IDA yield is about 70%), and only water preparation can be prepared, and its maximum annual output is 2000t (10% water preparation). In the 1990s, the production enterprises gradually decreased, and the output declined. 2) Enterprises that produce trimethyl phosphite themselves use the trimethyl phosphite production process to produce glyphosate. This method replaces methanol with water as the solvent, and uses sodium hydroxide as the catalyst instead of triethylamine, which reduces post-processing. The yield is about 65%, but because the selling price of trimethyl ester is higher than that of dimethyl ester, only the enterprises that produce trimethyl ester themselves can have a certain market competitiveness in their cost. 3) There are many enterprises using dimethyl phosphite process to produce glyphosate, and the scale of production equipment is relatively large. In recent years, this process has achieved a series of achievements by optimizing production process conditions, adopting advanced equipment, and automatic operating system. With the advancement of technology, the product quality index has reached the requirements of the international market, so this process is mainly used in our country. 4) Self-made (diethanolamine dehydrogenation oxidation) IDA or purchased IDA, using hydrogen peroxide to catalyze the oxidation of diglyphosate to prepare glyphosate. Raw material consumption quota: paraformaldehyde 500kg/t, methanol 500kg/t, glycine 700kg/t, triethylamine 50kg/t, dimethyl phosphite 1000kg/t, hydrochloric acid 3000kg/t.

Team Presentation