N-benzyl-N-phosphonomethyl-glycine
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal for 45h; Ambient temperature; | 99% |
In ethanol; hydrogen bromide |
Conditions | Yield |
---|---|
Calgon CENTAUR 80-100 mesh (149-177 μm) at 95℃; Product distribution / selectivity; | 98.6% |
Norit PK at 95℃; Conversion of starting material; | 98.3% |
Nuchar RGC at 95℃; Conversion of starting material; | 98.9% |
glycine
methyl (chloromethyl)(trifluoromethyl)phosphinate
A
trifluoromethan
B
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; Rate constant; | A 98% B 49% |
Aminomethylphosphonic acid
glyoxalic acid monohydrate
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
96% | |
In water |
N-<(diethoxyphosphonyl)methyl>glycine ethyl ester
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With bee venom In various solvent(s) at 37℃; for 6h; pH 8.7; | 95.3% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydrogenchloride; water for 28h; Reflux; | 95% |
N-acetylglyphosate
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydrogenchloride In water for 72h; pH-value; Time; Reflux; | 93.8% |
N,N’-bis(phosphonomethyl)-2,5-diketopiperazine
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydrogenchloride; water at 165℃; for 6h; Sealed tube; | 92% |
Conditions | Yield |
---|---|
palladium In water | 91% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With water In methanol for 12h; Reflux; | 90% |
Conditions | Yield |
---|---|
Stage #1: methyleneaminoacetonitrile With trimethyl phosphite; phosphorus trichloride In hexane; water at 0℃; for 20h; Inert atmosphere; Stage #2: With water; N,N-dimethyl-formamide for 18h; Reflux; | 90% |
1,4-di(carboxymethyl)-2,5-diketopiperazine
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
Stage #1: 1,4-di(carboxymethyl)-2,5-diketopiperazine With phosphorus(III) oxide; trifluorormethanesulfonic acid at 60 - 80℃; for 6h; Stage #2: With water at 150℃; for 12h; | 89.4% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; glycine With hydrogenchloride; phosphoric acid In water at 40℃; for 1h; Stage #2: With phosphoric acid In water at -8 - 45℃; for 2h; Temperature; | 87.78% |
trimethyl ester of <<(carboxymethyl)amino>methyl>phosphonic acid
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydrogenchloride for 4h; Heating; | 85% |
With hydrogenchloride for 4h; Heating; Yield given; | |
With hydrogenchloride; water for 6h; Heating; Yield given; |
N-phosphonomethyl-glycine ethyl ester
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With α-chymotrypsin In various solvent(s) at 25℃; for 6h; pH 7.8; | 80.2% |
dimethylsulfite
phosphonomethylimino-di-acetic acid
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With dihydrogen peroxide In water | 76% |
methyl N-phosphonomethylglycinate
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
75% | |
With hydrogenchloride | 71% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydrogen bromide for 12h; Heating; | 73.4% |
Conditions | Yield |
---|---|
With sulphur dichloride; dihydrogen peroxide In water | 71% |
With dihydrogen peroxide In water | 68% |
Conditions | Yield |
---|---|
With potassium hydroxide | A 60% B n/a |
(chloromethyl)phosphonothioic acid dichloride
glycine
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With sodium hydroxide In water for 40h; Heating; | 31% |
B
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydroxymethylphosphonic acid; hydrogen; 5 wt% Ru/carbon at 200℃; under 5171.62 Torr; for 17h; | A 29% B 8.9% |
With hydrogen; 5 wt% Ru/carbon at 200℃; under 5171.62 Torr; for 20.5h; | A 23.5% B 6.8% |
With hydrogen; Cl5H2ORu(2+)*2K(1+) at 200℃; under 5171.62 Torr; for 16h; | A 23.5% B 6.5% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide In water | 20% |
Conditions | Yield |
---|---|
5 wt% Ru/carbon at 200℃; under 5171.62 Torr; for 16h; | A 3.1% B 9.7% |
5 wt% Ru/carbon at 200℃; under 5171.62 Torr; for 16h; | A 2.9% B 8.4% |
Conditions | Yield |
---|---|
With hydrogenchloride; H2; CO; acetic acid | 5% |
N-(phosphonemethyl)glycine
dimethyl amine
N-(phosphonomethyl)glycine dimethylamine salt
Conditions | Yield |
---|---|
In toluene at 50 - 70℃; Concentration; Temperature; Large scale; | 99.3% |
at 70℃; under 1500.15 Torr; for 7h; Temperature; Pressure; Sealed tube; Large scale; | 99.8% |
In water at 20℃; for 3h; Temperature; Time; | 85% |
In water | |
In water at 5 - 50℃; under 750.075 Torr; Temperature; Pressure; Sealed tube; |
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With potassium hydroxide at 40℃; Stage #2: cetylpyridinium bromide In methanol at 20℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With potassium hydroxide at 50℃; Stage #2: 1-methylpyridinium bromide In water at 20℃; for 1h; | 99% |
N-(phosphonemethyl)glycine
N-methyl-N-butylpyrrolidinium bromide
1-butyl-1-methylpyrrolidinium glyphosate
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With sodium hydroxide at 30℃; Stage #2: N-methyl-N-butylpyrrolidinium bromide In water at 20℃; for 1h; | 99% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With ammonia In water at 95℃; for 1h; pH=6.5; Stage #2: With methanol; ethanol at 25℃; Product distribution / selectivity; | 98.3% |
Stage #1: N-(phosphonemethyl)glycine With ammonia In water at 95℃; for 1h; pH=6.5; Stage #2: With methanol; formaldehyd; water at 25℃; Product distribution / selectivity; | 98.1% |
With ammonium carbonate In ethanol at 20℃; for 0.5h; Product distribution / selectivity; Industry scale; | 98% |
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With sodium hydroxide at 50℃; Stage #2: cetyltrimethylammonium chloride In water at 20℃; for 1h; | 98% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
Stage #1: N-methyl-N-ethylpyrrolidinium bromide With sodium carbonate In acetonitrile at 30℃; for 3h; Stage #2: N-(phosphonemethyl)glycine In acetonitrile at 25℃; for 5h; | 97% |
Conditions | Yield |
---|---|
Stage #1: methanol; N-(phosphonemethyl)glycine With hydrogenchloride at 40℃; for 2h; Stage #2: With oxirane at 20℃; | 96% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With sodium hydroxide at 40℃; Stage #2: 1-methyl-3-octyloxymethylimidazolium iodide In water at 20℃; for 1h; | 96% |
Conditions | Yield |
---|---|
Stage #1: N-cetylpyridinium iodide With potassium hydroxide In 1,4-dioxane at 25℃; for 6h; Stage #2: N-(phosphonemethyl)glycine In 1,4-dioxane at 25℃; for 6h; | 96% |
ethanol
N-(phosphonemethyl)glycine
N-phosphonomethyl-glycine ethyl ester
Conditions | Yield |
---|---|
With thionyl chloride for 2h; Esterification; Heating; | 95% |
Stage #1: ethanol; N-(phosphonemethyl)glycine With hydrogenchloride at 45℃; for 3.5h; Stage #2: With triethylamine at 20℃; | 93% |
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With potassium hydroxide at 60℃; Stage #2: N-amyl-N-methylpiperidinium bromide In acetone at 20℃; for 1h; | 95% |
Conditions | Yield |
---|---|
Stage #1: N,N-didecyl-N,N-dimethylammonium bromide With sodium hydride In tetrahydrofuran at 65℃; for 1h; Stage #2: N-(phosphonemethyl)glycine In tetrahydrofuran at 30℃; for 1h; | 95% |
N-(phosphonemethyl)glycine
1-ethyl-3-methylimidazolium iodide
Conditions | Yield |
---|---|
Stage #1: 1-ethyl-3-methylimidazolium iodide With sodium hydroxide In acetone at 30℃; for 5h; Stage #2: N-(phosphonemethyl)glycine In acetone at 65℃; for 5h; | 95% |
Conditions | Yield |
---|---|
Stage #1: tetramethylammonium bromide With potassium carbonate In methanol at 25℃; for 6h; Stage #2: N-(phosphonemethyl)glycine In methanol at 65℃; for 3h; | 95% |
N-(phosphonemethyl)glycine
1-n-butyl-1-methylpiperidin-1-ium bromide
Conditions | Yield |
---|---|
Stage #1: N,N-butyl-methyl-piperidinium bromide With sodium hydroxide In acetone at 30℃; for 5h; Stage #2: N-(phosphonemethyl)glycine In acetone at 65℃; for 5h; | 93% |
Conditions | Yield |
---|---|
Stage #1: domiphen brominde With potassium hydroxide In 1,4-dioxane at 25℃; for 6h; Stage #2: N-(phosphonemethyl)glycine In 1,4-dioxane at 25℃; for 6h; | 92% |
Conditions | Yield |
---|---|
Stage #1: N-dodecylpyridinium chloride With sodium hydride In tetrahydrofuran at 65℃; for 1h; Stage #2: N-(phosphonemethyl)glycine In tetrahydrofuran at 30℃; for 1h; | 92% |
N-(phosphonemethyl)glycine
Conditions | Yield |
---|---|
Stage #1: N-(phosphonemethyl)glycine With potassium hydroxide at 40℃; Stage #2: 1-methyl-3-octylthiomethylimidazolium iodide In methanol at 20℃; for 1h; | 91% |
Conditions | Yield |
---|---|
Stage #1: cetyltrimethylammonium chloride With sodium carbonate In acetonitrile at 30℃; for 3h; Stage #2: N-(phosphonemethyl)glycine In acetonitrile at 25℃; for 5h; | 91% |
Initially patented and sold by Monsanto in the 1970s under the tradename Roundup, its U.S. patent expired in 2000. It is now also available in other formulations, e.g. Resolva 24H, which contains glyphosate and diquat. Glyphosate is the most used herbicide in the USA.In the US, 5-8 million pounds are used every year on lawns and yards and 85-90 million pounds are used annually in US agriculture.
Glyphosate (CAS NO.1071-83-6) was first discovered to have herbicidal activity in 1970 by John E. Franz, while working for Monsanto. Franz received the National Medal of Technology in 1987,and the Perkin Medal for Applied Chemistry. in 1990 for his discoveries.
When Glyphosate (CAS NO.1071-83-6) comes into contact with the soil it can be rapidly bound to soil particles and be inactivated. Unbound glyphosate can be degraded by bacteria.However, glyphosphate has been shown to increase the infection rate of wheat by fusarium head blight in fields that have been treated with glyphosphate.
In soils, half lives vary from as little as 3 days at a site in Texas, 141 days at a site in Iowa, to between 1–3 years in Swedish forest soils.It appears that higher latitude sites have the longest soil persistences such as in Canada and Scandinavia.
Glyphosate,with the CAS NO.1071-83-6, is an organic solid of odorless white crystals. It is a non-selective herbicide used on many food and non-food crops as well as non-crop areas such as roadsides. Glyphosate comes in many forms, including an acid and several salts. These can be either solids or an amber-colored liquid.
Physical properties about Glyphosate are: (1)ACD/LogP: 0.272; (2)ACD/LogD (pH 5.5): -3.35; (3)ACD/LogD (pH 7.4): -4.13; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 6; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.529; (12)Molar Refractivity: 31.051 cm3; (13)Molar Volume: 100.656 cm3; (14)Polarizability: 12.309 10-24cm3; (15)Surface Tension: 86.3440017700195 dyne/cm; (16)Density: 1.68 g/cm3; (17)Flash Point: 235.528 °C; (18)Enthalpy of Vaporization: 79.713 kJ/mol; (19)Boiling Point: 465.835 °C at 760 mmHg
Uses of Glyphosate: Glyphosate is effective in killing a wide variety of plants, including grasses, broadleaf, and woody plants. It has a relatively small effect on some clover species. By volume, it is one of the most widely used herbicides. It is commonly used for agriculture, horticulture, and silviculture purposes, as well as garden maintenance (including home use).
When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear eye/face protection;
3. Avoid release to the environment. Refer to special instructions safety data sheet;
4. Keep out of the reach of children;
5. Wear suitable gloves;
6. Wear suitable protective clothing;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9);
(2)InChIKey=XDDAORKBJWWYJS-UHFFFAOYSA-N;
(3)SmilesP(=O)(CNCC(=O)O)(O)O;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | LDLo | oral | 2143mg/kg (2143mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL) LUNGS, THORAX, OR RESPIRATION: FIBROSING ALVEOLITIS | Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 91, 1991. |
man | TDLo | oral | 1214mg/kg (1214mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" CARDIAC: CHANGE IN RATE | Human & Experimental Toxicology. Vol. 10, Pg. 103, 1991. |
mouse | LD50 | intraperitoneal | 130mg/kg (130mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Toxicology Letters. Vol. 1000(Sp, |
mouse | LD50 | oral | 1568mg/kg (1568mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Toxicology and Applied Pharmacology. Vol. 45, Pg. 319, 1978. |
quail | LD50 | oral | > 4640mg/kg (4640mg/kg) | Pesticide Manual. Vol. 9, Pg. 459, 1991. | |
rabbit | LD50 | oral | 3800mg/kg (3800mg/kg) | Pesticide & Toxic Chemical News. Vol. 7, Pg. 6, 1978. | |
rabbit | LD50 | skin | 7940mg/kg (7940mg/kg) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A222, Pg. 1984, | |
rat | LC50 | inhalation | > 12200mg/m3/4 (12200mg/m3) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A222, Pg. 1984, | |
rat | LD50 | intraperitoneal | 235mg/kg (235mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Toxicology Letters. Vol. 1000(Sp, |
rat | LD50 | oral | 4873mg/kg (4873mg/kg) | Toxicology and Applied Pharmacology. Vol. 45, Pg. 319, 1978. | |
rat | LD50 | oral | 4873mg/kg (4873mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Toxicology and Applied Pharmacology. Vol. 45, Pg. 319, 1978. |
women | LDLo | oral | 4gm/kg (4000mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 91, 1991. |
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