草甘膦：修订间差异

Glyphosate
	IUPAC名; N-(phosphonomethyl)glycine
别名	2-[(phosphonomethyl)amino]acetic acid；N-(膦酰基甲基)甘氨酸；草甘膦；农达；镇草宁；N-(膦酰甲基)氨基乙酸；N-(磷酰基甲基)甘氨酸
识别
CAS号	1071-83-6 ; ; 38641-94-0 (isopropylammmonium salt); 70393-85-0 (sesquisodium salt); 81591-81-3 (trimethylsulfonium salt)
PubChem	3496
ChemSpider	3376
SMILES	O=C(O)CNCP(=O)(O)O;
InChI	1/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9);
InChIKey	XDDAORKBJWWYJS-UHFFFAOYAE
EC编号	213-997-4
ChEBI	27744
RTECS	MC1075000
KEGG	C01705
性质
化学式	C3H8NO5P
摩尔质量	169.07 g·mol−1
外观	白色结晶粉末
密度	1.704 g/cm3 (20 °C)
熔点	184.5 °C
沸点	decomp. at 187 °C
溶解性（水）	1.01 g/100 mL (20 °C)
log P	−2.8
pKa	<2, 2.6, 5.6, 10.6
危险性
警示术语	R：R41, R51/53
安全术语	S：S2, S26, S39, S61
MSDS	InChem MSDS
欧盟编号	607-315-00-8
欧盟分类	Irritant (Xi); Dangerous for the environment (N)
	GHS危险性符号;
GHS提示词	DANGER
H-术语	H318, H411
P-术语	P273, P280, P305+351+338, P310, P501
闪点	non-flammable
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

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2013年4月3日 (三) 17:01的版本

草甘膦或嘉磷塞（Glyphosate；N-(phosphonomethyl)glycine），其商品名稱為年年春（Roundup）^[3]或農達^[4]、好你春、日日春、日產春、好伯春等^[5]，是一种廣效型^[6]的有机磷除草剂。它是一种非选择性内吸传导型茎叶处理除草剂，1970年由孟山都公司的化學家約翰·E.弗朗茨在1970年發現^[7]^[8]，其專利於2000年到期。草甘膦使用时一般将其制成异丙胺盐或钠盐。

嘉磷塞的除草性能优异，极易被植物叶片吸收并传导至植物全身，对一年生及多年生杂草都有很高的活性。透過基因改造，可使作物能耐嘉磷塞。

Called by experts in herbicides "virtually ideal" due to its broad spectrum and low toxicity compared with other herbicides,^[9] glyphosate was quickly adopted by farmers. Use increased even more when Monsanto introduced glyphosate-resistant crops, enabling farmers to kill weeds without killing their crops. In 2007 glyphosate was the most used herbicide in the United States agricultural sector, with 180 to 185 million pounds (82,000至84,000公噸) applied, and the second most used in home and garden market where users applied 5 to 8 million pounds (2,300至3,600公噸); additionally industry, commerce and government applied 13 to 15 million pounds (5,900至6,800公噸).^[10] While glyphosate has been approved by regulatory bodies worldwide and is widely used, concerns about its effects on humans and the environment persist.^[11]

Glyphosate's mode of action is to inhibit an enzyme involved in the synthesis of the aromatic amino acids: tyrosine, tryptophan and phenylalanine. It is absorbed through foliage and translocated to growing points. Because of this mode of action, it is only effective on actively growing plants; it is not effective as a pre-emergence herbicide.

Some crops have been genetically engineered to be resistant to it (i.e. Roundup Ready, also created by Monsanto Company). Such crops allow farmers to use glyphosate as a post-emergence herbicide against both broadleaf and cereal weeds, but the development of similar resistance in some weed species is emerging as a costly problem. Soy was the first Roundup Ready crop.

Chemistry

Glyphosate synthesis from chloroacetic acid

Glyphosate is an aminophosphonic analogue of the natural amino acid glycine, and the name is a contraction of gly(cine) phos(phon)ate. The molecule has several dissociable hydrogens, especially the first hydrogen of the phosphate group. The molecule tends to exist as a zwitterion where a phosphonic hydrogen dissociates and joins the amine group. Glyphosate is soluble in water to 12 g/L at room temperature.

Main deactivation path is hydrolysis to aminomethylphosphonic acid (AMPA).^[12]

Glyphosate was first discovered to have herbicidal activity in 1970 by John E. Franz, while working for Monsanto.^[13] Franz received the National Medal of Technology in 1987^[14] and the Perkin Medal for Applied Chemistry^[15] in 1990 for his discoveries. Franz was then inducted into the National Inventor's Hall of Fame in 2007.^[16]

Biochemistry

Glyphosate kills plants by interfering with the synthesis of the aromatic amino acids phenylalanine, tyrosine and tryptophan. It does this by inhibiting the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS), which catalyzes the reaction of shikimate-3-phosphate (S3P) and phosphoenolpyruvate to form 5-enolpyruvyl-shikimate-3-phosphate (ESP).^[17] ESP is subsequently dephosphorylated to chorismate, an essential precursor for the amino acids mentioned above.^[18] These amino acids are used in protein synthesis and to produce secondary metabolites such as folates, ubiquinones and naphthoquinone.

X-ray crystallographic studies of glyphosate and EPSPS show that glyphosate functions by occupying the binding site of the phosphoenolpyruvate, mimicking an intermediate state of the ternary enzyme substrates complex.^[19]^[20]

The enzyme that glyphosate inhibits, EPSPS, is found only in plants and micro-organisms. EPSPS is not present in animals, which instead obtain aromatic amino acids from their diet.^[21]

Glyphosate has also been shown to inhibit other plant enzymes,^[22]^[23] and also has been found to affect animal enzymes.^[24]

Glyphosphate is absorbed through foliage. Because of this mode of action, it is only effective on actively growing plants; it is not effective in preventing seeds from germinating.

Use

Glyphosate used as an alternative to mowing in an apple orchard in Ciardes, Italy

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.^[25] By volume, it is one of the most widely used herbicides.^[26] It is commonly used for agriculture, horticulture, and silviculture purposes, as well as garden maintenance (including home use).^[26]

In many cities, glyphosate is sprayed along the sidewalks and streets, as well as crevices in between pavement where weeds often grow. However, up to 24% of glyphosate applied to hard surfaces can be run off by water.^[27] Glyphosate contamination of surface water is highly attributed to urban use.^[28]

File:KillingRainforest.jpg

Herbicides sprayed over a coca field in Colombia

Glyphosate is one of a number of herbicides used by the United States and Colombian governments to spray coca fields through Plan Colombia. Its effects on legal crops and effectiveness in fighting the war on drugs have been disputed.^[29] There are reports that widespread application of glyphosate in attempts to destroy coca crops in South America have resulted in the development of glyphosate-resistant strains of coca nicknamed "Boliviana Negra", which have been selectively bred to be both "Roundup Ready" and larger and higher yielding than the original strains of the plant.^[30] However, there are no reports of glyphosate-resistant coca in the peer-reviewed literature. In addition, since spraying of herbicides is not permitted in Colombian national parks, this has encouraged coca growers to move into park areas, cutting down the natural vegetation, and establishing coca plantations within park lands.^[31]

Formulations and tradenames

Glyphosate is marketed in the United States and worldwide by many agrochemical companies in different solution strengths under many tradenames: Accord, Aquaneat, Aquamaster, Bronco, Buccaneer, Campain, Clearout 41 Plus, Expedite, Fallow Master, Genesis Extra I, Glyfos Induce, Glypro, GlyStar Induce, GlyphoMax Induce, Honcho, JuryR, Landmaster, MirageR, Pondmaster, Protocol, Ranger, Rascal, Rattler, Razor Pro, Rodeo, Roundup, I, Roundup Pro Concentrate, Roundup UltraMax, Roundup WeatherMax, Silhouette, Touchdown IQ.^[32]^[33]^[34]^[35]

Manufacturers include Dow AgroSciences; Du Pont; Cenex/Land O’Lakes, Helena, Platte, Riverside/Terra, and Zeneca.^[35]

Glyphosate is an acid molecule, but it is formulated as a salt for packaging and handling. Various salt formulations include isopropylamine, diammonium, monoammonium, or potassium. Some brands include more than one salt. Some companies report their product as acid equivalent (ae) of glyphosate acid, or some report it as active ingredient (ai) of glyphosate plus the salt, and others report both. In order to compare performance of different formulations it is critical to know how the products were formulated. Since the salt does not contribute to weed control and different salts have different weights, the acid equivalent is a more accurate method of expressing, and comparing concentrations.^[36] Adjuvant loading refers to the amount of adjuvant^[37]^[38] already added to the glyphosate product. Fully loaded products contain all the necessary adjuvants, including surfactant, some contain no adjuvant system; while other products contain only a limited amount of adjuvant (minimal or partial loading) and additional surfactants must be added to the spray tank before application.^[36] As of 2000 (just before Monsanto's patent on glyphosate expired) there were 400 commercial adjuvants from over 34 different companies available for use in commercial agriculture.^[39]^[40]

Products are supplied most commonly in formulations of 120, 240, 360, 480 and 680 g active ingredient per litre. The most common formulation in agriculture is 360 g, either alone or with added cationic surfactants.

For 360 g formulations, European regulations allow applications of up to 12 litres per hectare for control of perennial weeds such as couch grass. More commonly, rates of 3 litres per hectare are practiced for control of annual weeds between crops.^[41]

Monsanto's Roundup

File:Roundup herbicide logo.jpg

The Monsanto trademark for Roundup

Monsanto developed and patented the glyphosate molecule in the 1970s, and has marketed Roundup since 1973. It retained exclusive rights in the United States until its United States patent expired in September, 2000.

As of 2009, sales of the Roundup herbicide line of products represented about 10% of Monsanto's revenue due to competition from other producers of other glyphosate-based herbicides;^[42] the overall Roundup line of products (which includes GM seeds) represents about half of Monsanto's yearly revenue.^[43]

The active ingredient of Roundup is the isopropylamine salt of glyphosate. Another important ingredient in some formulations of Roundup is the surfactant POEA (polyethoxylated tallow amine), which has been found to be highly toxic to animals and to humans.^[44]^[45]^[46]^[47]

Monsanto also produces seeds which grow into plants genetically engineered to be tolerant to glyphosate, which are known as Roundup Ready crops. The genes contained in these seeds are patented. Such crops allow farmers to use glyphosate as a post-emergence herbicide against most broadleaf and cereal weeds. Soy was the first Roundup Ready crop, and was produced at Monsanto's Agracetus Campus located in Middleton, Wisconsin.

In November 2009, a French environment group (MDRGF) accused Monsanto of using chemicals in Roundup formulations not disclosed to the country's regulatory bodies, and demanded the removal of those products from the market.^[48]^[49]

Toxicity

Glyphosate is the active ingredient in herbicide formulations containing it. However, in addition to glyphosate salts, commercial formulations of glyphosate contain additives such as surfactants which vary in nature and concentration. Laboratory toxicology studies have suggested that other ingredients in combination with glyphosate may have greater toxicity than glyphosate alone.^[50] Toxicologists have studied glyphosate alone, additives alone, and formulations.

Glyphosate toxicity

Glyphosate has a United States Environmental Protection Agency (EPA) Toxicity Class of III (on a I to IV scale, where IV is least dangerous) for oral and inhalation exposure.^[51] Nonetheless, as with other herbicides, the EPA requires that products containing glyphosate carry a label that warns against oral intake, mandates the use of protective clothing, and instructs users not to re-enter treated fields for at least 4 hours.^[51]^[52] Glyphosate does not bioaccumulate and breaks down rapidly in the environment.^[53]

Human

The EPA considers glyphosate to be noncarcinogenic and relatively low in toxicity.^[51] The EPA considered a "worst case" dietary risk model of an individual eating a lifetime of food derived entirely from glyphosate-sprayed fields with residues at their maximum levels. This model indicated that no adverse health effects would be expected under such conditions.^[51]

Effects on fish and amphibians

Glyphosate is generally less persistent in water than in soil, with 12 to 60 day persistence observed in Canadian pond water, yet because glyphosate binds to soil, persistence of over a year have been observed in the sediments of ponds in Michigan and Oregon.^[51] In streams, maximum glyphosate concentrations were measured immediately post-treatment and dissipated rapidly.^[51] Glyphosate is "practically nontoxic to slightly toxic" for amphibians and fish.^[54]

Soil degradation, and effects on micro-organism and worms

When glyphosate comes into contact with the soil, it can be rapidly bound to soil particles and be inactivated.^[51]^[55] Unbound glyphosate can be degraded by bacteria.^[56]

In soils, half-lives vary from as little as three days at a site in Texas to 141 days at a site in Iowa.^[55] In addition, the glyphosate metabolite aminomethylphosphonic acid has been found in Swedish forest soils up to two years after a glyphosate application.^[57] Glyphosate adsorption to soil varies depending on the kind of soil.^[58]

It has been suggested that glyphosate can harm the bacterial ecology of soil and cause micronutrient deficiencies in plants,^[59] including nitrogen-fixing bacteria.^[60]

Additive toxicity

Polyethoxylated tallow amine

A review of the literature provided to the EPA in 1997 found that POEA was more toxic to fish than glyphosate^[61]

Formulation Toxicity

Human

Data from the California Environmental Protection Agency's Pesticide Illness Surveillance Program, which also tracks other agricultural chemicals, shows that glyphosate-related incidents are some of the most common.^[62]^[63] However, incident counts alone do not take into account the number of people exposed and the severity of symptoms associated with each incident.^[63] For example, if hospitalization were used as a measure of the severity of incidents, then glyphosate would be considered relatively safe; over a 13-year period in California, none of the 515 reported hospitalizations were attributed to glyphosate.^[63]

Deliberate ingestion of Roundup in quantities ranging from 85 to 200 ml has resulted in death within hours of ingestion, although it has also been ingested in quantities as large as 500 ml with only mild or moderate symptoms.^[64] There is a reasonable correlation between the amount of Roundup ingested and the likelihood of serious systemic sequelae or death. Ingestion of >85 ml of the concentrated formulation is likely to cause significant toxicity in adults. Corrosive effects – mouth, throat and epigastric pain and dysphagia – are common. Renal and hepatic impairment are also frequent and usually reflect reduced organ perfusion. Respiratory distress, impaired consciousness, pulmonary edema, infiltration on chest x-ray, shock, arrythmias, renal failure requiring haemodialysis, metabolic acidosis, and hyperkalaemia may occur in severe cases. Bradycardia and ventricular arrhythmias often present prior to death.

Dermal exposure to ready-to-use glyphosate formulations can cause irritation, and photo-contact dermatitis has been occasionally reported. These effects are probably due to the preservative Proxel (benzisothiazolin-3-one). Inhalation is a minor route of exposure, but spray mist may cause oral or nasal discomfort, an unpleasant taste in the mouth, or tingling and irritation in the throat. Eye exposure may lead to mild conjunctivitis. Superficial corneal injury is possible if irrigation is delayed or inadequate.^[50]

In vitro studies on human cells

A 2000 review concluded that "under present and expected conditions of new use, there is no potential for Roundup herbicide to pose a health risk to humans".^[65] A 2002 review by the European Union reached the same conclusion.^[66]

Glyphosate causes oxidative damage to human skin cells. Antioxidants such as vitamins C and E were found by one study to provide some protection against such damage, leading the authors to recommend that these chemicals be added to glyphosate formulations.^[67] Severe skin burns are very rare.^[50]

Endocrine disruptor debate

A study published in 2000 found that Roundup interfered with an enzyme involved in testosterone production in mouse cell culture.^[68] A study by the Seralini lab published in 2005 found that glyphosate interferes with aromatase, an estrogen biosynthesis enzyme, in cultures of human placental cells and that the Roundup formulation of glyphosate had stronger such activity.^[69] A follow up study by the Seralini lab, published in 2009, showed similar results in human liver cells.^[70] A study on rats published in 2010 found that administering Roundup Transorb orally to prepubescent rats at a dose of 0.25 mL/100 g of body weight, once a day for 30 days, reduced testosterone production and affected testicle morphology, but did not affect levels of estradiol and corticosterone.^[71]

Monsanto has responded, saying that (a) Roundup formulations do contain surfactants (detergents) to help the active ingredient penetrate the waxy cuticle of the plant. (b) The surfactants are indeed more toxic than the glyphosate. (c) "If you put a detergent of any sort on cells in a petri dish, the cells get sick (and will die if you get the concentration high enough or recover if you remove the detergent soon enough)"; (d) the cell types chosen in these studies and the parameters measured were selected more to score political points than to help fully describe the risks of glyphosate and surfactants; (e) the experiments are artificial and not helpful – no one is supposed to drink Roundup, and it is not ever put on naked cells (we all have skin and workers are meant to wear protective clothes.^[72]

In 2007, the EPA selected glyphosate for further screening through its Endocrine Disruptor Screening Program. Selection for this program is based on a compound's prevalence of use and does not imply particular suspicion of endocrine activity.^[73]

Genetic damage

A 2009 study on mice has found that a single intraperitoneal injection of Roundup in concentration of 25 mg/kg caused chromosomal aberrations and induction of micronuclei.^[74]

Other mammals

A review of the ecotoxicological data on Roundup shows there are at least 58 studies of the effects of Roundup itself on a range of organisms.^[54] This review concluded that "for terrestrial uses of Roundup minimal acute and chronic risk was predicted for potentially exposed non-target organisms".

In a 2001, three groups of pregnant rats were fed, respectively, a regular diet with clean water, a regular diet with 0.2 ml glyphosate/ml drinking water; and a regular diet with 0.4 ml glyphosate/ml drinking water. Glyphosate induces a variety of functional abnormalities in fetuses and pregnant rats.^[75] Also in recent mammalian research, glyphosate has been found to interfere with an enzyme involved testosterone production in mouse cell culture.^[68]

The acute oral toxicity of Roundup is > 5,000 mg/kg in the rat.^[76] It showed no toxic effects when fed to animals for two years, and only produced rare cases of reproductive effects when fed in extremely large doses to rodents and dogs. An increase in cancer rates in animal studies has not been demonstrated, and it is poorly absorbed in the digestive tract. Glyphosate has no significant potential to accumulate in animal tissue.^[26]

The EPA,^[77] the EC Health and Consumer Protection Directorate, and the UN World Health Organization have all concluded pure glyphosate is not carcinogenic. Opponents of glyphosate claim Roundup has been found to cause genetic damage, citing Peluso et al.^[78] The authors concluded the damage was "not related to the active ingredient, but to another component of the herbicide mixture".

Mammal research indicates oral intake of 1% glyphosate induces changes in liver enzyme activities in pregnant rats and their fetuses.^[79]

Laboratory studies have shown teratogenic effects of Roundup in animals.^[80]^[81] These reports have proposed that the teratogenic effects are caused by impaired retinoic acid signaling.^[82] News reports have supposed that regulators have been aware of these studies since 1980.^[83]

Effects on fish and amphibians

A study of various formulations of glyphosate found that "risk assessments based on estimated and measured concentrations of glyphosate that would result from its use for the control of undesirable plants in wetlands and over-water situations showed that the risk to aquatic organisms is negligible or small at application rates less than 4 kg/ha and only slightly greater at application rates of 8 kg/ha.".^[84]

Glyphosate formulations are much more toxic for amphibians and fish than glyphosate alone.^[54]^[85]^[86] "Aquaculture, freshwater and marine fisheries supply about 10% of world human calorie intake."^[87] A study published in 2010 proposed commercial glyphosate can cause neural defects and craniofacial malformations in African clawed frogs (Xenopus laevis). The experiments used frog embryos that were incubated with 1:5000 dilutions of a commercial glyphosate solution. The frog embryos suffered diminution of body size, alterations of brain morphology, reduction of the eyes, alterations of the branchial arches and otic placodes, alterations of the neural plate, and other abnormalities of the nervous system. The authors suggested glyphosate itself was responsible for the observed results because injection of pure glyphosate produced similar results in a chicken model.^[82]

Because of this known toxicity, only some formulations of glyphosate are registered for use in aquatic applications.^[88]^[89] Monsanto and other companies produce glyphosate products with alternative surfactants that are specifically formulated for aquatic use, for example "Biactive" and "AquaMaster".^[90] The glyphosate formulations registered for aquatic use have been found to have negligible adverse effects on sensitive amphibians.^[91]

Soil degradation and effects on micro-organism and worms

A laboratory study published in 1992 indicated that glyphosate formulations could harm earthworms^[92] and beneficial insects.^[93] However, the reported effect of glyphosate on earthworms has been criticized.^[54] The results conflict with results from field studies where no effects were noted for the number of nematodes, mites, or springtails after treatment with Roundup at 2 kilograms active ingredient per hectare.^[94]

A 2009 study using a RoundUp formulation has concluded that absorption into plants delays subsequent soil-degradation, and can increase glyphosate persistence in soil from two to six times.^[95]

Effect on plant health

A study published in 2005 found a correlation between an increase in the infection rate of wheat by fusarium head blight and the application of glyphosate, but the authors wrote: "because of the nature of this study, we could not determine if the association between previous GF (glyphosate formulation) use and FHB development was a cause-effect relationship".^[96] Other studies have found causal relationships between glyphosate and decreased disease resistance.^[97]

Resistance in weeds and microorganisms

Resistance evolves after a weed population has been subjected to intense selection pressure in the form of repeated use of a single herbicide.^[98]^[99] The first documented cases of weed resistance to glyphosate were found in Australia in 1996, involving rigid ryegrass (Lolium rigidum) near Orange, New South Wales.^[100]^[101] Weeds resistant to the herbicide have been called superweeds.^[102] As of 2010 in the United States 7 to 10 × 10⁶英畝（40,000平方公里） of soil was afflicted by those superweeds, or about 5% of the 170 million acres planted with corn, soybeans and cotton, the crops most affected, in 22 states.^[103] In 2006 farmers associations were reporting 103 biotypes of weeds within 63 weed species with herbicide resistance.^[104]> In 2009 Canada identified its first resistant weed, giant ragweed, and at that time fifteen weed species hadbeen confirmed as resistant to glyphosate.^[98]^[105]

In response, farmers are hand-weeding, using tractors to turn over soil between crops, and using other herbicides in addition to glyphosate. Agricultural biotech companies are also developing genetically engineered crops resistant to other herbicides. "Bayer is already selling cotton and soybeans resistant to glufosinate, another weedkiller. Monsanto's newest corn is tolerant of both glyphosate and glufosinate, and the company is developing crops resistant to dicamba, an older pesticide. Syngenta is developing soybeans tolerant of its Callisto product. And Dow Chemical is developing corn and soybeans resistant to 2,4-D, a component of Agent Orange, the defoliant used in the Vietnam War."^[103]

Palmer amaranth

In 2004, a glyphosate-resistant variation of Palmer amaranth, commonly known as pigweed, was found in Georgia and confirmed by a 2005 study.^[106] In 2005 resistance was also found in North Carolina.^[107] Glyphosate resistance followed the widespread use of Roundup Ready crops, which lead to an unprecedented selection pressure to glyphosate.^[107] The weed variation is now widespread in southeast United States.^[108] Cases are also reported in Texas^[108] and Virginia.^[109]

Conyza biotypes

Conyza bonariensis (also known as hairy fleabane and buva) and Conyza canadensis (known as horseweed or marestail), are other weed species that had lately developed glyphosate resistance.^[110]^[111]^[112] A 2008 study on the current situation of glyphosate resistance in South America concluded that "resistance evolution followed intense glyphosate use" and the utilization of glyphosate-resistant soybean crops is a factor encouraging increase in glyphosate use.^[113]

Ryegrass

Glyphosate resistant ryegrass (Lolium) has occurred in most of the Australian agricultural area and other areas of the world. All cases of evolution of resistance to glyphosate in Australia were characterized by intensive use of the herbicide while no other effective weed control practices were used. Studies indicate that resistant ryegrass does not compete well against non-resistant plants and their numbers decrease when not grown under conditions of glyphosate application.^[114]

Johnson grass

Glyphosate resistant Johnson grass (Sorghum halepense) has occurred in Roundup Ready soybean culture in Argentina.^[115]

Coca

Boliviana negra, also known as "supercoca", is a relatively new strain of coca that is resistant to glyphosate, which is a key ingredient in the multibillion-dollar aerial coca eradication campaign undertaken by the government of Colombia with United States financial and military backing known as Plan Colombia.^[116] Spraying Boliviana negra with glyphosate would serve to strengthen its growth by eliminating the non-resistant weeds surrounding it. Joshua Davis, writing in Wired magazine, found no evidence of CP4 EPSPS, a protein produced by the Roundup Ready soybean, suggesting Bolivana negra was not created in a laboratory but by selective breeding in the fields. According to Davis, the growing popularity of Boliviana negra amongst growers could have serious repercussions for the United States war on drugs.^[117]^[118]

Legal cases

False advertising

The New York Times reported that in 1996, "Dennis C. Vacco, the Attorney General of New York, ordered the company to pull ads that said Roundup was "safer than table salt" and "practically nontoxic" to mammals, birds and fish. The company withdrew the spots, but also said that the phrase in question was permissible under E.P.A. guidelines."^[119]

On Fri Jan 20, 2007, Monsanto was convicted in France of false advertising of Roundup for presenting it as biodegradable, and claiming it left the soil clean after use. Environmental and consumer rights campaigners brought the case in 2001 on the basis that glyphosate, Roundup's main ingredient, is classed as "dangerous for the environment" and "toxic for aquatic organisms" by the European Union.^[120] Monsanto appealed and the court upheld the verdict; Monsanto appealed again to the French Supreme Court, and in 2009 it also upheld the verdict.^[121]

Scientific fraud

On two occasions, the United States EPA has caught scientists deliberately falsifying test results at research laboratories hired by Monsanto to study glyphosate.^[122] The first incident involved Industrial Biotest Laboratories (IBT). The United States Justice Department closed the laboratory in 1978, and its leadership was found guilty in 1983 of charges of falsifying statements, falsifying scientific data submitted to the government, and mail fraud.^[123] In 1991, Don Craven, the owner of Craven Laboratories and three employees were indicted on 20 felony counts. Craven, along with fourteen employees were found guilty of similar crimes.^[124]

Monsanto has stated the Craven Labs investigation was started by the EPA after a pesticide industry task force discovered irregularities, that the studies have been repeated, and that Roundup's EPA certification does not now use any studies from Craven Labs or IBT.^[122]

Trade dumping allegations

United States companies have cited trade issues with glyphosate being dumped into the western world market areas by Chinese companies and a formal dispute was filed in 2010.^[125]^[126]

Genetically modified crops

Some micro-organisms have a version of 5-enolpyruvoyl-shikimate-3-phosphate synthetase (EPSPS) that is resistant to glyphosate inhibition. The version used in the initial round of genetically modified crops was isolated from Agrobacterium strain CP4 (CP4 EPSPS) that was resistant to glyphosate.^[127]^[128] This CP4 EPSPS gene was cloned and transfected into soybeans.

In 1996, genetically modified soybeans were made commercially available.^[129] Current glyphosate-resistant crops include soy, maize (corn), sorghum, canola, alfalfa, and cotton, with wheat still under development.

Genetically modified crops have become the norm in the United States. For example, in 2010, 70% of all the corn that was planted was herbicide-resistant; 78% of cotton, and 93% of all soybeans.^[130]。

理化性质

白色结晶，易溶于水、乙醇、丙酮、氯苯、煤油和二甲苯，不可燃，常温下稳定，易于运输。对人类低毒。^[65]

制取

以氯乙酸铵为原料，先与氢氧化钙反应得到亚氨基二乙酸钙盐，在硫酸钠作用下生成亚氨基二乙酸。然后用三氯化磷、甲醛与亚氨基二乙酸反应，得到双甘膦，最后用浓硫酸或过氧化氢氧化双甘膦，得到草甘膦。
从氯乙酸铵制取草甘膦
自产亚磷酸三甲酯的企业采用亚磷酸三甲酯生产工艺生产草甘膦。
采用亚磷酸二甲酯（膦酸二甲酯）生产工艺生产：亚磷酸二甲酯与甲醛、甘氨酸反应生成草甘膦二甲酯，然后水解得草甘膦。此法有收率高，纯度高的优点，是目前中国生产草甘膦的主要方法。^[131]
从亚磷酸二甲酯制取草甘膦

作用机制

草甘膦主要是阻碍芳香氨基酸的生物合成，即苯丙氨酸、色氨酸及酪氨酸通过莽草酸途径的合成。它对5-烯醇丙酮酰莽草酸-3-磷酸合酶（EPSP合酶）有抑制作用，该酶可以催化莽草酸-3-磷酸和烯醇丙酮磷酸向5-烯醇丙酮酰莽草酸-3-磷酸（EPSP）的转化，因此草甘膦干扰这一生物合成的酶促反应，导致莽草酸在生物体内的积累。^[132] 此外草甘膦也可以抑制其他植物酶^[133]^[134]和动物酶^[135]的活性。

草甘膦在高等植物内的代谢十分缓慢，曾测试出其代谢物为氨甲基膦酸和甲氨基乙酸。正由于草甘膦在植物体内具有高度的运转性能、缓慢的降解性能和高度的植物毒性，决定了它是一个理想的防除多年生杂草的除草剂。^[136]

目前正在研究对草甘膦有抗性植物的培养。生物化学家从微生物中筛选出体内含有EPSP过量的菌种，将其有关的基因导入到烟草和黄豆组织中，从而培养出能耐草甘膦的植株。^[137]^[138]

對人體影響

毒性及處理方法

草甘膦一般在口服後15分鐘內便可能產生嘔吐及喉部疼痛現象，另外接著可能產生腹痛及腹瀉症狀。病徵通常在服用量超過100毫升較明顯^[5]。中毒者不能透過催吐來解毒，而只能透過解除各種病徵來舒緩病況^[5]。

致癌性與轉基因食物

由於草甘膦的优异除草性能，透過基因改造，可使作物能耐草甘膦。不過，草甘膦本身是致癌物質^[139]，對人體有害，所以歐盟對食水中的殘留草甘膦含量有嚴格的規定^[140]。根據德國萊比錫大學於2011年12月進行的一項研究，在受驗的一批柏林市區居民的尿液樣本內，所有樣本均發現其殘留草甘膦含量比歐盟食水內的殘留標準高出5到20倍^[139]^[140]，足以證明草甘膦在人類的整條食物鏈內不斷殘留積累。所以現時有建議完全禁用草甘膦。

参见

参考资料

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