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Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat
SPAN · METALAXIL · Acylon · Jiashuangling · N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-dl-alanine methyl ester · Bleu · axyL · Fubol
Identifikatoren & physikalische Daten
| CAS No. | 57837-19-1 |
|---|---|
| Summenformel | C15H21NO4 |
| Durchschnittliche Molmasse | 279,33 g/mol |
| Monoisotopische Masse | 279,14705815 g/mol |
| SMILES | COCC(=O)N(c1c(C)cccc1C)C(C)C(=O)OC |
| InChIKey | ZQEIXNIJLIKNTD-UHFFFAOYSA-N |
| PubChem CID | 42586 |
| ChEMBL | CHEMBL105809 |
| ChEBI | CHEBI:82790 |
| EC No. | 260-979-7 |
| DTXSID | DTXSID6024175 |
| Lokaler Name | Methyl-N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninat |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 335 |
| SpringerMaterials Properties | Fusion temperature |
| Pestizide | Pesticide -> EPA IRISAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: ApprovedPesticides -> FungicidesPesticide and(or) Waste-water effluent contaminant |
| LogP (Verteilungskoeffizient) | log Kow = 1.651.75 |
| Dichte | 1.20 @ 20 °C1.651.1083 (rough estimate) |
| Color/Form | Fine, white powder... Colorless crystals ... . |
| Löslichkeit | In ethanol 400, acetone 450, toluene 340, n-hexane 11, n-octanol 68 (all g/l at 25 °C)In water, 8,400 mg/l @ 22 °CChloroform (Slightly), Methanol (Slightly)0.84 g/100 mL |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 295.9 °C @ 760 mm Hg564.6 °F422.1°C (rough estimate) |
| Decomposition | When heated to decomposition it emits toxic fumes of nitric oxides. |
| Schmelzpunkt | 71-72 °C71 - 72 °C159.8-161.6 °F72-73°C |
| Dampfdichte | 1.2 |
| Dampfdruck | 0.0000022 [mmHg]Vapor pressure: 293 uPa at 20 °C5.62X10-6 mm Hg @ 25 °C5.62x10-6 mmHg7.5 x 10-4 Pa (25 °C) |
| Brechungsindex | 1.5130 (estimate) |
| Flammpunkt | 100 °C |
| Lagerbedingungen | Sealed in dry,2-8°C |
| pKa (Säurekonstante) | 1.41±0.50(Predicted) |
| Aggregatzustand | Solid |
| Farbe | Off-White to Pale Beige |
| BRN | 2947777 |
| Henry-Konstante | 3.3×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3 |
| InChIKey | ZQEIXNIJLIKNTD-UHFFFAOYSA-N |
| SMILES | COCC(=O)N(C(C)C(=O)OC)c1c(C)cccc1C |
| CAS Datenbank | 57837-19-1(CAS DataBase Reference) |
| NIST chemische Informationen | Dl-alanine, n-(2,6-dimethylphenyl)-n-(methoxyacetyl)-, methyl ester(57837-19-1) |
| EPA chemische Informationen | Metalaxyl (57837-19-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Commission Regulation (EU) No 1141/2010Metalaxyl is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2010/28/EU, Reg. (EU) 2015/1885, Reg. (EU) 2017/2069, Reg. (EU) 2023/918, Reg. (EU) 2026/1826, Reg. (EU) No 540/2011Metalaxyl: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - DL-Alanine, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-, methyl ester: Environment tier I assessment |
| Gefahrenübersicht | An eye irritantCauses liver injury in high-dose feeding studiesNot likely to be a human carcinogen[EPA REDs] Injection into chick eggs causes malformations and embryo lethality[REPROTOX] May cause irritationMay cause skin sensitization[MSDSonline] |
| Special Reports | USEPA/Office of Pesticide ProgramsReregistration Eligibility Decision Document - Metalaxyl. EPA 738-R-94-017, September 1994. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 2, 2003: http://www.epa.gov/pesticides/reregistration/status.htm] |
| FIFRA-Anforderungen | As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Metalaxyl is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0081Pesticide type: fungicideRegistration Standard Date: 09/01/88Case Status: RED Approved 09/94OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.Active ingredient (AI): MetalaxylData Call-in (DCI) Date(s): 06/28/91, 01/24/95AI Status: RED Completed - OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.Tolerances are established for the combined residues of the fungicide metalaxyl (N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methylester) and its metabolites containing the 2,6-dimethylaniline moiety, and N-(2-hydroxymethyl-6-methylphenyl)-N-(methoxyacetyl)-alanine methyl ester, each expressed as metalaxyl equivalents, in or on the following food commodities: alfalfa, forgealfalfa, hayalmondalmond, hullsappleapple, wet pomaceapricot, driedasparagusavocadobeetbeet, sugarbeet, sugar, molassesbeet, sugar, rootsbeet, sugar, topsbeet, topsblueberrybroccoliBrussels sproutscabbagecattle, fatcattle, kidneycattle, livercattle, meatcattle, meat byproducts, except kidney and livercauliflowercitrus, oilcitrus, pulpclover, forageclover, haycottonseedcranberryeggfruit, citrusfruit, stone, groupginsenggoat, fatgoat, kidneygoat, livergoat, meatgoat, meat byproducts, except kidney and livergrain, ceral (except wheat, barley, and oats)grain, cropgrapegrass, foragegrass, hayhog, fathog, kidneyhog, liverhog, meathog, meat byproducts, except kidney and liverhop, dried conehop, greenhorse, fathorse, kidneyhorse, liverhorse, meathorse, meat byproducts, except kidney and liverleafy vegetables (except brassica) group (except spinach)leaves of root and tuber vegetables (human food or animal feed) grouplegume vegetable group (dry or succulent)lettuce, headmilkmustard greensonion, dry bulbonion, greenpeanut, haypeanut, mealpeanut, nutpeanut, shellspeanut, vinespineapplepineapple, fodderpineapple, forageplum, prune, driedpotato waste, dried, processedpotato, processed (including potato, chips)poultry, fatpoultry, kidneypoultry, liverpoultry, meatpoultry, meat byproducts, except kidney and liverraisinsraspberrysheep, fatsheep, kidneysheep, liversheep, meatsheep, meat byproducts, except kidney and liversoybean, grainsoybean, hullssoybean, mealstrawberrysunflowerssunflower, foragetomato, processedvegetables, brassica, leafy, group (except broccoli, cabbage, cauliflower, Brussels sprouts, and mustard greens)vegetable, cucurbit, groupvegetable, fruiting (except cucurbits) groupvegetable, legume, cannery wastevegetable, legume, foliagevegetable, root and tuber groupwalnut.Tolerances with regional registration (refer to section 180.1(n)) are established for the combined residues of the fungicide metalaxyl (N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methyl ester) and its metabolites containing the 2,6-dimethylaniline moiety, and N-(2-hydroxymethyl-6-methyl)-N-(methoxyacetyl)-alanine methylester, each expressed as metalaxyl, in or on the following raw agricultural commodity: papaya.Tolerances are established for indirect or inadvertent residues of metalaxyl in or on the food commodities when present therein as a result of the applicatiion of metalaxyl to growing crops listed in paragraph (a) of this section and other non-food crops to read as follows: barley, grainbarley, fodderbarley, milling fractionsbarley, strawgrain, cereal group (except wheat, barley and oats), foddergrain, cereal group (except wheat, barley and oats), foragegrain, cereal group (except wheat, barley and oats), strawoat, fodderoat, forageoat, grainoat milling fractionsoat, strawwheat, fodderwheat, foragewheat, grainwheat, milling fractionswheat, straw. |
| Hazard Classes and Categories | Acute Tox. 4 (99.5%)Acute toxicity - category 4Acute Tox. 4 * |
| Landesrichtlinien für Trinkwasser | (ME) MAINE 420 ug/L |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Allowable Tolerances | Tolerances are established for the combined residues of the fungicide metalaxyl (N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methylester) and its metabolites containing the 2,6-dimethylaniline moiety, and N-(2-hydroxymethyl-6-methylphenyl)-N-(methoxyacetyl)-alanine methyl ester, each expressed as metalaxyl equivalents, in or on the following food commodities: alfalfa, forge, 6.0 ppmalfalfa, hay, 20.0 ppmalmond, 0.5 ppmalmond, hulls, 10.0 ppmapple, 0.2 ppmapple, wet pomace, 0.4 ppmapricot, dried, 4.0 ppmasparagus, 7.0 ppmavocado, 4.0 ppmbeet, 0.1 ppmbeet, sugar, 0.1 ppmbeet, sugar, molasses, 1.0 ppmbeet, sugar, roots, 0.5 ppmbeet, sugar, tops, 10.0 ppmbeet, tops, 0.1 ppmblueberry, 2.0 ppmbroccoli, 2.0 ppmBrussels sprouts, 2.0 ppmcabbage, 1.0 ppmcattle, fat, 0.4 ppmcattle, kidney, 0.4 ppmcattle, liver, 0.4 ppmcattle, meat, 0.05 ppmcattle, meat byproducts, except kidney and liver, 0.05 ppmcauliflower, 1.0 ppmcitrus, oil, 7.0 ppmcitrus, pulp, 7.0 ppmclover, forage, 1.0 ppmclover, hay, 2.5 ppmcottonseed, 0.1 ppmcranberry, 4.0 ppmegg, 0.05 ppmfruit, citrus, 1.0 ppmfruit, stone, group, 1.0 pmmginseng, 3.0 ppmgoat, fat, 0.4 ppmgoat, kidney, 0.4 ppmgoat, liver, 0.4 ppmgoat, meat, 0.05 ppmgoat, meat byproducts, except kidney and liver, 0.05 ppmgrain, ceral (except wheat, barley, and oats), 0.1 ppmgrain, crop, 0.1 ppmgrape, 2.0 ppmgrass, forage, 10.0 ppmgrass, hay, 25.0 ppmhog, fat, 0.4 ppmhog, kidney, 0.4 ppmhog, liver, 0.4 ppmhog, meat, 0.05 ppmhog, meat byproducts, except kidney and liver, 0.05 ppmhop, dried cone, 20.0 ppmhop, green, 2.0 ppmhorse, fat, 0.4 ppmhorse, kidney, 0.4 ppmhorse, liver, 0.4 ppmhorse, meat, 0.05 ppmhorse, meat byproducts, except kidney and liver, 0.05 ppmleafy vegetables (except brassica) group (except spinach), 5.0 ppmleaves of root and tuber vegetables (human food or animal feed) group, 15.0 ppmlegume vegetable group (dry or succulent), 0.2 ppmlettuce, head, 5.0 ppmmilk, 0.02 ppmmustard greens, 5.0 ppmonion, dry bulb, 3.0 ppmonion, green, 10.0 ppmpeanut, hay, 20.0 pmmpeanut, meal, 1.0 ppmpeanut, nut, 0.2 ppmpeanut, shells, 2.0 ppmpeanut, vines, 20.0 ppmpineapple, 0.1 ppmpineapple, fodder, 0.1 ppmpineapple, forage, 0.1 ppmplum, prune, dried, 4.0 ppmpotato waste, dried, processed, 4.0 ppmpotato, processed (including potato, chips), 4.0 ppmpoultry, fat, 0.4 ppmpoultry, kidney, 0.4 ppmpoultry, liver, 0.4 ppmpoultry, meat, 0.05 ppmpoultry, meat byproducts, except kidney and liver, 0.05 ppmpotato, 0.5 ppmraisins, 6.0 ppmraspberry, 0.5 ppmsheep, fat, 0.4 ppmsheep, kidney, 0.4 ppmsheep, liver, 0.4 ppmsheep, meat, 0.05 ppmsheep, meat byproducts, except kidney and liver, 0.05 ppmsoybean, grain, 1.0 ppmsoybean, hulls, 2.0 ppmsoybean, meal, 2.0 ppmspinach, 10.0 ppmstrawberry, 10.0 ppmsunflowers, 0.1 ppmsunflower, forage, 0.1 ppmtomato, processed, 3.0 ppmvegetables, brassica, leafy, group (except broccoli, cabbage, cauliflower, Brussels sprouts, and mustard greens), 0.1 ppmvegetable, cucurbit, group, 1.0 ppmvegetable, fruiting (except cucurbits) group, 1.0 ppmvegetable, legume, cannery waste, 5.0 ppmvegetable, legume, foliage, 8.0 ppmvegetable, root and tuber group, 0.5 ppmwalnut, 0.5 ppm.Tolerances with regional registration (refer to section 180.1(n)) are established for the combined residues of the fungicide metalaxyl (N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methyl ester) and its metabolites containing the 2,6-dimethylaniline moiety, and N-(2-hydroxymethyl-6-methyl)-N-(methoxyacetyl)-alanine methylester, each expressed as metalaxyl, in or on the following raw agricultural commodity: papaya, 0.1 ppm.Tolerances are established for indirect or inadvertent residues of metalaxyl in or on the food commodities when present therein as a result of the applicatiion of metalaxyl to growing crops listed in paragraph (a) of this section and other non-food crops to read as follows: barley, grain, 0.2 ppmbarley, fodder, 2.0 ppmbarley, milling fractions, 1.0 ppmbarley, straw, 2.0 ppmgrain, cereal group (except wheat, barley and oats), fodder, 1.0 ppmgrain, cereal group (except wheat, barley and oats), forage, 1.0 ppmgrain, cereal group (except wheat, barley and oats), straw, 1.0 ppmoat, fodder, 2.0 ppmoat, forage, 2.0 ppmoat, grain, 0.2 ppmoat milling fractions, 1.0 ppmoat, straw, 2.0 ppmwheat, fodder, 2.0 ppmwheat, forage, 2.0 ppmwheat, grain, 0.2 ppmwheat, milling fractions, 1.0 ppmwheat, straw, 2.0 ppm. |
| Treatment | Consider gastric lavage, as well was dilution with milk or water after ingestion. Administer charcoal as a slurry following ingestionhowever, activated charcoal should not be given to patients ingesting strong acidic or basic caustic chemicals. In case of inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. Administer symptomatic treatment as necessary. (T36) |
| Wechselwirkungen | Because metalaxyl is used on tobacco, a 90 day smoke inhalation study was conducted. Male & female Fischer 344 rats were exposed to smoke form cigarettes containing 0, 130, 3,900, or 13,000 ppm of metalaxyl for 4 hr/day, 5 days/wk. The max air concn of metalaxyl was 5 ug/L. The concns in test cigarettes were 100-1,000 times avg residue levels & 30-100 times greater than the expected max residue levels. Although the study was limited in its ability to simulate human exposure, the results were adequate to demonstrate toxicological effects from exposures are unlikely beyond that from exposures associated with heavy smoking. The profile of residues in inhalable smoke indicated 30% was metalaxyl, 4% was 2,6-dimethylaniline, & 65% was unidentified material. |
| Zielorgane | Hepatic |
| Gesundheitliche Auswirkungen | ARDS/acute lung injury, burns of the esophagus or gastrointestinal tract can result from metalaxyl poisoning. (T36) |
| Ökotoxizitätswerte | LC50 Rainbow trout 130-132 mg/L /Conditions of bioassay not specified/LC50 Bluegill sunfish 139-150 mg/L /Conditions of bioassay not specified/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 30 to 284(2) indicate that metalaxyl is expected to have very high to moderate mobility in soil(SRC). Volatilization of metalaxyl from moist soil surfaces is not expected to be an important fate process(3) given an estimated Henry's Law constant of 3.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.62X10-6 mm Hg(4), and water solubility, 8,400 mg/l(4). Metalaxyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Metalaxyl undergoes fairly rapid degradation (half-life of approx 40 days) in soils incubated aerobically(5). Experiments with 14C-metalaxyl demonstrated that it was readily metabolized in soil with a history of fungicide treatment (half-life of 14 days) but not in a control soil(6). In a tobacco soil, rapid degradation of metalaxyl occurred with a half-life of 6 days(7). The main breakdown product of metalaxyl in soil was the acid metabolite(7).AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 30 to 284(2), indicates that metalaxyl is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.62X10-6 mm Hg(4), and water solubility, 8,400 mg/l(4). According to a classification scheme(5), an estimated BCF of 4(SRC), from its log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Photolysis of metalaxyl in aqueous solution using UV light with wavelengths greater than 290 nm resulted in 10% substrate transformation in 3 hours(8). Long time (65 hr) irradiation under artificial sunlight in the presence of humic acids resulted in 65% degradation of the chemical(8). Photolysis leads not only to rearrangement of the N-acyl group to the aromatic ring but also to demethoxylation, N-deacylation, and elimination of the methoxycarbonyl group from the molecule(8). Based on biodegradation studies in soil, metalaxyl is expected to biodegrade in aqueous systems(SRC). Metalaxyl undergoes fairly rapid degradation (half-life of approx 40 days) in soils incubated aerobically(9). Experiments with 14C-metalaxyl demonstrated that its was readily metabolized in soil with a history of fungicide treatment (half-life of 14 days) but not in a control soil(10).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metalaxyl, which has a vapor pressure of 5.62X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase metalaxyl is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 14 hours(SRC), calculated from its rate constant of 27X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase metalaxyl may be removed from the air by wet and dry deposition(SRC). Metalaxyl undergoes photolysis in water(4) and, by analogy, may undergo direct photolysis in the atmosphere(SRC). |
| Lebensmitteluntersuchungswerte | The concn of metalaxyl in two samples of wine from Italy were 0.27 and 2.2 mg/kg(1). The mean concn of metalaxyl in endive, lettuce, apples, and strawberries were 0.008 ppm (max, 0.14 ppmnumber of positive samples, 1.3%), 0.009 ppm (max, 0.38 ppmnumber of positive samples, 0.9%), 0.002 ppm (max, 0.08 ppmnumber of positive samples, 0.9%), and 0.009 ppm (max, 0.04 ppmnumber of positive samples, 1.4%), respectively(2). The mean concn of metalaxyl in cucumber and tomato from Egyptian markets in 1995 was 0.24 mg/kg (frequency, 1 of 47 samples) and 0.15 mg/kg (frequency, 1 of 62 samples), respectively(3). The mean concn of metalaxyl in cucumber and grapes from Egyptian markets in 1996 was 0.18 mg/kg (frequency, 2 of 94 samples) and 0.20 mg/kg (frequency, 1 of 47 samples), respectively(4). Metalaxyl was found in 4 of 6,391 samples of domestic agricultural commodities sampled between Oct 1, 1981 and Sept 20, 1986 in US at concns of 0.1, 0.5, 1.0, and 2.0 ppm, respectively(5). The mean concn of metalaxyl in grapes from Ontario, Canada between 1991-1995 was 0.23 ug/g (0.9% of sample positive)(6). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | Inhalation (L917)oral (L917)dermal (L917)eye contact (L917). |
| Toxizitätsübersicht | Binds to nAChRs in nervous systems. It also causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (T10, A590) |
| Average Daily Intake | As part of Belgian Total Diet study in 1991-1993, the avg daily intake of metalaxyl was 0.03 mg/kg/day(1). |
| Signs and Symptoms | Metalaxyl is mildly irritating to the skin and eyes. Exposure to metalaxyl often results in such nonspecific symptoms as headache, dizziness, weakness, and nausea. Metaxyl poisoning can produce an allergic hypersensitivity dermatitis or asthma with bronchospasm and wheezing with chronic exposure. (T36) |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN 1648 3/PG 2 |
| Zollcode | 29242990 |
| RTECS-Nr. | AY6910000 |
| R-Sätze (R) | 22-43-52/53-36-20/21/22-11 |
| Toxizität | LD50 in rats (mg/kg): 669 orally (Urech) |
| Gefahrensymbole | Xn,F |
| Sicherheitshinweise (S) | 13-24-37-46-61-36-26-16 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 57837-19-1(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Chronic 3Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
As an important fungicide group, acylanilides have a longer history than triazoles. Metalaxyl (44) is one of the most important fungicides in the group. It originates from the class of herbicidal chloroacetanilides, particularly metolachlor (45). Metolachlor, having a chiral carbon center and a chiral axis, is composed of four stereoisomers, the most herbicidally active one of which is the (αR, 1S)-isomer (32). For the stereoselective synthesis of this isomer, novel iridium-ferrocenyldiphosphine catalysts for the enantioselective hydrogenation of N-(2-ethyl-6-methylphenyl)- N-(1 -methoxymethyl)-ethylidene-amine are reported. In the most effective approach, the catalyst is generated in situ from [Ir(cod)Cl]2(cod = cyclooctadiene) and the ferrocenyldiphosphine ligand (R)-(S)-PPF-P(3,5-xyl)2 (46) (33).When the substrate to catalyst ratio is 106, the conversion is complete in 2 to 3 h, producing metolachlor in optical yields over 80% (34).
Verwenden
Metalaxyl is used for the control of air-borne pathogens by foliar application and of soil-borne pathogens by soil application on a wide range of crops. It is particularly useful against Oomycetes including soil-borne Phytophthora diseases.