Metalaxyl

Last updated
Metalaxyl
Metalaxyl.svg
Metalaxyl 3D BS.png
Names
IUPAC name
Methyl 2-[N-(2,6-dimethylphenyl)(methoxy)acetamido]propanoate
Other names
Methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.055.418 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 260-979-7
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: ZQEIXNIJLIKNTD-UHFFFAOYSA-N Yes check.svgY
  • COCC(=O)N(c1c(C)cccc1C)C(C)C(=O)OC
Properties
C15H21NO4
Molar mass 279.33 g/mol
AppearanceFine white powder
Density 1.20g/cm3 at 20 °C
Melting point 71 to 72 °C (160 to 162 °F; 344 to 345 K) [1]
Boiling point 295.9 °C (564.6 °F; 569.0 K) at 760 mm Hg
8,400 mg/L at 22 °C
log P 1.65 (octanol/water) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Metalaxyl is an acylalanine fungicide with systemic function. [3] Its chemical name is methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate. It can be used to control Pythium in a number of vegetable crops, and Phytophthora in peas. Metalaxyl-M is the ISO common name [4] and Ridomil Gold is the trade name for the optically pure (-) / D / R active stereoisomer, which is also known as mefenoxam. [5]

Contents

It is the active ingredient in the seed treatment agent Apron XL LS. [6]

The fungicide has suffered severe resistance problems. The fungicide was marketed for use against Phytophthora infestans . However, in the summer of 1980, in the Republic of Ireland, the crop was devastated by a potato blight epidemic after a resistant race of the oomycete appeared. [7] Irish farmers later successfully sued the company for their losses.[ citation needed ] Maximum pesticide residue limits for the EU/UK are set at 0.5 mg/kg for oranges and 1.0 mg/kg for apples.[ citation needed ] As early as 1998 Pythium was known to be widely developing resistance to metalaxyl [8] which was the most effective control at the time. [8] Various Pythium populations have been known to have resistance to mefenoxam since the 1980s [9] and metalaxyl since 1984. [10] There is wide variability in resistance/sensitivity between Pythium species, with some populations showing complete ineffectiveness. [9]

Synthesis

The first synthesis of metalaxyl was disclosed in patents filed by Ciba Geigy. [11]

Metalaxyl synthesis V1.svg

2,6-Xylidine is alkylated with methyl 2-bromopropionate to give an alanine derivative. This is further reacted with the acid chloride of methoxyacetic acid to yield racemic metalaxyl. [11] [12] The homochiral, single-isomer version of the chemical, which retains all its fungicidal activity, has been manufactured. [13]

Related Research Articles

<i>Phytophthora infestans</i> Species of single-celled organism

Phytophthora infestans is an oomycete or water mold, a fungus-like microorganism that causes the serious potato and tomato disease known as late blight or potato blight. Early blight, caused by Alternaria solani, is also often called "potato blight". Late blight was a major culprit in the 1840s European, the 1845–1852 Irish, and the 1846 Highland potato famines. The organism can also infect some other members of the Solanaceae. The pathogen is favored by moist, cool environments: sporulation is optimal at 12–18 °C (54–64 °F) in water-saturated or nearly saturated environments, and zoospore production is favored at temperatures below 15 °C (59 °F). Lesion growth rates are typically optimal at a slightly warmer temperature range of 20 to 24 °C.

<span class="mw-page-title-main">Captan</span> Chemical compound

Captan is a general use pesticide (GUP) that belongs to the phthalimide class of fungicides. It is a white solid, although commercial samples appear yellow or brownish.

<i>Pythium</i> Genus of single-celled organisms

Pythium is a genus of parasitic oomycetes. They were formerly classified as fungi. Most species are plant parasites, but Pythium insidiosum is an important pathogen of animals, causing pythiosis. The feet of the fungus gnat are frequently a vector for their transmission.

Phytophthora sojae is an oomycete and a soil-borne plant pathogen that causes stem and root rot of soybean. This is a prevalent disease in most soybean growing regions, and a major cause of crop loss. In wet conditions the pathogen produces zoospores that move in water and are attracted to soybean roots. Zoospores can attach to roots, germinate, and infect the plant tissues. Diseased roots develop lesions that may spread up the stem and eventually kill the entire plant. Phytophthora sojae also produces oospores that can remain dormant in the soil over the winter, or longer, and germinate when conditions are favourable. Oospores may also be spread by animals or machinery.

Acibenzolar-<i>S</i>-methyl Chemical compound

Acibenzolar-S-methyl is the ISO common name for an organic compound that is used as a fungicide. Unusually, it is not directly toxic to fungi but works by inducing systemic acquired resistance, the natural defence system of plants.

Phytophthora citrophthora, also known as brown rot of citrus, is a soil borne oomycete that infects several economically important citrus crops. A diagnostic symptom of P. citrophthora is gummosis, wherein lesions around the base of the tree exude sap. Other common symptoms include dark longitudinal lesions forming at the soil line, a sour smell, and eventual cracking of the bark. Advanced symptoms include yellowing and necrosis of the tree canopy. Girdling action caused by the pathogen around the trunk can often cause the collapse of the tree. Resistant lemon varieties have been developed and their implementation has been effective at controlling the spread of the disease. Fruits that have been infected with P. citrophthora exhibit symptoms of brown rot characterized by a distinct odor. This disease is most active in the moderate temperatures of spring, fall, and winter months, opposite of most other Phytophthora species.

<i>Phytophthora erythroseptica</i> Species of single-celled organism

Phytophthora erythroseptica—also known as pink rot along with several other species of Phytophthora—is a plant pathogen. It infects potatoes causing their tubers to turn pink and damages leaves. It also infects tulips (Tulipa) damaging their leaves and shoots.

<i>Phytophthora capsici</i> Species of single-celled organism

Phytophthora capsici is an oomycete plant pathogen that causes blight and fruit rot of peppers and other important commercial crops. It was first described by L. Leonian at the New Mexico State University Agricultural Experiment Station in Las Cruces in 1922 on a crop of chili peppers. In 1967, a study by M. M. Satour and E. E. Butler found 45 species of cultivated plants and weeds susceptible to P. capsici In Greek, Phytophthora capsici means "plant destroyer of capsicums". P. capsici has a wide range of hosts including members of the families Solanaceae and Cucurbitaceae as well as Fabaceae.

<span class="mw-page-title-main">Azoxystrobin</span> Chemical compound

Azoxystrobin is a broad spectrum systemic fungicide widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.

This article summarizes different crops, what common fungal problems they have, and how fungicide should be used in order to mitigate damage and crop loss. This page also covers how specific fungal infections affect crops present in the United States.

<span class="mw-page-title-main">Zinc bis(dimethyldithiocarbamate)</span> Chemical compound

Zinc dimethyldithiocarbamate is a coordination complex of zinc with dimethyldithiocarbamate. It is a pale yellow solid that is used as a fungicide, the sulfur vulcanization of rubber, and other industrial applications.

<span class="mw-page-title-main">Fluazinam</span> Chemical compound

Fluazinam is a broad-spectrum fungicide used in agriculture. It is classed as a diarylamine and more specifically an arylaminopyridine. Its chemical name is 3-chloro-N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamine. The mode of action involves the compound being an extremely potent uncoupler of oxidative phosphorylation in mitochondria and also having high reactivity with thiols. It is unique amongst uncouplers in displaying broad-spectrum activity against fungi and also very low toxicity to mammals due to it being rapidly metabolised to a compound without uncoupling activity. It was first described in 1992 and was developed by researchers at the Japanese company Ishihara Sangyo Kaisha.

Buckeye rot of tomato is caused by three species of pathogens in the genus Phytophthora: P. nicotianae var. parasitica, P. capsici, and P. drechsleri. It is an oomycete that thrives in warm, wet conditions and lives in the soil. It is characterized by a bull’s eye pattern of dark brown rotting on the tomato fruit, and affects fruit that is close to, or lying on the soil. The easiest management is to keep the plant out of contact with the soil, although other chemical methods can be very effective. This disease commonly occurs in the southeast and south central areas of the United States. The disease has affected a large portion of crop yield in the United States as well as India. The relatively small genome size of Phytophthora parasitica compared to Phytophthora infestans gives researchers the unique ability to further examine its ability to cause disease.

<span class="mw-page-title-main">Fludioxonil</span> Chemical compound

Fludioxonil is a synthetic phenylpyrrole chemical introduced by Ciba-Geigy in 1993 for use as a non-systemic fungicide. It is a structural analog of the natural fungicide pyrrolnitrin.

<span class="mw-page-title-main">Thiophanate-methyl</span> Chemical compound

Thiophanate-methyl is an organic compound with the formula C6H4(NHC(S)NH(CO)OCH3)2. The compound is a colorless or white solid, although commercial samples are generally tan-colored. It is prepared from o-phenylenediamine. It is a widely used fungicide used on tree, vine, and root crops.

<span class="mw-page-title-main">Agriculture in Maryland</span>

The US state of Maryland has large areas of fertile agricultural land in its coastal and Piedmont zones, though this land use is being encroached upon by urbanization. Agriculture is oriented to dairy farming for nearby large city milksheads, plus specialty perishable horticulture crops, such as cucumbers, watermelons, sweet corn, tomatoes, melons, squash, and peas.

<span class="mw-page-title-main">Pyraclostrobin</span> Agricultural fungicide, QoI, strobilurin

Pyraclostrobin is a quinone outside inhibitor (QoI)-type fungicide used in agriculture. Among the QoIs, it lies within the strobilurin chemical class.

<span class="mw-page-title-main">Boscalid</span> Chemical compound used to kill fungi

Boscalid is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases. It was first marketed by BASF in 2002 using their brand name Endura. The compound is an biphenyl amide derived inhibitor of succinate dehydrogenase.

<span class="mw-page-title-main">Strawberry cultivation in California</span>

Strawberries in the United States are almost entirely grown in California – 86% of fresh and 98% of frozen in 2017 – with Florida a distant second. Of that 30.0% was from Monterey, 28.6% from Ventura, 20.0% from Santa Barbara, 10.0% from San Luis Obispo, and 9.2% from Santa Cruz. The Watsonville/Salinas strawberry zone in Santa Cruz/Monterey, and the Oxnard zone in Ventura, contribute heavily to those concentrations.

3-(Difluoromethyl)-1-methyl-1<i>H</i>-pyrazole-4-carboxylic acid Chemical compound

3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid is a chemical compound which is used commercially as an intermediate to seven fungicides which act by inhibition of succinate dehydrogenase (SDHI). It consists of a pyrazole ring with difluoromethyl, methyl and carboxylic acid groups attached in specific positions.

References

  1. O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1058
  2. Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 134
  3. Sukul, P; Spiteller, M (2000). "Metalaxyl: persistence, degradation, metabolism, and analytical methods". Reviews of Environmental Contamination and Toxicology. 164: 1–26. PMID   12587832.
  4. "Compendium of Pesticide Common Names: metalaxyl". BCPC.
  5. Monkiedje, Adolphe; Spiteller, Michael (2002). "Effects of the phenylamide fungicides, mefenoxam and metalaxyl, on the microbiological properties of a sandy loam and a sandy clay soil". Biology and Fertility of Soils. 35 (6): 393–398. doi:10.1007/s00374-002-0485-1. S2CID   22642870.
  6. "bmz10s02.pdf" (PDF). Government of Manitoba. Archived from the original (PDF) on 2007-09-30.
  7. Working on potato blight in Northern Ireland
  8. 1 2 "Survey of Pythium Isolates for Resistance to Subdue (metalaxyl)" (PDF). UMass Amherst . Retrieved 2020-11-23.
  9. 1 2 Del Castillo Múnera, Johanna; Hausbeck, Mary K. (2016). "Characterization of Pythium Species Associated With Greenhouse Floriculture Crops in Michigan". Plant Disease . 100 (3). American Phytopathological Society: 569–576. doi: 10.1094/pdis-03-15-0296-re . ISSN   0191-2917. PMID   30688597.
  10. Sanders, P. L. (1984). "Failure of Metalaxyl to Control Pythium Blight on Turfgrass in Pennsylvania". Plant Disease . 68 (1). American Phytopathological Society: 776. doi:10.1094/pd-68-776. ISSN   0191-2917.
  11. 1 2 GBpatent 1500581,"Substituted amides and their use as fungicides",issued 1978-02-08, assigned to Ciba-Geigy AG
  12. Ishitani, Haruro; Yu, Zhibo; Ichitsuka, Tomohiro; Koumura, Nagatoshi; Onozawa, Shun-ya; Sato, Kazuhiko; Kobayashi, Shū (2022). "Two-Step Continuous-Flow Synthesis of Fungicide Metalaxyl through Catalytic C−N Bond-Formation Processes". Advanced Synthesis & Catalysis. 364: 18–23. doi:10.1002/adsc.202100898.
  13. Blaser, Hans-Ulrich; Spindler, Felix (1997). "Enantioselective catalysis for agrochemicals. The case histories of (S)–metolachlor, (R)–metalaxyl and clozylacon". Topics in Catalysis. 4 (3/4): 275–282. doi:10.1023/A:1019164928084.