Metrafenone is a benzophenone fungicide and is mainly used to control diseases such as powdery mildew and eyespot on crops such as cereals, grapes and cucumbers. It has attracted much attention due to its unique mechanism of action.
Product introduction
Product Name: Metrafenone
Other names: Flexity, Vivando
Chemical name: (3-bromo-6-methoxy-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone
Molecular formula: C19H21BrO5
Molecular weight: 409.271
CAS NO. : 220899-03-6
Structural formula:
Physical and chemical properties: The original drug is white to off-white crystals with a slight musty smell. Melting point: 99.2～100.8℃; Vapor pressure: 1.53×10-4 Pa (20℃); Solubility in water (mg/L, 20℃): 0.552 (pH5), 0.457 (pH7), 0.457 (pH 9). Solubility in organic solvents (g/L, 20°C): acetone 403, acetonitrile 165, dichloromethane 1950.
Mechanism of action
Metrafenone is classified into the B6 subgroup of the B family in the International Fungicide Resistance Action Committee (FRAC) and has a unique pathogenic actin action site. It can interfere with the formation of appressoria during powdery mildew fungus spore germination, hinder the establishment of polar actin tissue, inhibit the formation of mycelium tip cells and the normal growth and development of mycelium. This effectively inhibits the invasion of powdery mildew and controls the occurrence of diseases. It has obvious preventive and therapeutic effects.
Application scope
Application: It can be used to prevent and control powdery mildew in cereals, grapes, cucumbers, beans, strawberries and other crops. It can also be used for the prevention and control of diseases such as sugarcane eye spot, ginger eye spot, wheat stem rot, mushroom brown rot and mushroom Verticillium brown spot.
Common dosage forms: 42% metrafenone suspension; representative product: Yingteng
Usage technology: 90~180 g/hm2 spray.
Features
1. High activity: Metrafenone has several times higher bactericidal activity than triadimefon and cyprodinil.
2. Special mechanism of action: Metrafenone has a unique and novel mechanism of action. Unlike general fungicides, which act on the respiratory chain, cell wall, etc., Metrafenone directly acts on the cytoskeleton of the bacteria - actin, causing it to be destroyed and disintegrated. Causes abnormal branching of mycelium and slows down growth, thereby achieving the purpose of preventing and controlling powdery mildew.
3. No cross-resistance: Metrafenone has no cross-resistance with dimethylation inhibitors and anilinopyrimidine fungicides.
4. Special effects on powdery mildew: Metrafenone has a good bactericidal effect on powdery mildew bacteria that have developed resistance, and has good protection, treatment, eradication and inhibition of sporulation.
5. Good compoundability: It can be mixed with epoxiconazole, fluoxastrobin, boscalid and other ingredients.
Future compounding recommendations
Bixafen+Metrafenone: Can be used to control diseases of cereals, fruit trees, and vegetables, especially fungal diseases such as powdery mildew, rust, downy mildew, and damping off. The effect is significantly better than that of a single agent.
Trifloxystrobin + Metrafenone: Has good bactericidal effect, and its activity and bactericidal effect are not a simple superposition of each component. Compared with a single agent, in addition to having significant bactericidal effect, it is also safe for crops. The invention has significant control effect on powdery mildew.
Metrafenone + Fluopicolin: A formula with good synergy, which has better control effect than a single dose of fungicide, and can expand the control spectrum while reducing the risk of pathogenic bacteria developing resistance.
Metalaxyl + Metrafenone: In the application of preventing and controlling downy mildew, powdery mildew, etc., it has the advantages of good control effect, expanded bactericidal spectrum, delaying drug resistance and drug resistance.
Metrafenone + Cyanostrobin: It can be used to control powdery mildew and scab on wheat. It expands the bactericidal spectrum, has a long lasting effect, and is safe for wheat.
Metrafenone + Ethylpyridinol/ethylpyridinol sulfonate: It used to control powdery mildew on cucumbers, eggplants, bitter melons, melons, wheat, strawberries, mangoes, grapes, apples and chrysanthemums.
Metrafenone + Methoxyacrylates (azoxystrobin, mesostrobin, mesostrobin, tristrobin): After compounding, it has a synergistic effect on a variety of diseases that harm agricultural production and reduces the amount of pesticides used. It reduces the amount of pesticide residues on crops, reduces environmental pollution, is safe for humans and animals, has good environmental compatibility, and makes it difficult for diseases to become resistant to pesticides.
Metrafenone+Carbendazim/thiophanate-methyl/chlorothalonil: It has obvious synergistic effect after compounding, used to control cucumber, eggplant, bitter melon, melon, wheat, strawberry, mango, grape, apple and chrysanthemum of powdery mildew.
Metrafenone+Metrafenone: It can be used to prevent and control diseases of cereals, fruit trees and vegetables. It can especially be used to prevent and control fungal diseases such as grape downy mildew, pepper Phytophthora, potato late blight, rice sheath blight, cotton damping off, wheat powdery mildew and other fungal diseases. The effect is significantly better than that of a single agent.
Metrafenone + Triazole fungicides (epoconazole, tetrafluoroconazole, myconazole, myconazole): The compound has good bactericidal effect and low medication cost. And its activity and bactericidal effect are not a simple superposition of the activities of each component. Compared with the existing single preparation, in addition to having a significant bactericidal effect, it also has a significant control effect on crop powdery mildew.
Phylconazole + Fludioxonil + Metrafenone: It has obvious synergistic effect in preventing and treating wheat scab, wheat powdery mildew, wheat sheath blight, wheat rust, rice sheath blight and rapeseed sclerotinia. It will have important practical significance to increase social, economic and ecological benefits.
Synthetic Route
The core synthesis route: using 2-hydroxy-6-methylbenzoic acid methyl ester as raw material, after bromination, hydrolysis, and chlorination reactions, it is then reacted with 3,4,5-trimethoxytoluene to obtain Metrafenone.
Outlook
Powdery mildew is a worldwide disease that is common in many important crops, causes serious damage, and is difficult to control. As an excellent fungicide for controlling powdery mildew, Metrafenone's market demand in China will inevitably grow further. Although the production process of Metrafenone is relatively complex and requires multiple steps and reaction condition control, the production cost is relatively high and the price is relatively expensive. However, as the patent protection period of Metrafenone's compound expires, the continuous optimization of the production process will further promote its market application and development.
