Acequinoquinol is a naphthoquinone contact killer (with stomach toxicity) nematicide developed by DuPont (now Corteva) in 1975, and then DuPont transferred the rights and interests to Agro-Kanesho company, because of its low toxicity, safety, high efficiency and unique mechanism of action, it is widely used in fruit trees and vegetables abroad, especially citrus and apples to control citrus full catch mites, leaf mites, thin mites and other mites, and is also very effective against aphids and nematodes. DuPont did not apply for a patent for the ingredient in China, the patent period in other countries expired as early as 1987, with the growth and development of the domestic acaricide market in recent years, acaricide quinone has become a more concerned ingredient in China, at present, the ingredient is mainly developed by Zhejiang Yongnong Biology, Zhejiang Yongnong has applied for a number of synthetic patents around its intermediate "hennaquinone", and recently the preparation developed by it 15% acaricide quinone EW (trademark: legal protection) has entered the field efficacy test stage. It is expected to be launched to the market in 2024.
Product Introduction
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Quinone. English Name:acequinocyl
Chinese name:Acaricidal quinoneOther Names:Aquinone, AKD 2023, DPX 3792, Piton, Kanemite, ShuttleChemical Name:(3-dodecyl-1,4-dioxene-2-yl) acetateMolecular Formula:c24h32o4Relative molecular weight:CAS Login Number:Structural Formula:
Three-dimensional structural formula:
Physicochemical Properties:The pure product is a yellow powder with a melting point of 596℃。Vapor pressure 51×10-2pa (40℃)。Relative density 115(25℃)。Distribution coefficient kowlgp 62 (25℃)。henry's constant 97x10-2 pa?m3/mol。Solubility in water (20) 669μg/l;Solubility in other solvents (g l,20): n-hexane 44, toluene 450, dichloromethane 620, ketone 220, methanol 78、dmf190.Ethyl acetate 290, isopropanol 29, acetonitrile 28, DMSO 25, octanol 31, ethanol 23, xylene 730. Stability: Breaks down at 200. Hydrolyzed DT50 (dark place) for 74 days (pH = 4, 25), 5 (pH = 7, 25), 76 min (pH = 9, 25). Photolysis of DT5014min in water (pH=5, 25). Toxicity:Acute oral LD50: rat 5000mg kg, mouse GT; 5000mg/kg。rat acute percutaneous LD50 2000 mg kg. Rat inhalation LC50 084mg/l。It is slightly irritating to rabbit eyes and **. It is not allergenic to guinea pigs. Noel value: rat 90mg/(kg ?d), mouse 27 mg (kg·d), 5 mg (kg·d) for dogs. No reproductive toxicity (rats), no developmental effects (rats, rabbits), no carcinogenicity (rats, mice), no mutagenicity (AMES test DNA repair and chromosomal experiments).
Mechanism of action
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Quinone. Acaricide quinone is a naphthoquinone derivative, which belongs to the contact type acaricide, and has stomach toxicity. In mites, acarquinone is hydrolyzed into 2-dodecyl-3-hydroxy-1,4-naphthoquinone and is able to bind to qo sites on electron transfer channels in mitochondria, thereby inhibiting electron transport. This inhibition causes the mites' energy metabolism to be disturbed, eventually leading to their death.
Applications
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Quinone. Applicable crops:Used in citrus, apples, pears, peaches, cherry blossoms, melons, cucumbers, teas, ornamental plants, vegetables.
Prevention and control objects:citrus full-clawed mites, leaf mites, lean mites, tea yellow mites, apple red spiders; It is effective against eggs, larvae, and nymphs of many types of mites.
Development dosage form:15% acaricide quinone SC, 15% acaricide quinone EW
Application Technology:200-1000g hm2 for fruit trees, 150-450g hm2 for vegetables; Except for some strawberries and roses, there are no pesticide damage reports, and they cannot be mixed with strong alkaline pesticides.
Registration
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Quinone. There is no registration in the country
United States:In the 60s of the 20th century, the American Cyanamid Company, an American chemical company, registered acaricidal quinone, trade name: Kanemite
Japan:In 1970, Japan's Sankyo Corporation launched the acaricidal quinone product, trade name: shuttle
In 1975, Sumitomo Chemical Co., Ltd. of Japan launched the acaricidal quinone product, trade name: piton
Australia:In 2020, the acaricide kanemite (containing the active ingredient acaricidequinone) was launched in Australia by Alista
Synthetic routes
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Quinone. Synthesis of acaricidal quinone:
2-hydroxy-1,4-naphthoquinone (hennaquinone), methylamine, n-dodedehyde, acetyl chloride were used as starting materials, and acaricide quinone was obtained by condensation, deamine, hydrogenation, oxidation and esterification reactions. Its synthesis route is as follows:
Synthesis of 2-hydroxy-1,4-naphthoquinone:1,4 naphthoquinone was epoxidized with 31% hydrogen peroxide and alkaline hydrolysis in an alcohol-ether mixed solvent to obtain 2-hydroxy-1,4 naphthoquinone. Two-step yield 82%; The reaction formula is as follows:
Future compound recommendation
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Quinone. Dicaroquinone + tetradizine, **tin, phenylbutyltin, fluorodizine, bromodifen: It has a synergistic effect on a variety of pests that endanger agricultural production, reduces the amount of pesticides, reduces the amount of pesticides left on crops, reduces environmental pollution, is safe for humans and animals, has good environmental compatibility, and pests are not easy to produce resistance.
Acaricidal quinone + ethoxazole: the acaricidal composition of the present invention has a good control effect on harmful herbivorous mites, and the control effect on various resistant mites is particularly significant.
Acarcinomone + spirodilofen, pyrimidoxil, azolefenoxilate, butaflufenoxil: It can control a variety of harmful mites, and has obvious synergistic effect, and can reduce the amount of pesticides, reduce the amount of pesticides on crops, and reduce environmental pollution.
Acaricide quinone + pyridoxamine, thiobenone, quine mite ether, benzyl mite ether: it can prevent and control a variety of pests and mites, and has obvious synergistic effect, and can reduce the amount of pesticides, reduce the residue of pesticides on crops, and reduce environmental pollution.
Acaricidal quinone + pyridoxine, alkyne mite, bifenazide: it can prevent and control a variety of pests and mites, and has obvious synergistic effect, expands the acaricidal spectrum, and can reduce the amount of pesticides, reduce the residue of pesticides on crops, and reduce environmental pollution.
Acaricide quinone + avermectin, ivermectin, emamectin benzoate, mibacytin: This acaricidal combination makes full use of the respective mechanisms of action of the active components, so that the two components work synergistically, so that the acaricide can effectively delay or overcome the resistance of pests.
Dicarcinoxidine + Nitrile Dicofenolate: as a pesticide combination with low pesticide residue concentration and low dosage of toxic components for the control of citrus red spider.
Summary
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Quinone. Acaricide quinone is an old product that has already passed the patent period, it has high biological activity, special mechanism of action, environmental safety, has been one of the key development of acaricide products for many years, but the application and promotion in China is not much, I hope that with the efforts of excellent enterprises such as Yongnong, acaricide quinone can be industrialized as soon as possible, and fill the gap of naphthoquinone compounds in China's acaricide market.