WO2024120137A1 - Dérivé de benzamide isoxazoline substitué ou sel agrochimiquement acceptable de celui-ci, composition et utilisation associées - Google Patents

Dérivé de benzamide isoxazoline substitué ou sel agrochimiquement acceptable de celui-ci, composition et utilisation associées Download PDF

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Publication number
WO2024120137A1
WO2024120137A1 PCT/CN2023/131670 CN2023131670W WO2024120137A1 WO 2024120137 A1 WO2024120137 A1 WO 2024120137A1 CN 2023131670 W CN2023131670 W CN 2023131670W WO 2024120137 A1 WO2024120137 A1 WO 2024120137A1
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formula
pesticide
alkyl
acceptable salt
substituted benzamide
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PCT/CN2023/131670
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English (en)
Chinese (zh)
Inventor
葛家成
邢阳阳
马娥
刘明东
孙鹏
胡堂路
张亚弢
孙毅轩
孟维康
谢勇
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海利尔药业集团股份有限公司
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Publication of WO2024120137A1 publication Critical patent/WO2024120137A1/fr

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  • the present invention belongs to the technical field of pesticides, and specifically relates to a substituted benzamide isoxazoline derivative or its salt and composition acceptable as pesticides, and to the use of these compounds or its salt and composition acceptable as pesticides as insecticides or acaricides.
  • Benzamide isoxazoline compounds are a class of compounds with insecticidal activity that were first discovered and paid attention to by Ishihara Corporation. They have excellent biological activity against invertebrate pests. As the issue of global food security has received increasing attention, it is particularly important to improve agricultural production efficiency. Although research on benzoamide isoxazoline compounds has been ongoing for many years, a benzoamide isoxazoline compound with good rapid-acting properties, a broad insecticidal spectrum, and safety for crops has not been obtained.
  • the present invention provides a substituted benzamide isoxazoline derivative or its salt acceptable as a pesticide, a composition and its use, which has excellent biological activity against Lepidoptera, Homoptera and Thysanoptera pests and is not easy to produce cross-resistance with existing diamide compounds.
  • X 1 , X 2 , and X 3 are the same or different and are independently selected from F, Cl, Br, CN or NO 2 ;
  • R 1 is selected from halogen, CN, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl;
  • R2 is selected from H, CN, C1 - C6 alkyl, halogenated C1 - C6 alkyl, C2 - C6 alkenyl, C1 - C6 alkoxy, C3 - C6 cycloalkyl or C3 -C6 cycloalkyl-substituted C1 - C6 alkyl .
  • X 1 , X 2 , and X 3 are the same or different and are independently selected from F, Cl, Br or CN;
  • R 1 is selected from halogen, CN or C 1 -C 6 alkyl
  • R 2 is selected from C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted C 1 -C 6 alkyl.
  • X 1 , X 2 , and X 3 are the same or different and are independently selected from F, Cl or Br;
  • R1 is selected from F, Cl, Br, methyl, ethyl, propyl or butyl;
  • R2 is selected from methyl, ethyl, propyl, butyl , CH2Cl , CHCl2 , CCl3 , CH2F , CHF2 , CF3, CH2CF3 , CH2CH2F, CH2CHF2 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cyclopropyl substituted methyl.
  • X1 and X3 are the same or different and are selected from F or Cl;
  • R 1 is selected from CH 3 , F or CN;
  • X2 is F
  • R 1 is selected from CH 3 , F or CN;
  • R2 is selected from CH3 , CH2CF3 , cyclopropanyl , CH2CH2F , CH2CH3 or cyclopentanyl .
  • the pesticide-acceptable salt may be a salt obtained by reacting the substituted benzamide isoxazoline derivative of the present invention with a chemically acceptable acid, wherein the chemically acceptable acid may be an inorganic acid (such as hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid, etc.) or an organic acid (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzoic acid, etc.); the pesticide-acceptable salt may also be a salt obtained by reacting the substituted benzamide isoxazoline derivative of the present invention with a chemically acceptable base, wherein the chemically acceptable base may be an inorganic base (such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate) or an organic base (such as trimethylamine, triethylamine, etc.).
  • a chemically acceptable acid may be an inorganic acid (such as
  • the present invention also discloses an insecticidal or acaricidal composition, comprising an insecticidal or acaricidal effective amount of at least one of the substituted benzamide isoxazoline derivatives as described above or their pesticide-acceptable salts; further, it also comprises a formulation carrier or a formulation adjuvant.
  • the present invention also discloses a method for controlling plant pests or mites, comprising applying an insecticidal or acaricidal effective amount of at least one of the substituted benzamide isoxazoline derivatives as described above or its pesticide-acceptable salts or the insecticidal or acaricidal composition as described above on crops or pests or mites and/or their habitats.
  • Halogen or halogen refers to fluorine, chlorine, bromine and iodine.
  • C 1 -C 6 alkyl a straight or branched alkyl group having 1 to 6 carbon atoms, such as methyl Me, ethyl Et, n-propyl n-Pr, isopropyl i-Pr or n-butyl n-Bu, isobutyl i-Bu, sec-butyl s-Bu, tert-butyl t-Bu and the like.
  • Halogenated C 1 -C 6 alkyl a straight or branched chain alkyl group having 1 to 6 carbon atoms, wherein the hydrogen atoms on the alkyl group may be partially or completely substituted by halogen, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like.
  • the method for synthesizing the compound of formula I is specifically to prepare the compound of formula XI via the compounds of formula X, IX, VIII, VII, VI, V, IV, III, and II (in the chemical formulas listed below, unless otherwise defined, the substituents and symbols have the same meanings as the substituents and symbols defined in formula I)
  • the active compound of formula (I) of the present invention is suitable for controlling pests or mites, that is, controlling pests or mites, wherein the pests or mites refer to harmful or unwanted insects or mites, especially harmful or unwanted insects or mites encountered in agriculture, forestry, storage product protection and material protection and hygiene fields.
  • the compound of the present invention is active for both generally sensitive and resistant species, and is effective at all stages of the development of the pests or mites; the present invention also relates to a method for inhibiting pests or mites, which comprises applying a biologically effective amount of the compound of formula (I) to the insect location, insect habitat, pest habitat, area to be protected, or directly to the insect to be controlled.
  • the compound of the present invention can also be used to control other invertebrate pests or organisms.
  • the insect habitat, pest habitat or mite habitat refers to the environment where insects, pests or mites live or their eggs exist, including the surrounding air, food eaten or objects contacted.
  • insects, pests or mites live or their eggs exist, including the surrounding air, food eaten or objects contacted.
  • the active compound for example, by applying the active compound to the seeds of the plant (before planting), to the seedlings, or the planted cuttings, leaves, stems, fruits, grains and/or roots, or to the soil or other growth media (before or after crop planting), it is possible to control insects or mites that eat, destroy or contact edible agricultural products, ornamental plants, turf, pasture plants or other plants with economic value. It is also possible to protect these plants from diseases caused by viruses, fungi or bacteria by controlling sap-feeding pests such as whiteflies, planthoppers, aphids and aphids, etc.
  • controlling pests or mites refers to reducing the number of living insects, pests or mites, or reducing the number of viable eggs of insects, pests or mites.
  • the degree of reduction achieved by the compound depends on the application rate of the compound, the specific compound used and the target insect, pest or mite species, and at least an amount that can produce an effect must be used.
  • pests to which the insecticide of the present invention can be applied include, but are not limited to, lepidoptera, such as Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsiagemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphaniani idalis, Diatrae a grandiosella), Egyptian cutworm (Earias insulana), South American corn borer (Elasmopalpus lignosellus), Ligustrum lucidum (Eupoecilia ambiguella), Evetria bouliana, Feltia subterranea, Wax moth (
  • Beetles for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia serrata aurata), Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica
  • mosquitoes for example, Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucopus, Anopheles scutellariae ...
  • Thrips for example, Dichromothrips corbetti, Dichromothrips ssp, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;
  • Termites for example, Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis and Coptotermes formosanus;
  • Cockroaches for example, German cockroach (Blattella germanica), Blattella asahinae, American cockroach (Periplaneta americana), Japanese cockroach (Periplaneta japonica), brown cockroach (Periplaneta brunnea), Periplaneta fuligginosa, Australian cockroach (Periplaneta australasiae), and Oriental cockroach (Blatta orientalis);
  • Crickets, grasshoppers, locusts for example, Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus septemfasciata maroccanus), Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Brown Migratory Locust;
  • Arachnoidea such as spiders (Acarina), for example, the Argasidae, Ixodidae and Sarcoptidae, such as the Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentorvariabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes ovalis
  • Fleas order Siphonaptera
  • Ctenocephalides felis cat flea
  • Ctenocephalides canis dog flea
  • Xenopsylla cheopis chinese flea
  • Pulex irritans itch flea
  • Tunga penetrans skin flea
  • Nosopsyllus fasciatus skin flea
  • Silverfish domestic silverfish (Thysanura), for example, Lepisma saccharina and Thermobia domestica, centipedes (Chilopoda), for example, Scutigera coleoptrata, millipedes (Diplopoda), for example, Narceus spp., [0491] earwigs (Dermaptera), for example, Forficula auricularia, lice (Phthiraptera), for example, Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus urysternus, Haematopinus suis, Linognathus vituli, Bovicolabovis, Menopon gallinae, Menacanthus stramineus, and Solenopotes capillatus;
  • spiders such as ticks (Acarina), for example the families of soft ticks, hard ticks and scabies, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalo mma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Sarcoptes spp.
  • Eriophyidae such as Aculus pointedendali, Phyllocoptrata oleivora and Eriophyes sheldoni
  • Tarsonemidae such as Phytonemus pallidus and Polyphagotarsonemuslatus
  • Tenuipalpidae such as Brevipalpus phoenicis
  • Tetranychidae such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri and oligonychus pratensis.
  • the plant objects to which the pesticide of the present invention is applied are not particularly limited; for example, cereals (e.g., rice, barley, wheat, rye, oats, corn, sorghum, etc.), legumes (soybeans, adzuki beans, broad beans, peas, peanuts, etc.), fruit trees/fruits (apples, citrus, pears, grapes, peaches, Japanese apricots, cherries, walnuts, apricots, bananas, strawberries, etc.), vegetables (cabbage, tomatoes, spinach, cabbage, lettuce, onions, green onions, green peppers, etc.), root vegetables (carrots, potatoes, sweet potatoes, radishes, etc.), , lotus root, turnip, etc.), industrial crops (cotton, hemp, mulberry, balsam pear, rapeseed, sugar beet, hops, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.), berries (pumpkin, cucumber,
  • substituents were introduced on the N of the amide group to obtain a series of more efficient compounds with excellent activity for use in agricultural or forestry insecticides or mites. They have particularly good biological activity against pests such as Lepidoptera, Homoptera, and Thysanoptera, and have better biosafety.
  • the method for preparing the compounds of the present invention is described in the following technical schemes and examples.
  • the raw materials can be purchased from the market or can be prepared by methods known in the literature or as shown in the detailed description. It should be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention.
  • the specific raw materials and conditions in the synthetic route have been described below, it can be easily replaced with other similar raw materials and conditions, and these modifications or variations of the preparation method of the present invention such as various isomers of the compound are included within the scope of the present invention.
  • the preparation method described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, appropriate groups are protected during the reaction, etc.
  • the intermediate acid (520 mg, 1 mmol) was dissolved in dichloromethane (20 ml), HATU (420 mg, 1.1 eq) and DIPEA (390 mg, 3 eq) were added, and the mixture was stirred at room temperature for 0.5 h.
  • Trifluoroethylamine hydrochloride (270 mg, 2 mmol, 2 eq) and pyridine (0.5 ml) were added, and the mixture was stirred at room temperature overnight.
  • the product was obtained by LCMS detection.
  • the intermediate acid (535mg, 1mmol) was dissolved in dichloromethane (20ml), HATU (420mg, 1.1eq), DIPEA (390mg, 3eq) were added, and the mixture was stirred at room temperature for 0.5h. Ethylamine (2.0MinTHF, 1ml, 2eq) and pyridine (0.5ml) were added, and the mixture was stirred at room temperature overnight. The product was obtained by LCMS detection. The reaction solution was washed with dilute hydrochloric acid (1mol/L, 50ml*2), washed with saturated brine (50ml*2), dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product.
  • the intermediate acid (535mg, 1mmol) was dissolved in dichloromethane (20ml), HATU (420mg, 1.1eq), DIPEA (390mg, 3eq) were added, and the mixture was stirred at room temperature for 0.5h. Difluoroethylamine (81mg, 1mmol, 1eq) and pyridine (0.5ml) were added, and the mixture was stirred at room temperature overnight. The product was obtained by LCMS detection. The reaction solution was washed with dilute hydrochloric acid (1mol/L, 50ml*2), washed with saturated brine (50ml*2), dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product.
  • Soluble liquid Dissolve 10-50% of the compound of formula (I) and 5-20% of a wetting agent in 100% water and/or a water-soluble solvent to obtain the product.
  • Emulsifiable concentrate 10-70% of the compound of formula (I) and 5-10% of an emulsifier are dissolved in a water-insoluble organic solvent added to 100% to obtain the product.
  • Water emulsion Dissolve 5-30% of the compound of formula (I) and 1-10% of an emulsifier in 20-40% of a water-insoluble organic solvent. Use an emulsifier to introduce the mixture into 100% water and make a homogeneous emulsion to obtain the product.
  • Water dispersible granules Grind 10-70% of the compound of formula (I) under the addition of up to 100% of a dispersant and a wetting agent and convert it into water dispersible granules with the aid of industrial production equipment to obtain the product.
  • test compound was dissolved in N,N-dimethylformamide and then diluted to the desired concentration with water containing 0.1% Tween-80.
  • control compound A (specific structure is ),
  • control compound B (specific structure is ),
  • the reference compound C (specific structure is ),
  • the reference compound D (specific structure is ),
  • the reference compound E (specific structure is ),
  • the reference compound F (specific structure is ),
  • control compound G (specific structure is ),
  • the reference compound H (specific structure is ),
  • the leaf dipping method was used for indoor bioassay. Healthy and consistent third-instar larvae of diamondback moth were selected, and fresh cabbage leaves were placed in the drug solution with tweezers and immersed for 10 seconds before being taken out. After the drug solution was naturally dried, the cabbage leaves were placed in a culture dish lined with moisturizing filter paper, with 20 third-instar larvae of diamondback moth in each dish, and each treatment was repeated 4 times.
  • the number of dead diamondback moths was investigated 3 days after the drug was administered, and the mortality rate was calculated (retain integers).
  • the activities are as follows: at a concentration of 2 ppm, the compounds of the present application have a protective effect greater than 90% including 1-24, 29-46, 49-56, 62-68, 81, 89, 92, 101, 109, and 129; the control compounds A-I have a protective effect greater than 90% including compounds A, B, C, G, H, and I.
  • control compound and some of the compounds of the present invention were tested for low concentration activity, and the results are as follows:
  • the activity is as follows:
  • control compounds A-I showed a protective effect greater than 90% with compounds A, B, C, and G.
  • control compound and some of the compounds of the present invention were tested for low concentration activity, and the results are as follows:

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention relève du domaine des produits agrochimiques, et concerne en particulier, un dérivé d'isoxazoline de benzamide substitué ou un sel agrochimiquement acceptable de celui-ci, une composition et une utilisation associées. Un composé a la structure de formule (I). Dans la formule, la définition de chaque groupe est telle que définie dans la description. Le dérivé de benzamide isoxazoline substitué selon la présente invention a une activité insecticide ou acaricide efficace, est particulièrement approprié pour prévenir et traiter des organismes nuisibles et des acariens nuisibles tels que les lépidoptères, les homoptères, les thysanoptères et les acariens, et présente les avantages d'être à action rapide et d'avoir une applicabilité à large spectre.
PCT/CN2023/131670 2022-12-06 2023-11-15 Dérivé de benzamide isoxazoline substitué ou sel agrochimiquement acceptable de celui-ci, composition et utilisation associées WO2024120137A1 (fr)

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CN202211554927.0A CN115785017B (zh) 2022-12-06 2022-12-06 一种取代的苯酰胺异噁唑啉衍生物或其作为农药可接受的盐、组合物及其用途
CN202211554927.0 2022-12-06

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Publication number Priority date Publication date Assignee Title
CN115785017B (zh) * 2022-12-06 2023-12-08 海利尔药业集团股份有限公司 一种取代的苯酰胺异噁唑啉衍生物或其作为农药可接受的盐、组合物及其用途

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CN112174904A (zh) * 2019-07-01 2021-01-05 沈阳化工大学 一种异噁唑啉类化合物及其应用
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TWI812673B (zh) * 2018-02-12 2023-08-21 美商富曼西公司 用於防治無脊椎害蟲之萘異噁唑啉化合物
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US20090156643A1 (en) * 2006-03-10 2009-06-18 Nissan Chemical Industries, Ltd. Substituted isoxazoline compound and pesticide
US20100144797A1 (en) * 2007-03-07 2010-06-10 Takeshi Mita Isoxazoline-substituted benzamide compound and pest control agent
CN101778566A (zh) * 2007-08-17 2010-07-14 英特威国际有限公司 异噁唑啉组合物及其作为抗寄生虫药的用途
CN106999475A (zh) * 2014-12-22 2017-08-01 英特维特国际股份有限公司 异噁唑啉化合物用于治疗蠕形螨病的用途
CN112174904A (zh) * 2019-07-01 2021-01-05 沈阳化工大学 一种异噁唑啉类化合物及其应用
CN114605324A (zh) * 2022-03-28 2022-06-10 山东省联合农药工业有限公司 异噁唑啉取代的苯甲酰胺类衍生物及其制备方法与用途
CN115785017A (zh) * 2022-12-06 2023-03-14 海利尔药业集团股份有限公司 一种取代的苯酰胺异噁唑啉衍生物或其作为农药可接受的盐、组合物及其用途

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