CN111196773B - 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative and application thereof - Google Patents

2- (3-oxo-2-pentylcyclopentyl) acetamide derivative and application thereof Download PDF

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CN111196773B
CN111196773B CN201811363239.XA CN201811363239A CN111196773B CN 111196773 B CN111196773 B CN 111196773B CN 201811363239 A CN201811363239 A CN 201811363239A CN 111196773 B CN111196773 B CN 111196773B
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CN111196773A (en
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周繁
冉兆晋
魏婷婷
李继广
王芳
焦姣
王远
柴宝山
赵宪成
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Shenyang Research Institute of Chemical Industry Co Ltd
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    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
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Abstract

The invention belongs to the field of chemistry, and particularly relates to a 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative as shown in formula I, and application of the compound as shown in formula I in preparation of a plant growth regulator or a plant induced disease-resistant activator. The compound has a novel structure, and simultaneously has better plant-induced disease-resistant activity. And the compound with the general formula has good activity of inhibiting seed germination at high concentration and good safety (the compound still has good germination activity at high concentration treatment) without causing the seed to lose the germination activity.

Description

2- (3-oxo-2-pentylcyclopentyl) acetamide derivative and application thereof
Technical Field
The invention belongs to the field of chemistry, and particularly relates to a 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative and application of the compound in regulating plant growth or inducing and activating plant disease resistance.
Background
Plant Growth Regulators (PGRs) are generally any substance or mixture of substances used to accelerate or retard the rate of growth or maturation or to alter the development of plants or their products. PGRs affect the growth and differentiation of plants. More specifically, various Plant Growth Regulators (PGRs) may, for example, reduce plant height, stimulate seed germination, induce flowering, enhance leaf pigmentation, alter plant growth rate and alter timing and efficiency of fruiting. Plant Growth Regulators (PGRs) may exhibit significant growth regulating properties, which can result in increased yield of cultivated plants or harvested crops. Plant Growth Regulators (PGRs) have a concentration-dependent growth inhibitory effect, and growth of both monocotyledons and dicotyledons can be inhibited. Inhibiting vegetative growth of many cultivated plants allows more plants to be spread over the crop area, resulting in higher yields per unit area. It is desirable and advantageous in certain circumstances to inhibit vegetative growth of monocotyledonous plants, such as, for example, cultivated plants such as cereals. The above growth inhibition is of economic value. The use of Plant Growth Regulators (PGRs) to inhibit the high growth of cereals is also important, as shortening the stems reduces or completely eliminates the risk of lodging prior to harvesting. Plant Growth Regulators (PGRs) can cause stalk strengthening in cereal crops and this also resists lodging.
The existing plant growth regulators in the market are few in types, and cannot meet the specific needs of the existing agricultural production, so that the development of varieties with new applications and differences is urgently needed. The existing market has few varieties of medicines for inhibiting plant growth, the application range is limited, and the development of a new chemical entity plant growth regulator with a brand new structure has great agricultural application significance.
The pesticide has the advantages of rapidness, high efficiency, economy and the like, and occupies a dominant position in the prevention and control of crop diseases and insect pests. However, the use of a large amount of chemical pesticides not only pollutes the ecological environment, but also easily stimulates the variation of pathogenic protozoa to generate variation, thereby causing the phenomenon of pesticide resistance. In recent years, people pay more and more attention to food safety and ecological environment, particularly to crop quality and environmental protection, so that the limitation or reduction of the use of chemical pesticides with high toxicity and high residue is more and more paid more and more attention to society, and the development of novel biological and chemical agents is one of the key research directions in the field of crop pest control harm on the premise of keeping pesticide effect and environmental pollution-free.
The plant body has a strong disease-resistant mechanism, and finds that various biological and chemical factors can activate plant immune reaction, induce plants to resist environmental adversity stresses such as diseases, insects, grasses, drought, salt and alkali, low temperature, high temperature and the like, and the plant induced disease-resistant activator developed aiming at inducing the adversity stresses can be expected to partially replace chemical pesticides, thereby reducing the environmental pollution and the food harmful substance residue caused by high-toxicity chemical agents.
The existing plant induced disease-resistant activating agents in the market are few in types, and certain problems exist in the activity and the cost of the plant induced disease-resistant activating agents, so that the market popularization of the medicines is influenced. The development of the chemical entity plant resistance inducer with a brand new structure has great agricultural application significance, the dosage of the chemical entity plant resistance inducer is small (the dosage is less than that of common pesticides), the application is wide (multiple diseases are prevented simultaneously), the dosage of chemical pesticides can be reduced, and the pressure of the environment caused by the use of excessive chemicals is relieved.
Disclosure of Invention
The invention aims to provide a 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative and application of the compound in regulating plant growth or inducing and activating plant disease resistance.
In order to achieve the purpose, the invention adopts the technical scheme that:
a2- (3-oxo-2-pentylcyclopentyl) acetamide derivative, 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative is a compound of formula I:
Figure BDA0001867812580000021
wherein
Ar is unsubstituted or substituted by 1-5R1Substituted aryl or heteroaryl;
R1selected from halogen, nitro, cyano, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C1-C12Alkylthio radical, C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl group, C2-C12Alkenyl, halo C2-C12Alkenyl radical, C3-C12Alkenyloxy, halogeno C3-C12Alkenyloxy radical, C2-C12Alkynyl, halo C2-C12Alkynyl, C3-C12Alkynyloxy, halo C3-C12Alkynyloxy, halo C1-C12Alkylthio, halo C1-C12Alkylcarbonyl group, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, C2-C12Dialkylamino radical, C1-C12Alkylcarbonylamino, halo C1-C12Alkylcarbonylamino, C1-C12Alkylaminocarbonyl or halogeno C1-C12An alkylaminocarbonyl group.
Preferably, in the compound of formula I:
ar is unsubstituted or substituted by 1-5R1Substituted benzene, pyridine, pyrimidine, pyrazine, pyridazine, furan, thiophene, thiazole, pyrrole or imidazole;
R1selected from halogen, nitro, cyano, C1-C6Alkyl, haloC1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl group, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C3-C6Alkenyloxy, halogeno C3-C6Alkenyloxy radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C3-C6Alkynyloxy, halo C3-C6Alkynyloxy, halo C1-C6Alkylthio, halo C1-C6Alkylcarbonyl group, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, C2-C6Dialkylamino radical, C1-C6Alkylcarbonylamino, halo C1-C6Alkylcarbonylamino, C1-C6Alkylaminocarbonyl or halogeno C1-C6An alkylaminocarbonyl group.
Further preferably, in the compound represented by the formula I:
ar is unsubstituted or substituted by 1-5R1Substituted benzene, pyridine, pyrimidine, pyrazine, pyridazine, thiazole, pyrrole or imidazole;
R1selected from halogen, nitro, cyano, C1-C3Alkyl, halo C1-C3Alkyl radical, C1-C3Alkoxy, halo C1-C3Alkoxy radical, C1-C3Alkylthio radical, C1-C3Alkylcarbonyl group, C1-C3Alkoxycarbonyl group, C2-C3Alkenyl, halo C2-C3Alkenyl radical, C3-C4Alkenyloxy, halogeno C3-C4Alkenyloxy radical, C2-C3Alkynyl, halo C2-C3Alkynyl, C3-C4Alkynyloxy, halo C3-C4Alkynyloxy, halo C1-C3Alkylthio, halo C1-C3Alkylcarbonyl group, C1-C3Alkylamino, halogeno C1-C3Alkylamino radical, C2-C3Dialkylamino radical, C1-C3Alkylcarbonylamino, halo C1-C3Alkylcarbonylamino, C1-C3Alkylaminocarbonyl or halogeno C1-C3An alkylaminocarbonyl group.
Still further preferably, in the compound represented by formula I:
ar is unsubstituted or substituted by 1-5R1Substituted benzene, pyridine, pyrimidine, pyrazine or pyridazine;
R1selected from halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl group, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C3-C6Alkenyloxy, halogeno C3-C6Alkenyloxy radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C3-C6Alkynyloxy, halo C3-C6Alkynyloxy, halo C1-C6Alkylthio, halo C1-C6Alkylcarbonyl group, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, C2-C6Dialkylamino radical, C1-C6Alkylcarbonylamino, halo C1-C6Alkylcarbonylamino, C1-C6Alkylaminocarbonyl or halogeno C1-C6An alkylaminocarbonyl group.
Still further preferred are compounds of formula I wherein:
ar is unsubstituted or substituted by 1-5R1Substituted benzene, pyridine or pyrimidine;
R1selected from halogen, nitro, cyano, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio radical, C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl group, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C3-C6Alkenyloxy, halogeno C3-C6Alkenyloxy radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C3-C6Alkynyloxy, halo C3-C6Alkynyloxy, halo C1-C6Alkylthio, halo C1-C6Alkylcarbonyl group, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, C2-C6Dialkylamino radical, C1-C6Alkylcarbonylamino, halo C1-C6Alkylcarbonylamino, C1-C6Alkylaminocarbonyl or halogeno C1-C6An alkylaminocarbonyl group.
Still further preferred, in said compound of formula I:
ar is unsubstituted or substituted by 1-5R1Substituted benzenes;
R1selected from halogen, nitro, cyano, C1-C3Alkyl, halo C1-C3Alkyl radical, C1-C3Alkoxy, halo C1-C3Alkoxy radical, C1-C3Alkylthio radical, C1-C3Alkylcarbonyl group, C1-C3Alkoxycarbonyl group, C2-C3Alkenyl, halo C2-C3Alkenyl radical, C3-C4Alkenyloxy, halogeno C3-C4Alkenyloxy radical, C2-C3Alkynyl, halo C2-C3Alkynyl, C3-C4Alkynyloxy, halo C3-C4Alkynyloxy, halo C1-C3Alkylthio, halo C1-C3Alkylcarbonyl group, C1-C3Alkylamino, halogeno C1-C3Alkylamino radical, C2-C3Dialkylamino radical, C1-C3Alkylcarbonylamino, halo C1-C3Alkylcarbonylamino, C1-C3Alkylaminocarbonyl or halogeno C1-C3An alkylaminocarbonyl group.
Still further preferably, in the compound represented by formula I:
ar is unsubstituted or substituted by 1-5R1Substituted benzenes;
R1selected from halogen, nitro, cyano, methyl, methoxy or trifluoromethyl.
Most preferably, in the compound of formula I:
ar is 3-methylphenyl, 4-methylphenyl, 2, 4-dimethylphenyl, 4-fluorophenyl, 2, 4-difluorophenyl, 2-chlorophenyl, 3, 4-dichlorophenyl, 2-trifluoromethylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-nitrophenyl, 3-fluorophenyl, 3-chloro-4-fluorophenyl, 2-methyl-3-chlorophenyl, 4-tert-butylphenyl, 2-nitro-3-chlorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-cyano-3-chlorophenyl, 2-fluoro-4-bromophenyl, 2-fluoro-5-methylphenyl.
An application of the compound shown in the formula I in preparing a plant growth regulator or a plant induced disease-resistant activator.
Furthermore, the application of one or more compounds shown in the formula I in the preparation of plant growth regulators or plant induced disease-resistant activators; or, the application of one or more compounds shown in the formula I in the preparation of plant growth regulators or plant induced disease-resistant activators by mixing with agriculturally acceptable auxiliaries.
The plant growth regulating function is for improving crop characteristics including, but not limited to: emergence, crop yield, protein content, increased vigor, faster/delayed ripening, increased/delayed seed emergence speed, improved nutrient utilization efficiency, improved nitrogen utilization efficiency, improved water use efficiency, improved oil content and/or quality, improved digestibility, faster/more uniform ripening, improved flavour, improved starch content, more developed root systems (improved root growth), improved stress tolerance (e.g. to drought, heat, salinity, light, UV, moisture, cold), reduced ethylene (reduced production and/or accepted inhibition), increased tillering, increased plant height, larger leaves, fewer dead basal leaves, more robust tillers, greener leaf colour, pigment content, photosynthetic activity, less input requirements (such as fertilizer or water), less seed demand, more productive tillers, earlier flowering, early grain maturity, less plant toppling (lodging), increased shoot growth, enhanced plant vigor, increased plant density, and early and better germination. Are for example improved plant growth and plant development, better growth, more tillers, greener leaves, larger leaves, more biomass, better roots, improved stress tolerance of the plant, more grain yield, more harvested biomass, improved harvest quality (content of fatty acids, metabolites, oils etc.), more marketable products (e.g. improved size), improved processes (e.g. longer shelf life, better extraction of compounds), improved seed quality (sowing in the following season for seed production); or any other advantage familiar to those skilled in the art.
The compound shown in the formula I has a delaying function in plant growth regulation, can be used for delaying seed germination to obtain characters beneficial to agricultural production, and can have other functions in plant growth regulation by being mixed with other agriculturally acceptable auxiliary agents to prepare other plant growth regulators.
Wherein the main plants include cereal crops (rice, wheat, barley, oat, corn, millet, sorghum, etc.), potato crops (sweet potato, cassava, etc.), bean crops (soybean, broad bean, pea, mung bean, small bean, sweet broad bean, etc.) and fiber crops (cotton, hemp, silkworm, etc.), oil crops (peanut, rape, sesame, soybean, sunflower, etc.), sugar crops (beet, sugarcane, etc.), beverage crops (tea, coffee, cocoa, etc.), hobby crops (tobacco, etc.), medicinal crops (ginseng, fritillary, etc.), tropical crops (rubber, coconut, oil palm, sisal, etc.), melons (watermelon, melon, cantaloupe, papaya, etc.), and fruits, silkworm, vegetables (tomato, pepper, radish, cucumber, cabbage, celery, mustard tuber, shallot, garlic, various wild vegetables, etc.), flowers, bamboo shoots (such as orchid, etc.), vegetables, Bonsai, ornamental plants, and the like; also include fruit trees (apple, banana, citrus, peach, papaya), hops, pepper, seedlings and other horticultural crops.
The plant induced disease-resistant activator can be used for inducing and controlling the following diseases: oomycete diseases such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, loofah downy mildew, wax gourd downy mildew, melon downy mildew, Chinese cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, Chinese cabbage white rust), damping-off (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (hot pepper rot, loofah sponge rot, wax gourd blight), epidemic diseases (broad bean blight, cucumber blight, pumpkin blight, melon blight, hot pepper, leek blight, garlic blight, cotton blight, tomato blight, etc.; fungi imperfecti diseases such as wilt (sweet potato wilt, cotton wilt, sesame wilt, castor wilt, tomato wilt, bean wilt, cucumber wilt, pumpkin wilt, winter melon wilt, watermelon wilt, sweet melon wilt, hot pepper wilt, broad bean wilt, rape wilt, soybean wilt), root rot (hot pepper root rot, eggplant root rot, bean rot, cucumber root rot, bitter gourd root rot, cotton black root rot, broad bean root rot), damping off (seedling blight of cotton, sesame seedling blight, hot pepper seedling blight, cucumber damping off, cabbage stalk rot), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry leaf, hot pepper, bean disease, cucumber anthracnose, red sesame anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, eggplant disease, hot pepper anthracnose, vegetable bean disease, and cucumber blight, Balsam pear anthracnose, pumpkin anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, sunflower verticillium wilt, tomato verticillium wilt, hot pepper verticillium wilt, eggplant verticillium wilt), scab (pumpkin scab, wax gourd scab, melon scab), gray mold (boll gray mold, red ramie gray mold, tomato gray mold, hot pepper gray mold, bean gray mold, celery gray mold, spinach gray mold, kiwi gray mold), brown spot (cotton brown spot, jute brown spot, beet brown spot, peanut brown spot, pepper brown spot, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot, broad bean brown spot), black spot (flax brown spot, rape black spot, sesame black spot, sunflower black spot, castor black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato, Pepper black spot, eggplant black spot, bean black spot, cucumber black spot, celery black spot, carrot black rot, carrot black spot, apple black spot, peanut black spot), spot blight (tomato spot blight, pepper spot blight, celery spot blight), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean ring spot, sesame ring spot, bean ring spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem base rot (tomato stem base rot, bean stem base rot), and others (corn round spot, kenaf waist fold, rice blast, black sheath blight, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black spot, melon big spot, peanut net spot, tea leaf spot, red leaf spot, black leaf spot, peanut net spot, tea leaf spot, tomato black spot, potato leaf spot, potato black spot, tomato leaf spot, etc, Pepper white spot disease, white gourd leaf spot disease, celery black rot disease, spinach heart rot disease, kenaf leaf mold disease, kenaf spot disease, jute stem spot disease, soybean purple spot disease, sesame leaf spot disease, castor gray spot disease, tea brown leaf spot disease, eggplant brown orbicular spot disease, kidney bean red spot disease, bitter gourd leukoderma, watermelon spot disease, jute bottom rot disease, sunflower root stem rot disease, kidney bean carbon rot disease, soybean target spot disease, eggplant rod spore leaf spot disease, cucumber target spot disease, tomato leaf mold, eggplant leaf mold, broad bean red spot disease and the like); basidiomycete diseases such as rust (wheat stripe rust, wheat stalk rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (maize head smut, maize smut, sorghum head smut, sorghum loose smut, sorghum stalk smut, chestnut kernel smut, sugarcane head smut, kidney bean rust) and others (such as wheat sharp eyespot, rice sheath blight, etc.); ascomycetous diseases, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, towel gourd powdery mildew, pumpkin powdery mildew, wax gourd powdery mildew, melon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclerotinia rot, rape sclerotinia rot, soybean sclerotinia rot, peanut sclerotinia rot, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, kidney bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, bitter gourd sclerotinia rot, wax gourd sclerotinia rot, watermelon sclerotinia rot, celery sclerotinia rot), scab (apple scab, pear scab) and the like. Particularly, the compound has better inducing and controlling effects on cucumber downy mildew under lower dosage.
The plant induced disease-resistant activator can be used for inducing and controlling the following main viruses: tobacco mosaic virus, tobacco rattle virus, tobacco leaf curl virus, tobacco ringspot virus, tobacco etch virus, sweet potato feathery mottle virus, potato virus Y, potato leaf curl virus, potato virus X, potato virus S, potato virus A, potato spindle tuber viroid, sugarcane mosaic virus, sugarcane streak mosaic virus, cucumber mosaic virus, melon mosaic virus, squash mosaic virus, tomato spotted wilt virus, tomato sterility virus, beet curly top virus, alfalfa mosaic virus, banana bunchy top virus, banana streak virus, citrus tristeza virus, wheat yellow mosaic virus, wheat soil-borne mosaic virus, wheat spindle mosaic virus, barley yellow dwarf virus, cereal mosaic virus, rice dwarf virus, rice cluster dwarf virus, rice black-streaked dwarf virus, rice tooth dwarf virus, rice stripe leaf blight virus, potato stripe mosaic virus, potato leaf virus, potato virus X, potato virus, tomato yellow mosaic virus, tomato yellow dwarf virus, tomato yellow top virus, tomato yellow dwarf virus, rice dwarf virus, potato stripe, Rice white leaf virus, rice straw dwarfing virus, rice yellow leaf virus, rice yellow virus, rice donglu globular virus, rice yellow mottle virus, rice stripe necrosis virus, rice donglu baculovirus, rice necrosis mosaic virus, etc. Particularly, the compound has better induction control effect on tobacco mosaic virus under lower dosage.
The compound of the invention can be used as the plant induced disease-resistant activator.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
halogen: meaning fluoro, chloro, bromo or iodo.
Alkyl groups: straight-chain or branched alkyl radicals, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, cyclopentyl, n-hexyl, 2-hexyl, 3-hexyl, cyclohexyl, n-heptyl.
Cycloalkyl: substituted or unsubstituted heteroatom-containing cyclic alkyl groups, such as cyclopropyl, cyclopentyl, or cyclohexyl. Substituents such as methyl, halogen, and the like.
Heterocycloalkyl group: substituted or unsubstituted cyclic alkyl groups containing 1 or more heteroatoms of N, O, S, for example tetrahydrofuranyl, cyclopentylpiperidinyl. Substituents such as methyl, halogen, and the like.
Halogenated alkyl groups: straight-chain or branched alkyl groups in which the hydrogen atoms may be partially or completely substituted with halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like.
Alkoxy groups: straight or branched chain alkyl groups attached to the structure via oxygen atom linkages.
Haloalkoxy groups: straight-chain or branched alkoxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like.
Alkoxyalkyl groups: the alkoxy group is attached to the structure via an alkyl group. Such as-CH2OCH3，-CH2OCH2CH3。
Haloalkoxyalkyl groups: the hydrogen atoms on the alkyl group of the alkoxyalkyl group may be partially or fully substituted with halogen atoms. Such as-CH2OCH2CH2Cl。
Alkylthio group: straight or branched chain alkyl groups attached to the structure via a sulfur atom.
Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like.
Alkylamino group: straight or branched chain alkyl, linked to the structure via a nitrogen atom.
Haloalkylamino group: straight-chain or branched alkylamino groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms.
Alkenyl: straight-chain or branched alkenes, for example ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1, 2-allenyl and 2, 4-hexadienyl.
Halogenated alkenyl groups: straight-chain or branched alkenes in which the hydrogen atoms may be partially or completely replaced by halogen atoms.
Alkynyl: straight-chain or branched alkynes, for example ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. Alkynyl also includes groups consisting of multiple triple bonds, such as 2, 5-hexadiynyl.
Halogenated alkynyl group: straight-chain or branched alkynes, in which the hydrogen atoms may be partially or completely replaced by halogen atoms.
An alkenyloxy group: linear or branched alkenes linked to the structure via oxygen atoms.
Haloalkenyloxy: straight-chain or branched alkenyloxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms.
Alkynyloxy: straight or branched alkynes, linked to the structure via oxygen atom bonds.
Haloalkynyloxy: straight-chain or branched alkynyloxy, in which the hydrogen atoms may be partially or completely replaced by halogen atoms.
An alkylcarbonyl group: the linear or branched alkyl group is linked to the structure via a carbonyl group (-CO-), such as acetyl.
Halogenated alkylcarbonyl group: straight-chain or branched alkylcarbonyl whose hydrogen atoms on the alkyl group may be partially or fully substituted by halogen atoms, such as trifluoroacetyl.
Alkoxycarbonyl group: the alkoxy group is attached to the structure via a carbonyl group. Such as-COOCH3，-COOCH2CH3。
Halogenated alkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyl group may be partially or fully substituted by halogen atoms, e.g. -COOCH2CF3，-COOCH2CH2Cl, and the like.
Alkylcarbonylamino group: such as-NHCOCH3，-NHCOC(CH3)3。
Alkyl amino carbonyl: such as-C (═ O) NHCH3，-C(＝O)N(CH3)2。
Aryl groups and aryl moieties in arylalkyl, aryloxy, arylalkoxy, arylamino, and the like include phenyl, naphthyl, and the like.
Heteroaryl is a five or six membered ring containing 1 or more heteroatoms N, O, S. Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and the like.
Heteroaryl as well as heteroaryl moieties in heteroarylalkyl, heteroaryloxy, heteroarylalkoxy, etc., refer to five or six membered rings containing 1 or more N, O, S heteroatoms. Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoxazolyl, indolyl, and the like.
Some of the substituents of the compounds of formula I of the present invention are shown in tables 1-2, and some of the compounds of formula I of the present invention are illustrated by the specific compounds listed in Table 3, but are not intended to limit the present invention.
Figure BDA0001867812580000081
Ar is unsubstituted or substituted by 1-5R1Substituted phenyl or heteroarylA group; wherein the phenyl or heteroaryl group is shown in table 1 below.
Table 1:
phenyl radical Pyridyl radical Pyrimidinyl radicals Pyridazinyl radical Pyrazinyl radical
Furyl radical Thienyl radical Thiazolyl group Azole radical Imidazolyl group
Triazine radical
Ar is unsubstituted or substituted by 1-5R1Substituted benzene or heteroaryl, wherein R1As shown in table 2 below.
Table 2:
Figure BDA0001867812580000082
Figure BDA0001867812580000091
table 3:
Figure BDA0001867812580000092
Figure BDA0001867812580000101
the compounds of formula I of the present invention can be prepared according to the following method:
Figure BDA0001867812580000102
in the above reaction scheme, route one, the commercially available 2- (3-oxo-2-pentylcyclopentyl) acetic acid compound 1 and substituted aromatic amine compound 2 are reacted under the action of a condensing agent and a base to produce a compound of the general formula I;
route two, commercially available 2- (3-oxo-2-pentylcyclopentyl) acetic acid compound 1 was reacted with a chlorinating reagent to produce compound 3(2- (3-oxo-2-pentylcyclopentyl) acetyl chloride), compound 3 was reacted with compound 2 in the presence of a base to produce the compound of formula I.
In the above synthetic route: in the first scheme, the base is selected from potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide, etc.
In the first route, the condensing agent is selected from DCC, EDCI, HATU, HBTU, etc.
In scheme one, the reaction is carried out in a suitable solvent, which may be selected from, for example, ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, dimethylsulfoxide, acetone, or butanone.
Route two the chlorinating reagent for the chlorination step is selected from, for example, oxalyl chloride, thionyl chloride, phosphorus trichloride, phosphorus oxychloride, phosphorus pentachloride, etc.
The reaction of the chlorination step of scheme two is carried out in a suitable solvent, which may be selected from, for example, ethyl acetate, dichloromethane, tetrahydrofuran, toluene, xylene, benzene, and the like.
In the second route, the base for reacting the compound 3 generated after chlorination with the aromatic amine and the base is selected from potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide, etc.
The compound 3 generated after chlorination in the second route reacts with arylamine and base in a suitable solvent, such as ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, dimethyl sulfoxide, acetone or butanone.
The reaction temperature in route one and route two may be between room temperature and the boiling temperature of the solvent, typically 20-120 ℃.
The reaction time in route one and route two is from 30 minutes to 20 hours, usually 1-10 hours.
The invention has the advantages that:
the compound has a novel structure, and simultaneously has better plant-induced disease-resistant activity. And the compound of the general formula has good activity of inhibiting the germination of seeds at high concentration and good safety (the compound still has good germination activity at high concentration treatment) without causing the seeds to lose the germination activity.
Detailed Description
The following description of the embodiments is provided to assist in a comprehensive understanding of the invention as defined by the claims and their equivalents, and not as a limitation of the invention.
Example 1: synthesis of Compounds 1-4
Figure BDA0001867812580000111
A250 mL flask was charged with 3.0 g of 2- (3-oxo-2-pentylcyclopentyl) acetic acid, 3.0 g of oxalyl chloride, 150mL of dichloromethane, and three drops of DMF (N, N-dimethylformamide). The reaction was stirred at room temperature for 12 hours. After the reaction, the mixture was desolventized under reduced pressure, and 150mL of ethyl acetate, 1.5 g of p-toluidine and 2.0g of triethylamine were added thereto. The reaction was stirred at room temperature for 2 hours. After TLC monitoring of the reaction, the reaction was washed with 50 mL. times.3, the organic phase was dried over anhydrous sodium sulfate for 12 hours, desolventized under reduced pressure, and purified by column chromatography (eluent: ethyl acetate and petroleum ether (boiling range: 60-90 ℃ C.), volume ratio: 1:6) to give 2.3 g of 2- (3-oxo-2-pentylcyclopentyl) acetanilide, which was a white solid.
Example 2: synthesis of Compounds 1-4
Figure BDA0001867812580000121
A250 mL flask was charged with 3.0 g of 2- (3-oxo-2-pentylcyclopentyl) acetic acid, 5.0 g of EDCI (1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride), 2.0g of triethylamine, 1.5 g of p-toluidine, and 150mL of dichloromethane. The reaction was stirred at room temperature for 12 hours. After the reaction, the reaction mixture was washed with 50 mL. times.3, and the organic phase was dried over anhydrous sodium sulfate for 12 hours, then subjected to desolventizing under reduced pressure, and purified by column chromatography (eluent composed of ethyl acetate and petroleum ether (boiling range: 60-90 ℃ C.), volume ratio: 1:6) to give 2- (3-oxo-2-pentylcyclopentyl) acetyl-p-toluidine as a white solid, 1.7 g.
Other compounds of formula I can also be obtained according to the above synthetic route, and the other compound characterization data are as follows:
compounds 1 to 3:
1H NMR(600MHz,Chloroform-d)δ7.62(s,1H),7.38(s,1H),7.27(s,1H),7.20(d,J＝7.5Hz,1H),6.93(d,J＝7.1Hz,1H),2.70–2.60(m,1H),2.50–2.40(m,1H),2.34–2.25(m,6H),2.12(dt,J＝19.1,9.7Hz,1H),1.81(d,J＝9.5Hz,1H),1.53(dt,J＝30.2,9.0Hz,3H),1.43(t,J＝8.3Hz,1H),1.28–1.19(m,5H),0.85(t,J＝7.3Hz,3H)。
compounds 1-4:
1H NMR(600MHz,Chloroform-d)δ7.39(d,J＝8.3Hz,2H),7.14(d,J＝8.1Hz,2H),7.09(s,1H),2.68(dd,J＝14.5,4.9Hz,1H),2.47(ddq,J＝15.1,10.4,5.7,5.3Hz,1H),2.39–2.26(m,6H),2.15(dt,J＝19.1,8.9Hz,1H),1.84(dt,J＝10.5,5.5Hz,1H),1.59(d,J＝5.9Hz,2H),1.54–1.50(m,1H),1.45(ddt,J＝12.6,6.9,3.4Hz,1H),1.31–1.20(m,5H),0.86(t,J＝7.0Hz,3H)。
compounds 1-5:
1H NMR(600MHz,Chloroform-d)δ7.52(d,J＝8.5Hz,1H),7.11(d,J＝9.2Hz,1H),7.01(s,1H),7.00(s,1H),2.70(dd,J＝14.2,4.7Hz,1H),2.44(dd,J＝9.6,4.7Hz,1H),2.37–2.19(m,9H),2.13(dt,J＝19.0,10.0Hz,1H),1.87–1.78(m,1H),1.55(dd,J＝22.3,8.9Hz,3H),1.47–1.40(m,1H),1.26(s,5H),0.87(d,J＝6.9Hz,3H).
compounds 1-7:
1H NMR(600MHz,Chloroform-d)δ7.63(s,1H),7.49(d,J＝10.9Hz,1H),7.16(d,J＝8.1Hz,1H),6.91–6.71(m,1H),2.68(dd,J＝14.5,5.0Hz,1H),2.47(qt,J＝10.3,5.5Hz,1H),2.40–2.24(m,3H),2.15(dt,J＝18.9,9.2Hz,1H),1.83(dt,J＝10.8,5.6Hz,1H),1.59–1.50(m,3H),1.43(tt,J＝13.1,8.0Hz,1H),1.28–1.19(m,5H),0.85(t,J＝6.9Hz,3H)。
compounds 1-8:
1H NMR(600MHz,Chloroform-d)δ7.54(s,1H),7.47(dd,J＝8.9,4.8Hz,2H),7.01(t,J＝8.6Hz,2H),2.67(dd,J＝14.4,5.1Hz,1H),2.50–2.43(m,1H),2.32(dd,J＝14.1,8.8Hz,3H),2.19–2.10(m,1H),1.86–1.81(m,1H),1.60–1.52(m,3H),1.42(d,J＝9.1Hz,1H),1.24(s,5H),0.86(d,J＝6.9Hz,3H)。
compounds 1-11:
1H NMR(600MHz,Chloroform-d)δ8.36(d,J＝8.1Hz,1H),7.66(s,1H),7.38(d,J＝8.0Hz,1H),7.29–7.24(m,1H),7.07(d,J＝7.6Hz,1H),2.77(dd,J＝14.1,4.3Hz,1H),2.50–2.30(m,4H),2.22–2.10(m,1H),1.87(dt,J＝10.2,5.3Hz,1H),1.57(dd,J＝16.5,7.5Hz,2H),1.48–1.38(m,1H),1.36–1.16(m,6H),0.86(t,J＝7.0Hz,3H)。
compounds 1-12:
1H NMR(600MHz,Chloroform-d)δ7.64(s,2H),7.37(d,J＝8.1Hz,1H),7.24(t,J＝8.1Hz,1H),7.09(d,J＝7.9Hz,1H),2.67(dd,J＝14.4,4.7Hz,1H),2.46(qt,J＝10.1,5.4Hz,1H),2.39–2.21(m,3H),2.21–2.09(m,1H),1.82(dt,J＝10.8,5.6Hz,1H),1.63–1.47(m,3H),1.44(dd,J＝13.4,6.2Hz,1H),1.25(q,J＝6.2,5.3Hz,5H),0.85(d,J＝7.1Hz,3H)。
compounds 1-15:
1H NMR(600MHz,Chloroform-d)δ7.76(s,1H),7.61(d,J＝12.1Hz,1H),7.37(t,J＝7.0Hz,2H),2.72–2.63(m,1H),2.45(s,1H),2.34(dd,J＝16.0,8.7Hz,3H),2.16(dt,J＝18.7,9.7Hz,1H),1.84(d,J＝4.4Hz,1H),1.56(s,3H),1.41(d,J＝7.0Hz,1H),1.25(d,J＝18.5Hz,5H),0.85(d,J＝7.1Hz,3H)。
compounds 1-16:
1H NMR(600MHz,Chloroform-d)δ8.18(d,J＝7.4Hz,1H),7.63(d,J＝7.7Hz,1H),7.58(t,J＝7.8Hz,1H),7.44(s,1H),7.27(d,J＝4.4Hz,1H),2.76(dd,J＝14.4,3.8Hz,1H),2.45(dh,J＝15.1,5.5,5.0Hz,1H),2.41–2.26(m,3H),2.16(ddd,J＝18.9,11.0,8.9Hz,1H),1.86(d,J＝4.9Hz,1H),1.60(d,J＝5.6Hz,3H),1.48–1.39(m,1H),1.34–1.20(m,5H),0.87(t,J＝7.0Hz,3H)。
compounds 1-18:
1H NMR(600MHz,Chloroform-d)δ7.66(d,J＝8.3Hz,2H),7.59(d,J＝8.7Hz,3H),2.71(dd,J＝14.6,5.0Hz,1H),2.48(dt,J＝10.2,5.0Hz,1H),2.40–2.30(m,3H),2.23–2.12(m,1H),1.84(dt,J＝10.2,5.3Hz,1H),1.61–1.53(m,3H),1.44(d,J＝7.5Hz,1H),1.26(dd,J＝15.5,4.9Hz,5H),0.86(q,J＝6.9Hz,3H)。
compounds 1-23:
1H NMR(600MHz,Chloroform-d)δ7.88(s,1H),7.42(d,J＝8.8Hz,2H),6.89–6.77(m,2H),3.78(s,2H),2.64(dd,J＝14.2,4.5Hz,1H),2.52–2.39(m,1H),2.29(ddd,J＝10.1,9.2,5.9Hz,3H),2.12(dt,J＝19.3,9.8Hz,1H),1.86–1.75(m,1H),1.56–1.48(m,2H),1.47–1.34(m,1H),1.34–1.06(m,6H),0.86(t,J＝7.0Hz,3H)。
compounds 1-33:
1H NMR(600MHz,Chloroform-d)δ8.39(s,1H),8.31(s,1H),8.01(d,J＝8.0Hz,1H),7.95(d,J＝9.5Hz,1H),7.50(t,J＝8.2Hz,1H),2.77(dd,J＝14.4,4.9Hz,1H),2.57–2.28(m,4H),2.19(ddd,J＝18.7,10.8,8.7Hz,1H),1.94–1.85(m,1H),1.58(qt,J＝9.1,3.7Hz,3H),1.43(td,J＝11.4,9.5,5.8Hz,1H),1.30–1.16(m,5H),0.83(t,J＝6.9Hz,3H).
compounds 1-34:
1H NMR(600MHz,Chloroform-d)δ8.34(s,1H),8.21(d,J＝9.2Hz,2H),7.77(d,J＝9.2Hz,2H),2.78(dd,J＝14.4,4.6Hz,1H),2.57–2.28(m,4H),2.20(dd,J＝19.9,9.5Hz,1H),1.93–1.85(m,1H),1.63–1.53(m,3H),1.42(d,J＝9.3Hz,1H),1.24(dd,J＝10.3,5.0Hz,5H),0.84(t,J＝7.0Hz,3H).
compounds 1-48:
1H NMR(600MHz,Chloroform-d)δ7.75–7.70(m,1H),7.68(s,1H),7.39–7.32(m,1H),2.67(dd,J＝14.5,4.9Hz,1H),2.49–2.44(m,1H),2.37–2.28(m,3H),2.21–2.11(m,1H),1.83(dd,J＝10.0,5.0Hz,1H),1.60–1.53(m,3H),1.43(dd,J＝13.3,6.2Hz,1H),1.31(d,J＝24.7Hz,5H),0.87(d,J＝9.7Hz,3H)。
compounds 1-49:
1H NMR(600MHz,Chloroform-d)δ7.52(d,J＝7.2Hz,1H),7.16(d,J＝7.3Hz,1H),7.07(d,J＝6.0Hz,2H),2.66(d,J＝13.8Hz,1H),2.39(s,1H),2.25(d,J＝16.3Hz,5H),2.09(dd,J＝18.7,9.7Hz,1H),1.77(s,1H),1.52(t,J＝23.2Hz,4H),1.37(s,1H),1.20(s,5H),0.80(d,J＝6.0Hz,3H)。
compounds 1-50:
1H NMR(600MHz,Chloroform-d)δ7.43(d,J＝8.6Hz,2H),7.34(d,J＝8.6Hz,2H),7.31(s,1H),2.67(dd,J＝14.4,5.0Hz,1H),2.46(dd,J＝9.7,4.8Hz,1H),2.39–2.25(m,3H),2.19–2.08(m,1H),1.83(dt,J＝10.3,5.3Hz,1H),1.56(dd,J＝27.1,9.1Hz,3H),1.43(d,J＝8.8Hz,1H),1.30(s,14H),0.86(t,J＝7.0Hz,3H)。
compounds 1-52:
1H NMR(600MHz,Chloroform-d)δ8.21(s,1H),8.16(d,J＝8.4Hz,1H),7.46(t,J＝8.3Hz,1H),7.31(dd,J＝8.1,1.2Hz,1H),2.80–2.70(m,1H),2.47–2.33(m,3H),2.28(dddd,J＝12.6,8.3,5.8,2.3Hz,1H),2.15(ddd,J＝18.8,11.0,8.9Hz,1H),1.88–1.81(m,1H),1.62–1.47(m,3H),1.42(dtd,J＝11.2,9.0,4.9Hz,1H),1.34–1.19(m,5H),0.86(t,J＝7.1Hz,3H).
compounds 1-53:
1H NMR(600MHz,Chloroform-d)δ8.28(t,J＝8.5Hz,1H),7.35(s,1H),7.14(d,J＝8.9Hz,2H),2.74(dd,J＝14.5,4.6Hz,1H),2.52–2.28(m,4H),2.21–2.12(m,1H),1.85(dt,J＝10.5,5.3Hz,1H),1.58(d,J＝5.8Hz,3H),1.47–1.39(m,1H),1.31–1.21(m,5H),0.86(t,J＝7.0Hz,3H).
compounds 1-55:
1H NMR(600MHz,Chloroform-d)δ8.70(d,J＝6.4Hz,1H),7.70(s,1H),7.35(dd,J＝5.4,2.7Hz,1H),7.21(d,J＝9.8Hz,1H),2.83–2.75(m,1H),2.54–2.29(m,4H),2.22–2.12(m,1H),1.86(dt,J＝10.5,5.4Hz,1H),1.59(dd,J＝9.7,4.4Hz,3H),1.43(dd,J＝9.8,6.6Hz,1H),1.34–1.17(m,5H),0.85(t,J＝7.0Hz,3H).
compounds 1-57:
1H NMR(600MHz,Chloroform-d)δ8.35(d,J＝8.5Hz,1H),7.89(s,1H),7.53(t,J＝8.3Hz,1H),7.25(d,J＝8.1Hz,1H),2.86–2.78(m,1H),2.53–2.29(m,4H),2.22–2.13(m,1H),1.88(dd,J＝9.8,5.1Hz,1H),1.58(dd,J＝9.8,4.8Hz,3H),1.48–1.40(m,1H),1.28(dd,J＝15.7,8.7Hz,5H),0.86(t,J＝7.0Hz,3H).
compounds 1-58:
1H NMR(600MHz,Chloroform-d)δ8.23(t,J＝8.5Hz,1H),7.40(s,1H),7.29(d,J＝2.0Hz,1H),7.27(s,1H),2.74(dd,J＝14.5,4.7Hz,1H),2.54–2.27(m,4H),2.16(ddd,J＝18.5,11.0,8.8Hz,1H),1.85(dt,J＝10.9,5.4Hz,1H),1.62–1.49(m,3H),1.47–1.39(m,1H),1.35–1.19(m,5H),0.86(t,J＝7.0Hz,3H).
compounds 1-59:
1H NMR(600MHz,Chloroform-d)δ8.11(d,J＝6.9Hz,1H),7.43(s,1H),6.96(d,J＝10.8Hz,1H),6.85(s,1H),2.74(dd,J＝14.4,4.6Hz,1H),2.45(dt,J＝9.8,4.6Hz,1H),2.32(s,6H),2.20–2.10(m,1H),1.89–1.81(m,1H),1.62–1.54(m,3H),1.44(d,J＝8.7Hz,1H),1.32–1.18(m,5H),0.86(t,J＝7.0Hz,3H).
application example 1: the test method and the result of the tobacco mosaic virus induced disease resistance inhibition rate are as follows:
tobacco variety: liao cigarette 17
Dissolving a compound to be detected by dimethyl sulfoxide, preparing a solution with the concentration of 500mg/L and 100mg/L, selecting tobacco plants with the age of 5-6 leaves and consistent growth vigor, applying the drug on 2 leaves at the base part, inoculating tobacco mosaic virus at intervals of 7 days, and inoculating the first leaf above the drug-applied leaf to each plant. The inoculation method is friction inoculation, and inoculation venom is prepared: weighing 1g of fresh leaves with virus, grinding the leaves with 100ml of phosphate buffer with pH 7.0, then passing through 4 layers of gauze to obtain filtrate, adding a small amount of 60-mesh quartz sand during inoculation, dipping a small amount of inoculation liquid with fingers, lightly rubbing the front sides of the tobacco leaves, mastering the strength of the tobacco leaves just enough to cause slight wound on the leaf surfaces, taking tobacco without pesticide application as a control and taking activated ester or methyl jasmonate as a positive drug control, repeating the treatment for 3 times, and placing the inoculated plants in a sunlight greenhouse for culture. After 10 days, the investigation was carried out according to the following classification criteria (YC/T39-1996).
Level 0: no visible symptoms;
level 1: the heart leaves are chlorosis or bright veins appear;
and 3, level: the heart leaves are obviously flowering or shrinkage, and old leaves are not attacked;
and 5, stage: the heart leaves are obviously flowering or shrinkage, other leaves are diseased, and the leaves are slightly uneven;
and 7, stage: heart and leaf shrinkage deformity, and obvious leaf and leaf of other leaves;
and 9, stage: the leaves of the whole plant are shriveled and deformed and have dark green blotches.
And calculating disease indexes and prevention and treatment effects of the treatments according to the survey data.
The disease index is calculated according to the formula (1), and the calculation result retains the last two decimal points:
Figure BDA0001867812580000151
in the formula:
x is disease index;
Ni-number of diseased leaves in each stage;
i-relative progression;
n-survey total leaf number.
The prevention and treatment effect is calculated according to the formula (2):
Figure BDA0001867812580000152
in the formula:
p-control effect, in percent (%);
CK-placebo disease index;
PT-agent treatment disease index.
TABLE 4 inhibition rate of tobacco mosaic virus induced disease resistance by compounds
Figure BDA0001867812580000153
Figure BDA0001867812580000161
The data show that the compound shown in the formula I has better plant induced disease resistance activity.
Application example 2: the test method and the result of the germination inhibition rate of the wheat seeds are as follows:
seed treatment: sterilizing wheat seeds with 2% sodium hypochlorite aqueous solution for 15min, washing with sterile water, soaking seeds with 100(mg/L) and 500(mg/L) compounds 1-20 respectively for 24h, using water as Control (CK) and abscisic acid as positive control.
Germination test: seeds with full grains and consistent size are selected, inserted into sterilized culture dishes (diameter 9cm) containing 30mL of agar, 25 seeds per dish are placed in a constant temperature culture room at 25 ℃ under dark condition for germination test, and each treatment is repeated for 3 times. The germination number (based on the length of radicle as the standard for half of the length of seed) was recorded every day starting on day 2, and the germination test was terminated by day 8, and the germination potential (day 4) and germination rate (day 8) of the germinated seeds were measured, and the calculation formula was as follows.
Germination vigor (%) - (germination number in 4 d/test seed number) x 100%
Germination percentage (%) - (germination number in 8 d/test seed number) x 100%
TABLE 5 germination potential of wheat seeds with the action of the compounds
Figure BDA0001867812580000162
Figure BDA0001867812580000171
TABLE 6 germination rates of wheat seeds with the action of compounds
Figure BDA0001867812580000172
Figure BDA0001867812580000181
From the data in tables 5 and 6 above, it can be seen that the compounds described in claim of formula I can germinate (more than 90% of germination potential) after 4 days at low concentration of 100mg/L, whereas the control blank has completely germinated. Can germinate after 8 days (the germination rate is more than 90%). The compounds have good activity of inhibiting seed germination at low concentration, can delay seed germination, and can not cause the seed to lose the germination activity.
At 500mg/L treatment at high concentration, the germination potential was inhibited after 4 days (the germination potential was mostly between 30-10%). Most compounds also had good germination effects after 8 days (germination rates mostly ranged between more than 90-70%). The compounds have good activity of inhibiting the germination of seeds at high concentration and good safety (the compounds still have good germination activity under the treatment of high concentration) without causing the seeds to lose the germination activity.

Claims (4)

1. A 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative, characterized by: the 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative is a compound represented by formula I:
Figure DEST_PATH_IMAGE001
wherein
Ar is unsubstituted or substituted by 1-5R1Substituted phenyl;
R1selected from halogen, nitro, cyano, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12An alkoxy group.
2. A 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative according to claim 1, wherein: in the compounds of formula I:
ar is unsubstituted or substituted by 1-5R1Substituted benzenes;
R1selected from halogen, nitro, cyano, methyl, methoxy or trifluoromethyl.
3. A 2- (3-oxo-2-pentylcyclopentyl) acetamide derivative according to claim 1, wherein: in the compounds of formula I:
ar is 3-methylphenyl, 4-methylphenyl, 2, 4-dimethylphenyl, 4-fluorophenyl, 2, 4-difluorophenyl, 2-chlorophenyl, 3, 4-dichlorophenyl, 2-trifluoromethylphenyl, 4-methoxyphenyl, 3-nitrophenyl, 4-nitrophenyl, 3-fluorophenyl, 3-chloro-4-fluorophenyl, 2-methyl-3-chlorophenyl, 4-tert-butylphenyl, 2-nitro-3-chlorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-cyano-3-chlorophenyl, 2-fluoro-4-bromophenyl, 2-fluoro-5-methylphenyl.
4. Use of a compound of formula I according to any one of claims 1 to 3 in the preparation of a plant growth regulator or a plant-induced disease-resistant activator.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0521435A2 (en) * 1991-07-04 1993-01-07 B.A.T. Cigarettenfabriken GmbH Method to promote the production of secondary metabolites in plant cell cultures
CN106795101A (en) * 2014-10-20 2017-05-31 先正达参股股份有限公司 Herbicides compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0521435A2 (en) * 1991-07-04 1993-01-07 B.A.T. Cigarettenfabriken GmbH Method to promote the production of secondary metabolites in plant cell cultures
CN106795101A (en) * 2014-10-20 2017-05-31 先正达参股股份有限公司 Herbicides compounds

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* Cited by examiner, † Cited by third party
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