CN110041259A - Fluorine substituted pyrazolecarboxylic amine derivant and its preparation method and application - Google Patents
Fluorine substituted pyrazolecarboxylic amine derivant and its preparation method and application Download PDFInfo
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- CN110041259A CN110041259A CN201910422285.0A CN201910422285A CN110041259A CN 110041259 A CN110041259 A CN 110041259A CN 201910422285 A CN201910422285 A CN 201910422285A CN 110041259 A CN110041259 A CN 110041259A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
Abstract
The present invention provides fluorine substituted pyrazolecarboxylic amine derivants and its preparation method and application, and the present invention relates to fluorine substituted pyrazolecarboxylic aminated compounds, general formula of the chemical structure is shown in formula III:
Description
Technical field
Technical solution of the present invention is related to fluorine-containing substituted pyrazolecarboxylic aminated compounds, and in particular to 1- methyl -3- difluoromethyl
Pyrazole amine and 1- methyl-3-trifluoromethyl pyrazol amine derivant.
Background technique
Pyrazole derivatives have efficient, low toxicity, wide spectrum biological activity, the succinic acid to put goods on the market in nearly 20 years
There are about 70% or more in dehydrogenase inhibitor class fungicide kind all to contain a pyrazole heterocycle.Existing pyrazoles acyl reported in the literature
Amine compounds targetted mitochondria Respiratory Chain Complex I I be also known as succinate dehydrogenase (Du Shijie, waits, Pesticide Science journal, 2018
It (5): 545-556), is the fungicide of a kind of wide spectrum.Fungicide containing pyrazole heterocycle is various in style, living with excellent sterilization
Property.Wherein pyraclostrobin, (Zhang Kai waits, modern, 2018 (2): 8-11) are right in methoxy acrylic bactericide
The disease that phytopathogen in various crop generates, such as melon and fruit powdery mildew, downy mildew, anthracnose, leaf spot, scab, axis
The diseases such as maize ear rot, brown spot have preferable preventive effect, which has that dosage is few, good drug efficacy, and effect is fast, environmentally friendly equal spies
Point.
Pyrazole compound has wide research space, and the derivative containing pyrrazole structure improves tool to the activity of fungicide
It plays an important role.The popular research side that pyrazole group is China and foreign countries scientific research institutions and agro-chemical companies is introduced in pesticide molecule design
To.The multifarious fluorine-containing substituted pyrazolecarboxylic amine compounds of construction structure improve the bactericidal activity of target molecule, novel to researching and developing
The fungicide with broad-spectrum disease resistance have important more practical value.
To find and finding more efficient, wide spectrum, low toxicity, low ecological risk and the agriculture of without cross-resistance with existing fungicides
Design has been synthesized fluorine substituted pyrazolecarboxylic amine derivative by medicine lead compound, the present invention, while having carried out the biology of system
Active screening and evaluation, to find more high activities, low resistance risk and the high environment friendly agricultural candidate product of Environmental compatibility
Kind.
Summary of the invention
The technical problems to be solved by the present invention are: the synthetic method of fluorine substituted pyrazolecarboxylic aminated compounds is provided,
This kind of compound modulates agricultural, the bioactivity and its measuring method of gardening and health and forestry plant pathogen are provided, together
When application of these compounds in agriculture field, horticultural field, field of forestry and health field is provided.
The present invention solves technical solution used by the technical problem: having agriculture field, horticultural field, field of forestry
The general formula of the chemical structure of the fluorine substituted pyrazolecarboxylic aminated compounds of bactericidal activity is shown in formula III:
R1It is selected from: C1-C6Fluoro-alkyl, C1-C6Fluoroalkyl, C2-C6Fluoro alkenyl, C2-C6Fluoro alkynyl.
R1It preferably is selected from: trifluoromethyl, difluoromethyl.
The synthetic method of biaryl amide pyrazole compound of the invention is as follows:
The synthesis of fluorine-containing substituted pyrazolecarboxylic aminated compounds and the specific method of biological activity determination of the invention be divided into
Lower step:
A. the preparation of compound II:
28.3 mMs of pyrazoles acid compound I are added in 250 milliliters of twoport round-bottomed flasks, pyrazoles acid is selected from: 1- methyl-
- 4 pyrazole carboxylic acid of 3- trifluoromethyl, -4 pyrazole carboxylic acid of 1- methyl -3- difluoromethyl；It is suspended in t-butanol solution, nitrogen protection
Under, 36.91 mMs of diphenyl phosphate azides (DPPA) and 56.78 mMs of n,N-diisopropylethylamine are added at room temperature
(DPEA), half an hour is stirred at room temperature in reaction solution, and rear slow heating heating is stirred 4 hours under 80~90 degrees Celsius.Fully reacting
Afterwards, system is cooled into room temperature, is concentrated under reduced pressure and removes excess of solvent, residue purifies to change through 100~200 mesh silica gel column chromatographies
Object II is closed, the petroleum ether that eluant, eluent is 60~90 degrees Celsius: ethyl acetate, according to the difference of product, volume ratio 10: 1-8
: 1, yield 76-91%；The amount of compound II preparation and the volume of reaction vessel are expanded or shunk by corresponding proportion.
B. the preparation of compound III:
4 mMs of compound II are added in 50 milliliters of single necked round bottom flask, it is molten to add 8 milliliters of dry methylene chloride
4 milliliters of trifluoroacetic acids are added into reaction, are then stirred at room temperature 2 hours, end of reaction for liquid, and TLC monitors reaction solution, and discovery is former
Expect II fully reacting, stops reaction.Reaction solution is concentrated under reduced pressure, extra solvent and trifluoroacetic acid are removed.Water 40 is added
Milliliter, saturated aqueous sodium carbonate washing neutralize, are then extracted with ethyl acetate, isolate organic layer, organic layer saturated carbon
Sour hydrogen sodium is washed, saturated sodium-chloride is respectively washed one time, and anhydrous sodium sulfate is dry, is filtered, solvent is removed under reduced pressure, residue is through 100~200
Mesh silica gel column chromatography purifies to obtain compound III, the petroleum ether that eluant, eluent is 60~90 degrees Celsius: ethyl acetate, according to product
Difference, volume ratio 4: 1-2: 1, yield 89-93%；The amount of compound III preparation and the volume of reaction vessel are by corresponding ratio
Example is expanded or shunk.
C. the measurement of fluorine-containing substituted pyrazolecarboxylic aminated compounds III and its intermediate bactericidal activity of the invention:
The sterilization of fluorine-containing substituted pyrazolecarboxylic aminated compounds and its intermediate of the invention or bacteriostatic activity use thalli growth
The measurement of rate method, specific steps are as follows: take 1.8 milligrams of samples to be dissolved in 2 drop n,N-Dimethylformamide, then with containing a certain amount of
The aqueous solution of polysorbas20 emulsifier is diluted to the medicament of 500 mcg/mls, and reagent agent is aseptically respectively drawn to 1 milli
It rises in culture dish, then is separately added into 9 milliliters of PDA culture mediums, 50 mcg/ml drug containing tablets are made after shaking up, to add 1
The plate of milliliter aqua sterilisa does blank control, cuts bacterium disk along mycelia outer rim with 4 millimeters of diameter of punch, moves to drug containing tablet
On, in equilateral triangle to put, every processing is repeated 3 times, culture dish is placed on culture in 24 ± 1 degrees Celsius of constant incubators, to
Control colony diameter investigates each processing bacterium disk extension diameter after being extended to more than 2 centimetres, average, count compared with blank control
Opposite bacteriostasis rate is calculated, is the kind for most of typical plant pathogen that field actually occurs in China's agricultural production for examination strain
Belong to, code name and title are as follows: AS: tomato early blight bacterium, latin name are as follows: Alternaria solani, BC: cucumber grey mold
Germ, latin name are as follows: Botrytis cinerea, CA: peanut Cercospora bacteria, latin name are as follows: Cercospora
Arachidicola, GZ: fusarium graminearum, latin name are as follows: Gibberella zeae, PI: phytophthora infestans,
Latin name are as follows: Phytophthora infestans (Mont.) de Bary, PP: Botryosphaeria berengeriana f. sp, latin name are as follows:
Physalospora piricola, PS: Rhizoctonia solani Kuhn, latin name are as follows: Pellicularia sasakii, RC: cereal
Rhizoctonia, latin name are as follows: Rhizoctonia cerealis, SS: Sclerotinia sclerotiorum, latin name are as follows: Sclerotinia
sclerotiorum。
The present invention passes through specific preparation and the more specific fluorine-containing substituted pyrazolecarboxylic amine of explanation of biological activity determination embodiment
The synthesis and bioactivity and application of object III and its intermediate are closed, the embodiment is only used for illustrating the present invention rather than limit
The system present invention, especially bioactivity is merely illustrative of, rather than limits this patent, and specific embodiment is as follows:
Embodiment 1: the preparation of compound II-1:
28.3 mMs of pyrazoles acid compound I-1 are added in 250 milliliters of twoport round-bottomed flasks, pyrazoles acid is selected from: 1- first
- 4 pyrazole carboxylic acid of base -3- difluoromethyl；It is suspended in t-butanol solution, under nitrogen protection, 36.91 mmoles is added at room temperature
Half an hour is stirred at room temperature in that diphenyl phosphate azide and 56.78 mMs of n,N-diisopropylethylamine, reaction solution, rear to be slowly heated
Heating, is stirred 4 hours under 80~90 degrees Celsius.After fully reacting, system is cooled into room temperature, it is extra molten that removing is concentrated under reduced pressure
Agent, residue purify to obtain compound II-1 through 100~200 mesh silica gel column chromatographies, the petroleum ether that eluant, eluent is 60~90 degrees Celsius:
Ethyl acetate, according to the difference of product, volume ratio 10: 1-8: 1, yield 76-91%；The nuclear magnetic data of the compound is such as
Under:1H NMR (400MHz, CDCl3) δ 6.91 (s, 1H), 6.64 (t, J=54.7Hz, 1H), 3.73 (t, J=1.5Hz, 3H),
3.11 (s, 2H).The amount of compound II preparation and the volume of reaction vessel are expanded or shunk by corresponding proportion.The reason of compound II
Change parameter and structural parameters are shown in Table 1.
Embodiment 2: the preparation of compound III-1:
4 mMs of compound II-1 are added in 50 milliliters of single necked round bottom flask, add 8 milliliters of dry methylene chloride
4 milliliters of trifluoroacetic acids are added into reaction, are then stirred at room temperature 2 hours, end of reaction for solution, and TLC monitors reaction solution, work as original
Expect II fully reacting, then stops reacting.Reaction solution is concentrated under reduced pressure, extra solvent and trifluoroacetic acid are removed.Water is added
40 milliliters, saturated aqueous sodium carbonate washing neutralizes, and is then extracted with ethyl acetate, and isolates organic layer, organic layer saturation
Sodium bicarbonate is washed, saturated sodium-chloride is respectively washed one time, and anhydrous sodium sulfate is dry, is filtered, and is removed under reduced pressure solvent, residue through 100~
200 mesh silica gel column chromatographies purify to obtain compound III-1, the petroleum ether that eluant, eluent is 60~90 degrees Celsius: ethyl acetate, according to production
The difference of object, volume ratio 4: 1-2: 1, yield 89-93%；The compound1H NMR (400MHz, CDCl3): δ 7.48-
7.41 (m, 3H), 7.39-7.35 (m, 2H), 6.66 (s, 1H), 3.74 (s, 3H).The amount and reaction vessel of compound III preparation
Volume expanded or shunk by corresponding proportion.The physical and chemical parameter and structural parameters of compound III is shown in Table 1.
Embodiment 3: the bactericidal activity of fluorine-containing substituted pyrazolecarboxylic aminated compounds III and its intermediate of the invention measures knot
Fruit:
The frequently seen plants disease fungus code name and title that the present invention tests are as follows: AS: tomato early blight bacterium, latin name
Are as follows: Alternaria solani, BC: botrytis cinerea pers, latin name are as follows: Botrytis cinerea, CA: peanut foxiness
Germ, latin name are as follows: Cercospora arachidicola, GZ: fusarium graminearum, latin name are as follows: Gibberella
Zeae, PI: phytophthora infestans, latin name are as follows: Phytophthora infestans (Mont.) de Bary, PP: apple
Fruit Target spot pathogen, latin name are as follows: Physalospora piricola, PS: Rhizoctonia solani Kuhn, latin name are as follows:
Pellicularia sasakii, RC: Rhizoctonia cerealis, latin name are as follows: Rhizoctonia cerealis, SS: Sclerotina Sclerotiorum in Winter Rape
Core germ, latin name are as follows: Sclerotinia sclerotiorum, these strains represent field in agricultural production and occur
Most of pathogen kind.
Thalli growth rate method measurement result is shown in Table 2, and table 2 shows majority of compounds of the invention in 50 mcg/ml
In vitro has certain bacteriostatic activity to the thallus of test.Compound ydy02-8, ydy02-9 and ydy02-37 couple
The growth inhibitory effect of tomato early blight bacterium is up to 30%, has certain bacteriostasis.Compound ydy02-8, ydy02-36
Being up to 40% to the growth inhibitory effect of botrytis cinerea pers has preferable fungistatic effect.To the Activity Results of peanut Cercospora asparagagas
Show the inhibitory activity of compound ydy02-8, ydy02-9 40% or more, wherein compound ydy02-9 is to peanut foxiness
The activity of disease is that 63% fungistatic effect is excellent.Compound ydy02-8, ydy02- are shown to the active testing of fusarium graminearum
9, the bacteriostatic activity of ydy02-37 has preferable fungistatic effect 30% or more.The active testing of Phytophthora infestans
The result shows that the bacteriostatic activity of compound ydy02-8, ydy02-9, ydy02-36 are unobvious.Compound ydy02-8 is to apple wheel
The growth inhibitory effect of line germ has preferable fungistatic effect up to 30%.The active testing of Rhizoctonia solani Kuhn is shown
Ydy02-8, ydy02-9, ydy02-36, ydy02-37 have certain bacteriostatic activity.To the active testing table of Rhizoctonia cerealis
Bright, the bacteriostatic activity of compound ydy02-8, ydy02-9, ydy02-37 have centainly Rhizoctonia cerealis 30% or more
Inhibiting effect.Such compound, which inhibits unobvious to Sclerotinia sclerotiorum, to be shown to the active testing of Sclerotinia sclerotiorum.
Embodiment 4: fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate are in preparing composition pesticide
Application:
Fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate can prepare composition pesticide, the combination
Object includes fluorine-containing substituted pyrazolecarboxylic aminated compounds III and its intermediate of the invention as active constituent, the content of active constituent
For 0.1% to 99.9% weight, the table of the solid or liquid adjuvants of 99.9% to 0.1% weight and optional 0 to 50% weight
Face activating agent.
Embodiment 5: fluorine-containing substituted pyrazolecarboxylic aminated compounds III and its intermediate of the invention is preparing agriculture chemical compounding combination
Application in object:
Fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate can be with other commercially available agricultural chemicals, i.e. desinsection
Agent, acaricide, fungicide, antivirotic or activating plants agent compounding preparation pesticide complex composition, the complex composition include
This fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate and other commercially available agricultural chemicals, i.e. insecticide, acaricide,
Fungicide, antivirotic or activating plants agent as active constituent, fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its
Intermediate and other commercially available agricultural chemicals, i.e. insecticide, acaricide, fungicide, antivirotic or the ratio of activating plants agent are quality
Percentage 1%: 99% to 99%: 1%, the content of active constituent are 0.1% to 99.9% weight, 99.9% to 0.1% weight
Solid or liquid adjuvants and optional 0 to 50% weight surfactant.
Embodiment 6: fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate and insecticide composition are being prevented and treated
Application in agricultural and forestry and gardening plant insect pest:
All fluorine-containing substituted pyrazolecarboxylic aminated compounds III and its intermediate of the invention with it is any one in commodity insecticide
Kind or two kinds of combinations form Pesticidal combination and select for preventing and treating agricultural and forestry and gardening plant insect pest, the commodity insecticide
From: ground Asia Nong, Acetamiprid, emamectin benzoate, milbemectin, avermectin, pleocidin, cypermethrin, efficient chlorine cyanogen
Pyrethroids, Cyhalothrin, decis, Fenpropathrin, Beta- cyfloxylate, Lambda- Cyhalothrin, dichloro
Phenothrin, permethrin, allethrin, Biphenthrin, Permethrin, ethofenprox, flumethrin, fluvalinate,
Imidacloprid, Nitenpyram, imidaclothiz, thiacloprid, Diacloden, clothianidin, dinotefuran, clothianadin, Da Tenan, diflubenzuron, children of going out
Urea, Teflubenzuron, deinsectization be grand, flubenzuron, flufenoxuron, pyridine worm are grand, lufenuron, poisonous insect urea, penfluron, flucycloxuron, chlorfluazuron, piperazine worm
Urea, furan tebufenozide, tebufenozide, chlorine tebufenozide, methoxyfenozide, ring tebufenozide, flolimat, DDVP, quinalphos, pyridazine
Sulphur phosphorus, isoprocarb, sevin, Aphox, MTMC, Mobucin, cartap, Bassa, leaf disperse, carbaryl, rosickyite gram hundred
Prestige, carbosulfan, cartap, fenisobromolate, Hexythiazox, fenpyroximate, pyridaben, clofentezine, propargite, diafenthiuron, pymetrozine,
Envidor, spiral shell worm ester, spiral shell worm ethyl ester, butene-fipronil, azacyclotin, Buprofezin, Cupric sulfate, dimehypo, chlorantraniliprole, fluorine worm acyl
Amine, fluorine cyanogen insect amide, cyanogen insect amide, Tolfenpyrad, chlorfenapyr, pyrazinones, etoxazole, tebufenpyrad, young ketone of rattling away, Nylar, angstrom
Ma rhzomorph；The quality hundred of fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate in the Pesticidal combination
Point content is 1%-90%, and the surface of the solid or liquid adjuvants of 99% to 10% weight and optional 0 to 50% weight is living
Property agent, the ratio of fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate and aforementioned commodity insecticide is quality
Percentage 1%: 99% to 99%: 1%；The dosage form of Pesticidal combination processing is selected from: seed treatment emulsion, aqueous emulsion, big
It is granula, microemulsion, water-soluble granule, soluble thick agent, water-dispersible granules, poison grain, aerosol, blocky poison bait, sustained-release block, dense
Poison bait, CG/Encapsulated granule, micro-capsule suspension, Waterless Seed Dressing pulvis, missible oil, electrostatic spray agent, water-in-oil emulsion, oil in water emulsion,
Smoke candle, granula subtilis, smoke candle, smoke cartridge, smog stick, seed treatment suspending agent, smog piece, smog ball, granular poison bait, hot mist
Agent, fine granule, oil suspending agent, oil-dispersing property pulvis, sheet poison bait, dense jelly, sprinkles and pours agent, seed coat agent, liniment, suspension medicine paint
Emulsion, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume suspending agent, tracking pulvis, ultra-low volume
Any one in liquor, wet-mixing kind water-dispersible powder；The insect pest of the plant of the Pesticidal combination prevention and treatment is selected from: red spider,
Asiatic migrotory locust, reading room management, Chinese rice grasshopper, Patanga japonica (l.Bol.), single thorn mole cricket, Oriental burmeister, rice thrips, onion thrips, greenhouse Ji
It is horse, haplothrips aculeatus, Mai Jianguan thrips, Trialeurodes vaporariorum Westwood, Bemisia tabaci, rice green leafhopper, green leaf hopper, chlorita biguttula, spot clothing plant hopper, brown
The flat angle plant hopper of plant hopper, white backed planthopper, small brown rice planthopper, sugarcane, cotten aphid, green bugs, grain aphid, black peach aphid, kaoliang aphid, radish aphid,
Icerya purchasi, Pseudaulacaspis pentagona, unaspis shield kuwana, san jose scale, wax insect, ceroplastes rubens, Didesmococcus koreanus Borchs, pear lace bug, banana lace bug, thin corner piece
It is stinkbug, Orius minutus, slender rice bug, paddy fly, niphe elongata, scotinophora lurida, green rice bug, green plant bug, alfalfa plant bug, black striped plant bug, big
It is Chrysopa, beautiful Chrysopa, Chinese green lacewing, rain moth, casemaking clothes moth, oriental moth, brown slug moth, thosea siensis, gelechiid, pink bollworm, brachmia triannuella, small
Diamond-back moth, small heart-eating peach worm, eating-core bean worm, apple Spilonota lechriaspis, brown belt length leaf roller, Adoxophyes cyrtosema, striped rice borer, beans
Pod snout moth's larva, corn borer, yellow rice borer, Oeobia undalis, rice leaf roller, snout moth's larva, Notarchaderogata, dichocrocis punctiferalis, armyworm, prodenia litura, rice borer
Sandfly, beet armyworm, pink rice borer, bollworm, ancient cooking vessel point spark, black cutworm, big cutworm, yellow cutworm, steals poison at anomis flava
Moth, gypsymoth, palaearctic sweet potato, greenish brown hawk moth, straight grain rice hesperiidae, pelopidas mathias, Papilio xuthus, Common Mormon, cabbage butterfly, ramie
Red admiral, a ramie Huang a kind of butterfly harmful to crop plants, beans blister beetle, Venus ground beetle, wrinkle sheath ground beetle, wheat head ground beetle, pleonomus canaliculatus, Agriotes subrittatus Motschulsky, paddy spot
The small buprestid beetle of khapra beetle, attagenus piceus, citrus, golden edge buprestid beetle, yellow meal worm, dark mealworm, red flour beetle, confused flour beetle, verdigris are different beautiful
Cockchafer, H. parallela, holotrichia oblita, mulberry borer, longicorn beetle, nadezhdiella cantori, pink neck longicorn, big daikon leaf beetle, apelet
Leaf worm, aulacophora femoralis, phyllotreta striolata, Callosobruchus chinensis, pea weevil, broad bean weevil, sitophilus zea-mais, rice weevil, dolerus tritici, pear fruit sawfly, yellowish leukorrhea
Ichneumon wasp, armyworm white star ichneumon wasp, corn earworm hang cocoon ichneumon wasp, Campoletis chlorideae, snout moth's larva stain wart ichneumon wasp, mosquito, horsefly, wheat midge,
Contarinia tritici, citrus fruit fly, melonfly, wheat leaf ash latent fly, Americal rice leaf miner, Soybean stem borer, frit fly, Hylemyia Platura Meigen, green onion
Fly, radish fly, full skirt Exorista civilis, corn borer is strict posts fly；The plant of Pesticidal combination prevention and treatment is selected from: paddy, wheat, big
Wheat, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, semen viciae fabae, pea, mung bean, red bean, cotton, silkworm and mulberry,
Peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco,
Tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tuber, green onion, garlic, watermelon, muskmelon, "Hami" melon, pawpaw, apple, citrus, peach
Tree, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
Embodiment 7: fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate and antimicrobial combination are being prevented and treated
Application in agricultural and forestry and gardening plant disease:
All fluorine-containing substituted pyrazolecarboxylic aminated compounds III and its intermediate of the invention with it is any one in commodity fungicide
Kind or two kinds of combinations form bactericidal composition and select for preventing and treating agricultural and forestry and gardening plant disease, the commodity fungicide
From diazosulfide, tiadinil, it is abbreviated as TDL, tisocromide, first thiophene and lures amine, 4- methyl-1,2,3- thiadiazoles -5- formic acid,
4- methyl-1,2,3- thiadiazoles -5- sodium formates, 4- methyl-1 are 2,3- thiadiazoles -5- Ethyl formates, DL- beta-aminobutyric acid, different
Metsulfovax, English common name are as follows: isotianil, 3,4-, bis- chloroisothiazole -5- formic acid, 3,4-, bis- chloroisothiazole -5- formic acid
Sodium, 3,4-, bis- chloroisothiazole -5- Ethyl formate, virazole, antofine, Ningnanmycin or salicylic acid, cymoxanil, thiram, good fortune
U.S. zinc, Mancozeb, aliette, thiophanate-methyl, Bravo, enemy can pine, procymidone, fenpropidin, thiophanate methyl, Tobes
Saliva, Metalaxyl-M, flumorph, dimethomorph, mefenoxam, benalaxyl-M, double chlorine zarilamid, flusulfamide, first flusulfamide,
Thiophene fluorine bacterium amine, flutolanil, tecloftalam, ring propionyl bacterium amine, cyflufenamid, fenhexamid, zarilamid, Silthiopham, furametpyr,
Pyrrole metsulfovax, mandipropamid, zoxamide, fenfuram, carboxin, chlozolinate, iprodione, Fluoxastrobin, dimoxystrobin, fluorine are phonetic
Bacterium ester, kresoxim-methyl, SSF 126, orysastrobin, ZEN 90160, pyraclostrobin, trifloxystrobin, Enestroburin, alkene oxime amine, oxygen ring
Azoles, bromuconazole, Cyproconazole, difenoconazole, olefin conversion, efficient olefin conversion, epoxiconazole, benzoxazole, Fluquinconazole, Flusilazole,
Flutriafol, hexaconazole, glyoxalin, kind bacterium azoles, metconazole, nitrile bacterium azoles, penconazole, propiconazole, prothioconazoles, simeconazoles, penta azoles
Alcohol, tetraconazole, Triadimenol, triticonazole, bitertanol, probenazole, furidazol, imazalil, efficient imazalil, Prochloraz,
Fluorine bacterium azoles, Fenamidone, dislike imidazoles, pefurazoate, Famoxate, oxazole, hymexazol, Wakil, thiazole bacterium at cyazofamid
Amine, Grandox fumigant, octhilinone, benthiozole, dodemorph, butadiene morpholine, tridemorph, fenpiclonil, fludioxonil, fluazinam,
It is pyrifenox, ring pyridine bacterium amine, Boscalid, fluopicolide, pyridine bacterium amine, cyprodinil, fluorine mepanipyrim, ferimzone, mepanipyrim, phonetic
Mould amine, Fenarimol, nuarimol, chinomethionat, dithianon, ethoxyquin, oxyquinoline, the third oxygen quinoline, benzene oxygen quinoline
Quinoline, diethofencarb, iprovalicarb, benzene metsulfovax, Propamocarb, methasulfocarb, edifenphos, different rice blast net, pyrazophos, tolelofos-methyl,
Blasticidin-S, kasugarnycin, polyoxin, Polyoxin, valida, jinggangmeisu, streptomysin, metalaxyl, furalaxyl, benzene frost
Spirit, ofurace, mebenil, carbendazim, benomyl, thiophanate-methyl, triazolone, bupirimate, dimethirimol, second are phonetic
Phenol, difoltan, captan, folpet, vinclozolin, fluoromide, dimethachlon, Bravo, Isoprothiolane, kitazine, leaf
Withered azoles, pentachloronitrobenzene, Propineb, phosethyl-Al, sulphur, Bordeaux mixture, copper sulphate, copper oxychloride, cuprous oxide, hydrogen-oxygen
Change copper, metrafenone, Pencycuron, diclomezin, Rabcide, pyroquilon, volution bacterium amine, tricyclazole, triforine, more fruit pyridines, biguanides
Pungent salt, iminoctadine, botran, benzene flusulfamide, toluene flusulfamide, K-281, fenaminosulf, oxolinic acide, probenazole, bromine nitre
Alcohol, iodomethane, metham-sodium, enemy line ester, dazomet, nemamort, lythidathion, fensulfothion, thionazin, dichlofenthion, fosthietan,
Oxamyl, vikane, dichloropropylene, dichloro-isonicotinic acid, allyl isothiazole；Fluorine-containing substituted pyrazolecarboxylic aminated compounds of the invention
The total mass percentage of III and its intermediate in the bactericidal composition is 1%-90%, 99% to 10% weight
The surfactant of solid or liquid adjuvants and optional 0 to 50% weight, fluorine-containing substituted pyrazolecarboxylic amine chemical combination of the invention
The ratio of object III and its intermediate and aforementioned commodity fungicide is mass percent 1%: 99% to 99%: 1%；The sterilization
Composition processing dosage form be selected from: seed treatment emulsion, aqueous emulsion, big granula, microemulsion, water-soluble granule, soluble thick agent,
Water-dispersible granules, poison grain, aerosol, blocky poison bait, sustained-release block, dense poison bait, CG/Encapsulated granule, micro-capsule suspension, Waterless Seed Dressing
Pulvis, missible oil, electrostatic spray agent, water-in-oil emulsion, oil in water emulsion, smoke candle, granula subtilis, smoke candle, smoke cartridge, smog
Stick, seed treatment suspending agent, smog piece, smog ball, granular poison bait, thermal fog, medicine paint, fine granule, oil suspending agent, oil-dispersing property powder
Agent, dense jelly, sprinkles and pours agent, seed coat agent, liniment, suspended emulsion, film forming finish, soluble powder, seed treatment sheet poison bait
It is water solube powder, ultra-low volume suspending agent, tracking pulvis, ultra low volume liquids, any one in wet-mixing kind water-dispersible powder
Kind；The plant disease of the bactericidal composition prevention and treatment is selected from: seedling blight of rice, tomato root rot, the late blight of potato, tobacco are black
Shin disease, millet powdery mildew, downy mildew of garpe, downy mildew of lettuce, cucumber downy mildew, cucumber anthracnose；The bactericidal composition is suitable
Plant is selected from: paddy, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, semen viciae fabae,
Pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria,
Rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tuber, green onion, garlic, watermelon, sweet tea
Melon, "Hami" melon, pawpaw, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, basin
Scape.
Embodiment 8: fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate are combined with anti-plant virus agent
Application in prevention and treatment agricultural and forestry and gardening plant virus disease:
All fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate and appointing in commodity antiviral agent
The one or two kinds of combinations of meaning form antiviral composition for preventing and treating agricultural and forestry and gardening plant virus disease, the quotient
Product antiviral agent is selected from: diazosulfide, tiadinil, is abbreviated as TDL, isotianil, English common name are as follows:
Isotianil, 4- methyl-1,2,3- thiadiazoles -5- formic acid, 4- methyl-1,2,3- thiadiazoles -5- sodium formates, 4- methyl-1,
2,3- thiadiazoles -5- Ethyl formates, 3,4-, bis- chloroisothiazole -5- formic acid, 3,4-, bis- chloroisothiazole -5- sodium formate, 3,4- dichloro
Isothiazole -5- Ethyl formate, DL- β-aminobutyric acid, virazole, antofine, Ningnanmycin, tisocromide, first thiophene lure amine or bigcatkin willow
Acid, cytosintetidemycin, dichloro-isonicotinic acid, allyl isothiazole, well ridge azanol, jinggangmeisu；Fluorine-containing substituted pyrazolecarboxylic amine of the invention
The total mass percentage of compound III and its intermediate in the antiviral composition is 1%-90%, and 99% arrives
The surfactant of the solid or liquid adjuvants of 10% weight and optional 0 to 50% weight, fluorine-containing substituted pyrazolecarboxylic of the invention
The ratio of aminated compounds III and its intermediate and aforementioned commodity anti-plant virus agent is mass percent 1%: 99% to 99%
: 1%；The dosage form of the antiviral composition processing is selected from: seed treatment emulsion, aqueous emulsion, big granula, microemulsion, water solubility
Granula, soluble thick agent, water-dispersible granules, poison grain, aerosol, blocky poison bait, sustained-release block, dense poison bait, CG/Encapsulated granule, micro- glue
Capsule suspending agent, Waterless Seed Dressing pulvis, missible oil, electrostatic spray agent, water-in-oil emulsion, oil in water emulsion, smoke candle, granula subtilis, smog
Candle, smoke cartridge, smog stick, seed treatment suspending agent, smog piece, smog ball, granular poison bait, thermal fog, medicine paint, fine granule, oil
Suspension, sheet poison bait, dense jelly, sprinkles and pours agent, seed coat agent, liniment, suspended emulsion, film forming finish, solvable oil-dispersing property pulvis
Property pulvis, seed treatment water solube powder, ultra-low volume suspending agent, tracking pulvis, ultra low volume liquids, wet-mixing kind water dispersible
Any one in pulvis；The virus disease of the antiviral composition prevention and treatment is selected from: rice dwarf virus disease, yellow dwarf, striped leaf
Blight, fern leaf of tomato viral disease, Tomato yellow mosaic virus, pepper mosaic virus disease viral disease, tobacco veinal necrosis virus disease, maize dwarf mosaic
Disease, cauliflower mosaic virus, citrus virosis, cymbidium mosaic virus, cybidium ring spot virus；The antiviral composition is for preventing
The plant controlled is selected from: paddy, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, semen viciae fabae,
Pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria,
Rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tuber, green onion, garlic, watermelon, sweet tea
Melon, "Hami" melon, pawpaw, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, basin
Scape.
Embodiment 9: fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate are combined with acaricide and are being prevented and treated
Application in agricultural and forestry and gardening plant mite evil:
All fluorine-containing substituted pyrazolecarboxylic aminated compounds III and its intermediate of the invention with it is any one in commodity acaricide
Kind or two kinds of combinations form miticide composition and are used to prevent and treat agriculture harmful with forestry and gardening plant mite, the commodity acaricide choosing
From: azacyclotin, plictran, fenbutatin oxide, three phosphor tins, chlorfenviphos, dimethylvinphos, crotoxyphos, heptenophos, Menite, 2-dichloroethylk dimethyl phosphate,
Diothyl, imino-formyl chloride sulphur phosphorus, omethoate, dioxathion, Ethodan, methacrifos, Phosalone, methylpyrimidine sulphur phosphorus, quinalphos,
Kilval, propetamphos, dialifos, phosmet, acrinathrin, Biphenthrin, lambda-cyhalothrin, smart efficient cyhalothrin
Ester, Fenpropathrin, flucythrinate, flumethrin, taufluvalinate, brofluthrinate, Bifenazate, fenothiocarb, butocarboxim,
Talcord, thiofanox, benomyl, sok, carbosulfan, MTMC, promacyl, Carzol, single carbonamidine, medimeform,
Amitraz, Ergol, fenisobromolate, cyflumetofen, acequinocyl, Nissol, flufenoxuron, macro tetrolide, piericidin, Su Yun
Jin Su, tetranactin, avermectin, doractin, eprinomectin, ivermectin, selamectin, moxidectin, Dalmatian chrysanthemum
Element, nicotine, matrine, nimbin, rotenone, tebufenpyrad, pyridaben, fenpyroximate, clofentezine, propargite, Hexythiazox, spiral shell mite
Ester, fluacrypyrim, chlorfenizon, propargite, pyridaben；Fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate exist
Total mass percentage in the miticide composition is 1%-90%, the solid or liquid adjuvants of 99% to 10% weight,
And the surfactant of optional 0 to 50% weight, fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention and its intermediate with
The acaricidal ratio of commodity is mass percent 1%: 99% to 99%: 1%；The dosage form choosing of the miticide composition processing
From: seed treatment emulsion, aqueous emulsion, big granula, microemulsion, water-soluble granule, soluble thick agent, water-dispersible granules, poison grain,
Aerosol, blocky poison bait, sustained-release block, dense poison bait, CG/Encapsulated granule, micro-capsule suspension, Waterless Seed Dressing pulvis, missible oil, electrostatic spray
Agent, water-in-oil emulsion, oil in water emulsion, smoke candle, granula subtilis, smoke candle, smoke cartridge, smog stick, seed treatment suspending agent, cigarette
Mist piece, smog ball, granular poison bait, thermal fog, medicine paint, fine granule, oil suspending agent, oil-dispersing property pulvis, sheet poison bait, dense jelly,
It sprinkles and pours agent, seed coat agent, liniment, suspended emulsion, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume
Suspending agent, tracking pulvis, ultra low volume liquids, any one in wet-mixing kind water-dispersible powder；The miticide composition is anti-
The mite evil controlled is selected from: mite evil is selected from the harmful mite of Tetranychidae, Tenuipalpidae, furan line mite, Eriophyidae, tetranychus telarius category, Eriophyidae, these
Harmful mite is worldwide Agricultural Mites, forestry harmful mites, gardening harmful mite and hygienic harmful mite；Plant of the miticide composition for prevention and treatment
It is selected from: paddy, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, garden pea, semen viciae fabae, pea, green
Beans, red bean, cotton, silkworm and mulberry, peanut, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil
Palm fibre, sisal hemp, tobacco, tomato, capsicum, radish, cucumber, Chinese cabbage, celery, hot pickled mustard tuber, rape, green onion, garlic, watermelon, muskmelon, Hami
Melon, pawpaw, apple, citrus, peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
The chemical structure and physical and chemical parameter of the fluorine-containing substituted pyrazolecarboxylic aminated compounds III of the invention of table 1. and its intermediate
Bacteriostatic activity (50 micrograms/milli of the fluorine-containing substituted pyrazolecarboxylic aminated compounds III of connection of the invention of table 2. and its intermediate
Inhibiting rate/the % risen)
| Serial number | Compound number | AS | BC | CA | GZ | PI | PP | PS | RC | SS |
| 1 | ydy02-8 | 33 | 46 | 43 | 37 | 8 | 30 | 20 | 36 | 7 |
| 2 | ydy02-9 | 36 | 37 | 63 | 33 | 8 | 15 | 17 | 38 | 4 |
| 3 | ydy02-36 | 23 | 49 | 0 | 28 | 5 | 7 | 12 | 24 | 7 |
| 4 | ydy02-37 | 31 | 42 | 0 | 33 | 15 | 24 | 17 | 38 | 4 |
| 5 | Boscalid | 90 | 95 | 53 | 57 | 23 | 58 | 22 | 35 | 100 |
| 6 | Fluxapyroxad | 95 | 100 | 50 | 67 | 54 | 82 | 54 | 86 | 100 |
AS: tomato early blight bacterium, latin name are as follows: Alternaria solani, BC: botrytis cinerea pers, latin name
Are as follows: Botrytis cinerea, CA: peanut Cercospora bacteria, latin name are as follows: Cercospora arachidicola, GZ: small
Wheat gibberellic hypha, latin name are as follows: Gibberella zeae, PI: phytophthora infestans, latin name are as follows:
Phytophthora infestans (Mont.) de Bary, PP: Botryosphaeria berengeriana f. sp, latin name are as follows: Physalospora
Piricola, PS: Rhizoctonia solani Kuhn, latin name are as follows: Pellicularia sasakii, RC: Rhizoctonia cerealis, Latin
Name are as follows: Rhizoctonia cerealis, SS: Sclerotinia sclerotiorum, latin name are as follows: Sclerotinia
sclerotiorum。
Claims (10)
1. fluorine substituted pyrazolecarboxylic amine derivant, it is characterised in that: have the general structure as shown in formula III:
Wherein:
R1It is selected from: C1-C6Fluoro-alkyl, C1-C6Fluoroalkyl, C2-C6Fluoro alkenyl, C2-C6Fluoro alkynyl.
2. fluorine-containing substituted pyrazolecarboxylic aminated compounds III, R according to claim 11It preferably is selected from: trifluoromethyl, difluoromethyl.
3. according to claim 1 with the specific synthetic route of fluorine-containing substituted pyrazolecarboxylic amine derivant III and side described in claim 2
Method are as follows:
The definition of the substituent group is as described in claim 1, and the definition of preferred substituents is as claimed in claim 2；Specific synthesis
Method is divided into following steps:
A. the preparation of intermediate II:
Reaction preparation is stirred at room temperature in DPEA and solvent tertiary butanol by starting material I and DPPA in intermediate II, wherein starting is former
Expect that the definition of I and the substituent group in intermediate II is as described in claim 1, the definition of preferred substituents is as claimed in claim 2；
B. the preparation of fluorine-containing substituted pyrazolecarboxylic amine III:
Reaction preparation is stirred at room temperature by intermediate II and trifluoroacetic acid in fluorine-containing substituted pyrazolecarboxylic amine III, wherein intermediate II and mesh
The definition for marking the substituent group in the fluorine-containing substituted pyrazolecarboxylic amine III of product is as described in claim 1, the definition of preferred substituents such as right
It is required that described in 2.
4. claim 1 and fluorine-containing substituted pyrazolecarboxylic amine derivant III as claimed in claim 2 and its intermediate prepare it is agricultural
Purposes in fungicide.
5. a kind of composition pesticide, it includes power claim 1 and fluorine-containing substituted pyrazolecarboxylic amine derivants as claimed in claim 2
III and its intermediate can prepare composition pesticide, and the composition includes claim 1 and as claimed in claim 2 fluorine-containing takes
For pyrazoles amine derivant III and its intermediate as active constituent, the content of active constituent is 0.1% to 99.9% weight,
The surfactant of the solid or liquid adjuvants of 99.9% to 0.1% weight and optional 0 to 50% weight.
6. a kind of pesticide complex composition, it includes claim 1 and fluorine-containing substituted pyrazolecarboxylic amine as claimed in claim 2 are derivative
Object III and its intermediate can prepare pesticide complex composition, which includes claim 1 and claim 2 institute
As active constituent, active constituent contains the fluorine-containing substituted pyrazolecarboxylic amine derivant III and its intermediate and commercially available agricultural chemical stated
Amount is 0.1% to 99.9% weight, the solid or liquid adjuvants of 99.9% to 0.1% weight and optional 0 to 50% weight
Surfactant.
7. a kind of agricultural bactericidal composition, it includes claim 1 and fluorine-containing substituted pyrazolecarboxylic amine as claimed in claim 2 are derivative
Object III and intermediate can prepare agricultural bactericidal composition, and the composition includes claim 1 and as claimed in claim 2 contains
As active constituent, the content of active constituent is 0.1% to 99.9% weight for fluorine substituted pyrazolecarboxylic amine derivant III and its intermediate
Amount, the surfactant of the solid or liquid adjuvants of 99.9% to 0.1% weight and optional 0 to 50% weight.
8. a kind of agricultural bactericidal complex composition, it includes claims 1 and fluorine-containing substituted pyrazolecarboxylic amine as claimed in claim 2
Derivative III and its intermediate and other it is bactericide compounded be used as active constituent, fluorine-containing substituted pyrazolecarboxylic amine derivant III and its
The ratio of intermediate and other fungicide is mass percent 1%: 99% to 99%: 1%, and the content of active constituent arrives for 1%
99% weight, the solid or liquid adjuvants of 99% to 1% weight.
9. a kind of agricultural insecticidal, mite killing complex composition, it includes claims 1 and fluorine-containing substitution pyrrole as claimed in claim 2
Azoles amine derivant III and its intermediate and other Insecticidal and acaricidal agents compounding are used as active constituent, and fluorine-containing substituted pyrazolecarboxylic amine spreads out
Biological III and its intermediate and other worms, acaricidal ratio are mass percent 1%: 99% to 99%: 1%, active constituent
Content be 1% to 99% weight, the solid or liquid adjuvants of 99% to 1% weight.
10. a kind of anti-plant virus agent complex composition, it includes claims 1 and fluorine-containing substitution pyrrole as claimed in claim 2
Azoles amine derivant III and its intermediate and other anti-plant virus agents compounding are used as active constituent, fluorine-containing substituted pyrazolecarboxylic amine
The ratio of derivative III and its intermediate and other anti-plant virus agents is mass percent 1%: 99% to 99%: 1%, living
Property ingredient content be 1% to 99% weight, the solid or liquid adjuvants of 99% to 1% weight.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005090313A1 (en) * | 2004-03-18 | 2005-09-29 | Pfizer Limited | N-(1-arylpyrazol-4l)sulfonamides and their use as parasiticides |
| WO2016144849A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Thienopyrazine inhibitors of irak4 activity |
| WO2016144846A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidine inhibitors of irak4 activity |
| WO2016144847A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrrolopyridazine inhibitors of irak4 activity |
| WO2016144848A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrrolotriazine inhibitors of irak4 activity |
| CN105980362A (en) * | 2014-01-10 | 2016-09-28 | 旭硝子株式会社 | Ethereal oxygen-containing perfluoroalkyl group-substituted pyrazole compound and production method therefor |
| WO2017019804A2 (en) * | 2015-07-28 | 2017-02-02 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
-
2019
- 2019-05-17 CN CN201910422285.0A patent/CN110041259A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005090313A1 (en) * | 2004-03-18 | 2005-09-29 | Pfizer Limited | N-(1-arylpyrazol-4l)sulfonamides and their use as parasiticides |
| CN105980362A (en) * | 2014-01-10 | 2016-09-28 | 旭硝子株式会社 | Ethereal oxygen-containing perfluoroalkyl group-substituted pyrazole compound and production method therefor |
| WO2016144849A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Thienopyrazine inhibitors of irak4 activity |
| WO2016144846A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidine inhibitors of irak4 activity |
| WO2016144847A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrrolopyridazine inhibitors of irak4 activity |
| WO2016144848A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrrolotriazine inhibitors of irak4 activity |
| WO2017019804A2 (en) * | 2015-07-28 | 2017-02-02 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
Non-Patent Citations (1)
| Title |
|---|
| JONGWON LIM，等: "Discovery of 5‑Amino‑N‑(1H‑pyrazol-4-yl)pyrazolo[1,5‑a]pyrimidine-3-carboxamide Inhibitors of IRAK4", 《ACS MED. CHEM. LETT.》 * |
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