CN110041260A - A kind of multi-substituted pyrazol amide derivatives and its preparation method and application - Google Patents
A kind of multi-substituted pyrazol amide derivatives and its preparation method and application Download PDFInfo
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- 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
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- 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
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Abstract
The present invention provides a kind of multi-substituted pyrazol amide derivatives and its preparation method and application, and the present invention relates to a kind of multi-substituted pyrazol amide derivatives, general formula of the chemical structure is shown in formula IV:
Description
Technical field
Technical solution of the present invention is related to multi-substituted pyrazol amides compound, and in particular to 1- aryl -3- difluoromethyl
Pyrazole amide and 1- aryl -3- trifluoromethyl pyrazol amide derivatives.
Background technique
Multi-substituted pyrazol structural unit skeleton shows good chemical characteristic and potential bioactivity, in pharmaceutical chemistry
Field occupies an important position.Chemistry of pesticide researcher constantly carries out research and probe, power to multi-substituted pyrazol Hete rocyclic derivatives
It asks and is found to have efficient, less toxic, wide spectrum biological activity pesticide species.Multi-substituted pyrazol is present in multiple insecticide varieties
In, wherein Fipronil have efficient insecticidal activity, in various crop Lepidoptera and coleopteran pest it is effective, (Li Min,
Equal, pesticide science and management, 2014,35 (6): 4-6) but since its safety issue has partially been disabled.
Pyrrazole structure widely exists in multiple fungicide kinds, and (Liang Ying waits, pesticide, 2005 (11): 491-495) is outstanding
It is succinate dehydrogenase inhibitors fungicide kind.The succinate dehydrogenase inhibitors class sterilization to put goods on the market in nearly 20 years
There are about 70% or more in agent kind all to contain a pyrazole heterocycle.Existing pyrazole amide targeting compounds mitochondria reported in the literature
Respiratory Chain Complex I I is also known as succinate dehydrogenase (Du Shijie waits, Pesticide Science journal, 2018 (5): 545-556), is a kind of
The fungicide of wide spectrum.Fungicide containing pyrazole heterocycle is various in style, has excellent bactericidal activity.Methoxy acrylic
Wherein pyraclostrobin in fungicide, (Zhang Kai waits, modern, 2018 (2): 8-11) is to the pathogenic in various crop
The disease that bacterium generates, such as melon and fruit powdery mildew, downy mildew, anthracnose, leaf spot, scab, spike rot, brown spot disease have
Preferable preventive effect, the medical instrument have the features such as dosage is few, and good drug efficacy, effect is fast, environmentally friendly.
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 design feature of the comprehensive existing fungicide containing pyrazol framework introduces pyrazolyl in pesticide molecule design
Group, the multifarious pyrazole amide derivatives of construction structure improve the bactericidal activity of target molecule, and novel to research and development have
The fungicide of broad-spectrum disease resistance has 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
Medicine lead compound, the present invention have synthesized multi-substituted pyrazol structure and the same MOLECULE DESIGN of pyrazole group introducing a kind of polysubstituted
Pyrazole amide derivatives, while the screening and evaluation of the bioactivity of system have been carried out, to find more high activities, low resistance
Risk and the high environment friendly agricultural candidate variety of Environmental compatibility.
Summary of the invention
The technical problems to be solved by the present invention are: providing the synthetic method of a kind of multi-substituted pyrazol amide derivatives, mention
For this kind of compound modulates agricultural, the bioactivity and its measuring method of gardening and health and forestry plant pathogen, simultaneously
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 a kind of multi-substituted pyrazol amide derivatives of bactericidal activity is shown in formula IV:
R1、R2、R3、R4、R5、R6It is selected from: hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy, C1-C6Haloalkoxy
Base, C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, hydroxyl, C3-C6Naphthenic base, substituted piperazine
The phenyl or C that pyridine -1- base, substituted morpholine -1- base, substituted nafoxidine -1- base, phenyl or halogen replace1-C6
Alkyl-substituted phenyl or C1-C6The phenyl or C that halogenated alkyl replaces3-C6The benzene that the phenyl or nitro that naphthenic base replaces replace
Base or C2-C6The phenyl or C that alkenyl replaces2-C6The phenyl or C that halogenated alkenyl replaces3-C6Cycloalkenyl replace phenyl or
C2-C6The phenyl or C of alkynyl substituted2-C6The phenyl or C that halo alkynyl replaces3-C6Phenyl, pyridyl group or the halogen that cycloalkynyl radical replaces
The pyridyl group or C that element replaces1-C6Alkyl-substituted pyridyl group or C1-C6The pyridyl group or C that halogenated alkyl replaces3-C6Cycloalkanes
The pyridyl group or C that the pyridyl group or nitro that base replaces replace2-C6The pyridyl group or C that alkenyl replaces2-C6Halogenated alkenyl replaces
Pyridyl group or C3-C6The pyridyl group or C that cycloalkenyl replaces2-C6The pyridyl group or C of alkynyl substituted2-C6What halo alkynyl replaced
Pyridyl group or C3-C6The pyrimidine radicals or C that pyridyl group, pyrimidine radicals or the halogen that cycloalkynyl radical replaces replace1-C6It is alkyl-substituted phonetic
Piperidinyl or C1-C6The pyrimidine radicals or C that halogenated alkyl replaces3-C6The pyrimidine radicals for pyrimidine radicals or the nitro substitution that naphthenic base replaces,
Or C2-C6The pyrimidine radicals or C that alkenyl replaces2-C6The pyrimidine radicals or C that halogenated alkenyl replaces3-C6The pyrimidine radicals of cycloalkenyl substitution,
Or C2-C6The pyrimidine radicals or C of alkynyl substituted2-C6The pyrimidine radicals or C that halo alkynyl replaces3-C6Pyrimidine radicals, the quilt of cycloalkynyl radical substitution
Five yuan or the six membered heteroaryl, substituted five yuan or hexa-atomic miscellaneous containing 1 or 2 S atom containing 1 or 2 N atom replaced
It is aryl, substituted five yuan containing 1 or 2 O atom or six membered heteroaryl, substituted containing 1 N atom and 1 S atom
Five yuan or six membered heteroaryl, substituted five yuan containing 1 N atom and 1 O atom or six membered heteroaryl contain 2 N atoms and 1
Substituted five yuan of a S atom or six membered heteroaryl, substituted five yuan or hexa-atomic miscellaneous containing 2 N atoms and 1 O atom
Aryl；Above-mentioned five yuan or six membered heteroaryl are selected from: substituted furyl, thienyl, pyrrole radicals, imidazole radicals, pyrazolyl, thiazole
Base, isothiazolyl, oxazolyl, isoxazolyl, oxadiazoles base, thiadiazolyl group, pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, three
Piperazine base, tetrazine base, indyl, benzothienyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazole base, benzo thiophene
Oxazolyl, diazosulfide base, benzoxazolyl, the quinolyl of isomerization, the isoquinolyl of isomerization, phthalazinyl, quinoxalinyl,
The silicon substrate that quinazolyl, cinnoline base or naphthyridines base, alkyl or alkenyl replace.
R1It preferably is selected from: trifluoromethyl, difluoromethyl, chlorine；R2It preferably is selected from: hydrogen, trifluoromethyl；R3It preferably is selected from: trifluoromethyl,
Hydrogen, fluorine, chlorine, bromine；R4It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine；R5It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine；R6It is preferred that
From: trifluoromethyl, hydrogen, fluorine, chlorine, bromine.
Halogen is fluorine, chlorine, bromine or iodine in above-mentioned definition；
The alkyl, alkenyl or alkynyl are straight chain or branch alkyl；Alkyl itself or portion as other substituent groups
It is selected from methyl, ethyl, propyl, butyl, amyl, hexyl and its isomers, isomers is selected from isopropyl, isobutyl group, Zhong Ding
Base, tert-butyl, isopentyl or tertiary pentyl；
The halogenated alkyl group is selected from the group containing one or more identical or different halogen atoms, the alkyl halide
Base is selected from CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CF3CH2、CH3CF2、CF3CF2Or CCl3CCl2；
Described naphthenic base itself or as other substituent groups part be selected from cyclopropyl, cyclobutyl, cyclopenta or cyclohexyl；
Described alkenyl itself or as other substituent groups part be selected from vinyl, allyl, 1- acrylic, butene-2-
Base, butylene -3- base, amylene -1- base, amylene -3- base, hexene -1- base or 4- methyl-3-pentenyl；
Described alkynyl itself or as other substituent groups part be selected from acetenyl, propine -1- base, propine -2- base, fourth
Alkynes -1- base, crotonylene-base, 1- methyl -2- butynyl, hexin -1- base or 1- ethyl -2- butynyl.
The synthetic method of multi-substituted pyrazol amide derivatives of the invention is as follows:
Wherein, substituent R1、R2、R3、R4、R5、R6It is defined as described above；R1It preferably is selected from: trifluoromethyl, difluoromethyl, chlorine；
R2It preferably is selected from: hydrogen, trifluoromethyl；R3It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine；R4Preferably be selected from: trifluoromethyl, hydrogen, fluorine, chlorine,
Bromine；R5It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine；R6It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine.
The synthesis of multi-substituted pyrazol amide derivatives and the specific method of biological activity determination of the invention is divided into following
Step:
A. the preparation of compound II:
3 mMs of compound I are first added in 100 milliliters of reaction round-bottomed flasks, methylene chloride solution, ice water is added
Bath, temperature are down to zero degree, and n,N-Dimethylformamide (DMF) 2 drips, 6 mMs of oxalyl chloride solutions are slowly added dropwise, are added dropwise,
It is slowly increased to room temperature, is stirred at room temperature 2 hours；After contact plate monitors fully reacting, first it is concentrated under reduced pressure, it is molten removes extra oxalyl chloride
Liquid and methylene chloride.It is spare to obtain crude product II.Compound II preparation amount and reaction vessel volume by corresponding proportion expand or
It reduces.
B. the preparation of compound IV:
3 mMs of compound III are added in 100 milliliters of round-bottomed flasks, methylene chloride solution and acid binding agent is added
Triethylamine, ice bath are cooled to zero degree, and crude product II is dissolved with dichloro, is added drop-wise in reaction solution, after stirring two hours, contact plate prison
After surveying fully reacting, water is added, is repeatedly extracted with dichloromethane solution, merges organic layer dichloromethane layer, use saturated sodium-chloride
Organic layer is washed, anhydrous sodium sulfate is dry, filters, solvent is removed under reduced pressure, and residue is purified 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 6: 1-2: 1 is obtained white
Color solid chemical compound IV, yield 62-95%.The amount of compound IV preparation and the volume of reaction vessel are expanded or are contracted by corresponding proportion
It is small.
C. the measurement of multi-substituted pyrazol amide derivatives IV bactericidal activity of the invention:
The sterilization of multi-substituted pyrazol amide derivatives IV of the invention or bacteriostatic activity are measured using thalli growth rate method, tool
Body step are as follows: take 1.8 milligrams of samples to be dissolved in 2 drop n,N-Dimethylformamide, then emulsified with containing a certain amount of polysorbas20
The aqueous solution of agent is diluted to the medicament of 500 mcg/mls, and reagent agent is aseptically respectively drawn to 1 milliliter in culture dish
It is interior, then 9 milliliters of PDA culture mediums are separately added into, 50 mcg/ml drug containing tablets are made after shaking up, to add 1 milliliter of aqua sterilisa
Plate does blank control, cuts bacterium disk along mycelia outer rim with 4 millimeters of diameter of punch, moves in drug containing tablet, is in equilateral three
Angular to put, every processing is repeated 3 times, and culture dish is placed on culture, colony diameter to be compareed in 24 ± 1 degrees Celsius of constant incubators
Each processing bacterium disk extension diameter is investigated after being extended to more than 2 centimetres, is averaged, and is calculated compared with blank control relatively antibacterial
Rate is the kind of most of typical plant pathogen that field actually occurs in China's agricultural production for examination strain, code name and
Title is 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, GZ: fusarium graminearum, latin name are as follows: Gibberella zeae, PI: potato evening
Epidemic disease bacterium, 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。
The beneficial effects of the present invention are: having carried out guide's optimization to multi-substituted pyrazol amide derivatives IV, and to polysubstituted
Pyrazole amide derivatives IV has carried out the screening of bacteriostatic activity.
The present invention is by specific preparation and biological activity determination embodiment is more specific illustrates multi-substituted pyrazol amide derivative
The synthesis of object IV and bioactivity and application, the embodiment, which is only used for illustrating the present invention, to be not intended to limit the present invention, especially
It is that bioactivity is merely illustrative of, rather than limits this patent, specific embodiment is as follows:
Embodiment 1: the preparation of compound II-1:
3 mMs of multi-substituted pyrazol acid I-1 is added in 100 milliliters of single necked round bottom flask, 30 milliliters of dichloromethanes are added
Alkane solution, ice-water bath, temperature are down to zero degree, and n,N-Dimethylformamide two is dripped, and 6 mMs of oxalyl chloride solutions are slowly added dropwise, and drip
It adds complete, is slowly increased to room temperature, is stirred at room temperature 2 hours；After contact plate monitors fully reacting, first it is concentrated under reduced pressure, it is extra to remove
Oxalyl chloride solution and methylene chloride.It is spare to obtain crude product II-1.The amount of compound II-1 preparation and the volume of reaction vessel press phase
Ratio is answered to expand or shrink.
Embodiment 2: the preparation of compound IV-1:
3 mMs of compound III-1 are added in 100 milliliters of single necked round bottom flask, with 30 milliliters of dry methylene chloride
6 mMs of triethylamine is added into reaction for dissolution, after adding, ice bath stirring 10 minutes, then dripped into reaction system
3 mMs of compound II-1 with 5 milliliters of dry methylene chloride dissolutions are added；Ice bath stirring 30 minutes, rear chamber after adding
15 milliliters of water is added in temperature stirring 4 hours, after reaction, reaction solution, and methylene chloride extracts three times, isolates organic layer, have
Machine layer is washed one time with saturated sodium-chloride, and anhydrous sodium sulfate is dry, is filtered, solvent is removed under reduced pressure, residue is through 100~200 mesh silicon
It is gel column chromatography eluting to obtain compound IV, the petroleum ether that eluant, eluent is 60~90 degrees Celsius: ethyl acetate, volume ratio 4: 1,
Yield 75%；The compound1H NMR (400MHz, CDCl3): δ 8.32 (s, 1H), 8.27 (s, 1H), 7.54 (t, J=
6.6Hz, 4H), 6.77 (t, J=54.4Hz, 1H), 3.91 (s, 3H).The physical and chemical parameter and structural parameters of compound IV is shown in Table 1.
Embodiment 3: the bactericidal activity measurement result of multi-substituted pyrazol amide derivatives IV of the invention:
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, GZ: gibberella saubinetii
Germ, 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.These
Strain represents the kind for most of pathogen that field occurs in agricultural production.
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.Chemical combination is shown to the Activity Results of tomato early blight bacterium
Object shows certain bacteriostatic activity, and wherein ydy02-70 relative performance is excellent, bacteriostatic activity 72%.To gray mold of cucumber
The active testing of bacterium shows that compound ydy02-95, ydy02-100, ydy02-107, ydy02-108, ydy02-114's is antibacterial
Activity is 90% or more, activity and acid amide fungicides Boscalid (inhibiting rate to botrytis cinerea pers is 95%) and fluorine azoles
Bacterium amide (inhibiting rate to gray mold of cucumber germ is 98%) is quite.Chemical combination is shown to the active testing of fusarium graminearum
Object ydy02-68, ydy02-69, ydy02-70, ydy02-99, ydy02-101 bacteriostatic activity are 70% or more, above compound
Bactericidal activity be higher by commercialization acid amide fungicides activity Boscalid (being 53% to the inhibiting rate of fusarium graminearum) and exist
17% or more and fluxapyroxad (being 65% to the inhibiting rate of fusarium graminearum) 5% or more.Phytophthora infestans
Active testing the result shows that, the bacteriostatic activity of compound ydy02-70, ydy02-99, ydy02-110 is 50% or more, activity
Acid amide fungicides Boscalid (inhibiting rate of Phytophthora infestans is 39%) is higher by 10% or more, with fluorine azoles bacterium acyl
Amine (inhibiting rate of Phytophthora infestans is 63%) is quite.To the active testing of Botryosphaeria berengeriana f. sp show ydy02-65,
For the bacteriostatic activity of ydy02-70, ydy02-102, ydy02-110 70% or more, activity is higher than acid amide fungicides Boscalid
(being 61% to the inhibiting rate of Botryosphaeria berengeriana f. sp) nearly 10%, with fluxapyroxad (to the inhibiting rate of Botryosphaeria berengeriana f. sp,
76%) substantially quite.Ydy02-70, ydy02-94, ydy02-95, ydy02- are shown to the active testing of Rhizoctonia solani Kuhn
99, for the bacteriostatic activity of ydy02-100, ydy02-101, ydy02-104, ydy02-110 50% or more, activity is higher than amides
Fungicide Boscalid (inhibiting rate to Rhizoctonia solani Kuhn is 43%).Chemical combination is shown to the active testing of Rhizoctonia cerealis
Object ydy02-69, ydy02-70, ydy02-94, ydy02-95, ydy02-99, ydy02-100, ydy02-101, ydy02-102,
For the bacteriostatic activity of ydy02-110 90% or more, activity is higher than the (inhibition to Rhizoctonia cerealis of acid amide fungicides Boscalid
Rate be 29%) 60% or more, quite with fluxapyroxad (inhibiting rate to Rhizoctonia cerealis is 92%), above compound its
Middle ydy02-69, ydy02-70, ydy02-99, ydy02-100 reach 100% to the inhibiting rate of Rhizoctonia cerealis.To Sclerotina Sclerotiorum in Winter Rape
The active testing of core germ show compound ydy02-65, ydy02-70, ydy02-93, ydy02-95, ydy02-100,
The bacteriostatic activity of ydy02-107, ydy02-108, ydy02-109, ydy02-110 90% or more, sterilize with amides by activity
(inhibiting rate to Sclerotinia sclerotiorum is for agent Boscalid (being 88% to the inhibiting rate of Sclerotinia sclerotiorum) and fluxapyroxad
95%) quite.
Embodiment 4: multi-substituted pyrazol amide derivatives IV of the invention is preparing the application in composition pesticide:
Multi-substituted pyrazol amide derivatives IV of the invention and its intermediate can prepare composition pesticide, the composition packet
Containing multi-substituted pyrazol amide derivatives IV and its intermediate of the invention as active constituent, the content of active constituent is 0.1%
To 99.9% weight, the surface-active of the solid or liquid adjuvants of 99.9% to 0.1% weight and optional 0 to 50% weight
Agent.
Embodiment 5: the application of multi-substituted pyrazol amide derivatives IV of the invention in preparation pesticide complex composition:
Multi-substituted pyrazol amide derivatives IV of the invention and its intermediate can with other commercially available agricultural chemicals, i.e., insecticide,
Acaricide, fungicide, antivirotic or activating plants agent compounding preparation pesticide complex composition, which includes this hair
Bright multi-substituted pyrazol amide derivatives IV and its intermediate and other commercially available agricultural chemicals, i.e. insecticide, fungicide, resist acaricide
Viral agent or activating plants agent are as active constituent, multi-substituted pyrazol amide derivatives IV of the invention and its intermediate and other
Commercially available agricultural chemical, i.e. insecticide, acaricide, fungicide, antivirotic or activating plants agent ratio be mass percent 1%:
99% to 99%: 1%, the content of active constituent is 0.1% to 99.9% weight, the solid or liquid of 99.9% to 0.1% weight
The surfactant of body auxiliary agent and optional 0 to 50% weight.
Embodiment 6: multi-substituted pyrazol amide derivatives IV and insecticide composition of the invention prevention and treatment agricultural and forestry with
And the application in gardening plant insect pest:
All multi-substituted pyrazol amide derivatives IV of the invention are combined with any one or two kinds in commodity insecticide
It forms Pesticidal combination and is selected from for preventing and treating agricultural and forestry and gardening plant insect pest, the commodity insecticide: ground Asia Nong, pyridine
Worm amidine, emamectin benzoate, milbemectin, avermectin, pleocidin, cypermethrin, effective cypermethrin, three cyfluthrins
Pyrethroids, decis, Fenpropathrin, Beta- cyfloxylate, Lambda- Cyhalothrin, permethrin, benzyl chloride
Pyrethroids, allethrin, Biphenthrin, Permethrin, ethofenprox, flumethrin, fluvalinate, imidacloprid, alkene pyridine worm
Amine, imidaclothiz, thiacloprid, Diacloden, clothianidin, dinotefuran, clothianadin, Da Tenan, diflubenzuron, d ichlorbenzuron, Teflubenzuron, deinsectization
Grand, flubenzuron, flufenoxuron, pyridine worm be grand, lufenuron, poisonous insect urea, penfluron, flucycloxuron, chlorfluazuron, piperazine worm urea, furan tebufenozide,
Tebufenozide, chlorine tebufenozide, methoxyfenozide, ring tebufenozide, flolimat, DDVP, quinalphos, pyridaphethione, isoprocarb, west
Denapon, Aphox, MTMC, Mobucin, cartap, Bassa, leaf disperse, carbaryl, Benfuracard micro, 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, Flubendiamide, fluorine cyanogen insect amide,
Cyanogen insect amide, Tolfenpyrad, chlorfenapyr, pyrazinones, etoxazole, tebufenpyrad, rattle away young ketone, Nylar, emaricin；Of the invention
Mass percentage of the multi-substituted pyrazol amide derivatives IV in the Pesticidal combination is 1%-90%, 99% to 10% weight
The surfactant of the solid or liquid adjuvants of amount and optional 0 to 50% weight, multi-substituted pyrazol amide derivative of the invention
The ratio of object IV and aforementioned commodity insecticide is mass percent 1%: 99% to 99%: 1%；The Pesticidal combination processing
Dosage form is selected from: seed treatment emulsion, aqueous emulsion, big granula, microemulsion, water-soluble granule, soluble thick agent, water dispersible grain
Agent, 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 pulvis, sheet poison
Bait, dense jelly sprinkle and pour agent, seed coat agent, liniment, suspended emulsion, film forming finish, soluble powder, seed treatment water soluble powder
Agent, ultra-low volume suspending agent, tracking pulvis, ultra low volume liquids, any one in wet-mixing kind water-dispersible powder；It is described to kill
The insect pest of the plant of worm composition for preventing and controlling is selected from: red spider, Asiatic migrotory locust, reading room management, Chinese rice grasshopper, Patanga japonica (l.Bol.), single thorn
It is mole cricket, Oriental burmeister, rice thrips, onion thrips, greenhouse thrips, haplothrips aculeatus, Mai Jianguan thrips, Trialeurodes vaporariorum Westwood, Bemisia tabaci, black
Caudal lobe cicada, green leaf hopper, chlorita biguttula, spot clothing plant hopper, brown paddy plant hopper, white backed planthopper, small brown rice planthopper, the flat angle plant hopper of sugarcane, cotten aphid, wheat two
Pitch aphid, 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 stinkbug, Orius minutus, slender rice bug, paddy fly, niphe elongata, scotinophora lurida, rice
Acrosternumhilare, green plant bug, alfalfa plant bug, black striped plant bug, chrysopa septempunctata, beautiful Chrysopa, Chinese green lacewing, rain moth, casemaking clothes moth, oriental moth, brown slug moth,
It is thosea siensis, gelechiid, pink bollworm, brachmia triannuella, diamondback moth, small heart-eating peach worm, eating-core bean worm, apple Spilonota lechriaspis, brown
Belt length leaf roller, Adoxophyes cyrtosema, striped rice borer, bean-pod borer, corn borer, yellow rice borer, Oeobia undalis, rice leaf roller, snout moth's larva, cotton roll
Leaf open country snout moth's larva, dichocrocis punctiferalis, armyworm, prodenia litura, rice green caterpillar, anomis flava, beet armyworm, pink rice borer, bollworm, ancient cooking vessel point Buddha's warrior attendant
Brill, big cutworm, yellow cutworm, steals poison moth, gypsymoth, palaearctic sweet potato, greenish brown hawk moth, straight grain rice hesperiidae, laid paddy at black cutworm
Hesperid, Papilio xuthus, Common Mormon, cabbage butterfly, pyrameis indica, a ramie Huang a kind of butterfly harmful to crop plants, beans blister beetle, Venus ground beetle, wrinkle sheath ground beetle,
The small buprestid beetle of wheat head ground beetle, pleonomus canaliculatus, Agriotes subrittatus Motschulsky, khapra beetle, attagenus piceus, citrus, golden edge buprestid beetle, yellow meal worm,
Dark mealworm, red flour beetle, confused flour beetle, verdigris different beetle, H. parallela, holotrichia oblita, mulberry borer, longicorn beetle,
Nadezhdiella cantori, pink neck longicorn, big daikon leaf beetle, daicon leaf beetle, 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, a bollworm tooth lip Ji
Bee, snout moth's larva stain wart ichneumon wasp, mosquito, horsefly, wheat midge, contarinia tritici, citrus fruit fly, melonfly, wheat leaf ash latent fly, America
Liriomyza bryoniae, Soybean stem borer, frit fly, Hylemyia Platura Meigen, onion fly, radish fly, full skirt Exorista civilis, corn borer is strict posts fly；The desinsection group
The plant of Researches On Hydrate Prevention is selected from: paddy, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, Holland
Beans, semen viciae fabae, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, rape, sesame, sunflower, beet, sugarcane, coffee, cocoa, people
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, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya,
Orchid, potted landscape.
Embodiment 7: multi-substituted pyrazol amide derivatives IV and antimicrobial combination of the invention prevention and treatment agricultural and forestry with
And the application in gardening plant disease:
All multi-substituted pyrazol amide derivatives IV of the invention are combined with any one or two kinds in commodity fungicide
It forms bactericidal composition and is selected from for preventing and treating agricultural and forestry and gardening plant disease, the commodity fungicide: benzo thiophene two
Azoles, tiadinil are abbreviated as TDL, tisocromide, first thiophene and lure amine, 4- methyl-1,2,3- thiadiazoles -5- formic acid, 4- methyl-1, and 2,
3- thiadiazoles -5- sodium formate, 4- methyl-1,2,3- thiadiazoles -5- Ethyl formates, DL- beta-aminobutyric acid, isotianil, English
Literary common name are as follows: isotianil, 3,4-, bis- chloroisothiazole -5- formic acid, 3,4-, bis- chloroisothiazole -5- sodium formate, 3,4- dichloro are different
Thiazole -5- Ethyl formate, virazole, antofine, Ningnanmycin or salicylic acid, cymoxanil, thiram, ziram, Mancozeb,
Aliette, thiophanate-methyl, Bravo, enemy can pine, procymidone, fenpropidin, thiophanate methyl, thiophanate, Metalaxyl-M, fluorine
Quinoline, 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, double alkynes acyls
Bacterium amine, zoxamide, fenfuram, carboxin, chlozolinate, iprodione, Fluoxastrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, benzene
Oxygen bacterium amine, orysastrobin, ZEN 90160, pyraclostrobin, trifloxystrobin, Enestroburin, alkene oxime amine, oxygen ring azoles, bromuconazole, cyclopropyl
Azoles alcohol, difenoconazole, olefin conversion, efficient olefin conversion, epoxiconazole, benzoxazole, Fluquinconazole, Flusilazole, Flutriafol, hexaconazole,
Glyoxalin, kind bacterium azoles, metconazole, nitrile bacterium azoles, penconazole, propiconazole, prothioconazoles, simeconazoles, Tebuconazole, tetraconazole, three
Azoles alcohol, triticonazole, bitertanol, probenazole, furidazol, imazalil, efficient imazalil, Prochloraz, fluorine bacterium azoles, cyazofamid,
Fenamidone dislikes imidazoles, pefurazoate, Famoxate, oxazole, hymexazol, Wakil, Guardian, Grandox fumigant, pungent thiophene
Ketone, benthiozole, dodemorph, butadiene morpholine, tridemorph, fenpiclonil, fludioxonil, fluazinam, pyrifenox, ring pyridine bacterium
Amine, Boscalid, fluopicolide, pyridine bacterium amine, cyprodinil, fluorine mepanipyrim, ferimzone, mepanipyrim, pyrimethanil, chlorobenzene pyrimidine
Alcohol, nuarimol, chinomethionat, dithianon, ethoxyquin, oxyquinoline, the third oxygen quinoline, quinoxyfen, diethofencarb, isopropyl
Bacterium amine, benzene metsulfovax, Propamocarb, methasulfocarb, edifenphos, different rice blast net, pyrazophos, tolelofos-methyl, blasticidin-S, spring thunder are mould
Element, Polyoxin, valida, jinggangmeisu, streptomysin, metalaxyl, furalaxyl, M 9834, ofurace, goes out at polyoxin
Become rusty amine, carbendazim, benomyl, thiophanate-methyl, triazolone, bupirimate, dimethirimol, ethirimol, difoltan, gram bacterium
Pellet, folpet, vinclozolin, fluoromide, dimethachlon, Bravo, Isoprothiolane, kitazine, Yekuzuo, pentachloro- nitro
Benzene, Propineb, phosethyl-Al, sulphur, Bordeaux mixture, copper sulphate, copper oxychloride, cuprous oxide, Kocide SD, metrafenone,
Pencycuron, diclomezin, Rabcide, pyroquilon, volution bacterium amine, tricyclazole, triforine, more fruit pyridines, the pungent salt of biguanides, biguanides are pungent
Amine, botran, benzene flusulfamide, toluene flusulfamide, K-281, fenaminosulf, oxolinic acide, probenazole, bronopol, iodomethane,
Metham-sodium, enemy line ester, dazomet, nemamort, lythidathion, fensulfothion, thionazin, dichlofenthion, fosthietan, oxamyl, sulphur
Acyl fluorides, dichloropropylene, dichloro-isonicotinic acid, allyl isothiazole；Multi-substituted pyrazol amide derivatives IV of the invention is in the sterilization
Total mass percentage in composition is 1%-90%, the solid or liquid adjuvants of 99% to 10% weight and optional 0
To the surfactant of 50% weight, the ratio of multi-substituted pyrazol amide derivatives IV of the invention and aforementioned commodity fungicide is
Mass percent 1%: 99% to 99%: 1%；The dosage form of the bactericidal composition processing is selected from: seed treatment emulsion, water and milk
Agent, 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, medicine paint, fine granule, oil suspending agent, oil-dispersing property pulvis, sheet poison bait, dense jelly, sprinkles and pours agent, seed coat agent, smearing thermal fog
Agent, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume suspending agent, tracking pulvis, surpasses suspended emulsion
Any one in low capacity liquor, wet-mixing kind water-dispersible powder；The plant disease of the bactericidal composition prevention and treatment is selected from: rice
Seedling pythium rot, tomato root rot, the late blight of potato, tobacco black shank, millet powdery mildew, downy mildew of garpe, downy mildew of lettuce,
Cucumber downy mildew, cucumber anthracnose；The applicable plant of the bactericidal composition 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
Fiber crops, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, trailing plants
Fore-telling, cucumber, Chinese cabbage, celery, hot pickled mustard tuber, green onion, garlic, watermelon, muskmelon, "Hami" melon, pawpaw, apple, citrus and peach, tea, hill
Dish, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
Embodiment 8: multi-substituted pyrazol amide derivatives IV of the invention combined with anti-plant virus agent prevention and treatment agricultural and
Application in forestry and gardening plant virus disease:
Any one in all multi-substituted pyrazol amide derivatives IV of the invention and commodity antiviral agent or two kinds
Combination forms antiviral composition for preventing and treating agricultural and forestry and gardening plant virus disease, the commodity antiviral agent
Be selected from: diazosulfide, tiadinil are 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- formic acid second
Ester, 3,4-, bis- chloroisothiazole -5- formic acid, 3,4-, bis- chloroisothiazole -5- sodium formate, 3,4-, bis- chloroisothiazole -5- Ethyl formate,
DL- beta-aminobutyric acid, virazole, antofine, Ningnanmycin, tisocromide, first thiophene lure amine or salicylic acid, cytosintetidemycin, dichloro different
Niacin, allyl isothiazole, well ridge azanol, jinggangmeisu；Multi-substituted pyrazol amide derivatives IV of the invention is described antiviral
Total mass percentage in composition is 1%-90%, the solid or liquid adjuvants of 99% to 10% weight and optional 0
To the surfactant of 50% weight, multi-substituted pyrazol amide derivatives IV of the invention and aforementioned commodity anti-plant virus agent
Ratio is mass percent 1%: 99% to 99%: 1%；The dosage form of the antiviral composition processing is selected from: seed treatment cream
Agent, 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, grain
Shape poison bait, thermal fog, medicine paint, fine granule, oil suspending agent, oil-dispersing property pulvis, sheet poison bait, dense jelly, sprinkle pour agent, seed coat agent,
Liniment, suspended emulsion, film forming finish, soluble powder, seed treatment water solube powder, ultra-low volume suspending agent, tracking powder
Agent, ultra low volume liquids, any one in wet-mixing kind water-dispersible powder；The virus disease of the antiviral composition prevention and treatment
It is selected from: rice dwarf virus disease, yellow dwarf, stripe virus disease, fern leaf of tomato viral disease, Tomato yellow mosaic virus, chilli pepper mosaic virus
Disease, tobacco veinal necrosis virus disease, maize dwarf mosaic, cauliflower mosaic virus, citrus virosis, cymbidium mosaic virus, sword-leaved cymbidium
Ring spot virus；Plant of the antiviral composition for prevention and treatment 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, Xiang
Certain herbaceous plants with big flowers, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, Huang
Melon, Chinese cabbage, celery, hot pickled mustard tuber, green onion, garlic, watermelon, muskmelon, "Hami" melon, pawpaw, apple, citrus and peach, tea, wild vegetables, bamboo
Bamboo shoot, hops, pepper, banana, papaya, orchid, potted landscape.
Embodiment 9: multi-substituted pyrazol amide derivatives IV of the invention combined with acaricide prevention and treatment agricultural and forestry with
And the application in gardening plant mite evil:
All multi-substituted pyrazol amide derivatives IV of the invention are combined with any one or two kinds in commodity acaricide
It forms miticide composition and is selected from for preventing and treating agricultural and forestry and gardening plant mite evil, the commodity acaricide: azacyclotin, three
Ring tin, fenbutatin oxide, three phosphor tins, chlorfenviphos, dimethylvinphos, crotoxyphos, heptenophos, Menite, 2-dichloroethylk dimethyl phosphate, Diothyl, chloromethane
Phosmet, omethoate, dioxathion, Ethodan, methacrifos, Phosalone, methylpyrimidine sulphur phosphorus, quinalphos, Kilval, amine third
Fear, dialifos, phosmet, acrinathrin, Biphenthrin, lambda-cyhalothrin, smart gamma cyhalothrin, first cyanogen chrysanthemum
Ester, flucythrinate, flumethrin, taufluvalinate, brofluthrinate, Bifenazate, fenothiocarb, butocarboxim, Talcord, long
Imitate prestige, benomyl, sok, carbosulfan, MTMC, promacyl, Carzol, single carbonamidine, medimeform, Amitraz, benzene
Benzyl formate, fenisobromolate, cyflumetofen, acequinocyl, Nissol, flufenoxuron, macro tetrolide, piericidin, thuringiensin, mite killing
Element, avermectin, doractin, eprinomectin, ivermectin, selamectin, moxidectin, pyrethrin, nicotine, hardship
Ginseng alkali, rotenone, tebufenpyrad, pyridaben, fenpyroximate, clofentezine, propargite, Hexythiazox, Envidor, fluacrypyrim, kills at nimbin
Mite ester, propargite, pyridaben；The total quality of multi-substituted pyrazol amide derivatives IV of the invention in the miticide composition
Percentage composition is 1%-90%, the surface work of the solid or liquid adjuvants of 99% to 10% weight and optional 0 to 50% weight
Property agent, multi-substituted pyrazol amide derivatives IV of the invention and the acaricidal ratio of the commodity are mass percent 1%: 99%
To 99%: 1%；The dosage form of the miticide composition processing is selected from: seed treatment emulsion, aqueous emulsion, big granula, microemulsion, water
Dissolubility granula, 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, particle
Agent, oil-dispersing property pulvis, sheet poison bait, dense jelly, sprinkles and pours agent, seed coat agent, liniment, suspended emulsion, film forming oil oil suspending agent
Agent, soluble powder, seed treatment water solube powder, ultra-low volume suspending agent, tracking pulvis, ultra low volume liquids, wet-mixing kind
Any one in water-dispersible powder；The mite evil of the miticide composition prevention and treatment is selected from: mite evil is selected from Tetranychidae, false spider mite
Section, furan line mite, Eriophyidae, tetranychus telarius category, Eriophyidae harmful mite, these harmful mites are worldwide Agricultural Mites, forestry harmful mites, gardening
Harmful mite and hygienic harmful mite；Plant of the miticide composition for prevention and treatment is selected from: paddy, wheat, barley, oat, corn, height
Fine strain of millet, sweet potato, potato, cassava, soybean, garden pea, semen viciae fabae, pea, mung bean, red bean, cotton, silkworm and mulberry, peanut, sesame, Xiang
Certain herbaceous plants with big flowers, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, capsicum, radish, Huang
Melon, Chinese cabbage, celery, hot pickled mustard tuber, rape, green onion, garlic, watermelon, muskmelon, "Hami" melon, pawpaw, apple, citrus, peach, tea, hill
Dish, bamboo shoots, hops, pepper, banana, papaya, orchid, potted landscape.
The chemical structure and physical and chemical parameter of the multi-substituted pyrazol amide derivatives IV of the invention of table 1.
The chemical structure and physical and chemical parameter (Continued) of the multi-substituted pyrazol amide derivatives IV of the invention of table 1.
The bacteriostatic activity (inhibiting rate/% of 50 mcg/mls) of the multi-substituted pyrazol amide derivatives IV of the invention of table 2.
| Serial number | Compound number | AS | BC | GZ | PI | PP | PS | RC | SS |
| 1 | ydy02-64 | 33 | 54 | 30 | 21 | 15 | 17 | 48 | 3 |
| 2 | ydy02-65 | 44 | 80 | 43 | 33 | 77 | 34 | 58 | 93 |
| 3 | ydy02-66 | 33 | 56 | 31 | 23 | 18 | 24 | 39 | 24 |
| 4 | ydy02-67 | 51 | 70 | 52 | 38 | 28 | 22 | 61 | 63 |
| 5 | ydy02-68 | 46 | 66 | 76 | 31 | 32 | 24 | 56 | 84 |
| 6 | ydy02-69 | 64 | 88 | 72 | 46 | 48 | 46 | 100 | 89 |
| 7 | ydy02-70 | 72 | 88 | 76 | 54 | 75 | 63 | 100 | 95 |
| 8 | ydy02-93 | 43 | 86 | 47 | 26 | 44 | 43 | 71 | 90 |
| 9 | ydy02-94 | 57 | 77 | 61 | 45 | 49 | 51 | 96 | 76 |
| 10 | ydy02-95 | 59 | 91 | 63 | 42 | 56 | 57 | 96 | 95 |
| 11 | ydy02-96 | 51 | 80 | 53 | 29 | 32 | 49 | 61 | 66 |
| 12 | ydy02-97 | 22 | 50 | 14 | 13 | 2 | 38 | 29 | 32 |
| 13 | ydy02-98 | 49 | 75 | 63 | 39 | 54 | 46 | 82 | 61 |
| 14 | ydy02-99 | 68 | 82 | 73 | 58 | 61 | 65 | 100 | 85 |
| 15 | ydy02-100 | 51 | 91 | 67 | 45 | 54 | 59 | 100 | 95 |
| 16 | ydy02-101 | 59 | 77 | 78 | 47 | 37 | 51 | 98 | 76 |
| 17 | ydy02-102 | 54 | 66 | 65 | 39 | 73 | 49 | 96 | 73 |
| 18 | ydy02-103 | 49 | 73 | 63 | 37 | 63 | 43 | 67 | 71 |
| 19 | ydy02-104 | 54 | 84 | 47 | 45 | 49 | 54 | 43 | 73 |
| 20 | ydy02-107 | 33 | 91 | 41 | 34 | 45 | 29 | 66 | 100 |
| 21 | ydy02-108 | 33 | 94 | 52 | 36 | 23 | 29 | 68 | 100 |
| 22 | ydy02-109 | 41 | 89 | 61 | 40 | 54 | 41 | 75 | 100 |
| 23 | ydy02-110 | 61 | 85 | 55 | 53 | 77 | 61 | 98 | 96 |
| 24 | ydy02-111 | 50 | 89 | 52 | 47 | 54 | 43 | 74 | 85 |
| 25 | ydy02-112 | 20 | 0 | 9 | 9 | 14 | 14 | 14 | 73 |
| 26 | ydy02-113 | 17 | 51 | 25 | 15 | 21 | 27 | 17 | 31 |
| 27 | ydy02-114 | 48 | 94 | 64 | 45 | 57 | 49 | 86 | 85 |
| 28 | Fluxapyroxad | 92 | 98 | 65 | 63 | 76 | 68 | 92 | 95 |
| 29 | Boscalid | 86 | 95 | 53 | 39 | 61 | 43 | 29 | 88 |
AS: tomato early blight bacterium, latin name are as follows: .Alternaria solani, BC: botrytis cinerea pers, Latin
Name are as follows: Botrytis cinerea, GZ: fusarium graminearum, latin name are as follows: Gibberella zeae, PI: potato evening
Epidemic disease bacterium, 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 (9)
1. a kind of multi-substituted pyrazol amide derivatives, it is characterised in that: have the general structure as shown in formula IV:
Wherein:
R1、R2、R3、R4、R5、R6It is selected from: hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy,
C2-C6Alkenyl, C2-C6Halogenated alkenyl, C2-C6Alkynyl, C2-C6Halo alkynyl, hydroxyl, C3-C6Naphthenic base, substituted piperidines -1-
The phenyl or C that base, substituted morpholine -1- base, substituted nafoxidine -1- base, phenyl or halogen replace1-C6Alkyl takes
The phenyl or C in generation1-C6The phenyl or C that halogenated alkyl replaces3-C6The phenyl or C that the phenyl or nitro that naphthenic base replaces replace2-
C6The phenyl or C that alkenyl replaces2-C6The phenyl or C that halogenated alkenyl replaces3-C6The phenyl or C that cycloalkenyl replaces2-C6Alkynyl
Substituted phenyl or C2-C6The phenyl or C that halo alkynyl replaces3-C6What phenyl, pyridyl group or the halogen that cycloalkynyl radical replaces replaced
Pyridyl group or C1-C6Alkyl-substituted pyridyl group or C1-C6The pyridyl group or C that halogenated alkyl replaces3-C6What naphthenic base replaced
The pyridyl group or C that pyridyl group or nitro replace2-C6The pyridyl group or C that alkenyl replaces2-C6The pyridyl group of halogenated alkenyl substitution,
Or C3-C6The pyridyl group or C that cycloalkenyl replaces2-C6The pyridyl group or C of alkynyl substituted2-C6Halo alkynyl replace pyridyl group or
C3-C6The pyrimidine radicals or C that pyridyl group, pyrimidine radicals or the halogen that cycloalkynyl radical replaces replace1-C6Alkyl-substituted pyrimidine radicals or C1-
C6The pyrimidine radicals or C that halogenated alkyl replaces3-C6The pyrimidine radicals or C that the pyrimidine radicals or nitro that naphthenic base replaces replace2-C6Alkenyl
Substituted pyrimidine radicals or C2-C6The pyrimidine radicals or C that halogenated alkenyl replaces3-C6The pyrimidine radicals or C that cycloalkenyl replaces2-C6Alkynyl
Substituted pyrimidine radicals or C2-C6The pyrimidine radicals or C that halo alkynyl replaces3-C6Pyrimidine radicals that cycloalkynyl radical replaces substituted contains 1
Or five yuan of 2 N atoms or six membered heteroaryl, substituted five yuan containing 1 or 2 S atom or six membered heteroaryl, contain 1
Or substituted five yuan or six membered heteroaryl, substituted five yuan or hexa-atomic containing 1 N atom and 1 S atom of 2 O atoms
Heteroaryl, substituted five yuan containing 1 N atom and 1 O atom or six membered heteroaryl, containing 2 N atoms and 1 S atom
Substituted five yuan or six membered heteroaryl, substituted five yuan or six membered heteroaryl containing 2 N atoms and 1 O atom；It is above-mentioned
Five yuan or six membered heteroaryl are selected from: substituted furyl, thienyl, pyrrole radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazole
Base, oxazolyl, isoxazolyl, oxadiazoles base, thiadiazolyl group, pyridyl group, pyridazinyl, pyrimidine radicals, pyrazinyl, triazine radical, tetrazine
Base, indyl, benzothienyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazole base, benzothiazolyl, benzo
Thiadiazolyl group, benzoxazolyl, the quinolyl of isomerization, the isoquinolyl of isomerization, phthalazinyl, quinoxalinyl, quinazolyl,
The silicon substrate that cinnoline base or naphthyridines base, alkyl or alkenyl replace；
Halogen is fluorine, chlorine, bromine or iodine in above-mentioned definition；
The alkyl, alkenyl or alkynyl are straight chain or branch alkyl；Alkyl itself or as other substituent groups part select
From methyl, ethyl, propyl, butyl, amyl, hexyl and its isomers, isomers is selected from isopropyl, isobutyl group, sec-butyl, uncle
Butyl, isopentyl or tertiary pentyl；
The halogenated alkyl group is selected from the group containing one or more identical or different halogen atoms, the halogenated alkyl choosing
From CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CF3CH2、CH3CF2、CF3CF2Or CCl3CCl2；
Described naphthenic base itself or as other substituent groups part be selected from cyclopropyl, cyclobutyl, cyclopenta or cyclohexyl；
Described alkenyl itself or as other substituent groups part be selected from vinyl, allyl, 1- acrylic, butene-2-base, fourth
Alkene -3- base, amylene -1- base, amylene -3- base, hexene -1- base or 4- methyl-3-pentenyl；
Described alkynyl itself or as other substituent groups part be selected from acetenyl, propine -1- base, propine -2- base, butine -1-
Base, crotonylene-base, 1- methyl -2- butynyl, hexin -1- base or 1- ethyl -2- butynyl.
2. multi-substituted pyrazol amide derivatives IV according to claim 1, R1It preferably is selected from: trifluoromethyl, difluoromethyl, chlorine；R2
It preferably is selected from: hydrogen, trifluoromethyl；R3It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine；R4Preferably be selected from: trifluoromethyl, hydrogen, fluorine, chlorine,
Bromine；R5It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine；R6It preferably is selected from: trifluoromethyl, hydrogen, fluorine, chlorine, bromine.
3. according to claim 1 with the specific synthetic route and method of multi-substituted pyrazol amide derivatives IV described in claim 2
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 a small amount of DMF and methylene chloride by starting material I and oxalyl chloride in intermediate II, wherein
The definition of starting material I and the substituent group in intermediate II is as described in claim 1, the definition of preferred substituents such as claim
Described in 2；
B. the preparation of multi-substituted pyrazol amide IV:
Multi-substituted pyrazol amide IV is by intermediate II and intermediate III and methylene chloride and acid binding agent Et3N is stirred in room temperature
Mix reaction preparation, wherein the definition of intermediate II and intermediate III and the substituent group in target product multi-substituted pyrazol amide IV
As described in claim 1, the definition of preferred substituents is as claimed in claim 2.
4. claim 1 and multi-substituted pyrazol amide derivatives IV as claimed in claim 2 and its intermediate are preparing agricultural kill
Purposes in epiphyte pharmaceutical.
5. a kind of composition pesticide, it includes claim 1 and multi-substituted pyrazol amide derivatives IV as claimed in claim 2 and
Wherein mesosome can prepare composition pesticide, and the composition includes claim 1 and multi-substituted pyrazol acyl as claimed in claim 2
Amine derivative IV and its intermediate are as active constituent, and the content of active constituent is 0.1% to 99.9% weight, and 99.9% arrives
The surfactant of the solid or liquid adjuvants of 0.1% weight and optional 0 to 50% weight.
6. a kind of pesticide complex composition, it includes claims 1 and multi-substituted pyrazol amide derivatives as claimed in claim 2
IV and its intermediate can prepare pesticide complex composition, which includes claim 1 and as claimed in claim 2
As active constituent, the content of active constituent is for multi-substituted pyrazol amide derivatives IV and its intermediate and commercially available agricultural chemical
0.1% to 99.9% weight, the surface of the solid or liquid adjuvants of 99.9% to 0.1% weight and optional 0 to 50% weight
Activating agent.
7. a kind of agricultural bactericidal complex composition, it includes claims 1 and multi-substituted pyrazol amide as claimed in claim 2 to spread out
Biological IV and its intermediate are bactericide compounded as active constituent, multi-substituted pyrazol amide derivatives IV and its intermediate with other
Ratio with other fungicide is mass percent 1%: 99% to 99%: 1%, and the content of active constituent is 1% to 99% weight
Amount, the solid or liquid adjuvants of 99% to 1% weight.
8. a kind of agricultural insecticidal, mite killing complex composition, it includes claims 1 and multi-substituted pyrazol as claimed in claim 2
Amide derivatives IV and its intermediate and other Insecticidal and acaricidal agents compounding are used as active constituent, multi-substituted pyrazol amide derivatives
The ratio of IV and its intermediate and other fungicide is mass percent 1%: 99% to 99%: 1%, and the content of active constituent is
1% to 99% weight, the solid or liquid adjuvants of 99% to 1% weight.
9. a kind of activating plants agent complex composition, it includes claims 1 and multi-substituted pyrazol amide as claimed in claim 2
Derivative I V and its intermediate and other plant activator compounding be used as active constituent, multi-substituted pyrazol amide derivatives IV 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.
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