CN106883176A - Pyrazole amide derivative, its preparation method and application - Google Patents
Pyrazole amide derivative, its preparation method and application Download PDFInfo
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- CN106883176A CN106883176A CN201510932834.0A CN201510932834A CN106883176A CN 106883176 A CN106883176 A CN 106883176A CN 201510932834 A CN201510932834 A CN 201510932834A CN 106883176 A CN106883176 A CN 106883176A
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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
- C07D231/16—Halogen atoms or nitro radicals
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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
- 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
- A01N47/20—N-Aryl derivatives thereof
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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
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Abstract
The invention provides the pyrazole amide compound that a class has following general structure (E)：
Description
Technical field
The present invention relates to pyrazole amide derivative.
Background technology
Patent document WO2005028485, WO2007065661, WO2007000462, WO2008014905,
WO2007003540, WO2006120219, WO2007031323, US2009176844 have reported a class has efficient sterilizing activity
Compound, with following general structure (I)：
Patent document WO2007141009, WO2007144174, WO2007134799, WO2008151828,
WO2008148570、WO2009024342、WO2009003672、WO2009/127726、WO2009/127722、WO2009/
127718 have reported the similar Fungicidal compounds of a class, with following general structure (II)：
In above-mentioned two class formation, Q represents the aryl of substitution.
Patent document US5039693 reports develop the similar Pesticidal compound Tolfenpyrad of a class, with following structure
Formula (III)：
The undisclosed herein described compound of prior art, also not publicly said structure leads to formula (I), (II) and (III) institute
Show that compound has agrochemicals eelworm-killing activity.
The content of the invention
The present invention provides pyrazole amide compound, with following general structure (E)：
Wherein：
R1 is selected from hydrogen, halogen, C1- C10Straight or branched alkyl, C1- C10Straight or branched haloalkyl；
R2 is selected from hydrogen, halogen, C1- C10Straight or branched alkyl, C1- C10Straight or branched haloalkyl, C1- C10Directly
Chain or branched alkoxy, C1- C10Straight or branched halogenated alkoxy；
R3 is selected from hydrogen, halogen；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1- C10Straight or branched alkyl, C1- C10Straight or branched halogen
Substituted alkyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1- C10Straight or branched alkyl,
C2- C10Straight or branched alkenyl, C2- C10Straight or branched alkynyl, C1- C10Straight or branched haloalkyl, C1- C10Straight chain
Or branched alkoxy, C1- C10Straight or branched alkylthio group, phenoxy group, C1- C10Straight or branched halogenated alkoxy, carboxyl or
Its alkali metal salt, carboxyl C1- C10Straight or branched alkyl ester, carboxyl C1- C10Straight or branched alkyl halide base ester, C1- C10Directly
Chain or branched alkylthio, formamido, N-C1-10Alkyl or phenyl replaces formamido；
R8, R9, R10 are separately located in any one possible position of phenyl ring.
The present invention provide general structure (E) shown in pyrazole amide compound, the substituent R 1 be selected from hydrogen, halogen,
C1- C10Straight or branched alkyl, C1- C10Straight or branched haloalkyl.Preferably, the substituent R 1 is selected from hydrogen, halogen
Element, C1- C6Straight or branched alkyl, C1- C6Straight or branched haloalkyl.It may further be preferable that the substituent R 1 is selected
From hydrogen, halogen, C1- C4Straight or branched alkyl, C1- C4Straight or branched haloalkyl.It is even furthermore preferable that described
Substituent R 1 is selected from hydrogen, methyl, ethyl, the tert-butyl group, halogen, halogenated methyl, halogenated ethyl.Most preferably, the substitution
Base R1 is selected from hydrogen, methyl, ethyl, the tert-butyl group, trifluoromethyl.
The present invention provide general structure (E) shown in pyrazole amide compound, the substituent R 2 be selected from hydrogen, halogen,
C1- C10Straight or branched alkyl, C1- C10Straight or branched haloalkyl, C1- C10Straight or branched alkoxyl, C1- C10Directly
Chain or side chain halogenated alkoxy.Preferably, the substituent R 2 is selected from hydrogen, halogen, C1- C6Straight or branched alkyl, C1-
C6Straight or branched haloalkyl, C1- C6Straight or branched alkoxyl, C1- C6Straight or branched halogenated alkoxy.It is further excellent
Choosing, the substituent R 2 is selected from hydrogen, halogen, C1- C4Straight or branched alkyl, C1- C4Straight or branched haloalkyl,
C1- C4Straight or branched alkoxyl, C1- C4Straight or branched halogenated alkoxy.It is even furthermore preferable that the substitution base
R2 is selected from hydrogen, methyl, ethyl, isopropyl, halogenated methyl, halogenated ethyl.Most preferably, the substituent R 2 is selected from first
Base, ethyl, isopropyl, difluoromethyl, trifluoromethyl.
The pyrazole amide compound shown in general structure (E) that the present invention is provided, the substituent R 3 is selected from hydrogen, halogen.
Preferably, the substituent R 3 is selected from hydrogen, chlorine, bromine.
The pyrazole amide compound shown in general structure (E) that the present invention is provided, the substituent R 4, R5, R6, R7 independence
Ground is selected from hydrogen, halogen, C1- C10Straight or branched alkyl, C1- C10Straight or branched haloalkyl.The substituent R 4, R5,
R6, R7 are independently selected from that is, R4, R5, R6 and R7 can be with identical, it is also possible to different.Preferably, the substituent R 4, R5,
R6, R7 are independently selected from hydrogen, halogen, C1- C6Straight or branched alkyl, C1- C6Straight or branched haloalkyl.It is further excellent
Choosing, the substituent R 4, R5, R6, R7 is independently selected from hydrogen, halogen, C1- C4Straight or branched alkyl, C1- C4Straight chain
Or branched haloalkyl.It is even furthermore preferable that the substituent R 4, R5, R6, R7 independently selected from hydrogen, halogen, methyl,
Halogenated methyl.Most preferably, the substituent R 4, R5, R6, R7 is independently selected from hydrogen or methyl.
The pyrazole amide compound shown in general structure (E) that the present invention is provided, the substituent R 8, R9, R10 is independently
Selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1- C10Straight or branched alkyl, C2- C10Straight or branched alkenyl,
C2- C10Straight or branched alkynyl, C1- C10Straight or branched haloalkyl, C1- C10Straight or branched alkoxyl, C1- C10Directly
Chain or branched alkylthio, phenoxy group, C1- C10Straight or branched halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1- C10
Straight or branched alkyl ester, carboxyl C1- C10Straight or branched alkyl halide base ester, C1- C10Straight or branched alkylthio group, formamide
Base, N-C1-10Alkyl or phenyl replaces formamido.The substituent R 8, R9, R10 is independently selected from that is, R8, R9 and R10 can
With identical, it is also possible to different.Preferably, the substituent R 8, R9, R10 is independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl
Base, sulfydryl, C1- C6Straight or branched alkyl, C2- C6Straight or branched alkenyl, C2- C6Straight or branched alkynyl, C1- C6Directly
Chain or branched haloalkyl, C1- C6Straight or branched alkoxyl, C1- C6Straight or branched alkylthio group, phenoxy group, C1- C6Directly
Chain or side chain halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1- C6Straight or branched alkyl ester, carboxyl C1- C6Straight chain
Or branched haloalkyl ester, C1- C4Straight or branched alkylthio group, formamido, N-C1-6Alkyl or phenyl replaces formamido.
It may further be preferable that the substituent R 8, R9, R10 is independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1- C4
Straight or branched alkyl, C2- C4Straight or branched alkenyl, C2- C4Straight or branched alkynyl, C1- C4Straight or branched alkyl halide
Base, C1- C4Straight or branched alkoxyl, C1- C4Straight or branched alkylthio group, phenoxy group, C1- C4Straight or branched alkyl halide
Epoxide, carboxyl or its alkali metal salt, carboxyl C1-4Straight or branched alkyl ester, carboxyl C1-4Straight or branched alkyl halide base ester,
C1- C4Straight or branched alkylthio group, formamido, N-C1-4Alkyl or phenyl replaces formamido.It is even furthermore preferable that
The substituent R 8, R9, R10 is independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, methyl, ethyl, isopropyl, halo isopropyl
Base, the tert-butyl group, halogenated methyl, acetenyl, methoxyl group, ethyoxyl, halogenated methoxy, carboxyl or its alkali metal salt, formic acid C1~4Directly
Chain or branched alkyl ester, formic acid C2~4Straight or branched alkyl halide base ester, C1- C4Straight or branched alkylthio group, formamido,
N-C1-4Alkyl or phenyl replaces formamido.Most preferably, the substituent R 8, R9, R10 is independently selected from hydrogen, halogen
Element, nitro, itrile group, methyl, ethyl, trifluoromethyl, perfluoroisopropyl, the tert-butyl group, acetenyl, methoxyl group, ethyoxyl, fluoroform
Epoxide, carboxyl or its alkali metal salt ,-CON (Me)2、-CONHPh、-CONH2、-S-CH3、-OPh、-COOCH(CF3)2、--
COOCH2CF2CHFCF3、-COOCH2CF3、-CON(Me)2、-COOCH3Or-CONHPh.
The pyrazole amide compound shown in general structure (E) that the present invention is provided, the substituent R 8, R9, R10 is independently
Positioned at any one possible position of phenyl ring.I.e. R8, R9, R10 may be located at the position that any one may be substituted on phenyl ring.
Typical compound with following E-a general structures involved in the present invention is listed in the table below 1.
Typical compound involved by table 1, structural formula [E-a]
Typical compound with following E-b general structures involved in the present invention is listed in the table below 2.
Typical compound involved by table 2, structural formula [E-b]
It is present invention also offers the preparation method of the pyrazole amide compound shown in the general structure (E) including following
Step：
The definition of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 in above-mentioned reaction equation and preferably as previously described.
The above-mentioned first step is reacted：R1R2R3 substitution pyrazoles chlorobenzoyl chloride (A), R4-R7 substitution aminoethanol (B) and
In chloralkane or ethers (such as) organic solvent, reaction 0.5~24 is small under 0 DEG C to organic solvent reflux temperature for acid binding agent
When obtain intermediate N hydroxyl second class pyrazole amide (C).Preferably, the acid binding agent is preferably triethylamine or Anhydrous potassium carbonate.
Preferably, the chloralkane be selected from dichloromethane, 1,2- dichloroethanes and carbon tetrachloride in one kind, two or three.
Preferably, the ethers be selected from ether, tetrahydrofuran or Isosorbide-5-Nitrae-dioxane in one kind, two or three.Preferably,
The mol ratio of the pyrazoles chlorobenzoyl chloride (A) of the R1R2R3 substitutions, the aminoethanol (B) of R4-R7 substitutions and acid binding agent between
It is 1:1~1.1:1~1.2.
Second step reacts：The phenyl isocyanate (D) of N- hydroxyl second class pyrazole amide (C) and R8-R10 substitutions is in chloro
In alkane or ether organic solvent, reaction obtains general structure in 0.5~24 hour under 0 DEG C to organic solvent reflux temperature
(E) pyrazole amide derivatives shown in.Preferably, the chloralkane is selected from dichloromethane, 1,2- dichloroethanes and tetrachloro
Change carbon in one kind, two or three.Preferably, the ethers is selected from ether, tetrahydrofuran or Isosorbide-5-Nitrae-dioxane
It is a kind of, two or three.Preferably, N- hydroxyls second class pyrazole amide (C) and the phenyl isocyanate (D) of R8-R10 substitutions
Mol ratio is preferably 1:1~1.2.
The present invention also provides a kind of agrochemicals nematicide, and the agrochemicals nematicide contains 0.1~99%
Pyrazole amide compound shown in general structure (E), remaining is agriculturally acceptable carrier.Preferably, agriculturalization
Nematicide contains the pyrazole amide compound shown in 5~90% general structure (E).
The formulation of the agrochemicals nematicide, can be liquor, missible oil, suspending agent, aqueous suspension, microemulsion, emulsion,
Pulvis, wettable powder, soluble powder, granule or capsule.
The carrier used in the formulation of the agrochemicals nematicide at least includes two kinds, and wherein at least one is surface
Activating agent.Carrier can be solid or liquid.Suitable solid carrier includes natural or synthesis clay and silicate, for example
Natural silica and diatomite；Magnesium silicate such as talcum；Magnesiumaluminumsilicate such as kaolinite, kaolin, montmorillonite and mica；White carbon
Black, calcium carbonate, precipitated calcium carbonate；Calcium sulfate；Lime stone；Sodium sulphate；Amine salt such as ammonium sulfate, hexamethylene diamine.Liquid-carrier bag
Water and organic solvent are included, when solvent or diluent is done with water, organic solvent can also be used as adjuvant or antifreeze additive.Properly
Organic solvent include aromatic hydrocarbons such as benzene, dimethylbenzene, toluene etc.；Chlorohydrocarbon, such as chlorobenzene, vinyl chloride, chloroform, dichloro
Methane etc.；Aliphatic hydrocarbon, such as petroleum distillate, hexamethylene, light mineral oil；Alcohols, such as isopropanol, butanol, ethylene glycol, the third three
Alcohol and cyclohexanol etc.；And their ether and ester；Also ketone, such as acetone, cyclohexanone and dimethylformamide and N- first
Base-pyrrolidones.
Surfactant can be emulsifying agent, dispersant or wetting agent；Can be ionic or nonionic.It is non-from
Subtype emulsifying agent such as polyoxyethylene fatty acid fat, polyoxyethylene aliphatic alcohol ether, Polyoxyethylene fatty ammonia, and commercially available emulsification
Agent：Agriculture breast 2201B, agriculture breast 0203B, agriculture breast 100#, agriculture breast 500#, agriculture breast 600#, agriculture breast 600-2#, agriculture breast 1601, agriculture breast
2201st, agriculture breast NP-10, agriculture breast NP-15, agriculture breast 507#, agriculture breast OX-635, agriculture breast OX-622, agriculture breast OX-653, agriculture breast OX-
667th, peaceful breast 36#.Dispersant includes sodium lignin sulfonate, pull open powder, calcium lignosulfonate, condensation compound of methyl naphthalene sulfonic acid and formaldehyde
Deng.Wetting agent is：Sldium lauryl sulfate, neopelex, Negel etc..
These preparations can be prepared by general method.For example, active material is mixed with liquid flux and/or solid carrier
Close, while adding surfactant such as emulsifying agent, dispersant, stabilizer, wetting agent, other auxiliary agents can also be added such as：Bonding
Agent, defoamer, oxidant etc..
Pyrazole amide compound and agrochemicals nematicide shown in the general structure (E) of present invention offer are suitable for
Preventing and treating nematode, is especially suitable for preventing and treating the nematode of crops and pine tree, is particularly suitable for preventing and treating root-knot nematode and cyst roundworm.
The present invention provide general structure (E) shown in pyrazole amide compound compared with prior art, with following excellent
Point：
(1) with preferable eelworm-killing activity：Preferable effect is shown to root-knot nematode under 50mg/L dosage；
(2) it is good to the part crop such as security such as wheat, soybean, cotton, paddy rice, vegetables with preferable selectivity；
(3) with rational toxicity, eco-toxicity and Environmental compatibility.
Specific embodiment
The present invention is further described with reference to specific embodiment, but does not limit the invention to these tools
Body implementation method.One skilled in the art would recognize that present invention encompasses being potentially included in Claims scope
All alternatives, improvement project and equivalents.
First, prepared by compound
The preparation of the intermediate of embodiment 1 (C-1)
3.75 grams of 2- amino -1- propyl alcohol (B-1) of input, 6.3 grams of triethylamines, 50ml in dry reaction device, single-necked flask
Dichloromethane, is slowly dropped into 11.20 grams of 50ml of the 3- ethyl -1- methyl chloro- 1H- pyrazoles -5- formyl chlorides (A-1) of -4- under ice bath
Dichloromethane solution, is stirred at room temperature 1 hour after dripping off, and places 3 hours, and TLC separates (solvent after precipitation：Ethyl acetate), obtain
To 10.9 grams of white solid (C-1).The white solid (C-1) for obtaining be 3- ethyls-N- (1- hydroxypropyl -2- bases) -1- methyl -
1H- pyrazoles -5- formamides.
Above-mentioned (B) is also changed to the system such as 2- amino -1- propyl alcohol (DL), 2-amino-2-methyl-1-propanol, ethylaminoethanol
Obtain corresponding intermediate (C).
The preparation of the target compound of embodiment 2 (E-1)
Weigh intermediate (C-1) obtained in 10mmol embodiments 1 and 10mmol4- sevoflurane isopropyl based isocyanates (D-
1) in single-necked flask, 20ml tetrahydrofurans make solvent, are stirred overnight at room temperature, concentration, and (solvent is V (acetic acid for TLC separation
Ethyl ester): V (petroleum ether)=4:1 mixed liquor), obtain 2.50 grams of target product (E-1).The nuclear magnetic data of target product (E-1)
It is as follows：
Nuclear-magnetism：1H-NMR(ppm)：
δ 1.22~1.27 (t, 3H), 1.33~1.35 (d, 3H), 2.60~2.64 (q, 2H), 4.10 (s, 3H), 4.26~
4.29 (m, 2H), 4.50~4.52 (m, 1H), 6.77~6.78 (d, 1H), 7.01 (s, 1H), 7.52~7.55 (m, 4H).
All compounds of E-1 to E-95 can be synthesized using same method.
2nd, preparation is prepared
The wettable powder agent prescription of embodiment 3
By percentage to the quality, by 15% compound (compound described in Tables 1 and 2), 5% lignosulfonates
(Mq), 1% ethoxylated dodecyl alcohol (JFC), 40% diatomite and 44% precipitated calcium carbonate equably mix, powder
It is broken, obtain final product wettable powder.
The emulsifiable concentrate formulation of embodiment 4
By percentage to the quality, by 10% compound (compound described in Tables 1 and 2), 5% No. 500 (calcium of agriculture breast
Salt), 5% agriculture breast 602,5% METHYLPYRROLIDONE and 75% dimethylbenzene heating stirring it is uniform, obtain final product missible oil.
The Granular formulations of embodiment 5
By percentage to the quality, by 5% compound (compound described in Tables 1 and 2), 1% polyvinyl alcohol (PVA),
4% naphthalenesulfonic acid-formaldehyde condensate (NMO) and 90% clay equably mix, and crush.Then added to this 100 parts of mixtures
20 parts of water, mediate, and use extruding granulating machine, are made the particle of 14-32 mesh, dry, and obtain final product granule.
3rd, biological activity determination
The following method of nematicidal activity evaluation experimental evidence is carried out：
It is the water solution system of 100ppm that compound E experimental concentrations are prepared in test tube, wherein plant growth nutrient is added,
Tomato seedling grows wherein, is inoculated with root-knot nematode and cyst roundworm, the root knot number of observation tomato root.
Investigation method and grade scale
Classification：0：0-5 root knot；
5：6-10 root knot；
10：11-20 root knot；
20：More than 20 root knots.
Inhibiting rate %=(CK root knots number-sample root knot number)/CK root knot number × 100%
Under 100mg/L (every milligram active matter/liter) concentration, the inhibiting rate of E1-E68, E72, E81, E82 to root-knot nematode
Both greater than 80%.
Activity evaluation shows：The pyrazole amide compound shown in general structure (E) that the present invention is provided has good
Eelworm-killing activity, particularly there is activity well to root-knot nematode and cyst roundworm.
Claims (12)
1. pyrazole amide compound, with following general structure (E)：
Wherein：
R1 is selected from hydrogen, halogen, C1- C10Straight or branched alkyl, C1- C10Straight or branched haloalkyl；
R2 is selected from hydrogen, halogen, C1- C10Straight or branched alkyl, C1- C10Straight or branched haloalkyl, C1- C10Straight chain or
Branched alkoxy, C1- C10Straight or branched halogenated alkoxy；
R3 is selected from hydrogen, halogen；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1- C10Straight or branched alkyl, C1- C10Straight or branched alkyl halide
Base；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1- C10Straight or branched alkyl, C2-
C10Straight or branched alkenyl, C2- C10Straight or branched alkynyl, C1- C10Straight or branched haloalkyl, C1- C10Straight chain or branch
Chain alkoxy, C1- C10Straight or branched alkylthio group, phenoxy group, C1- C10Straight or branched halogenated alkoxy, carboxyl or its alkali
Slaine, carboxyl C1- C10Straight or branched alkyl ester, carboxyl C1- C10Straight or branched alkyl halide base ester, C1- C10Straight chain or
Branched alkylthio, formamido, N-C1-10Alkyl or phenyl replaces formamido；
R8, R9, R10 are separately located in any one possible position of phenyl ring.
2. according to the pyrazole amide compound described in claim 1, it is characterised in that in the general structure (E)：
R1 is selected from hydrogen, halogen, C1- C6Straight or branched alkyl, C1- C6Straight or branched haloalkyl；
R2 is selected from hydrogen, halogen, C1- C6Straight or branched alkyl, C1- C6Straight or branched haloalkyl, C1- C6Straight chain or branch
Chain alkoxy, C1- C6Straight or branched halogenated alkoxy；
R3 is selected from hydrogen, halogen；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1- C6Straight or branched alkyl, C1- C6Straight or branched haloalkyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1- C6Straight or branched alkyl, C2- C6
Straight or branched alkenyl, C2- C6Straight or branched alkynyl, C1- C6Straight or branched haloalkyl, C1- C6Straight or branched alkane
Epoxide, C1- C6Straight or branched alkylthio group, phenoxy group, C1- C6Straight or branched halogenated alkoxy, carboxyl or its alkali metal
Salt, carboxyl C1- C6Straight or branched alkyl ester, carboxyl C1- C6Straight or branched alkyl halide base ester, C1- C4Straight or branched alkane
Sulfenyl, formamido, N-C1-6Alkyl or phenyl replaces formamido.
3. according to the pyrazole amide compound described in claim 2, it is characterised in that in the general structure (E)：
R1 is selected from hydrogen, halogen, C1- C4Straight or branched alkyl, C1- C4Straight or branched haloalkyl；
R2 is selected from hydrogen, halogen, C1- C4Straight or branched alkyl, C1- C4Straight or branched haloalkyl, C1- C4Straight chain or branch
Chain alkoxy, C1- C4Straight or branched halogenated alkoxy；
R3 is selected from hydrogen, halogen；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1- C4Straight or branched alkyl, C1- C4Straight or branched haloalkyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1- C4Straight or branched alkyl, C2- C4
Straight or branched alkenyl, C2- C4Straight or branched alkynyl, C1- C4Straight or branched haloalkyl, C1- C4Straight or branched alkane
Epoxide, C1- C4Straight or branched alkylthio group, phenoxy group, C1- C4Straight or branched halogenated alkoxy, carboxyl or its alkali metal
Salt, carboxyl C1-4Straight or branched alkyl ester, carboxyl C1-4Straight or branched alkyl halide base ester, C1- C4Straight or branched alkylthio group,
Formamido, N-C1-4Alkyl or phenyl replaces formamido.
4. according to the pyrazole amide compound described in claim 3, it is characterised in that in the general structure (E)：
R1 is selected from hydrogen, methyl, ethyl, the tert-butyl group, halogen, halogenated methyl, halogenated ethyl；
R2 is selected from hydrogen, methyl, ethyl, isopropyl, halogenated methyl, halogenated ethyl；
R3 is selected from hydrogen, halogen；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, methyl, halogenated methyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, methyl, ethyl, isopropyl, haloisopropyl, uncle
Butyl, halogenated methyl, acetenyl, methoxyl group, ethyoxyl, halogenated methoxy, carboxyl or its alkali metal salt, formic acid C1~4Straight chain or
Branched alkyl ester, formic acid C2~4Straight or branched alkyl halide base ester, C1- C4Straight or branched alkylthio group, formamido, N-C1-4
Alkyl or phenyl replaces formamido.
5. according to the pyrazole amide compound described in claim 4, it is characterised in that in the general structure (E)：
R1 is selected from hydrogen, methyl, ethyl, the tert-butyl group, trifluoromethyl；
R2 is selected from methyl, ethyl, isopropyl, difluoromethyl, trifluoromethyl；
R3 is selected from hydrogen, chlorine, bromine；
R4, R5, R6, R7 are independently selected from hydrogen or methyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, methyl, ethyl, trifluoromethyl, perfluoroisopropyl, tertiary fourth
Base, acetenyl, methoxyl group, ethyoxyl, trifluoromethoxy, carboxyl or its alkali metal salt ,-CON (Me)2、-CONHPh、-CONH2、-
S-CH3、-OPh、-COOCH(CF3)2、--COOCH2CF2CHFCF3、-COOCH2CF3、-CON(Me)2、-COOCH3Or-CONHPh.
6. according to the pyrazole amide compound described in claim 1, it is characterised in that in the general structure (E)：R4 and R5 chains
The carbon atom that the carbon atom for connecing is connected with R6 and R7 is chiral configuration body and/or optical isomer.
7. according to the pyrazole amide compound described in claim 1, it is characterised in that the preparation side of the pyrazole amide compound
Method includes：
8. according to the pyrazole amide compound described in claim 7, it is characterised in that：
(1) in chloralkane or ether organic solvent, under acid binding agent effect, under 0 DEG C to organic solvent reflux temperature, institute
State the pyrazoles -5- formyl chlorides shown in general structure (A) and obtain general structure with the aminoethanol reaction shown in general structure (B)
(C) the intermediate N hydroxyl second class pyrazoles -5- acid amides shown in；
(2) in chloralkane or ether organic solvent, under 0 DEG C to organic solvent reflux temperature, shown in general structure (C)
Intermediate N hydroxyl second class pyrazoles -5- acid amides obtains general structure (E) with the phenyl isocyanate reaction shown in general structure (D)
Shown pyrazoles -5- amide compounds.
9. according to the pyrazole amide compound described in claim 8, it is characterised in that：
The acid binding agent is triethylamine and/or Anhydrous potassium carbonate；
The chloralkane be selected from dichloromethane, 1,2- dichloroethanes and carbon tetrachloride in one kind, two or three；
The ethers be selected from ether, tetrahydrofuran or 1,4- dioxane in one kind, two or three；
Aminoethanol shown in pyrazoles chlorobenzoyl chloride, general structure (B) and acid binding agent three shown in the general structure (A) it
Between mol ratio be 1:1~1.1:1~1.2；
Intermediate N hydroxyl second class pyrazole amide shown in the general structure (C) and the phenyl isocyanic acid shown in general structure (D)
The mol ratio of ester is 1:1~1.2.
10. according to the pyrazole amide compound that one of claim 1-9 is described, it is characterised in that the pyrazole amide compound is used
In preventing and treating nematode.
11. a kind of agrochemicals nematicides, it is characterised in that the agrochemicals nematicide contains 0.1~99% structure
Pyrazole amide compound shown in formula (E).
12. according to the agrochemicals nematicide described in claim 11, it is characterised in that the agrochemicals nematicide
Formulation be liquor, missible oil, suspending agent, aqueous suspension, microemulsion, emulsion, pulvis, wettable powder, soluble powder, granule or
Capsule.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001054481A2 (en) * | 2000-01-28 | 2001-08-02 | Rohm And Haas Company | Enhanced propertied pharmaceuticals |
| WO2001055124A1 (en) * | 2000-01-28 | 2001-08-02 | Nihon Bayer Agrochem K.K. | Isothiazolecarboxylic acid derivatives and their use as microbicides |
| WO2001056358A2 (en) * | 2000-01-28 | 2001-08-09 | Rohm And Haas Company | Enhanced propertied pesticides |
| CN104725316A (en) * | 2013-12-20 | 2015-06-24 | 浙江省化工研究院有限公司 | Pyrazole amide derivative, and preparation method and applications thereof |
-
2015
- 2015-12-15 CN CN201510932834.0A patent/CN106883176A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001054481A2 (en) * | 2000-01-28 | 2001-08-02 | Rohm And Haas Company | Enhanced propertied pharmaceuticals |
| WO2001055124A1 (en) * | 2000-01-28 | 2001-08-02 | Nihon Bayer Agrochem K.K. | Isothiazolecarboxylic acid derivatives and their use as microbicides |
| WO2001056358A2 (en) * | 2000-01-28 | 2001-08-09 | Rohm And Haas Company | Enhanced propertied pesticides |
| CN104725316A (en) * | 2013-12-20 | 2015-06-24 | 浙江省化工研究院有限公司 | Pyrazole amide derivative, and preparation method and applications thereof |
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