CN105801485A - Phenyl pyrazole amide derivatives as well as preparation method and application thereof - Google Patents
Phenyl pyrazole amide derivatives as well as preparation method and application thereof Download PDFInfo
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Abstract
本发明公开了一类结构通式(E)所示的苯基连吡唑酰胺化合物及其制备方法：各取代基定义见说明书。本发明提供的苯基连吡唑酰胺化合物适合用于防治线虫。The invention discloses a class of phenylpyrazole amide compounds represented by general structural formula (E) and a preparation method thereof: For the definition of each substituent, see the description. The phenylpyrazole amide compound provided by the invention is suitable for controlling nematodes.
Description
Technical field
The present invention relates to a class phenyl and connect pyrazole amide derivatives.
Background technology
Patent documentation WO2005028485, WO2007065661, WO2007000462, WO2008014905, WO2007003540, WO2006120219, WO2007031323, US2009176844 have reported a class and have had the compound of efficient sterilizing activity, have following general structure (I):
Patent documentation WO2007141009, WO2007144174, WO2007134799, WO2008151828, WO2008148570, WO2009024342, WO2009003672, WO2009/127726, WO2009/127722, WO2009/127718 have reported the Fungicidal compounds that a class is similar, have following general structure (II):
In above-mentioned two class formations, Q represents the aryl replaced.
Prior art does not disclose said structure formula (I) with compound shown in compound shown in general structure (II) or similar said structure formula (I) and general structure (II) for the nematicide report of agrochemicals.
Summary of the invention
It is an object of the invention to provide a class phenyl and connect pyrazole amide compound, there is following general structure (E):
Wherein:
R1, R11, R12 are independently selected from hydrogen, halogen, itrile group, nitro, C1-C10Alkyl, C1-C10Haloalkyl, C1-C10Alkoxyl or C1-C10Halogenated alkoxy；
R1, R11, R12 may be located at any one possible position of phenyl ring；
R2 is selected from hydrogen, halogen, C1-C10Alkyl, C1-C10Haloalkyl, C1-C10Alkoxyl or C1-C10Halogenated alkoxy；
R3 is selected from hydrogen, halogen, C1-C10Alkyl or C1-C10Haloalkyl；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1-C10Alkyl or C1-C10Haloalkyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1-C10Alkyl, C2-C10Thiazolinyl, C2-C10Alkynyl, C1-C10Haloalkyl, C1-C10Alkoxyl, C1-C10Alkylthio group, phenoxy group, C1-C10Halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1～10Arrcostab, carboxyl C1～10Haloalkyl ester, C1-C10Alkylthio group, formamido, N-C1～10Alkyl or phenyl substituted formyl amido；
R8, R9, R10 may be located at any one possible position of phenyl ring.
Group described above, such as alkyl, haloalkyl, alkoxyl, halogenated alkoxy, thiazolinyl, alkynyl, alkylthio group, carboxyalkyl ester, carboxy halo Arrcostab, alkylthio group, N-alkyl or phenyl substituted formyl amido etc., both include straight chain group, also include all possible branched group.
As the preferred mode of one, phenyl shown in said structure formula (E) connects in pyrazole amide compound:
R1, R11, R12 preferably are selected from hydrogen, halogen, itrile group, nitro, C independently1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxyl or C1-C6Halogenated alkoxy；
R2 preferably is selected from hydrogen, halogen, C1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxyl or C1-C6Halogenated alkoxy；
R3 preferably is selected from hydrogen, halogen, C1-C6Alkyl or C1-C6Haloalkyl；
R4, R5, R6, R7 preferably are selected from hydrogen, halogen, C independently1-C6Alkyl or C1-C6Haloalkyl；
R8, R9, R10 preferably are selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C independently1-C6Alkyl, C2-C6Thiazolinyl, C2-C6Alkynyl, C1-C6Haloalkyl, C1-C6Alkoxyl, C1-C6Alkylthio group, phenoxy group, C1-C6Halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1～6Arrcostab, carboxyl C1～6Haloalkyl ester, C1-C4Alkylthio group, formamido, N-C1～6Alkyl or phenyl substituted formyl amido.
As it is preferred that mode, phenyl shown in said structure formula (E) connects in pyrazole amide compound:
R1, R11, R12 preferably are selected from hydrogen, halogen, C independently1-C4Alkyl or C1-C4Haloalkyl；
R2 preferably is selected from hydrogen, halogen, C1-C4Alkyl, C1-C4Haloalkyl, C1-C4Alkoxyl or C1-C4Halogenated alkoxy；
R3 preferably is selected from hydrogen, halogen, C1-C4Alkyl or C1-C4Haloalkyl；
R4, R5, R6, R7 preferably are selected from hydrogen, halogen, C independently1-C4Alkyl or C1-C4Haloalkyl；
R8, R9, R10 preferably are selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C independently1-C4Alkyl, C2-C4Thiazolinyl, C2-C4Alkynyl, C1-C4Haloalkyl, C1-C4Alkoxyl, C1-C4Alkylthio group, phenoxy group, C1-C4Halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1～4Arrcostab, carboxyl C1～4Haloalkyl ester, C1-C4Alkylthio group, formamido, N-C1～4Alkyl or phenyl substituted formyl amido.
As further preferred mode, phenyl shown in said structure formula (E) connects in pyrazole amide compound:
R1, R11, R12 preferably are selected from hydrogen, methyl, ethyl, the tert-butyl group, halogen, halogenated methyl or halogenated ethyl independently；
R2 preferably is selected from hydrogen, halogen, methyl, ethyl, halogenated methyl or halogenated ethyl；
R3 preferably is selected from hydrogen, halogen, methyl or halogenated methyl；
R4, R5, R6, R7 preferably are selected from hydrogen, halogen, methyl or halogenated methyl independently；
R8, R9, R10 preferably are selected from hydrogen, halogen, nitro, itrile group, hydroxyl, methyl, ethyl, isopropyl, haloisopropyl, the tert-butyl group, halogenated methyl, acetenyl, methoxyl group, ethyoxyl, C independently1-C4Alkylthio group, phenoxy group, halogenated methoxy, carboxyl or its alkali metal salt, formic acid C1～4Arrcostab, formic acid C1～4Haloalkyl ester, C1-C4Alkylthio group, formamido, N-C1～4Alkyl or phenyl substituted formyl amido.
As most preferred mode, phenyl shown in said structure formula (E) connects in pyrazole amide compound:
R1, R11, R12 are independently selected from hydrogen, methyl, chlorine, the tert-butyl group or trifluoromethyl；
R2 is selected from methyl, a methyl fluoride, difluoromethyl or trifluoromethyl；
R3 is selected from hydrogen or methyl；
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, perfluoroisopropyl, the tert-butyl group, acetenyl, methoxyl group, ethyoxyl, fluoro-methoxy, carboxyl or its alkali metal salt ,-CON (CH3)2、-CONHPh、-CONH2、-S-CH3、-OPh、-COOCH(CF3)2、--COOCH2CF2CHFCF3、-COOCH2CF3Or-COOCH3。
As the preferred mode of one, phenyl shown in said structure formula (E) connects in pyrazole amide compound, and the carbon that the described carbon being connected with R4 and R5 is connected with R6 and R7 is chiral configuration body and/or optical isomer.
Typical compound shown in following general structural formula provided by the present invention (E-a) is listed in table one.
Table one: the typical compound involved by structural formula [E-a]
The typical compound of following general structural formula provided by the present invention (E-b) is listed in table two.
Table two: the typical compound involved by structural formula [E-b]
| Numbering | R1,R11,R12 | R6 | R7 | Chiral carbon | R8,R9,R10 |
| E83 | 2-CH3 | CH3 | CH3 | 2,4,6-3Cl | |
| E84 | 4-CH3 | CH3 | CH3 | 4-NO2 | |
| E85 | 4-CH3 | CH3 | H | (R) | 3,4-2F |
| E86 | 4-CH3 | CH3 | H | (S) | 3,4-2F |
| E87 | 4-Et | CH3 | CH3 | 3,4-2F | |
| E88 | H | H | H | 3,4-2F | |
| E89 | 4-CF3 | H | H | 3,4-2F | |
| E90 | The 4-tert-butyl group | H | H | 3,4-2F | |
| E91 | 4-nitro | H | H | 3,4-2F | |
| E92 | 2,4-2Cl | H | H | 3,4-2F | |
| E9E3 | 4-bromine | H | H | 2,4,6-3Cl | |
| E94 | 2,6-2Cl | H | H | 3,4-2F | |
| E95 | 2,4,6-3Cl | H | H | 3,4-2F | |
| E96 | 4-OCH3 | H | H | 3,4-2F | |
| E97 | 4-CN | H | H | 3,4-2F |
| E98 | 4-OCF3 | H | H | 3,4-2F | |
| E99 | 4-CF(CF3)2 | H | H | 3,4-2F | |
| E100 | 4-CH3 | H | H | 4-CH=CH2 | |
| E101 | 4-CH3 | H | H | 4-acetenyl | |
| E102 | 4-CH3 | H | H | 4-COOCH3 | |
| E103 | 4-CH3 | H | H | 4-COOH | |
| E104 | 4-CH3 | H | H | 4--CONH2 | |
| E105 | 4-CH3 | H | H | 4--S-CH3 | |
| E106 | 4-CH3 | H | H | 4--CONHPh | |
| E107 | 4-CH3 | H | H | 4--CON(Me)2 |
The present invention also provides for the preparation method that the phenyl shown in general structure (E) connects pyrazole amide compound, comprises the following steps: reactions steps (1):
Reactions steps (2):
The definition of the R1-R12 in described reaction equation and preferably as previously mentioned.
As the preferred mode of one, described in above-mentioned preparation method, step (1) carries out in accordance with the following methods: in organic solvent, under acid binding agent effect, under 0 DEG C～organic solvent reflux temperature, the pyrazoles Benzenecarbonyl chloride. shown in described general structure (A) and the aminoethanol shown in general structure (B) are obtained by reacting the N-hydroxyethyl pyrazole amide shown in general structure (C).
As the preferred mode of one, described in above-mentioned preparation method, step (2) carries out in accordance with the following methods: in organic solvent, under 0 DEG C～organic solvent reflux temperature, the N-hydroxyethyl pyrazole amide shown in general structure (C) and the phenyl isocyanate shown in general structure (D) are obtained by reacting the pyrazole amide compound shown in general structure (E).
Above-mentioned organic solvent is preferably chloralkane or ethers, and described chloralkane is it is preferred that from dichloromethane, 1,2-dichloroethanes or carbon tetrachloride；Described acid binding agent is preferably triethylamine and/or Anhydrous potassium carbonate；Mol ratio between aminoethanol and acid binding agent three shown in pyrazoles Benzenecarbonyl chloride. shown in described general structure (A), general structure (B) is preferably 1:1～1.1:1～1.2；The mol ratio of the N-hydroxyethyl pyrazole amide shown in described general structure (C) and the phenyl isocyanate shown in general structure (D) is preferably 1:1～1.2.
Phenyl shown in general structure provided by the invention (E) connects pyrazole amide compound and is suitable for preventing and treating nematicide, is particularly suitable for the nematicide of preventing and treating crops and pinaster, it is possible to prepare agrochemicals nematicide as main active.Described agrochemicals nematicide can be formulated into liquor, cream, suspending agent, aqueous suspension, microemulsion, Emulsion, powder, wettable powder, soluble powder, granule or capsule.Described Emulsion includes aqueous emulsion, and described granule includes water-dispersible granules.Pyrazole amide derivatives shown in general structure of the present invention (E) is particularly suitable for.
When being formulated in agrochemicals nematicide, the weight ratio accounted in agrochemicals nematicide of the pyrazole amide derivatives shown in general structure of the present invention (E) is 5～90%, and all the other are the carrier being agriculturally suitable for.Carrier at least includes two kinds, and at least one of which is surfactant.Carrier can be solid or liquid.Suitable solid carrier includes natural or synthesis clay and silicate, for instance natural silica and kieselguhr；Magnesium silicate is Talcum such as；Magnesiumaluminumsilicate is kaolinite, Kaolin, montmorillonite and Muscovitum such as；White Carbon black, calcium carbonate, precipitated calcium carbonate；Calcium sulfate；Limestone；Sodium sulfate；Amine salt is ammonium sulfate, hexamethylene diamine such as.Liquid-carrier includes water and organic solvent, and when making solvent or diluent of water, organic solvent also can be used as adjuvant or antifreeze additive.Suitable organic solvent includes aromatic hydrocarbons such as benzene, dimethylbenzene, toluene etc.；Chlorohydrocarbon, for instance chlorobenzene, vinyl chloride, chloroform, dichloromethane etc.；Aliphatic hydrocarbon, for instance petroleum distillate, hexamethylene, light mineral oil；Alcohols, for instance isopropanol, butanol, ethylene glycol, glycerol and Hexalin etc.；And their ether and ester；Also has ketone, for instance acetone, Ketohexamethylene and dimethylformamide and N-methyl-pyrrolidon.
Surfactant can be emulsifying agent, dispersant or wetting agent；It can be ion-type or non-ionic.Nonionic emulsifier such as polyoxyethylene fatty acid fat, polyoxyethylene aliphatic alcohol ether, Polyoxyethylene fatty ammonia, and commercially available emulsifying 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 2201, 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-667, peaceful breast 36#.Dispersant includes sodium lignin sulfonate, pulls open powder, calcium lignosulfonate, condensation compound of methyl naphthalene sulfonic acid and formaldehyde etc..Wetting agent is: sodium laurylsulfate, dodecylbenzene sodium sulfonate, Negel etc..
Agrochemicals nematicide of the present invention can be prepared by general method.Such as, active substance is mixed with liquid flux and/or solid carrier, be simultaneously introduced surfactant such as emulsifying agent, dispersant, stabilizer, wetting agent, it is also possible to add other auxiliary agent such as binding agent, defoamer, oxidant etc..
Phenyl provided by the invention connects pyrazole amide compound compared with prior art, has the advantage that
(1) there is good eelworm-killing activity: under 50mg/L dosage, root-knot nematode and cyst roundworm are shown good effect；
(2) having good selectivity, to part crop, such as the safety such as Semen Tritici aestivi, Semen sojae atricolor, Cotton Gossypii, Oryza sativa L., vegetable is good；
(3) there is rational toxicity, eco-toxicity and Environmental compatibility.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is further described, but does not limit the invention to these detailed description of the invention.One skilled in the art would recognize that and present invention encompasses all alternatives, improvement project and the equivalents potentially included in Claims scope.
One, prepared by compound
Embodiment 1: the preparation of intermediate (C-1)
Dry reaction device, 10 mMs of 2-amino-1-propanol (B) are put in single port flask, 12 mMs of triethylamines, 100 milliliters of dichloromethane, 10 mMs of 3-difluoromethyl-1-(2 it are slowly dropped under ice bath, the chloro-4-trifluoromethyl of 6-2) the 30ml dichloromethane solution of-1H-pyrazoles-4-formyl chloride (A), 1 hour it is stirred at room temperature after dripping off, place 3 hours, after precipitation, TLC separates (developing solvent: ethyl acetate), obtain white solid (C-1) 3-(difluoromethyl)-N-(1-hydroxypropan-2-yl)-1-phenyl-1H-pyrazole-4-carboxamide.
Above-mentioned (B) is also changed to 2-amino-1-propanol (L-type), 2-amino-2-methyl-1-propanol, and ethylaminoethanol etc. prepares corresponding intermediate (C-1).
Embodiment 2: the preparation of target compound (E-2)
Weigh the prepared intermediate (C-1) of 10 mMs of embodiments 1 in single port flask, 20ml oxolane makees solvent, instill the 10 mMs of chloro-phenyl isocyanate of 2-methyl-3-(D), stir overnight under room temperature, concentration, TLC separates (mixed liquor that developing solvent is V (ethyl acetate): V (petroleum ether)=4:1), obtaining target product (E-2), its nuclear magnetic data is as follows:
Nuclear-magnetism1HNMR(600MHz,CDCl3): δ 8.04 (s, 1H), 7.72 (s, 2H), 7.51 (t, J=54Hz, 1H), 7.19 (d, J=7.9Hz, 1H), 7.10 (t, J=8.1Hz, 1H), 6.94 (s, 1H), 6.82 (s, 1H), 4.52-4.47 (m, 1H), 4.38 (dd, J=11.3,7.9Hz, 1H), 4.20 (dd, J=11.6,3.4Hz, 1H), 2.26 (s, 3H), 1.31 (d, J=6.5Hz, 3H).
Use all compounds that same method can synthesize E-1～E-107.
Two, preparation preparation
Embodiment 3: wettable powder agent prescription
Compound (E-a or E-b) by 15%, the lignosulfonates (M of 5%q), the polyoxyethylene lauryl ether (JFC) of 1%, the kieselguhr of 35% and the precipitated calcium carbonate of 44% mix equably, pulverize, obtain wettable powder.
Embodiment 4: emulsifiable concentrate formulation
Compound (E-a or E-b) by 10%, 5% agriculture breast 500 (calcium salts), the agriculture breast 602 of 5%, the METHYLPYRROLIDONE of 5% and 75% dimethylbenzene heated and stirred uniform, obtain cream.
Embodiment 5: Granular formulations
Compound (E-a or E-b) by 5%, the polyvinyl alcohol (PVA) of 1%, 4% naphthalenesulfonic acid-formaldehyde condensate (NMO) and 90% clay mix equably; pulverize; then 20 parts of water are added to these 100 parts of mixture; mediate; with extruding granulating machine; make the granule of 14～32 orders, dry, obtain granule.
Three, biological activity determination
The following method of nematicidal activity evaluation experimental evidence carries out:
In test tube, preparation compound E experimental concentration is the water solution system of 50ppm, wherein adds plant growth nutrient, and tomato seedling grows wherein, inoculates root-knot nematode and cyst roundworm, observes the root knot number of Fructus Lycopersici esculenti root after 20 days.
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.
Suppression ratio %=(CK root knot number-sample root knot number)/CK root knot number × 100%
Activity evaluation shows: the phenyl shown in general structure provided by the invention (E) connects pyrazole amide compound and has good eelworm-killing activity, particularly root-knot nematode and cyst roundworm are had good activity, " mg/L " refer both to every milligram of active matter/liter.
Under 50mg/L concentration, the suppression ratio of cyst roundworm both is greater than 80% by E1～E12, E14, E16, E19, E22～E34, E50～E61 and E77；The suppression ratio of root-knot nematode both is greater than 80% by E1～E15, E19, E20, E22～E34, E40, E44～E72 and E78.
Claims (14)
1. a class phenyl connects pyrazole amide compound, has following general structure (E):
Wherein:
R1, R11, R12 are independently selected from hydrogen, halogen, itrile group, nitro, C1-C10Alkyl, C1-C10Haloalkyl, C1-C10Alkoxyl or C1-C10Halogenated alkoxy；
R1, R11, R12 may be located at any one possible position of phenyl ring；
R2 is selected from hydrogen, halogen, C1-C10Alkyl, C1-C10Haloalkyl, C1-C10Alkoxyl or C1-C10Halogenated alkoxy；
R3 is selected from hydrogen, halogen, C1-C10Alkyl or C1-C10Haloalkyl；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1-C10Alkyl or C1-C10Haloalkyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1-C10Alkyl, C2-C10Thiazolinyl, C2-C10Alkynyl, C1-C10Haloalkyl, C1-C10Alkoxyl, C1-C10Alkylthio group, phenoxy group, C1-C10Halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1～10Arrcostab, carboxyl C1～10Haloalkyl ester, C1-C10Alkylthio group, formamido, N-C1～10Alkyl or phenyl substituted formyl amido；
R8, R9, R10 may be located at any one possible position of phenyl ring.
2. the phenyl described in claim 1 connects pyrazole amide compound, it is characterised in that described in:
R1, R11, R12 are independently selected from hydrogen, halogen, itrile group, nitro, C1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxyl or C1-C6Halogenated alkoxy；
R2 is selected from hydrogen, halogen, C1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxyl or C1-C6Halogenated alkoxy；
R3 is selected from hydrogen, halogen, C1-C6Alkyl or C1-C6Haloalkyl；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1-C6Alkyl or C1-C6Haloalkyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1-C6Alkyl, C2-C6Thiazolinyl, C2-C6Alkynyl, C1-C6Haloalkyl, C1-C6Alkoxyl, C1-C6Alkylthio group, phenoxy group, C1-C6Halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1～6Arrcostab, carboxyl C1～6Haloalkyl ester, C1-C4Alkylthio group, formamido, N-C1～6Alkyl or phenyl substituted formyl amido.
3. the phenyl described in claim 2 connects pyrazole amide compound, it is characterised in that described in:
R1, R11, R12 are independently selected from hydrogen, halogen, C1-C4Alkyl or C1-C4Haloalkyl；
R2 is selected from hydrogen, halogen, C1-C4Alkyl, C1-C4Haloalkyl, C1-C4Alkoxyl or C1-C4Halogenated alkoxy；
R3 is selected from hydrogen, halogen, C1-C4Alkyl or C1-C4Haloalkyl；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, C1-C4Alkyl or C1-C4Haloalkyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, sulfydryl, C1-C4Alkyl, C2-C4Thiazolinyl, C2-C4Alkynyl, C1-C4Haloalkyl, C1-C4Alkoxyl, C1-C4Alkylthio group, phenoxy group, C1-C4Halogenated alkoxy, carboxyl or its alkali metal salt, carboxyl C1～4Arrcostab, carboxyl C1～4Haloalkyl ester, C1-C4Alkylthio group, formamido, N-C1～4Alkyl or phenyl substituted formyl amido.
4. the phenyl described in claim 3 connects pyrazole amide compound, it is characterised in that described in:
R1, R11, R12 are independently selected from hydrogen, methyl, ethyl, the tert-butyl group, halogen, halogenated methyl or halogenated ethyl；
R2 is selected from hydrogen, halogen, methyl, ethyl, halogenated methyl or halogenated ethyl；
R3 is selected from hydrogen, halogen, methyl or halogenated methyl；
R4, R5, R6, R7 are independently selected from hydrogen, halogen, methyl or halogenated methyl；
R8, R9, R10 are independently selected from hydrogen, halogen, nitro, itrile group, hydroxyl, methyl, ethyl, isopropyl, haloisopropyl, the tert-butyl group, halogenated methyl, acetenyl, methoxyl group, ethyoxyl, C1-C4Alkylthio group, phenoxy group, halogenated methoxy, carboxyl or its alkali metal salt, formic acid C1～4Arrcostab, formic acid C1～4Haloalkyl ester, C1-C4Alkylthio group, formamido, N-C1～4Alkyl or phenyl substituted formyl amido.
5. the phenyl described in claim 3 connects pyrazole amide compound, it is characterised in that described in:
R1, R11, R12 are independently selected from hydrogen, methyl, chlorine, the tert-butyl group or trifluoromethyl；
R2 is selected from methyl, a methyl fluoride, difluoromethyl or trifluoromethyl；
R3 is selected from hydrogen or methyl；
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, perfluoroisopropyl, the tert-butyl group, acetenyl, methoxyl group, ethyoxyl, fluoro-methoxy, carboxyl or its alkali metal salt ,-CON (CH3)2、-CONHPh、-CONH2、-S-CH3、-OPh、-COOCH(CF3)2、--COOCH2CF2CHFCF3、-COOCH2CF3Or-COOCH3。
6. the phenyl described in claim 1 connects pyrazole amide compound, it is characterised in that the carbon that the described carbon being connected with R4 and R5 is connected with R6 and R7 is chiral configuration body and/or optical isomer.
7. the phenyl described in claim 1 connects pyrazole amide compound, it is characterised in that the phenyl shown in described formula (E) connects pyrazole amide compound and prepares in accordance with the following methods:
Reactions steps (1):
Reactions steps (2):
8. the phenyl described in claim 7 connects pyrazole amide compound, it is characterised in that:
In described reactions steps (1), in organic solvent, under acid binding agent effect, under 0 DEG C～organic solvent reflux temperature, the pyrazoles Benzenecarbonyl chloride. shown in described general structure (A) and the aminoethanol shown in general structure (B) are obtained by reacting the N-hydroxyethyl pyrazole amide shown in general structure (C)；
In described reactions steps (2), in organic solvent, under 0 DEG C～organic solvent reflux temperature, the N-hydroxyethyl pyrazole amide shown in general structure (C) and the phenyl isocyanate shown in general structure (D) are obtained by reacting the pyrazole amide compound shown in general structure (E).
9. the phenyl described in claim 8 connects pyrazole amide compound, it is characterized in that described organic solvent is chloralkane or ethers, described acid binding agent is triethylamine and/or Anhydrous potassium carbonate, mol ratio between aminoethanol and acid binding agent three shown in pyrazoles Benzenecarbonyl chloride. shown in described general structure (A), general structure (B) is 1:1～1.1:1～1.2, and the mol ratio of the N-hydroxyethyl pyrazole amide shown in described general structure (C) and the phenyl isocyanate shown in general structure (D) is 1:1～1.2.
10. the phenyl described in claim 9 connects pyrazole amide compound, it is characterised in that described chloralkane is selected from dichloromethane, 1,2-dichloroethanes or carbon tetrachloride.
11. connect pyrazole amide compound according to the phenyl one of claim 1～10 Suo Shu, it is characterised in that described phenyl connects pyrazole amide compound for preventing and treating nematicide.
12. the phenyl described in claim 11 connects pyrazole amide compound, it is characterised in that described phenyl connects pyrazole amide compound for preventing and treating the nematicide of crops and pinaster.
13. connect pyrazole amide compound according to the phenyl one of claim 1～10 Suo Shu, it is characterised in that described phenyl connects pyrazole amide compound for preparing agrochemicals nematicide.
14. the phenyl described in claim 13 connects pyrazole amide compound, it is characterised in that described phenyl connects pyrazole amide compound, and to account for the weight ratio in agrochemicals nematicide be 5～90%, all the other are the carrier being agriculturally suitable for.
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Effective date of registration: 20200217 Address after: 310023 No. 926, Xixi Road, Hangzhou, Zhejiang, Xihu District Co-patentee after: Sinochem Lantian Co., Ltd. Patentee after: Zhejiang Research Institute of Chemical Industry, Ltd. Co-patentee after: Sinochem Corporation Address before: 310023 No. 926, Xixi Road, Hangzhou, Zhejiang, Xihu District Co-patentee before: Sinochem Lantian Co., Ltd. Patentee before: Zhejiang Research Institute of Chemical Industry, Ltd. |