CN107235905A - A kind of 5 pyrazol acid amide compounds of the ether structure containing hexichol and preparation method thereof - Google Patents
A kind of 5 pyrazol acid amide compounds of the ether structure containing hexichol and preparation method thereof Download PDFInfo
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- CN107235905A CN107235905A CN201710635967.0A CN201710635967A CN107235905A CN 107235905 A CN107235905 A CN 107235905A CN 201710635967 A CN201710635967 A CN 201710635967A CN 107235905 A CN107235905 A CN 107235905A
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- acid amide
- ether structure
- amide compounds
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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
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses 5 pyrazol acid amide compounds of a kind of ether structure containing hexichol and preparation method thereof, 5 pyrazol acid amide compounds of the ether structure containing hexichol have below formula：
Description
Technical field
The present invention relates to a class noval chemical compound and application thereof, the 5- pyrazol acid amides of specifically a kind of ether structure containing hexichol
Compound and preparation method thereof.
Background technology
N- alkyl-pyrazoles -5- benzamide types are the compounds with desinsection and acaricidal activity newly reported the nineties, with it
Unique mechanism of action, it is safe and efficient, receive much concern the characteristics of no interactions resistance and small consumption.Representative Cultivars such as tebufenpyrad and azoles
Insect amide.Tolfenpyrad (tolfenpyad) is the new varieties that Mitsubishi Chemical releases, and the mechanism of action is similar to tebufenpyrad, insecticidal spectrum
Extensively, to phosphorus wing order, Semiptera, thrips and mite class are effective, with action of contace poison.
The pyrazole amide of the ether structure containing hexichol has desinsection and bactericidal activity, and daybreak etc. [CN106336380A] is reported perhaps
Compound A1 and A2 synthesis, it has preventive and therapeutic action to powdery mildew of cucumber and rice sheath blight disease.
The pyrazoles 4- benzamide compound A3 containing difluoromethyl of Yang Guangfu etc. [WO2015058444] synthesis, to paddy rice line
Rot has certain therapeutic effect.
The insecticidal activity of the chloro- 3- ethyls -1- methyl isophthalic acids H- pyrazoles -5- formamides of N- (2- Phenoxyphenyls) 4- is not researched and developed
Report.
The content of the invention
It is an object of the invention to provide a kind of 5- pyrazol acid amide compounds of ether structure containing hexichol as insecticide
And preparation method thereof.
The present invention uses following technical scheme：
A kind of 5- pyrazol acid amide compounds of ether structure containing hexichol, the 5- pyrazol acid amides of the ether structure containing hexichol
Compound has following structural formula：
It is preferred that, described R1One kind in hydrogen, halogen, C1-C10 alkyl, C1-C10 alkoxies；R2Selected from hydrogen, halogen
One kind in element, C1-C10 alkyl；R3One kind in hydrogen, halogen, C1-C10 alkyl；R4Selected from hydrogen or halogen；M is O or S；
R5One kind in hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, difluoromethyl, a methyl fluoride, methoxyl group, trifluoromethoxy；R6Choosing
One kind from hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, difluoromethyl, a methyl fluoride, methoxyl group, trifluoromethoxy；R7It is selected from
One kind in hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, difluoromethyl, a methyl fluoride, methoxyl group, trifluoromethoxy.
A kind of preparation method of the 5- pyrazol acid amide compounds of the ether structure containing hexichol, including：2- phenoxybenzamines and 4-
Chloro- 3- ethyls -1- methyl isophthalic acids H- pyrazoles -5- formic acid is raw material, through one under the conditions of catalyst, alkali, condensing agent and organic solvent
Step reaction synthesising target compound.
It is preferred that, described 2- phenoxybenzamines and the rate of charge of the chloro- 3- ethyls -1- methyl isophthalic acids H- pyrazoles -5- formic acid of 4-
For 1:1.
It is preferred that, described organic solvent is dichloromethane, chloroform or tetrahydrofuran.
It is preferred that, described condensing agent is EDCI or DCC.
It is preferred that, described catalyst is HOBt.
It is preferred that, described alkali is triethylamine.
A kind of application of the 5- pyrazol acid amide compounds of ether structure containing hexichol, the 5- pyrazoles of the ether structure containing hexichol
Amides compound as insecticide application.
It is preferred that, 5- pyrazol acid amide compounds the answering as the insecticide for killing mythimna separata of the ether structure containing hexichol
With.
The 5- pyrazol acid amide compounds for the ether structure containing hexichol that the present invention is provided, its chemical entitled N- (2- phenoxy group benzene
Base) the chloro- 3- ethyls -1- methyl isophthalic acids H- pyrazoles -5- formamides of 4-, structural formula is as follows：
The preparation method of the 5- pyrazol acid amide compounds for the ether structure containing hexichol that the present invention is provided, prepares reaction as follows：
Beneficial effects of the present invention are as follows：
The chloro- 3- ethyls -1- methyl isophthalic acids H- pyrazoles -5- formamides of N- (2- Phenoxyphenyls) 4- of the present invention have desinsection work
Property, can be as preparing insecticide.
Embodiment
Following examples are intended to illustrate invention rather than limitation of the invention further.
Embodiment 1
A kind of preparation method of the 5- pyrazol acid amide compounds of the ether structure containing hexichol：By the chloro- 3- ethyls -1- methyl of 4- -
1H- pyrazoles -5- carboxylic acids (1.50g, 7.9mmol), 2- phenoxybenzamines (1.47g, 7.9mmol) are dissolved in 80mL dichloromethane,
Add Et3N (1.60g, 15.8mmol), is subsequently added EDCI (1.82g, 9.5mmol), HOBt (1.29g, 9.5mmol), reaction
3.0h, TLC detection reaction are complete, add dichloromethane (20ml) dilution, and 50mL is washed 3 times, 50mL saturated common salts water washing one
Secondary, water layer is extracted with dichloromethane, merges organic layer, and anhydrous sodium sulfate drying, precipitation, crude product obtains red with pillar layer separation
Brown liquid 1.8g, yield：64%.
1HNMR(400MHz,CDCl3)δ：1.22 (t, J=7.6Hz, 3H, CH2CH3, pyrazole) and .2.61 (q, J=
7.6Hz,2H,CH2CH3,pyrazole),4.18(s,3H,CH3,pyrazole),6.95-7.13(m,1H,C6H4,C6H5),
7.33-7.37(m,2H,C6H5), 8.57 (d, J=8.0Hz, 1H, C6H4),9.22(s,1H,NH)。HRMS(EI)(calcd.m/
z)：355.1082(355.1088,M+)。
Embodiment 2
The insecticidal activity assay of the 5- pyrazol acid amide compounds of the ether structure containing hexichol
1) test objective
Virulence of the general sieve compound of the embodiment of the present invention 1 under for examination concentration to worm target, evaluates the work of its desinsection indoors
Property.
2) experimental condition
Target is mythimna separata (Mythimaseparata)
3) experimental design
Test medicine：The compound of embodiment 1
Experimental concentration：Screening concentration is 500mg/L and 100mg/L.
4) test method
The compound of example 1 is configured to 5.0%EC preparations with emulsifying agent (Tween-80) and DMF, plus distilled water diluting is configured to
Concentration liquid needed for determining.Screening concentration is 500mg/L, chemicals treatment amount of liquid medicine 10mL.Reference《In national south pesticides discovery
The heart gives birth to mark quasi-ordering》, insecticidal activity of the compound of example 1 to mythimna separata (Mythimaseparata) is tested using leaf dipping method.
Mythimna separata:Dried in the shade naturally after the maize leaves sheared in right amount section is fully infiltrated in the decoction prepared, be put into and be lined with filter
In the culture dish of paper, observation indoor feeding and observation are placed in after connecing mythimna separata 3 age mid-term larva, 15/ware, capping mark.Examined after 3d
Come to an end fruit.Polypide is touched with writing brush, it is reactionless to be considered as dead worm.
5) general sieve result
Pass through the general sieve of the inhibitory activity to mythimna separata of the 5- pyrazol acid amide compounds of the ether structure containing hexichol；Screening concentration is
500mg/L and 100mg/L, general sieve result is included in table 1.
Embodiment 1 has certain inhibitory activity under 500mg/L concentration to mythimna separata, and inhibiting rate is 100%.
Claims (10)
1. a kind of 5- pyrazol acid amide compounds of ether structure containing hexichol, it is characterised in that：The 5- of the described ether structure containing hexichol
Pyrazol acid amide compounds have following structural formula：
2. a kind of 5- pyrazol acid amide compounds of ether structure containing hexichol according to claim 1, it is characterised in that：It is described
R1One kind in hydrogen, halogen, C1-C10 alkyl, C1-C10 alkoxies；R2One in hydrogen, halogen, C1-C10 alkyl
Kind；R3One kind in hydrogen, halogen, C1-C10 alkyl；R4Selected from hydrogen or halogen；M is O or S；R5Selected from hydrogen, fluorine, chlorine, bromine,
One kind in iodine, trifluoromethyl, difluoromethyl, a methyl fluoride, methoxyl group, trifluoromethoxy；R6Selected from hydrogen, fluorine, chlorine, bromine, iodine,
One kind in trifluoromethyl, difluoromethyl, a methyl fluoride, methoxyl group, trifluoromethoxy；R7Selected from hydrogen, fluorine, chlorine, bromine, iodine, three
One kind in methyl fluoride, difluoromethyl, a methyl fluoride, methoxyl group, trifluoromethoxy.
3. a kind of preparation method of the 5- pyrazol acid amide compounds of the ether structure as claimed in claim 1 containing hexichol, its feature
It is, including：2- phenoxybenzamines and the chloro- 3- ethyls -1- methyl isophthalic acids H- pyrazoles -5- formic acid of 4- are raw material, catalyst, alkali,
Through single step reaction synthesising target compound under the conditions of condensing agent and organic solvent.
4. a kind of preparation method of the 5- pyrazol acid amide compounds of ether structure containing hexichol according to claim 3, it is special
Levy and be：The rate of charge of described 2- phenoxybenzamines and the chloro- 3- ethyls -1- methyl isophthalic acids H- pyrazoles -5- formic acid of 4- is 1:1.
5. a kind of preparation method of the 5- pyrazol acid amide compounds of ether structure containing hexichol according to claim 3, it is special
Levy and be：Described organic solvent is dichloromethane, chloroform or tetrahydrofuran.
6. a kind of preparation method of the 5- pyrazol acid amide compounds of ether structure containing hexichol according to claim 3, it is special
Levy and be：Described condensing agent is EDCI or DCC.
7. a kind of preparation method of the 5- pyrazol acid amide compounds of ether structure containing hexichol according to claim 3, it is special
Levy and be：Described catalyst is HOBt.
8. a kind of preparation method of the 5- pyrazol acid amide compounds of ether structure containing hexichol according to claim 3, it is special
Levy and be：Described alkali is triethylamine.
9. a kind of application of the 5- pyrazol acid amide compounds of the ether structure as claimed in claim 1 containing hexichol, it is characterised in that：
The 5- pyrazol acid amide compounds of the described ether structure containing hexichol as insecticide application.
10. a kind of application of the 5- pyrazol acid amide compounds of ether structure containing hexichol according to claim 8, its feature exists
In：The 5- pyrazol acid amide compounds of the described ether structure containing hexichol as kill mythimna separata insecticide application.
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Citations (3)
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|---|---|---|---|---|
| JPH02129171A (en) * | 1988-11-08 | 1990-05-17 | Nissan Chem Ind Ltd | Pyrazolecarboxanilide derivative and agent for controlling harmful life |
| CN1226244A (en) * | 1996-07-24 | 1999-08-18 | 拜尔公司 | Carbanilides used as pesticides |
| JP2006290883A (en) * | 2005-03-17 | 2006-10-26 | Nippon Nohyaku Co Ltd | Substituted heterocycle carboxylic anilide derivative, its intermediate and chemical for agriculture and horticulture and method for using the same |
-
2017
- 2017-07-31 CN CN201710635967.0A patent/CN107235905A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02129171A (en) * | 1988-11-08 | 1990-05-17 | Nissan Chem Ind Ltd | Pyrazolecarboxanilide derivative and agent for controlling harmful life |
| CN1226244A (en) * | 1996-07-24 | 1999-08-18 | 拜尔公司 | Carbanilides used as pesticides |
| JP2006290883A (en) * | 2005-03-17 | 2006-10-26 | Nippon Nohyaku Co Ltd | Substituted heterocycle carboxylic anilide derivative, its intermediate and chemical for agriculture and horticulture and method for using the same |
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Effective date of registration: 20180808 Address after: 438011 Guangming Road (Rudd Village), chemical industrial park, HuangZhou Railway Station, Huanggang, Hubei Applicant after: Wuhan Hua Bang chemical new material Co., Ltd. Address before: 300202 Xinian Square, Jiefang South Road, Hexi District, Tianjin 6-411 Applicant before: Yang Zihui |
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