CN108892646A - Chloro- 2- pyrazinamide class compound of a kind of 6- containing diphenyl ether base and the preparation method and application thereof - Google Patents
Chloro- 2- pyrazinamide class compound of a kind of 6- containing diphenyl ether base and the preparation method and application thereof Download PDFInfo
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- CN108892646A CN108892646A CN201810876501.4A CN201810876501A CN108892646A CN 108892646 A CN108892646 A CN 108892646A CN 201810876501 A CN201810876501 A CN 201810876501A CN 108892646 A CN108892646 A CN 108892646A
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- chloro
- diphenyl ether
- ether base
- containing diphenyl
- class compound
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- YSFQVLZBAHEKBN-BJUGOGSMSA-N C=C/N=C(/C(NC(C(F)=C1)=CCC1F)=O)\C(O/C=C/C=C\C(C(F)(F)F)=C)=N Chemical compound C=C/N=C(/C(NC(C(F)=C1)=CCC1F)=O)\C(O/C=C/C=C\C(C(F)(F)F)=C)=N YSFQVLZBAHEKBN-BJUGOGSMSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
Abstract
The present invention relates to the preparation methods and application of the chloro- 2- pyrazinamide class compound of 6- containing diphenyl ether base, the chloro- 2- pyrazinamide class compound of the 6- containing diphenyl ether base, with 4- phenoxybenzamine or 2- phenoxybenzamine for the first reactant, with 6- chloropyrazine -2- formic acid for the second reactant, first reactant and the second reactant are dissolved in reaction dissolvent, synthesized through single step reaction.Beneficial effects of the present invention are：The chloro- 2- pyrazinamide class compound of 6- containing diphenyl ether base of the invention has activity of weeding and insecticidal effect, can be used as herbicide or insecticidal materials.
Description
Technical field
The present invention relates to a kind of compound and its applications, and in particular to a kind of chloro- 2- pyrazinamide of 6- containing diphenyl ether base
Class compound and the preparation method and application thereof.
Background technique
Pyrazinamide class compound has extensive medicine and pesticide activity, in pesticide field, Nihon Nihyaku Co., Ltd
In the Pyraziflumid that 2014 release, exploitation code name is NNF-0721.It is mainly used for rice, fruit tree, vegetables and lawn etc.,
Preventing and treating powdery mildew, scab, gray mold, sclerotiniose, ring spot, fruit blotch and coin pinta etc., effective component dosage is 100~
375g/hm2 is the fungicide kind with market potential.The structural formula of Pyraziflumid is：
Having document report pyrazinamide class compound in recent years has potential activity of weeding, Tumova in 2005
The compound A of equal reports has preferable activity of weeding under 3.72X10-5mol/L concentration；The report such as Engel.S of BASF AG
Road compound B has good preventive effect to red heart Chenopodiaceae, clearvers and herba setariae viridis under 250g/hm2 dosage.
The structural formula of compound A is：
The structural formula of compound B is：
But currently, pyrazinamide class compound there has been no the listing of the kind of herbicide, research and develop such compound have compared with
Big value.
Summary of the invention
Of the existing technology in order to solve the problems, such as, the present invention provides a kind of chloro- 2- pyrazine acyls of 6- containing diphenyl ether base
Aminated compounds and the preparation method and application thereof, the chloro- 2- pyrazinamide class compound of 6- containing diphenyl ether base have weeding and kill
The features such as worm.
The object of the present invention is to provide a kind of chloro- 2- pyrazinamide class compounds of 6- containing diphenyl ether base.
The chloro- 2- pyrazinamide class compound of the 6- containing diphenyl ether base of specific embodiment according to the present invention, it is described to contain
6- chloropyrazine -2- the amides compound of diphenyl ether base has the following structure formula (I) or (II)：
It is the chloro- N- of 6- (2- Phenoxyphenyl) pyrazine -2- formamide, chemical structural formula shown in chemical structure formula (I)
It (II) is the chloro- N- of 6- (4- Phenoxyphenyl) pyrazine -2- formamide shown in.
It is a further object to provide a kind of chloro- 2- pyrazinamide class compounds of 6- prepared containing diphenyl ether base
Method.
The chloro- 2- pyrazinamide class chemical combination of 6- described in the preparation of specific embodiment according to the present invention containing diphenyl ether base
The method of object, the described method comprises the following steps：With 4- phenoxybenzamine or 2- phenoxybenzamine for the first reactant, with 6- chlorine
Pyrazine -2- formic acid is the second reactant, and the first reactant and the second reactant are dissolved in reaction dissolvent, synthesized through single step reaction
Compound (I) or (II).
The chloro- 2- pyrazinamide class chemical combination of 6- described in the preparation of specific embodiment according to the present invention containing diphenyl ether base
The method of object, wherein the molar ratio of first reactant and second reactant is 1.0:1.
The chloro- 2- pyrazinamide class chemical combination of 6- described in the preparation of specific embodiment according to the present invention containing diphenyl ether base
The method of object, wherein the reaction dissolvent is the mixture of alkali, condensing agent and organic solvent.
The chloro- 2- pyrazinamide class chemical combination of 6- described in the preparation of specific embodiment according to the present invention containing diphenyl ether base
The method of object, wherein the organic solvent is methylene chloride, chloroform, n,N-Dimethylformamide or tetrahydrofuran.
The chloro- 2- pyrazinamide class chemical combination of 6- described in the preparation of specific embodiment according to the present invention containing diphenyl ether base
The method of object, wherein the condensing agent is EDCl.
The Chinese of EDCl is 1- ethyl-(3- dimethylaminopropyl) carbodiimide hydrochloride.
The chloro- 2- pyrazinamide class chemical combination of 6- described in the preparation of specific embodiment according to the present invention containing diphenyl ether base
The method of object, wherein the alkali is triethylamine.
Preparation reaction is as follows：
It is also another object of the present invention to provide the chloro- 2- pyrazinamide class compounds of the 6- containing diphenyl ether base described in one kind
Or the application of its pharmaceutically acceptable salt.
The chloro- 2- pyrazinamide class compound of the 6- containing diphenyl ether base of specific embodiment according to the present invention or
The application of its pharmaceutically acceptable salt, the chloro- 2- pyrazinamide class compound of the 6- containing diphenyl ether base or its drug
Application of the acceptable salt as herbicide on.
The chloro- 2- pyrazinamide class compound of the 6- containing diphenyl ether base of specific embodiment according to the present invention
Using, further, the 6- chloropyrazine -2- amides compound containing diphenyl ether base or its pharmaceutically acceptable salt is made
For the application of preventive effect broadleaf weed.
The chloro- 2- pyrazinamide class compound of the 6- containing diphenyl ether base of specific embodiment according to the present invention
Using, further, the chloro- 2- pyrazinamide class compound of the 6- containing diphenyl ether base or its pharmaceutically acceptable salt
Preparing the application in insecticidal materials.Such as：Using containing the 6- chloropyrazine -2- amides compound containing diphenyl ether base or
Its pharmaceutically acceptable salt, the carrier permitted in pharmaceutics or with the compound or its pharmaceutically acceptable salt to live
Property ingredient the mixed combination with pharmaceutical excipient or diluent, prepare insecticidal materials.
Beneficial effects of the present invention are：The chloro- 2- pyrazinamide class compound of 6- containing diphenyl ether base of the invention has and removes
Careless activity and insecticidal effect, can be used as herbicide or insecticidal materials.
The compound of the present invention simple synthetic method, raw material are easy to get, and synthesis cost is low, and product stability is good.
The chloro- 2- pyrazinamide class compound of 6- containing diphenyl ether base of the invention has the cauline leaf process of shepherd's purse preferable
Preventive effect, respectively 99.49% and 98.63%；Also there is very high activity of weeding to Amaranthus retroflexus, inhibiting rate is close to 100%.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, technical solution of the present invention will be carried out below
Detailed description.Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Base
Embodiment in the present invention, those of ordinary skill in the art are obtained all without making creative work
Other embodiment belongs to the range that the present invention is protected.
Embodiment 1
The chloro- N- of 6- (2- Phenoxyphenyl) pyrazine -2- formamide, structural formula are：
Preparation method is：
0.185g (i.e. 1.0mmol) 2- phenoxybenzamine, 0.158g (i.e. 1.0mmol) 6- chlorine pyrrole are added in reaction flask
Then 0.202g (i.e. 2.0mmol) Et is added in piperazine -2- formic acid and 30ml methylene chloride3N adds 0.287mg (1.5mmol)
EDCl, 0.20g (i.e. 1.5mmol) HOBt reacts 2.5 hours at 25 DEG C, and TLC detects fully reacting, and reaction terminates, reaction solution
With water washing 2 times, saturated common salt water washing 1 time, organic phase is dry with anhydrous sodium sulfate, and precipitation obtains crude product, and ethyl alcohol recrystallization obtains
Brick-red solid is the chloro- N- of 6- (2- Phenoxyphenyl) pyrazine -2- formamide, m.p (fusing point)：138-140 DEG C, yield：
79.0%；1H NMR(400MHz,CDCl3)δ：9.62(s,1H,NH),9.58(s,1H,pyrazine), 8.83(s,1H,
), pyrazine 8.54 (s, 1H, C6H4), 7.82 (d, J=8.4Hz, 2H, C6H4), 7.33-7.42 (m, 2H, C6H4),
7.00–7.15(m,4H,C6H5).HRMS(EI)(calcd.m/z)： 325.0612(325.0618,M+).
Embodiment 2
The chloro- N- of 6- (2- Phenoxyphenyl) pyrazine -2- formamide, structural formula are：
Preparation method is：
0.185g (i.e. 1.0mmol) 2- phenoxybenzamine, 0.158g (i.e. 1.0mmol) 6- chlorine pyrrole are added in reaction flask
Then 0.202g (i.e. 2.0mmol) is added in piperazine -2- formic acid and 30ml chloroform (n,N-Dimethylformamide or tetrahydrofuran)
Et3N adds 0.287mg (1.5mmol) EDCl, 0.20g (i.e. 1.5mmol) HOBt, reacts 2.5 hours at 25 DEG C, TLC
Fully reacting is detected, reaction terminates, and reaction solution is with water washing 2 times, and saturated common salt water washing 1 time, organic phase is with anhydrous sodium sulfate
Dry, precipitation obtains crude product, and it is the chloro- N- of 6- (2- Phenoxyphenyl) pyrazine -2- formamide that ethyl alcohol recrystallization, which obtains brick-red solid,
M.p (fusing point)：138-140 DEG C, yield：79.0%；1H NMR(400MHz,CDCl3)δ：9.62(s, 1H,NH),9.58(s,
1H, pyrazine), 8.83 (s, 1H, pyrazine), 8.54 (s, 1H, C6H4), 7.82 (d, J=8.4Hz, 2H, C6H4),
7.33–7.42(m,2H,C6H4),7.00–7.15(m, 4H,C6H5).HRMS(EI)(calcd.m/z)：325.0612
(325.0618,M+)。
Embodiment 3
The structural formula of the chloro- N- of 6- (4- Phenoxyphenyl) pyrazine -2- formamide is：
Preparation method is：
0.185g (i.e. 1.0mmol) 4- phenoxybenzamine, 0.158g (i.e. 1.0mmol) 6- chlorine pyrrole are added in reaction flask
Then 0.202g (i.e. 2.0mmol) Et is added in piperazine -2- formic acid and 30ml methylene chloride3N adds 0.287mg (1.5mmol)
EDCl, 0.20g (i.e. 1.5mmol) HOBt reacts 2.0 hours at 25 DEG C, and TLC detects fully reacting, and reaction terminates, reaction solution
With water washing 2 times, saturated common salt water washing 1 time, organic phase is dry with anhydrous sodium sulfate, and precipitation obtains crude product, and ethyl alcohol recrystallization obtains
White solid, m.p (fusing point)：160-162 DEG C, yield：83.0%；1H NMR(400MHz,CDCl3)δ：9.66(s, 1H,
), NH 9.53 (s, 1H, pyrazine), 8.82 (s, 1H, pyrazine), 8.61 (s, 1H, C6H4), 7.74 (d, J=8.4Hz,
2H,C6H4),7.31–7.39(m,2H,C6H4),6.95–7.13(m, 4H,C6H5).HRMS(EI)(calcd.m/z)：
325.0610(325.0618M+)。
Embodiment 4
The structural formula of the chloro- N- of 6- (4- Phenoxyphenyl) pyrazine -2- formamide is：
Preparation method is：
0.185g (i.e. 1.0mmol) 4- phenoxybenzamine, 0.158g (i.e. 1.0mmol) 6- chlorine pyrrole are added in reaction flask
Then 0.202g (i.e. 2.0mmol) is added in piperazine -2- formic acid and 30ml chloroform (n,N-Dimethylformamide or tetrahydrofuran)
Et3N adds 0.287mg (1.5mmol) EDCl, 0.20g (i.e. 1.5mmol) HOBt, reacts 2.0 hours at 25 DEG C, TLC
Fully reacting is detected, reaction terminates, and reaction solution is with water washing 2 times, saturated common salt water washing 1 time, organic phase anhydrous sodium sulfate
Dry, precipitation obtains crude product, and ethyl alcohol recrystallization obtains white solid, m.p (fusing point)：160-162 DEG C, yield：83.0%； 1H NMR
(400MHz,CDCl3)δ：9.66(s,1H,NH),9.53(s,1H,pyrazine),8.82(s, 1H,pyrazine),8.61
(s, 1H, C6H4), 7.74 (d, J=8.4Hz, 2H, C6H4), 7.31-7.39 (m, 2H, C6H4), 6.95-7.13 (m, 4H,
C6H5).HRMS(EI)(calcd.m/z)：325.0610(325.0618 M+).
The Herbicidal of 6- chloropyrazine -2- amides compound containing diphenyl ether base
Test dose：2000g/hm2。
Test method
Experiment 1：Soil treatment：Herba eleusines indicae, herba digitariae, Descurainia sophia, Chenopodiaceae, Amaranthus retroflexus, shepherd's purse seed are sown into after vernalization shows money or valuables one carries unintentionally
In plastic flowerpot (diameter 10cm, deep 12cm are packed into the loam for being derived from Qingdao Agricultural University campus), every basin sows 10, sowing
Earthing 0.5cm afterwards.Flowerpot after planting is put into the square plate equipped with clear water, is soaked from bottom, and test compound is then sprayed.Point
The compound that other Example 1 and embodiment 3 obtain is dissolved with a small amount of methylene chloride, respectively plus in right amount 1% Tween-80 respectively
Sprayable emulsion is made in aqueous solution, vortex oscillation.Every time when test, 20mL lotion 3WP-2000 type walking spray tower is taken to spray
For mist in flowerpot soil table, spray head is 9501EVS Fan spray head, capacity of sprinkler 450Lha-1.Experiment sets 3 repetitions, comparison liquid
Using the lotion of methylene chloride containing equivalent and Tween-80, flowerpot soil table is sparged.Flowerpot is moved back into laboratory, room temperature after spraying
Culture, as desired by flowerpot bottom-irrigating.It takes within the 21st day after application aerial part to weigh fresh weight, calculates fresh weight inhibition rate.
The calculation method of fresh weight inhibition rate is as follows：
Experiment 2：Cauline leaf process：Herba eleusines indicae, herba digitariae, Descurainia sophia, Chenopodiaceae, Amaranthus retroflexus, shepherd's purse seed are sown into after vernalization shows money or valuables one carries unintentionally
In plastic flowerpot (diameter 10cm, deep 12cm are packed into the loam for being derived from Qingdao Agricultural University campus), every basin sows 5, after planting
Earthing 0.5cm.Flowerpot after planting is soaked from bottom, is cultivated in laboratory to gramineae weed 3-4 leaf phase, broadleaf weeds 4-
The 6 leaf phases, in the lotion to cauline leaf for spraying the compound that embodiment 1 and embodiment 3 obtain.Lotion preparation method and spray condition are same
Experiment 1.Flowerpot is moved back into laboratory after spraying, incubated at room temperature is watered as needed.Experiment sets 3 repetitions, and comparison liquid, which uses, to be contained
The lotion of equivalent methylene chloride and Tween-80, sparges on cauline leaf.It takes within the 21st day after application aerial part to weigh fresh weight, calculates
Fresh weight inhibition rate.The calculation method of fresh weight inhibition rate is as follows：
As a result：By to the general sieve of the activity of weeding for obtaining pyrazinamide analog derivative containing diphenyl ether base, dosage 2000g/
hm2When, cauline leaf is sprayed and soil treatment, as a result such as table 1：
The activity of weeding for the compound that 1 embodiment 1 of table and embodiment 3 obtain
As it can be seen from table 1 the compound that embodiment 1 and embodiment 3 obtain is in 2000g/hm2Under dosage, to shepherd's purse
Cauline leaf process have preferable preventive effect, respectively 99.49% and 98.63%；Also there is very high activity of weeding to Amaranthus retroflexus, inhibits
Rate is close to 100%, activity of weeding with higher.
The insecticidal activity assay of the chloro- 2- pyrazinamide class compound of 6- containing diphenyl ether base
Experimental concentration：500mg/L.
The chloro- N- of 6- made from the embodiment 1 of certain mass (2- Phenoxyphenyl) pyrrole is weighed with assay balance (0.0001g)
The chloro- N- of 6- (4- Phenoxyphenyl) pyrazine -2- formamide made from piperazine -2- formamide and embodiment 3, with containing 1% Tween-80 cream
The DMF dissolution of agent is configured to 1% mother liquor, is then diluted with distilled water spare.
Test method
Spray-on process：It is aphis craccivora for examination target, i.e., respectively sprays the Broad Bean Leaves for connecing aphis craccivora under Potter spray tower
Mist processing, aphis craccivora is placed in 20~22 DEG C of observation ward and cultivates after processing, investigation result after 48h.Polypide is touched with writing brush, without anti-
It should be regarded as dead worm.Test.
Test result
6- made from the chloro- N- of 6- made from embodiment 1 (2- Phenoxyphenyl) pyrazine -2- formamide and embodiment 3 is chloro-
N- (4- Phenoxyphenyl) pyrazine -2- formamide has certain inhibitory activity to aphis craccivora under 500mg/L concentration,
Lead to aphis craccivora food refusal, peels.
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
Those familiar with the art in the technical scope disclosed by the present invention, can easily think of the change or the replacement, and should all contain
Lid is within protection scope of the present invention.Therefore, protection scope of the present invention should be based on the protection scope of the described claims.
Claims (10)
1. a kind of chloro- 2- pyrazinamide class compound of 6- containing diphenyl ether base, which is characterized in that the 6- chlorine containing diphenyl ether base
Pyrazine -2- amides compound has the following structure formula (I) or (II)：
。
2. a kind of method for preparing the chloro- 2- pyrazinamide class compound of the 6- described in claim 1 containing diphenyl ether base, feature
It is, the described method comprises the following steps：With 4- phenoxybenzamine or 2- phenoxybenzamine for the first reactant, with 6- chlorine pyrrole
Piperazine -2- formic acid is the second reactant, the first reactant and the second reactant is dissolved in reaction dissolvent, through single step reaction synthesisization
It closes object (I) or (II).
3. the preparation method of the chloro- 2- pyrazinamide class compound of the 6- according to claim 2 containing diphenyl ether base, feature
It is, the molar ratio of first reactant and second reactant is 1.0:1.
4. the preparation method of the chloro- 2- pyrazinamide class compound of the 6- according to claim 2 containing diphenyl ether base, feature
It is, the reaction dissolvent is the mixture of alkali, condensing agent and organic solvent.
5. the preparation method of the chloro- 2- pyrazinamide class compound of the 6- according to claim 3 containing diphenyl ether base, feature
It is, the organic solvent is methylene chloride, chloroform, n,N-Dimethylformamide or tetrahydrofuran.
6. the preparation method of the chloro- 2- pyrazinamide class compound of the 6- according to claim 2 containing diphenyl ether base, feature
It is, the condensing agent is EDCl.
7. the preparation method of the chloro- 2- pyrazinamide class compound of the 6- according to claim 2 containing diphenyl ether base, feature
It is, the alkali is triethylamine.
8. a kind of chloro- 2- pyrazinamide class compound of 6- as described in claim 1 containing diphenyl ether base or its pharmaceutically may be used
Application of the salt of receiving as herbicide.
9. the chloro- 2- pyrazinamide class compound of the 6- according to claim 8 containing diphenyl ether base or its can pharmaceutically connect
The application for the salt received, which is characterized in that the 6- chloropyrazine -2- amides compound containing diphenyl ether base or its pharmaceutically may be used
Application of the salt of receiving as preventive effect broadleaf weed.
10. a kind of chloro- 2- pyrazinamide class compound of 6- as described in claim 1 containing diphenyl ether base or its pharmaceutically may be used
The salt of receiving is preparing the application in insecticidal materials.
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| CN108997228A (en) * | 2018-07-30 | 2018-12-14 | 陈磊 | The preparation method and application of 6- chloropyrazine -2- amides compound containing diphenyl ether base |
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2018
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| EP1428817A1 (en) * | 2001-09-18 | 2004-06-16 | Ishihara Sangyo Kaisha, Ltd. | ACID AMIDE DERIVATIVES, PROCESS FOR PRODUCING THESE, AND PEST CONTROL AGENT CONTAINING THESE |
| 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 |
| WO2007125749A1 (en) * | 2006-04-26 | 2007-11-08 | Nihon Nohyaku Co., Ltd. | Pyrazinecarboxamide derivative and plant disease-controlling agent comprising the same |
| CN104193675A (en) * | 2014-07-24 | 2014-12-10 | 浙江工业大学 | Nicotinoylhydrazine compound with insecticidal activity as well as preparation method and application of nicotinoylhydrazine compound |
| CN108314656A (en) * | 2018-02-27 | 2018-07-24 | 浙江工业大学 | Unsaturated hydrocarbons pyrimidine thio-ether type compounds and the preparation method and application thereof |
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