CN115677536A - Synthetic method and application of cyantraniliprole and derivatives thereof - Google Patents
Synthetic method and application of cyantraniliprole and derivatives thereof Download PDFInfo
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- CN115677536A CN115677536A CN202211341291.1A CN202211341291A CN115677536A CN 115677536 A CN115677536 A CN 115677536A CN 202211341291 A CN202211341291 A CN 202211341291A CN 115677536 A CN115677536 A CN 115677536A
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- phenamacril
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- 239000005889 Cyantraniliprole Substances 0.000 title description 3
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 title description 3
- YKRQBWKLHCEKQH-KHPPLWFESA-N ethyl (z)-3-amino-2-cyano-3-phenylprop-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/N)C1=CC=CC=C1 YKRQBWKLHCEKQH-KHPPLWFESA-N 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- -1 imine hydrochloride Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 13
- 241000209140 Triticum Species 0.000 claims abstract description 11
- 235000021307 Triticum Nutrition 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 10
- 206010039509 Scab Diseases 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 6
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000008359 benzonitriles Chemical class 0.000 claims abstract description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 9
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 238000003756 stirring Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000003899 bactericide agent Substances 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000223195 Fusarium graminearum Species 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- CDUQMGQIHYISOP-UHFFFAOYSA-N 2-cyano-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(C#N)=CC1=CC=CC=C1 CDUQMGQIHYISOP-UHFFFAOYSA-N 0.000 description 2
- DLWNSEPEXSGNLO-UHFFFAOYSA-N 3-chloro-2-cyano-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(C#N)=C(Cl)C1=CC=CC=C1 DLWNSEPEXSGNLO-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 241000784413 Fusarium asiaticum Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000006013 carbendazim Substances 0.000 description 2
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LINOMUASTDIRTM-QGRHZQQGSA-N deoxynivalenol Chemical compound C([C@@]12[C@@]3(C[C@@H](O)[C@H]1O[C@@H]1C=C(C([C@@H](O)[C@@]13CO)=O)C)C)O2 LINOMUASTDIRTM-QGRHZQQGSA-N 0.000 description 2
- 229930002954 deoxynivalenol Natural products 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- LINOMUASTDIRTM-UHFFFAOYSA-N vomitoxin hydrate Natural products OCC12C(O)C(=O)C(C)=CC1OC1C(O)CC2(C)C11CO1 LINOMUASTDIRTM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NZAGWJNJPABEAE-UHFFFAOYSA-N 2-bromo-2-cyanoacetic acid Chemical compound OC(=O)C(Br)C#N NZAGWJNJPABEAE-UHFFFAOYSA-N 0.000 description 1
- JLQRIXWUYHCQNC-UHFFFAOYSA-N 2-chloro-3-phenylprop-2-enenitrile Chemical group N#CC(Cl)=CC1=CC=CC=C1 JLQRIXWUYHCQNC-UHFFFAOYSA-N 0.000 description 1
- WLKDAZQHOLJYQE-UHFFFAOYSA-N 2-cyano-3-(2,3-dichlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C(C#N)=CC1=CC=CC(Cl)=C1Cl WLKDAZQHOLJYQE-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 1
- XDJAAZYHCCRJOK-UHFFFAOYSA-N 4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1 XDJAAZYHCCRJOK-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000221778 Fusarium fujikuroi Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthetic method and application of phenamacril and derivatives thereof. In the method, cyanobenzene or substituted cyanobenzene is used as a raw material, and an imine hydrochloride intermediate is obtained by the processes of low-temperature stirring, crystallization and the like in an ethanol solution of hydrogen chloride. In an ethanol solution, the intermediate is further reacted with ethyl cyanoacetate in a reflux manner, and the phenamacril is obtained after separation and purification. The method has the characteristics of simple preparation process, high product yield and the like. The prepared phenamacril and derivatives thereof have control effects on wheat scab.
Description
Technical Field
The invention relates to the technical field of pesticides, and particularly relates to a synthetic method and application of phenamacril and derivatives thereof.
Background
Cyanostrobin (Phenaacril, 2-cyano-3-amino-3-ethyl phenylacrylate, test code: JS399-19, CAS 3336-69-4), belongs to 2-cyanoacrylate bactericides, and is synthesized by Jiangsu base, the national center for pesticide creation in the south, 1998. The bactericide enters a field test in 2001 and obtains a Chinese invention patent, and temporary registration of pesticides is completed in 2007. The novel compound suspending agent has novel structure and unique action mode, and the original drug and 25 percent of the suspending agent are slightly toxic and safe to the environment. Through popularization and application in recent years, the sale amount of the phenamacril leaps the first place of creating pesticides in China.
The cyhalothrin is a fusarium specialized bactericide, has strong inhibition effect on the growth of hyphae of fusarium graminearum (fusarium graminearum), fusarium asiaticum (f.asiaticum), bakanae rice (f.fujikuroi) and the like, has good protection and treatment effect on wheat scab and bakanae rice bakanae disease in fields, is superior to carbendazim with the same dosage, and becomes a novel bactericide for preventing and treating wheat scab and bakanae rice disease. The cyhalothrin-methyl not only can effectively treat the drug-resistant group of carbendazim in the field and prevent and control the occurrence of wheat scab, but also can delay the wheat aging, increase the wheat yield and reduce the pollution level of Deoxynivalenol (DON) toxin, has no cross resistance with the existing bactericide, and has novel action mechanism.
The synthetic method of the phenamacril has been reported more. In 1943, it was reported that amidine and cyanoacetate are condensed to produce two products, wherein the yield of the target product is only 28%, and the yield of the method is very low and difficult to purify. The synthetic method reported in 1973 is that 3-phenyl-cyanoacrylate and chlorine are added to generate 2,3_ dichloro-3-phenyl-2-cyanoacrylate, then the elimination reaction is carried out in the presence of an acid binding agent or at high temperature to obtain 3-chloro-3-phenyl-2-cyanoacrylate, and finally the 3-chloro-3-phenyl-2-cyanoacrylate and ammonia water are mixed to obtain the target product. The yield of the benzene line is very low, and most of the product is 2-chloro-3-phenyl acrylonitrile which is a byproduct. The preparation method by directly reacting various (substituted) thiobenzoyl with 2-bromocyanoacetate was reported in 1976, but had the problem that the raw material was difficult to obtain. In 1983, the following methods were reported in the literature: the method is characterized by comprising the steps of firstly, carrying out addition reaction on 3-phenyl-2-cyanoacrylate and triethyl phosphite, then brominating and eliminating the product, and finally reacting the product with ammonia water. 2014 reports a method using benzonitrile as a raw material, namely introducing hydrogen chloride gas into an ethanol solution to obtain an imine hydrochloride intermediate, and refluxing the imine hydrochloride intermediate and ethyl cyanoacetate in the ethanol solution to obtain the phenamacril. The method needs to continuously introduce hydrogen chloride gas, and is dangerous.
Analyzing the synthesis method of the phenamacril and the derivatives thereof, the problems existing in the synthesis process are that raw materials which are difficult to obtain are needed and the reaction conditions are harsh.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a simple and reliable method for synthesizing the phenamacril and the derivatives thereof. The invention aims to solve another technical problem of providing the pesticide application of the phenamacril and the derivatives thereof.
In order to solve the technical problems, the invention adopts the technical scheme that:
a method for synthesizing phenamacril and derivatives thereof comprises the steps of taking cyanobenzene or substituted cyanobenzene as a raw material, stirring at low temperature in an ethanol solution of hydrogen chloride, and performing suction filtration to obtain an imine hydrochloride intermediate; then refluxing imine hydrochloride and ethyl cyanoacetate in ethanol solution, and obtaining the phenamacril or derivatives thereof by silica gel column chromatography.
The method for synthesizing the cyantraniliprole and the derivatives thereof is characterized in that the concentration of hydrogen chloride in an ethanol solution of the hydrogen chloride is not less than 3 mol.L -1 。
The synthesis method of the cyanamide and the derivatives thereof has the advantage that the reaction time of the imine hydrochloride is 24-48 hours.
The method for synthesizing the cyanamide and the derivatives thereof uses benzonitrile as a raw material, and obtains an imine hydrochloride intermediate through ethanol solution of hydrogen chloride and suction filtration.
The imine hydrochloride intermediate prepared has the following structural formula:
the synthesis method of the phenamacril and the derivatives thereof has the specific reaction formula:
the structure formula of the prepared phenamacril is as follows:
the obtained phenamacril can be used for preventing and treating wheat scab.
Has the advantages that: compared with the prior art, the synthesis method is simple and reliable, the product yield is high, the prepared imine hydrochloride intermediate can be used for preparing the phenamacril, and the prepared phenamacril has good control effect on wheat scab.
Detailed Description
The present invention will be described in further detail with reference to examples.
EXAMPLE 1 Synthesis of imine hydrochloride
Synthesis of imine hydrochloride: 4-Methoxybenzonitrile (8.4 mmol) and 1,2-dichloroethane (2 mL) were sequentially added to a 50mL single-necked flask, and stirred at low temperature for 15min, then anhydrous ethanol-hydrogen chloride solution (84 mmol) was added, and stirring at low temperature was continued for 1.5d. After standing at low temperature and suction filtration, 0.60g (3.62 mmol) of yellow solid is obtained with a yield of 42.86%.
1 H NMR(300MHz，DMSO-d6)δ11.12(s，1H，H-NH)，8.03(dd，J＝8.9，1.8Hz，2H，H-3，5)，7.00(dd，J＝8.9，1.8Hz，2H，H-2，6)，4.65-4.51(m，2H，H-8)，1.46(td，J＝7.0，1.7Hz，3H，H-9)； 13 C NMR(75MHz，DMSO-d6)δ170.63，164.81，132.12，129.86，116.50，115.95，69.39，19.25，13.98.ESI-MS Calculated for：C 9 H 12 NO + [M+H] + ：150.0913，found：150.0919。
Example 2 Synthesis of Cyanoxastrobin
The intermediate 1 (3.62 mmol) and ethanol (10 mL) were added sequentially to a 25mL three-necked flask, triethylamine (4 mmol) was added dropwise, stirring was carried out for 0.5h, the temperature was raised under reflux, ethyl cyanoacetate (3 mmol) was added, and the reflux was continued for 6h. After cooling to room temperature, the solvent was distilled off under reduced pressure, 10mL of DCM was added to dissolve the extract, 15mL of water was washed with the organic phase (. Times.3), 15mL of saturated brine was washed with water (. Times.3), dried over anhydrous sodium sulfate, suction filtered, distilled under reduced pressure, and subjected to silica gel column chromatography (PE: EA = I: 1) to obtain 252mg (1.08 mmol) of a white product with a yield of 33.94%.
1 H-NMR(300MHz，CDCl 3 )δ9.44(s，1H，H-NH 2 )，7.70-7.57(m，2H，H-3，5)，7.20(t，J＝8.5Hz，2H，H-2，6)，5.71(s，1H，H-NH 2 )，4.31(q，J＝7.1Hz，2H，H-11)，1.38(t，J＝7.1Hz，3H，H-12)； 13 C NMR(75MHz，CDCl3)δ168.17，167.44，129.96，129.36，129.25，117.65，115.87，115.58，76.58，60.33，13.70。
Example 3 indoor virulence determination of Cyanostrobin on Gibberella zeae
The indoor toxicity of the phenamacril and the derivatives thereof to the wheat scab germ is measured by adopting a hypha growth rate method for the synthesized compound. Inoculating the PH-1 strain on a PDA culture medium plate, growing for 3 days in an incubator at 25 ℃, punching a bacterial dish with the diameter of 5mm on the growth edge of a bacterial colony by using a puncher, and then inoculating the bacterial dish on the PDA culture medium plate containing the phenamacril with different concentration gradients. Each strain was measured after continuous culture in an incubator at 25 ℃ for 3 to 5 daysThe hypha growth inhibition ratio was calculated according to the following formula with respect to the colony diameter of (1) with respect to the strain grown on the plate containing no agent as a control, and the experiment was repeated 2 times with 3 repetitions of each treatment. According to the logarithm (X) of the concentration of the medicament and the probability value (Y) corresponding to the inhibition ratio, calculating the cyanogen alkene bacterium ester EC of the strain 50 。
Indoor toxicity EC of Cyanostrobin against wheat scab 50 It was 0.2622. Mu.g/mL.
Claims (7)
1. A synthetic method of cyanamide and derivatives thereof is characterized in that benzonitrile or substituted benzonitrile is used as a raw material, stirred at low temperature in an ethanol solution of hydrogen chloride, and filtered to obtain an imine hydrochloride intermediate; then refluxing the mixture of imine hydrochloride and ethyl cyanoacetate in an ethanol solution, and carrying out silica gel column chromatography to obtain the phenamacril.
2. The method for synthesizing the phenamacril and the derivatives thereof according to claim 1, wherein the concentration of the hydrogen chloride in the ethanol solution of the hydrogen chloride is not less than 3 mol.L -1 。
3. The method for synthesizing the cyanamide and the derivatives thereof as claimed in claim 1, wherein the reaction time for synthesizing the imine hydrochloride is 24-48 hours.
4. The method for synthesizing the cyanoenamine ester and derivatives thereof according to claim 1, wherein the structural formula of the imine hydrochloride intermediate is:
5. the method for synthesizing the cyanamide and the derivatives thereof according to claim 1, characterized in that the specific reaction formula is:
6. an imine hydrochloride intermediate obtained by the synthetic method of any one of claims 1 to 5, phenamacril, or a derivative thereof.
7. The application of the phenamacril and the derivatives thereof in preventing and treating wheat scab.
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