CN114249692A - 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot - Google Patents
2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot Download PDFInfo
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- CN114249692A CN114249692A CN202111543293.4A CN202111543293A CN114249692A CN 114249692 A CN114249692 A CN 114249692A CN 202111543293 A CN202111543293 A CN 202111543293A CN 114249692 A CN114249692 A CN 114249692A
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- imidazole
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- benzoyl
- arylamine
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- 241000209140 Triticum Species 0.000 title claims abstract description 77
- 235000021307 Triticum Nutrition 0.000 title claims abstract description 77
- 150000001875 compounds Chemical class 0.000 title claims abstract description 46
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- -1 6-substituted 2-fluorobenzoic acid Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 5
- FJKUOCCQEBLPNX-UHFFFAOYSA-N 8-hydroxyquinoline N-oxide Chemical compound C1=C[N+]([O-])=C2C(O)=CC=CC2=C1 FJKUOCCQEBLPNX-UHFFFAOYSA-N 0.000 claims description 5
- 239000003899 bactericide agent Substances 0.000 claims description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 4
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- JWCPZKNBPMSYND-UHFFFAOYSA-N propan-2-yl 4-aminobenzoate Chemical compound CC(C)OC(=O)C1=CC=C(N)C=C1 JWCPZKNBPMSYND-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
- 229910019213 POCl3 Inorganic materials 0.000 claims description 2
- 229910006124 SOCl2 Inorganic materials 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 241000223195 Fusarium graminearum Species 0.000 abstract description 6
- 241001515802 Pseudofusarium Species 0.000 abstract description 4
- 238000011161 development Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 description 14
- 238000001514 detection method Methods 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 229940064734 aminobenzoate Drugs 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 description 4
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 description 4
- 239000005825 Prothioconazole Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 235000012015 potatoes Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000010902 straw Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- XNTIGDVFBDJLTQ-UHFFFAOYSA-N 2-chloro-6-fluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1Cl XNTIGDVFBDJLTQ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241000233791 Ustilago tritici Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- LBQMIAVIGLLBGW-UHFFFAOYSA-N 2,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1F LBQMIAVIGLLBGW-UHFFFAOYSA-N 0.000 description 1
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 description 1
- MDAZJVAIZVUWDE-UHFFFAOYSA-N 2-bromo-6-fluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1Br MDAZJVAIZVUWDE-UHFFFAOYSA-N 0.000 description 1
- FGGANNUSBMZDMT-UHFFFAOYSA-N C=1C=CC=NC=1C(=O)NC1CCC1 Chemical class C=1C=CC=NC=1C(=O)NC1CCC1 FGGANNUSBMZDMT-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001451172 Fusarium pseudograminearum Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot, which is characterized by having a structure shown in a formula I:
the R is1、R2is-H, -F, -Cl, -Br, -I, -CN, -CF3，‑CHO，‑C1‑C4Alkyl or-C1‑C4or-O-R3And said R is1、R2Not H at the same time; the R is3is-C1‑C4Alkyl or-C1‑C4A haloalkyl or aryl group of (a); said combination ofThe compound I has excellent inhibitory activity on wheat take-all and fusarium graminearum and pseudofusarium graminearum which can cause wheat stem basal rot, and can be simultaneously applied to control of wheat take-all and wheat stem basal rot. The synthesis reaction of the compound I has the advantages of few steps, simple, smooth and safe process and easy purification of products, and is suitable for large-scale synthesis and development.
Description
Technical Field
The invention relates to the field of compounds for preventing and treating crop diseases and insect pests, in particular to a 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot and a preparation method thereof.
Background
Due to the development of agricultural modernization, the agricultural cultivation mode is changed greatly, and straw returning is a main agricultural operation mode. However, because the crop straws have the characteristic of breeding and carrying pathogenic bacteria, the risk and the occurrence degree of crop diseases are increased to a certain extent by returning the straws to the field.
Therefore, in recent years, the occurrence and damage of wheat take-all and wheat stem-base rot are on a trend of increasing year by year, and become a great threat to high quality and high yield of wheat. The development and application of a new medicament for preventing and treating the wheat take-all and wheat stem basal rot play an important role in the development of agricultural modernization. A series of wheat take-all disease control active compounds are disclosed in US005482974A, US006028101A, US005994270A and world patent WO9307751a1, but only silthiopham disclosed in US005486621A is commercially available and used for the control of wheat take-all disease. However, silthiopham is only effective for controlling wheat take-all, and with the continuous use of silthiopham, wheat take-all in some regions has developed resistance thereto, resulting in failure of control. Recently, European Journal of Medicinal Chemistry 200 (2020) 112463 and CN111187227A disclose a triazole benzoylarylamine derivative which has an excellent inhibitory activity against Ustilago tritici and also has an inhibitory activity against pathogenic bacteria causing Ustilago tritici, but the activity is not sufficiently high. WO2020058160A1 discloses a cyclobutyl picolinamide derivative which can be used for controlling wheat basal stem rot, but the activity of controlling wheat take-all is not reported.
Therefore, currently, in the prior art, there are still few varieties of bactericides capable of simultaneously and efficiently preventing and treating various root diseases of wheat, particularly take-all disease and stem rot disease of wheat. Therefore, the problem of providing an active compound capable of simultaneously and efficiently preventing and treating the wheat take-all and the wheat stem basal rot and a preparation method thereof is worthy of research.
Disclosure of Invention
In order to solve the defects in the prior art, the invention provides the 2-imidazole benzoyl arylamine antibacterial active compound which has excellent control effects on wheat take-all and wheat stem rot, cheap and easily-obtained synthetic raw materials, smooth, simple and safe synthetic process and easy purification of products, and the preparation method thereof.
The object of the invention is achieved in that:
a2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot has a structure shown in formula I:
the R is1、R2is-H, -F, -Cl, -Br, -I, -CN, -CF3，-CHO，-C1-C4Alkyl or-C1-C4or-O-R3And said R is1、R2Not H at the same time; the R is3is-C1-C4Alkyl or-C1-C4A haloalkyl or aryl group of (a).
The 2-imidazole benzoyl arylamine active compound is R1、R2is-H, -F, -Cl, -Br, and said R1、R2Not H at the same time, the structure of the catalyst is as follows:
the R is1When it is-F, -Cl, -Br, R2Is H.
The R is1Is F, R2Is H.
A preparation method of 2-imidazole benzoyl arylamine active compounds for preventing and treating wheat take-all and wheat stem rot is characterized in that the active compounds are synthesized in the following mode:
firstly, a substituted 2-fluorobenzoic acid (II) is condensed with 4-aminobenzoic acid isopropyl (III) under a set reaction condition A to obtain an intermediate IV, which is specifically shown as a reaction formula 1:
The reaction condition A is as follows: 1-10 mol equivalent of substituted 2-fluorobenzoic acid (II) including SOCl2、PCl3、POCl3、PCl5Or oxalyl chloride in the presence of a chlorinating agent; in a solvent comprising dichloromethane, chloroform, toluene, N-dimethylformamide, ethyl acetate, THF or acetonitrile at-10oC, reacting for 1-10 hours within the range of reflux temperature to convert into corresponding acyl chloride; reacting with 1-4 molar equivalent of 4-aminobenzoic isopropyl ester (III) in the presence of 0.5-5 molar equivalent of catalyst comprising triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate or potassium acetate at room temperature to reflux temperature for 0.5-10 hours;
or substituted 2-fluorobenzoic acid (II) and 4-aminobenzoic acid isopropyl ester (III) in a solvent comprising dichloromethane, chloroform, toluene, N-dimethylformamide, ethyl acetate, THF or acetonitrile, in the presence of a condensing agent comprising Dicyclohexylcarbodiimide (DCC), Diisopropylcarbodiimide (DIC) or 1- (3-dimethylaminopropyl) -3-Ethylcarbodiimide (EDCI), catalysed by a catalyst comprising 1-hydroxybenzotriazole (HOBt), 4-Dimethylaminopyridine (DMAP) or N-hydroxy-7-azabenzotriazole (HOAt), in the presence of a catalyst comprising 1-hydroxybenzotriazole (HOBt), 4-Dimethylaminopyridine (DMAP) or N-hydroxy-7-azabenzotriazole (HOAt)oC, reacting for 1-15 hours at a reflux temperature to obtain the product;
in the reaction shown in the reaction formula 1, the feeding molar ratio of II to III to the condensing agent is 1: 0.8-5: 0.8-4, and the dosage of the catalyst relative to the substituted 2-fluorobenzoic acid is 0-200 mol%;
the target product I is obtained by reacting an intermediate IV with imidazole under a set condition B, and is specifically shown in a reaction formula 2:
reaction formula 2
The reaction condition B is as follows: the intermediate IV and imidazole are catalyzed by 0-10% molar equivalent of CuI and 8-hydroxyquinoline-N-oxide in a solvent comprising toluene, dimethyl sulfoxide (DMSO) or N, N-Dimethylformamide (DMF) by taking 1-3 molar equivalent of alkali metal carbonate comprising sodium carbonate, potassium carbonate or cesium carbonate as a base and 50-10% molar equivalent of CuI and 8-hydroxyquinoline-N-oxide oC～130 oCWithin the temperature range, reacting for 5-18 hours, and selectively determining whether CuI and 8-hydroxyquinoline-N-oxide are used as catalysts or not;
in the reaction formula 2, the feeding molar ratio of the intermediate IV to imidazole is 1: 0.8-6.
The composition containing the compound I is applied to prevention and control of crop diseases.
Has the positive and beneficial effects that: (1) in the aspect of preventing and treating the wheat take-all disease, the activity of the compound is obviously superior to that of a specific medicament silthiopham for preventing and treating the wheat take-all disease; in the aspect of preventing and treating the basal rot of wheat, the activity of the compound preparation approaches or reaches the activity level of a commercial medicament prothioconazole. Therefore, the compound has the characteristic of simultaneously preventing and treating the wheat take-all and the wheat stem basal rot, and provides alternative methods, measures and choices for preventing and treating the wheat take-all and the wheat stem basal rot and guaranteeing the production safety of wheat. (2) The compound has the advantages of cheap and easily obtained raw materials, short synthesis steps, smooth, simple and safe synthesis process and easy purification of products, thereby being easy to popularize and apply.
Detailed Description
The invention will be further described with reference to specific examples:
example 1
Synthesis of 4- [ (2-imidazol-1-yl) -6-fluorobenzamido ] isopropyl benzoate
Step 1: 5.7 mmol of 2, 6-difluorobenzoic acid was put into a three-neck reaction flask containing 50 mL of dichloromethane and equipped with a reflux and gas absorption device, and 22.7 mmol of thionyl chloride (SOCl) was slowly added under normal temperature conditions2) And 1 ml of DMF, and the temperature is raised to 40oC, heating and reacting for 4 hours. TLC detection reaction is completed, the solvent and excessive thionyl chloride are removed under negative pressure, then 50 mL of fresh toluene is added into the reaction bottle, 6.1 mmol of 4-isopropyl aminobenzoate is weighed and added into the reaction bottle in batches at 100%oReacting for 4 hours at the temperature of C; after TLC detection reaction is finished, neutralizing, washing and desolventizing reaction liquid to obtain a crude product of 4- (2, 6-difluorobenzamide) isopropyl benzoate, and then separating by column chromatography to obtain a white solid;
step 2: 1.5 mmol of isopropyl 4- (2, 6-difluorobenzamido) benzoate, 2.2 mmol of imidazole and 3.0 mmol of anhydrous potassium carbonate (K)2CO3) Put into a three-necked reaction flask containing 20 mL of dimethyl sulfoxide (DMSO) and heated at 100 deg.CoReacting for 12 hours at the temperature of C; filtering after TLC detection reaction, distilling off part of solvent from filtrate under negative pressure, adding 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, distilling off solvent under negative pressure, and separating by column chromatography to obtain white solid 4- [ (2-imidazole-1-yl) -6-fluorobenzamide]Isopropyl benzoate (1). Yield 70%, melting point: 203-205oC；1H NMR (400 Hz, DMSO-d 6)δ: 11.10 (s, 1H), 7.93-7.88 (m, 3H), 7.75-7.67 (m, 3H), 7.55-7.39 (m, 3H), 7.03 (s, 1H), 5.15-5.09 (m, 1H), 1.32-1.30 (d, J = 6.0 Hz, 6H). 13C NMR (100 Hz, DMSO-d 6)δ: 165.1, 161.1, 159.1 (d, J = 245.6 Hz), 142.7, 137.7, 135.9 (d, J = 5.8 Hz), 132.6 (d, J = 9.5 Hz), 130.7, 129.8, 126.2, 122.4 (d, J = 2.6 Hz), 122.2 (d, J = 16.1 Hz), 120.8, 119.5, 116.1 (d, J = 21.3 Hz), 68.4, 22.2。
Example 2
Synthesis of 4- [ (2-imidazol-1-yl) -6-chlorobenzoylamino ] benzoic acid isopropyl ester
Step 1: 5 mmol of 2-fluoro-6-chlorobenzoic acid was put into a three-neck flask containing 50 mL of dichloromethane with reflux and gas absorption device, and 6 mmol of oxalyl chloride (COCl) was slowly added thereto at normal temperature2And several drops of DMF are added, and the reaction is carried out for 4 hours under the condition of heat preservation. TLC detection until the reaction is complete, removing the solvent and excess oxalyl chloride under negative pressure, adding 50 mL of fresh toluene into the reaction flask, weighing 10 mmol of 4-isopropyl aminobenzoate, adding into the reaction flask in batches, and reacting at 100 deg.CoReacting for 4 hours at the temperature of C; after TLC detection reaction is finished, neutralizing, washing and desolventizing reaction liquid to obtain a crude product of 4- (2-fluoro-6-chlorobenzoylamino) isopropyl benzoate, and then separating by column chromatography to obtain a white solid;
step 2: 2 mmol of isopropyl 4- (2-fluoro-6-chlorobenzoylamino) benzoate, 4 mmol of imidazole and 3.0 mmol of anhydrous cesium carbonate (Cs)2CO3) Into a three-necked reaction flask containing 20 mL of N, N-Dimethylformamide (DMF), and heating at 110 deg.CoAnd reacting for 10 hours at the temperature of C. Filtering after TLC detection reaction, distilling off part of solvent from filtrate under negative pressure, adding 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, distilling off solvent under negative pressure, and separating by column chromatography to obtain white solid 4- [ (2-imidazole-1-yl) -6-chlorobenzamide]Isopropyl benzoate (2). Yield 61%, melting point: 182-184oC；1H NMR (400 Hz, DMSO-d 6)δ: 11.06 (s, 1H), 7.92-7.89 (m, 2H), 7.84 (s, 1H), 7.75-7.65 (m, 4H), 7.58-7.56 (dd, J = 1.2 Hz, J = 8.0 Hz, 1H), 7.37 (s, 1H), 7.00 (s, 1H), 5.15-5.08 (m, 1H), 1.32-1.30 (d, J = 6.4 Hz, 6H). 13C NMR (100 Hz, DMSO-d 6)δ: 165.2, 162.9, 142.7, 137.9, 135.9, 133.4, 132.0, 131.4, 130.7, 129.8, 129.7, 126.1, 125.6, 121.1, 119.5, 68.4, 22.2。
Example 3
Synthesis of 4- [ (2-imidazol-1-yl) -6-bromobenzamide ] isopropyl benzoate
Step 1: 5 mmol of 2-fluoro-6-bromobenzoic acid is put into a three-mouth reaction bottle containing 50 mL of dichloromethane and provided with a reflux device and a gas absorption device, and 6 mmol of thionyl chloride SOCl is slowly added under the condition of normal temperature2And a few drops of DMF are added, and the reaction is carried out for 6h under the condition of heat preservation. TLC detection reaction is completed, the solvent and excessive thionyl chloride are removed under negative pressure, then 50 mL of fresh toluene is added into the reaction bottle, 7.5 mmol of 4-isopropyl aminobenzoate is weighed and added into the reaction bottle in batches at 100%oReacting for 6 hours at the temperature of C; after TLC detection reaction is finished, the reaction solution is neutralized, washed and desolventized to obtain a crude product of 4- (2-fluoro-6-bromobenzoylamino) isopropyl benzoate, and then the crude product is separated by column chromatography to obtain a white solid.
Step 2: 2 mmol of isopropyl 4- (2-fluoro-6-bromobenzoylamide) benzoate, 6 mmol of imidazole and 2 mmol of anhydrous cesium carbonate (Cs)2CO3) Into a three-necked reaction flask containing 20 mL of N, N-Dimethylformamide (DMSO), 5 mol% of 8-hydroxyquinoline nitroxide and CuI were added at the same time, and the mixture was stirred at 110 deg.CoAnd reacting for 10 hours at the temperature of C. Filtering after TLC detection reaction, distilling off part of solvent from filtrate under negative pressure, adding 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, distilling off solvent under negative pressure, and separating by column chromatography to obtain white solid which is 4- [ (2-imidazole-1-yl) -6-bromobenzoyl formamide]Isopropyl benzoate (3). Yield 65%, melting point: 135-136oC；1H NMR (400 Hz, DMSO-d 6)δ: 11.0 (s, 1H), 7.92-7.83 (m, 4H), 7.67-7.59 (m, 4H), 7.36 (s, 1H), 6.99 (s, 1H), 5.15-5.08 (m, 1H), 1.32-1.30 (d, J = 6.0 Hz, 6H). 13C NMR (100 MHz, DMSO-d6) δ: 165.2, 163.9, 142.8, 138.0, 135.9, 135.5, 132.9, 132.2, 130.7, 129.6, 126.1, 121.2, 120.5, 119.5, 68.4, 22.2。
Example 4
Synthesis of 4- [ (2-imidazol-1-yl) -5-fluorobenzamido ] isopropyl benzoate
Step 1: 5 mmol of 2, 5-difluorobenzoic acid are placed in a three-neck reaction flask with reflux and gas absorption means and 50 mL of dichloromethane at 0oAdding 7.5 mmol of Dicyclohexylcarbodiimide (DCC) and 1-hydroxybenzotriazole (HOBt) under the condition of C, and stirring for 1h under heat preservation; then 6 mmol of 4-isopropyl aminobenzoate is added into the reaction system at 0 DEGoC, stirring for 1 hour, and then stirring for 6 hours at normal temperature. Then 50 mL of water was added to the reaction flask and filtered. The filtrate is extracted by dichloromethane and desolventized to obtain a crude product of the isopropyl 4- (2, 5-difluorobenzamide) benzoate, and then the crude product is separated by column chromatography to obtain a white solid.
Step 2: 1.5 mmol of isopropyl 4- (2, 5-difluorobenzamido) benzoate, 2.2 mmol of imidazole and 3.0 mmol of anhydrous potassium carbonate (K)2CO3) Put into a three-necked reaction flask containing 20 mL of dimethyl sulfoxide (DMSO) and heated at 100 deg.CoAnd reacting for 12 hours at the temperature of C. Filtering after TLC detection reaction, distilling off part of solvent from filtrate under negative pressure, adding 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, distilling off solvent under negative pressure, and separating by column chromatography to obtain white solid 4- [ (2-imidazole-1-yl) -5-fluorobenzamido]Isopropyl benzoate (4). Yield 53%, melting point 218-oC；1H NMR (400 Hz, DMSO-d 6)δ: 10.80 (s, 1H), 7.92-7.89 (d, J = 8.8 Hz, 2H), 7.81 (s, 1H), 7.71-7.54 (m, 5H), 7.33 (s, 1H), 6.99 (s, 1H), 5.14-5.08 (m, 1H), 1.32-1.30 (d, J = 6.0 Hz, 6H). 13C NMR (100 Hz, DMSO-d 6)δ: 165.2, 164.5, 161.4 (d,J = 245.8 Hz), 143.1, 138.0, 135.4 (d, J = 7.5 Hz), 131.2 (d, J = 2.8 Hz), 130.6, 129.4, 129.1 (d, J = 8.9 Hz), 125.7, 121.3, 119.5, 118.3 (d, J = 22.5 Hz), 116.1 (d, J = 24.5 Hz), 68.4, 22.2。
Activity test of Compounds of examples 1 to 4
The biological activity of the compound is tested by adopting a hypha growth rate method, and the pathogenic bacteria to be tested are wheat take-all pathogen, fusarium graminearum and pseudofusarium graminearum which can cause basal rot of wheat stems, and are respectively from pathology laboratories of plant protection academy of agriculture university in Henan. Firstly, weighing 200 g of peeled fresh potatoes, heating and boiling the potatoes for 20 min by using 1L of distilled water, filtering out uncooked potatoes by using gauze, adding 20 g of glucose and 15 g of agar into filtrate, fully stirring the mixture until the glucose and the agar are completely dissolved, and then fixing the volume to 1L by using the distilled water; then at 120oAnd C, performing moist heat sterilization for 20 minutes, and cooling to obtain the PDA culture medium.
Then, a test sample with proper concentration is prepared by using dimethyl sulfoxide (DMSO) as a solvent, and a proper amount of surfactant Tween is added for standby. Remove 1 mL of the appropriate concentration of test sample solution and melt and cool to 50oFully mixing 9 mL of PDA culture medium of C, and then pouring into a sterile culture dish to cool to room temperature; making the wheat take-all pathogen, fusarium graminearum and pseudofusarium graminearum cultured on a PDA plate for 5 days into fungus cakes by using a puncher with the diameter of 5 mm, then inoculating the fungus cakes in the center of a PDA plate containing the medicine in an inverted manner, and taking a plate culture medium without the medicine as a reference. Each dose was set at 4 concentrations of 100 mg/L, 50 mg/L, 10 mg/L, 1 mg/L, 3 replicates per concentration, at 25oC, culturing in an incubator for 6 days in the dark, investigating the colony diameter, and calculating the relative inhibition rate of each concentration [ relative inhibition rate = (blank control colony growth diameter-medicament treatment colony growth diameter)/blank control colony growth diameter x 100%]. The relative inhibition rates of the various concentrations of the compounds of the examples are shown in table 1:
TABLE 1 bacteriostatic Activity of example Compounds 1-4
The data in the table 1 show that the compound has higher toxicity to wheat take-all pathogen, and the inhibition rate of the compound is obviously superior to that of control medicaments of silthiopham and prothioconazole; on the other hand, the inhibition activity of the compound of the invention on fusarium graminearum and fusarium pseudograminearum which can cause the basal rot of wheat is also obviously superior to that of a control medicament silthiopham, and approaches or reaches the activity level of the control medicament prothioconazole. Therefore, the compound can be simultaneously applied to the control of wheat take-all and wheat stem basal rot, reduces the control times of wheat diseases and the use amount of medicament varieties, and plays an important role in the fine simplification of wheat cultivation and the green control of wheat diseases.
Comparative examples
Synthesis of 4- [ (1,2, 3-triazol-2-yl) -6-chlorobenzamido ] isopropyl benzoate
Step 1: 5 mmol of 2-fluoro-6-chlorobenzoic acid is put into a three-mouth reaction bottle containing 50 mL of dichloromethane and provided with a reflux and gas absorption device, and 6 mmol of thionyl chloride (SOCl) is slowly added under the condition of normal temperature2) And 1 ml of DMF, and reacting for 4 hours under the condition of heat preservation. TLC detection reaction is completed, the solvent and excessive thionyl chloride are removed under negative pressure, then 50 mL of fresh toluene is added into the reaction bottle, 10 mmol of 4-isopropyl aminobenzoate is weighed and added into the reaction bottle in batches, and the mixture is stirred at 100 DEGoAnd reacting for 4 hours at the temperature of C. After TLC detection reaction is finished, the reaction solution is neutralized, washed and desolventized to obtain a crude product of 4- (2-fluoro-6-chlorobenzoylamino) isopropyl benzoate, and then white solid is obtained by column chromatography separation.
Step 2: 2 mmol of isopropyl 4- (2-fluoro-6-chlorobenzoylamino) benzoate, 4 mmol of 2H- (1,2, 3-triazole) and 3.0 mmol of cesium carbonate anhydrous (Cs)2CO3) Into a three-necked reaction flask containing 20 mL of N, N-Dimethylformamide (DMF), and heating at 110 deg.CoAnd reacting for 10 hours at the temperature of C. Filtering after TLC detection reaction, evaporating partial solvent from filtrate under negative pressure, adding 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, and performing negative pressureThe solvent was distilled off, and then separated by column chromatography to give 4- [ (1,2, 3-triazol-2-yl) -6-chlorobenzamide as a white solid]Isopropyl benzoate (2). Yield 32%, melting point: 164-165oC.1H NMR (400 Hz, DMSO-d 6)δ: 10.95 (s, 1H), 8.08 (s, 1H), 8.02-8.00 (dd, J = 3.6 Hz, J = 5.6 Hz, 1H), 7.94-7.92 (d, J = 8.4 Hz, 2H), 7.74-7.69 (m, 4H), 5.16-5.10 (m, 1H), 1.33-1.32 (d, J = 6.0 Hz, 6H). 13C NMR (100Hz, DMSO-d 6)δ: 165.3, 163.1, 143.6, 137.6, 137.4, 132.4, 131.8, 130.7, 129.7, 129.6, 125.5, 121.4, 119.3, 68.3, 22.2。
The evaluation of the activity of the compounds of comparative examples was carried out according to the methods of examples 1 to 4, and the specific results are shown in Table 2.
Table 2 evaluation of bacteriostatic activity of comparative example compound
As can be seen from Table 2, if, for comparison, the imidazole function in the ortho position to the amide of the compound of the invention is replaced by 2HThe activity of the 1,2, 3-triazole on wheat take-all and fusarium graminearum causing wheat stem rot is reduced sharply, and almost no activity is shown under the tested concentration, which indicates that the heterocyclic structure at the ortho position of the amide has specific influence on the activity.
The compound disclosed by the invention has two outstanding advantages: (1) the compound bactericide has excellent inhibition effects on wheat take-all and fusarium graminearum and pseudofusarium graminearum which can cause wheat stem basal rot, can be used for simultaneously preventing and treating wheat take-all and wheat stem basal rot, is obviously superior to control silthiopham and prothioconazole, and provides alternative methods, measures and choices for simultaneously preventing and treating wheat take-all and wheat stem basal rot. (2) The compound has the advantages of cheap and easily-obtained synthetic raw materials, short synthetic steps, smooth, simple and safe synthetic process, easy purification of products, low product cost and easy popularization and application.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes may be made to the present invention by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot is characterized by having a structure shown in a formula I:
the R is1、R2is-H, -F, -Cl, -Br, -I, -CN, -CF3，-CHO，-C1-C4Alkyl or-C1-C4or-O-R3And said R is1、R2Not H at the same time; the R is3is-C1-C4Alkyl or-C1-C4A haloalkyl or aryl group of (a).
2. The 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot according to claim 1, wherein R is1、R2is-H, -F, -Cl, -Br, and said R1、R2Not H at the same time.
3. The 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot according to claim 2, is characterized in that: said R1When it is-F, -Cl, -Br, R2Is H.
4. The 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot according to claim 2, is characterized in that: said R1is-F, R2Is H.
5. A process for the preparation of 2-imidazole benzoyl arylamine active compounds for the control of wheat take-all and wheat stalk rot according to any one of claims 1 to 4, characterized in that they are synthesized by:
6. the preparation method of the 2-imidazole benzoyl arylamine active compound for preventing and treating the wheat take-all and wheat stem rot as claimed in claim 5, characterized in that: the reaction condition A is as follows: 1-10 mol equivalent of substituted 2-fluorobenzoic acid (II) including SOCl2、PCl3、POCl3、PCl5Or oxalyl chloride in a solvent comprising dichloromethane, chloroform, toluene, N-dimethylformamide, ethyl acetate, THF or acetonitrile at-10oC, reacting for 1-10 hours in a reflux temperature range to obtain corresponding acyl chloride, and reacting with 1-4 equivalents of 4-aminobenzoic acid isopropyl ester (III) in the presence of 0.5-5 molar equivalents of a catalyst comprising triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate or potassium acetate for 0.5-10 hours at a room temperature to reflux temperature;
or substituted 2-fluorobenzoic acid (II) and 4-aminobenzoic acid isopropyl ester (III) in a solvent comprising dichloromethane, chloroform, toluene, N-dimethylformamide, ethyl acetate, THF or acetonitrile, in the presence of a condensing agent comprising Dicyclohexylcarbodiimide (DCC), Diisopropylcarbodiimide (DIC) or 1- (3-dimethylaminopropyl) -3-Ethylcarbodiimide (EDCI), catalysed by a catalyst comprising 1-hydroxybenzotriazole (HOBt), 4-Dimethylaminopyridine (DMAP) or N-hydroxy-7-azabenzotriazole (HOAt), in the presence of a catalyst comprising 1-hydroxybenzotriazole (HOBt), 4-Dimethylaminopyridine (DMAP) or N-hydroxy-7-azabenzotriazole (HOAt)oC, reacting for 1-15 hours at a reflux temperature to obtain the product;
in the reaction of the reaction formula 1, the feeding molar ratio of II to III and the condensing agent is 1: 0.8-5: 0.8-4, and the dosage of the catalyst is 0-200 mol% relative to 5, 6-substituted 2-fluorobenzoic acid.
7. The preparation method of the 2-imidazole benzoyl arylamine active compound for preventing and treating the wheat take-all and wheat stem rot as claimed in claim 5, wherein the reaction condition B is as follows: reacting the intermediate IV and imidazole in a solvent comprising toluene, dimethyl sulfoxide (DMSO) or N, N-Dimethylformamide (DMF) for 5-18 hours at the temperature of 50-130 ℃ under the catalysis of 0-10% molar equivalent of CuI and 8-hydroxyquinoline-N-oxide by taking 1-3 molar equivalents of alkali carbonate comprising sodium carbonate, potassium carbonate or cesium carbonate as a base; i.e., the selectivity, determines whether to use CuI and 8-hydroxyquinoline-N-oxide as catalysts or no catalyst.
8. The preparation method of the 2-imidazole benzoyl arylamine active compound for preventing and treating the wheat take-all and wheat stem rot as claimed in claim 5, characterized in that: in the reaction formula 2, the feeding molar ratio of the intermediate IV to imidazole is 1: 0.8-6.
9. Use of an active compound of the 2-imidazole benzoyl arylamine type according to claim 1,2,3 or 4, characterized in that: the composition containing the active compound can be applied to the control of crop diseases including wheat take-all and wheat stem rot.
10. Use of an active compound of the 2-imidazole benzoyl arylamine type according to claim 1,2,3 or 4, characterized in that: the active compound component and the agriculturally acceptable carrier form a bactericide or the active compound component, other bactericidal active components and the agriculturally acceptable carrier form a bactericide in a composite manner, and the bactericide can be applied to prevention and treatment of crop diseases.
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