CN114249692B - 2-imidazole benzamide active compound for preventing and treating wheat take-all and wheat stem basal rot - Google Patents
2-imidazole benzamide active compound for preventing and treating wheat take-all and wheat stem basal rot Download PDFInfo
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- 241000209140 Triticum Species 0.000 title claims abstract description 82
- 235000021307 Triticum Nutrition 0.000 title claims abstract description 82
- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 44
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 65
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 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
- 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 13
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 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
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 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
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002360 preparation method Methods 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 3
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
- -1 6-substituted 2-fluorobenzoic acid Chemical class 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
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 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
- 239000003899 bactericide agent Substances 0.000 claims 2
- KAJZGRFYZKWYDX-UHFFFAOYSA-N benzalamide Chemical compound NC(=O)CC(C)=CC1=CC=CC=C1 KAJZGRFYZKWYDX-UHFFFAOYSA-N 0.000 claims 2
- 229950008586 benzalamide Drugs 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 241000223195 Fusarium graminearum Species 0.000 abstract description 7
- 241001451172 Fusarium pseudograminearum Species 0.000 abstract description 4
- 238000011161 development Methods 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 241000894006 Bacteria Species 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 238000001514 detection method Methods 0.000 description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 9
- 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
- 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
- 239000000047 product 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
- 239000005825 Prothioconazole Substances 0.000 description 4
- 238000010521 absorption reaction Methods 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 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000010902 straw Substances 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
- HCGLAUOYDLTCJV-UHFFFAOYSA-N 2-cyclobutylpyridine Chemical compound C1CCC1C1=CC=CC=N1 HCGLAUOYDLTCJV-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 244000052616 bacterial pathogen Species 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
- 239000001963 growth medium Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000012360 testing method 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
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 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 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 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
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment 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
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 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
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (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 is 1 、R 2 is-H, -F, -Cl, -Br, -I, -CN, -CF 3 ，‑CHO，‑C 1 ‑C 4 Alkyl or-C of (2) 1 ‑C 4 Haloalkyl or-O-R 3 And said R 1 、R 2 Not simultaneously H; the R is 3 is-C 1 ‑C 4 Alkyl or-C of (2) 1 ‑C 4 Haloalkyl or aryl; the compound I has excellent inhibitory activity on wheat take-all bacteria and fusarium graminearum and fusarium pseudograminearum which can cause wheat stem rot, and can be simultaneously applied to control of the wheat take-all and the wheat stem rot. The synthesis reaction of the compound I has few steps, simple, smooth and safe process, and the product is easy to purify and suitable for large-scale synthesis and development.
Description
Technical Field
The invention relates to the field of compounds for preventing and controlling crop diseases and insect pests, in particular to a 2-imidazole benzoyl aromatic amine active compound for preventing and controlling wheat take-all and wheat stem rot and a preparation method thereof.
Background
The development of agricultural modernization greatly changes the agricultural cultivation mode, and straw returning becomes a main operation mode of agriculture. However, because crop straws have the characteristics of breeding and carrying pathogenic bacteria, the occurrence risk and 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 hazard of wheat take-all disease and wheat stem-based rot tend to be aggravated year by year, and the occurrence and hazard of wheat take-all disease and wheat stem-based rot become a great threat for high quality and high yield of wheat. Development and application of new agents for preventing and treating wheat take full rot and wheat stem rot play an important role in development of agricultural modernization. U.S. patent No. 005482974A, US006028101A, US005994270a and world patent No. WO9307751A1 disclose a series of wheat take-all controlling active compounds, but only silthiopham disclosed in U.S. patent No. 005486621a is commercially available and used for the control of wheat take-all. However, silthiopham is effective only for controlling wheat take-all, and with continued use of silthiopham, wheat take-all in a part of areas has developed resistance thereto, resulting in failure of control. Recently, european Journal of Medicinal Chemistry (2020) 112463 and CN111187227a disclose triazole benzamide derivatives which have excellent inhibitory activity against wheat take-all pathogens, but the activity is not sufficiently high although they have inhibitory activity against pathogens causing wheat stem rot. WO2020058160A1 discloses a cyclobutyl pyridine amide derivative which can be used for preventing and treating wheat stem rot, but the preventing and treating activity of the cyclobutyl pyridine amide derivative on wheat take-all is not reported yet.
Therefore, few germicides capable of simultaneously and efficiently preventing and treating various root diseases of wheat, especially wheat take-all and wheat stem-based rot exist in the prior art. Thus, the active compound capable of simultaneously and efficiently preventing and treating wheat take-all and wheat stem-based rot and the preparation method thereof are a problem worthy of research.
Disclosure of Invention
In order to solve the defects in the prior art, the invention provides the 2-imidazole benzoyl aromatic amine antibacterial active compound which has excellent control effect on wheat take-all and wheat stem rot, has cheap and easily available synthetic raw materials, smooth and simple synthetic process, is safe and is easy to purify the product, and the preparation method thereof.
The object of the invention is achieved in that:
2-imidazole benzamide active compound for preventing and treating wheat take-all and wheat stem basal rot has a structure shown in a formula I:
the R is 1 、R 2 is-H, -F, -Cl, -Br, -I, -CN, -CF 3 ，-CHO，-C 1 -C 4 Alkyl or-C of (2) 1 -C 4 Haloalkyl or-O-R 3 And said R 1 、R 2 Not simultaneously H; the R is 3 is-C 1 -C 4 Alkyl or-C of (2) 1 -C 4 Haloalkyl or aryl groups of (a).
The active compound of the 2-imidazole benzamide and the R 1 、R 2 is-H, -F, -Cl, -Br, and R is 1 、R 2 And not simultaneously H, and comprises the following structures:
the R is 1 When the compound is-F, -Cl, -Br, R 2 H.
The R is 1 Is F, R 2 H.
A preparation method of a 2-imidazole benzamide active compound for preventing and treating wheat take-all and wheat stem rot, wherein the active compound is synthesized by the following steps:
firstly, condensing the substituted 2-fluorobenzoic acid (II) with isopropyl 4-aminobenzoate (III) under a set reaction condition A to obtain an intermediate IV, wherein the intermediate IV is specifically shown as a reaction formula 1:
reaction 1
The reaction condition A is as follows: 1 to 10 molar equivalents of substituted 2-fluorobenzoic acid (II) comprising SOCl 2 、PCl 3 、POCl 3 、PCl 5 Or oxalyl chloride in the presence of a chlorinating agent; in a solvent comprising dichloromethane, chloroform, toluene, N-dimethylformamide, ethyl acetate, THF or acetonitrile at-10 o C, reacting for 1-10 hours in a reflux temperature range to convert into corresponding acyl chloride; then in the presence of 0.5-5 molar equivalents of catalyst comprising triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate or potassium acetate, reacting with 1-4 molar equivalents of isopropyl 4-aminobenzoate (III) for 0.5-10 hours at room temperature to reflux temperature;
or substituted 2-fluorobenzoic acid (II) and isopropyl 4-aminobenzoate (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) in the presence of a catalyst comprising 1-hydroxybenzotriazole (HOBt), 4-Dimethylaminopyridine (DMAP) or N-hydroxy-7-azabenzotriazol (HOAt), in the presence of a catalyst comprising-10 o C, reacting for 1-15 hours at the reflux temperature;
in the reaction of the reaction formula 1, the feeding mole ratio of II to III and 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 percent;
the target product I is obtained by reacting an intermediate IV with imidazole under a set condition B, and is specifically shown as a reaction formula 2:
reaction 2
The reaction condition B is as follows: intermediate IV and imidazole in a solvent comprising toluene, dimethylsulfoxide (DMSO) or N, N-Dimethylformamide (DMF) in 1 to 3 molar equivalents comprising sodium carbonate, potassium carbonate orAlkali metal carbonate of cesium carbonate is used as alkali, and is catalyzed by 0 to 10 mol percent of equivalent CuI and 8-hydroxyquinoline-N-oxide at 50 percent oC ～130 oC In the temperature range, the reaction is carried out for 5 to 18 hours, and whether CuI and 8-hydroxyquinoline-N-oxide are used as catalysts or not can be selectively determined;
in the reaction formula 2, the feeding mole ratio of the intermediate IV to the imidazole is 1:0.8-6.
The composition containing the compound I is applied to the control of crop diseases.
Has the positive beneficial effects that: (1) The activity of the compound in the aspect of preventing and treating wheat take-all disease is obviously superior to that of the special-effect medicament silthiopham for preventing and treating wheat take-all disease; in the aspect of preventing and controlling the wheat stem basal rot, the activity of the composition is close to or reaches the activity level of the commercial medicament prothioconazole. Therefore, the compound has the characteristic of simultaneously preventing and treating wheat take-all and wheat stem rot, and provides an alternative method, measure and selection for preventing and treating wheat take-all and wheat stem rot and guaranteeing wheat production safety. (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 is further illustrated by the following examples:
example 1
Synthesis of isopropyl 4- [ (2-imidazol-1-yl) -6-fluorobenzamido ] benzoate
Step 1: 5.7 mmol of 2, 6-difluorobenzoic acid was introduced into a three-port reaction flask containing 50 mL dichloromethane and equipped with reflux and gas absorption means, and 22.7 mmol of thionyl chloride (SOCl) was slowly added at room temperature 2 ) And 1 ml DMF, heating to 40 o C continues to heat reaction 4 h. TLC detection reaction is completed, solvent is removed under negative pressure andexcess thionyl chloride was then added to the reaction flask with 50. 50 mL fresh toluene and 6.1 mmol isopropyl 4-aminobenzoate was weighed and added to the reaction flask in portions at 100 o Reaction 4 h at temperature C; after the TLC detection reaction is finished, the reaction solution is neutralized, washed and desolventized to obtain a crude product of isopropyl 4- (2, 6-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, 6-difluorobenzamide) benzoate, 2.2 mmol of imidazole and 3.0 mmol of anhydrous potassium carbonate (K 2 CO 3 ) Putting into a three-port reaction bottle containing 20 mL dimethyl sulfoxide (DMSO) at 100 o Reaction 12 h at temperature C; filtering after TLC detection reaction, evaporating part of solvent from filtrate under negative pressure, adding 20. 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, evaporating solvent under negative pressure, and separating by column chromatography to obtain white solid which is 4- [ (2-imidazole-1-yl) -6-fluorobenzamide]Isopropyl benzoate (1). Yield 70%, melting point: 203-205 o C； 1 H 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). 13 C 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 isopropyl 4- [ (2-imidazol-1-yl) -6-chlorobenzoylamino ] benzoate
Step 1: 5 mmol of 2-fluoro-6-chlorobenzoic acid is put into a three-port reaction bottle containing 50 mL methylene dichloride and provided with a reflux and gas absorption device, and the reaction bottle is slowly operated at normal temperatureOxalyl chloride (COCl) was added in an amount of 6 mmol 2 And a few drops of DMF, incubation reaction 4 h. TLC detection reaction was completed, solvent and excess oxalyl chloride were removed under negative pressure, then 50 mL fresh toluene was added to the reaction flask, and 10 mmol of isopropyl 4-aminobenzoate was added to the reaction flask in portions, at 100 o Reaction 4 h at temperature C; after the TLC detection reaction is finished, the reaction solution is neutralized, washed and desolventized to obtain a crude product of isopropyl 4- (2-fluoro-6-chlorobenzoylamino) benzoate, and then a white solid is obtained through column chromatography separation;
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 2 CO 3 ) Put into a three-port reaction flask with 20 mL of N, N-Dimethylformamide (DMF), at 110 o The reaction was carried out at C for 10 hours. Filtering after TLC detection reaction, evaporating part of solvent from filtrate under negative pressure, adding 20. 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, evaporating solvent under negative pressure, and separating by column chromatography to obtain white solid which is 4- [ (2-imidazole-1-yl) -6-chlorobenzoylamino]Isopropyl benzoate (2). Yield 61%, melting point: 182-184 o C； 1 H 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). 13 C 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 isopropyl 4- [ (2-imidazol-1-yl) -6-bromobenzamide ] benzoate
Step 1: 5 mmol of 2-fluoro-6-bromobenzoic acid are introduced into a solution of 50 mL dichloromethane with reflux and gas6 mmol of thionyl chloride SOCl is slowly added into a three-port reaction bottle of an absorption device under the normal temperature condition 2 And a few drops of DMF, incubation reaction 6h. TLC detection of the reaction was completed, the solvent and excess thionyl chloride were removed under negative pressure, then 50. 50 mL fresh toluene was added to the reaction flask, and 7.5 mmol of isopropyl 4-aminobenzoate was added to the reaction flask in portions at 100 o Reaction 6h at temperature C; after the TLC detection reaction is finished, the reaction liquid is neutralized, washed and desolventized to obtain a crude product of isopropyl 4- (2-fluoro-6-bromobenzamide) benzoate, and then a white solid is obtained through column chromatography separation.
Step 2: 2 mmol of isopropyl 4- (2-fluoro-6-bromobenzamide) benzoate, 6 mmol of imidazole and 2 mmol of anhydrous cesium carbonate (Cs 2 CO 3 ) Put into a three-port reaction flask with 20 mL of N, N-Dimethylformamide (DMSO), 5 mol% of 8-hydroxyquinoline oxynitride and CuI are added at the same time, at 110 o The reaction was carried out at C for 10 hours. Filtering after TLC detection reaction, evaporating part of solvent from filtrate under negative pressure, adding 20. 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, evaporating solvent under negative pressure, and separating by column chromatography to obtain white solid which is 4- [ (2-imidazole-1-yl) -6-bromobenzamide]Isopropyl benzoate (3). Yield 65%, melting point: 135-136 o C； 1 H 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). 13 C NMR (100 MHz, DMSO-d 6 ) 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 isopropyl 4- [ (2-imidazol-1-yl) -5-fluorobenzamido ] benzoate
Step 1: 5 mmol of 2, 5-difluorobenzoic acid was put into a solution containing 50 mL dichloroIn a three-port reaction flask with reflux and gas absorbing device for methane, the reaction flask is 0 o Under the condition of C, 7.5 mmol Dicyclohexylcarbodiimide (DCC) and 1-hydroxybenzotriazole (HOBt) are added, and the mixture is stirred for 1h under the condition of heat preservation; then 6 mmol of isopropyl 4-aminobenzoate was added to the reaction system at 0 o C is stirred for 1 hour, and then stirred for 6 hours at normal temperature. Then 50 mL water was added to the reaction flask and filtered. The filtrate is extracted with methylene dichloride, desolventized to obtain a crude product of 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-difluorobenzamide) benzoate, 2.2 mmol of imidazole and 3.0 mmol of anhydrous potassium carbonate (K 2 CO 3 ) Putting into a three-port reaction bottle containing 20 mL dimethyl sulfoxide (DMSO) at 100 o Reaction 12 h at temperature C. Filtering after TLC detection reaction, evaporating part of solvent from filtrate under negative pressure, adding 20. 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, evaporating solvent under negative pressure, and separating by column chromatography to obtain white solid which is 4- [ (2-imidazole-1-yl) -5-fluorobenzamide]Isopropyl benzoate (4). Yield 53%, melting point 218-219 o C； 1 H 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). 13 C 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 tested pathogenic bacteria are wheat take-all pathogen, fusarium graminearum and Fusarium pseudograminearum which can cause wheat stem basal rot and are respectively from pathology laboratories of plant protection college of Henan agricultural university. Firstly, 200 parts of g are weighed out and peeledBoiling the fresh potato with distilled water 1L for 20 min, filtering out the uncooked potato with gauze, adding glucose 20 g and agar 15 g into the filtrate, stirring thoroughly until it is completely dissolved, and fixing volume with distilled water to 1L; then at 120 o And C, carrying out damp heat sterilization for 20 minutes, and cooling to obtain the PDA culture medium.
Then, a sample for test with proper concentration is prepared by taking dimethyl sulfoxide (DMSO) as a solvent, and a proper amount of surfactant Tween is added for standby. Remove a sample solution 1 mL of a suitable concentration and melt and cool to 50 o PDA medium 9 mL of C was thoroughly mixed and then poured into sterile petri dishes to cool to room temperature; wheat take-all germ, fusarium graminearum and fusarium graminearum cultured on a PDA plate for 5 days are made into bacterial cakes by a puncher with the diameter of 5 mm, and then the bacterial cakes are inoculated in the center of the PDA plate containing the medicine in a reverse buckling mode, and the flat plate culture medium without the medicine is used as a control. Each agent was set at 100 mg/L, 50 mg/L, 10 mg/L, 1 mg/L4 concentrations, 3 replicates per concentration, 25 o Culturing in a C incubator for 6 days in dark, investigating colony diameters, and calculating relative inhibition rate of each concentration [ relative inhibition rate= (growth diameter of blank colony-growth diameter of medicament-treated colony)/growth diameter of blank colony multiplied by 100%]. The relative inhibition ratios for each concentration of the compounds of the examples are shown in Table 1:
table 1 bacteriostatic activity of Compounds 1 to 4 of examples
The data in the table 1 show that the compound has higher toxicity to wheat take-all germ, and the inhibition rate of the compound is obviously better than that of the 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 wheat stem basal rot is also obviously superior to that of the 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 rot, reduces the times of control of wheat diseases and the use quantity of medicament varieties, and plays an important role in simplifying wheat cultivation and controlling green wheat diseases.
Comparative examples
Synthesis of isopropyl 4- [ (1, 2, 3-triazol-2-yl) -6-chlorobenzoylamino ] benzoate
Step 1: 5 mmol of 2-fluoro-6-chlorobenzoic acid is put into a three-port reaction flask which is filled with 50 mL methylene dichloride and is provided with a reflux and gas absorption device, and 6 mmol of thionyl chloride (SOCl) is slowly added under normal temperature condition 2 ) And 1 ml DMF, incubation reaction 4 h. TLC detection of the reaction was completed, the solvent and excess thionyl chloride were removed under negative pressure, then 50 mL fresh toluene was added to the reaction flask, and 10 mmol of isopropyl 4-aminobenzoate was added to the reaction flask in portions at 100 o Reaction 4 h at temperature C. After the TLC detection reaction is finished, the reaction liquid is neutralized, washed and desolventized to obtain a crude product of isopropyl 4- (2-fluoro-6-chlorobenzoylamino) benzoate, and then a white solid is obtained through 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 anhydrous cesium carbonate (Cs 2 CO 3 ) Put into a three-port reaction flask with 20 mL of N, N-Dimethylformamide (DMF), at 110 o Reaction 10h at temperature C. Filtering after TLC detection reaction, evaporating part of solvent from filtrate under negative pressure, adding 20. 20 ml warm water, extracting with ethyl acetate for 3 times, drying organic phase, evaporating solvent under negative pressure, and separating by column chromatography to obtain white solid which is 4- [ (1, 2, 3-triazole-2-yl) -6-chlorobenzoylamino]Isopropyl benzoate (2). Yield 32%, melting point: 164-165 o C. 1 H 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). 13 C 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 activity evaluation 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 antibacterial activity of comparative example compounds
As can be seen from Table 2, if, by way of comparison, the imidazole function in the ortho position of the amide of the compound of the invention is replaced by 2H-1,2, 3-triazole, which shows little activity at the tested concentration against wheat take-all and wheat stalk rot causing fusarium graminearum, indicating that the heterocyclic structure in the ortho position of the amide has a specific effect on activity.
The compounds disclosed in the present invention have two outstanding advantages: (1) The composition has excellent inhibition effect on wheat take-all bacteria and fusarium graminearum and fusarium pseudograminearum which can cause wheat stem rot, can be used for simultaneously preventing and treating the wheat take-all and the wheat stem rot, is obviously superior to control silthiopham and prothioconazole, and provides an alternative method, measure and selection for simultaneously preventing and treating the wheat take-all and the wheat stem 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, lower 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, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (9)
1. The 2-imidazole benzamide active compound for preventing and treating wheat take-all and wheat stem basal rot is characterized by having a structure shown in a formula I:
the R is 1 、R 2 is-H, -F, -Cl, -Br, -I, -CN, -CF 3 And said R 1 、R 2 And not H at the same time.
2. The 2-imidazole benzalamide active compound for preventing and treating wheat take-all and wheat stem rot according to claim 1, which is characterized in that: said R is 1 When the compound is-F, -Cl, -Br, R 2 H.
3. The 2-imidazole benzalamide active compound for preventing and treating wheat take-all and wheat stem rot according to claim 1, which is characterized in that: said R is 1 is-F, R 2 H.
4. A process for the preparation of 2-imidazole benzarylamides active compounds for the prevention and treatment of wheat take-all and wheat stem rot as claimed in any one of claims 1 to 3, characterized by the synthesis by:
5. the method for preparing the 2-imidazole benzarylamine active compound for preventing and treating wheat take-all and wheat stem rot according to claim 4, which is characterized by comprising the following steps: the reaction condition A is as follows: 1 to 10 molar equivalents of substituted 2-fluorobenzoic acid (II) comprising SOCl 2 、PCl 3 、POCl 3 、PCl 5 Or oxalyl chloride in the presence of a chlorinating agent comprising dichloromethane, chloroform, toluene, N-dimethylformamide, ethyl acetate, THF or acetonitrileIn a solvent, at-10 o C is reacted for 1 to 10 hours to be converted into corresponding acyl chloride, and then reacted with 1 to 4 equivalents of isopropyl 4-aminobenzoate (III) for 0.5 to 10 hours at room temperature to reflux temperature in the presence of 0.5 to 5 molar equivalents of catalyst comprising triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate or potassium acetate;
or substituted 2-fluorobenzoic acid (II) and isopropyl 4-aminobenzoate (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) in the presence of a catalyst comprising 1-hydroxybenzotriazole (HOBt), 4-Dimethylaminopyridine (DMAP) or N-hydroxy-7-azabenzotriazol (HOAt), in the presence of a catalyst comprising-10 o C is obtained after reaction for 1 to 15 hours under the reflux temperature,
the molar ratio of II to III and condensing agent is 1:0.8-5:0.8-4, and the catalyst is 0-200 mol% relative to the usage of 5, 6-substituted 2-fluorobenzoic acid.
6. The method for preparing the 2-imidazole benzarylamine active compound for preventing and treating wheat take-all and wheat stem rot according to claim 5, wherein the reaction condition B is: the intermediate IV and imidazole react in a solvent comprising toluene, dimethyl sulfoxide (DMSO) or N, N-Dimethylformamide (DMF) with 1-3 molar equivalents of alkali metal carbonate comprising sodium carbonate, potassium carbonate or cesium carbonate as a base under the catalysis of 0-10% molar equivalents of CuI and 8-hydroxyquinoline-N-oxide at a temperature ranging from 50 ℃ to 130 ℃ for 5-18 hours.
7. The method for preparing the 2-imidazole benzarylamine active compound for preventing and treating wheat take-all and wheat stem rot according to claim 4, which is characterized by comprising the following steps: in the reaction formula 2, the feeding mole ratio of the intermediate IV to the imidazole is 1:0.8-6.
8. Use of a 2-imidazole benzarylamine active compound according to claim 1 or 2 or 3, characterized in that: the composition containing the active compound is applied to the control of crop diseases such as wheat take-all and wheat stem rot.
9. Use of a 2-imidazole benzarylamine active compound according to claim 1 or 2 or 3, characterized in that: the bactericide formed by the active compound component and the agronomically acceptable carrier or the bactericide formed by the active compound component and other bactericidal active components and the agronomically acceptable carrier is applied to the control of crop diseases such as wheat take-all and wheat stem-based rot.
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