CN103651352B - New application of N-(2-phenoxy benzene) benzamide compound as agricultural bactericide - Google Patents
New application of N-(2-phenoxy benzene) benzamide compound as agricultural bactericide Download PDFInfo
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 9
- 239000003899 bactericide agent Substances 0.000 title claims abstract description 8
- -1 benzamide compound Chemical class 0.000 title abstract description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title abstract 4
- 230000001580 bacterial effect Effects 0.000 claims abstract description 55
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- 241000894006 Bacteria Species 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 241000223218 Fusarium Species 0.000 claims description 2
- 241001330975 Magnaporthe oryzae Species 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
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- 239000000575 pesticide Substances 0.000 abstract description 5
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- 230000005764 inhibitory process Effects 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 241000526118 Fusarium solani f. radicicola Species 0.000 description 6
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- 206010039509 Scab Diseases 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 241001272684 Xanthomonas campestris pv. oryzae Species 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
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- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 3
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- 241000607992 Vogesella oryzae Species 0.000 description 1
- 241000589649 Xanthomonas campestris pv. campestris Species 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
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- 238000007865 diluting Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
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- YHAAAWMTEKLUJM-UHFFFAOYSA-N n-(2-phenoxyphenyl)benzamide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1OC1=CC=CC=C1 YHAAAWMTEKLUJM-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a new application of an N-(2-phenoxy benzene) benzamide compound as an agricultural bactericide. According to the research on multiple phytopathogens by adopting the N-(2-phenoxy benzene) benzamide compound, the N-(2-phenoxy benzene) benzamide compound has relatively good inhibiting effects on the phytopathogenic bacterial and funguses, so that a novel stable, efficient, harmfulless, green chemical pesticide can be provided.
Description
Technical Field
The invention relates to a new application of N- (2-phenoxybenzene) benzamide compounds as agricultural fungicides, belonging to the field of pesticides.
Background
N- (2-phenoxybenzene) benzamide compounds are benzamide compounds containing diphenyl ether structures, have wide application in the pharmaceutical industry, and can be used as amine immunizing agents [ US5310760(1994) ], analgesics [ US2004043378(2004) ], bactericides [ WO2013116823 (2013) ], Alzheimer's disease [ WO 2019630548 (2013) ], diabetes [ WO2001023347(2001) ], cardiovascular diseases [ US20040082641(2004) ], and the like.
However, the application of N- (2-phenoxybenzene) benzamide compounds as agricultural bactericides is not seen at present.
Disclosure of Invention
The invention aims to expand the application of N- (2-phenoxybenzene) benzamide compounds and provide a new application of the N- (2-phenoxybenzene) benzamide compounds as agricultural bactericides.
The N- (2-phenoxybenzene) benzamide compound is a compound shown as the following general formula (I):
wherein,
R1is methyl, chlorine atom;
R2is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl, methoxy, trifluoromethyl;
R3is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl, methoxy or trifluoromethyl.
Furthermore, the invention provides a new application of the N- (2-phenoxybenzene) benzamide compound as an agricultural bactericide.
Wherein the agricultural fungicide is an inhibitor of a plant pathogenic bacterium or fungus.
Furthermore, the plant pathogenic bacteria are rice bacterial blight, cotton angular leaf spot, corn bacterial blight, potato soft rot, cabbage black rot, cabbage soft rot, ginger bacterial wilt or tobacco bacterial wilt.
The plant pathogenic fungi are Magnaporthe grisea, Rhizoctonia solani, Fusarium graminearum, Botrytis cinerea, potato late blight, tobacco anthracnose, cabbage black spot, apple rot, grape black pox or corn leaf spot.
The inventor carries out deep research on the activity of N- (2-phenoxybenzene) benzamide on various plant pathogenic bacteria, and the experimental result shows that the compound has a good inhibiting effect on the plant pathogenic bacteria, so that a new thought is provided for developing the compound into a new green chemical pesticide.
The foregoing aspects of the present invention will be described in further detail with reference to specific embodiments. This is not to be construed as limiting the invention.
Detailed Description
The N- (2-phenoxybenzene) benzamides of the examples are all from the institute for pesticide and crop protection of Sichuan university, and the phytopathogens to be tested are from Sichuan university, institute for Onchial institute of science, China center for general microbiological culture Collection, and Sichuan academy of agricultural sciences.
Example 1 CompoundsPreparation of
20mL of 2mol/L NaOH aqueous solution, 5.0mmol of o-aminodiphenyl ether and 2mL of 1, 4-dioxane are added into a conical flask, and the mixture is cooled to 0 ℃ in an ice water bath, and 10.0mmol of o-methylbenzoyl chloride is slowly added inwards. After the dropwise addition, the mixture was allowed to continue stirring at room temperature for 2 hours. Then adding water, extracting with ethyl acetate for three times, combining organic layers, and sequentially using 2mol of organic layerThe aqueous solution of/L NaOH is washed with clear water and anhydrous Na2SO4Drying, and removing the solvent by rotary evaporation to obtain a crude product. Purifying the crude product by a medium-pressure preparative chromatograph, wherein an eluent is petroleum ether: ethyl acetate = 1: 1, a yellow solid was obtained in 70.5% yield.
1H-NMR(400MHz,CDCl3):2.48(3H,s),6.92(1H,d),7.05-7.07(3H,m),7.11-7.15(1H,t),7.19-7.24(2H,m),7.28-7.30(2H,d),7.50(1H,d),7.76-7.77(2H,d),8.45(1H,s),8.65(1H,d)。
Example 2 CompoundsPreparation of
20mL of 2mol/L NaOH aqueous solution, 5.0mmol of 4-chloro-o-aminodiphenyl ether and 2mL of 1, 4-dioxane are added into a conical flask, the mixture is cooled to 0 ℃ in an ice water bath, and 10.0mmol of o-methylbenzoyl chloride is slowly added inwards. After the dropwise addition, the mixture was allowed to continue stirring at room temperature for 2 hours. Then adding water, extracting with ethyl acetate for three times, combining organic layers, sequentially washing the organic layers with 2mol/L NaOH aqueous solution, clear water and anhydrous Na2SO4Drying, and removing the solvent by rotary evaporation to obtain a crude product. Purifying the crude product by a medium-pressure preparative chromatograph, wherein an eluent is petroleum ether: ethyl acetate = 1: 1, a yellow solid was obtained in 57.4% yield.
1H-NMR(400MHz,CDCl3):2.48(3H,s),6.79-6.82(1H,d),6.95-6.98(1H,d),7.05-7.07(1H,t),7.21-7.24(2H,m),7.28-7.30(2H,d),7.50(2H,d),7.76-7.77(2H,d),8.49(1H,s),8.65(1H,d)。
Example 3 CompoundsPreparation of
20mL of 2mol/L NaOH aqueous solution, 50mmol of 2, 4-dichloro-o-aminodiphenyl ether and 2mL of 1, 4-dioxane are cooled to 0 ℃ in an ice water bath, and 10.0mmol of o-methylbenzoyl chloride is slowly added dropwise inwards. After the dropwise addition, the mixture was allowed to continue stirring at room temperature for 2 hours. Then adding water, extracting with ethyl acetate for three times, combining organic layers, sequentially washing the organic layers with 2mol/L NaOH aqueous solution, clear water and anhydrous Na2SO4Drying, and removing the solvent by rotary evaporation to obtain a crude product. Purifying the crude product by a medium-pressure preparative chromatograph, wherein an eluent is petroleum ether: ethyl acetate = 1: 1, a yellow solid was obtained in 66.4% yield.
1H-NMR(400MHz,CDCl3):2.48(3H,s),6.79-6.82(1H,d),6.98-7.00(1H,d),7.03-7.07(1H,t),7.19-7.24(2H,m),7.28-7.30(2H,d),7.50(1H,d),7.76-7.77(2H,d),8.49(1H,s),8.65(1H,d)。
Example 4 CompoundsPreparation of
20mL of 2mol/L NaOH aqueous solution, 5.0mmol of o-aminodiphenyl ether and 2mL of 1, 4-dioxane are added into a conical flask, the mixture is cooled to 0 ℃ in an ice water bath, and 10.0mmol of o-chlorobenzoyl chloride is slowly added inwards. After the dropwise addition, the mixture was allowed to continue stirring at room temperature for 2 hours. Then adding water, extracting with ethyl acetate for three times, combining organic layers, sequentially washing the organic layers with 2mol/L NaOH aqueous solution, clear water and anhydrous Na2SO4Drying, and removing the solvent by rotary evaporation to obtain a crude product. Purifying the crude product by a medium-pressure preparative chromatograph, wherein an eluent is petroleum ether: ethyl acetate = 1: 1, a yellow solid was obtained in 62.7% yield.
1H-NMR(400MHz,CDCl3):6.85(1H,d),6.98-7.00(1H,d),7.05-7.09(3H,m),7.15-7.18(2H,m),7.25-7.28(2H,d),7.48(1H,d),7.70-7.72(2H,d),8.50(1H,s),8.63(1H,d)。
Examples5 CompoundsPreparation of
20mL of 2mol/L NaOH aqueous solution, 5.0mmol of 4-chloro-o-aminodiphenyl ether and 2mL of 1, 4-dioxane are added into a conical flask, the mixture is cooled to 0 ℃ in an ice water bath, and 10.0mmol of o-chlorobenzoyl chloride is slowly added inwards dropwise. After the dropwise addition, the mixture was allowed to continue stirring at room temperature for 2 hours. Then adding water, extracting with ethyl acetate for three times, combining organic layers, sequentially washing the organic layers with 2mol/L NaOH aqueous solution, clear water and anhydrous Na2SO4Drying, and removing the solvent by rotary evaporation to obtain a crude product. Purifying the crude product by a medium-pressure preparative chromatograph, wherein an eluent is petroleum ether: ethyl acetate = 1: 1, a yellow solid was obtained in 73.2% yield.
1H-NMR(400MHz,CDCl3):6.90(1H,d),6.99-7.02(1H,d),7.04-7.06(1H,m),7.13(1H,t),7.18-7.21(2H,m),7.28-7.30(2H,d),7.50(1H,d),7.70-7.72(2H,d),8.48(1H,s),8.65(1H,d)。
Example 6 CompoundsPreparation of
20mL of 2mol/L NaOH aqueous solution, 5.0mmol of 2, 4-dichloro-o-aminodiphenyl ether and 2mL of 1, 4-dioxane are added into a conical flask, the mixture is cooled to 0 ℃ in an ice water bath, and 10.0mmol of o-chlorobenzoyl chloride is slowly added inwards. After the dropwise addition, the mixture was allowed to continue stirring at room temperature for 2 hours. Then adding water, extracting with ethyl acetate for three times, combining organic layers, sequentially washing the organic layers with 2mol/L NaOH aqueous solution, clear water and anhydrous Na2SO4Drying, and removing the solvent by rotary evaporation to obtain a crude product. Purifying the crude product by a medium-pressure preparative chromatograph, wherein an eluent is petroleum ether: ethyl acetate = 1: 1, a yellow solid was obtained in 65.6% yield.
1H-NMR(400MHz,CDCl3):6.85(1H,d),6.98-7.00(1H,d),7.05(1H,t),7.15-7.18(2H,m),7.25-7.28(2H,d),7.48(1H,d),7.70-7.72(2H,d),8.50(1H,s),8.63(1H,d)。
EXAMPLE 7 determination of the fungicidal Activity of N- (2-Phenoxyphenyl) benzamides against phytopathogenic bacteria and fungi
1 test plant pathogenic bacteria
1.1 test for plant pathogenic bacteria
Rice bacterial blight (Xanthomonas oryzae v. oryzae), cotton angular leaf spot (Xanthomonas campestris pv. malvacearum), corn bacterial wilt (Pantoea stewartsp. stewartii), tobacco bacterial wilt (Pseudomonas solanacearum pv. tabaci), potato soft rot (Erwinia anovora. carotovora), ginger bacterial wilt (Ralstoniasenapaceae), cabbage black rot (Xanthomonas campestris pv. Campestris), cabbage soft rot (Erwinia anovora).
1.2 test for phytopathogenic fungi
Pyricularia oryzae (PiriculariaonyzaeCav), Rhizoctonia solani (Rhizoctonia solani), Gibberella graminis (Fusarium graminearum), Microsporum zeae (Bipolariismatis), Phytophthora infestans (Phytophthora infestans), Nicotiana tabacum (Colletochumconica), Blakebia brassicae (Alternaria), Botrytiscirea solani (Botrytiscirea), apple rot (Cytospora. sp), and Vitis vinifera (Sphacelalophora pellinum).
2, experimental method:
2.1 determination of bacteriostatic activity of N- (2-phenoxybenzene) benzamide compounds on plant pathogenic bacteria
The colony inhibition (%) was determined by the growth rate method:
the plant pathogenic bacteria of 1.1 are respectively diluted to a certain concentration, added into a liquid culture medium of the N- (2-phenoxybenzene) benzamide compound (the final concentration of the N- (2-phenoxybenzene) benzamide compound is prepared into a series of N- (2-phenoxybenzene) benzamide compound concentration gradient culture media by adopting a test tube double dilution method), each series is inoculated with a test bacteria suspension, each concentration is repeated for 3 times, and sterile water is used as blank control. After culturing at 35-38 deg.C for 18-24 hr, the serial cultures are subjected to bacteria count by gradient dilution method, and colony inhibition rate is determined according to colony number, and the formula is as follows:
2.2 determination of bacteriostatic activity of N- (2-phenoxybenzene) benzamide compounds on plant pathogenic fungi
Determination of hypha relative inhibition (%) by the medium method containing toxin:
diluting N- (2-phenoxybenzene) benzamide compound with sterile water, mixing with PDA culture medium, preparing a series of drug-containing flat plates with uniform thickness by a double dilution method at the final concentration of the N- (2-phenoxybenzene) benzamide compound, and repeating the treatment 3 times by using sterile water as a blank control. After the culture medium is solidified, inoculating the test fungus cake of plant pathogenic fungi on the solidified culture medium, culturing at 27-28 deg.C for 3-5 days, measuring the diameter of the fungus cake to be 0.4cm, and calculating the inhibition rate of hypha growth by cross method.
3 results of the experiment
The results of the determination of the bacteriostatic activity of the N- (2-phenoxybenzene) benzamide compounds on the plant pathogenic bacteria are shown in tables 1, 2, 3, 4, 5 and 6. As is clear from the results in tables 1, 2, 3, 4, 5 and 6, the N- (2-phenoxybenzene) benzamide compounds have a good inhibitory effect on phytopathogenic bacteria.
TABLE 1 relative inhibition (%). of the compound of example 1 at 20mg/L against plant pathogenic bacteria
| Bacterial strain | Colony inhibition (%) | Bacterial strain | Colony inhibition (%) |
| Bacterial blight of rice | 87.3 | Cotton angular leaf spot germ | 96.4 |
| Bacterial wilt of corn | 99.2 | Bacterial wilt of tobacco | 97.8 |
| Soft rot of potato | 78.4 | Soft rot of Chinese cabbage | 91.0 |
| Cabbage black rot | 85.6 | Ginger bacterial wilt | 92.5 |
TABLE 2 relative inhibition (%). of the compound of example 2 at 20mg/L against plant pathogenic bacteria
| Bacterial strain | Colony inhibition (%) | Bacterial strain | Colony inhibition (%) |
| Bacterial blight of rice | 89.2 | Cotton angular leaf spot germ | 92.5 |
| Bacterial wilt of corn | 84.2 | Bacterial wilt of tobacco | 97.6 |
| Soft rot of potato | 87.9 | Soft rot of Chinese cabbage | 89.6 |
| Cabbage black rot | 81.0 | Ginger bacterial wilt | 88.7 |
TABLE 3 relative inhibition (%). of the Compound of example 3 at 20mg/L against plant pathogenic bacteria
| Bacterial strain | Colony inhibition (%) | Bacterial strain | Colony inhibition (%) |
| Bacterial blight of rice | 14.5 | Cotton angular leaf spot germ | 78.9 |
| Bacterial wilt of corn | 58.9 | Bacterial wilt of tobacco | 56.9 |
| Soft rot of potato | 89.7 | Soft rot of Chinese cabbage | 37.3 |
| Cabbage black rot | 67.8 | Ginger bacterial wilt | 89.9 |
TABLE 4 relative inhibition (%). of the Compound of example 4 against plant pathogenic bacteria at 20mg/L
| Bacterial strain | Colony inhibition (%) | Bacterial strain | Colony inhibition (%) |
| Bacterial blight of rice | 78.5 | Cotton angular leaf spot germ | 97.3 |
| Bacterial wilt of corn | 77.9 | Bacterial wilt of tobacco | 92.5 |
| Soft rot of potato | 73.9 | Soft rot of Chinese cabbage | 86.9 |
| Cabbage black rot | 45.8 | Ginger bacterial wilt | 84.0 |
TABLE 5 relative inhibition (%). of the Compound of example 5 at 20mg/L against plant pathogenic bacteria
| Bacterial strain | Colony inhibition (%) | Bacterial strain | Colony inhibition (%) |
| Bacterial blight of rice | 78.1 | Cotton angular leaf spot germ | 78.9 |
| Bacterial wilt of corn | 83.5 | Bacterial wilt of tobacco | 76.5 |
| Soft rot of potato | 84.6 | Soft rot of Chinese cabbage | 88.9 |
| Cabbage black rot | 92.6 | Ginger bacterial wilt | 82.6 |
TABLE 6 relative inhibition (%). of the Compound of example 6 at 20mg/L against plant pathogenic bacteria
| Bacterial strain | Colony inhibition (%) | Bacterial strain | Colony inhibition (%) |
| Bacterial blight of rice | 80.6 | Cotton angular leaf spot germ | 93.3 |
| Bacterial wilt of corn | 84.9 | Bacterial wilt of tobacco | 91.0 |
| Soft rot of potato | 90.5 | Soft rot of Chinese cabbage | 88.6 |
| Cabbage black rot | 94.3 | Ginger bacterial wilt | 84.6 |
The results of the measurement of the inhibitory activity of N- (2-phenoxybenzene) benzamide compounds against phytopathogenic fungi are shown below (see tables 7, 8, 9, 10, 11, and 12). As is clear from the results in tables 7, 8, 9, 10, 11 and 12, the N- (2-phenoxybenzene) benzamide compounds also have a good inhibitory effect on phytopathogenic fungi.
TABLE 7 relative inhibition (%), at 20mg/L, of the compound of example 1 against phytopathogenic fungi
| Bacterial strain | Relative inhibition ratio (%) | Bacterial strain | Relative inhibition ratio (%) |
| Magnaporthe grisea | 78.0 | Rhizoctonia solani of rice | 60.9 |
| Wheat scab germ | 53.1 | Corn leaf spot germ | 66.3 |
| Black spot of Chinese cabbage | 46.2 | Late blight of potato | 25.3 |
| Botrytis cinerea | 68.3 | Tobacco anthracnose pathogen | 48.6 |
| Rot of apple | 35.8 | Blackpox fungus grape | 49.2 |
TABLE 8 relative inhibition (%). of the compound of example 2 at 20mg/L against phytopathogenic fungi
| Bacterial strain | Relative inhibition ratio (%) | Bacterial strain | Relative inhibition ratio (%) |
| Magnaporthe grisea | 79.6 | Rhizoctonia solani of rice | 91.0 |
| Wheat scab germ | 65.6 | Corn leaf spot germ | 45.0 |
| Black spot of Chinese cabbage | 45.9 | Late blight of potato | 88.7 |
| Botrytis cinerea | 48.7 | Tobacco anthracnose pathogen | 56.3 |
| Rot of apple | 60.9 | Blackpox fungus grape | 86.5 |
TABLE 9 relative inhibition (%). of the compound of example 3 at 20mg/L against phytopathogenic fungi
| Bacterial strain | Relative inhibition ratio (%) | Bacterial strain | Relative inhibition ratio (%) |
| Magnaporthe grisea | 78.1 | Rhizoctonia solani of rice | 89.2 |
| Wheat scab germ | 52.7 | Corn leaf spot germ | 68.7 |
| Black spot of Chinese cabbage | 72.3 | Late blight of potato | 66.3 |
| Botrytis cinerea | 66.7 | Tobacco anthracnose pathogen | 58.7 |
| Rot of apple | 74.2 | Blackpox fungus grape | 86.9 |
TABLE 10 relative inhibition (%). of the compound of example 4 at 20mg/L against phytopathogenic fungi
| Bacterial strain | Relative inhibition ratio (%) | Bacterial strain | Relative inhibition ratio (%) |
| Magnaporthe grisea | 92.0 | Rhizoctonia solani of rice | 71.6 |
| Wheat scab germ | 17..9 | Corn leaf spot germ | 89.9 |
| Black spot of Chinese cabbage | 89.7 | Late blight of potato | 90.6 |
| Botrytis cinerea | 4.7 | Tobacco anthracnose pathogen | 94.3 |
| Rot of apple | 18.9 | Blackpox fungus grape | 75.0 |
TABLE 11 relative inhibition (%). of example 5 compound at 20mg/L against phytopathogenic fungi
| Bacterial strain | Relative inhibition ratio (%) | Bacterial strain | Relative inhibition ratio (%) |
| Magnaporthe grisea | 13.4 | Rhizoctonia solani of rice | 72.2 |
| Wheat scab germ | 49.1 | Corn leaf spot germ | 77.8 |
| Black spot of Chinese cabbage | 48.9 | Late blight of potato | 86.7 |
| Botrytis cinerea | 21.0 | Tobacco anthracnose pathogen | 78.9 |
| Rot of apple | 41.4 | Blackpox fungus grape | 93.3 |
TABLE 12 relative inhibition (%). of the compound of example 6 at 20mg/L against phytopathogenic fungi
| Bacterial strain | Relative inhibition ratio (%) | Bacterial strain | Relative inhibition ratio (%) |
| Magnaporthe grisea | 87.0 | Rhizoctonia solani of rice | 77.4 |
| Wheat scab germ | 27.4 | Corn leaf spot germ | 45.3 |
| Black spot of Chinese cabbage | 66.5 | Late blight of potato | 88.9 |
| Botrytis cinerea | 12.6 | Tobacco anthracnose pathogen | 56.8 |
| Rot of apple | 34.1 | Blackpox fungus grape | 100 |
In conclusion, the N- (2-phenoxybenzene) benzamide compound has good broad-spectrum bactericidal activity on plant pathogenic bacteria, is developed into a novel stable, efficient and nontoxic green chemical pesticide, and has wide prospects.
Claims (4)
- The new application of the N- (2-phenoxybenzene) benzamide compound as an agricultural bactericide is characterized in that the N- (2-phenoxybenzene) benzamide compound is a compound shown as the following general formula (I):wherein,R1is methyl, chlorine atom;R2is a hydrogen atomFluorine atom, chlorine atom, bromine atom, methyl group, methoxy group, trifluoromethyl group;R3is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl, methoxy or trifluoromethyl.
- 2. The new use as claimed in claim 1, characterized in that the agricultural fungicide is an inhibitor of phytopathogenic bacteria or fungi.
- 3. The use according to claim 2, characterized in that the phytopathogenic bacteria are rice bacterial blight, cotton angular leaf blight, corn bacterial blight, potato soft rot, cabbage black rot, cabbage soft rot, ginger bacterial wilt or tobacco bacterial wilt.
- 4. The use according to claim 2, characterized in that the phytopathogenic fungus is Pyricularia oryzae, Rhizoctonia solani, Gibberella cerealis, Botrytis cinerea, Phytophthora infestans, Nicotiana tabacum, Blakeslea brassicae, Malus pumila, Vibrio viticola or Zea mays.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1450993A (en) * | 1999-07-20 | 2003-10-22 | 道农业科学公司 | Fungicidal heterocyclic aromatic amides and their compositions methods of use and preparation |
| CN1764657A (en) * | 2003-03-24 | 2006-04-26 | 巴斯福股份公司 | Trifluoromethyl-thiophene carboxylic acid anilides and use thereof as fungicides. |
| WO2011026107A1 (en) * | 2009-08-31 | 2011-03-03 | University Of Notre Dame Du Lac | Phthalanilate compounds and methods of use |
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| CN1450993A (en) * | 1999-07-20 | 2003-10-22 | 道农业科学公司 | Fungicidal heterocyclic aromatic amides and their compositions methods of use and preparation |
| CN1764657A (en) * | 2003-03-24 | 2006-04-26 | 巴斯福股份公司 | Trifluoromethyl-thiophene carboxylic acid anilides and use thereof as fungicides. |
| WO2011026107A1 (en) * | 2009-08-31 | 2011-03-03 | University Of Notre Dame Du Lac | Phthalanilate compounds and methods of use |
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