CN105284819B - 2 [1 (base of benzofuran 5) imido epoxide] acid amides as bactericide application - Google Patents
2 [1 (base of benzofuran 5) imido epoxide] acid amides as bactericide application Download PDFInfo
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Abstract
The application in killing the bactericide of Rhizoctonia solani Kuhn or wheat powdery mildew is being prepared the present invention relates to [1 (base of the benzofuran 5) imido epoxide] acid amides of 2 shown in chemical constitution Formulas I or its salt：Wherein, R is selected from hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkyl；Hydroxyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or C3~C4Branched alkoxy；R1、R2It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkyl；N is selected from：0、1；X1、X5It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X2、X4It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X3It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or C3~C4Branched alkoxy, fluorine, chlorine, bromine or iodine.
Description
Technical field
The present invention relates to the new application of a class compound, specifically 2- [1- (benzofuran -5- bases) imido epoxide] acid amides
It is used as the application for preparing bactericide.
Background technology
The white urea of first oximino ether bactericide mould (Cymoxan) was found from 1974 so far, about the activity of the class formation
Compound, which is continued to bring out, [has the progress of the oximido ether compound of bioactivity.Modern, 2008,7 (2)：6-10].
By choosing, active lead compound is into oxime, and introduce heterocycle compared with high bioactivity into oxime ether be New pesticides discovery
One of study hotspot.Willow love equality [Chinese patent CN 98112665.0；Central China Normal University's journal (natural science edition),
2004,38 (1)：66-68] describe 4 kinds of 3,3- dimethyl -1- (1,2,4- triazol-1-yl) diacetylmonoxime benzylic ethers preparation and
It is under 100mg/L dosage to Pyricularia oryzae, Rhizoctonia solani Kuhn, Sclerotinia sclerotiorum, cotton rhizoctonia solani and wheat scab
The mycelia of bacterium has bactericidal action.
Chinese invention patent describes 1- (1,2,4- triazol-1-yl) ketoxime ethers and oxime ether amide and its bactericidal activity [1-
(1,2,4- triazol-1-yl) ketoxime ether and its as the application for preparing bactericide, Chinese invention patent,
ZL201110112389.5,2013.3.13 are authorized；1- (1,2,4- triazolyl) ketoxime ether-acylamides and its application, Chinese invention are special
Profit, ZL201110154877.2,2013.6.12 is authorized].
Chinese patent [201010553848.9] is described researches and develops a series of compounds in preparation non-amino based on benzofuranol
Application in formate ester agricultural chemicals, Chinese patent [ZL 201010533786.5] describes a series of 4- (benzofuran -5-
Base) -2- benzyl imino thiazoles preparation and its be used as the application of antineoplastic, Chinese patent [A of CN 102786515] description
A series of preparation method of 2- (2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) morpholine and its as preparing antidepression
Medicine application.Chinese patent describes the non-amino formate ester agricultural chemicals or other functional compounds researched and developed based on benzofuranol, specifically
The Chinese invention patent of the preparation and application of compound：4- (benzofuran -5- bases) -2- benzyls imino thiazoles and its conduct are anti-swollen
The application of tumor medicine, ZL201010533786.5,2012.7.25 is authorized；4- (benzofuran -5- bases) -2- fragrant aminos thiazoles and
Its preparation method and application, ZL201010553848.9,2012.7.4 are authorized；5- [2- (benzyl imino group) thiazole-4-yl] furans
Phenolic ether is authorized as the application for preparing bactericide, ZL201110102467.3,2013.3.27；4- (benzofuran -5- bases) -2-
Benzyl imino thiazole is authorized as the application for preparing herbicide, ZL201110102443.8,2013.6.5；5- [2- (benzyl imido
Base) thiazole-4-yl] furans phenolic ether and its be used as the application for preparing insecticide, ZL201110102455.0,2013.6.12 authorize；
5- (2- fragrant aminos thiazole-4-yl) benzofuranol ether compounds and preparation method with activity of weeding,
ZL201210016277.4,2014.8.13 are authorized；2- (2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) morpholines and its system
Preparation Method and application, ZL201210106643.5,2014.7.23 are authorized；4- (benzofuran -5- bases) -2- phenylaminos thiazole is made
For the application of bactericide, ZL201310111413.2,2014.5.28 is authorized；2- (2- benzyls hydrazono-) -4- (benzofuran -5-
Base) thiazole and preparation method and application, ZL201310109794.0,2015.4.1 is authorized；2- (1,2,4- triazole -1- first
Base) -2- (benzofuran -5- bases)-DOXs and its application, CN201310247669.6,2013.6.20；N-[4-
(benzofuran -5- bases) thiazol-2-yl] acid amides and preparation method and application, CN201310308471.4,2013.7.22.
The content of the invention
It is an object of the invention to provide (benzofuran -5- the bases) -2- of the 1- shown in chemical constitution Formulas I (1,2,4- triazole -1-
Base) application of ketoxime ether-acylamide or its salt in the bactericide of Rhizoctonia solani Kuhn or wheat powdery mildew is killed in preparation：
Wherein, R is selected from hydrogen, C1~C2Alkyl, C3~C4Straight or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Directly
Chain alkoxy or branched alkoxy；R1、R2It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight or branched alkyl；N is selected from：0、1；X1、
X5Choosing is white：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl；X2、X4It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chain
Alkyl or branched alkyl；X3It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, C1~C2Alkoxy, C3~C4
Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or iodine；Its salt is selected from：Hydrochloride, hydrobromate, sulfate, nitrate, phosphorus
Hydrochlorate, mesylate, benzene sulfonate, tosilate, malate, lactate, succinate or butene dioic acid salt.
The present invention provides N- phenyl -2- [1- (benzofuran -5- bases) imido epoxide] acid amides shown in chemical constitution Formula II
Preparing the application in killing the bactericide of Rhizoctonia solani Kuhn or wheat powdery mildew：
Wherein, R is selected from hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkyl；Hydroxyl, C1~C2Alkoxy, C3
~C4Unbranched alkoxy or C3~C4Branched alkoxy；R1、R2It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkane
Base；N is selected from：0、1；X1、X5It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X2、X4It is selected from：
Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X3It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl
Or C3~C4Branched alkyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or C3~C4Branched alkoxy, fluorine, chlorine, bromine or iodine.
The present invention provides N- benzyls -2- [1- (benzofuran -5- bases) imido epoxide] acid amides shown in chemical constitution formula III
Preparing the application in killing the bactericide of Rhizoctonia solani Kuhn or wheat powdery mildew：
Wherein, R is selected from hydrogen, C1~C2Alkyl, C3~C4Straight or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Directly
Chain alkoxy or branched alkoxy；R1、R2It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight or branched alkyl；X1、X2、X3、X4、X5
It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl.
N- (4- fluorophenyls) -2- [1- (2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- that the present invention is provided
(1,2,4- triazol-1-yl) second imido epoxide] acetamide, N- (4- chlorphenyls) -2- [1- (2,2- dimethyl -2,3- dihydrobenzos
Furans -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide, N- (2- aminomethyl phenyls) -2- [1- (7- methoxies
Base -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide, N-
(2,6- 3,5-dimethylphenyl) -2- [1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- tri-
Azoles -1- bases) second imido epoxide] acetamide, N- (2,6- 3,5-dimethylphenyl) -2- [1- (7- ethyoxyls -2,2- dimethyl -2,3- bis-
Hydrogen benzofuran -5- bases) -2- (1,2,4- triazole ring -1- bases) second imido epoxide] acetamide, N- (4- fluorophenyls) -2- [1- (7-
Ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetyl
Amine, N- (4- chlorphenyls) -2- [1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- tri-
Azoles -1- bases) second imido epoxide] acetamide, N- phenyl -2- [1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -
5- yls) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide or N- (4- chlorphenyls) -2- [1- (7- propoxyl group -2,2-
Dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide kills rice in preparation
Application in the bactericide of sheath blight fungus or wheat powdery mildew.
N- benzyls -2- [1- (2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- that the present invention is provided
Triazol-1-yl) second imido epoxide] acetamide, N- benzyls -2- [1- (7- methoxyl group -2,2- dimethyl -2,3- dihydrobenzo furans
Mutter -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide or N- benzyls -2- [1- (7- propoxyl group -2,2- diformazans
Base -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] in preparation to kill rice line withered for acetamide
Application in the bactericide of germ or wheat powdery mildew.
The present invention has the following advantages that compared with prior art：2- [1- (benzofuran -5- bases) imido that the present invention is provided
Epoxide] acid amides have kill Rhizoctonia solani Kuhn or wheat powdery mildew activity.
Embodiment
Following examples are intended to illustrate invention rather than limitation of the invention further.
Embodiment 1
The preparation of 2- [1- (benzofuran -5- bases) imido epoxide] acid amides (I)
Wherein, R is selected from hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkyl；Hydroxyl, C1~C2Alkoxy, C3
~C4Unbranched alkoxy or C3~C4Branched alkoxy；R1、R2It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkane
Base；N is selected from：0、1；X1、X5It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X2、X4It is selected from：
Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X3It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl
Or C3~C4Branched alkyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or C3~C4Branched alkoxy, fluorine, chlorine, bromine or iodine.
According to Chinese patent [1- (benzofuran -5- bases) -2- (1,2,4- triazol-1-yl) ketoxime ether-acylamides and its preparation
Method is disclosed with application, CN104327055A, 2015.2.4] prepare 2- [1- (benzofuran -5- bases) imido epoxide] acid amides.
Embodiment 2
The bactericidal activity of 2- [1- (benzofuran -5- bases) imido epoxide] acid amides is determined
1 test objective
2- [1- (benzofuran -5- bases) imido epoxide] acid amides is determined indoors under for examination concentration to various pathogens
Virulence, its bactericidal activity of preliminary assessment.
2 experimental conditions
2.1 for examination target
Rhizoctonia solani Kuhn (Rhizoctonia solani), strain is maintained in refrigerator, experiment before 2-3 days it is oblique from test tube
Face is inoculated into culture dish, is cultivated and is for experiment under preference temperature.Experiment is potato agar culture medium with culture medium
(PDA)。
Wheat powdery mildew (Blumeria graminis) preserves spore with wheat seedling and is for experiment.
2.2 condition of culture
Condition of culture for target after examination target and experiment is 25 ± 5 DEG C of temperature, relative humidity 75 ± 5%
2.3 instrument and equipment
Beaker, pipette, graduated cylinder, culture dish, high-pressure sterilizing pot, constant temperature biochemical cultivation case, greenhouse etc..
3 experimental designs
3.1 test medicine
2- [1- (benzofuran -5- bases) imido epoxide] acid amides (I)：
Wherein, R is selected from hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkyl；Hydroxyl, C1~C2Alkoxy, C3
~C4Unbranched alkoxy or C3~C4Branched alkoxy；R1、R2It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chain or C3~C4Branched alkane
Base；N is selected from：0、1；X1、X5It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X2、X4It is selected from：
Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl or C3~C4Branched alkyl；X3It is selected from：Hydrogen, C1~C2Alkyl, C3~C4Straight chained alkyl
Or C3~C4Branched alkyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or C3~C4Branched alkoxy, fluorine, chlorine, bromine or iodine.
3.2 experimental concentration
Broad Bean Leaves method and pot-culture method drug concentration set 500mg/L
3.3 medicaments are prepared
Active compound：Aequum is weighed with a ten thousandth electronic balance；
Solvent：DMF (DMF), 0.2%；
Emulsifying agent：Tween80,0.1%；l
General sieve is determined：0.0500g samples accurately are weighed, are dissolved with 0.20mLDMF, emulsifying agent containing 0.1%Tween80 is added
Sterilized water 98.8ml, stir, be configured to 500mg/L strength solutions standby.
4 test methods
Reference《Pesticide bioactivity evaluates SOP》.
Rhizoctonia solani Kuhn：Broad Bean Leaves method is used with reference to the raw standard method NY/T1156.5-2006 that surveys, clip broad bean is susceptible
The blade of kind, puts in culture dish, with sprayer by the wet vacuum side of blade of 500mg/L compound liquid medicine jets, after natural air drying, with connecing
Plant device and the one side that a diameter of 6.0mm bacteria cakes have mycelia is inoculated in processing central vane, protectiveness is tested 24 after chemicals treatment
Hour inoculation, is placed in growth cabinet after inoculation, is trained under conditions of 26~28 DEG C of temperature, relative humidity 80%~90%
Support.Depending on blank control incidence, prevention effect is calculated.
Wheat powdery mildew：Pot-culture method is used with reference to the raw standard method NY/T1156.4-2006 that surveys, from seedling length to 2
The susceptible variety wheat seedling of the leaf phase of leaf~3, is dried 500mg/L compounds medicine liquid spray on wheat seedling with spray-on process naturally,
The Powdery Mildew Fresh spores produced on wheat leaf blade of falling ill in 24 hours uniformly are shaken off to be inoculated on wheat seedling, often handled not
Less than 3 basins, per 10 plants of basin, protectiveness experiment is inoculated with for 24 hours after chemicals treatment, is then put and is cultivated under suitable condition.According to sky
White control incidence classification investigation, calculates prevention effect.
Experiment sets solvent control.
5 investigation methods and biological evaluation method
5.1 investigation method
Routine observation record blade, the incidence of plant and mycelial growth situation after processing, according to disease index and bacterium
Silk diameter, calculates preventive effect and inhibiting rate.
Growth inhibition ratio (%)=(control colony diameter-processing colony diameter) × 100/ (control colony diameter -6mm).
Wheat powdery mildew；It is classified and is investigated according to blank control incidence.Using following stage division：
0 grade：It is disease-free；1 grade：Lesion area accounts for less than the 5% of full wafer leaf area；3 grades：Lesion area accounts for full wafer leaf area
6%~15%；5 grades：Lesion area accounts for the 16%~25% of full wafer leaf area；7 grades：Lesion area accounts for the 26% of full wafer leaf area
~50%；9 grades：Lesion area accounts for more than the 50% of full wafer leaf area.
According to survey data, the disease index and formula (2) for calculating each processing by formula (1) calculate prevention effect.
In formula：X represents disease index, and Ni represents the sick numbers of sheets at different levels, and i represents relative value of series, and N represents to investigate total number of sheets.
In formula：P represents prevention effect, and CK represents blank control disease index, and PT represents chemicals treatment disease index.
6 Activity Results
General sieve result：2- [1- (benzofuran -5- bases) imido epoxide] acid amides is to Rhizoctonia solani Kuhn and wheat powdery mildew
Prevention effect be included in table 1~2.
Prevention effect of the 2- of table 1 [1- (benzofuran -5- bases) imido epoxide] acid amides to Rhizoctonia solani Kuhn
Prevention effect of the 2- of table 2 [1- (benzofuran -5- bases) imido epoxide] acid amides to wheat powdery mildew
2- [1- (benzofuran -5- bases) imido epoxide] acid amides has bactericidal activity, available for preparing bactericide.
Claims (2)
1. the compound or its salt shown in chemical constitution Formula II kills the bactericide of Rhizoctonia solani Kuhn or wheat powdery mildew in preparation
In application：
It is characterized in that the compound shown in Formula II is selected from：N- (4- fluorophenyls) -2- [1- (2,2- dimethyl -2,3- dihydrobenzos
Furans -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide, N- (4- chlorphenyls) -2- [1- (2,2- diformazans
Base -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide, N- (2- methylbenzenes
Base) [1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second is sub- by -2-
Aminooxy group] acetamide, N- (2,6- 3,5-dimethylphenyl) -2- [1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -
5- yls) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide, N- (2,6- 3,5-dimethylphenyl) -2- [1- (7- ethyoxyls -
2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazole ring -1- bases) second imido epoxide] acetamide, N-
(4- fluorophenyls) -2- [1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazole -1-
Base) second imido epoxide] acetamide, N- (4- chlorphenyls) -2- [1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -
5- yls) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide, N- phenyl -2- [1- (7- propoxyl group -2,2- dimethyl -
2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide or N- (4- chlorphenyls) -2-
[1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide]
Acetamide；Its salt is selected from：Hydrochloride, hydrobromate, sulfate, nitrate, phosphate, mesylate, benzene sulfonate, to toluene
Sulfonate, malate, lactate, succinate or butene dioic acid salt.
2. the compound or its salt shown in chemical constitution formula III kills the bactericide of Rhizoctonia solani Kuhn or wheat powdery mildew in preparation
In application：
It is characterized in that the compound shown in formula III is selected from：N- benzyls -2- [1- (2,2- dimethyl -2,3- Dihydrobenzofuranes -
5- yls) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide, N- benzyls -2- [1- (7- methoxyl groups -2,2- dimethyl -
2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetamide or N- benzyls -2- [1- (7-
Propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazol-1-yl) second imido epoxide] acetyl
Amine；Its salt is selected from：Hydrochloride, hydrobromate, sulfate, nitrate, phosphate, mesylate, benzene sulfonate, p-methyl benzenesulfonic acid
Salt, malate, lactate, succinate or butene dioic acid salt.
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