CN103524422A - Benzimidazole derivative, and preparation method and purpose thereof - Google Patents

Benzimidazole derivative, and preparation method and purpose thereof Download PDF

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Publication number
CN103524422A
CN103524422A CN201310473947.XA CN201310473947A CN103524422A CN 103524422 A CN103524422 A CN 103524422A CN 201310473947 A CN201310473947 A CN 201310473947A CN 103524422 A CN103524422 A CN 103524422A
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benzimidizole derivatives
dissolved
organic layer
obtains
structural formula
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CN103524422B (en
Inventor
梅向东
司伟杰
宁君
张涛
张兰祥
董梦雅
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Institute of Plant Protection of Chinese Academy of Agricultural Sciences
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Institute of Plant Protection of Chinese Academy of Agricultural Sciences
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • 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
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Abstract

The invention discloses a benzimidazole derivative, and a preparation method and purpose thereof. A structural formula is as follows; and R1 is one selected from the group consisting of H, F, Cl, Br, CH3 and NO3, and the substituted position of -OR2 is ortho- position, meta-position or para- position. The benzimidazole derivative can be applied to control of nematodes, and mainly control of plant parasitic nematodes, such as root-knot nematode, M. incognita, M. javanica, M. arenaria and M. hapla; and the benzimidazole derivative can also be used as a fungicide for prevention of various pathogenic bacteria. The benzimidazole derivative can effectively control plant pests, mites, nematodes and bacteria, and can be used in agricultural control of pest and pathogenic bacteria.

Description

Benzimidizole derivatives and its production and use
Technical field
The present invention relates to Insecticiding-miticiding technical field, particularly relate to benzimidizole derivatives and its production and use.
Background technology
Along with the development of economic society, people require more and more higher to agriculture economic benefit, but the harm of Agricultural pests evil mite has had a strong impact on output and the quality of agricultural-food, and for example aphid can endanger various plants, and the honeydew of its secretion can cause sooty mold; The multiple cresss such as small cabbage moth harm Chinese cabbage, wild cabbage, affect quality of vegetable, so kill pests evil mite seem more and more important.
Summary of the invention
In view of this, the object of the invention is to propose a kind of benzimidizole derivatives and its production and use, effectively to control plant insect, evil mite, nematode and germ.
Based on above-mentioned purpose, the structural formula of benzimidizole derivatives provided by the invention is as follows:
Figure BDA0000394124050000011
Wherein, R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of ,-OR 2the position replacing is a kind of in ortho position, a position and contraposition, and R 2be selected from
Figure BDA0000394124050000012
with
Figure BDA0000394124050000014
in a kind of.
Alternatively, described benzimidizole derivatives makes by following steps:
Hydroxy benzaldehyde and sodium bisulfite are dissolved in aqueous ethanolic solution, under room temperature, stir 0.3-0.8 hour, the mixture that suction filtration reaction obtains, obtains hydroxybenzene methylsulfonic acid acid sodium;
Described hydroxybenzene methylsulfonic acid acid sodium and substituted o-phenylenediamine are dissolved in DMF, backflow 1-3 hour, the mixture then reaction being obtained is poured in ice, suction filtration, recrystallization obtains intermediate;
Described intermediate and triethylamine are dissolved in methylene dichloride, cryosel is bathed and is cooled to-3～-8 ℃, acyl chloride compound is dissolved in to methylene dichloride and is made into solution of acid chloride, then described solution of acid chloride is joined in the reaction system of described intermediate and triethylamine, naturally be warming up to 24～28 ℃, continue stirring reaction 1～1.2h; The organic layer that separating reaction obtains, then, successively by washing, dry, concentrated this organic layer separated with silica gel column chromatography, obtains described benzimidizole derivatives;
Wherein, the structural formula of described substituted o-phenylenediamine is
Figure BDA0000394124050000021
The structural formula of described intermediate is
The structural formula of described acyl chloride compound is R 2-Cl,
R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of,
R 2be selected from
Figure BDA0000394124050000023
Figure BDA0000394124050000024
with
Figure BDA0000394124050000025
in a kind of.
The present invention also provides the method for the above-mentioned benzimidizole derivatives of preparation, comprises the following steps:
Hydroxy benzaldehyde and sodium bisulfite are dissolved in aqueous ethanolic solution, under room temperature, stir 0.3-0.8 hour, the mixture that suction filtration reaction obtains, obtains hydroxybenzene methylsulfonic acid acid sodium;
Described hydroxybenzene methylsulfonic acid acid sodium and substituted o-phenylenediamine are dissolved in DMF, backflow 1-3 hour, the mixture then reaction being obtained is poured in ice, suction filtration, recrystallization obtains intermediate;
Described intermediate and triethylamine are dissolved in methylene dichloride, cryosel is bathed and is cooled to-3～-8 ℃, acyl chloride compound is dissolved in to methylene dichloride and is made into solution of acid chloride, then described solution of acid chloride is joined in the reaction system of described intermediate and triethylamine, naturally be warming up to 24～28 ℃, continue stirring reaction 1～1.2h; The organic layer that separating reaction obtains, then, successively by washing, dry, concentrated this organic layer separated with silica gel column chromatography, obtains described benzimidizole derivatives;
Wherein, the structural formula of described substituted o-phenylenediamine is
Figure BDA0000394124050000031
The structural formula of described intermediate is
Figure BDA0000394124050000032
The structural formula of described acyl chloride compound is R 2-Cl,
R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of,
R 2be selected from
Figure BDA0000394124050000033
Figure BDA0000394124050000034
with
Figure BDA0000394124050000035
in a kind of.
Alternatively, described hydroxy benzaldehyde is selected from Benzaldehyde,2-hydroxy, a kind of in 3-hydroxy benzaldehyde and 4-hydroxy benzaldehyde.
Alternatively, in described aqueous ethanolic solution, the volume ratio of second alcohol and water is 1:0.9～1.2.
Preferably, in the step of described washing organic layer, adopt water washing organic layer 2～4 times, the volume that at every turn washs institute's water is 1.3～1.8 times of organic layer volume.
Preferably, the organic layer after washing described in employing anhydrous magnesium sulfate drying.
Alternatively, described silica gel is 100～200 orders, and eluent is sherwood oil and ethyl acetate, and the volume ratio of described sherwood oil and ethyl acetate is 4～1:1.
The present invention also provides the purposes of above-mentioned benzimidizole derivatives, and described benzimidizole derivatives is used for desinsection, kills mite and sterilization.
As can be seen from above, the present invention a kind of novel benzimidazole derivatives is provided, benzimidizole derivatives provided by the invention can be for controlling various agricultural, gardens and the harmful insect of warehousing, as lepidopteran, Diptera, Homoptera and some are without vertebra insect, as mite class.Particularly: Aphis gossypii(cotten aphid), Myzus persicae(black peach aphid), Lipaphis erysimi(vegetable aphid) Plutella xylostella(small cabbage moth), Nilaparvata lugens(brown paddy plant hopper), Tetranychus cinnabarinus(carmine spider mite) Pieris brassicae(large white butterfly), Anopheles spp. (Anopheles), Culex spp(Culex).Also can be for control nematode, main control plant nematode, as root knot nematode, Meloidogyne incognita (M.incognita), javanese root knot nematode (M.javanica), peanut root-knot nematode (M.arenaria) and northern root knot nematode (M.hapla).Also can be used as sterilant, prevent and treat multiple pathogenic bacteria.This benzimidizole derivatives can be controlled plant insect, evil mite, nematode and germ effectively, can be applied in the upper prevention and elimination of disease and pests of agricultural, pathogenic bacteria.
Embodiment
For making the object, technical solutions and advantages of the present invention clearer, below in conjunction with specific embodiment, the present invention is described in more detail.
The structural formula of benzimidizole derivatives provided by the invention is as follows:
Figure BDA0000394124050000041
Wherein, R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of ,-OR 2the position replacing is a kind of in ortho position, a position and contraposition, and R 2be selected from
Figure BDA0000394124050000043
with
Figure BDA0000394124050000044
in a kind of.
The concrete array mode of part of compounds is referring to table 1:
Table 1
Figure BDA0000394124050000045
Figure BDA0000394124050000051
Figure BDA0000394124050000061
Figure BDA0000394124050000071
Figure BDA0000394124050000081
Figure BDA0000394124050000091
Figure BDA0000394124050000101
Figure BDA0000394124050000121
Figure BDA0000394124050000131
The present invention also provides the preparation method of described benzimidizole derivatives, and its synthetic route is as follows:
Figure BDA0000394124050000141
Wherein, R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of ,-OR 2the position replacing is a kind of in ortho position, a position and contraposition, and R 2be selected from
Figure BDA0000394124050000142
Figure BDA0000394124050000143
with in a kind of.
Wherein, rt is room temperature room temperature, and rf is that reflux refluxes, and ice-salt baths cryosel is bathed.
The preparation method of embodiment 1(compound 14)
By 0.04mol(4.88g) p-Hydroxybenzaldehyde and 0.04mol(4.16g) sodium bisulfite be dissolved in (volume ratio of second alcohol and water is 1:1) in 40ml aqueous ethanolic solution, under room temperature, stir 0.5h.The mixture that suction filtration reaction obtains, obtains 7.7g para hydroxybenzene methylsulfonic acid acid sodium, and yield is 86%.
By 0.01mol(2.26g) para hydroxybenzene methanesulfonic sodium and 0.01mol(1.08g) O-Phenylene Diamine is dissolved in the DMF of 30ml, backflow 2h; Then mixture reaction being obtained is poured in ice, suction filtration, and recrystallization obtains 1.14g2-(2-hydroxybenzene)-1 hydrogen-benzoglyoxaline, and yield is 54%.
Nuclear magnetic data: 1hNMR, 300MHz, interior mark TMS, solvent C DCl 3, d:7.93 (d, 2H), 7.57 (br, 1H), 7.55 (m, 2H), 7.21 (m, 2H), 6.93 (d, 2H), 5.35 (br, 1H).
By 4mmol(0.84g) 2-(2-hydroxybenzene)-1 hydrogen-benzoglyoxaline and 4mmol(0.42g) triethylamine be dissolved in 8ml methylene dichloride, cryosel is bathed and to be cooled to-5 ℃.By 4mmol(0.64g) first cyanogen chrysanthemum acyl chlorides is dissolved in the first cyanogen chrysanthemum solution of acid chloride that 8ml methylene dichloride is made into 0.05mol/l, it is slowly added in the reaction system of 2-(2-hydroxybenzene)-1 hydrogen-benzoglyoxaline and triethylamine, naturally be warming up to 26 ℃, continue stirring reaction 1h.The organic layer that separating reaction obtains, with the water washing organic layer of 1.5 times of volumes 3 times, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally use separated (the 100-200 order silica gel of silica gel column chromatography, eluent is sherwood oil: ethyl acetate=4:1-1:1), obtain product 1.1g, yield 82%.The structural formula of products therefrom is:
Figure BDA0000394124050000151
Nuclear magnetic data: 1hNMR, 300MHz, interior mark TMS, solvent C DCl 3, d:7.92 (d, 2H), 7.59 (br, 1H), 7.53 (m, 2H), 7.21 (m, 2H), 6.93 (d, 2H), 1.07 (d, 13H).
The preparation method of embodiment 2(compound 15)
By 0.04mol(4.88g) p-Hydroxybenzaldehyde and 0.04mol(4.16g) sodium bisulfite be dissolved in (volume ratio of second alcohol and water is 1:1.2) in 50ml aqueous ethanolic solution, under room temperature, stir 0.6h.The mixture that suction filtration reaction obtains, obtains 7.7g para hydroxybenzene methylsulfonic acid acid sodium, and yield is 86%.
By 0.01mol(2.26g) para hydroxybenzene methanesulfonic sodium and 0.01mol(1.08g) O-Phenylene Diamine is dissolved in the DMF of 35ml, backflow 1.5h; Then mixture reaction being obtained is poured in ice, suction filtration, and recrystallization obtains 1.14g2-(2-hydroxybenzene)-1 hydrogen-benzoglyoxaline, and yield is 54%.
Nuclear magnetic data: 1hNMR, 300MHz, interior mark TMS, solvent C DCl 3, d:7.93 (d, 2H), 7.57 (br, 1H), 7.55 (m, 2H), 7.21 (m, 2H), 6.93 (d, 2H), 5.35 (br, 1H).
By 4mmol(0.84g) 2-(2-hydroxybenzene)-1 hydrogen-benzoglyoxaline and 4mmol(0.42g) triethylamine be dissolved in 7ml methylene dichloride, cryosel is bathed and to be cooled to-7 ℃.3-methyl-2-(4-chloro-phenyl-4mmol(0.92g)) butyryl chloride is dissolved in 3-methyl-2-(4-chloro-phenyl-that 8ml methylene dichloride is made into 0.05mol/l) butyryl chloride solution, it is slowly added in the reaction system of 2-(2-hydroxybenzene)-1 hydrogen-benzoglyoxaline and triethylamine, naturally be warming up to 28 ℃, continue stirring reaction 1.2h.The organic layer that separating reaction obtains, with the water washing organic layer of 1.8 times of volumes 2 times, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally use separated (the 100-200 order silica gel of silica gel column chromatography, eluent is sherwood oil: ethyl acetate=4:1-1:1), obtain product 1.2g, yield 74%.The structural formula of products therefrom is:
Figure BDA0000394124050000161
Nuclear magnetic data: 1HNMR, 300MHz, interior mark TMS, solvent C DCl3, d:7.96 (d, 2H), 7.57 (br, 2H), 7.35 (m, 4H), 7.24 (m, 3H), 7.05 (d, 2H), 3.37 (s, 1H), 2.44(m, 1H), 1.17 (t, 3H), 0.75 (m, 3H).
The preparation method of embodiment 3(compound 30)
By 0.04mol(4.88g) p-Hydroxybenzaldehyde and 0.04mol(4.16g) sodium bisulfite be dissolved in (volume ratio of second alcohol and water is 1:0.9) in 45ml aqueous ethanolic solution, under room temperature, stir 0.3h.The mixture that suction filtration reaction obtains, obtains 7.7g para hydroxybenzene methylsulfonic acid acid sodium, and yield is 86%.
By 0.01mol(2.26g) para hydroxybenzene methanesulfonic sodium and 0.01mol(1.26g) 4-fluorine O-Phenylene Diamine is dissolved in the DMF of 30ml, backflow 3h; Then mixture reaction being obtained is poured in ice, suction filtration, and recrystallization obtains 1.14g2-(2-hydroxybenzene)-1 hydrogen-(4-fluorine) benzoglyoxaline, and yield is 50%.
Nuclear magnetic data: 1hNMR, 300MHz, interior mark TMS, solvent C DCl 3, d:7.93 (d, 2H), 7.57 (br, 1H), 7.55 (m, 2H), 7.21 (m, 2H), 6.939 (d, 2H), 5.35 (br, 1H).
By 4mmol(0.91g) 2-(2-hydroxybenzene)-1 hydrogen-(4-fluorine) benzoglyoxaline and 4mmol(0.42g) triethylamine be dissolved in 10ml methylene dichloride, cryosel is bathed and to be cooled to-8 ℃.By 4mmol(0.92g) 3-methyl-2-(4-chloro-phenyl-) butyryl chloride is dissolved in 3-methyl-2-(4-chloro-phenyl-that 8ml methylene dichloride is made into 0.05mol/l) butyryl chloride solution, it is slowly added in the reaction system of 2-(2-hydroxybenzene)-1 hydrogen-(4-fluorine) benzoglyoxaline and triethylamine, naturally be warming up to 28 ℃, continue stirring reaction 1.1h.The organic layer that separating reaction obtains, with the water washing organic layer of 1.3 times of volumes 4 times, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally use separated (the 100-200 order silica gel of silica gel column chromatography, eluent is sherwood oil: ethyl acetate=4:1-1:1), obtain product 1.2g, yield 74%.The structural formula of products therefrom is:
Figure BDA0000394124050000171
Nuclear magnetic data: 1hNMR, 300MHz, interior mark TMS, solvent C DCl 3, d:7.98 (d, 2H), 7.57 (br, 2H), 7.35 (m, 4H), 7.24 (m, 3H), 7.05 (d, 2H), 3.37 (s, 1H), 2.44 (m, 1H), 1.17 (t, 3H), 0.75 (m, 3H).
The preparation method of embodiment 4(compound 74)
By 0.04mol(4.88g) p-Hydroxybenzaldehyde and 0.04mol(4.16g) sodium bisulfite be dissolved in (volume ratio of second alcohol and water is 1:1.1) in 38ml aqueous ethanolic solution, under room temperature, stir 0.8h.The mixture that suction filtration reaction obtains, obtains 7.7g para hydroxybenzene methylsulfonic acid acid sodium, and yield is 86%.
By 0.01mol(2.26g) para hydroxybenzene methanesulfonic sodium and 0.01mol(1.22g) 4-methyl-o-phenylenediamine is dissolved in the DMF of 30ml, backflow 1h; Then mixture reaction being obtained is poured in ice, suction filtration, and recrystallization obtains 1.1g2-(2-hydroxybenzene)-1 hydrogen-(4-methyl) benzoglyoxaline, and yield is 51%.
Nuclear magnetic data 1hNMR, 300MHz, interior mark TMS, solvent C DCl 3, d:7.93 (d, 2H), 7.57 (br, 1H), 7.55 (m, 2H), 7.21 (m, 2H), 6.93 (d, 2H), 5.35 (br, 1H), 2.34 (s, 3H).
By 4mmol(0.89g) 2-(2-hydroxybenzene)-1 hydrogen-(4-methyl) benzoglyoxaline and 4mmol(0.42g) triethylamine be dissolved in 10ml methylene dichloride, cryosel is bathed and to be cooled to-3 ℃.By 4mmol(0.64g) first cyanogen chrysanthemum acyl chlorides is dissolved in the first cyanogen chrysanthemum solution of acid chloride that 8ml methylene dichloride is made into 0.05mol/l, it is slowly added in the reaction system of 2-(2-hydroxybenzene)-1 hydrogen-(4-methyl) benzoglyoxaline and triethylamine, naturally be warming up to 24 ℃, continue stirring reaction 1.1h.The organic layer that separating reaction obtains, with the water washing organic layer of 1.5 times of volumes 3 times, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally use separated (the 100-200 order silica gel of silica gel column chromatography, eluent is sherwood oil: ethyl acetate=4:1-1:1), obtain product 1.1g, yield 71%.The structural formula of products therefrom is:
Figure BDA0000394124050000172
Nuclear magnetic data: 1hNMR, 300MHz, interior mark TMS, solvent C DCl 3, d:7.92 (d, 2H), 7.59 (br, 1H), 7.53 (m, 2H), 7.21 (m, 2H), 6.93 (d, 2H), 2.34 (s, 3H), 1.07 (d, 13H).
Benzimidizole derivatives provided by the invention can be for controlling various agricultural, gardens and the harmful insect of warehousing, as lepidopteran, Diptera, Homoptera and some are without vertebra insect, as mite class.Particularly: Aphis gossypii(cotten aphid), Myzus persicae(black peach aphid), Lipaphis erysimi(vegetable aphid) Plutella xylostella(small cabbage moth), Nilaparvata lugens(brown paddy plant hopper), Tetranychus cinnabarinus(carmine spider mite) Pieris brassicae(large white butterfly), Anopheles spp. (Anopheles), Culex spp(Culex).
Benzimidizole derivatives provided by the invention can be for control nematode, main control plant nematode, as root knot nematode, Meloidogyne incognita (M.incognita), javanese root knot nematode (M.javanica), peanut root-knot nematode (M.arenaria) and northern root knot nematode (M.hapla).
Benzimidizole derivatives provided by the invention also can be used as sterilant, prevents and treats multiple pathogenic bacteria.
Benzimidizole derivatives provided by the invention is made to the composition of various ways, as pulvis, wettable powder, granula, missible oil, suspension agent etc., application and soil, plant, seed.In order effectively to prevent and treat harmful insect, evil mite, nematode etc., when described benzimidizole derivatives is made to corresponding composition, in composition, contain the described benzimidizole derivatives of 15%-90% massfraction.
Adopt benzimidizole derivatives provided by the invention to carry out bioactive mensuration to several insects and mites, measuring method is: benzimidizole derivatives is with after dmso solution, adopt the aqueous solution containing 0.1% tween 100 by benzimidizole derivatives solution dilution to desired concn.
With Myxus persicae(black peach aphid), Plutella xylostella(small cabbage moth), Nilaparvata lugens(brown paddy plant hopper), Tetranychus cinnabarinus(carmine spider mite) be target, adopt airbrush spray method and immersion method to carry out insecticidal activity evaluation, airbrush spray method spray pressure is that 10psi (is roughly equal to 0.7kg/cm 2), spouting liquid is 0.5ml, the mortality ratio of 48-72h investigation target after processing.
Specific operation process is as follows:
(1) to the control of aphid (spray method): 20mg benzimidizole derivatives is dissolved in to the stoste that 2ml dimethyl sulfoxide (DMSO) forms 10mg/ml, then with the aqueous solution containing 0.1% tween 100, stoste is diluted to finite concentration.With manual sprayer, use testing liquid, be sprayed on the blade that contains suitable aphid (about 30-50 aphid/leaf), until testing liquid flows out blade both sides.Every kind of each concentration of compound repeats 3 times.Blank is only processed with the aqueous solution containing 0.1% tween 100.Under the condition of 23 ℃ and relative humidity 40%, blade is kept to 2-3 days, record sum and the death toll of aphid on every leaf, calculate mortality ratio.
(2) to the control of small cabbage moth (immersion method): 20mg benzimidizole derivatives is dissolved in to the stoste that 2ml dimethyl sulfoxide (DMSO) forms 10mg/ml, then with the aqueous solution containing 0.1% tween 100, stoste is diluted to finite concentration.The disk that Caulis et Folium Brassicae capitatae blade is cut into diameter 7cm left and right soaks 5-10s in certain density testing liquid, and taking-up is dried, and places 10-20 small cabbage moth on every blade, preservative film sealing, and the medicine of each concentration repeats 3 times.24 ℃ of temperature, humidity 70%, raises 24-48h, records total borer population and the dead borer population of each culture dish.
(3) to the control of brown paddy plant hopper (spray method and systematic testing): rice shoot is immersed in the water of two portions glass cylinder bottom, bottom is used wire-mesh screen to prop rice shoot, then use scotch tape to connect two portions of glass cylinder, each is processed with three cylinders.20mg benzimidizole derivatives is dissolved in to the stoste that is made into 10mg/ml in 2ml dimethyl sulfoxide (DMSO), with the aqueous solution containing 0.1% tween 100, stoste is diluted to different concns.The testing liquid of 0.5ml and solvent control and blank are sprayed in glass cylinder.Systematic testing, adds stoste in the water of testing rice shoot and is made into different concns.In foliar spray and systematic testing, after dispenser 3h, brown paddy plant hopper nymph in 3 age is introduced in cylinder.The test unit (cylinder) of processing is placed in 28 ℃ of temperature, in the growth room of humidity 70%, within 2 days and 6 days, carries out observed and recorded.
(4) to the control of carmine spider mite (medicine embrane method): benzimidizole derivatives is become to the liquid of different concns by acetone diluted, 3 repetitions of each concentration, from the liquid having diluted, drawing 1.2ml adds in 1.5ml centrifuge tube, rotate gently centrifuge tube, make medicament form uniform medicine film at inside pipe wall, outwell unnecessary liquid, be put into ventilation and treat that acetone volatilizees completely, contrast is separately by acetone treatment, and method is identical.In each medicine film pipe, place 30 one-tenth mites that health is consistent, 24h under indoor normal raising condition, checks mortality ratio.Death standard: touch polypide with writing brush, only have 1 foot to move or the complete motionless death that is.Contrast mortality ratio is less than 10% for effectively measuring.
(5) control to Anopheles Sinensis Larvae: benzimidizole derivatives is diluted to the liquid of different concns with the dechlorination tap water that contains 0.1% tween, after Anopheles Sinensis Larvae is tamed in the tap water of dechlorination, choose respectively in the same size, activity 40 of 3 instar larvaes rapidly, be placed in the liquid of different concns, each concentration repeats 3 times, using the tap water of not offeing medicine as blank, the mortality ratio of larva after computing 2h.
Test result is as follows:
Table 2
Figure BDA0000394124050000191
Figure BDA0000394124050000201
It should be noted that, benzimidizole derivatives provided by the invention can be used with the form of composition, for desinsection, kill mite, described composition comprises acceptable carrier in benzimidizole derivatives and phytology.Can be coated with spraying, Local treatment, seed, the various ways such as microcapsule, system absorptions, bait applies described composition, to reach the object of control insect.Described composition can be concentrated solid or liquid formulations (be dispersed in water and can use) or granular recipe.The dispersion majority of described benzimidizole derivatives is water suspending agent or the emulsion of being made by the concentrated formula of benzimidizole derivatives.These water dissolvables, aqueous suspension and can emulsifying property formula be to be commonly referred to as wettable powder or wetting properties granula.They are uniform mixtures of active compound (being benzimidizole derivatives), inert support and tensio-active agent, and the concentration of active compound is the 10%-90% of massfraction normally.Carrier is montmorillonitic clay, diatomite, silicate and convex-concave rod clay normally, accounts for the 0.5%-10% of wettable powder (grain) agent.Tensio-active agent can be naphthalenesulfonate, sulfonated alkyl naphathalene, alkyl sulfuric ester and nonionic surface active agent etc.
Also described benzimidizole derivatives can be dissolved in suitable organic solvent, with solution form redispersion, use.Insecticidal/acaricidal agent is used in liquid vehicle with activeconstituents conventionally, according to the concentration of activeconstituents, determines rate of utilization, and carrier is water normally.Conventionally activity component concentration is that 10mg/kg-5000mg/kg concentration can well be controlled, just enough for most compound 10mg/kg-500mg/kg.The place of using compound can be any place that insect or mite class are assembled, as the surface of vegetable crop, fruit, ornamental plant, buildings, soil etc.Compound of the present invention can be used with one or more sterilants, sterilant together with weedicide, also can sequential application.
As can be seen here, benzimidizole derivatives provided by the invention can be controlled plant insect, evil mite, nematode and germ effectively, can be applied in the upper prevention and elimination of disease and pests of agricultural, pathogenic bacteria.
Those of ordinary skill in the field are to be understood that: the foregoing is only specific embodiments of the invention; be not limited to the present invention; within the spirit and principles in the present invention all, any modification of making, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.

Claims (9)

1. a benzimidizole derivatives, is characterized in that, its structural formula is as follows:
Figure FDA0000394124040000011
Wherein, R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of ,-OR 2the position replacing is a kind of in ortho position, a position and contraposition, and R 2be selected from
Figure FDA0000394124040000012
Figure FDA0000394124040000013
with
Figure FDA0000394124040000014
in a kind of.
2. benzimidizole derivatives according to claim 1, is characterized in that, described benzimidizole derivatives makes by following steps:
Hydroxy benzaldehyde and sodium bisulfite are dissolved in aqueous ethanolic solution, under room temperature, stir 0.3-0.8 hour, the mixture that suction filtration reaction obtains, obtains hydroxybenzene methylsulfonic acid acid sodium;
Described hydroxybenzene methylsulfonic acid acid sodium and substituted o-phenylenediamine are dissolved in DMF, backflow 1-3 hour, the mixture then reaction being obtained is poured in ice, suction filtration, recrystallization obtains intermediate;
Described intermediate and triethylamine are dissolved in methylene dichloride, cryosel is bathed and is cooled to-3～-8 ℃, acyl chloride compound is dissolved in to methylene dichloride and is made into solution of acid chloride, then described solution of acid chloride is joined in the reaction system of described intermediate and triethylamine, naturally be warming up to 24～28 ℃, continue stirring reaction 1～1.2h; The organic layer that separating reaction obtains, then, successively by washing, dry, concentrated this organic layer separated with silica gel column chromatography, obtains described benzimidizole derivatives;
Wherein, the structural formula of described substituted o-phenylenediamine is
Figure FDA0000394124040000015
The structural formula of described intermediate is
Figure FDA0000394124040000016
The structural formula of described acyl chloride compound is R 2-Cl,
R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of,
R 2be selected from
Figure FDA0000394124040000022
with
Figure FDA0000394124040000023
in a kind of.
3. a method of preparing benzimidizole derivatives claimed in claim 1, is characterized in that, comprises the following steps:
Hydroxy benzaldehyde and sodium bisulfite are dissolved in aqueous ethanolic solution, under room temperature, stir 0.3-0.8 hour, the mixture that suction filtration reaction obtains, obtains hydroxybenzene methylsulfonic acid acid sodium;
Described hydroxybenzene methylsulfonic acid acid sodium and substituted o-phenylenediamine are dissolved in DMF, backflow 1-3 hour, the mixture then reaction being obtained is poured in ice, suction filtration, recrystallization obtains intermediate;
Described intermediate and triethylamine are dissolved in methylene dichloride, cryosel is bathed and is cooled to-3～-8 ℃, acyl chloride compound is dissolved in to methylene dichloride and is made into solution of acid chloride, then described solution of acid chloride is joined in the reaction system of described intermediate and triethylamine, naturally be warming up to 24～28 ℃, continue stirring reaction 1～1.2h; The organic layer that separating reaction obtains, then, successively by washing, dry, concentrated this organic layer separated with silica gel column chromatography, obtains described benzimidizole derivatives;
Wherein, the structural formula of described substituted o-phenylenediamine is
Figure FDA0000394124040000024
The structural formula of described intermediate is
Figure FDA0000394124040000025
The structural formula of described acyl chloride compound is R 2-Cl,
R 1be selected from H, F, Cl, Br, CH 3, NO 3in a kind of,
R 2be selected from
Figure FDA0000394124040000026
Figure FDA0000394124040000031
with in a kind of.
4. the preparation method of benzimidizole derivatives according to claim 3, is characterized in that, described hydroxy benzaldehyde is selected from Benzaldehyde,2-hydroxy, a kind of in 3-hydroxy benzaldehyde and 4-hydroxy benzaldehyde.
5. the preparation method of benzimidizole derivatives according to claim 3, is characterized in that, in described aqueous ethanolic solution, the volume ratio of second alcohol and water is 1:0.9～1.2.
6. the preparation method of benzimidizole derivatives according to claim 3, is characterized in that, in the step of described washing organic layer, adopts water washing organic layer 2～4 times, and the volume that at every turn washs institute's water is 1.3～1.8 times of organic layer volume.
7. the preparation method of benzimidizole derivatives according to claim 6, is characterized in that, adopts the organic layer after washing described in anhydrous magnesium sulfate drying.
8. the preparation method of benzimidizole derivatives according to claim 3, is characterized in that, described silica gel is 100～200 orders, and eluent is sherwood oil and ethyl acetate, and the volume ratio of described sherwood oil and ethyl acetate is 4～1:1.
9. the purposes of benzimidizole derivatives according to claim 1, is characterized in that, described benzimidizole derivatives is used for desinsection, kills mite and sterilization.
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