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CN103524422B - 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
CN103524422B
CN103524422B CN201310473947.XA CN201310473947A CN103524422B CN 103524422 B CN103524422 B CN 103524422B CN 201310473947 A CN201310473947 A CN 201310473947A CN 103524422 B CN103524422 B CN 103524422B
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benzimidizole derivatives
organic layer
dissolved
preparation
structural formula
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CN103524422A (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

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses a benzimidazole derivative, and a preparation method and purpose thereof. The structural formula is shown in the description, 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 the economic benefit of agricultural, but the harm of Agricultural pests evil mite has had a strong impact on the seed output and quality of agricultural-food, and such as aphid can endanger various plants, and the honeydew of its secretion can cause sooty mold; Multiple cress such as small cabbage moth harm Chinese cabbage, wild cabbage etc., affects quality of vegetable, and therefore kill pests evil mite seems 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:
Wherein, R 1be selected from H, F, Cl, Br, CH 3, NO 3in one ,-OR 2the position replaced is the one in ortho position, a position and contraposition, and R 2be selected from
with in one.
Alternatively, described benzimidizole derivatives is obtained by following steps:
Hydroxy benzaldehyde and sodium bisulfite are dissolved in aqueous ethanolic solution, stirred at ambient temperature 0.3-0.8 hour, the mixture that suction filtration is obtained by reacting, obtain hydroxybenzene methylsulfonic acid acid sodium;
Be dissolved in DMF by described hydroxybenzene methylsulfonic acid acid sodium and substituted o-phenylenediamine, backflow 1-3 hour, then pour in ice by the mixture be obtained by reacting, suction filtration, recrystallization obtains intermediate;
Described intermediate and triethylamine are dissolved in methylene dichloride, cryosel bath is cooled to-3 ~-8 DEG C, acyl chloride compound is dissolved in 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 DEG C, continue stirring reaction 1 ~ 1.2h; The organic layer that separating reaction obtains, then successively by washing, dry, be concentratedly separated this organic layer with silica gel column chromatography, namely obtain described benzimidizole derivatives;
Wherein, the structural formula of described substituted o-phenylenediamine is
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 one,
R 2be selected from
with in one.
The present invention also provides the method preparing above-mentioned benzimidizole derivatives, comprises the following steps:
Hydroxy benzaldehyde and sodium bisulfite are dissolved in aqueous ethanolic solution, stirred at ambient temperature 0.3-0.8 hour, the mixture that suction filtration is obtained by reacting, obtain hydroxybenzene methylsulfonic acid acid sodium;
Be dissolved in DMF by described hydroxybenzene methylsulfonic acid acid sodium and substituted o-phenylenediamine, backflow 1-3 hour, then pour in ice by the mixture be obtained by reacting, suction filtration, recrystallization obtains intermediate;
Described intermediate and triethylamine are dissolved in methylene dichloride, cryosel bath is cooled to-3 ~-8 DEG C, acyl chloride compound is dissolved in 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 DEG C, continue stirring reaction 1 ~ 1.2h; The organic layer that separating reaction obtains, then successively by washing, dry, be concentratedly separated this organic layer with silica gel column chromatography, namely obtain described benzimidizole derivatives;
Wherein, the structural formula of described substituted o-phenylenediamine is
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 one,
R 2be selected from
with in one.
Alternatively, described hydroxy benzaldehyde is selected from Benzaldehyde,2-hydroxy, the one 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 of each washing water used is 1.3 ~ 1.8 times of organic layer volume.
Preferably, the organic layer after washing described in anhydrous magnesium sulfate drying is adopted.
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 provides a kind of novel benzimidazole derivatives, benzimidizole derivatives provided by the invention may be used for controlling the harmful insect of various agricultural, gardens and warehousing, as lepidopteran, Diptera, Homoptera and some are without vertebra insect, as mite class.Particularly: Aphisgossypii(cotten aphid), Myzus persicae(black peach aphid), Lipaphis erysimi(vegetable aphid) Plutellaxylostella(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 may be used for preventing and treating 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 M hapla (M.hapla).Also as sterilant, multiple pathogenic bacteria can be prevented and treated.This benzimidizole derivatives can control plant insect, evil mite, nematode and germ effectively, can be applied in agriculturally prevention and elimination of disease and pests, pathogenic bacteria.
Embodiment
For making the object, technical solutions and advantages of the present invention clearly understand, 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:
Wherein, R 1be selected from H, F, Cl, Br, CH 3, NO 3in one ,-OR 2the position replaced is the one in ortho position, a position and contraposition, and R 2be selected from
with in one.
The concrete array mode of part of compounds is see table 1:
Table 1
The present invention also provides the preparation method of described benzimidizole derivatives, and its synthetic route is as follows:
Wherein, R 1be selected from H, F, Cl, Br, CH 3, NO 3in one ,-OR 2the position replaced is the one in ortho position, a position and contraposition, and R 2be selected from
with in one.
Wherein, rt and room temperature room temperature, rf and 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, stirred at ambient temperature 0.5h.The mixture that suction filtration is obtained by reacting, obtain 7.7g para hydroxybenzene methylsulfonic acid acid sodium, 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 pour in ice by the mixture be obtained by reacting, suction filtration, 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 bath is cooled to-5 DEG C.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 DEG C, continue stirring reaction 1h.The organic layer that separating reaction obtains, with the water washing organic layer 3 times of 1.5 times of volumes, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally be separated (100-200 order silica gel with 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:
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, stirred at ambient temperature 0.6h.The mixture that suction filtration is obtained by reacting, obtain 7.7g para hydroxybenzene methylsulfonic acid acid sodium, 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 pour in ice by the mixture be obtained by reacting, suction filtration, 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 bath is cooled to-7 DEG C.3-methyl-2-(4-chloro-phenyl-4mmol(0.92g)) butyryl chloride is dissolved in the 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 DEG C, continue stirring reaction 1.2h.The organic layer that separating reaction obtains, with the water washing organic layer 2 times of 1.8 times of volumes, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally be separated (100-200 order silica gel with 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:
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, stirred at ambient temperature 0.3h.The mixture that suction filtration is obtained by reacting, obtain 7.7g para hydroxybenzene methylsulfonic acid acid sodium, 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 pour in ice by the mixture be obtained by reacting, suction filtration, 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 bath is cooled to-8 DEG C.By 4mmol(0.92g) 3-methyl-2-(4-chloro-phenyl-) butyryl chloride is dissolved in the 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 DEG C, continue stirring reaction 1.1h.The organic layer that separating reaction obtains, with the water washing organic layer 4 times of 1.3 times of volumes, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally be separated (100-200 order silica gel with 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:
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, stirred at ambient temperature 0.8h.The mixture that suction filtration is obtained by reacting, obtain 7.7g para hydroxybenzene methylsulfonic acid acid sodium, 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 pour in ice by the mixture be obtained by reacting, suction filtration, 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 bath is cooled to-3 DEG C.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 DEG C, continue stirring reaction 1.1h.The organic layer that separating reaction obtains, with the water washing organic layer 3 times of 1.5 times of volumes, then with the organic layer after anhydrous magnesium sulfate drying washing, refilter, concentrate this organic layer, finally be separated (100-200 order silica gel with 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:
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 may be used for controlling the harmful insect of various agricultural, gardens and 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), Tetranychuscinnabarinus(carmine spider mite) Pieris brassicae(large white butterfly), Anopheles spp. (Anopheles), Culex spp(Culex).
Benzimidizole derivatives provided by the invention may be used for preventing and treating 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 M hapla (M.hapla).
Benzimidizole derivatives provided by the invention also as sterilant, can prevent and treat multiple pathogenic bacteria.
Benzimidizole derivatives provided by the invention is made the composition of various ways, as pulvis, wettable powder, granula, missible oil, suspension agent etc., application and soil, plant, seed.In order to harmful insect, evil mite, nematode etc. effectively can be prevented and treated, when described benzimidizole derivatives is made corresponding composition, the described benzimidizole derivatives containing 15%-90% massfraction in composition.
Benzimidizole derivatives provided by the invention is adopted to carry out bioactive mensuration to several insects and mites, measuring method is: after benzimidizole derivatives dmso solution, to adopt benzimidizole derivatives solution dilution containing the aqueous solution of 0.1% tween 100 to desired concn.
With Myxus persicae(black peach aphid), Plutella xylostella(small cabbage moth), Nilaparvatalugens(brown paddy plant hopper), Tetranychus cinnabarinus(carmine spider mite) be target, adopt airbrush spray method and immersion method to carry out insecticidal activity qualification, airbrush spray method spray pressure is that 10psi (is roughly equal to 0.7kg/cm 2), spouting liquid is 0.5ml, and after process, 48-72h investigates the mortality ratio of target.
Specific operation process is as follows:
(1) to the control (spray method) of aphid: 20mg benzimidizole derivatives to be dissolved in 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.Use manual sprayer to use testing liquid, be sprayed on the blade containing suitable aphid (about 30-50 head aphid/leaf), until testing liquid flows out blade both sides.Often kind of each concentration of compound repeats 3 times.Blank is only with the aqueous solution process containing 0.1% tween 100.Under 23 DEG C of conditions with relative humidity 40%, blade is kept 2-3 days, record sum and the death toll of aphid on every sheet leaf, calculate mortality ratio.
(2) to the control (immersion method) of small cabbage moth: 20mg benzimidizole derivatives to be dissolved in 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.Caulis et Folium Brassicae capitatae blade is cut into the disk of diameter about 7cm, in certain density testing liquid, soak 5-10s, taking-up is dried, and every sheet blade is placed 10-20 head small cabbage moth, and preservative film seals, and the medicine of each concentration repeats 3 times.Temperature 24 DEG C, humidity 70%, raises 24-48h, records total borer population of each culture dish and dead borer population.
(3) to the control (spray method and systematic testing) of brown paddy plant hopper: rice shoot is immersed in the water bottom two portions glass cylinder, bottom uses wire-mesh screen to prop rice shoot, then scotch tape is used to connect two portions of glass cylinder, each process three cylinders.20mg benzimidizole derivatives is dissolved in the stoste being 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 test rice shoot and is made into different concns.In foliar spray and systematic testing, after dispenser 3h, brown paddy plant hopper 3 nymph in age is introduced in cylinder.The test unit (cylinder) of process is placed in temperature 28 DEG C, in the growth room of humidity 70%, within 2 days and 6 days, carries out observed and recorded.
(4) to the control (medicine embrane method) of carmine spider mite: liquid benzimidizole derivatives acetone diluted being become different concns, each concentration 3 repetition, from the liquid diluted, draw 1.2ml adds in 1.5ml centrifuge tube, rotate centrifuge tube gently, make medicament form uniform medicine film at inside pipe wall, outwell unnecessary liquid, be put into ventilation and treat that acetone volatilizees completely, contrast independent acetone treatment, method is identical.Place the consistent one-tenth mite of 30 health in each medicine film pipe, 24h under indoor normal rearing conditions, checks mortality ratio.Death standard: touch polypide with writing brush, only has 1 foot dynamic or be completely motionlessly death.Contrast mortality ratio is less than 10% for effectively measuring.
(5) to the control of Anopheles Sinensis Larvae: liquid benzimidizole derivatives being diluted to different concns with the dechlorination tap water containing 0.1% tween, after Anopheles Sinensis Larvae is tamed in the tap water of dechlorination, choose in the same size, activity 3 instar larvae 40 rapidly respectively, 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
It should be noted that, benzimidizole derivatives provided by the invention can be used in the form of compositions, for desinsection, kill mite, described composition comprises acceptable carrier in benzimidizole derivatives and phytology.The various ways such as, microcapsule, Systemic absorption, bait coated with spraying, Local treatment, seed can apply described composition, to reach the object controlling 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 the water suspending agent or emulsion be made up of the Concentrated formulations of benzimidizole derivatives.These water dissolvables, aqueous suspension and can emulsifying property formula be commonly referred to as wettable powder or wettable granular.They are uniform mixtures of active compound (i.e. benzimidizole derivatives), inert support and tensio-active agent, the 10%-90% of the concentration of active compound normally massfraction.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 can be dissolved in suitable organic solvent by described benzimidizole derivatives, redispersion uses in the form of a solution.Insecticidal/acaricidal agent uses in a liquid carrier with activeconstituents usually, and the concentration according to activeconstituents determines rate of utilization, and carrier is water normally.Usual activity component concentration is that 10mg/kg-5000mg/kg concentration can well control, just enough for most compound 10mg/kg-500mg/kg.Use the place of compound can be any place that insect or mite class are assembled, as the surface, soil etc. of vegetable crop, fruit, ornamental plant, buildings.Compound of the present invention can be used together with weedicide with one or more sterilants, sterilant, also can sequential application.
As can be seen here, benzimidizole derivatives provided by the invention can control plant insect, evil mite, nematode and germ effectively, can be applied in agriculturally prevention and elimination of disease and pests, 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 amendment made, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.

Claims (7)

1. a benzimidizole derivatives, is characterized in that, its structural formula is as follows:
Wherein, R 1be selected from F, Cl, Br, CH 3, NO 2in one ,-OR 2the position replaced is the one in ortho position, a position and contraposition, and R 2be selected from
in one.
2. prepare a method for benzimidizole derivatives according to claim 1, it is characterized in that, comprise the following steps:
Hydroxy benzaldehyde and sodium bisulfite are dissolved in aqueous ethanolic solution, stirred at ambient temperature 0.3-0.8 hour, the mixture that suction filtration is obtained by reacting, obtain hydroxybenzene methylsulfonic acid acid sodium;
Be dissolved in DMF by described hydroxybenzene methylsulfonic acid acid sodium and substituted o-phenylenediamine, backflow 1-3 hour, then pour in ice by the mixture be obtained by reacting, suction filtration, recrystallization obtains intermediate;
Described intermediate and triethylamine are dissolved in methylene dichloride, cryosel bath is cooled to-3 ~-8 DEG C, acyl chloride compound is dissolved in 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 DEG C, continue stirring reaction 1 ~ 1.2h; The organic layer that separating reaction obtains, then successively by washing, dry, be concentratedly separated this organic layer with silica gel column chromatography, namely obtain described benzimidizole derivatives;
Wherein, the structural formula of described substituted o-phenylenediamine is
The structural formula of described intermediate is
The structural formula of described acyl chloride compound is R 2-Cl,
R 1be selected from F, Cl, Br, CH 3, NO 2in one,
R 2be selected from
in one.
3. the preparation method of benzimidizole derivatives according to claim 2, is characterized in that, described hydroxy benzaldehyde is selected from Benzaldehyde,2-hydroxy, the one in 3-hydroxy benzaldehyde and 4-hydroxy benzaldehyde.
4. the preparation method of benzimidizole derivatives according to claim 2, is characterized in that, in described aqueous ethanolic solution, the volume ratio of second alcohol and water is 1:0.9 ~ 1.2.
5. the preparation method of benzimidizole derivatives according to claim 2, is characterized in that, in the step of described washing organic layer, adopts water washing organic layer 2 ~ 4 times, and the volume of each washing water used is 1.3 ~ 1.8 times of organic layer volume.
6. the preparation method of benzimidizole derivatives according to claim 5, is characterized in that, adopts the organic layer after washing described in anhydrous magnesium sulfate drying.
7. the preparation method of benzimidizole derivatives according to claim 2, 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.
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