CN101759649B - Benzimidazole amide bactericide - Google Patents
Benzimidazole amide bactericide Download PDFInfo
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- CN101759649B CN101759649B CN2008101844609A CN200810184460A CN101759649B CN 101759649 B CN101759649 B CN 101759649B CN 2008101844609 A CN2008101844609 A CN 2008101844609A CN 200810184460 A CN200810184460 A CN 200810184460A CN 101759649 B CN101759649 B CN 101759649B
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Abstract
The present invention relates to a novel benzimidazole amide compound and an application thereof as an agricultural bactericide, belonging to the technical field of pesticides. The compound has the structural formula disclosed in the specification, wherein R represents an alkyl group with a carbon chain length of C2-C4, specifically an ethyl, a propyl, a normal-butyl and an isobutyl; an alkenylwith a carbon chain length of C2-C4, specifically a vinyl, an allyl, an isopropenyl and an isobutenyl; a halogenated alkyl with a carbon chain length of C1-C2, specifically a chloromethyl group, a brooethyl, a 2-chloroethane and a 2-bromomethyl; and different substituted aryl groups specifically refer to a parachloro-penyl methyl, a p-bromophenyl methyl, a p-methoxybenzene methyl, a p-nitro phenyl; and a furfuryl.
Description
Technical field
Technical scheme of the present invention relates to a class benzimidazole amide bactericide, belongs to technical field of pesticide.
Background technology
Crop pest is to cause the agricultural-food underproduction, the important factor that quality descends, and chemical prevention then is the major technique means of control of crop disease.The organic synthesis sterilant is the main part in the present disinfectant use in agriculture, also is the important component part of modern pesticide industry.But the problem that can not be ignored is that along with a large amount of uses of organic synthesis sterilant, crop pathogens has shown resistance or resistance in various degree.For addressing this problem, constantly developing various new type bactericides is lasting problems that pesticide industry faces.
After nineteen sixty-eight found that F-1991 has the good characteristic of control fungal disease, the sterilization idiocratic of benzimidazoles compound had caused the close attention of each big agricultural chemicals company, and has successfully developed disinfectant use in agriculture such as derosal, thiabendazole successively.Benzimidazole germicide has good interior suction conductivity as a kind of sterilant of broad spectrum in making object, therefore can be used for multiple occasions such as seed treatment, soil treatment and cauline leaf spraying.But the defective of this series bactericidal agent maximum is to use and has just produced comparatively serious resistance soon, reports that so far the plant pathogenic fungi that benzimidazole germicide is developed immunity to drugs has hundreds of fungies of 56 genus at least.
The present invention has designed the benzimidazole amide compounds of a class formation novelty, and its constructional feature is that general formula introduced a carbonyl and amide group on imidazole ring.The compound of the type reports seldom that in the literature its bacteriostatic activity does not then appear in the newspapers.
Summary of the invention
The benzimidazole amide compound that the purpose of this invention is to provide a class formation novelty.
Purpose of the present invention also provides the purposes of benzimidazole amide compound as disinfectant use in agriculture.
Benzimidazole amide compound provided by the invention has the general structure shown in the formula (I).
R representative in the formula:
(1) carbon chain lengths is the alkyl of C2～C4, specifically is meant ethyl, propyl group, normal-butyl, isobutyl-;
(2) carbon chain lengths is the thiazolinyl of C2～C4, specifically is meant vinyl, propenyl, pseudoallyl, isobutenyl;
(3) carbon chain lengths is the haloalkyl of C1～C2, specifically is meant chloromethyl, brooethyl, 2-chloroethyl, 2-bromotrifluoromethane;
(4) the different aryl that replace specifically are meant to chlorophenylmethyl, to Brombenzyl, to mehtoxybenzyl, p-nitrophenyl.
(5) furfuryl.
Benzimidazole amide provided by the invention can obtain by following synthetic route:
R representative in the formula:
(1) carbon chain lengths is the alkyl of C2～C4, specifically is meant ethyl, propyl group, normal-butyl, isobutyl-;
(2) carbon chain lengths is the thiazolinyl of C2～C4, specifically is meant vinyl, propenyl, pseudoallyl, isobutenyl;
(3) carbon chain lengths is the haloalkyl of C1～C2, specifically is meant chloromethyl, brooethyl, 2-chloroethyl, 2-bromotrifluoromethane;
(4) the different aryl that replace specifically are meant to chlorophenylmethyl, to Brombenzyl, to mehtoxybenzyl, p-nitrophenyl.
(5) furfuryl.
Benzimidazole amide compound provided by the invention has that raw material is simple, synthesis step is few, reaction yield and the high characteristics of product purity.
Benzimidazole amide compound provided by the invention has well good prevention effect to vegetable diseases such as cucumber downy mildew and graw mold of tomato.
Embodiment
Help to understand the present invention by following embodiment, but do not limit content of the present invention.
Embodiment one
1.1-(third-1-alkene-2-yl)-3-propionyl-1H-benzimidazolyl-2 radicals-ketone is synthetic
In the reaction flask of water trap is housed, the O-Phenylene Diamine and the 220mL dimethylbenzene that add 54g (0.5mol), after heated and stirred refluxes, slowly drip methyl aceto acetate 71.5g (0.55mol) and 20mL dimethylbenzene mixed solution, after dripping off, the stirring and refluxing azeotropic dehydration does not only appear as to there being the globule, continues stirring and refluxing 2h again.Reaction is finished, and crystallization is separated out in cooling, and filtration, drying get white particulate crystallization 76.5g (productive rate 87.9%), are intermediate 1-pseudoallyl-1,3-dihydro-2H-benzimidazolyl-2 radicals-ketone, 120～122 ℃ of fusing points.Get the intermediate 1-pseudoallyl-1 of 1.74g (0.01mol), the triethylamine of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone and 0.0lmol is dissolved in the toluene of 30mL, normal temperature drips the propionyl chloride solution (the 0.92g acrylate chloride is dissolved in the 10mL toluene) of 0.01mol down, stirring at normal temperature 5～8h, wash three times, dry, precipitation promptly get target compound 2.15g (productive rate 93.4%), 126～128 ℃ of fusing points.
Embodiment two
2.1-acryl-3-(third-1-alkene-2-yl)-1H-benzimidazolyl-2 radicals-ketone is synthetic
Intermediate 1-pseudoallyl-1, synthesizing of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone is identical with embodiment one.Get the intermediate 1-pseudoallyl-1 of 1.74g (0.01mol), the triethylamine of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone and 0.01mol is dissolved in the toluene of 30mL, normal temperature drips the acrylate chloride solution (the 0.90g acrylate chloride is dissolved in the 10mL toluene) of 0.01mol down, stirring at normal temperature 5～8h, wash three times, dry, precipitation promptly get target compound 2.11g (productive rate 92.5%), 108～110 ℃ of fusing points.
Embodiment three
3.1-(synthesizing of 3-chlorine propionyl-3-(third-1-alkene-2-yl)-1H-benzimidazolyl-2 radicals-ketone
Intermediate 1-pseudoallyl-1, synthesizing of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone is identical with embodiment one.Get the intermediate 1-pseudoallyl-1 of 1.74g (0.01mol), the triethylamine of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone and 0.01mol is dissolved in the toluene of 30mL, normal temperature drips the 3-chlorpromazine chloride solution (1.26g 3-chlorpromazine chloride is dissolved in the 10mL toluene) of 0.01mol down, stirring at normal temperature 5～8h, wash three times, dry, precipitation promptly get target compound 2.23g (productive rate 84.4%), 110～112 ℃ of fusing points.
Embodiment four
4.4-chloro acetyl-3-(third-1-alkene-2-yl)-1H-benzimidazolyl-2 radicals-ketone is synthetic
Intermediate 1-pseudoallyl-1, synthesizing of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone is identical with embodiment one.Get the intermediate 1-pseudoallyl-1 of 1.74g (0.01mol), the triethylamine of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone and 0.01mol is dissolved in the toluene of 30mL, normal temperature drips 2-(4-chloro-phenyl-) chloride solution (1.88g 2-(4-chloro-phenyl-) Acetyl Chloride 98Min. is dissolved in the 10mL toluene) of 0.01mol down, stirring at normal temperature 5～8h, wash three times, dry, precipitation promptly get target compound 3.09g (productive rate 94.8%), 90～92 ℃ of fusing points.
Embodiment five
5.1-(furans-2 acyl group)-3-(third-1-alkene-2-yl)-1H-benzimidazolyl-2 radicals-ketone is synthetic
Intermediate 1-pseudoallyl-1, synthesizing of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone is identical with embodiment one.Get the intermediate 1-pseudoallyl-1 of 1.74g (0.01mol), the triethylamine of 3-dihydro-2H-benzimidazolyl-2 radicals-ketone and 0.01mol is dissolved in the toluene of 30mL, normal temperature drips furans-2-solution of acid chloride (1.30g furans-2-acyl chlorides is dissolved in the 10mL toluene) of 0.01mol down, stirring at normal temperature 5～8h, wash three times, dry, precipitation promptly get target compound 2.28g (productive rate 85.1%), 104～106 ℃ of fusing points.
Embodiment six
6. the stripped bacteriostatic activity of benzimidazole amide compound
Adopt and suppress the stripped bacteriostatic activity that the spore germination method is measured benzimidazole amide compound provided by the invention.Get the spore suspension that is made into proper concn for the spore of examination pathogenic bacteria, under 10 * 10 low power lens, there are 80～100 spores in each visual field.Test compound is made into the methyl alcohol of series concentration gradient, mixes with spore suspension, get one after another drop of being added on the depression slide, every processing repeats for 3 times.Behind the cultivation 6h that preserves moisture under 25 ℃, check the sprouting of contrast spore.After the germination rate of contrast reaches 85%, check the germination rate of all processing.Is sprouting with spore germ tube length greater than spore short radius person.Other establishes not dosing and is treated to blank, the positive contrast of derosal.Its result is as shown in table 1.Be calculated as follows the inhibition spore germination rate:
The stripped bacteriostatic activity of table 1 benzimidazole amide compound
Embodiment seven
7.1-acryl-3-(third-1-alkene-2-yl)-1H-benzimidazolyl-2 radicals-ketone control graw mold of tomato field test
With reference to the method for " GB/T 17980.28-2000 pesticide field efficacy medicine test criterion () bactericidal agent for preventing and treating eliminating vegetable botrytis ", " 1-acryl-3-(third-1-alkene-2-yl)-1H-benzimidazolyl-2 radicals-ketone " provided by the invention carried out control graw mold of tomato field control effectiveness test.The result shows that when spraying medicine concentration was 200 μ g/mL, its protection effect and result of treatment were respectively 67.6% and 53.5%; When spraying medicine concentration was 500 μ g/mL, its protection effect and result of treatment were respectively 92.3% and 87.0%.
Claims (2)
1. the benzimidazole amide compound has following structural formula
Wherein R be ethyl, propyl group, normal-butyl, isobutyl-, vinyl, propenyl, pseudoallyl, isobutenyl, chloromethyl, brooethyl, 2-chloroethyl, 2-bromotrifluoromethane, to chlorophenylmethyl, to Brombenzyl, to mehtoxybenzyl, p-nitrophenyl or furfuryl.
2. compound as claimed in claim 1 is as the purposes of disinfectant use in agriculture.
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| CN2008101844609A CN101759649B (en) | 2008-12-23 | 2008-12-23 | Benzimidazole amide bactericide |
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| CN2008101844609A CN101759649B (en) | 2008-12-23 | 2008-12-23 | Benzimidazole amide bactericide |
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| CN101759649B true CN101759649B (en) | 2011-07-20 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102816121B (en) * | 2011-06-12 | 2016-03-23 | 西北农林科技大学农药研究所 | 1-acyl group-3-pseudoallyl benzo imidazolone derivatives is as the purposes of anti-bacterial drug |
| CN102584714A (en) * | 2012-02-17 | 2012-07-18 | 玛耀生物医药（上海）有限公司 | Preparation method of 1-isopropenyl-2-benzimidazolone |
| CN103664791A (en) * | 2012-09-12 | 2014-03-26 | 西北农林科技大学农药研究所 | Derivative of 1-acyl benzimidazolone and use thereof as agricultural fungicide |
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Non-Patent Citations (2)
| Title |
|---|
| J. Davoll，et al..Some N-Substituted 2-Oxobenzimidazolines.《J. Chem. Soc.》.1960,314-318. * |
| Valdas Laurinavicius,et al..A Novel Application of Heterocyclic Compounds for Biosensors Based on NAD, FAD, and PQQ Dependent Oxidoreductases.《Monatshefte fur Chemie》.1999,第130卷1269-1281. * |
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