CN111087363B - N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis and preparation method thereof - Google Patents

N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis and preparation method thereof Download PDF

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CN111087363B
CN111087363B CN202010012316.8A CN202010012316A CN111087363B CN 111087363 B CN111087363 B CN 111087363B CN 202010012316 A CN202010012316 A CN 202010012316A CN 111087363 B CN111087363 B CN 111087363B
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bromoacetamide
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CN111087363A (en
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唐子龙
谭宇欢
文御豪
彭丽芬
万义超
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Hunan University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • 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
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

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Abstract

The invention provides an N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis and a preparation method thereof. The compound is prepared by reacting a benzothiazole compound or a benzimidazole compound with a bromoacetyl compound in the presence of an organic solvent and a catalyst, and the preparation method has the advantages of easily available raw materials and low production cost, and can obtain a high-yield product by only one-step reaction. Meanwhile, the compound has good inhibition effect on the activity of crop germs, especially has obvious inhibition effect on the activity of wheat scab, cucumber gray mold, phytophthora capsici, sclerotinia sclerotiorum, rice sheath blight or rice blast and other germs, and well ensures the yield of crops.

Description

N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis and preparation method thereof
Technical Field
The invention relates to a crop bacteriostatic compound, in particular to an N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostatic and a preparation method thereof, belonging to the technical field of pesticides.
Background
Among the crop infectious diseases, there are two main fungal diseases and bacterial diseases, wherein the fungal diseases account for about 80% of the diseases. Because the fungal diseases and the bacterial diseases have different origins, the control method and the medicament use are also different.
Effects of fungal diseases on crops: the plant growth regulator can cause the expansion and division of crop cells, root swelling or goiter of damaged parts, downy mildew, saprophytic bacteria and weak parasitic bacteria, tissue necrosis of storage organs such as flowers, fruits, root tubers, tubers and the like of crops and generative tissue necrosis of crops, wherein pathogenic fungi without spores mainly invade roots and stem bases to cause root rot and stem base rot and mainly invade leading tissues of the crops to cause systemic diseases of the whole plant, such as blight, verticillium wilt and the like. The types and kinds of fungal diseases cause disease symptoms to vary widely. However, any fungal disease occurs at any site, and any symptom appears, and hyphae and spores are produced under humid conditions. This is the main basis for judging fungal diseases.
Bacterial diseases are mainly characterized by: necrosis and rot, wilting and deformity. Necrosis, rot and deformity are the result of bacteria breaking down thin cell wall tissues. The disease spots are polygonal spots on the leaves of the reticular veins, and yellow halo is formed around the disease spots. The spots on the hypertrophic tissue or fruit are mostly circular. On soft and tender meat and juicy tissues, the tissues die and are easy to rot. Some parts are damaged and then have accelerated pathological changes to form tumors, which are mostly generated on roots or stems. Wilting is the result of cell invasion of vascular bundles and may occur locally or fully. After vascular bundle cells are damaged, water and nutrient substances cannot be normally conveyed, and plant wilting death can be caused. The cellular diseases have no hypha and spore, the scab surface has no mildew, but the pus (except for root cancer germ) overflows, and the scab surface is smooth, which is the main basis for diagnosing the bacterial diseases. One of the effective methods of effectively preventing crops from being damaged by pathogenic bacteria is to inhibit the physiological activity of pathogenic bacteria through medicaments, further inhibit the proliferation and the diffusion of the crops, compress the living space of the pathogenic bacteria, and further reduce or even eliminate the damage of the pathogenic bacteria to the crops.
Benzothiazole derivatives have a wide range of biological properties, among which the amide-linked benzothiazole structures are also part of biologically active compounds, such as herbicides, antivirals, androgen receptor antagonists, dipeptidyl peptidase IV inhibitors. Benzimidazole has anticancer, antimicrobial, antiviral, anti-HIV, anti-inflammatory, antioxidant, antihypertensive and antidiabetic effects; the amide compound also has the activities of killing insects, weeding, resisting tumors, sterilizing and the like. However, there is no report of the use of N- (substituted benzothiazolyl) -2-bromoacetamide or N- (benzimidazolyl) -2-bromoacetamide compounds for inhibiting crop species. Therefore, we investigated the inhibitory activities of these compounds against Fusarium graminearum, Botrytis cinerea, Phytophthora capsici, Sclerotinia sclerotiorum, Rhizoctonia solani and Pyricularia oryzae.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides an N-heterocyclic substituted-2-bromoacetamide compound for inhibiting bacteria of crops and a preparation method thereof. The compound has simple preparation method and easily obtained raw materials, has better inhibition effect on the activity of crop germs, particularly has obvious inhibition effect on the activity of wheat scab, cucumber gray mold, phytophthora capsici, sclerotinia sclerotiorum, rice sheath blight or rice blast and other germs, and well ensures the yield of crops.
In order to achieve the above purpose, the technical scheme provided by the invention is as follows:
according to a first embodiment of the present invention, there is provided an N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis, characterized in that: the compounds are of the general structural formula (I):
Figure BDA0002357587690000021
wherein, in the formula (I), R is H or C1-C2Alkyl or C1-C2An alkoxy group. X is NH or S.
Preferably, R is selected from one of H, methyl, ethyl, methoxy and ethoxy.
Preferably, R is selected from H, 6-CH3O radical, 6-CH3One of the groups.
Preferably, the N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis is one or more selected from the following compounds:
n- (benzothiazolyl) -2-bromoacetamide:
Figure BDA0002357587690000022
n- (6-methylbenzothiazolyl) -2-bromoacetamide:
Figure BDA0002357587690000023
n- (6-methoxybenzothiazolyl) -2-bromoacetamide:
Figure BDA0002357587690000024
n- (benzimidazolyl) -2-bromoacetamide:
Figure BDA0002357587690000031
according to a second embodiment of the present invention there is provided a process for the preparation of the N-heterocyclic substituted-2-bromoacetamides compounds of the first embodiment having the general structural formula (I):
Figure BDA0002357587690000032
wherein, in the formula (I), R is H or C1-C2Alkyl or C1-C2An alkoxy group. X is NH or S.
The preparation method comprises the following steps:
A) reacting a compound with a general structural formula (II) with bromoacetyl bromide to obtain an N-heterocyclic substituted-2-bromoacetamide compound with a general structural formula (I):
Figure BDA0002357587690000033
preferably, R is selected from one of H, methyl, ethyl, methoxy and ethoxy.
Preferably, R is selected from H, 6-CH3O、6-CH3One kind of (1).
Preferably, X is selected from one of N and S.
Preferably, in step a), the compound having the general structural formula (II) is reacted with bromoacetyl bromide in an organic solvent in the presence of a catalyst. The organic solvent is selected from one or more of Dichloromethane (DCM), dichloroethane, chloroform, diethyl ether and toluene. Preferably Dichloromethane (DCM).
Preferably, in step a), the catalyst is triethylamine or pyridine. Preferably triethylamine
Preferably, in step a), the molar ratio of the amount of the compound having the general structural formula (II) added to the amount of bromoacetyl bromide added is: 1:0.8-4, preferably 1:1-3, more preferably 1: 1.1-2.
Preferably, the molar ratio of the amount of catalyst added to the amount of compound having the general structural formula (II) is: 1:0.5-2.5, preferably 1:0.8-3, preferably 1: 1-2.
Preferably, the mass ratio of the added amount of the organic solvent to the added amount of the compound having the general structural formula (II) is: 5-80:1, preferably 10-60:1, more preferably 20-50: 1.
Preferably, step a) is specifically: the compound of general structural formula (II) and the catalyst (e.g. triethylamine) are weighed out in proportion and dissolved in an organic solvent (e.g. in DCM). Bromoacetyl bromide is then weighed out in proportion and dissolved in an organic solvent (e.g. in DCM). Then dropwise adding the bromoacetyl bromide solution into a system containing the compound with the structural general formula (II) by using a constant pressure dropping funnel to perform reaction (the reaction temperature is 0-20 ℃, the reaction temperature is preferably 1-15 ℃, the reaction time is preferably 2-10 ℃, and the reaction time is 0.1-24h, the reaction time is preferably 1-18h, and the reaction time is more preferably 2-12 h). And finally, tracking and detecting by adopting a TLC plate until the reaction is finished, removing the solvent (for example, removing the residual solvent by reducing pressure), and separating and purifying by column chromatography to obtain the N-heterocyclic substituted-2-bromoacetamide compound (a yellow white solid target product) with the structural general formula (I).
According to a third embodiment of the present invention, there is provided the use of the N-heterocyclic substituted-2-bromoacetamide compound of the first embodiment or the N-heterocyclic substituted-2-bromoacetamide compound of the second embodiment for crop bacteriostasis. The N-heterocyclic substituted-2-bromoacetamide compound for inhibiting the bacteria of crops is used for inhibiting one or more of wheat scab, cucumber botrytis cinerea, phytophthora capsici leonian, sclerotinia sclerotiorum, rice sheath blight bacteria or rice blast bacteria.
In the present invention, there is provided a novel N-heterocyclic substituted-2-bromoacetamide compound useful as an agricultural pathogen inhibitor, which is obtained by organically binding a benzothiazole compound (e.g., 2-aminobenzothiazole, 2-amino-6-methylbenzothiazole, 2-amino-6-methoxybenzothiazole) or a benzimidazole compound (e.g., 2-aminobenzimidazole) and a bromoacetamide compound (e.g., bromoacetyl bromide) in the presence of a catalyst and a solvent, wherein the benzothiazole group in the benzothiazole compound or the benzimidazole group in the benzimidazole compound and the bromoacetamide group in the bromoacetamide compound are bound to each other, that is, the N atom on the amino group in the bromoacetamide compound and the C atom at position 2 in the benzothiazole compound (or benzimidazole compound) form a covalent bond to form a bond Novel substituted compounds of (1). The N-heterocyclic substituted-2-bromoacetamide compound with excellent activity inhibition on crop pathogens is obtained by substituting a specific group at a specific position on a mother nucleus (when a bromoacetamide compound is used as the mother nucleus, the substituted group refers to a compound with H substituted on an N atom, and the substituted group refers to benzothiazole or benzimidazolyl, when a benzothiazole compound is used as the mother nucleus, the substituted group refers to a compound with H substituted on a C atom at the position 2, and the substituted group refers to bromoacetamide. The compound has especially obvious activity inhibiting effect on one or more of wheat scab, cucumber gray mold, pepper phytophthora, rape sclerotinia sclerotiorum, rice sheath blight or rice blast.
In the present invention, N-heterocyclic substituted-2-bromoacetamides having the general structural formula (I):
Figure BDA0002357587690000041
wherein, in the formula (I), R is H or C1-C2Alkyl or C1-C2An alkoxy group. X is N or S.
Preferably, R is selected from one of H, methyl, ethyl, methoxy and ethoxy. Preferably, R is selected from H, 6-CH3O radical, 6-CH3One of the groups. Wherein 6-CH3The radical O means that the radical R is-CH3O and as a substituent on C atom number 6. Same principle, 6-CH3Radical means that the radical R is-CH3And as a substituent on the C atom No. 6.
In the present invention, an N-heterocyclic substituted-2-bromoacetamide compound having the general structural formula (I) is prepared by reacting a compound having the general structural formula (II) (a benzothiazole compound or a benzimidazole compound) with bromoacetyl bromide:
Figure BDA0002357587690000051
wherein R is selected from one of H, methyl, ethyl, methoxy and ethoxy. Preferably, R is selected from H, 6-CH3O radical, 6-CH3One of the groups. And X is selected from one of N and S.
Further, the compound having the general structural formula (II) and the catalyst (preferably triethylamine) are dissolved in an organic solvent (for example, in DCM), and reaction solution B is obtained after complete dissolution. Bromoacetyl bromide is dissolved in an organic solvent (e.g., in DCM) and reaction solution C is obtained after complete dissolution. The reaction solution C is added dropwise (at a dropping rate of 1 to 5 drops per second, preferably 2 to 3 drops per second) to the reaction solution B by using a constant pressure dropping funnel to carry out the reaction (at a reaction temperature of 0 to 20 ℃, preferably 1 to 15 ℃, more preferably 2 to 10 ℃, for a reaction time of 0.1 to 24 hours, preferably 1 to 18 hours, more preferably 2 to 10 hours). Dropwise adding while reacting, adopting a TLC plate to track and detect until the reaction is finished, finally removing the solvent (for example, removing residual solvent by decompression), and then carrying out column chromatography separation and purification to obtain a yellowish white solid target product, namely the N-heterocyclic substituted-2-bromoacetamide compound with the structural general formula (I).
More specifically, the N-heterocyclic substituted-2-bromoacetamide compound with the structural general formula (I) is prepared by the following steps:
2-aminobenzothiazole reacts with bromoacetyl bromide in a dichloromethane solvent under the catalysis of triethylamine to generate N- (benzothiazolyl) -2-bromoacetamide:
Figure BDA0002357587690000052
further, 2-amino-6-methylbenzothiazole reacts with bromoacetyl bromide in a dichloromethane solvent under the catalysis of triethylamine to generate N- (6-methylbenzothiazolyl) -2-bromoacetamide:
Figure BDA0002357587690000053
further, 2-amino-6-methoxybenzothiazole reacts with bromoacetyl bromide in a dichloromethane solvent under the catalysis of triethylamine to generate N- (6-methoxybenzothiazolyl) -2-bromoacetamide:
Figure BDA0002357587690000061
further, 2-aminobenzimidazole reacts with bromoacetyl bromide in a dichloromethane solvent under the catalysis of triethylamine to generate N- (benzimidazolyl) -2-bromoacetamide:
Figure BDA0002357587690000062
in the present invention, the N-heterocyclic substituted-2-bromoacetamide compound may be referred to simply as a bromoacetamide compound or an amide compound.
Compared with the prior art, the invention has the following beneficial technical effects:
1. the N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis has obvious inhibition on the activity of crop germs, and especially has obvious inhibition effect on the activity of germs of wheat scab, cucumber gray mold, phytophthora capsici, sclerotinia sclerotiorum, rice sheath blight or rice blast.
2. The N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis has the advantages of simple preparation method, cheap and easily obtained raw materials, high yield and capability of obtaining a target product by only one-step reaction.
Detailed Description
The technical solution of the present invention is illustrated below, and the claimed scope of the present invention includes, but is not limited to, the following examples.
According to an embodiment provided by the invention, an N-heterocyclic substituted-2-bromoacetamide compound for crop bacteriostasis is provided, which is characterized in that: the compounds are of the general structural formula (I):
Figure BDA0002357587690000063
wherein, in the formula (I), R is H or C1-C2Alkyl or C1-C2An alkoxy group. X is N or S.
Preferably, R is selected from one of H, methyl, ethyl, methoxy and ethoxy.
Preferably, R is selected from H, 6-CH3O radical, 6-CH3One of the groups.
Example 1
Synthesis of N- (benzothiazolyl) -2-bromoacetamide:
3.01g (20mmol) of 2-aminobenzothiazole and 2.23g (22mmol) of triethylamine are weighed and added into a 250mL round-bottom flask containing 80mL of dichloromethane solvent; then 4.85g (24mmol) of bromoacetyl bromide is dissolved in 15ml of dichloromethane and is dripped into a round-bottom flask by using a constant pressure dropping funnel, and the mixture reacts for 7 hours at the temperature of 0-5 ℃, and is tracked and detected by a TLC plate until the reaction is finished; removing the solvent under reduced pressure, and purifying by column chromatography to obtain a target product as a yellow-white solid with a yield of 73.4% and a melting point (mp): 150.6-151.1 ℃.
1H NMR(500MHz,CDCl3)δ7.84(t,J＝8.1Hz,2H),7.49(t,J＝7.7Hz,1H),7.37(t,J＝7.6Hz,1H),7.26(s,1H),4.09(s,1H).
13C NMR(125MHz,DMSO)δ166.09,157.66,148.42,131.48,126.26,123.82,121.83,120.73,28.63.
Example 2
Synthesis of N- (6-methylbenzothiazolyl) -2-bromoacetamide:
3.29g (20mmol) of 2-amino-6-methylbenzothiazole and 2.23g (22mmol) of triethylamine are weighed and added into a 250mL round-bottom flask containing 80mL of dichloromethane solvent; then 4.85g (24mmol) of bromoacetyl bromide is dissolved in 15ml of dichloromethane and is dripped into a round-bottom flask by using a constant pressure dropping funnel, and the mixture reacts for 7 hours at the temperature of 0-5 ℃, and is tracked and detected by a TLC plate until the reaction is finished; removing the solvent under reduced pressure, and purifying by column chromatography to obtain yellowish white solid product with yield of 78.5% and melting point (mp): 157.0 to 157.7 ℃.
1H NMR(500MHz,DMSO)δ7.78(s,1H),7.66(d,J＝8.2Hz,1H),7.27(d,J＝8.7Hz,1H),4.22(d,J＝13.8Hz,2H),2.42(s,3H).
13C NMR(125MHz,DMSO)δ172.19,156.92,146.48,133.30,131.75,127.70,121.56,120.35,61.45,21.22.
Example 3
Synthesis of N- (6-methoxybenzothiazolyl) -2-bromoacetamide:
3.61g (20mmol) of 2-amino-6-methoxybenzothiazole and 2.23g (22mmol) of triethylamine are weighed and added into a 250mL round-bottom flask containing 80mL of dichloromethane solvent; then 4.85g (24mmol) of bromoacetyl bromide is dissolved in 15ml of dichloromethane and is dripped into a round-bottom flask by using a constant pressure dropping funnel, and the mixture reacts for 7 hours at the temperature of 0-5 ℃, and is tracked and detected by a TLC plate until the reaction is finished; removing the solvent under reduced pressure, and purifying by column chromatography to obtain yellowish white solid product with yield of 80.9%, melting point (mp): 154.0 to 154.6 ℃.
1H NMR(500MHz,CDCl3)δ7.71(d,J＝8.9Hz,1H),7.39–7.19(m,1H),7.06(dd,J＝8.9,2.5Hz,1H),4.05(s,2H),3.87(s,3H).
13C NMR(126MHz,DMSO)δ171.76,165.72,155.42,142.49,132.78,121.10,114.85,104.72,55.59,28.58.
Example 4
Synthesis of N- (benzimidazolyl) -2-bromoacetamide:
2.66g (20mmol) of 2-aminobenzimidazole and 2.23g (22mmol) of triethylamine are weighed and added into a 250mL round-bottom flask containing 80mL of dichloromethane solvent; then 4.85g (24mmol) of bromoacetyl bromide is dissolved in 15ml of dichloromethane and is dripped into a round-bottom flask by using a constant pressure dropping funnel, and the mixture reacts for 7 hours at the temperature of 0-5 ℃, and is tracked and detected by a TLC plate until the reaction is finished; removing the solvent under reduced pressure, and purifying by column chromatography to obtain yellowish white solid product with yield of 81.6%, melting point (mp): 185.6-187.2 ℃.
1H NMR(500MHz,DMSO)δ7.52(dd,J＝5.8,3.2Hz,2H),7.20(dd,J＝5.8,3.1Hz,2H),4.22(s,2H).
13C NMR(126MHz,DMSO)δ168.11,150.27,129.50,122.99,111.33,43.88.
Example 5
Example 1 was repeated except that diethyl ether was used instead of Dichloromethane (DCM); pyridine was used instead of triethylamine.
Example 6
Example 2 was repeated except that chloroform was used instead of Dichloromethane (DCM); the reaction temperature in the step A) is 8 ℃, and the reaction time is 4 h.
Example 7
Example 3 was repeated except that toluene was used instead of Dichloromethane (DCM).
Examples of Activity Effect test
The antibacterial activity of N- (benzothiazolyl) -2-bromoacetamide, N- (6-methylbenzothiazolyl) -2-bromoacetamide, N- (6-methoxybenzothiazolyl) -2-bromoacetamide and N- (benzimidazolyl) -2-bromoacetamide was tested in an ex vivo manner.
The method comprises the steps of taking wheat scab, cucumber gray mold, phytophthora capsici, sclerotinia sclerotiorum, rice sheath blight and rice blast as test materials for bactericidal activity test, dissolving a test reagent in acetone, and diluting the test reagent into 500g/mL liquid medicine by using 200g/mL sorpol-144 emulsifier. Under the aseptic operating condition, 1mL of compound solution is sucked by a pipette and added into a sterilized plate, then 9mL of sterilized PDA culture medium is added into the plate by a pipette, and the mixture is uniformly mixed to prepare a drug-containing plate with corresponding concentration. Cutting the cultured pathogenic bacteria from the edge of the bacterial colony by using a sterilization puncher with the diameter of 4mm under the aseptic condition, inoculating the bacterial cake to the center of a drug-containing flat plate by using an inoculator after a culture medium is solidified, and culturing in an incubator at a proper temperature. Blank control was performed without drug. Culturing each treatment in an incubator at 24 + -1 deg.C, observing and measuring colony diameter after 72 hr, vertically measuring the diameter of each colony by cross method, and averaging.
Growth inhibition (%) × (control colony diameter-treated colony diameter)/(control colony diameter-4 mm) × 100.
The drug concentration was 50. mu.g/mL.
The bactericidal activity test results are shown in the following table. As can be seen from the table, the target compounds all have excellent inhibitory activity against the test germs, wherein:
the compound N- (benzothiazolyl) -2-bromoacetamide has 100% inhibition rate on phytophthora capsici, rice blast, sclerotium naportum, cucumber gray mold and rice sheath blight germ.
The compound N- (6-methylbenzothiazolyl) -2-bromoacetamide has the inhibition rate of 100 percent on gibberella zeae, phytophthora capsici, sclerotium naportum, botrytis cinerea and rhizoctonia solani.
The compound N- (6-methoxy benzothiazolyl) -2-bromoacetamide has 100% inhibition rate on phytophthora capsici and rhizoctonia solani.
The compound N- (benzimidazolyl) -2-bromoacetamide has the inhibition rate of 100 percent on phytophthora capsici, rice blast and rhizoctonia solani.
Bacteriostatic activity test result table
Figure BDA0002357587690000091

Claims (1)

  1. The application of N-heterocyclic substituted-2-bromoacetamide compounds in crop bacteriostasis is characterized in that: the compound is used for inhibiting one or more of phytophthora capsici, rhizoctonia solani or magnaporthe oryzae; the compounds are of the general structural formula (I):
    Figure FDA0003491070470000011
    wherein, in the formula (I), R is H; x is NH.
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