CN110818707A - Compound containing fused heterocyclic structure, preparation method and application thereof, and bactericide - Google Patents
Compound containing fused heterocyclic structure, preparation method and application thereof, and bactericide Download PDFInfo
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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Abstract
The invention relates to the field of pesticides and bactericides, and discloses a compound containing a fused heterocyclic structure, a preparation method and application thereof, and a bactericide, wherein the compound containing the fused heterocyclic structure has a structure shown in a formula (1) or a formula (2). The compound has excellent control effect on plant diseases caused by various oomycete pathogenic bacteria such as phytophthora infestans, phytophthora capsici, pythium ultimum, phytophthora nicotianae, peronophythora litchi, peronospora cubensis and the like, is obviously superior to a conventional oomycete disease control medicament dimethomorph, and has good market development prospect.
Description
Technical Field
The invention relates to the field of pesticide bactericides, in particular to a compound containing a fused heterocyclic structure and a preparation method thereof, application of the compound containing the fused heterocyclic structure in preventing and treating plant oomycete diseases, application of the compound containing the fused heterocyclic structure as a pesticide bactericide and a bactericide.
Background
The oomycetes are one of the important pathogenic bacteria causing plant diseases, have the characteristics of wide parasitic range, strong destructiveness, large harmfulness, rapid development and the like, and can harm most of main economic crops such as potatoes, tomatoes, hot peppers, grapes, tobaccos, hot peppers and the like. Meanwhile, diseases caused by the pesticide are difficult to control, so that great loss is brought to agricultural production.
The main plant pathogenic bacteria of the oomycetes comprise phytophthora infestans, phytophthora capsici, pythium ultimum, phytophthora litchi, peronospora cubensis and the like. Of these, phytophthora infestans is a typical pathogen that triggers late blight outbreaks in potatoes that have led to the occurrence of the historically well-known irish hunger 39313. Other phytopathogens can cause serious diseases, such as phytophthora capsici easily causes diseases of crops such as hot pepper, tomato, eggplant and melon, and downy mildew of melons and fruits caused by cucumber downy mildew.
The control of oomycete diseases is increasingly difficult, at present, chemical control is still the most simple and effective method in control measures, and a protective bactericide with multiple action sites and a systemic bactericide with single action site are mainly used in production. However, with the prolonged and long-term abuse of these fungicides, severe resistance to many pathogenic bacteria has developed. Therefore, the development of novel oomycete bactericides without cross-resistance is an urgent development direction in the field.
Disclosure of Invention
The invention aims to provide a novel compound containing a fused heterocyclic structure to achieve a good effect of preventing and treating oomycete diseases at a low concentration.
In order to achieve the above objects, the present invention provides, in a first aspect, a fused heterocyclic structure-containing compound having a structure represented by formula (1) or formula (2), or an agrochemically acceptable salt, hydrate or solvate thereof,
in a second aspect, the present invention provides a method for preparing a fused heterocyclic structure-containing compound according to the first aspect, the method comprising: under the condition of nucleophilic substitution reaction, the compound shown in the formula (2-1) and the compound shown in the formula (11) or the formula (21) are subjected to contact reaction,
in a third aspect, the present invention provides the use of the fused heterocyclic structure-containing compound of the first aspect or an agrochemically acceptable salt, hydrate or solvate thereof for controlling plant oomycete diseases.
In a fourth aspect, the present invention provides the use of the fused heterocyclic structure-containing compound according to the first aspect or an agrochemically acceptable salt, hydrate or solvate thereof as an agricultural fungicide.
In a fifth aspect, the present invention provides a fungicide, which comprises an active ingredient and an adjuvant, wherein the active ingredient comprises at least one of the fused heterocyclic structure-containing compound according to the first aspect of the present invention or an agrochemically acceptable salt, hydrate and solvate thereof.
The compound containing the fused heterocyclic structure or the agrochemically acceptable salt, hydrate and solvate thereof provided by the invention can effectively prevent and treat plant oomycete diseases.
Experiments show that the compound has excellent control effect on plant diseases caused by various oomycete pathogenic bacteria such as phytophthora infestans, phytophthora capsici, pythium ultimum, phytophthora nicotianae, peronophythora litchi, peronospora cubensis and the like, is obviously superior to a conventional oomycete disease control medicament dimethomorph, and has good market development prospect.
The specific bactericidal activity of the compound provided by the invention can reach or even exceed that of the best-effect fluorothiazole acetophenone in the existing commercial bactericide.
In addition, as various oomycete pathogenic bacteria such as cucumber downy mildew pathogenic bacteria, phytophthora capsici, phytophthora infestans and the like have resistance to traditional medicaments such as dimethomorph, cyazofamid, amisulbrom and the like, the compound provided by the invention can effectively prevent and treat mutant strains which have resistance to the existing bactericide. Therefore, the compound of the invention has important significance for developing a novel oomycete bactericide without cross resistance.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
As described above, the first aspect of the present invention provides a fused heterocyclic structure-containing compound having a structure represented by formula (1) or formula (2), or an agrochemically acceptable salt, hydrate or solvate thereof,
as described above, the second aspect of the present invention provides a method for producing a fused heterocyclic structure-containing compound according to the first aspect, the method comprising: under the condition of nucleophilic substitution reaction, the compound shown in the formula (2-1) and the compound shown in the formula (11) or the formula (21) are subjected to contact reaction,
preferably, the nucleophilic substitution reaction is carried out in the presence of a basic reagent and in an anhydrous environment.
Preferably, the alkaline agent is at least one of sodium hydride, potassium carbonate and cesium carbonate.
When the nucleophilic substitution reaction of the present invention is carried out under basic conditions, the basic conditions may be provided by a solvent such as tetrahydrofuran.
Preferably, the contact reaction is carried out in the presence of a solvent, preferably at least one selected from the group consisting of dichloromethane, tetrahydrofuran, N-dimethylformamide, acetonitrile and acetone.
Preferably, the conditions of the contact reaction include: the reaction temperature is 0-60 ℃, and the reaction time is 2-48 h.
In the present invention, the compound represented by the formula (2-1) can be obtained commercially or can be synthesized according to the structural formula by a method of the prior art. The present invention provides methods for preparing the compound represented by formula (2-1) in examples, which are exemplary, and those skilled in the art should not be construed as limiting the present invention.
Preferably, in the second aspect of the present invention, the compound represented by formula (2-1) and the compound represented by formula (11) or formula (21) are used in a molar ratio of 1: (1-3); more preferably 1: (1.2-2.4).
In the second aspect of the present invention, the product obtained after the contact reaction may be further subjected to a post-treatment process conventionally used in the art to obtain a product with higher purity, for example, the post-treatment operation process comprises: extraction, washing, rotary evaporation, column chromatography, recrystallization and the like, and the present invention is not particularly limited thereto as long as the aforementioned fused heterocyclic structure-containing compound of the present invention can be obtained.
As described above, the third aspect of the present invention provides the use of the fused heterocyclic structure-containing compound of the first aspect described above or an agrochemically acceptable salt, hydrate, and solvate thereof for controlling plant oomycete diseases.
Preferably, the plant oomycete diseases include diseases caused by at least one of phytophthora infestans, phytophthora capsici, pythium ultimum, phytophthora nicotianae, phytophthora litchi and peronospora cubensis.
It should be noted that the structures represented by the aforementioned formulae (1) and (2) of the present invention each have an R configuration and an S configuration, respectively, and the inventors of the present invention have found in their studies that the R configuration, the S configuration, and the racemic structure of the compounds of the structures represented by the formulae (1) and (2) each have an excellent fungicidal activity. In order to briefly explain the effects of the compounds of the present invention, hereinafter, the racemic modification of the compounds of the present invention is used without particular mention, and those skilled in the art should not be construed as limiting the present invention.
As described above, the fourth aspect of the present invention provides the use of the fused heterocyclic structure-containing compound according to the first aspect described above or an agrochemically acceptable salt, hydrate or solvate thereof as an agricultural fungicide.
As described above, the fifth aspect of the present invention provides a fungicide composed of an active ingredient and an adjuvant, the active ingredient including at least one of the fused heterocyclic structure-containing compound according to the first aspect described above or an agrochemically acceptable salt, hydrate, and solvate thereof.
Preferably, the content of the active ingredient is 1 to 99.9% by weight; more preferably, the content of the active ingredient is 5 to 95% by weight.
Preferably, the dosage form of the bactericide is at least one selected from emulsifiable solution, suspending agent, wettable powder, granules, aqueous solution, poison bait, mother liquor and mother powder.
In the present invention, the adjuvant may be various adjuvants conventionally used in the art, and may be, for example, a surfactant, a solvent, etc.
The present invention will be described in detail below by way of examples.
In the following examples, the various starting materials used are commercially available in chemical purity, unless otherwise specified.
Example 1
This example is intended to illustrate the preparation of a compound represented by the formula (2-1).
(1) Adding 1, 3-dichloroacetone (1mol) into 1L of 2M ethyl ether hydrochloride solution at 25 ℃, adding tert-butyl nitrite (1mol), continuing to react for 10 hours at 25 ℃, removing ethyl ether after the reaction is finished, cooling to obtain a crude product of the compound shown in the formula (2-2), washing with 1-chlorobutane, filtering, and collecting a filter cake; and recrystallizing the filtrate, filtering, drying the filter cake to obtain the compound shown in the formula (2-2), and combining the two batches to obtain the pure product of the compound shown in the formula (2-2).
(2) Adding sodium bicarbonate (5mol) into 1L dichloromethane solution of the compound (1mol) shown in the formula (2-2) at the temperature of 25 ℃, slowly adding 2, 6-difluorostyrene (1mol), continuously stirring for reacting for 4 hours, filtering after the reaction is finished, and removing the solvent in the filtrate to obtain the compound shown in the formula (2-3) which is directly used for the next reaction.
(3) Sequentially adding a compound (1mol) shown in a formula (2-3), 4-aminothiocarbonyltetrahydropyridine-1 (2H) -tert-butyl formate (1.1mol) and sodium bromide (0.1mol) into 2.5L of acetone, heating and refluxing the reaction system for 12H, removing the acetone after the reaction is finished, adding 2L of water, extracting with 500mL of 3 ethyl acetate, combining organic phases, drying and concentrating to obtain a crude product of the compound shown in the formula (2-4), and further performing column chromatography purification by using an elution system formed by silica gel, petroleum ether and ethyl acetate to finally obtain a pure product of the compound shown in the formula (2-4);
(4) after the completion of the reaction, 100mL of concentrated hydrochloric acid was added to 500mL of a methanol solution of the compound represented by the formula (2-4) (0.5mol), and the mixture was reacted at 25 ℃ for 6 hours, 2M aqueous sodium hydroxide solution was added to adjust the pH to 7, and the mixture was extracted with 500mL of 5 ethyl acetate, and the organic phases were combined, dried and concentrated to obtain the compound represented by the formula (2-5).
(5) Triethylamine (0.15mol) was added to a solution of the compound represented by formula (2-5) (0.1mol) in 500mL of anhydrous dichloromethane, the temperature was decreased to 0 ℃, bromoacetyl bromide (0.12mol) was further added slowly, the reaction was carried out at 25 ℃ for 3 hours, after the completion of the reaction, 1M hydrochloric acid solution was added to adjust pH to 3, the mixture was extracted with 200mL × 2 of dichloromethane, the organic phases were combined, dried and concentrated to obtain the compound represented by formula (2-1).
Example 2
This example illustrates the preparation of a compound of formula (1).
Sodium hydride (1.5mmol) was added to a solution of the compound represented by the formula (11) (1.2mmol) in 10mL of DMF at 0 ℃ to react at 0 ℃ for 0.5h, then the compound represented by the formula (2-1) (1mmol) was added thereto and the reaction was continued at 25 ℃ for 6 h. After the reaction is finished, the compound shown in the formula (1) is obtained by extraction, washing, concentration and column chromatography purification.
White solid, m.p.135-136 ℃,1H NMR(600MHz,CDCl3)δ8.56(d,J＝4.8Hz,1H),7.84(d,J＝8.4Hz,1H),7.67(s,1H),7.33–7.28(m,1H),7.20(dd,J＝8.4,4.8Hz,1H),6.92(t,J＝8.4Hz,2H),6.08(t,J＝10.8Hz,1H),5.45(s,2H),4.58(d,J＝13.8Hz,1H),4.04(d,J＝13.8Hz,1H),3.81(dd,J＝17.2,12.0Hz,1H),3.64(dd,J＝17.2,9.0Hz,1H),3.33(t,J＝12.6Hz,2H),2.86(t,J＝12.6Hz,1H),2.27(d,J＝13.2Hz,1H),2.16(d,J＝13.2Hz,1H),1.93–1.75(m,2H).13C NMR(101MHz,DMSO-d6) δ 175.08,164.77,162.03(d, J-8.1 Hz),159.55(d, J-8.1 Hz),152.25,150.87,150.07,144.42,131.47(t, J-11.1 Hz),130.51,120.06,119.98,117.99,115.70(t, J-17.2 Hz),112.38(d, J-6.1 Hz),112.19(d, J-6.1 Hz),72.18(d, J-3.0 Hz),48.62,44.05,41.39,41.27,32.37,31.88.HRMS calculated value hrc25H21F2IN6O2S[M+H]+635.05322. Found 635.20365.
Example 3
This example illustrates the preparation of a compound of formula (2).
Sodium hydride (1.5mmol) was added to a solution of the compound represented by the formula (21) (1.2mmol) in 10mL of DMF at 0 ℃ to react at 0 ℃ for 0.5h, then the compound represented by the formula (2-1) (1mmol) was added thereto and the reaction was continued at 25 ℃ for 6 h. After the reaction is finished, the compound shown in the formula (2) is obtained by extraction, washing, concentration and column chromatography purification.
White solid, m.p.132-133 ℃,1H NMR(600MHz,CDCl3)δ8.58(d,J＝4.8Hz,1H),8.08(d,J＝8.4Hz,1H),7.68(s,1H),7.38–7.28(m,1H),7.22(dd,J＝8.4,4.8Hz,1H),6.93(t,J＝8.4Hz,2H),6.09(t,J＝10.8Hz,1H),5.41(s,2H),4.59(d,J＝13.8Hz,1H),4.04(d,J＝13.8Hz,1H),3.82(dd,J＝17.4,12.0Hz,1H),3.64(dd,J＝17.4,9.0Hz,1H),3.35(t,J＝12.6Hz,2H),2.88(t,J＝12.6Hz,1H),2.28(d,J＝13.2Hz,1H),2.17(d,J＝13.2Hz,1H),1.91(q,J＝13.2,12.6Hz,1H),1.81(q,J＝14.4,13.2Hz,1H).13C NMR(151MHz,CDCl3) δ 174.26,164.52,162.22(d, J-5.1 Hz),160.55(d, J-5.1 Hz),152.30,151.52,150.23,145.21,132.83,130.60(t, J-6.1 Hz),129.26,118.75,117.84,117.66,115.78(t, J-11.1 Hz),113.68,111.97,111.82,72.89,48.52,44.66,42.02,41.58,40.27,32.50,31.81 HRMS calcd C25H21ClF2N6O2S[M+Na]+565.09955. Found 565.09960.
Test example 1: activity for inhibiting cucumber downy mildew
The testing and investigation method refers to SOP-SC-1098 cucumber downy mildew potting method in disinfectant roll written by KANGZHONG and KUBAOGEN Standard operation Specification for testing biological Activity of pesticides.
The control results are shown in table 1.
TABLE 1
As can be seen from Table 1, the compound has good control effect on cucumber downy mildew, and the control effect is 100% or close to 100% at four administration concentrations of 20mg/L to 0.625mg/L, is equivalent to that of a control medicament, namely fluorothiazole pyrithylone, and is comprehensively superior to control medicaments, namely dimethomorph and amisulbrom, for the cucumber downy mildew.
Test example 2: inhibiting oomycete pathogens: in vitro activity of phytophthora capsici and phytophthora infestans hypha growth
The test method adopts a microplate method to measure the indoor biological activity of the medicament
Phytophthora capsici: inoculating target bacteria in PDB or V8 liquid culture medium, shaking for 96 hr, filtering, collecting fresh mycelium, weighing 0.1g mycelium, adding into 50mL PDB liquid culture medium, mashing the mycelium with tissue mashing machine into small mycelium segments, making mycelium segment suspension, and standing at 4 deg.C.
Phytophthora infestans: the phytophthora infestans is inoculated on a V8 culture medium plate and cultured for 12 days, after a large amount of sporangia are generated, sterile water is added, the plate is transferred to a refrigerator at 4 ℃ and placed for 1 hour, and then the plate is transferred to room temperature to induce the release of zoospores. After the zoospores are fully released, the concentration of the prepared spores is 105spore/mL spore suspension, at 4 ℃ until use.
The test agent is prepared into 2000mg/L mother liquor by dimethyl sulfoxide, then diluted into 0.1mg/L concentration by sterile water, and placed at 4 ℃ for standby.
Sequentially adding spore suspension (mycelium suspension) and series gradient liquid medicine prepared in advance into each micropore according to the amount of 100 mul +100 mul, placing 96-well micropore plate into an incubator at 25 ℃ (Phytophthora infestans 18 ℃) for static culture, and detecting OD of each treatment by using a microplate reader after 3-4 days (Phytophthora infestans 7 days)595(absorbance at 595 nm) value. Calculating the indoor toxicity of the medicament to the target bacteria. The test results are shown in table 2.
TABLE 2
*90％≦A≦100％
As can be seen from Table 2, the compound of the invention has good inhibition effect on the growth of hyphae of phytophthora capsici and phytophthora infestans, and the inhibition rate is more than 90% under the administration concentration of 0.1mg/L, which is equivalent to that of a control medicament, namely fluorothiazole pyrithylone.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (10)
1. A compound containing a fused heterocyclic structure or an agrochemically acceptable salt, hydrate and solvate thereof, the compound having a structure shown by formula (1) or formula (2),
2. a method for preparing a fused heterocyclic structure-containing compound according to claim 1, which comprises: under the condition of nucleophilic substitution reaction, the compound shown in the formula (2-1) and the compound shown in the formula (11) or the formula (21) are subjected to contact reaction,
3. the method of claim 2, wherein the nucleophilic substitution reaction is carried out in the presence of a basic reagent and in an anhydrous environment;
preferably, the alkaline agent is at least one of sodium hydride, potassium carbonate and cesium carbonate.
4. The method of claim 2 or 3, wherein the conditions of the contact reaction comprise: the reaction temperature is 0-60 ℃, and the reaction time is 2-48 h.
5. Use of the fused heterocyclic structure-containing compound according to claim 1 or an agrochemically acceptable salt, hydrate or solvate thereof for controlling plant oomycete diseases.
6. The use according to claim 5, wherein the plant oomycete diseases include diseases caused by at least one of Phytophthora infestans, Phytophthora capsici, Pythium ultimum, Phytophthora nicotianae, Phytophthora litchi and Peronospora cucumerinum.
7. Use of the fused heterocyclic structure-containing compound according to claim 1 or an agrochemically acceptable salt, hydrate or solvate thereof as an agricultural fungicide.
8. A fungicide comprising an active ingredient and an auxiliary material, wherein the active ingredient comprises at least one of the fused heterocyclic structure-containing compound according to claim 1 or an agrochemically acceptable salt, hydrate and solvate thereof.
9. The bactericide as claimed in claim 8, wherein the content of said active ingredient is 1 to 99.9% by weight.
10. The bactericide according to claim 9, wherein the bactericide is in a form selected from at least one of emulsifiable concentrate, suspension, wettable powder, dust, granule, aqueous solution, poison bait, mother liquor and mother powder.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478805A (en) * | 2006-07-27 | 2015-04-01 | 杜邦公司 | Fungicidal azocyclic amides |
| US20160242416A1 (en) * | 2015-02-23 | 2016-08-25 | E I Du Pont De Nemours And Company | Fungicidal isoxazoline carbinols |
| WO2017138069A1 (en) * | 2016-02-08 | 2017-08-17 | 株式会社エス・ディー・エス バイオテック | Germicidal composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478805A (en) * | 2006-07-27 | 2015-04-01 | 杜邦公司 | Fungicidal azocyclic amides |
| US20160242416A1 (en) * | 2015-02-23 | 2016-08-25 | E I Du Pont De Nemours And Company | Fungicidal isoxazoline carbinols |
| WO2017138069A1 (en) * | 2016-02-08 | 2017-08-17 | 株式会社エス・ディー・エス バイオテック | Germicidal composition |
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