CN113717155A - (1,2,3, 4-tetrahydroquinolyl) -2-substituted pyrimidineaminoacetophenone compound and preparation method and application thereof - Google Patents
(1,2,3, 4-tetrahydroquinolyl) -2-substituted pyrimidineaminoacetophenone compound and preparation method and application thereof Download PDFInfo
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- CN113717155A CN113717155A CN202111130395.3A CN202111130395A CN113717155A CN 113717155 A CN113717155 A CN 113717155A CN 202111130395 A CN202111130395 A CN 202111130395A CN 113717155 A CN113717155 A CN 113717155A
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
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- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention discloses a (1,2,3, 4-tetrahydroquinolyl) -2-substituted pyrimidineaminoacetophenone compound and a preparation method and application thereof. The structural formula of the (1,2,3, 4-tetrahydroquinolyl) -2-substituted pyrimidineaminoacetophenone compound, the preparation method and the application thereof is shown in the formula I. The invention introduces pyrimidinamine fragment into 2-amino- (1,2,3, 4-tetrahydroquinoline-1-yl) ethanone compound to obtain (1,2,3, 4-tetrahydroquinoline-1-yl) -2- (substituted pyrimidinamine) ethanone compound, the structure is novel, the preparation method is simple, the raw materials are easy to obtain, and harmful byproducts are not easy to generate; the compound of the invention shows inhibition effect on various pathogenic fungi, in particular to rapeThe sclerotinia sclerotiorum and the apple canker have obvious inhibition effect and can be used as agricultural bactericide; the compound of the invention has an inhibiting effect on various agricultural pests, especially has an obvious inhibiting effect on diamondback moths and armyworms, can be used as an agricultural insecticide, and has great application value.
Description
Technical Field
The invention belongs to the field of agricultural chemicals, and particularly relates to a (1,2,3, 4-tetrahydroquinolyl) -2-substituted pyrimidinylaminoacetone compound, and a preparation method and application thereof.
Background
Plant fungal diseases and agricultural insect pests severely affect crop yield and quality, causing substantial irreparable losses to agricultural production. On the other hand, some pathogenic fungi and agricultural pests are also harmful to humans and other organisms. With the abuse and unreasonable application of pesticides, the existing commercial pesticide has the problems of more residues, increased resistance, environmental pollution and the like. Therefore, the development of novel broad-spectrum, efficient and environment-friendly green pesticides to replace the existing commercial varieties is urgently needed.
Tetrahydroquinoline and its derivatives are widely present in natural products and are reported to have various biological activities, such as the pharmaceutical field in 2021 years tetcurot et al (ACS chem.neurosci.,2021,12,746) reported activity for treating alzheimer's disease, in 2021 years Derun l et al (ACS med.chem.lett.,2021,12,389) reported antitumor activity, in 2014 years Keller p.a. et al (ACS med.chem.lett.,2014,5,496) reported antiparasitic activity. A series of compounds reported by Yun L. et al (CN 105330644) in 2016 in the agricultural field can be used as bactericides. Kitamura s. et al (bioorg.med.chem.lett.,2014,24,1715) reported that a series of compounds could be used as ecdysone agonists in 2014.
The reports of pyrimidinamine pesticides dates back to 1957 for the first time. Then, many world famous pesticide companies such as Zhengda, Pasteur, Bayer, DuPont, Yinong Dong and the like have research, and the research lasts for more than 60 years before and after. The compound shows excellent biological activity regardless of the 2-position substitution or the 4-position substitution. The existing commercial pesticides such as azoxystrobin, pyrimethanil, mepanipyrim, fluoxamid and the like all contain pyrimidine structures. Therefore, the pyrimidine pesticide has good commercial prospect.
At present, no technical scheme for introducing a pyrimidinamine fragment into a 2-amino- (1,2,3, 4-tetrahydroquinoline-1-yl) ethanone compound to obtain a new compound exists, and no report on related bactericidal activity or insecticidal activity is found.
Disclosure of Invention
The invention aims to provide a (1,2,3, 4-tetrahydroquinoline) -2-substituted pyrimidinamido ethanone compound and a preparation method and application thereof, wherein a pyrimidinamido fragment is introduced into a 2-amino- (1,2,3, 4-tetrahydroquinoline-1-yl) ethanone compound to obtain a (1,2,3, 4-tetrahydroquinoline-1-yl) -2- (substituted pyrimidinamido) ethanone compound with a novel structure, and the compound has an inhibiting effect on various pathogenic fungi and agricultural pests.
The (1,2,3, 4-tetrahydroquinolyl) -2-substituted pyrimidinylamino ethanone compound, namely the (1,2,3, 4-tetrahydroquinolin-1-yl) -2- (substituted pyrimidinylamino) ethanone compound, is a compound with a structure shown in a formula I;
in the formula I, Z is selected from Z1Or Z2Wherein
R1、R2、R3The substitution mode is mono-substitution, di-substitution or multi-substitution;
R1、R2、R3the same or different, each independently selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, halo-di (C)1-C12Alkylamino), C1-C12Alkylthio, halo C1-C12Alkylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, C2-C12Alkenyloxy, halogeno C2-C12Alkenyloxy radical, C2-C12Alkynyloxy, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkylamino carbonyloxy, halo C1-C12Alkylamino carbonyloxy radical, C1-C12Alkylsulfonyloxy and halo C1-C12One or more of alkylsulfonyloxy;
m is an integer of 0 to 7.
In the above compounds, the halogen may be selected from fluorine, chlorine, bromine or iodine.
In the above compounds, preferably, R1、R2、R3Are the same or different and are each independently selected from C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, halo-di (C)1-C6Alkylamino), C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkylamino carbonyloxy, halo C1-C6Alkylamino carbonyloxy radical, C1-C6Alkylsulfonyloxy and halo C1-C6One or more of alkylsulfonyloxy groups.
By way of example, the compounds of formula I are selected from the group consisting of, but not limited to, compounds having the following group definitions;
compound I-01: wherein
R3＝H；m＝1；
Compound I-02: wherein
R3＝H；m＝1；
Compound I-03: wherein
R3＝H；m＝1；
Compound I-04: wherein
R3＝H；m＝1；
Compound I-05: wherein
R3＝H；m＝1；
Compound I-06: wherein
R3＝H；m＝1；
Compound I-07: wherein
R3＝H；m＝1；
Compound I-08: wherein
R3＝H；m＝1；
Compound I-09: wherein
R3＝H；m＝1；
Compound I-10: wherein
R3＝H；m＝1；
Compound I-11: wherein
R3＝H；m＝1；
Compound I-12: wherein
R3＝H；m＝1；
Compound I-13: wherein
R3＝H；m＝1；
Compound I-14: wherein
R3＝H；m＝1；
Compound I-15: wherein
R3＝H；m＝1；
Compound I-16: wherein
R3＝H；m＝1。
The invention provides a preparation method of a compound shown in a formula I, which comprises the following steps:
carrying out nucleophilic substitution reaction on a compound shown in a formula II and a compound shown in a formula III in an organic solvent under the action of an acid binding agent to obtain a compound shown in a formula I;
in the formula II, R3M is defined as formula I; in formula III, Z is as defined for formula I.
In the above preparation method, the organic solvent may be at least one selected from the group consisting of methyl acetate, N-dimethylformamide, toluene, xylene, methanol, ethanol and tetrahydrofuran.
The temperature of the nucleophilic substitution reaction can be 70-120 ℃, and specifically can be reflux temperature, such as 78 ℃ or 70 ℃; the nucleophilic substitution reaction time can be 4-12 hours, specifically 6 hours.
The molar ratio of the compound of formula II to the compound of formula III may be 1: (1-5), specifically 1: 1.2.
the acid-binding agent can be at least one selected from sodium hydroxide, potassium hydroxide, sodium carbonate, cesium carbonate, potassium carbonate, triethylamine and N, N-diisopropylethylamine; the molar ratio of the acid-binding agent to the compound shown in the formula II can be (1.2-3): 1, specifically 1.5: 1.
the nucleophilic substitution reaction can be carried out under the action of a catalyst; the catalyst can be selected from at least one of potassium iodide and sodium iodide; the molar ratio of the catalyst to the compound represented by the formula II can be (0.01-0.05): 1, specifically, it may be 0.03: 1.
in the present invention, the compounds of formula II can be synthesized by reference to the following documents: WO2008060626a 2; organic & Biomolecular Chemistry, 2011, 9, 872; US20060270688a 1; US20170020858a 1.
The invention further provides application of the compound shown in the formula I or a pharmaceutical composition containing the compound shown in the formula I as or in preparation of an agricultural bactericide.
In the above application, the agricultural fungicide is a fungicide for controlling the following plant pathogens: at least one of sclerotinia sclerotiorum, bakanae disease of rice, canker of apple, rhizoctonia solani, magnaporthe oryzae, botrytis cinerea, fusarium graminearum, pythium aphanidermatum and phytophthora capsici.
The invention further provides application of the compound shown in the formula I or a pharmaceutical composition containing the compound shown in the formula I as or in preparation of agricultural pesticides.
In the above application, the agricultural insecticide is an insecticide for controlling the following agricultural pests: the agricultural pests are at least one of diamondback moth, armyworm, cotton bollworm and spodoptera frugiperda.
The invention has the following beneficial effects:
the (1,2,3, 4-tetrahydroquinoline-1-yl) -2- (substituted pyrimidinamine) ethanone compound provided by the invention has a novel structure, the preparation method is simple to operate, raw materials are easy to obtain, and harmful byproducts are not easy to generate; the compound shows an inhibiting effect on various pathogenic fungi, particularly has an obvious inhibiting effect on sclerotinia sclerotiorum and apple rot pathogen, and can be used as an agricultural bactericide for preventing and treating the plant diseases. The compound has an inhibiting effect on various agricultural pests, particularly has an obvious inhibiting effect on diamondback moths and armyworms, can be used as an agricultural insecticide for preventing and treating the agricultural pests, and has a great application value.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
EXAMPLE 1 preparation of (1,2,3, 4-tetrahydroquinolin-1-yl) -2- (substituted pyrimidinamino) ethanones I-01
A50 mL single vial was charged with 0.57g (3mmol) of 2-amino- (1,2,3, 4-tetrahydroquinolin-1-yl) ethanone, 10mL of anhydrous ethanol, 0.58g (4.5mmol,1.5eq) of N, N-diisopropylethylamine, 0.41g (3.6mmol,1.2eq) of 2-chloropyrimidine, 0.02g (0.09mmol,0.03eq) of potassium iodide, and refluxed at 78 ℃ for 6 hours. After the reaction is completed, the mixture is filtered by suction, and after decompression and desolventization, 50mL of ethyl acetate is added, the mixture is washed by water for three times, and is washed by saturated sodium bicarbonate once, and organic phases are combined. After decompression desolventizing, recrystallizing by absolute ethyl alcohol, filtering, washing a filter cake by water, and drying to obtain 0.65g of white solid with the yield of 82%.
Following the same procedure as described above for the preparation of compound I-01, only Z, R in formula I3The substitution is carried out according to the corresponding substituent groups shown in the table 1 to obtain the products I-01-I-07.
EXAMPLE 2 preparation of (1,2,3, 4-tetrahydroquinolin-1-yl) -2- (substituted pyrimidinamino) ethanones I-12
A50 mL single vial was charged with 0.57g (3mmol) of 2-amino- (1,2,3, 4-tetrahydroquinolin-1-yl) ethanone, 10mL of anhydrous ethanol, 0.58g (4.5mmol,1.5eq) of N, N-diisopropylethylamine, 0.54g (3.6mmol,1.2eq) of 4, 6-dichloropyrimidine, and 0.02g (0.09mmol,0.03eq) of potassium iodide sequentially, and refluxed at 70 ℃ for 6 hours. After the reaction is completed, the mixture is filtered by suction, and after decompression and desolventization, 50mL of ethyl acetate is added, the mixture is washed by water for three times, and is washed by saturated sodium bicarbonate once, and organic phases are combined. Vacuum desolventizing and column chromatography purifying (V)Petroleum ether:VEthyl acetate15: 1) and drying to obtain 0.76g of white solid with the yield of 85 percent.
Following the same procedure as described above for the preparation of compound I-12, only Z, R in formula I3The substitution is carried out according to the corresponding substituent groups shown in the table 1 to obtain the products I-08 to I-16.
The appearance, melting point and yield of the compounds of formula I part are shown in table 1 and the nuclear magnetic hydrogen spectroscopy data are shown in table 2.
The structures of the compounds of the formula I are correct through verification.
TABLE 1 appearance, melting Point and yield of partial Compounds of formula I
TABLE 2 nuclear magnetic hydrogen spectra data for compounds of formula I
Example 4 inhibitory Activity of Compounds of formula I against plant pathogenic fungi
The bactericidal activity of the compound of the formula I is measured by adopting a hypha growth rate method, and the tested strains are rape sclerotium, rice bakanae, apple rot, wheat gibberella, rice blast, phytophthora capsici, rice sheath blight and pythium aphanidermatum.
Respectively weighing the compound of the formula I and a reference medicament flutolanil under aseptic conditions, preparing a mother solution with the concentration of 10000 mug/mL by using dimethyl sulfoxide, respectively sucking the prepared liquid medicine with the concentration of 10000 mug/mL by using a pipette, adding the liquid medicine into a prepared potato glucose agar (PDA) culture medium which is sterilized and cooled to 50 ℃, fully and uniformly mixing to prepare a 50 mug/mL culture medium with medicaments, pouring the culture medium into a culture dish with the diameter of 9cm, repeating each medicament for 4 times by 15mL in each dish, and preparing a PDA plate with the medicaments after the culture medium with the medicaments in the dish is cooled and solidified. And (3) setting dimethyl sulfoxide as a solvent blank control, preparing a bacterial cake with the diameter of 5mm along the edge of a bacterial colony on a prepared pathogenic bacteria flat plate, respectively inoculating the bacterial cake between a PDA flat plate with a drug and a control PDA flat plate, and then placing the bacterial cake in an incubator at 25 ℃ for dark culture. After the colonies in the blank PDA plates had grown sufficiently, the diameter of each treated colony was measured by the cross method and the average value was taken.
The hyphal growth inhibition rate was calculated using the following formula:
the in vitro bacteriostatic activity data (50mg/L) for the partial compounds of formula I are shown in Table 3.
TABLE 3 in vitro bacteriostatic activity data (50mg/L) for partial compounds of formula I
It can be seen from table 3 that the compounds of formula I provided by the present invention all have some inhibitory activity against the 8 plant pathogens tested. Especially, the inhibition rate of a plurality of compounds on the apple canker pathogen and the sclerotinia rot pathogen exceeds 80 percent, the inhibition rate of partial compounds on the pathogenic bacteria exceeds 90 percent, for example, the inhibition effect of the compound I-01 on the sclerotium rot pathogen is better than that of a control medicament flutolanil; the inhibition effect of the compounds I-01, I-06 and I-14 on apple canker is better than that of a control medicament flutolanil.
The experiments prove that the compound of the formula I has good inhibitory activity on apple rot and sclerotinia sclerotiorum, and can be used as an agricultural bactericide for preventing and treating the plant pathogenic bacteria.
EXAMPLE 5 pesticidal Activity of Compounds of formula I against plant pests
The insecticidal activity evaluation is carried out by adopting a leaf dipping method proposed by the International Resistance Action Committee (IRAC), and the test insects are plutella xylostella, armyworm, cotton bollworm and spodoptera frugiperda.
First, after dissolving the compound in a small amount of DMSO, the compound was serially diluted with 0.05% tween aqueous solution to different concentrations of drug solutions to be tested. Soaking the leaves in the liquid medicine to be tested for 3-5 seconds, taking out, treating a control group with 0.05% Tween aqueous solution, repeating each experiment three times (20 larvae are reused each time), placing in a culture dish which is paved with filter paper and has the diameter of 10cm, drying at room temperature, inoculating 20 heads of the test insects into each culture dish, culturing under a proper condition, and recording the death rate of the larvae after 96 hours. The larvae were considered dead if they were not induced to move normally when contacted with a brush.
Calculating mortality
Calculating mortality and correcting mortality
Wherein P1 is the mortality rate of the treatment, K is the number of dead insects, and N is the total number of insects treated.
Where P2 is corrected mortality, P1 is treatment mortality, and P0 is blank control mortality. If the blank mortality is greater than 20%, the experiment should be redone.
The insecticidal activity data for the partial compounds of formula I are shown in table 4.
TABLE 4 pesticidal activity results for partial compounds of formula I
As can be seen from Table 4, some of the compounds of formula I provided by the present invention have insecticidal activity against the tested plutella xylostella, armyworm, Heliothis armigera and Spodoptera frugiperda. Particularly, part of the compounds have obvious control effect on diamondback moths and armyworms, for example, the lethality of the compound I-06 to the diamondback moths at the concentration of more than 10ppm is 100 percent and is equivalent to that of a contrast medicament, namely chlorantraniliprole; the lethality of compound I-14 to armyworm above 25ppm concentration was 100%, comparable to the control agent chlorantraniliprole. Has the prospect of being used as an agricultural insecticide to prevent and control agricultural pests such as diamondback moth and armyworm.
The above examples are only for describing the preferred embodiments of the present invention, and are not intended to limit the scope of the present invention, and various modifications and improvements made to the technical solution of the present invention by those skilled in the art without departing from the spirit of the design of the present invention should fall within the protection scope defined by the claims of the present invention.
Claims (10)
1. A compound of the formula I, wherein,
in the formula I, Z is selected from Z1Or Z2Wherein
R1、R2、R3The substitution mode is mono-substitution, di-substitution or multi-substitution;
R1、R2、R3the same or different, each independently selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy radical, C3-C12Cycloalkyl radical, C1-C12Alkylamino, halogeno C1-C12Alkylamino radical, di (C)1-C12Alkyl) amino, halo-di (C)1-C12Alkylamino), C1-C12Alkylthio, halo C1-C12Alkylthio radical, C2-C12Alkenyl radical, C2-C12Alkynyl, C2-C12Alkenyloxy, halogeno C2-C12Alkenyloxy radical, C2-C12Alkynyloxy, C1-C12Alkylsulfonyl, halo C1-C12Alkylsulfonyl radical, C1-C12Alkylcarbonyl, halo C1-C12Alkylcarbonyl group, C1-C12Alkoxycarbonyl, halo C1-C12Alkoxycarbonyl group, C1-C12Alkylamino carbonyloxy, halo C1-C12Alkylamino carbonyloxy radical, C1-C12Alkylsulfonyloxy and halo C1-C12One or more of alkylsulfonyloxy;
m is an integer of 0 to 7.
2. The compound of claim 1, wherein: the halogen is selected from fluorine, chlorine, bromine or iodine;
R1、R2、R3are the same or different and are each independently selected from C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkyl radical, C1-C6Alkylamino, halogeno C1-C6Alkylamino radical, di (C)1-C6Alkyl) amino, halo-di (C)1-C6Alkylamino), C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, C1-C6Alkylsulfonyl, halo C1-C6Alkylsulfonyl radical, C1-C6Alkylcarbonyl, halo C1-C6Alkylcarbonyl group, C1-C6Alkoxycarbonyl, halo C1-C6Alkoxycarbonyl group, C1-C6Alkylamino carbonyloxy, halo C1-C6Alkylamino carbonyloxy radical, C1-C6Alkylsulfonyloxy and halo C1-C6One or more of alkylsulfonyloxy groups.
3. A process for the preparation of a compound of formula I as claimed in any one of claims 1 or 2, comprising the steps of:
carrying out nucleophilic substitution reaction on a compound shown in a formula II and a compound shown in a formula III in an organic solvent under the action of an acid binding agent to obtain a compound shown in a formula I;
in the formula II, R3M is defined as formula I; in formula III, Z is as defined for formula I.
4. The production method according to claim 3, characterized in that: the organic solvent is at least one selected from methyl acetate, N-dimethylformamide, toluene, xylene, methanol, ethanol and tetrahydrofuran;
the temperature of the nucleophilic substitution reaction is 70-120 ℃, and the time is 4-12 hours.
5. The production method according to claim 3 or 4, characterized in that: the molar ratio of the compound shown in the formula II to the compound shown in the formula III is 1: (1-5).
6. The production method according to any one of claims 3 to 5, characterized in that: the acid-binding agent is selected from at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, cesium carbonate, potassium carbonate, triethylamine and N, N-diisopropylethylamine; the molar ratio of the acid-binding agent to the compound shown in the formula II is (1.2-3): 1; and/or the presence of a gas in the gas,
the nucleophilic substitution reaction is carried out under the action of a catalyst; the catalyst is selected from at least one of potassium iodide and sodium iodide; the molar ratio of the catalyst to the compound shown in the formula II is (0.01-0.05): 1.
7. use of a compound according to claim 1 or 2 or a pharmaceutical composition comprising a compound according to claim 1 or 2 as or in the preparation of an agricultural fungicide.
8. An agricultural fungicide according to claim 7, characterized in that: the agricultural bactericide is a bactericide for preventing and treating the following plant pathogenic bacteria: at least one of sclerotinia sclerotiorum, bakanae disease of rice, canker of apple, rhizoctonia solani, magnaporthe oryzae, botrytis cinerea, fusarium graminearum, pythium aphanidermatum and phytophthora capsici.
9. Use of a compound according to claim 1 or 2 or a pharmaceutical composition comprising a compound according to claim 1 or 2 as or in the preparation of an agricultural insecticide.
10. An agricultural insecticide as claimed in claim 9, wherein: the agricultural insecticide is an insecticide for preventing and controlling the following agricultural pests: the agricultural pests are at least one of diamondback moth, armyworm, cotton bollworm and spodoptera frugiperda.
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