CN104557620A - Strobilurin compound containing nitrohydrazinecarboximidamide structure as well as preparation method and application of strobilurin compound - Google Patents

Abstract

The invention discloses a methoxyacrylate compound containing a nitroaminoguanidine structure, a preparation method and an application thereof. The general structural formula of the compound is shown in formula I, wherein, R ₁ is H, C ₁ to C ₁₀ saturated or unsaturated aliphatic hydrocarbon group, phenyl, substituted phenyl, pyridin-2-yl, substituted pyridin-2-yl , Pyridin-3-yl, substituted pyridin-3-yl, pyridin-4-yl, substituted pyridin-4-yl, thiazol-2-yl, substituted thiazol-2-yl, furan-2-yl, substituted furan-2 -yl, benzyl, substituted benzyl, phenethyl, substituted phenethyl, 2-hydroxy-1-naphthyl or 3-substituted phenylpropan-2-yl; _R2 is hydrogen or C1～C10 alkyl . Insecticidal and fungicidal activity experiments show that the compound represented by the formula (I) has good biological activity, can effectively prevent crops from being attacked by pests and harmful bacteria, and can be used as a plant insecticide and fungicide.

Description

A kind of methoxyacrylate compound containing nitro aminoguanidine structure and its preparation method and application

technical field

The invention belongs to the technical field of agricultural chemicals, and in particular relates to a methoxyacrylate compound containing a nitroaminoguanidine structure and a preparation method and application thereof.

Background technique

Insecticides currently on the market only prevent and control plant pests caused by harmful insects, but have no effect on plant diseases caused by harmful bacteria; fungicides on the market only have preventive effects on plant diseases caused by harmful bacteria It has a control effect, but has no effect on plant pests caused by harmful insects. Plant diseases and insect pests often occur at the same time, which requires simultaneous killing of harmful insects and harmful bacteria on plants. The conventional method is to use one or more insecticides in conjunction with one or more fungicides to simultaneously kill Kill harmful insects and harmful germs, so as to prevent and control plant diseases and insect pests. However, the combined use of insecticides and fungicides will lead to cumbersome spraying operations. It is necessary to measure one or more insecticides and one or more fungicides according to a specific ratio, and the cost of spraying will increase accordingly. There are many types of drugs, and the amount of drug residues on plants will increase accordingly.

Therefore, there is an urgent need to develop a drug with both bactericidal and insecticidal activity to prevent and control plant diseases and insect pests, so as to simplify the application operation, reduce the cost, and reduce the residue of the drug on the plant.

Contents of the invention

The technical problem solved by the present invention is how to prepare a drug with both bactericidal activity and insecticidal activity to prevent and control plant diseases and insect pests.

In order to solve the above technical problems, the present invention provides a methoxyacrylate compound containing a nitroaminoguanidine structure.

The methoxyacrylate compound containing nitroaminoguanidine structure provided by the present invention has a structural formula as shown in formula I:

In the above formula I, R ₁ is C ₁ ~ C ₁₀ (such as C ₁ ~ C ₅ ) saturated or unsaturated aliphatic hydrocarbon group, phenyl, substituted phenyl, pyridin-2-yl, substituted pyridin-2-yl, pyridin- 3-yl, substituted pyridin-3-yl, pyridin-4-yl, substituted pyridin-4-yl, thiazol-2-yl, substituted thiazol-2-yl, furan-2-yl, substituted furan-2-yl, Benzyl, substituted benzyl, phenethyl, substituted phenethyl, 2-hydroxy-1-naphthyl or 3-substituted phenylpropan-2-yl;

Wherein, the saturated or unsaturated aliphatic hydrocarbon group can be straight chain or branched;

The substituted phenyl, substituted pyridin-2-yl, substituted pyridin-3-yl, substituted pyridin-4-yl, substituted thiazol-2-yl, substituted furan-2-yl, substituted benzyl, substituted phenethyl and The substituents in 3-substituted phenylpropan-2-yl can be selected from any of the following: halogen, hydroxyl, nitro, C ₁ ~C ₈ alkyl, fluorinated C ₁ ~C ₄ alkyl (such as trifluoromethyl), C ₁ -C ₅ alkoxy (thio) group, cyano group, aryloxy group (such as: phenoxy group), etc.

R ₂ is hydrogen or C ₁ -C ₁₀ (such as C ₁ -C ₅ ) alkyl such as methyl, ethyl, etc.

The compound shown in the formula I provided by the present invention can specifically be any of the following in Table 1:

Compound shown in Table 1 Formula I

The methoxyacrylate compound containing nitroaminoguanidine structure shown in the formula I provided by the present invention is prepared according to the method comprising the following steps:

Under the action of a base, react the compound shown in formula II with the compound shown in formula III to obtain a system containing the compound shown in formula I.

In the above formula II, the definitions of R ₁ and R ₂ are the same as the definitions of R ₁ and R ₂ in formula I, respectively.

In the above formula III, L represents a leaving group such as Cl, Br, I, OTos (p-toluenesulfonyloxy) or OTf (trifluoromethanesulfonate).

In the above method, the base is an inorganic base, and the base may specifically be sodium hydride, sodium carbonate, potassium carbonate, cesium carbonate or sodium amide.

The molar ratio of the base to the compound represented by formula II is 0.5-1.5:1, specifically 0.724:1, 0.8:1.

The molar ratio of the compound represented by the formula II to the compound represented by the formula III is 1:1-2.1, specifically 1:1.685, 1:1.75.

The reaction is carried out in an organic solvent, and the organic solvent may specifically be N,N-dimethylformamide or acetonitrile.

The temperature of the reaction is from 0° C. to the reflux temperature of the organic solvent.

The reaction time is 1 h to 6 h, specifically 2.5 h.

In the above method, the system containing the compound represented by formula I contains a large amount of insoluble solids.

The above method also includes the step of isolating the compound represented by formula I from the system containing the compound represented by formula I. The specific operation is as follows: first filter the system to remove insoluble solids, then precipitate the obtained filtrate to obtain a crude product, and finally recrystallize the crude product to obtain the compound shown in formula I.

The compound represented by the formula III is prepared according to existing methods, such as referring to the methods provided in European patents EP203606 and EP254426.

The present invention also provides the application of the methoxyacrylate compound containing the nitroaminoguanidine structure represented by formula I.

The purposes of the methoxyacrylate compound containing nitroaminoguanidine structure shown in the formula I provided by the present invention is its application in the following aspects:

1) for the preparation of plant insecticides; 2) for the preparation of plant fungicides; 3) for the preparation of plant disease inhibitors.

The invention also provides 1) plant insecticide or preparation; 2) plant fungicide or preparation; 3) plant disease inhibitor.

The plant insecticidal drug or preparation and/or bactericidal drug or preparation and/or plant disease inhibitor provided by the present invention, their active ingredient is a methoxyacrylate compound containing a nitroaminoguanidine structure shown in formula I.

The mass percent content of the active ingredient in the plant insecticidal drug or preparation and/or plant fungicidal drug or preparation and/or plant disease inhibitor is 0.01%-99.99%.

The plant insecticidal drug or preparation and/or plant fungicidal drug or preparation and/or plant disease inhibitor can be processed into any acceptable dosage form as required. Examples include suspensions, emulsions, aerosols, wettable powders, emulsifiable concentrates, and granules.

The compound represented by formula I provided by the present invention and the plant insecticide or preparation containing the compound as an active ingredient can control and eliminate a wide range of pests.

The pests are exemplified as follows:

Homoptera pests include pests of Aphididae, Amylinidae, Planthoppers, Psyllididae, Leafhoppers and Scaloididae. Aphididae pests can specifically be cotton aphid, soybean aphid, green peach aphid, peach aphid, radish aphid or cabbage aphid; planthopper pests can specifically be brown planthopper or rice planthopper; whitefly pests can specifically be Bemisia tabaci The pests of the Leafhopper family can specifically be the black-tailed leafhopper;

Lepidoptera pests include noctuidae and xylostella. Specific pests of the Noctuidae family may be beet armyworm, Spodoptera litura or cotton bollworm; specific pests of the Plutella xylostidae family may be diamondback moth.

The compound represented by formula I provided by the present invention and the plant fungicide or preparation containing the compound as an active ingredient can control and eliminate a wide range of germs.

The target pathogens of the compound represented by formula I provided by the present invention and the plant fungicidal drug or preparation with the compound as an active ingredient are Ascomycetes, Basidiomycetes, Oomycetes, Deuteromycetes, Phycomycetes and/or Fungi in the class Hyphomycetes.

The compound represented by the formula I provided by the present invention and the plant disease inhibitor containing the compound as an active ingredient can control and eliminate a wide range of diseases.

The diseases can specifically be cotton blight, tomato late blight, pepper phytophthora, apple ring spot, watermelon anthracnose, melon fruit rot and cucumber gray mold.

Another object of the present invention is to provide a method for controlling plant pests, germs and diseases.

The method for controlling plant pests, germs and diseases provided by the present invention is to apply the plant insecticide or preparation and/or plant fungicide or preparation and/or plant disease inhibitor provided by the present invention to plant leaves and/or on the fruit and/or seeds, or

Applying the plant insecticidal drug or preparation and/or plant fungicidal drug or preparation and/or plant disease inhibitor provided by the present invention in the environment where plant leaves and/or fruits and/or seeds are growing or expected to grow;

The application concentration of the active ingredient of the plant insecticide or preparation and/or plant fungicide or preparation and/or plant disease inhibitor is 1-1000 mg/L, such as 1-50 mg/L.

Detailed ways

The present invention will be described below through specific examples, but the present invention is not limited thereto.

The experimental methods used in the following examples are conventional methods unless otherwise specified; the reagents and biological materials used in the following examples can be obtained from commercial sources unless otherwise specified.

The pathogenic bacteria involved in the following examples are as follows:

Cotton Rhizoctonia solani (Wang Weijuan; Lu Xiuyun; Li Baoqing; Guo Qinggang; Li Shezeng; Ma Ping; Research on the mycelial fusion group of Rhizoctonia solani and its pathogenicity in Hebei Province[J]; Journal of North China Agricultural Science; 2010 Year S1 period);

Tomato late blight pathogen (Kang Ligong; Jiang Jingbin, Li Jingfu, Xu Xiangyang; Research on biological characteristics of tomato late blight pathogen (Ⅱ); Journal of Northeast Agricultural University; Volume 39 Issue 11);

Phytophthora capsici (Sun Xiuwen; Zhang Xiuguo; Pathogenicity differentiation and DNA polymorphism analysis of Phytophthora capsici in different regions; Journal of Changjiang University (Natural Science Edition) Agricultural Science Volume; 2008 Issue 03);

Apple ring spot fungus (Li Changhuai, Chen Xiuhui; Comprehensive control technology for apple ring spot [J]; Journal of Fruit Trees; 1989-03);

Melon anthracnose (Fang Li; Agrobacterium-mediated transformation of Fusarium graminearum and melon anthracnose and preliminary screening of pathogenic mutants [D]; Zhejiang University; 2005);

Pythium melon and fruit (He Shuishan, Zhang Bingxin, Ge Qixin; Study on the infection process of Pythium melon and fruit zoospores on tomato and begonia[J]; Acta Phytopathology; 1992-02);

Botrytis cinerea (Wang Guiqing; Sun Hua; Effect of Liaoasarum essential oil on cell wall degrading enzyme activity of Botrytis cinerea in vitro; Journal of Huazhong Agricultural University; Vol. 28, No. 6).

Taking compound 24 as an example, the preparation method of the methoxyacrylate compound containing nitroaminoguanidine structure shown in formula I provided by the present invention is illustrated below.

Embodiment 1, the preparation of compound 24

(1) Preparation of 1-nitro-3-aminoguanidine

Put a 100mL three-neck bottle in an oil bath, and put in 2.0g (19.2mmol) of nitroguanidine and 25mL of water in sequence. While heating to 55° C. under magnetic stirring, 1.3 g (21.6 mmol) of 85% hydrazine hydrate was slowly added dropwise from the dropping funnel. Keep the material temperature at 55°C and continue the reaction for 15 minutes. When the nitroguanidine solid dissolves and turns into an orange-yellow clear liquid, quickly cool it in an ice-salt water bath, and slowly add concentrated hydrochloric acid dropwise to adjust the pH to 5-6, and continue to cool in an ice-salt water bath overnight. Filter under reduced pressure and dry naturally in a fume hood. Recrystallized with water to obtain 1.6 g of light yellow crystals, yield 70%, melting point 191-192°C (document: melting point 187-188°C, yield 50%).

The structural characterization data are as follows:

¹ H NMR (DMSO-d ₆ )δ: 9.33(s,1H,C=N H ),8.27(s,1H,-N H NO ₂ ),7.56(s,1H,-N H NH ₂ ),4.69 (s,2H,-NHN H ₂ ).

(2) Preparation of 1-nitro-4-n-pentanal aminoguanidine

Into a 250mL three-neck flask, 11.9g (0.1mol) of 1-nitro-3-aminoguanidine, 100mL of anhydrous methanol and 0.6mL of glacial acetic acid were successively added. Heating to boiling under magnetic stirring, slowly added 9.5 g (0.11 mol) of n-valeraldehyde and 10 mL of anhydrous methanol solution dropwise from the dropping funnel. After the dropwise addition was completed, the mixture was heated to reflux and reacted at reflux for 3.5 hours. Cool down, pour into 150ml of ice water, solid precipitates out, let stand overnight. The resulting crude product was recrystallized from ethyl acetate to obtain 16.3 g of a white solid with a yield of 87% and a melting point of 101-103°C.

The structural characterization data are as follows:

0.93(t,3H),1.34-1.40(m,2H),1.50-1.55(m,2H),2.30-2.36(m,2H),6.99(brs,1H),7.73(t,1H),8.74( brs,1H), 10.89(brs,1H).

(3) Preparation of Compound 24

Into a 250mL three-necked flask, put 5g (0.0267mol) of 1-nitro-4-n-valeraldehyde aminoguanidine successively, 2.67gK ₂ CO ₃ (0.01934mol) and 100mL of acetonitrile, stir rapidly for 1 hour, slowly raise the temperature and add 12.8 g (0.045 mol) of the compound shown in formula III (L is bromine), continued to react for 2.5 hours after reflux, stopped the reaction, left to cool, there was a large amount of insoluble solids at the bottom of the three-necked flask, filtered off the solids (mostly salts), and the filtrate After precipitating, use ethyl acetate and petroleum ether to make a saturated solution, slowly volatilize, and obtain 2.1 g of white powder after repeated recrystallization, with a melting point of 160-162°C and a yield of 20%.

The structural characterization data are as follows:

0.84(t,J=7.2,3H,CH ₃ ),1.13-1.26(m,2H,CH ₂ ),1.31-1.41(m,2H,CH ₂ ),2.17-2.24(m,2H,CH ₂ ), 3.74(s,3H,=CHO CH ₃ ),3.89(s,3H,COOCH ₃ ),4.85(s,1H, ArCH ₂ ),5.28(s,1H, ArCH ₂ ),6.91-7.28(m, 5H, 4ArH, 1=CH O), 7.62 (brs, 1H, C=NH), 7.63 (s, 1H, -CH=N) 9.14 (brs, 1H, =NH)

HRMS [M+Na]: Calculated: 414.1748; Found: 414.1747.

Compound 1-25 was prepared using a method similar to the above example, and the structural characterization data of the prepared compound 1-25 are shown in Table 2.

Table 2 Structural characterization data of compound 1-25

The insecticidal activity of compound shown in embodiment 2, formula I to soybean aphid is measured

The soybean aphids used in this experiment were provided by artificial breeding of the Agricultural College of China Agricultural University.

Operation process: Determination of insecticidal activity by the drug film method. Use a puncher to punch out circular leaves with a size of 20 mm on the cultivated bean leaves, soak the leaves in 50 μg/mL liquid medicine for 5 seconds, then take them out and dry them on absorbent paper, and spread them in the groove of a petri dish. Put a thin layer of agar on it, put the dried leaves into the grooves of the petri dish, put about 20 artificially raised bean aphids in each groove, and finally seal it with plastic wrap (good air permeability), and place it in an artificial climate In the box, control the temperature at 25±1°C, and check the results after 48 hours.

Judgment criteria for death: the individual pests that touch the insect body lightly and cannot crawl normally are regarded as dead.

Corrected mortality rate (%) = (sample mortality rate - blank control mortality rate) / (1 - blank control mortality rate) × 100%

The test results are shown in Table 3.

The insecticidal activity test result (48h) of part compound shown in table 3 formula I to soybean aphid

serial number Total number of insects Number of dead insects Fatality (%) CK (0.5% Triton solution) 154 8 5.2 imidacloprid 66 57 86.4 11 34 twenty one 61.8 12 44 27 61.4 13 38 25 65.8 14 59 42 71.2 15 31 twenty two 71.0 16 39 twenty two 56.4 17 28 5 17.9 18 42 15 35.7 19 43 17 39.5 20 61 32 52.5 twenty one 58 44 75.9 twenty two 60 55 91.7 twenty three 52 41 78.8 twenty four 43 25 58.1 25 48 34 70.8

It can be seen from Table 3 that the target compounds generally have good activity on soybean aphids, among which the inhibitory activity of compound 21 and compound 23 on soybean aphids is equivalent to that of imidacloprid on soybean aphids, and the inhibitory activity of compound 22 on soybean aphids is high Inhibitory activity of imidacloprid against soybean aphids.

Embodiment 3, the insecticidal activity test of the compound shown in formula I to peach aphid

Green peach aphid is a wide-feeding pest, with nearly 300 species of host plants, and damages plant growth by sucking the juice in leaf tissue. In addition, green peach aphid is also the main vector of various plant viruses. The object of this experiment was 3-day-old nymphs of peach aphid, which were collected from the peach tree population in Baiwangshan area, Haidian District, Beijing.

Operation process: Determination of insecticidal activity by dipping method. Cut the leaf with aphids into a shape with a suitable size and number of insects, then take it out after soaking in the prepared medicinal solution for 5 seconds, absorb the excess medicinal solution from the leaves, record the total number of insects after drying, and put it on a filter paper with moisturizing In a petri dish, seal it with plastic wrap, place it in a light incubator, control the temperature at 25±1°C, and check the results after 24 hours.

Judgment criteria for death: the individual pests that touch the insect body lightly and cannot crawl normally are regarded as dead.

Corrected mortality rate (%) = (sample mortality rate - blank control mortality rate) / (1 - blank control mortality rate) × 100%

The results are shown in Table 4.

The insecticidal activity assay result (24h) of some compounds shown in table 4 formula I to peach aphid

serial number _LC50 (μg/mL) serial number _LC50 (μg/mL) imidacloprid 0.3 1 117.8 6 1.9 2 161.1 7 0.2 3 26.9 8 26.3 4 4.0 9 12.8 5 2.5 10 12.9

It can be seen that the target compounds have higher activity against peach aphid, and the activity of compound 7 is equivalent to that of the reference drug imidacloprid.

Embodiment 4, the compound shown in formula I are to the insecticidal activity test of aphid aphid

The aphid is distributed in 25 provinces across the country. It can host a variety of fruit trees and family plants, and is very harmful. Often, adults and nymphs gather on new shoots and the back of leaves to suck juice, and the damaged leaves lose their green color and move toward the back of the leaves. For vertical rolls, white wax powder accumulates in the rolled leaves. When it is severe, the leaves fall early and the young shoots dry up. The excretion of honeydew often causes soot pollution. In this experiment, the samples of Aphid spp. were collected from the peach tree population in Baiwangshan area, Haidian District, Beijing.

Operation process: Determination of insecticidal activity by spray method. Cut the leaves with aphids into shapes with appropriate size and number of insects, put them in a petri dish, and then put the petri dish under a gas compression spray tower for spraying, the spray volume is 1mL per dish, and seal it with plastic wrap after spraying , placed in a light incubator, control the temperature at 25±1°C, and check the results after 24 hours.

Judgment criteria for death: the individual pests that touch the insect body lightly and cannot crawl normally are regarded as dead.

Corrected mortality rate (%) = (sample mortality rate - blank control mortality rate) / (1 - blank control mortality rate) × 100%

The results are shown in Table 5.

The compound shown in table 5 formula I is to the insecticidal test result (24h) of A.

serial number _LC50 (μg/mL) serial number _LC50 (μg/mL) imidacloprid 30.4 1 28.7 6 19.0 2 2.0 7 38.9

3 45.1 8 41.9 4 22.3 9 7.6 5 18.3 10 9.8

It can be seen that this type of compound has very good activity against the aphid, most of which are higher than the reference drug imidacloprid.

Embodiment 5, the in vitro bactericidal activity assay of the compound shown in formula I to plant pathogenic bacteria

Cotton blight pathogen (Rhizogonia solani), tomato late blight pathogen (tomato infestation pathogen), capsicum phytophthora pathogen (Pytophthora capsici), apple ring spot pathogen (apple ring pattern) provided by the Institute of Plant Protection, Chinese Academy of Agricultural Sciences pathogen), watermelon anthracnose pathogen (melon anthracnose), melon and fruit pythium pathogen (melon and fruit pythium), cucumber gray mold pathogen (Botrytis cinerea) are the measurement objects, and the growth rate method is used for determination.

Operation procedure: All the compounds represented by formula I were prepared at 50 μg/mL. Under sterile conditions, pick the test strain cake and place it in the center of the PDA medium plate containing different drug concentrations. Take the blank PDA medium as the control and culture it in a constant temperature incubator at 25°C. Each gradient was tested 3 times in parallel.

According to the growth of the colonies in the blank control petri dish, the growth of the mycelium of the pathogenic bacteria was investigated. After the colonies in the blank control were fully grown, the colony diameters of each treatment were measured by the cross method. The formula for calculating mycelial growth inhibition rate is as follows:

The results of the bactericidal test are shown in Table 6.

Compound shown in table 6 formula I is to the in vitro bactericidal activity assay result (50 μ g/mL) of phytopathogen

It can be seen from Table 6 that the target compound has good antibacterial activity against a variety of plant pathogens. Although its broad spectrum is slightly worse than that of the reference drug azoxystrobin, some compounds have higher activity than azoxystrobin against specific pathogens. , such as some compounds (4, 5, 6, 7, 12, 13, 14, 15, 16, 17, 18, 19, 22 and 25) are stronger than azoxystrobin on cucumber gray mold, and compound 18 has The inhibition rate of C. cinerea was 77.4%, which was much higher than the inhibition rate (51.1%) of azoxystrobin on C. cinerea. The inhibitory rate of compound 3 to apple ring pattern is equivalent to that of azoxystrobin, and compound 2 has better inhibition to apple ring pattern and cucumber Botrytis cinerea, which can be used as a special agent for the control of these diseases.

Claims (9)

1. Compound shown in formula I: In formula I, R ₁ is a C ₁ ~C ₁₀ saturated or unsaturated aliphatic hydrocarbon group, phenyl, substituted phenyl, pyridin-2-yl, substituted pyridin-2-yl, pyridin-3-yl, substituted pyridin-3-yl Base, pyridin-4-yl, substituted pyridin-4-yl, thiazol-2-yl, substituted thiazol-2-yl, furan-2-yl, substituted furan-2-yl, benzyl, substituted benzyl, phenethyl Base, substituted phenethyl, 2-hydroxy-1-naphthyl or 3-substituted phenylpropan-2-yl; Wherein, the saturated or unsaturated aliphatic hydrocarbon group is straight chain or branched; The substituted phenyl, substituted pyridin-2-yl, substituted pyridin-4-yl, substituted thiazol-2-yl, substituted furan-2-yl, substituted benzyl, substituted phenethyl and 3-substituted phenylpropane- The substituents in the 2-yl group are all selected from any one of the following: halogen, hydroxyl, nitro, C ₁ -C ₈ alkyl, fluorinated C ₁ -C ₄ alkyl, C ₁ -C ₅ alkane Oxygen, C ₁ to C ₅ alkylthio, C ₁ to C ₅ alkoxy, cyano and aryloxy; R ₂ is hydrogen or a C ₁ -C ₁₀ alkyl group. 2. A method for preparing the compound shown in formula I, comprising the following steps: reacting the compound shown in formula II with the compound shown in formula III under the action of a base to obtain a system containing the compound shown in formula I; In formula II, the definitions of _R1 and _R2 are the same as the definitions of _R1 and _R2 in formula I in claim 1; In formula III, L represents a leaving group: Cl, Br, I, p-toluenesulfonyloxy or trifluoromethanesulfonate. 3. The method according to claim 2, characterized in that: The base is an inorganic base, and the inorganic base is selected from at least one of the following: sodium hydride, sodium carbonate, potassium carbonate, cesium carbonate or sodium amide; The molar ratio of the base to the compound represented by formula II is 0.5-1.5:1; The substance ratio of the compound represented by the formula II to the compound represented by the formula III is 1:1-2.1; The reaction is carried out in an organic solvent, and the organic solvent is N,N-dimethylformamide or acetonitrile; The temperature of the reaction is from 0°C to the reflux temperature of the solvent; The reaction time is 1h-6h. 4. The application of the compound according to claim 1 or the pharmaceutical composition containing said compound in the preparation of the following products: 1) plant insecticide; 2) plant fungicide; 3) plant disease inhibitor. 5. application according to claim 4, is characterized in that: described plant insecticide is the insecticide of killing Homoptera pest and/or Lepidoptera pest; Described Homoptera pest is following six Pests of at least one family in the following families: Aphididae, Amyridae, Planthoppers, Psyllidae, Leafhoppers and Scaloides; the Lepidoptera pests are Noctuidae and/or Plutethidae; The target pathogens of the plant fungicide are fungi in the class Ascomycetes, Basidiomycetes, Oomycetes, Deuteromycetes, Phycomycetes and/or Hyphomycetes; The diseases are cotton blight, tomato late blight, pepper phytophthora, apple ring spot, watermelon anthracnose, melon fruit rot and cucumber gray mold. 6. A plant insecticide or preparation whose active ingredient is the compound represented by formula I in claim 1, wherein the mass percentage of the active ingredient in the plant insecticide or preparation is 0.01%-99.99%. 7. A plant fungicide or preparation, the active ingredient of which is the compound represented by formula I in claim 1, wherein the mass percentage of the active ingredient in the plant insecticide or preparation is 0.01%-99.99%. 8. A plant disease inhibitor whose active ingredient is the compound represented by formula I in claim 1, wherein the mass percentage of the active ingredient in the plant insecticide or preparation is 0.01%-99.99%. 9. A method for preventing and controlling plant pests and/or germs and/or diseases is to use the plant insecticidal drug or preparation described in claim 6 and/or the plant fungicidal drug or preparation described in claim 7 and/or the right The plant disease inhibitor described in claim 8 is applied on plant leaves and/or fruits and/or seeds; Or, the plant insecticidal drug or preparation described in claim 6 and/or the plant fungicidal drug or preparation described in claim 7 and/or the plant disease inhibitor described in claim 8 are applied to plant leaves and/or fruits and and/or the environment in which the seed is growing or expected to grow; The application concentration of the plant insecticidal drug or preparation and/or the plant fungicidal drug or preparation and/or the active ingredient of the plant disease inhibitor is 1-1000 mg/L.