CN107383120A - A kind of glycosyl naphthalimide derivative and preparation method and application - Google Patents

A kind of glycosyl naphthalimide derivative and preparation method and application Download PDF

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CN107383120A
CN107383120A CN201710639194.3A CN201710639194A CN107383120A CN 107383120 A CN107383120 A CN 107383120A CN 201710639194 A CN201710639194 A CN 201710639194A CN 107383120 A CN107383120 A CN 107383120A
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formula
compound
cauzs
glycosyl
pharmaceutically acceptable
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CN107383120B (en
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张建军
沈生强
杨青
陈威
王道全
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China Agricultural University
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Abstract

The invention discloses a kind of glycosyl naphthalimide derivative and preparation method and application.Glycosyl naphthalimide derivative or its pharmaceutically acceptable salt of the present invention, shown in the structural formula such as formula (I) or formula (II) of the glycosyl naphthalimide derivative, CAUZS A, CAUZS B are designated as respectively.Glycosyl naphthalimide derivative of the present invention has target enzyme inhibition activity and insecticidal activity.

Description

A kind of glycosyl naphthalimide derivative and preparation method and application
Technical field
The present invention relates to a kind of glycosyl naphthalimide derivative and preparation method and application, belongs to agricultural chemical compound preparation Field.
Background technology
Chitin is the straight-chain polysaccharide being made up of the 2-Acetamido-2-deoxy-D-glucose residue of glucosides key connection, and it is widely present in Fungi, invertebrate Mollusca, protozoa, Coelenterata, among Annelida.The metabolism of chitin can It is divided into the hydrolysis metabolism of the anabolism, chitin of chitin.The anabolism of chitin includes the intracellular of a series of complex, born of the same parents Outer biochemical and physiological conversion, and many of which physiology course does not understand still；In addition, chitin synthetase inhibitor such as acylureas The definite mechanism of action of class is also indefinite.And the hydrolytic process research ground of chitin is more thorough；In chitin hydrolytic process, Chitin is first chitin oligo saccharide by chitin restriction endonuclease and chitobiose enzyme hydrolysis, then be hydrolyzed to N- second by β-N-acetylmuramic glycanchydrolase Acylamino- hexose.
Rational design based on target is the important method of New pesticides discovery, because it has with strong points, security is high etc. Extensive concern of the advantage by researcher.Because the hydrolysis metabolism of the growth and development process and chitin of agricultural pests is close Correlation, and be free of chitin in high animal and plant body, therefore the relevant enzyme for being directed to chitin hydrolytic process is novel pesticide in recent years The study hotspot of target.
The family β of insect 20-N-acetylmuramic glycanchydrolase participates in the multiple physiology courses of insect, as Hex1 single-minded can be hydrolyzed with β The chitin oligosaccharides substrate of 1-4 glucosides key connections, is mainly expressed in the epidermis in insect molting period, and RNA disturbs the gene energy Insect is enough caused normally to be casted off a skin in growth course and dead.Therefore, for insect β-N-acetylmuramic glycanchydrolase (Ofhex1) inhibitor molecules of design have the important application prospect as novel pesticide.
The content of the invention
It is an object of the invention to provide a kind of glycosyl naphthalimide derivative and preparation method and application, glycosyl of the present invention Naphthalimide derivative has target enzyme inhibition activity and insecticidal activity.
A kind of glycosyl naphthalimide derivative provided by the invention or its pharmaceutically acceptable salt, its structural formula such as formula (I) or shown in formula (II), CAUZS-A, CAUZS-B are designated as respectively：
In formula (I) and formula (II), R1And R2It is hydrogen, nitro, halogen, C1~C4 alkoxies and C1~C4 alkyl-substituted At least one of amino；A is 2,3,5,6；B is 2,3,4；C is 2,3,4,5,6；
The structural formula of the alkyl-substituted amino of C1~C4 is as shown in Equation 1,
In formula 1, R3And R4It is at least one of C1~C4 alkyl；
The halogen includes at least one of fluorine, chlorine, bromine and iodine.
Present invention also offers the preparation method of compound CAUZS-A shown in above-mentioned formula (I), comprise the following steps：
1) compound shown in formula (III) is reacted in the basic conditions with compound shown in formula (IV), obtained shown in formula (V) Compound；
2) by the deprotection base in the basic conditions of compound shown in formula (V), that is, compound CAUZS- shown in formula (I) is obtained A；
Wherein, in formula (IV) and formula (V), R1It is alkyl-substituted for hydrogen, nitro, halogen, C1~C4 alkoxies and C1~C4 At least one of amino；A is 2,3,5,6；B is 2,3,4；R5For acetyl group, benzoyl, chloracetyl, tri-chloroethoxy carbonyl At least one of base and levulinic acyl group；R6For at least one of chlorine, bromine and iodine；The alkyl-substituted amino of C1~C4 Structural formula as shown in the formula 1.
In compound CAUZS-A preparation method shown in above-mentioned formula (I), in step 1), the examination of the alkalescence condition use Agent is at least one of sodium carbonate, potassium carbonate, sodium acid carbonate, saleratus and sodium hydride；
The temperature of the reaction can be 60~80 DEG C, and concretely 75 DEG C, the time can be 8~24h, concretely 10h, 8 ~10h, 10~24h or 8~20h；
In step 2), reagent that the alkalescence condition uses for sodium methoxide, methanol ammonia, methanol first ammonia and caustic alcohol in extremely Few one kind；The temperature of the reaction can be room temperature, and the time can be 12~48h, concretely 24h, 12~24h, 24~48h or 10 ~30h；
The mol ratio of compound shown in formula (III), compound shown in formula (IV) and compound shown in formula (V) is 1：0.5~ 2.5：0.5~2.5, concretely 2.1:2.5:1.6；
Step 1) and 2) in, include extraction, drying and the step of column chromatography.
Present invention also offers the preparation method of compound CAUZS-B shown in above-mentioned formula (II), comprise the following steps：
1) compound shown in formula (VI) is reacted with compound shown in formula (VII) in the basic conditions to obtain formula (VIII) institute Show compound；
2) by deprotection obtains compound CAUZS-B shown in formula (II) in the basic conditions formula (VIII) Suo Shi.
Wherein, in formula (VI) and formula (VII), R2Substitute for hydrogen, nitro, halogen, C1~C4 alkoxies and C1~C4 alkyl At least one of amino；C is 2,3,4,5,6；R7For acetyl group, benzoyl, chloracetyl, trichloro-ethoxycarbonyl and second At least one of acyl propiono；The structural formula of the alkyl-substituted amino of C1~C4 is as shown in the formula 1.
Compound CAUZS-B preparation method shown in above-mentioned formula (II), in step 1), reagent that the alkalescence condition uses For at least one of sodium carbonate, potassium carbonate, sodium acid carbonate, saleratus and sodium hydride；
The temperature of the reaction is room temperature, and concretely 25 DEG C, the time can be 8~24h, concretely 20h, 8~20h, 20~24h or 10~24h；
In step 2), reagent that the alkalescence condition uses for sodium methoxide, methanol ammonia, methanol first ammonia and caustic alcohol in extremely Few one kind；The temperature of the reaction is room temperature, and the time can be 12~48h, concretely 24h, 12~24h, 24~48h or 10~ 30h；
The mol ratio of compound shown in formula (III), compound shown in formula (IV) and compound shown in formula (V) is 1：0.5~ 2.5：0.5~2.5, concretely 2.8:2.8:1.7；
Step 1) and 2) in, include extraction, drying and the step of column chromatography.
In the present invention, the room temperature refers to 10~30 DEG C.
Invention further provides the glycosyl naphthalimide derivative or its medicine shown in above-mentioned formula (I) or formula (II) Acceptable salt is following 1) -3 on) in it is any in application：
1) application in insect β-N-acetylmuramic glycanchydrolase inhibitor is prepared；
2) desinsection；
3) insecticide is prepared.
Present invention also offers a kind of insect β-N-acetylmuramic glycanchydrolase inhibitor, its active component is the glycosyl naphthoyl Imine derivative or its pharmaceutically acceptable salt.
Present invention also offers a kind of insecticide, its active component be the glycosyl naphthalimide derivative or its pharmaceutically Acceptable salt.
The formulation of above-mentioned insecticide is pharmaceutically acceptable formulation；The formulation includes missible oil, wettable powder, suspension At least one of agent, pulvis, soluble powder, aqua, water dispersible granules, fumicants, granule and seed coat agent.
Present invention also offers a kind of insecticide emulsifiable concentrate, and it includes the material composition of following weight/mass percentage compositions：1~10% The glycosyl naphthalimide derivative or its pharmaceutically acceptable salt, 5~15% emulsifying agents, 0.1~1% bleeding agent and surplus Formed for solvent；
The emulsifying agent is surfactant, the surfactant include agriculture breast 0203B, 0208, GFC, OP-10 and tell Temperature at least one of -60；
The bleeding agent includes at least one of JFC-2, TX-10, FP-T, OX-408, OX-406, N-2 and UC-12A；
The solvent is toluene and/or dimethylbenzene.
Insecticide emulsifiable concentrate of the present invention specifically includes the material composition of following weight/mass percentage compositions：The 10% glycosyl naphthalene Imide derivative or its pharmaceutically acceptable salt, 5% emulsifying agent, 0.2% bleeding agent and surplus form for solvent.
Present invention also offers a kind of insecticide wettable powder, and it includes the material composition of following mass parts：15~50 Part glycosyl naphthalimide derivative or its pharmaceutically acceptable salt, 10~20 parts of surfactants and 30~75 parts of white carbon It is black；
The surfactant include SP-408, APG-810, TA-15, AOS, NNO, MF, AEC, M4600, SP-2728 and At least one of VESTVACO.
Insecticide wettable powder of the present invention specifically includes the material composition of following mass parts：20 parts of glycosyl naphthalenes Imide derivative or its pharmaceutically acceptable salt, 10 parts of surfactants and 70 parts of White Carbon blacks.
The present invention has advantages below：
The present invention synthesizes the novel glycosyl naphthalimide of structure using insect β-N-acetylmuramic glycanchydrolase as biological targets Class compound.Glycosyl naphthalimide compound or its pharmaceutically acceptable salt of the present invention have good target enzyme level Activity and insecticidal activity, part of compounds exceed comparison medicament HEXAFLUMURON to the insecticidal activity of diamondback moth and black peach aphid.Institute of the present invention Stating compound, there is very high pesticide research to be worth.
Brief description of the drawings
Fig. 1 is compound CAUZS-A-01 hydrogen nuclear magnetic resonance spectrogram.
Fig. 2 is compound CAUZS-A-01 carbon-13 nmr spectra figure.
Fig. 3 is compound CAUZS-B-01 hydrogen nuclear magnetic resonance spectrogram.
Fig. 4 is compound CAUZS-B-01 carbon-13 nmr spectra figure.
Embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
Material used, reagent etc., unless otherwise specified, are commercially obtained in following embodiments.
Embodiment 1, compound CAUZS-A
Compound CAUZS-A-01, R1=hydrogen, a=2, b=2, R5=OAc, R6=Br is prepared according to following reaction scheme, Comprise the following steps that：
(1)-O- acetyl group-the 2- of 2- bromoethyl 2- acetylaminohydroxyphenylarsonic acids 3,4,6- tri- are added in 100mL round-bottomed flask to take off Thio-β-D- the glucopyranosides (1.0g, 2.1mmol) of oxygen -1-, 2- (2- amino-ethyls) -1H- benzos [de] isoquinolin -1,3 (2H)-diketone (0.61g, 2.5mmol), Anhydrous potassium carbonate (0.32g, 2.3mmol), 40mL acetonitriles, in 75 DEG C under nitrogen protection Under the conditions of react 10h, TLC monitoring reactions are complete.Filter, column chromatography for separation obtains faint yellow solid 1.1g after filtrate concentration, receives Rate 83.1%.
Structural identification data is as follows：1H NMR (300MHz, DMSO) δ 8.57-8.44 (m, 4H, ArH), 7.99 (d, J= 9.3Hz, 1H, NH), 7.93-7.83 (m, 2H, ArH), 5.07 (t, J=9.7Hz, 1H, H-3), 4.86 (t, J=9.8Hz, 1H, ), H-4 4.71 (d, J=10.5Hz, 1H, H-1), 4.22-4.09 (m, 3H, H-6b, CH2NC=O), 4.00 (dd, J=12.2, 2.2Hz,1H,H-6a),3.92–3.81(m,2H,H-2,H-5),2.92–2.78(m,4H,2CH2),2.77–2.57(m,2H, SCH2),1.98,1.97,1.92(3s,9H,3OAc),1.76(s,3H,NAc).13C NMR(75MHz,DMSO)δ170.13, 169.75,169.39,169.24,163.65,134.35,131.35,130.77,127.47,127.26,122.19,83.60, 74.76,73.86,68.67,62.15,52.23,48.78,46.14,39.11,29.17,22.74,20.56,20.53, 20.45.
(2) products therefrom (1.0g, 1.6mmol) in (1), 10mL methanol are added in 50mL round-bottomed flask, 10mL satisfies And methanolic ammonia solution, 25 DEG C of room temperature, reaction 24h, concentration, column chromatography purify to obtain white solid 0.74g, yield 91.3%.
Structural identification data is as follows：1H NMR(300MHz,DMSO)δ8.53–8.40(m,4H,ArH),7.91–7.81(m, 2H, ArH), 7.71 (d, J=9.3Hz, 1H, NHAc), 5.01 (d, J=4.7Hz, 1H, OH), 4.96 (d, J=5.3Hz, 1H, ), OH 4.49 (br s, 1H, OH), 4.36 (d, J=10.3Hz, 1H, H-1), 4.17-4.08 (m, 2H, H-3, H-4), 3.66 (dd, J=11.4,3.4Hz, 1H, H-6b), 3.57-3.38 (m, 2H, H-2, H-6a), 3.31-3.20 (m, 1H, H-5), 3.15- 3.05(m,2H,ArCH2),2.85–2.72(m,4H,2CH2),2.72–2.54(m,2H,SCH2),1.79(s,3H,NAc).
13C NMR(75MHz,DMSO)δ169.05,163.64,134.36,131.41,130.82,127.53,127.32, 122.26,84.37,81.26,75.71,70.63,61.35,54.73,48.90,46.39,39.57,29.83,23.17.
Other formulas are that CAUZS-A series compound can be prepared according to the method described above.Particular compound numbering, Substituted radical, physicochemical data are as shown in table 1, and the proton nmr spectra of Structural Identification, mass spectrometric data are as shown in table 2.
The numbering of the CAUZS-A episode compounds of table 1, substituted radical, physicochemical data
The CAUZS-A episode compounds proton nmr spectra of table 2, mass spectrometric data
(Pos：The positive ion mode of mass spectroscopy；Neg：The negative ion mode of mass spectroscopy)
The preparation of embodiment 2, compound CAUZS-B
Compound CAUZS-B-01, R2=hydrogen, c=2, R7=OAc is prepared according to following reaction scheme, is comprised the following steps that：
(1) added in 100mL round-bottomed flask 2- acetylaminohydroxyphenylarsonic acids 3,4,6- tri--O- acetyl group -2- deoxidations -1- it is thio - β-D- glucopyranoses 1g (1.0g, 2.8mmol), 2- (2- bromoethyls) -1H- benzos [de] isoquinolin -1,3 (2H)-diketone (0.84g, 2.8mmol), Anhydrous potassium carbonate (0.46g, 3.4mmol), 40mL acetone, 20mL water, (25 DEG C) reaction 20h of room temperature, TLC monitoring reactions are complete.Revolving removes acetone, adds dichloromethane and water extraction, organic phase washing, dries, rotation is except organic molten After agent, column chromatography purifies to obtain white solid 1.4g, yield 85.3%.
Structural identification data is as follows：1H NMR (300MHz, DMSO) δ 8.60 (d, J=7.3Hz, 2H, Ar-H), 8.25 (d, J=8.2Hz, 2H, Ar-H), 7.78 (t, J=7.8Hz, 2H, Ar-H), 5.80 (d, J=9.5Hz, 1H, NH), 5.27-5.12 (m, 2H, H-3, H-4), 4.90 (d, J=10.5Hz, 1H, H-1), 4.60 (ddd, J=13.3,9.1,6.8Hz, 1H, CH2N), 4.40–4.11(m,4H,CH2N, H-6b, H-6a, H-2), 3.83 (ddd, J=9.3,4.4,2.2Hz, 1H, H-5), 3.25- 2.96(m,2H,SCH2),2.07,2.05,2.04(3s,9H,3OAc),1.78(s,3H,NAc).13C NMR(75MHz,DMSO)δ 170.12,169.76,169.40,169.22,163.38,134.51,131.44,130.88,127.55,127.33,122.16, 83.96,75.02,73.75,68.69,62.05,52.17,39.97,27.55,22.71,20.55,20.51,20.47.
(2) products therefrom (1.0g, 1.7mmol) in (1), 10mL methanol are added in 50mL round-bottomed flask, 10mL satisfies And methanolic ammonia solution, 24h, concentration are reacted, column chromatography purifies to obtain white solid 0.72g, yield 92.3%.
Structural identification data is as follows：1H NMR(300MHz,DMSO)δ8.57–8.43(m,4H,ArH),7.94–7.84(m, 2H, ArH), 7.74 (d, J=9.4Hz, 1H, NHAc), 5.05 (d, J=4.8Hz, 1H, OH), 5.01 (d, J=5.3Hz, 1H, ), OH 4.50 (d, J=10.3Hz, 1H, H-1), 4.45 (t, J=6.0Hz, 1H, OH), 4.34-4.21 (m, 2H, H-3, H-4), 3.70 (dd, J=11.3,6.0Hz, 1H, H-6b), 3.56 (dd, J=19.5,9.6Hz, 1H, H-2), 3.47 (dd, J=11.4, 5.6Hz,1H,H-6a),3.33–3.26(m,1H,H-5),3.22–3.10(m,2H,CH2N),2.99–2.74(m,2H,SCH2), 1.74(s,3H,NAc).13C NMR(75MHz,CDCl3)δ169.07,163.39,134.51,131.43,130.91,127.53, 127.33,122.14,84.86,81.40,75.62,70.54,61.35,54.64,39.98,27.59,23.11.
Other formulas are that CAUZS-B series compound can be prepared according to the method described above.Part of compounds numbering, Substituted radical, physicochemical data are shown in Table 3, and the proton nmr spectra of Structural Identification, mass spectrometric data are shown in Table 4.
The numbering of the CAUZS-B episode compounds of table 3, substituted radical, physicochemical data
Table 4CAUZS-B episode compounds proton nmr spectra, mass spectrometric data
(Pos：The positive ion mode of mass spectroscopy；Neg：The negative ion mode of mass spectroscopy)
The preparation of embodiment 3, compound CAUZS-A-01 missible oil
Take compound CAUZS-A-01 10g, emulsifying agent (agriculture breast 0208) 5g, bleeding agent (JFC-2) 0.2g, then with molten Agent dimethylbenzene constant volume obtains the missible oil that weight/mass percentage composition is 10%.
Other formulas can be prepared into according to the method described above for the missible oil of CAUZS-A, CAUZS-B compound in the present invention Arrive.
The preparation of embodiment 4, compound CAUZS-A-01 wettable powders
Compound CAUZS-A-01 20g in the embodiment of the present invention 1, surfactant (NNO) 10g, White Carbon black 70g are taken, is passed through After co-grinding, the wettable powder that weight/mass percentage composition is 20% is obtained.
Other formulas are that the wettable powder of CAUZS-A, CAUZS-B compound can be according to the method described above in the present invention It is prepared.
Embodiment 5, the enzyme inhibition activity measure of formula CAUZS-A, CAUZS-B compound
Activity determination method：With p-nitrophenyl -2- acetylaminohydroxyphenylarsonic acid 2- deoxidation-β-D- glucopyranosides (pNP- β - GlcNAc it is) test substrate, by enzyme with surveying enzyme activity buffer solution (20mM NaH2PO4, pH6.8) mixed in 96 orifice plates to final volume For 54 μ L, 6 μ L 5mM pNP- β-GlcNAc initial actions are added, 25 DEG C of incubation 5min, 60 μ L 0.5M sodium carbonate is added and terminates Reaction, absorption value is determined in 405nm.
Compound inhibitory activity assay method：By the inhibitor of enzyme and various concentrations (to be made in the embodiment of the present invention 1 and 2 Standby obtained compound, it is specific as shown in table 5) in incubation at room temperature 10min, and respectively under 0.1mM and 0.2mM concentration with The above method determines enzyme activity.Part of compounds is as shown in table 5 below to insect β-N-acetylmuramic glycanchydrolase Ofhex1 inhibitory activity.
As shown in Table 5, CAUZS-A, CAUZS-B of the present invention are inhibited to Ofhex1 enzymes.
Inhibitory activity of table 5 CAUZS-A, CAUZS-B episode compound to Ofhex1 enzymes
Embodiment 6, the insecticidal activity assay that formula of the present invention is CAUZS-A, CAUZS-B compound
Assay method：Blade is handled using infusion process, inspection result after 3 days, touches polypide, it is impossible to is normally creeped individual stereoscopic For death, its corrected mortality (%) is calculated.Compared with comparison medicament HEXAFLUMURON, judge medicament virulence size.Part of compounds Insecticidal activity data be shown in Table 6.
It is following to supply examination target：
Diamondback moth (Plutella xylostella Linnaeus), picks up from Beijing's vegetable fields in 2006, uses indoors Brassicaceous vegetable blade is raised, and rearing conditions are room temperature (27 ± 1) DEG C, humidity 80%, intensity of illumination 2000lux, light It is daily 12h according to the time.Indoors under rearing conditions, medicament work is carried out with 3 consistent instar larvaes of worm age, body weight and physiological status Property screening test.
Black peach aphid (Myzus persicae Sulzer), picks up from Handan in Hebei province cotton field, manually feed is long-term indoors The population of raising.Agent activity screening test is carried out with worm age, body weight and the consistent larva of physiological status.
The insecticidal activity of table 6 CAUZS-A, CAUZS-B episode compound

Claims (10)

1. a kind of glycosyl naphthalimide derivative or its pharmaceutically acceptable salt, it is characterised in that：The glycosyl naphthalimide Shown in the structural formula of derivative such as formula (I) or formula (II), CAUZS-A, CAUZS-B are designated as respectively：
In formula (I) and formula (II), R1And R2It is hydrogen, nitro, halogen, C1~C4 alkoxies and the alkyl-substituted amino of C1~C4 At least one of；A is 2,3,5,6；B is 2,3,4；C is 2,3,4,5,6；
The structural formula of the alkyl-substituted amino of C1~C4 is as shown in Equation 1,
In formula 1, R3And R4It is at least one of C1~C4 alkyl；
The halogen includes at least one of fluorine, chlorine, bromine and iodine.
2. compound CAUZS-A preparation method, comprises the following steps shown in formula described in claim 1 (I)：
1) compound shown in formula (III) is reacted in the basic conditions with compound shown in formula (IV), obtains chemical combination shown in formula (V) Thing；
2) by the deprotection base in the basic conditions of compound shown in formula (V), that is, compound CAUZS-A shown in formula (I) is obtained；
Wherein, in formula (IV) and formula (V), R1For in hydrogen, nitro, halogen, C1~C4 alkoxies and the alkyl-substituted amino of C1~C4 At least one；A is 2,3,5,6；B is 2,3,4；R5For acetyl group, benzoyl, chloracetyl, trichloro-ethoxycarbonyl and second At least one of acyl propiono；R6For at least one of chlorine, bromine and iodine；The structure of the alkyl-substituted amino of C1~C4 Formula is as shown in the formula 1.
3. compound CAUZS-B preparation method, comprises the following steps shown in formula described in claim 1 (II)：
1) compound shown in formula (VI) is reacted with compound shown in formula (VII) in the basic conditions to obtain formula (VIII) shownization Compound；
3) by deprotection obtains compound CAUZS-B shown in formula (II) in the basic conditions formula (VIII) Suo Shi.
Wherein, in formula (VI) and formula (VII), R2For hydrogen, nitro, halogen, C1~C4 alkoxies and the alkyl-substituted amino of C1~C4 At least one of；C is 2,3,4,5,6；R7For acetyl group, benzoyl, chloracetyl, trichloro-ethoxycarbonyl and acetyl propionyl At least one of base；The structural formula of the alkyl-substituted amino of C1~C4 is as shown in the formula 1.
4. the preparation method according to Claims 2 or 3, it is characterised in that：
Prepare in compound CAUZS-A method shown in the formula (I)：In step 1), reagent that the alkalescence condition uses for At least one of sodium carbonate, potassium carbonate, sodium acid carbonate, saleratus and sodium hydride；
The temperature of the reaction is 60~80 DEG C, and the time is 8~24h
In step 2), the reagent that the alkalescence condition uses is at least one in sodium methoxide, methanol ammonia, methanol first ammonia and caustic alcohol Kind；The temperature of the reaction is room temperature, and the time is 12~48h；
Step 1) and 2) in, include extraction, drying and the step of column chromatography；
Prepare in compound CAUZS-B method shown in the formula (II)：In step 1), reagent that the alkalescence condition uses for At least one of sodium carbonate, potassium carbonate, sodium acid carbonate, saleratus and sodium hydride；
The temperature of the reaction is room temperature, and the time is 8~24h；
In step 2), the reagent that the alkalescence condition uses is at least one in sodium methoxide, methanol ammonia, methanol first ammonia and caustic alcohol Kind；The temperature of the reaction is room temperature, and the time is 12~48h；
Step 1) and 2) in, include extraction, drying and the step of column chromatography.
5. the glycosyl naphthalimide derivative or its pharmaceutically acceptable salt shown in claim 1 formula (I) or formula (II) Following 1) -3) in it is any in application：
1) application in insect β-N-acetylmuramic glycanchydrolase inhibitor is prepared；
2) desinsection；
3) insecticide is prepared.
A kind of 6. insect β-N-acetylmuramic glycanchydrolase inhibitor, it is characterised in that：The active component of the inhibitor is claim 1 The glycosyl naphthalimide derivative or its pharmaceutically acceptable salt.
A kind of 7. insecticide, it is characterised in that：The active component of the insecticide is that glycosyl naphthalimide described in claim 1 derives Thing or its pharmaceutically acceptable salt.
8. insecticide according to claim 7, it is characterised in that：Described insecticide is pharmaceutically acceptable formulation；Institute Stating formulation includes missible oil, wettable powder, suspending agent, pulvis, soluble powder, aqua, water dispersible granules, fumicants, granule At least one of with seed coat agent.
A kind of 9. insecticide emulsifiable concentrate, it is characterised in that：It includes the material composition of following weight/mass percentage compositions：1~10% right It is required that the 1 glycosyl naphthalimide derivative or its pharmaceutically acceptable salt, 5~15% emulsifying agents, 0.1~1% bleeding agent Formed with surplus for solvent；
The emulsifying agent is surfactant, the surfactant include agriculture breast 0203B, 0208, GFC, OP-10 and tween- At least one of 60；
The bleeding agent includes at least one of JFC-2, TX-10, FP-T, OX-408, OX-406, N-2 and UC-12A；
The solvent is toluene and/or dimethylbenzene.
A kind of 10. insecticide wettable powder, it is characterised in that：It includes the material composition of following mass parts：15~50 parts of power Profit requires the 1 glycosyl naphthalimide derivative or its pharmaceutically acceptable salt, 10~20 parts of surfactants and 30~75 Part White Carbon black；
The surfactant include SP-408, APG-810, TA-15, AOS, NNO, MF, AEC, M4600, SP-2728 and At least one of VESTVACO.
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