CN113016806B - Application of coumarin derivatives in preventing and treating plant viruses, killing bacteria and killing insects - Google Patents
Application of coumarin derivatives in preventing and treating plant viruses, killing bacteria and killing insects Download PDFInfo
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- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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Abstract
The invention belongs to the technical field of pesticides, and particularly relates to application of coumarin derivatives in plant virus resistance, sterilization and insect killing.
Description
Technical Field
The invention relates to application of coumarin derivatives in the aspects of plant virus prevention and control, sterilization and disinsection, belonging to the technical field of pesticides.
Background
Coumarin, the simplest member of the oxacyclic compounds known as benzo-2-pyrones, occurs naturally in plants and microorganisms. Coumarin was isolated from tonka beans (coumarouna odorata) as early as 1820. At present, nearly 1000 kinds of coumarin compounds which have been successfully isolated by human beings exist widely in metabolites of plants and microorganisms of Rutaceae, Umbelliferae, Leguminosae, Compositae, Orchidaceae, Thymelaeaceae, Solanaceae and the like. According to the types and positions of substituents on a benzene ring and pyrone, the coumarin can be classified into simple coumarin, pyranocoumarin, furocoumarin, other coumarins and the like.
The coumarin compound contains pi-pi conjugated system in its structure, so that it has rich electrons and good charge transport property. The coumarin compound can be combined with various active sites in organisms in a non-covalent interaction mode (pi-pi electron interaction, hydrogen bond, metal coordination, van der waals force and the like), so that the coumarin compound has extremely wide biological activity, such as various biological activities of sterilization, cancer resistance, virus resistance and the like.
Disclosure of Invention
The invention aims to provide application of coumarin derivatives in the aspects of plant virus prevention and control, sterilization and disinsection. Wherein the coumarin derivative is a compound with a structure shown in the following general formula:
wherein R is1、R2、R3And R4Each independently selected from one or more of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, or R2And R3Are combined into
R is substituted or unsubstituted phenyl, thiophene-3-group and phenoxy, and the substituted phenyl is shown in the formula (I):
wherein R is5、R6、R7、R8And R9Each independently selected from one or more of hydrogen, methyl, methoxy, fluoro, chloro and nitro.
The coumarin derivative has excellent plant virus resisting activity, can well inhibit tobacco mosaic virus, pepper virus, rice virus, tomato virus, sweet potato virus, melon virus, corn dwarf mosaic virus and the like, can effectively prevent and treat virus diseases of various crops such as tobacco, pepper, rice, tomato, cucurbits and vegetables, grains, vegetables, beans and the like, and is particularly suitable for preventing and treating the tobacco mosaic virus.
The coumarin derivative with the general formula can be directly used as a plant virus inhibitor, can also be added with an agriculturally acceptable carrier for use, and can also be used with other plant virus resisting agents such as diazosulfide (BTH), Tiadinil (TDL), 4-methyl-1, 2, 3-thiadiazole-5-formic acid (TDLA), DL-beta-aminobutyric acid (BABA), ribavirin, ningnanmycin, phenanthroindolizidine alkaloid antofine, bitriazole compounds XY-13 and XY-30, virus A, salicylic acid, polyhydroxy dinaphthalene and amino-oligosaccharin to form interactive compositions, and the compositions have synergistic effects and some have additive effects.
The coumarin derivative with the general formula shows bactericidal activity on the following 14 pathogenic bacteria, wherein the 14 pathogenic bacteria comprise: cucumber wilt, peanut brown spot, apple ring rot, tomato early blight, wheat scab, potato late blight, rape sclerotium, cucumber gray mold, rice sheath blight, phytophthora capsici, rice bakanae, wheat sheath blight, corn speck and watermelon anthrax.
The coumarin derivative has the activity of killing armyworm, cotton bollworm, corn borer and mosquito larva.
The coumarin derivatives with the general formula can be directly used as insecticidal bactericides, can be used together with agriculturally acceptable carriers, and can also be combined with other insecticidal bactericides such as chlorfenapyr, chlorantraniliprole, pyraclostrobin and the like, and the compositions have synergistic effects and additive effects.
Detailed Description
The invention provides a coumarin derivative, which is a compound shown in a general formula:
wherein R is1、R2、R3And R4Each independently selected from one or more of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, or R2And R3Are combined into
R is substituted or unsubstituted phenyl, thiophene-3-group and phenoxy, and the substituted phenyl is shown in the formula (I):
wherein R is5、R6、R7、R8And R9Each independently selected from one or more of hydrogen, methyl, methoxy, fluoro, chloro and nitro.
In the present invention, specific examples of the alkyl group of C1 to C6 may be, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, and the like.
The alkoxy group having C1 to C6 may be an alkoxy group formed by the above-mentioned specific examples of the alkyl group satisfying the definition of 1 to 6 carbon atoms.
In a preferred embodiment of the present invention, the compound represented by the general formula (xxxv) is one selected from the group consisting of compounds represented by the following formulae:
5-isopropyl-3- (3-methoxyphenyl) -8-methyl-2H-chroman-2-one (a);
5-isopropyl-8-methyl-3-p-tolyl-2H-chroman-2-one (b);
5-isopropyl-8-methyl-3-o-tolyl-2H-chroman-2-one (c);
5-isopropyl-3- (3-methoxyphenyl) -8-methyl-2H-chroman-2-one (d);
5-isopropyl-8-methyl-3- (3, 4, 5-trimethoxyphenyl) -2H-chroman-2-one (e);
5-isopropyl-8-methyl-3-phenoxy-2H-chroman-2-one (f);
3- (2-fluorophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (g);
3- (4-bromophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (H);
3- (2, 4-dichlorophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (i);
5-isopropyl-8-methyl-3- (4-nitrophenyl) -2H-chroman-2-one (j);
5-isopropyl-8-methyl-3- (thiophene-3) -2H-chroman-2-one (k);
6, 8-di-tert-butyl-p-tolyl-2H-chroman-2-one (l);
6, 8-di-tert-butyl-3- (3, 4, 5-methoxyphenyl) -2H-chroman-2-one (m);
6, 8-di-tert-butyl-3- (4-methoxybenzene) -2H-chroman-2-one (n);
6, 8-di-tert-butyl-3- (2-fluorophenyl) -2H-chroman-2-one (o);
8-methoxy-3- (3, 4, 5-trimethoxyphenyl) -2H-chroman-2-one (p);
3- (3, 4, 5-trimethoxyphenyl) -2H-benzo [ g ] chroman-2-one (q).
The invention provides application of the coumarin derivatives in the aspect of plant virus activity resistance.
The coumarin derivative provided by the invention has excellent plant virus resistance activity, can well inhibit tobacco mosaic virus, pepper virus, rice virus, tomato virus, sweet potato virus, melon virus, maize dwarf mosaic virus and the like, can effectively prevent and treat virus diseases of various crops such as tobacco, pepper, rice, tomato, cucurbits and vegetables, grains, vegetables, beans and the like, and is particularly suitable for preventing and treating the tobacco mosaic virus. The coumarin derivative shown in the general formula shows good activity of resisting tobacco mosaic virus.
The coumarin derivative provided by the invention can be directly used as a plant virus inhibitor, can also be used by adding an agriculturally acceptable carrier, and can also be used with other plant virus resisting agents such as diazosulfide (BTH), Tiadinil (TDL), 4-methyl-1, 2, 3-thiadiazole-5-formic acid (TDLA), DL-beta-aminobutyric acid (BABA), ribavirin, ningnanmycin, phenanthroindolizidine alkaloid antofine, bitriazole compounds XY-13 and XY-30, virus A, salicylic acid, polyhydroxy dinaphthalene aldehyde and amino-oligosaccharin to form an interactive composition.
In view of obtaining higher activity against plant viruses, the coumarin derivative is preferably selected from one or more of the following compounds:
5-isopropyl-3- (3-methoxyphenyl) -8-methyl-2H-chroman-2-one (a);
5-isopropyl-8-methyl-3-p-tolyl-2H-chroman-2-one (b);
5-isopropyl-8-methyl-3-o-tolyl-2H-chroman-2-one (c);
5-isopropyl-3- (3-methoxyphenyl) -8-methyl-2H-chroman-2-one (d);
5-isopropyl-8-methyl-3- (3, 4, 5-trimethoxyphenyl) -2H-chroman-2-one (e);
5-isopropyl-8-methyl-3-phenoxy-2H-chroman-2-one (f);
3- (2-fluorophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (g);
3- (4-bromophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (H);
3- (2, 4-dichlorophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (i);
5-isopropyl-8-methyl-3- (4-nitrophenyl) -2H-chroman-2-one (j);
5-isopropyl-8-methyl-3- (thiophene-3) -2H-chroman-2-one (k);
6, 8-di-tert-butyl-p-tolyl-2H-chroman-2-one (l);
6, 8-di-tert-butyl-3- (3, 4, 5-methoxyphenyl) -2H-chroman-2-one (m);
6, 8-di-tert-butyl-3- (4-methoxybenzene) -2H-chroman-2-one (n);
6, 8-di-tert-butyl-3- (2-fluorophenyl) -2H-chroman-2-one (o);
8-methoxy-3- (3, 4, 5-trimethoxyphenyl) -2H-chroman-2-one (p);
3- (3, 4, 5-trimethoxyphenyl) -2H-benzo [ g ] chroman-2-one (q).
The invention also provides a method for resisting plant viruses by using the coumarin derivatives as plant virus inhibitors.
The invention provides the application of the coumarin derivatives in killing plant pathogenic bacteria.
The coumarin derivative provided by the invention has higher bactericidal activity, and particularly aims at one or more of pathogenic bacteria causing cucumber wilt, peanut brown spots, apple ring lines, tomato early blight, wheat scab, potato late blight, rape sclerotium, cucumber gray mold, rice sheath blight, phytophthora capsici, rice bakanae, wheat sheath blight, corn speckles and watermelon anthracnose.
Wherein, the compounds a to g and i to n have good bactericidal activity on the sclerotium rolfsii, which shows that the coumarin compounds have unique curative effect on the sclerotium rolfsii. f and g have bactericidal activity on various fungi such as sclerotium of colza, gray mold of cucumber, rice sheath blight, etc., especially have very good effects on wheat sheath blight, the inhibition rates are respectively as high as 92.6% and 92.2%, and the inhibition rates are equivalent to commercialized chlorothalonil.
The coumarin derivative provided by the invention has high insecticidal activity, and has high insecticidal activity on one or more of armyworm, cotton bollworm, corn borer and mosquito larva.
Wherein, the lethality of the armyworm of the compounds f and i is 100% under the concentration condition of 200 mug/mL, the concentration is reduced to 100 mug/mL, and the lethality of i to the armyworm is still 100%. The compound i still has the best activity for the cotton bollworm and the corn borer, the insecticidal rate is 100 percent under the condition of 600/200 mu g/mL concentration, and the insecticidal rate can still reach 50 percent for the cotton bollworm even if the concentration is reduced to 100 mu g/mL.
The coumarin derivative provided by the invention can be directly used as an insecticide and bactericide, can be added with an agriculturally acceptable carrier, and can also be combined with other insecticide and bactericide such as chlorfenapyr, chlorantraniliprole, pyraclostrobin and the like, and the compositions have synergistic effect and additive effect.
The invention also provides a method for killing insects by using the coumarin derivative as an insecticide.
The invention also provides a method for sterilizing by using the coumarin derivative as a bactericide.
The following examples and biological test results are provided to further illustrate the invention and are not meant to limit the invention.
Example 1: the activity against tobacco mosaic virus was determined by the following procedure:
1. virus purification and concentration determination:
performed with reference to the specification of tobacco mosaic virus SOP compiled by the institute of life, institute of elements of south kayak university. The virus crude extract is centrifuged by 2 times of polyethylene glycol, the concentration is measured, and then the virus crude extract is refrigerated at 4 ℃ for standby.
2. Compound solution preparation:
after weighing, dissolving the original medicine with DMF to prepare a mother solution with the concentration of 1 multiplied by 105 mug/mL, and then diluting the mother solution with an aqueous solution containing 1 thousandth of Tween 80 to the required concentration; the ningnanmycin preparation is directly diluted by adding water.
3. The Shanxi tobacco leaves with the proper age are inoculated by rubbing and washed by running water, and the virus concentration is 10 mug/mL. Cutting off after drying, cutting along the vein of the leaf, soaking the left and right half leaves in 1 ‰ of expectorant water and medicinal preparation respectively, taking out after 30 min, performing moisture-keeping culture at suitable illumination temperature, repeating for 1 time and 3 times for each 3 leaves. And recording the number of the disease spots after 3 days, and calculating the control effect.
4. The protection effect of the living body is as follows:
selecting 3-5 leaf-period Saxisi tobacco with uniform growth, spraying the whole plant, repeating for 3 times, and setting 1 ‰ Tween 80 aqueous solution as control. After 24 hours, the leaf surfaces are scattered with carborundum (500 meshes), the virus liquid is dipped by a writing brush, the whole leaf surfaces are lightly wiped for 2 times along the branch vein direction, the lower parts of the leaf surfaces are supported by palms, the virus concentration is 10 mu g/mL, and the inoculated leaf surfaces are washed by running water. And recording the number of the disease spots after 3 days, and calculating the control effect.
5. Therapeutic action in vivo:
selecting 3-5 leaf-stage Saxismoke with uniform growth vigor, inoculating virus with whole leaf of writing brush at a virus concentration of 10 μ g/mL, and washing with running water after inoculation. After the leaves are harvested, the whole plant is sprayed with the pesticide, the treatment is repeated for 3 times, and a 1 per mill tween 80 aqueous solution is set for comparison. After 3 days, the number of lesions was recorded and the control effect was calculated.
6. Inactivation of living body
Selecting 3-5 leaf-period Saxismoke with uniform growth, mixing the preparation with virus juice of the same volume, inactivating for 30 min, performing friction inoculation with virus concentration of 20 μ g/mL, washing with running water after inoculation, repeating for 3 times, and setting Tween 80 water solution of 1 ‰ as reference. The number of lesions was counted after 3 days, and the results were calculated.
Inhibition (%) < percent [ (control number of scorched spots-number of treated scorched spots)/control number of scorched spots ]. times.100%
TABLE 1 test results for Tobacco Mosaic Virus (TMV) resistance
Most of coumarin compounds have inhibiting effect on tobacco mosaic virus in three modes of living body passivation, living body treatment and living body protection, and b, e, g, l and n have excellent anti-TMV activity in three modes of living body passivation, living body treatment and living body protection, and have equivalent effect to commercial ribavirin. Under the condition of 500 mu g/mL concentration, the relative inhibition rates of three modes of the compound e are 53.4 +/-2.3%, 47.0 +/-3.2% and 44.5 +/-0.4%, under the condition of 100 mu g/mL concentration, the relative inhibition rates are 20.2 +/-0.8, 12.9 +/-2.0 and 16.1 +/-1.0, the effect is equivalent to that of commercial ribavirin, and the relative inhibition rates of the compound n under three modes of in-vivo inactivation, in-vivo treatment and in-vivo protection are 49.2 +/-1.1%, 53.3 +/-3.7% and 41.5 +/-2.9%, the activity is higher than that of ribavirin, and particularly, the effect of the therapeutic activity is equivalent to that of commercial ningnanmycin.
Example 2: the bactericidal activity was determined by the following procedure:
taking tomato early blight as an example, other bacteria can be replaced.
In vitro test method: inoculating the tomato early blight bacteria to PDA culture medium, culturing for 7 days, preparing bacterial dish with diameter of 4cm at colony edge with puncher, inoculating to PDA culture medium containing 50 μ g/ml and no medicine, culturing for 4 days, measuring colony diameter, and comparing with control to calculate the inhibition percentage of the medicine.
TABLE 2 in vitro bactericidal Activity test results
The compounds a to g and i to n have good bactericidal activity on rape sclerotium, which shows that the coumarin compounds have unique curative effect on the rape sclerotium. f and g have bactericidal activity on various fungi such as sclerotium of colza, gray mold of cucumber, rice sheath blight, etc., especially have very good effects on wheat sheath blight, the inhibition rates are respectively as high as 92.6% and 92.2%, and the inhibition rates are equivalent to commercialized chlorothalonil.
Example 3: the insecticidal activity is measured by the following procedure:
activity test of armyworm, cotton bollworm and corn borer
Leaf soaking method. After the required concentration is prepared, soaking leaves with the diameter of about 5-6cm into the liquid medicine for 5-6 seconds, taking out, putting on absorbent paper for airing, putting in a designated culture dish, inoculating 10-head 3-year larvae, putting in an insect-raising room at 27 +/-1 ℃ for observing for 3-4 days, and then checking the result.
Activity assay for mosquito larvae
Experimental method of mosquito larvae: culex pipiens light subspecies, normal population raised indoors. Weighing about 5mg of test compound into a penicillin drug bottle, adding 5mL of acetone (or a suitable solvent), and shaking to dissolve to obtain 1000 μ g/mL of mother liquor. 0.5mL of mother liquor is transferred and added into a 100mL beaker filled with 89.9mL of water, 10 heads of young mosquito larvae of 4 years old are selected and poured into the beaker together with 10mL of feeding liquid, and the concentration of the liquid medicine is 5 mug/mL. The sample is placed in a standard processing chamber, and the result is checked for 24 h.
An aqueous solution containing 0.5mL of the experimental solvent was used as a blank.
TABLE 3 insecticidal bioassay Activity data
The coumarin compound has a remarkable insecticidal effect, wherein the lethality of the armyworm of the compounds f and i is 100% under the concentration condition of 200 mu g/mL, the concentration is reduced to 100 mu g/mL, and the lethality of i to the armyworm is still 100%. The compound i still has the best activity for the cotton bollworm and the corn borer, the insecticidal rate is 100 percent under the condition of 600/200 mu g/mL concentration, and the insecticidal rate can still reach 50 percent for the cotton bollworm even if the concentration is reduced to 100 mu g/mL.
Claims (4)
1. The application of coumarin derivatives in preventing and treating plant viruses, plant pathogenic bacteria and pests is disclosed, wherein the coumarin derivatives are compounds shown in a general formula:
wherein R is1Is one of methyl, tertiary butyl and methoxyl;
R2is hydrogen, R3Is one of hydrogen and tert-butyl, or R2And R3Are combined into
R4Is one of hydrogen and isopropyl;
r is substituted phenyl, thiophene-3-group and phenoxy, and the substituted phenyl is shown in a formula (I):
wherein R is5Is one of hydrogen, methyl, fluorine and chlorine; r6Is one of hydrogen and methoxy; r7Is one of hydrogen, methyl, methoxyl, chlorine, bromine and nitryl; r 8Is one of hydrogen and methoxy; r9Is hydrogen and R5～R8At least one is not hydrogen; the plant pathogenic bacteria are one or more of plant pathogenic bacteria causing cucumber wilt, peanut brown spots, apple ring lines, tomato early blight, wheat scab, potato late blight, rape sclerotium, rice sheath blight, phytophthora capsici, rice bakanae, wheat sheath blight, corn speckles and watermelon anthrax.
2. The application of the coumarin derivative in the aspects of preventing and treating plant viruses, killing bacteria and killing insects according to claim 1, wherein the compound shown in the general formula is one of the compounds shown in the following formula:
5-isopropyl-3- (3-methoxyphenyl) -8-methyl-2H-chroman-2-one (a);
5-isopropyl-8-methyl-3-p-tolyl-2H-chroman-2-one (b);
5-isopropyl-8-methyl-3-o-tolyl-2H-chroman-2-one (c);
5-isopropyl-8-methyl-3- (3, 4, 5-trimethoxyphenyl) -2H-chroman-2-one (e);
5-isopropyl-8-methyl-3-phenoxy-2H-chroman-2-one (f);
3- (2-fluorophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (g);
3- (4-bromophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (H);
3- (2, 4-dichlorophenyl) -5-isopropyl-8-methyl-2H-chroman-2-one (i);
5-isopropyl-8-methyl-3- (4-nitrophenyl) -2H-chroman-2-one (j);
5-isopropyl-8-methyl-3- (thiophene-3) -2H-chroman-2-one (k);
6, 8-di-tert-butyl-p-tolyl-2H-chroman-2-one (l);
6, 8-di-tert-butyl-3- (3, 4, 5-methoxyphenyl) -2H-chroman-2-one (m);
6, 8-di-tert-butyl-3- (4-methoxybenzene) -2H-chroman-2-one (n);
6, 8-di-tert-butyl-3- (2-fluorophenyl) -2H-chroman-2-one (o);
8-methoxy-3- (3, 4, 5-trimethoxyphenyl) -2H-chroman-2-one (p);
3- (3, 4, 5-trimethoxyphenyl) -2H-benzo [ g ] chroman-2-one (q).
3. Use according to claim 1, against a plant virus which is tobacco mosaic virus.
4. The use according to claim 1, which is directed against insects being one or more of armyworm, Helicoverpa armigera, Sesamia zeae and mosquito larvae.
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