CN113016805B - Application of phthalide derivatives in preventing and treating plant virus, killing bacteria, killing insects and killing mites - Google Patents
Application of phthalide derivatives in preventing and treating plant virus, killing bacteria, killing insects and killing mites 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
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Abstract
The present invention belongs to the field of pesticide technologyThe phthalide derivatives are compounds shown in a general formula.
Description
Technical Field
The invention relates to application of phthalide derivatives in the aspects of preventing and treating plant viruses, killing bacteria, killing insects and killing mites, belonging to the technical field of pesticides.
Background
The phthalide component is one of characteristic active components of plants of Umbelliferae, and mainly exists in Apium, cnidium, Eugenia, Angelica, Paeonia, and Angelica. In addition, the secondary metabolites of other plants, such as Amaryllidaceae, Apocynaceae, Gentianaceae, and some fungi and bacteria, also contain phthalides and their derivatives. They are mainly divided into monomeric and dimeric phthalides, which are commonly used as pharmaceuticals in asia, europe and north america. The first reports on phthalide appeared at the end of the 19 th century and they were identified by Ciamician and Silber as the odor component of celery essential oil. In the first half of the twentieth century, phthalides were isolated from the traditional drugs, cnidium officinale, angelica sinensis, and Laveria officinalis, which are commonly used as food seasonings.
The biological activity of the gossypol biogenesis synthesis precursor semi-gossypol in the aspects of resisting Tobacco Mosaic Virus (TMV), sterilizing and killing insects is superior to that of gossypol, wherein the activity of semi-gossypol lactone is the best. The phthalide compounds have a structure similar to that of the semi-gossypol lactone, and the research on the pesticide activity of the compounds is less at present.
Disclosure of Invention
The invention aims to provide application of phthalide derivatives in the aspects of preventing and treating plant viruses, killing bacteria, killing insects and killing mites. Wherein the phthalide derivatives are compounds with the structure shown in the following general formula:
wherein R is1、R2、R3And R4Each independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy;
r is substituted or unsubstituted phenyl, thiophene-2-yl, and the substituent of the substituted phenyl is independently selected from one or more of halogen, alkyl of C1-C6, and alkoxy of C1-C6.
The phthalide derivatives with the general formula have 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, grains, vegetables, beans and the like, and is particularly suitable for preventing and treating the tobacco mosaic virus.
The phthalide derivatives 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 Benzothiadiazole (BTH), Tiadinil (TDL), 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid (TDLA), DL-beta-aminobutyric acid (BABA), ribavirin, ningnanmycin, phenanthroindolizidine alkaloid antine 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 performance synergism and certain performance addition effects.
The phthalide derivatives with the general formula of the invention show bactericidal activity to the following 14 pathogenic bacteria: cucumber wilt, peanut brown spots, apple ring spots, 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.
The phthalide derivatives with the general formula have the activity of killing aphids, tetranychus cinnabarinus adults and diamondback moths.
The phthalide derivatives with the general formula can be directly used as an insecticidal, acaricidal and bactericidal agent, can be added with an agriculturally acceptable carrier for use, and can also be used in combination with other insecticidal, acaricidal and bactericidal agents such as tebufenpyrad, chlorfenapyr, etoxazole, fenpyroximate, pyraclostrobin and the like, and the compositions have synergistic effects and additional effects.
Detailed Description
The invention provides a phthalide derivative which is a compound shown as a general formula:
wherein R is1、R2、R3And R4Each independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy;
r is substituted or unsubstituted phenyl, thiophene-2-yl, and the substituent of the substituted phenyl is independently selected from one or more of halogen, alkyl of C1-C6, and alkoxy of C1-C6.
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.
Specific examples of halogens may be, for example: fluorine, chlorine, bromine, iodine, and the like.
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:
3-benzylidene isobenzofuran-1 (3H) -one (a);
3- (3-methylbenzylidene) isobenzofuran-1 (3H) -one (b);
3- (4-butylbenzylidene) isobenzofuran-1 (3H) -one (c);
3- (4-tert-butylbenzylidene) isobenzofuran-1 (3H) -one (d);
3- (4-methoxybenzylidene) isobenzofuran-1 (3H) -one (e);
3- (3-chlorobenzylidene) isobenzofuran-1 (3H) -one (f);
3- (4-bromobenzylidene) isobenzofuran-1 (3H) -one (g);
3- (2-bromobenzylidene) isobenzofuran-1 (3H) -one (H);
3- (thiophene-2-methylene) isobenzofuran-1 (3H) -one (i);
3-benzylidene-5-methoxyisobenzofuran-1 (3H) -one (j);
3-benzylidene-6-methylisobenzofuran-1 (3H) -one (k);
3-benzylidene-5-chloroisobenzofuran-1 (3H) -one (l);
3-benzylidene-5-fluoroisobenzofuran-1 (3H) -one (m).
The invention provides application of the phthalide derivatives in the aspect of plant virus activity resistance.
The phthalide derivatives provided by the invention have 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, grains, vegetables, beans and the like, and is particularly suitable for preventing and treating the tobacco mosaic virus. The phthalide derivatives shown in the general formula show good activity of resisting tobacco mosaic virus.
The phthalide derivatives provided by the invention can be directly used as plant virus inhibitors, can also be used together with agriculturally acceptable carriers, and can also be used together 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 interactive compositions.
In view of obtaining higher activity against plant viruses, the phthalide derivatives of the present invention are preferably selected from one or more of the following compounds:
3-benzylidene isobenzofuran-1 (3H) -one (a);
3- (3-methylbenzylidene) isobenzofuran-1 (3H) -one (b);
3- (4-butylbenzylidene) isobenzofuran-1 (3H) -one (c);
3- (4-tert-butylbenzylidene) isobenzofuran-1 (3H) -one (d);
3- (4-methoxybenzylidene) isobenzofuran-1 (3H) -one (e);
3- (3-chlorobenzylidene) isobenzofuran-1 (3H) -one (f);
3- (4-bromobenzylidene) isobenzofuran-1 (3H) -one (g);
3- (2-bromobenzylidene) isobenzofuran-1 (3H) -one (H);
3- (thiophene-2-methylene) isobenzofuran-1 (3H) -one (i);
3-benzylidene-5-methoxyisobenzofuran-1 (3H) -one (j);
3-benzylidene-6-methylisobenzofuran-1 (3H) -one (k);
3-benzylidene-5-chloroisobenzofuran-1 (3H) -one (l);
3-benzylidene-5-fluoroisobenzofuran-1 (3H) -one (m).
The invention also provides a method for resisting plant viruses by using the phthalide derivatives as plant virus inhibitors.
The invention provides the application of the phthalide derivatives in killing phytopathogen.
The phthalide derivatives provided by the invention have higher activity of killing plant pathogenic bacteria, and especially aim 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 specks and watermelon anthrax.
Particularly, the phthalide derivatives of the invention show good bactericidal activity. Wherein, the inhibition rate of the compounds a and l on the ring rot apple is up to more than 80%. The compound a and the like have good activity of killing plant pathogenic bacteria on various pathogenic bacteria such as sclerotium rot of colza, gray mold of cucumber, rice sheath blight and the like, and the inhibition rate of various bacteria reaches more than 80 percent. The compound l has applicability to various strains, has an inhibition rate of more than 85 percent on ring rot of apple and rhizoctonia cerealis, has an inhibition rate of 95.7 percent on sclerotium of rape, and has the effect equivalent to that of commercial chlorothalonil.
The phthalide derivatives provided by the invention have high insecticidal and acaricidal activity, and have high activity on one or more of diamondback moth, aphid and tetranychus cinnabarinus.
Particularly, in the phthalide derivatives, the aphid killing rate of the compounds d and f is 80% and 90% respectively under the concentration condition of 600 mu g/mL, the lethality rate of the compounds a and i to tetranychus cinnabarinus becomes 90%, and almost all compounds have good insecticidal effect on diamond back moths. Under the condition of 200 mug/mL concentration, the inhibition rate of the compounds a, d, e, f and i is still as high as 100%, and even when the concentration is reduced to 10 mug/mL, the lethality rate of the compounds a and f is still 60% and 70%.
The phthalide derivatives provided by the invention can be directly used as an insecticidal, acaricidal and bactericidal agent, can be added with an agriculturally acceptable carrier for use, and can also be used in combination with other insecticidal, acaricidal and bactericidal agents such as tebufenpyrad, chlorfenapyr, etoxazole, fenpyroximate, pyraclostrobin and the like, and the compositions have synergistic effects and additional effects.
The invention also provides a method for killing insects and mites by using the phthalide derivatives as an insecticide and acaricide.
The invention also provides a method for sterilizing by adopting the phthalide derivatives as a plant pathogenic bactericide.
The following examples and biological test results are presented 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 scabs after 3 days, and calculating the control effect.
5. In vivo therapeutic action:
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 results of the Activity test against Tobacco Mosaic Virus (TMV)
The anti-tobacco mosaic virus activity result shows that part of phthalide compounds such as e, i and m show good relative inhibition rate in three test modes of living passivation, living treatment and living protection. Wherein the activity of the compound e (three modes of in vivo inactivation, treatment activity and in vivo protection against tobacco mosaic virus are respectively (41.2 +/-4.4%, 34.4 +/-3.5%, 45.1 +/-2.7% and 500 mu g/mL), the antiviral activity of the compound i (46.4 +/-1.1%, 38.7 +/-0.5%, 42.0 +/-3.2% and 500 mu g/mL), and the antiviral activity of the compound m (40.7 +/-3.6%, 35 +/-1.8%, 34 +/-4.1% and 500 mu g/mL) is equivalent to that of commercial variegated ribavirin (39.4 +/-1.3%, 37.7 +/-0.9%, 41.2 +/-1.5% and 500 mu g/mL).
Example 2: the bactericidal activity was measured 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 m all show certain bactericidal activity on the ring rot apple germs, the vast majority is more than 50 percent, and the inhibition rate of the compounds a and l is as high as more than 80 percent. The compound a and the like have good bactericidal activity on various pathogenic bacteria such as sclerotium of colza, cucumber gray mold, rice sheath blight and the like, and the inhibition rate of various pathogenic bacteria reaches more than 80 percent. The compound l has the best bactericidal activity, has applicability to various strains, has the inhibition rate on apple ring rot and wheat sheath blight bacteria of more than 85 percent, has the inhibition rate on rape sclerotium of 95.7 percent, and has the effect equivalent to that of commercialized chlorothalonil.
Example 3: the insecticidal and acaricidal activity is measured by the following procedure:
activity assay of aphids
The test insects are normal groups of aphids (Aphis laburni Kaltenbach) and broad bean leaves fed in a laboratory. Weighing the medicines, adding 1mL of DMF for dissolving, adding two drops of Tween-20 emulsifier, adding a certain amount of distilled water, and stirring uniformly to prepare the liquid medicine with the required concentration. Soaking the leaves of broad beans with aphids (about 60) in the medicament for 5 seconds, taking out and lightly drying, sucking the redundant medicament with filter paper, then inserting the branches of the broad beans into water-absorbing sponge, covering the branches with glass covers, sealing with gauze, checking the result for 96 hours, and repeating the steps for 3 times for each compound. The control was prepared by adding the emulsifier and solvent to distilled water and stirring the mixture uniformly.
Activity test of tetranychus cinnabarinus to form mites
When the dwarf beans for experiments grow to two true leaves, plants with regular growth vigor, 4-5 square centimeters of leaf area and about 10 centimeters of plant height are selected for inoculation of insects, and the quantity of each plant is controlled to be about 60-100. And after the inoculation of the insects for 24 hours, carrying out medicament treatment. The medicament treatment adopts a plant dipping method, and the dipping time is 5 seconds. After the plants are taken out of the liquid medicine, the plants are shaken slightly to throw off the redundant liquid medicine, then the plants are moved into a water culture tank and placed at room temperature. The results were examined under binoculars 24 hours after treatment. (three replicates were averaged).
Plutella xylostella larva Activity test
The leaf dipping method proposed by the International Resistance Action Commission (IRAC) was used. 2mg of the drug sample was weighed into a 10mL beaker on an analytical balance, dissolved in 50. mu.L of dimethylformamide (analytical grade), and added with 10mL of water to prepare 200. mu.g/mL of drug solution. Dipping the cabbage leaves with straight-head ophthalmological forceps for 2-3 seconds, and throwing off residual liquid. 1 tablet at a time, 3 tablets per sample. And the samples are sequentially placed on the processing paper according to the sample marking sequence. After the liquid medicine is dried, the liquid medicine is put into a straight pipe with the length of 10cm and provided with a mark, 2-year-old plutella xylostella larvae are inoculated, and the pipe orifice is covered by gauze. The experimental treatments were placed in a standard treatment chamber and the results checked after 96 h. Each compound was repeated 3 times. The control was prepared by adding the emulsifier and solvent to distilled water and stirring the mixture uniformly.
TABLE 3 insecticidal and acaricidal activity data
The phthalide compounds have remarkable insecticidal and acaricidal effects, wherein the aphid killing rates of the compounds d and f are respectively 80% and 90% under the concentration condition of 600 mu g/mL, the lethality rates of the compounds a and i to tetranychus cinnabarinus mites are 90% under the concentration condition of 600 mu g/mL, the phthalide compounds have excellent lethality rates to diamond back moths, almost all the compounds have good insecticidal activity to diamond back moths, the lethality rates of all the compounds except the compound c are up to 100% under the concentration condition of 600 mu g/mL, and the lethality rates of the compounds a, e, d, f and i to the diamond back moths are respectively 90%, 90%, 70% and 80% under the concentration condition of 100 mu g/mL. Especially, the compounds a and f still have the killing rate of 60 percent and 70 percent on the plutella xylostella under the condition of low concentration of 10 mu g/mL.
Claims (2)
1. An application of phthalide derivatives in the aspect of preventing and treating plant viruses, plant pathogenic bacteria and plant pests and mites is disclosed, wherein the phthalide derivatives are compounds shown in a general formula:
wherein R is1、R2Is hydrogen or methyl;
R3is one of hydrogen, methoxy, fluorine and chlorine;
R4is one of hydrogen and methyl;
r is substituted or unsubstituted phenyl and thiophen-2-yl, the substituent of the substituted phenyl is independently selected from one of methyl, n-butyl, tert-butyl, methoxy, chlorine and bromine,
the plant virus is tobacco mosaic virus, the plant pathogenic bacteria are one or more of cucumber wilt, peanut brown spot, apple ring spot, tomato early blight, wheat gibberella, potato late blight, rape sclerotium, cucumber gray mold, rice sheath blight, phytophthora capsici, rice bakanae, wheat sheath blight, corn microspur and watermelon anthracnose, and the plant pest mites are diamondback moth, aphid and tetranychus cinnabarinus adult mites.
2. The phthalide derivative as claimed in claim 1, wherein the compound represented by the formula is selected from one of the compounds represented by the following formulas:
3- (3-methylbenzylidene) isobenzofuran-1 (3H) -one (b);
3- (4-butylbenzylidene) isobenzofuran-1 (3H) -one (c);
3- (4-tert-butylbenzylidene) isobenzofuran-1 (3H) -one (d);
3- (4-methoxybenzylidene) isobenzofuran-1 (3H) -one (e);
3- (3-chlorobenzylidene) isobenzofuran-1 (3H) -one (f);
3- (4-bromobenzylidene) isobenzofuran-1 (3H) -one (g);
3- (2-bromobenzylidene) isobenzofuran-1 (3H) -one (H);
3- (thiophene-2-methylene) isobenzofuran-1 (3H) -one (i);
3-benzylidene-5-methoxyisobenzofuran-1 (3H) -one (j);
3-benzylidene-6-methylisobenzofuran-1 (3H) -one (k);
3-benzylidene-5-chloroisobenzofuran-1 (3H) -one (l);
3-benzylidene-5-fluoroisobenzofuran-1 (3H) -one (m).
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