CN112624970B - Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization - Google Patents
Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization Download PDFInfo
- Publication number
- CN112624970B CN112624970B CN201910902385.3A CN201910902385A CN112624970B CN 112624970 B CN112624970 B CN 112624970B CN 201910902385 A CN201910902385 A CN 201910902385A CN 112624970 B CN112624970 B CN 112624970B
- Authority
- CN
- China
- Prior art keywords
- oxide
- quinoline
- phenylquinoline
- methyl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention belongs to the technical field of pesticides, and particularly relates to application of 8-site aryl-substituted quinoline nitrogen oxide in plant virus resistance and sterilization, wherein the 8-site aryl-substituted quinoline nitrogen oxide derivative is a compound shown in a formula (I).
Description
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to application of 8-site aryl substituted quinoline nitric oxide in plant virus resistance and sterilization.
Background
Quinoline is an important fine chemical raw material and is mainly used for synthesizing medicines, pesticides, dyes and various chemical auxiliaries. Many quinoline compounds are important medical intermediates, and the quinoline is mainly used for synthesizing antimalarial drugs, such as malaquine, chloroquine phosphate, and aminophenol quinoline; the antipyretic analgesic drug, cinchophene; the medicines for resisting amebiasis, such as quiiodumine, chloroiodoquine, diiodoquine, etc. Many substituted quinoline nitroxides are important drugs, such as 4-amino-5-nitroquinoline nitroxide which has the function of inhibiting tumor growth, and methylquinoline nitroxide and 4-nitro-3-chloroquinoline derivatives thereof have remarkable antibacterial and antifungal effects.
Many derivatives of quinoline are important pesticide varieties, such as 7-chloroquinoline nitrogen oxide which can be used as a herbicide for broadleaf weeds in grain planting; the substituted 8-aminoquinoline has phytotoxin activity and can be used for preparing herbicides; quinoline ester of carbamic acid, quinoline-8-carboxylic acid derivative and salt thereof have good insecticidal activity; the copper salt of 8-hydroxyquinoline is a very effective bactericide, and the quinoxyfen is also called fast nophene, is a quinoline fungicide newly introduced by the Yinong company of Dow in the United states in recent years, belongs to phenoxy quinoline bactericides, and can play a role in protecting the fungicide.
Disclosure of Invention
The invention provides an application of 8-position aryl substituted quinoline nitrogen oxide derivatives in the aspects of plant virus resistance and sterilization, wherein the 8-position aryl substituted quinoline nitrogen oxide derivatives are compounds shown in a formula (I):
wherein R is 1 、R 2 、R 3 、R 4 、R 5 And R 6 Each independently selected from one or more of hydrogen, halogen, phenyl, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkoxycarbonyl, or R 2 And R 3 Closed ring is
R is substituted or unsubstituted phenyl, 1-naphthyl and 2-naphthyl, and the substituent of the substituted phenyl is independently selected from one or more of halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, trifluoromethyl, nitro, phenyl and C2-C6 alkoxycarbonyl.
The 8-position aryl substituted quinoline nitrogen oxide derivative of the general formula (I) has plant virus resisting 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, melon and vegetable, grain, vegetable, bean and the like, and is particularly suitable for preventing and treating the tobacco mosaic virus diseases. The 8-position aryl substituted quinoline nitrogen oxide derivative shown in the general formula (I) shows good activity against Tobacco Mosaic Virus (TMV).
The 8-position aryl substituted quinoline nitrogen oxide derivative of the general formula (I) shows bactericidal activity on 14 plant pathogenic bacteria causing 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 leonian, rice bakanae disease, wheat sheath blight, corn microspore and watermelon anthracnose.
Detailed Description
The invention provides an 8-bit aryl substituted quinoline nitrogen oxide derivative, wherein the 8-bit aryl substituted quinoline nitrogen oxide derivative is a compound shown in a formula (I):
wherein R is 1 、R 2 、R 3 、R 4 、R 5 And R 6 Each independently selected from one or more of hydrogen, halogen, phenyl, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkoxycarbonyl, or R 2 And R 3 Closed ring is
R is substituted or unsubstituted phenyl, 1-naphthyl and 2-naphthyl, and the substituent of the substituted phenyl is independently selected from one or more of halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, trifluoromethyl, nitro, phenyl and C2-C6 alkoxycarbonyl;
in the present invention, specific examples of the alkyl group of C1 to C6 may be, for example: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, and the like;
the C1-C6 alkoxy group 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;
the alkoxycarbonyl group having 2 to 6 carbon atoms may be an alkoxycarbonyl group formed by the above-mentioned specific examples of the alkyl group satisfying the definition of 2 to 6 carbon atoms;
preferably, R 1 、R 2 、R 3 、R 4 、R 5 And R 6 Each independently selected from hydrogen, F, cl, br, I, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-pentylButoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, phenyl, methoxycarbonyl, ethoxy, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, or R 2 And R 3 Is closed by a ring of
Preferably, R is substituted or unsubstituted phenyl, 1-naphthyl, 2-naphthyl; the substituents of the substituted phenyl are independently selected from one or more of hydrogen, F, cl, br, I, cyano, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, trifluoromethyl, nitro, phenyl, methoxycarbonyl, ethoxy, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl and n-pentoxycarbonyl;
in a preferred embodiment of the present invention, the compound represented by formula (I) is one selected from compounds represented by the following formulae:
8-phenylquinoline-1-oxide (I-aa);
6-fluoro-8-phenylquinoline-1-oxide (I-ba);
6-chloro-8-phenylquinoline-1-oxide (I-ca);
6-bromo-8-phenylquinoline-1-oxide (I-da);
6-methyl-8-phenylquinoline-1-oxide (I-ea);
6-methoxy-8-phenylquinoline-1-oxide (I-fa);
6-methoxycarbonyl-8-phenylquinoline-1-oxide (I-ga);
2-methyl-8-phenylquinoline-1-oxide (I-ha);
2, 8-diphenylquinoline-1-oxide (I-ia);
4-methyl-8-phenylquinoline-1-oxide (I-ja);
3-chloro-8-phenylquinoline-1-oxide (I-ka);
5-chloro-8-phenylquinoline-1-oxide (I-la);
7-chloro-8-phenylquinoline-1-oxide (I-ma);
2, 6-dimethyl-8-phenylquinoline-1-oxide (I-na);
7-chloro-2-methyl-8-phenylquinoline-1-oxide (I-oa);
6-methoxy-2-methyl-8-phenylquinoline-1-oxide (I-pa);
4-chloro-6-fluoro-8-phenylquinoline-1-oxide (I-qa);
4-phenylphenanthridine-5-oxide (I-ra);
8- (4-fluorophenyl) quinoline-1-oxide (I-ab);
8- (4-chlorophenyl) quinoline-1-oxide (I-ac);
8- (4-bromophenyl) quinoline-1-oxide (I-ad);
8- (4-methylphenyl) quinoline-1-oxide (I-ae);
8- (4-tert-butylphenyl) quinoline-1-oxide (I-af);
8- ([ 1,1' -diphenyl ] -4-) quinoline-1-oxide (I-ag);
8- (4-cyanophenyl) quinoline-1-oxide (I-ah);
8- (4-trifluoromethylphenyl) quinoline-1-oxide (I-ai);
8- (4-methoxycarbonylphenyl) quinoline-1-oxide (I-aj);
8- (2-chlorophenyl) quinoline-1-oxide (I-ak);
8- (3-chlorophenyl) quinoline-1-oxide (I-al);
8- (3-methoxyphenyl) quinoline-1-oxide (I-am);
8- (3-nitrophenyl) quinoline-1-oxide (I-an);
8- (3-trifluoromethylphenyl) quinoline-1-oxide (I-ao);
8- (3, 4-dichlorophenyl) quinoline-1-oxide (I-ap);
8- (3, 5-difluorophenyl) quinoline-1-oxide (I-aq);
8- (3, 4, 5-trichlorophenyl) quinoline-1-oxide (I-ar);
8- (naphthalen-2-yl) quinoline-1-oxide (I-as).
The invention provides application of the 8-site aryl substituted quinoline nitrogen oxide derivative in the aspect of plant virus resisting activity.
The 8-aryl substituted quinoline nitrogen oxide 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, grains, vegetables, beans and the like, and is particularly suitable for preventing and treating the tobacco mosaic virus diseases. The 8-position aryl substituted quinoline nitrogen oxide derivative shown in the general formula (I) shows good activity against Tobacco Mosaic Virus (TMV).
From the viewpoint of obtaining higher anti-plant virus activity, the 8-position aryl-substituted quinoline nitrogen oxide derivative of the present invention is preferably selected from one or more of the following compounds:
8-phenylquinoline-1-oxide (I-aa);
6-fluoro-8-phenylquinoline-1-oxide (I-ba);
6-chloro-8-phenylquinoline-1-oxide (I-ca);
6-bromo-8-phenylquinoline-1-oxide (I-da);
6-methyl-8-phenylquinoline-1-oxide (I-ea);
6-methoxy-8-phenylquinoline-1-oxide (I-fa);
6-methoxycarbonyl-8-phenylquinoline-1-oxide (I-ga);
2-methyl-8-phenylquinoline-1-oxide (I-ha);
2, 8-diphenylquinoline-1-oxide (I-ia);
4-methyl-8-phenylquinoline-1-oxide (I-ja);
3-chloro-8-phenylquinoline-1-oxide (I-ka);
5-chloro-8-phenylquinoline-1-oxide (I-la);
7-chloro-8-phenylquinoline-1-oxide (I-ma);
2, 6-dimethyl-8-phenylquinoline-1-oxide (I-na);
7-chloro-2-methyl-8-phenylquinoline-1-oxide (I-oa);
6-methoxy-2-methyl-8-phenylquinoline-1-oxide (I-pa);
4-chloro-6-fluoro-8-phenylquinoline-1-oxide (I-qa);
4-phenylphenanthridine-5-oxide (I-ra);
8- (4-fluorophenyl) quinoline-1-oxide (I-ab);
8- (4-chlorophenyl) quinoline-1-oxide (I-ac);
8- (4-bromophenyl) quinoline-1-oxide (I-ad);
8- (4-methylphenyl) quinoline-1-oxide (I-ae);
8- (4-tert-butylphenyl) quinoline-1-oxide (I-af);
8- ([ 1,1' -diphenyl ] -4-) quinoline-1-oxide (I-ag);
8- (4-cyanophenyl) quinoline-1-oxide (I-ah);
8- (4-trifluoromethylphenyl) quinoline-1-oxide (I-ai);
8- (4-methoxycarbonylphenyl) quinoline-1-oxide (I-aj);
8- (2-chlorophenyl) quinoline-1-oxide (I-ak);
8- (3-chlorophenyl) quinoline-1-oxide (I-al);
8- (3-methoxyphenyl) quinoline-1-oxide (I-am);
8- (3-nitrophenyl) quinoline-1-oxide (I-an);
8- (3-trifluoromethylphenyl) quinoline-1-oxide (I-ao);
8- (3, 4-dichlorophenyl) quinoline-1-oxide (I-ap);
8- (3, 5-difluorophenyl) quinoline-1-oxide (I-aq);
8- (3, 4, 5-trichlorophenyl) quinoline-1-oxide (I-ar);
8- (naphthalen-2-yl) quinoline-1-oxide (I-as).
The invention provides application of the 8-site aryl substituted quinoline nitrogen oxide derivative in the aspect of preventing and treating plant fungal diseases.
The 8-position aryl substituted quinoline nitrogen oxide derivative provided by the invention has higher bactericidal activity, and particularly aims at one or more of pathogenic bacteria causing cucumber wilt, peanut brown spot, apple ring spot, tomato early blight, wheat scab, potato late blight, rape sclerotium, cucumber gray mold, rice sheath blight, phytophthora capsici, rice bakanae, wheat sheath blight, corn microspore and watermelon anthrax.
Particularly, the 8-site aryl substituted quinoline nitrogen oxide derivative shows good bactericidal activity, the bacteriostatic activity of most compounds to ring rot apple is more than 60% at the concentration of 50mg/L, and the bacteriostatic activity of I-ac, I-af, I-ag, I-ai, I-aj, I-ak, I-al, I-ao, I-ap, I-aq, I-ar and I-as to more than 10 plant pathogenic bacteria at the concentration of 50mg/L is more than 60%, even the bacteriostatic activity to part of plant pathogenic bacteria reaches 100% at the concentration of 50mg/L, and the in-vitro bacteriostatic activity of I-ac, I-ai and I-ap to 14 common plant pathogenic bacteria tested at the concentration of 50mg/L is equivalent to that of commercial variety chlorothalonil.
Wherein the EC of the compound I-ac on sclerotium of rape 50 The EC for Compound I-af on sclerotia of Brassica napus with a value of 7.2762 50 EC of 9.9752 for Compound I-ag against sclerotium rolfsii, botrytis cinerea and Rhizoctonia solani 50 The values are 6.1495, 9.9081 and 8.5903 respectively, and the EC of the compound I-ai on Gibberella tritici, potato late blight, rape sclerotium and cucumber gray mold 50 The values are 7.6846, 9.3864, 9.7573 and 8.4731 respectively, the EC of the compounds I-ap on Gibberella tritici and Sclerotinia sclerotiorum 50 Values of 8.8075 and 6.5983, respectively, EC of Compounds I-aq on Gibberella tritici and sclerotia brassicae 50 Values of 9.7188 and 8.6336, respectively, EC of Compound I-ag against Gibberella tritici, sclerotinia sclerotiorum, botrytis cinerea and Rhizoctonia solani 50 The values were 9.2489, 1.4667, 9/3255 and 7.4742, respectively.
The following examples are intended to further illustrate the invention but are not intended 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 according to the tobacco mosaic virus SOP specifications compiled by the institute of elements institute of university, south kayaki. 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 along the midleaf vein, soaking the left and right half leaves in 1 ‰ warm water and medicinal preparation for 30min, culturing under proper illumination temperature for 1 time, and repeating for 3 times. And recording the number of the scabs after 3 days, and calculating the control effect.
4. In vitro effect:
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. Collecting, cutting along the midleaf vein, soaking the left and right half leaves in 1 ‰ expectoration water and medicinal preparation respectively, taking out after 30min, performing moisture-keeping culture at suitable illumination temperature, repeating for 1 time and 3 times for 3 leaves. And recording the number of the disease spots after 3 days, and calculating the control effect.
5. Protection of living body:
selecting 3-5 leaf-stage Saxiyan with uniform growth, spraying the whole plant, repeating each treatment 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 rubbed 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.
6. Therapeutic action in vivo:
selecting 3-5 leaf-stage Shanxi tobacco with uniform growth vigor, inoculating virus with whole leaf of writing brush, wherein the virus concentration is 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 the scabs is recorded, and the control effect is calculated.
7. 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 30min, 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 (%) = [ (control number of scorched spots-number of treated scorched spots)/control number of scorched spots ]. Times.100%
TABLE 1 test results of the activity of the compounds against Tobacco Mosaic Virus (TMV)
The compounds all showed certain anti-TMV activity. Wherein the anti-TMV activity of the compounds I-ac, I-ak, I-al, I-ar and I-as is better than that of ribavirin (38.1 +/-1.2, 37.6 +/-0.8, 39.4 +/-1.8 and 500mg/L of the three modes of inhibition activity of inactivation, biotherapy and protection of the ribavirin in vivo) at the concentration of 500mg/L, and the anti-TMV activity of the compounds I-aa, I-ca and I-aj is equivalent to that of ribavirin (11.5 +/-0.7, 14.0 +/-2.3, 12.6 +/-0.5 and 100mg/L of the three modes of inhibition activity of inactivation, biotherapy and protection of the ribavirin in vivo) at the concentration of 100 mg/L.
Example 2: the bactericidal activity was determined by the following procedure:
for example, tomato early blight can be replaced by other bacteria.
In vitro test method: inoculating the pathogenic bacteria to PDA culture medium, culturing for 7 days, preparing bacterial dish with diameter of 4cm at colony edge, inoculating to PDA culture medium containing 50mg/L and no medicine, culturing for 4 days, measuring colony diameter, and comparing with control to calculate the inhibition percentage of the medicine.
Table 2 results of the bacteriostatic activity test of the compounds
The bacteriostatic activity of most compounds on ring rot apple is more than 60% under the concentration of 50mg/L, and the bacteriostatic activity of I-ac, I-af, I-ag, I-ai, I-aj, I-ak, I-al, I-ao, I-ap, I-aq, I-ar and I-as on more than 10 plant pathogenic bacteria under the concentration of 50mg/L is more than 60%, even the bacteriostatic activity on part of plant pathogenic bacteria reaches 100% under the concentration of 50mg/L, and the in vitro bacteriostatic activity of I-ac, I-ai and I-ap on 14 common plant pathogenic bacteria tested under the concentration of 50mg/L is equivalent to the activity of commercial variety chlorothalonil.
Wherein the EC of the compound I-ac on sclerotium of colza 50 The EC for Compound I-af on sclerotia of Brassica napus with a value of 7.2762 50 EC of 9.9752 for Compound I-ag against sclerotium rolfsii, botrytis cinerea and Rhizoctonia solani 50 The values are 6.1495, 9.9081 and 8.5903 respectively, and the EC of the compound I-ai on Gibberella tritici, potato late blight, rape sclerotium and cucumber gray mold 50 Values of 7.6846, 9.3864, 9.7573 and 8.4731, respectively, the EC of the compounds I-ap on Gibberella tritici and Sclerotinia sclerotiorum 50 Values of 8.8075 and 6.5983, respectively, EC of Compounds I-aq on Gibberella tritici and sclerotia brassicae 50 The values are 9.7188 and 8.6336, respectively, and the EC of the compound I-ag for Gibberella tritici, sclerotinia sclerotiorum, botrytis cinerea and Rhizoctonia solani 50 The values were 9.2489, 1.4667, 9/3255 and 7.4742, respectively.
TABLE 3 test results of bacteriostatic activity of compound I-ac and EC thereof 50 Value of
TABLE 4 test results of bacteriostatic activity of compound I-af and EC thereof 50 Value of
TABLE 5 test results of bacteriostatic activity of compound I-ag and its EC 50 Value of
TABLE 6 test results of antibacterial activity of compound I-ai and its EC 50 Value of
TABLE 7 antibacterial activity test results of compound I-ap and EC thereof 50 Value of
TABLE 8 antibacterial activity test results of compound I-aq and EC thereof 50 Value of
TABLE 9 bacteriostatic Activity of Compound I-arResults of sexual tests and their EC 50 Value of
Claims (2)
1. An application of 8-position aryl substituted quinoline nitrogen oxide derivatives in the aspects of resisting plant viruses and preventing and treating plant fungal diseases, wherein the 8-position aryl substituted quinoline nitrogen oxide derivatives are compounds shown in a formula (I):
wherein R is 1 Selected from hydrogen, methyl, phenyl, R 2 Selected from hydrogen and chlorine atoms, R 3 Selected from hydrogen, chlorine atoms, methyl radicals, R 4 Hydrogen of choice, R 5 Selected from halogen, methyl, methoxy, methoxycarbonyl, R 6 Selected from chlorine atoms, or R 2 And R 3 Closed ring is
R is substituted or unsubstituted phenyl, the substituent of the substituted phenyl is selected from halogen, cyano, phenyl, n-butyl, trifluoromethyl, nitro and methoxycarbonyl, and R is also 2-naphthyl;
the plant virus targeted by the application is tobacco mosaic virus;
the application aims at plant fungi which are one or more of plant pathogenic bacteria causing 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.
2. The use of the 8-aryl substituted quinoline nitroxide derivatives as claimed in claim 1 for resisting plant viruses and controlling plant fungal diseases, wherein the compound represented by formula (I) is one selected from the compounds represented by the following formulae:
8-phenylquinoline-1-oxide (I-aa);
6-fluoro-8-phenylquinoline-1-oxide (I-ba);
6-chloro-8-phenylquinoline-1-oxide (I-ca);
6-bromo-8-phenylquinoline-1-oxide (I-da);
6-methyl-8-phenylquinoline-1-oxide (I-ea);
6-methoxy-8-phenylquinoline-1-oxide (I-fa);
6-methoxycarbonyl-8-phenylquinoline-1-oxide (I-ga);
2-methyl-8-phenylquinoline-1-oxide (I-ha);
2, 8-diphenylquinoline-1-oxide (I-ia);
4-methyl-8-phenylquinoline-1-oxide (I-ja);
3-chloro-8-phenylquinoline-1-oxide (I-ka);
5-chloro-8-phenylquinoline-1-oxide (I-la);
7-chloro-8-phenylquinoline-1-oxide (I-ma);
2, 6-dimethyl-8-phenylquinoline-1-oxide (I-na);
7-chloro-2-methyl-8-phenylquinoline-1-oxide (I-oa);
6-methoxy-2-methyl-8-phenylquinoline-1-oxide (I-pa);
4-chloro-6-fluoro-8-phenylquinoline-1-oxide (I-qa);
4-phenylphenanthridine-5-oxide (I-ra);
8- (4-fluorophenyl) quinoline-1-oxide (I-ab);
8- (4-chlorophenyl) quinoline-1-oxide (I-ac);
8- (4-bromophenyl) quinoline-1-oxide (I-ad);
8- (4-methylphenyl) quinoline-1-oxide (I-ae);
8- (4-tert-butylphenyl) quinoline-1-oxide (I-af);
8- ([ 1,1' -diphenyl ] -4-) quinoline-1-oxide (I-ag);
8- (4-cyanophenyl) quinoline-1-oxide (I-ah);
8- (4-trifluoromethylphenyl) quinoline-1-oxide (I-ai);
8- (4-methoxycarbonylphenyl) quinoline-1-oxide (I-aj);
8- (2-chlorophenyl) quinoline-1-oxide (I-ak);
8- (3-chlorophenyl) quinoline-1-oxide (I-al);
8- (3-methoxyphenyl) quinoline-1-oxide (I-am);
8- (3-nitrophenyl) quinoline-1-oxide (I-an);
8- (3-trifluoromethylphenyl) quinoline-1-oxide (I-ao);
8- (3, 4-dichlorophenyl) quinoline-1-oxide (I-ap);
8- (3, 5-difluorophenyl) quinoline-1-oxide (I-aq);
8- (3, 4, 5-trichlorophenyl) quinoline-1-oxide (I-ar);
8- (naphthalen-2-yl) quinoline-1-oxide (I-as).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910902385.3A CN112624970B (en) | 2019-09-24 | 2019-09-24 | Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910902385.3A CN112624970B (en) | 2019-09-24 | 2019-09-24 | Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112624970A CN112624970A (en) | 2021-04-09 |
| CN112624970B true CN112624970B (en) | 2022-10-28 |
Family
ID=75283179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910902385.3A Active CN112624970B (en) | 2019-09-24 | 2019-09-24 | Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112624970B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115777715B (en) * | 2022-07-11 | 2024-02-02 | 杭州师范大学 | Application of hydroxychloroquine sulfate in prevention of plant virus ACMV and method thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1207771A (en) * | 1968-03-18 | 1970-10-07 | Warner Lambert Pharmaceutical | Anti-virally active quinoline derivatives |
| LT2751083T (en) * | 2011-08-31 | 2018-03-26 | Otsuka Pharmaceutical Co., Ltd. | Quinolone compound |
-
2019
- 2019-09-24 CN CN201910902385.3A patent/CN112624970B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN112624970A (en) | 2021-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI581711B (en) | Compositions for the protection of agrarian corps, the use thereof and method for controlling phytopathogenic fungi in agrarian crops | |
| CN112624970B (en) | Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization | |
| JP2017197557A (en) | Fungal alternative oxidase inhibitors | |
| CN113016814B (en) | Application of tryptanthrin derivative in treatment of plant virus and germ diseases | |
| CN114213403B (en) | 1,2,4-oxadiazole-5-formamide derivative and preparation method and application thereof | |
| WO2015135360A1 (en) | Gossypol aromatic amine schiff base derivative and preparation method and plant virus resistant use thereof | |
| WO2015083438A1 (en) | Agricultural and horticultural chemical, plant disease control method and plant disease control product | |
| WO2015083436A1 (en) | Agricultural and horticultural chemical, plant disease control method and plant disease control product | |
| TW201208569A (en) | Novel heterocyclic alkanol derivatives | |
| WO2015083437A1 (en) | Agricultural and horticultural chemical, plant disease control method and plant disease control product | |
| CN101925583A (en) | Pyridazine derivatives useful as fungicides and for treatment of cancer | |
| CN113016805B (en) | Application of phthalide derivatives in preventing and treating plant virus, killing bacteria, killing insects and killing mites | |
| CN113016806B (en) | Application of coumarin derivatives in preventing and treating plant viruses, killing bacteria and killing insects | |
| CN111349088B (en) | Indole-based heterocyclic compounds, preparation method thereof and application thereof in controlling plant diseases | |
| AU2011291626A1 (en) | Synergistic algicidal compositions including hydrazone derivatives and copper | |
| CN111349089A (en) | Indole heterocyclic compound, preparation method thereof and application thereof in preventing and treating plant diseases | |
| JP2017001998A (en) | 1,4-benzothiazine-1,3-dione or -1,1,3-trione derivative and bactericide containing the same as effective component | |
| CN115521267A (en) | Benzenesulfonamide compound containing N-5-chloroisoxazole malonate structure, preparation method and application | |
| CN110156685B (en) | Aromatic cyclopentenopyridine, and synthesis method and application thereof | |
| CN110759911B (en) | Carboline derivative, preparation method thereof and application thereof in preventing and treating plant viruses, killing bacteria and killing insects | |
| EP3328201B1 (en) | Application of 7-carboxybenzo[1,2,3]thiadiazole amides as plant stimulants | |
| CN113999231A (en) | Alhaginine A derivative, preparation thereof and application thereof in preventing and treating plant virus and bacterial diseases | |
| CN111349080A (en) | Indole acylhydrazone compound, preparation method thereof and application of indole acylhydrazone compound in prevention and treatment of plant diseases | |
| CN110642782B (en) | (S) -2- (2-chloronicotinylamino) propyl propionate derivative and preparation method and application thereof | |
| CN115246835B (en) | Aldrisin derivative containing hydrazone structure and preparation and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |