CN111285801B - Pyridine amide compound and application - Google Patents

Pyridine amide compound and application Download PDF

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CN111285801B
CN111285801B CN201811496746.0A CN201811496746A CN111285801B CN 111285801 B CN111285801 B CN 111285801B CN 201811496746 A CN201811496746 A CN 201811496746A CN 111285801 B CN111285801 B CN 111285801B
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王刚
杨辉斌
兰杰
郝泽生
李志念
陈霖
李斌
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • 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

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Abstract

The invention belongs to the field of bactericides. Relates to a pyridine amide compound and a sterilization application thereof. The pyridine amide compound is shown as a general formula I:

Description

Pyridine amide compound and application
Technical Field
The invention belongs to the field of bactericides. Relates to a pyridine amide compound and a sterilization application thereof.
Background
Since fungicides are resistant to diseases after a period of use, there is a continuing need to invent new and improved compounds and compositions having fungicidal activity.
The bactericidal activity of picolinamide compounds has been reported. For example, JP58096069 discloses compound KC (compound 2 in the patent) and its bactericidal activity.
Figure GDA0004036490850000011
In the prior art, the pyridine amide compounds with the structure shown as the general formula I are not reported.
Disclosure of Invention
The invention aims to provide a pyridine amide compound with better bactericidal activity, which can be applied to the prevention and the treatment of diseases in agriculture.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a pyridine amide compound is shown as a general formula I,
Figure GDA0004036490850000012
in the formula:
R 1 selected from hydrogen, halogen, nitro, cyano, C 1 -C 12 Alkyl or C 1 -C 12 A haloalkyl group of (a);
R 2 is selected from C 1 -C 12 Alkyl groups of (a);
the compound shown in the general formula I can also be a chiral compound, and the configuration of the chiral compound is selected from R configuration, S configuration or RS mixed configuration.
The preferable technical scheme in the invention is that in the general formula I:
R 1 selected from hydrogen, halogen, nitro, C 1 -C 6 Alkyl or C 1 -C 6 Haloalkyl of (a);
R 2 is selected from C 1 -C 8 Alkyl groups of (a);
or, the chiral compound shown in the general formula I, wherein the configuration of the chiral compound is selected from R configuration, S configuration or RS mixture.
A further preferred technical solution in the present invention is, in the general formula I:
R 1 selected from hydrogen, fluoro, chloro, bromo, iodo, nitro, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoroisopropyl;
R 2 selected from methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, pentyl, 2-pentyl, hexyl or 2-hexyl; or, the chiral compound shown in the general formula I, wherein the configuration of the chiral compound is selected from R configuration, S configuration or RS mixture.
A particularly preferred embodiment of the present invention is represented by the general formula I:
R 1 selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl or trifluoromethyl;
R 2 selected from 2-pentyl or 2-hexyl;
or, the chiral compound shown in the general formula I has a configuration selected from an R configuration, an S configuration or an RS mixture.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
alkyl means straight or branched chain forms such as methyl, ethyl, n-propyl, isopropyl, and the like. Haloalkyl refers to an alkyl group substituted with one or more halogen atoms, such as chloroethyl, trifluoromethyl, difluoromethyl, heptafluoroisopropyl, and the like. Halogen means fluorine, chlorine, bromine, iodine.
The compound I with the general formula can be prepared by the following method:
Figure GDA0004036490850000021
wherein L represents a leaving group.
The compound of the general formula II and the compound of the general formula III react in a proper solvent and in the presence of a proper alkali at the temperature of-10 ℃ to the boiling point of the proper solvent for 0.5 to 48 hours to prepare the compound I.
Suitable solvents are selected from dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran, dioxane, N-dimethylformamide or dimethyl sulfoxide, and the like.
Suitable bases include hydrogen compounds of alkali metals such as lithium, sodium or potassium, such as sodium hydride, hydroxides of alkali metals such as lithium, sodium or potassium, such as sodium hydroxide, and also carbonates of alkali metals such as sodium carbonate, and also organic bases such as triethylamine, sodium tert-butoxide, etc.
The compounds of formula II are commercially available reagents or are prepared from their corresponding acids.
The compounds of formula III may be prepared by reference to the following references: bioorganic & Medicinal Chemistry,2012, 20 (3): 1213-1221; WO2005117909; pesticide, 2007, 46 (5): 307-309.
Table 1 lists the structure and physical properties of some of the compounds of formula I.
Figure GDA0004036490850000022
Table 1 structural and physical properties of some compounds of formula I
Figure GDA0004036490850000023
Figure GDA0004036490850000031
Figure GDA0004036490850000041
Figure GDA0004036490850000051
Figure GDA0004036490850000061
Figure GDA0004036490850000071
Of partial compounds 1 H NMR(600MHz，CDCl 3 ) The data are as follows:
compound 12:9.83 (s, 1H), 8.80 (d, J =3.9Hz, 1H), 8.24 (d, J =7.9Hz, 1H), 7.84 (d, J =8.2hz, 1h), 7.63 (dd, J1=7.9hz, J 2 ＝4.7Hz，1H)，7.22(t，J＝8.2Hz，1H)，6.73(d，J＝8.2Hz，1H)，3.85(s，3H)，2.26(s，3H).
Compound 26:9.82 (s, 1H), 8.81 (d, J =4.6hz, 1h), 8.24 (d, J =8.0hz, 1h), 7.83 (d, J =8.2hz, 1h), 7.63 (dd, J =8.2hz, 1h) 1 ＝8.0Hz，J 2 ＝4.8Hz，1H)，7.19(t，J＝8.2Hz，1H)，6.72(d，J＝8.2Hz，1H)，4.05(q，J＝7.0Hz，2H)，2.26(s，3H)，1.44(t，J＝7.0Hz，3H).
Compound 54:9.81 (s, 1H), 8.80 (d, J =3.8hz, 1h), 8.23 (d, J =7.9hz, 1h), 7.82(d，J＝8.1Hz，1H)，7.62(dd，J 1 ＝8.0Hz，J 2 ＝4.7Hz，1H)，7.18(t，J＝8.2Hz，1H)，6.74(d，J＝8.2Hz，1H)，4.53(q，1H)，2.25(s，3H)，1.34(d，J＝6.1Hz，6H).
Compound 82:9.80 (s, 1H), 8.80 (d, J =4.6hz, 1h), 8.24 (d, J =8.0hz, 1h), 7.81 (d, J =8.1hz, 1h), 7.62 (dd, J =8.1hz, 1h), and 1 ＝7.9Hz，J 2 ＝4.8Hz，1H)，7.18(t，J＝8.2Hz，1H)，6.73(d，J＝8.2Hz，1H)，4.31(q，1H)，2.25(s，3H)，1.81-1.71(m，1H)，1.69-1.61(m，1H)，1.30(d，J＝6.1Hz，3H)，0.99(t，J＝7.4Hz，3H).
compound 99:10.09 (s, 1H), 8.64-8.62 (m, 1H), 8.31 (d, J =7.8Hz, 1H), 7.90 (td, J) 1 ＝7.7Hz，J 2 ＝1.6Hz，1H)，7.86(d，J＝8.1Hz，1H)，7.47(ddd，J 1 ＝7.5Hz，J 2 ＝4.8Hz，J 3 ＝1.1Hz 1H)，7.19(t，J＝8.2Hz，1H)，6.71(t，J＝9.8Hz，1H)，4.38(dd，J 1 ＝12.1Hz，J 2 ＝6.1Hz，1H)，2.28(s，3H)，1.80-1.73(m，1H)，1.62-1.53(m，1H)，1.53-1.38(m，2H)，1.30(d，J＝6.1Hz，3H)，0.95(t，J＝7.3Hz，3H).
Compound 101:9.92 (s, 1H), 8.54 (d, J =7.6hz, 1h), 7.89-7.87 (m, 1H), 7.84-7.83 (m, 1H), 7.43-7.41 (m, 1H), 7.19-7.17 (m, 1H), 6.72-6.71 (m, 1H), 4.36 (q, 1H), 2.25 (s, 3H), 1.80-1.73 (m, 1H), 1.61-1.54 (m, 1H), 1.53-1.39 (m, 2H), 1.30 (d, J =6.1hz, 3h), 0.91 (t, J =7.3hz, 3h).
Compound 102:9.95 (s, 1H), 8.58 (d, J =7.6hz, 1h), 8.11-8.09 (m, 1H), 7.84-7.83 (m, 1H), 7.34-7.32 (m, 1H), 7.19-7.17 (m, 1H), 6.72-6.71 (m, 1H), 4.36 (q, 1H), 2.25 (s, 3H), 1.80-1.73 (m, 1H), 1.61-1.54 (m, 1H), 1.53-1.39 (m, 2H), 1.30 (d, J =6.1hz, 3h), 0.91 (t, J =7.3hz, 3h).
Compound 104:9.59 (s, 1H), 8.78-8.77 (m, 1H), 7.95-7.93 (m, 1H), 7.75-7.73 (m, 1H), 7.67-7.65 (m, 1H), 7.17-7.15 (m, 1H), 6.74-6.72 (m, 1H), 4.38 (q, 1H), 2.25 (s, 3H), 1.78-1.74 (m, 1H), 1.57-1.45 (m, 3H), 1.30 (d, J =6.1hz, 3h), 0.94 (t, J =7.3hz, 3h).
Compound 105:10.26 (s, 1H), 8.47-8.46 (m, 1H), 7.80-7.79 (m, 1H), 7.65-7.63 (m, 1H), 7.37-7.35 (m, 1H), 6.95-6.92 (m, 1H), 6.71-6.70 (m, 1H), 4.33-4.39 (m, 1H), 2.82 (s, 3H), 2.25 (s, 3H), 1.78-1.74 (m, 1H), 1.57-1.45 (m, 3H), 1.28 (d, J =6.1hz, 3h), 0.94 (t, J =7.3hz, 3h).
Compound 110:9.80 (s, 1H), 8.81-8.78 (m, 1H), 8.23 (d, J =7.9hz, 1h), 7.81 (d, J =8.1hz, 1h), 7.62 (dd, J =8.1hz, 1h) 1 ＝8.0Hz，J 2 ＝4.7Hz，1H)，7.18(t，J＝8.2Hz，1H)，6.73(d，J＝8.2Hz，1H)，4.38(dd，J 1 ＝12.1Hz，J 2 ＝6.1Hz，1H)，2.25(s，3H)，1.79-1.72(m，1H)，1.60-1.53(m，1H)，1.53-1.39(m，2H)，1.29(d，J＝6.1Hz，3H)，0.94(t，J＝7.3Hz，3H).
Compound 127:10.09 (s, 1H), 8.61 (d, J =4.4hz, 1h), 8.29 (d, J =7.8hz, 1h), 7.88 (dd, J = 4hz, 1h) 1 ＝10.3Hz，J 2 ＝4.5Hz，2H)，7.44(dd，J 1 ＝7.2Hz，J 2 ＝4.9Hz，1H)，7.19(t，J＝8.2Hz，1H)，6.71(t，J＝7.9Hz，1H)，4.36(dd，J 1 ＝12.1Hz，J 2 ＝6.1Hz，1H)，2.28(s，3H)，1.82-1.77(m，1H)，1.74-1.65(m，1H)，1.65-1.56(m，1H)，1.53-1.41(m，1H)，1.41-1.33(m，2H)，1.30(d，J＝6.1Hz，3H)，0.91(t，J＝7.1Hz，3H).
Compound 129:9.92 (s, 1H), 8.54 (d, J =4.4hz, 1h), 7.87-7.89 (m, 1H), 7.84-7.83 (m, 1H), 7.43-7.41 (m, 1H), 7.17-7.19 (m, 1H), 6.73-6.71 (m, 1H), 4.39-4.36 (m, 1H), 2.25 (s, 3H), 1.77-1.43 (m, 6H), 1.30 (d, J =6.1hz, 3h), 0.95 (t, J =7.1hz, 3h).
Compound 130:9.95 (s, 1H), 8.59-8.58 (m, 1H), 8.11-8.09 (m, 1H), 7.84-7.83 (m, 1H), 7.33-7.31 (m, 1H), 7.19-7.16 (m, 1H), 6.73-6.71 (m, 1H), 4.40-4.35 (m, 1H), 2.24 (s, 3H), 1.79-1.43 (m, 6H), 1.30 (d, J =6.1hz, 3h), 0.94 (t, J =7.1hz, 3h).
Compound 132:9.59 (s, 1H), 8.79-8.78 (m, 1H), 7.96-7.94 (m, 1H), 7.76-7.75 (m, 1H), 7.68-7.66 (m, 1H), 7.18-7.15 (m, 1H), 6.74-6.72 (m, 1H), 4.37-4.35 (m, 1H), 2.26 (s, 3H), 1.79-1.34 (m, 6H), 1.30 (d, J =6.1hz, 3h), 0.93 (t, J =7.1hz, 3h).
Compound 133:10.26 (s, 1H), 8.47-8.46 (m, 1H), 7.80-7.77 (m, 1H), 7.64-7.63 (m, 1H), 7.37-7.35 (m, 1H), 7.19-7.16 (m, 1H), 6.71-6.68 (m, 1H), 6.34-6.31 (m, 1H), 4.37-4.29 (m, 1H), 2.82 (s, 3H), 2.26 (s, 3H), 1.76-1.33 (m, 6H), 1.30 (d, J =6.1hz, 3h), 0.91 (t, J =7.1hz, 3h).
Compound 138:9.80 (s, 1H), 8.80 (d, J =4.4hz, 1h), 8.24 (d, J =8.0hz, 1h), 7.81 (d, J =8.3hz, 1h), 7.64-7.60 (m, 1H), 7.18 (t, J =8.1hz, 1h), 6.73 (d, J =8.4hz, 1h), 4.36 (dd, J, H) 1 ＝11.9Hz，J 2 ＝5.9Hz，1H)，2.25(s，3H)，1.80-1.76(m，1H)，1.72-1.64(m，1H)，1.64-1.55(m，1H)，1.52-1.41(m，1H)，1.41-1.33(m，2H)，1.30(d，J＝6.0Hz，3H)，0.91(t，J＝6.7Hz，3H).
Compound 143:9.80 (s, 1H), 8.79 (s, 1H), 8.22 (d, J =7.9hz, 1h), 7.81 (d, J =8.1hz, 1h), 7.61 (dd, J =8.1hz, 1h), and combinations thereof 1 ＝8.0Hz，J 2 ＝4.7Hz，1H)，7.18(t，J＝8.2Hz，1H)，6.73(d，J＝8.2Hz，1H)，4.38(dd，J 1 ＝12.1Hz，J 2 ＝6.1Hz，1H)，2.25(s，3H)，1.79-1.72(m，1H)，1.60-1.53(m，1H)，1.53-1.39(m，2H)，1.30(d，J＝6.1Hz，3H)，0.94(t，J＝7.3Hz，3H).
Compound 144:9.80 (s, 1H), 8.80 (s, 1H), 8.24 (d, J =7.9hz, 1h), 7.81 (d, J =8.1hz, 1h), 7.62 (dd, J =8.1hz, 1h) 1 ＝8.0Hz，J 2 ＝4.7Hz，1H)，7.18(t，J＝8.2Hz，1H)，6.73(d，J＝8.2Hz，1H)，4.38(dd，J 1 ＝12.1Hz，J 2 ＝6.1Hz，1H)，2.25(s，3H)，1.79-1.72(m，1H)，1.60-1.53(m，1H)，1.53-1.39(m，2H)，1.30(d，J＝6.1Hz，3H)，0.94(t，J＝7.3Hz，3H).
The invention also comprises the use of the compounds of the general formula I for controlling diseases, in particular diseases of the classes Oomycetes (Oomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomycetes), deuteromycetes (Deuteromycetes), plasmodiophoromycetes (Plasmodiophoromycetes), chytridiomycetes (Chytridiomycetes) and Zygomycetes (Zygomycetes).
Examples of certain diseases under the class names listed above may be mentioned including but not limited to:
wheat rust, wheat powdery mildew, wheat scab, wheat root rot, wheat sharp eyespot, wheat take-all, wheat glume blight, cucumber downy mildew, cucumber anthracnose, cucumber fusarium wilt, cucumber gray mold, grape downy mildew, tomato early blight, tomato late blight, rice sheath blight, rice blast, watermelon gummy stem blight, peanut scab, peanut black spot, citrus scab, pepper root rot, cotton verticillium wilt, cotton wilt, rape black stem disease, rape sclerotinia rot, pear scab, ginseng rot, corn rust, corn curvularia, corn northern leaf spot, corn stalk rot, apple ring rot, apple rot, mango leaf spot. The invention also comprises a sterilization composition using the compound in the general formula I as an active component. The weight percentage of the compound of the general formula I as an active component in the sterilization composition is between 1 and 99 percent. The bactericidal composition also comprises an agriculturally acceptable carrier.
The compositions of the present invention may be administered in the form of a formulation. The compounds of formula I are dissolved or dispersed as active ingredients in carriers or formulated so as to be more easily dispersed for use as fungicides. For example: these chemicals can be formulated as wettable powders or emulsifiable concentrates. In these compositions, at least one liquid or solid carrier is added, and when necessary, a suitable surfactant may be added.
The technical scheme of the invention also comprises a method for preventing and treating diseases, which comprises the following steps: the bactericidal composition is applied to the diseases or the growth medium thereof. An effective amount of from 10 grams per hectare to 1000 grams per hectare is generally preferred.
For certain applications, for example in agriculture, one or more other insecticides, fungicides, herbicides, plant growth regulators or fertilizers and the like may be added to the fungicidal compositions of the present invention, thereby providing additional advantages and effects.
The invention has the advantages that:
compared with the known pyridine amide compounds, the pyridine amide compounds have novel structures, have unexpected high bactericidal activity, have high bactericidal activity under lower dosage, are high in efficiency, reduce the using amount of pesticides, reduce the cost and reduce the pollution to the environment.
Detailed Description
The following synthetic examples, biological activity assay examples, are intended to further illustrate the invention, but are not intended to limit the invention.
Synthetic examples
Example 1 preparation of compound 110:
Figure GDA0004036490850000091
3-trifluoromethylpyridine-2-carboxylic acid (200 mg, 1.05 mmol), 10 ml of toluene and 1 ml of thionyl chloride were added to a reaction flask, and the mixture was refluxed for 2 hours, and excess thionyl chloride and solvent were removed for further use. 2-methyl-3- (pentyl-2-oxy) aniline (202 mg, 1.05 mmol) was dissolved in 10 ml dichloromethane and 1 ml triethylamine was added. And dissolving the prepared acyl chloride in dichloromethane, dropwise adding the mixture into the mixed solution, and reacting for 2 hours at normal temperature. The reaction mixture was poured into 30 ml of water, extracted with dichloromethane three times, and the organic layer was taken and washed with a saturated aqueous sodium bicarbonate solution and a saturated brine in this order, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether = 1: 3) to give 100 mg of compound 110 in 25.8% yield.
Example 2 preparation of compound 138:
Figure GDA0004036490850000101
3-trifluoromethylpyridine-2-carboxylic acid (200 mg, 1.05 mmol), 10 ml of toluene and 1 ml of thionyl chloride were added to a reaction flask, and the mixture was refluxed for 2 hours, and excess thionyl chloride and solvent were removed for further use. 2-methyl-3- (hexyl-2-oxy) aniline (217 mg, 1.05 mmol) was dissolved in 10 ml dichloromethane and 1 ml triethylamine was added. And dissolving the prepared acyl chloride in dichloromethane, dropwise adding the mixture into the mixed solution, and reacting for 2 hours at normal temperature. The reaction mixture was poured into 30 ml of water, extracted with dichloromethane three times, and the organic layer was taken and washed with a saturated aqueous sodium bicarbonate solution and a saturated brine in this order, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether = 1: 3) to obtain 150 mg of compound 138 in 37.3% yield.
Other compounds of formula I of the present invention may be synthesized by reference to the methods described above.
Examples of measurement of biological Activity
EXAMPLE 3 measurement of fungicidal Activity
The compounds of the present invention obtained as described above were used to test various diseases of plants. The method of testing is as follows:
(1) In vivo protective Activity test
The test was performed using potted seedling assay. Selecting potted cucumber seedlings with consistent growth in two leaf stages as test host plants of cucumber downy mildew; selecting potted wheat seedlings with consistent growth in two leaf periods as test host plants of wheat powdery mildew, and selecting potted corn seedlings with consistent growth in two leaf periods as test host plants of corn rust. Foliar spray treatments were carried out with the compounds of the present invention at the designed concentrations. And additionally arranging a blank control sprayed with clear water, repeating for 3 times, and performing disease inoculation the next day after treatment. After inoculation, the plants are placed in a climatic chamber for humid cultivation (temperature: 25 ℃ day, 20 ℃ night, relative humidity: 95-99%). After the test material is cultured for 24h, the test material is moved to a greenhouse for culture, and plants which do not need to be subjected to moisture-preserving culture are directly inoculated and cultured in the greenhouse. The control is taken to evaluate the disease prevention effect of the compound after full disease (usually a week). Results investigation was conducted with reference to the American society for Plant Diseases, A Manual of Association, which is designated 100-0, with "100" representing no disease and "0" representing the most severe degree of disease.
Some of the test results are as follows:
the prevention effect on the corn rust disease is as follows:
according to the test method, in some tested compounds, the following compounds have better control effect on the corn rust at the concentration of 400ppm, and the compounds with the control effect of more than or equal to 80 percent are the compounds 12, 26, 54, 82, 101, 102, 104, 105, 110, 127, 129, 130, 132, 138, 143 and 144.
Compounds 82, 110 and 138 were selected for parallel assays of corn rust control activity with the known compound KC, according to the test methods above. The test results are shown in Table 2.
Table 2: comparison of the Effect of some of the Compounds of the invention on corn rust control with known Compounds
Figure GDA0004036490850000102
Figure GDA0004036490850000111
(2) In vitro test for bacteriostatic activity
The measurement method is as follows: a high-throughput screening method is adopted, namely a compound sample to be detected is prepared into a liquid to be detected with required concentration by using a proper solvent (the type of the solvent is acetone, methanol, DMF, and the like, and is selected according to the dissolving capacity of the solvent to the sample). Under an ultraclean working environment, adding the solution to be tested into micropores of a 96-hole culture plate, adding the pathogen propagule suspension into the micropore, placing the treated culture plate in a constant-temperature incubator for culture, and investigating after 24 hours. During investigation, the germination or growth condition of the pathogen propagules is visually observed, and the bacteriostatic activity of the compound is evaluated according to the germination or growth condition of the control treatment.
The in vitro bacteriostatic activity (expressed as inhibition) of some compounds was tested as follows:
rice blast germs:
among some tested compounds, the following compounds have good control effect at the concentration of 25ppm, and the inhibition rate is more than or equal to 80%: compounds 110 and 127.

Claims (5)

1. A pyridine amide compound is shown as a general formula I:
Figure FDF0000020685100000011
in the formula:
R 1 is selected from trifluoromethyl;
R 2 selected from 2-pentyl or 2-hexyl.
2. The compound of claim 1, wherein the compound of formula I is further a chiral compound, and the chiral compound configuration is selected from an R configuration, an S configuration, or an RS mixed configuration.
3. Use of a picolinamide compound according to claim 1, wherein: the compound of the general formula I is used for preparing medicines for controlling agricultural, forestry or non-treatment target plant diseases.
4. A germicidal composition, characterized by: the bactericidal composition takes the compound shown as the general formula I in claim 1 as an active component and an agriculturally or forestry acceptable carrier, and the weight content of the compound shown as the general formula I in the composition as the active component is 1-99%.
5. A method of controlling plant disease, comprising: applying an effective dose of 10 to 1000 grams per hectare of the composition of claim 4 to a medium in which the disease or its growth is to be controlled.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5896069A (en) * 1981-11-30 1983-06-07 Ishihara Sangyo Kaisha Ltd 2-pyridinecarboxylic acid anilide compound and agricultural and horticultural fungicide containing the same
CN104649973A (en) * 2013-11-25 2015-05-27 中国中化股份有限公司 Pyrazole amide compound and application thereof
CN108349895A (en) * 2015-09-07 2018-07-31 拜耳作物科学股份公司 Substituted 2- difluoromethyls-nicotine (thio) formailide derivative and its purposes as fungicide

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RU2017132315A (en) * 2015-02-18 2019-03-18 Байер Кропсайенс Акциенгезельшафт SUBSTITUTED 2-DIFLUOROMETHYL-NICOTINE (THIO) CARBOXANILIDE DERIVATIVES AND THEIR APPLICATION AS FUNGICIDES

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5896069A (en) * 1981-11-30 1983-06-07 Ishihara Sangyo Kaisha Ltd 2-pyridinecarboxylic acid anilide compound and agricultural and horticultural fungicide containing the same
CN104649973A (en) * 2013-11-25 2015-05-27 中国中化股份有限公司 Pyrazole amide compound and application thereof
CN108349895A (en) * 2015-09-07 2018-07-31 拜耳作物科学股份公司 Substituted 2- difluoromethyls-nicotine (thio) formailide derivative and its purposes as fungicide

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