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CN105646395B - A kind of thiazole amide compound and its application - Google Patents

A kind of thiazole amide compound and its application Download PDF

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CN105646395B
CN105646395B CN201410720849.6A CN201410720849A CN105646395B CN 105646395 B CN105646395 B CN 105646395B CN 201410720849 A CN201410720849 A CN 201410720849A CN 105646395 B CN105646395 B CN 105646395B
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compound
formula
alkyl
amide compound
thiazole amide
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CN105646395A (en
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吕亮
李玉钢
单中刚
张稳
陈宣明
吴沙沙
刘吉永
王刚
陈霖
李斌
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Abstract

The invention belongs to bactericide field, specifically a kind of thiazole amide compound and its application.Thiazole amide compound, as shown in formula I：

Description

A kind of thiazole amide compound and its application
Technical field
The invention belongs to bactericide field, specifically a kind of thiazole amide compound and its application.
Background technology
Due to bactericide in use for some time, disease can produce resistance to it, therefore, it is necessary to constantly invent new With improved bactericidal compound and composition.
The bactericidal activity of thiazole amide compound is it has been reported that as JPS5657776 discloses compound K C (in patent Compound 1) bactericidal activity.
In the prior art, thiazole amide compound of the structure as shown in formula I of the present invention has no report.
The content of the invention
It is an object of the invention to provide a kind of thiazole amide compound and its application.
To achieve the above object, technical scheme is as follows：
A kind of thiazole amide compound, as shown in formula I：
In formula：
R1Selected from C1-C3Alkyl, C2-C6Alkenyl, C2-C6Alkynyl, C3-C6Cycloalkyl, C1-C6Haloalkyl, C2-C6Haloalkene Base, C2-C6Halo alkynyl or C3-C6Halogenated cycloalkyl；
R2Selected from C1-C6Alkyl, C1-C6Haloalkyl, C3-C6Cycloalkyl；
R3Selected from C1-C6Alkyl；
R4Selected from C1-C6Alkyl, C2-C6Alkenyl, C2-C6Alkynyl, C3-C6Cycloalkyl, C1-C6Haloalkyl, C2-C6Haloalkene Base, C2-C6Halo alkynyl or C3-C6Halogenated cycloalkyl；
X is selected from halogen.
Preferable technical scheme is in the present invention, in formula I：
R1Selected from C1-C3Alkyl, C2-C4Alkenyl, C2-C4Alkynyl, C3-C6Cycloalkyl, C1-C3Haloalkyl, C2-C4Haloalkene Base, C2-C4Halo alkynyl or C3-C6Halogenated cycloalkyl；
R2Selected from C1-C3Alkyl, C1-C3Haloalkyl or C3-C6Cycloalkyl；
R3Selected from C1-C3Alkyl；
R4Selected from C1-C4Alkyl, C2-C4Alkenyl, C2-C4Alkynyl, C3-C6Cycloalkyl, C1-C3Haloalkyl, C2-C4Haloalkene Base, C2-C4Halo alkynyl or C3-C6Halogenated cycloalkyl；
X is selected from fluorine, chlorine, bromine or iodine.
Further preferred technical scheme is in the present invention, in formula I：
R1Selected from methyl, ethyl or trifluoromethyl；
R2Selected from methyl, ethyl, isopropyl, trifluoromethyl or cyclopropyl；
R3Selected from methyl or ethyl；
R4Selected from methyl, ethyl, propyl group, butyl, vinyl, acetenyl, cyclopropyl, cyclobutyl, cyclopenta or cyclohexyl；
X is selected from fluorine, chlorine, bromine or iodine.
In general formula compound I given above definition, collect term used and be typically defined as follows：
Alkyl refers to straight or branched form, such as methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, Zhong Ding The groups such as base, tertiary butyl, n-pentyl, isopentyl, n-hexyl.Cycloalkyl includes cyclopropyl, cyclobutyl, Cvclopropvlmethvl, methyl Cyclopropyl etc..Haloalkyl refers to the group that alkyl is optionally substituted with one or more halogen atoms.Alkenyl refers to straight or branched alkenyl, Such as 1- acrylic, 2- acrylic.Alkynyl refers to straight or branched alkynyl, such as 1- propinyls, 2-propynyl.Halogen refers to Fluorine, chlorine, bromine, iodine.
A kind of application of thiazole amide compound, the compound of Formula I are used to prepare control agricultural, forestry or non-controlled Treat the medicine of purpose disease.
A kind of bactericidal composition, bactericidal composition are using compound shown in the formula I as active component and agricultural or woods The acceptable carrier of industry, the weight content of active component is 1-99% in composition.
A kind of method for controlling plant disease, described composition is applied with the effective dose of 10 grams to 1000 grams of per hectare In in the disease for needing to control or the medium of its growth.
The compound of Formula I of the present invention can be prepared by the following method, and outer except as otherwise indicating, each group definition is same in reaction equation Before.
In the presence of Compounds of formula II and alkali of the compound of formula III in suitable solvent, suitable, temperature is -10 DEG C 0.5-48 hours obtained target compound I is reacted under to the solvent boiling point for reacting suitable.
Suitable solvent is selected from dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrochysene Furans, dioxane, N,N-dimethylformamide or dimethyl sulfoxide (DMSO) etc..
Suitable alkali includes the alkali metal such as hydrogen compound of lithium, sodium or potassium such as sodium hydride, the alkali metal such as hydrogen of lithium, sodium or potassium Oxide such as sodium hydroxide, it can also be carbonate such as sodium carbonate or the organic base such as triethylamine, the tert-butyl alcohol of alkali metal Sodium etc..
The record that Compounds of formula II refers to preparation method in JPH05125065 and WO2014024119 documents is obtained .
Compound of formula III refers to JP2008189592；Agricultural chemicals, 2007,46 (5):Preparation method in 307-309 documents Record obtained.
Table 1 lists the structure and physical property of partial Formula I.
Compound R1 R2 R3 R4 X Physical property (fusing point DEG C)
1 Me Me Me Me F Crocus oil
2 Me Me Me Me Cl Yellow solid (79-80)
3 Me Me Me Me Br
4 Me Me Me Me I
5 Me Et Me Me F Brown oil liquid
6 Me Et Me Me Cl Brown oil liquid
7 Me Et Me Me Br Brown oil liquid
8 Me Et Me Me I
9 Me i-Pr Me Me F
10 Me i-Pr Me Me Cl
11 Me i-Pr Me Me Br
12 Me i-Pr Me Me I
13 Me cyc-Pr Me Me F
14 Me cyc-Pr Me Me Cl
15 Me cyc-Pr Me Me Br
16 Me cyc-Pr Me Me I
17 Me Me Me Et F
18 Me Me Me Et Cl
19 Me Me Me Et Br
20 Me Me Me Et I
21 Me Me Me n-Pr F Brown oil
22 Me Me Me n-Pr Cl
23 Me Me Me n-Pr Br
24 Me Me Me n-Pr I
25 Me Me Et Et F Brown oil
26 Me Me Et Et Cl
27 Me Me Et Et Br
28 Me Me Et Et I
29 Me CF3 Me Me F Yellow solid (81-83)
30 Me CF3 Me Me Cl Yellow solid (87-89)
31 Me CF3 Me Me Br Brown oil liquid
32 Me CF3 Me Me I
33 Me CF3 Me Et F Brown solid (57-59)
34 Me CF3 Me n-Pr F Brown oil
35 Me CF3 Et Et F Brown solid (52-55)
36 CF3 Me Me Me F Brown solid (90-91)
37 CF3 Me Me Me Cl Yellow solid (92-93)
38 CF3 Me Me Me Br Yellow oily liquid
39 CF3 Me Me Me I
40 CF3 CF3 Me Me F Light brown is solid (122-123)
41 CF3 CF3 Me Me Cl Yellow solid (89-90)
42 CF3 CF3 Me Me Br
43 CF3 CF3 Me Me I
44 CF3 Et Me Me F Yellow solid (87-88)
45 CF3 Et Me Me Cl White solid (95-96)
46 CF3 Et Me Me Br
47 CF3 Et Me Me I
Part of compounds1H NMR(300MHz,CDCl3) data are as follows：
Compound 1：8.00~8.03 (m, 1H), 7.65 (s, 1H), 6.97~7.04 (m, 1H), 6.56~6.61 (m, 1H), 4.48~4.56 (m, 1H), 2.74 (s, 3H), 2.71 (s, 3H), 1.33 (d, 6H)
Compound 2：8.13 (s, 1H), 8.01 (s, 1H), 7.20~7.24 (m, 1H), 6.58~6.61 (m, 1H), 4.53 ~4.57 (m, 1H), 2.75 (s, 3H), 2.68 (s, 3H), 1.33 (d, 6H, J=6.0Hz)
Compound 5：8.00-8.03(m,1H),7.64(s,1H),6.97-7.04(m,1H),6.57-6.60(m,1H), 4.50-4.54(m,1H),3.06-3.14(q,2H),2.72(s,3H),1.25-1.39(m,9H)。
Compound 6：8.14-8.15(d,1H),8.01(s,1H),7.24-7.27(d,1H),6.58-6.62(dd,1H), 4.48-4.62(m,1H),3.12-3.15(q,2H),2.73(s,3H),1.25-1.57(m,9H)。
Compound 7：7.34(s,1H),7.19-7.28(m,1H),6.97-6.99(d,1H),6.67-6.70(d,1H), 4.56-4.59(m,1H),3.05-3.13(q,2H),2.71(s,3H),1.25-1.45(m,9H)。
Compound 21：8.00~8.03 (m, 1H), 7.65 (s, 1H), 6.97~7.04 (m, 1H), 6.56~6.60 (m, 1H), 4.33~4.35 (m, 1H), 2.74 (s, 3H), 2.71 (s, 3H), 1.34~1.73 (m, 4H), 1.29 (d, 3H), 0.91~ 0.98(m,3H)。
Compound 25：8.01~8.04 (m, 1H), 7.65 (s, 1H), 6.97~7.04 (m, 1H), 6.57~6.62 (m, 1H), 4.08~4.12 (m, 1H), 2.74 (s, 3H), 2.71 (s, 3H), 1.63~1.74 (m, 4H), 0.96 (t, 6H).
Compound 29：7.96~8.06 (m, 2H), 6.99~7.06 (m, 1H), 6.61~6.66 (m, 1H), 4.49~ 4.53(m,1H),2.77(s,3H),1.35(d,6H)。
Compound 30：8.26 (s, 1H), 8.08~8.09 (m, 1H), 7.26~7.29 (m, 1H), 6.65~6.69 (m, 1H), 4.53~4.61 (m, 1H), 2.78 (s, 3H), 1.34 (d, 6H).
Compound 31：7.74(s,1H),7.23-7.28(m,1H),6.99-7.02(d,1H),6.72-6.74(d,1H), 4.56-4.60(m,1H),2.77(s,3H),1.29-1.33(d,6H)。
Compound 33：7.96~8.06 (m, 2H), 6.99~7.06 (m, 1H), 6.61~6.67 (m, 1H), 4.24~ 4.30 (m, 1H), 2.78 (s, 3H), 1.55~1.78 (m, 2H), 1.29 (d, 3H), 0.98 (t, 3H).
Compound 34：7.97~8.06 (m, 2H), 6.99~7.05 (m, 1H), 6.60~6.66 (m, 1H), 4.31~ 4.34 (m, 1H), 2.78 (s, 3H), 1.38~1.73 (m, 4H), 1.29 (d, 3H), 0.94 (t, 3H).
Compound 35：7.98~8.07 (m, 2H), 6.99~7.05 (m, 1H), 6.62~6.67 (m, 1H), 4.07~ 4.11 (m, 1H), 2.77 (s, 3H), 1.63~1.72 (m, 4H), 0.96 (t, 6H).
Compound 36：7.96-7.99(m,1H),7.80(s,1H),7.01-7.07(m,1H),6.61-6.67(m,1H), 4.48-4.54(m,1H),2.86(s,3H),1.33-1.39(d,6H)。
Compound 37：8.19(s,1H),8.10-8.12(d,1H),7.26-7.30(d,1H),6.66-6.69(dd,1H), 4.55-4.61(m,1H),2.89(s,3H),1.35-1.36(d,6H)。
Compound 38：7.52(s,1H),7.23-7.28(m,1H),6.98-7.01(d,1H),6.72-6.74(dd,1H), 4.55-4.60(m,1H),2.80(s,3H),1.34-1.36(d,6H)。
Compound 40：8.18(s,1H),7.94(brs,1H),7.03-7.08(dd,1H),6.66-6.70(m,1H), 4.49-4.55(m,1H),1.28-1.30(d,6H)。
Compound 41：8.40(s,1H),8.03(s,1H),7.29-7.32(d,1H),6.69-7.73(dd,1H),4.43- 4.60(m,1H),1.34-1.36(d,6H)。
Compound 44：7.97-8.00(dd,1H),7.79(s,1H),7.02-7.07(dd,1H),6.62-6.66(m, 1H),4.50-4.56(m,1H),3.14-3.19(q,2H),1.41-1.44(t,3H),1.33-1.35(d,6H)。
Compound 45：8.18(s,1H),8.14-8.15(d,1H),7.30-7.32(d,2H),6.68-6.71(dd,1H), 4.57-4.63(m,1H),3.22-3.26(q,2H),1.44-1.48(t,3H),1.37-1.38(d,6H)。
The compound of above-mentioned record is compared with known thiazole amide compound, thiazole amide compound of the invention With high bactericidal activity.Therefore, the purposes for controlling plant disease is used for present invention additionally comprises compound of Formula I, to prevent and treat oomycetes Guiding principle (Oomycetes), Ascomycetes (Ascomycetes), Basidiomycetes (Basidiomycetes), deuteromycetes (Deuteromycetes), Plasmodiophoromycetes (Plasmodiophoromycetes), Chytridiomycetes (Chytridiomycetes) and knot Close bacterium subclass (Zygomycetes) disease.
What the example of some diseases of the guiding principle being listed above under one's name can be mentioned that includes but is not limited to：
Wheat rust, rice sheath blight disease, wheat sharp eyespot, cucumber downy mildew, downy mildew of garpe, wheat powdery mildew, tomato Early blight, cucumber anthracnose, rice blast, wheat scab, root rotof flax, watermelon grafting, Peanut Scab, peanut Black spot, citrus scab, tomato late blight, Fusarium solani, cotton verticillium wilt, rape black stem, take-all, banana Leaf spot, wheat scab, pear scab, Curvularia disease, cotton wilt, ginseng rust rot, the leaf blight of corn, the mango base of a fruit The rotten disease of maize ear rot, cucumber fusarium axysporum, ring rot of apple, apple corruption bacterium, gray mold of cucumber, sclerotinia sclerotiorum, sigatoka, wheat Glume blight.
Present invention additionally comprises the bactericidal composition using compound of Formula I as active component.Conduct in the bactericidal composition The weight percentage of the compound of Formula I of active component is between 1-99%.Also include agricultural or woods in the bactericidal composition Acceptable carrier in industry.
The composition of the present invention can be applied in the form of preparation.Compound of Formula I is dissolved or dispersed in as active component In carrier or be configured to preparation so as to as sterilization use when it is more readily dispersible.Such as：These chemicals can be made into wettable Property pulvis or missible oil.In these compositions, a kind of liquid or solid carrier is at least added, and can be added when needed suitable When surfactant.
Technical scheme also includes the method for preventing and treating fungus damage：The bactericidal composition of the present invention is imposed on to described evil On bacterium or its somatomedin.The more suitable effective amount generally selected is 10 grams to 1000 grams of per hectare.
It is one or more other for some applications, such as can agriculturally be added in the bactericidal composition of the present invention Insecticide, bactericide, herbicide, plant growth regulator or fertilizer etc., it thus can produce the advantages of additional and effect.
It should be appreciated that in scope defined by the claims of the present invention, various conversion and change can be carried out.
Embodiment
Following synthesis example, raw test result can be used to further illustrate the present invention, but be not intended to limit the present invention.
Synthesize example
The synthesis of the compound 13 of embodiment 1
The chloro- 5- isopropoxy anilines of 2- (210 milligrams, 1.131 mMs), triethylamine (137 millis are added into reaction bulb Gram, 1.357 mMs) and 10 milliliters of dichloromethane, 2,4-two trifluoromethyl thiazole-5- formyl chlorides (321 of lower dropwise addition are stirred at room temperature Milligram, 1.131 mMs) 10 milliliters of dichloromethane solution.Drop finishes, and reacts 1.5 hours at room temperature, reaction solution is poured into 30 milliliters In water, organic layer is taken, organic layer is dried, subtracted with saturated sodium bicarbonate aqueous solution, saturated common salt water washing, anhydrous magnesium sulfate respectively Pressure steams solvent to the greatest extent.Residue passes through chromatography over CC (leacheate：Ethyl acetate：Petroleum ether=20：1,10：1) 210 milligrams are obtained Compound 13, yellow solid, 89-90 DEG C of fusing point.
The synthesis of the compound 41 of embodiment 2
The chloro- 5- isopropoxy anilines of 2- (220 milligrams, 1.185 mMs), triethylamine (144 millis are added into reaction bulb Gram, 1.422 mMs) and 10 milliliters of dichloromethane, lower dropwise addition 4- Ethyl-2-Methyl thiazole -5- formyl chlorides (225 are stirred at room temperature Milligram, 1.185 mMs) 10 milliliters of dichloromethane solution.Drop finishes, and reacts and finishes after 1.5h.Reaction solution is poured into 30 milliliters of water In, organic layer is taken, organic layer is dried with saturated sodium bicarbonate aqueous solution, saturated common salt water washing, anhydrous magnesium sulfate respectively, decompression Steam solvent to the greatest extent.Residue passes through chromatography over CC (leacheate：Ethyl acetate：Petroleum ether=10：1) 150 milligrams of compounds are obtained 41, brown oil.
The synthesis of the compound 44 of embodiment 3
The fluoro- 5- isopropoxy anilines of 2- (200 milligrams, 1.182 mMs), triethylamine (144 millis are added into reaction bulb Gram, 1.418 mMs) and 10 milliliters of dichloromethane, lower dropwise addition 2- trifluoromethyls -4- ethyl thiazole -5- formyl chlorides are stirred at room temperature 10 milliliters of the dichloromethane solution of (288 milligrams, 1.182 mMs).Drop finishes, and reacts and finishes after 1.5 hours.Reaction solution is poured into 30 In milliliter water, organic layer is taken, organic layer is done with saturated sodium bicarbonate aqueous solution, saturated common salt water washing, anhydrous magnesium sulfate respectively Dry, solvent to the greatest extent is steamed in decompression.Residue passes through chromatography over CC (leacheate：Ethyl acetate：Petroleum ether=20：1) 110 milligrams are obtained Compound 44, yellow solid, 87-88 DEG C of fusing point.
Other compound of Formula I of the present invention can refer to above method synthesis.
Biological activity determination example
The measure of the bactericidal activity of embodiment 4
The multiple diseases of plant are tested with the compounds of this invention of above-mentioned acquisition.The method of experiment is as follows：
(1) live body protection activity is tested
Experiment uses potted plant seedling determination method.Two consistent leaf phase potted plant cucumber seedlings of growth selection are as cucumber downy mildew Experiment host plant；Experiment host plant of the two consistent leaf phase potted plant wheat seedlings of growth selection as wheat powdery mildew, Experiment host plant of the two consistent leaf phase potted plant corn seedlings of growth selection as corn rust.With the compounds of this invention according to Design concentration carries out foliar spray processing.The another blank control for setting spray clear water, 3 repetitions, carry out disease and connect within second day after processing Kind.After inoculation, plant is placed on moisturizing culture (temperature in phjytotron：25 DEG C of daytime, 20 DEG C of night, relative humidity：95- 99%).After test material culture 24h, dislocation hot-house culture, by do not need moisturizing culture plant directly in warm indoor inoculation simultaneously Culture.(being usually week age) carries out compound protection effect assessment after band control fully morbidity.As a result investigation is with reference to the U.S. The pathology of plants can write《A Manual of Assessment Keys for Plant Diseases》, with 100~0 come table Show, the disease-free occurring degree that most serious is represented with " 0 " level is represented with " 100 " level.
Partial test result is as follows：
To the preventive effect of cucumber downy mildew：
Part is in the compound of examination, following compounds prevention effect when concentration is 400ppm is preferable, preventive effect >=80%： Compound 34.
To the preventive effect of wheat powdery mildew：
Part is in the compound of examination, following compounds prevention effect when concentration is 400ppm is preferable, preventive effect >=80%： Compound 1,30,34.
According to above method, choose compound 1 and 30 and known compound KC (known compound KC referring to, The record of compound 1 prepares in JPS5657776) carry out preventing and treating the active parallel determination of wheat powdery mildew.Result of the test It is shown in Table 2.
Table 2：Part the compounds of this invention and comparisons of the KC to wheat powdery mildew preventive effect
To the preventive effect of corn rust：
Part is in the compound of examination, following compounds prevention effect when concentration is 400ppm is preferable, preventive effect >=80%： Compound 1,29,30,34,35.
According to above method, the parallel survey that compound 1 with known compound KC prevent and treat corn rust activity is chosen It is fixed.Result of the test is shown in Table 3.
Table 3：Part the compounds of this invention and comparisons of the KC to corn rust preventive effect
(2) Antifungal Activity in Vitro is tested
Assay method is as follows：Using high-throughput screening method, i.e., by test compound sample with suitable solvent (solvent Species such as acetone, methanol, DMF etc., and selected according to its solvability to sample) solvent, acetone solution can be specifically used, Concentration prepare liquid needed for being made into.Under ultra-clean working environment, prepare liquid is added in the micropore of 96 well culture plates, then by cause of disease Bacterium breeding liquid suspension is added thereto, and the culture plate after processing, which is placed in constant incubator, to be cultivated, and is investigated after 24 hours. The sprouting of pathogen brood body or growing state, and the sprouting according to control treatment or growing state are estimated during investigation, evaluates chemical combination Thing bacteriostatic activity.
The Antifungal Activity in Vitro of part of compounds (represents) that test result is as follows with inhibiting rate：
Rice blast fungus：
Part is supplied in the compound of examination, and following compounds prevention effect when concentration is 25ppm is preferable, and inhibiting rate >= 80%：Compound 34,35.

Claims (6)

  1. A kind of 1. thiazole amide compound, as shown in formula I：
    In formula：
    R1Selected from C1-C3Alkyl；
    R2Selected from C1-C6Alkyl or C1-C6Haloalkyl；
    R3Selected from C1-C6Alkyl；
    R4Selected from C1-C6Alkyl；
    X is selected from halogen.
  2. 2. according to the thiazole amide compound described in claim 1, it is characterised in that in formula I：
    R1Selected from C1-C3Alkyl；
    R2Selected from C1-C3Alkyl or C1-C3Haloalkyl；
    R3Selected from C1-C3Alkyl；
    R4Selected from C1-C4Alkyl；
    X is selected from fluorine, chlorine, bromine or iodine.
  3. 3. according to the thiazole amide compound described in claim 1, it is characterised in that in formula I：
    R1Selected from methyl；
    R2Selected from methyl or trifluoromethyl；
    R3Selected from methyl or ethyl；
    R4Selected from methyl, ethyl, propyl group or butyl；
    X is selected from fluorine, chlorine, bromine or iodine.
  4. A kind of 4. application of thiazole amide compound according to described in claim 1, it is characterised in that：
    The compound of Formula I is used for the medicine for preparing control agricultural, forestry or non-treatment purpose disease.
  5. A kind of 5. bactericidal composition, it is characterised in that：Bactericidal composition is with compound shown in the formula I described in claim 1 For active component and agricultural or the acceptable carrier of forestry, the weight in composition as the compound of Formula I of active component contains Measure as 1-99%.
  6. A kind of 6. method for controlling plant disease, it is characterised in that：Composition described in claim 5 is arrived for 10 grams with per hectare 1000 grams of effective dose is imposed on the medium of the disease for needing to control or its growth.
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CN108069905B (en) * 2016-11-09 2020-08-04 沈阳中化农药化工研发有限公司 Pyrazole amide compound and application thereof
CN111440127B (en) * 2019-01-17 2022-07-26 青岛农业大学 Thiazole amide compound and preparation and application thereof
CN114560826B (en) * 2022-03-02 2024-06-25 安徽理工大学 Thiazole amide compound containing diphenyl ether group and preparation method and application thereof

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