CN111440127B - Thiazole amide compound and preparation and application thereof - Google Patents
Thiazole amide compound and preparation and application thereof Download PDFInfo
- Publication number
- CN111440127B CN111440127B CN201910041976.6A CN201910041976A CN111440127B CN 111440127 B CN111440127 B CN 111440127B CN 201910041976 A CN201910041976 A CN 201910041976A CN 111440127 B CN111440127 B CN 111440127B
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- Prior art keywords
- amide compound
- thiazole amide
- preparation
- methylphenyl
- application
- Prior art date
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- -1 Thiazole amide compound Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229920000742 Cotton Polymers 0.000 claims abstract description 3
- 201000010099 disease Diseases 0.000 claims abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 3
- 241000207199 Citrus Species 0.000 claims abstract 2
- 235000020971 citrus fruits Nutrition 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 2
- 241000233866 Fungi Species 0.000 abstract description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003385 bacteriostatic effect Effects 0.000 abstract description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 abstract 1
- 241000223218 Fusarium Species 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- CITIOELQTFSEGI-UHFFFAOYSA-N 2-chloro-n-(4-methylphenyl)acetamide Chemical compound CC1=CC=C(NC(=O)CCl)C=C1 CITIOELQTFSEGI-UHFFFAOYSA-N 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000000005 bacterial plant pathogen Species 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a thiazole amide compound and preparation and application thereof. The structural general formula of the thiazole amide compounds is as follows:
wherein the X group is selected from methylene (-CH) 2 -), oxygen (O), amino (-NH), aminomethyl (-NCH) 3 -), azoisopropyl (-N-CH (CH) 3 ) 2 ) And sulfur (S); the R group is selected from phenyl, p-methylphenyl, p-nitrophenyl, p-fluorophenyl, p-hydroxyphenyl, p-methoxyphenyl, 3-chloro-2-methylphenyl, 5-chloro-2-methylphenyl. The thiazole amide compound has excellent bacteriostatic activity on apple rot fungi, cotton fusarium wilt fungi, citrus anthracnose and the like, and can be used for preventing and treating crop diseases.
Description
Technical Field
The invention relates to a thiazole amide compound and preparation and application thereof, in particular to the field of agricultural fungicides.
Background
The invention relates to a thiazole compound, which is a compound with wide agricultural and medical bioactivity, and an acyl arylamine compound, which is a compound with wide bioactivity, wherein the compound has a thiazole structure segment and an acyl arylamine structure segment, and has excellent bactericidal activity and a novel structure.
Disclosure of Invention
The invention aims to provide a novel thiazole amide compound and a preparation method thereof, which can be used for preventing and treating crop diseases in agriculture.
The technical scheme of the invention is as follows:
the invention provides a thiazole amide compound, which has the following structural general formula:
wherein the X group is selected from methylene (-CH) 2 -), oxygen (O),Amino (-NH), aminomethyl (-NCH) 3 -), azoisopropyl (-N-CH (CH) 3 ) 2 ) And sulfur (S); the R group is selected from phenyl, p-methylphenyl, p-nitrophenyl, p-fluorophenyl, p-hydroxyphenyl, p-methoxyphenyl, 3-chloro-2-methylphenyl, 5-chloro-2-methylphenyl.
The reaction formula for synthesizing the thiazole amide compound is as follows:
in the formula, X and R are defined as above, and an intermediate II is prepared by the reaction of amine cyanide, carbon disulfide, potassium hydroxide and dimethyl sulfate; reacting chloroacetyl chloride with the intermediate III to obtain an intermediate IV; and finally, carrying out one-pot reaction on an intermediate II, morpholine or piperidine and the like, sodium sulfide, an intermediate IV and potassium carbonate in an organic solvent at 70-80 ℃ to prepare the target compound I. The organic solvent is selected from dipolar aprotic solvents such as N, N-dimethylformamide and dimethyl sulfoxide.
The compound of the invention has good bactericidal action on various agricultural plant pathogenic bacteria.
Detailed Description
Typical preparation of the Compounds
Example 1
40% potassium hydroxide solution (70 g, 0.5 mol) was added dropwise with stirring to a mixed solution of 75 ml of acetone and 30% ammonium cyanide (35 g, 0.25 mol) over 15 minutes. Reducing the temperature of the reaction system to 10-15 ℃, adding carbon disulfide (19.5 g, 0.254 mol), and maintaining the temperature at 10-15 ℃ for reaction for 2 hours. Heating to 20-25 ℃, standing for layering, recovering an organic layer, heating a water layer to 40-45 ℃, dropwise adding dimethyl sulfate (64 g, 0.5 mol) into the water layer, and finishing addition after 1 hour. Heating and refluxing the reaction mixture for 5 hours, then cooling to 5-10 ℃, maintaining the temperature for 0.5 hour, separating out a precipitate, filtering,drying to obtain light yellow intermediate II 33.9 g, yield 93%. M.p. 49-51 ℃. 1 H-NMR(CDCl 3 , 400MHz)
δ: 2.65(s, 6H)。
Adding the intermediate III-b (30 mmol, 3.21 g) into a mixed solution of 15 mL of saturated sodium acetate and 15 mL of glacial acetic acid, dropwise adding (31 mmol, 2.5 mL) chloroacetyl chloride at 0 ℃, controlling the temperature not to exceed 8 ℃ in the dropwise adding process, stirring at room temperature for reacting for 2.5 hours after the addition is finished, separating out a precipitate, filtering, washing the obtained precipitate with water, and drying in vacuum to obtain 4.99 g of N- (4-methylphenyl) -2-chloroacetamide intermediate (IV-b) with the yield of 91%. M.p, 168.5-169 ℃. 1 H-NMR(CDCl 3 ,400MHz) δ: 2.33(s, 3H), 4.18(s, 2H), 7.16(d, 2H), 7.42(d, 2H)。
Dissolving intermediate II (0.2 mol, 29.25 g) in 350 ml of N, N-dimethylformamide, adding piperidine (0.2 mol, 17 g), and heating the reaction mixture to 75 ℃ with stirring for 1 hour; then adding Na to the reaction mixture 2 S.9H 2 O (0.2 mol, 48 g), reaction at 75 ℃ for 1.5 hours; the reaction temperature is reduced to 50 ℃, an intermediate IV-b (0.3 mol, 54.9 g) is added, the mixture is stirred and reacted for 2 hours at 50 ℃, the reaction mixture is poured into 1.5L of ice water, the mixture is quickly stirred, precipitates are separated out, filtered, washed by water and dried at room temperature to obtain 53 g of crude products of the target I-b, the crude products of the target I-b are recrystallized by 95 percent ethanol to obtain 40.5 g of target I-b, and the yield is 64 percent. M.p, 216.4-216.6 ℃. 1 H-NMR (400 MHz, CDCl 3 ):δ 7.40 (d, 2H, J = 8.4 Hz, Ar-H), 7.11(d, 2H, J = 8.0 Hz, Ar-H), 6.47 (bs,1H, -CONH-), 6.06 (bs, 2H, -NH 2 ), 3.49 (bs, 4H, 2×-CH 2 -), 2.31 (s, 3H, Ar-CH 3 ), 1.67 (bs, 6H, 3×-CH 2 -)。
Example 2 bacteriostatic Activity assay
Taking a certain amount of the test liquid medicine obtained in the embodiment 1, dissolving the test liquid medicine by using acetone and fixing the volume to obtain a test liquid medicine, placing a proper amount of the test liquid medicine into a PDA (personal digital assistant) sterilized culture dish with the temperature of about 100 ml and 60 ℃, shaking up the test liquid medicine, pouring the test liquid medicine into the sterilized culture dish with the diameter of 60 mm, cooling and solidifying the test liquid medicine, respectively transferring bacterial cakes with consistent growth and the diameter of 4 mm, taking a sterilized culture medium with the same amount of acetone as a blank control, and repeating the steps for 3 times every treatment. Culturing in 25 deg.C constant temperature incubator for a certain time, measuring colony diameter, calculating antibacterial rate, and calculating effective medium concentration EC 50 . Such as EC against apple rot fungi 50 19.1ppm, EC against Cotton wilt 50 24.3ppm, EC against Colletotrichum citrinum 50 It was 14.7 ppm.
Claims (3)
1. A thiazole amide compound has a structural formula as follows:
。
2. a process for the preparation of thiazoleamides according to claim 1, which comprises the following reaction scheme:
。
3. the use of thiazolamides according to claim 1 for controlling crop diseases caused by apple rot, cotton wilt, or citrus anthracnose.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910041976.6A CN111440127B (en) | 2019-01-17 | 2019-01-17 | Thiazole amide compound and preparation and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910041976.6A CN111440127B (en) | 2019-01-17 | 2019-01-17 | Thiazole amide compound and preparation and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111440127A CN111440127A (en) | 2020-07-24 |
| CN111440127B true CN111440127B (en) | 2022-07-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910041976.6A Expired - Fee Related CN111440127B (en) | 2019-01-17 | 2019-01-17 | Thiazole amide compound and preparation and application thereof |
Country Status (1)
| Country | Link |
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| CN (1) | CN111440127B (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1043127A (en) * | 1988-11-29 | 1990-06-20 | 孟山都公司 | Substituted thiazole and mycocide purposes thereof |
| JP2007302617A (en) * | 2006-05-12 | 2007-11-22 | Mitsui Chemicals Inc | Heterocyclic derivative and method for using the derivative as insecticide |
| WO2010007389A1 (en) * | 2008-07-15 | 2010-01-21 | Cancer Research Technology Limited | 5 -amidothiazole derivatives and their use as checkpoint kinase inhibitors |
| AU2014277506A1 (en) * | 2013-06-07 | 2016-01-21 | Jiangsu Hengrui Medicine Co., Ltd. | Bisulfate of Janus kinase (JAK) inhibitor and preparation method therefor |
| CN105646395A (en) * | 2014-12-02 | 2016-06-08 | 沈阳中化农药化工研发有限公司 | Thiazole amide compound and application thereof |
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| CN106715424A (en) * | 2014-06-05 | 2017-05-24 | 拜耳作物科学股份公司 | Bicyclic compounds as pesticides |
-
2019
- 2019-01-17 CN CN201910041976.6A patent/CN111440127B/en not_active Expired - Fee Related
Patent Citations (7)
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|---|---|---|---|---|
| CN1043127A (en) * | 1988-11-29 | 1990-06-20 | 孟山都公司 | Substituted thiazole and mycocide purposes thereof |
| JP2007302617A (en) * | 2006-05-12 | 2007-11-22 | Mitsui Chemicals Inc | Heterocyclic derivative and method for using the derivative as insecticide |
| WO2010007389A1 (en) * | 2008-07-15 | 2010-01-21 | Cancer Research Technology Limited | 5 -amidothiazole derivatives and their use as checkpoint kinase inhibitors |
| AU2014277506A1 (en) * | 2013-06-07 | 2016-01-21 | Jiangsu Hengrui Medicine Co., Ltd. | Bisulfate of Janus kinase (JAK) inhibitor and preparation method therefor |
| CN106715424A (en) * | 2014-06-05 | 2017-05-24 | 拜耳作物科学股份公司 | Bicyclic compounds as pesticides |
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| One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles;D. Thomae et al.;《Tetrahedron》;20091231;scheme 4，table2，scheme2 * |
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| CN111440127A (en) | 2020-07-24 |
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