CN111440127B - A kind of thiazole amide compound and its preparation and application - Google Patents
A kind of thiazole amide compound and its preparation and application Download PDFInfo
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- 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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- -1 thiazole amide compound Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 241000207199 Citrus Species 0.000 claims abstract description 3
- 229920000742 Cotton Polymers 0.000 claims abstract description 3
- 235000020971 citrus fruits Nutrition 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
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 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
- 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
- 241000233866 Fungi Species 0.000 abstract 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
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 150000001875 compounds Chemical class 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 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
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 239000000243 solution Substances 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 244000000003 plant pathogen Species 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
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003557 thiazoles Chemical class 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
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- 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
Description
技术领域technical field
本发明为一种噻唑酰胺类化合物及其制备和应用，具体涉及农用杀菌剂领域。The invention relates to a thiazole amide compound and its preparation and application, in particular to the field of agricultural fungicides.
背景技术Background technique
噻唑类化合物是一类具有广泛农用和医用生物活性的化合物，而酰基芳胺类化合物是一类具有广泛生物活性的化合物，该发明涉及化合物中既有噻唑结构片段，又有酰基芳胺结构片段，是一种具有优异杀菌活性的结构新颖的化合物。Thiazole compounds are a class of compounds with a wide range of agricultural and medical biological activities, and acyl arylamine compounds are a class of compounds with a wide range of biological activities, the invention relates to compounds in which there are both thiazole structural fragments and acyl arylamine structural fragments. , is a novel compound with excellent bactericidal activity.
发明内容SUMMARY OF THE INVENTION
本发明的目的在于提供一种新的噻唑酰胺类化合物及其制备方法，其可用于农业上以防治作物病害。The purpose of the present invention is to provide a new thiazole amide compound and a preparation method thereof, which can be used in agriculture to prevent and treat crop diseases.
本发明的技术方案如下：The technical scheme of the present invention is as follows:
本发明提供一种噻唑酰胺类化合物，其结构通式如下：The present invention provides a kind of thiazole amide compound, and its general structural formula is as follows:
其中，X基团选自亚甲基（-CH2-）、氧（O）、氨基（-NH）、氮甲基（-NCH3-）、氮异丙基（-N-CH(CH3)2）及硫（S）；R基团选自苯基、对甲基苯基、对硝基苯基、对氟苯基、对羟基苯基、对甲氧基苯基、3-氯-2-甲基苯基、5-氯-2-甲基苯基。Wherein, the X group is selected from methylene (-CH 2 -), oxygen (O), amino (-NH), nitrogen methyl (-NCH 3 -), nitrogen isopropyl (-N-CH(CH 3 ) 2 ) and sulfur (S); R group is selected from phenyl, p-methylphenyl, p-nitrophenyl, p-fluorophenyl, p-hydroxyphenyl, p-methoxyphenyl, 3-chloro- 2-methylphenyl, 5-chloro-2-methylphenyl.
合成噻唑酰胺类化合物的反应式如下：The reaction formula for synthesizing thiazole amides is as follows:
式中X, R定义同上，首先由氰化胺与二硫化碳、氢氧化钾和硫酸二甲酯反应制备中间体Ⅱ；氯乙酰氯与中间体Ⅲ反应得到中间体Ⅳ；最后由中间体Ⅱ、吗啉或哌啶等、硫化钠、中间体Ⅳ及碳酸钾在有机溶剂中、于70～80℃一锅反应制备目标化合物Ⅰ。有机溶剂选择N,N-二甲基甲酰胺、二甲亚砜等偶极非质子溶剂。In the formula, X and R are as defined above. First, intermediate II is prepared by the reaction of cyanamide with carbon disulfide, potassium hydroxide and dimethyl sulfate; intermediate IV is obtained by the reaction of chloroacetyl chloride with intermediate III; The target compound I is prepared by a one-pot reaction of sodium sulfide, intermediate IV and potassium carbonate in an organic solvent at 70-80 °C. Dipolar aprotic solvents such as N,N-dimethylformamide and dimethyl sulfoxide are selected as organic solvents.
本发明的化合物对多种农业植物病原菌具有很好的杀菌作用。The compound of the present invention has good bactericidal effect on various agricultural plant pathogens.
具体实施方式Detailed ways
化合物的典型制备Typical preparation of compounds
实施例1Example 1
将40%的氢氧化钾溶液（70 g, 0.5 mol）搅拌下滴加到75毫升丙酮和30%的氰化胺（35 g, 0.25 mol）的混合溶液中，15分钟滴加完毕。将反应体系温度降至10～15℃，加入二硫化碳（19.5 g, 0.254 mol），维持温度10～15℃反应2小时。升温至20～25℃，静置分层，回收有机层，水层升温至40～45℃，向水层中滴加硫酸二甲酯(64 g, 0.5 mol)，1小时加毕。将反应混合物加热回流5小时，然后降温至5～10℃，维持此温度0.5小时，析出沉淀，过滤，干燥得浅黄色中间体Ⅱ33.9克，收率93%。M.p.: 49～51℃。1H-NMR(CDCl3, 400MHz)A 40% potassium hydroxide solution (70 g, 0.5 mol) was added dropwise to a mixed solution of 75 mL of acetone and 30% cyanamide (35 g, 0.25 mol) under stirring, and the dropwise addition was completed in 15 minutes. The temperature of the reaction system was lowered to 10-15 °C, carbon disulfide (19.5 g, 0.254 mol) was added, and the temperature was maintained at 10-15 °C for 2 hours. The temperature was raised to 20-25°C, left to stand for stratification, the organic layer was recovered, the water layer was heated to 40-45°C, and dimethyl sulfate (64 g, 0.5 mol) was added dropwise to the water layer, and the addition was completed in 1 hour. The reaction mixture was heated to reflux for 5 hours, then cooled to 5-10°C, maintained at this temperature for 0.5 hours, precipitated out, filtered, and dried to obtain 33.9 g of pale yellow Intermediate II with a yield of 93%. Mp: 49～51℃. 1 H-NMR (CDCl 3 , 400MHz)
δ: 2.65(s, 6H)。δ: 2.65(s, 6H).
将中间体Ⅲ-b（30 mmol, 3.21 g）加入到15毫升饱和醋酸钠和15毫升冰醋酸的混合溶液中，0℃下滴加（31 mmol, 2.5 mL）氯乙酰氯，滴加过程控制温度不超过8℃，加毕，室温搅拌反应2.5小时，析出沉淀，过滤，所得沉淀用水洗涤，真空干燥得4.99克N-（4-甲基苯基）-2-氯乙酰胺中间体（Ⅳ-b），收率91%。M.p:168.5～169℃。1H-NMR(CDCl3,400MHz) δ:2.33(s, 3H), 4.18(s, 2H), 7.16(d, 2H), 7.42(d, 2H)。Intermediate III-b (30 mmol, 3.21 g) was added to a mixed solution of 15 mL of saturated sodium acetate and 15 mL of glacial acetic acid, and (31 mmol, 2.5 mL) chloroacetyl chloride was added dropwise at 0 °C, and the dropwise process was controlled The temperature did not exceed 8 °C, after the addition was completed, the reaction was stirred at room temperature for 2.5 hours, a precipitate was precipitated, filtered, the obtained precipitate was washed with water, and dried in vacuo to obtain 4.99 g of N-(4-methylphenyl)-2-chloroacetamide intermediate (IV) -b), yield 91%. Mp: 168.5～169℃. 1 H-NMR (CDCl 3 , 400 MHz) δ: 2.33(s, 3H), 4.18(s, 2H), 7.16(d, 2H), 7.42(d, 2H).
将中间体Ⅱ（0.2 mol, 29.25 g）溶于350毫升N,N-二甲基甲酰胺，加入哌啶(0.2mol, 17 g)，将反应混合物搅拌加热至75℃反应1小时；然后向反应混合物中加入Na2S.9H2O(0.2 mol, 48 g)，75℃反应1.5小时；把反应温度降至50℃，加入中间体Ⅳ-b（0.3 mol,54.9 g），50℃搅拌反应2小时，将反应混合物倾入1.5L的冰水中，快速搅拌，析出沉淀，过滤，水洗涤沉淀，室温干燥，得目标物I-b粗品53克，用95%乙醇重结晶得40.5克目标物I-b，收率64%。M.p: 216.4-216.6℃。1H-NMR (400 MHz, CDCl3):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-)。Intermediate II (0.2 mol, 29.25 g) was dissolved in 350 mL of N,N-dimethylformamide, piperidine (0.2 mol, 17 g) was added, and the reaction mixture was stirred and heated to 75 °C for 1 hour; Na 2 S.9H 2 O (0.2 mol, 48 g) was added to the reaction mixture, and the reaction was carried out at 75 °C for 1.5 hours; the reaction temperature was lowered to 50 °C, intermediate IV-b (0.3 mol, 54.9 g) was added, and the mixture was stirred at 50 °C Reacted for 2 hours, poured the reaction mixture into 1.5L of ice water, stirred rapidly, separated out the precipitate, filtered, washed the precipitate with water, and dried at room temperature to obtain 53 grams of target Ib crude product, which was recrystallized with 95% ethanol to obtain 40.5 grams of target Ib , the yield is 64%. Mp: 216.4-216.6°C. 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 , -CON H -), 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 -).
实施例2 抑菌活性测定 Example 2 Determination of antibacterial activity
取一定量实施例1，用丙酮溶解并定容得供试药液，将该药液适量置于100毫升60℃左右PDA灭菌培养皿中，摇匀，倒入直径60毫米的灭菌培养皿中，冷却凝固后，分别移接生长一致、直径为4毫米的菌饼，以加入等量丙酮的灭菌培养基作为空白对照，每处理设3次重复。放入25℃恒温培养箱中培养一定时间后，测量菌落直径，计算抑菌率，求取有效中浓度EC50。如对苹果腐烂菌的EC50为19.1ppm, 对棉花枯萎菌的EC50为24.3ppm，对柑橘炭疽菌EC50为14.7ppm。Take a certain amount of Example 1, dissolve and dilute with acetone to obtain the test medicinal solution, place an appropriate amount of the medicinal solution in 100 ml of a PDA sterilized petri dish at about 60°C, shake it up, and pour it into a sterilized culture dish with a diameter of 60 mm. In the dish, after cooling and solidification, the bacterial cakes with uniform growth and diameter of 4 mm were transferred respectively, and the sterilized medium with the same amount of acetone was used as a blank control, and each treatment was repeated 3 times. After being placed in a 25°C constant temperature incubator for a certain period of time, the diameter of the colony was measured, the bacteriostatic rate was calculated, and the effective medium concentration EC 50 was obtained. For example, the EC 50 for apple rot is 19.1 ppm, the EC 50 for cotton wilt is 24.3 ppm, and the EC 50 for citrus anthracis is 14.7 ppm.
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