CN105061396B - 一种酰胺衍生物及其制备方法 - Google Patents
一种酰胺衍生物及其制备方法 Download PDFInfo
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- CN105061396B CN105061396B CN201510496487.1A CN201510496487A CN105061396B CN 105061396 B CN105061396 B CN 105061396B CN 201510496487 A CN201510496487 A CN 201510496487A CN 105061396 B CN105061396 B CN 105061396B
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- chloropyridine
- amide derivatives
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- 238000002360 preparation method Methods 0.000 title claims abstract description 40
- 150000001408 amides Chemical class 0.000 title claims description 28
- 239000000575 pesticide Substances 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 7
- -1 cyclopenta Chemical group 0.000 claims description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 239000003208 petroleum Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 12
- 238000004440 column chromatography Methods 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
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- 239000003480 eluent Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical class ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical class CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 235000015424 sodium Nutrition 0.000 claims 2
- UJHSIDUUJPTLDY-UHFFFAOYSA-N (2-nitrophenyl)-phenylmethanone Chemical class [O-][N+](=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 UJHSIDUUJPTLDY-UHFFFAOYSA-N 0.000 claims 1
- MFYLRNKOXORIPK-UHFFFAOYSA-N (3-nitrophenyl)-phenylmethanone Chemical class [O-][N+](=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 MFYLRNKOXORIPK-UHFFFAOYSA-N 0.000 claims 1
- ZYMCBJWUWHHVRX-UHFFFAOYSA-N (4-nitrophenyl)-phenylmethanone Chemical class C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 ZYMCBJWUWHHVRX-UHFFFAOYSA-N 0.000 claims 1
- RLYUNPNLXMSXAX-UHFFFAOYSA-N 5-methylthiazole Chemical compound CC1=CN=CS1 RLYUNPNLXMSXAX-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
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- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
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- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000005909 ethyl alcohol group Chemical group 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
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- 229910052708 sodium Inorganic materials 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 4
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- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
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- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
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- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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Abstract
本发明属于农药技术领域，具体涉及一种3‑(3,3‑二氯烯丙氧基)‑1‑(3‑氯吡啶‑2‑基)‑吡唑‑5‑甲酰胺衍生物及其制备方法和包括上述衍生物的农药组合物。本发明3‑(3,3‑二氯烯丙氧基)‑1‑(3‑氯吡啶‑2‑基)‑吡唑‑5‑甲酰胺衍生物抑菌活性高，适用于农业领域、林业领域以及园艺领域的植物病害和病毒病害的防治，有效的防治农作物病虫害。
Description
技术领域
本发明属于农药技术领域，具体涉及一种酰胺衍生物3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物及其制备方法和包含上述衍生物的农药组合物。
背景技术
含氮杂环类化合物具有较高的生理和药理活性，在农药的开发中具有重要价值，其中吡唑为含有两个氮原子的1,2-二氮唑五元杂环。含吡唑环的化合物具有较高的生物活性，从1946年Thmaposon第一次报道了2-吡唑-5-酮可以抑制生物生长及1949年美国Rubber公司合成了吡唑类的叶面喷洒杀菌剂之后，吡唑类化合物在农药领域取得了飞速发展，例如Geigy.s.A.公司于1952年把吡唑环引入氨基甲酸酯、有机磷制备了吡唑威、异索威、吡唑硫磷、吡唑氧磷和敌蝇威等农用杀虫剂。
而近年，商品化或即将商品化的含吡唑杂环的农药品种更加众多，特别是近年迅猛发展起来的吡唑酰胺类杀菌剂，拜耳司开发的吡唑酰胺杀菌剂Bixafen,先正达发现并开发的Isopyrazam,巴斯夫公司公布的化合物fluxapyroxad和先正达处于研究开发后期的杀菌剂Sedaxane(张一宾,世界农药,2014,4(36):31-33.)。这些农药品种的共同特点是含有吡唑杂环的酰胺类化合物，具有较高的杀菌活性。
发明内容
本发明的目的之一在于提供一种酰胺衍生物3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物，生物活性高。
本发明的目的之二在于提供上述的酰胺衍生物3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物的制备方法。
本发明的目的之三还在于提供一种农药组合物，包括上述的酰胺衍生物3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物。
为实现上述目的，本发明采用如下技术方案：
一种酰胺衍生物，所述的酰胺衍生物为3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物，化学结构通式如下：
其中，R为甲基、异丙基、环丙基、环戊基、环己基、苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-氰基苯基、3-氰基苯基、4-氰基苯基、2-N,N-二甲基氨基苯基、3-N,N-二甲基氨基苯基、4-N,N-二甲基氨基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、吡啶-2-基、吡啶-3-基、吡啶-4-基、2-苯基苯基、2-对氟苯基苯基、2-对氯苯基苯基或者5-甲基噻唑-2-基。
上述的酰胺衍生物的制备方法，包括以下步骤：
(1)3-氯-2-肼基吡啶的制备：
a.在三口圆底烧瓶中加入0.3～0.4mol 2,3-二氯吡啶、0.8～1.0mol的水合肼，加入320～360mL乙醇溶解，磁力搅拌，60～70℃条件下回流10～13h；
b.反应完成后停止加热，冷却，有白色针状晶体析出，减压过滤，洗涤晶体，晾干，即得到3-氯-2-肼基吡啶；
(2)5-氧代吡唑烷-2-(3-氯吡啶-2-基)-3-酸乙酯的制备：
c.在三口圆底烧瓶中加入90～120mL无水乙醇，分批加入0.08～0.1mol金属钠，得乙醇钠溶液，接着加入0.05～0.06mol3-氯-2-肼基吡啶，加热60～70℃至回流，回流状态下滴加0.06～0.08mol马来酸二乙酯，滴毕，继续回流2～2.5h；
d.反应结束后，冷却至30～40℃，加入0.08～0.1mol冰醋酸酸化，浓缩反应液，重结晶，得到5-氧代吡唑烷-2-(3-氯吡啶-2-基)-3-酸乙酯；
(3)3-羟基-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯的制备：
向单口圆底烧瓶中加入0.04～0.05mol 5-氧代吡唑烷-2-(3-氯吡啶-2-基)3-酸乙酯，100～120mL乙腈，4～5mL 98％浓硫酸，搅拌5～10min，之后加入0.05～0.06molK2S2O8，搅拌回流4.5～5.5h，冷却至室温，得到褐色溶液，浓缩，所得残余物柱层析纯化；
(4)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯的制备：
将3-羟基-1-(3-氯吡啶-2-基)-5-酸乙酯基吡唑0.9～1.1mmol和1.1～1.3mmol1,1,3-三氯丙烯、3～5mL丙酮在碱性条件下搅拌14～16h，过滤，滤液浓缩，得到3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯；
(5)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸的制备：
e.将0.9～1.1mmol 3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯在1.5～1.7mmol氢氧化锂，加入5～8mL的甲醇溶液溶解，搅拌回流10～15h；
f.反应结束后，浓缩，加入蒸馏水，洗涤滤液2～3次，水相用盐酸酸化至pH为4.8～5.2，析出白色沉淀，减压过滤，将滤饼干燥，即得产物；
(6)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑甲酰胺衍生物的制备：
g.将1～1.2mmol有机胺溶解在5～5.5mL二氯甲烷溶液中，在反应瓶中加入0.8～1.0mmol 3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸，1.2～1.5mmol二环己基碳二亚胺DCC，1.2～1.5mmol的三乙胺TEA，0.04～0.05mmol的4-二甲氨基吡啶DMAP，磁力搅拌，抽真空，惰性气体保护下缓慢滴加上述二氯甲烷溶液，滴加完毕，25～30℃继续反应20～25min；
h.反应结束后，减压抽滤，在滤液中加入0.8～1.5g硅胶吸附产品，浓缩至干，柱层析纯化，得到产品。
根据上述的酰胺衍生物的制备方法，步骤(3)所述的柱层析条件为：200～300目硅胶，洗脱剂为石油醚和乙酸乙酯的混合溶液，两者体积比为3:1。
根据上述的酰胺衍生物的制备方法，步骤(6)所述的柱层析条件为：200～300目硅胶柱，洗脱用洗脱剂为石油醚和乙酸乙酯，两者体积比为3:1～10:1。
根据上述的酰胺衍生物的制备方法，所述的石油醚沸点为60～90℃。
根据上述的酰胺衍生物的制备方法，步骤(4)所述的碱性条件为1.5～2mmol K2CO3和0.01～0.05mmol的KI。
根据上述的酰胺衍生物的制备方法，步骤(5)所述的洗涤用溶剂为石油醚和乙酸乙酯混合溶剂。
根据上述的酰胺衍生物的制备方法，所述的石油醚和乙酸乙酯的体积比为1:1。
上述的制备方法的化学通式表示为：
一种农药组合物，包括上述的酰胺衍生物3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物。
根据上述的农药组合物，还包括农药杀虫剂，所述的农药杀虫剂为毒死蜱、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、氰戊菊酯、高效氰戊菊酯、氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、Beta-氟氯氰菊酯、氟氯氰菊酯、Lambda-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、功夫菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、啶虫脒、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、Noviflumuron即多氟脲、氟螨脲、Novaluron即双苯氟脲、氟啶脲、Bay sir 6874即{1-[(3.5-二氯-4)4-硝基苯氧基苯基3-3-(2-氯苯)-脲}、Bay SIR-8514即[1-(4-三氟甲氧基苯基)-3-(2-氯苯)-脲]、嗪虫脲、Bistrifluron即双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、乐果、氧化乐果、敌敌畏、乙酰甲胺磷、三唑磷、喹硫磷、哒嗪硫磷、氯唑磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、丙硫克百威、丁硫克百威、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、丙硫克百威、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、丁烯氟虫腈、三唑锡、噻嗪酮、灭线磷、氟虫腈、杀虫单、杀虫双、氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、唑虫酰胺、吡螨胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素中的任意一种或几种组合。
根据上述的农药组合物，还包括农药杀菌剂，所述的农药杀菌剂为苯并噻二唑、噻酰菌胺、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺(isotianil)、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、水杨酸、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、代森锰锌、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑中的任意一种或几种的组合。
本发明的积极有益效果：
本发明3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物抑菌活性高，适用于农业领域、林业领域以及园艺领域的植物病害和病毒病害的防治，有效的防治农作物病虫害。
本发明3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物化学收率高，纯度高，制备方法简单，生产成本低，易于操作。
具体实施方式
下面结合一些具体实施例对本发明进一步说明。
实施例1
一种酰胺衍生物，所述的酰胺衍生物为3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物，化学结构通式如下：
其中R为甲基。
上述的酰胺衍生物的制备方法，包括以下步骤：
(1)3-氯-2-肼基吡啶的制备：
a.在三颈烧瓶中加入0.3mol 2,3-二氯吡啶、0.85mol的水合肼，加入350mL乙醇溶解，磁力搅拌，70℃条件下回流12h；
b.反应完成后停止加热，冷却，有白色针状晶体析出，减压过滤，洗涤晶体，晾干，即得到3-氯-2-肼基吡啶，收率为80％，纯度≥98％，1H NMR(400MHz,CDCl3)：δ:8.32(d,1H)，7.64(d,1H)，7.01(d,1H)，4.22(s,1H)，2.14(s,2H)；
(2)5-氧代吡唑烷-2-(3-氯吡啶-2-基)-3-酸乙酯的制备：
c.在三口圆底烧瓶中加入100mL无水乙醇，分批加入0.08mol金属钠，得乙醇钠溶液，接着加入0.05mol3-氯-2-肼基吡啶，加热70℃至回流，回流状态下滴加0.07mol马来酸二乙酯，滴毕，继续回流2h；
d.反应结束后，冷却至40℃，加入0.08mol冰醋酸酸化，浓缩反应液，重结晶，得到5-氧代吡唑烷-2-(3-氯吡啶-2-基)-3-酸乙酯，收率为75％，纯度≥95％，1H NMR(400MHz,CDCl3)：δ:8.31(d,1H)，8.07(s,1H)，7.84-6.78(m,2H)，4.33(d,2H)，3.54(t,1H)，2.63(d,2H)，1.56(q,3H)；
(3)3-羟基-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯的制备：
向单口圆底烧瓶中加入0.04mol 5-氧代吡唑烷-2-(3-氯吡啶-2-基)3-酸乙酯，116mL乙腈，4.26mL 98％浓硫酸，搅拌5min，之后加入0.05mol K2S2O8，搅拌回流5h，冷却至室温，得到褐色溶液，浓缩，所得残余物柱层析纯化，洗脱，收率为80％，纯度≥95％，1H NMR(400MHz,CDCl3)：δ:8.47(d,1H)，7.92(d,1H)，7.64(m,1H)，6.83(s,1H)，5.21(s,1H)，4.29(t,2H)，1.56(q,3H)；
(4)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯的制备：
将3-羟基-1-(3-氯吡啶-2-基)-5-酸乙酯基吡唑1mmol和1.2mmol 1,1,3-三氯丙烯、4mL丙酮在碱性条件下搅拌15h，过滤，滤液浓缩，得到3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯，收率为75％，纯度≥95％，1H NMR(400MHz,CDCl3)：δ:8.35(d,1H)，7.86(d,1H)，7.65(m,1H)，6.72(s,1H)，6.25(q,1H)，4.97(d,2H)，4.38(t,2H)，1.43(q,3H)；
(5)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸的制备：
e.将1mmol 3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯在1.5mmol氢氧化锂，加入5mL的甲醇溶液溶解，搅拌回流10～15h；
f.反应结束后，浓缩，加入蒸馏水，石油醚和乙酸乙酯混合溶剂(两者体积比为1:1)洗涤滤液3次，水相用1.0mol/L的盐酸酸化至pH为5，析出白色沉淀，减压过滤，将滤饼干燥，即得产物，收率为87％，纯度≥95％，1H NMR(400MHz,CDCl3)：δ:11.32(s,1H)，8.26(d,1H)，7.97(d,1H)，7.68(d,1H)，6.32(s,1H)，6.14(q,1H)，4.61(d,2H)；
(6)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑甲酰胺衍生物的制备：
g.将1mmol甲胺、5mL二氯甲烷溶液加入到反应瓶中，然后加入0.9mmol 3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸，1.2mmol二环己基碳二亚胺DCC，1.2mmol的三乙胺TEA，0.05mmol的4-二甲氨基吡啶DMAP，磁力搅拌，抽真空，惰性气体保护下缓慢滴加上述二氯甲烷溶液，滴加完毕，25℃继续反应20min；
h.反应结束后，减压抽滤，在滤液中加入1.0g硅胶吸附产品，在旋蒸仪上浓缩至干，柱层析纯化，即得产品，产品的纯度≥97％。
步骤(3)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合溶液，两者体积比为3:1。
步骤(6)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合溶液，两者体积比为5:1。
所述的石油醚沸点为60～90℃。
步骤(4)所述的碱性条件为1.5mmol K2CO3和0.01mmol的KI。
步骤(5)所述的洗涤用溶剂为石油醚和乙酸乙酯混合溶剂。
所述的石油醚和乙酸乙酯的体积比为1:1。
实施例2～40与上述实施例基本原理类似，不重述，有些不同的是：R分别为异丙基、环丙基、环戊基、环己基、苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-氰基苯基、3-氰基苯基、4-氰基苯基、2-N,N-二甲基氨基苯基、3-N,N-二甲基氨基苯基、4-N,N-二甲基氨基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、吡啶-2-基、吡啶-3-基、吡啶-4-基、2-苯基苯基、2-对氟苯基苯基、2-对氯苯基苯基、5-甲基噻唑-2-基。
实施例2～40的3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑甲酰胺衍生物的制备方法与实施例1相似，相同之处不重述，有些不同的是，步骤(5)所述的有机胺R-NH2分别与所述的R基团相对应。
上述实施例1～40所制备的3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物的理化参数见表1。
表1 本发明实施例1～40制备的3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物理化参数
本发明的实施例1～40所述的3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物抑制病原真菌生长活性的测定实验：
测试方法：菌体生长率测定法。
具体过程是：(1)取5mg实施例1～40任意所述的3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物溶解在适量二甲基甲酰胺内，然后用含有一定量吐温20乳化剂水溶液稀释至500μg/mL的药剂，将供试药剂在无菌条件下各吸取1mL注入培养皿内，再分别加入9毫升培养基，摇匀后制成50μg/mL含药平板，以添加1mL灭菌水的平板做空白对照。
(2)用直径4mm的打孔器沿菌丝外缘切取菌盘，移至含药平板上，呈等边三角形摆放，每处理重复3次，将培养皿放在24±1℃恒温培养箱内培养，待对照菌落直径扩展到2～3cm后调查各处理菌盘扩展直径，求平均值，与空白对照比较计算相对抑菌率。
供试菌种：为多种代表在我国农业生产中田间实际发生的大部分植物病原菌的种属，AS：番茄早疫病菌(Alternaria solani)；BC：黄瓜灰霉病菌(Botrytis cinerea)；CA：花生褐斑病菌(Cercospora arachidicola)；GZ：小麦赤霉病菌(Gibberella zeae)；PI：马铃薯晚疫病菌(Phytophthora infestans(Mont.)de Bary)；PP：苹果轮纹病菌(Physalosporapiricola)；PS：水稻纹枯病菌(Pellicularia sasakii)；RC：禾谷丝核菌(Rhizoctoniacerealis)；SS：油菜菌核病菌(Sclerotinia sclerotiorum)。
实验结果见表2。
表2 3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物的生物活性(/％)
结果分析：从表2可以看出，本发明实施例1～40的3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物抑制病原真菌生长的生物活性高。
Claims (9)
1.一种酰胺衍生物，其特征在于，所述的酰胺衍生物为3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物，化学结构通式如下：
其中，R为甲基、异丙基、环丙基、环戊基、环己基、苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、3-溴苯基、4-溴苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-氰基苯基、3-氰基苯基、4-氰基苯基、2-N,N-二甲基氨基苯基、3-N,N-二甲基氨基苯基、4-N,N-二甲基氨基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、吡啶-2-基、吡啶-3-基、吡啶-4-基、2-苯基苯基、2-对氟苯基苯基、2-对氯苯基苯基或者5-甲基噻唑-2-基。
2.一种权利要求1所述的酰胺衍生物的制备方法，其特征在于，包括以下步骤：
(1)3-氯-2-肼基吡啶的制备：
a.在三口圆底烧瓶中加入0.3～0.4mol 2,3-二氯吡啶、0.8～1.0mol的水合肼，加入320～360mL乙醇溶解，磁力搅拌，60～70℃条件下回流10～13h；
b.反应完成后停止加热，冷却，有白色针状晶体析出，减压过滤，洗涤晶体，晾干，即得到3-氯-2-肼基吡啶；
(2)5-氧代吡唑烷-2-(3-氯吡啶-2-基)-3-酸乙酯的制备：
c.在三口圆底烧瓶中加入90～120mL无水乙醇，分批加入0.08～0.1mol金属钠，得乙醇钠溶液，接着加入0.05～0.06mol3-氯-2-肼基吡啶，加热60～70℃至回流，回流状态下滴加0.06～0.08mol马来酸二乙酯，滴毕，继续回流2～2.5h；
d.反应结束后，冷却至30～40℃，加入0.08～0.1mol冰醋酸酸化，浓缩反应液，重结晶，得到5-氧代吡唑烷-2-(3-氯吡啶-2-基)-3-酸乙酯；
(3)3-羟基-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯的制备：
向单口圆底烧瓶中加入0.04～0.05mol 5-氧代吡唑烷-2-(3-氯吡啶-2-基)3-酸乙酯，100～120mL乙腈，4～5mL 98％浓硫酸，搅拌5～10min，之后加入0.05～0.06mol K2S2O8，搅拌回流4.5～5.5h，冷却至室温，得到褐色溶液，浓缩，所得残余物柱层析纯化；
(4)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯的制备：
将3-羟基-1-(3-氯吡啶-2-基)-5-酸乙酯基吡唑0.9～1.1mmol和1.1～1.3mmol 1,1,3-三氯丙烯、3～5mL丙酮在碱性条件下搅拌14～16h，过滤，滤液浓缩，得到3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯；
(5)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸的制备：
e.将0.9～1.1mmol 3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸乙酯在1.5～1.7mmol氢氧化锂，加入5～8mL的甲醇溶液溶解，搅拌回流10～15h；
f.反应结束后，浓缩，加入蒸馏水，洗涤滤液2～3次，水相用盐酸酸化至pH为4.8～5.2，析出白色沉淀，减压过滤，将滤饼干燥，即得产物；
(6)3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑甲酰胺衍生物的制备：
g.将1～1.2mmol有机胺溶解在5～5.5mL二氯甲烷溶液中，在反应瓶中加入0.8～1.0mmol 3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-5-吡唑甲酸，1.2～1.5mmol二环己基碳二亚胺DCC，1.2～1.5mmol的三乙胺TEA，0.04～0.05mmol的4-二甲氨基吡啶DMAP，磁力搅拌，抽真空，惰性气体保护下缓慢滴加上述二氯甲烷溶液，滴加完毕，25～30℃继续反应20～25min；
h.反应结束后，减压抽滤，在滤液中加入0.8～1.5g硅胶吸附产品，浓缩至干，柱层析纯化，得到产品。
3.根据权利要求2所述的酰胺衍生物的制备方法，其特征在于，步骤(3)所述的柱层析条件为：200～300目硅胶，洗脱剂为石油醚和乙酸乙酯的混合溶液，两者体积比为3:1。
4.根据权利要求2所述的酰胺衍生物的制备方法，其特征在于，步骤(6)所述的柱层析条件为：200～300目硅胶柱，洗脱用洗脱剂为石油醚和乙酸乙酯，两者体积比为3:1～10:1。
5.根据权利要求3或者4所述的酰胺衍生物的制备方法，其特征在于，所述的石油醚沸点为60～90℃。
6.根据权利要求2所述的酰胺衍生物的制备方法，其特征在于，步骤(4)所述的碱性条件为1.5～2mmol K2CO3和0.01～0.05mmol的KI。
7.根据权利要求2所述的酰胺衍生物的制备方法，其特征在于，步骤(5)所述的洗涤用溶剂为石油醚和乙酸乙酯混合溶剂。
8.根据权利要求7所述的酰胺衍生物的制备方法，其特征在于，所述的石油醚和乙酸乙酯的体积比为1:1。
9.一种农药组合物，其特征在于，包括权利要求1所述的酰胺衍生物3-(3,3-二氯烯丙氧基)-1-(3-氯吡啶-2-基)-吡唑-5-甲酰胺衍生物。
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