CN103923013A - 一种吡唑肟醚酯类化合物及用途 - Google Patents
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- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- 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
- A01N43/48—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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- Health & Medical Sciences (AREA)
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Abstract
本发明公开了一种吡唑肟醚酯类化合物及其在制备杀菌剂方面的应用。
Description
技术领域
本发明属于农用杀菌剂领域。具体涉及一种吡唑肟醚酯类化合物及其在制备杀菌剂方面的应用。
技术背景
肟菌酯，英文名称：Trifloxystrobin，是从天然产物Strobilurins成功开发的一种广谱高效的含氟杀菌剂，2000年由Bayer公司推入市场。其作用机理独特，对环境友好，对作物安全，是继三唑类杀菌剂之后的又一类重要的杀菌剂(Pest Manag.Sci.2002，58，649.；Angew.Chem.Int.Ed.1999，38，13281)。
目前，肟菌酯中的肟醚酯结构在农药研究中受到广泛关注。沈阳化工研究院推出了自主开发的烯肟菌酯，该化合物在较低剂量下对多种作物病菌具有较好的防治效果；将肟醚酯基团与吡唑环相连得到了对红蜘蛛有很好防治效果的唑螨酯；将肟醚酯拼接上脲类基团得到了具有优秀杀虫杀螨活性的氟螨脲；将肟醚酯与乙酸甲酯或甲酸甲酯基相连得到了具有很好除草活性的氟草醚酯。由此可见，肟醚基团在杀虫、杀螨、杀菌、除草等领域都有广泛的应用，说明该类结构具有较高的生物活性。
从新农药创制的角度出发，以活性基团拼接原理为指导思想，将肟菌酯的肟醚酯毒杀基团引入唑菌胺酯的N-芳基-3-氧代吡唑结构，设计并合成了一种吡唑肟醚酯类化合物。通过杀菌活性测试，发现该类化合物具有较好的杀菌活性，有望开发成为农药新品种。
发明内容
本发明的目的在于提供一种在很小的剂量下就具有杀菌活性的新型吡唑肟醚酯类化合物，并提供一种该化合物的制备方法。
本发明的技术方案如下：
本发明提供一种吡唑肟醚酯类化合物，如通式I所示：
其中，R(n)中n＝1-5取代，R(n)分别选自氢、卤素、氰基、硝基、C1-C6烷基、C2---C6烯基、C2C6炔基、C1-C6卤代烷基、C1-C6烷氧基、C1--C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基，其中所述的卤代基中的卤素选自氟、氯、溴或碘中的一种或几种。
可以用下表1中列出的化合物来说明本发明，但并不限定本发明。
表1
| 编号 | R(n) |
| 1 | 3-CF3 |
| 2 | 2-CH3 |
| 3 | 4-Cl |
| 4 | 3-CF3-4-F |
| 5 | 3-Cl |
| 6 | 3-F |
| 7 | 4-OCF3 |
| 8 | 4-CH(CH3)2 |
通式I所示的吡唑肟醚酯类化合物由N-芳基-3-羟基吡唑和(E)-2-(2-溴甲基苯基)-2-羰基乙酸甲酯-O-甲基酮肟通过取代反应制得，可参照文献J.Heterocyclic Chem.2010，49，1370等。
本发明的化合物可以制备杀菌剂，可应用在油菜菌核病敏感菌株Sclerotinia sclerotiorum、蔬菜灰霉病敏感菌株Botryris cinerea Pers.、小麦赤霉病敏感菌株Gibbrella zeae(Schw.)Petch、小麦纹枯病敏感菌株Rhizoctorua solani或稻瘟病菌Pyricularia oryzae Cav等菌引起的多种病害。
本发明的新型吡唑肟醚酯类化合物可以用作多种作物的病害防治，包括人参、西洋参、三七、白术、贝母、砂仁、菊花、枸杞或百合的药用植物；小麦、玉米、水稻、马铃薯、甜菜、花生或棉花的大田植物；白菜、番茄、黄瓜、辣椒或扁豆的蔬菜作物；桃、梨、葡萄或草莓的园艺作物；君子兰或芦荟的花卉。杀菌活性测定的具体实施方式
以表1中的化合物进行杀菌效果评定，同时选取唑菌胺酯作为对照。以油菜菌核病敏感菌株Sclerotinia sclerotiorum、蔬菜灰霉病敏感菌株Botryris cinerea Pers.、小麦赤霉病敏感菌株Gibbrella zeae(Schw.)Petch、小麦纹枯病敏感菌株Rhizoctorua solani、稻瘟病菌Pyricularia oryzae Cav作为靶标，以盆栽子叶期黄瓜苗为试验作物，处理药剂量：离体：10ppm、1ppm、0.1ppm；活体：1000ppm，以清水对照进行杀菌活性试验。离体和活体试验方法可参照专利CN103275009A和CN103613542A等。部分测试结果如下：
表1离体杀菌活性结果表
表2活体杀菌活性结果表
分级标准：A级：抑制率≥90％；B级：90％>抑制率≥70％；C级：70％>抑制率≥50％；D级：50％>抑制率。
虽然已经用优选实施例详述了本发明，然而其并非用于限定本发明。任何本领域的技术人员，在不脱离本发明的精神和范围的情况下，应当可以作出各种修改与变更。因此本发明的保护范围应当视为所附的权利要求书所限定的范围。
Claims (3)
1.一种吡唑肟醚酯类化合物，如通式I所示：
其中：
R(n)中n＝1-5取代，R(n)分别选自氢、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基，其中所述的卤代基中的卤素选自氟、氯、溴或碘中的一种或几种。
2.一种如权利要求1中任一所述的化合物在制备杀菌剂方面的应用。
3.一种如权利要求2所述的用途，其中所述的菌为油菜菌核病敏感菌株、蔬菜灰霉病敏感菌株、小麦赤霉病敏感菌株、小麦纹枯病敏感菌株或稻瘟病菌。
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999011129A1 (en) * | 1997-09-04 | 1999-03-11 | E.I. Du Pont De Nemours And Company | Enantiomerically enriched compositions and their pesticidal use |
| CN1306506A (zh) * | 1998-07-16 | 2001-08-01 | 诺瓦提斯公司 | 苯基－甲氧亚氨基－乙酸衍生物农药 |
| US6589974B1 (en) * | 1999-12-22 | 2003-07-08 | Bayer Aktiengesellschaft | Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides |
| CN103275009A (zh) * | 2013-06-13 | 2013-09-04 | 南京工业大学 | 一种含芳基甲氧基丙烯酸酯的氯代吡唑类化合物、制备方法及用途 |
| CN103613542A (zh) * | 2013-11-19 | 2014-03-05 | 南京工业大学 | 一种含(e)-甲氧基亚氨基苯乙酸甲酯的芳基吡唑类化合物、制备方法及用途 |
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- 2014-04-29 CN CN201410175075.3A patent/CN103923013A/zh active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999011129A1 (en) * | 1997-09-04 | 1999-03-11 | E.I. Du Pont De Nemours And Company | Enantiomerically enriched compositions and their pesticidal use |
| CN1306506A (zh) * | 1998-07-16 | 2001-08-01 | 诺瓦提斯公司 | 苯基－甲氧亚氨基－乙酸衍生物农药 |
| US6589974B1 (en) * | 1999-12-22 | 2003-07-08 | Bayer Aktiengesellschaft | Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides |
| CN103275009A (zh) * | 2013-06-13 | 2013-09-04 | 南京工业大学 | 一种含芳基甲氧基丙烯酸酯的氯代吡唑类化合物、制备方法及用途 |
| CN103613542A (zh) * | 2013-11-19 | 2014-03-05 | 南京工业大学 | 一种含(e)-甲氧基亚氨基苯乙酸甲酯的芳基吡唑类化合物、制备方法及用途 |
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