CN103951619A - 一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物及用途 - Google Patents

一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物及用途 Download PDF

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CN103951619A
CN103951619A CN201410208190.6A CN201410208190A CN103951619A CN 103951619 A CN103951619 A CN 103951619A CN 201410208190 A CN201410208190 A CN 201410208190A CN 103951619 A CN103951619 A CN 103951619A
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alkyl
methoxyl
compounds containing
containing aryl
carbonyl
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刘媛媛
吕坤志
李�杰
胡来凤
高尚
蒋露露
徐光辉
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Southeast university chengxian college
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

本发明公开了一种结构如通式(I)的含芳基吡唑的甲氧亚氨基乙酰胺类化合物。式中R(n)选自氰基，硝基，烷基，烯基，炔基，卤代烷基，烷氧基，卤代烷氧基，烷硫基，烷基羰基，烷氧基羰基，烷基氨基，氟，溴，碘。本发明还公开了该类化合物在制备杀菌剂方面的应用。

Description

一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物及用途
技术领域
本发明属于农用杀菌剂领域。具体涉及一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物及其在制备杀菌剂方面的应用。
技术背景
烯肟菌胺，化学名称：(E，E，E)-N-甲基-2-[((((1-甲基-3-(2，6-二氯苯基)-2-丙烯基)亚氨基)氧基)甲基)苯基]-2-甲氧基亚氨基乙酰胺，俗称：SYP-1620，是沈阳化工研究院1999年发现的以天然抗生素为先导化合物的新型甲氧基丙烯酸酯类杀菌剂，2003年获得中国发明专利(专利号：ZL00110143.9)。烯肟菌胺杀菌谱广，活性高，具有预防和治疗作用，对多种植物病害均有良好的防治效果，且对环境友好，对作物安全，其药效团甲氧亚氨基乙酰胺结构在新农药的研发中受到广泛关注(molecules2010，13，9024-9034)。
从杀菌剂创制的角度出发，以类同合成法和活性基团拼接原理为指导思想，将烯肟菌胺的甲氧亚氨基乙酰胺毒杀基团引入唑菌胺酯的N-芳基吡唑结构，设计并合成了一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物。通过杀菌活性测试，发现该类化合物具有良好的杀菌活性，有望开发成为杀菌剂新品种。
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含芳基吡唑的甲氧亚氨基乙酰胺类化合物。
本发明的技术方案如下：
本发明提供一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物，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、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 2-CH3
2 4-F
3 3-CF3-4-F
4 4-CF3
5 3-CF3
6 4-OCF3
7 4-OCH3
8 4-CH(CH3)2
9 4-CF(CF3)2
10 4-Br
11 3-F
12 3-I
13 2，4-NO2
14 3，4-OCH3
15 3，4，5-OCH3
通式I所示的含芳基吡唑的甲氧亚氨基乙酰胺类化合物由N-芳基-3-羟基吡唑和(E)-N-甲基-2-(2-溴甲基苯基)-2-甲氧基亚氨基乙酰胺通过取代反应制得，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Sclerotiniasclerotiorum、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、水稻纹枯病敏感菌株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。
对照药剂：烯肟菌胺和唑菌胺酯。
靶标：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、水稻纹枯病敏感菌株Rhizoctorua solani、稻瘟病菌Pyricularia oryzae Cav。
试验作物：盆栽子叶期黄瓜苗。
处理药剂量：离体：10ppm、1ppm、0.1ppm；活体：1000ppm。
离体试验方法和活体试验方法参照专利CN103275009A和CN103613542A等，具体结果见下表1，表2。
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力要求书所限定的范围。

Claims (2)

1.一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物，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、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。
CN201410208190.6A 2014-05-16 2014-05-16 一种含芳基吡唑的甲氧亚氨基乙酰胺类化合物及用途 Pending CN103951619A (zh)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3031325A1 (en) 2014-12-10 2016-06-15 Basf Se Method for combating soybean rust comprising treating soybean with (2E)-2-[2-[[1-(2,4-substi-tuted-phenyl)pyrazol-3-yl]oxymeth¬yl]-3-sub¬stituted-phenyl]-2-methoxyimino-n-methyl-acet-amides
CN105924435A (zh) * 2016-06-23 2016-09-07 浙江工业大学 一种取代的吡唑乙酰胺类化合物及其制备方法和应用

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3031325A1 (en) 2014-12-10 2016-06-15 Basf Se Method for combating soybean rust comprising treating soybean with (2E)-2-[2-[[1-(2,4-substi-tuted-phenyl)pyrazol-3-yl]oxymeth¬yl]-3-sub¬stituted-phenyl]-2-methoxyimino-n-methyl-acet-amides
CN105924435A (zh) * 2016-06-23 2016-09-07 浙江工业大学 一种取代的吡唑乙酰胺类化合物及其制备方法和应用

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Application publication date: 20140730