CN117903078A - 一类含3,4-二氯异噻唑的酰胺衍生物及其制备方法和用途 - Google Patents
一类含3,4-二氯异噻唑的酰胺衍生物及其制备方法和用途 Download PDFInfo
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- CN117903078A CN117903078A CN202410111068.0A CN202410111068A CN117903078A CN 117903078 A CN117903078 A CN 117903078A CN 202410111068 A CN202410111068 A CN 202410111068A CN 117903078 A CN117903078 A CN 117903078A
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- amide derivative
- ester hydrochloride
- percent
- methyl ester
- dichloroisothiazole
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- 150000001408 amides Chemical class 0.000 title claims abstract description 90
- KYOUKUFLSLXHNL-UHFFFAOYSA-N 3,4-dichloro-1,2-thiazole Chemical compound ClC1=CSN=C1Cl KYOUKUFLSLXHNL-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
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- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 29
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 239000005962 plant activator Substances 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 239000000642 acaricide Substances 0.000 claims abstract description 18
- 239000003899 bactericide agent Substances 0.000 claims abstract description 16
- 239000002917 insecticide Substances 0.000 claims abstract description 10
- 238000001308 synthesis method Methods 0.000 claims abstract description 5
- 239000012752 auxiliary agent Substances 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims description 83
- -1 2- (methylthio) ethyl Chemical group 0.000 claims description 78
- 241000196324 Embryophyta Species 0.000 claims description 68
- 239000007788 liquid Substances 0.000 claims description 51
- 239000007787 solid Substances 0.000 claims description 41
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 claims description 8
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- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
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- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001424 substituent group Chemical group 0.000 claims description 3
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- XFNUTZWASODOQK-UHFFFAOYSA-N (1-ethoxycarbonylcyclopropyl)azanium;chloride Chemical compound Cl.CCOC(=O)C1(N)CC1 XFNUTZWASODOQK-UHFFFAOYSA-N 0.000 claims description 2
- SCGWHMHVOQPGLS-DFWYDOINSA-N (3s)-3-amino-4-methoxy-4-oxobutanoic acid;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC(O)=O SCGWHMHVOQPGLS-DFWYDOINSA-N 0.000 claims description 2
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 2
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- MSSXWKAJMRSAGF-UHFFFAOYSA-N 3,4-dichloro-1,2-thiazole-5-carbonyl chloride Chemical compound ClC(=O)C=1SN=C(Cl)C=1Cl MSSXWKAJMRSAGF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- MFUPLHQOVIUESQ-JEDNCBNOSA-N [(2s)-1,5-dimethoxy-1,5-dioxopentan-2-yl]azanium;chloride Chemical compound Cl.COC(=O)CC[C@H](N)C(=O)OC MFUPLHQOVIUESQ-JEDNCBNOSA-N 0.000 claims description 2
- DWAYENIPKPKKMV-ILKKLZGPSA-N [(2s)-3-(1h-imidazol-3-ium-4-yl)-1-methoxy-1-oxopropan-2-yl]azanium;dichloride Chemical compound Cl.Cl.COC(=O)[C@@H](N)CC1=CN=CN1 DWAYENIPKPKKMV-ILKKLZGPSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- QOMQXHIJXUDQSS-DFWYDOINSA-N hydron;methyl (2s)-2,4-diamino-4-oxobutanoate;chloride Chemical compound Cl.COC(=O)[C@@H](N)CC(N)=O QOMQXHIJXUDQSS-DFWYDOINSA-N 0.000 claims description 2
- SWVMLNPDTIFDDY-UHFFFAOYSA-N hydron;methyl 2-amino-3-phenylpropanoate;chloride Chemical compound Cl.COC(=O)C(N)CC1=CC=CC=C1 SWVMLNPDTIFDDY-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
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- FORVAIDSGSLRPX-RGMNGODLSA-N methyl (2s)-2,6-diaminohexanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CCCCN FORVAIDSGSLRPX-RGMNGODLSA-N 0.000 claims description 2
- XNFNGGQRDXFYMM-PPHPATTJSA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate;hydrochloride Chemical compound Cl.C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 XNFNGGQRDXFYMM-PPHPATTJSA-N 0.000 claims description 2
- VXYFARNRGZWHTJ-FVGYRXGTSA-N methyl (2s)-2-amino-3-(4-hydroxyphenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 VXYFARNRGZWHTJ-FVGYRXGTSA-N 0.000 claims description 2
- NDBQJIBNNUJNHA-DFWYDOINSA-N methyl (2s)-2-amino-3-hydroxypropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CO NDBQJIBNNUJNHA-DFWYDOINSA-N 0.000 claims description 2
- KUGLDBMQKZTXPW-JEDNCBNOSA-N methyl (2s)-2-amino-3-methylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)C(C)C KUGLDBMQKZTXPW-JEDNCBNOSA-N 0.000 claims description 2
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- MEVUPUNLVKELNV-JEDNCBNOSA-N methyl (2s)-2-amino-4-methylsulfanylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CCSC MEVUPUNLVKELNV-JEDNCBNOSA-N 0.000 claims description 2
- XKVHMRBXIJTLBM-JEDNCBNOSA-N methyl (2s)-2-amino-5-(diaminomethylideneamino)pentanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CCCN=C(N)N XKVHMRBXIJTLBM-JEDNCBNOSA-N 0.000 claims description 2
- IYUKFAFDFHZKPI-DFWYDOINSA-N methyl (2s)-2-aminopropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](C)N IYUKFAFDFHZKPI-DFWYDOINSA-N 0.000 claims description 2
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明提供了一类含3,4‑二氯异噻唑的酰胺衍生物及其制备方法和用途,具体涉及一类衍生物,其化学结构通式见式I:I:
Description
技术领域
本发明的技术方案属于农药领域,具体涉及含3,4-二氯异噻唑的酰胺衍生物及其制备方法和用途。
背景技术
农药作为植物保护的重要手段之一,对解决病虫草害问题以及提高粮食作物产量起着极为重要的作用,是关系国家稳定和经济发展的战略物资。但随着农药的大量使用,病虫草害的抗药性、农药残留和环境污染等问题也随之产生,因此高效、低毒、低残留和环境友好的新农药的创制成为研究的重中之重(邵旭升等.世界农药,2020,42(04):16-24)。因此,具有广谱、低毒、无抗药性风险和滞后及长持效期、与其他杀菌剂混用具有协同或者增效作用等特点的“绿色生态农药”植物激活剂成为了绿色农药创制的重要方向。但目前植物激活剂的发展存在着先导分子少、作用机制研究不明确、靶向设计困难等问题。
异噻菌胺(isotianil)是拜尔与住友化学共同研发的防治稻瘟病植物激活剂(Himmler,et al.WO2004002968)。包括异噻菌胺在内的异噻唑甲酰胺类化合物在植物中具有增强植物诱导活性,预防性施用或者在发病早期使用,多种生物因子和非生物因子可激活植物自身的防卫性抗性反应即系统诱导抗性,并影响病原菌生活史的多个环节,从而使植物对多种真菌、细菌、昆虫和病毒产生广谱的自我保护作用;异噻菌胺能提供长期残留药效和更小的施用有效成分的剂量,适合引发植物防御性使植物不受致病的真菌、细菌和病毒及害虫的侵害,能够用来在处理后一定时期内保护植物不受上述有害生物体的侵害。申请人所在课题组前期设计的一系列3,4-二氯异噻唑甲酰胺及甲酸酯衍生物在低浓度下诱导植物的抗病活性优于异噻菌胺(陈晓燕等.CN102942565A.2016-01-27)。本发明保留3,4-二氯异噻唑,设计合成了系列含3,4-二氯异噻唑的酰胺衍生物,其在较低浓度下展现出良好的免疫诱导活性,可作为植物激活剂的候选分子。
发明内容
本发明所要解决的技术问题是:提供一类新的含3,4-二氯异噻唑的酰胺衍生物的合成方法,提供这类化合物调控农业、园艺和卫生以及林业植物害虫和植物病原物的生物活性及其测定方法,同时提供这些化合物在农业领域、园艺领域、林业领域以及卫生领域中的应用。
本发明解决该技术问题所采用的技术方案是:具有农业领域、园艺领域、林业领域杀虫、杀螨活性、杀菌活性、抗植物病毒活性、诱导植物产生抗病活性的含3,4-二氯异噻唑的酰胺衍生物的化学结构通式如I所示:
I:
其中,R1、R2、R3选自:取代烷基、取代烯基、氢、取代炔基、取代环烷基、取代环烯基、取代环炔基、取代烷氧基、取代烯氧基、取代炔氧基、取代的苯基、取代杂环基;
所述杂环基选自:呋喃基、噻吩基、咪唑基、吡唑基、吡啶基、吡喃基、吲哚基、嘧啶基、三嗪基、异吲哚基等含N或/和含硫的三元环基、四元环基、五元环基、六元环基。
R3还选自:Li、Na、K、Ca、Mg。
n选自1、3、4。
上述取代基优选:
R1选自:1-甲基乙基、1-甲基丙基、氢、2-(甲硫基)乙基、咪唑-4-甲基、2-甲基丙基、吲哚-3-甲基、3-甲氧基-3-氧代丙基、甲基、苯甲基、环己基甲基、甲基、苯甲基、对苯酚甲基、2-氨基-2-氧代乙基、羟甲基、乙氧基、3-胍基丙基、4-氨基丁基、羧甲基;R2选自氢、甲基;R3选自氢、钠、甲基、乙基、丙基、丁基、异丙基;n选自1、3、4。
本发明的含3,4-二氯异噻唑的酰胺衍生物I的合成路线如下:
本发明所述含3,4-二氯异噻唑的酰胺衍生物I的合成方法为以下步骤:
A.化合物I的制备:
在室温下,将1当量的氨基甲酸酯盐酸盐2加入二氯甲烷中,再加入2当量的三乙胺,室温搅拌1分钟后,加入1.1当量化合物1,室温搅拌6小时,加入20毫升碳酸氢钠溶液淬灭,水相用二氯甲烷萃取,合并有机相,用饱和食盐水洗有机相三次,并用无水硫酸钠干燥,减压除去溶剂,残余物经200~300目硅胶柱层析纯化,洗脱剂为乙酸乙酯/石油醚,得到含3,4-二氯异噻唑的酰胺衍生物I;所述氨基甲酸酯盐酸盐选自:2-氨基-3-苯基丙酸甲酯盐酸盐、1-氨基环丙烷-1-甲酸乙酯盐酸盐、环亮氨酸甲酯盐酸盐、2-氨基异丁酸甲酯盐酸盐、2-氨基-3-环己基丙酸甲酯盐酸盐、1-氨基环己烷羧酸甲酯盐酸盐、L-缬氨酸甲酯盐酸盐、L-异亮氨酸甲酯盐酸盐、L-蛋氨酸甲酯盐酸盐、L-组氨酸甲酯二盐酸盐、L-亮氨酸叔丁酯盐酸盐、L-色氨酸甲酯盐酸盐、L-谷氨酸二甲酯盐酸盐、甘氨酸甲酯盐酸盐、L-丙氨酸甲酯盐酸盐、L-苯丙氨酸甲酯盐酸盐、L-酪氨酸甲酯盐酸盐、L-天冬酰胺甲酯盐酸盐、L-丝氨酸甲酯盐酸盐、L-苏氨酸甲酯盐酸盐、L-精氨酸甲酯盐酸盐、L-赖氨酸甲酯盐酸盐、L-天冬氨酸甲酯盐酸盐、L-脯氨酸甲酯盐酸盐、D-3-氨基丁酸、β-氨基丁酸。
B.含3,4-二氯异噻唑的酰胺衍生物I的用途:
本发明提供了含3,4-二氯异噻唑的酰胺衍生物I在制备杀真菌剂中的用途,所述真菌为:番茄早疫病菌,其拉丁名为:Alternaria solani、黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、花生褐斑病菌,其拉丁名为:Cercospora arachidicola、禾谷镰孢病菌,其拉丁名为:Fusarium graminearum、苹果轮纹病菌,其拉丁名为:Physalosporapiricola、水稻纹枯病菌,其拉丁名为:Rhizoctonia solani、油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorum。
本发明提供了含3,4-二氯异噻唑的酰胺衍生物I在制备植物免疫激活剂用于防治真菌病害中的用途,所述真菌为病害:番茄早疫病,其拉丁名为:Alternaria solani、黄瓜灰霉病,其拉丁名为:Botrytis cinerea、花生褐斑病,其拉丁名为:Cercosporaarachidicola、禾谷镰孢病,其拉丁名为:Fusarium graminearum、苹果轮纹病,其拉丁名为:Physalospora piricola、水稻纹枯病,其拉丁名为:Rhizoctonia solani、油菜菌核病,其拉丁名为:Sclerotinia sclerotiorum。
本发明提供了含3,4-二氯异噻唑的酰胺衍生物I在制备抗烟草花叶病毒剂中的用途。
本发明提供了含3,4-二氯异噻唑的酰胺衍生物I在制备植物激活剂用于诱导烟草抗烟草花叶病毒中的用途。
本发明提供了含3,4-二氯异噻唑的酰胺衍生物I在制备杀虫、杀螨剂中的用途。
本发明提供了含3,4-二氯异噻唑的酰胺衍生物I在防治农业和林业以及园艺植物虫害中的用途。
本发明提供了含3,4-二氯异噻唑的酰胺衍生物I适用于防治农业和林业以及园艺植物的虫害和病原物以及诱导植物产生对植物虫害和病原物的防御能力,上述农药组合物包括农用杀菌组合物、农用杀虫组合物、农用抗植物病毒组合物、农用植物激活剂组合物,所诉组合物包含3,4-二氯异噻唑的酰胺衍生物作为活性成分;该组合物包含0.1%到99.9%重量的活性成分,99.9%到0.1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
C.含3,4-二氯异噻唑的酰胺衍生物I与的组合物及其用途:
含3,4-二氯异噻唑的酰胺衍生物I与商品农药共同形成一种农用组合物施用;所述商品农药选自:杀虫剂、杀菌剂、抗植物病毒剂、杀螨剂、植物激活剂中的一种或几种。该组合物含3,4-二氯异噻唑的酰胺衍生物I和其他商品杀虫剂、杀菌剂、抗植物病毒剂、杀螨剂、植物激活剂复配作为活性成分;该组合物活性成分的含量为1%∶99%到99%∶1%重量,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。具体的组合情况如下:
所述含3,4-二氯异噻唑的酰胺衍生物I与所述杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害;
所述杀虫剂选自:烯虫酯、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、七氟甲醚菊酯、氯氟醚菊酯、高效氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、β-氟氯氰菊酯、λ-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、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、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、多氟脲、氟螨脲、双苯氟脲、氟啶脲、嗪虫脲、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、敌敌畏、喹硫磷、哒嗪硫磷、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、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、三唑锡、噻嗪酮、杀虫单、杀虫双、氯虫酰胺、四氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、丁烯氟虫腈、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素、戊吡虫胍;
所述含3,4-二氯异噻唑的酰胺衍生物I在所述杀虫组合物中的质量百分含量是1%-90%;优选地,所述含3,4-二氯异噻唑的酰胺衍生物I与所述杀虫剂的比例为质量百分比1%∶99%到99%∶1%;
所述杀虫组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;
所述杀虫组合物防治的植物虫害选自:草地贪夜蛾、红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫;
所述杀虫组合物防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
所述含3,4-二氯异噻唑的酰胺衍生物I与所述杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害;
所述杀菌剂选自:苯并噻二唑、噻酰菌胺、甲噻诱胺、DL-β-氨基丁酸、异噻菌胺、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、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、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、萎锈灵、氧化萎锈灵、麦锈灵、甲呋酰胺、灭锈胺、氟酰胺、呋吡菌胺、噻呋酰胺、啶酰菌胺、吡噻菌胺、吡唑萘菌胺、联苯吡菌胺、氟吡菌酰胺、氟唑环菌胺、氟唑菌酰胺、氟唑菌苯胺、苯丙烯氟菌唑、异丙噻菌胺、氟唑菌酰羟胺、氟苯醚酰胺、氟醚菌酰胺、双炔酰菌胺、苯酰菌胺、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、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、噻呋酰胺、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、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、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、丰索磷、虫线磷、除线磷、杀线威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑;
所述含3,4-二氯异噻唑的酰胺衍生物I在所述杀菌组合物中总的质量百分含量是1%-90%;所述含3,4-二氯异噻唑的酰胺衍生物I与所述杀菌剂的比例为质量百分比1%∶99%到99%∶1%;
所述杀菌组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;
所述杀菌组合物防治的植物病害选自:稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病;
所述杀菌组合物适用的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
所述含3,4-二氯异噻唑的酰胺衍生物I与所述抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害;
所述抗病毒药剂选自:苯并噻二唑、噻酰菌胺、异噻菌胺DL-β-氨基丁酸、2,6-二氯异烟酸、N-氰甲基-2-氯异烟酰胺、烯丙异噻唑、病毒唑、安托芬、宁南霉素、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈霉素、盐酸吗啉胍;
所述含3,4-二氯异噻唑的酰胺衍生物I在所述抗病毒组合物中总的质量百分含量是1%-90%;优选地,所述含3,4-二氯异噻唑的酰胺衍生物I与所述抗植物病毒剂的比例为质量百分比1%∶99%到99%∶1%;
所述抗病毒组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;
所述抗病毒组合物防治的病毒病害选自:水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒;
所述抗病毒组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
所述含3,4-二氯异噻唑的酰胺衍生物I与所述杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害;
所述杀螨剂选自:敌敌畏、庚烯磷、速灭磷、二溴磷、嘧啶磷、氯甲亚胺硫磷、乙硫磷、虫螨畏、伏杀硫磷、甲基嘧啶硫磷、喹硫磷、蚜灭多、胺丙畏、氯亚胺硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、丁硫速灭威、蜱虱威、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵;
所述含3,4-二氯异噻唑的酰胺衍生物I在所述杀螨组合物中总的质量百分含量是1%-90%;所述含3,4-二氯异噻唑的酰胺衍生物I与所述杀螨剂的比例为质量百分比1%∶99%到99%∶1%;
所述杀螨组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;
所述杀螨组合物防治的螨害选自:螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨,所述害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨;
所述杀螨组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
所述含3,4-二氯异噻唑的酰胺衍生物I与所述植物免疫激活剂中的任意一种或两种组合形成植物免疫激活剂组合物用于防治农业和林业以及园艺植物病害;
所述植物激活剂药剂选自:苯并噻二唑、异噻菌胺、S-诱抗素、寡糖链蛋白、氨基寡糖素、香菇多糖、氟唑活化酯、低聚糖素、几丁聚糖、毒氟磷、DL-β-氨基丁酸、2,6-二氯异烟酸、N-氰甲基-2-氯异烟酰胺、烯丙异噻唑、甲噻诱胺、冠菌素、水杨酸、井冈霉素、超敏蛋白、昆布素、吡唑醚菌酯、烯丙异噻唑噻菌灵;
所述含3,4-二氯异噻唑的酰胺衍生物I在所述植物免疫激活剂组合物中总的质量百分含量是1%-90%;优选地,所述含3,4-二氯异噻唑的酰胺衍生物I与所述植物免疫激活剂的比例为质量百分比1%∶99%到99%∶1%;
所述植物免疫激活剂组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;
所述抗植物免疫激活剂组合物防治的病害选自:稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病、水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒;
所述植物免疫激活剂组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
本发明所述含3,4-二氯异噻唑的酰胺衍生物I的生物活性测定如下:
本发明的含3,4-二氯异噻唑的酰胺衍生物I的杀菌活性测定:
本发明的含3,4-二氯异噻唑的酰胺衍生物I的杀菌或抑菌活性采用菌体生长率测定法,具体步骤为:取1.8毫克样品溶解在2滴二甲基亚砜中,然后用含有一定量吐温20乳化剂的水溶液稀释至500微克/毫升的药剂,将供试药剂在无菌条件下各吸取1毫升于培养皿内,再分别加入9毫升PDA培养基,摇匀后制成50微克/毫升含药平板,以添加1毫升灭菌水的平板做空白对照,用直径4毫米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摄氏度恒温培养箱内培养,待对照菌落直径扩展到2-3厘米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,供试菌种为我国农业生产中田间实际发生的大部分典型植物病原菌的种属,其代号和名称如下:A.s:番茄早疫病菌,其拉丁名为:Alternaria solani、B.c:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、C.a:花生褐斑病菌,其拉丁名为:Cercospora arachidicola、F.g:禾谷镰孢病菌,其拉丁名为:Fusarium graminearum、P.p:苹果轮纹病菌,其拉丁名为:Physalospora piricola、R.c:禾谷丝核病菌,其拉丁名为:Rhizoctonia cerealis、S.s:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorum。
本发明的含3,4-二氯异噻唑的酰胺衍生物I的活体免疫诱导活性测定:
本发明的含3,4-二氯异噻唑的酰胺衍生物I的对拟南芥霜霉菌的免疫诱导活性采用孢子计数法,具体步骤为:取1.8毫克样品溶解在2滴N,N-二甲基甲酰胺中,然后用含有一定量吐温20乳化剂的水溶液稀释至100微摩尔/升的药剂。将拟南芥(Col-0)种子播种在生长室的土壤中,在16小时光照(22摄氏度)/8小时黑暗(20摄氏度)循环生长2周后,向20株拟南芥幼苗分别喷洒1毫升100微摩尔/升浓度的药剂;以不含试验化合物的0.2%DMF(N,N-二甲基甲酰胺)作为对照。化学处理24小时后,将收集分离得到的带有拟南芥霜霉菌的幼苗在无菌水中涡旋,然后用血球计数器计数确定水中孢子数目,将稀释至5×104孢子/毫升的拟南芥霜霉菌孢子液接种弄至拟南芥幼苗上。接种后,将幼苗置于温度为18摄氏度、湿度为80-100%的培养箱中,观察7天。为确定孢子数量,将收集的幼苗在无菌水中涡旋,然后用血球计数器计数,与对照比较计算相对抑菌率。每个处理包括三个重复。
本发明的有益效果是:对含3,4-二氯异噻唑的酰胺衍生物I进行了合成,并对含3,4-二氯异噻唑的酰胺衍生物I进行了抑菌活性的筛选和诱导植物抗真菌病害、细菌病害、病毒病害的活性筛选。
本发明通过特定制备和生物活性测定实施例更加具体说明含3,4-二氯异噻唑的酰胺衍生物I的合成与生物活性及应用,所述实施例仅用于具体说明本发明而非限制本发明,尤其是生物活性仅是举例说明,而非限制本专利,具体实施方式如下:
实施例1:化合物I-14的制备:
在100毫升单口圆底烧瓶中将甘氨酸甲酯盐酸盐(126.0毫克,1.0毫摩尔)溶于20毫升二氯甲烷中,再加入2当量三乙胺(0.29毫升,2.0毫摩尔),室温搅拌1分钟后,加入1.1当量3,4-二氯异噻唑-5-甲酰氯(0.16毫升,1.1毫摩尔),室温搅拌6小时,加入20毫升碳酸氢钠溶液淬灭,用20毫升二氯甲烷萃取三遍,合并有机相,用20毫升饱和食盐水洗有机相三次,并用无水硫酸钠干燥,减压除去溶剂,残余物经200~300目硅胶柱层析纯化,洗脱剂为乙酸乙酯/石油醚=1∶5(体积比),得到229毫克淡黄色固体I-14,产率为85%,本发明合成的化合物的化学结构和理化参数见表1和表2。
实施例2:本发明的3,4-二氯异噻唑的酰胺衍生物I的抑菌活性测定结果:
本发明测试的常见植物病原真菌代号和名称如下:A.s:番茄早疫病菌,其拉丁名为:Alternaria solani、B.c:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、C.a:花生褐斑病菌,其拉丁名为:Cercospora arachidicola、F.g:禾谷镰孢病菌,其拉丁名为:Fusarium graminearum、P.p:苹果轮纹病菌,其拉丁名为:Physalospora piricola、R.s:水稻纹枯病菌,其拉丁名为:Rhizoctonia solani、S.s:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorum。这些菌种具有很好的代表性,能够代表农业生产中田间发生的大部分病原菌的种属。
菌体生长率法测定结果见表3,表3表明,在50微克/毫升时,茉莉酸甲酯(MeJA)和商品化植物激活剂的BTH、ISO、TDL作为阳性对照开展了新化合物I的生物活性测定。结果表明,本发明合成的化合物本身对于7种病原菌在离体条件下的杀菌活性并不显著,符合植物激活剂本身没有离体或者离体活性低的特点。
实施例3:本发明的3,4-二氯异噻唑的酰胺衍生物I的活体免疫诱导活性测定:
本发明测试的活体免疫活性所用的菌为拟南芥霜霉菌,测试结果见表4,表4表明,在50微摩尔/升时,本发明合成的所有化合物的诱导抗病活性均在70%以上,均高出阳性对照化合物ISO在30%以上,其中,I-1、I-2、I-3、I-4、I-5、I-6、I-8、I-9、I-10、I-11、I-12、I-13、I-14对拟南芥霜霉菌的诱导抗病活性在85%以上,均比对照药ISO的38%还要多45%以上,且I-4、I-9、I-11、I-12、I-13、I-14对拟南芥霜霉菌的诱导抗病活性达到了100%,高于阳性对照药ISO和MeJA的38%和26%,与BTH的99%在数值上非常接近。降低浓度测试的结果发现,在10微摩尔/升时,阳性对照ISO仅有13%的诱导抗病活性,几乎丧失了生物活性,而化合物I-1、I-2、I-3、I-4、I-5、I-6、I-8、I-9、I-10、I-11、I-12、I-13、I-14对拟南芥霜霉菌的诱导抗病活性均在45%以上,其中I-4、I-14诱导抗病活性高达90%以上,优于阳性对照药BTH。综合实施例3的结果发现,本发明的化合物属于植物激活剂;植物激活剂的特点是具有广谱的抗病活性,本发明的化合物对植物病院真菌、细菌和病毒的效果与其诱导拟南芥抗霜霉病菌的活性相当,均显著高于阳性对照ISO。
实施例4:本发明的含3,4-二氯异噻唑的酰胺衍生物I在制备农药组合物中的应用:
本发明的含3,4-二氯异噻唑的酰胺衍生物I制备农药组合物,该组合物含本发明的含3,4-二氯异噻唑的酰胺衍生物I为活性成分,活性成分的质量百分含量为0.1%到99.9%,固体或液体助剂的质量百分含量为99.9%到0.1%,此外还含有任选0到25%质量百分含量的表面活性剂。
实施例5:本发明的含3,4-二氯异噻唑的酰胺衍生物I在制备农药复配组合物中的应用:
本发明的含3,4-二氯异噻唑的酰胺衍生物I可与其他商品农药,即杀虫剂、杀螨剂、杀菌剂、抗病毒剂或植物激活剂复配制备农药复配组合物,该复配组合物包含本发明的含3,4-二氯异噻唑的酰胺衍生物I和商品农药,即杀虫剂、杀螨剂、杀菌剂、抗病毒剂或植物激活剂作为活性成分,本发明的含3,4-二氯异噻唑的酰胺衍生物I与其他商品农药,即杀虫剂、杀螨剂、杀菌剂、抗病毒剂或植物激活剂的比例为质量百分比1%∶99%到99%∶1%,活性成分的质量百分含量为0.1%到99.9%,99.9%到0.1%质量百分含量的固体或液体助剂,以及任选0到25%质量百分含量的表面活性剂。
实施例6:本发明的含3,4-二氯异噻唑的酰胺衍生物I与植物激活剂组合在防治农业和林业以及园艺植物虫害中的应用:
本发明的含3,4-二氯异噻唑的酰胺衍生物I与商品植物免疫激活剂中的任意一种或两种组合形成植物免疫激活剂组合物用于防治农业和林业以及园艺植物病害;
所述植物激活剂药剂选自:苯并噻二唑、异噻菌胺、S-诱抗素、寡糖链蛋白、氨基寡糖素、香菇多糖、氟唑活化酯、低聚糖素、几丁聚糖、毒氟磷、DL-β-氨基丁酸、2,6-二氯异烟酸、N-氰甲基-2-氯异烟酰胺、烯丙异噻唑、甲噻诱胺、冠菌素、水杨酸、井冈霉素、超敏蛋白、昆布素、吡唑醚菌酯、烯丙异噻唑噻菌灵;
本发明的含3,4-二氯异噻唑的酰胺衍生物I在所述植物免疫激活剂组合物中总的质量百分含量是1%-90%;优选地,所述含3,4-二氯异噻唑的酰胺衍生物I与所述植物免疫激活剂的比例为质量百分比1%∶99%到99%∶1%;
所述植物免疫激活剂组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;
本发明的抗植物免疫激活剂组合物防治的病害选自:稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病、水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒;
本发明的植物免疫激活剂组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例7:本发明的含3,4-二氯异噻唑的酰胺衍生物I与杀虫剂组合在防治农业和林业以及园艺植物虫害中的应用:
本发明的含3,4-二氯异噻唑的酰胺衍生物I与商品杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害,所述商品杀虫剂选自:烯虫酯、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、七氟甲醚菊酯、氯氟醚菊酯、高效氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、β-氟氯氰菊酯、λ-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氟胺氰菊酯、吡虫啉、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、多氟脲、氟螨脲、双苯氟脲、氟啶脲、嗪虫脲、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、敌敌畏、喹硫磷、哒嗪硫磷、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、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、三唑锡、噻嗪酮、杀虫单、杀虫双、氯虫酰胺、四氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、丁烯氟虫腈、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素、戊吡虫胍;本发明的含3,4-二氯异噻唑的酰胺衍生物I在所述杀虫组合物中的质量百分含量是1%-90%,本发明的含3,4-二氯异噻唑的酰胺衍生物I与前述商品杀虫剂的比例为质量百分比1%∶99%到99%∶1%;所述杀虫组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀虫组合物适用的植物虫害选自:草地贪夜蛾、红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫;所述杀虫组合物适用的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例8:本发明的含3,4-二氯异噻唑的酰胺衍生物I与杀菌剂组合在防治农业和林业以及园艺植物病害中的应用:
本发明的含3,4-二氯异噻唑的酰胺衍生物I与商品杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害,所述商品杀菌剂选自:苯并噻二唑、噻酰菌胺、甲噻诱胺、异噻菌胺、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、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、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、萎锈灵、氧化萎锈灵、麦锈灵、甲呋酰胺、灭锈胺、氟酰胺、呋吡菌胺、噻呋酰胺、啶酰菌胺、吡噻菌胺、吡唑萘菌胺、联苯吡菌胺、氟吡菌酰胺、氟唑环菌胺、氟唑菌酰胺、氟唑菌苯胺、苯丙烯氟菌唑、异丙噻菌胺、氟唑菌酰羟胺、氟苯醚酰胺、氟醚菌酰胺、双炔酰菌胺、苯酰菌胺、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、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、噻呋酰胺、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、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、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、丰索磷、虫线磷、除线磷、丁硫环磷、杀线威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑;本发明的含3,4-二氯异噻唑的酰胺衍生物I在所述杀菌组合物中总的质量百分含量是1%-90%,本发明的含3,4-二氯异噻唑的酰胺衍生物I与前述商品杀菌剂的量百分比为1%∶99%到99%∶1%;所述杀菌组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀菌组合物适用的植物病害选自:稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病;所述杀菌组合物适用的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例9:本发明的含3,4-二氯异噻唑的酰胺衍生物I与抗植物病毒剂组合在防治农业和林业以及园艺植物病毒病害中的应用:
本发明的含3,4-二氯异噻唑的酰胺衍生物I与商品抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害,所述商品抗病毒药剂选自:苯并噻二唑、噻酰菌胺、异噻菌胺、病毒唑、安托芬、宁南霉素、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈霉素、盐酸吗啉胍;本发明的含3,4-二氯异噻唑的酰胺衍生物I在所述抗病毒组合物中总的质量百分含量是1%-90%,本发明的含3,4-二氯异噻唑的酰胺衍生物I与前述商品抗植物病毒剂的比例为质量百分比1%∶99%到99%∶1%;所述抗病毒组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述抗病毒组合物防治的病毒病害选自:水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒;所述抗病毒组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例10:本发明的含3,4-二氯异噻唑的酰胺衍生物I与杀螨剂组合在防治农业和林业以及园艺植物螨害中的应用:
本发明的含3,4-二氯异噻唑的酰胺衍生物I与商品杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害,所述商品杀螨剂选自:敌敌畏、庚烯磷、速灭磷、二溴磷、嘧啶磷、氯甲亚胺硫磷、乙硫磷、虫螨畏、伏杀硫磷、甲基嘧啶硫磷、喹硫磷、蚜灭多、胺丙畏、氯亚胺硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、丁硫速灭威、蜱虱威、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵;本发明的含3,4-二氯异噻唑的酰胺衍生物I在所述杀螨组合物中总的质量百分含量是1%-90%,本发明的含3,4-二氯异噻唑的酰胺衍生物I与所述商品杀螨剂的比例为质量百分比1%∶99%到99%∶1%;所述杀螨组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀螨组合物防治的螨害选自:螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨,这些害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨;所述杀螨组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
工业实用性
本发明提供一类含3,4-二氯异噻唑的酰胺衍生物;本发明所述衍生物能够调控农业、园艺和卫生以及林业植物害虫和植物病原物的生物活性,可用于农业领域、园艺领域、林业领域杀虫、杀螨、杀菌、抗植物病毒、诱导植物产生抗病性,具有较好的经济价值和应用前景。
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表3本发明的含3,4-二氯异噻唑的酰胺衍生物I的抑菌活性(50微克/毫升的抑制率/%)
序号 | 化合物编号 | A.s | B.c | C.a | F.g | P.p | R.s | S.s |
1 | I-1 | 30 | 42 | 29 | 10 | 19 | 26 | 28 |
2 | I-2 | 51 | 56 | 43 | 42 | 49 | 51 | 37 |
3 | I-3 | 34 | 44 | 23 | 8 | 26 | 0 | 21 |
4 | I-4 | 29 | 15 | 26 | 13 | 9 | 0 | 2 |
5 | I-5 | 52 | 46 | 28 | 39 | 41 | 50 | 36 |
6 | I-6 | 49 | 68 | 28 | 24 | 39 | 45 | 31 |
7 | I-7 | 42 | 20 | 29 | 4 | 13 | 0 | 6 |
8 | I-8 | 28 | 35 | 24 | 4 | 17 | 10 | 16 |
9 | I-9 | 38 | 53 | 30 | 18 | 28 | 34 | 31 |
10 | I-10 | 38 | 31 | 34 | 18 | 28 | 10 | 26 |
11 | I-11 | 43 | 66 | 43 | 26 | 44 | 47 | 47 |
12 | I-12 | 37 | 28 | 28 | 19 | 28 | 8 | 22 |
13 | I-13 | 29 | 19 | 23 | 0 | 17 | 0 | 10 |
14 | I-14 | 24 | 21 | 32 | 10 | 17 | 22 | 23 |
15 | MeJA | 5 | 0 | 17 | 15 | 9 | 7 | 5 |
16 | BTH | 13 | 17 | 18 | 12 | 19 | 74 | 5 |
17 | TDL | 43 | 55 | 43 | 42 | 44 | 65 | 43 |
18 | ISO | 9 | 36 | 17 | 15 | 17 | 34 | 5 |
A.s:番茄早疫病菌,其拉丁名为:Alternaria solani、B.c:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、C.a:花生褐斑病菌,其拉丁名为:Cercospora arachidicola、F.g:禾谷镰孢病菌,其拉丁名为:Fusarium graminearum、P.p:苹果轮纹病菌,其拉丁名为:Physalospora piricola、R.s:水稻纹枯病菌,其拉丁名为:Rhizoctonia solani、S.s:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorum。
表4本发明的含3,4-二氯异噻唑的酰胺衍生物I诱导拟南芥抗拟南芥霜霉菌的活体活性(抑制率/%)
序号 | 化合物编号 | 浓度(微摩尔/升) | 抑制率 |
1 | I-1 | 50 | 98 |
2 | I-1 | 10 | 45 |
3 | I-2 | 50 | 97 |
4 | I-2 | 10 | 57 |
5 | I-3 | 50 | 94 |
6 | I-3 | 10 | 55 |
7 | I-4 | 50 | 100 |
8 | I-4 | 10 | 93 |
9 | I-5 | 50 | 98 |
10 | I-5 | 10 | 66 |
11 | I-6 | 50 | 94 |
12 | I-6 | 10 | 63 |
13 | I-7 | 50 | 70 |
14 | I-8 | 50 | 97 |
15 | I-8 | 10 | 62 |
16 | I-9 | 50 | 100 |
17 | I-9 | 10 | 64 |
18 | I-10 | 50 | 87 |
19 | I-10 | 10 | 62 |
20 | I-11 | 50 | 100 |
21 | I-11 | 10 | 61 |
22 | I-12 | 50 | 100 |
23 | I-12 | 10 | 75 |
24 | I-13 | 50 | 100 |
25 | I-13 | 10 | 63 |
26 | I-14 | 50 | 100 |
27 | I-14 | 10 | 94 |
28 | ISO | 50 | 38 |
29 | ISO | 10 | 13 |
30 | BTH | 50 | 99 |
31 | BTH | 10 | 91 |
32 | MeJA | 50 | 26 |
Claims (10)
1.一类含3,4-二氯异噻唑的酰胺衍生物,其特征在于同时含有3,4-二氯异噻唑和酰胺的结构,具有如式I所示的结构通式:
其中,R1、R2、R3选自:取代烷基、取代烯基、氢、取代炔基、取代环烷基、取代环烯基、取代环炔基、取代烷氧基、取代烯氧基、取代炔氧基、取代的苯基、取代杂环基;
所述杂环基选自:呋喃基、噻吩基、咪唑基、吡唑基、吡啶基、吡喃基、吲哚基、嘧啶基、三嗪基、异吲哚基等含N或/和含硫的三元环基、四元环基、五元环基、六元环基;
R3还选自:Li、Na、K、Ca、Mg。
n选自1、3、4;
上述取代基优选:
R1选自:1-甲基乙基、1-甲基丙基、氢、2-(甲硫基)乙基、咪唑-4-甲基、2-甲基丙基、吲哚-3-甲基、3-甲氧基-3-氧代丙基、甲基、苯甲基、环己基甲基、甲基、苯甲基、对苯酚甲基、2-氨基-2-氧代乙基、羟甲基、乙氧基、3-胍基丙基、4-氨基丁基、羧甲基;R2选自氢、甲基;R3选自氢、钠、甲基、乙基、丙基、丁基、异丙基;n选自1、3、4。
2.根据权利要求1所述含3,4-二氯异噻唑的酰胺类衍生物I的具体合成路线如下:
所述取代基R1的定义如权利要求1所述;
根据权利要求1所述含3,4-二氯异噻唑的酰胺类衍生物I的具体合成方法如下:
具体合成方法为以下步骤:
A.化合物I的制备:
化合物I由3,4-二氯异噻唑-5-甲酰氯和氨基酸或氨基酸的酯或氨基酸的盐反应制备:
在室温下,将1当量的氨基甲酸酯盐酸盐2 加入二氯甲烷中,再加入2当量的三乙胺,室温搅拌1分钟后,加入1.1当量化合物1/>室温搅拌6小时,加入20毫升碳酸氢钠溶液淬灭,水相用二氯甲烷萃取,合并有机相,用饱和食盐水洗有机相三次,并用无水硫酸钠干燥,减压除去溶剂,残余物经200~300目硅胶柱层析纯化,洗脱剂为乙酸乙酯/石油醚,得到合3,4-二氯异噻唑的酰胺衍生物I;所述氨基甲酸酯盐酸盐选自:2-氨基-3-苯基丙酸甲酯盐酸盐、1-氨基环丙烷-1-甲酸乙酯盐酸盐、环亮氨酸甲酯盐酸盐、2-氨基异丁酸甲酯盐酸盐、2-氨基-3-环己基丙酸甲酯盐酸盐、1-氨基环己烷羧酸甲酯盐酸盐、L-缬氨酸甲酯盐酸盐、L-异亮氨酸甲酯盐酸盐、L-蛋氨酸甲酯盐酸盐、L-组氨酸甲酯二盐酸盐、L-亮氨酸叔丁酯盐酸盐、L-色氨酸甲酯盐酸盐、L-谷氨酸二甲酯盐酸盐、甘氨酸甲酯盐酸盐、L-丙氨酸甲酯盐酸盐、L-苯丙氨酸甲酯盐酸盐、L-酪氨酸甲酯盐酸盐、L-天冬酰胺甲酯盐酸盐、L-丝氨酸甲酯盐酸盐、L-苏氨酸甲酯盐酸盐、L-精氨酸甲酯盐酸盐、L-赖氨酸甲酯盐酸盐、L-天冬氨酸甲酯盐酸盐、L-脯氨酸甲酯盐酸盐、D-3-氨基丁酸、β-氨基丁酸。
3.权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物I在制备农用杀菌剂中的用途,所述杀菌剂防治的对象选自:番茄早疫病菌、黄瓜灰霉病菌、花生褐斑病菌、禾谷镰孢病菌、苹果轮纹病菌、水稻纹枯病菌、油菜菌核病菌、植物病毒病。
4.权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物I在制备植物激活剂中的用途,所述植物激活剂防治的对象选自:番茄早疫病、黄瓜灰霉病、花生褐斑病、禾谷镰孢病、苹果轮纹病、水稻纹枯病、油菜菌核病、植物病毒病。
5.一种农用杀菌组合物,该组合物包含权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物作为活性成分;该组合物包含0.1%到99.9%重量的活性成分,99.9%到0.1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
6.一种植物激活组合物,该组合物包含权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物作为活性成分;该组合物包含0.1%到99.9%重量的活性成分,99.9%到0.1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
7.一种农用杀菌复配组合物,其包含权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物和其他商品杀菌剂复配作为活性成分;活性成分含3,4-二氯异噻唑的酰胺衍生物与其他商品杀菌剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,及选自0到25%重量的表面活性剂。
8.一种农用杀虫、杀螨复配组合物,其包含权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物和其他商品杀虫、杀螨剂复配作为活性成分;活性成分含3,4-二氯异噻唑的酰胺衍生物与其他商品杀虫、杀螨剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,及选自0到25%重量的表面活性剂。
9.一种抗植物病毒剂复配组合物,其包含权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物和其他商品抗植物病毒剂复配作为活性成分;活性成分含3,4-二氯异噻唑的酰胺衍生物与其他商品抗植物病毒剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,及选自0到25%重量的表面活性剂。
10.一种植物激活剂复配组合物,其包含权利要求1所述的含3,4-二氯异噻唑的酰胺衍生物和其他商品植物激活剂复配作为活性成分;活性成分含3,4-二氯异噻唑的酰胺衍生物与其他商品植物激活剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,及选自0到25%重量的表面活性剂。
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