CN1491212A - 吡咯甲酰胺作为杀真菌剂的应用 - Google Patents
吡咯甲酰胺作为杀真菌剂的应用 Download PDFInfo
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- CN1491212A CN1491212A CNA028047559A CN02804755A CN1491212A CN 1491212 A CN1491212 A CN 1491212A CN A028047559 A CNA028047559 A CN A028047559A CN 02804755 A CN02804755 A CN 02804755A CN 1491212 A CN1491212 A CN 1491212A
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- 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
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
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- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本发明涉及新的通式(I)的吡咯甲酰胺,其中R1是CF3、CF2H或CFH2,R2是氢或氟;R3是氢或氟;和R4是氢、氟、氯、溴、甲基、CF3、OCF3或SCF3。通式(I)化合物具有保护植物的性能,适合于保护植物免受植物病原微生物的侵害。
Description
本发明涉及新的具有杀菌活性,特别是杀真菌活性的吡咯甲酰胺。本发明还涉及这些物质的制备,涉及包含至少一种新化合物作为活性成分的农药组合物,涉及上述组合物的制备以及这些活性成分或组合物在农业和园艺上的应用,用来控制或预防植物病原微生物,特别是真菌对植物的侵染。
本发明的吡咯甲酰胺具有通式I的结构
其中,
R1是CF3、CF2H或CFH2;
R2是氢或氟;
R3是氢或氟;和
R4是氢、氟、氯、溴、甲基、CF3、OCF3或SCF3。
令人惊奇地发现通式I化合物表现出更高的生物活性,使其更适宜于农业和园艺上的实际应用。
通式I的化合物中存在不对称的碳原子,这些化合物指的是光学上的旋光活性体,本发明涉及纯的异构体,如对映异构体和非对映异构体,还涉及所有可能的异构体的混合物,例如:非对映体的混合物、外消旋物或外消旋体的混合物。
通式I化合物的优选方案是这些化合物,其中
R1是CF3、CF2H或CFH2;或
R1是CF3;或
R2是氢或氟;或
R2是氢;或
R2是氟;或
R3是氢或氟;或
R3是氢;或
R3是氟;或
R4是氢、氯、甲基、CF3或OCF3;或
R4是氢或甲基;或
R4是氢,或
R2、R3和R4都是氢。
在通式I的化合物中下面一组化合物是优选的,其中
R1是CF3、CF2H或CFH2;
R2是氢或氟;
R3是氢或氟;和
R4是氢、氯、甲基、CF3或OCF3(亚组A)。
在亚组A中,以下化合物是优选的,其中
R1是CF3、CF2H或CFH2;
R2是氢;
R3是氢或氟;和
R4是氢、氯、甲基、CF3或OCF3(亚组A1)。
亚组A的通式I化合物的另一组化合物是以下化合物,其中
R1是CF3、CF2H或CFH2;
R2是氟;
R3是氢或氟;和
R4是氢、氯、甲基、CF3或OCF3(亚组A2)。
在这些亚组中,优选的化合物是其中R2、R3和R4都是氢的化合物。
优选的个别的化合物是:
1-甲基-4-三氟甲基-1H-吡咯-3-甲酸(4’-溴代联苯-2-基)酰胺;
1-甲基-4-二氟甲基-1H-吡咯-3-甲酸(4’-溴代联苯-2-基)酰胺。
通式I的化合物可以根据下面方案中的反应来制备。(Ac代表乙酰基)。
A)吡咯甲酸的合成:
路线1(Tosmic路线)
方案1
路线2(三氟乙酰乙酸路线,类似于JP-07157466)
方案2
碱1=NaHCO3、Na2CO3、KHCO3、K2CO3、CaCO3和其它碱
碱2=NaOH、KOH、NaH、KH、n-BuLi和其它碱
通式II中R2=H的吡咯甲酸的合成在WO-00/09482中描述。
通式II中R2是氟的吡咯甲酸的合成可根据方案2A或2B来进行。
方案2A
F+-试剂 =N-氟-二(苯基磺酰基)胺、N-氟-N-甲基甲苯-4-磺酰胺、2-氟-3,3-二甲基-2,3-二氢-1,2-苯并异噻唑-1,1-二氧化物、1-氟-对称-可力丁 四氟硼酸
LDA=二异丙基氨基化锂
方案2B
B)胺III的合成
方案3
(AlX3优选地是AlCl3;溶剂:水、DMF、THF、CH2Cl2、CHCl3、ClCH2CH2Cl、等)
C)酰胺的合成
方案4
碱=N(C2H5)3、Hünig-碱、Na2CO3、K2CO3和其它碱
吡咯甲酸II在溶剂的存在下与活化剂如亚硫酰氯、五氯化磷或草酸(或草酰氯)在0℃至回流温度条件下反应,反应时间30分钟至24小时,得到相应的酰基氯。有代表性的溶剂是甲苯、苯、二甲苯、己烷、环己烷、氯仿或二氯甲烷。获得的酰基氯正常情况下不离析。通式I中的新的甲酰胺优选地由下列反应获得,将活性吡咯甲酸与通式III的芳香胺在溶剂如甲苯、苯、二甲苯、己烷、环己烷、氯仿或二氯甲烷的存在下和酸结合剂如三乙胺、Hünig碱、碳酸钠、碳酸钾或碳酸氢钠的存在下于0℃至回流温度条件下反应。优选地,方案4中的整个反应系列以一个单容器反应来进行。
通式II中R1是CHF2的甲酸氟化物中间体可根据下面的反应路线获得。
方案5
其中,Q是基团
如通式I部分所定义,和X是F、-N(CH3)2、-N(C2H5)2、-N(CH2CH2OCH3)2或
试剂F3S-X是已知的,例如,J.Org.Chem,1999,(64),7048.
方案5的最后反应步骤包括一个偶联(酰胺化作用)反应,在1至2当量的空间位阻碱如DABCO(1,4-二氮杂二环[2.2.2]辛烷)的存在下加几滴乙腈作为接触介质进行反应较为有利,80℃至140℃的温度下加热反应混合物2至3小时直到反应发生。经过冷却步骤等后处理程序,得到最后的通式I中R1是CHF2的产物。
化合物B及其合成是专门用来生产本发明活性成分的,因此代表了本发明的另一特征。同样的新的化合物A以及上述的酯也是本发明的一部分。化合物A可通过下面反应获得。
方案6
其中,R*是C1-C6烷基、或Si(C1-C6烷基)3,和L是一离去基团如卤原子、-O-Tos等。反应步骤3是罗森蒙德(Rosenmund)反应的改进形式,在本领域是未知的,因此代表了本发明的另一特征。特别是第一步中的反应剂组合SOCl2/DMF或草酰二氯/DMF、催化量的DMF、可随意选择的惰性溶剂和第二步:还原条件如Pb在活性炭上,温度为0℃至+10℃,优选地0℃至+5℃,和在叔胺如Hünig-碱的存在下更有利。
另外,方案6中的3,4-二酯-1-甲基吡咯可根据(R.K.Huisgen,US3,285,931)获得,在方案7中概述。
方案7
现在我们惊奇地发现通式I的新化合物在保护植物抵抗由病原真菌以及细菌和病毒引起的病害中具有非常宽的活性谱。
通式I的化合物可被用于农业及其相关的领域,用作控制植物害虫的活性成分,这些新化合物在低施用率下就有良好的活性,对植物具有较好的耐受性,并且对环境安全。它们具有非常优异的药物性、保护性和内吸性,被用来保护多种作物。通式I中的化合物可用来抑制或杀死那些发生在各种有益农作物的植物体或植物体的部分器官(果实、花、叶。茎、块茎、根)上的害虫,同时也保护了后来长出的各植物部分如免受植物病原微生物的侵染。
通式I的化合物也可以作为修饰剂来处理植物繁殖材料,特别是种子(果实、块茎、谷粒)和植物插条(如水稻),以防止真菌的侵染和植物病原真菌在土壤中的发生。
化合物I对下面各纲的植物病原真菌是有效的,例如:半知菌类(如葡萄孢属、梨孢属、长孺孢属、镰孢菌属、壳针孢属、尾孢属和链格孢属)和担子菌纲(如丝核菌属、驼孢菌属、柄锈菌属),另外,它们对子囊菌纲(如黑星菌属和白粉菌属、叉丝单囊壳属、链核盘菌属、钩丝壳属)和卵菌纲(如疫霉属、腐霉属、单轴霉属)也是有效的,特别是对白粉病(白粉病菌)具有显著的活性,另外,通式I中的新化合物对植物病原细菌和病毒(如黄单孢杆菌、假单孢杆菌、梨火疫病菌以及烟草花叶病毒)也是有效的。
在本发明范围内,可以被保护的有代表性的目标作物包括如下的作物品种:谷类(小麦、大麦、黑麦、燕麦、水稻、玉米、高梁以及有关的种);甜菜(糖用甜菜和饲料甜菜);仁果、核果和浆果(苹果、梨、李、桃、杏、樱桃、草莓、悬钩子和黑刺莓);豆科植物(菜豆、扁豆、豌豆、大豆);油料作物(油菜、芥菜、罂粟、油橄榄、向日葵、椰子果、蓖麻、可可豆、花生);瓜类作物(南瓜、黄瓜、甜瓜);纤维作物(棉花、亚麻、大麻、黄麻);柑橘类的水果(橙子、柠檬、柚子、柑橘);蔬菜(菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯、红辣椒);樟科(lauraceae)(鳄梨、樟属、樟脑)或其它作物,如:烟草、坚果(nuts)、咖啡、茄子、甘蔗、茶叶、胡椒、藤、蛇麻草、香蕉和天然橡胶以及观赏植物。
通式I的化合物可以直接施用,优选地与该领域中常用的助剂混和使用,为此,它们通常用公知的方法加工成乳油、包衣糊剂(coatablepastes)、直接喷施或稀释后再喷施的液剂、稀乳剂、可湿性粉剂、可溶性粉剂、粉剂、颗粒剂以及包在聚合物中的胶囊剂,这些组合物各种剂型的选用和施用的方法,如喷洒、喷雾、喷粉、撒播、包膜或浇注,可以根据想要防治的目的作物和当时的环境而进行选择,这些组合物还可以包含其它的助剂,如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂和肥料、微量元素原料或其它制剂来获得特殊的效果。
合适的载体和助剂可以是固体的或液体的,是那些在剂型加工技术中有用的物质,例如天然的或经过加工的矿物质、溶剂、分散剂、润湿剂、增粘剂、增稠剂、粘合剂或肥料。这些载体如WO97/33890中所描述。
通式I的化合物经常以组合物的形式使用,施用到作物田或要防治的植物上,同时或之后施用另一种化合物,这些化合物可以是肥料或微量元素原料或其它影响植物生长的制剂。它们也可以是选择性的除草剂以及杀虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种上述制剂的混合物,如果需要还可再加入载体、表面活性剂或该领域常用的施用促进剂。
通式I化合物可与其它杀菌剂混和使用,一些情况下可得到预想不到的增效效果。混和成分特别优选地是唑类,如氧环唑、BAY14120、联苯三唑醇、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、氧唑菌、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、抑霉唑、亚胺唑、种菌唑、叶菌唑、睛菌唑、稻瘟酯、戊菌唑、啶斑肟、咪鲜胺、丙环唑、simeconazole、戊唑醇、四氟醚唑、三唑酮、三唑醇、氟菌唑、灭菌唑;嘧啶甲醇类,如环丙嘧啶醇、氯苯嘧啶醇、氟苯嘧啶醇;2-氨基-嘧啶类,如乙嘧吩磺酸酯、二甲嘧吩、乙嘧吩;吗啉类,如十二环吗啉、苯锈啶、丁苯吗啉、螺恶茂胺、十三吗啉;苯胺嘧啶类,如嘧菌环胺、嘧菌胺、嘧霉胺;吡咯类,如拌种咯、咯菌腈;苯酰胺类,如苯霜灵、呋霜灵、甲霜灵、R-甲霜灵、呋酰胺、恶霉灵;苯并咪唑类,如苯菌灵、多菌灵、咪菌威、麦穗宁、噻菌灵;二羧酰亚胺类,如乙菌利、菌核利、异菌脲、甲菌利、腐霉利、乙烯菌核利;羧酰胺类,如萎锈灵、呋菌胺、氟酰胺、灭锈胺、氧化萎锈灵、溴氟唑菌;胍类,如双胍辛醋酸盐、多果定、双胍辛;甲氧基丙烯酸酯类(strobilurines),如嘧菌酯、苯氧菌酯、苯氧菌胺、SSF-129、肟菌酯、啶氧菌酯、BAS500F(建议名:唑菌胺酯)、BAS20;二硫代氨基甲酸酯类,如福美铁、代森锰锌、代森锰、代森联、丙森锌、福美双、代森锌、福美锌;N-卤甲基硫代四氢苯邻二甲酰亚胺类,如敌菌丹、克菌丹、抑菌灵、氟氯菌核利、灭菌丹、甲苯氟磺胺;铜混合物,如波尔多液、氢氧化铜、王铜、硫酸铜、氧化亚铜、代森锰铜、喹啉铜;硝基酚衍生物类,如敌螨普、肽菌酯;有机磷衍生物类,如,敌瘟磷、异稻瘟净、稻瘟灵、氯瘟磷、吡菌磷、甲基立枯磷;各种其它杀菌剂,如噻二唑素-S-甲基、敌菌灵、杀草有效丹(benthiavalicarb)、灭瘟素、灭螨猛、地茂散、百菌清、cyflufenamid、霜脲氰、二氯萘醌、哒菌清、氯硝胺、乙霉威、烯酰吗啉、SYP-LI90(建议名:氟吗啉)、二氰蒽醌、噻唑菌胺、土菌灵、恶唑酮菌、咪唑菌酮、氰菌胺、三苯锡、嘧菌腙、氟啶胺、磺菌胺、环酰菌胺、三乙膦酸铝、恶霉灵、iprovalicarb、IKF-916(氰霜唑)、春雷霉素、磺菌威、metrafenone、nicobifen、戊菌隆、四氯苯酞、多抗霉素、烯丙苯噻唑、霜霉威、咯喹酮、喹氧灵、五氯硝基苯、硫磺粉、咪唑嗪、三环唑、嗪胺灵、有效霉素、zoxamide(RH7281)。
一种优选地施用通式I化合物或包含至少一种上述化合物的农药组合物的方法是叶面施用,施用的次数和用量要根据相应病原物的侵染危害程度而定,但是,用通式I的化合物的液体制剂淋湿植物所在的场所或者向土壤中施用这些化合物的固体剂型例如颗粒剂(土壤施药),这些化合物也可以经由土壤渗透到植物的根部(内吸作用),对于水稻,这样的颗粒剂可施用到大水漫灌的稻田中,通式I的化合物也可以用到种子(包衣)上,用液体剂型的杀菌剂浸泡种子或块茎,或用固体剂型对它们进行包衣。
这些制剂,也就是包括通式I化合物的组合物,如果需要还可包含固体或液体助剂,可用该领域公知的方法来制备,典型的是将该化合物与添加剂,如溶剂、固体载体和任选的一种表面活性化合物(表面活性剂)混和和/或研磨。
农药制剂通常含有0.1~99%,优选地0.1~95%重量的通式I化合物,含有99.9~1%,优选地99.8~5%重量的固体或液体助剂,和0~25%,优选地0.1~25%重量的表面活性剂。
较好的施用量一般为每公顷(ha)5g至2kg的活性成分(a.i.),优选地10g~1kg a.i./ha,更优选地20g~600g a.i./ha,当被用作浸种剂时,一般的剂量为每公斤的种子用10mg~1g活性物质。
但是,优选地作为浓缩物被加工成商业产品,施用时通常用稀释后的制剂。
下面的非限制的实施例更详细的阐述了上述的发明,温度指的是摄氏度,下面的缩写词将会用到:
m.p.=熔点;b.p.=沸点,“NMR”表示核磁共振谱,MS代表质谱,“%”为重量百分比,除非相应的制剂指明用其它的单位。
实施例1
1-甲基-4-三氟甲基-1H-吡咯-3-甲酸(4’-溴代联苯-2-基)酰胺
1-甲基-4-三氟甲基-1H-吡咯-3-甲酸(0.42g,2.2mmol)和草酰氯(0.30g,2.4mmol)的二氯甲烷(20ml)溶液于催化量的DMF存在下室温搅拌3小时。然后得到的酰基氯溶液慢慢的加入到2-(4’-溴苯基)苯胺(0.55g,2.2mmol)和三乙胺(0.33g,3.3mmol)的15ml二氯甲烷溶液中。得到的混合物再在室温下搅拌16小时。加入乙酸乙酯,有机相用水洗涤两次,通过Na2SO4干燥有机相,用水泵真空装置除去溶剂,得到的粗产物最后用柱色谱(硅胶;洗脱液:乙酸乙酯/己烷=1∶2)进行纯化,得到0.52g 1-甲基-4-三氟甲基-1H-吡咯-3-甲酸(4’-溴代联苯-2-基)酰胺,黄色粉末,熔点为163-164℃。
下面的通式I化合物用相似的路线相似的方法制备。
表1
化合物 | R1 | R2 | R3 | R4 | 物理参数,m.p.℃ |
1.1 | CF3 | H | H | H | 163-164 |
1.2 | CF2H | H | H | H | 166-167 |
1.3 | CFH2 | H | H | H | |
1.4 | CF3 | F | H | H | 树脂,M+=411 |
1.5 | CF2H | F | H | H | 树脂,M+=423 |
1.6 | CFH2 | F | H | H | |
1.7 | CF3 | H | 6-F | H | |
1.8 | CF2H | H | 6-F | H | |
1.9 | CF3 | F | 6-F | H | |
1.10 | CF2H | F | 6-F | H |
实施例2:4-甲酰基-1-甲基-1H-吡咯甲酸乙酯
21.6g(0.11mol)1-甲基-1H-吡咯(pyrrazole)-3,4-二甲酸单乙酯和14.9g(0.117mol)草酰氯的150ml二氯甲烷溶液在催化量的无水DMF存在下室温搅拌3小时。3小时后用水泵真空装置分出溶剂,粗酰基氯(21.5g)溶解在400ml的无水四氢呋喃中。加入14.2g(0.11mol)N,N-二异丙基乙胺(Hünig-碱)后,混合物在6.0g 10%Pd/C存在下0°-5℃用氢进行氢化5.5小时,然后过虑掉催化剂,水泵真空装置除去溶剂。粗产物用硅胶的快速色谱法(洗脱液:叔丁甲醚/己烷1∶5)纯化。得产物16g 4-甲酰基-1-甲基-1H-吡咯甲酸乙酯,黄色粉末;m.p.:75°-76℃。
实施例3: 4-甲酰基-1-甲基-1H-吡咯甲酸
向4.6g(0.0255mol)4-甲酰基-1-甲基-1H-吡咯甲酸乙酯的90ml乙醇溶液中加入2.1g(0.031mol)85%氢氧化钾的20ml水溶液,产生轻微的放热反应。得到的混合物+80℃下搅拌2小时,然后真空蒸掉溶剂混合物EtOH/H2O。得到的油溶解在100ml水中,用乙酸乙酯洗涤两次。然后20ml的2N氯化氢溶液在冷却的条件下慢慢加入到水相中。过虑出沉淀固体,用水洗涤,真空电炉中干燥沉淀物获得纯酸产物:3.6g 4-甲酰基-1-甲基-1H-吡咯甲酸,微黄色粉末;m.p.:178°-180℃。
实施例3:
4-二氟甲基-1-甲基-1H-吡咯-3-羰酰氟
向冷却的2.6g(0.017mol)4-甲酰基-1-甲基-1H-吡咯甲酸的70ml二氯甲烷溶液中加入11.0g(0.068mol)二乙胺硫三氟化物(diethylaminosulfurtrifluoride)(DAST)的10ml二氯甲烷溶液,在此过程中温度保持在0°至+2℃。然后混合物在0℃下搅拌30分钟,再在室温下放置16小时。反应混合物加入乙酸乙酯中,用冰水和盐水洗涤两次。水泵真空装置除去溶剂,干燥后,残余物用硅胶的快速色谱法(洗脱液:己烷/乙酸乙酯2∶1)纯化,得产物:1.95g 4-二氟甲基-1-甲基-1H-吡咯-3-羰酰氟,褐色固体;m.p.:53°-54℃。
表2中通式B的中间体可用相似的方法获得。
表2
化合物 No. | R* | 物理参数(m.p.[℃]) |
1.1 | CH3 | |
1.2 | C2H5 | 76-77 |
1.3 | C3H7-n | |
1.4 | C4H9-n | |
1.5 | C6H13-n | |
1.6 | Si(CH3)3 |
通式I化合物的制剂实施例
制备通式I化合物制剂如乳油、液剂、颗粒剂、粉剂和可湿性粉剂的工作程序在WO97/33890中描述。
生物实施例:杀真菌效果
实施例B-1:对隐匿柄锈菌(Puccinia recondita)/小麦(小麦叶锈病)的
效果
生长一周的小麦植株cv.Arina在喷雾室中用加工好的用于测试的化合物(0.02%的活性成分)进行处理,处理后一天在供试的小麦植株上通过喷施孢子悬浮液(1×105个夏孢子/ml)接种,在20℃,95%的相对湿度条件下经过2天的孵育期,再在20℃,60%相对湿度的温室条件下孵育8天,接种10天后测算发病率。
在该实验中,表1中的化合物表现出了良好的活性(<20%受到侵染)。使用化合物1.1、1.2、1.4和1.5实际上完全防止了侵染(0-5%受到侵染)。
实施例B-2:对白叉丝单囊壳菌(Podosphaera leucotricha)/苹果(苹果
白粉病)的效果
生长五周的苹果苗cv.Mclntosh在喷雾室中用加工好的用于测试的化合物(0.002%的活性成分)进行处理,处理后一天在供试的植株上通过抖动被苹果白粉病菌侵染的植物接种,在22℃、60%相对湿度,14/10h(白昼/黑暗)的光照条件下,经过12天的孵育期后测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出较强的效果(<20%受到侵染)。
实施例B-3:对苹果黑星菌(Venturia inaequalis)/苹果(苹果疮痂病)
的效果
生长四周的苹果苗cv.Mclntosh在喷雾室中用加工好的用于测试的化合物(0.02%的活性成分)进行处理,处理后一天在供试的植株上喷施孢子悬浮液(4×105个分生孢子/ml),21℃、95%相对湿度的条件下孵育4天,再在21℃、60%相对湿度的温室条件下孵育4天,然后再在21℃、95%相对湿度的条件下经过4天的孵育期后测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出较强的效果(<20%受到侵染)。
实施例B-4:对禾谷白粉菌(Erysiphe graminis)/大麦(大麦白粉病)的
效果
生长一周的大麦植株cv.Express在喷雾室中用加工好的用于测试的化合物(0.02%的活性成分)进行处理,处理后一天在供试的植株上通过抖动被侵染植物上的白粉病菌来接种,在20℃/18℃(白天/黑夜),相对湿度60%的温室条件下,经过6天的孵育期后测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出较强的效果(<20%受到侵染)。
实施例B-5:对灰葡萄孢菌(Botrytis cinerea)/苹果(苹果灰霉病)的效
果
在苹果cv.Golden Delicious的果实上钻3个孔,每孔滴入30μl加工好的用于测试的化合物(0.002%的活性成分),2小时后用吸管吸50μl灰葡萄孢菌的孢子悬浮液(4×105个分生孢子/ml)滴到处理部位,在22℃的生长室中经过7天的孵育期,测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出非常强的效果(<10%受到侵染)。
实施例B-6:对灰葡萄孢菌(Botrytis cinerea)/葡萄(葡萄灰霉病)的
效果
生长五周的葡萄苗cv.Gutedel在喷雾室中用加工好的用于测试的化合物(0.002%的活性成分)进行处理,处理后2天在供试植株上喷施孢子悬浮液(1×106个分生孢子/ml),在21℃、95%相对湿度的温室条件下,经过4天的孵育期,测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出非常强的效果(<10%受到侵染)。
实施例B-7:对灰葡萄孢菌(Botrytis cinerea)/番茄(番茄灰霉病)的效
果
生长四周的番茄植株cv.Roter Gnom在喷雾室中用加工好的用于测试的化合物(0.002%的活性成分)进行处理,处理后2天在供试番茄植株上喷施孢子悬浮液(1×105个分生孢子/ml),在20℃、95%相对湿度的生长室中,经过4天的孵育期后测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出非常强的效果(<10%受到侵染)。
实施例B-8:对圆核腔菌(Pyrenophora teres)/大麦(大麦网斑病)的效
果
生长一周的大麦植株cv.Express在喷雾室中用加工好的用于测试的化合物(0.002%的活性成分)进行处理,处理后2天向供试的植株上喷施孢子悬浮液(3×104个分生孢子/ml)来接种,20℃,95%相对湿度的条件下孵育2天,再在20℃,60%相对湿度的温室条件下,经过2天的孵育期,接种后4天测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出较强的效果(<20%受到侵染)。
实施例B-9:对颖枯壳针孢菌(Septoria nodorum)/小麦(小麦颖枯病)
的效果
生长一周的小麦植株cv.Arina在喷雾室中用加工好的用于测试的化合物(0.02%的活性成分)进行处理,一天后在供试的小麦植株上喷施孢子悬浮液(5×105个分生孢子/ml)进行接种,在20℃,95%相对湿度的条件下经过1天的孵育期后,再在20℃,60%的相对湿度的温室条件下孵育10天,接种11天后测算发病率。
在该实验中,表1中的化合物显示出了良好的活性。化合物1.1、1.2、1.4和1.5表现出较强的效果(<20%受到侵染)。
Claims (11)
2.根据权利要求1的通式I化合物,其中,R4是氢、氯、甲基、CF3或OCF3。
3.根据权利要求2的通式I化合物,其中,R2是氢。
4.根据权利要求2的通式I化合物,其中,R2是氟。
5.根据权利要求1的通式I化合物,该化合物选自
1-甲基-4-三氟甲基-1H-吡咯-3-甲酸(4’-溴代联苯-2-基)酰胺或
1-甲基-4-二氟甲基-1H-吡咯-3-甲酸(4’-溴代联苯-2-基)酰胺。
7.控制微生物和防止植物遭受侵染的组合物,其中,有效成分是权利要求1所述的化合物,和一种适合的载体。
8.一种控制或防止作物遭受植物病原微生物侵染的方法,该方法包括将权利要求1中所述的通式I化合物施用到植物、植物的部分器官或其生长的场所。
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