CN1315943A - 5-氨基吡唑衍生物用于防治微生物的用途 - Google Patents
5-氨基吡唑衍生物用于防治微生物的用途 Download PDFInfo
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- CN1315943A CN1315943A CN99810381A CN99810381A CN1315943A CN 1315943 A CN1315943 A CN 1315943A CN 99810381 A CN99810381 A CN 99810381A CN 99810381 A CN99810381 A CN 99810381A CN 1315943 A CN1315943 A CN 1315943A
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- 244000005700 microbiome Species 0.000 title claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 22
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- 229910052799 carbon Inorganic materials 0.000 claims description 87
- -1 trifluoromethylthio, difluoro methylthio group Chemical group 0.000 claims description 68
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- 125000003545 alkoxy group Chemical group 0.000 claims description 22
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
部分已知的式(Ⅰ)的5-氨基吡唑衍生物特别适用于防治不希望的微生物以保护作物和材料,其中R1、R2、R3、R4、R5和Y具有说明书中给出的定义。本发明还涉及新的式(Ⅰa)和(Ⅰc)的5-氨基吡唑衍生物,其中R1、R2、R3、R5、R9、R10、R11和Y具有说明书中给出的定义,以及制备这些新物质的方法。
Description
本发明涉及5-氨基吡唑衍生物用于防治不希望的微生物的用途,所述的5-氨基吡唑衍生物中有一些是已知的。
已知有一些5-氨基吡唑衍生物适于防治动物害虫(参见WO-A96-21653)。然而,这些物质用于抗不希望的微生物的用途迄今为止尚未见有述。
现已发现下式(Ⅰ)的5-氨基吡唑衍生物特别适合于在作物保护和材料保护中防治不希望的微生物,其中R1代表烷基、环烷基、烷氧基烷基或卤代烷基,R2代表氢、卤素、氰基、硝基、卤代烷硫基、烷氧基羰基或链烯基氧基羰基,R3代表任选被取代的烷基或任选被取代的环烷基,R4代表氢、烷基或任选被取代的环烷基,Y代表任选被取代的链烷二基或链烯二基,和R5代表任选被取代的芳基或任选被取代的芳氧基。
令人惊奇的是,根据本发明可以使用的式(Ⅰ)的5-氨基吡唑衍生物显示出比结构上最相似的作用方向相同的现有技术物质好得多的杀微生物活性。
式(Ⅰ)提供了根据本发明可以使用的5-氨基吡唑衍生物的一般定义。
R1优选代表具有1-4个碳原子的烷基、具有3-7个碳原子的环烷基、在烷基部分具有1-4个碳原子和在烷氧基部分具有1-4个碳原子的烷氧基烷基,或代表具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷基。
R2优选代表氢、氟、氯、溴、氰基、硝基、三氟甲硫基、二氟甲硫基、在烷氧基部分具有1-4个碳原子的烷氧基羰基,或代表在链烯氧基部分具有2-4个碳原子的链烯氧基羰基。
R3优选代表任选被氰基取代的具有1-4个碳原子的烷基或代表任选被相同或不同的选自卤素和具有1-4个碳原子的烷基的取代基取代1-3次的具有3-6个碳原子的环烷基。
R4优选代表氢、具有1-4个碳原子的烷基或代表任选被相同或不同的选自卤素和具有1-4个碳原子的烷基的取代基取代1-3次的具有3-6个碳原子的环烷基。
Y优选代表任选被卤素和/或具有3-6个碳原子的环烷基一或二取代的具有1-4个碳原子的链烷二基或具有2-4个碳原子的链烯二基。
R5优选代表苯基或苯氧基,它们各可以被相同或不同的选自下列的取代基一至四取代:卤素、硝基、氰基、C1-C12-烷基、C1-C12-烷氧基、C1-C12-烷硫基、C1-C12-卤代烷基、C1-C12-卤代烷氧基、C1-C12-卤代烷硫基、C2-C12-链烯基、C1-C4-烷氧基-C2-C12-链烯基、C1-C4-烷硫基-C2-C12-链烯基、C2-C12-卤代链烯基、羧基、在烷基部分具有1-4个碳原子的羟基亚氨基烷基、在烷氧基部分具有1-4个碳原子和在烷基部分具有1-4个碳原子的烷氧基亚氨基烷基、在链烯氧基部分具有2-4个碳原子和在烷基部分具有1-4个碳原子的链烯氧基亚氨基烷基、在烷基部分具有1-6个碳原子的烷基羰基、在烷基部分具有1-4个碳原子的烷基羰基氧基,或者被苯基、苯氧基、苯硫基、苄基、苄氧基和/或吡啶氧基取代,这后六个基团本身又可以被相同或不同的选自下列的取代基一至三取代:卤素、硝基、氰基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基和C1-C4-卤代烷硫基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R6代表苯基或吡啶基,它们各可以被相同或不同的选自下列的取代基一至三取代:卤素、具有1-4个碳原子的烷基、具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷基和具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷氧基,或
R7代表具有1-6个碳原子的烷基或在烷氧基部分具有1-6个碳原子和在烷基部分具有1-6个碳原子的烷氧基烷基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R8代表具有1-6个碳原子的烷基、苄基或吡啶基甲基,其中后两个基团可以被相同或不同的选自下列的取代基一至三取代:卤素、具有1-4个碳原子的烷基、具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷基和具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷氧基,或
R1特别优选代表甲基、乙基、正-或异-丙基或正-、异-、仲-或叔-丁基,环丙基,代表甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、三氟甲基、二氟甲基、氟甲基、1-氯-1-乙基或1-氟-1-乙基。
R2特别优选代表氢、氟、氯、溴、氰基、硝基、三氟甲硫基、二氟甲硫基、甲氧基羰基、乙氧基羰基、正-或异-丙氧基羰基、正-、异-、仲-或叔-丁氧基羰基或烯丙氧基羰基。
R3特别优选代表甲基、乙基、正-或异-丙基或正-、异-、仲-或叔-丁基,或代表2-氰基乙基、环丙基、环戊基或环己基,其中后三个基团可以被相同或不同的选自氟、氯、甲基和乙基的基团一至三取代。
R4特别优选代表氢、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基,或代表环丙基、环戊基或环己基,其中后三个基团可以被相同或不同的选自氟、氯、甲基和乙基的基团一至三取代。
Y特别优选代表下列各式基团:-CH2-、-CH(CH3)-、-CH2CH2-、-CH(C2H5)-、-CH(C3H7-i)-、-CHF-、-CHCl-、-CH(环丙基)-或-CH=CH-。
R5特别优选代表苯基或苯氧基,它们各可以被相同或不同的选自下列的取代基一至四取代:氟、氯、溴、硝基、氰基、甲基、乙基、正-或异-丙基或正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基或正-、异-、仲-或叔-丁氧基、甲硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基、二氟甲硫基、羧基、在烷基部分具有1或2个碳原子的羟基亚氨基烷基、在烷氧基部分具有1-4个碳原子和在烷基部分具有1或2个碳原子的烷氧基亚氨基烷基、在链烯氧基部分具有2-4个碳原子和在烷基部分具有1或2个碳原子的链烯氧基亚氨基烷基、在烷基部分具有1-4个碳原子的烷基羰基、在烷基部分具有1-4个碳原子的烷基羰基氧基,或者被苯基、苯氧基、苯硫基、苄基、苄氧基和/或吡啶氧基取代,这后六个基团本身又可以被相同或不同的选自下列的取代基一至三取代:氟、氯、溴、硝基、氰基、甲基、乙基、叔丁基、甲硫基、甲氧基、乙氧基、正-或异-丙氧基或正-、异-、仲-或叔-丁氧基、三氟甲基、三氟甲氧基、二氟甲氧基和三氟甲硫基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R6代表苯基或吡啶基,它们各可以被相同或不同的选自下列的取代基一至三取代:氟、氯、溴、甲基、乙基、正丙基、具有1或2个碳原子和1-3个氟-、氯-和/或溴-原子的卤代烷基和具有1或2个碳原子和1-3个氟-、氯-和/或溴-原子的卤代烷氧基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中
R7代表具有1-4个碳原子的烷基或在烷氧基部分具有1-4个碳原子和在烷基部分具有1-4个碳原子的烷氧基烷基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R8代表具有1-4个碳原子的烷基、苄基或吡啶基甲基,其中后两个基团可以被相同或不同的选自下列的取代基一至三取代:氟、氯、溴、甲基、乙基、正丙基、具有1或2个碳原子和1-3个氟、氯和/或溴原子的卤代烷基和具有1或2个碳原子和1-3个氟、氯和/或溴原子的卤代烷氧基,或
R5代表下式基团:
R1非常特别优选代表甲基、乙基、异丙基、叔丁基、甲氧基甲基、1-氯-1-乙基、1-氟-1-乙基或环丙基,
R2非常特别优选代表氢、氯、溴、氰基、硝基、甲氧基羰基、乙氧基羰基或烯丙氧基羰基,
R3非常特别优选代表甲基、乙基、异丙基、叔丁基、环丙基或2-氰基乙基,
R4非常特别优选代表氢、甲基、乙基、异丙基或环丙基,
Y非常特别优选代表下列各式基团:-CH2-、-CH(CH3)-、-CH2-CH2-或-CH=CH-。
R5非常特别优选代表苯基或苯氧基,它们各可以被相同或不同的选自下列的取代基一至三取代:氟、氯、溴、硝基、氰基、甲基、乙基、正-和异-丙基、正-、异-、仲-和叔-丁基、甲氧基、乙氧基、正-和异-丙氧基、正-、异-、仲-和叔-丁氧基、甲硫基、三氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基、羧基、羟基亚氨基甲基、羟基亚氨基乙基、在烷氧基部分具有1-4个碳原子和在烷基部分具有1或2个碳原子的烷氧基亚氨基烷基、在烷基部分具有1或2个碳原子的烯丙氧基亚氨基烷基、甲基羰基、乙基羰基、甲基羰基氧基或乙基羰基氧基,或者被苯基、苯氧基、苯硫基、苄基、苄氧基和/或吡啶氧基取代,这后六个基团本身又可以被相同或不同的选自下列的取代基一至三取代:氟、氯、溴、硝基、氰基、甲基、叔丁基、甲硫基、甲氧基、乙氧基、正-和异-丙氧基、正-、异-、仲-和叔-丁氧基、三氟甲基、三氟甲氧基、二氟甲氧基和三氟甲硫基,或
R7代表甲基、乙基、正丙基或在烷氧基部分具有1-4个碳原子和在烷基部分具有1或2个碳原子的烷氧基烷基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R8代表甲基、乙基、正丙基、苄基或吡啶基甲基,其中后两个基团可以被相同或不同的选自下列的取代基一至三取代:氟、氯、溴、甲基、乙基、正丙基、三氟甲基和三氟甲氧基,或
取代基的给定定义可以按需要相互组合。此外,取代基的单个定义也可以不用。
一些可用于本发明的式(Ⅰ)的5-氨基吡唑衍生物是已知的(参见WO-A 96-21653)。
式(Ⅰa)的5-氨基吡唑衍生物是新的,其中a)R9代表氯,
R10代表基团,和R11代表氢,或b)R9和R11各代表氢,和
R10代表氢,和
R11代表氯、溴、甲氧基或三氟甲基。
式(Ⅰa)的5-氨基吡唑衍生物可以如下制备:
使用上述方法也可以制备式(Ⅰ)中的其它5-氨基吡唑衍生物。
式(Ⅰc)的5-氨基吡唑衍生物也是新的,其中R1、R2、R3、R5和Y具有表1中给出的意义。
表1
表1(续)
表1(续)
表1(续)
表1(续)
表1中列出的5-氨基吡唑衍生物同样通过上述方法制备。使用5-氨基-3-乙基-4-乙氧羰基-1-甲基吡唑和(3-氯苯基)乙酰氯为原料,本发明方法(a)的过程可以通过下式等式具体说明:
作为进行本发明方法(a)原料需要的式(Ⅱ)的5-氨基吡唑和(Ⅲ)的酰卤是已知的或可以通过已知方法制备(参见WO-A 96-21653)。
用于进行本发明方法(a)的合适的酸结合剂是所有的常规的无机或有机碱。优选使用碱金属或碱土金属的氢氧化物、碳酸盐或碳酸氢盐以及还有含氮碱。可以提到的例子是氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄基胺、二异丙基胺、吡啶、喹啉、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)和二氮杂双环十一烯(DBU)。
用于进行本发明方法(a)的合适的稀释剂是所有常用于这类反应的有机溶剂。
优选使用任选卤代的脂族或芳族烃、醚或腈类,例如环己烷、甲苯、氯苯、氯仿、二氯甲烷、二氯乙烷、二噁烷、四氢呋喃、乙醚或乙腈。
当进行本发明方法(a)时,反应温度可以在较宽的范围内变化。通常,反应在-40℃~+150℃、优选在0℃~100℃之间的温度下进行。
本发明方法(a)一般在常压下进行。然而,也可以在加压或减压下进行。
当进行本发明方法(a)时,一般每摩尔式(Ⅱ)的5-氨基吡唑使用1-2摩尔、优选1-1.5摩尔的式(Ⅲ)的酰卤。后处理通过常规方法进行。
作为进行本发明方法(b)原料需要的式(Ⅰb)的5-氨基吡唑衍生物是本发明可以使用的化合物。它们可以通过本发明方法(a)制备。
用于进行本发明方法(b)的合适的氯化剂是所有常用于引入氯的试剂。优选使用氯气、氯氧酸及其盐,例如次氯酸钠或次氯酸钾,还有氯化物,例如磺酰氯、二氯化二硫和五氯化磷。
用于进行本发明方法(b)的合适的稀释剂是所有常用于这类反应的有机溶剂。
优选使用任选卤代的脂族或芳族烃、醚或腈类,例如环己烷、甲苯、氯苯、氯仿、二氯甲烷、二氯乙烷、二噁烷、四氢呋喃、乙醚或乙腈。
用于进行本发明方法(b)的合适的催化剂是所有的常用于该类反应的反应促进剂。优选使用氯化氢、乙酸钠和游离基形成剂如偶氮异丁腈或二苯甲酰基过氧化物。
当进行本发明方法(b)时,反应温度同样可以在较宽的范围内变化。通常,反应在-40℃~+120℃、优选在0℃~80℃之间的温度下进行。
本发明方法(b)一般在常压下进行。然而,也可以在加压下进行。
当进行本发明方法(b)时,一般每摩尔式(Ⅰb)的5-氨基吡唑衍生物使用1-2摩尔、优选1-1.5摩尔的氯化剂。后处理也是通过常规方法进行。
根据本发明可使用的化合物具有强的杀微生物活性,并且可以用来在农作物保护和材料保护中防治不期望的微生物,例如真菌和细菌。
农作物保护中使用杀真菌剂来防治根肿菌(Plasmodiophoromycetes),卵孢真菌(Oomycetes),壶菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌纲(Deutermycetes)。
农作物保护中使用杀细菌剂来防治假单孢菌科(Pseudomonadaceae),根瘤菌科(Rhizobiaceae),肠杆菌科(Enterobacteriaceae),棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)。
作为例子可以提到上述一般名称下的真菌病和细菌病的一些病原体,但是不受此限制:黄单孢菌属种类(Xanthomonas),例如田野稻黄单孢菌变种(Xanthomonas campestris pv.oryzae);假单孢菌属种类(Pseudomonas),例如丁香黄瓜角斑病假单孢菌变种(Pseudomonas syringae pv.lachrymans);欧文氏杆菌属种类(Erwinia),例如解淀粉欧文氏杆菌(Erwiniaamylovora);腐霉属种类(Pythium),例如终极腐霉(Pythium ultimum);疫霉属种类(Phytophthora),例如蔓延疫霉(Phytophthora infestans);假霜霉属种类(Pseudoperonospora),例如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);单轴霉属种类(Plasmopara),例如葡萄生单轴霉(Plasmopara viticola);盘梗霉属种类(Bremia),例如莴苣盘梗霉(Bremia lactucae);霜霉属种类(Peronospora),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronospora brassicae);白粉菌属种类(Erysiphe),例如禾白粉菌(Erysiphe graminis);单丝壳菌属种类(Sphaerotheca),例如苍耳单丝壳菌(Sphaerothecafuliginea);柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaeraleucotricha);黑星菌属种类(Venturia),例如苹果黑星菌(Venturia inaequalis);核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pyrenophora graminea)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));旋孢菌属种类(Cochliobolus),例如禾旋孢菌(Cochliobolus sativus)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));单胞锈菌属种类(Uromyces),例如疣顶单胞锈菌(Uromycesappendiculatus);柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Puccinia recondita);核盘菌属种类(Sclerotinia),例如油菜核盘菌(SclerotiniaSclerotiorum);腥黑粉菌属种类(Tilletia),例如小麦网腥黑粉菌(Tilletia caries);黑粉菌属种类(Ustilago),例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);薄膜革菌属种类(Pellicularia),例如佐佐木氏薄膜革菌(Pelliculariasasakii);Pyricularia种类,例如Pyricularia oryzae;镰孢属种类(Fusarium),例如大刀镰孢(Fusarium culmorum);葡萄孢属种类(Botrytis),例如灰色葡萄孢(Botrytis cinerea);壳针孢属种类(Septoria),例如颖枯壳针孢(Septoria nodorum);小球腔菌属种类(Leptosphaeria),例如颖枯小球腔菌(Leptosphaerianodorum);尾孢属种类(Cercospora),例如Cercospora canescens;链格孢属种类(Alternaria),例如甘蓝黑斑病链格孢(Alternariabrassicae);假尾孢属种类(Pseudocercosporella),例如Pseudocercosporellaherpotrichoides。
植物对在防治植物病害所需要的浓度时的活性化合物具有好的耐受性的事实允许处理植物的地上部分,植物繁殖根株和种子,和处理土壤。
根据本发明可以使用的活性化合物特别用于防治稻上的Pyricularia oryzae和防治谷物病害,例如柄锈菌属种类(Puccinia),白粉菌属种类(Erysiphe)和镰孢属种类(Fusarium)。此外,本发明的物质成功地用来抗黑星菌属种类(Venturia),柄球菌属种类(Podosphaera)和单丝壳菌属种类(Sphaerotheca)。它们还具有非常好的体外作用。
根据本发明可以使用的活性化合物也可以用来提高农作物产量。此外,它们具有低毒性并且为植物所很好耐受。
在材料保护中,本发明化合物可以被用来保护工业材料不受不希望微生物的感染和破坏。
本说明书中的工业材料理解为是指制备出来用于工业应用的无生命材料。例如,意指受本发明活性化合物保护不受微生物改变或破坏的工业材料可以是粘合剂,胶料,纸张和纸板,纺织品,皮革,木材,涂料组合物和塑料制品,冷却润滑剂和其它能被微生物感染或破坏的材料。要保护的材料的范围内也可以提到生产工厂的部分,例如冷却水循环,其可能受微生物繁殖的不利影响。本发明范围内可以提到的工业材料优选是粘合剂,胶料,纸张和纸板,皮革,木材,涂料,冷却润滑剂和导热液,特别优选木材。
可以提到的能导致工业材料降解或改变的微生物是例如细菌,真菌,酵母,藻和粘液生物。本发明活性化合物优选作用于真菌,特别是霉菌,使木材退色和使木材遭破坏的真菌(担子菌纲),还杀粘液生物体和藻。
作为举例,可以提到下面属种:链格孢属(Alternaria),例如纤细链格孢(Alternaria tenuis),曲霉属(Aspergillus),例如黑色曲霉(Aspergillus niger),毛壳霉属(Chaetomium),例如球毛壳霉(Chaetomium globosum),粉孢革菌属(Coniophora),例如单纯粉孢革菌(Coniophora puetana),香菇属(Lentinus),例如虎皮香菇(Lentinus tigrinus),青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum),多孔菌属(Polyporus),例如变色多孔菌(Polyporus versicolor),短柄霉属(Aureobasidium),例如出芽短柄霉(Aureobasidium pullulans),Sclerophoma,例如Sclerophoma pityophila,木霉属(Trichoderma),例如绿色木霉(Trichoderma viride),埃希氏杆菌属(Escherichia),例如大肠埃希氏杆菌(Escherichia coli),假单孢菌属(Pseudomonas),例如铜绿假单孢菌(Pseudomonasaeruginosa),葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcusaureus)。
根据其特殊的物理和/或化学性质,活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂和包裹在聚合物中和用于种子的包被组合物中的细微胶囊,以及ULV冷雾和暖雾制剂。
这些制剂可以用已知的方式制备,例如,将活性化合物与扩充剂即液体溶剂,加压液化气体和/或固体载体混合,任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。如果使用的扩充剂是水,则也可以用例如有机溶剂作助溶剂。下面是主要适合用作液体溶剂的溶剂:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲亚砜,还有水。液化气体扩充剂或栽体理解为指常温常压下是气体的液体,例如气雾抛射剂,例如卤代烃,或者还有丁烷,丙烷,氮和二氧化碳。合适的固体栽体是:例如磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐。用于颗粒剂的适合的固体载体是:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,或者还有有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎。适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐或者还有蛋白质水解产物;适合的分散剂是:例如,木素亚硫酸盐废液和甲基纤维素。
制剂中,可以使用增粘剂,如羧甲基纤维素和天然和合成的粉状、颗粒或乳胶形式的聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,或者还有天然磷脂,如脑磷脂和卵磷脂和合成磷脂。其它的添加剂可以是矿物油和植物油。
可以使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和痕量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
根据本发明可使用的活性化合物可以以本身或者以其制剂也可以与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂混合使用,例如以扩大作用范围或者防止抗药性产生。在很多情况下实现增效作用,即混合物的活性超过了各个组分的活性。
混合物中共同成分的例子是下面的化合物:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacryl-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,epoxiconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,
quinconazole,五氯硝基苯(PCNB),quinoxyfen,
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-a-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基)-氨基甲酸异丙酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘代甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-N-碳酰苯胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫代氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴代甲基)戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫代氰酰甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基)-1-氧代-1H-茚-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑啉基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-硫代苯二羧酸酯,
顺-1-(4-氯代苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉]盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑啉基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲烷亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸钠盐,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
bromopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,阿凡曼菌素,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡咯-3-腈,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,chloethocarb,chlorethoxyfos,chlorfenapyr,毒虫畏,定虫隆,氯甲硫磷,N-[(6-氯-3-吡啶基)-甲基]-N’-氰基-N-甲基-乙亚胺酰胺,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,
甲基毒虫畏,敌噁磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,异阿凡曼菌素,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NC184,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyridaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,zetamethrin。
也可能是与其它已知的活性化合物例如除草剂,肥料和生长调节物质的混合物。
活性化合物可以使用其自身或者以其制剂形式或者以从中制备的使用形式使用,例如即用型溶液,混悬剂,可湿粉剂,糊剂,可溶粉剂,细粉剂和颗粒剂。以常规方法使用,例如通过浇灌,喷雾,弥雾,散播,撒细粉,发泡,刷涂在其上等。此外还能通过超低体积方法施用活性化合物,或者将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
当使用根据本发明可以使用的活性化合物作为杀真菌剂时,施用比例可以在相当宽的范围内变化,取决于施用类型。处理植物部分时,活性化合物施用比例一般是0.1和10000g/ha之间,优选在10-1000g/ha之间。在处理种子时,活性化合物施用比例一般是每千克种子用0.001-50g,优选0.01-10g。处理土壤情况下,活性化合物施用比例一般是0.1和10000g/ha之间,优选在1和5000g/ha之间。
用来保护工业材料的组合物一般以1-95%重量比的量,优选10-75%重量比的量含有活性化合物。
根据本发明可以使用的活性化合物的使用浓度取决于要防治的微生物的种类和发生情况,和取决于要保护的材料的组成。最佳施用比例可以通过试验系列确定。一般情况下,使用浓度在以要保护的材料为基础的0.001-5%重量比范围内,优选0.05-1.0%重量比。
如果适当,通过加入其它抗微生物活性化合物,杀真菌剂,杀细菌剂,除草剂,杀昆虫剂或者其它扩大活性范围或者获得特殊效果例如另外的抗昆虫的保护作用的活性化合物,可以提高根据本发明要在材料保护中使用的活性化合物或组合物、浓缩物或者从中制备的很一般的制剂的活性和活性范围。这些混合物具有比本发明化合物更广范围的活性。
本发明活性化合物的制备和应用通过下面的实施例详细说明。制备实施例实施例1
室温下,向0.99g(0.005mol)5-氨基-4-乙氧羰基-3-乙基-1-甲基吡唑在80ml二氯甲烷中的溶液中加入0.47g(0.006mol)吡啶。然后在同样的温度下滴加1.11g(0.006mol)4-甲氧基苯基乙酰氯在20ml二氯甲烷中的溶液。将混合物在室温下搅拌过夜,然后回流24小时。冷却后,将反应混合物用稀盐酸和稀的碳酸氢钠水溶液洗涤。有机相用硫酸镁干燥、过滤并蒸发至干。
室温下,向1.25g(0.01mol)5-氨基-3-乙基-1-甲基吡唑在120ml二氯甲烷中的溶液中加入0.95g(0.012mol)吡啶。然后在同样的温度下滴加3.37g(0.012mol)4-(4-氯苯氧基)苯基乙酰氯在30ml二氯甲烷中的溶液。将混合物在室温下搅拌过夜,然后依次用稀盐酸和稀的碳酸氢钠水溶液洗涤。有机相用硫酸镁干燥、过滤并蒸发至干。
得到3.10g(理论量的84%)的5-(4-(4-氯苯氧基)苯基乙酰基氨基)-3-乙基-1-甲基吡唑,为棕色油状物。
0℃下,向0.92g(0.0025mol)5-(4-(4-氯苯氧基)苯基乙酰基氨基)-3-乙基-1-甲基吡唑(实施例2)在l0ml二氯甲烷中的溶液中加入0.37g(0.00275mol)磺酰氯。将混合物在室温下搅拌过夜,然后用10ml二氯甲烷稀释,依次用水、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗涤,用硫酸镁干燥、过滤并蒸发至干。
得到0.80g(理论量的79%)的4-氯-5-(4-(4-氯苯氧基)苯基乙酰基氨基)-3-乙基-1-甲基吡唑,为棕色油状物。1H-NMR(CDCl3):=1.21,2.57,3.63,3.77,6.82,6.92-7.04,7.30-7.35ppm。实施例4
0℃下,向0.92g(0.0025mo1)5-(4-(4-氯苯氧基)苯基乙酰基氨基)-3-乙基-1-甲基吡唑(实施例2)在10ml二氯甲烷中的溶液中加入0.44g(0.00275mol)溴。将混合物在室温下搅拌过夜,然后用10ml二氯甲烷稀释,依次用水、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗涤,用硫酸镁干燥、过滤并蒸发至干。
得到0.90g(理论量的80%)的4-溴-5-(4-(4-氯苯氧基)苯基乙酰基氨基)-3-乙基-1-甲基吡唑,为棕色油状物。
室温下,向3.19g(0.02mol)5-氨基-4-氯-3-乙基-1-甲基吡唑(实施例Ⅳ-1)在120ml二氯甲烷中的溶液中加入1.90g(0.024mol)吡啶。然后在同样的温度下滴加5.60g(0.024mol)4-溴苯基乙酰氯在30ml二氯甲烷中的溶液。将混合物在室温下搅拌过夜,然后用稀盐酸和稀的碳酸氢钠水溶液洗涤。有机相用硫酸镁干燥、过滤并蒸发至干。
得到4.61g(理论量的63%)的5-(4-溴苯基乙酰基)-氨基-4-氯-3-乙基-1-甲基吡唑,为无色固体,熔点167-168℃。
表2中所列的式(Ⅰ)的5-氨基吡唑衍生物同样按照上述方法制备。
表2(续)
表2(续)实施例89
将1.0g(4.70mmol)5-氨基-3-乙基-4-乙氧羰基-1-甲基吡唑、0.75g(9.40mmol)吡啶和10ml二氯甲烷的混合物与1.07g(5.60mmol)(3-氯苯基)乙酰氯混合并在20℃下搅拌18小时。然后,将反应混合物与二氯甲烷和水混合。分离有机相,依次用10%的盐酸水溶液和饱和碳酸氢钠水溶液洗涤,然后用硫酸镁干燥、过滤并减压浓缩。得到0.97g(理论量的59%)的5-(3-氯苯基乙酰基)-氨基-3-乙基-4-乙氧羰基-1-甲基吡唑,为油状液体形式。
LogP(酸性的):2.65。
表3中所列的式(Ⅰ)的5-氨基吡唑衍生物同样按照上述方法制备。
室温下,将26.74g(75mmol)5-(4-溴苯基乙酰基)氨基-4-氯-3-乙基-1-甲基吡唑和117ml的2M碳酸钠水溶液在搅拌下滴加到5.25g(4.5mmol)的四(三苯基膦)钯和150ml甲苯的混合物中。然后,剧烈搅拌下,在室温下滴加20.48g(82.5mmol)4-三氟甲氧基苯基硼酸在75ml乙醇中的溶液。将反应混合物先加热回流16小时,然后冷却到室温,与水和乙醚混合。分离有机相,用氯化钠水溶液洗涤,用硫酸镁干燥、过滤并减压浓缩。剩余的产物在硅胶上用二氯甲烷/乙酸乙酯=1∶1的混合物进行色谱。得到16.94g(理论量的52%)的上面给出的化合物,为固体形式,熔点174℃。
表4
表4(续)
表4(续)
应用实施例
实施例A
白粉病(Erysiphe)试验(小麦)/保护性的
溶剂:25份重量的N,N-二甲基乙酰胺
乳化剂:0.6份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以给定的施用比例,用活性化合物制剂喷雾幼小植物。
喷雾层风干后,将麦类白粉病(Erysiphe graminis f.sp.tritici)的孢子撒在植物上。
植物放置在温度大约20℃且相对空气湿度是大约80%的温室中以促进霉农疱的生长。
接种后7天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物、施用比例和试验结果。
表A
实施例B
圆核腔菌(Pyrenophora teres)试验(大麦)/治愈性的
溶剂:25份重量的N,N-二甲基乙酰胺
乳化剂:0.6份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验治愈性活性,用圆核腔菌(Pyrenophora teres)分生孢子悬浮液对幼小植物喷雾。将植物保留在20℃和100%相对空气湿度的培养室中48小时,然后以所述施用比例的活性化合物制剂对植物喷雾。
植物放置在温度大约20℃且相对空气湿度是大约80%的温室中。
接种后7天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物,施用比例和试验结果。
表B
圆核腔菌(Pyrenophora teres)试验(大麦)/治愈性的
实施例C
柄球菌属(Podosphaera)试验(苹果)/保护性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以给定的施用比例的活性化合物制剂喷雾幼小植物。喷雾层风干后,用苹果霉病原体Podosphaera leucotricha的孢子水悬浮液接种植物。然后植物放置在温度大约23℃且相对空气湿度是大约70%的温室中。
接种后10天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物,施用比例和试验结果。
表C
柄球菌属(Podosphaera)试验(苹果)/保护性的
实施例D
单丝壳菌属(Sphaerotheca)试验(黄瓜)/保护性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以给定的施用比例的活性化合物制剂喷雾幼小植物。喷雾层风干后,用苍耳单丝壳菌(Sphaerotheca fuliginea)的孢子水悬浮液接种植物。然后植物放置在温度大约23℃且相对空气湿度是大约70%的温室中。
接种后10天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物,施用比例和试验结果。
表D
单丝壳菌属(Sphaerotheca)试验(黄瓜)/保护性的
实施例E
黑星菌属(Venturia)试验(苹果)/保护性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以给定的施用比例的活性化合物制剂喷雾幼小植物。喷雾层风干后,用苹果病原菌苹果黑星菌(Venturia inaequalis)的分生孢子水悬浮液接种植物,然后将植物保留在大约20℃和100%相对空气湿度的培养室中1天。
然后,将植物放置在温度大约21℃且相对空气湿度是大约90%的温室中。
接种后12天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物,施用比例和试验结果。
表E
Claims (9)
2.根据权利要求1的用途,其特征在于使用取代基定义如下的式(Ⅰ)的5-氨基吡唑衍生物,其中
R1代表具有1-4个碳原子的烷基、具有3-7个碳原子的环烷基、在烷基部分具有1-4个碳原子和在烷氧基部分具有1-4个碳原子的烷氧基烷基,或代表具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷基,
R2代表氢、氟、氯、溴、氰基、硝基、三氟甲硫基、二氟甲硫基、在烷氧基部分具有1-4个碳原子的烷氧基羰基,或代表在链烯氧基部分具有2-4个碳原子的链烯氧基羰基,
R3代表任选被氰基取代的具有1-4个碳原子的烷基或代表任选被相同或不同的选自卤素和具有1-4个碳原子的烷基的取代基取代1-3次的具有3-6个碳原子的环烷基,
R4代表氢、具有1-4个碳原子的烷基或代表任选被相同或不同的选自卤素和具有1-4个碳原子的烷基的取代基取代1-3次的具有3-6个碳原子的环烷基,
Y代表任选被卤素和/或具有3-6个碳原子的环烷基一或二取代的具有1-4个碳原子的链烷二基,和
R5代表苯基或苯氧基,它们各可以被相同或不同的选自下列的取代基一至四取代:卤素、硝基、氰基、C1-C12-烷基、C1-C12-烷氧基、C1-C12-烷硫基、C1-C12-卤代烷基、C1-C12-卤代烷氧基、C1-C12-卤代烷硫基、C2-C12-链烯基、C1-C4-烷氧基-C2-C12-链烯基、C1-C4-烷硫基-C2-C12-链烯基、C2-C12-卤代链烯基、羧基、在烷基部分具有1-4个碳原子的羟基亚氨基烷基、在烷氧基部分具有1-4个碳原子和在烷基部分具有1-4个碳原子的烷氧基亚氨基烷基、在链烯氧基部分具有2-4个碳原子和在烷基部分具有1-4个碳原子的链烯氧基亚氨基烷基、在烷基部分具有1-6个碳原子的烷基羰基、在烷基部分具有1-4个碳原子的烷基羰基氧基,或者被苯基、苯氧基、苯硫基、苄基、苄氧基和/或吡啶氧基取代,这后六个基团本身又可以被相同或不同的选自下列的取代基一至三取代:卤素、硝基、氰基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基和C1-C4-卤代烷硫基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R6代表苯基或吡啶基,它们各可以被相同或不同的选自下列的取代基一至三取代:卤素、具有1-4个碳原子的烷基、具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷基和具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷氧基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R7代表具有1-6个碳原子的烷基或在烷氧基部分具有1-6个碳原子和在烷基部分具有1-6个碳原子的烷氧基烷基,或
R5代表苯基或苯氧基,它们各被下式基团单取代:其中R8代表具有1-6个碳原子的烷基、苄基或吡啶基甲基,其中后两个基团可以被相同或不同的选自下列的取代基一至三取代:卤素、具有1-4个碳原子的烷基、具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷基和具有1-4个碳原子和1-5个相同或不相同的卤原子的卤代烷氧基,或
3.防治农作物保护和材料保护中的不期望微生物的方法,其特征在于对微生物和/或其栖生地施用权利要求1的式(Ⅰ)的5-氨基吡唑衍生物。
6.杀微生物组合物,其特征在于它们含有至少一种权利要求4的式(Ⅰa)的5-氨基吡唑衍生物和扩充剂和/或表面活性剂。
7.制备杀微生物组合物的方法,其特征在于将权利要求4的式(Ⅰa)的5-氨基吡唑衍生物与扩充剂和/或表面活性剂混合。
9.杀微生物组合物,其特征在于它们含有至少一种权利要求8的式(Ⅰc)的5-氨基吡唑衍生物和扩充剂和/或表面活性剂。
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EP (1) | EP1107956A2 (zh) |
JP (1) | JP2002525272A (zh) |
CN (1) | CN1315943A (zh) |
AU (1) | AU5622599A (zh) |
DE (1) | DE19838708A1 (zh) |
WO (1) | WO2000011951A2 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103012393A (zh) * | 2007-07-11 | 2013-04-03 | 先正达参股股份有限公司 | 用作杀真菌剂的异噻唑和吡唑衍生物 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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AU664392B2 (en) * | 1991-10-18 | 1995-11-16 | Monsanto Technology Llc | Fungicides for the control of take-all disease of plants |
US6903093B2 (en) * | 2000-10-06 | 2005-06-07 | Monsanto Technology Llc | Seed treatment with combinations of pyrethrins/pyrethroids and thiamethoxam |
AU2003289105A1 (en) * | 2002-12-25 | 2004-07-22 | Sumitomo Chemical Company, Limited | Phenylpyrazole compound and method of controlling plant disease with the same |
TW200621152A (en) * | 2004-09-06 | 2006-07-01 | Basf Ag | (Hetero)cyclylcarboxamides for controlling harmful fungi |
Family Cites Families (4)
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JPS62138475A (ja) | 1985-12-12 | 1987-06-22 | Tokuyama Soda Co Ltd | ピラゾ−ル化合物 |
JPS63313773A (ja) * | 1987-06-16 | 1988-12-21 | Tokuyama Soda Co Ltd | ピラゾ−ル化合物 |
JPS63312773A (ja) | 1987-06-16 | 1988-12-21 | Mitsubishi Electric Corp | ファクシミリ受信装置 |
DE19500789A1 (de) | 1995-01-13 | 1996-07-18 | Bayer Ag | Acylierte 5-Aminopyrazole |
-
1998
- 1998-08-26 DE DE19838708A patent/DE19838708A1/de not_active Withdrawn
-
1999
- 1999-08-18 EP EP99942879A patent/EP1107956A2/de not_active Withdrawn
- 1999-08-18 US US09/763,428 patent/US6444612B1/en not_active Expired - Fee Related
- 1999-08-18 AU AU56225/99A patent/AU5622599A/en not_active Abandoned
- 1999-08-18 JP JP2000571015A patent/JP2002525272A/ja active Pending
- 1999-08-18 WO PCT/EP1999/006043 patent/WO2000011951A2/de not_active Application Discontinuation
- 1999-08-18 CN CN99810381A patent/CN1315943A/zh active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103012393A (zh) * | 2007-07-11 | 2013-04-03 | 先正达参股股份有限公司 | 用作杀真菌剂的异噻唑和吡唑衍生物 |
Also Published As
Publication number | Publication date |
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AU5622599A (en) | 2000-03-21 |
WO2000011951A2 (de) | 2000-03-09 |
JP2002525272A (ja) | 2002-08-13 |
US6444612B1 (en) | 2002-09-03 |
DE19838708A1 (de) | 2000-03-02 |
WO2000011951A3 (de) | 2000-05-25 |
EP1107956A2 (de) | 2001-06-20 |
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