CN108366562A - 杀微生物的苯基脒衍生物 - Google Patents
杀微生物的苯基脒衍生物 Download PDFInfo
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- CN108366562A CN108366562A CN201680073709.1A CN201680073709A CN108366562A CN 108366562 A CN108366562 A CN 108366562A CN 201680073709 A CN201680073709 A CN 201680073709A CN 108366562 A CN108366562 A CN 108366562A
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- halogenated
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- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
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- 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
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- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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Abstract
具有式(I)的化合物其中R1、R2、R3、R4、R5、R6、R7、R8和X是如在权利要求1中所定义的。此外,本发明涉及包括具有式(I)的化合物的农用化学品组合物,涉及这些组合物的制备,并且涉及这些化合物或组合物在农业或园艺中用于对抗、预防或控制植物、收获的粮食作物、种子或非生命材料被致植物病的微生物、特别是真菌侵染的用途。
Description
本发明涉及新颖的苯基脒衍生物,例如,作为活性成分,这些苯基脒衍生物具有杀微生物活性、特别是杀真菌活性。本发明还涉及这些苯基脒衍生物的制备,涉及在这些苯基脒衍生物的制备中有用的中间体,涉及这些中间体的制备,涉及包括这些苯基脒衍生物中至少一种的农用化学品组合物,涉及这些组合物的制备并且涉及这些苯基脒衍生物或组合物在农业或园艺中用于控制或防止植物、收获的粮食作物、种子或非生命材料被致植物病的微生物、特别是真菌侵染的用途。
在WO 00/46184中描述了某些杀真菌的苯基脒化合物。
现在已经出人意料地发现某些新颖的苯基脒衍生物具有有利的杀真菌特性。
因此本发明提供了具有式(I)的化合物
共甲,
R1和R2各自独立地选自C1-C4烷基和C3-C8环烷基;或
R1和R2连同它们所附接的氮原子一起形成三元至六元饱和的环状基团,该环状基团可以任选地含有一个氧原子或一个硫原子;
R3是氢、卤素或C1-C4烷基;
R4是C1-C4烷基或C1-C4卤代烷基;
R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C8环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、芳基(任选地被一至三个R7基团取代)、芳基(C1-C4)烷基(其中该芳基任选地被一至三个R7基团取代)、杂芳基(C1-C4)烷基(其中该杂芳基任选地被一至三个R7基团取代)和杂芳基(任选地被一至三个R7基团取代);
X是NR8、O或S;
每个R7独立地选自卤素、氰基、羟基、氨基、硝基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C3-C6环烷硫基、C1-C4烷基亚磺酰基、C1-C4卤代烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯基氧基、C2-C6卤代烯基氧基、C2-C6炔基、C3-C6环烷基C2-C6炔基、C2-C6炔基氧基、芳基、芳基(C1-C4)烷基、芳基氧基、杂芳基、杂芳基(C1-C4)烷基和杂芳基氧基;并且
R8选自氢、C1-C4烷基、C1-C4烷氧基和C3-C8环烷基;或其盐或N-氧化物。
在第二方面,本发明提供了一种农用化学品组合物,该组合物包括具有式(I)的化合物。
具有式(I)的化合物可以用于控制致植物病的微生物。因此,为了控制植物病原体,可以将根据本发明所述的具有式(I)的化合物、或包括具有式(I)的化合物的组合物直接施用到该植物病原体、或植物病原体的场所,特别是易受植物病原体攻击的植物。
因此,在第三方面,本发明提供了如在此描述的具有式(I)的化合物、或包括具有式(I)的化合物的组合物用以控制植物病原体的用途。
在另外的方面,本发明提供了控制植物病原体的方法,该方法包括将如在此所描述的具有式(I)的化合物、或包括具有式(I)的化合物的组合物施用到所述植物病原体、或所述植物病原体的场所,特别是易受植物病原体攻击的植物。
具有式(I)的化合物在控制致植物病的真菌上是特别有效的。
因此,在又另外的方面,本发明提供了如在此描述的具有式(I)的化合物、或包括具有式(I)的化合物的组合物用以控制致植物病的真菌的用途。
在另外的方面,本发明提供了控制致植物病的真菌的方法,该方法包括将如在此所描述的具有式(I)的化合物、或包括具有式(I)的化合物的组合物施用到所述致植物病的真菌、或所述致植物病的真菌的场所、特别是易受致植物病的真菌攻击的植物。
其中取代基被表示为可任选地经取代的,这是指它们可以带有或可以不带有一个或多个相同的或不同的取代基,例如一至三个取代基。正常地,同时存在不多于三个这样的任选的取代基。当基团被表示为被取代时,例如烷基,这包括是其他基团的一部分的那些基团,例如烷硫基中的烷基。
术语“卤素”是指氟、氯、溴或碘,优选是氟、氯或溴。
烷基取代基可以是直链的或者是支链的。取决于提到的碳原子的数量,烷基其本身或作为另一取代基的部分是例如甲基、乙基、正丙基、正丁基、正戊基、正己基和它们的异构体,例如异丙基、异丁基、仲丁基、叔丁基或异戊基。
烯基取代基(单独或作为较大基团的一部分,例如烯基氧基)可以处于直链或支链的形式,并且这些烯基部分可以是(适当时)具有(E)-或(Z)-构型。实例是乙烯基和烯丙基。该烯基基团优选地是C2-C6,更优选地是C2-C4并且最优选地是C2-C3烯基基团。
炔基取代基(单独或作为较大基团(例如炔基氧基)的一部分)可以处于直链或支链的形式。实例是乙炔基和炔丙基。该炔基基团优选地是C2-C6、更优选地是C2-C4并且最优选地是C2-C3炔基基团。
卤代烷基基团(单独或作为较大基团的一部分,例如卤代烷基氧基)可能包含一个或多个相同或不同的卤素原子并且,例如,可以代表CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CF2Cl、CF3CH2、CH3CF2、CF3CF2或CCl3CCl2。
卤代烯基基团(单独或作为较大基团的一部分,例如卤代烯基氧基)是烯基基团,其分别被一个或多个相同或不同的卤素原子取代,并且是,例如2,2-二氟乙烯基或1,2-二氯-2-氟-乙烯基。
烷氧基指的是基团-OR,其中R是正如上面所定义的烷基。烷氧基基团包括,但不限于:甲氧基、乙氧基、1-甲基乙氧基、丙氧基、丁氧基、1-甲基丙氧基和2-甲基丙氧基。
氰基指的是-CN基团。
硝基指的是-NO2基团。
氨基指的是-NH2基团。
羟基(“hydroxy1”或“hydroxy”)代表-OH基团。
环烷基可以是饱和的或部分不饱和的,优选是完全饱和的,并且是例如环丙基、环丁基、环戊基、环己基、或环己烯基。
芳基基团(单独或作为较大基团的一部分,例如像芳基氧基、芳基-烷基)是芳香族环体系,它们可以处于单-、双-或三环的形式。此类环的实例包括苯基、萘基、蒽基、茚基或菲基。优选的芳基基团是苯基与萘基、苯基是最优选的。在芳基部分被认为被取代的情况下,该芳基部分优选地被一至四个取代基取代,最优选地被一至三个取代基取代。
杂芳基基团(单独或作为较大基团的一部分,例如像杂芳基氧基、杂芳基-烷基)是芳香族环体系,这些体系包括至少一个杂原子并且由单环或两个或更多个稠合环组成。优选地,单环将包含多达三个杂原子并且双环体系包含多达四个杂原子,这些杂原子将优选地选自氮、氧以及硫。单环基团的实例包括吡啶基、哒嗪基、嘧啶基、吡嗪基、吡咯基、吡唑基、咪唑基、***基(例如,[1,2,4]***基)、呋喃基、噻吩基(thiophenyl)、噁唑基、异噁唑基、噁二唑基、噻唑基、异噻唑基以及噻二唑基。双环基团的实例包括嘌呤基、喹啉基、噌啉基、喹喔啉基、吲哚基、吲唑基、苯并咪唑基、苯并噻吩基以及苯并噻唑基。优选单环的杂芳基基团,吡啶基是最优选的。在杂芳基部分被认为被取代的情况下,该杂芳基部分优选地被一至四个取代基取代,最优选地被一至三个取代基取代。
杂环基基团或杂环(单独或作为较大基团的一部分,例如杂环基-烷基)是非芳香族环结构,其包含多达10个原子,这些原子包括选自O、S和N的一个或多个(优选一个、两个或三个)杂原子。单环基团的实例包括氧杂环丁烷基、4,5-二氢-异噁唑基、硫杂环丁烷基、吡咯烷基、四氢呋喃基、[1,3]二氧戊环基、哌啶基、哌嗪基、[1,4]二氧杂环己基、咪唑烷基、[1,3,5]噁二嗪烷基(oxadiazinanyl)、六氢-嘧啶基、[1,3,5]三嗪烷基(triazinanyl)以及吗啉基或其氧化的形式,例如1-氧代-硫杂环丁基以及1,1-二氧代-硫杂环丁基。双环基团的实例包括2,3-二氢-苯并呋喃基、苯并[1,4]二氧戊环基、苯并[1,3]二氧戊环基、色满基以及2,3-二氢-苯并-[1,4]-二噁英基。在杂环基部分被认为被取代的情况下,该杂环基部分优选地被一至四个取代基取代,最优选地被一至三个取代基取代。
在具有式(I)的化合物中存在一个或多个可能不对称的碳原子指的是该化合物能以光学异构体形式,即对映体或非对映体的形式,存在。作为围绕单键的受限的旋转的结果,还可能存在阻转异构体。式(I)旨在包括所有那些可能的异构体形式及其混合物。本发明包括具有式(I)的化合物的所有那些可能的异构体形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体。本发明包括针对具有式(I)的化合物的所有可能的互变异构形式。
在每种情况下,根据本发明的具有式(I)的化合物是处于游离形式、被氧化的形式如N-氧化物、或盐的形式(例如农艺学上可用的盐的形式)。
N-氧化物是叔胺的氧化形式或含氮杂芳香族化合物的氧化形式。例如,A.Albini和S.Pietra于1991年在博卡拉顿(Boca Raton)CRC出版社出版的名为“Heterocyclic N-oxides[杂环N-氧化物]”一书中描述了它们。
R1、R2、R3、R4、R5、R6、R7、R8和X的优选值是以其任何组合如以下列出的:
优选地,R1和R2各自独立地是C1-C4烷基。
更优选地,R1和R2各自独立地选自甲基、乙基、丙基和异丙基。
甚至更优选地,R1和R2各自独立地选自甲基、乙基和异丙基。
最优选地,R1是甲基并且R2是乙基或异丙基。
优选地,R3是氢、氟、氯、或C1-C4烷基。
更优选地,R3是氢或C1-C3烷基。
甚至更优选地,R3是氢或C1-C2烷基。
最优选地,R3是氢或甲基。
优选地,R4是C1-C3烷基或C1-C3卤代烷基。
更优选地,R4是C1-C2烷基或C1-C2卤代烷基。
甚至更优选地,R4是甲基或乙基。
最优选地,R4是甲基。
尤其优选的是如果R3是氢并且R4是甲基或R3是甲基并且R4是甲基。
最优选的是如果R3和R4都是甲基。
优选地,R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C8环烷基、C2-C6烯基、苯基(任选地被一至三个R7基团取代)、苯基(C1-C4)烷基(其中该苯基任选地被一至三个R7基团取代)、吡唑基(C1-C4)烷基(其中该吡唑任选地被一至三个R7基团取代)和吡啶基(任选地被一至三个R7基团取代)。
更优选地,R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C5环烷基、苯基(任选地被一个或两个R7基团取代)和吡啶基(任选地被一个或两个R7基团取代)。
甚至更优选地,R5和R6各自独立地选自C1-C2卤代烷基、苯基(任选地被一个或两个R7基团取代)、乙基、正丙基、异丙基、正丁基、异丁基、新戊基、环丙基、环丁基或环戊基。
最优选地,R5是CF3、CClF2或CF2CF3并且R6是苯基(任选地被一个甲基基团和/或一个或两个卤素原子(优选氟或氯)取代)、正丙基、异丙基、正丁基、异丁基或新戊基。
优选地,X是NR8或O。
更优选地,X是N-C1-C4烷基或O。
甚至更优选地,X是N-甲基或O。
最优选地,X是O。
优选地,每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、苯基、苄基、苯氧基、吡啶基、吡啶基甲基和吡啶基氧基。
更优选地,每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4烷基羰基、C2-C6炔基、苯基、苯氧基和吡啶基。
甚至更优选地,每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C6炔基和苯基。
最优选地,每个R7独立地选自卤素、氰基、C1-C2烷基、C1-C2卤代烷基和C1-C2卤代烷氧基。
优选地,R8是氢、C1-C4烷基或C1-C4烷氧基。
更优选地,R8是氢或C1-C4烷基。
甚至更优选地,R8是氢、或甲基。
最优选地,R8是甲基。
在具有式(I)的化合物中,提供了根据本发明的实施例,如以下列出。
实施例1提供了具有式(I)的化合物、以及其盐或N-氧化物,如以上所定义的。
实施例2提供了根据实施例1所述的化合物,其中R1和R2各自独立地是C1-C4烷基。
实施例3提供了根据实施例1或2所述的化合物,其中R3是氢、氟、氯、或C1-C4烷基。
实施例4提供了根据实施例1、2或3中任一项所述的化合物,其中R4是C1-C3烷基或C1-C3卤代烷基。
实施例5提供了根据实施例1、2、3或4中任一项所述的化合物,其中R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C8环烷基、C2-C6烯基、苯基(任选地被一至三个R7基团取代)、苯基(C1-C4)烷基(其中该苯基任选地被一至三个R7基团取代)、吡唑基(C1-C4)烷基(其中该吡唑任选地被一至三个R7基团取代)和吡啶基(任选地被一至三个R7基团取代),其中每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、苯基、苄基、苯氧基、吡啶基、吡啶基甲基和吡啶基氧基。
实施例6提供了根据实施例1、2、3、4、或5中任一项所述的化合物,其中X是NR8或O,其中R8是氢、C1-C4烷基或C1-C4烷氧基。
实施例7提供了根据实施例1、2、3、4、5、或6中任一项所述的化合物,其中R1和R2各自独立地选自甲基、乙基、丙基和异丙基。
实施例8提供了根据实施例1、2、3、4、5、6、或7中任一项所述的化合物,其中R3是氢或C1-C3烷基。
实施例9提供了根据实施例1、2、3、4、5、6、7、或8中任一项所述的化合物,其中R4是C1-C2烷基或C1-C2卤代烷基。
实施例10提供了根据实施例1、2、3、4、5、6、7、8、或9中任一项所述的化合物,其中R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C5环烷基、苯基(任选地被一个或两个R7基团取代)和吡啶基(任选地被一个或两个R7基团取代),其中每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4烷基羰基、C2-C6炔基、苯基、苯氧基和吡啶基。
实施例11提供了根据实施例1、2、3、4、5、6、7、8、9或10中任一项所述的化合物,其中X是N-C1-C4烷基或O。
实施例12提供了根据实施例1、2、3、4、5、6、7、8、9、10或11中任一项所述的化合物,其中R1和R2各自独立地选自甲基、乙基和异丙基。
实施例13提供了根据实施例1、2、3、4、5、6、7、8、9、10、11或12中任一项所述的化合物,其中R3是氢或C1-C2烷基。
实施例14提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12或13中任一项所述的化合物,其中R4是甲基或乙基。
实施例15提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13或14中任一项所述的化合物,其中R5和R6各自独立地选自C1-C2卤代烷基、苯基(任选地被一个或两个R7基团取代)、乙基、正丙基、异丙基、正丁基、异丁基、新戊基、环丙基、环丁基或环戊基,其中每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C6炔基和苯基。
实施例16提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14或15中任一项所述的化合物,其中R1是甲基并且R2是乙基或异丙基。
实施例17提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15或16中任一项所述的化合物,其中R3是氢或甲基。
实施例18提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16或17中任一项所述的化合物,其中R4是甲基。
实施例19提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17或18中任一项所述的化合物,其中R5是CF3、CClF2或CF2CF3。
实施例20提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18或19中任一项所述的化合物,其中R6是苯基(任选地被一个甲基基团和/或一个或两个卤素原子(优选氟或氯)取代)、正丙基、异丙基、正丁基、异丁基或新戊基。
实施例21提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19或20中任一项所述的化合物,其中X是N-甲基或O。
实施例22提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20或21中任一项所述的化合物,其中R3是氢并且R4是甲基或R3是甲基并且R4是甲基。
实施例23提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21或22中任一项所述的化合物,其中R3和R4都是甲基。
实施例24提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22或23中任一项所述的化合物,其中X是O。
根据本发明的一组优选的化合物是具有式(I-1)的那些,其是具有式(I)的化合物,其中R1和R2各自独立地是C1-C4烷基;R3是氢、氟、氯、或C1-C4烷基;R4是C1-C3烷基或C1-C3卤代烷基;R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C8环烷基、C2-C6烯基、苯基(任选地被一至三个R7基团取代)、苯基(C1-C4)烷基(其中该苯基任选地被一至三个R7基团取代)、吡唑基(C1-C4)烷基(其中该吡唑任选地被一至三个R7基团取代)和吡啶基(任选地被一至三个R7基团取代);X是NR8或O;每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、苯基、苄基、苯氧基、吡啶基、吡啶基甲基和吡啶基氧基;并且R8是氢、C1-C4烷基或C1-C4烷氧基;或其盐或N-氧化物。
根据本发明的另一组优选的化合物是具有式(I-2)的那些,其是具有式(I)的化合物,其中R1和R2各自独立地选自甲基、乙基、丙基和异丙基;R3是氢或C1-C3烷基;R4是C1-C2烷基或C1-C2卤代烷基;R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C5环烷基、苯基(任选地被一个或两个R7基团取代)和吡啶基(任选地被一个或两个R7基团取代);X是N-C1-C4烷基或O;并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4烷基羰基、C2-C6炔基、苯基、苯氧基和吡啶基;或其盐或N-氧化物。
根据本发明的另一组优选的化合物是具有式(I-3)的那些,其是具有式(I)的化合物,其中R1和R2各自独立地选自甲基、乙基和异丙基;R3是氢或C1-C2烷基;R4是甲基或乙基;R5和R6各自独立地选自C1-C2卤代烷基、苯基(任选地被一个或两个R7基团取代)、乙基、正丙基、异丙基、正丁基、异丁基、新戊基、环丙基、环丁基或环戊基;X是N-甲基或O;并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C6炔基和苯基;或其盐或N-氧化物。
根据本发明的另一组优选的化合物是具有式(I-4)的那些,其是具有式(I)的化合物,其中R1是甲基并且R2是乙基或异丙基;R3是氢或甲基;R4是甲基;R5是CF3、CClF2或CF2CF3;R6是苯基(任选地被一个甲基基团和/或一个或两个卤素原子、优选氟或氯取代)、正丙基、异丙基、正丁基、异丁基或新戊基;并且X是O;或其盐或N-氧化物。
根据本发明的另一组化合物是具有式(IK)的那些,其是具有式(I)的化合物,
其中
R1和R2各自独立地选自C1-C4烷基和C3-C8环烷基;或
R1和R2连同它们所附接的氮原子一起形成三元至六元饱和的环状基团,该环状基团可以任选地含有一个氧原子或一个硫原子;
R3是氢、卤素或C1-C4烷基;
R4是C1-C4烷基或C1-C4卤代烷基;
R5和R6各自独立地选自C1-C4烷基、C1-C4卤代烷基、C3-C8环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、芳基(任选地被一至三个R7基团取代)和杂芳基(任选地被一至三个R7基团取代);
X是NR8、O或S;
每个R7独立地选自卤素、氰基、羟基、氨基、硝基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C3-C6环烷硫基、C1-C4烷基亚磺酰基、C1-C4卤代烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯基氧基、C2-C6卤代烯基氧基、C2-C6炔基、C3-C6环烷基C2-C6炔基、C2-C6炔基氧基、芳基、芳基(C1-C4)烷基、芳基氧基、杂芳基、杂芳基(C1-C4)烷基和杂芳基氧基;并且
R8选自氢、C1-C4烷基、C1-C4烷氧基和C3-C8环烷基;或其盐或N-氧化物。
在具有式(IK)的化合物中,R1、R2、R3、R4、R5、R6、R7、R8和X的优选值以其任何组合是如以下列出的:
优选地,R1和R2各自独立地是C1-C4烷基。
更优选地,R1和R2各自独立地选自甲基、乙基和异丙基。
甚至更优选地,R1和R2各自独立地选自甲基和乙基。
最优选地,R1是甲基并且R2是乙基。
优选地,R3是氢或C1-C4烷基。
更优选地,R3是氢或C1-C3烷基。
甚至更优选地,R3是氢或C1-C2烷基。
最优选地,R3是氢或甲基。
优选地,R4是C1-C3烷基或C1-C3卤代烷基。
更优选地,R4是C1-C2烷基或C1-C2卤代烷基。
甚至更优选地,R4是甲基或乙基。
最优选地,R4是甲基。
尤其优选的是如果R3是氢并且R4是甲基或R3是甲基并且R4是甲基。
最优选的是如果R3和R4都是甲基。
优选地,R5和R6各自独立地选自C1-C4烷基、C1-C4卤代烷基、C3-C8环烷基、C2-C6炔基、苯基(任选地被一至三个R7基团取代)和吡啶基(任选地被一至三个R7基团取代);
更优选地,R5和R6各自独立地选自C1-C4烷基、C1-C4卤代烷基、苯基(任选地被一个或两个R7基团取代)和吡啶基(任选地被一个或两个R7基团取代);
甚至更优选地,R5和R6各自独立地选自C1-C4卤代烷基、苯基(任选地被一个或两个R7基团取代)、正丙基、正丁基或吡啶基(任选地被一个或两个R7基团取代);
最优选地,R5是C1-C2卤代烷基(尤其是C1-C2氟烷基)并且R6是苯基(任选地被一个或两个卤素原子(优选氟)取代)、正丁基或C1-C2氟烷基。
优选地,X是NR8或O。
更优选地,X是N-C1-C4烷基或O。
甚至更优选地,X是N-甲基或O。
最优选地,X是O。
优选地,每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、苯基、苄基、苯氧基、吡啶基、吡啶基甲基和吡啶基氧基。
更优选地,每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4烷基羰基、C2-C6炔基、苯基、苯氧基和吡啶基。
甚至更优选地,每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C6炔基和苯基。
最优选地,每个R7独立地选自卤素、氰基、C1-C4卤代烷基和C1-C4卤代烷氧基。
优选地,R8是氢、C1-C4烷基或C1-C4烷氧基。
更优选地,R8是氢或C1-C4烷基。
甚至更优选地,R8是氢、或甲基。
最优选地,R8是甲基。
在具有式(IK)的化合物中,提供了根据本发明的实施例,如以下列出。
实施例IK1提供了具有式I的化合物、以及其盐或N-氧化物,如以上所定义的。
实施例IK2提供了根据实施例IK1所述的化合物,其中R1和R2各自独立地是C1-C4烷基。
实施例IK3提供了根据实施例IK1或IK2所述的化合物,其中R3是氢或C1-C4烷基。
实施例IK4提供了根据实施例IK1、IK2或IK3中任一项所述的化合物,其中R4是C1-C3烷基或C1-C3卤代烷基。
实施例IK5提供了根据实施例IK1、IK2、IK3或IK4中任一项所述的化合物,其中R5和R6各自独立地选自C1-C4烷基、C1-C4卤代烷基、C3-C8环烷基、C2-C6炔基、苯基(任选地被一至三个R7基团取代)和吡啶基(任选地被一至三个R7基团取代),并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、苯基、苄基、苯氧基、吡啶基、吡啶基甲基和吡啶基氧基。
实施例IK6提供了根据实施例IK1、IK2、IK3、IK4或IK5中任一项所述的化合物,其中X是NR8或O并且R8是氢、C1-C4烷基或C1-C4烷氧基。
实施例IK7提供了根据实施例IK1、IK2、IK3、IK4、IK5或IK6中任一项所述的化合物,其中R1和R2各自独立地选自甲基、乙基和异丙基。
实施例IK8提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6或IK7中任一项所述的化合物,其中R3是氢或C1-C3烷基。
实施例IK9提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7或IK8中任一项所述的化合物,其中R4是C1-C2烷基或C1-C2卤代烷基。
实施例IK10提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8或IK9中任一项所述的化合物,其中R5和R6各自独立地选自C1-C4烷基、C1-C4卤代烷基、苯基(任选地被一个或两个R7基团取代)和吡啶基(任选地被一个或两个R7基团取代),并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4烷基羰基、C2-C6炔基、芳基、芳基氧基和杂芳基。
实施例IK11提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9或IK10中任一项所述的化合物,其中X是N-C1-C4烷基或O。
实施例IK12提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10或IK11中任一项所述的化合物,其中R1和R2各自独立地选自甲基和乙基。
实施例IK13提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11或IK12中任一项所述的化合物,其中R3是氢或C1-C2烷基。
实施例IK14提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12或IK13中任一项所述的化合物,其中R4是甲基或乙基。
实施例IK15提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13或IK14中任一项所述的化合物,其中R5和R6各自独立地选自C1-C4卤代烷基、苯基(任选地被一个或两个R7基团取代)、正丙基、正丁基或吡啶基(任选地被一个或两个R7基团取代),并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C6炔基和苯基。
实施例IK16提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13、IK14或IK15中任一项所述的化合物,其中X是N-甲基或O。
实施例IK17提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13、IK14、IK15或IK16中任一项所述的化合物,其中R1是甲基并且R2是乙基。
实施例IK18提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13、IK14、IK15、IK16或IK17中任一项所述的化合物,其中R3是氢或甲基。
实施例IK19提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13、IK14、IK15、IK16、IK17或IK18中任一项所述的化合物,其中R4是甲基。
实施例IK20提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13、IK14、IK15、IK16、IK17、IK18或IK19中任一项所述的化合物,其中R5是C1-C2卤代烷基(尤其是C1-C2氟烷基),并且R6是苯基(任选地被一个或两个卤素原子(优选氟)取代)、正丁基或C1-C2氟烷基。
实施例IK21提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13、IK14、IK15、IK16、IK17、IK18、IK19或IK20中任一项所述的化合物,其中R3是氢并且R4是甲基或R3是甲基并且R4是甲基。
实施例IK22提供了根据实施例IK1、IK2、IK3、IK4、IK5、IK6、IK7、IK8、IK9、IK10、IK11、IK12、IK13、IK14、IK15、IK16、IK17、IK18、IK19、IK20或IK21中任一项所述的化合物,其中R3和R4都是甲基。
一组优选的具有式(IK)的化合物是具有式(IK-1)的那些,其是具有式(IK)的化合物,其中R1和R2各自独立地是C1-C4烷基;R3是氢或C1-C4烷基;R4是C1-C3烷基或C1-C3卤代烷基;R5和R6各自独立地选自C1-C4烷基、C1-C4卤代烷基、C3-C8环烷基、C2-C6炔基、苯基(任选地被一至三个R7基团取代)和吡啶基(任选地被一至三个R7基团取代);X是NR8或O;每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、苯基、苄基、苯氧基、吡啶基、吡啶基甲基和吡啶基氧基;并且R8是氢、C1-C4烷基或C1-C4烷氧基;或其盐或N-氧化物。
另一组优选的具有式(IK)的化合物是具有式(IK-2)的那些,其是具有式(IK)的化合物,其中R1和R2各自独立地选自甲基、乙基和异丙基;R3是氢或C1-C3烷基;R4是C1-C2烷基或C1-C2卤代烷基;R5和R6各自独立地是C1-C4烷基、C1-C4卤代烷基、苯基(任选地被一个或两个R7基团取代)或吡啶基(任选地被一个或两个R7基团取代);X是N-C1-C4烷基或O;并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4烷基羰基、C2-C6炔基、芳基、芳基氧基和杂芳基;或其盐或N-氧化物。
另一组优选的具有式(IK)的化合物是具有式(IK-3)的那些,其是具有式(IK)的化合物,其中R1是甲基并且R2是乙基或异丙基;或者,可替代地,R1和R2都是乙基;R3是氢或甲基(优选甲基);R4是甲基;R5是CF3、CClF2或CF2CF3(优选CF3);R6是苯基(任选地被一个甲基基团和/或一个或两个卤素原子、优选氟或氯取代)、正丙基、异丙基、正丁基、异丁基或新戊基;或者,可替代地,R6是环丙基;并且X是O;或其盐或N-氧化物。
另一组优选的具有式(IK)的化合物是具有式(IK-4)的那些,其是具有式(IK)的化合物,其中R1和R2各自独立地是甲基或乙基;R3是氢或C1-C2烷基;R4是甲基或乙基;R5和R6各自独立地选自C1-C4卤代烷基、苯基(任选地被一个或两个R7基团取代)、正丙基、正丁基和吡啶基(任选地被一个或两个R7基团取代);X是N-甲基或O;并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C6炔基和苯基;或其盐或N-氧化物。
根据本发明所述的化合物可以具有许多益处,尤其包括针对保护植物对抗由真菌引起的疾病的有利水平的生物活性或对于用作农用化学品活性成分的优越特性(例如,更高的生物活性、有利的活性谱、增加的安全性、改进的物理-化学特性、或增加的生物可降解性)。
在下表1至33中示出了具有式(I)的化合物的具体实例。
在以下的表P之后的表1至33的每一个提供具有式(IA)的98种化合物
其中R2、R3、R4、R5和X是如表P所定义的,并且R6是分别如表1至33所定义的。
因此表1个体化了98种具有式(IA)的化合物,其中对于表P的每一行,R6是如在表1中所定义的。类似地,表2个体化了98种具有式(IA)的化合物,其中对于表P的每一行,R6是如在表2中所定义的;表3至33以此类推。
表P
表1:该表披露了具有式IA的98种化合物1.001至1.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物1.001具有以下结构:
表2:该表披露了具有式IA的98种化合物2.001至2.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表3:该表披露了具有式IA的98种化合物3.001至3.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表4:该表披露了具有式IA的98种化合物4.001至4.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表5:该表披露了具有式IA的98种化合物5.001至5.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表6:该表披露了具有式IA的98种化合物6.001至6.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表7:该表披露了具有式IA的98种化合物7.001至7.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表8:该表披露了具有式IA的98种化合物8.001至8.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表9:该表披露了具有式IA的98种化合物9.001至9.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表10:该表披露了具有式IA的98种化合物10.001至10.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表11:该表披露了具有式IA的98种化合物11.001至11.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表12:该表披露了具有式IA的98种化合物12.001至11.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表13:该表披露了具有式IA的98种化合物13.001至13.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表14:该表披露了具有式IA的98种化合物14.001至14.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表15:该表披露了具有式IA的98种化合物15.001至15.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表16:该表披露了具有式IA的98种化合物16.001至16.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表17:该表披露了具有式IA的98种化合物17.001至17.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表18:该表披露了具有式IA的98种化合物18.001至18.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表19:该表披露了具有式IA的98种化合物19.001至19.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表20:该表披露了具有式IA的98种化合物20.001至20.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表21:该表披露了具有式IA的98种化合物21.001至21.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表22:该表披露了具有式IA的98种化合物22.001至22.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表23:该表披露了具有式IA的98种化合物23.001至23.098,其中R6是
其中井号(hash mark)表示R6与分子的剩余部分的附接点,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。
表24:该表披露了具有式IA的98种化合物24.001至24.098,其中R6是乙基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物24.021具有以下结构:
表25:该表披露了具有式IA的98种化合物25.001至25.098,其中R6是丙基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物25.021具有以下结构:
表26:该表披露了具有式IA的98种化合物26.001至26.098,其中R6是丁基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物26.021具有以下结构:
表27:该表披露了具有式IA的98种化合物27.001至27.098,其中R6是-CH2CH(CH3)2,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物27.021具有以下结构:
表28:该表披露了具有式IA的98种化合物28.001至28.098,其中R6是环己基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物28.021具有以下结构:
表29:该表披露了具有式IA的98种化合物29.001至29.098,其中R6是异丙基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物29.021具有以下结构:
表30:该表披露了具有式IA的98种化合物30.001至30.098,其中R6是环戊基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物30.021具有以下结构:
表31:该表披露了具有式IA的98种化合物31.001至31.098,其中R6是环丙基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物31.021具有以下结构:
表32:该表披露了具有式IA的98种化合物32.001至32.098,其中R6是-(CH2)C(CH3)3,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物32.021具有以下结构:
表33:该表披露了具有式IA的98种化合物33.001至33.098,其中R6是烯丙基,并且其中变量R2、R3、R4、R5和X具有在表P的相应行中给出的具体含义。例如,化合物33.021具有以下结构:
本发明的化合物可以如在以下方案中所示来制备,其中(除非另外说明)每一变量的定义是如以上针对具有式(I)的化合物所定义的。
具有式(I)的化合物(其中R1、R2、R3、R4、R5、R6和X是如针对式(I)所定义的)可以通过将具有式(II)的化合物(其中R1、R2、R3、R4和X是如针对式(I)所定义的,并且Hal是卤素(优选溴或碘))与具有式(III)的化合物(其中R5和R6是如针对式(I)所定义的)和强碱(例如正丁基锂或叔丁基锂)转化来获得。这在下面的方案1中示出。
方案1
具有式(II)的化合物(其中R1、R2、R3、R4和X是如针对式(I)所定义的,并且Hal是卤素(优选溴或碘))可以通过将具有式(IV)的化合物(其中R3、R4和X是如针对式(I)所定义的,并且Hal是卤素(优选溴或碘))与具有式(V)的化合物(其中R1和R2是如针对式(I)所定义的,并且R9是C1-C4烷基)转化来获得。这在下面的方案2中示出。
方案2
具有式(IV)的化合物(其中R3、R4和X是如针对式(I)所定义的,并且Hal是卤素(优选溴或碘))可以通过将具有式(VI)的化合物(其中R3、R4和X是如针对式(I)所定义的)与卤化剂(例如溴、N-溴代琥珀酰亚胺或N-碘代琥珀酰亚胺)转化来获得。这在下面的方案3中示出。
方案3
具有式(VI)的化合物(其中R3、R4、和X是如针对式(I)所定义的)可以通过将具有式(VII)的化合物(其中R3、R4、和X是如针对式(I)所定义的)在还原条件下(例如通过催化氢化)或在Bechamp反应的条件下转化来获得。这在下面的方案4中示出。
方案4
具有式(VII-A)的化合物(其中R3和R4是如针对式(I)所定义的)可以通过将具有式(VIII)的化合物(其中R3是如针对式(I)所定义的)与具有式(IX)的化合物(其中R4是如针对式(I)所定义的并且R10是卤素(优选氯或溴)或磺酸酯(优选甲磺酸酯))以及与碱(例如氢化钠或碳酸钾)转化来获得。这在下面的方案5中示出。
方案5
具有式(VII-B)的化合物(其中R3和R4是如针对式(I)所定义的)可以通过将具有式(X)的化合物(其中R3是如针对式(I)所定义的)与具有式(IX)的化合物(其中R4是如针对式(I)所定义的并且R10是卤素(优选氯或溴)或磺酸酯(优选甲磺酸酯))以及与碱(例如氢化钠或碳酸钾)转化来获得。这在下面的方案6中示出。
方案6
可替代地,具有式(I)的化合物(其中R1、R2、R3、R4、R5、R6和X是如针对式(I)所定义的)可以通过将具有式(XI)的化合物(其中R3、R4、R5、R6和X是如针对式(I)所定义的)与具有式(V)的化合物(其中R1和R2是如针对式(I)所定义的,并且R9是C1-C4烷基)转化来获得。这在下面的方案7中示出。
方案7
具有式(XI)的化合物(其中R3、R4、R5、R6和X是如针对式(I)所定义的)可以通过将具有式(XII)的化合物(其中R3、R4、R5、R6和X是如针对式(I)所定义的)在还原条件下(例如通过催化氢化)或在Bechamp反应的条件下转化来获得。这在下面的方案8中示出。
方案8
具有式(XII)的化合物(其中R3、R4、R5、R6和X是如针对式(I)所定义的)可以通过将具有式(XIII)的化合物(其中R3、R4、R5和X是如针对式(I)所定义的)与具有式(XIV)的化合物(其中R6是如针对式(I)所定义的,并且R11是Li、MgCl或MgBr)转化来获得。这在下面的方案9中示出。
方案9
具有式(XIII-A)的化合物(其中R3、R4和R5是如针对式(I)所定义的)可以通过将具有式(XV)的化合物(其中R3和R5是如针对式(I)所定义的)与具有式(IX)的化合物(其中R4是如针对式(I)所定义的并且R10是卤素(优选氯或溴)或磺酸酯(优选甲磺酸酯))以及与碱(例如氢化钠或碳酸钾)转化来获得。这在下面的方案10中示出。
方案10
具有式(XV)的化合物(其中R3和R5是如针对式(I)所定义的)可以通过将具有式(XVI)的化合物(其中R3是如针对式(I)所定义的)与具有式(XVII)的化合物(其中R5是如针对式(I)所定义的并且R12是羟基或卤素(优选氯)和路易斯酸(例如氯化铁(III)或氯化铝(III))转化来获得。这在下面的方案11中示出。
方案11
具有式(XVIII)的化合物(其中R3、R4和X是如针对式(I)所定义的)可以通过将具有式(VI)的化合物(其中R3、R4和X是如针对式(I)所定义的)与具有式(XIX)的化合物在酸性条件下(例如借助于对甲苯磺酸)转化来获得。这在下面的方案12中示出。
方案12
以上方案中所述的某些中间体是新颖的并且如此形成本发明的另一个方面。
具有式(I)的这些化合物可以例如作为活性成分用于农业和相关领域,来控制植物害虫或用于非生物材料上来控制腐败微生物或潜在地对人类有害的生物。该新颖化合物的特色是使用比率低但活性高,植物耐受良好以及不危害环境。它们有非常有用的治疗的、预防的和***性的特质并且可以用于保护无数栽培植株。具有式(I)的化合物可以用于抑制或破坏在多种不同的有用植物作物的植物或植物部分(果实、花、叶子、茎、块茎、根)上出现的有害生物,同时还保护了例如稍后生长的那些植物部分免于致植物病的微生物的侵害。
还可能使用具有式(I)的化合物作为杀真菌剂。如本文使用的术语“杀真菌剂”意指控制、修饰或防止真菌生长的化合物。术语“杀真菌有效量”意指能够对真菌生长产生影响的这样一种化合物或这样的化合物的组合的量。控制或修饰的影响包括所有从自然发育的偏离,如杀死、阻滞等,并且防止包括在植物内或上面防止真菌感染的屏障或其他防御构造。
还有可能使用具有式I的化合物作为用于处理植物繁殖材料,例如种子(例如果实、块茎或谷粒)或植物插条(例如稻)的拌种剂(dressing agent),用于保护对抗真菌侵染连同对抗在土壤中存在的致植物病的真菌。可以在种植以前用包括具有式(I)的化合物的组合物处理繁殖材料:例如可以在播种以前涂敷种子。还可以通过在液体配制品中浸渍种子或通过用固体配制品包衣它们,从而将具有式(I)的化合物施用至谷物(包衣)。还可以在种植繁殖材料时,将组合物施用至种植位点,例如在播种期间施用至种子的犁沟。本发明还涉及处理植物繁殖材料的这样的方法,并且涉及如此处理的植物繁殖材料。
此外,根据本发明所述的这些化合物可以用于控制相关领域的真菌,这些领域是例如在工业材料(包括木材以及与木材有关的工业产品)的保护中、在食品存储中、在卫生管理中。
此外,本发明还可以用于保护非生命材料(例如木料、墙板和涂料)免受真菌攻击。
具有式(I)的化合物和含有它们的杀真菌组合物可以用于控制由广泛的真菌植物病原体引起的植物疾病。它们有效地控制广泛的植物疾病,如观赏植物、草皮、蔬菜、大田、谷类、以及水果作物的叶病原体。
可以被控制的疾病的这些真菌和真菌载体连同致植物病细菌和病毒是例如:
伞枝梨头霉、链格孢属、丝囊霉属、壳二孢属、曲霉属(包括黄曲霉、烟曲霉、构巢曲霉、黑曲霉、土曲霉)、短梗霉属(包括出芽短梗霉(A.pullulans))、皮炎芽生菌、小麦白粉病菌、莴苣盘梗霉(Bremia lactucae)、葡萄座腔菌属(包括葡萄溃疡病菌(B.dothidea)、树花地衣葡萄座腔菌(B.obtusa))、葡萄孢属(包括灰葡萄孢(B.cinerea))、假丝酵母属(包括白色念珠菌、光滑球念珠菌(C.glabrata)、克鲁斯念珠菌(C.krusei)、萄牙念珠菌(C.1usitaniae)、***滑念珠菌(C.parapsilosis)、热带念珠菌(C.tropicalis))、Cephaloascus fragrans、长喙壳属、尾孢属(包括褐斑病菌(C.arachidicola))、晚斑病菌(Cercosporidium personatum)、枝孢霉属、麦角菌、
粗球孢子菌、旋孢腔菌属、炭疽菌属(包括香蕉炭疽病菌(C.musae))、
新型隐球菌、间座壳属(Diaporthe spp)、亚隔孢壳属、内脐蠕孢属、痂囊腔菌属、
表皮癣菌属、梨火疫病菌、白粉菌属(包括菊科白粉菌(E.cichoracearum))、
葡萄顶枯病菌(Eutypa lata)、镰刀菌属(包括大刀镰刀菌、禾谷镰刀菌、F.镰刀菌、串珠镰刀菌、胶孢镰刀菌、茄病镰刀菌、尖孢镰刀菌、层出镰刀菌)、小麦全蚀病菌(Gaeumannomyces graminis)、藤仓赤霉菌(Gibberella fujikuroi)、煤烟病菌(Gloeodespomigena)、香蕉炭疽盘长孢菌(Gloeosporium mmusarum)、苹果炭疽病菌(Glomerellacingulate)、葡萄球座菌(Guignardia bidwellii)、植物受桧胶锈菌(Gymnosporangiumjuniperi-virginianae)、长蠕孢属、驼孢锈菌属、组织胞浆菌属(包括荚膜组织胞浆菌(H.capsulatum))、红线病菌、Leptographium lindbergi、辣椒白粉病菌(Leveillula taurica)、松针散盘壳(Lophodermium seditiosum)、雪霉叶枯菌(Microdochium nivale)、小孢子菌属、链核盘菌属、毛霉属、球腔菌属(包括禾生球腔菌、苹果黑点病菌(M.Pomi))、树梢枯病菌、云杉病菌、副球孢子菌属、青霉属(包括指状青霉、意大利青霉)、霉样真霉属、指霜霉属(包括玉蜀黍指霜霉、菲律宾霜指霉和高粱指霜霉)、霜霉属、颖枯壳针孢、豆薯层锈菌、桑黄火木针层孔菌(Phellinu igniarus)、瓶霉蚁属、茎点霉属、葡萄生拟茎点菌(Phomopsis viticola)、疫霉菌属(包括致病疫霉菌)、单轴霉属(包括霍尔斯单轴霉菌、葡萄霜霉病菌(P.viticola))、格孢腔菌属、叉丝单囊壳属(包括白叉丝单囊壳(P.leucotricha))、禾谷多粘菌(Polymyxa graminis)、甜菜多粘菌(Polymyxabetae)、小麦基腐病菌(Pseudocercosporella herpotrichoides)、假单胞菌属、假霜霉属(包括黄瓜霜霉病菌、葎草假霜霉)、Pseudopeziza tracheiphila、霜霉属属(包括大麦柄锈菌(P.hordei)、小麦叶锈病菌(P.recondita)、条形柄锈菌(P.Striiformis)、小麦褐锈菌(P.triticina))、埋核盘菌属、核腔菌属、梨孢属(包括稻瘟病菌(P.oryzae))、腐霉属(包括终极腐霉菌)、柱隔孢属、丝核菌属、微小根毛霉(Rhizomucor pusillus)、少根根霉、喙孢属、丝孢菌属(包括尖端赛多孢子菌和多育赛多孢子菌)、煤点病(Schizothyrium pomi)、核盘菌属、小核菌属、壳针孢属(包括颖枯壳针孢(S.nodorum)、小麦壳针孢(S.tritici))、草莓白粉病菌(Sphaerotheca macularis)、棕丝单囊壳(Sphaerotheca fusca)(黄瓜白粉病菌(Sphaerotheca fuliginea))、孢子丝菌属(Sporothorix)、颖枯壳多孢(Stagonosporanodorum)、匍柄霉属(Stemphylium)、毛韧革菌(Stereum hirsutum)、水稻枯纹病菌(Thanatephorus cucumeris)、根串珠霉(Thielaviopsis basicola)、腥黑粉菌属、木霉属(包括哈茨木霉、拟康氏木霉、绿色木霉)、
毛癣菌属、核瑚菌属、葡萄钩丝壳、条黑粉菌属(Urocystis)、黑粉菌属(Ustilago)、黑星菌属(包括苹果黑星菌(V.inaequalis))、轮枝孢属以及黄单胞菌属。
具体地,具有式(I)的化合物和含有它们的杀真菌组合物可以用于控制由担子菌纲、子囊菌纲、卵菌纲和/或半知菌纲、Blasocladiomycete、壶菌纲、球囊菌纲(Glomeromycete)和/或粒毛盘菌纲(Mucoromycete)中的广谱的真菌植物病原体引起的植物疾病。
这些病原体可以包括:
卵菌纲,包括疫霉病,如由辣椒疫霉菌、致病疫霉菌、大豆疫霉菌、草莓疫莓菌(Phytophthora fragariae)、烟草疫霉菌(Phytophthora nicotianae)、樟疫霉(Phytophthora cinnamomi)、柑橘生疫霉(Phytophthora citricola)、柑橘褐腐疫霉(Phytophthora citrophthora)和马铃薯绯腐病菌(Phytophthora erythroseptica)引起的那些;腐霉病,例如由瓜果腐霉菌、强雄腐霉菌(Pythium arrhenomanes)、禾生腐霉菌、畸雌腐霉菌(Pythium irregulare)和终极腐霉菌引起的那些;由霜霉目诸如大葱霜霉菌(Peronospora destructor)、白菜霜霉菌、葡萄霜霉菌、向日葵霜霉菌、黄瓜霜霉菌、白锈菌(Albugo Candida)、水稻霜霉病和莴苣霜霉菌引起的疾病;以及其他,例如螺壳状丝囊霉、Labyrinthula zosterae、高梁霜指霉(Peronosclerospora sorghi)和禾生指梗霉(Sclerospora graminicola)。
子囊菌纲,包括斑纹病、斑点病、瘟病或疫病和/或腐病,例如由如下引起的那些:格孢菌目如大蒜白斑病菌(Stemphylium solani)、Stagonospora tainanensis、油橄榄环梗孢菌、玉米大斑病菌(Setosphaeria turcica)、Pyrenochaeta lycoperisici、枯叶格孢腔菌、实腐茎点霉(Phoma destructiva)、Phaeosphaeria herpotrichoides、Phaeocryptocus gaeumannii、Ophiosphaerella graminicola、小麦全蚀病(Ophiobolusgraminis)、十字花科小球腔菌(Leptosphaeria maculans)、软腐病菌(Hendersoniacreberrima)、壳针孢叶枯病菌(Helminthosporium triticirepentis)、玉米大斑病菌(Setosphaeria turcica)、大豆内脐蠕孢(Drechsleraglycines)、西瓜蔓枯病菌(Didymella bryoniae)、油橄榄孔雀斑病菌(Cycloconium oleagineum)、多主棒孢菌、禾旋孢腔菌、火龙果黑斑病菌(Bipolaris cactivora)、苹果黑星病菌、圆核腔菌、燕麦草核腔菌(Pyrenophora tritici-repentis)、互隔链格孢菌、芸苔链格孢菌(Alternariabrassicicola)、茄链格孢菌和西红柿链格孢菌(Alternaria tomatophila);煤炱目(Capnodiales)如小麦壳针孢、颖枯壳针孢、大豆壳针孢(Septoria glycines)、落花生尾孢菌(Cercospora arachidicola)、大豆灰斑病菌、玉米灰斑病菌、荠白斑病菌(Cercosporella capsellae)以及麦叶白霉(Cercosporellaherpotrichoides)、桃疮痂病菌(Cladosporium carpophilum)、散生枝孢(Cladosporium effusum)、褐孢霉(Passalorafulva)、尖孢枝孢(Cladosporium oxysporum)、Dothistroma septosporum、葡萄褐斑病菌(Isariopsis clavispora)、香蕉黑条叶斑病菌、禾生球腔菌(Mycosphaerellagraminicola)、散梗菌绒孢菌(Mycovellosiella koepkeii)、Phaeoisariopsisbataticola、葡萄褐斑病菌(Pseudocercospora vitis)、小麦基腐病菌、甜菜叶斑病菌、柱隔孢叶斑病菌(Ramularia collo-cygni);粪壳菌目如小麦全蚀病菌、稻瘟病菌(Magnaporthe grisea)、稻梨孢、间座壳目如榛子东部枯萎病菌、Apiognomoniaerrabunda、Cytospora platani、大豆北方茎溃疡病菌、毁灭性座盘孢(Disculadestructiva)、草莓日规壳菌(Gnomonia fructicola)、葡萄苦腐病菌、核桃黑盘壳菌(Melanconium juglandinum)、葡萄生拟茎点菌(Phomopsis viticola)、胡桃溃疡病菌(Sirococcus clavigignenti-juglandacearum)、干孢盾壳椿启介菌(Tubakia dryina)、Dicarpella spp.、苹果树腐烂病菌(Valsa ceratosperma);以及其他,如Actinothyriumgraminis、豌豆壳二孢、黄曲霉、烟曲霉菌、构巢曲霉、番木瓜座糙孢菌、叶斑病菌(Blumeriella jaapii)、假丝酵母属、煤炱病菌(Capnodium ramosum)、Cephaloascusspp.、麦类条斑病菌(Cephalosporium gramineum)、奇异长喙壳(Ceratocystisparadoxa)、毛壳菌属、拟白膜盘菌(Hymenoscyphus pseudoalbidus)、球孢子菌属、李属柱孢霉(Cylindrosporium padi)、双壳菌(Diplocarpon malae)、Drepanopezizacampestris、痂囊腔菌(Elsinoe ampelina)、黑附球菌、表皮癣菌属、葡萄顶枯病、白地霉、禾谷绒座壳(Gibellina cerealis)、高粱胶尾孢(Gloeocercospora sorghi)、煤烟病菌(Gloeodes pomigena)、Gloeosporium perennans;毒麦内生真菌(Gloeotiniatemulenta)、Griphospaeria corticola、利尼球梗孢(Kabatiella lini)、小孢粘束孢(Leptographium microsporum)、Leptosphaerulinia crassiasca、Lophodermiumseditiosum、禾谷盘二孢菌(Marssonina graminicola)、雪霉叶枯菌、美澳型核果褐腐病菌、稻云形病(Monographella albescens)、甜瓜黑点根腐病菌、丝环盘菌属(Naemacyclusspp.)、新榆枯萎病菌、巴西副球孢子菌、扩展青霉、杜鹃盘多毛孢霉(Pestalotiarhododendri)、霉样真霉属(Petriellidium)、无柄盘菌属、大豆茎褐腐病菌、Phyllachorapomigena、杂食动物瘤梗孢(Phymatotrichum omnivora)、隐秘囊孢菌(Physalosporaabdila)、烟草囊孢壳(Plectosporium tabacinum)、马铃薯皮斑病菌、苜蓿假盘菌(Pseudopeziza medicaginis)、芸薹埋核盘菌(Pyrenopeziza brassicae)、高粱座枝孢(Ramulispora sorghi)、Rhabdocline pseudotsugae、大麦云纹病菌(Rhynchosporiumsecalis)、稻帚枝杆孢(Sacrocladium oryzae)、足放线病菌属(Scedosporium)、仁果裂盾菌、核盘菌、小核盘菌;小核菌属、雪腐病核瑚菌(Typhula ishikariensis)、玛丽盘双端毛孢(Seimatosporium mariae)、Lepteutypa cupressi、Septocyta ruborum、Sphacelomaperseae、Sporonema phacidioides、千年枣眼点病菌(Stigmina palmivora)、Tapesiayallundae、梨外囊菌(Taphrina bullata)、棉花黑根腐病菌(Thielviopsis basicola)、Trichoseptoria fructigena、蝇粪病菌(Zygophiala jamaicensis);白粉病,例如由白粉菌目如小麦白粉病菌、蓼白粉病菌、葡萄钩丝壳、黄瓜白粉病菌(Sphaerotheca fuligena)、白叉丝单囊壳、Podospaera macularis、二孢白粉菌(Golovinomyces cichoracearum)、鞑靼内丝白粉菌(Leveillula taurica)、扩散叉丝壳、Oidiopsis gossypii、榛球针壳(Phyllactinia guttata)以及Oidium arachidis引起的那些;霉,例如由葡萄座腔菌如***壳菌(Dothiorella aromatica)、连续色二孢(Diplodia seriata)、比德瓦里球座菌(Guignardia bidwellii)、灰霉菌(Botrytis cinerea)、大葱孢盘菌(Botryotiniaallii)、蚕豆孢盘菌(Botryotinia fabae)、扁桃壳梭菌(Fusicoccum amygdali)、龙眼焦腐病菌(Lasiodiplodia theobromae)、茶生大茎点霉(Macrophoma theicola)、菜豆壳球孢菌、葫芦科叶点霉(Phyllosticta cucurbitacearum)引起的那些;炭疽病,例如由小丛壳(Glommerelales)如盘长孢状刺盘孢、瓜类炭疽菌、棉花炭疽病菌、围小丛壳、以及禾生炭疽菌引起的那些;以及枯萎病或疫病,例如由肉座菌目如笔直顶孢霉、紫麦角菌、黄色镰刀菌、禾谷镰刀菌、大豆猝死综合症病菌(Fusarium virguliforme)、尖孢镰刀菌、胶孢镰刀菌、古巴尖孢镰孢(Fusarium oxysporum f.sp.cubense)、Gerlachia nivale、藤仓赤霉、玉米赤霉、胶枝霉属、疣孢漆斑菌、Nectria ramulariae、绿色木霉、粉红聚端孢菌以及鳄梨根腐病原菌(Verticillium theobromae)引起的那些。
担子菌纲,包括黑穗病,例如由黑粉菌目如稻曲病菌、小麦散黑穗病菌、小麦散黑粉菌菌、玉米黑粉病菌引起的那些,锈病例如由柄锈菌如Cerotelium fici、云杉帚锈病菌(Chrysomyxa arctostaphyli)、番薯鞘锈菌(Coleosporium ipomoeae)、咖啡驼孢锈菌(Hemileia vastatrix)、落花生柄锈菌、Puccinia cacabata、禾柄锈菌、隐匿柄锈菌、高粱柄锈菌、大麦柄锈菌、大麦条形柄锈菌(Puccinia striiforrnis f.sp.Hordei)、小麦条形柄锈菌(Puccinia striiformis f.sp.Secalis)、榛膨痂锈菌(Pucciniastrum coryli);或锈菌目如松疱锈病菌、美洲苹果锈病菌(Gymnosporangium juniperi-virginianae)、杨树叶锈病菌(Melampsora medusae)、豆薯层锈菌(Phakopsora pachyrhizi)、短尖多胞锈菌(Phragmidium mucronatum)、Physopella ampelosidis、变色疣双胞锈菌(Tranzscheliadiscolor)以及蚕豆单孢锈菌(Uromyces viciae-fabae)引起的那些;以及其他腐病和疾病,例如由隐球菌属、茶饼病菌、Marasmiellus inoderma、小菇属、丝黑穗病菌(Sphacelotheca reiliana)、雪腐病核瑚菌(Typhula ishikariensis)、冰草条黑粉菌(Urocystis agropyri)、Itersonilia perplexans、伏革菌(Corticium invisum)、地衣状伏革菌(Laetisaria fuciformis)、Waitea circinata、立枯丝核菌、Thanetephoruscucurmeris、大丽花叶黑粉菌(Entyloma dahliae)、Entylomella microspora、沼湿草尾孢黑粉菌(Neovossia moliniae)和小麦网腥黑穗病菌(Tilletia caries)引起的那些。
芽枝霉纲,如玉蜀黍节壶菌(Physoderma maydis)。
粒毛盘菌纲(Mucoromycete),如笋瓜花腐病菌(Choanephora cucurbitarum);毛霉属;少根根霉,
连同由与以上列出的那些紧密相关的其他物种和属引起的疾病。
除了它们的杀真菌活性之外,这些化合物和包括它们的组合物还可以具有针对细菌如梨火疫病菌、软腐欧文氏菌(Erwinia caratovora)、野油菜黄单胞菌、丁香假单胞菌、马铃薯疮痂病菌(Strptomyces scabies)和其他相关物种连同某些原生动物的活性。
在本发明的范围内,有待保护的目标作物和/或有用植物典型地包括多年生和一年生作物,例如浆果植物,例如黑莓、蓝莓、蔓越莓、树莓以及草莓;谷类,例如大麦、玉米(maize或corn)、小米、燕麦、水稻、黑麦、高粱、黑小麦以及小麦;纤维植物,例如棉花、亚麻、***、黄麻和剑麻;大田作物,例如糖甜菜和饲料甜菜、咖啡豆、啤酒花、芥菜、油菜(卡诺拉)、罂粟、甘蔗、向日葵、茶以及烟草;果树,例如苹果、杏、鳄梨、香蕉、樱桃、柑橘、油桃、桃、梨以及李子;草,例如百慕大草、蓝草、本特草、蜈蚣草、牛毛草、黑麦草、圣奥古斯丁草以及结缕草;药草,如罗勒、琉璃苣、细香葱、胡荽、薰衣草、独活草、薄荷、牛至、荷兰芹、迷迭香、鼠尾草以及百里香;豆类,例如菜豆、小扁豆、豌豆以及大豆;坚果,例如杏仁、腰果、落花生、榛子、花生、山核桃、开心果以及核桃;棕榈植物,例如油棕榈;观赏植物,例如花卉、灌木和树;其他树木,例如可可、椰子、橄榄以及橡胶;蔬菜,例如芦笋、茄子、西兰花、卷心菜、胡萝卜、黄瓜、大蒜、莴苣、西葫芦、甜瓜、秋葵、洋葱、胡椒、马铃薯、南瓜、大黄、菠菜以及番茄;以及葡萄藤,例如葡萄。
根据本发明的有用植物和/或目标作物包括常规的连同遗传增强或遗传工程处理的品种,例如像抗虫的(例如Bt.和VIP品种)连同抗病的、耐除草剂的(例如耐草甘膦和草丁膦的玉米品种,在商品名和下可商购)以及耐受线虫的品种。通过举例的方式,适合的遗传增强或遗传工程处理的作物品种包括Stoneville 5599BR棉花和Stoneville 4892BR棉花品种。
术语“有用植物”和/或“目标作物”应当理解为还包括由于常规育种方法或基因工程方法而赋予了对除草剂(像溴草腈)或除草剂类的(例如像HPPD抑制剂、ALS抑制剂,如氟嘧磺隆、氟丙磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮酰-莽草酸-3-磷酸-合酶(5-enol-pyrovyl-shikimate-3-phosphate-synthase))抑制剂、GS(谷氨酰胺合酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)的耐受性的有用植物。已经通过常规育种方法(诱变)变得对咪唑啉酮例如甲氧咪草烟具有耐受力的作物的一个实例是夏季油菜(卡诺拉(Canola))。已经通过基因工程方法使其对除草剂或除草剂类耐受的作物的实例包括抗草甘膦和抗草丁膦玉蜀黍品种,它们是在和商标名下可商购的。
术语“有用植物”和/或“目标作物”应被理解为包括天然地或已经赋予对有害昆虫的抗性的那些。这包括通过使用重组DNA技术转化从而例如能够合成一种或多种选择性作用毒素的植物,这些毒素例如是从如产毒素的细菌已知的。可以被表达的毒素的实例包括δ-内毒素,营养期杀虫蛋白(Vip),细菌定殖线虫的杀虫蛋白,以及由蝎子、蛛形纲动物、黄蜂和真菌产生的毒素。已经被修饰为表达苏云金芽孢杆菌毒素的作物的实例是Bt maize(先正达种子公司(Syngenta Seeds))。包括编码杀昆虫抗性并且由此表达多于一种毒素的多于一种基因的作物的实例是(先正达种子公司)。作物或其种子材料还可以是对多种类型的有害生物具有抗性(当通过遗传修饰产生时的所谓的叠加转基因事件)。例如,植物可以具有表达杀昆虫蛋白同时耐受除草剂的能力,例如Herculex(陶氏益农公司(Dow AgroSciences),先锋良种国际公司(Pioneer Hi-Bred International))。
术语“有用植物”和/或“目标作物”可以理解为也包括已经通过使用重组DNA技术转换了的,以至于能够合成有选择性活性的抗致病性物质,例如,所谓的“致病机理相关的蛋白”(PRPs,见例EP-A-0392225)。例如,通过EP-A-0 392225、WO 95/33818,和EP-A-0353191,这种抗致病性物质和能够合成这种抗致病性物质的转基因植物的实例是已知的。生产这种转基因植物的方法对精通艺术的人是来说是众所周知的并且例如上面的出版物中有描述这种方法。
可通过转基因植物表达的毒素包括,例如杀昆虫蛋白质,例如来自于枯草芽孢杆菌或日本甲虫芽孢杆菌的杀昆虫蛋白质;或来自于苏云金芽孢杆菌的杀昆虫蛋白质,例如δ-内毒素,例如Cry1Ab、CrylAc、Cry1F、CrylFa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或线虫寄生性细菌的杀昆虫蛋白质,例如光杆状茵属或致病杆菌属,例如发光光杆状茵、嗜线虫致病杆菌;由动物产生的毒素,例如蝎毒素、蜘蛛毒素、黄蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,例如链霉菌毒素;植物凝集素,例如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,例如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯贮存蛋白(patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),例如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,例如3-羟基类固醇氧化酶、蜕皮类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕皮激素抑制剂、HMG-COA-还原酶,离子通道阻断剂,例如钠通道或钙通道阻断剂,保幼激素酯酶,利尿激素受体、芪合酶、联苄合酶、几丁酶和葡聚糖酶。
另外,在本发明背景下,δ-内毒素例如Cry1Ab、Cry1Ac、Cry1F、CrylFa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A应理解为显然还包括混合型毒素、截短的毒素和经修饰的毒素。混合型毒素是通过那些蛋白的不同结构域的新组合重组产生的(参见例如,WO 02/15701)。截短的毒素(例如截短的Cry1Ab)是已知的。在经修饰的毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在这种氨基酸置换中,优选将非天然存在的蛋白酶识别序列***毒素中,例如在Cry3A055的情况下,一种组织蛋白酶-G-识别序列被***Cry3A毒素(参见WO03/018810)。
这样的毒素或能够合成这样的毒素的转基因植物的更多实例披露于例如EP-A-0374753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备这样的转基因植物的方法对于本领域的普通技术人员而言通常是已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367 474、EP-A-0 401 979以及WO90/13651中已知。
包括在转基因植物中的毒素使得植物对有害昆虫有耐受性。这些昆虫可以存在于任何昆虫分类群,但尤其是通常在甲虫(鞘翅目)、双翅昆虫(双翅目)以及蝴蝶(鳞翅目)中发现。
包含一种或多种编码杀昆虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。这样的植物的实例是:产率(玉米品种,表达Cry1Ab毒素);产率Gard(玉米品种,表达Cry3Bb1毒素);产率Gard(玉米品种,表达Cry1AB以及Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素以及实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(PAT));NuCOTN(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac和Cry2Ab毒素);(棉花品种,表达Vip3A和Cry1Ab毒素);(马铃薯品种,表达Cry3A毒素);GT Advantage(GA21耐草甘膦性状),CB Advantage(Bt11玉米螟(CB)性状)以及
这样的转基因作物的其他实例是:
1.Bt11玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del’Hobit)27,F-31790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt11玉米还转基因表达PAT酶以实现对除草剂草丁膦铵盐的耐受性。
2.Bt176玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del’Hobit)27,F-31790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt176玉米还转基因地表达PAT酶以实现对除草剂草丁膦铵的耐受性。
3.MIR604玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Cheminde l’Hobit)27,F-31790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使之具有昆虫抗性的玉米。此毒素是通过***组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。此类转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自孟山都欧洲公司(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔,比利时,登记号C/DE/02/9。MON863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传改性的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草丁膦铵的耐受性。
7.NK603×MON 810玉米,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON810杂交,由常规育种的杂交玉米品种构成。NK603×MON 810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白质CP4EPSPS,使之耐除草剂(含有草甘膦),以及由苏云金芽孢杆菌库尔斯塔克亚种获得的Cry1Ab毒素,使之耐某些鳞翅目昆虫,包括欧洲玉米螟。
如在此使用的术语“场所”是指植物在其中或其上生长的地方,或栽培植物的种子被播种的地方,或者种子将要被置于土壤中的地方。它包括土壤、种子以及幼苗,连同建立的植被。
术语“植物”是指植物的所有有形部分,包括种子、幼苗、幼树、根、块茎、茎、秆、叶和果实。
术语“植物繁殖材料”应当理解为表示植物的生殖部分,如种子,这些部分可以用于该植物的繁殖,以及营养性材料,如插条或块茎(例如马铃薯)。可以提及,例如种子(在严格意义上)、根、果实、块茎、球茎、根茎以及植物的部分。还可以提及在发芽后或破土后将被移植的发芽植物和幼小植物。这些幼小植物可以通过浸渍进行完全或部分处理而在移植之前进行保护。优选地,“植物繁殖材料”应当理解为表示种子。
在此提及的使用其俗名的杀有害生物剂是已知的,例如,从“杀有害生物剂手册(The Pesticide Manual)”,15版,英国作物保护委员会(British Crop ProtectionCouncil)2009。
具有式(I)的化合物能以未修饰的形式使用,或者优选地,与配制品领域中常规使用的佐剂一起使用。为此目的,它们可以按已知方式便利地配制为可乳化的浓缩物、可包衣的糊剂、直接可喷雾的或可稀释的溶液或悬浮液、稀释乳液、可湿性粉剂、可溶性粉剂、尘粉剂(dust)、颗粒以及还有封装物,例如在聚合物的物质中。对于这些组合物的类型,根据预期的目的以及盛行环境来选择施用方法,如喷洒、雾化、撒粉、播散、包衣或倾倒。这些组合物还可以含有另外的佐剂,如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂,以及肥料、微量营养素供体或其他用于获得特殊效果的配制品。
合适的载体以及佐剂(例如对于农业用途)可以是固体或液体的并且是在配制品技术中有用的物质,例如天然或再生的矿物物质、溶剂、分散体、湿润剂、增粘剂、增稠剂、粘合剂或肥料。例如这样的载体在WO97/33890中有描述。
悬浮液浓缩物是活性化合物的高度分散的固体颗粒悬浮于其中的水性配制品。这样的配制品包括抗沉降剂和分散剂,并且可以进一步包括湿润剂,以增强活性,以及消泡剂和晶体生长抑制剂。在使用时,将这些浓缩物稀释在水中,并且通常作为喷雾剂施用至有待处理的区域。活性成分的量可以范围是该浓缩物的0.5%到95%。
可湿性粉剂是处于在水中或其他液态载体中容易分散的高度分散的颗粒形式。这些颗粒包含保存在固体基质里的活性成分。典型的固体基质包括漂白土、高岭土、硅石和其他容易湿化的有机或无机固体。可湿性粉剂通常包含从5%到95%的活性成分加上少量的润湿剂、分散剂或乳化剂。
可乳化浓缩物是在水中或其他液体中可分散的均匀的液体组合物并且可以完全由活性化合物与一种液体或固体乳化剂组成,或者还可以包含一种液态载体,例如二甲苯、重芳香族石脑油、异佛尔酮和其他不挥发有机溶剂。使用时,将这些可乳化浓缩物分散在水中或其他液体中并且通常以喷雾施用于待处理的区域。活性成分的量可以范围是该浓缩物的0.5%到95%。
颗粒配制品包括挤出物和较粗颗粒两者,并且通常不用稀释地施用于需要处理的区域。用于颗粒配制品的典型载体包括沙、漂白土、凹凸棒石粘土、膨润土、蒙脱土、蛭石、珍珠岩、碳酸钙、砖、浮石、叶蜡石、高岭土、白云石、灰泥、木粉、碎玉米穗轴、碎花生壳、糖、氯化钠、硫酸钠、硅酸钠、硼酸钠、氧化镁、云母、氧化铁、氧化锌、氧化钛、氧化锑、冰晶石、石膏、硅藻土、硫酸钙以及其他有机或无机的吸收活性化合物或被活性化合物包衣的材料。颗粒配制品通常含有5%到25%的活性成分,这些成分可以包括表面活性剂,如重芳族石脑油、煤油和其他石油馏分、或者植物油;和/或粘着剂,如糊精、胶粘剂或合成树脂。
尘剂是活性成分与高度分散的固体(如滑石、粘土、面粉以及其他有机与无机的作为分散剂和载体的固体)的可自由流动的混合物。
微囊典型地为包裹在惰性多孔壳内的活性成分的微滴或颗粒,该惰性多孔壳允许以可控的速率让包住的材料逃逸到环境中。包囊的微滴的直径典型地为1微米到50微米。包裹的液体典型地构成该胶囊重量的50%至95%并且除了活性化合物外还可以包括溶剂。包囊的颗粒通常是多孔颗粒,其中多孔膜将颗粒孔口密封,从而将活性种类以液体形式保存在颗粒孔内部。颗粒的直径的范围典型地是从1毫米至1厘米并且优选地1毫米至2毫米。颗粒通过挤出、凝聚或成球形成,或者是天然存在的。这样的材料的实例为蛭石、烧结粘土、高岭土、凹凸棒石粘土、锯屑和碳精粒。壳或膜材料包括天然和合成橡胶、纤维材料、苯乙烯-丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯和淀粉黄原酸酯。
用于农用化学应用的其他有用配制品包括活性成分在溶剂(如丙酮、烷基化萘、二甲苯和其他有机溶剂)中的简单溶液,在该溶剂中活性成分以所希望的浓度完全溶解。也可以使用加压的喷雾剂,其中由于低沸点分散剂溶剂载体的蒸发活性成分以高度分散的形式分散。
在上述配制品类型中对于配制本发明的组合物有用的合适的农用佐剂和载体是本领域的普通技术人员熟知的。
可以利用的液态载体包括例如水、甲苯、二甲苯、石脑油、作物油、丙酮、甲基乙基酮、环己酮、乙酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、氯苯、环己烷、环己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松香酸二甘醇酯、二甘醇丁基醚、二甘醇***、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲醚、二丙二醇二苯甲酸酯、二丙二醇(diproxitol)、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸亚乙酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乙二醇、乙二醇丁醚、乙二醇甲醚、γ-丁内酯、甘油、甘油二乙酸酯、甘油一乙酸酯、甘油三乙酸酯、十六烷、己二醇、乙酸异戊酯、乙酸异冰片酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异丙叉丙酮、甲氧基丙醇、甲基异戊酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八酸、乙酸辛胺酯、油酸、油胺、邻二甲苯、苯酚、聚乙二醇(PEG400)、丙酸、丙二醇、丙二醇单甲醚、对二甲苯、甲苯、磷酸三乙酯、三甘醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、甲醇、乙醇、异丙醇、以及更高分子量的醇类如戊醇、四氢糠醇、己醇、辛醇等,乙二醇、丙二醇、甘油以及N-甲基-2-吡咯烷酮。水通常是用以稀释浓缩物的选用载体。
合适的固体载体包括例如滑石、二氧化钛、叶腊石粘土、硅石、凹凸棒石粘土、硅藻土(kieselguhr)、白垩、硅藻土(diatomaxeous earth)、石灰、碳酸钙、膨润土、漂白土、棉子壳、小麦粉、大豆粉、浮石、木粉、核桃壳粉以及木质素。
在所述液体和固体组合物中可有利地采用广泛的表面活性剂,尤其是被设计为可在施用前用载体稀释的那些。这些试剂在使用时通常按重量计组成配制品的从0.1%到15%。它们在性质上可以是阴离子的、阳离子的、非离子的或聚合的并且可以作为乳化剂、润湿剂、悬浮剂或以其他目的采用。典型的表面活性剂包括烷基硫酸酯,例如二乙醇铵十二烷基硫酸酯;烷芳基磺酸盐,例如十二烷基苯磺酸钙;烷基酚-环氧烷加成产物,例如壬基酚C18乙氧基化物;醇-环氧烷加成产物,例如十三烷基醇-C16乙氧基化物;皂,例如硬脂酸钠;烷基萘磺酸盐,例如二丁基萘磺酸钠;磺基琥珀酸盐的二烷基酯,例如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,例如山梨糖醇油酸酯;季胺类,例如氯化十二烷基三甲基铵;脂肪酸的聚乙二醇酯,例如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及单和二烷基磷酸酯盐。
通常在农业组合物中使用的其他辅助剂包括结晶作用抑制剂、粘度改性剂、悬浮剂、喷雾液滴改性剂、颜料、抗氧化剂、发泡剂、防泡剂、遮光剂、相容性试剂、消泡剂、掩蔽剂、中和剂和缓冲剂、腐蚀抑制剂、染料、增味剂、铺展剂、渗透助剂、微量营养素、柔润剂、润滑剂以及固着剂。
本发明还提供了一种包含根据本发明的具有式(I)的化合物连同一种或者多种杀有害物剂、植物营养素或者植物肥料的组合物的用途。该组合还可包括使用任何手段,例如常规育种或基因修饰结合到植物中的特定植物性状。
植物营养素或植物肥料的适宜实例是硫酸钙(CaSO4)、硝酸钙(Ca(NO3)2.4H2O)、碳酸钙(CaCO3)、硝酸钾(KNO3)、硫酸镁(MgSO4)、磷酸氢钾(KH2PO4)、硫酸锰(MnSO4)、硫酸铜(CuSO4)、硫酸锌(ZnSO4)、氯化镍(NiCl2)、硫酸钴(CoSO4)、氢氧化钾(KOH)、氯化钠(NaCl)、硼酸(H3BO3)及其金属盐(Na2MoO4)。营养素能以按重量计5%至50%,优选按重量计10%至25%,或者各自按重量计15%至20%的量存在。优选的另外的营养素是尿素((NH2)2CO)、蜜胺(C3H6N6)、氧化钾(K2O)和无机硝酸盐。最优选的另外的植物营养素是氧化钾。在优选的另外的营养素是尿素的情况下,它能以按重量计1%至20%,优选按重量计2%至10%,或者按重量计3%至7%的量存在。
杀虫剂的适合的实例是无环氨基酸(acycloamino acid)杀真菌剂、脂肪族氮杀真菌剂、酰胺杀真菌剂、苯胺杀真菌剂、抗生素杀真菌剂、芳香族杀真菌剂、含砷杀真菌剂、芳基苯基酮杀真菌剂、苯甲酰胺杀真菌剂、苯甲酰苯胺杀真菌剂、苯并咪唑杀真菌剂、苯并噻唑杀真菌剂、植物杀真菌剂、桥联联苯基杀真菌剂、氨基甲酸酯杀真菌剂、苯氨甲酸酯杀真菌剂、康唑杀真菌剂、铜杀真菌剂、二甲酰亚胺杀真菌剂、二硝基苯酚杀真菌剂、二硫代氨基甲酸酯杀真菌剂、二硫戊环杀真菌剂、糠酰胺杀真菌剂、糠苯胺杀真菌剂、酰肼真菌剂、咪唑杀真菌剂、汞杀真菌剂、吗啉杀真菌剂、有机磷杀真菌剂、有机锡杀真菌剂、氧硫杂环己二烯(oxathiin)杀真菌剂、噁唑杀真菌剂、苯硫酰胺杀真菌剂、多硫化物杀真菌剂、吡唑杀菌剂、吡啶杀真菌剂、嘧啶杀真菌剂、吡咯杀真菌剂、季铵杀真菌剂、喹啉杀真菌剂、醌杀真菌剂、喹喔啉杀真菌剂、嗜球果伞素杀真菌剂、磺酰苯胺(sulfonanilide)杀真菌剂、噻二唑杀真菌剂、噻唑杀真菌剂、噻唑烷杀真菌剂、硫代氨基甲酸酯杀真菌剂、噻吩杀真菌剂、三嗪杀真菌剂、***杀真菌剂、***并嘧啶杀真菌剂、尿素杀真菌剂、缬氨酰胺(valinamide)杀真菌剂、锌杀真菌剂、苯甲酰脲、氨基甲酸酯、氯化烟酰、二酰肼、二酰胺、菲普鲁来斯(fiprole)、大环内酯、硝基亚胺类(nitroimine)、硝基亚甲基类(nitromethylenes)、有机氯、有机磷酸盐、有机硅、有机锡、苯基吡唑、磷酸酯、拟除虫菊酯、多杀霉素(spinosyns)、特特拉姆酸衍生物、特窗酸衍生物、抗生素杀线虫剂、阿维菌素杀线虫剂、植物杀线虫剂、氨基甲酸酯杀线虫剂、肟氨基甲酸酯杀线虫剂、有机磷杀线虫剂、食线虫的真菌或细菌、酰胺除草剂、苯胺除草剂、含砷除草剂、芳基丙氨酸除草剂、芳氧基苯氧基丙酸除草剂、苯并呋喃基除草剂、苯甲酸除草剂、苯并噻唑除草剂、苯甲酰基环己二酮除草剂、氨基甲酸酯除草剂、苯氨甲酸酯除草剂、氯乙酰苯胺除草剂、氯三嗪除草剂、环己烯肟除草剂、环丙基异噁唑除草剂、二甲酰亚胺除草剂、二硝基苯胺除草剂、二硝基苯酚除草剂、二苯基醚除草剂、二硫代氨基甲酸酯除草剂、氟烷基三嗪除草剂、卤代脂肪族除草剂、咪唑啉酮除草剂、无机除草剂、甲氧基三嗪除草剂、甲基硫代三嗪除草剂、腈除草剂、硝基苯基醚除草剂、有机磷除草剂、噁二唑酮除草剂、噁唑除草剂、苯氧基除草剂、苯氧基乙酸除草剂、苯氧基丁酸除草剂、苯氧基丙酸除草剂、苯二胺除草剂、苯脲除草剂、邻苯二甲酸除草剂、吡啶甲酸除草剂、吡唑除草剂、哒嗪除草剂、哒嗪酮除草剂、吡啶除草剂、嘧啶二胺除草剂、嘧啶基氧基苄胺除草剂、嘧啶基磺酰脲除草剂、季铵除草剂、喹啉羧酸除草剂、磺酰胺除草剂、磺酰苯胺(sulfonanilide)除草剂、磺酰脲除草剂、噻二唑基脲除草剂、硫代酰胺除草剂、硫代氨基甲酸酯除草剂、硫代碳酸酯除草剂、硫脲除草剂、三嗪除草剂、三嗪酮除草剂、三嗪基磺酰脲除草剂、***除草剂、***酮除草剂、***并嘧啶除草剂、尿嘧啶除草剂、脲除草剂、微生物、植物提取物、信息素、微生物制剂(macrobial)以及其他生物制剂。
本发明的另一方面涉及控制或防止植物(例如有用植物(例如作物))、它们的繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料免于被昆虫或致植物病的或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)侵染的方法,该方法包括将具有式I的化合物或优选的如以上定义的单独的化合物作为活性成分施用至这些植物、植物的各部分或至其场所、它们的繁殖材料、或非生命材料的任何部分。
控制或防止是指将被昆虫或致植物病的或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)的侵染减少至这样一个被证明改进的水平。
控制或防止作物被致植物病微生物(尤其是真菌)或昆虫侵染的优选的方法是叶面施用,该方法包括施用具有式(I)的化合物、或含有至少一种所述化合物的农用化学组合物。施用频率和施用比率将取决于受相应的病原体或昆虫侵染的风险。然而,具有式(I)的化合物还可以通过用液体配制品浸泡该植物的场所或者通过将处于固体形式的化合物例如以颗粒形式施用到土壤(土壤施用)而经由土壤通过根(内吸作用)渗透该植物。在水稻作物中,可以将这样的颗粒施用到灌水的稻田中。具有式(I)的化合物还可以通过用一种杀真菌剂的液体配制品浸渍种子或块茎、或用一种固体配制品对其进行涂覆而施用到种子(包衣)上。
配制品(例如含有具有式(I)的化合物、以及(如果希望的话)固体或液体佐剂或用于包囊具有式(I)的化合物的单体的组合物)可以按已知方式制备,典型地通过将化合物与增充剂(例如溶剂、固体载体以及,任选地表面活性化合物(表面活性剂))进行密切地混合和/或研磨。
组合物的施用方法、也就是说控制以上提及的类型的有害生物的方法,例如喷洒、雾化、撒粉、涂刷、敷料、散射或浇注,选择这些方式以适合当时环境的既定目标;以及这些组合物用于控制以上提及的类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1ppm与1000ppm之间,优选地在0.1ppm与500ppm之间的活性成分。每公项的施用量优选是每公项1g到2000g活性成分,更优选是10到1000g/ha,最优选是10到600g/ha。当作为种子浸泡试剂使用时,适宜的剂量是从10mg至1g活性物质/kg种子。
当这些组合物用于处理种子时,比率为0.001g至50g具有式(I)的化合物/kg种子、优选地从0.01g至10g/kg种子一般是足够的。
适当地,预防性(意指在疾病发展之前)或治愈性(意指疾病发展之后)施用根据本发明的具有式(I)的化合物的组合物。
本发明的组合物能以任何常规形式使用,例如,以双包装、干种子处理用的粉剂(DS)、种子处理用的乳液(ES)、种子处理用的可流动性浓缩物(FS)、种子处理用的溶液(LS)、种子处理用的水分散性粉剂(WS)、种子处理用的胶囊悬浮液(CF)、种子处理用的凝胶(GF)、乳液浓缩物(EC)、悬浮液浓缩物(SC)、悬浮乳液(SE)、胶囊悬浮液(CS)、水分散性粒剂(WG)、可乳化性粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、分散性油悬剂(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮剂(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可湿性粉剂(WP)或与农业上可接受的佐剂组合的任何技术上可行的配制品的形式。
能以常规方式生产这样的组合物,例如通过混合活性成分与适当的配制惰性剂(稀释剂、溶剂、填充剂及任选地其他配制成分,如表面活性剂、杀生物剂、防冻剂、粘着剂、增稠剂及提供辅佐效果的化合物)。还可以使用意欲长期持续药效的常规缓释配制品。特别得,待以喷雾形式,如水可分散性浓缩物(例如EC、SC、DC、OD、SE、EW、EO以及类似物)、可湿性粉剂及颗粒施用的配制品,可包含表面活性剂例如湿润剂和分散剂及提供辅佐效果的其他化合物,例如甲醛与萘磺酸盐、烷芳基磺酸盐、木质素磺酸盐、脂肪烷基硫酸盐及乙氧基化烷基酚和乙氧基化脂肪醇的缩合产物。
使用本发明的组合及稀释剂,以合适的拌种配制品形式,例如具有对种子的良好粘着性的水性悬浮液或干粉剂形式,用自身已知的方式将拌种配制品施用至种子。这样的拌种配制品在本领域是已知的。拌种配制品可以含有包囊形式的单一活性成分或活性成分的组合,例如作为缓释胶囊或微胶囊。
通常,配制品包括按重量计从0.01%至90%的活性成分,从0至20%的农业上可接受的表面活性剂及10%至99.99%的固体或液体配制惰性剂和一种或多种辅助剂,该活性剂是由至少具有式(I)的化合物与组分(B)和(C)一起,以及任选地其他活性剂(特别是杀微生物剂或防腐剂或类似物)组成的。按重量计,组合物的浓缩形式通常包含在约2%与80%之间,优选在约5%与70%之间的活性剂。按重量计,配制品的施用形式可以例如包含从0.01%至20%,优选从0.01%至5%的活性剂。而商用的产品将优选地被配制为浓缩物,该最终使用者将通常使用稀释的配制品。
然而优选的是将商业产品配制为浓缩物,最终使用者通常使用稀释的配制品。
实例
接下来的实例用来阐明本发明。本发明的某些化合物与已知的化合物的区别可以在于在低施用率下更大的疗效,这可以由本领域的普通技术人员使用在实例中概述的实验程序,使用更低的施用率(如果必要的话)例如,50ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm或0.2ppm来证实。
贯穿本说明书,以摄氏度给出温度并且“m.p.”是指熔点。LC/MS是指液相色谱-质谱,并且该装置的说明和方法是:
配制品实例
将该活性成分与这些佐剂充分混合并且将混合物在适合的研磨机中充分研磨,从而提供可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
将该活性成分与这些佐剂充分混合并且将混合物在适当的研磨机中充分研磨,从而提供可以直接用于种子处理的粉末。
可乳化浓缩物
在植物保护中可以使用的具有任何所要求的稀释度的乳液可以通过用水稀释从这种浓缩物获得。
通过将该活性成分与载体混合并且将混合物在适合的研磨机中研磨而获得即用型尘剂。这样的粉剂还可以用于种子的干拌种。
挤出机颗粒
将该活性成分与这些佐剂混合并且研磨,并且将混合物用水润湿。将混合物挤出并且然后在空气流中干燥。
涂覆的颗粒剂
活性成分[具有式(I)的化合物] 8%
聚乙二醇(分子量200) 3%
高岭土 89%
将该精细研磨的活性成分在混合器中均匀地施用到用聚乙二醇湿润的高岭土上。以此方式获得无尘的包衣的颗粒剂。
悬浮液浓缩物
将精细地研磨的活性成分与佐剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩液可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、浇注或浸渍进行保护。
种子处理用的可流动性浓缩物
将精细地研磨的活性成分与佐剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩液可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、浇注或浸渍进行保护。
缓释的胶囊悬浮液
将28份的具有式(I)的化合物的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8∶1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的粒度。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将所述混合物搅拌直至聚合反应完成。
将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮液配制品包含28%的活性成分。该介质胶囊的直径是8-15微米。
将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
制备实例
使用上文和下文,以及还有在WO 08/101682(第22-33页)和WO 12/146125(第370-378页)中描述的技术连同本领域技术人员总体上已知的另外的技术,可以制备具有式(I)的化合物。
实例1:此实例阐明了N-乙基-N′-[4-(1-羟基-1-苯基-乙基)-5-甲氧基-2-甲基-苯基]-N-甲基-甲脒的制备
a)4-溴-5-甲氧基-2-甲基-苯胺的制备
分部分添加N-溴代琥珀酰亚胺(1.28g,7.29mmol)至冰冷却的(0℃-5℃)5-甲氧基-2-甲基-苯胺(1.0g,7.29mm0l)在CHCl3(15mL)中的溶液中。将所得溶液在0℃下搅拌60分钟,加热至室温并用CH2Cl2过滤。将该混合物用水性NaHCO3(+2mLNa2S2O3溶液)、盐水洗涤并经MgSO4干燥。通过过滤除去固体,并且真空除去挥发物。将残余物通过硅胶快速色谱法进行纯化以提供呈灰白色固体的标题化合物。
1H NMR(400MHz,CDCl3):δ7.17(s,1H),6.27(s,1H),3.82(s,3H),3.53-3.73(br.s.,2H),2.08(s,3H)。
b)N′-(4-溴-5-甲氧基-2-甲基-苯基)-N-乙基-N-甲基-甲脒的制备
在室温下,向4-溴-5-甲氧基-2-甲基-苯胺(1.4g,6.48mmol)和对甲苯磺酸(0.05g,0.32mmol)在甲苯(13mL)中的悬浮液添加N-(二甲氧基甲基)-N-甲基-乙胺(1.3g,9.7mmol)。将所得澄清溶液加热至50℃并在此温度下搅拌24h。冷却至室温后,将该反应混合物用乙酸乙酯稀释、用水性NaHCO3、盐水洗涤并经MgSO4干燥。通过过滤除去固体,并且真空除去挥发物。将残余物通过硅胶快速色谱法进行纯化以提供呈淡黄色固体的标题化合物。
1H NMR(400MHz,CDCl3):δ7.40(br.s.,1H),7.26(s,1H),6.33(s,1H),3.85(s,3H),3.34(br.s.,2H),3.00(s,3H),2.16(s,3H),1.22(t,3H)。
c)N-乙基-N′-[4-(1-羟基-1-苯基-乙基)-5-甲氧基-2-甲基-苯基]-N-甲基-甲脒 的制备
在N2气氛下,将N′-(4-溴-5-甲氧基-2-甲基-苯基)-N-乙基-N-甲基-甲脒(0.10g,0.35mmol)在干四氢呋喃(3.5mL)中的溶液冷却至-78℃,并缓慢添加叔丁基锂(1.5M于戊烷中,0.49mL,0.74mmol)。将反应在-78℃下老化5min,并且然后逐滴添加1-苯基乙酮(0.044g,0.37mmol)。除去冷却浴,允许反应加热至室温并再搅拌10min。添加水性NaHCO3并且将该混合物用EtOAc萃取。将有机层用盐水洗涤、经MgSO4干燥、过滤并在真空中浓缩。将残余物通过硅胶快速色谱法进行纯化以提供呈白色固体的标题化合物。
1H NMR(400MHz,CDCl3):δ7.41(br.s.,1H),7.28-7.34(m,2H),7.12-7.25(m,4H),6.32(s,1H),4.64(s,1H),3.51(s,3H),3.20-3.47(br.s,2H),3.00(s,3H),2.24(s,3H),1.80(s,3H),1.21(t,3H)。
实例2:此实例阐明了N-乙基-N'-[4-[1-羟基-2-甲基-1-(三氟甲基)丙基]-5-甲氧基-2-甲基-苯基]-N-甲基-甲脒的制备
a)N-乙基-N'-[5-甲氧基-2-甲基-4-(2-甲基丙酰基)苯基]-N-甲基-甲脒的制备
在20℃至40℃之间的温度下(温度由添加速率控制),在N2气氛下在干四氢呋喃(3.5 mL)中的N’-(4-溴-5-甲氧基-2-甲基-苯基)-N-乙基-N-甲基-甲脒(2.Og,7.01mmol)溶液逐滴添加到LiCl(O.33g,7.71mmol)和Mg切屑(0.26g,7.02mmol)在干四氢呋喃(3.5mL)中的悬浮液中。完成添加后,将反应在40℃下老化1h,并且然后将该混合物冷却至0℃。逐滴添加N-甲氧基-N,2-二甲基一丙酰胺(1.01g,7.33mmol),并将反应混合物在1h内逐渐加热至RT。添加NH4Cl水溶液并将该混合物用EtOAc萃取。将有机层用水、盐水洗涤,经MgSO4干燥,过滤并在真空中浓缩。将残余物通过硅胶快速色谱法进行纯化以提供呈淡黄色油状物的标题化合物。
1H NMR(400 MHz,CDCl3)67.47(br.s,2H),6.30(s,1H),3.85(s,3H),3.25-3.60(m,3H),3.02(s,3H),2.18(s,3H),1.59(s,IH),1.23(t,3H),1.13(d,6H)。
b)N-乙基-N'-『4-『1-羟基-2-甲基-1-(三氟甲基)丙基]-5-甲氧基-2-甲基-苯 基]-N-甲基-甲脒的制备
在40℃下,将三甲基(三氟甲基)硅烷(0.26g,1.81mmol)逐滴添加到N-乙基-N’-[5-甲氧基-2-甲基-4-(2-甲基丙酰基)苯基]-N-甲基-甲脒(0.50g,1.81mmol)和csF(0.03g,O.18 mmol)在甲苯(9mL)中的溶液。将所得混合物在40℃下老化3h,然后添加第二部分三甲基(三氟甲基)硅烷(O.13g,O.91mmol),并且将反应再搅拌30min,然后在真空中浓缩成棕色油状物。
将该残余物吸收进甲醇(7mL),用碳酸钾(O.37g,2.71mmol)和水性氢氧化钠(2M,3滴)处理,加热至40℃并在该温度下搅拌24h。然后添加水性NailCO3溶液,并将乳液用EtOAc萃取。将有机层用水、盐水洗涤,经MgS04干燥,过滤并在真空中浓缩。将残余物通过硅胶快速色谱法进行纯化以提供呈淡棕色固体的标题化合物(m.p.:57℃-59℃)。
1H NMR(400 MHz,CDCl3)67.47(br s,1H),7.07(s,1H),6.56(br s,1H),6.40(s,1H),3.90(s,3H),3.22-3.66(m,2H),3.03(s,3H),2.46—2.66(m,1H),2.22(s,3H),1.25(t,3H),1.16(d,3H),O.87(d,3H)。
表E:具有式(I)的化合物的物理数据
使用类似于上文所述的那些和/或本领域技术人员总体上已知的常用合成技术,以及WO 12/146125(第370-378页)和WO 08/101682(第22-33页)中描述的那些的技术来制备表E中具有式(I)化合物。
所使用的HPLC方法
方法A:
在来自沃特斯10的质谱仪(ACQUITY UPLC)(SQD,SQDII或ZQ单四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正离子或负离子,毛细管:3.00kV,锥孔范围:30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及一个来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器。15溶剂脱气装置,二元泵,加热的管柱室以及二极管阵列检测器。柱:沃特斯UPLCHSS T3,1.8mm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:10%-100%B,在1.2min内;流量(ml/min)0.85。
生物学实例
小麦白粉病菌(Blumeria graminis f.sp.tritici,Erysiphe graminis
f.sp.Tritici)/小麦/叶圆片预防性(小麦上的白粉病)
将小麦叶碎片栽培品种坎斯勒(cv.Kanzler)置于多孔板(24孔规格)的琼脂上,并且用稀释在水中的配制的测试化合物喷雾。在施用后1天之后,通过在测试板上方摇动白粉病感染的植物来接种这些叶圆片。在人工气候室中的24h黑暗随后是12h光照/12h黑暗的一个光照方案下,在20℃和60%rh下培育接种的叶圆片,并且在未处理的检验叶碎片上出现适当的疾病损害水平时(施用后6-8天),作为与未处理的相比时的疾病控制百分比来评估化合物的活性。
在这一测试中,当在相同条件下与示出大规模的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
E1.001、E1.003、E1.004、E1.005、E1.006、E1.007、E1.010、E1.011、E1.013、E1.014、E1.015、E1.016、E1.017、E1.018、E1.019、E1.020、E1.021、E1.022、E1.023、E1.024、E1.025、E1.026、E1.027、E1.029、E1.030、E1.031、E1.032、E1.033、E1.034、E1.035、E1.037、E1.038、E1.039、E1.040、E1.041、E1.042、E1.043、E1.044、E1.045、E1.046、E1.047、E1.048、E1.049、E1.050、E1.051、E1.052、E1.053、E1.054、E1.055、E1.056、E1.057、E1.058、E1.059、E1.060、E1.061、E1.062、E1.063、E1.064、E1.065、E1.066、E1.067、E1.068、E1.069、E1.070、E1.071、E1.072、E1.074、E1.075、E1.076、E1.077、E1.078、E1.079、E1.080、E1.081、E1.082、E1.083、E1.084、E1.086、E1.087、E1.088、E1.089、E1.090、E1.091、E1.092、E1.093、E1.094、E1.095、E1.098、E1.099、E1.100、E1.101、E1.102、E1.103、E1.104、E1.105、E1.106、E1.107、E1.108、E1.109、E1.112、E1.113、E1.114、E1.117、E1.118、E1.119、E1.120、E1.121、E1.122、E1.123、E1.126
豆薯层锈菌/大豆/叶圆片预防法(大豆锈病)
在喷雾室中,将四周龄大豆植物用稀释于水中的配制的测试化合物进行喷雾。在施用后一天,从处理的植物上切割下叶圆片并置于24孔板中的琼脂上。将叶圆片通过用孢子悬浮液在它们的下方叶表面上进行喷雾来接种。在人工气候室中在黑暗中在20℃和75%rh下的24-36小时的孵育期之后,然后用12h光照/天和75%rh将叶圆片保持在20℃。在未处理的检验植物上出现适当的疾病水平时(施用后12-14天),评估被疾病覆盖的叶圆片面积百分数。
在这一测试中,当在相同条件下与示出大规模的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
E1.001、E1.002、E1.003、E1.004、E1.005、E1.006、E1.007、E1.010、E1.011、E1.014、E1.015、E1.016、E1.017、E1.018、E1.020、E1.022、E1.023、E1.024、E1.026、E1.027、E1.029、E1.030、E1.031、E1.033、E1.034、E1.035、E1.037、E1.044、E1.045、E1.046、E1.047、E1.048、E1.049、E1.050、E1.051、E1.052、E1.053、E1.054、E1.055、E1.056、E1.057、E1.058、E1.059、E1.061、E1.062、E1.063、E1.064、E1.065、E1.066、E1.067、E1.068、E1.069、E1.070、E1.071、E1.072、E1.074、E1.075、E1.076、E1.077、E1.078、E1.081、E1.082、E1.083、E1.084、E1.086、E1.087、E1.088、E1.089、E1.090、E1.091、E1.093、E1.095、E1.096、E1.099、E1.100、E1.101、E1.102、E1.103、E1.104、E1.105、E1.106、E1.111、E1.112、E1.114、E1.117、E1.118、E1.119、E1.120、E1.121、E1.122、E1.123、E1.124、E1.125、E1.126
小麦隐匿柄锈菌/小麦/叶圆片预防法(褐锈病)
将小麦叶碎片栽培品种坎斯勒(cv.Kanzler)置于多孔板(24孔规格)的琼脂上,并且用稀释在水中的配制的测试化合物喷雾。在施用后1天,用真菌的孢子悬浮液接种叶圆片。在人工气候室中的12h光照/12h黑暗的一个光照方案下,在19℃和75%rh下培育接种的叶碎片,并且在未处理的检验叶碎片上出现适当的疾病损害水平时(施用后7-9天),作为与未处理的相比时的疾病控制百分比来评估化合物的活性。
在这一测试中,当在相同条件下与示出大规模的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
E1.001、E1.002、E1.003、E1.004、E1.005、E1.006、E1.007、E1.008、E1.009、E1.010、E1.011、E1.013、E1.014、E1.015、E1.016、E1.017、E1.018、E1.019、E1.020、E1.021、E1.022、E1.023、E1.024、E1.025、E1.026、E1.027、E1.028、E1.029、E1.030、E1.031、E1.032、E1.033、E1.034、E1.035、E1.036、E1.046、E1.047、E1.048、E1.049、E1.050、E1.051、E1.052、E1.053、E1.054、E1.055、E1.056、E1.057、E1.058、E1.059、E1.060、E1.061、E1.062、E1.063、E1.064、E1.065、E1.066、E1.067、E1.068、E1.069、E1.070、E1.071、E1.072、E1.073、E1.074、E1.075、E1.076、E1.077、E1.078、E1.079、E1.080、E1.081、E1.082、E1.083、E1.084、E1.086、E1.087、E1.088、E1.089、E1.092、E1.093、E1.094、E1.095、E1.098、E1.099、E1.100、E1.101、E1.103、E1.104、E1.105、E1.106、E1.107、E1.108、E1.109、E1.110、E1.111、E1.112、E1.116、E1.117、E1.118、E1.119、E1.120、E1.121、E1.122、E1.123、E1.124、E1.125、E1.126
小麦隐匿柄锈菌/小麦/叶圆片治疗法(褐锈病)
将小麦叶碎片栽培品种坎斯勒(cv.Kanzler)置于多孔板(24孔规格)内的琼脂上。用真菌的孢子悬浮液接种这些叶碎片。在19℃和75%rh下,在黑暗中储存这些板。在接种后1天,施用在水中稀释的配制的测试化合物。在人工气候室中的12h光照/12h黑暗的一个光照方案下,在19℃和75%rh下培育叶碎片,并且在未处理的检验叶碎片上出现适当的疾病损害水平时(施用6-8天),评估化合物的活性,作为与未处理的相比的百分比疾病控制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
E1.001、E1.002、E1.003、E1.004、E1.005、E1.006、E1.007、E1.008、E1.009、E1.010、E1.011、E1.013、E1.014、E1.015、E1.016、E1.017、E1.018、E1.019、E1.020、E1.021、E1.022、E1.023、E1.024、E1.025、E1.026、E1.027、E1.028、E1.029、E1.030、E1.031、E1.032、E1.033、E1.034、E1.035、E1.036、E1.037、E1.038、E1.039、E1.040、E1.041、E1.042、E1.043、E1.044、E1.045、E1.046、E1.047、E1.048、E1.049、E1.050、E1.051、E1.052、E1.053、E1.054、E1.055、E1.056、E1.057、E1.058、E1.059、E1.060、E1.061、E1.062、E1.063、E1.064、E1.065、E1.066、E1.067、E1.068、E1.069、E1.070、E1.071、E1.072、E1.074、E1.075、E1.076、E1.077、E1.078、E1.079、E1.080、E1.081、E1.082、E1.083、E1.084、E1.085、E1.086、E1.087、E1.088、E1.089、E1.090、E1.091、E1.092、E1.093、E1.094、E1.095、E1.098、E1.099、E1.100、E1.101、E1.102、E1.103、E1.104、E1.105、E1.106、E1.107、E1.108、E1.109、E1.110、E1.111、E1.112、E1.113、E1.114、E1.116、E1.117、E1.118、E1.119、E1.120、E1.121、E1.122、E1.123、E1.124、E1.125、E1.126。
Claims (15)
1.一种具有式(I)的化合物:
其中,
R1和R2各自独立地选自C1-C4烷基和C3-C8环烷基;或
R1和R2连同它们所附接的氮原子一起形成三元至六元饱和的环状基团,该环状基团可以任选地含有一个氧原子或一个硫原子;
R3是氢、卤素或C1-C4烷基;
R4是C1-C4烷基或C1-C4卤代烷基;
R5和R6各自独立地选自C1-C6烷基,C1-C6卤代烷基,C3-C8环烷基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,芳基(任选地被一至三个R7基团取代),芳基(C1-C4)烷基,其中该芳基任选地被一至三个R7基团取代,杂芳基(C1-C4)烷基,其中该杂芳基任选地被一至三个R7基团取代,和杂芳基(任选地被一至三个R7基团取代);
X是NR8、O或S;
每个R7独立地选自卤素、氰基、羟基、氨基、硝基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C3-C6环烷硫基、C1-C4烷基亚磺酰基、C1-C4卤代烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯基氧基、C2-C6卤代烯基氧基、C2-C6炔基、C3-C6环烷基C2-C6炔基、C2-C6炔基氧基、芳基、芳基(C1-C4)烷基、芳基氧基、杂芳基、杂芳基(C1-C4)烷基和杂芳基氧基;并且
R8选自氢、C1-C4烷基、C1-C4烷氧基和C3-C8环烷基;或其盐或N-氧化物。
2.根据权利要求1所述的化合物,其中R1和R2各自独立地是C1-C4烷基。
3.根据权利要求1或2所述的化合物,其中R3是氢、氟、氯、或C1-C4烷基。
4.根据权利要求1、2或3中任一项所述的化合物,其中R4是C1-C3烷基或C1-C3卤代烷基。
5.根据权利要求1、2、3或4中任一项所述的化合物,其中R5和R6各自独立地选自C1-C6烷基,C1-C6卤代烷基,C3-C8环烷基,C2-C6烯基,苯基(任选地被一至三个R7基团取代),苯基(C1-C4)烷基,其中该苯基任选地被一至三个R7基团取代,吡唑基(C1-C4)烷基,其中该吡唑任选地被一至三个R7基团取代,和吡啶基(任选地被一至三个R7基团取代),并且其中每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基羰基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、苯基、苄基、苯氧基、吡啶基、吡啶基甲基和吡啶基氧基。
6.根据权利要求1、2、3、4或5中任一项所述的化合物,其中X是NR8或O,其中R8的氢、C1-C4烷基或C1-C4烷氧基。
7.根据权利要求1、2、3、4、5或6中任一项所述的化合物,其中R1和R2各自独立地选自甲基、乙基、丙基和异丙基。
8.根据权利要求1、2、3、4、5、6或7中任一项所述的化合物,其中R3是氢或C1-C3烷基。
9.根据权利要求1、2、3、4、5、6、7或8中任一项所述的化合物,其中R5和R6各自独立地选自C1-C6烷基、C1-C6卤代烷基、C3-C5环烷基、苯基(任选地被一个或两个R7基团取代)和吡啶基(任选地被一个或两个R7基团取代),并且其中每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4烷基羰基、C2-C6炔基、苯基、苯氧基和吡啶基。
10.根据权利要求1、2、3、4、5、6、7、8或9中任一项所述的化合物,其中X是O。
11.根据权利要求1所述的化合物,其中R1和R2各自独立地选自甲基、乙基和异丙基;R3是氢或C1-C2烷基;R4是甲基或乙基;R5和R6各自独立地选自C1-C2卤代烷基、苯基(任选地被一个或两个R7基团取代)、乙基、正丙基、异丙基、正丁基、异丁基、新戊基、环丙基、环丁基或环戊基;X是N-甲基或O;并且每个R7独立地选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C6炔基和苯基;或其盐或N-氧化物。
12.根据权利要求1所述的化合物,其中
R1是甲基并且R2是乙基或异丙基;或者,可替代地,R1和R2都是乙基;
R3是氢或甲基(优选甲基);
R4是甲基;
R5是CF3、CClF2或CF2CF3(优选CF3);
R6是苯基(任选地被一个甲基基团和/或一个或两个卤素原子、优选氟或氯取代)、正丙基、异丙基、正丁基、异丁基或新戊基;或者,可替代地,R6是环丙基;并且
X是O;或其盐或N-氧化物。
13.一种组合物,包含杀真菌有效量的如权利要求1-12中任一项所述的具有式(I)的化合物。
14.根据权利要求13所述的组合物,其中该组合物进一步包括至少一种另外的活性成分和/或稀释剂。
15.一种对抗、预防或控制致植物病的疾病的方法,该方法包括向植物病原体、植物病原体的场所、或易受植物病原体攻击的植物、或其繁殖材料施用杀真菌有效量的如在权利要求1-12中任一项所述的具有式(I)的化合物或包括杀真菌有效量的如在权利要求1-12中任一项所述的具有式(I)的化合物的组合物。
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BR112019009515A2 (pt) * | 2016-11-15 | 2019-07-30 | Syngenta Participations Ag | derivados de fenilamidina microbiocidas |
AU2018254010B2 (en) | 2017-04-20 | 2022-05-12 | Pi Industries Ltd. | Novel phenylamine compounds |
EP3625215B1 (en) | 2017-05-18 | 2023-09-13 | PI Industries Ltd | Formimidamidine compounds useful against phytopathogenic microorganisms |
EP3638032A1 (en) * | 2017-06-14 | 2020-04-22 | Syngenta Participations AG | Fungicidal compositions |
EA202091234A1 (ru) | 2017-11-21 | 2020-10-05 | Зингента Партисипейшнс Аг | Фунгицидные композиции |
BR112020011083A2 (pt) * | 2017-12-04 | 2020-11-17 | Syngenta Participations Ag | derivados de fenilamidina microbiocidas |
WO2019202459A1 (en) | 2018-04-16 | 2019-10-24 | Pi Industries Ltd. | Use of 4-substituted phenylamidine compounds for controlling disease rust diseases in plants |
EP3643175A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Ternary pesticidal mixtures containing metyltetraprole and fenpropimorph |
AR120427A1 (es) | 2019-11-12 | 2022-02-16 | Pi Industries Ltd | Composición agroquímica que comprende compuestos de fenilamidina 4-sustituidos |
WO2022117650A1 (en) | 2020-12-02 | 2022-06-09 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068656A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
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EP3389379A1 (en) | 2018-10-24 |
IL259986A (en) | 2018-07-31 |
US10723695B2 (en) | 2020-07-28 |
US20180362451A1 (en) | 2018-12-20 |
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MX2018007292A (es) | 2018-09-06 |
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JP2019505492A (ja) | 2019-02-28 |
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