CN110709395A - 杀微生物的噁二唑衍生物 - Google Patents
杀微生物的噁二唑衍生物 Download PDFInfo
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- CN110709395A CN110709395A CN201880036275.7A CN201880036275A CN110709395A CN 110709395 A CN110709395 A CN 110709395A CN 201880036275 A CN201880036275 A CN 201880036275A CN 110709395 A CN110709395 A CN 110709395A
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- Prior art keywords
- methyl
- compound
- hydrogen
- phenyl
- ccn
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- 239000001257 hydrogen Substances 0.000 claims description 71
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- 125000001424 substituent group Chemical group 0.000 claims description 51
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 27
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Abstract
可用作杀有害生物剂、尤其可用作杀真菌剂的具有式(I)的化合物,其中取代基是如在权利要求1中所定义的。
Description
本发明涉及杀微生物的噁二唑衍生物,例如作为活性成分,这些噁二唑衍生物具有杀微生物活性,特别是杀真菌活性。本发明还涉及包含这些噁二唑衍生物中的至少一种的农用化学组合物,涉及这些化合物的制备方法,并且涉及这些噁二唑衍生物或组合物在农业或园艺中用于控制或预防植物、收获的粮食作物、种子或非生命材料被植物病原性微生物、优选真菌侵染的用途。
WO 2015/185485、WO 2017/085098和WO 2017/085100描述了取代的噁二唑用于防治植物病原性真菌的用途。
根据本发明,提供了一种具有式(I)的化合物:
其中
n是0或1或2;
R1和R2独立地选自氢、氟、氯、甲基;
R3和R4独立地选自氢或氟;
其中R1至R4中的至少两个是C-H;
R5和R6独立地表示氢或甲基;
Z表示选自Z-1、Z-2、Z-3、Z-4、Z-5或Z-6的基团,
其中:
X表示C(=O)或S(O)2;并且
(i)Z-1中的B1和B2独立地表示N或C-R7,并且Z-1中的B3表示C(R7)(R8)、O、S、NR9或C(=O);
(ii)Z-2中的B1表示C(R7)(R8)、O、S、NR9或C(=O),并且Z-2中的B2和B3独立地表示N或C-R7;
(iii)Z-3中的B1、B2、B3和B4独立地表示N或C-R7;
(iv)Z-4中的B1和B2独立地表示N或C-R7,并且Z-4中的B3和B4独立地表示C(R7)(R8)、O、S、NR9或C(=O),其前提是B3和B4中仅一个可以是O或S;
(v)Z-5中的B2和B3独立地表示N或C-R7,并且Z-5中的B1和B4独立地表示C(R7)(R8)、O、S、NR9或C(=O);并且
(vi)Z-6中的B1和B2独立地表示C(R7)(R8)、O、S、NR9或C(=O),并且Z-6中的B3和B4独立地表示N或C-R7,其前提是B1和B2中仅一个可以是O或S;并且
R7表示或R7和R8独立地表示氢、卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;
R9表示氢、C1-6烷基、C3-6烯基、C3-6炔基、C3-6环烷基、C1-6烷氧基、C(O)R10、C(O)OR10、C(O)N(R10)R11、S(O)2R10或S(O)2N(R10)R11,其中C1-6烷基、C3-6烯基、C3-6炔基、C3-6环烷基和C1-6烷氧基任选地被卤素或氰基取代;或R9表示苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;
R10表示氢、C1-3烷基、C3-4环烷基、C3-4环烷基C1-2烷基、C1-2烷氧基C1-4烷基,其中C1-3烷基、C3-4环烷基、C3-4环烷基C1-2烷基和C1-2烷氧基C1-4烷基任选地被卤素或氰基取代;并且
R11表示氢、氨基、氟、氯、甲基、乙基、二氟甲基、三氟甲基、甲氧基、N-甲胺或二甲胺;或者
其盐或N-氧化物。
出人意料地,已经发现了,为实际目的,具有式(I)的新颖化合物有着非常有利水平的用来保护植物免受由真菌引起的疾病的生物活性。
根据本发明的第二方面,提供了一种包含杀真菌有效量的具有式(I)的化合物的农用化学组合物。此种农业组合物可以进一步包含至少一种另外的活性成分和/或农用化学上可接受的稀释剂或载体。
根据本发明的第三方面,提供了一种控制或预防有用植物被植物病原性微生物侵染的方法,其中将杀真菌有效量的具有式(I)的化合物、或包含这种化合物作为活性成分的组合物施用至这些植物、其部分或其场所。
根据本发明的第四方面,提供了具有式(I)的化合物作为杀真菌剂的用途。根据本发明的这个特定方面,该用途可以不包括通过手术或疗法来治疗人体或动物体的方法。
如本文使用的,术语“卤素(halogen或halo)”是指氟(fluorine,fluoro)、氯(chlorine,chloro)、溴(bromine,bromo)或碘(iodine,iodo),优选氟、氯或溴。
如本文使用的,氰基意指-CN基团。
如本文使用的,氨基意指-NO2基团。
如本文使用的,术语“C1-6烷基”是指仅由碳原子和氢原子组成的直链的或支链的烃链基团,该烃链基团不含不饱和度,具有从一至六个碳原子,并且通过单键附接至分子的其余部分。C1-4烷基、C1-3烷基和C1-2烷基应相应地解释。C1-6烷基的实例包括但不限于甲基、乙基、正丙基、1-甲基乙基(异丙基)、正丁基和1-二甲基乙基(叔丁基)。“C1-C2亚烷基”基团是指C1-2烷基的相应定义,不同之处在于此种基团是通过两个单键附接至分子的其余部分。C1-2亚烷基的实例是-CH2-和-CH2CH2-。
如本文使用的,术语“C1-6烷氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C1-6烷基基团。术语C1-4烷氧基、C1-3烷氧基和C1-2烷氧基应相应地解释。C1-6烷氧基的实例包括但不限于甲氧基、乙氧基、丙氧基、异丙氧基和叔丁氧基。
如本文使用的,术语“C1-4卤代烷基”是指被一个或多个相同的或不同的卤素原子取代的如上一般定义的C1-4烷基基团。C1-4卤代烷基的实例包括但不限于氟甲基、氟乙基、二氟甲基、三氟甲基、2,2,2-三氟乙基、以及3,3,3-三氟丙基。
如本文使用的,术语“C3-6烯基”是指仅由碳原子和氢原子组成的直链的或支链的烃链基团,所述烃链基团含有至少一个可以是(E)-构型或(Z)-构型的双键、具有从三至六个碳原子、通过单键附接至分子的剩余部分。C3-6烯基的实例包括但不限于丙-1-烯基、烯丙基(丙-2-烯基)以及丁-1-烯基。
如本文使用的,术语“C3-6炔基”是指仅由碳原子和氢原子组成的直链的或支链的烃链基团,所述烃链基团包含至少一个三键、具有从三至六个碳原子、并且通过单键附接至分子的剩余部分。C3-6炔基的实例包括但不限于丙-1-炔基、炔丙基(丙-2-炔基)。
如本文使用的,术语“C1-2烷氧基C1-4烷基”是指具有式Rb-O-Ra-的基团,其中Rb是如上一般定义的C1-2烷基基团,并且Ra是如上一般定义的C1-4亚烷基基团。
如本文使用的,术语“C3-6环烷基”是指饱和或部分不饱和并且包含3至6个碳原子的稳定的单环基团。C3-4环烷基应相应地解释。C3-6环烷基的实例包括但不限于环丙基、环丁基、环戊基、环戊烯-1-基、环戊烯-3-基、以及环己烯-3-基。
如本文使用的,术语“C3-4环烷基C1-2烷基”是指通过如上定义的C1-2亚烷基基团附接至分子的剩余部分的如上定义的C3-4环烷基环。C3-4环烷基C1-2烷基的实例包括但不限于环丙基-甲基和环丁基-乙基。
在具有式(I)的化合物中一个或多个可能的不对称碳原子的存在意味着所述化合物能以手性异构体形式存在,即对映异构体或非对映异构体的形式。作为围绕单键的受限旋转的结果,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形式以及其混合物。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(包括内酰胺-内酰亚胺互变异构和酮-烯醇互变异构)(当存在时)。本发明包括具有式(I)的化合物的所有可能的互变异构体形式。
在每种情况下,根据本发明的具有式(I)的所述化合物是呈游离形式、氧化形式(作为N-氧化物)、共价水合形式、或盐形式(如农艺学上可用的或农用化学上可接受的盐形式)。
N-氧化物是叔胺的氧化形式或含氮杂芳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。
以下清单提供了关于根据本发明的具有式(I)的化合物的取代基n、R1、R2、R3、R4、R5、R6、Z(包括Z-1、Z-2、Z-3、Z-4、Z-5、Z-6)、R7、R8、R9、R10和R11的定义、包括优选的定义。对于这些取代基中的任何一个,以下给出的任何定义都可以结合以下或在本文件中的其他地方给出的任何其他取代基的任何定义。
n是0或1或2。优选地,n是1。
R1和R2独立地选自氢、氟、氯、甲基,并且R3和R4独立地选自氢或氟,其中R1至R4中的至少两个是C-H。在本发明的一些实施例中,包含R1至R4的6元环是亚苯基(其中R1至R4是氢),氟亚苯基(其中R1是C-F且R2至R4是氢或R3是C-F且R1、R2和R4是氢)或二氟亚苯基(其中R1和R3是C-F并且R2和R4是氢)基团。
R5和R6独立地表示氢或甲基。优选地,R5是氢或甲基,并且R6是氢。更优选地,R5和R6是氢。
Z表示选自Z-1或Z-2或Z-3或Z-4或Z-5或Z-6的基团。
X表示C(=O)或S(O)2。在本发明的一些实施例中,X是C(=O)。在本发明的其他实施例中,X是S(O)2。
优选地,Z-1选自:
优选地,其中Z-1任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、或苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基,并且
R9是氢、C1-4烷基、C3-4烯基、C3-4炔基、C3-6环烷基、C1-4烷氧基、C(O)R10、或C(O)OR10,其中R10是氢或C1-4烷基;或者
更优选地,其中Z-1任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、或苯基或被1、2或3个独立地选自氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基的取代基取代的苯基,并且
R9是氢、甲基、乙基或C(O)R10,其中R10是氢或甲基。
优选地,Z-2选自:
优选地,其中Z-2任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基,并且
R9是氢、C1-4烷基、C3-4烯基、C3-4炔基、C3-6环烷基、C1-4烷氧基、C(O)R10、或C(O)OR10,其中R10是氢或C1-4烷基;或者
更优选地,其中Z-2任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、苯基或被1、2或3个独立地选自氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基的取代基取代的苯基,并且
R9是氢、甲基、乙基或C(O)R10,其中R10是氢或甲基;或者
甚至更优选地,其中Z-2任选地被1或2个独立地选自以下的取代基取代:氟、氯、溴、氰基、甲基、甲氧基和三氟甲基,并且R9是氢或甲基。
优选地,Z-3选自:
优选地,其中Z-3任选地被1、2或3个(根据R7)独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;或者
更优选地,其中Z-3任选地被1、2或3个(根据R7)独立地选自以下的取代基取代:卤素、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、苯基或被1、2或3个独立地选自氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基的取代基取代的苯基,或者
甚至更优选地,其中Z-3任选地被1或2个(根据R7)独立地选自以下的取代基取代:氟、氯、溴、氰基、甲基、甲氧基和三氟甲基,或者
还更优选地,Z-3任选地被1或2个独立地选自卤素(包括氟和溴)、氰基、C1-4烷基、C1-2氟烷基或C1-4烷氧基的取代基取代。
优选地,Z-4选自:
优选地,其中Z-4任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;或者
更优选地,其中Z-4任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、苯基或被1、2或3个独立地选自氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基的取代基取代的苯基。
优选地,Z-5选自:
优选地,其中Z-5任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;或者
更优选地,其中Z-5任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、苯基或被1、2或3个独立地选自氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基的取代基取代的苯基。
优选地,Z-6选自:
优选地,其中Z-6任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;或者
更优选地,其中Z-6任选地被1、2或3个(根据R7或R7/R8)独立地选自以下的取代基取代:卤素、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、苯基或被1、2或3个独立地选自氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基的取代基取代的苯基。
优选地,根据式(I)的化合物选自表2至17(下文)中列出的化合物2.01至2.28至17.01至17.28或如表A至F(下文)中所示的化合物A-1至A-4,B-1至B-7,C-1至C-18,D-1,E-1和F-1。
优选地,在本发明的根据式(I)的化合物中:
n是1;
R1至R4是氢,R1是C-F且R2至R4是氢,R3是C-F且R1、R2和R4是氢,或R1和R3是C-F且R2和R4是氢。
R5是氢或甲基并且R6是氢;并且
Z是Z-1,其中Z-1选自:
并且其中Z-1任选地被1、2或3个独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基,并且R9是氢、C1-4烷基、C3-4烯基、C3-4炔基、C3-6环烷基、C1-4烷氧基、C(O)R10、或C(O)OR10,其中R10是氢或C1-4烷基。
更优选地,
n是1;
R1至R4是氢;
R5和R6是氢;并且
Z是Z-1,其中Z-1选自:
其中Z-1任选地被1或2个独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素或C1-4烷基的取代基取代的苯基,并且R9是氢、C1-4烷基或C(O)R10,其中R10是氢或C1-4烷基。
优选地,在本发明的根据式(I)的化合物中:
n是1;
R1至R4是氢,R1是C-F且R2至R4是氢,R3是C-F且R1、R2和R4是氢,或R1和R3是C-F且R2和R4是氢。
R5是氢或甲基并且R6是氢;并且
Z是Z-2,其中Z-2选自:
其中Z-2任选地被1、2或3个独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基,并且R9是氢、C1-4烷基、C3-4烯基、C3-4炔基、C3-6环烷基、C1-4烷氧基、C(O)R10、或C(O)OR10,其中R10是氢或C1-4烷基。
更优选地,
n是1;
R1至R4是氢;
R5和R6是氢;并且
Z是Z-2,其中Z-2选自:
其中Z-2任选地被1或2个独立地选自卤素、氰基、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代,并且R9是氢或C1-4烷基。
优选地,在本发明的根据式(I)的化合物中:
n是1;
R1至R4是氢,R1是C-F且R2至R4是氢,R3是C-F且R1、R2和R4是氢,或R1和R3是C-F且R2和R4是氢。
R5是氢或甲基并且R6是氢;并且
Z是Z-3,其中Z-3选自:
其中Z-3任选地被1、2或3个(根据R7)独立地选自以下的取代基取代:卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基。
更优选地,
n是1;
R1至R4是氢;
R5和R6是氢;并且
Z是Z-3,其中Z-3选自:
其中Z-3任选地被1或2个独立地选自卤素(包括氟和溴)、氰基、C1-4烷基、C1-2氟烷基或C1-4烷氧基的取代基取代。
本发明的化合物可以是如由式(I-a)或式(I-b)表示的具有式(I)的化合物的对映异构体,其中n是1,并且R5和R6不同(参见下文),或者确实当n是2时并且仅在与R5和R6结合的两个碳位置之一处,R5和R6不同。
同样地,本发明的化合物可以是具有式(I)的化合物的非对映异构体,当n是2时,并且其中在与R5和R6结合的两个碳位置中的每一个处是不同的。
应理解,当在水性介质中时,根据本发明的具有式(I)的化合物可以呈与在CF3-噁二唑基序处的相应的共价水合的形式(即,如下文所示的具有式(I-I)和式(I-II)的化合物,其可以以互变异构体形式存在,如具有式(I-Ib)和式(I-IIb)的化合物)的可逆平衡存在。此动态平衡对于具有式(I)的化合物的生物活性可能是重要的。关于本发明的具有式(I)的化合物的n、R1、R2、R3、R4、R5、R6、Z(包括Z-1、Z-2、Z-3、Z-4、Z-5、Z-6)、R7、R8、R9、R10和R11的指定通常适用于具有式(I-I)和(I-Ib)以及式(I-II)和(I-IIb)的化合物,以及如由表2至17中的化合物2.01至2.28至17.01至17.28或分别如表A至F所示的化合物A-1至A-4,B-1至B-7,C-1至C-18,D-1,E-1和F-1表示的n、R1、R2、R3、R4、R5、R6、Z(包括Z-1、Z-2、Z-3、Z-4、Z-5、Z-6)、R7、R8、R9、R10和R11的组合的具体披露内容。
本发明的化合物可以如在以下方案1至10中所示来制备,其中(除非另外说明)每一变量的定义是如上对于具有式(I)的化合物所定义的。
具有式(I)的化合物可以从具有式(III)的化合物(其中X是F、Cl、Br、I、或OSO2Me)制备,通过在-78℃与25℃之间的温度下在合适的溶剂(例如二甲基甲酰胺、丙酮或四氢呋喃)中在碱(例如六甲基二硅氮锂(lithium hexamethyldisilylazide)、正丁基锂、Cs2CO3、CSF、K2CO3或NaH)的存在下用具有式(II)的化合物进行处理。此外,一些反应可能仅在较高温度下和/或在催化剂体系(如CuI/二甲基乙二胺或Pd(OAc)2/Xantphos存在下进行。对于相关实例,参见:WO 2004/087646;WO 2013/132253;Garcia,M.等人Org.Biomol.Chem.[有机与生物分子化学]2004,11,1633;Guyonner,M.和Baudoin,O.Org.Lett.[有机快报]2012,14,398;Philipps,D.P.等人Tetrahedron Lett.[四面体快报]2009,50,7293。此反应示于方案1中。
可替代地,具有式(I)的化合物、或具有式(XII)的化合物可以分别从具有式(IV)或(IVa)的化合物,通过在25℃与75℃之间的温度下在合适的溶剂(如四氢呋喃或乙醇)中在碱(例如,吡啶或4-二甲基氨基吡啶)的存在下用三氟乙酸酐处理来制备。对于相关实例,参见:WO 2003/028729和WO 2010/045251。此反应示于方案2中。
具有式(IV)和(IVa)的化合物可以分别从具有式(V)和(Va)的化合物,通过在0℃与65℃之间的温度下在合适的溶剂(如甲醇)中在碱(如三乙胺)的存在下用羟胺盐酸盐处理它们来制备。对于相关实例,参见Kitamura,S.等人Chem.Pharm.Bull.[化学与药学通报](2001),49,268和WO 2013/066838。此反应示于方案3中。
具有式(V)和(Va)的化合物可以分别从具有式(VI)和(VIa)的化合物(其中V是Br或I),通过在100℃与120℃之间的升高的温度下在合适的溶剂(例如,二甲基甲酰胺或N-甲基吡咯烷酮)中与合适的氰化物试剂(如Pd(0)/Zn(CN)2或CuCN)进行金属促进的反应来制备。对于相关实例,参见US 2007/0155739和WO 2009/022746。此反应示于方案4中。
具有式(VI)的化合物(其中V是Br或I、或CN)(还对应于化合物(V))可以从具有式(VIII)的化合物(其中X是F、Cl、Br、I、或OSO2Me),通过在-78℃与25℃之间的温度下在合适的溶剂(例如二甲基甲酰胺、丙酮或四氢呋喃)中在碱(例如六甲基二硅氮锂、正丁基锂、Cs2CO3、CSF、K2CO3或NaH)的存在下用具有式(II)的化合物进行处理来制备。此外,一些反应可能仅在较高温度下和/或在催化剂体系(如CuI/二甲基乙二胺或Pd(OAc)2/Xantphos存在下进行。对于相关实例,参见:WO 2004/087646;WO 2013/132253;Garcia,M.等人Org.Biomol.Chem.[有机与生物分子化学]2004,11,1633;Guyonner,M.和Baudoin,O.Org.Lett.[有机快报]2012,14,398;Philipps,D.P.等人Tetrahedron Lett.[四面体快报]2009,50,7293。此反应示于方案5中。
具有式(VII)的化合物(即,具有式(VI)的化合物(其中R5是H))(其中V是Br、I、或CN)可以从具有式(IX)的羰基化合物,通过在0℃与100℃之间的温度下在合适的溶剂(例如甲醇或乙醇)中在碱(如三乙胺)的存在下用具有式(II)的化合物处理;随后添加还原剂(例如NaBH4或NaBH3CN)来制备。对于相关实例,参见:WO 2013/071232和WO 2013/066838。此反应示于方案6中。
具有式(VIII)的化合物(其中V是Br、I或CN且X是Cl或Br)是可商购的,或者可以从具有式(VIa)的化合物,通过在55℃与100℃之间的温度下在合适的溶剂(如四氯甲烷)中在紫外线的存在下用卤素源(例如,N-溴代琥珀酰亚胺(NBS)或N-氯代琥珀酰亚胺(NCS))和自由基引发剂(如(PhCO2)2或偶氮二异丁腈(AIBN))进行处理来制备。关于相关实例,参见Liu,S.等人Syntheis[合成](2001),14,2078和Kompella,A.等人Org.Proc.Res.Dev.[有机加工研究与开发](2012),16,1794。此反应示于方案7中。具有式(VIa)的化合物是可商购的。
可替代地,具有式(VIII)的化合物(其中X是Cl、Br、I或OSO2Me)是可商购的,或者可以从具有式(X)的化合物(其中V是Br、I或CN),通过在0℃与80℃之间的温度下在合适的溶剂(例如,二氯甲烷或1,2-二氯乙烷)中在三苯基膦的存在下用卤素源(例如,CBr4、CCl4或I2)进行处理或者用甲磺酰氯(ClSO2Me)进行处理来制备。对于相关实例,参见Liu,H.等人Bioorg.Med.Chem.[生物有机与药物化学](2008),16,10013;WO 2014/020350;和Kompella,A.等人.Bioorg.Med.Chem.Lett[生物有机与药物化学快报](2001),1,3161。具有式(X)的化合物是可商购的。此反应示于方案8中。
具有式(IX)的化合物(其中V是Br、I或CN)是可商购的,或者可以从具有式(XI)的化合物(当R5是H时的化合物(X)),通过在25℃与110℃之间的温度下在合适的溶剂(例如,二噁烷或二氯甲烷)中用氧化试剂(例如KMnO4或MnO2)进行处理来制备。对于相关实例,参见WO 2003/0087940和WO 2008/104306。具有式(XI)的化合物是可商购的。此反应示于方案9中。
具有式(III)的化合物(其中X是Cl或Br)可以从具有式(XII)的化合物,通过在紫外光的存在下在55℃与100℃之间的温度下在合适的溶剂(如四氯甲烷)中用卤素源(例如N-溴代琥珀酰亚胺(NBS)或N-氯代琥珀酰亚胺(NCS))和自由基引发剂(例如(PhCO2)2或偶氮二异丁腈(AIBN))进行处理来制备。关于相关实例,参见Liu,S.等人Synthesis[合成](2001),14,2078和Kompella,A.等人Org.Proc.Res.Dev.[有机加工研究与开发](2012),16,1794。此反应示于方案10中。
如已指示的,出人意料地,现在已经发现,为实际目的,本发明的具有式(I)的化合物具有非常有利水平的用来保护植物免受由真菌引起的疾病的生物活性。
具有式(I)的化合物可以在农业部门和相关使用领域中用作例如用于控制植物有害生物的活性成分,或者在非生命材料上用于控制腐败微生物或对人潜在有害的有机体。这些新颖化合物的特色是施用比率低但活性高、植物耐受良好以及不危害环境。它们有非常有用的治疗的、预防的和系统性的特性并且可以用于保护很多栽培植株。具有式(I)的化合物可以用于抑制或破坏在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,同时还保护了稍后生长的那些植物部分免于例如植物病原性微生物的侵害。
本发明进一步涉及用于通过处理植物或植物繁殖材料和/或收获的粮食作物来控制或预防易受微生物攻击的植物或植物繁殖材料和/或收获的食物作物的侵染的方法,其中将有效量的具有式(I)的化合物施用至所述植物、其部分或其场所。
还能使用具有式(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、改变或预防真菌生长的化合物。术语“杀真菌有效量”在使用时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,并且预防包括在植物内或上面预防真菌感染的屏障或其他防御构造。
还可以能够使用具有式(I)的化合物作为用于处理植物繁殖材料(例如,种子,如果实、块茎或谷粒)或植物插条的拌种剂,用于保护对抗真菌感染连同对抗土壤里存在的植物病原性真菌。可以在种植前用包含具有式(I)的化合物的组合物处理繁殖材料:例如可以在播种前拌种。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,将具有式(I)的活性化合物施用至谷粒(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,具有式(I)的化合物可以在相关领域中用于控制真菌,例如用于工业材料(包括木材以及与木材有关的工业产品)保护、食品储存、卫生管理。
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)的化合物例如针对疾病的真菌和真菌载体以及植物病原性细菌和病毒是有效的。这些疾病的真菌和真菌载体以及植物病原性细菌和病毒是例如:
伞枝梨头霉、链格孢属物种、丝囊霉属物种、壳二孢属物种、曲霉属物种(包括黄曲霉、烟曲霉、构巢曲霉、黑曲霉、土曲霉)、短梗霉属物种(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)、葡萄座腔菌属物种(包括葡萄溃疡病菌(B.dothidea)、树花地衣葡萄座腔菌(B.obtusa))、葡萄孢属物种(包括灰葡萄孢(B.cinerea))、念珠菌属物种(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.lusitaniae)、近平滑念珠菌(C.parapsilosis)、热带念珠菌(C.tropicalis))、Cep卤代ascus fragrans、长喙壳属物种、尾孢属物种(包括褐斑病菌(C.arachidicola))、晚斑病菌(Cercosporidium personatum)、枝孢霉属物种、麦角菌、粗球孢子菌、旋孢腔菌属物种、炭疽菌属物种(包括香蕉炭疽病菌(C.musae))、新型隐球菌、间座壳属(Diaporthe)物种、亚隔孢壳属物种、内脐蠕孢属物种、痂囊腔菌属物种、表皮癣菌属物种、梨火疫病菌、白粉菌属物种(包括菊科白粉菌(E.cichoracearum))、葡萄顶枯病菌(Eutypa lata)、镰刀菌属物种(包括大刀镰刀菌、禾谷镰刀菌、F.langsethiae、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(Gaeumannomycesgraminis)、藤仓赤霉菌(Gibberella fujikuroi)、煤烟病菌(Gloeodes pomigena)、香蕉炭疽盘长孢菌(Gloeosporium musarum)、苹果炭疽病菌(Glomerella cingulate)、葡萄球座菌(Guignardia bidwellii)、植物受桧胶锈菌(Gymnosporangium juniperi-virginianae)、长蠕孢属物种、驼孢锈菌属物种、组织胞浆菌属物种(包括荚膜组织胞浆菌(H.capsulatum))、红线病菌、Leptographium lindbergi、辣椒白粉病菌(Leveillulataurica)、松针散盘壳(Lophodermium seditiosum)、雪霉叶枯菌(Microdochium nivale)、小孢子菌属物种、链核盘菌属物种、毛霉属物种、球腔菌属物种(包括禾生球腔菌、苹果黑点病菌(M.pomi))、树梢枯病菌、云杉病菌、副球孢子菌属物种、青霉属物种(包括指状青霉、意大利青霉)、霉样真霉属物种、指霜霉属物种(包括玉蜀黍指霜霉、菲律宾霜指霉和高粱指霜霉)、霜霉属物种、颖枯壳针孢、豆薯层锈菌、桑黄火木针层孔菌(Phellinus igniarus)、瓶霉蚁属物种、茎点霉属物种、葡萄生拟茎点菌(Phomopsis viticola)、疫霉菌属物种(包括致病疫霉菌)、单轴霉属物种(包括霍尔斯单轴霉菌、葡萄霜霉病菌(P.viticola))、格孢腔菌属物种、叉丝单囊壳属物种(包括白叉丝单囊壳(P.leucotricha))、禾谷多粘菌(Polymyxa graminis)、甜菜多粘菌(Polymyxa betae)、小麦基腐病菌(Pseudocercosporella herpotrichoides)、假单胞菌属物种、假霜霉属物种(包括黄瓜霜霉病菌、葎草假霜霉)、Pseudopeziza tracheiphila、霜霉属物种(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))、埋核盘菌属物种、核腔菌属物种、梨孢属物种(包括稻瘟病菌(P.oryzae))、腐霉属物种(包括终极腐霉菌)、柱隔孢属物种、丝核菌属物种、微小根毛霉(Rhizomucor pusillus)、少根根霉、喙孢属物种、丝孢菌属物种(包括尖端赛多孢子菌和多育赛多孢子菌)、煤点病(Schizothyrium pomi)、核盘菌属物种、小核菌属物种、壳针孢属物种(包括颖枯壳针孢(S.nodorum)、小麦壳针孢(S.tritici))、草莓白粉病菌(Sphaerothecamacularis)、棕丝单囊壳(Sphaerotheca fusca)(黄瓜白粉病菌(Sphaerothecafuliginea))、孢子丝菌属(Sporothorix)物种、颖枯壳多孢(Stagonospora nodorum)、匍柄霉属(Stemphylium)物种。毛韧革菌(Stereum hirsutum)、水稻枯纹病菌(Thanatephoruscucumeris)、根串珠霉(Thielaviopsis basicola)、腥黑粉菌属物种、木霉属物种(包括哈茨木霉、拟康氏木霉、绿色木霉)、毛癣菌属物种、核瑚菌属物种、葡萄钩丝壳、条黑粉菌属(Urocystis)物种、黑粉菌属(Ustilago)物种、黑星菌属物种(包括苹果黑星菌(V.inaequalis))、轮枝孢属物种、以及黄单胞菌属物种。
具有式(I)的化合物可以用于例如草坪,观赏植物如花卉、灌木、阔叶树木或常绿植物,例如松柏类,以及树木注入、有害生物管理等。
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,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,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、大麻、黄麻以及剑麻;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。
术语“有用植物”应当理解为还包括由于常规育种方法或基因工程致使其对除草剂(像溴草腈)或除草剂类(例如像HPPD抑制剂、ALS抑制剂,例如氟嘧磺隆、氟丙磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮-莽草酸-3-磷酸-合成酶)抑制剂、GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)耐受的有用植物。已经通过常规育种方法(诱变)致使对咪唑啉酮(例如甲氧咪草烟)耐受的作物的实例是夏季油菜(卡诺拉)。已经通过基因工程方法致使对除草剂或除草剂类耐受的作物的实例包括草甘膦和草丁膦抗性玉米品种,它们在Herculex和商标名下是可商购的。
术语“有用植物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的有用植物,这些毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
此类植物的实例是:(玉米品种,表达CryIA(b)毒素);YieldGard(玉米品种,表达CryIIIB(b1)毒素);YieldGard(玉米品种,表达CryIA(b)和CryIIIB(b1)毒素);(玉米品种,表达Cry9(c)毒素);Herculex(玉米品种,表达CryIF(a2)毒素和获得对除草剂草铵膦按盐耐药性的酶膦丝菌素N-乙酰基转移酶(PAT));NuCOTN(棉花品种,表达CryIA(c)毒素);Bollgard(棉花品种,表达CryIA(c)毒素);Bollgard(棉花品种,表达CryIA(c)和CryIIA(b)毒素);(棉花品种,表达VIP毒素);(马铃薯品种,表达CryIIIA毒素);GT Advantage(GA21耐草甘膦性状)、CBAdvantage(Bt11玉米螟(CB)性状)、RW(玉米根虫性状)以及
术语“作物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的作物植物,这些毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
可由此类转基因植物表达的毒素包括例如,来自蜡样芽胞杆菌或日本金龟子芽孢杆菌的杀昆虫蛋白;或者来自苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或者营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或细菌定植线虫的杀昆虫蛋白,例如光杆状菌属某些种(Photorhabdus spp.)或致病杆菌属某些种(Xenorhabdus spp.),如发光杆菌(Photorhabdus luminescens)、嗜线虫致病杆菌(Xenorhabdus nematophilus);由动物产生的毒素,如蝎毒素、蛛毒素、蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素,植物凝集素类(lectin),如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类(agglutinin);蛋白酶抑制剂,如胰蛋白酶抑制剂、丝蛋白酶抑制剂、马铃薯糖蛋白、胱抑素、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻毒素、玉米-RIP、相思豆毒素、丝瓜籽蛋白、皂草素或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕化类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕化素抑制剂、HMG-COA-还原酶、离子通道阻断剂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、几丁质酶和葡聚糖酶。
进一步地,在本发明的背景下,δ-内毒素(例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C)或营养期杀虫蛋白(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插入毒素中,例如像在Cry3A055的情况下,一种组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
这样的毒素或能够合成这样的毒素的转基因植物的实例披露于例如EP-A-0 374753、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通常是本领域技术人员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 367474、EP-A-0 401 979和WO 90/13651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。此类植物的实例是:(玉米品种,表达Cry1Ab毒素);YieldGard(玉米品种,表达Cry3Bb1毒素);YieldGard(玉米品种,表达Cry1Ab和Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素和获得对除草剂草铵膦按盐耐药性的酶膦丝菌素N-乙酰基转移酶(PAT));NuCOTN(棉花品种,表达Cry1Ac毒素);(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
此类转基因作物的另外的实例是:
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-31 790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酶以获得对除草剂草铵膦铵盐的耐受性。
2.Bt176玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,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玉米还转基因表达酶PAT以获得对除草剂草铵膦铵盐的耐受性。
3.MIR604玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,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。此毒素是通过插入组织蛋白酶-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。MON 863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(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/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。遗传修饰的玉米,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(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/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON810玉米转基因地表达由土壤杆菌属物种菌株CP4获得的蛋白质CP4 EPSPS(使之耐除草剂(含有草甘膦)),以及还有由苏云金芽孢杆菌库尔斯塔克亚种(Bacillusthuringiensis subsp.kurstaki)获得的Cry1Ab毒素(使之耐某些鳞翅目昆虫,包括欧洲玉米螟)。
具有式(I)的化合物(包括表2至17(下文)中描述的任何化合物2.01至2.28至17.01至17.28,或如表A至F(下文)中所示的化合物A-1至A-4,B-1至B-7,C-1至C-18,D-1,E-1和F-1)可用于控制或预防植物病原性疾病、尤其是大豆植物上的植物病原性真菌(如豆薯层锈菌)。
具体地,表达毒素例如杀虫蛋白如δ-内毒素(例如Cry1Ac(Cry1Ac Bt蛋白))的转基因大豆植物。相应地,这可以包括包含事件MON87701(参见美国专利号8,049,071以及相关申请和专利,以及WO 2014/170327A1(例如参见参考Intacta RR2 PROTM大豆的段落[008]))、事件MON87751(美国专利申请公开号2014/0373191)或事件DAS-81419(美国专利号8632978以及相关申请和专利)的转基因大豆植物。
其他转基因大豆植物可以包含事件SYHT0H2-HPPD耐受性(美国专利申请公开号2014/0201860以及相关申请和专利)、事件MON89788-草甘膦耐受性(美国专利号7,632,985以及相关申请和专利)、事件MON87708-麦草畏耐受性(美国专利申请公开号US 2011/0067134以及相关申请和专利)、事件DP-356043-5-草甘膦以及ALS耐受性(美国专利申请公开号US 2010/0184079以及相关申请和专利)、事件A2704-12-草铵膦耐受性(美国专利申请公开号US 2008/0320616以及相关申请和专利)、事件DP-305423-1-ALS耐受性(美国专利申请公开号US 2008/0312082以及相关申请和专利)、事件A5547-127-草铵膦耐受性(美国专利申请公开号US 2008/0196127以及相关申请和专利)、事件DAS-40278-9-对2,4-二氯苯氧基乙酸和芳氧基苯氧基丙酸酯的耐受性(参见WO 2011/022469、WO 2011/022470、WO 2011/022471、以及相关申请和专利)、事件127-ALS耐受性(WO 2010/080829以及相关申请和专利)、事件GTS 40-3-2-草甘膦耐受性、事件DAS-68416-4-2,4-二氯苯氧基乙酸以及草铵膦耐受性、事件FG72-草甘膦和异噁唑草酮耐受性、事件BPS-CV127-9-ALS耐受性以及GU262-草铵膦耐受性或事件SYHT04R-HPPD耐受性。
如本文使用的术语“场所”意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”应当被理解为表示该植物的生殖部分,例如种子,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。
具有式(I)的化合物能以未修饰的形式使用,或者优选地,连同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、尘剂、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、粘合剂或肥料类。这样的载体例如描述在WO 97/33890中。
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。此类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。活性成分的量的范围可以是从该浓缩物的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。这些颗粒含有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。可湿性粉剂通常含有从5%到95%的活性成分加上少量的润湿剂、分散剂或乳化剂。
可乳化的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液体或固体乳化剂组成,或者还可以含有液态载体,如二甲苯、重芳族石脑油、异佛尔酮和其他不挥发有机溶剂。在使用时,将这些浓缩物分散在水中或其他液体中,并且通常作为喷雾剂施用至有待处理的区域。活性成分的量的范围可以是从该浓缩物的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至需要处理的区域。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%至25%的活性组分,这些成分可包括表面活性剂例如重芳烃挥发油、煤油和其他石油馏分,或植物油;和/或粘着剂如糊精、胶或合成树脂。
尘粉剂是活性成分与高度分散的固体(例如滑石、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。
微囊典型地是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(例如丙酮、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、二甘醇丁醚、二甘醇乙醚、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盐如月桂基硫酸二乙醇铵;烷基芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚-氧化烯加成产物,如壬基酚-C18乙氧基化物;醇-氧化烯加成产物,如十三烷醇-C16乙氧基化物;皂,如硬脂酸钠;烷基萘磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯的盐,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季胺类,如月桂基三甲基氯化铵;脂肪酸的聚氧乙烯酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单和二烷基酯的盐。
通常在农业组合物中使用的其他佐剂包括结晶作用抑制剂、粘度调节剂、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。
此外,进一步地,其他杀生物的活性成分或组合物可以与本发明的组合物组合,并且用于本发明的方法中并且同时地或顺序地随着本发明的组合物施用。当同时施用时,这些另外的活性成分可以连同本发明的组合物一起配制或混合于例如喷雾罐中。这些另外的杀生物的活性成分可以是杀真菌剂、除草剂、杀昆虫剂、杀细菌剂、杀螨剂、杀线虫剂和/或植物生长调节剂。
本文提及的使用其俗名的杀有害生物剂是已知的,例如,从“The PesticideManual[杀有害生物剂手册]”,第15版,英国作物保护委员会(British Crop ProtectionCouncil)2009。
此外,本发明的组合物还可以与一种或多种系统获得性抗性诱导剂(“SAR”诱导剂)一起施用。SAR诱导剂是已知的并且描述于例如美国专利号US 6,919,298中,并且包括例如水杨酸盐以及商用的SAR诱导剂阿拉酸式苯-S-甲基。
具有式(I)的化合物通常以农用化学组合物的形式使用并且可以与另外的化合物同时地或顺序地施用至作物区域或有待处理的植物。例如,这些另外的化合物可以是影响植物生长的肥料或微量营养素供体或其他制剂。它们还可以是选择性除草剂或非选择性除草剂,连同杀昆虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种这些制剂的混合物,如果希望的话连同配制品领域中通常使用的另外的载体、表面活性剂或促进施用的佐剂一起。
具有式(I)的化合物可以按控制或保护对抗植物病原性微生物的(杀真菌的)组合物的形式使用,所述组合物包含作为活性成分的至少一种具有式(I)的化合物或至少一种优选的如本文所定义的个别化合物(处于游离形式或处于农用化学上可用的盐形式)和至少一种上述佐剂。
因此,本发明提供了包含至少一种具有式(I)的化合物、农业上可接受的载体和任选地佐剂的组合物,优选杀真菌组合物。农业上可接受的载体是例如适用于农业用途的载体。农业载体在本领域是熟知的。优选地,除了包含具有式(I)的化合物,所述组合物可以包含至少一种或多种杀有害生物活性化合物,例如另外的杀真菌活性成分。
具有式(I)的化合物可以是组合物的唯一活性成分,或者适当时它可以与一种或多种另外的活性成分(如杀有害生物剂、杀真菌剂、增效剂、除草剂或植物生长调节剂)混合。在一些情况下,另外的活性成分会导致出人意料的协同活性。
合适的另外的活性成分的实例包括以下项: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、三唑杀真菌剂、三唑并嘧啶杀真菌剂、尿素杀真菌剂、缬氨酰胺(valinamide)杀真菌剂、以及锌杀真菌剂。
合适的另外的活性成分的实例还包括以下项:3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸甲氧基-[1-甲基-2-(2,4,6-三氯苯基)-乙基]-酰胺、1-甲基-3-二氟甲基-1H-吡唑-4-甲酸(2-二氯亚甲基-3-乙基-1-甲基-茚满-4-基)-酰胺(1072957-71-1)、1-甲基-3-二氟甲基-1H-吡唑-4-甲酸(4’-甲基硫烷基-联苯基-2-基)-酰胺、1-甲基-3-二氟甲基-4H-吡唑-4-甲酸[2-(2,4-二氯-苯基)-2-甲氧基-1-甲基-乙基]-酰胺、(5-氯-2,4-二甲基-吡啶-3-基)-(2,3,4-三甲氧基-6-甲基-苯基)-甲酮、(5-溴-4-氯-2-甲氧基-吡啶-3-基)-(2,3,4-三甲氧基-6-甲基-苯基)-甲酮、2-{2-[(E)-3-(2,6-二氯-苯基)-1-甲基-丙-2-烯-(E)-亚基氨基氧基甲基]-苯基}-2-[(Z)-甲氧基亚氨基]-N-甲基-乙酰胺、3-[5-(4-氯-苯基)-2,3-二甲基-异噁唑烷-3-基]-吡啶、(E)-N-甲基-2-[2-(2,5-二甲基苯氧基甲基)苯基]-2-甲氧基-亚氨基乙酰胺、4-溴-2-氰基-N,N-二甲基-6-三氟甲基苯并咪唑-1-磺酰胺、a-[N-(3-氯-2,6-二甲苯基)-2-甲氧基乙酰胺基]-y-丁内酯、4-氯-2-氰基-N,N-二甲基-5-对甲苯基咪唑-1-磺酰胺、N-烯丙基-4,5,-二甲基-2-三甲基甲硅烷基噻吩-3-甲酰胺、N-(l-氰基-1,2-二甲基丙基)-2-(2,4-二氯苯氧基)丙酰胺、N-(2-甲氧基-5-吡啶基)-环丙烷甲酰胺、(.+-.)-顺式-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇、2-(1-叔丁基)-1-(2-氯苯基)-3-(1,2,4-三唑-1-基)-丙-2-醇、2’,6’-二溴-2-甲基-4-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺、1-咪唑基-1-(4’-氯苯氧基)-3,3-二甲基丁-2-酮、(E)-2-[2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基]3-甲氧基丙烯酸甲酯、(E)-2-[2-[6-(2-硫代酰胺基苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[6-(2-氟苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[6-(2,6-二氟苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[3-(嘧啶-2-基氧基)苯氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[3-(5-甲基嘧啶-2-基氧基)-苯氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[3-(苯基-磺酰基氧基)苯氧基]苯基-3-甲氧基丙烯酸甲酯、(E)-2-[2-[3-(4-硝基苯氧基)苯氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-苯氧基苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-(3,5-二甲基-苯甲酰基)吡咯-1-基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-(3-甲氧基苯氧基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2[2-(2-苯基乙烯-1-基)-苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-(3,5-二氯苯氧基)吡啶-3-基]-3-甲氧基丙烯酸甲酯、(E)-2-(2-(3-(1,1,2,2-四氟乙氧基)苯氧基)苯基)-3-甲氧基丙烯酸甲酯、(E)-2-(2-[3-(α-羟基苄基)苯氧基]苯基)-3-甲氧基丙烯酸甲酯、(E)-2-(2-(4-苯氧基吡啶-2-基氧基)苯基)-3-甲氧基丙烯酸甲酯、(E)-2-[2-(3-正丙基氧基-苯氧基)苯基]3-甲氧基丙烯酸甲酯、(E)-2-[2-(3-异丙基氧基苯氧基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[3-(2-氟苯氧基)苯氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-(3-乙氧基苯氧基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-(4-叔丁基-吡啶-2-基氧基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[3-(3-氰基苯氧基)苯氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[(3-甲基-吡啶-2-基氧基甲基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[6-(2-甲基-苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-(5-溴-吡啶-2-基氧基甲基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-(3-(3-碘吡啶-2-基氧基)苯氧基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2-[2-[6-(2-氯吡啶-3-基氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸甲酯、(E),(E)-2-[2-(5,6-二甲基吡嗪-2-基甲基肟基甲基)苯基]-3-甲氧基丙烯酸甲酯、(E)-2-{2-[6-(6-甲基吡啶-2-基氧基)嘧啶-4-基氧基]苯基}-3-甲氧基-丙烯酸甲酯、(E),(E)-2-{2-(3-甲氧基苯基)甲基肟基甲基]-苯基}-3-甲氧基丙烯酸甲酯、(E)-2-{2-(6-(2-叠氮基苯氧基)-嘧啶-4-基氧基]苯基}-3-甲氧基丙烯酸甲酯、(E),(E)-2-{2-[6-苯基嘧啶-4-基)-甲基肟基甲基]苯基}-3-甲氧基丙烯酸甲酯、(E),(E)-2-{2-[(4-氯苯基)-甲基肟基甲基]-苯基}-3-甲氧基丙烯酸甲酯、(E)-2-{2-[6-(2-正丙基苯氧基)-1,3,5-三嗪-4-基氧基]苯基}-3-甲氧基丙烯酸甲酯、(E),(E)-2-{2-[(3-硝基苯基)甲基肟基甲基]苯基}-3-甲氧基丙烯酸甲酯、3-氯-7-(2-氮杂-2,7,7-三甲基-辛-3-烯-5-炔)、2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺、3-碘-2-丙炔醇、4-氯苯基-3-碘炔丙基缩甲醛、3-溴-2,3-二碘-2-丙烯基乙基氨基甲酸酯、2,3,3-三碘烯丙醇、3-溴-2,3-二碘-2-丙烯醇、3-碘-2-丙炔基正丁基氨基甲酸酯、3-碘-2-丙炔基正己基氨基甲酸酯、3-碘-2-丙炔基环己基-氨基甲酸酯、3-碘-2-丙炔基苯基氨基甲酸酯;苯酚衍生物,例如三溴苯酚、四氯酚、3-甲基-4-氯酚、3,5-二甲基-4-氯酚、苯氧乙醇、二氯酚、邻苯基苯酚、间苯基苯酚、对苯基苯酚、2-苄基-4-氯酚、5-羟基-2(5H)-呋喃酮;4,5-二氯二噻唑啉酮、4,5-苯并二噻唑啉酮、4,5-三亚甲基二噻唑啉酮、4,5-二氯-(3H)-1,2-二巯基-3-酮、3,5-二甲基-四氢-1,3,5-噻二嗪-2-硫酮、N-(2-对氯苯甲酰乙基)-氯化六甲撑四胺、活化酯、八九十混酸(acypetacs)、棉铃威、阿苯达唑、杀螟丹(aldimorph)、蒜素、烯丙醇、辛唑嘧菌胺、吲唑磺菌胺、阿姆巴(amobam)、氨丙膦酸(ampropylfos)、敌菌灵、福美砷(asomate)、金色制霉素(aureofungin)、阿扎康唑、阿扎芬定(azafendin)、氧化福美双杀菌剂(azithiram)、嘧菌酯、钡多硫化物、苯霜灵、苯霜灵-M、麦锈灵(benodanil)、苯菌灵、敌菌腙、丙唑草隆(bentaluron)、苯噻菌胺、苯噻硫氰、氯化苄烷铵、节烯酸(benzamacril)、苯杂吗(benzamorf)、苯甲羟肟酸、苯并烯氟菌唑(benzovindiflupyr)、黄连素、百杀辛(bethoxazin)、双苯三唑醇(biloxazol)、乐杀螨、联苯基、联苯三唑醇、硫双二氯酚、联苯吡菌胺(bixafen)、杀稻瘟菌素-S、啶酰菌胺、溴菌腈、糠菌唑、乙嘧酚磺酸酯、丁硫啶、丁胺多硫化钙、敌菌丹、克菌丹、吗菌威、多菌灵、多菌灵盐酸盐、萎锈灵、加普胺、香芹酮、CGA41396、CGA41397、灭螨猛、壳聚糖、灭痕唑(chlobenthiazone)、双胺灵、氯醌、氯芬唑、地茂散、氯化苦、百菌清、克氯得(chlorozolinate)、乙菌利、氯咪巴唑、克霉唑、克拉康(clozylacon)、含铜的化合物如乙酸铜、碳酸铜、氢氧化铜、环烷酸铜、油酸铜、氯氧化铜、氧基喹啉铜、硅酸铜、硫酸铜、树脂酸铜、铬酸铜锌和波尔多混合物、甲酚、硫杂灵、福美铜氯(cuprobam)、亚铜的氧化物、氰霜唑、环菌胺(cyclafuramid)、放线菌酮、环氟菌胺、霜脲氰、氰菌灵(cypendazole)、环唑醇、嘧菌环胺、棉隆、咪菌威、癸磷锡、脱氢乙酸、二-2-吡啶基二硫化物1,1’-二氧化物、抑菌灵(dichlofluanid)、哒菌清、二氯萘醌、氯硝胺、双氯酚、菌核利、苄氯三唑醇、双氯氰菌胺、乙霉威、苯醚甲环唑、野燕枯、二氟林、O,O-二异丙基-S-苄基硫代磷酸盐、地美福唑(dimefluazole)、菌核净、地美康唑(dimetconazole)、烯酰吗啉、二甲嘧酚、烯唑醇、烯唑醇-M、敌螨通、敌螨普、邻敌螨消、硝戊酯(dinopenton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、二苯胺、双吡硫翁、戒酒硫、灭菌磷(ditalimfos)、二噻农、二硫基醚、十二烷基二甲基氯化铵、十二环吗啉、多地辛、多果定、十二烷基胍醋酸盐、敌菌酮、敌瘟磷、烯肟菌酯(enestroburin)、氟环唑、乙环唑、代森硫(etem)、噻唑菌胺、乙嘧酚、乙氧喹、乙蒜素(ethilicin)、(Z)-N-苄基-N([甲基(甲基-硫代亚乙基氨基-氧基羰基)氨基]硫基)-β-丙氨酸乙酯、土菌灵、恶唑菌酮、咪唑菌酮、地克松、咪菌腈、氯苯嘧啶醇、腈苯唑、甲呋酰胺、环酰菌胺、种衣酯、氰菌胺、拌种咯、fenpicoxamid、苯锈啶、丁苯吗啉、胺苯吡菌酮、三苯锡醋酸盐、三苯基氢氧化锡、福美铁、嘧菌腙、氟啶胺、咯菌腈、氟美托、氟吗啉、氟吡菌胺(flupicolide)、氟吡菌酰胺、唑呋草、三氟苯唑(fluotrimazole)、氟嘧菌酯、氟喹唑、氟硅唑、磺菌胺、氟酰胺(flutanil)、氟酰胺(flutolanil)、粉唑醇、氟唑菌酰胺、灭菌丹、甲醛、三乙膦酸、麦穗宁、呋霜灵、福拉比、二甲呋酰胺、呋菌唑、糠醛、茂谷乐、呋菌隆、果绿定、灰黄霉素、双胍辛胺、丙烯酸喹啉酯(halacrinate)、六氯苯、六氯丁二烯、六氯酚、己唑醇、环己硫磷(hexylthiofos)、汞加芬(hydrargaphen)、羟基异噁唑、恶霉灵、抑霉唑、抑霉唑硫酸盐、亚胺唑、双胍辛胺、双胍辛胺三乙酸酯、枯瘟净(inezin)、碘代丙炔基丁基甲胺酸酯(iodocarb)、种菌唑、ipfentrifluconazole、异稻瘟净、异菌脲、丙森锌、异丙基丁基氨基甲酸酯、稻瘟灵、吡唑萘菌胺、异噻菌胺、氯苯咪菌酮(isovaledione)、浸种磷(izopamfos)、春雷霉素、醚菌酯-甲基、LY186054、LY211795、LY248908、代森锰锌、双炔酰菌胺、代森锰、邻酰胺、咪卡病西(mecarbinzid)、精甲霜灵、氯氟醚菌唑(mefentrifluconazole)、嘧菌胺、灭锈胺、氯化汞、氯化亚汞、消螨多(meptyldinocap)、甲霜灵、精甲霜灵-M、威百亩、肼叉噁唑酮(metazoxolon)、叶菌唑、磺菌威、呋菌胺、甲基溴、甲基碘、异硫氰酸甲酯、代森联、代森联-锌、苯氧菌胺、苯菌酮、噻菌胺、代森环(milneb)、吗啉胍(moroxydine)、腈菌唑、甲菌利(myclozolin)、代森钠(nabam)、那他霉素、田安、福美镍、硝基苯乙烯、酞菌酯、氟苯嘧啶醇、异噻菌酮、呋酰胺、有机汞化合物类、肟醚菌胺、蛇床子素(osthol)、噁霜灵(oxadixyl)、环氧嘧磺隆、奥辛-铜(oxine-copper)、噁喹酸、欧伯克唑(oxpoconazole)、氧化萎锈灵、苯吡醇(parinol)、稻瘟酯、戊菌唑、戊菌隆、戊苯吡菌胺、五氯酚、吡噻菌胺、氰烯菌酯、叶枯净、氯瘟磷(phosdiphen)、疫霉灵-Al、磷酸类、苯酞、啶氧菌酯、粉病灵、多氨基甲酸酯、多氧菌素D、多氧瑞莫(polyoxrim)、代森联(polyram)、烯丙苯噻唑、咪鲜胺、腐霉利、普罗帕脒(propamidine)、霜霉威、丙环唑、丙森锌、丙酸、丙氧喹啉、硫菌威(prothiocarb)、丙硫菌唑、氟唑菌酰羟胺(pydiflumetofen)、比锈灵、唑菌胺酯、唑胺菌酯(pyrametrostrobin)、唑菌酯、定菌磷、吡菌苯威、啶菌腈(pyridinitril)、啶斑肟、嘧霉胺、吡奥芬酮(pyriofenone)、咯喹酮、吡氯灵(pyroxychlor)、氯吡呋醚、吡咯尼林、季铵化合物、羟基喹啉基乙酮(quinacetol)、醌菌腙(quinazamid)、唑喹菌酮(quinconazole)、灭螨猛、喹氧灵、五氯硝基苯、吡咪唑(rabenzazole)、蛔蒿素(santonin)、环苯吡菌胺(sedaxane)、硅噻菌胺、硅氟唑、西克唑(sipconazole)、五氯酚钠、螺环菌胺、链霉素、硫、戊苯砜(sultropen)、戊唑醇、异丁乙氧喹啉(tebfloquin)、叶枯酞、四氯硝基苯、福代硫(tecoram)、氟醚唑、噻苯达唑、噻二氟(thiadifluor)、噻菌腈(thicyofen)、噻氟菌胺、2-(硫氰基甲硫基)苯并噻唑、硫菌灵-甲基、克杀螨(thioquinox)、塞仑、噻酰菌胺、亚胺唑(timibenconazole)、硫氰苯甲酰胺(tioxymid)、立枯磷-甲基、对甲抑菌灵、三唑酮、三唑醇、威菌磷(triamiphos)、嘧菌醇(triarimol)、丁三唑、咪唑嗪、三环唑、十三吗啉、肟菌酯、啶虫咪(triflumazole)、嗪氨灵、氟菌唑、灭菌唑、烯效唑、福美甲胂(urbacide)、井岗霉素、霜霉灭(valifenalate)、威百、乙烯菌核利、氰菌胺(zarilamid)、代森锌、福美锌以及苯酰菌胺。
本发明的化合物也可以与驱蠕虫药剂组合使用。这样的驱蠕虫药剂包括选自大环内酯类化合物的化合物,如伊维菌素、阿维菌素、阿巴美丁、依马克丁、依立诺克丁、多拉克汀、司拉克丁、莫昔克丁、奈马克丁以及米尔倍霉素衍生物,如在EP-357460、EP-444964以及EP-594291中所述。另外的驱蠕虫药剂包括半合成及生物合成阿维菌素/米尔倍霉素衍生物,如在US-5015630、WO-9415944以及WO-9522552中所述的那些。另外的驱蠕虫药剂包括苯并咪唑类,例如阿苯达唑、坎苯达唑、芬苯达唑、氟苯达唑、甲苯达唑、奥芬达唑、奥苯达唑、帕苯达唑、以及该类别的其他成员。另外的驱蠕虫药剂包括咪唑并噻唑类以及四氢嘧啶类,例如四咪唑、左旋咪唑、双羟萘酸噻嘧啶、奥克太尔或莫仑太尔。另外的驱蠕虫药剂包括杀吸虫剂(如三氯苯达唑和氯舒隆)以及杀绦虫剂(如吡喹酮和依西太尔)。
本发明的化合物可以与对郝青酰胺(paraherquamide)/马可氟汀(marcfortine)类驱蠕虫药剂的衍生物及类似物以及抗寄生虫噁唑啉(如在US-5478855、US-4639771和DE-19520936中所披露的)组合使用。
本发明的化合物可以与如WO 96/15121中所述的一般种类二氧代吗啉抗寄生虫剂的衍生物及类似物以及还与驱蠕虫活性的环状缩酚肽(如WO 96/11945、WO 93/19053、WO93/25543、EP 0 626 375、EP 0 382 173、WO 94/19334、EP 0 382 173和EP 0 503 538中所述的那些)组合使用。
本发明的化合物可以与其他杀体外寄生虫药组合使用;例如,氟虫腈;拟除虫菊酯;有机磷酸酯;昆虫生长调节剂(如虱螨脲);蜕皮激素促效剂(如虫酰肼等);新烟碱(如吡虫啉等)。
本发明的化合物可以与萜烯生物碱类组合使用,例如国际专利申请公开号WO 95/19363或WO 04/72086中所述的那些,特别是其中所披露的化合物。
可以与本发明的化合物组合使用的这样的生物活性化合物的其他实例包括但不限于以下项:
有机磷酸酯:乙酰甲胺磷、甲基吡噁磷、乙基谷硫磷、甲基谷硫磷、溴硫磷、乙基溴硫磷、硫线磷、四氯乙磷(chlorethoxyphos)、毒死蜱、氯芬磷、氯甲磷、内吸磷、内吸磷-S-甲基、内吸磷-S-甲基砜、氯亚胺硫磷、二嗪磷、敌敌畏、百治磷、乐果、乙拌磷、乙硫磷、灭线磷、氧嘧啶磷、伐灭磷、苯线磷、杀螟硫磷、丰索磷、倍硫磷、吡氟硫磷、地虫磷、安果、噻唑磷、庚烯磷、氯唑磷、异丙磷、异噁唑磷、马拉硫磷、虫螨畏、甲胺磷、杀扑磷、甲基对硫磷、速灭磷、久效磷、二溴磷、氧乐果、甲基氧代内吸磷、对氧磷、对硫磷、甲基对硫磷、稻丰散、伏杀硫磷、硫环磷、磷克、亚胺硫磷、磷胺、甲拌磷、肟硫磷、虫螨磷、虫螨磷-甲基、丙溴磷、丙虫磷、proetamphos、丙硫磷、吡唑硫磷、哒嗪硫磷、喹硫磷、硫灭克磷、替美磷、特丁磷、丁基嘧啶磷、司替罗磷、二甲硫吸磷(thimeton)、三唑磷、敌百虫、灭蚜硫磷。
氨基甲酸酯:棉铃威、涕灭威、2-仲丁苯基甲基氨基甲酸酯、丙硫克百威、甲萘威、克百威、丁硫克百威、地虫威、乙硫苯威、苯氧威、芬硫克、呋线威、HCN-801、异丙威、茚虫威、灭虫威、灭多虫、5-甲基-间-异丙苯基丁炔基(甲基)氨基甲酸酯、杀线威、抗蚜威、残杀威、硫双威、久效威、唑蚜威、UC-51717。
拟除虫菊酯:氟丙菊酯、烯丙菊酯、顺式氯氰菊酯、5-苄基-3-呋喃甲基(E)-(1R)-顺式-2,2-二甲基-3-(2-氧代硫杂环戊烷-3-亚基甲基)环丙烷甲酸酯、联苯菊酯、β-氟氯氰菊酯、氟氯氰菊酯、a-氯氰菊酯、β-氯氰菊酯、生物丙烯菊酯、生物丙烯菊酯((S)-环戊基异构体)、生物苄呋菊酯、联苯菊酯、NCI-85193、乙氰菊酯、三氟氯氰菊酯、氯氰菊酯、苯氰菊酯、溴氰菊酯、烯炔菊酯、高氰戊菊酯、醚菊酯、五氟苯菊酯、甲氰菊酯、氰戊菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯(D异构体)、炔咪菊酯、三氟氯氰菊酯、λ-高效氯氟氰菊酯、苄氯菊酯、苯醚菊酯、炔丙菊酯、除虫菊酯(天然产物)、苄呋菊酯、胺菊酯、四氟苯菊酯、θ-氯氰菊酯、氟硅菊酯、t-氟胺氰菊酯、七氟菊酯、四溴菊酯、ζ-氯氰菊酯。
节肢动物生长调节剂:a)甲壳质合成抑制剂:苯甲酰脲:定虫隆、除虫脲、氟佐隆、氟螨脲、氟虫脲、氟铃脲、虱螨脲、双苯氟脲、伏虫脲、杀虫脲、噻嗪酮、苯虫醚、噻螨酮、乙螨唑、四螨嗪(chlorfentazine);b)蜕皮激素拮抗剂:氯虫酰肼、甲氧虫酰肼、虫酰肼;c)保幼激素类似物:吡丙醚、烯虫酯(包括S-烯虫酯)、苯氧威;d)脂质生物合成抑制剂:螺螨酯。
其他抗寄生虫药:灭螨醌、双甲脒、AKD-1022、ANS-118、印楝素、苏云金杆菌、杀虫磺、联苯肼酯、乐杀螨、溴螨酯、BTG-504、BTG-505、毒杀芬、杀螟丹、敌螨酯、杀虫脒、溴虫腈、环虫酰肼、噻虫胺、赛灭净、敌克隆登(diacloden)、杀螨隆、DBI-3204、二活菌素、二羟基甲基二羟基吡咯烷、敌螨通、敌螨普、硫丹、乙虫腈、醚菊酯、喹螨醚、氟螨嗪(flumite)、MTI-800、唑螨酯、嘧螨酯、氟螨噻、溴氟菊酯、氟螨嗪、三氟醚、苄螨醚(fluproxyfen)、苄螨醚(halofenprox)、氟蚁腙、IKI-220、水硅钠石、NC-196、印度薄荷草(neem guard)、尼敌诺特呋喃(nidinorterfuran)、烯啶虫胺、SD-35651、WL-108477、啶虫丙醚、克螨特、普罗芬布特(protrifenbute)、吡蚜酮、哒螨酮、嘧螨醚、NC-1111、R-195、RH-0345、RH-2485、RYI-210、S-1283、S-1833、SI-8601、氟硅菊酯、硅罗玛汀(silomadine)、多杀菌素、吡螨胺、三氯杀螨砜、四抗菌素、噻虫啉、杀虫环、噻虫嗪、唑虫酰胺、唑蚜威、三乙多杀菌素、三活菌素、增效炔醚、波塔雷克(vertalec)、YI-5301。
生物剂:苏云金芽孢杆菌亚莎华亚种(Bacillus thuringiensis ssp aizawai)、苏云金芽孢杆菌库斯塔克亚种(kurstaki)、苏云金芽孢杆菌δ内毒素、杆状病毒、昆虫病原细菌、病毒以及真菌。
杀细菌剂:金霉素、土霉素、链霉素。
其他生物剂:恩氟沙星、非班太尔、喷沙西林、美洛昔康、头孢氨苄、卡那霉素、匹莫苯丹、克仑特罗、奥美拉唑、硫姆林、贝那普利、吡唑虫啶(pyriprole)、头孢喹肟、氟苯尼考、布舍瑞林、头孢维星、托拉菌素、头孢噻呋、卡洛芬、美氟腙、吡喹酮、三氯苯达唑。
具有式(I)的化合物与活性成分的以下混合物是优选的。缩写“TX”意指选自由以下组成的组的一种化合物:表2至17(下文)中描述的化合物2.01至2.28至17.01至17.28,或如表A至F(下文)中所示的化合物A-1至A-4,B-1至B-7,C-1至C-18,D-1,E-1和F-1。
佐剂,该佐剂选自由以下组成的物质组:石油(别名)(628)+TX,
杀螨剂,该杀螨剂选自由以下组成的物质组:1,1-双(4-氯苯基)-2-乙氧基乙醇(IUPAC名称)(910)+TX、2,4-二氯苯基苯磺酸酯(IUPAC/化学文摘名)(1059)+TX、2-氟-N-甲基-N-1-萘乙酰胺(IUPAC名称)(1295)+TX、4-氯苯基苯基砜(IUPAC名称)(981)+TX、阿巴美丁(1)+TX、灭螨醌(3)+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、α-氯氰菊酯(202)+TX、赛硫磷(870)+TX、磺胺螨酯[CCN]+TX、氨基硫代盐(872)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、杀螨特(881)+TX、三氧化二砷(882)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、益棉磷(44)+TX、保棉磷(azinphos-methyl)(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(azacyclotin)(46)+TX、偶氮磷(azothoate)(889)+TX、苯菌灵(62)+TX、苯诺沙磷(benoxafos)(别名)[CCN]+TX、苯螨特(benzoximate)(71)+TX、苯甲酸苄酯(IUPAC名称)[CCN]+TX、联苯肼酯(74)+TX、氟氯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯(别名)+TX、溴烯杀(bromocyclene)(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、溴螨酯(bromopropylate)(94)+TX、噻嗪酮(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁基哒螨灵(butylpyridaben)(别名)+TX、石硫合剂(calcium polysulfide)(IUPAC名称)(111)+TX、毒杀芬(campheechlor)(941)+TX、氯灭杀威(carbanolate)(943)+TX、甲萘威(115)+TX、克百威(carbofuran)(118)+TX、卡波硫磷(947)+TX、CGA 50’439(研究代码)(125)+TX、灭螨猛(chinomethionat)(126)+TX、杀螨醚(chlorbenside)(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、敌螨(968)+TX、杀螨酯(chlorfenson)(970)+TX、敌螨特(chlorfensulfide)(971)+TX、氯芬磷(131)+TX、乙酯杀螨醇(chlorobenzilate)(975)+TX、伊托明(chloromebuform)(977)+TX、灭虫脲(chloromethiuron)(978)+TX、丙酯杀螨醇(chloropropylate)(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(chlorthiophos)(994)+TX、瓜菊酯(cinerin)I(696)+TX、瓜菊酯II(696)+TX、瓜菊酯类(cinerins)(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺(别名)[CCN]+TX、库马磷(174)+TX、克罗米通(别名)[CCN]+TX、巴毒磷(crotoxyphos)(1010)+TX、硫杂灵(1013)+TX、果虫磷(cyanthoate)(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、三氯氟氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(demephion)(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(demeton)(1038)+TX、甲基内吸磷(224)+TX、内吸磷-O(1038)+TX、甲基内吸磷-O(224)+TX、内吸磷-S(1038)+TX、甲基内吸磷-S(224)+TX、磺吸磷(demeton-S-methylsulfon)(1039)+TX、杀螨隆(226)+TX、氯亚胺硫磷(dialifos)(1042)+TX、二嗪磷(227)+TX、苯氟磺胺(230)+TX、敌敌畏(236)+TX、甲氟磷(dicliphos)(别名)+TX、开乐散(242)+TX、百治磷(243)+TX、遍地克(1071)+TX、甲氟磷(dimefox)(1081)+TX、乐果(262)+TX、二甲杀螨霉素(dinacti)(别名)(653)+TX、消螨酚(dinex)(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(dinobuton)(269)+TX、敌螨普(dinocap)(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、二硝酯(1090)+TX、硝戊酯(dinopenton)(1092)+TX、硝辛酯(dinosulfon)(1097)+TX、硝丁酯(dinoterbon)(1098)+TX、敌恶磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、双硫仑(别名)[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、苯氧炔螨(dofenapyn)(1113)+TX、多拉克汀(别名)[CCN]+TX、硫丹(294)+TX、因毒磷(endothion)(1121)+TX、EPN(297)+TX、依立诺克丁(别名)[CCN]+TX、乙硫磷(309)+TX、益硫磷(ethoate-methyl)(1134)+TX、乙螨唑(etoxazole)(320)+TX、乙嘧硫磷(etrimfos)(1142)+TX、抗螨唑(fenazaflor)(1147)+TX、喹螨醚(328)+TX、苯丁锡(fenbutatin oxide)(330)+TX、苯硫威(fenothiocarb)(337)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(别名)+TX、唑螨酯(fenpyroximate)(345)+TX、芬螨酯(fenson)(1157)+TX、氟硝二苯胺(fentrifanil)(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(fluacrypyrim)(360)+TX、氟佐隆(1166)+TX、氟螨噻(flubenzimine)(1167)+TX、氟螨脲(366)+TX、氟氰戊菊酯(flucythrinate)(367)+TX、联氟螨(fluenetil)(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(flumethrin)(372)+TX、氟杀螨(fluorbenside)(1174)+TX、氟胺氰菊酯(fluvalinate)(1184)+TX、FMC 1137(研究代码)(1185)+TX、抗螨脒(405)+TX、抗螨脒盐酸盐(405)+TX、安硫磷(formothion)(1192)+TX、胺甲威(formparanate)(1193)+TX、γ-HCH(430)+TX、果绿啶(glyodin)(1205)+TX、苄螨醚(halfenprox)(424)+TX、庚烯醚(heptenophos)(432)+TX、十六碳烷基环丙烷甲酸酯(IUPAC/化学文摘名)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(isocarbophos)(别名)(473)+TX、异丙基O-(甲氧基氨基硫代磷酰基)水杨酸酯(IUPAC名称)(473)+TX、伊维菌素(别名)[CCN]+TX、茉莉菊酯(jasmolin)I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(jodfenphos)(1248)+TX、林丹(430)+TX、虱螨脲(490)+TX、马拉硫磷(492)+TX、丙螨氰(malonoben)(1254)+TX、灭蚜磷(mecarbam)(502)+TX、地安磷(mephosfolan)(1261)+TX、甲硫芬(别名)[CCN]+TX、虫螨畏(methacrifos)(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、溴甲烷(537)+TX、速灭威(metolcarb)(550)+TX、速灭磷(556)+TX、自克威(mexacarbate)(1290)+TX、米尔螨素(557)+TX、米尔贝肟(milbemycin oxime)(别名)[CCN]+TX、丙胺氟磷(mipafox)(1293)+TX、久效磷(561)+TX、茂硫磷(morphothion)(1300)+TX、莫昔克丁(别名)[CCN]+TX、二溴磷(naled)(567)+TX、NC-184(化合物代码)+TX、NC-512(化合物代码)+TX、氟蚊灵(nifluridide)(1309)+TX、尼柯霉素(别名)[CCN]+TX、戊氰威(nitrilacarb)(1313)+TX、戊氰威(nitrilacarb)1:1氯化锌络合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、氧乐果(omethoate)(594)+TX、杀线威(602)+TX、亚异砜磷(oxydeprofos)(1324)+TX、砜拌磷(oxydisulfoton)(1325)+TX、pp’-DDT(219)+TX、对硫磷(615)+TX、氯菊酯(626)+TX、石油油料(别名)(628)+TX、芬硫磷(1330)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀硫磷(637)+TX、硫环磷(phosfolan)(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、甲基嘧啶磷(652)+TX、氯化松节油(polychloroterpenes)(传统名称)(1347)+TX、杀螨霉素(polynactins)(别名)(653)+TX、丙氯诺(1350)+TX、丙溴磷(662)+TX、蜱虱威(promacyl)(1354)+TX、克螨特(671)+TX、胺丙畏(propetamphos)(673)+TX、残杀威(678)+TX、乙噻唑磷(prothidathion)(1360)+TX、发硫磷(prothoate)(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊素(pyrethrins)(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(pyridaphenthion)(701)+TX、嘧螨醚(pyrimidifen)(706)+TX、嘧硫磷(1370)+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(研究代码)(1382)+TX、RA-17(研究代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(schradan)(1389)+TX、硫线磷(sebufos)(别名)+TX、塞拉菌素(selamectin)(别名)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(sophamide)(1402)+TX、季酮螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(研究代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(sulfluramid)(750)+TX、治螟磷(sulfotep)(753)+TX、硫黄(754)+TX、SZI-121(研究代码)(757)+TX、氟胺氰菊酯(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(terbam)(别名)+TX、司替罗磷(777)+TX、三氯杀螨砜(tetradifon)(786)+TX、杀螨霉素(tetranactin)(别名)(653)+TX、杀螨硫醚(tetrasul)(1425)+TX、久效威(thiafenox)(别名)+TX、抗虫威(thiocarboxime)(1431)+TX、久效威(thiofanox)(800)+TX、甲基乙拌磷(thiometon)(801)+TX、克杀螨(1436)+TX、苏力菌素(thuringiensin)(别名)[CCN]+TX、威菌磷(triamiphos)(1441)+TX、苯噻螨(triarathene)(1443)+TX、三唑磷(820)+TX、唑呀威(triazuron)(别名)+TX、敌百虫(824)+TX、氯苯乙丙磷(trifenofos)(1455)+TX、甲杀螨霉素(trinactin)(别名)(653)+TX、蚜灭多(847)+TX、氟吡唑虫(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
杀藻剂,该杀藻剂选自由以下组成的物质组:百杀辛(bethoxazin)[CCN]+TX、二辛酸铜(IUPAC名称)(170)+TX、硫酸铜(172)+TX、cybutryne[CCN]+TX、二氯萘醌(dichlone)(1052)+TX、双氯酚(232)+TX、茵多酸(295)+TX、三苯锡(fentin)(347)+TX、熟石灰[CCN]+TX、代森钠(nabam)(566)+TX、灭藻醌(quinoclamine)(714)+TX、醌萍胺(quinonamid)(1379)+TX、西玛津(730)+TX、三苯基乙酸锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX,
驱蠕虫剂,该驱蠕虫剂选自由以下组成的物质组:阿巴美丁(1)+TX、克芦磷酯(1011)+TX、多拉克汀(别名)[CCN]+TX、埃玛菌素(291)+TX、埃玛菌素苯甲酸酯(291)+TX、依立诺克丁(别名)[CCN]+TX、伊维菌素(别名)[CCN]+TX、米尔贝肟(别名)[CCN]+TX、莫昔克丁(别名)[CCN]+TX、哌嗪[CCN]+TX、司拉克丁(selamectin)(别名)[CCN]+TX、多杀菌素(737)和托布津(thiophanate)(1435)+TX,
杀鸟剂,该杀鸟剂选自由以下组成的物质组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX,
杀细菌剂,该杀细菌剂选自由以下组成的物质组:1-羟基-1H-吡啶-2-硫酮(IUPAC名称)(1222)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、8-羟基喹啉硫酸盐(446)+TX、溴硝醇(97)+TX、二辛酸铜(IUPAC名称)(170)+TX、氢氧化铜(IUPAC名称)(169)+TX、甲酚[CCN]+TX、双氯酚(232)+TX、双吡硫翁(1105)+TX、多地辛(1112)+TX、敌磺钠(fenaminosulf)(1144)+TX、甲醛(404)+TX、汞加芬(别名)[CCN]+TX、春雷霉素(483)+TX、春雷霉素盐酸盐水合物(483)+TX、二(二甲基二硫代氨基甲酸)镍(IUPAC名称)(1308)+TX、三氯甲基吡啶(nitrapyrin)(580)+TX、辛噻酮(octhilinone)(590)+TX、奥索利酸(606)+TX、土霉素(611)+TX、羟基喹啉硫酸钾(446)+TX、噻菌灵(probenazole)(658)+TX、链霉素(744)+TX、链霉素倍半硫酸盐(744)+TX、叶枯酞(766)+TX、和硫柳汞(别名)[CCN]+TX,
生物试剂,该生物试剂选自由以下组成的物质组:棉褐带卷蛾GV(别名)(12)+TX、放射形土壤杆菌(别名)(13)+TX、钝绥螨属物种(Amblyseius spp.)(别名)(19)+TX、芹菜夜蛾NPV(别名)(28)+TX、原樱翅缨小蜂(Anagrus atomus)(别名)(29)+TX、短距蚜小蜂(Aphelinus abdominalis)(别名)(33)+TX、棉蚜寄生蜂(Aphidius colemani)(别名)(34)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)(别名)(35)+TX、苜蓿银纹夜蛾NPV(别名)(38)+TX、坚强芽孢杆菌(Bacillus firmus)(别名)(48)+TX、球形芽孢杆菌(Bacillussphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillus thuringiensisBerliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensissubsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensissubsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillus thuringiensissubsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillusthuringiensis subsp.kurstaki)(学名)(51)+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subsp.tenebrionis)(学名)(51)+TX、球孢白僵菌(Beauveriabassiana)(别名)(53)+TX、布氏白僵菌(Beauveria brongniartii)(别名)(54)+TX、普通草蛉(Chrysoperla carnea)(别名)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(别名)(178)+TX、苹果蠹蛾GV(别名)(191)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)(别名)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(别名)(254)+TX、丽蚜小蜂(Encarsiaformosa)(学名)(293)+TX、桨角蚜小蜂(Eretmocerus eremicus)(别名)(300)+TX、谷实夜蛾NPV(别名)(431)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(H.megidis)(别名)(433)+TX、斑长足瓢虫(Hippodamia convergens)(别名)(442)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)(别名)(488)+TX、盲蝽(Macrolophuscaliginosus)(别名)(491)+TX、甘蓝夜蛾NPV(别名)(494)+TX、黄阔柄跳小蜂(Metaphycushelvolus)(别名)(522)+TX、黄绿绿僵菌(Metarhizium anisopliae var.acridum)(学名)(523)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)(学名)(523)+TX、欧洲新松叶蜂(Neodiprion sertifer)NPV和红头新松叶蜂(N.lecontei)NPV(别名)(575)+TX、小花蝽属物种(别名)(596)+TX、玫烟色拟青霉(Paecilomycesfumosoroseus)(别名)(613)+TX、智利小植绥螨(Phytoseiulus persimilis)(别名)(644)+TX、甜菜夜蛾核多角体病毒(Spodoptera exigua multicapsid nuclear polyhedrosisvirus)(学名)(741)+TX、毛蚊线虫(Steinernema bibionis)(别名)(742)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(别名)(742)+TX、夜蛾斯氏线虫(别名)(742)+TX、格氏线虫(Steinernema glaseri)(别名)(742)+TX、锐比斯氏线虫(Steinernema riobrave)(别名)(742)+TX、Steinernema riobravis(别名)(742)+TX、蝼蛄斯氏线虫(Steinernemascapterisci)(别名)(742)+TX、斯氏线虫属物种(Steinernema spp.)(别名)(742)+TX、赤眼蜂属物种(别名)(826)+TX、西方盲走螨(Typhlodromus occidentalis)(别名)(844)和蜡蚧轮枝菌(Verticillium lecanii)(别名)(848)+TX,解淀粉枯草芽孢杆菌变种菌株FZB24(可从美国,弗吉尼亚州24153,塞勒姆市,企业环行街5400号,诺维信生物制品有限公司(Novozymes Biologicals Inc.,5400Corporate Circle,Salem,VA 24153,U.S.A.)获得,并且以商标名是已知的)+TX,
土壤消毒剂,该土壤消毒剂选自由以下组成的物质组:碘甲烷(IUPAC名称)(542)和溴甲烷(537)+TX,
化学不育剂,该化学不育剂选自由以下组成的物质组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)(别名)[CCN]+TX、白消安(别名)[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)(别名)[CCN]+TX、六甲蜜胺(hemel)[CCN]+TX、六甲磷(hempa)[CCN]+TX、甲基涕巴(metepa)[CCN]+TX、甲硫涕巴(methiotepa)[CCN]+TX、甲基唑磷嗪(methyl apholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)(别名)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)(别名)[CCN]+TX、硫涕巴(别名)[CCN]+TX、曲他胺(别名)[CCN]和尿烷亚胺(别名)[CCN]+TX,
昆虫信息素,该昆虫信息素选自由以下组成的物质组:(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇(IUPAC名称)(222)+TX、(E)-十三碳-4-烯-1-基乙酸酯(IUPAC名称)(829)+TX、(E)-6-甲基庚-2-烯-4-醇(IUPAC名称)(541)+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯(IUPAC名称)(779)+TX、(Z)-十二碳-7-烯-1-基乙酸酯(IUPAC名称)(285)+TX、(Z)-十六碳-11-烯醛(IUPAC名称)(436)+TX、(Z)-十六碳-11-烯-1-基乙酸酯(IUPAC名称)(437)+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯(IUPAC名称)(438)+TX、(Z)-二十-13-烯-10-酮(IUPAC名称)(448)+TX、(Z)-十四碳-7-烯-1-醛(IUPAC名称)(782)+TX、(Z)-十四碳-9-烯-1-醇(IUPAC名称)(783)+TX、(Z)-十四碳-9-烯-1-基乙酸酯(IUPAC名称)(784)+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯(IUPAC名称)(283)+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯(IUPAC名称)(780)+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯(IUPAC名称)(781)+TX、14-甲基十八碳-1-烯(IUPAC名称)(545)+TX、4-甲基壬-5-醇与4-甲基壬-5-酮(IUPAC名称)(544)+TX、α-多纹素(alpha-multistriatin)(别名)[CCN]+TX、西部松小蠹集合信息素(brevicomin)(别名)[CCN]+TX、十二碳二烯醇(codlelure)(别名)[CCN]+TX、可得蒙(codlemone)(别名)(167)+TX、诱蝇酮(cuelure)(别名)(179)+TX、环氧十九烷(disparlure)(277)+TX、十二碳-8-烯-1-基乙酸酯(IUPAC名称)(286)+TX、十二碳-9-烯-1-基乙酸酯(IUPAC名称)(287)+TX、十二碳-8+TX、10-二烯-1-基乙酸酯(IUPAC名称)(284)+TX、dominicalure(别名)[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚(别名)[CCN]+TX、南部松小蠹集合信息素(frontalin)(别名)[CCN]+TX、诱虫十六酯(gossyplure)(别名)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(别名)(421)+TX、诱杀烯混剂II(别名)(421)+TX、诱杀烯混剂III(别名)(421)+TX、诱杀烯混剂IV(别名)(421)+TX、己诱剂(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)(别名)[CCN]+TX、小蠢烯醇(ipsenol)(别名)[CCN]+TX、金龟子性诱剂(japonilure)(别名)(481)+TX、三甲基二氧三环壬烷(lineatin)(别名)[CCN]+TX、litlure(别名)[CCN]+TX、粉纹夜蛾性诱剂(looplure)(别名)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、megatomoic acid(别名)[CCN]+TX、诱虫醚(methyl eugenol)(别名)(540)+TX、诱虫烯(muscalure)(563)+TX、十八碳-2,13-二烯-1-基乙酸酯(IUPAC名称)(588)+TX、十八碳-3,13-二烯-1-基乙酸酯(IUPAC名称)(589)+TX、贺康彼(orfralure)(别名)[CCN]+TX、椰蛀犀金龟聚集信息素(oryctalure)(别名)(317)+TX、非乐康(ostramone)(别名)[CCN]+TX、诱虫环(siglure)[CCN]+TX、sordidin(别名)(736)+TX、食菌甲诱醇(sulcatol)(别名)[CCN]+TX、十四碳-11-烯-1-基乙酸酯(IUPAC名称)(785)+TX、地中海实蝇引诱剂(839)+TX、地中海实蝇引诱剂A(别名)(839)+TX、地中海实蝇引诱剂B1(别名)(839)+TX、地中海实蝇引诱剂B2(别名)(839)+TX、地中海实蝇引诱剂C(别名)(839)和trunc-call(别名)[CCN]+TX,
昆虫驱避剂,该昆虫驱避剂选自由以下组成的物质组:2-(辛基硫代)乙醇(IUPAC名称)(591)+TX、避蚊酮(butopyronoxyl)(933)+TX、丁氧基(聚丙二醇)(936)+TX、己二酸二丁酯(IUPAC名称)(1046)+TX、邻苯二甲酸二丁酯(1047)+TX、丁二酸二丁酯(IUPAC名称)(1048)+TX、避蚊胺[CCN]+TX、驱蚊灵(dimethyl carbate)[CCN]+TX、邻苯二甲酸二甲酯[CCN]+TX、乙基己二醇(1137)+TX、己脲[CCN]+TX、甲喹丁(methoquin-butyl)(1276)+TX、甲基新癸酰胺[CCN]+TX、草氨酸盐(oxamate)[CCN]和派卡瑞丁[CCN]+TX,
杀昆虫剂,该杀昆虫剂选自由以下组成的物质组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-二(4-乙基苯基)乙烷(IUPAC名称)(1056)+TX、1,2-二氯丙烷(IUPAC/化学文摘名称)(1062)+TX、带有1,3-二氯丙烯的1,2-二氯丙烷(IUPAC名称)(1063)+TX、1-溴-2-氯乙烷(IUPAC/化学文摘名称)(916)+TX、乙酸2,2,2-三氯-1-(3,4-二氯苯基)乙基酯(IUPAC名称)(1451)+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯(IUPAC名称)(1066)+TX、二甲基氨基甲酸2-(1,3-二硫杂环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1109)+TX、硫氰酸2-(2-丁氧基乙氧基)乙基酯(IUPAC/化学文摘名称)(935)+TX、甲基氨基甲酸2-(4,5-二甲基-1,3-二氧环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1084)+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇(IUPAC名称)(986)+TX、2-氯乙烯基二乙基磷酸酯(IUPAC名称)(984)+TX、2-咪唑啉酮(IUPAC名称)(1225)+TX、2-异戊酰基茚满-1,3-二酮(IUPAC名称)(1246)+TX、甲基氨基甲酸2-甲基(丙-2-炔基)氨基苯基酯(IUPAC名称)(1284)+TX、月桂酸2-硫氰基乙基酯(IUPAC名称)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名称)(917)+TX、二甲基氨基甲酸3-甲基-1-苯基吡唑-5-基酯(IUPAC名称)(1283)+TX、甲基氨基甲酸4-甲基(丙-2-炔基)氨基-3,5-二甲苯基酯(IUPAC名称)(1285)+TX、二甲基氨基甲酸5,5-二甲基-3-氧代环己-1-烯基酯(IUPAC名称)(1085)+TX、阿巴美丁(1)+TX、乙酰甲胺磷(2)+TX、啶虫脒(4)+TX、家蝇磷(别名)[CCN]+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、丙烯腈(IUPAC名称)(861)+TX、棉铃威(15)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、氯甲桥萘(864)+TX、烯丙菊酯(17)+TX、阿洛氨菌素(别名)[CCN]+TX、除害威(866)+TX、α-氯氰菊酯(202)+TX、α-蜕皮激素(别名)[CCN]+TX、磷化铝(640)+TX、赛硫磷(870)+TX、硫代酰胺(872)+TX、灭害威(873)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、新烟碱(877)+TX、乙基杀扑磷(883)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、印楝素(别名)(41)+TX、甲基吡啶磷(42)+TX、谷硫磷-乙基(44)+TX、谷硫磷-甲基(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ内毒素类(别名)(52)+TX、六氟硅酸钡(别名)[CCN]+TX、多硫化钡(IUPAC/化学文摘名称)(892)+TX、熏菊酯[CCN]+TX、Bayer 22/190(研究代码)(893)+TX、Bayer 22408(研究代码)(894)+TX、噁虫威(58)+TX、丙硫克百威(60)+TX、杀虫磺(66)+TX、β-氟氯氰菊酯(194)+TX、β-氯氰菊酯(203)+TX、联苯菊酯(76)+TX、生物烯丙菊酯(78)+TX、生物烯丙菊酯S-环戊烯基异构体(别名)(79)+TX、戊环苄呋菊酯(bioethanomethrin)[CCN]+TX、生物氯菊酯(908)+TX、除虫菊酯(80)+TX、二(2-氯乙基)醚(IUPAC名称)(909)+TX、双三氟虫脲(83)+TX、硼砂(86)+TX、溴灭菊酯(别名)+TX、溴苯烯磷(914)+TX、溴杀烯(918)+TX、溴-DDT(别名)[CCN]+TX、溴硫磷(920)+TX、溴硫磷-乙基(921)+TX、合杀威(924)+TX、噻嗪酮(99)+TX、畜虫威(926)+TX、脱甲基丁嘧啶磷(butathiofos)(927)+TX、丁酮威(103)+TX、丁酯膦(932)+TX、丁酮砜威(104)+TX、丁基哒螨灵(别名)+TX、硫线磷(109)+TX、砷酸钙[CCN]+TX、氰化钙(444)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、甲萘威(115)+TX、克百威(118)+TX、二硫化碳(IUPAC/化学文摘名称)(945)+TX、四氯化碳(IUPAC名称)(946)+TX、三硫磷(947)+TX、丁硫克百成(119)+TX、杀螟丹(123)+TX、杀螟丹盐酸盐(123)+TX、西伐丁(别名)(725)+TX、冰片丹(960)+TX、氯丹(128)+TX、开蓬(963)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、氯氧磷(129)+TX、溴虫腈(130)+TX、毒虫畏(131)+TX、定虫隆(132)+TX、氯甲磷(136)+TX、氯仿[CCN]+TX、三氯硝基甲烷(141)+TX、氯辛硫磷(989)+TX、灭虫吡啶(990)+TX、毒死蜱(145)+TX、毒死蜱-甲基(146)+TX、虫螨磷(994)+TX、环虫酰肼(150)+TX、灰菊素I(696)+TX、灰菊素II(696)+TX、灰菊素类(696)+TX、顺式苄呋菊酯(cis-resmethrin)(别名)+TX、顺式苄呋菊酯(cismethrin)(80)+TX、功夫菊酯(别名)+TX、除线威(999)+TX、氯氰碘柳胺(别名)[CCN]+TX、噻虫胺(165)+TX、乙酰亚砷酸铜[CCN]+TX、砷酸铜[CCN]+TX、油酸铜[CCN]+TX、蝇毒磷(174)+TX、畜虫磷(1006)+TX、克罗米通(别名)[CCN]+TX、巴毒磷(1010)+TX、克芦磷酯(1011)+TX、冰晶石(别名)(177)+TX、CS708(研究代码)(1012)+TX、苯腈膦(1019)+TX、杀螟睛(184)+TX、果虫磷(1020)+TX、环虫菊酯[CCN]+TX、乙氰菊酯(188)+TX、氟氯氰菊酯(193)+TX、三氯氟氰菊酯(196)+TX、氯氰菊酯(201)+TX、苯氰菊酯(206)+TX、环丙马秦(209)+TX、畜蜱磷(别名)[CCN]+TX、d-柠檬烯(别名)[CCN]+TX、d-四甲菊酯(别名)(788)+TX、DAEP(1031)+TX、棉隆(216)+TX、DDT(219)+TX、单甲基克百威(decarbofuran)(1034)+TX、溴氰菊酯(223)+TX、田乐磷(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(1038)+TX、内吸磷-甲基(224)+TX、内吸磷-O(1038)+TX、内吸磷-O-甲基(224)+TX、内吸磷-S(1038)+TX、内吸磷-S-甲基(224)+TX、磺吸磷(demeton-S-methylsulphon)(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(1042)+TX、二胺磷(1044)+TX、二嗪磷(227)+TX、异氯磷(1050)+TX、除线磷(1051)+TX、敌敌畏(236)+TX、迪克力弗斯(dicliphos)(别名)+TX、迪克莱赛尔(dicresyl)(别名)[CCN]+TX、百治磷(243)+TX、地昔尼尔(244)+TX、狄氏刑(1070)+TX、二乙基5-甲基吡唑-3-基磷酸酯(IUPAC名称)(1076)+TX、除虫脲(250)+TX、二羟丙茶碱(dilor)(别名)[CCN]+TX、四氟甲醚菊酯[CCN]+TX、甲氟磷(1081)+TX、地麦威(1085)+TX、乐果(262)+TX、苄菊酯(1083)+TX、甲基毒虫畏(265)+TX、敌蝇威(1086)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、丙硝酚(1093)+TX、戊硝酚(1094)+TX、达诺杀(1095)+TX、呋虫胺(271)+TX、苯虫醚(1099)+TX、蔬果磷(1100)+TX、二氧威(1101)+TX、敌恶磷(1102)+TX、乙拌磷(278)+TX、苯噻乙双硫磷(dithicrofos)(1108)+TX、DNOC(282)+TX、多拉克汀(别名)[CCN]+TX、DSP(1115)+TX、蜕皮激素(别名)[CCN]+TX、EI 1642(研究代码)(1118)+TX、依马克丁(291)+TX、依马克丁苯甲酸酯(291)+TX、EMPC(1120)+TX、烯炔菊酯(292)+TX、硫丹(294)+TX、因毒磷(1121)+TX、异狄氏剂(1122)+TX、EPBP(1123)+TX、EPN(297)+TX、保幼醚(1124)+TX、依立诺克丁(别名)[CCN]+TX、高氰戊菊酯(302)+TX、牛津郡丙硫磷(etaphos)(别名)[CCN]+TX、乙硫苯威(308)+TX、乙硫磷(309)+TX、乙虫腈(310)+TX、益硫磷-甲基(1134)+TX、灭线磷(312)+TX、甲酸乙酯(IUPAC名称)[CCN]+TX、乙基-DDD(别名)(1056)+TX、二溴化乙烯(316)+TX、二氯化乙烯(化学名称)(1136)+TX、环氧乙烷[CCN]+TX、醚菊酯(319)+TX、乙嘧硫磷(1142)+TX、EXD(1143)+TX、氨磺磷(323)+TX、苯线磷(326)+TX、抗螨唑(1147)+TX、皮蝇磷(1148)+TX、苯硫威(1149)+TX、芬氟司林(1150)+TX、杀螟硫磷(335)+TX、丁苯威(336)+TX、嘧酰虫胺(fenoxacrim)(1153)+TX、苯氧威(340)+TX、吡氯氰菊酯(1155)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(别名)+TX、丰索磷(1158)+TX、倍硫磷(346)+TX、倍硫磷-乙基[CCN]+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、氟啶虫酰胺(358)+TX、氟虫酰胺(CAS登记号:272451-65-7)+TX、氟氯双苯隆(flucofuron)(1168)+TX、氟环脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、嘧虫胺[CCN]+TX、氟虫脲(370)+TX、三氟醚菊酯(1171)+TX、氟氯苯菊酯(372)+TX、氟胺氰菊酯(1184)+TX、FMC 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60-38(研究代码)(1328)+TX、芬硫磷(1330)+TX、苯醚菊酯(630)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀硫磷(637)+TX、硫环磷(1338)+TX、亚胺硫磷(638)+TX、对氯硫磷(1339)+TX、磷胺(639)+TX、磷化氢(IUPAC名称)(640)+TX、辛硫磷(642)+TX、辛硫磷-甲基(1340)+TX、甲胺嘧磷(pirimetaphos)(1344)+TX、抗蚜威(651)+TX、乙基嘧啶磷(1345)+TX、甲基嘧啶磷(652)+TX、聚氯二环戊二烯异构体类(IUPAC名称)(1346)+TX、聚氯萜类(传统名称)(1347)+TX、亚砷酸钾[CCN]+TX、硫氰酸钾[CCN]+TX、丙炔菊酯(655)+TX、早熟素I(别名)[CCN]+TX、早熟素II(别名)[CCN]+TX、早熟素III(别名)[CCN]+TX、乙酰嘧啶磷(primidophos)(1349)+TX、丙溴磷(662)+TX、丙氟菊酯[CCN]+TX、蜱虱威(1354)+TX、猛杀威(1355)+TX、丙虫磷(1356)+TX、胺丙畏(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、丙硫磷(686)+TX、发硫磷(1362)+TX、丙苯烃菊酯(protrifenbute)[CCN]+TX、吡蚜酮(688)+TX、吡唑硫磷(689)+TX、定菌磷(693)+TX、苄呋菊酯(pyresmethrin)(1367)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊酯类(696)+TX、哒螨灵(699)+TX、啶虫丙醚(700)+TX、哒嗪硫磷(701)+TX、嘧螨醚(706)+TX、嘧硫磷(1370)+TX、吡丙醚(708)+TX、苦木提取物(quassia)(别名)[CCN]+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷-甲基(1376)+TX、畜宁磷(1380)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(研究代码)(1382)+TX、雷复尼特(别名)[CCN]+TX、苄呋菊酯(719)+TX、鱼藤酮(722)+TX、RU 15525(研究代码)(723)+TX、RU 25475(研究代码)(1386)+TX、尼亚那(ryania)(别名)(1387)+TX、利阿诺定(传统名称)(1387)+TX、沙巴藜芦(别名)(725)+TX、八甲磷(1389)+TX、硫线磷(别名)+TX、塞拉菌素(别名)[CCN]+TX、SI-0009(化合物代码)+TX、SI-0205(化合物代码)+TX、SI-0404(化合物代码)+TX、SI-0405(化合物代码)+TX、氟硅菊酯(728)+TX、SN72129(研究代码)(1397)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟化钠(IUPAC/化学文摘名称)(1399)+TX、六氟硅酸钠(1400)+TX、五氯酚钠(623)+TX、硒酸钠(IUPAC名称)(1401)+TX、硫氰酸钠[CCN]+TX、苏硫磷(1402)+TX、多杀菌素(737)+TX、螺甲螨酯(739)+TX、螺虫乙酯(CCN)+TX、萨尔科福隆(sulcofuron)(746)+TX、萨尔科福隆钠(sulcofuron-sodium)(746)+TX、氟虫胺(750)+TX、治螟磷(753)+TX、磺酰氟(756)+TX、硫丙磷(1408)+TX、焦油(别名)(758)+TX、τ-氟胺氰菊酯(398)+TX、噻螨威(1412)+TX、TDE(1414)+TX、虫酰肼(762)+TX、吡螨胺(763)+TX、丁基嘧啶磷(764)+TX、氟苯脲(768)+TX、七氟菊酯(769)+TX、双硫磷(770)+TX、TEPP(1417)+TX、环戊烯丙菊酯(1418)+TX、叔丁威(terbam)(别名)+TX、特丁硫磷(773)+TX、四氯乙烷[CCN]+TX、杀虫畏(777)+TX、四甲菊酯(787)+TX、θ氯氰菊酯(204)+TX、噻虫啉(791)+TX、塞芬诺克斯(thiafenox)(别名)+TX、噻虫嗪(792)+TX、苯噻硫磷(thicrofos)(1428)+TX、克虫威(1431)+TX、杀虫环(798)+TX、杀虫环草酸氢盐(798)+TX、硫双威(799)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、虫线磷(1434)+TX、杀虫单(thiosultap)(803)+TX、杀虫双(thiosultap-sodium)(803)+TX、苏云金素(别名)[CCN]+TX、唑虫酰胺(809)+TX、四溴菊酯(812)+TX、四氟苯菊酯(813)+TX、反式苄氯菊酯(transpermethrin)(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、唑呀威(别名)+TX、敌百虫(824)+TX、三氯偏磷酸-3(trichlormetaphos-3)(别名)[CCN]+TX、毒壤膦(1452)+TX、三氯丙氧磷(1455)+TX、杀铃脲(835)+TX、混杀威(840)+TX、烯虫硫酯(1459)+TX、蚜灭磷(847)+TX、甲烯氟虫腈(vaniliprole)[CCN]+TX、藜芦定(别名)(725)+TX、藜芦碱(别名)(725)+TX、XMC(853)+TX、灭杀威(854)+TX、YI-5302(化合物代码)+TX、ζ-氯氰菊酯(205)+TX、泽塔米林(zetamethrin)(别名)+TX、磷化锌(640)+TX、丙硫恶唑磷(zolaprofos)(1469)以及ZXI8901(研究代码)(858)+TX、氰虫酰胺[736994-63-19]+TX、氯虫酰胺[500008-45-7]+TX、唑螨氰(cyenopyrafen)[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、氟虫吡喹(pyrifluquinazon)[337458-27-2]+TX、乙基多杀菌素(spinetoram)[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶(sulfoxaflor)[946578-00-3]+TX、丁虫腈(flufiprole)[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯(tetramethylfluthrin)[84937-88-2]+TX、三氟苯嘧啶(triflumezopyrim)(披露于WO2012/092115中)+TX,
杀软体动物剂,该杀软体动物剂选自由以下组成的物质组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(cloethocarb)(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺-乙醇胺(576)+TX、五氯酚(623)+TX、五氯苯氧化钠(623)+TX、噻螨威(tazimcarb)(1412)+TX、硫双威(799)+TX、三丁基氧化锡(913)+TX、蜗螺杀(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、三苯基乙酸锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、吡唑虫啶(pyriprole)[394730-71-3]+TX,
杀线虫剂,该杀线虫剂选自由以下组成的物质组:AKD-3088(化合物代码)+TX、1,2-二溴-3-氯丙烷(IUPAC/化学文摘名)(1045)+TX、1,2-二氯丙烷(IUPAC/化学文摘名)(1062)+TX、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1,3-二氯丙烯(233)+TX、3,4-二氯四氢噻吩1,1-二氧化物(IUPAC/化学文摘名)(1065)+TX、3-(4-氯苯基)-5-甲基罗丹宁(IUPAC名称)(980)+TX、5-甲基-6-硫代-1,3,5-噻二嗪-3-基乙酸(IUPAC名称)(1286)+TX、6-异戊烯基氨基嘌呤(别名)(210)+TX、阿巴美丁(1)+TX、乙酰虫腈[CCN]+TX、棉铃威(15)+TX、涕灭威(aldicarb)(16)+TX、涕灭砜威(aldoxycarb)(863)+TX、AZ 60541(化合物代码)+TX、苯氯噻(benclothiaz)[CCN]+TX、苯菌灵(62)+TX、丁基哒螨灵(butylpyridaben)(别名)+TX、硫线磷(cadusafos)(109)+TX、克百威(carbofuran)(118)+TX、二硫化碳(945)+TX、丁硫克百威(119)+TX、氯化苦(141)+TX、毒死蜱(145)+TX、除线威(cloethocarb)(999)+TX、细胞分裂素(cytokinins)(别名)(210)+TX、棉隆(216)+TX、DBCP(1045)+TX、DCIP(218)+TX、除线特(diamidafos)(1044)+TX、除线磷(dichlofenthion)(1051)+TX、二克磷(dicliphos)(别名)+TX、乐果(262)+TX、多拉克汀(别名)[CCN]+TX、埃玛菌素(291)+TX、埃玛菌素苯甲酸酯(291)+TX、依立诺克丁(别名)[CCN]+TX、灭线磷(312)+TX、二溴乙烷(316)+TX、苯线磷(fenamiphos)(326)+TX、吡螨胺(fenpyrad)(别名)+TX、丰索磷(1158)+TX、噻唑磷(fosthiazate)(408)+TX、丁硫环磷(fosthietan)(1196)+TX、糠醛(别名)[CCN]+TX、GY-81(研究代码)(423)+TX、速杀硫磷(heterophos)[CCN]+TX、碘甲烷(IUPAC名称)(542)+TX、异酰胺磷(isamidofos)(1230)+TX、氯唑磷(isazofos)(1231)+TX、伊维菌素(别名)[CCN]+TX、激动素(kinetin)(别名)(210)+TX、甲基减蚜磷(mecarphon)(1258)+TX、威百亩(519)+TX、威百亩钾盐(别名)(519)+TX、威百亩钠盐(519)+TX、溴甲烷(537)+TX、异硫氰酸甲酯(543)+TX、米尔贝肟(milbemycin oxime)(别名)[CCN]+TX、莫昔克丁(别名)[CCN]+TX、疣孢漆斑菌(Myrothecium verrucaria)组合物(别名)(565)+TX、NC-184(化合物代码)+TX、杀线威(602)+TX、甲拌磷(636)+TX、磷胺(639)+TX、磷虫威(phosphocarb)[CCN]+TX、克线丹(sebufos)(别名)+TX、司拉克丁(selamectin)(别名)[CCN]+TX、多杀菌素(737)+TX、叔丁威(terbam)(别名)+TX、特丁磷(terbufos)(773)+TX、四氯噻吩(IUPAC/化学文摘名)(1422)+TX、thiafenox(别名)+TX、虫线磷(thionazin)(1434)+TX、三唑磷(triazophos)(820)+TX、唑呀威(triazuron)(别名)+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(别名)(210)+TX、氟噻虫砜(fluensulfone)[318290-98-1]+TX,
硝化抑制剂,该硝化抑制剂选自由以下组成的物质组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX,
植物活化剂,该植物活化剂选自由以下组成的物质组:活化酯(acibenzolar)(6)+TX、活化酯-S-甲基(6)+TX、噻菌灵(probenazole)(658)和大虎杖(Reynoutriasachalinensis)提取物(别名)(720)+TX,
杀鼠剂,该杀鼠剂选自由以下组成的物质组:2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、α-氯代醇[CCN]+TX、磷化铝(640)+TX、安妥(880)+TX、三氧化二砷(882)+TX、碳酸钡(891)+TX、双鼠脲(912)+TX、溴鼠隆(89)+TX、溴敌隆(91)+TX、溴鼠胺(92)+TX、氰化钙(444)+TX、氯醛糖(127)+TX、氯鼠酮(140)+TX、胆钙化醇(别名)(850)+TX、氯灭鼠灵(1004)+TX、克灭鼠(1005)+TX、杀鼠萘(175)+TX、杀鼠嘧啶(1009)+TX、鼠得克(246)+TX、噻鼠灵(249)+TX、敌鼠(273)+TX、钙化醇(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、氟鼠啶(1183)+TX、氟鼠啶盐酸盐(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氰化氢(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、溴甲烷(537)+TX、鼠特灵(1318)+TX、毒鼠磷(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(1371)+TX、海葱糖苷(1390)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟乙酸钠(735)+TX、士的宁(745)+TX、硫酸铊[CCN]+TX、杀鼠灵(851)以及磷化锌(640)+TX,
增效剂,该增效剂选自由以下组成的物质组:2-(2-丁氧基乙氧基)乙基胡椒酸酯(IUPAC名称)(934)+TX、5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮(IUPAC名称)(903)+TX、具有橙花叔醇的法呢醇(别名)(324)+TX、MB-599(研究代码)(498)+TX、MGK264(研究代码)(296)+TX、增效醚(piperonyl butoxide)(649)+TX、增效醛(piprotal)(1343)+TX、增效酯(propyl isomer)(1358)+TX、S421(研究代码)(724)+TX、增效散(sesamex)(1393)+TX、芝麻林素(sesasmolin)(1394)和亚砜(1406)+TX,
动物驱避剂,该动物驱避剂选自由以下组成的物质组:蒽醌(32)+TX、氯醛糖(127)+TX、环烷酸铜[CCN]+TX、王铜(171)+TX、二嗪磷(227)+TX、二环戊二烯(化学名称)(1069)+TX、双胍辛盐(guazatine)(422)+TX、双胍辛乙酸盐(422)+TX、灭虫威(530)+TX、吡啶-4-胺(IUPAC名称)(23)+TX、塞仑(804)+TX、混杀威(trimethacarb)(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX,
杀病毒剂,所述杀病毒剂选自由以下组成的物质组:衣马宁(别名)[CCN]和利巴韦林(别名)[CCN]+TX,
创伤保护剂,该创伤保护剂选自由以下组成的物质组:氧化汞(512)+TX、辛噻酮(octhilinone)(590)和甲基托布津(802)+TX,
以及生物活性化合物,该生物活性化合物选自由以下组成的组:唑嘧菌胺[865318-97-4]+TX、吲唑磺菌胺[348635-87-0]+TX、阿扎康唑[60207-31-0]+TX、苯并烯氟菌唑(benzovindiflupyr)[1072957-71-1]+TX、联苯三唑醇[70585-36-3]+TX、联苯吡菌胺[581809-46-3]+TX、糠菌唑[116255-48-2]+TX、丁香菌酯[850881-70-8]+TX、环丙唑醇[94361-06-5]+TX、苯醚甲环唑[119446-68-3]+TX、烯唑醇[83657-24-3]+TX、烯肟菌酯[238410-11-2]+TX、氟环唑[106325-08-0]+TX、腈苯唑[114369-43-6]+TX、胺苯吡菌酮[473798-59-3]+TX、氟喹唑[136426-54-5]+TX、氟硅唑[85509-19-9]+TX、粉唑醇[76674-21-0]+TX、氟唑菌酰胺[907204-31-3]+TX、氟吡菌酰胺[658066-35-4]+TX、烯肟菌胺[366815-39-6]+TX、异丙噻菌胺(isofetamid)[875915-78-9]+TX、己唑醇[79983-71-4]+TX、抑霉唑[35554-44-0]+TX、亚胺唑[86598-92-7]+TX、种菌唑[125225-28-7]+TX、ipfentrifluconazole[1417782-08-1]+TX、异噻菌胺[224049-04-1]+TX、曼德斯宾[173662-97-0](可以根据在WO 2010/093059中描述的程序制备)+TX、氯氟醚菌唑[1417782-03-6]+TX、叶菌唑[125116-23-6]+TX、腈菌唑[88671-89-0]+TX、多效唑[76738-62-0]+TX、稻瘟酯[101903-30-4]+TX、戊苯吡菌胺[494793-67-8]+TX、戊菌唑[66246-88-6]+TX、丙硫菌唑[178928-70-6]+TX、啶斑肟(pyrifenox)[88283-41-4]+TX、咪鲜胺[67747-09-5]+TX、丙环唑[60207-90-1]+TX、硅氟唑(simeconazole)[149508-90-7]+TX、戊唑醇[107534-96-3]+TX、氟醚唑[112281-77-3]+TX、三唑酮[43121-43-3]+TX、三唑酮[55219-65-3]+TX、氟菌唑[99387-89-0]+TX、灭菌唑[131983-72-7]+TX、三环苯嘧醇[12771-68-5]+TX、氯苯嘧啶醇[60168-88-9]+TX、氟氯苯嘧啶醇[63284-71-9]+TX、乙嘧酚磺酸酯(bupirimate)[41483-43-6]+TX、甲菌定(dimethirimol)[5221-53-4]+TX、乙菌定(ethirimol)[23947-60-6]+TX、十二环吗啉[1593-77-7]+TX、苯锈啶(fenpropidin)[67306-00-7]+TX、丁苯吗啉[67564-91-4]+TX、螺环菌胺[118134-30-8]+TX、十三吗啉[81412-43-3]+TX、嘧菌环胺[121552-61-2]+TX、嘧菌胺[110235-47-7]+TX、嘧霉胺(pyrimethanil)[53112-28-0]+TX、拌种咯[74738-17-3]+TX、咯菌腈(fludioxonil)[131341-86-1]+TX、氟茚唑菌胺(fluindapyr)[1383809-87-7]+TX、苯霜灵(benalaxyl)[71626-11-4]+TX、呋霜灵(furalaxyl)[57646-30-7]+TX、甲霜灵[57837-19-1]+TX、R-甲霜灵[70630-17-0]+TX、呋酰胺[58810-48-3]+TX、恶霜灵(Oxadixyl)[77732-09-3]+TX、苯菌灵[17804-35-2]+TX、多菌灵[10605-21-7]+TX、咪菌威(debacarb)[62732-91-6]+TX、麦穗宁[3878-19-1]+TX、噻苯达唑[148-79-8]+TX、乙菌利(chlozolinate)[84332-86-5]+TX、菌核利(dichlozoline)[24201-58-9]+TX、异菌脲(Iprodione)[36734-19-7]+TX、甲菌利(myclozoline)[54864-61-8]+TX、腐霉利(procymidone)[32809-16-8]+TX、乙烯菌核利(vinclozoline)[50471-44-8]+TX、啶酰菌胺(boscalid)[188425-85-6]+TX、萎锈灵[5234-68-4]+TX、甲呋酰苯胺[24691-80-3]+TX、福多宁(flutolanil)[66332-96-5]+TX、氟酰胺(Flutolanil)[958647-10-4]+TX、灭锈胺[55814-41-0]+TX、氧化萎锈灵[5259-88-1]+TX、吡噻菌胺(penthiopyrad)[183675-82-3]+TX、噻呋菌胺[130000-40-7]+TX、双胍盐[108173-90-6]+TX、多果定(dodine)[2439-10-3][112-65-2](游离碱)+TX、双胍辛胺(iminoctadine)[13516-27-3]+TX、嘧菌酯[131860-33-8]+TX、醚菌胺[149961-52-4]+TX、烯肟菌酯{Proc.BCPC,Int.Congr.,Glasgow.2003,1,93}+TX、氟嘧菌酯[361377-29-9]+TX、甲基醚菌酯[143390-89-0]+TX、苯氧菌胺[133408-50-1]+TX、肟菌酯[141517-21-7]+TX、肟醚菌胺[248593-16-0]+TX、啶氧菌酯[117428-22-5]+TX、唑菌胺酯[175013-18-0]+TX、唑菌酯[862588-11-2]+TX、福美铁[14484-64-1]+TX、代森锰锌[8018-01-7]+TX、代森锰[12427-38-2]+TX、代森联[9006-42-2]+TX、甲代森锌(propineb)[12071-83-9]+TX、塞仑[137-26-8]+TX、代森锌[12122-67-7]+TX、福美锌[137-30-4]+TX、敌菌丹(captafol)[2425-06-1]+TX、克菌丹[133-06-2]+TX、苯氟磺胺[1085-98-9]+TX、唑啶草(fluoroimide)[41205-21-4]+TX、灭菌丹[133-07-3]+TX、对甲抑菌灵[731-27-1]+TX、波尔多(bordeaux)混合物[8011-63-0]+TX、氢氧化铜(copperhydroxid)[20427-59-2]+TX、氯化铜(copperoxychlorid)[1332-40-7]+TX、硫酸铜(coppersulfat)[7758-98-7]+TX、氧化铜(copperoxid)[1317-39-1]+TX、代森锰铜(mancopper)[53988-93-5]+TX、喹啉铜(oxine-copper)[10380-28-6]+TX、敌螨普(dinocap)[131-72-6]+TX、酞菌酯(硝基thal-isopropyl)[10552-74-6]+TX、克瘟散[17109-49-8]+TX、异稻瘟净(iprobenphos)[26087-47-8]+TX、稻瘟灵(isoprothiolane)[50512-35-1]+TX、氯瘟磷(phosdiphen)[36519-00-3]+TX、克菌磷(pyrazophos)[13457-18-6]+TX、甲基立枯磷(tolclofos-methyl)[57018-04-9]+TX、活化酯-S-甲基(acibenzolar-S-methyl)[135158-54-2]+TX、敌菌灵[101-05-3]+TX、苯噻菌胺[413615-35-7]+TX、灭瘟素(blasticidin)-S[2079-00-7]+TX、灭螨猛(chinomethionat)[2439-01-2]+TX、地茂散(chloroneb)[2675-77-6]+TX、百菌清[1897-45-6]+TX、环氟菌胺[180409-60-3]+TX、霜脲氰[57966-95-7]+TX、二氯萘醌(dichlone)[117-80-6]+TX、双氯氰菌胺(diclocymet)[139920-32-4]+TX、哒菌酮(diclomezine)[62865-36-5]+TX、氯硝胺(dicloran)[99-30-9]+TX、乙霉威(diethofencarb)[87130-20-9]+TX、烯酰吗啉[110488-70-5]+TX、SYP-LI90(Flumorph)[211867-47-9]+TX、二噻农(dithianon)[3347-22-6]+TX、噻唑菌胺(ethaboxam)[162650-77-3]+TX、土菌灵(etridiazole)[2593-15-9]+TX、恶唑菌酮[131807-57-3]+TX、咪唑菌酮(fenamidone)[161326-34-7]+TX、稻瘟酰胺(Fenoxanil)[115852-48-7]+TX、三苯锡(fentin)[668-34-8]+TX、嘧菌腙(ferimzone)[89269-64-7]+TX、氟啶胺(fluazinam)[79622-59-6]+TX、氟吡菌胺(fluopicolide)[239110-15-7]+TX、磺菌胺(flusulfamide)[106917-52-6]+TX、环酰菌胺[126833-17-8]+TX、乙膦酸-铝[39148-24-8]+TX、恶霉灵(hymexazol)[10004-44-1]+TX、丙森锌[140923-17-7]+TX、IKF-916(氰霜唑(Cyazofamid))[120116-88-3]+TX、春雷霉素(kasugamycin)[6980-18-3]+TX、磺菌威(methasulfocarb)[66952-49-6]+TX、苯菌酮[220899-03-6]+TX、戊菌隆(pencycuron)[66063-05-6]+TX、稻瘟酞[27355-22-2]+TX、哌碳唑[500207-04-5]+TX、多氧霉素(polyoxins)[11113-80-7]+TX、噻菌灵(probenazole)[27605-76-1]+TX、霜霉威[25606-41-1]+TX、碘喹唑酮(proquinazid)[189278-12-4]+TX、吡啶氟美芬(pydiflumetofen)[1228284-64-7]+TX、唑胺菌酯[915410-70-7]+TX、咯喹酮(pyroquilon)[57369-32-1]+TX、pyriofenone[688046-61-9]+TX、吡菌苯威[799247-52-2]+TX、啶菌恶唑[847749-37-5]+TX、喹氧灵[124495-18-7]+TX、五氯硝苯[82-68-8]+TX、硫[7704-34-9]+TX、Timorex GoldTM(来自斯托克顿集团(Stockton Group)的含有茶树油的植物提取物)+TX、tebufloquin[376645-78-2]+TX、噻酰菌胺[223580-51-6]+TX、咪唑嗪(triazoxide)[72459-58-6]+TX、tolprocarb[911499-62-2]+TX、氯啶菌酯[902760-40-1]+TX、三环唑[41814-78-2]+TX、嗪氨灵[26644-46-2]+TX、有效霉素[37248-47-8]+TX、霜霉灭(valifenalate)[283159-90-0]+TX、苯酰菌胺(zoxamide)(RH7281)[156052-68-5]+TX、双炔酰菌胺(mandipropamid)[374726-62-2]+TX、吡唑萘菌胺(isopyrazam)[881685-58-1]+TX、氰烯菌酯+TX、氟唑环菌胺(sedaxane)[874967-67-6]+TX、抗倒酯-乙基(trinexapac-ethyl)[95266-40-3]+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺(披露于WO 2007/048556中)+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3’,4’,5’-三氟-联苯基-2-基)-酰胺(披露于WO 2006/087343中)+TX、[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(环丙基羰基)氧基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-6,12-二羟基-4,6a,12b-三甲基-11-氧代-9-(3-吡啶基)-2H,11H萘并[2,1-b]吡喃并[3,4-e]吡喃-4-基]甲基-环丙甲酸酯[915972-17-7]+TX以及1,3,5-三甲基-N-(2-甲基-1-氧丙基)-N-[3-(2-甲基丙基)-4-[2,2,2-三氟-1-甲氧基-1-(三氟甲基)乙基]苯基]-1H-吡唑-4-甲酰胺[926914-55-8]+TX,
或生物活性化合物,该生物活性化合物选自由以下组成的组:N-[(5-氯-2-异丙基-苯基)甲基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-吡唑-4-甲酰胺(可以根据在WO2010/130767中所述的程序来制备)+TX、2,6-二甲基-1H,5H-[1,4]二硫杂[2,3-c:5,6-c’]二吡咯-1,3,5,7(2H,6H)-四酮(可以根据在WO 2011/138281中所述的程序来制备)+TX、6-乙基-5,7-二氧代-吡咯并[4,5][1,4]二硫杂[1,2-c]异噻唑-3-甲腈+TX、4-(2-溴-4-氟-苯基)-N-(2-氯-6-氟-苯基)-2,5-二甲基-吡唑-3-胺(可以根据在WO 2012/031061中所述的程序来制备)+TX、3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-茚满-4-基)-1-甲基-吡唑-4-甲酰胺(可以根据在WO 2012/084812中所述的程序来制备)+TX、CAS 850881-30-0+TX、3-(3,4-二氯-1,2-噻唑-5-基甲氧基)-1,2-苯并噻唑1,1-二氧化物(可以根据在WO 2007/129454中所述的程序来制备)+TX、2-[2-[(2,5-二甲基苯氧基)甲基]苯基]-2-甲氧基-N-甲基-乙酰胺+TX、3-(4,4-二氟-3,4-二氢-3,3-二甲基异喹啉-1-基)喹诺酮(可以根据在WO 2005/070917中所述的程序来制备)+TX、2-[2-氟-6-[(8-氟-2-甲基-3-喹啉基)氧基]苯基]丙-2-醇(可以根据在WO 2011/081174中所述的程序来制备)+TX、2-[2-[(7,8-二氟-2-甲基-3-喹啉基)氧基]-6-氟-苯基]丙-2-醇(可以根据在WO 2011/081174中所述的程序来制备)+TX、氟噻唑吡乙酮+TX[1003318-67-9]、叔-丁基N-[6-[[[(1-甲基四唑基-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸酯+TX、N-[2-(3,4-二氟苯基)苯基]-3-(三氟甲基)吡嗪-2-甲酰胺(可以根据在WO 2007/072999中所述的程序来制备)+TX、3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺(可以根据在WO 2014/013842中所述的程序来制备)+TX、2,2,2-三氟乙基N-[2-甲基-1-[[(4-甲基苯甲酰基)氨基]甲基]丙基]氨基甲酸酯+TX、(2RS)-2-[4-(4-氯苯氧基)-α,α,α-三氟-o-甲苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇+TX、(2RS)-2-[4-(4-氯苯氧基)-α,α,α-三氟-o-甲苯基]-3-甲基-1-(1H-1,2,4-三唑-1-基)丁-2-醇+TX、2-(二氟甲基)-N-[(3R)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-[3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、N’-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX、N’-[4-(4,5-二氯噻唑-2-基)氧基-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒(可以根据在WO 2007/031513中所述的程序来制备)+TX、[2-[3-[2-[1-[2-[3,5-双(二氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]噻唑-4-基]-4,5-二氢异噁唑-5-基]-3-氯-苯基]甲烷磺酸酯(可以根据在WO 2012/025557中所述的程序来制备)+TX、丁-3-炔基N-[6-[[(Z)-[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸酯(可以根据在WO 2010/000841中所述的程序来制备)+TX、2-[[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基]-4H-1,2,4-三唑-3-硫酮(可以根据在WO 2010/146031中所述的程序来制备)+TX、甲基N-[[5-[4-(2,4-二甲基苯基)三唑-2-基]-2-甲基-苯基]甲基]氨基甲酸酯+TX、3-氯-6-甲基-5-苯基-4-(2,4,6-三氟苯基)哒嗪(可以根据在WO 2005/121104中所述的程序来制备)+TX、2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1,2,4-三唑-1-基)丙-2-醇(可以根据在WO 2013/024082中所述的程序来制备)+TX、3-氯-4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪(可以根据在WO 2012/020774中所述的程序来制备)+TX、4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪-3-甲腈(可以根据在WO 2012/020774中所述的程序来制备)+TX、(R)-3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺(可以根据在WO 2011/162397中所述的程序来制备)+TX、3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-茚满-4-基)-1-甲基-吡唑-4-甲酰胺(可以根据在WO 2012/084812中所述的程序来制备)+TX、1-[2-[[1-(4-氯苯基)吡唑-3-基]氧基甲基]-3-甲基-苯基]-4-甲基-四唑-5-酮(可以根据在WO 2013/162072中所述的程序来制备)+TX、1-甲基-4-[3-甲基-2-[[2-甲基-4-(3,4,5-三甲基吡唑-1-基)苯氧基]甲基]苯基]四唑-5-酮(可以根据在WO 2014/051165中所述的程序来制备)+TX、(Z,2E)-5-[1-(4-氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯酰胺+TX、(4-苯氧基苯基)甲基2-氨基-6-甲基-吡啶-3-甲酸酯+TX、N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基吡唑-4-甲酰胺[1255734-28-1](可以根据在WO 2010/130767中所述的程序来制备)+TX、3-(二氟甲基)-N-[(R)-2,3-二氢-1,1,3-三甲基-1H-茚-4-基]-1-甲基吡唑-4-甲酰胺[1352994-67-2]+TX、N’-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX、N’-[4-(4,5-二氯-噻唑-2-基氧基)-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒+TX、N’-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX、N’-[4-(4,5-二氯-噻唑-2-基氧基)-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒+TX、(fenpicoxamid[517875-34-2])+TX(如WO 2003/035617中所描述的)、2-(二氟甲基)-N-(1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-(3-乙基-1,1-二甲基-茚满-4-基)吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-(1,1-二甲基-3-丙基-茚满-4-基)吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-(3-异丁基-1,1-二甲基-茚满-4-基)吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-[(3R)-1,1,3-三甲基茚满-4-基]吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-[(3R)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、以及2-(二氟甲基)-N-[(3R)-1,1-二甲基-3-丙基-茚满-4-基]吡啶-3-甲酰胺+TX,其中,这些甲酰胺化合物中的每一种都可以根据WO 2014/095675和/或WO2016/139189中所述的程序来制备。
在活性成分之后的括号中的参考,例如[3878-19-1]是指化学文摘登记号。上文描述的混合配伍物是已知的。当活性成分包括在“The Pesticide Manual[杀有害生物剂手册]”[The Pesticide Manual-A World Compendium[杀有害生物剂手册-全球概览];第13版;编辑:C.D.S.TomLin;The British Crop Protection Coimcil[英国农作物保护委员会]]中,它们在其中以上文对于特定化合物的圆括号中所给出的条目编号来描述;例如化合物“阿巴美丁”以条目编号(1)来描述。其中“[CCN]”是对于上文的特定化合物来加上的,所述的化合物包括在“Compendium of Pesticide Common Names[农药通用名概要]”中,其可以在互联网[A.Wood;Compendium of Pesticide Common Names,1995-2004]上获得;例如,化合物“乙酰虫腈”描述于互联网地址http://www.alanwood.net/pesticides/acetoprole.html中。
多数活性成分通过上文中所谓的“通用名”来表示,在不同的情形中使用相应的“ISO通用名”或其它“通用名”。若名称不是“通用名”,则所使用的名称种类以特定化合物的圆括号中所给出的名称来代替;在这种情况下,使用IUPAC名称、IUPAC/化学文摘名、“化学名称”、“惯用名”、“化合物名称”或“开发代码”,或若既不使用那些名称之一也不使用“通用名”,则使用“别名”。“CAS登记号”意指化学文摘登记号。
选自表2至17(下文)中描述的一种化合物2.01至2.28至17.01至17.28,或如表A至F(下文)中所示的化合物A-1至A-4,B-1至B-7,C-1至C-18,D-1,E-1和F-1的具有式(I)的化合物的活性成分混合物和如上所述的活性成分优选地是处于从100:1至1:6000的混合比率、尤其是从50:1至1:50、更尤其是处于从20:1至1:20的比率、甚至更尤其是从10:1至1:10、非常尤其是从5:1和1:5,特别优选的是从2:1至1:2的比率,并且从4:1至2:1的比率同样是优选的、尤其是处于1:1、或5:1、或5:2、或5:3、或5:4、或4:1、或4:2、或4:3、或3:1、或3:2、或2:1、或1:5、或2:5、或3:5、或4:5、或1:4、或2:4、或3:4、或1:3、或2:3、或1:2、或1:600、或1:300、或1:150、或1:35、或2:35、或4:35、或1:75、或2:75、或4:75、或1:6000、或1:3000、或1:1500、或1:350、或2:350、或4:350、或1:750、或2:750、或4:750的比率。那些混合比率是按重量计的。
如上所述的混合物可以被用于控制有害生物的方法中,该方法包括将含如上文所述的混合物的组合物施用于有害生物或其环境中,通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法除外。
包含选自表2至17(下文)中描述的一种化合物2.01至2.28至17.01至17.28,或如表A至F(下文)中所示的化合物A-1至A-4,B-1至B-7,C-1至C-18,D-1,E-1和F-1的具有式(I)的化合物以及一种或多种如上所述的活性成分的混合物可以例如以单一的“掺水即用”的形式施用,以组合的喷雾混合物(该混合物由这些单一活性成分组分的单独配制品构成)(如“桶混制剂”)施用,并且当以顺序的方式(即,一个在另一个适度短的时期之后,例如几小时或几天)施用时组合使用这些单独活性成分来施用。施用选自表2至17(下文)中描述的化合物2.01至2.28至17.01至17.28,或如表A至F(下文)中所示的化合物A-1至A-4,B-1至B-7,C-1至C-18,D-1,E-1和F-1的具有式(I)的化合物以及一种或多种如上所述的活性成分的顺序对于实施本发明而言并不是至关重要的。
根据本发明的组合物还可以包含其他固体或液体助剂,例如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅酮油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物(I)的用途也是本发明的主题。
本发明的另一个方面涉及具有式(I)的化合物的或优选的如本文所定义的个别化合物的、包含至少一种具有式(I)的化合物或至少一种优选的如以上定义的个别化合物的组合物的、或包含至少一种具有式(I)的化合物或至少一种优选的如以上定义的个别化合物与如上所述的其他杀真菌剂或杀昆虫剂混合的杀真菌或杀昆虫混合物的用于控制或预防植物(例如有用植物(如作物植物))、其繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料被昆虫或植物病原性微生物(优选真菌有机体)侵染的用途。
本发明的另一方面涉及控制或预防植物(例如有用植物(如作物植物))、其繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料被昆虫或植物病原性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,所述方法包括将具有式(I)的化合物或优选的如以上定义的个别化合物作为活性成分施用至所述植物、所述植物的部分或其场所、其繁殖材料、或所述非生命材料的任何部分。
控制或预防意指被植物病原性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。
控制或预防作物植物被植物病原性微生物(尤其是真菌有机体)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湿透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)的化合物也可以通过以下方式施用于种子(包衣):将种子或块茎用杀真菌剂的液体配制品浸渍,或用固体配制品对它们包衣。
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。
有利的施用比率通常是从5g至2kg的活性成分(a.i.)/公顷(ha),优选从10g至1kga.i./ha,最优选从20g至600g a.i./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。
当本发明所述的组合用于处理种子时,比率为0.001至50g具有式(I)的化合物/kg种子、优选从0.01至10g/kg种子,这一般是足够的。
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)施用包含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)、水分散性颗粒(WG)、可乳化性颗粒(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。特别地,有待以喷雾形式(如水分散性浓缩物(例如EC、SC、DC、OD、SE、EW、EO等)、可湿性粉剂及颗粒)施用的配制品可以含有表面活性剂(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、烷基芳基磺酸盐、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,所述配制品包括按重量计从0.01%至90%的活性剂、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佐剂,所述活性剂由至少具有式(I)的化合物任选地连同其他活性剂(特别是杀微生物剂或防腐剂等)一起组成。按重量计,组合物的浓缩形式通常含有在约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含有从0.01%至20%、优选从0.01%至5%的活性剂。然而商用的产品将优选地被配制为浓缩物,最终使用者将通常使用稀释的配制品。
然而优选的是将商用的产品配制为浓缩物,最终使用者将通常使用稀释的配制品。
表1(下文)披露了如对于式(T-1)所定义的根据化合物的变量n和取代基R1、R2、R3、R4、R5和R6的28种组合(化合物1.01至1.28)。式(T-1)对应于如针对本发明定义的式(I)。
表2至17(在表1之后)中的每一个使得28种具有式(T-1)的另外的单独化合物可得,其中Z是如在表2至17(式T-2至T-17)中具体定义的,这些表引用表1(其中具体定义了n、R1、R2、R3、R4、R5和R6)。
表1
表2:此表披露了具有式(T-2)的化合物2.01至2.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表3:此表披露了具有式(T-3)的化合物3.01至3.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表4:此表披露了具有式(T-4)的化合物4.01至4.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表5:此表披露了具有式(T-5)的化合物5.01至5.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表6:此表披露了具有式(T-6)的化合物6.01至6.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表7:此表披露了具有式(T-7)的化合物7.01至7.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表8:此表披露了具有式(T-8)的化合物8.01至8.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表9:此表披露了具有式(T-9)的化合物9.01至9.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表10:此表披露了具有式(T-10)的化合物10.01至10.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表11:此表披露了具有式(T-11)的化合物11.01至11.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表12:此表披露了具有式(T-12)的化合物12.01至12.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表13:此表披露了具有式(T-13)的化合物13.01至13.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表14:此表披露了具有式(T-14)的化合物14.01至14.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表15:此表披露了具有式(T-15)的化合物15.01至15.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表16:此表披露了具有式(T-16)的化合物16.01至16.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
表17:此表披露了具有式(T-17)的化合物17.01至17.28,其是具有式(I)的化合物,其中n、R1、R2、R3、R4、R5和R6具有在表1中给出的具体含义。
实例
接下来的实例用来阐明本发明。本发明的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。
具有式(I)的化合物可以具有任何数量的益处,尤其包括针对保护植物免受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(包括改善的作物耐受性)、改进的物理-化学特性、或增加的生物可降解性)。
贯穿本说明书,以摄氏度(℃)给出温度并且“mp”是指熔点。LC/MS意指液相色谱法-质谱法,并且对装置和方法(方法A、B、C、D、E和F)的描述如下:
LC/MS装置和方法A的描述是:
在来自沃特斯公司(Waters)的质谱仪(SQD、SQDII单四极杆质谱仪)上记录光谱,所述质谱仪配备有电喷雾源(极性:正离子和负离子,毛细管:3.00kV,锥孔范围(Conerange):30V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h,质量范围:100至900Da)以及来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:沃特斯UPLC HSS T3,1.8μm,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
LC/MS装置和方法B的描述是:
来自沃特斯公司的ACQUITY SQD质谱仪(单四极杆质谱仪)
离子化方法:电喷雾极性:正离子
毛细管(kV)3.00,锥孔(V)30.00,萃取器(V)3.00,源温度(℃)150,去溶剂化温度(℃)400,锥孔气体流量(L/Hr)60,去溶剂化气体流量(L/Hr)700
质量范围:100至800Da
DAD波长范围(nm):210至400
方法:用以下HPLC梯度条件的沃特斯ACQUITY UPLC
(溶剂A:水/甲醇9:1,0.1%甲酸和溶剂B:乙腈,0.1%甲酸)
柱类型:沃特斯ACQUITY UPLC HSS T3;柱长:30mm;柱内径:2.1mm;粒度:1.8微米;温度:60℃。
LC/MS装置和方法C的描述是:
在来自沃特斯公司的质谱仪(ACQUITY UPLC)(SQD,SQDII单四极杆质谱仪)上记录光谱,所述质谱仪配备有电喷雾源(极性:正离子或负离子,毛细管:3.0kV,锥孔:30V,萃取器:3.00V,源温度:150℃,去溶剂化温度:400℃,锥孔气体流量:60L/hr,去溶剂化气体流量:700L/hr,质量范围:140至800Da),DAD波长范围(nm):210至400,以及来自沃特斯公司的Acquity UPLC:溶剂脱气装置、二元泵、经加热的柱室以及二极管阵列检测器。柱:沃特斯公司的UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水/甲醇9:1,0.1%甲酸,B=乙腈+0.1%甲酸,梯度:0%-100%B,在2.5min内;流量(ml/min)0.75
LC/MS装置和方法D的描述是:
仪器:-
质谱仪:来自安捷伦科技公司(Agilent Technologies)的6410三重四极杆质谱仪
HPLC:安捷伦1200系列HPLC
优化的质谱参数:-
离子化方法:电喷雾(ESI)
极性:正和负极性转换
扫描类型:MS2扫描
毛细管(kV):4.00
碎裂电压(V):100.00
气体温度(℃):350
气体流量(L/min):11
喷雾器气体(psi):45
质量范围:110至1000Da
DAD波长范围(nm):210至400
优化的色谱参数:-
梯度条件
(溶剂A:水,0.1%甲酸和溶剂B:乙腈,0.1%甲酸)
柱类型:KINETEX EVO C18;柱长:50mm;柱内径:4.6mm;粒度:2.6μ;温度:40℃。
LC/MS装置和方法E的描述是:
仪器:-
质谱仪:来自沃特斯公司的ACQUITY SQD质谱仪
HPLC:UPLC‘H’级
优化的质谱参数:-
离子化方法:电喷雾(ESI)
极性:正和负极性转换
扫描类型:全扫描
毛细管(kV):3.00
锥孔电压(V):41.00
源温度(℃):150
去溶剂化气体流量(L/Hr):1000
去溶剂化温度(℃):500
锥孔气体流量(L/Hr):50
质量范围:110至800Da
PDA波长范围:210至400nm极性
优化的色谱参数:-
梯度条件:
溶剂A:含0.1%甲酸的水:乙腈::95:5v/v
溶剂B:含0.05%甲酸的乙腈
柱类型:沃特斯ACQUITY UPLC HSS T3 C18;柱长:30mm;柱内径:2.1mm;粒度:1.8μ;温度:40℃。
LC/MS装置和方法F的描述是:
在来自沃特斯公司的质谱仪(SQD、SQDII单四极杆质谱仪)上记录光谱,所述质谱仪配备有电喷雾源(极性:正离子和负离子,毛细管:3.00kV,锥孔范围:30V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h,质量范围:100至900Da)以及来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:沃特斯UPLC HSS T3,1.8μm,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2.7min内;流量(ml/min)0.85。
在必要时,在对映异构体意义上纯的最终化合物可以在适当时从外消旋材料经由标准物理分离技术(如反相手性色谱法)或通过立体选择性合成技术(例如通过使用手性起始材料)获得。
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合适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合适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的乳液可以通过用水稀释从这种浓缩物中获得。
通过将该活性成分与载体混合并且将混合物在合适的研磨机中研磨而获得即用型尘粉剂。此类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,并且将该混合物用水润湿。将混合物挤出并且然后在空气流中干燥。
包衣颗粒剂
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。使用此类稀释物,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雾、浇灌或浸渍进行保护。
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。使用此类稀释物,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雾、浇灌或浸渍进行保护。
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。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。
缩写清单:
AIBN=偶氮二异丁腈
DIPEA=N,N-二异丙基乙胺
EtOAc=乙酸乙酯
EtOH=乙醇
HCl=盐酸
mp=熔点
MeOH=甲醇
NaOH=氢氧化钠
NBS=N-溴代琥珀酰亚胺
RT=室温
Rt=保留时间(以分钟计)
TFAA=三氟乙酸酐
THF=四氢呋喃
制备实例
相应地可以使用上述以及下述的合成技术制备具有式(I)的化合物。
实例1:此实例阐明了1-甲基-4-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]四唑-5-酮(表B的化合物B-6)的制备
步骤1:N’-羟基-4-甲基-苯甲脒的制备
在室温下,向4-甲基苯甲腈(35g,0.29mol)在乙醇(220mL)和水(440mL)中的搅拌悬浮液中添加盐酸羟胺(41.1g,0.58mol)、碳酸钾(65.4g,0.47mol)和8-羟基喹啉(0.22g,1.5mmol)。将反应混合物在80℃下加热4小时。将混合物冷却至室温,并用2N HCl稀释至pH8。在减压下蒸发乙醇。将混合物过滤、用水洗涤并在真空下干燥,以提供标题化合物。LC/MS(方法A)保留时间=0.23分钟,151.0(M+H)。
步骤2:3-(对甲苯基)-5-(三氟甲基)-1,2,4-噁二唑的制备
在0℃下向N’-羟基-4-甲基-苯甲脒(38.7g,0.25mol)在2-甲基四氢呋喃(750mL)中的搅拌溶液中添加TFAA。将反应混合物在15℃下搅拌两小时,并且然后用水稀释。将有机层分离,依次用碳酸氢钠溶液、氯化铵溶液和水洗涤,经硫酸钠干燥,过滤并蒸发至干燥。将粗产物通过硅胶快速色谱法(750g预填充柱)用庚烷/EtOAc 99:1至90:10纯化,以提供呈澄清油状物的标题化合物,其在储存时固化。
LC/MS(方法A)保留时间=1.15分钟,未检测到质量。
1H NMR(400MHz,CDCl3)δppm:8.00(d,2H),7.32(d,2H),2.45(s,3H)。
19F NMR(400MHz、CDCl3)δppm:-65.41(s)。
步骤3a:3-[4-(溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑的制备
在氩气下,将3-(对甲苯基)-5-(三氟甲基)-1,2,4-噁二唑(56.0g,0.24mol)和NBS(45.4g,0.25mol)在四氯甲烷(480mL)中的搅拌混合物加热至70℃。添加AIBN(4.03g,24mmol),并且将反应混合物在65℃下搅拌18小时。将混合物冷却至室温并用二氯甲烷和水稀释。分离层。将有机层用碳酸氢钠溶液洗涤,经硫酸钠干燥,过滤并蒸发至干燥。将粗残余物通过硅胶快速色谱法(750g预填充柱)用环己烷/EtOAc 100:0至95:5纯化,以提供呈白色固体的标题化合物,mp:58℃-63℃。
1H NMR(400MHz,CDCl3)δppm:8.11(d,2H),7.55(d,2H),4.53(s,2H)。
19F NMR(400MHz、CDCl3)δppm:-65.32(s)。
3-[4-(二溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑被分离为呈白色固体的副产物,mp:61℃-66℃。
1H NMR(400MHz,CDCl3)δppm:8.15(d,2H),7.73(d,2H),6.68(s,1H)。
19F NMR(400MHz、CDCl3)δppm:-65.34(s)。
步骤3b:从3-[4-(二溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑制备3-[4-(溴甲
基)苯基]-5-(三氟甲基)-1,2,4-噁二唑
在5℃下,向在乙腈(95mL)、水(1.9mL)和DIPEA(6.20ml,35.7mmol)中的3-[4-(溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑和3-[4-(二溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑的搅拌的1:9比例混合物(10.2g)中添加亚磷酸二乙酯(4.7mL,35.7mmol)。将混合物在5℃-10℃下搅拌两小时,添加水和1M HCl,并且将乙腈在减压下蒸发。将白色浆料用二氯甲烷萃取三次。将合并的有机层经硫酸钠干燥,并且过滤。将溶剂在减压下除去,并且使所得粗残余物通过硅胶快速色谱法(40g预填充柱)用环己烷/EtOAc 99:1至9:1纯化,以提供3-[4-(溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑。
1H NMR(400MHz,CDCl3)δppm:8.11(d,2H),7.55(d,2H),4.53(s,2H)。
19F NMR(400MHz、CDCl3)δppm:-65.32(s)。
步骤4:1-甲基-4-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]四唑-5-
酮的制备
将3-[4-(溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑(150mg)、1,2-二氢-1-甲基-5H-四唑-5-酮(69mg)、和碳酸钾(130mg)在乙腈(4.7mL)中的溶液在微波炉中在120℃下加热30分钟。将固体通过过滤除去并且用乙酸乙酯洗涤,并且蒸发母液以便给出粗残余物,将其通过反相HPLC纯化以便提供81mg呈白色固体的标题化合物(53%),mp:104℃-106℃。
LC/MS(方法A)保留时间=1.51分钟,327(M+H)。
1H NMR(400MHz,CDCl3)δppm:8.11(d,2H),7.54(d,2H),5.18(s,2H),3.62(s,3H)。
实例2:此实例阐明了2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-3H-异噻唑1,1-二氧化物(表A的化合物A-1)的制备
向2,3-二氢异噻唑-1,1-二氧化物(100mg)在乙腈(0.617mL)中的溶液中添加碳酸钾(240mg)。将混合物在60℃下搅拌。然后,添加3-[4-(溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑(257mg,0.83935mmol,1当量)。在60℃下继续搅拌3小时。然后蒸发溶剂,并将粗残余物通过硅胶色谱法(使用环己烷/乙酸乙酯梯度)纯化,以便提供230mg呈浅黄色油状物的标题化合物(79%)。
LC/MS(方法A)保留时间=0.98分钟,346(M+H)。
1H NMR(400MHz,CDCl3)δppm:8.15(d,2H),7.60(d,2H),6.90(m,1H),6.78(m,1H),4.48(s,2H),3.91(m,2H)。
实例3:此实例阐明了6-溴-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]哒嗪-3-酮(表C的化合物C-2)的制备
将3-[4-(溴甲基)苯基]-5-(三氟甲基)-1,2,4-噁二唑(200mg)溶解在乙腈(6mL)中。向此溶液中添加碳酸钾(172mg)。然后一次性添加3-溴-1,6-二氢-6-氧代哒嗪(140mg)。将所得的悬浮液在环境温度下搅拌18小时。然后将固体通过过滤除去、用乙酸乙酯洗涤并蒸发溶剂。将粗残余物通过硅胶快速色谱法(使用环己烷/乙酸乙酯梯度作为洗脱液)纯化。因此,获得234mg呈白色固体的标题化合物(94%),mp:106.5℃-107.6℃。
LC/MS(方法A)保留时间=1.07分钟,401,403(M+H)。
1H NMR(400MHz,CDCl3)δppm:8.09(d,2H),7.57(d,2H),7.27(d,1H),6.84(d,1H),5.32(s,2H)。
实例4:此实例阐明了1-甲基-4-[2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙基]四唑-5-酮(表D的化合物D-1)的制备
步骤1:4-(2-溴乙基)-N’-羟基-苯甲脒的制备
在环境温度下,向4-(2-溴乙基)苯甲腈(2.0g)在乙醇(32mL)中的溶液中添加盐酸羟胺(1.3g),然后在0℃下逐滴添加三乙胺(6.0mL)。将反应混合物在环境温度下搅拌12小时。然后蒸发溶剂,并且将粗残余物用于下一步而无需进一步纯化。
步骤2:3-[4-(2-溴乙基)苯基]-5-(三氟甲基)-1,2,4-噁二唑的制备
将来自步骤1的粗产物溶于四氢呋喃(60mL)中,冷却至0℃,并且然后逐滴添加三氟乙酸酐(6.0g)。观察到沉淀物的形成,并且将温度升至5℃。然后在0°下添加吡啶(3.1ml)。使反应混合物加温至环境温度并搅拌18小时。然后添加水(100mL),并且将混合物用乙酸乙酯(3份300mL)萃取,合并的有机层先用1N HCl(2份50mL)洗涤并且然后用盐水(50mL)洗涤、经无水硫酸钠干燥并蒸发溶剂。将粗产物通过硅胶色谱法(用环己烷/乙酸乙酯梯度作为洗脱液)纯化。因此,获得1.75g呈无色胶状物的3-[4-(2-溴乙基)苯基]-5-(三氟甲基)-1,2,4-噁二唑(57%)。
1H NMR(400MHz,CDCl3)δppm:8.09(d,2H),7.39(d,2H),3.62(t,2H),3.26(t,2H)。
19F NMR(377MHz、CDCl3)δppm:-65.39(s)。
步骤3:1-甲基-4-[2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙基]四唑-
5-酮的制备
将来自步骤2的3-[4-(2-溴乙基)苯基]-5-(三氟甲基)-1,2,4-噁二唑(150mg)、4-甲基-1H-四唑-5-酮(56mg)溶于乙腈(10.0mL)中,然后添加碳酸钾(130mg)。将反应混合物在85℃下搅拌16小时。然后将混合物用水和乙酸乙酯萃取,将有机层用水洗涤两次、然后用盐水洗涤、经无水硫酸钠干燥,并蒸发溶剂。将残余物通过硅胶快速色谱法(使用环己烷/乙酸乙酯梯度作为洗脱液)纯化。因此,获得70mg呈白色固体的标题化合物(44%),mp:92℃-94℃。
1H NMR(400MHz,CDCl3)δppm:8.08(d,2H),7.39(d,2H),4.26(t,2H),3.62(s,3H),3.25(t,2H)。
19F NMR(377MHz、CDCl3)δppm:-65.37(s)。
表A:具有式(I)的化合物的熔点(mp)和/或LC/MS数据:
表B:具有式(I)的化合物的熔点(mp)和/或LC/MS数据:
表C:具有式(I)的化合物的熔点(mp)和/或LC/MS数据:
表D:具有式(I)的化合物的熔点(mp)和/或LC/MS数据:
表E:具有式(I)的化合物的熔点(mp)和/或LC/MS数据:
表F:具有式(I)的化合物的熔点(mp)和/或LC/MS数据:
生物学实例
在孔板中叶圆片测试的一般实例:
从生长于温室中的植物上切割不同植物物种的叶圆片或叶段。将切割的叶圆片或叶段置于多孔板(24孔规格)中的水琼脂上。在接种之前(预防性)或之后(治疗性),将叶圆片用测试溶液喷雾。将待测试的化合物制备成DMSO溶液(最大10mg/ml),将其在就要喷雾之前用0.025%Tween20稀释至适当浓度。根据对应的测试系统,在限定的条件(温度、相对湿度、光等)下孵育接种的叶圆片或叶段。取决于病害系统,接种后3至14天,进行疾病水平的单评估。然后计算相对于未处理的检验叶圆片或叶段的疾病控制百分比。
在孔板中液体培养测试的一般实例:
将真菌的菌丝体片段或分生孢子(从所述真菌的液体培养物或从低温储存物新鲜制备)直接混入营养肉汤中。将测试化合物(最大10mg/ml)的DMSO溶液通过因子50用0.025%的Tween20进行稀释,并且将10μl的这种溶液用移液管移取到微量滴定板(96孔规格)中。然后将包含该真菌孢子/菌丝体片段的营养肉汤添加到其中,从而给出测试化合物的终浓度。将测试板在24℃和96%相对湿度的黑暗中进行孵育。取决于病害系统,2至7天之后通过光度法测定真菌生长的抑制,并且计算相对于未处理的检验物而言的抗真菌活性百分比。
实例1:针对小麦隐匿柄锈菌(Puccinia recondita f.sp.tritici)的杀真菌活
性/小麦/叶圆片预防法(褐锈病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用之后1天,将这些叶圆片用真菌的孢子悬浮液进行接种。在气候室中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育经接种的叶段,并且在未处理的对照叶段中出现适当水平的疾病损害时(施用后7-9天),作为与未处理的相比的疾病控制百分比来评估化合物的活性。
当与在相同条件下显示出广泛的疾病发展的未处理的对照相比时,来自表A至D的以下化合物在200ppm下给出对小麦隐匿柄锈菌的至少80%的控制:
化合物(来自表A):A-1、A-2、A-4。
化合物(来自表B):B-1、B-3、B-4、B-5、B-6、B-7。
化合物(来自表C):C-1、C-2、C-4、C-5、C-6、C-7、C-8、C-9、C-10、C-11、C-12、C-13、C-14、C-15、C-16、C-17、C-18。
化合物(来自表D):D-1。
化合物(来自表E):
化合物(来自表F):F-1。
实例2:针对小麦隐匿柄锈菌的杀真菌活性/小麦/叶圆片治疗法(褐锈病)
将小麦叶段栽培品种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,在黑暗中储存板。在接种后1天,施用在水中稀释的配制的测试化合物。在气候室中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育叶段,并且在未处理的对照叶段中出现适当水平的疾病损害时(施用后6-8天),作为与未处理的相比的疾病控制百分比来评估化合物的活性。
当与在相同条件下显示出广泛的疾病发展的未处理的对照相比时,来自表A至D的以下化合物在200ppm下给出对小麦隐匿柄锈菌的至少80%的控制:
化合物(来自表A):A-1、A-2。
化合物(来自表B):B-1、B-3、B-4、B-5、B-6。
化合物(来自表C):C-1、C-2、C-3、C-4、C-5、C-6、C-7、C-8、C-9、C-10、C-11、C-12、C-13、C-14、C-15、C-16、C-17、C-18。
化合物(来自表D):D-1。
化合物(来自表E):
化合物(来自表F):
实例3:针对豆薯层锈菌的杀真菌活性/大豆/叶圆片预防法(亚洲大豆锈病)
将大豆叶圆片置于多孔板(24孔规格)中的水琼脂上,并且用稀释于水中的配制的测试化合物进行喷雾。施用后一天,通过在下部叶表面喷雾孢子悬浮液来接种叶圆片。在气候室中,在黑暗中在20℃和75%rh下的24-36小时的孵育期之后,用12h照明/天和75%rh将叶圆片保持在20℃。当在未处理的对照叶圆片中出现适当水平的疾病损害时(施用后12-14天),作为与未处理的相比的疾病控制百分比来评估化合物的活性。
当与在相同条件下显示出广泛的疾病发展的未处理的对照相比时,来自表A至D的以下化合物在200ppm下给出对豆薯层锈菌的至少80%的控制:
化合物(来自表A):A-1、A-2、A-3、A-4。
化合物(来自表B):B-1、B-3、B-4、B-5、B-6、B-7。
化合物(来自表C):C-1、C-2、C-4、C-5、C-6、C-7、C-8、C-9、C-10、C-11、C-12、C-13、C-14、C-15。
化合物(来自表D):D-1。
化合物(来自表E):
化合物(来自表F):
实例4:针对瓜类小丛壳(Glomerella lagenarium)(瓜类炭疽菌(Colletotrichum
lagenarium))液体培养物的杀真菌活性/黄瓜/预防法(炭疽病)
将来自低温储存的真菌分生孢子直接混入营养肉汤(PDB-马铃薯右旋糖肉汤)中。在将试验化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下孵育并且施用3-4天以后通过光度测定测量对生长的抑制。
当与在相同条件下显示出广泛的疾病发展的未处理的对照相比时,来自表A至D的以下化合物在20ppm下给出对瓜类小丛壳的至少80%的控制:
化合物(来自表A):A-1、A-2、A-3。
化合物(来自表B):B-1、B-2、B-3、B-4、B-5、B-6、B-7。
化合物(来自表C):C-1、C-2、C-4、C-5、C-6、C-7、C-8、C-9、C-10、C-11、C-12、C-13、C-14、C-15、C-16、C-17、C-18。
化合物(来自表D):D-1。
化合物(来自表E):
化合物(来自表F):F-1。
Claims (15)
1.一种具有式(I)的化合物:
其中
n是0或1或2;
R1和R2独立地选自氢、氟、氯、甲基;
R3和R4独立地选自氢或氟;
其中R1至R4中的至少两个是C-H;
R5和R6独立地表示氢或甲基;
Z表示选自Z-1、Z-2、Z-3、Z-4、Z-5或Z-6的基团,
其中:
X表示C(=O)或S(O)2;并且
(i)Z-1中的B1和B2独立地表示N或C-R7,并且Z-1中的B3表示C(R7)(R8)、O、S、NR9或C(=O);
(ii)Z-2中的B1表示C(R7)(R8)、O、S、NR9或C(=O),并且Z-2中的B2和B3独立地表示N或C-R7;
(iii)Z-3中的B1、B2、B3和B4独立地表示N或C-R7;
(iv)Z-4中的B1和B2独立地表示N或C-R7,并且Z-4中的B3和B4独立地表示C(R7)(R8)、O、S、NR9或C(=O),其前提是B3和B4中仅一个可以是O或S;
(v)Z-5中的B2和B3独立地表示N或C-R7,并且Z-5中的B1和B4独立地表示C(R7)(R8)、O、S、NR9或C(=O);并且
(vi)Z-6中的B1和B2独立地表示C(R7)(R8)、O、S、NR9或C(=O),并且Z-6中的B3和B4独立地表示N或C-R7,其前提是B1和B2中仅一个可以是O或S;并且
R7表示或R7和R8独立地表示氢、卤素、氰基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;
R9表示氢、C1-6烷基、C3-6烯基、C3-6炔基、C3-6环烷基、C1-6烷氧基、C(O)R10、C(O)OR10、C(O)N(R10)R11、S(O)2R10或S(O)2N(R10)R11,其中C1-6烷基、C3-6烯基、C3-6炔基、C3-6环烷基和C1-6烷氧基任选地被卤素或氰基取代;或R9表示苯基或被1、2或3个独立地选自卤素、C1-4烷基、C1-4卤代烷基或C1-4烷氧基的取代基取代的苯基;
R10表示氢、C1-3烷基、C3-4环烷基、C3-4环烷基C1-2烷基、C1-2烷氧基C1-4烷基,其中C1-3烷基、C3-4环烷基、C3-4环烷基C1-2烷基和C1-2烷氧基C1-4烷基任选地被卤素或氰基取代;并且
R11表示氢、氨基、氟、氯、甲基、乙基、二氟甲基、三氟甲基、甲氧基、N-甲胺或二甲胺;或者
其盐或N-氧化物。
2.根据权利要求1所述的化合物,其中,n是1。
3.根据权利要求1或权利要求2所述的化合物,其中:
R1至R4是氢;
R1是C-F并且R2至R4是氢;
R3是C-F并且R1、R2和R4是氢;或者
R1和R3是C-F并且R2和R4是氢。
4.根据权利要求1至3中任一项所述的化合物,其中,R5和R6是氢。
5.根据权利要求1至4中任一项所述的化合物,其中,X是C(=O)。
7.根据权利要求1至4中任一项所述的化合物,其中,Z是Z-2。
9.根据权利要求1至4中任一项所述的化合物,其中,Z是Z-3。
11.根据权利要求10所述的化合物,其中,Z-3任选地被1或2个独立地选自氟、氯、溴、氰基、甲基、甲氧基和三氟甲基的取代基取代。
12.一种农用化学组合物,其包含杀真菌有效量的根据权利要求1至11中任一项所述的具有式(I)的化合物。
13.根据权利要求12所述的组合物,其进一步包含至少一种另外的活性成分和/或农用化学上可接受的稀释剂或载体。
14.一种用于控制或预防有用植物被植物病原性微生物侵染的方法,其中将杀真菌有效量的根据权利要求1至11中任一项所述的具有式(I)的化合物、或包含这种化合物作为活性成分的组合物施用至所述植物、其部分或其场所。
15.根据权利要求1至11中任一项所述的具有式(I)的化合物作为杀真菌剂的用途。
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