CN112789265B - 杀微生物的化合物 - Google Patents
杀微生物的化合物 Download PDFInfo
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- CN112789265B CN112789265B CN201980064993.XA CN201980064993A CN112789265B CN 112789265 B CN112789265 B CN 112789265B CN 201980064993 A CN201980064993 A CN 201980064993A CN 112789265 B CN112789265 B CN 112789265B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 347
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- 239000000417 fungicide Substances 0.000 claims abstract description 69
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- 230000000855 fungicidal effect Effects 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 52
- 239000004480 active ingredient Substances 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
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- 238000001356 surgical procedure Methods 0.000 claims description 3
- IXTZEOKWEVPSCD-YBEGLDIGSA-N methyl (Z)-2-[5-(4-cyclopropyltriazol-2-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate Chemical compound C1(CC1)C1=NN(N=C1)C=1C=CC(=C(O\C(\C(=O)OC)=C/OC)C=1)C IXTZEOKWEVPSCD-YBEGLDIGSA-N 0.000 claims description 2
- VRMCMMDGLHFHPD-BOPFTXTBSA-N C(C)(C)C1=NN(C=C1)C=1C=CC(=C(O\C(\C(=O)OC)=C/OC)C=1)C Chemical compound C(C)(C)C1=NN(C=C1)C=1C=CC(=C(O\C(\C(=O)OC)=C/OC)C=1)C VRMCMMDGLHFHPD-BOPFTXTBSA-N 0.000 claims 2
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- DNNWUKXLLJWILD-UVTDQMKNSA-N methyl (Z)-2-[5-[3-(1,1-difluoroethyl)pyrazol-1-yl]-2-methylphenoxy]-3-methoxyprop-2-enoate Chemical compound CC(C(C=C1)=NN1C1=CC(O/C(/C(OC)=O)=C\OC)=C(C)C=C1)(F)F DNNWUKXLLJWILD-UVTDQMKNSA-N 0.000 claims 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- 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
- A01N43/64—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
Abstract
披露了具有式(I)的化合物,其中取代基是如权利要求1所定义的,所述化合物可用作杀有害生物剂,尤其可用作杀真菌剂。
Description
本发明涉及杀微生物的甲氧基丙烯酸酯衍生物,例如作为活性成分,所述甲氧基丙烯酸酯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甲氧基丙烯酸酯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,并且涉及这些甲氧基丙烯酸酯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。
EP 0 212 859和WO 01/00562描述了甲氧基丙烯酸酯衍生物用于对抗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
X是CH或N;
R1选自由以下组成的组:氢、卤素、C1-C3烷基和环丙基;
R2选自由以下组成的组:氢、卤素、甲基和甲氧基;
R3选自由以下组成的组:氢、卤素、甲基和甲氧基;
R4选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、氰基C1-C6烷基-、环丙基C1-C6烷基-、甲氧基C3-C6烯基-、环丙基C2-C6烯基-、甲氧基C3-C4炔基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、环丙基C1-C6烷氧基-、C1-C3烷氧基C1-C3烷氧基-、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、甲氧基C1-C6烷基硫烷基-、环丙基C1-C6烷基硫烷基-、C1-C3烷基硫烷基C1-C2烷基-、C3-C6环烷基、C3-C6卤代环烷基、甲氧基C3-C6环烷基-、环丙基C3-C6环烷基-、C1-C2烷基C3-C6环烷基-、-C(R6)=NOR6和-CH2C(R6)=NOR6;
R5选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、环丙基C1-C6烷基-、甲氧基C3-C6烯基-、环丙基C2-C6烯基-、甲氧基C3-C4炔基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、环丙基C1-C6烷氧基-、C1-C3烷氧基C1-C3烷氧基-、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、甲氧基C1-C6烷基硫烷基-、环丙基C1-C6烷基硫烷基-、C1-C3烷基硫烷基C1-C2烷基-、C3-C6环烷基、C3-C6卤代环烷基、甲氧基C3-C6环烷基-、环丙基C3-C6环烷基-、C1-C2烷基C3-C6环烷基-、-C(R6)=NOR6和-CH2C(R6)=NOR6;
并且其中R4和R5不都是氢;
每个R6独立地是氢或C1-C3烷基;
或其农艺学上可接受的盐;
或其N-氧化物。
已经发现了,具有式(I)的新颖化合物具有非常有利水平的生物活性来保护植物免受由真菌引起的疾病。
根据本发明的第二方面,提供了一种农用化学组合物,其包含杀真菌有效量的具有式(I)的化合物和农用化学上可接受的稀释剂或载体。这样一种农业组合物可以进一步包含至少一种另外的活性成分。
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所述植物、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,所述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,羟基意指-OH基团。
如本文使用的,术语“C1-C6烷基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,所述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剩余部分。C1-C4烷基和C1-C2烷基应相应地解释。C1-C6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)。
如本文使用的,术语“氰基C1-C6烷基”是指如上一般定义的C1-C6烷基,其被一个或多个氰基取代。
如本文使用的,术语“环丙基C1-C6烷基-”是指如上一般定义的C1-C6烷基,其被一个或多个环丙基取代。
如本文使用的,术语“C1-C6烷氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C1-C6烷基。C1-C6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-C6卤代烷基”是指如上一般定义的C1-C6烷基,其被一个或多个相同或不同的卤素原子取代。C1-C4卤代烷基应相应地解释。C1-C6卤代烷基的实例包括但不限于氯甲基、氟甲基、氟乙基、二氟甲基、三氟甲基和2,2,2-三氟乙基。
如本文使用的,术语“C1-C6卤代烷氧基”是指如上所定义的C1-C6烷氧基,其被一个或多个相同或不同的卤素原子取代。C1-C4卤代烷氧基应相应地解释。C1-C6卤代烷氧基的实例包括但不限于氟甲氧基、二氟甲氧基、氟乙氧基、三氟甲氧基和三氟乙氧基。
如本文使用的,术语“环丙基C1-C6烷氧基-”是指如上一般定义的C1-C6烷氧基,其被一个或多个环丙基取代。
如本文使用的,术语“C2-C6烯基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,所述烃链基团含有至少一个可以具有(E)-或(Z)-构型的双键,具有从二至六个碳原子,通过单键附接至分子的其余部分。C3-C6烯基应相应地解释。C2-C6烯基的实例包括但不限于丙-1-烯基、烯丙基(丙-2-烯基)和丁-1-烯基。
如本文使用的,术语“C2-C6卤代烯基”是指如上一般定义的C2-C6烯基,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“甲氧基C3-C6烯基-”是指如上一般定义的C3-C6烯基,其被一个或多个甲氧基取代。
如本文使用的,术语“环丙基C2-C6烯基-”是指如上一般定义的C2-C6烯基,其被一个或多个环丙基取代。
如本文使用的,术语“C2-C3炔基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,所述烃链基团含有至少一个三键,具有从二至三个碳原子,并且通过单键附接至分子的剩余部分。C2-C3炔基的实例包括但不限于丙-1-炔基和炔丙基(丙-2-炔基)。
如本文使用的,术语“甲氧基C3-C4炔基-”是指如上一般定义的C3-C4炔基,其被一个或多个甲氧基取代。
如本文使用的,术语“环丙基C2-C3炔基-”是指如上一般定义的C2-C3炔基,其被一个或多个环丙基取代。
如本文使用的,术语“C2-C3卤代炔基”是指如上一般定义的C2-C3炔基,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C1-C3烷氧基C1-C3烷基-”是指具有式Ra-O-Rb-的基团,其中Ra是如上一般定义的C1-C3烷基,并且Rb是如上一般定义的C1-C3亚烷基。
如本文使用的,术语“C1-C3烷氧基C1-C3烷氧基-”是指具有式Ra-O-Rb-O-的基团,其中Ra是如上一般定义的C1-C3烷基,并且Rb是如上一般定义的C1-C3烷基。
如本文使用的,术语“C1-C6烷基硫烷基”是指具有式-SRa的基团,其中Ra是如上一般定义的C1-C6烷基。
如本文使用的,术语“C1-C6卤代烷基硫烷基”是指如上所定义的C1-C6烷基硫烷基,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“甲氧基C1-C6烷基硫烷基”是指如上定义的C1-C6烷基硫烷基,其被一个或多个甲氧基取代。
如本文使用的,术语“环丙基C1-C6烷基硫烷基”是指如上定义的C1-C6烷基硫烷基,其被一个或多个环丙基取代。
如本文使用的,术语“C1-C3烷基硫烷基C1-C2烷基-”是指具有式Ra-S-Rb-的基团,其中Rb是如上一般定义的C1-C3烷基,并且Ra是如上一般定义的C1-C2亚烷基。
如本文使用的,术语“C3-C6环烷基”是指稳定的单环基团,其是饱和的或部分不饱和的并且含有3至6个碳原子。C3-C4环烷基应相应地解释。C3-C6环烷基的实例包括但不限于环丙基、环丁基、环戊基和环己基。
如本文使用的,术语“C3-C6卤代环烷基”是指如上一般定义的C3-C6环烷基,其被一个或多个相同或不同的卤素原子取代。C3-C4卤代环烷基应相应地解释。
如本文使用的,术语“甲氧基C3-C6环烷基”是指如上定义的C3-C6环烷基,其被一个或多个甲氧基取代。
如本文使用的,术语“环丙基C3-C6环烷基”是指如上定义的C3-C6环烷基,其被一个或多个环丙基取代。
如本文使用的,术语“C1-C2烷基C3-C6环烷基-”是指如上定义的C3-C6环烷基,其被如上定义的C1-C2烷基取代。
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(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)的化合物处于游离形式、处于共价水合形式或处于盐形式(例如,农艺学上可用的或农用化学上可接受的盐形式)。
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X、R1、R2、R3、R4、R5和R6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。
X是CH或N。优选地,X是CH。
在另一个实施例中,X是N。
R1选自由以下组成的组:氢、卤素、C1-C3烷基和环丙基。优选地,R1选自由以下组成的组:氢、氯、溴、甲基、乙基和环丙基。更优选地,R1选自由以下组成的组:氯、溴、甲基、乙基和环丙基。甚至更优选地,R1选自由以下组成的组:氯、溴和甲基。最优选地,R1是甲基。
R2选自由以下组成的组:氢、卤素、甲基和甲氧基。优选地,R2选自由以下组成的组:氢、氟、甲基和甲氧基。更优选地,R2选自由以下组成的组:氢、氟和甲基。甚至更优选地,R2是氢或甲基。最优选地,R2是氢。
R3选自由以下组成的组:氢、卤素、甲基和甲氧基。优选地,R3选自由以下组成的组:氢、氟、氯、甲基和甲氧基。更优选地,R3选自由以下组成的组:氢、氟和甲基。甚至更优选地,R3是氢或甲基。最优选地,R3是氢。
R4选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、氰基C1-C6烷基-、环丙基C1-C6烷基-、甲氧基C3-C6烯基-、环丙基C2-C6烯基-、甲氧基C3-C4炔基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、环丙基C1-C6烷氧基-、C1-C3烷氧基C1-C3烷氧基-、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、甲氧基C1-C6烷基硫烷基-、环丙基C1-C6烷基硫烷基-、C1-C3烷基硫烷基C1-C2烷基-、C3-C6环烷基、C3-C6卤代环烷基、甲氧基C3-C6环烷基-、环丙基C3-C6环烷基-、C1-C2烷基C3-C6环烷基-、-C(R6)=NOR6和-CH2C(R6)=NOR6。
优选地,R4选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、氰基C1-C6烷基-、环丙基C1-C6烷基-、甲氧基C3-C6烯基-、环丙基C2-C6烯基-、甲氧基C3-C4炔基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、C1-C3烷基硫烷基C1-C2烷基-、C3-C6环烷基、C3-C6卤代环烷基、C1-C2烷基C3-C6环烷基-和-C(R6)=NOR6。
更优选地,R4选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、环丙基C1-C6烷基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、C3-C6环烷基、C3-C6卤代环烷基和-C(R6)=NOR6。
甚至更优选地,R4选自由以下组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基。
甚至还更优选地,R4选自由以下组成的组:卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基。
又甚至还更优选地,R4选自由以下组成的组:氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、三氟甲基、三氟乙基、异丙氧基、正丙氧基、环丙基和环丁基。
在一个实施例中,R4选自由以下组成的组:氯、溴、碘、氰基、甲基、乙基、正丙基、异丙基、乙基丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基乙炔基、乙烯基、丙-1-烯基、1-甲基丙-1-烯基、丙-1-炔基、二氟甲基、三氟甲基、1,1-二氟乙基、1,1,2,2,2-五氟乙基、三氟-1-甲基-乙基、三氟甲基乙烯基、甲基环丙基、甲氧基、乙氧基、异丙氧基、正丙氧基、二氟甲氧基、甲氧基甲基、三氟甲基硫烷基、甲基硫烷基甲基、环丙基、环丁基、环戊基、环己基、环己烯-1-基、氟代环丙基、2,2-二氟环丙基、-C(CH3)=NOCH3、-C(CH3)=NOCH2CH3和-C(CH3)=NOH。
R5选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、环丙基C1-C6烷基-、甲氧基C3-C6烯基-、环丙基C2-C6烯基-、甲氧基C3-C4炔基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、环丙基C1-C6烷氧基-、C1-C3烷氧基C1-C3烷氧基-、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、甲氧基C1-C6烷基硫烷基-、环丙基C1-C6烷基硫烷基-、C1-C3烷基硫烷基C1-C2烷基-、C3-C6环烷基、C3-C6卤代环烷基、甲氧基C3-C6环烷基-、环丙基C3-C6环烷基-、C1-C2烷基C3-C6环烷基-、-C(R6)=NOR6和-CH2C(R6)=NOR6。
优选地,R5选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C3-C6环烷基和C3-C6卤代环烷基。
更优选地,R5选自由以下组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基。
甚至更优选地,R5选自由以下组成的组:氢、卤素、甲基、乙基、异丙基、叔丁基、乙氧基、环丙基、环戊基和三氟甲基。
甚至还更优选地,R5选自由以下组成的组:氢、卤素、甲基和三氟甲基。最优选地,R5是氢。
在一个实施例中,R5选自由以下组成的组:氢、氯、溴、碘、氰基、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、异丙烯基、乙炔基、三氟甲基、甲氧基甲基、异丙基硫烷基、环丙基、环丁基、环戊基、环己基、-C(CH3)=NOCH2CH3和-C(CH3)=NOH。
条件是R4和R5不都是氢。
每个R6独立地是氢或C1-C3烷基。优选地,每个R6是C1-C3烷基,最优选地,每个R6是甲基。
优选地,在本发明的根据式(I)的化合物中:
X是CH或N;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、环丙基C1-C6烷基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、C3-C6环烷基、C3-C6卤代环烷基和-C(R6)=NOR6;
R5选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C3-C6环烷基和C3-C6卤代环烷基;
每个R6独立地是氢或C1-C3烷基。
更优选地,在本发明的根据式(I)的化合物中:
X是CH;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、环丙基C1-C6烷基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、C3-C6环烷基、C3-C6卤代环烷基和-C(R6)=NOR6;
R5选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C3-C6环烷基和C3-C6卤代环烷基;
每个R6独立地是氢或C1-C3烷基。
甚至更优选地,在本发明的根据式(I)的化合物中:
X是CH;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基;
R5选自由以下组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基。
甚至还更优选地,在本发明的根据式(I)的化合物中,
X是CH;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、三氟甲基、三氟乙基、异丙氧基、正丙氧基、环丙基和环丁基;
R5是氢。
在一个替代性优选实施例中,在本发明的根据式(I)的化合物中:
X是CH;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、环丙基C1-C6烷基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、C3-C6环烷基、C3-C6卤代环烷基和-C(R6)=NOR6;
R5选自由以下组成的组:卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C3-C6环烷基和C3-C6卤代环烷基;
每个R6独立地是氢或C1-C3烷基。
在一个替代性更优选实施例中,在本发明的根据式(I)的化合物中:
X是CH;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基;
R5选自由以下组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基。
在一个替代性优选实施例中,在本发明的根据式(I)的化合物中:
X是N;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C3卤代炔基、环丙基C1-C6烷基-、环丙基C2-C3炔基-、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C1-C6卤代烷基硫烷基、C3-C6环烷基、C3-C6卤代环烷基和-C(R6)=NOR6;
R5选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C2-C6烯基、C2-C3炔基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基C1-C3烷基-、C1-C6烷基硫烷基、C3-C6环烷基和C3-C6卤代环烷基;
每个R6独立地是氢或C1-C3烷基。
在一个替代性更优选实施例中,在本发明的根据式(I)的化合物中:
X是N;
R1是甲基;
R2是氢;
R3是氢;
R4选自由以下组成的组:卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基;
R5选自由以下组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基和C3-C6卤代环烷基。
在一个甚至更优选的实施例中,根据式(I)的化合物选自由下表E和F中列出的化合物E-1至E-118和F-1至F-13组成的组。
在一个实施例中,根据本发明的具有式(I)的化合物可用于对抗在线粒体细胞色素b中含有突变的植物病原性真菌(例如烟草赤星病菌(Alternaria alternata)、豆薯层锈菌(Phakopsora pachyrhizi)、葡萄生单轴霉(Plasmopara viticola)、核盘菌(Sclerotinia sclerotiorum)或小麦壳针孢(Septoria tritici),也被称为禾生球腔菌(Mycosphaerella graminicola),所述突变赋予对Qo抑制剂(例如,嗜球果伞素类,例如嘧菌酯、唑菌胺酯和肟菌酯或咪唑菌酮或噁唑菌酮)的抗性。
在另一个实施例中,根据本发明的具有式(I)的化合物可用于对抗在线粒体细胞色素b中含有突变的植物病原性真菌(例如烟草赤星病菌(Alternaria alternata)、葡萄生单轴霉(Plasmopara viticola)、核盘菌(Sclerotinia sclerotiorum)或小麦壳针孢(Septoria tritici),也被称为禾生球腔菌(Mycosphaerella graminicola),所述突变赋予对Qo抑制剂(例如,嗜球果伞素类,例如嘧菌酯、唑菌胺酯和肟菌酯或咪唑菌酮或噁唑菌酮)的抗性,其中所述突变是G143A。
在另一个实施例中,根据本发明的具有式(I)的化合物可用于对抗在线粒体细胞色素b中含有突变的植物病原性真菌(例如豆薯层锈菌(Phakopsora pachyrhizi)),所述突变赋予对Qo抑制剂(例如,嗜球果伞素类,例如嘧菌酯、唑菌胺酯和肟菌酯或咪唑菌酮或噁唑菌酮)的抗性,其中所述突变是F129L。
在另一个实施例中,本发明还涉及一种控制或预防植物中植物病原性真菌侵扰的方法(例如烟草赤星病菌(Alternaria alternata)、豆薯层锈菌(Phakopsorapachyrhizi)、葡萄生单轴霉(Plasmopara viticola)、核盘菌(Sclerotiniasclerotiorum)或小麦壳针孢(Septoria tritici),也被称为禾生球腔菌(Mycosphaerellagraminicola),优选豆薯层锈菌(Phakopsora pachyrhizi)),其中所述植物病原性真菌在线粒体细胞色素b中包含突变,从而赋予对Qo抑制剂(例如,嗜球果伞素类,例如嘧菌酯、唑菌胺酯和肟菌酯或咪唑菌酮或噁唑菌酮)的抗性,所述方法包括将杀真菌有效量的具有式(I)的化合物施用至所述植物、其部分或其场所。
抗性的水平以及因此对杀真菌剂的性能的影响可以通过使用‘抗性因子(RF)’测量。抗性因子可以通过用对于‘抗性’真菌菌株提供预设水平的疾病控制(即50%)的杀真菌剂的浓度除以对于相同真菌物种的‘易感’菌株提供相同水平的疾病控制的杀真菌剂的浓度来计算(RF=抗性菌株的EC50值/敏感菌株的EC50值)。尽管没有设置规则,但可以定义三个类别:1)RF≥50=抗性菌株,2)5≤RF<50=较不敏感的菌株(灵敏度变化),和3)RF<5=敏感菌株。
为了获得抗性真菌菌株,研究者会定位其中相关抗性已经在文献中报告的宿主作物以及地理区域。然后,从这些位置/宿主作物收集被目标疾病感染的叶片样品,并送至实验室,在那里将分离出纯净的培养物。真菌培养物的抗性表型是通过以下方式确定的:进行全剂量应答生物测定,并且将生物测定结果与类似的针对相同物种的已知易感菌株的生物测定结果进行比较。可替代地,如果对于相关物种的抗性机制是已知的,则真菌菌林的抗性基因型可以通过分子技术(例如qPCR)来确定。
可以如以下方案所示制备根据本发明的具有式(I)的化合物,其中X、R1、R2、R3、R4、R5和R6如对式(I)所定义。
根据本发明的具有式(I)的化合物,其中X、R1、R2、R3、R4和R5如对式(I)所定义可以如下获得:将具有式(II)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11是卤素(优选氯、溴或碘)或拟卤素(例如-OSO2CH3、-OSO2CF3或-OSO2(CF2)3CF3)和具有式(III)的化合物,其中X、R4和R5如对具有式(I)的化合物所定义,在碱如K2CO3、钯化合物如三(二亚苄基丙酮)二钯(0)和支持性膦配体如2-二叔丁基膦基-3,4,5,6-四甲基-2',4',6'-三异丙基-1,1'-联苯在有机溶剂如甲苯中在20℃-110℃之间的温度下进行转换。此类转换描述于Angew.Chem.Int.Ed.[应用化学国际版本]2011,第8944页中,并示于方案1中。
方案1
可替代地,具有式(I)的化合物可以如下获得:由具有式(IV)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,且R12如方案2所定义,以及具有式(III)的化合物,其中X、R4和R5如对具有式(I)的化合物所定义,在惰性有机溶剂如二氯甲烷中,在碱诸如吡啶和铜盐如Cu(OAc)2存在下。这在方案2中示出。
方案2
具有式(IV)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R12如方案2所定义,可以由具有式(II)的化合物,其中R1、R2、R3和R11如上所定义获得:通过用碱如乙酸钾、乙硼烷物质R12-R12(其中R12如方案3中所定义)、钯化合物如三(二亚苄基丙酮)二钯(0)和支持性膦配体如2-二环己基膦基-2',4',6'-三异丙基-1,1'-联苯,在有机溶剂如四氢呋喃或乙醇中进行处理,任选地接着进行硼烷基团水解或酯基转移反应。这在方案3中示出。
方案3
具有式(II)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11如上所定义,可以由具有式(V)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,R11如上所定义且R13是H或C1-C4烷基获得:通过用碱如甲醇钠和甲酰化剂如甲酸甲酯处理以生成具有式(Va)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,R11如上所定义且R14是H或甲基,接着在碱如K2CO3存在下用试剂如硫酸二甲酯进行甲基化。这在方案4中示出。
方案4
具有式(V)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,R11如上所定义且R13是H或C1-C4烷基,可以由具有式(VI)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11如上所定义获得:通过在有机溶剂如N-甲基吡咯烷酮中用碱如K2CO3和具有式(VII)的烷基化剂处理。这在方案5中示出。
方案5
具有式(VI)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11如上所定义,是可商购的或通过本领域技术人员熟知并描述于March’s Advanced OrganicChemistry[马奇氏高级有机化学],Smith和March,第6版,Wiley[威利出版社],2007中的标准官能团转换容易地由可商购的化合物制备的。
可替代地,具有式(I)的化合物,其中X、R1、R2、R3、R4和R5如对式(I)所定义,可以由具有式(VIII)的化合物,其中X、R1、R2、R3、R4和R5如对具有式(I)的化合物所定义且R13是H或C1-C4烷基获得:通过用碱如甲醇钠和甲酰化剂如甲酸甲酯处理以生成具有式(IX)的化合物,其中X、R1、R2、R3、R4和R5如对具有式(I)的化合物所定义且R14是H或甲基,接着在碱如K2CO3存在下用试剂如硫酸二甲酯进行甲基化。这在方案6中示出。
方案6
具有式(VIII)的化合物,其中X、R1、R2、R3、R4和R5如对具有式(I)的化合物所定义且R13是H或C1-C4烷基,可以如下获得:由具有式(V)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,R13是H或C1-C4烷基且R11是卤素(优选氯、溴、碘)或拟卤素(例如-OSO2CH3、-OSO2CF3或-OSO2(CF2)3CF3)和具有式(III)的化合物,其中X、R4和R5如对具有式(I)的化合物所定义,在碱如K2CO3、钯化合物如三(二亚苄基丙酮)二钯(0)和支持性膦配体如2-二叔丁基膦基-3,4,5,6-四甲基-2',4',6'-三异丙基-1,1'-联苯在有机溶剂如甲苯中在20℃-110℃之间的温度下。这在方案7中示出。
方案7
具有式(III)的化合物,其中X、R4和R5如对具有式(I)的化合物所定义的制备是本领域技术人员熟知的,并且在科学文献中具有充分的先例。
可替代地,某些具有式(I)的化合物可以如下制备:由具有式(I-a)的化合物,其中X、R1、R2、R3和R5如对具有式(I)的化合物所定义且R14为卤素(优选氯、溴或碘)或拟卤素(例如,-OSO2CH3、-OSO2CF3或-OSO2(CF2)3CF3),在偶联试剂和基于过渡金属的催化剂存在下。针对偶联剂、催化剂和溶剂不存在特别的限制,只要是在普通偶联反应中使用的,如在“Cross-Coupling Reactions:A Practical Guide(Topics in Current Chemistry)[交叉偶联反应:实用指南(当代化学专题)]”,Norio Miyaura和S.L.Buchwald编辑(施普林格版本),或“Metal-Catalyzed Cross-Coupling Reactions[金属催化的交叉偶联反应]”,Armin de Meijere和Diederich编辑(WILEY-VCH版本)中所描述的那些。这示于方案8中。
方案8
此外,具有式(I)的化合物,其中R1、R2、R3、R4和R5如上所定义且X为CH,可以如下制备:由具有式(IIa)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,经由包括重氮化和还原的一锅法反应序列得到具有式(X)的肼盐,其中R1、R2和R3如对具有式(I)的化合物所定义,接着用具有式(XI)的化合物,其中Rz是氢或C1-C4烷基且R4和R5如对具有式(I)的化合物所定义进行环化。对于相关实例,参见WO 2018/104214。这示于方案9中。
方案9
可替代地,具有式(XII)的化合物可以如下制备:由具有式(XIII)的化合物经由在合适的溶剂(例如MeOH或乙醇)中在还原剂(例如氢气、氯化铵、甲酸或肼)存在下在25℃与65℃之间的温度下使用金属(例如,Pd/C、铁或雷尼镍)进行硝基还原反应。在某些情况下,当施加压力增加时,获得改善的反应性能。对于相关实例,参见:Yoshii,Y.等人,Chem.Commun.(2015),51,1070;Takeshiba,H.等人,欧洲专利申请(1997)807631。硝基还原反应后可以接着是在亚硝酸盐源(例如,NaNO2或异戊基亚硝酸盐)和铜源(例如,CuCN)存在下在可接受的溶剂系统如水性乙腈中,在合适的温度(例如0℃至100℃)下,进行自由基-亲核芳族取代反应(桑德迈尔(Sandmeyer))。此反应示于方案10中。
方案10
根据本发明的具有式(XIII)的化合物,其中X、R1、R2、R3、R4和R5如对式(I)所定义可以如下获得:将具有式(XIV)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11是卤素(优选氯、溴或碘)或拟卤素(例如-OSO2CH3、-OSO2CF3或-OSO2(CF2)3CF3)和具有式(III)的化合物,其中X、R4和R5如对具有式(I)的化合物所定义,在碱如K2CO3、金属化合物如三(二亚苄基丙酮)二钯(0)和任选的支持性膦配体如2-二叔丁基膦基-3,4,5,6-四甲基-2',4',6'-三异丙基-1,1'-联苯在有机溶剂如甲苯中在20℃-110℃之间的温度下进行转换。此类转换描述于Angew.Chem.Int.Ed.[应用化学国际版本](2011),第8944页中,并示于方案11中。
此外,具有式(XIII)的化合物可以如下获得:由具有式(XIV)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11是卤素,以及具有式(III)的化合物,其中R4和R5如对具有式(I)的化合物所定义,任选在碱如吡啶或K2CO3并且任选在铜盐如Cu(OAc)2存在下在合适的惰性有机溶剂如二氯甲烷中。这在方案11中示出。
方案11
可替代地,具有式(XII)的化合可以如下制备:由具有式(VI)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11是卤素(优选氯、溴或碘)或拟卤素(例如-OSO2CH3、-OSO2CF3或-OSO2(CF2)3CF3),以及具有式(III)的化合物,其中X、R4和R5如对具有式(I)的化合物所定义,在碱(例如,K2CO3)、铜化合物(例如CuI)和任选的共试剂(例如N,N’-二甲基-1,2-乙二胺或N,N’-二甲基-1,2-环己二胺)在合适的有机溶剂(例如,甲苯或二噁烷)存在下在20℃-150℃之间的温度下。此类转换描述于ACS Omega 2018,3,1955或WO2013083604中,并示于方案12中。
方案12
可替代地,具有式(XIIa)的化合可以如下制备:由具有式(VIa)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R11是卤素(优选氯、溴或碘)或拟卤素(例如-OSO2CH3、-OSO2CF3或-OSO2(CF2)3CF3)且R15是苯酚官能团的合适保护基团(例如甲硅烷基、醚基、苄基),以及具有式(III)的化合物,其中X、R4和R5如对具有式(I)的化合物所定义,在碱(例如,K2CO3)、铜化合物(例如CuI)和任选的共试剂(例如N,N’-二甲基-1,2-乙二胺或N,N’-二甲基-1,2-环己二胺)存在下在合适的有机溶剂(例如,甲苯或二噁烷)中在20℃-150℃之间的温度下。此类转换描述于ACS Omega 2018,3,1955-1969或WO 2013083604中,并示于方案13中。
方案13
可替代地,具有式(XVII)的化合物可以如下制备:由具有式(XV)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R13是H或C1-C4烷基且R16如方案14中所定义,在亚硝酸盐源(例如,NaNO2或异戊基亚硝酸盐)存在下在酸性条件下(例如,H2SO4或HBF4)和铜源(例如,CuSO4或CuCN)在可接受的溶剂体系中在合适的温度(例如0℃至100℃)下与化合物(XVI)进行亲核芳族取代反应。此类转换描述于CN 101580477或Journal of IowaAcademy of Science[爱荷华科学院杂志]2010,116,27-35,并示于方案14中。
方案14
可替代地,具有式(XVII)的化合物可以如下制备:由具有式(XVIII)的化合物,其中X、R1、R2、R3、R4和R5如对具有式(I)的化合物所定义且R13是H或C1-C4烷基且R16如方案15中所定义,在碱(例如Cs2CO3)、催化剂(铜源;例如CuI或CuO)存在下,任选在共试剂(1,10-邻菲咯啉)存在下,在可接受的溶剂系统(例如甲苯)中在合适的温度(例如0℃至110℃)下与化合物(XVI)进行亲核芳族取代反应。此类转换描述于WO 2007010082或WO 200837626中,并示于方案15中。
方案15
可替代地,具有式(XVIIc)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R13是H或C1-C4烷基,可以由具有式(XIX)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义获得:通过任选在有机溶剂如N-甲基吡咯烷酮中用碱(例如Cs2CO3或K2CO3)和具有式(VII)的烷基化剂处理。
具有式(XX)的化合物,其中R1、R2、R3和R13如上所定义,可以如下制备:由具有式(XVIIc)的化合物经由在合适的溶剂(例如MeOH或乙醇)中在还原剂(例如氢气、氯化铵、甲酸或肼)存在下在25℃与65℃之间的温度下使用金属(例如,Pd/C、铁或雷尼镍)进行硝基还原反应。在某些情况下,当施加压力增加时,获得改善的反应性能。
这在方案16中示出。
方案16
可替代地,具有式(XVIIc)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R13是H或C1-C4烷基,可由具有式(XXI)的化合物,其中R1、R2、R3如上所定义且R17是卤素获得:通过在碱(例如Cs2CO3)、催化剂(铜源;例如CuI)存在下在可接受的溶剂系统(例如DMSO水溶液)中在合适的温度(例如0℃至120℃)下用具有式(XVI)的化合物处理。此类转换由Xiao,Yan等人描述于J.Org.Chem.[有机化学杂志]2013,78,5804-5809中,并示于方案17中。
方案17
可替代地,具有式(XXIV)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R18是OH、OR15、OR19、NO2、NH2、R12,其中R15是苯酚官能团的合适保护基团,R19是任选取代的C1-C4烷基(例如,乙酸酯官能团),且R12是方案18中定义的乙硼烷物质,可以由具有式(XXII)的化合物,其中R1、R2、R3和R18如上所定义获得:经由包括硝基官能团的选择性还原的顺序以得到具有式(XXIII)的化合物,其中R1、R2、R3和R18如上所定义,接着进行包括重氮化和用具有式(III)的化合物,其中R4、R5和X如对式(I)的化合物所定义取代相应的重氮盐的一锅法反应序列。该序列示出于方案18中。
硝基还原反应可以在合适的溶剂(例如MeOH或乙醇)中在还原剂(例如氢气、氯化铵、甲酸或肼)存在下在25℃与65℃之间的温度下使用金属(例如,Pd/C、铁或雷尼镍)进行。在某些情况下,当施加压力增加时,获得改善的反应性能。对于相关实例,参见:J.Org.Chem.[有机化学杂志]1980,45,4992;Bull.Chem.Soc.Jpn.[日本化学学会通报]1983,56,3159。还原反应后可以接着是在酸性条件(例如AcOH或H2SO4)中的亚硝酸盐源(例如,NaNO2或异戊基亚硝酸盐)和铜源(例如,Cu(OAc)2)存在下在可接受的溶剂系统如甲醇中,在合适的温度(例如0℃至100℃)下,进行一锅法反应重氮化-取代反应。对于相关实例,参见:Chem.Eur.J.[欧洲化学杂志]2014,20,14619。该序列示出于方案18中。
方案18
R18=OH,OR15,OR19NO2,NH2,R12
R15=苯酚保护基团;R19=任选取代的C1-C4烷基
特别地,化合物(XIII),其中R1、R2、R3、R4、R5和X如对具有式(I)的化合物所定义,可以由具有式(XXIIa)的化合物,其中R1、R2、R3、R4、R5和X如对具有式(I)的化合物所定义获得:经由包括选择性还原硝基官能团的序列得到具有式(XXIIIa)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,接着进行包括重氮化和用具有式(III)的化合物,其中R4、R5和X如对具有式(I)的化合物所定义取代相应的重氮盐的一锅法反应序列,如方案19中所述。
硝基还原反应可以在合适的溶剂(例如MeOH或乙醇)中在还原剂(例如氢气、氯化铵、甲酸或肼)存在下在25℃与65℃之间的温度下使用金属(例如,Pd/C、铁或雷尼镍)进行。在某些情况下,当施加压力增加时,获得改善的反应性能。对于相关实例,参见:J.Org.Chem.[有机化学杂志]1980,45,4992;Bull.Chem.Soc.Jpn.[日本化学学会通报]1983,56,3159。还原反应后可以接着是在酸性条件(例如AcOH或H2SO4)中的亚硝酸盐源(例如,NaNO2或异戊基亚硝酸盐)和铜源(例如,Cu(OAc)2)存在下在可接受的溶剂系统如甲醇中,在合适的温度(例如0℃至100℃)下,进行一锅法反应重氮化-取代反应,以得到化合物(XIII);对于相关实例,参见:Chem.Eur.J.[欧洲化学杂志]2014,20,14619。
具有式(XXV)的化合物,其中R1、R2、R3、R4、R5和X如对具有式(I)的化合物所定义,可以经由具有式(XIII)的化合物(其中R1、R2、R3、R4、R5和X如对具有式(I)的化合物所定义)的硝基官能团的还原来获得。硝基还原反应可以在合适的溶剂(例如MeOH或乙醇)中在还原剂(例如氢气、氯化铵、甲酸或肼)存在下在25℃与65℃之间的温度下使用金属(例如,Pd/C、铁或雷尼镍)进行。在某些情况下,当施加压力增加时,获得改善的反应性能。对于相关实例,参见:J.Org.Chem.[有机化学杂志]1980,45,4992;Bull.Chem.Soc.Jpn.[日本化学学会通报]1983,56,3159。该序列示出于方案19中。
方案19
可替代地,具有式(XIII)的化合物,其中R1、R2、R3、R4、R5和X如对具有式(I)的化合物所定义,可由具有式(XXIIIa)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义获得:经由在亚硝酸盐源(例如,NaNO2或异戊基亚硝酸盐)和铜源(例如,CuBr)存在下在可接受的溶剂系统如水性乙腈中,在合适的温度(例如0℃至100℃)下,进行桑德迈尔反应,得到具有式(XXI)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R17是卤素,接着在铜源(例如CuO或CuI)作为催化剂和配体(例如肟衍生的双、三、四齿衍生的配体)存在下在可接受的溶剂体系中(例如乙腈)在合适的温度(例如,0℃至82℃)下用具有式(III)的化合物(其中R4、R5和X如对具有式(I)的化合物所定义)进行取代,如Taillefer,M.等人在Eur.J.Org.Chem.[欧洲有机化学杂志]2004,4,695-709中所报告的。该序列示出于方案20中。
方案20
可替代地,具有式(XXVII)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义,可由具有式(XXVI)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R12如方案21中所定义,在氧化剂(例如H2O2、O2)存在下在水性介质中在合适的温度(例如20℃至100℃)下获得。对于相关实例,参见:Luo,D.P.等人,Adv.Synth.Cat.[先进合成与催化]中,2019,361,961-964。此反应示于方案21中。
方案21
可替代地,具有式(XXIX)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R16如方案22中所定义,可如下制备:由具有式(XXVIII)的化合物,其中R1、R2和R3如对具有式(I)的化合物所定义且R16如方案22中所定义,经由在合适的溶剂(例如MeOH或乙醇)中在还原剂(例如氢气、氯化铵、甲酸或肼)存在下在25℃与65℃之间的温度下使用金属(例如,Pd/C、铁或雷尼镍)进行硝基还原反应。在某些情况下,当施加压力增加时,获得改善的反应性能。对于相关实例,参见:Yoshii,Y.等人,Chem.Commun.2015,51,1070;Takeshiba,H.等人,欧洲专利申请(1997)807631。还原反应后可以接着是在亚硝酸盐源(例如,NaNO2或异戊基亚硝酸盐)和铜源(例如,CuCN)存在下在可接受的溶剂系统如水性乙腈中,在合适的温度(例如0℃至100℃)下,进行桑德迈尔反应。此反应示于方案22中。
方案22
可替代地,具有式(I)的这些化合物(其中X、R1、R2、R3、R4和R5是如上所定义的)可以通过使用本领域的普通技术人员已知的标准合成技术转化另一种密切相关的具有式I的化合物(或其类似物)来获得。非详尽的实例包括氧化反应、还原反应、氢化反应、水解反应、偶联反应、芳香族亲核或亲电取代反应、亲核取代反应、烷基化反应、亲核加成反应以及卤化反应。
先前方案中所描述的官能团相互转化是本领域技术人员已知的。可以在以下中找到反应条件的广泛列表:Comprehensive Organic Functional Group Transformations[综合有机官能团转换],A.R.Katritzky,O.Meth-Cohn和C.W.Rees.编辑Pergamon Press[培格曼出版社](Elsevier Science Ltd.),Tarrytown,NY.1995;或综合有机转换:AGuide to Functional Group Preparations[官能团制备指南],Richard C编辑。Larock,Wiley-VCH,New York 1999。
如果合成产生异构体的混合物,则分离通常不一定是必需的,因为在某些情况下,各个异构体可以在后处理用于使用期间或在施用期间(例如在光、酸或碱的作用下)相互转化。此种转化也可以在使用后发生,例如在处理过的植物中在植物处理中或在要控制的有害真菌中。
如已指示的,现在已经发现,本发明的具有式(I)的新颖化合物具有非常有利水平的生物活性来保护植物免受由真菌引起的疾病。
可以在农业部门和相关领域中使用具有式(I)的化合物,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使用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在低施用率下具有优异的活性,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植物病原性微生物的侵害。
本发明进一步涉及一种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、改变或防止真菌生长的化合物。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。
还能使用具有式(I)的化合物作为处理植物繁殖材料(例如,种子,如果实、块茎或谷物)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,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)、粟、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,例如百慕达草、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、豌豆和大豆;坚果,例如杏仁、腰果、落花生、榛子、花生、山核桃、开心果和核桃;棕榈植物,例如油棕榈;观赏植物,例如花、灌木和树;其他树木,例如可可树、椰子树、橄榄树以及橡胶树;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、菠菜和番茄;和葡萄藤,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-丙酮酰-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,来自蜡样芽孢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,例如光杆状菌属物种(Photorhabdus spp.)或致病杆菌属物种(Xenorhabdus spp.),诸如发光杆菌(Photorhabdus luminescens)、嗜线虫致病杆菌(Xenorhabdus nematophilus);由动物产生的毒素,诸如蝎毒素、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(agglutinin);蛋白酶抑制剂,诸如胰蛋白酶抑制剂、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),诸如蓖麻毒素、玉蜀黍-RIP、相思豆毒素、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,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、离子通道阻断剂诸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)。
此类毒素或能够合成此类毒素的转基因植物的实例披露于例如EP-A-0 374 753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备此类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。这样的昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
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);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/>
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玉蜀黍,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蜀黍。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MON 810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(包括化合物E-1至E-118或F-1至F-13中的任一种)或包含具有式(I)的化合物的根据本发明的杀真菌组合物可用于控制或预防大豆植物上的植物病原性疾病、尤其是植物病原性真菌(如豆薯层锈菌)。
具体地,表达毒素例如杀昆虫蛋白如δ-内毒素(例如Cry1Ac(Cry1Ac Bt蛋白))的转基因大豆植物。因此,这可以包括转基因大豆植物,其包含事件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(例如参见关于IntactaRR2PROTM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)。
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US2010/0184079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US2008/0312082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。
具有式(I)的化合物(包括化合物E-1至E-118或F-1至F-13中的任一种)或包含具有式(I)的化合物的根据本发明的杀真菌组合物可用于控制或预防大豆植物上的植物病原性疾病、尤其是植物病原性真菌(如豆薯层锈菌)。具体地,在科学文献中存在已知的某些优良大豆植物品种,其中赋予对特定豆薯层锈菌的一定程度免疫力或抗性的R基因堆叠已在植物基因组中渗入,参见例如:“Fighting Asian Soybean Rust[与亚洲大豆锈病战斗]”,Langenbach C等人,Front Plant Science[植物科学前沿]7(797)2016)。
优良植物是来自优良品系的任何植物,因此优良植物是来自优良品种的代表性植物。农民或大豆育种者可商购的优良大豆品种的非限制性实例包括:AG00802、A0868、AG0902、A1923、AG2403、A2824、A3704、A4324、A5404、AG5903、AG6202、AG0934、AG1435、AG2031、AG2035、AG2433、AG2733、AG2933、AG3334、AG3832、AG4135、AG4632、AG4934、AG5831、AG6534、和AG7231(阿斯格罗种子公司(Asgrow Seeds),德梅因(Des Moines),爱荷华州,美国);BPR0144RR、BPR 4077NRR和BPR 4390NRR(生物植物研究所(Bio Plant Research),营点(Camp Point),伊利诺伊州,美国);DKB17-51和DKB37-51(迪卡白遗传公司(DeKalbGenetics),迪卡尔布(DeKalb),伊利诺伊州,美国);DP 4546RR,、和DP 7870RR(三角洲和松树陆地公司(Delta&Pine Land Company),卢博克市(Lubbock),德克萨斯州(Tex.),美国);JG 03R501、JG 32R606CADD和JG 55R503C(JGL有限公司(JGL Inc.),格林卡斯尔(Greencastle),印第安纳州,美国);NKS13-K2(先正达种子公司NK部门(NK Division ofSyngenta Seeds),黄金谷(Golden Valley),明尼苏达洲(Minnesota),美国);90M01、91M30、92M33、93M11、94M30、95M30、97B52、P008T22R2、P16T17R2、P22T69R、P25T51R、P34T07R2、P35T58R、P39T67R、P47T36R、P46T21R、和P56T03R2(先锋良种国际有限公司(Pioneer Hi-Bred International),庄士敦(Johnston),爱荷华州,美国);SG4771NRR和SG5161NRR/STS(大豆遗传学有限责任公司(Soygenetics,LLC,),拉斐特(Lafayette),印第安纳州,美国);S00-K5、S11-L2、S28-Y2、S43-B1、S53-A1、S76-L9、S78-G6、S0009-M2、S007-Y4、S04-D3、S14-A6、S20-T6、S21-M7、S26-P3、S28-N6、S30-V6、S35-C3、S36-Y6、S39-C4、S47-K5、S48-D9、S52-Y2、S58-Z4、S67-R6、S73-S8、和S78-G6(先正达种子公司,亨德森市(Henderson),肯塔基州(Ky.),美国);Richer(北极星种业有限责任公司(Northstar SeedLtd.),亚伯达省(Alberta),加拿大);14RD62(斯汀种子公司(Stine Seed Co.),爱荷华州,美国);或Armor 4744(阿莫尔种子有限责任公司(Armor Seed,LLC),阿拉斯加州,美国)。
因此,在另一个优选的实施例中,使用具有式(I)的化合物(包括化合物E-1至E-118或F-1至F-13中的任一种)或包含具有式(I)的化合物的根据本发明的杀真菌组合物控制优良大豆植物品种上的豆薯层锈菌(包括其杀真菌抗性菌株,如下所述),其中赋予对特定豆薯层锈菌的一定程度免疫力或抗性的R基因堆叠已在植物基因组中渗入。从所述用途可以预期产生许多益处,例如改进的生物活性,有利或更宽的活性谱(包括豆薯层锈菌的敏感和抗性菌株),增加的安全性,改进的作物耐受性,协同相互作用或增强特性,改进的起效或更长持续残留活性,减少有效控制植物病原菌(豆薯层锈菌)所需的化合物和组合物的施用次数和/或降低其施用率,从而实现有益的抗性-管理实践,降低的环境影响和减少的操作员暴露。
在科学文献中已经报道了豆薯层锈菌的杀真菌抗性菌株,其中观察到对一种或多种杀真菌剂具有抗性的菌株,所述一种或多种杀真菌剂来自以下杀真菌作用模式类别的至少每一种:甾醇去甲基化抑制剂(DMI)、醌外抑制剂(QoI)和琥珀酸脱氢酶抑制剂(SDHI)。参见例如:“Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors,and corresponding resistancemechanisms[豆薯层锈菌对苯醌外部抑制剂和去甲基化抑制剂的敏感性,以及相应的耐药机制].”Schmitz HK等人,Pest Manag Sci[有害生物管理学](2014)70:378-388;“Firstdetection of a SDH variant with reduced SDHI sensitivity in Phakopsorapachyrhizi[在豆薯层锈菌中首次检测到具有降低的SDHI敏感性的SDH变体]”K等人,J Plant Dis Prot[植物疾病保护杂志](2018)125:21-2;“Competitive fitness ofPhakopsora pachyrhiziisolates with mutations in the CYP51 and CYTB genes[具有CYP51和CYTB基因突变的豆薯层锈菌分离株的竞争适应性].”Klosowski AC等人,Phytopathology[植物病理学](2016)106:1278-1284;“Detection of the F129Lmutation in the cytochrome bgene in Phakopsora pachyrhizi[豆薯层锈菌细胞色素b基因中F129L突变的检测].”Klosowski AC等人,Pest Manag Sci[有害生物管理学](2016)72:1211-1215。
因此,在优选的实施例中,使用具有式(I)的化合物(包括化合物E-1至E-118或F-1至F-13中的任一种)或包含具有式(I)的化合物的根据本发明的杀真菌组合物控制豆薯层锈菌,该豆薯层锈菌对来自以下杀真菌MoA类别的任一种的一种或多种杀真菌剂具有抗性:甾醇去甲基化抑制剂(DMI)、醌外抑制剂(QoI)和琥珀酸脱氢酶抑制剂(SDHI)。
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、叶子和果实。
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,所述部分可以用于植物的繁殖,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,如喷雾、雾化、撒粉、播散、包衣或倾倒。所述组合物还可以含有另外的辅助剂,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。
合适的载体以及辅助剂,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所述浓缩物的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所述浓缩物的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石脑油、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,所述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,在所述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辅助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运载体。
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、砂藻土(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,如壬基苯酚-C.sub.18乙氧基化物;醇-氧化烯加成产物,如十三烷醇-C.sub.16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,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辅助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,例如,从“The Pesticide Manual[杀有害生物剂手册]”,第15版,英国作物保护委员会(British Crop Protection Council)2009已知的。
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作物。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辅助剂一起。
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作为活性成分(处于游离形式或处于农用化学上可用的盐形式)和上述佐剂中的至少一种。
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合农业用途的载体。农业载体在本领域是熟知的。优选地,除了包括具有式(I)的化合物,所述组合物可以包括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。
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: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-磺胺、a-[N-(3-氯-2,6-二甲苯基)-2-甲氧基乙酰胺]-y-丁内酯、4-氯-2-氰基-N,N-二甲基-5-对甲苯基咪唑-1-磺胺、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-正丙氧基-苯氧基)苯基]3-甲氧基丙烯酸甲酯、(E)-2-[2-(3-异丙氧基苯氧基)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,如三溴苯酚、四氯苯酚、3-甲基-4-氯苯酚、3,5-二甲基-4-氯苯酚、苯氧乙醇、二氯苯酚、邻苯基苯酚、间苯基苯酚、对苯基苯酚、2-苄基-4-氯苯酚、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)-1,2-二硫基-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(am丙基fos)、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、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-氨基丙酸乙酯、土菌灵、噁唑菌酮、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、苯吡克咪德、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、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、噁霉灵、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、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、环氧嘧磺隆、氟噻唑吡乙酮(oxathiapiprolin)、奥辛-铜(oxine-copper)、噁喹酸、欧伯克唑(oxpoconazole)、氧化萎锈灵、多效唑、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、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、和苯酰菌胺。
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,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、帕苯达唑以及所述类别的其他成员。另外的驱蠕虫药剂包括咪唑并噻唑类以及四氢嘧啶类,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外寄生虫药组合使用;例如,氟虫腈;拟除虫菊酯;有机磷酸酯类;昆虫生长调节剂如氯芬奴隆;蜕皮激素激动剂如虫酰肼等;新烟碱类如吡虫啉等。
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:
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、苏云金芽孢杆菌、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、克仑特罗、奥美拉唑、硫姆林、贝那普利、皮瑞普(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。
因此,具有式(I)的化合物可与一种或多种其他活性成分组合使用以提供各种杀真菌混合物。此类混合物的特定实例包括(其中“I”代表具有式(I)的化合物):选自由以下各项组成的物质组的化合物:石油+I、1,1-双(4-氯苯基)-2-乙氧基乙醇+I、2,4-二氯苯基苯磺酸酯+I、2-氟-N-甲基-N-1-萘乙酰胺+I、4-氯苯基苯基砜+I、乙酰虫腈+I、涕灭砜威+I、赛硫磷(amidithion)+I、果满磷(amidothioate)+I、胺吸磷+I、胺吸磷草酸氢盐+I、双甲脒+I、杀螨特+I、三氧化二砷+I、偶氮苯+I、偶氮磷(azothoate)+I、苯菌灵+I、苯噁磷(benoxafos)+I、苯甲酸苄酯+I、联苯吡菌胺(bixafen)+I、溴氰戊菊酯+I、溴烯杀+I、溴硫磷+I、溴螨酯+I、噻嗪酮+I、丁酮威+I、丁酮砜威+I、丁基哒螨酮(butylpyridaben)+I、石硫合剂+I、毒杀芬+I、氯灭杀威(carbanolate)+I、三硫磷+I、螨蜱胺+I、灭螨猛+I、杀螨醚;+I、杀虫脒+I、杀虫脒盐酸盐+I、杀螨醇+I、杀螨酯+I、敌螨丹+I、乙酯杀螨醇+I、伊托明(chloromebuform)+I、灭虫隆+I、丙酯杀螨醇+I、虫螨磷+I、瓜叶菊素I+I、瓜叶菊素II+I、瓜菊酯(cinerins)+I、氯生太尔+I、蝇毒磷+I、克罗米通+I、巴毒磷+I、硫杂灵杀菌剂(cufraneb)+I、果虫磷+I、DCPM+I、DDT+I、田乐磷+I、田乐磷-O+I、田乐磷-S+I、甲基内吸磷+I、内吸磷-O+I、内吸磷-O-甲基+I、内吸磷-S+I、内吸磷-S-甲基+I、内吸磷-S-甲基亚砜(demeton-S-methylsulfon)+I、苯氟磺胺+I、敌敌畏+I、dicliphos+I、除螨灵(dienochlor)+I、甲氟磷+I、消螨酚+I、消螨酚-diclexine+I、消螨普-4+I、消螨普-6+I、邻敌螨消(dinocton)+I、硝戊酯(dinopenton)+I、硝辛酯杀螨剂(dinosulfon)+I、硝丁酯+I、敌杀磷+I、二苯砜+I、双硫仑+I、DNOC+I、苯氧炔螨(dofenapyn)+I、多拉菌素+I、因毒磷+I、依立诺克丁+I、益硫磷+I、乙嘧硫磷+I、抗螨唑+I、苯丁锡+I、苯硫威+I、fenpyrad+I、唑螨酯+I、胺苯吡菌酮+I、芬螨酯+I、fentrifanil+I、氟螨噻+I、氟环脲+I、联氟螨+I、氟杀螨+I、FMC 1137+I、伐虫脒+I、伐虫脒盐酸盐+I、藻螨威(formparanate)+I、γ-HCH+I、果绿啶+I、苄螨醚+I、环丙烷甲酸十六烷基酯+I、水胺硫磷+I、茉酮菊素I+I、茉酮菊素II+I、碘硫磷+I、林丹+I、特螨腈(malonoben)+I、灭蚜磷+I、地胺磷+I、甲硫芬+I、虫螨畏+I、甲基溴+I、速灭威+I、兹克威+I、米尔贝肟+I、丙胺氟磷+I、久效磷+I、茂硫磷+I、莫昔克丁+I、二溴磷+I、4-氯-2-(2-氯-2-甲基-丙基)-5-[(6-碘-3-吡啶基)甲氧基]哒嗪-3-酮+I、氟蚁灵+I、华光霉素+I、戊氰威+I、戊氰威1:1氯化锌复合物+I、氧乐果+I、异亚砜磷+I、砜拌磷+I、pp'-DDT+I、对硫磷+I、氯菊酯+I、芬硫磷+I、伏杀硫磷+I、硫环磷+I、磷胺+I、多氯萜烯(polychloroterpenes)+I、浏阳霉素(polynactins)+I、丙氯诺+I、蜱虱威+I、残杀威+I、乙噻唑磷+I、发硫磷+I、除虫菊素I+I、除虫菊素II+I、除虫菊素+I、哒嗪硫磷+I、嘧啶磷+I、喹硫磷+I、喹硫磷+I、R-1492+I、甘氨硫磷+I、鱼藤酮+I、八甲磷+I、克线丹(sebufos)+I、赛拉菌素+I、苏硫磷+I、SSI-121+I、舒非仑+I、氟虫胺+I、治螟磷+I、硫+I、氟螨嗪+I、氟胺氰菊酯+I、TEPP+I、叔丁威(terbam)+I、三氯杀螨砜+I、杀螨硫醚+I、thiafenox+I、抗虫威+I、久效威+I、甲基乙拌磷+I、克杀螨+I、苏云金素+I、威菌磷+I、苯螨噻+I、三唑磷+I、唑呀威(triazuron)+I、三氯丙氧磷(trifenofos)+I、三活菌素+I、蚜灭磷+I、氟吡唑虫+I、苯赛清(bethoxazin)+I、二辛酸铜+I、硫酸铜+I、环丙特丁嗪(cybutryne)+I、二氯萘醌+I、双氯酚+I、茵多酸+I、三苯锡+I、熟石灰+I、代森钠+I、灭藻醌+I、醌萍胺(quinonamid)+I、西玛津+I、三苯基乙酸锡+I、三苯基氢氧化锡+I、育畜磷+I、哌嗪+I、硫菌灵+I、氯醛糖+I、倍硫磷+I、吡啶-4-胺+I、马钱子碱+I、1-羟基-1H-吡啶-2-硫酮+I、4-(喹喔啉-2-基氨基)苯磺酰胺+I、8-羟基喹啉硫酸盐+I、溴硝丙二醇+I、氢氧化铜+I、愈创木酚+I、双吡硫翁+I、多地辛+I、敌磺钠+I、甲醛+I、汞加芬+I、春雷霉素+I、春雷霉素盐酸盐水合物+I、双(二甲基二硫代氨基甲酸酯)镍+I、三氯甲基吡啶+I、辛噻酮+I、喹菌酮+I、土霉素+I、羟基喹啉硫酸钾+I、烯丙异噻唑+I、链霉素+I、链霉素倍半硫酸盐+I、叶枯酞+I、硫柳汞+I、棉褐带卷蛾颗粒体病毒(Adoxophyes orana GV)+I、放射形土壤杆菌(Agrobacterium radiobacter)+I、钝绥螨属物种(Amblyseius spp.)+I、芹菜夜蛾核多角体病毒(Anagrapha falcifera NPV)+I、Anagrus atomus+I、短距蚜小蜂(Aphelinus abdominalis)+I、棉蚜寄生蜂(Aphidius colemani)+I、食蚜瘿蚊(Aphidoletes aphidimyza)+I、苜蓿银纹夜蛾核多角体病毒(Autographa californicaNPV)+I、球形芽孢杆菌(Bacillus sphaericus Neide)+I、布氏白僵菌(Beauveriabrongniartii)+I、草蜻蛉(Chrysoperla carnea)+I、孟氏隐唇瓢虫(Cryptolaemusmontrouzieri)+I、苹果蠹蛾颗粒体病毒(Cydia pomonella GV)+I、西伯利亚离颚茧蜂(Dacnusa sibirica)+I、豌豆潜叶蝇姬小蜂(Diglyphus isaea)+I、丽蚜小蜂(Encarsiaformosa)+I、桨角蚜小蜂(Eretmocerus eremicus)+I、嗜菌异小杆线虫(Heterorhabditisbacteriophora)和H.megidis+I、会聚长足瓢虫(Hippodamia convergens)+I、橘粉介壳虫寄生蜂(Leptomastix dactylopii)+I、盲蝽(Macrolophus caliginosus)+I、甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)+I、Metaphycus helvolus+I、黄绿绿僵菌(Metarhizium anisopliae var.acridum)+I、金龟子绿僵菌小孢变种(Metarhiziumanisopliae var.anisopliae)+I、松黄叶蜂核型多角体病毒(Neodiprion sertifer NPV)和红头松树叶蜂核多角体病毒(N.lecontei NPV)+I、小花蝽属物种(Orius spp.)+I、玫烟色拟青霉(Paecilomyces fumosoroseus)+I、智利捕植螨(Phytoseiulus persimilis)+I、毛蚊线虫(Steinernema bibionis)+I、小卷蛾斯氏线虫(Steinernema carpocapsae)+I、夜蛾斯氏线虫(Steinernema feltiae)+I、格氏斯氏线虫(Steinernema glaseri)+I、Steinernema riobrave+I、Steinernema riobravis+I、蝼蛄斯氏线虫(Steinernemascapterisci)+I、斯氏线虫属物种(Steinernema spp.)+I、赤眼蜂属物种(Trichogrammaspp.)+I、西方盲走螨(Typhlodromus occidentalis)+I、蜡蚧轮枝菌(Verticilliumlecanii)+I、唑磷嗪+I、双(氮丙啶)甲氨基膦硫化物(bisazir)+I、白消安+I、迪麦替夫(dimatif)+I、六甲蜜胺+I、六甲基磷酰三胺+I、不育胺+I、甲硫涕巴+I、甲基不育特+I、不孕啶(morzid)+I、氟幼脲+I、三吖啶基氧化磷+I、硫代六甲磷(thiohempa)+I、唾替派+I、曲他胺+I、乌瑞替派+I、(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇+I、(E)-十三碳-4-烯-1-基乙酸酯+I、(E)-6-甲基庚-2-烯-4-醇+I、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯+I、(Z)-十二碳-7-烯-1-基乙酸酯+I、(Z)-十六碳-11-烯醛+I、(Z)-十六碳-11-烯-1-基乙酸酯+I、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯+I、(Z)-二十碳-13-烯-10-酮+I、(Z)-十四碳-7-烯-1-醛+I、(Z)-十四碳-9-烯-1-醇+I、(Z)-十四碳-9-烯-1-基乙酸酯+I、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯+I、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯+I、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯+I、14-甲基十八-1-烯+I、4-甲基壬-5-醇与4-甲基壬-5-酮+I、α-多纹素(alpha-multistriatin)+I、西松大小蠹素(brevicomin)+I、十二碳二烯醇(codlelure)+I、十二碳二烯醇(codlemone)+I、诱蝇酮+I、雌舞毒蛾引诱剂(disparlure)+I、十二碳-8-烯-1基乙酸酯+I、十二碳-9-烯-1-基乙酸酯+I、十二碳-8+I、10-二烯-1-基乙酸酯+I、dominicalure+I、4-甲基辛酸乙酯+I、丁香酚+I、南部松小蠹诱剂(frontalin)+I、诱杀烯混剂(grandlure)+I、诱杀烯混剂I+I、诱杀烯混剂II+I、诱杀烯混剂III+I、诱杀烯混剂IV+I、己诱剂(hexalure)+I、小蠹二烯醇(ipsdienol)+I、小蠹烯醇(ipsenol)+I、日本丽金龟引诱剂(japonilure)+I、里尼汀(lineatin)+I、litlure+I、粉纹夜蛾性诱剂(looplure)+I、诱杀酯(medlure)+I、蒙托么克酸(megatomoic acid)+I、甲基丁香酚+I、诱虫烯(muscalure)+I、十八-2,13-二烯-1-基乙酸酯+I、十八-3,13-二烯-1-基乙酸酯+I、orfralure+I、椰蛀犀金龟聚集信息素(oryctalure)+I、ostramone+I、诱虫环+I、索地丁(sordidin)+I、食菌甲诱醇(sulcatol)+I、十四-11-烯-1-基乙酸酯+I、诱蝇羧酯+I、诱蝇羧酯A+I、诱蝇羧酯B1+I、诱蝇羧酯B2+I、诱蝇羧酯C+I、创科尔(trunc-call)+I、2-(辛基硫代)乙醇+I、避蚊酮+I、丁氧基(聚丙二醇)+I、己二酸二丁酯+I、邻苯二甲酸二丁酯+I、琥珀酸二丁酯+I、避蚊胺+I、驱蚊灵+I、避蚊酯+I、乙基己二醇+I、己酰胺(hexamide)+I、甲喹丁(methoquin-butyl)+I、甲基新癸酰胺(methylneodecanamide)+I、草氨酸盐(oxamate)+I、埃卡瑞丁+I、1-二氯-1-硝基乙烷+I、1,1-二氯-2,2-双(4-乙基苯基)乙烷+I、1,2-二氯丙烷与1,3-二氯丙烯+I、1-溴-2-氯乙烷+I、2,2,2-三氯-1-(3,4-二氯苯基)乙酸乙酯+I、2-乙基亚磺酰基乙基甲基磷酸2,2-二氯乙烯基酯+I、2-(1,3-二硫戊环-2-基)苯基二甲基氨基甲酸酯+I、2-(2-丁氧基乙氧基)乙基硫氰酸酯+I、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯、2-(4-氯-3,5-二甲基苯氧基)乙醇+I、2-氯乙烯基二乙基磷酸酯+I、2-咪唑烷酮+I、2-异戊酰茚满-1,3-二酮+I、2-甲基(丙-1-炔基)氨基苯基甲基氨基甲酸酯+I、2-硫氰乙基月桂酸酯+I、3-溴-1-氯丙-1-烯+I、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯+I、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基甲基氨基甲酸酯+I、5,5-二甲基-3-氧代环己基-1-烯基二甲基氨基甲酸酯+I、阿维菌素+I、丙烯腈+I、艾氏剂+I、阿洛氨菌素+I、除害威+I、蜕皮激素+I、磷化铝+I、灭害威+I、新烟碱+I、乙基杀扑磷+I、甲基吡噁磷+I、苏云金芽孢杆菌δ内毒素+I、六氟硅酸钡+I、多硫化钡+I、熏虫菊酯(barthrin)+I、拜耳22/190+I、拜耳22408+I、高效氟氯氰菊酯+I、高效氯氰菊酯+I、苄呋烯菊酯(bioethanomethrin)+I、生物氯菊酯(biopermethrin)+I、双(2-氯乙基)醚+I、硼砂+I、溴苯烯磷+I、溴-DDT+I、合杀威+I、畜虫威+I、特嘧硫磷(butathiofos)+I、丁酯膦butonate+I、砷酸钙+I、氰化钙+I、二硫化碳+I、四氯化碳+I、杀螟丹盐酸盐+I、藜芦碱+I、冰片丹+I、氯丹+I、开蓬+I、氯仿+I、氯化苦+I、氯腈肟磷+I、氯吡唑磷(chlorprazophos)+I、顺式苄呋菊酯(cis-resmethrin)+I、顺式苄呋菊酯(cismethrin)+I、三氟氯氰菊酯+I、巴黎绿+I、砷酸铜+I、油酸铜+I、畜虫磷+I、冰晶石+I、CS 708+I、苯腈膦+I、杀螟睛+I、环虫菊酯+I、赛灭磷+I、右旋胺菊酯+I、DAEP+I、棉隆+I、一甲呋喃丹(decarbofuran)+I、除线特+I、异氯磷+I、除线磷+I、dicresyl+I、环虫腈+I、狄氏剂+I、5-甲基吡唑-3-基磷酸二乙酯+I、dilor+I、四氟甲醚菊酯+I、地麦威+I、苄菊酯+I、甲基毒虫畏+I、敌蝇威+I、丙硝酚(dinoprop)+I、戊硝酚+I、地乐酚+I、苯虫醚+I、蔬果磷+I、噻喃磷(dithicrofos)+I、DSP+I、脱皮甾酮+I、EI 1642+I、EMPC+I、EPBP+I、牛津郡丙硫磷(etaphos)+I、乙硫苯威+I、甲酸乙酯+I、二溴化乙烯+I、二氯化乙烯+I、环氧乙烷+I、EXD+I、皮蝇磷+I、双乙威+I、杀螟硫磷+I、氧嘧酰胺(fenoxacrim)+I、吡氯氰菊酯+I、丰索磷+I、乙基倍硫磷(fenthion-ethyl)+I、氟氯双苯隆(flucofuron)+I、丁苯硫磷+I、磷吡酯+I、丁环硫磷+I、呋线威+I、抗虫菊+I、双胍辛盐+I、双胍辛乙酸盐+I、四硫代碳酸钠+I、苄螨醚+I、HCH+I、HEOD+I、七氯+I、速杀硫磷+I、HHDN+I、氰化氢+I、喹啉威+I、IPSP+I、氯唑磷+I、碳氯灵+I、异艾氏剂+I、异柳磷+I、移栽灵+I、稻瘟灵+I、噁唑磷+I、保幼激素I+I、保幼激素II+I、保幼激素III+I、克来范+I、烯虫炔酯+I、砷酸铅+I、溴苯膦+I、啶虫磷+I、噻唑磷(lythidathion)+I、甲基氨基甲酸间丙苯基酯+I、磷化镁+I、叠氮磷+I、四甲磷+I、灭蚜硫磷+I、氯化亚汞+I、甲亚砜磷+I、威百亩(metam)+I、威百亩-钾+I、威百亩-钠+I、甲烷磺酰氟+I、丁烯胺磷+I、烯虫酯+I、甲醚菊酯+I、甲氧滴滴涕+I、异硫氰酸甲酯+I、甲基氯仿+I、二氯甲烷+I、噁虫酮+I、灭蚁灵+I、萘肽磷+I、萘+I、NC-170+I、烟碱+I、硫酸烟碱+I、硝虫噻嗪+I、原烟碱+I、O-5-二氯-4-碘苯基O-乙基乙基硫代磷酸酯+I、O,O-二乙基O-4-甲基-2-氧代-2H-色满-7-基硫代磷酸酯+I、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代磷酸酯+I、O,O,O',O'-四丙基二硫代焦磷酸酯+I、油酸+I、对二氯苯+I、甲基对硫磷+I、五氯苯酚+I、月桂酸五氯苯酯+I、PH 60-38+I、芬硫磷+I、对氯硫磷+I、磷化氢+I、甲基辛硫磷+I、甲胺嘧磷+I、多氯环戊二烯异构体+I、亚砷酸钾+I、硫氰化钾+I、早熟素I+I、早熟素II+I、早熟素III+I、酰胺嘧啶磷+I、丙氟菊酯(profluthrin)+I、猛杀威+I、丙硫磷+I、吡菌磷+I、反灭虫菊+I、quassia+I、甲基喹硫磷+I、畜宁磷+I、雷复沙奈+I、苄呋菊酯+I、鱼藤酮+I、噻恩菊酯+I、鱼尼汀+I、利阿诺定+I、赛藜芦)+I、八甲磷+I、克线丹(sebufos)+I、SI-0009+I、蛾蝇腈+I、亚砷酸钠+I、氰化钠+I、氟化钠+I、六氟硅酸钠+I、五氯酚酸钠+I、硒酸钠+I、硫氰酸钠+I、sulcofuron+I、sulcofuron-钠+I、硫酰氟+I、硫丙磷+I、焦油+I、噻螨威+I、TDE+I、丁基嘧啶磷+I、双硫磷+I、环戊烯丙菊酯+I、四氯乙烷+I、噻氯磷+I、杀虫环+I、杀虫环草酸盐+I、虫线磷+I、thiosultap+I、杀虫双+I、四溴菊酯+I、反氯菊酯+I、唑蚜威+I、乐乃松-3(trichlormetaphos-3)+I、毒壤膦+I、混杀威+I、三氟甲氧威+I、氯啶菌酯+I、烯虫硫酯+I、藜芦定+I、藜芦碱+I、XMC+I、zetamethrin+I、磷化锌+I、唑虫磷(zolaprofos)+I、和氯氟醚菊酯+I、四氟醚菊酯+I、双(三丁基锡)氧化物+I、溴乙酰胺+I、磷酸铁+I、灭绦灵-醇胺+I、三丁基氧化锡+I、丁吡吗啉+I、蜗螺杀(trifenmorph)+I、1,2-二溴-3-氯丙烷+I、1,3-二氯丙烯+I、3,4-二氯四氢噻吩1,1-二氧化物+I、3-(4-氯苯基)-5-甲基罗丹宁+I、5-甲基-6-硫酮基-1,3,5-噻二嗪基-3-基乙酸+I、6-异戊烯基氨基嘌呤+I、benclothiaz+I、细胞分裂素+I、DCIP+I、糠醛+I、isamidofos+I、激动素+I、疣孢漆斑菌组合物+I、四氯噻吩+I、二甲酚+I、玉米素+I、乙基黄原酸钾+I、活化酯+I、活化酯-S-甲基+I、大虎杖提取物+I、α-氯乙醇+I、antu+I、碳酸钡+I、双鼠脲+I、溴鼠隆+I、溴敌隆+I、溴鼠胺+I、氯鼠酮+I、胆钙化醇+I、氯灭鼠灵+I、克鼠灵+I、杀鼠醚+I、鼠立死+I、鼠得克+I、噻鼠灵+I、敌鼠+I、麦角钙化醇+I、氟鼠酮+I、氟乙酰胺+I、氟鼠啶+I、氟鼠啶盐酸盐+I、鼠特灵+I、毒鼠磷+I、磷+I、鼠完+I、灭鼠优+I、红海葱+I、氟乙酸钠+I、硫酸铊+I、杀鼠灵+I、2-(2-丁氧基乙氧基)乙基胡椒基酯+I、5-(1,3-苯并二噁唑-5-基)-3-己基环己-2-烯酮+I、法尼醇与橙花叔醇+I、增效炔醚(verbutin)+I、MGK 264+I、增效醚+I、增效醛+I、丙基异构体+I、S421+I、增效散+I、芝麻林素(sesasmolin)+I、增效砜+I、蒽醌+I、环烷酸铜+I、氧氯化铜+I、二环戊二烯+I、福美双+I、环烷酸锌+I、福美锌+I、衣马宁(imanin)+I、三氮唑核苷+I、氧化汞+I、甲基硫菌灵+I、氧环唑+I、联苯三唑醇+I、糠菌唑+I、环丙唑醇+I、苯醚甲环唑+I、烯唑醇+I、氟环唑+I、腈苯唑+I、氟喹唑+I、氟硅唑+I、粉唑醇+I、呋吡菌胺+I、己唑醇+I、抑霉唑+I、亚胺唑+I、种菌唑+I、叶菌唑+I、腈菌唑+I、多效唑(paclobutrazole)+I、稻瘟酯+I、戊菌唑+I、丙硫菌唑+I、啶斑肟+I、咪鲜胺+I、丙环唑+I、氯啶菌酯+I、硅氟唑+I、戊唑醇+I、四氟醚唑+I、三唑酮+I、三唑醇+I、氟菌唑+I、灭菌唑+I、嘧啶醇+I、氯苯嘧啶醇+I、氟苯嘧啶醇+I、乙嘧酚磺酸酯+I、二甲嘧酚+I、乙嘧酚+I、十二环吗啉+I、苯锈啶+I、丁苯吗啉+I、螺环菌胺+I、十三吗啉+I、嘧菌环胺+I、嘧菌胺+I、嘧霉胺+I、拌种咯+I、咯菌腈+I、苯霜灵+I、呋霜灵+I、甲霜灵+I、R-甲霜灵+I、呋酰胺+I、噁霜灵+I、多菌灵+I、咪菌威+I、麦穗宁+I、噻菌灵+I、乙菌利+I、菌核利+I、甲菌利(myclozoline)+I、腐霉利(procymidone)+I、vinclozoline+I、啶酰菌胺+I、萎锈灵+I、甲呋酰胺+I、氟酰胺+I、灭锈胺+I、氧化萎锈灵+I、吡噻菌胺+I、噻氟菌胺+I、多果定+I、双胍辛胺+I、嘧菌酯+I、醚菌胺+I、烯肟菌酯+I、烯肟菌胺+I、氟菌螨酯+I、氟嘧菌酯+I、醚菌酯+I、苯氧菌胺+I、肟菌酯+I、肟醚菌胺+I、啶氧菌酯+I、吡唑醚菌酯+I、唑胺菌酯+I、唑菌酯+I、福美铁+I、代森锰锌+I、代森锰+I、代森联+I、丙森锌+I、代森锌+I、敌菌丹+I、克菌丹+I、氟氯菌核利+I、灭菌丹+I、甲苯磺菌胺+I、波尔多液+I、氧化铜+I、代森锰铜+I、喹啉铜+I、酞菌酯+I、敌瘟磷+I、iprobenphos+I、氯瘟磷+I、甲基立枯磷+I、敌菌灵+I、苯噻菌胺酯+I、灰瘟素+I、氯苯甲醚+I、百菌清+I、环氟菌胺+I、霜脲氰+I、双氯氰菌胺+I、哒菌酮+I、氯硝胺+I、乙霉威+I、烯酰吗啉+I、氟吗啉+I、二氰蒽醌+I、噻唑菌胺+I、土菌灵+I、噁唑菌酮+I、咪唑菌酮+I、稻瘟酰胺+I、嘧菌腙+I、氟啶胺+I、氟吡菌胺+I、磺菌胺+I、氟苯吡菌胺+I、环酰菌胺(fenhexamid)+I、三乙膦酸铝+I、噁霉灵+I、缬霉威+I、氰霜唑+I、磺菌威+I、苯菌酮+I、戊菌隆+I、四氯苯酞+I、多抗霉素+I、霜霉威+I、pyribencarb+I、丙氧喹啉+I、咯喹酮+I、甲氧苯唳菌(pyriofenone)+I、喹氧灵+I、五氯硝基苯+I、噻酰菌胺(tiadinil)+I、咪唑嗪+I、三环唑+I、嗪氨灵+I、井冈霉素+I、霜霉灭+I、苯酰菌胺+I、双炔酰菌胺+I、吡唑萘菌胺+I、氟唑环菌胺+I、苯并烯氟菌唑+I、氟唑菌酰羟胺+I、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+I、isoflucypram+I、异噻菌胺+I、dipymetitrone+I、6-乙基-5,7-二氧代-吡咯并[4,5][1,4]二噻英并[1,2-c]异噻唑-3-甲腈+I、2-(二氟甲基)-N-[3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+I、4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪-3-甲腈+I、(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+I、4-(2-溴-4-氟-苯基)-N-(2-氯-6-氟-苯基)-2,5-二甲基-吡唑-3-胺+I、4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺+I、氟茚唑菌胺(fluindapyr)+I、甲香菌酯(coumethoxystrobin)+I、氯苯醚酰胺+I、dichlobentiazox+I、mandestrobin+I、3-(4,4-二氟-3,4-二氢-3,3-二甲基异喹啉-1-基)喹诺酮+I、2-[2-氟-6-[(8-氟-2-甲基-3-喹啉基)氧基]苯基]丙-2-醇+I、氟噻唑吡乙酮(oxathiapiprolin)+I、N-[6-[[[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸叔丁酯+I、pyraziflumid+I、inpyrfluxam+I、trolprocarb+I、氯氟醚菌唑(mefentrifluconazole)+I、ipfentrifluconazole+I、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+I、N'-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+I、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+I、[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]甲基磺酸酯+I、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]氨基甲酸丁-3-炔基酯+I、N-[[5-[4-(2,4-二甲基苯基)三唑-2-基]-2-甲基-苯基]甲基]氨基甲酸甲酯+I、3-氯-6-甲基-5-苯基-4-(2,4,6-三氟苯基)哒嗪+I、pyridachlometyl+I、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+I、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+I、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+I、aminopyrifen+I、唑嘧菌胺+I、吲唑磺菌胺(amisulbrom)+I、氟唑菌苯胺+I、(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+I、florylpicoxamid+I、fenpicoxamid+I、tebufloquin+I、ipflufenoquin+I、quinofumelin+I、噻吩酰菌酮(isofetamid)+I、N-[2-[2,4-di氯-苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+I、N-[2-[2-氯-4-(三氟甲基)苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+I、苯噻菌酯(benzothiostrobin)+I、氰烯菌酯+I、5-氨基-1,3,4-噻二唑-2-硫醇锌盐(2:1)+I,氟吡菌酰胺+I、氟噻唑菌腈(flutianil)+I、氟醚菌酰胺+I、pyrapropoyne+I、picarbutrazox+I、2-(二氟甲基)-N-(3-乙基-1,1-二甲基-茚满-4-基)吡啶-3-甲酰胺+I、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+I、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+I、metyltetraprole+I、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+I、α-(1,1-二甲基乙基)-α-[4'-(三氟甲氧基)[1,1'-联苯基]-4-基]-5-吡啶甲醇+I、fluoxapiprolin+I,烯肟菌酯+I、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+I、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫烷基-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+I、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-thioxo-4H-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+I、抗倒酯+I、丁香菌酯+I、中生菌素+I、噻菌铜+I、噻唑锌+I、amectotractin+I、异菌脲+I。
(N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙烷甲酰胺+I、N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+I、N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+I、1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+I、1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+I、3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+I、N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+I、4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+I、5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+I、1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡唑-4-甲酸乙酯+I、N,N-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-1,2,4-三唑-3-胺+I)。此段落中的化合物可以由WO 2017/055473、WO 2017/055469、WO 2017/093348和WO 2017/118689中描述的方法制备。
2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+I(此化合物可以由WO 2017/029179中描述的方法制备)。
2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+I(此化合物可以由WO 2017/029179中描述的方法制备)。
3-[2-(1-氯环丙基)-3-(2-氟苯基)-2-羟基-丙基]咪唑-4-甲腈+I(此化合物可以由WO 2016/156290中描述的方法制备)。
3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-甲腈+I(此化合物可以由WO 2016/156290中描述的方法制备)。
2-氨基-6-甲基吡啶-3-甲酸(4-苯氧基苯基)甲酯+I(此化合物可以由WO 2014/006945中描述的方法制备)。
2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']联吡咯-1,3,5,7(2H,6H)-四酮+I(此化合物可以由WO 2011/138281中描述的方法制备)。
N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]硫代苯甲酰胺+I。
N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+I。
(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯酰胺+I(此化合物可以由WO 2018/153707中描述的方法制备)。
N'-(2-氯-5-甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+I。
N'-[2-氯-4-(2-氟苯氧基)-5-甲基-苯基]-N-乙基-N-甲基-甲脒+I(此化合物可以由WO 2016/202742中描述的方法制备)。
2-(二氟甲基)-N-[(3S)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+I(此化合物可以由WO 2014/095675中描述的方法制备);
上文描述的混合配伍物是已知的。在活性成分包括在“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]]中的情况下,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。在“[CCN]”在上文添加到特定化合物的情况下,所述的化合物包括在“Compendium of Pesticide Common Names[杀有害生物剂通用名纲要]”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。
以上所述的活性成分中大部分在上文是通过所谓的“通用名”、相关的“ISO通用名”或在个别情况下使用的另一个“通用名”来提及。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”、“传统名称”、“化合物名称”或“研究代码”,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。
具有式(I)化合物和如上所述的活性成分的活性成分混合物优选地是以从100:1至1:6000的混合比率,尤其是处于从50:1至1:50,更尤其是从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,特别优选地是从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,尤其是比率为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。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,所述方法包括将含如上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。
包含具有式(I)的化合物以及一种或多种如以上描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,以组合的喷洒混合物(该混合物由这些单一活性成分的单独配制品构成)(例如“桶混制剂”)施用,并且当以顺序的方式(即,一个在另一个适当短的时期之后,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。具有式(I)的化合物与如上所述的一种或多种活性成分的施用的顺序对于实施本发明并不是关键的。
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以及具有式(I)的化合物用于制备这些组合物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的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防止植物(例如有用植物(例如作物植物))、其繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料免于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单独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,所述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所述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)渗透所述植物。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(例如包含具有式(I)的化合物、以及(如果希望的话)固体或液体辅助剂或用于封装具有式(I)的化合物的单体的组合物)可以按已知方式进行制备,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辅助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(如润湿剂和分散剂)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辅助剂,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。
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,60ppm、20ppm或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“m.p.”意指熔点。LC/MS意指液相色谱-质谱,并且所述装置和方法的描述如下:
方法G:
光谱记录在来自沃特斯公司的质谱仪(SQD、SQDII单四极杆质谱仪)上,其装备有一种电喷射源(极性:正离子和负离子),毛细管电压: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:100Da至900Da)和来自沃特斯公司的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:Waters 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
方法H:
光谱记录在来自沃特斯公司的质谱仪(SQD、SQDII单四极杆质谱仪)上,其装备有一种电喷射源(极性:正离子和负离子),毛细管电压: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:100Da至900Da)和来自沃特斯公司的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:Waters 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
方法I:
在来自沃特斯公司的质谱仪(ACQUITY UPLC)(SQD、SQDII或ZQ单四极杆质谱仪)上记录光谱,所述质谱仪配备有电喷射源(极性:正离子或负离子;毛细管电压(kV)3.5,锥孔电压(V)30.00,提取器(V)3.00,源温度(℃)150,去溶剂化温度(℃)400,锥孔反吹气体流量(L/Hr)60,去溶剂化气体流量(L/Hr)700,质量范围:140Da至800Da)和来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室以及二极管阵列检测器。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。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ACQUITY UPLC HSS T3;柱长:30mm;柱内径:2.1mm;粒度:1.8μm;温度:60℃,DAD波长范围(nm):210至400。溶剂梯度A:水/甲醇9:1,0.1%甲酸,以及溶剂B:乙腈,0.1%甲酸
方法J:
在来自安捷伦科技公司(Agilent Technologies)的质谱仪(6410三重四极质谱仪)上记录光谱,所述质谱仪配备有电喷射源(正和负极性转换,毛细管电压(kV)4.00,扫描类型MS2扫描,碎裂电压(V)100.00,气体温度(℃):350,气体流量:11L/min,雾化器气体(psi):45,质量范围:110Da至1000Da)和Agilent 1200系列HPLC:DAD波长范围:210至400nm,柱:KINETEX EVO C18,柱长:50mm,柱内径:4.6mm,粒度:2.6μm,柱箱温度:40℃
梯度条件:
溶剂A:含0.1%甲酸的水:乙腈::95:5v/v
溶剂B:含0.1%甲酸的乙腈
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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(例如反相手性色谱法)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
将所述活性成分与辅助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。
将所述活性成分与辅助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。
通过将所述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粉剂。此类粉剂还可以用于种子的干拌种。
挤出机颗粒剂
将所述活性成分与辅助剂混合并且研磨,并且将所述混合物用水润湿。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
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从所述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、倾倒或浸渍进行保护。
种子处理用的可流动性浓缩物
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从所述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、倾倒或浸渍进行保护。
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。向此乳液中加入在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加入0.25份的增稠剂以及3份的分散剂进行稳定。所述胶囊悬浮液配制品包含28%的活性成分。所述介质胶囊的直径是8微米-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。
缩写列表:
CDCl3 =氯仿-d
℃ =摄氏度
DCM =二氯甲烷
DMF =二甲基甲酰胺
DMSO =二甲基亚砜
d =二重峰
EtOAc =乙酸乙酯
h =小时
HCl =盐酸
M =摩尔
min =分钟
MHz =兆赫兹
mp =熔点
Pd2(dba)3 =三(二亚苄基丙酮)二钯(0)
ppm =百万分率
RT =室温
Rt =保留时间
rh =相对湿度
s =单峰
t =三重峰
THF =四氢呋喃
LCMS =液相色谱-质谱(用于LC/MS分析的装置和方法的描述在上文给出)
制备实例:
实例A1:(Z)-2-[5-(4-环丙基三唑-2-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(F-8)的制备
步骤1:
在室温下向5-溴-2-甲基苯酚(53.47mmol,10.00g)和2-溴乙酸甲酯(1.5当量,80.20mmol,12.27g,7.44mL)在四氢呋喃(0.5mol/L,106.9mL)中的溶液中添加碳酸钾(2当量,106.9mmol,14.78g),并将浅棕色悬浮液加热至65℃持续2h,然后冷却至室温过夜。将反应混合物用EtOAc稀释并且用水洗涤。将水相用EtOAc萃取,并且将总的合并的有机相用水、盐水洗涤,经Na2SO4干燥,过滤,并且在真空中浓缩,以得到呈棕色液体的2-(5-溴-2-甲基-苯氧基)乙酸甲酯(47.22mmol,15.89g,88%产率)。粗制油被残留的2-溴乙酸甲酯轻微污染,但不经进一步纯化直接用于下一步。
LCMS(方法H),Rt=1.59min,MS:(M+1)=259,261;1H NMR(400MHz,CDCl3)δppm2.25(s,3H)3.84(s,3H)4.66(s,2H)6.84(d,1H)7.05(m,2H)
步骤2:
第1部分:在室温下在氩气中向2-(5-溴-2-甲基苯氧基)乙酸酯(20.8g,80.3mmol)和甲酸甲酯(6.0当量,482mmol,29.5g,30.5mL)在四氢呋喃(0.5mol/L,161mL)中溶液中分批添加甲醇钠(20当量,161mmol,9.13g)。反应轻微放热,并在室温水浴的帮助下保持在30℃以下。将反应混合物在室温下搅拌1h并通过缓慢添加NaHCO3饱和水溶液进行淬灭。将两相分离并且将水相用EtOAc萃取。将总的合并的有机层用NaHCO3饱和水溶液、盐水洗涤,用Na2SO4干燥,过滤并在真空中浓缩,以得到2-(5-溴-2-甲基-苯氧基)-3-羟基-丙-2-烯酸甲酯,其无需进一步纯化即可直接用于下一步。
LCMS(方法G),Rt=0.80和0.90min,MS:(M+1)=287,289
第2部分:在室温下在氩气中向粗2-(5-溴-2-甲基-苯氧基)-3-羟基-丙-2-烯酸甲酯和硫酸二甲酯(1.2当量,93.2mmol,11.8g,8.8mL)在DMF(0.5mol/L,155mL)中的溶液中添加碳酸钾(1.5当量,117mmol,16.3g),并将反应混合物在室温搅拌2h。将所述反应混合物通过缓慢添加水来淬灭,并用EtOAc萃取混合物。将总的合并的有机层用NaHCO3的饱和水溶液、盐水洗涤,用Na2SO4干燥,过滤并在真空中浓缩。将残余物通过快速色谱法纯化(环己烷:EtOAc),得到呈灰白色固体的(Z)-2-(5-溴-2-甲基-苯氧基)-3-甲氧基-丙-2-烯酸甲酯(59.6mmol,18.0g,75%产率)。
LCMS(方法G),Rt=1.02min,MS:(M+1)=301,303;1H NMR(400MHz,CDCl3)δppm2.31(s,3H)3.74(s,3H)3.91(s,3H)6.86(d,1H)7.05(m,2H)7.35(s,1H)
步骤3:
在氩气下将四甲基-t-BuXphos(0.10当量,0.066mmol,0.033g)和Pd2(dba)3(0.05当量,0.033mmol,0.031g)在1mL甲苯中的溶液在110℃下加热3min,然后将混合物冷却至室温。在室温下将预先形成的钯催化剂转移到(Z)-2-(5-溴-2-甲基-苯氧基)-3-甲氧基-丙-2-烯酸甲酯(0.66mmol,0.20g)、4-环丙基-2H-三唑(1.1当量,0.73mmol,0.080g)和碳酸钾(2.0当量,1.33mmol,0.184g)在甲苯(0.2mol/L,3.3mL)中的混合物中,将所得的深棕色悬浮液加热至110℃持续1h。允许该反应混合物冷却至室温,并且然后添加EtOAc。将有机相用水洗涤,并将水相用EtOAc萃取。将总的合并的有机层用盐水洗涤,用Na2SO4干燥,过滤并在真空中浓缩。将残余物通过快速色谱法纯化(环己烷:EtOAc),得到(Z)-2-[5-(4-环丙基三唑-2-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(0.23mmol,0.075g,34%产率)。
LCMS(方法G),Rt=1.07min,MS:(M+1)=330;1H NMR(400MHz,CDCl3)δppm 0.88(m,2H)1.04(m,2H)2.03(m,1H)2.40(s,3H)3.74(s,3H)3.91(s,3H)7.24(d,1H)7.40(s,1H)7.41(d,1H)7.46(s,1H)7.58(dd,1H)
实例A2:(Z)-3-甲氧基-2-[2-甲基-5-[3-(三氟甲基)吡唑-1-基]苯氧基]丙-2-烯酸甲酯(E-105)的制备
在氩气下将四甲基-t-BuXphos(0.10当量,0.050mmol,0.025g)和Pd2(dba)3(0.05当量,0.025mmol,0.024g)在1mL甲苯中的溶液在110℃下加热3分钟。然后允许该混合物冷却至室温。在室温下将预先形成的活性钯催化剂转移到(Z)-2-(5-溴-2-甲基-苯氧基)-3-甲氧基-丙-2-烯酸甲酯(0.50mmol,0.15g)、3-(三氟甲基)-1H-吡唑(1.2当量,0.60mmol,0.082g)和碳酸钾(2.0当量,1.0mmol,0.138g)在甲苯(0.2mol/L,2.5mL)中的混合物中,将所得的深棕色悬浮液加热至110℃持续1h。允许该反应混合物冷却至室温,并且然后添加EtOAc。将有机相用水洗涤,并将水相用EtOAc萃取。将总的合并的有机层用盐水洗涤,用Na2SO4干燥,过滤并在真空中浓缩。将残余物通过快速色谱法纯化(环己烷:EtOAc),得到呈白色固体的(Z)-3-甲氧基-2-[2-甲基-5-[3-(三氟甲基)吡唑-1-基]苯氧基]丙-2-烯酸甲酯(0.28mmol,0.10g,56%产率)。
mp:154-156℃;LCMS(方法G),Rt=1.07min,MS:(M+1)=357;1H NMR(400MHz,CDCl3)δppm 2.40(s,3H)3.75(s,3H)3.93(s,3H)6.69(m,1H)7.10(d,1H)7.19-7.30(m,2H)7.40(s,1H)7.87(m,1H)
实例A3:(Z)-2-[5-(3-碘吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(E-78)的制备
步骤1:
在室温下向(Z)-2-(5-溴-2-甲基-苯氧基)-3-甲氧基-丙-2-烯酸甲酯(66.4mmol,20.0g)在1,4-二噁烷(133mL)中的溶液中添加双(频哪醇合)二硼(1.10当量,73.1mmol,18.7)、乙酸钾(2.00当量,133mmol,13.6g)和1,1'-双(二苯基膦基)二茂铁-钯(II)二氯化物二氯甲烷络合物(0.025当量,1.66mmol,1.38g),然后将反应混合物在100℃(内部温度94℃)加热90min。将深棕色悬浮液用EtOAc稀释,并添加水。分离层并用EtOAc萃取水相。将总的合并的有机层用盐水洗涤,用Na2SO4干燥,过滤并在真空中浓缩。将残余物通过快速色谱法纯化(环己烷:EtOAc),得到米色湿晶体固体,将其用少量己烷研磨,过滤并在真空中干燥,得到呈白色固体的(Z)-3-甲氧基-2-[2-甲基-5-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯氧基]丙-2-烯酸甲酯(32.6mmol,12.0g,49%产率)。
LCMS(方法H),Rt=1.82min,MS:(M+1)=349;1H NMR(400MHz,CDCl3)δppm 1.34(s,12H)2.39(s,3H)3.72(s,3H)3.89(s,3H)7.12(s,1H)7.19(d,1H)7.34(s,1H)7.39(d,1H)
步骤2:
向(Z)-3-甲氧基-2-[2-甲基-5-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯氧基]丙-2-烯酸甲酯(14.4mmol,5.00g)在四氢呋喃:水混合物(4:1V/V,72mL)中的溶液中添加高碘酸钠(3.00当量,43.1mmol,9.31g),然后添加盐酸溶液(2.0M,0.25当量,3.59mmol,1.79mL)。将获得的白色悬浮液在室温下搅拌4h,然后添加EtOAc和水。分离层并用EtOAc萃取水相。将总的合并的有机层用盐水洗涤,用Na2SO4干燥,过滤并浓缩,以得到呈白色固体的[3-[(Z)-2-甲氧基-1-甲氧基羰基-乙烯基氧基]-4-甲基-苯基]硼酸(12.1mmol,3.58g,84%产率)。
LCMS(方法H),Rt=1.00min,MS:(M+H)=367;1H NMR(400MHz,DMSO-d6)δppm 2.23(s,3H)3.64(s,3H)3.85(s,3H)7.12(m,2H)7.33(d,1H)7.54(s,1H)7.96(brs,2H)
步骤3:
在室温下在空气中向[3-[(Z)-2-甲氧基-1-甲氧基羰基-乙烯基氧基]-4-甲基-苯基]硼酸(0.28mmol,0.075g)、3-碘-1h-吡唑(1.1当量,0.31mmol,0.060g)和碳酸钠(1.5当量,0.42mmol,0.045g)在N,N-二甲基乙酰胺(0.33mol/L,0.85mL)中的悬浮液中添加乙酸铜(II)(0.25当量,0.070mmol,0.013g)和吡啶(0.50当量,0.141mmol,0.011g,0.012mL),并将反应混合物在80℃加热过夜。将混合物用EtOAc稀释,并用NH4Cl水溶液(2.5mol/L)淬灭。分离层并用EtOAc萃取水相。将合并的有机层用盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将残余物通过快速色谱法进行纯化,以得到呈白色固体的(Z)-2-[5-(3-碘吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(0.12mmol,0.057g,44%产率)。
mp:156-159℃;LCMS(方法H),Rt=1.69min,MS:(M+1)=415;1H NMR(400MHz,CDCl3)δppm 2.39(s,3H)3.74(s,3H)3.92(s,3H)6.60(d,1H)7.06(d,1H)7.14(dd,1H)7.22(d,1H)7.38(s,1H)7.66(d,1H)
实例A4:(Z)-2-[5-(3-环己基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(E-36)的制备
步骤1:
程序:在室温下向(Z)-2-[5-(3-碘吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(0.18mmol,0.075g)、碳酸铯(2.5当量,0.45mmol,0.148g)和环己-1-烯-1-基硼酸(1.75当量,0.32mmol,0.040g)在1,4-二噁烷(0.25mol/L,0.73mL)和水(0.40mL/mmol,0.072mL)中的溶液中添加CATACXIUM-Pd-G3(0.10当量,0.018mmol,0.014g),并将反应混合物在100℃加热80min。允许该反应混合物冷却至室温,经Na2SO4垫过滤。将垫用EtOAc洗涤,并且在真空中浓缩滤液。将残余物通过快速色谱法进行纯化,以得到呈米色固体的(Z)-2-[5-[3-(环己烯-1-基)吡唑-1-基]-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(0.10mmol,0.040g,57%产率)。
mp:108-110℃;LCMS(方法H),Rt=2.05min,MS:(M+1)=369;1H NMR(400MHz,CDCl3)δppm 1.69(m,2H)1.78(m,2H)2.23(m,2H)2.36(s,3H)2.52(m,2H)3.72(s,3H)3.90(s,3H)6.40(m,1H)6.46(d,1H)7.09(s,1H)7.19(m,2H)7.36(s,1H)7.74(d,1H)
步骤2:
在室温下向(Z)-2-[5-[3-(环己烯-1-基)吡唑-1-基]-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(0.060mmol,0.022g)在乙酸乙酯(0.1mol/L,0.60mL)和正己烷(0.1mol/L,0.60mL)中的溶液中添加Pd/C(5%wt,0.05当量,0.006g)。使用气球用氢气吹扫反应混合物。在室温下搅拌该反应混合物,直到通过LCMS不再观察到起始材料。将黑色悬浮液过滤通过硅藻土和二氧化硅垫,并用EtOAc洗涤。在真空中浓缩滤液,以得到呈米色固体的(Z)-2-[5-(3-环己基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯(0.049mmol,0.020g,81%产率)。
mp:85-89℃;LCMS(方法H),Rt=2.06min,MS:(M+1)=371;1H NMR(400MHz,CDCl3)δppm 1.39-1.50(m,4H)1.54-1.59(m,1H)1.72-1.79(m,1H)1.80-1.88(m,2H)2.02(m,2H)2.37(s,3H)2.71-2.82(m,1H)3.73(s,3H)3.91(s,3H)6.24(d,1H)7.05(s,1H)7.19(m,2H)7.37(s,1H)7.72(d,1H)
表E:具有式(I)的化合物的物理数据
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表F:具有式(I)的化合物的物理数据
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实例B:生物学实例/测试方法:
实例B1:茄链格孢菌(Alternaria solani)/番茄/叶圆片(早枯病)将番茄叶圆片栽培品种Baby置于多孔板(24孔格式)中的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后2天,用真菌的孢子悬浮液接种所述叶圆片。在气候箱中,在12/12h(照明/黑暗)的光方案下,在23℃/21℃(白天/夜晚)和80%rh(相对湿度)下孵育接种的叶圆片,并且化合物活性被评估为,在未处理的检验叶圆片上出现适当水平的疾病损害时(施用以后5-7天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对茄链格孢菌给出至少80%的控制:
E-1、E-15、E-16、E-17、E-21、E-27、E-29、E-30、E-34、E-36、E-39、E-57、E-58、E-60、E-64、E-67、E-68、E-70、E-80、E-82、E-83、E-85、E-88、E-98、E-99、E-105、E-113、F-1、F-2、F-4、F-5、F-10、F-13
实例B2:灰葡萄孢菌(Botryotinia fuckeliana或Botrytis cinerea)/液体培养(灰霉病)
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(沃格尔(Vogels)肉汤(broth))中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔格式)中之后,添加含有真菌孢子的营养肉汤。将测试板在24℃下进行孵育并且在施用后3-4天通过光度法确定生长抑制。
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,以下化合物在20ppm处对灰葡萄孢菌给出至少80%的控制:
E-5、E-6、E-16、E-23、E-24、E-25、E-29、E-30、E-31、E-32、E-33、E-34、E-35、E-36、E-37、E-38、E-39、E-40、E-42、E-43、E-44、E-46、E-47、E-48、E-49、E-50、E-51、E-52、E-53、E-54、E-55、E-57、E-58、E-59、E-60、E-61、E-64、E-65、E-66、E-75、E-80、E-81、E-82、E-85、E-86、E-87、E-88、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-116、F-8
实例B3:瓜小丛壳菌(Glomerella lagenarium)(瓜类炭疽菌(Colletotrichum
lagenarium))/液体培养(炭疽病)
将来自冷冻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。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔格式)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下进行孵育并且在施用之后3-4天通过光度法测量对生长的抑制。
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,以下化合物在20ppm处对瓜小丛壳菌给出至少80%的控制:
E-5、E-6、E-7、E-12、E-14、E-15、E-16、E-18、E-19、E-20、E-21、E-23、E-24、E-25、E-26、E-27、E-28、E-29、E-30、E-31、E-32、E-33、E-34、E-35、E-36、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-47、E-48、E-49、E-50、E-51、E-52、E-53、E-54、E-57、E-58、E-59、E-60、E-61、E-64、E-65、E-66、E-67、E-68、E-69、E-70、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-86、E-87、E-88、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-110、E-111、E-112、E-113、E-114、E-115、E-116、E-117、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-9、F-10、F-11、F-12、F-13
实例B4:小麦白粉病菌(Blumeria graminis f.sp.tritici,Erysiphe graminisf.sp.tritici)/小麦/叶圆片预防性(小麦上的白粉病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔格式)中的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后1天,通过在这些测试板之上摇动白粉病感染的植物来接种叶圆片。在气候箱中,在24h黑暗、随后是12h光照/12h黑暗的光照方案下,在20℃和60%rh下孵育经接种的叶圆片,并且在未处理的检验叶段上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,以下化合物在200ppm下给出对小麦白粉病菌的至少80%的控制:
E-3、E-4、E-7、E-15、E-16、E-17、E-18、E-19、E-22、E-24、E-25、E-26、E-27、E-28、E-29、E-32、E-34、E-35、E-38、E-39、E-40、E-41、E-42、E-44、E-45、E-47、E-48、E-50、E-51、E-54、E-57、E-58、E-59、E-60、E-61、E-64、E-66、E-67、E-68、E-69、E-70、E-75、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-86、E-87、E-88、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-108、E-109、E-111、E-114、E-115、E-116、E-117、E-118、F-1、F-4、F-5、F-6、F-7、F-8、F-9、F-10、F-11、F-12、F-13
实例B5:黄色镰刀菌(Fusarium culmorum)/小麦/小穗预防性(赤霉病)
将小麦小穗栽培品种Monsun置于多孔板(24孔格式)中的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后1天,用真菌的孢子悬浮液接种所述小穗。在气候室中,在72h半黑暗随后是12h光照/12h黑暗的光照方案下,在20℃和60%rh下孵育接种的小穗,并且化合物的活性被评估为,在未处理的检查小穗上出现适当水平的病害损害时(施用后6-8天),与未处理的相比的病害控制百分比。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,以下化合物在200ppm下给出对黄色镰刀菌的至少80%的控制:
E-68、E-92、E-103、E-117
实例B6:颖枯壳针孢(Phaeosphaeria nodorum,Septoria nodorum)/小麦/叶圆片预防性(颖斑枯病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔格式)中的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后2天,用真菌的孢子悬浮液接种所述叶圆片。在气候箱中,在12h光照/12h黑暗的光照方案下,在20℃和75%rh下孵育接种的测试叶圆片,并且化合物的活性被评估为,在未处理的检验叶圆片上出现适当水平的疾病损害时(施用后5-7天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对颖枯壳针孢给出至少80%的控制:
E-1、E-2、E-3、E-4、E-6、E-7、E-11、E-19、E-20、E-24、E-26、E-29、E-30、E-31、E-32、E-36、E-40、E-42、E-44、E-45、E-47、E-48、E-49、E-50、E-53、E-54、E-57、E-58、E-59、E-60、E-65、E-66、E-67、E-68、E-70、E-75、E-78、E-81、E-82、E-83、E-84、E-85、E-86、E-88、E-90、E-92、E-94、E-96、E-99、E-100、E-101、E-103、E-104、E-105、E-110、E-111、E-112、E-113、E-114、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-10、F-11、F-12、F-13实例B7:雪腐明梭孢(Monographella nivalis)(雪霉叶枯菌(Microdochium nivale))/液体培养(谷类根腐病)
将来自冷冻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。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔格式)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下进行孵育并且在施用之后4-5天通过光度法确定对生长的抑制。
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,以下化合物在20ppm处对雪腐明梭孢给出至少80%的控制:
E-1、E-2、E-3、E-4、E-5、E-6、E-7、E-9、E-10、E-11、E-12、E-14、E-15、E-16、E-17、E-18、E-19、E-20、E-21、E-22、E-23、E-24、E-25、E-26、E-27、E-28、E-29、E-30、E-31、E-32、E-33、E-34、E-35、E-36、E-37、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-47、E-48、E-49、E-50、E-51、E-52、E-53、E-54、E-55、E-57、E-58、E-59、E-60、E-61、E-64、E-65、E-66、E-67、E-68、E-69、E-70、E-75、E-76、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-86、E-87、E-88、E-89、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-108、E-109、E-110、E-111、E-112、E-113、E-114、E-115、E-116、E-117、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-9、F-11、F-12、F-13
实例B8:落花生球腔菌(Mycosphaerella arachidis)(落花生尾孢菌(Cercosporaarachidicola))/液体培养(早期叶斑病)
将来自冷冻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。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔格式)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下进行孵育并且在施用之后4-5天通过光度法确定对生长的抑制。
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,以下化合物在20ppm处对落花生球腔菌给出至少80%的控制:
E-1、E-2、E-3、E-4、E-5、E-6、E-7、E-9、E-10、E-11、E-12、E-14、E-15、E-16、E-17、E-18、E-19、E-20、E-21、E-22、E-23、E-24、E-25、E-26、E-27、E-28、E-29、E-30、E-31、E-32、E-33、E-34、E-35、E-36、E-37、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-47、E-48、E-49、E-50、E-51、E-52、E-53、E-54、E-55、E-57、E-58、E-59、E-60、E-61、E-64、E-65、E-66、E-67、E-68、E-69、E-70、E-75、E-76、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-86、E-87、E-88、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-108、E-109、E-110、E-111、E-112、E-113、E-114、E-115、E-116、E-117、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-9、F-10、F-11、F-12、F-13
实例B9:豆薯层锈菌/大豆/预防性(大豆锈病)
将大豆叶圆片置于多孔板(24孔格式)内的琼脂中并且喷洒试验溶液。干燥之后,将叶圆片用真菌孢子悬浮液接种。适当的孵育之后,化合物的活性12dpi(孵育之后的天数)被评定为防止性杀真菌活性。
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,以下化合物在200ppm处对豆薯层锈菌给出至少80%的控制:
E-1、E-5、E-11、E-26、E-29、E-31、E-32、E-36、E-38、E-40、E-41、E-42、E-44、E-45、E-46、E-48、E-54、E-60、E-66、E-67、E-68、E-69、E-70、E-75、E-78、E-83、E-88、E-90、E-92、E-94、E-95、E-96、E-100、E-101、E-104、E-105、E-110、E-111、E-112、E-113、E-114、E-115、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8
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,以下化合物在200ppm下给出对豆薯层锈菌的至少50%的控制:
E-1、E-2、E-3、E-4、E-5、E-7、E-11、E-20、E-26、E-27、E-29、E-30、E-31、E-32、E-35、E-36、E-37、E-38、E-40、E-41、E-42、E-44、E-45、E-46、E-47、E-48、E-50、E-51、E-52、E-54、E-57、E-58、E-59、E-60、E-61、E-64、E-66、E-67、E-68、E-69、E-70、E-75、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-87、E-88、E-89、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-110、E-111、E-112、E-113、E-114、E-115、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8
实例B10:致病疫霉菌(Phytophthora infestans)/番茄/叶圆片预防性(晚疫病)
将番茄叶圆片置于多孔板(24孔格式)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。在施用之后1天,将叶圆片用真菌的孢子悬浮液进行接种。在气候箱中,在24h黑暗、随后是12h照明/12h黑暗的光照方案下,在16℃和75%rh下孵育接种的叶圆片,并且化合物的活性被评估为,在未处理的检验叶圆片中出现适当水平的疾病损害时(施用后5-7天),与未处理的相比的疾病控制百分比。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,以下化合物在200ppm下给出对致病疫霉菌的至少80%的控制:
E-1、E-3、E-4、E-5、E-6、E-7、E-12、E-18、E-19、E-20、E-21、E-22、E-23、E-24、E-25、E-26、E-29、E-30、E-31、E-32、E-34、E-35、E-36、E-38、E-39、E-40、E-43、E-44、E-45、E-46、E-47、E-48、E-49、E-50、E-52、E-53、E-54、E-57、E-58、E-59、E-60、E-61、E-67、E-70、E-76、E-78、E-80、E-81、E-82、E-83、E-87、E-88、E-90、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-110、E-113、E-114、E-116、E-118、F-1、F-2、F-4、F-5、F-6、F-8、F-9、F-10、F-11、F-12、F-13
实例B11:葡萄生单轴霉/葡萄/叶圆片预防性(晚疫病)
将葡萄藤叶圆片置于多孔板(24孔格式)中的水琼脂培养基上,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,将叶圆片用真菌的孢子悬浮液进行接种。在气候箱中,在12h照明/12h黑暗的光照方案下,在19℃和80%rh下孵育所述接种的叶圆片,并且化合物活性被评估为,在未处理的检验叶圆片中出现适当水平的疾病损害时(施用后6-8天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对葡萄生单轴霉给出至少80%的控制:
E-1、E-2、E-3、E-5、E-6、E-7、E-11、E-12、E-18、E-19、E-20、E-21、E-23、E-24、E-25、E-26、E-27、E-28、E-29、E-30、E-31、E-32、E-33、E-34、E-35、E-36、E-37、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-47、E-48、E-49、E-50、E-51、E-52、E-53、E-54、E-57、E-58、E-59、E-60、E-61、E-64、E-65、E-66、E-67、E-68、E-69、E-70、E-75、E-76、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-87、E-88、E-89、E-90、E-92、E-94、E-95、E-96、E-98、E-99、E-100、E-101、E-103、E-105、
E-106、E-109、E-110、E-111、E-112、E-113、E-114、E-116、E-117、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-9、F-10、F-11、F-12、F-13
实例B12:小麦隐匿柄锈菌(Puccinia recondita f.sp.tritici)/小麦/叶圆片治疗法(褐锈病)
将小麦叶段栽培品种将Kanzler置于多孔板(24孔格式)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。在气候箱中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育叶段,并且化合物的活性被评估为,在未处理的检验叶段中出现适当水平的疾病损害时(施用后6-8天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对小麦隐匿柄锈菌给出至少80%的控制:
E-5、E-7、E-11、E-15、E-16、E-17、E-18、E-20、E-21、E-23、E-24、E-25、E-26、E-27、E-28、E-29、E-30、E-31、E-32、E-35、E-36、E-37、E-38、E-39、E-40、E-41、E-42、E-43、E-45、E-46、E-47、E-48、E-49、E-51、E-57、E-58、E-60、E-64、E-65、E-66、E-67、E-68、E-69、E-70、E-77、E-80、E-82、E-88、E-90、E-92、E-94、E-95、E-96、E-99、E-101、E-103、E-110、E-112、E-114、E-115、E-116、E-117、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-9、F-11、F-12、F-13
实例B13:小麦隐匿柄锈菌/小麦/叶圆片预防性(褐锈病)
将小麦叶段栽培品种将Kanzler置于多孔板(24孔格式)中的琼脂上,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,将叶圆片用真菌的孢子悬浮液进行接种。在气候箱中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育接种的叶段,并且化合物的活性被评估为,在未处理的检验叶段中出现适当水平的疾病损害时(施用后7-9天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对小麦隐匿柄锈菌给出至少80%的控制:
E-1、E-2、E-3、E-4、E-5、E-6、E-7、E-11、E-12、E-15、E-16、E-17、E-18、E-19、E-20、E-21、E-22、E-23、E-24、E-25、E-26、E-27、E-28、E-29、E-30、E-31、E-32、E-33、E-34、E-35、E-36、E-37、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-47、E-48、E-49、E-50、E-51、E-52、E-53、E-54、E-55、E-57、E-58、E-59、E-60、E-61、E-65、E-66、E-67、E-68、E-69、E-70、E-75、E-76、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-86、E-87、E-88、E-89、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-106、E-107、E-108、E-109、E-110、E-113、E-114、E-115、E-116、E-117、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-9、F-10、F-11、F-12、F-13
实例B14:稻瘟病菌(Magnaporthe grisea)(稻梨孢(Pyricularia oryzae))/稻/叶圆片预防(稻瘟病(Rice Blast))
将稻叶段栽培品种将Ballila置于多孔板(24孔格式)的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后2天,用真菌的孢子悬浮液接种所述叶段。在气候箱中,在24h黑暗,随后是12h光照/12h黑暗的光照方案下,在22℃和80%rh下孵育接种的叶段,并且化合物的活性被评估为,在未处理的检验叶片段中出现适当的疾病损害水平时(施用后5-7天之后),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对稻瘟病菌给出至少80%的控制:
E-1、E-2、E-5、E-6、E-7、E-10、E-11、E-12、E-18、E-19、E-20、E-24、E-25、E-26、E-27、E-29、E-30、E-31、E-32、E-34、E-35、E-36、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-47、E-49、E-50、E-51、E-52、E-53、E-57、E-58、E-59、E-60、E-61、E-64、E-65、E-68、E-69、E-70、E-76、E-78、E-80、E-81、E-82、E-83、E-85、E-86、E-88、E-90、E-92、E-98、E-99、E-100、E-103、E-104、E-105、E-110、E-112、E-113、E-114、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-10、F-11、F-12、F-13
实例B15:圆核腔菌(Pyrenophora teres)/大麦/叶圆片预防性(网斑病)
将大麦叶段栽培品种Hasso的叶段置于多孔板(24孔格式)的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后2天之后用真菌的孢子悬浮液接种所述叶段。在气候箱中,在12h光照/12h黑暗的光照方案下,在20℃和65%rh下孵育接种的叶段,并且化合物的活性被评估为,在未处理的检验叶段上出现适当水平的疾病损害时(施用后5-7天),与未处理的相比的疾病控制。
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,以下化合物在200ppm处对圆核腔菌给出至少80%的控制:
E-1、E-2、E-12、E-34、E-36、E-38、E-39、E-42、E-44、E-45、E-54、E-67、E-70、E-75、E-78、E-81、E-82、E-83、E-89、E-105、E-108、E-109、E-112、E-114、E-118、F-1、F-2、F-4、F-5、F-7、F-10、F-11、F-12、F-13
实例B16:终极腐霉(Pythium ultimum)/液体培养(苗期猝倒病)
将新鲜培养的真菌液体培养物的菌丝体片段以及卵孢子直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔格式)中以后,添加含有真菌菌丝体/孢子的混合物的营养肉汤。将这些测试板在24℃下进行孵育并且在施用之后2-3天通过光度法确定对生长的抑制。
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,以下化合物在20ppm处对终极腐霉给出至少80%的控制:
E-5、E-7、E-21、E-68、E-80、E-92、E-103、F-9
实例B17:水稻纹枯病菌(立枯丝核菌)/液体培养(根腐病,猝倒病):
将真菌的新生长的液体培养物的菌丝体片段直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将试验化合物的(DMSO)溶液置于微量滴定板(96孔格式)中之后,添加含有真菌材料的营养肉汤。将测试板在24℃下进行孵育并且在施用后3-4天通过光度法确定生长抑制。
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,以下化合物在20ppm处对水稻纹枯病菌给出至少80%的控制:
E-23、E-24、E-30、E-31、E-32、E-34、E-35、E-36、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-48、E-50、E-52、E-53、E-57、E-58、E-59、E-60、E-65、E-67、E-68、E-69、E-98、E-101
实例B18:核盘菌/液体培养(棉状腐病)
将真菌的新生长的液体培养物的菌丝体片段直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将试验化合物的(DMSO)溶液置于微量滴定板(96孔格式)中之后,添加含有真菌材料的营养肉汤。将测试板在24℃下进行孵育并且在施用后3-4天通过光度法确定生长抑制。
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,以下化合物在20ppm处对核盘菌给出至少80%的控制:
E-18、E-19、E-20、E-23、E-24、E-36、E-67、E-68、E-69、E-117、F-3、F-7
实例B19:禾生球腔菌(小麦壳针孢)/液体培养(叶枯病(Septoria blotch))
将来自冷冻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。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔格式)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下进行孵育并且在施用之后4-5天通过光度法确定对生长的抑制。
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,以下化合物在20ppm处对禾生球腔菌给出至少80%的控制:
E-1、E-2、E-3、E-4、E-5、E-6、E-7、E-9、E-10、E-11、E-12、E-14、E-15、E-16、E-17、E-18、E-19、E-20、E-21、E-22、E-23、E-24、E-25、E-26、E-27、E-28、E-29、E-30、E-31、E-32、E-33、E-34、E-35、E-36、E-37、E-38、E-39、E-40、E-41、E-42、E-43、E-44、E-45、E-46、E-47、E-48、E-49、E-50、E-51、E-52、E-53、E-54、E-55、E-57、E-58、E-59、E-60、E-61、E-64、E-65、E-66、E-67、E-68、E-69、E-70、E-75、E-76、E-77、E-78、E-80、E-81、E-82、E-83、E-84、E-85、E-86、E-87、E-88、E-89、E-90、E-91、E-92、E-94、E-95、E-96、E-97、E-98、E-99、E-100、E-101、E-103、E-104、E-105、E-107、E-108、E-109、E-110、E-113、E-114、E-115、E-116、E-117、E-118、F-1、F-2、F-3、F-4、F-5、F-6、F-7、F-8、F-9、F-10、F-11、F-12、F-13
对比数据:
将本发明的化合物E-15、E-40、E-42、E-70、E-92、E-105、F-8、F-9的生物活性与参考化合物X-1进行比较。参考化合物X-1在EP 0212 859的第13页上作为第140号化合物具体公开。
数据表示为生物学测试中每种化合物针对如上所述的瓜小丛壳菌(实例B3)、小麦隐匿柄锈菌/预防性(实例B13)、圆核腔菌(实例B15)和禾生球腔菌(实例B19)的疾病控制百分比。下表C1中具体描述了每个生物学测试的测试率。
表C1:对比数据
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实例D:比较光稳定性数据
将本发明的化合物E-40、E-41、E-42、E-44、E-67、E-68、E-70、E-88、E-90、E-92、E-101和E-105的光稳定性数据与参考化合物X-1进行比较。
表中测量每种化合物的光稳定性数据的测试方法为D1,具体如下所述。光稳定性测定的目的是在严格受控且可重复的环境中确定单个测试化合物的稳定性,从而允许比较它们的光稳定性。
方法:将化合物溶于甲醇(HPLC级)中,得到1g/L储备溶液。将化合物储备溶液(2μl)点样到3D打印支架中的显微镜载玻片上,并放入Atlas Suntest中。Suntest的光谱输出功率设置为750W/m2,在非常明亮的英国夏季,这被认为是每日最大(正午)辐照度水平的典型。在特定的时间点,将载玻片从Suntest中取出,并放入4D小瓶中。将由50:40:10H2O:MeCN:THF(1mL)组成的洗涤溶剂添加到小瓶中并涡旋混合。然后将所得溶液二次取样到HPLC小瓶中进行分析。将具有光电二极管阵列的Waters UPLC系统与Waters反相柱(BEHC18,100x2.1mm x 1.7μm)和流速为0.6mL/min的乙腈(HPLC级)酸化水(0.2%甲酸)流动相一起使用。峰检测处于在最佳波长下,并且峰面积用于定量。
使用可归因于测试化合物的峰面积的初始测量值与后续测量值来提供3h时剩余的%母体。
表D1-光稳定性数据
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实例E:针对豆薯层锈菌(大豆锈病)的比较生物活性:
将本发明的化合物E-40、E-92、E-105、F-2和F-6的生物活性与参考化合物X-1、X-2和X-3进行比较。参考化合物X-1在EP0212859的第13页上具体公开为化合物140,参考化合物X-3在WO 01/00562的第61页上具体公开为化合物1-91。
方法:将大豆叶圆片置于多孔板(24孔格式)内的琼脂中并且喷洒试验溶液。干燥之后,将叶圆片用真菌孢子悬浮液接种。适当的孵育之后,化合物的活性12dpi(孵育之后的天数)被评定为防止性杀真菌活性。
数据表示为下表E1中所述的生物学测试中每种化合物的疾病控制百分比和测试率。
表E1-针对豆薯层锈菌(大豆锈病)的比较生物活性:
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Claims (9)
1.选自下组的化合物:(Z)-3-甲氧基-2-[2-甲基-5-(3-丙基吡唑-1-基)苯氧基]丙-2-烯酸甲酯、(Z)-2-[4-氟-5-(3-异丙基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-2-[4-氟-2-甲基-5-[3-(三氟甲基)吡唑-1-基]苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-3-甲氧基-2-[2-甲基-5-(3-仲丁基吡唑-1-基)苯氧基]丙-2-烯酸甲酯、(Z)-2-[5-[3-(1-氟环丙基)吡唑-1-基]-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-2-[5-[3-(1,1-二氟乙基)吡唑-1-基]-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-2-[5-(3-异丙氧基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-2-[5-(3-环丁基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-2-[5-(3-异丁基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-2-[5-(3-异丙基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯、(Z)-3-甲氧基-2-[2-甲基-5-(4-丙基三唑-2-基)苯氧基]丙-2-烯酸甲酯、(Z)-3-甲氧基-2-[2-甲基-5-[4-(三氟甲基)三唑-2-基]苯氧基]丙-2-烯酸甲酯和(Z)-2-[5-(4-环丙基三唑-2-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯。
2.根据权利要求1所述的化合物,其中所述化合物是:
(Z)-2-[5-(3-环丁基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯。
3.根据权利要求1所述的化合物,其中所述化合物是:
(Z)-2-[5-(3-异丙基吡唑-1-基)-2-甲基-苯氧基]-3-甲氧基-丙-2-烯酸甲酯。
4.根据权利要求1所述的化合物,其中所述化合物是:
(Z)-3-甲氧基-2-[2-甲基-5-(3-丙基吡唑-1-基)苯氧基]丙-2-烯酸甲酯。
5.根据权利要求1所述的化合物,其中所述化合物是:
(Z)-3-甲氧基-2-[2-甲基-5-(4-丙基三唑-2-基)苯氧基]丙-2-烯酸甲酯。
6.一种农用化学组合物,其包含杀真菌有效量的根据权利要求1至5中任一项所述的化合物、以及农用化学上可接受的稀释剂或载体。
7.根据权利要求6所述的组合物,其进一步包含至少一种另外的活性成分。
8.一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根据权利要求1至5中任一项所述的化合物或包含所述化合物作为活性成分的组合物施用于所述植物、其部分或其场所。
9.根据权利要求1至5中任一项所述的化合物作为杀真菌剂的用途,前提条件是所述用途不包括通过手术或疗法来治疗人体或动物体的方法。
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WO2020079111A1 (en) | 2020-04-23 |
EP3867230A1 (en) | 2021-08-25 |
US20210363107A1 (en) | 2021-11-25 |
BR112021007145A2 (pt) | 2021-07-20 |
UY38420A (es) | 2020-05-29 |
JP2022504945A (ja) | 2022-01-13 |
AR116628A1 (es) | 2021-05-26 |
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