CN104394693B - 杀真菌吡唑混合物 - Google Patents
杀真菌吡唑混合物 Download PDFInfo
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- CN104394693B CN104394693B CN201380018012.0A CN201380018012A CN104394693B CN 104394693 B CN104394693 B CN 104394693B CN 201380018012 A CN201380018012 A CN 201380018012A CN 104394693 B CN104394693 B CN 104394693B
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- Prior art keywords
- antifungal
- compound
- methyl
- component
- formula
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- 239000000203 mixture Substances 0.000 title claims abstract description 231
- 229940121375 antifungal agent Drugs 0.000 title claims description 235
- 230000000843 anti-fungal effect Effects 0.000 title claims description 230
- 150000003217 pyrazoles Chemical class 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 355
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims abstract description 80
- 201000010099 disease Diseases 0.000 claims abstract description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 60
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 26
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 25
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
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- 241000196324 Embryophyta Species 0.000 claims description 107
- 241000894006 Bacteria Species 0.000 claims description 76
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- 230000015572 biosynthetic process Effects 0.000 claims description 51
- 238000002360 preparation method Methods 0.000 claims description 46
- 239000000417 fungicide Substances 0.000 claims description 45
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- 239000003153 chemical reaction reagent Substances 0.000 claims description 35
- 239000000460 chlorine Substances 0.000 claims description 34
- 239000003112 inhibitor Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
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- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000005784 Fluoxastrobin Substances 0.000 claims description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 8
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- 239000005788 Fluxapyroxad Substances 0.000 claims description 7
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 7
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 claims description 7
- 150000002632 lipids Chemical class 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 claims description 6
- NNPRCLUGHFXSOU-UHFFFAOYSA-N 4-chloro-n-[cyano(ethoxy)methyl]benzamide Chemical compound CCOC(C#N)NC(=O)C1=CC=C(Cl)C=C1 NNPRCLUGHFXSOU-UHFFFAOYSA-N 0.000 claims description 6
- 239000005740 Boscalid Substances 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
- 239000005799 Isopyrazam Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 229930182764 Polyoxin Natural products 0.000 claims description 6
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 6
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 claims description 6
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 claims description 6
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims description 6
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 claims description 6
- 230000014616 translation Effects 0.000 claims description 6
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims description 5
- ZGOAEMCMBVUNMX-UHFFFAOYSA-N 1,1'-biphenyl;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CC=CC=C1C1=CC=CC=C1 ZGOAEMCMBVUNMX-UHFFFAOYSA-N 0.000 claims description 5
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 5
- SBUKOHLFHYSZNG-UHFFFAOYSA-N 4-dodecyl-2,6-dimethylmorpholine Chemical compound CCCCCCCCCCCCN1CC(C)OC(C)C1 SBUKOHLFHYSZNG-UHFFFAOYSA-N 0.000 claims description 5
- GOFJDXZZHFNFLV-UHFFFAOYSA-N 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C GOFJDXZZHFNFLV-UHFFFAOYSA-N 0.000 claims description 5
- 239000005755 Cyflufenamid Substances 0.000 claims description 5
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Abstract
本发明公开了一种杀真菌组合物,其包含(a)至少一种化合物,所述化合物选自式1的化合物、其N‑氧化物和盐,其中R1为F、Cl或Br;R2为H或F;并且R3为Cl或Br;和(b)至少一种杀真菌化合物,所述杀真菌化合物选自本文所公开的(b1)至(b13)。本发明还公开了一种用于控制由真菌植物病原体引起的植物病害的方法,其包括向植物或其部分、或向植物种子施加杀真菌有效量的式1的化合物、其N‑氧化物或盐(例如,作为上述组合物中的组分)。本发明还公开了可用于制备式(1)的化合物的过程中间体化合物。
Description
技术领域
本发明涉及某些吡唑衍生物、它们的N-氧化物和盐、用于其制备的过程中间体、和包含此类吡唑衍生物的混合物和组合物、以及将此类咪唑衍生物及其混合物和组合物作为杀真菌剂使用的方法。
背景技术
控制由真菌植物病原体引起的植物病害在获得高农作物效率中是极其重要的。对观赏作物、蔬菜作物、大田作物、谷类作物和果树作物有损害的植物病害可造成产量显著降低,从而导致消费成本上升。植物病害除了通常具有高破坏性之外,还可能难以控制,并且可发展对商业杀真菌剂的抗性。为此,许多产品可商购获得,但是持续需要更有效、更经济、更低毒性、对环境更安全或具有不同作用位点的新型杀真菌化合物。除了引入新型杀真菌剂以外,常常使用杀真菌剂的组合以有利于病害控制,拓宽控制范围并延缓抗性发展。此外,杀真菌剂的某些杰出组合展示了超出累加(即协同)的功效,从而提供商业上具有重要价值水平的植物病害控制度。本领域认识到,具体杀真菌剂组合的优点将根据以下这些因素而不同:具体的植物品种和待治疗的植物病害、以及在感染真菌植物病原体之前还是之后治疗植物。因此,需要新型的有利组合来提供多种选择,以最大程度地满足具体的植物病害控制需求。此类组合现已被发现。美国专利公布US 2011/0319430 A1公开了某些杀真菌吡唑类,但是未公开本发明的杀真菌混合物。
发明内容
本发明涉及一种杀真菌组合物(即,组合、混合物),其包含:
(a)至少一种化合物,所述化合物选自式1的化合物(包括所有立体异构体)、其N-氧化物和盐:
其中
R1为F、Cl或Br;
R2为H或F;并且
R3为Cl或Br;和
(b)至少一种杀真菌化合物,所述杀真菌化合物选自:
(b1)
其中Rb20和Rb21独立地为CH3、CF2H或CF3;每个Rb22独立地为卤素或氰基;n为0、1、2或3;并且L为直接键或-CH2O-,其中左边的键连接至二氢异唑环,并且右边的键连接至苯环(在式B1)中;
(b2)
其中Rb1为或
(b3)
其中Rb2为-CH2OC(O)CH(CH3)2、-C(O)CH3、-CH2OC(O)CH3、C(O)OCH2CH(CH3)2
或
(b4)
其中Rb3为CH3或F;
(b5)
(b6)
其中Rb4为-(CH2)4CH3、-C(CH3)3或-(CH2)2C≡CH;
(b7)
(b8)
(b9)
其中Rb5为H或F,并且Rb6为-CF2CHFCF3或-CF2CF2H;
(b10)
其中
Rb7为或
Rb8为H、卤素或C1-C2烷基;
Rb9为C1-C8烷基、C1-C8卤代烷基或C2-C8烷氧基烷基;
Rb10为卤素、C1-C2烷基或C1-C2卤代烷基;
Rb11为卤素、C1-C2烷基或C1-C2卤代烷基;
Rb12为C1-C2烷基;
Rb13为H、卤素或C1-C2烷基;
Rb14为C1-C2烷基或C1-C2卤代烷基;
Rb15为H、C1-C2烷基或C1-C2卤代烷基;
W为CH或N;
Y为CH或N;并且
Z为CH或N;
(b10a)
(b10b)
(b11)
(b12)
(b13)
以及它们的盐。
本发明还涉及一种杀真菌组合物,其包含:(a)至少一种化合物,所述化合物选自式1的化合物,(b)至少一种杀真菌化合物,所述杀真菌化合物选自上述式B1至B13及其盐,并且还包含(c)至少一种附加的化合物或试剂,所述附加的化合物或试剂为生物活性的。
本发明还涉及包含上述组合物中的一种的组合物,所述上述组合物包含组分(a)和(b)以及至少一种附加组分,所述附加组分选自表面活性剂、固体稀释剂和液体稀释剂。
本发明还涉及用于控制由真菌植物病原体引起的植物病害的方法,所述方法包括向植物或其部分或向植物种子施用杀真菌有效量的上述组合物中的一种。
前述方法还可描述为用于保护植物或植物种子免受由真菌病原体引起的病害的方法,所述方法包括向植物(或其部分)或植物种子施用杀真菌有效量的上述组合物中的一种(直接施用到植物或植物种子上,或通过环境(例如生长介质)施用)。
本发明还涉及上述式1的化合物、或其N-氧化物或盐。本发明还涉及杀真菌组合物,所述杀真菌组合物包含式1的化合物、或其N-氧化物或盐,以及至少一种附加组分,所述附加组分选自表面活性剂、固体稀释剂和液体稀释剂。本发明还涉及用于保护植物或植物种子免受由真菌病原体引起的病害的方法,所述方法包括向植物或植物种子施用杀真菌有效量的式1的化合物、或其N-氧化物或盐。
本发明还涉及式14的化合物,
其中R3为Cl或Br。
本发明还涉及式17的化合物,
其中
R1为F、Cl或Br;
R2为H或F;
R3为Cl或Br;并且
R32为H、CH3、CH2CH3或(CH2)2CH3;具体地前提条件是当R1为H时,或当R1和R2各自为F时,则R32为H。
本发明还涉及式20的化合物,
其中R1为F、Cl或Br,并且R2为H或F,具体地其中R1为Br,并且R2为F。
本发明还涉及式22的化合物,
其中R1为F、Cl或Br;R2为H或F;R3为Cl或Br;并且M为Na或K。
式14、17、20和22的化合物可用作用于制备式1的化合物的过程中间体,所述式1的化合物可用作本发明组合物中的组分(a)。
具体实施方式
如本文所用,术语“包括”、“包含”、“内含”、“涵盖”、“具有”、“含有”、“包容”、“容纳”、“特征在于”或者其任何其它变型旨在涵盖非排他性的包括,以任何明确指明的限定为条件。例如,包含一系列元素的组合物、混合物、工艺或方法不必仅限于那些元素,而是可以包括未明确列出的其它元素,或此类组合物、混合物、工艺或方法的其它固有元素。
连接短语“由...组成”不包括任何没有指定的元素、步骤或成分。如果是在权利要求中,则此类词限制权利要求,以不包含除了通常与之伴随的杂质以外不是所述那些的物质。当短语“由...组成”出现在权利要求主体的条款中,而不是紧接前言之后,则它仅限制此条款中描述的元素;其它元素没有被排除在作为整体的权利要求之外。
连接短语“基本上由...组成”用于限定组合物或方法,所述组合物或方法除了字面公开的那些以外,还包括物质、步骤、部件、组分或元素,前提条件是这些附加的物质、步骤、部件、组分或元素没有在很大程度上影响受权利要求书保护的本发明的基本特征和一种或多种新型特征。术语“基本上由...组成”居于“包含”和“由...组成”的中间。
当申请人已经用开放式术语如“包含”定义了本发明或其一部分,则应易于理解(除非另外指明),说明书应被解释为,还使用术语“基本上由...组成”或“由...组成”描述本发明。
此外,除非有相反的明确说明,“或”是指包含性的“或”,而不是指排他性的“或”。例如,以下中任一者均满足条件A或B:A是真的(或存在的)且B是假的(或不存在的)、A是假的(或不存在的)且B是真的(或存在的)以及A和B都是真的(或存在的)。
同样,涉及元素或组分例证(即出现)次数的位于本发明元素或组分前的不定冠词“一个”和“一种”旨在是非限制性的。因此,应将“一个”或“一种”理解为包括一个/一种或至少一个/一种,并且元素或组分的词语单数形式也包括复数形式,除非有数字明显表示单数。
如本公开和权利要求中所述,“植物”包括所有生命阶段的植物界成员,尤其是种子植物(裸子植物),所述生命阶段包括植物幼苗阶段(例如发芽的种子发育成幼苗)和成熟繁殖阶段(例如开花和结种的植物)。植物的部分包括通常生长在生长介质(例如土壤)表面下的向地性部分如根部、块茎、鳞茎和球茎,以及在生长介质上方生长的部分诸如叶(包括叶茎和叶片)、花、果实和种子。
如本文所述,单独或以词语的组合使用的术语“幼苗”是指由种子的胚胎发育的植物幼苗。
术语“登记号”是指化学文摘登记号。
在式(17和22)中画成波形线的单键带代表可存在E或Z异构体或E与Z异构体的混合物。垂直穿过键的虚线代表该键将取代基片段连接至分子的剩余部分(例如,式B2中的Rb1)。
与本发明的组合物和方法有关的化合物可以一种或多种立体异构体的形式存在。多种立体异构体包括对映异构体、非对映异构体、阻转异构体和几何异构体。本领域的技术人员将会知道,当一种立体异构体相对于一种或多种另一立体异构体富集时,或当与一种或多种另一立体异构体分离时,其可能更具活性和/或可能表现出有益效果。另外,本领域的技术人员知道如何分离、富集、和/或选择性地制备所述立体异构体。本发明组合物中的化合物可作为立体异构体的混合物、单独的立体异构体或以光学活性形式存在。
用于制备杂环的N-氧化物如吡唑类的合成方法是本领域技术人员很熟知的,包括使用过氧酸(如过乙酸和间氯过氧苯甲酸(MCPBA))、过氧化氢、烷基氢过氧化物(如叔丁基氢过氧化物)、过硼酸钠和双环氧乙烷(如二甲基双环氧乙烷)来氧化杂环。制备N-氧化物的这些方法已广泛描述和综述于文献中,参见例如:T.L.Gilchrist的ComprehensiveOrganicSynthesis,第7卷,第748-750页,S.V.Ley编辑,Pergamon Press;M.Tisler和B.Stanovnik的Comprehensive HeterocyclicChemistry,第3卷,第18-20页,A.J.Boulton和A.McKillop编辑,Pergamon Press;M.R.Grimmett和B.R.T.Keene的Advances inHeterocyclicChemistry,第43卷,第149-161页,A.R.Katritzky编辑,Academic Press;M.Tisler和B.Stanovnik的Advances inHeterocyclic Chemistry,第9卷,第285-291页,A.R.Katritzky和A.J.Boulton编辑,Academic Press;以及G.W.H.Cheeseman和E.S.G.Werstiuk的Advances inHeterocyclic Chemistry,第22卷,第390-392页,A.R.Katritzky和A.J.Boulton编辑,Academic Press。
本领域的技术人员认识到,由于在环境中和生理条件下化合物的盐与它们相应的非盐形式处于平衡,因此盐与非盐形式具有共同的生物用途。因此,单独和在混合物中的式1的化合物的各种盐可用于控制由真菌植物病原体引起的植物病害(即为农业上适宜的)。式1的化合物的盐包括与无机酸或有机酸形成的酸加成盐,所述酸如氢溴酸、盐酸、硝酸、磷酸、硫酸、乙酸、丁酸、富马酸、乳酸、马来酸、丙二酸、草酸、丙酸、水杨酸、酒石酸、4-甲苯磺酸、或戊酸。因此,本发明涉及化合物的混合物,所述化合物选自式1、其N-氧化物及其农业上适宜的盐。并且,对于式B1至B13的许多化合物而言,可存在生物学上类似的盐形式。
选自式1、其立体异构体、互变异构体、N-氧化物和盐的化合物通常以多于一种的形式存在,从而式1包括式1表示的所有晶体和非晶体形式的化合物。非晶体形式包括为固体的实施例如蜡和树胶,以及为液体的实施例如溶液和熔融物。晶体形式包括代表基本上单一晶型体的实施例,和代表多晶型体(即不同晶型)混合物的实施例。术语“多晶型体”涉及可以不同晶型结晶的化合物具体晶型,这些晶型在晶格中具有不同的分子排列和/或构象。虽然多晶型体可具有相同的化学组成,但是它们也可具有不同的组成,这应归因于是否存在微弱或强力键合于晶格内的共结晶的水或其它分子。多晶型体可具有不同的化学、物理和生物特性,如晶体形状、密度、硬度、颜色、化学稳定性、熔点、吸湿性、可悬浮性、溶解速率和生物利用度。本领域的技术人员将会知道,相对于由式1表示的相同化合物的另一种多晶型体或多晶型体混合物,由式1表示的化合物的多晶型体可表现出有益效果(例如制备可用制剂的适宜性、改善的生物性能)。由式1表示的化合物的具体多晶型体的制备和分离可通过本领域技术人员已知的方法实现,包括例如采用所选溶剂和温度进行结晶。式B1至B13的化合物(包括其盐)通常还可以多于一种的形式存在。
在包括下述那些的本发明的实施例中,除非在实施例中另外指明,与式1相关的包括其N-氧化物和盐,并且除非另外定义,与“式1的化合物”相关的包括发明内容中指定的取代基的定义。此外,除非另外指明,与式B1至B13相关的包括其盐。
实施例1:组合物,其包含发明内容中所述的组分(a)和(b),其中式1中,R2为F。
实施例2:组合物,其包含发明内容中所述的组分(a)和(b),其中式1中,R2为H。
实施例3:组合物,其包含发明内容或实施例1或2中所述的组分(a)和(b),其中组分(a)不包含式1的化合物的N-氧化物。
实施例4:组合物,其包含发明内容或实施例3中所述的组分(a)和(b),其中组分(a)包含选自以下的化合物:
4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物1)、
4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物10)、
N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物9)、
4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物12)、
4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物8)、
4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物6)、
4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物2)、
4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物3)、
N-(2-氯-6-氟苯基)-4-(2-氯-4-氟甲基)-1,3-二甲基-1H-吡唑-5-胺(化合物5)、
4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物11)、
4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物4)、以及
4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物7)
(其中化合物编号在索引表A中确定)。
实施例5:根据实施例4所述的组合物,其中所述组分(a)包含化合物1。
实施例6:根据实施例4所述的组合物,其中所述组分(a)包含化合物2。
实施例7:根据实施例4所述的组合物,其中所述组分(a)包含化合物3。
实施例8:根据实施例4所述的组合物,其中所述组分(a)包含化合物4。
实施例9:根据实施例4所述的组合物,其中所述组分(a)包含化合物5。
实施例10:根据实施例4所述的组合物,其中所述组分(a)包含化合物6。
实施例11:根据实施例4所述的组合物,其中所述组分(a)包含化合物7。
实施例12:根据实施例4所述的组合物,其中所述组分(a)包含化合物8。
实施例13:根据实施例4所述的组合物,其中所述组分(a)包含化合物9。
实施例14:根据实施例4所述的组合物,其中所述组分(a)包含化合物10。
实施例15:根据实施例4所述的组合物,其中所述组分(a)包含化合物11。
实施例16:根据实施例4所述的组合物,其中所述组分(a)包含化合物12。
实施例17:组合物,其包含发明内容或实施例1至16中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b1)的杀真菌化合物。
实施例17a:组合物,其包含发明内容或实施例1至17中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b1a)的杀真菌化合物。
实施例17b:组合物,其包含发明内容或实施例1至17a中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b1b)的杀真菌化合物。
实施例18:组合物,其包含发明内容或实施例1至17b中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b2)的杀真菌化合物。
实施例19:组合物,其包含发明内容或实施例1至18中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b3)的杀真菌化合物。
实施例20:组合物,其包含发明内容或实施例1至19中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b4)的杀真菌化合物。
实施例21:组合物,其包含发明内容或实施例1至20中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b5)的杀真菌化合物。
实施例22:组合物,其包含发明内容或实施例1至21中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b6)的杀真菌化合物。
实施例23:组合物,其包含发明内容或实施例1至22中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b7)的杀真菌化合物。
实施例24:组合物,其包含发明内容或实施例1至23中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b8)的杀真菌化合物。
实施例25:组合物,其包含发明内容或实施例1至24中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b9)的杀真菌化合物。
实施例26:组合物,其包含发明内容或实施例1至25中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b10)的杀真菌化合物。
实施例26a:组合物,其包含发明内容或实施例1至26中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b10a)的杀真菌化合物。
实施例26b:组合物,其包含发明内容或实施例1至26a中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b10b)的杀真菌化合物。
实施例27:组合物,其包含发明内容或实施例1至26b中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b11)的杀真菌化合物。
实施例28:组合物,其包含发明内容或实施例1至27中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b12)的杀真菌化合物。
实施例28a:组合物,其包含发明内容或实施例1至28中任一项所述的组分(a)和(b),其中组分(b)包含至少一种选自(b13)的杀真菌化合物。
实施例29:组合物,其包含发明内容或实施例1至28a中任一项所述的组分(a)和(b),还包含(c)至少一种附加的化合物或试剂,所述附加化合物或试剂为生物活性的。
实施例30:根据实施例29所述的组合物,其中所述组分(c)包含至少一种选自以下的杀真菌化合物:
(c1)苯并咪唑氨基甲酸甲酯(MBC)杀真菌剂;
(c2)二酰亚胺杀真菌剂;
(c3)脱甲基抑制剂(DMI)杀真菌剂;
(c4)苯基酰胺杀真菌剂;
(c5)胺/吗啉杀真菌剂;
(c6)磷脂生物合成抑制剂杀真菌剂;
(c7)酰胺杀真菌剂;
(c8)羟基(2-氨基-)嘧啶杀真菌剂;
(c9)苯胺基嘧啶杀真菌剂;
(c10)N-苯基氨基甲酸酯杀真菌剂;
(c11)醌外部抑制剂(QoI)杀真菌剂;
(c12)苯基吡咯杀真菌剂;
(c13)喹啉杀真菌剂;
(c14)类脂过氧化抑制剂杀真菌剂;
(c15)黑素生物合成抑制剂-还原酶(MBI-R)杀真菌剂;
(c16)黑素生物合成抑制剂-脱水酶(MBI-D)杀真菌剂;
(c17)羟基苯胺杀真菌剂;
(c18)角鲨烯-环氧酶抑制剂杀真菌剂;
(c19)多抗霉素杀真菌剂;
(c20)苯基脲杀真菌剂;
(c21)醌内部抑制剂(QiI)杀真菌剂;
(c22)苯甲酰胺杀真菌剂;
(c23)烯醇式吡喃糖醛酸抗生素杀真菌剂;
(c24)己吡喃糖基抗生素杀真菌剂;
(c25)吡喃葡糖基抗生素:蛋白质合成杀真菌剂;
(c26)吡喃葡糖基抗生素:海藻糖酶和肌醇生物合成杀真菌剂;
(c27)氰基乙酰胺肟杀真菌剂;
(c28)氨基甲酸酯杀真菌剂;
(c29)氧化磷酸化解偶联杀真菌剂;
(c30)有机锡杀真菌剂;
(c31)羧酸杀真菌剂;
(c32)杂芳族杀真菌剂;
(c33)膦酸酯杀真菌剂;
(c34)邻氨甲酰基苯甲酸杀真菌剂;
(c35)苯并三嗪杀真菌剂;
(c36)苯-磺酰胺杀真菌剂;
(c37)哒嗪酮杀真菌剂;
(c38)噻吩-甲酰胺杀真菌剂;
(c39)嘧啶酰胺杀真菌剂;
(c40)羧酸酰胺(CAA)杀真菌剂;
(c41)四环素抗生素杀真菌剂;
(c42)硫代氨基甲酸酯杀真菌剂;
(c43)苯甲酰胺杀真菌剂;
(c44)寄主植物防御诱导型杀真菌剂;
(c45)多位点接触活性杀真菌剂;
(c46)杀真菌剂,所述杀真菌化合物不是组分(a)和组分(c1)至(c45)的杀真菌剂;以及
(c1)至(c46)的化合物的盐。
实施例31:根据实施例29或30所述的组合物,其中所述组分(c)包含至少一种选自以下的化合物:阿拉酸式苯-S-甲基、aldimorph、唑嘧菌胺(ametoctradin)、吲唑磺菌胺、敌菌灵、戊环唑、嘧菌酯、苯霜灵、苯霜灵-M、麦锈灵、苯菌灵、苯噻菌胺、异丙基苯噻菌胺、bethoxazin、乐杀螨、联苯、联苯三唑醇、联苯吡菌胺、杀稻瘟菌素-S、啶酰菌胺、糠菌唑、乙嘧酚磺酸酯、丁硫啶、萎锈灵、环丙酰菌胺、敌菌丹、克菌丹、多菌灵、地茂散、百菌清、乙菌利、克霉唑、铜盐(诸如波尔多液(三元硫酸铜)、氢氧化铜和王铜)、赛座灭、环氟菌胺、霜脲氰、环丙唑醇、嘧菌环胺、抑菌灵、双氯氰菌胺、哒菌清、氯硝胺、乙霉威、醚唑、二氟林、甲菌定、烯酰吗啉、醚菌胺、烯唑醇、烯唑醇-M、敌螨普、二噻农、十二环吗啉、多果定、敌瘟磷、烯肟菌酯、氟环唑、乙环唑、噻唑菌胺、乙嘧酚、土菌灵、唑菌酮、咪唑菌酮、氯苯嘧啶醇、腈苯唑、甲呋酰胺、环酰菌胺、氰菌胺、拌种咯、苯锈啶、丁苯吗啉、胺苯吡菌酮、三苯基乙酸锡、三苯基氯化锡、三苯基氢氧化锡、福美铁、嘧菌腙、氟啶胺、咯菌腈、flumetover、氟吗啉、氟吡菌胺(也称为picobenzamid)、氟吡菌酰胺、氟酰亚胺、氟嘧菌酯、氟喹唑、氟硅唑、磺菌胺、flutianil(2-[[2-氟-5-(三氟甲基)苯基]硫代]-2-[3-(2-甲氧基苯基)-2-亚噻唑烷基]乙腈)、氟酰胺、粉唑醇、氟唑菌酰胺(fluxapyroxad)、灭菌丹、三乙膦酸铝、麦穗宁、呋霜灵、福拉比、己唑醇、霉灵、双胍盐、抑霉唑、亚胺唑、双胍辛胺、丁基甲氨酸碘代丙炔酯、种菌唑、异稻瘟净、异菌脲、丙森锌、稻瘟灵、吡唑萘菌胺(isopyrazam)、异噻菌胺、春雷霉素、醚菌酯、代森锰锌、双炔酰菌胺、代森锰、灭锈胺、消螨多、甲霜灵、甲霜灵-M、叶菌唑、磺菌威、代森联、苯氧菌胺、嘧菌胺、苯菌酮、腈菌唑、萘替芬、甲胂铁铵(甲基胂酸铁)、氟苯嘧啶醇、辛噻酮、呋酰胺、肟醚菌胺、霜灵、喹酸、咪唑、氧化萎锈灵、氧四环素、戊菌唑、戊菌隆、戊苯吡菌胺、吡噻菌胺、稻瘟酯、磷酸及其盐、苯酞、啶氧菌酯、粉病灵、多抗霉素、噻菌灵、咪鲜安、腐霉利、霜霉威、霜霉威-盐酸盐、丙环唑、丙森锌、丙氧喹啉、硫菌威、丙硫菌唑、唑菌胺酯、唑胺菌酯、唑菌酯、定菌磷、吡菌苯威(pyribencarb)、稗草畏、啶斑肟、嘧霉胺、pyriofenone、咯喹酮、吡咯尼群、喹唑、灭螨猛、快诺芬、五氯硝基苯、sedaxane、硅噻菌胺、硅氟唑、螺环菌胺、链霉素、硫、戊唑醇、tebufloquin、克枯烂、四氯硝基苯、特比萘芬、氟醚唑、噻菌灵、噻呋灭、硫菌灵、甲基硫菌灵、福美双、噻酰菌胺、甲基立枯磷、对甲抑菌灵、三唑酮、三唑醇、嘧菌醇、triazoxide、三环唑、十三吗啉、氟菌唑、三环唑、肟菌酯、嗪氨灵、垂吗酰胺、灭菌唑、烯效唑、井冈霉素、valifenalate(valiphenal)、乙烯菌核利、代森锌、福美锌、苯酰菌胺、N′-[4-[4-氯-3-(三氟甲基)苯氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒、5-氯-6-(2,4,6-三氟苯基)-7-(4-甲基哌啶-1-基)[1,2,4]三唑并[1,5-a]嘧啶(BAS600)、N-[2-[4-[[3-(4-氯苯基)-2-丙炔-1-基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲基磺酰基)氨基]丁酰胺、N-[2-[4-[[3-(4-氯苯基)-2-丙炔-1-基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(乙基磺酰基)氨基]丁酰胺、2-丁氧基-6-碘-3-丙基-4H-1-苯并吡喃-4-酮、3-[5-(4-氯苯基)-2,3-二甲基-3-异唑烷基]吡啶、N-[1-[[[1-(4-氰基苯基)乙基]磺酰基]甲基]丙基]氨基甲酸4-氟苯酯、N-[[(环丙基甲氧基)氨基][6-(二氟甲氧基)-2,3-二氟苯基]亚甲基]苯乙酰胺、α-(甲氧基亚氨基)-N-甲基-2-[[[1-[3-(三氟甲基)苯基]乙氧基]亚氨基]甲基]苯乙酰胺、N′-[4-[4-氯-3-(三氟甲基)苯氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、2-[[[[3-(2,6-二氯苯基)-1-甲基-2-丙烯-1-叉基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基苯乙酰胺、1-[(2-丙烯硫基)羰基]-2-(1-甲基乙基)-4-(2-甲基苯基)-5-氨基-1H-吡唑-3-酮、乙基-6-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、N-[4-[[[[(1-甲基-1H-四唑-5-基)苯基亚甲基]氨基]氧基]甲基-2-噻唑基]氨基甲酸戊酯、N-[6-[[[[(1-甲基-1H-四唑-5-基)苯基亚甲基]氨基]氧基]甲基-2-吡啶基]氨基甲酸戊酯、2-[(3-溴-6-喹啉基)氧基]-N-(1,1-二甲基-2-丁炔-1-基)-2-(甲硫基)乙酰胺、2-[(3-乙炔基-6-喹啉基)氧基]-N-[1-(羟甲基)-1-甲基-2-丙炔-1-基]-2-(甲硫基)乙酰胺、N-(1,1-二甲基-2-丁炔-1-基)-2-[(3-乙炔基-6-喹啉基)氧基]-2-(甲硫基)乙酰胺以及N′-[4-[[3-[(4-氯苯基)甲基]-1,2,4-噻二唑-5-基]氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒。
实施例32:根据实施例31所述的组合物,其中组分(c)包含至少一种选自以下的化合物:嘧菌酯、联苯吡菌胺、啶酰菌胺(啶酰菌胺)、糠菌唑、多菌灵、百菌清、环氟菌胺、环丙唑醇、醚唑、醚菌胺、氟环唑、乙环唑、唑菌酮、腈苯唑、苯锈啶、丁苯吗啉、氟吡菌酰胺、氟硅唑、氟唑菌酰胺(fluxapyroxad)、己唑醇、种菌唑、吡唑萘菌胺、醚菌酯、叶菌唑、苯氧菌胺/苯氧菌胺、苯菌酮、腈菌唑、戊菌唑、吡噻菌胺、啶氧菌酯、咪鲜安、丙环唑、丙氧喹啉、丙硫菌唑、唑菌胺酯、唑胺菌酯、唑菌酯、pyriofenone、快诺芬、sedaxane、戊唑醇、肟菌酯以及灭菌唑。
实施例33:根据实施例32所述的组合物,其中组分(c)包含至少一种选自以下的化合物:嘧菌酯、联苯吡菌胺、啶酰菌胺、环氟菌胺、环丙唑醇、醚唑、氟环唑、氟吡菌酰胺、吡唑萘菌胺、醚菌酯、叶菌唑、苯菌酮、腈菌唑、吡噻菌胺、啶氧菌酯、唑菌胺酯、唑胺菌酯、唑菌酯、pyriofenone、丙氧喹啉、丙硫菌唑、快诺芬、sedaxane、戊唑醇以及肟菌酯。
实施例34:组合物,其包含发明内容或实施例1至33中任一项所述的组分(a)和(b),其中所述组合物还包含组分(c),至少一种无脊椎害虫控制化合物或试剂。
作为实施例,值得注意的是一种组合物,所述组合物包含发明内容和实施例1至34中任一项所述的组分(a)和(b),其中组分(b1)为(b1a)(即式B1a)
还值得注意的是,涉及发明内容或本文所述任何实施例,包括实施例1-34中所述的组合物的杀真菌组合物或方法中的任一种,其中组分(b)不包含式B13的化合物(b13)或盐。还值得注意的是,涉及发明内容或本文所述任何实施例,包括实施例1-34中所述的组合物的杀真菌组合物或方法中的任一种,其中组分(b)还不包含式B10a的化合物(b10a)、式B10b的化合物(b10b),或其盐。
可以任何方式组合本发明的实施例,包括上述实施例1-34以及本文所述的任何其它实施例。此外,本发明的实施例,包括上文实施例1-34以及本文所述的任何其它实施例,以及它们的任何组合,涉及本发明的方法。此外,本文所述的本发明的实施例以及它们的组合涉及式1的化合物以及用于它们的制备的中间体,诸如式14、17、20和22的化合物。
值得注意的是,本文所述的实施例,包括实施例1至34中任一项所述的组合物,其中与式1相关的包括其盐但是不包括其N-氧化物;因此,短语“式1的化合物”可由短语“式1的化合物或其盐”代替。在该组合物中值得注意的是,组分(a)包含式1的化合物或其盐。
作为实施例,还值得注意的是本发明的杀真菌组合物包含实施例1至34中任一项所述的组合物(例如,以杀真菌有效量存在)以及至少一种附加的组分,所述附加的组分选自表面活性剂、固体稀释剂和液体稀释剂。
本发明的实施例还包括用于控制由真菌植物病原体引起的植物病害的方法,所述方法包括向植物或其部分,或向植物种子或幼苗施用杀真菌有效量的实施例1至34中任一项所述的组合物(例如作为包括如本文所述的制剂成分的组合物)。本发明的实施例还包括用于保护植物或植物种子免受由真菌病原体引起的病害的方法,所述方法包括向植物或植物种子施用杀真菌有效量的实施例1至34中任一项所述的组合物。
本发明的一些实施例涉及控制主要折磨植物叶的植物病害或防止该植物病害和/或向植物叶(即,植物而不是种子)施用本发明的组合物。优选的使用方法包括涉及上述优选组合物的那些;并且以特别效果被控制的病害包括由真菌植物病原体引起的植物病害。根据本发明使用的杀真菌剂的组合可有利于病害控制并且延缓抗性发展。
如发明内容中所述,本发明的一个方面涉及一种组合物,所述组合物包含作为组分(a)的至少一种化合物,所述化合物选自式1、其N-氧化物、及其盐。可使用如方案1-16中所述的下列方法和变型中的一种或多种来制备式1的化合物。除非另外指明,下式1-23的化合物中的R1、R2、R3、R32和M的定义如上述发明内容中所定义。式6a和6b是式6的各种子集;式10a是式10的子集;并且式17a是式17的互变异构的子集。除非另外指明,对于每个子集式的取代基如对于其母体式所定义。
如方案1中所示,式1的化合物可通过使式2的1H-吡唑化合物与各种甲基化试剂(例如式3)诸如碘甲烷、磺酸甲酯(如甲磺酸甲酯(OMs)或甲苯磺酸甲酯(OTs))或磷酸三甲酯,优选在诸如1,8-二-氮杂二环[5.4.0]十一碳-7-烯、碳酸钾或氢氧化钾的有机或无机碱存在下,并且在诸如N,N-二甲基甲酰胺(DMF)、四氢呋喃(THF)、甲苯或水的溶剂中反应来制备。
方案1
如方案2中所示,式1的化合物可通过使式4的化合物与包含离去基团G(例如,卤素或(卤)烷基磺酸酯)的式5的芳族化合物,任选地在金属催化剂存在下,并且一般在碱和诸如N,N-二甲基甲酰胺或二甲基亚砜的极性非质子溶剂存在下反应来制备。例如,其中苯环包含吸电子取代基的式5的化合物通过从环上直接取代离去基团G来反应,从而提供式1的化合物。式5的化合物可商购获得,或者它们的制备在本领域中是已知的。
方案2
根据方案2的方法,对于其中芳环缺乏足够的吸电子取代基的式4的化合物与式5的化合物的反应,或者为了改善反应速率、收率或产品纯度,金属催化剂(例如,金属或金属盐)的用量在从催化量至高达过量的范围内可有利于期望的反应。通常对于这些条件,G为Br或I或磺酸酯,诸如OS(O)2CF3或OS(O)2(CF2)3CF3。例如,可使用铜盐复合物(例如,CuI与N,N′-二甲基乙二胺、脯氨酸或吡啶)、钯复合物(例如三(二亚苄基丙酮)二钯(0))或钯盐(例如乙酸钯)与配体诸如4,5-双(二苯基膦基)-9,9-二甲基氧杂蒽(即“Xantphos”)、2-二环己基膦基-2′,4′,6′-三异丙基联苯(即“Xphos”)或2,2′-双(二苯基膦基)-1,1′-联二萘(即(“BINAP”),在碱诸如碳酸钾、碳酸铯、苯氧化钠或叔-丁醇钠的存在下,在诸如N,N-二甲基甲酰胺、1,2-二甲氧基乙烷、二甲基亚砜、1,4-二氧戊环或甲苯的溶剂中,任选地与醇如乙醇混合。作为另外一种选择,如方案3中所示,式1的化合物可通过使式6的化合物(即5-溴吡唑或其它在5-位上被离去基团取代的吡唑类)与式7的化合物在类似于上文对于方案2所述的那些金属催化的条件下反应来制备。式7的化合物可商购获得,或者它们的制备在本领域中是已知的。
方案3
如方案4中所示,其中G为Br或I的式6的化合物可通过使式4的5-氨基吡唑在重氮化条件下,在包含溴或碘的铜盐的存在下,或然后与包含溴或碘的铜盐组合进行反应来制备。例如,在CuBr2存在下,在溶剂如乙腈中向式4的5-氨基吡唑溶液中加入叔-丁基亚硝酸盐以提供对应的式6的5-溴吡唑。同样,通过在通常包含相同的卤原子的无机酸(对于G为I而言,如HI水溶液)的存在下,用亚硝酸钠在溶剂诸如水、乙酸或三氟乙酸中的溶液处理,随后根据本领域技术人员熟知的一般方法用相应的铜(I)或铜(II)盐处理,可将式4的5-氨基吡唑转化成重氮盐并然后转化成相应的式6的5-卤吡唑。
方案4
如方案5中所示,式6a的5-溴吡唑(即式6,其中G为Br)可通过使式8的5-羟基吡唑与三溴化磷反应来制备,如Tetrahedron Lett 2000,41(24),4713中所述。
方案5
如方案6中所示,式8的5-羟基吡唑还可被用于制备式6b的5-氟烷基磺酰基(例如,5-三氟甲烷磺酰基、5-九氟丁基磺酰基)吡唑(即式6,其中G为氟烷基磺酰基),如在Synlett,2004年,第5卷,第795页中所述。
方案6
如方案7中所示,式1的化合物可通过使式9的4-溴或碘代吡唑类与式10的有机金属化合物在过渡金属催化的交叉偶联反应条件下反应来制备。使式9的4-溴或碘代吡唑与硼酸、三烷基锡、锌或式10的有机镁试剂,在具有适当的配体(例如三苯基膦(PPh3)、二亚苄基丙酮(dba)、二环己基(2′,6′-二甲氧基[1,1′-联苯]-2-基)膦(SPhos))的钯或镍催化剂和碱(如果需要的话)存在下反应,提供对应的式1的化合物。例如,其中M为B(OH)2、B(OC(CH3)2C(CH3)2O))或B(O-i-Pr)3 的取代的芳基硼酸或衍生物,例如式10,与式9的4-溴-或4-碘吡唑在双(三苯基膦)二氯化钯(II)和碱水溶液诸如碳酸钠或氢氧化钾的存在下,在溶剂诸如1,4-二氧戊环、1,2-二甲氧基乙烷、甲苯或乙醇中反应,或在无水条件下与配体如氧化膦或磷酸盐配体(例如,二苯基膦氧化物)和氟化钾在溶剂如1,4-二氧戊环中反应(参见Angewandte Chemie,国际版2008,47(25),4695-4698),以提供对应的式1化合物。
方案7
如方案8中所示,式4的化合物可通过使用如对于方案7的方法所述的过渡金属催化交叉偶联反应条件,使式11的化合物与式10a的化合物(例如式10的化合物,其中M为B(OH)2)反应来制备。
方案8
如方案9中所示,其中G为Br或I的式9的吡唑类通过使4-位上未取代的吡唑类(式12)与卤化试剂诸如溴、亚溴酸钠、N-溴琥珀酰亚胺(NBS)或N-碘琥珀酰亚胺(NIS),在溶剂诸如乙酸、乙腈、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或1,4-二氧戊环或水与上述溶剂的混合物中,在环境温度至溶剂沸点范围内的温度下反应而容易地制备。
方案9
如方案10中所示,使用类似于用于方案9的方法的那些反应条件,其中式13的吡唑可转化成式11的中间体,其可用于制备如在方案8中所述的式4的化合物。式13的化合物不仅可由本领域已知的方法制备,而且可商购获得。
方案10
如方案11中所示,式12的化合物可通过类似于用于方案2的方法的那些工序由对应的式13的化合物制备。式13的化合物可商购获得或可通过本领域已知的方法制备。
方案11
可用于制备式4的5-氨基吡唑的一般方法是本领域熟知的;参见,例如dournalPraktische Chemie(Leipzig)1911,83,171和J.Am.Chem.Soc.1954,76,501。此类方法如方案12中所示。
方案12
相似地,可用于制备式8的5-羟基吡唑的一般方法是本领域熟知的;参见,例如Annalen der Chemie 1924,436,88。此类方法如方案13中所示。
方案13
如方案14中所示,根据本领域已知的一般方法,式1的化合物可使式17的化合物与甲基肼(式15)在溶剂诸如乙醇或甲醇中,并任选地在酸或碱催化剂诸如乙酸、哌啶或甲醇钠存在下缩合来制备。方案14的方法通过合成实例1的步骤C和合成实例2的步骤B来举例说明。
方案14
以类似于方案14的方法的方式,式2的化合物可通过使式17的化合物与肼缩合类似地制备。该方法描述于Chemistry of Heterocyclic Compounds 2005,41(1),105-110中。
如方案15中所示,式17的化合物(其中,R32为H或低级烷基,诸如CH3、CH2CH3或(CH2)2CH3)可通过使式18对应的烯酮二硫缩酮化合物与式19的化合物,任选地在碱诸如氢化钠或乙基氯化镁的存在下,在溶剂诸如甲苯、四氢呋喃或二甲氧基甲烷中,在-10℃至所述溶剂沸点范围内的温度下反应来制备。参见,例如J.Heterocycl.Chem.1975,12(1),139。可用于制备式18化合物的方法在本领域中是已知的。
方案15
如方案16中所示,其中R32为低级烷基(例如甲基、乙基、正丙基)的式17的化合物和式17a(即,式17的互变异构体,其中R32为H)的化合物可由式20的对应异硫氰酸酯化合物与式21的芳基丙酮化合物的缩合反应开始以获得式22的中间体化合物来制备,所述中间体化合物为式17a的硫代酰胺的盐。式22的中间体化合物可如合成实例1的步骤C所述按原样使用,或如合成实例2的步骤A和B所述在进一步转化之前分离。可用于制备式22的化合物的碱包括钠或钾的氢化物、醇盐、氢氧化物或碳酸盐,诸如氢化钠、叔丁醇钾、乙醇钠、氢氧化钾、氢氧化钠或碳酸钾。还可使用胺碱(例如,三乙胺或N,N-二异丙基乙胺)来进行式20和21的化合物的缩合。多种溶剂是可用的,诸如四氢呋喃、醚、甲苯、N,N-二甲基甲酰胺、醇类(例如,乙醇)、酯(例如,乙酸乙酯或乙酸异丙酯)、或它们的混合物。选择与所选的碱相容的溶剂,如本领域所熟知的。反应温度可在-78℃至溶剂沸点的范围内。一种可用的碱和溶剂的混合物为叔丁醇钾的四氢呋喃溶液,在-70至0℃下,向其中加入式20的异硫氰酸酯和式21的羰基化合物的溶液,它们可混合成一种溶液或分别添加,优选加入羰基化合物,随后加入异硫氰酸酯。式22的盐化合物可被酸化以形成式17a的酮基硫代酰胺化合物或用R32X1(式23)烷基化以形成式17的对应化合物,其中R32为低级烷基(例如,甲基、乙基、正丙基)且X1为离核体(即,亲核反应离去基团诸如Br、I、OS(O)2CH3)。该一般方法在化学文献中已知;参见,例如,Zhurnal Organicheskoi Khimii 1982,18(12),2501。用于制备其中R32为甲基的式17的非分离中间体化合物的方案16的方法由合成实例1的步骤C举例说明。用于制备式22的分离的中间体化合物的方案16的方法由合成实例2的步骤A举例说明。
方案16
式17a的酮基硫代酰胺还可通过使对应的酮基硫代酰胺与硫化试剂诸如Lawesson试剂或P2Ss反应来制备;参见例如,Helv.Chim.Act.1998,81(7),1207。
本领域的技术人员应认识到,各种官能团可被转变成其它官能团,以提供不同的式1的化合物。例如,用于制备式1的化合物的中间体可包含芳族硝基,其可被还原成氨基,然后经由本领域熟知的反应如Sandmeyer反应,被转换成各种卤化物,从而提供式1的化合物。
上述反应还可在许多情况下以轮流页序进行,诸如可通过下文对于取代的吡唑类的一般制备所举例说明的反应来制备用于方案2中反应的1H吡唑类。
应认识到,上述用于制备式1的化合物的某些试剂和反应条件可能不与中间体中存在的某些官能团相容。在这些情况下,将保护/去保护序列或官能团互变体加入到合成中将有助于获得所期望的产物。保护基团的使用和选择对化学合成领域的技术人员来讲将是显而易见的(参见例如Greene,T.W.Wuts,P.G.M.Protective Groups in OrganicSynthesis,第2版;Wiley:New York,1991)。本领域的技术人员将认识到,在一些情况下,在按照任何单独方案中的描述引入指定试剂后,可能需要实施没有详细描述的额外常规合成步骤以完成式1的化合物的合成。本领域的技术人员还将认识到,可能需要以与制备式1的化合物时所示的具体页序不同的页序来实施上文方案中示出的步骤的组合。本领域的技术人员还将认识到,本文所述的式1的化合物和中间体可经历各种亲电反应、亲核反应、自由基反应、有机金属反应、氧化反应和还原反应,以引入取代基或修饰现有的取代基。
无需进一步详尽说明,据信本领域的技术人员使用上述合成具体实施方式可将本发明以其最大限度利用。因此,以下合成例子应理解为仅是例证性的,而不以任何方式限制本发明的公开内容。以下合成例子中的步骤示出了整个合成转化中每个步骤的过程,并且用于每个步骤的原料不必由其过程描述于其他步骤中的具体制备步骤制得。百分比均按重量计,除非是色谱溶剂混合物或除非另外指明。色谱溶剂混合物的份数和百分比均按体积计,除非另外指明。除非另有说明,否则1H NMR谱由四甲基硅烷在CDCl3中以ppm的低场报道;“s”表示单峰、“br s”表示宽单峰、“d”表示双峰,“dd”表示双二重峰,“t”表示三重峰,“dt”表示双重三重峰,“m”表示多重峰。
合成实例1
4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基
-
1H-吡唑-5-胺(化合物4)
的制备
步骤A:1-(2-溴-4-氟苯基)-2-丙酮
的制备将甲醇钠的甲醇溶液(25%,34mL,157mmol)与甲苯(200mL)混合。然后使用Dean-Stark分水器在90℃下蒸馏出甲醇。在溶液冷却至70℃之后,由滴液漏斗经过20min,在机械搅拌下,添加溶解于乙酸乙酯(40mL)中的2-溴-4-氟苯乙腈(21.4g,100mmol)。此时,加入附加的甲苯(150mL),以有利于大量的淡粉色沉淀的搅拌。将反应混合物倾注到水中,并且分离有机相。酸化水相并用乙酸乙酯萃取该水相。干燥乙酸乙酯相并在减压下浓缩以提供作为粗制油的中间体化合物α-乙酰基-2-溴-4-氟苯乙腈。
在硫酸(60%,170mL)中搅拌所述粗制油,并使反应混合物回流6.5h。然后用己烷(2×100mL)萃取所述反应混合物,并且将经混合的己烷萃取物用水和盐水洗涤,干燥(MgSO4)并在减压下浓缩,以产生为黄色油状标题化合物(14.7g),其无需进一步纯化而用于步骤C中。
1H NMRδ7.33(m,1H),7.18(m,1H),7.01(m,1H),3.85(s,2H),2.23(s,3H)。
步骤B:1-氯-3-氟-2-异氰硫酸苯酯
的制备向2-氯-6-氟苯胺(5.0g,34mmol)的氯苯(52mL)溶液中加入二氯硫化碳(硫光气)(5.1g,45mmol)和DMF(0.27mL)。反应混合物回流2h,然后浓缩以留下为棕色油的标题化合物(6.15g),其无需进一步纯化而用于步骤C中。
1H NMRδ7.18(m,2H),7.07(m,1H)。
步骤C:4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺的制
备
在0℃下,经过5分钟,向叔丁醇钾(0.41g,3.3mmol)的THF(20mL)溶液中加入1-(2-溴-4-氟苯基)-2-丙酮(即,步骤A的产物)(0.70g,3.0mmol)的THF(10mL)溶液。持续搅拌1h,然后使温度下降至-10℃。经过6分钟,添加1-氯-3-氟-2-异氰硫酸苯酯(即,步骤B的产物)(0.57g,3.0mmol)的THF(10mL)溶液,并持续搅拌15分钟以提供包含中间体化合物3-(2-溴-4-氟苯基)-4-[(2-氯-6-氟苯基)氨基]-4-巯基-3-丁烯-2酮钾盐(1∶1)的反应混合物,所述中间体化合物为α-乙酰基-2-溴-N-(2-氯-6-氟苯基)-4-氟苯乙烷硫代酰胺的钾盐。加入碘甲烷(0.54g,3.8mmol),并且移除冷却浴以提供包含中间体化合物3-(2-溴-4-氟苯基)-4-[(2-氯-6-氟苯基)氨基]-4-(甲硫基)-3-丁烯-2-酮的反应混合物。5min后,连续快速地加入水(0.2mL,11mmol)、冰醋酸(0.53mL,9.1mmol)和甲基肼(0.81mL,15mmol),并且将反应混合物加热至回流并持续6h。然后在减压下浓缩粗制反应混合物并通过MPLC(0至100%乙酸乙酯的己烷溶液作为洗脱液)纯化以提供灰白色固体状标题产物(0.55g)。
1H NMRδ7.24(m,1H),7.04(m,1H),6.95(m,1H),6.87(m,1H),6.78(m,1H),6.68(m,1H),5.45(d,1H),3.80(s,3H),2.10(s,3H)。
实例2
4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺(化合物11)
的制备
步骤A:3-(2-溴-4-氟苯基)-4-[(2,6-二氟苯基)氨基]-4-巯基-3-丁烯-2-酮钾盐
(1∶1)的制备
在30min内,向借助于冰浴冷却至6℃的1-(2-溴-4-氟苯基)-2-丙酮(23.4g,101mmol)的甲基叔丁基醚(300mL)溶液中加入叔丁醇钾的四氢呋喃溶液(1.0M,100mL,100mmol)。在添加约90mL的叔丁醇钾溶液的过程中,将反应混合物的温度维持在6-8℃,然后在剩余的叔丁醇钾溶液的添加过程中除去冰浴。
在叔丁醇钾溶液添加完成之后,反应混合物为在12℃下的淡黄色溶液。将反应混合物在12-16℃下搅拌30min。然后将反应混合物冷却至3℃,并在20min内添加1,3-二氟-2-异氰硫酸苯酯(17.4g,102mmol)的甲基叔丁基醚(50mL)溶液,同时将反应混合物的温度维持在3和5℃之间。然后,在90min内将所得的黄色浆液缓慢加热至12℃。混合物用己烷(100mL)稀释并冷却至8℃,然后通过过滤分离固体产物。将产物在70℃的真空炉中干燥过夜,以提供黄色固体状标题产物(32.3g)。
1H NMR(DMSO-d6)δ14.36(s,1H),7.38(dd,1H),7.22(dd,1H),7.17(m,1H),7.06(dd,1H),6.99(t,2H),1.50(s,3H)。
步骤B:4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺
的制备在65℃下,将3-(2-溴-4-氟苯基)-4-[(2,6-二氟苯基)氨基]-4-巯基-3-丁烯-2酮钾盐(1∶1)(即步骤A的产物)(32.3g,73.4mmol)、乙酸(44g,73mmol)和甲肼(109mmol)在乙醇(200mL)中的搅拌混合物加热3h。然后在15min内使温度上升至70℃。在30min内,向淡黄色浑浊反应混合物中加入水(200mL)。在2h内将所得的黄色浆液冷却至8℃,然后在8℃下保持30min以上。固体通过过滤收集,用含水乙醇冲洗(按体积计,1∶4EtOH-H2O),并在70℃的真空炉中干燥以提供黄色固体(25g)
状标题产物。
1H NMRδ7.23(dd,1H),7.06(dd,1H),6.89(dt,1H),6.68(m,3H),5.15(br s,1H),3.81(s,3H),2.11(s,3H)。
通过本文所述的工序连同本领域已知的方法,可制备下表1中所公开的化合物。
表1
表2-5公开了可用作用于制备式1的化合物、其N-氧化物和盐的过程中间体的具体化合物。这些表中的“注释”栏表示代表性化合物的物理特性数据(例如,1H NMR谱、一个或多个MS母离子、熔程)。质谱(MS)作为通过向所述分子加成H+(分子量为1)所形成的最高同位素丰度母离子(M+1)的分子量报道,采用大气压化学电离(Ap+)通过质谱仪观察。未报道包含一个或多个较低丰度(例如37Cl、81Br)的较高原子量同位素的分子离子的存在。在一些情况下,还报道了M-1离子。
如方案12所述,式14的化合物是用于制备作为式1的化合物的中间体的式4的化合物的可用过程中间体,所述式1化合物可用作本发明组合物中的组分(a)。例证性的式14的化合物为表2中所具体描述的那些。
表2
注释2-1:1H NMR(CDCl3)δ87.49(m,1H),7.25(m,1H),7.11(m,1H),5.14(s,1H),2.36(s,3H)。
注释2-2:1H NMR(CDCl3)δ87.49(m,2H),7.41(m,1H),7.17(m,1H),5.20(s,1H),2.35(s,3H)。
如方案14所述,包括式17a(式17互变异构体,其中R32为H)的式17化合物是用于制备式1的化合物的可用过程中间体,所述式1的化合物可用作本发明组合物中的组分(a)。例证性的式17和17a的化合物为表3a和3b中所具体描述的那些。
表3a
注释3a-1:1H NMR(CDCl3)δδ15.36(s,1H),8.09(d,1H),7.62(br s,1H),7.52(dd,1H),7.42(q,1H),7.37(d,1H),7.29(t,1H),7.19(m,2H),1.82(s,3H)。
注释3a-2:MS 420(M+1)。熔点134-135℃。
注释3a-3:1H NMR(CDCl3)δ15.29(s,1H),7.53(dd,1H),7.43(dd,1H),7.29(m,1H),7.19(dt,1H),6.95(t,2H),6.82(s,1H),1.81(s,3H)。
表3b
注释3b-1:1H NMR(CDCl3)δ12.76(s,1H),7.66(d,1H),7.43(m,2H),7.32(q,1H),7.24(t,1H),7.10(m,2H),1.89(s,3H),1.84(s,3H)。
注释3b-2:MS 459.8(M+1),457.9(M-1)。
注释3b-3:MS 372.0(M+1)。
注释3b-4:MS 433.8(M+1)。
注释3b-5:1H NMR(CDCl3)δ12.53(s,1H),7.42(dd,1H),7.32(dd,1H),7.22(m,1H),7.08(dt,1H),6.97(t,2H),1.92(s,3H),1.89(s,3H)。
注释3b-6:MS 433.8(M+1),431.8(M-1)。
注释3b-7:MS 477.8(M+1),475.8(M-1)。
如方案16所述,式20的化合物是用于制备作为式1的化合物中间体的式17和17a的化合物的可用过程中间体,所述式1的化合物可用作本发明组合物中的组分(a)。例证性的式20的化合物为表4中所具体描述的那些。
表4
注释4-1:参见合成实例1,步骤B的1H NMR谱。
注释4-2:1HNMR(CDCl3)δ7.36(m,1H),7.10(m,1H)。19F NMR(CDCl3)δ-114.93(m,1F)。
如方案16所述,式22的化合物是用于制备作为式1的化合物中间体的式17和17a化合物的可用过程中间体,所述式1的化合物可用作本发明组合物中的组分(a)。例证性的式22的化合物为表5中所具体描述的那些。
表5
注释5-1:熔点115-118℃。
注释5-2:1H NMR(DMSO-d6)δ15.09(s,1H),8.98(d,1H),7.39(d,1H),7.35(d,1H),7.21(dd,1H),7.10(m,2H),6.90(t,1H),1.49(s,3H)。
注释5-3:参见合成实例2,步骤B的1HNMR谱。
显然,现在已发现式1的2,6-取代的苯胺-吡唑化合物,相比于其中连接到R1和R2的苯环在相对于将苯环连接到分子剩余部分的键的对位处具有非氢取代基的对应化合物,具有显著改善的药代动力学特性。具体地,在脊椎动物中,已发现式1的化合物与对位取代的类似物相比具有显著减少的进入脂肪的分配,从而降低生物累积的可能性。此外,除了在脊椎动物中具有更有利的药代动力学特性,还已发现其中R2为F的式1的2,6-取代的苯氨基-吡唑化合物,当苯基对位未取代时,保持对抗诸如由叶枯病菌(Septoria tritici)引起的植物真菌病害的显著高的活性。因为它们的非常可取的生物特性,所以式1的化合物作为组分(a)与组分(b)的杀真菌化合物以及本发明组合物中作为组分(c)的任选地其它生物活性化合物或试剂组合是非常有用的。此外,可用于制备式1的化合物的过程中间体,诸如式14、17、20和22的化合物相应地特别有用。
式1的化合物的药代动力学特性可使用药物科学中已知的多种分析方法来测量。在涉及单一口服剂量的一个例证性方法中,三只雄性和三只雌性大鼠经由管饲法接收单剂量测检物。在投配之前,然后在0.25、0.5、1、2、4、8、12、24h以及其后每隔24h直至死亡,立即经由尾静脉收集大约0.25mL血液。死亡时,还收集脂肪以确定死亡时所述脂肪∶血浆比率。将血液收集到包含乙二胺四乙酸(EDTA)的试管中,并以2500×g离心以便将血浆与血细胞分离。然后使用例如乙腈和蛋白质沉淀板(如,Strata Impact蛋白质沉淀板,Phenomenex,Torrance,CA,U.S.A.的产品型号CEO-7565)按照板提供的说明,通过蛋白质沉淀来萃取所述血浆。作为另外一种选择,血浆仅用乙腈萃取、涡旋(即,使用涡旋混合器混合)并离心以使蛋白质成粒状。在移除蛋白质以后,通过液相色谱法-质谱仪(LC/MS)对血浆进行母体化合物和/或代谢物进行分析。脂肪通过有机溶剂诸如乙腈均化并萃取。然后通过LC/MS对提取物进行母体化合物和/或代谢物分析。然后使用非线性模型软件(例如,得自Pharsight,Cary,NC,U.S.A.的WinNonlinTM)分析血浆药代动力学数据以确定在血浆中所施用化合物的半衰期、施用后达到最大血浆浓度时的时间(Tmax)、最大血浆浓度(Cmax)、以及血浆浓度曲线下的面积(AUC)。因为脂肪的分析需要大鼠死亡,脂肪数据在单个时间点处获得(即大鼠死亡的时间)。然而,通过使用在距投配时间的不同间隔后死亡的多只大鼠,确定脂肪的此类参数作为Cmax。使用上述方法,发现在索引表A中认定的化合物3、4和5,相比于其中连接至R1和R2的苯环在相对于将苯环连接到分子剩余部分的键的对位处具有非氢取代基的对应化合物,具有显著减小的进入脂肪的分配。
在包含(a)至少一种选自式1、其N-氧化物和盐的化合物,与(b)至少一种选自组分(b)的杀真菌化合物的组合物中,组分(b)选自组分(b1)至(b13),即分别为式B1至B13,包括其盐。
组分(b1)涉及式B1的化合物
其中Rb20和Rb21独立地为CH3、CF2H或CF3;每个Rb22独立地为卤素或氰基;n为0、1、2或3;并且L为直接键或-CH2O-,其中左边的键连接至二氢异唑环,并且右边的键连接至苯环。值得注意的是,作为其中L为直接键的式B1的化合物的例子为(b1a)式B1a的化合物
其为1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)H-吡唑-1-基]乙酮(登记号1003318-67-9)。特别值得注意的是(b1aa),并且式B1a-R的R对映体
其为1-[4-[4-[5-R(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)H-吡唑-1-基]乙酮(登记号1003319-79-6)。其中L为-CH2O-的式B1的化合物的例子包括(b1b)式B1b的化合物
其为1-[4-[4-[5-[(2,6-2氟苯氧基)甲基]-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮。用于制备式B1的化合物的方法描述于PCT专利公布WO 2008/013622和PCT专利申请PCT/US11/64324中。
组分(b2)涉及式B2的化合物
其中Rb1为或
式B2的化合物的例子包括(b2a)(2-氯-6-氟苯基)甲基2-[1-[2-[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基]-4-哌啶基]-4-噻唑甲酸乙酯(登记号1299409-40-7)和(b2b)(1R)-1,2,3,4-四氢-1-萘基2-[1-[2-[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基]-4-哌啶基]-4-噻唑甲酸乙酯(登记号1299409-42-9)。用于制备式B2的化合物的方法描述于PC专利公布WO 2009/132785和WO 2011/051243中。
组分(b3)涉及式B3的化合物
其中Rb2为-CH2OC(O)CH(CH3)2、-C(O)CH3、-CH2OC(O)CH3、-C(O)OCH2CH(CH3)2或
式B3的化合物的例子包括(b3a)[[4-甲氧基-2-[[[(3S,7R,8R,9S)-9-甲基-8-(2-甲基-1-氧丙氧基)-2,6-二氧-7-(苯基甲基)-1,5-二氧庚环-3-基]氨基]羰基]-3-吡啶基]氧基]甲基2-甲基丙酸酯(登记号517875-34-2)、(b3b)(3S,6S,7R,8R)-3-[[[3-(乙酰氧基)-4-甲氧基-2-吡啶基]羰基]氨基]-6-甲基-4,9-二氧-8-(苯基甲基)-1,5-二氧庚环-7-基2-甲基丙酸酯(登记号234112-93-7)、(b3c)(3S,6S,7R,8R)-3-[[[3-[(乙酰氧基)甲氧基]-4-甲氧基-2-吡啶基]羰基]氨基]-6-甲基-4,9-二氧-8-(苯基甲基)-1,5-二氧庚环-7-基2-甲基丙酸酯(登记号517875-31-9)、(b3d)(3S,6S,7R,8R)-3-[[[4-甲氧基-3-[[(2-甲基丙氧基)羰基]氧基]-2-吡啶基]羰基]氨基]-6-甲基-4,9-二氧-8-(苯基甲基)-1,5-二氧庚环-7-基2-甲基丙酸酯(登记号328256-72-0)、以及(b3e)N-[[3-(1,3-苯并二氧杂环戊烯-5-基甲氧基)-4-甲氧基-2-吡啶基]羰基]-O-[2,5-双脱氧-3-O-(2-甲基-1-氧代丙基)-2-(苯基甲基)-L-arabinonoyl]-L-丝氨酸,(1→4′)-内酯(登记号1285706-70-8)。用于制备式B3的化合物的方法描述于PCT专利公布WO 99/40081、WO 2001/014339、WO 2003/035617和WO 2011044213中。
组分(b4)涉及式B4的化合物
其中Rb3为CH3或F。
式B4的化合物的例子包括(b4a)5-氟-2-[(4-甲基苯基)甲氧基]-4-嘧啶胺(登记号1174376-25-0)和(b4b)5-氟-2-[(4-氟苯基)甲氧基]-4-嘧啶胺(登记号1174376-11-4)。式B4的化合物可通过描述于PCT专利公布WO 2009/094442中的方法来制备。
组分(b5)涉及式B5的化合物
其为5,8-二氟-N-[2-[3-甲氧基-4-[[4-(三氟甲基)-2-吡啶基]氧基]苯基]乙基]-4-氨基喹唑啉(登记号1210070-31-7)。式B5的化合物可通过描述于PCT专利公布WO2010/025451中的方法来制备。
组分(b6)涉及式B6的化合物
其中Rb4为-(CH2)4CH3、-C(CH3)3或-(CH2)2C≡CH。
式B6化合物的例子包括:(b6a)[6-[[[(Z)-[(1-甲基-1H-四唑-5-基)苯亚甲基]氨基]氧基]甲基]-2-吡啶基]氨基甲酸戊酯(登记号500207-05-6)、(b6b)1,1-二甲基乙基N-[6-[[[(Z)-[(1-甲基-1H-四唑-5-基)苯亚甲基]氨基]氧基]甲基]-2-吡啶基]氨基甲酸酯(登记号500207-04-5)、以及(b6c)3-丁炔-1-基N-[6-[[[(Z)-[(1-甲基-1H-四唑-5-基)苯亚甲基]氨基]氧基]甲基]-2-吡啶基]氨基甲酸酯(登记号1202946-82-4)。式B6的化合物可通过描述于PCT专利公布WO 2003/016303中的方法来制备。
组分(b7)涉及式B7的化合物
其为N-(3′,4′-二氟[1,1′-联苯基]-2-基)-3-(三氟甲基)-2-对二氮苯酰胺(登记号942515-63-1)。式B7的化合物可通过描述于PCT专利公布WO 2007/072999中的方法来制备。
组分(b8)涉及式B8的化合物
其为N-[2-(2,4-二氯苯基)-2-甲氧基-1-甲基乙基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺(登记号1092400-95-7)。式B8的化合物可通过描述于PCT专利公布WO 2008/148570中的方法来制备。
组分(b9)涉及式B9的化合物
其中Rb5为H或F,并且Rb6为-CF2CHFCF3或-CF2CF2H。式B9的化合物的例子为(b9a)3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺(登记号1172611-40-3)和(b9b)3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺(登记号923953-98-4)。式B9的化合物可通过描述于PCT专利公布WO2007/017450中的方法来制备。
组分(b10)涉及式B10的化合物
其中
Rb7为或
Rb8为H、卤素或C1-C2烷基;
Rb9为C1-Cs烷基、C1-Cs卤代烷基或C2-Cs烷氧基烷基;
Rb10为卤素、C1-C2烷基或C1-C2卤代烷基;
Rb11为卤素、C1-C2烷基或C1-C2卤代烷基;
Rb12为C1-C2烷基;
Rb13为H、卤素或C1-C2烷基;
Rb14为C1-C2烷基或C1-C2卤代烷基;
Rb15为H、C1-C2烷基或C1-C2卤代烷基;
W为CH或N;
Y为CH或N;并且
Z为H或N。
组分(b10a)涉及isofetamid(IKF-5411),其为N-[1,1-二甲基-2-[2-甲基-4-(1-甲基乙氧基)苯基]-2-氧代乙基]-3-甲基-2-噻吩甲酰胺(登记号875915-78-9),即,式B10a的化合物
该化合物以及组分(b10)的化合物可通过PCT专利公布WO 2006/016708和WO2007/069777中所述的方法来制备。
组分(b10b)涉及tolprocarb(MTF-0301),其为2,2,2-三氟乙基N-[(1S)-2-甲基-1-[[(4-甲基苯甲酰基)氨基]甲基]丙基]氨基甲酸酯(登记号911499-62-2),即式B10b的化合物
该化合物可通过美国专利公布US 2007/0049635A1中所述的方法来制备。
组分(b11)涉及式B11的化合物
其为(αR)-2-[(2,5-二甲基苯氧基)甲基]-α-甲氧基-N-甲基苯乙酰胺(登记号394657-24-0)。式B11的化合物可通过描述于PCT专利公布WO 95/27693中的方法来制备。
组分(b12)涉及式B12的化合物
其为2,6-二甲基-1H,5H-[1,4]二噻烯[2,3-c5,6-c′]联吡咯-1,3,5,7(2H,6H)-四酮(登记号16114-35-5)。式B12的化合物可通过描述于专利公布3364229中的方法来制备。
组分(b13)涉及式B13的化合物
其为N-环丙基-3-(二氟甲基)-5-氟-1-甲基-N-[[2-(1-甲基乙基)苯基]甲基]-1H-吡唑-4-甲酰胺(登记号1255733-83-5)。式B13的化合物可通过描述于PCT专利公布WO2010/130767中的方法来制备。
上述组合物通常将由组分(a)和(b)的协同作用提供对植物病害的改善的控制(即,预防和/或治愈),所述组合物包含如下组分的组合:(a)至少一种化合物,所述化合物选自式1的化合物,包括其N-氧化物和盐,连同(b)至少一种杀真菌组分,所述杀真菌组分选自式B1至B13,包括其盐。改善的植物病害控制可通过更广谱或更长持续时间的植物病害控制,或抗性发展的延迟来显示。组分(a)和(b)的作用可以互补地累加或甚至大于通过协同作用的累加。
本发明还涉及一种杀真菌组合物,其包含:(a)至少一种化合物,所述化合物选自式1的化合物,(b)至少一种杀真菌化合物,所述杀真菌化合物选自上述式B1至B13,并且还包含(c)至少一种附加化合物或试剂,所述附加化合物或试剂为生物活性的。因此,组分(a)与组分(b)的组合物还可与(c)一种或多种其它生物学活性化合物或试剂混合以形成多组分杀虫剂,从而赋予甚至更广谱的农业保护,所述生物学活性化合物或试剂包括杀虫剂、杀线虫剂、杀细菌剂、杀螨剂、除草剂、除草剂安全剂、生长调节剂诸如昆虫蜕皮抑制剂和生根刺激剂、化学不育剂、化学信息素、拒斥剂、诱虫剂、信息素、取食刺激剂、植物营养素、其它生物学活性化合物或昆虫病原细菌、病毒或真菌。这些农用保护剂的一般参考文献包括ThePesticide Manual,第13版,C.D.S.(Tomlin编辑,British Crop Protection Council,Farnham,Surrey,U.K.,2003)和The BioPesticide Manual,第2版(L.G.Copping编辑,British Crop Protection Council,Farnham,Surrey,U.K.,2001)。
更具体的方面涉及所述真菌组合物,其中组分(c)包含至少一种附加的化合物,即杀真菌剂(即,附加的杀真菌化合物)。在本发明的组合物中,组分(c)中的附加的杀真菌化合物通常选自(c1)苯并咪唑氨基甲酸甲酯杀真菌剂;(c2)二酰亚胺杀真菌剂;(c3)脱甲基抑制剂(DMI)杀真菌剂;(c4)苯基酰胺杀真菌剂;(c5)胺/吗啉杀真菌剂;(c6)磷脂生物合成抑制剂杀真菌剂;(c7)酰胺杀真菌剂;(c8)羟基(2-氨基-)嘧啶杀真菌剂;(c9)苯胺基嘧啶杀真菌剂;(c10)N-苯基氨基甲酸酯杀真菌剂;(c11)醌外部抑制剂(QoI)杀真菌剂;(c12)苯基吡咯杀真菌剂;(c13)喹啉杀真菌剂;(c14)类脂过氧化抑制剂杀真菌剂;(c15)黑素生物合成抑制剂-还原酶(MBI-R)杀真菌剂;(c16)黑素生物合成抑制剂-脱水酶(MBI-D)杀真菌剂;(c17)羟基苯胺杀真菌剂;(c18)角鲨烯-环氧酶抑制剂杀真菌剂;(c19)多抗霉素杀真菌剂;(c20)苯基脲杀真菌剂;(c21)醌内部抑制剂(QiI)杀真菌剂;(c22)苯甲酰胺杀真菌剂;(c23)烯醇式吡喃糖醛酸抗生素杀真菌剂;(c24)己吡喃糖基抗生素杀真菌剂;(c25)吡喃葡糖基抗生素:蛋白质合成杀真菌剂;(c26)吡喃葡糖基抗生素:海藻糖酶和肌醇生物合成杀真菌剂;(c27)氰基乙酰胺肟杀真菌剂;(c28)氨基甲酸酯杀真菌剂;(c29)氧化磷酸化解偶联杀真菌剂;(c30)有机锡杀真菌剂;(c31)羧酸杀真菌剂;(c32)杂芳族杀真菌剂;(c33)膦酸酯杀真菌剂;(c34)邻氨甲酰基苯甲酸杀真菌剂;(c35)苯并三嗪杀真菌剂;(c36)苯-磺酰胺杀真菌剂;(c37)哒嗪酮杀真菌剂;(c38)噻吩-甲酰胺杀真菌剂;(c39)嘧啶酰胺杀真菌剂;(c40)羧酸酰胺(CAA)杀真菌剂;(c41)四环素抗生素杀真菌剂;(c42)硫代氨基甲酸酯杀真菌剂;(c43)苯甲酰胺杀真菌剂;(c44)寄主植物防御诱导型杀真菌剂;(c45)多位点接触活性杀真菌剂;(c46)杀真菌剂,所述杀真菌剂不是组分(a)和组分(c1)至(c45)的杀真菌剂;以及(c1)至(c46)的化合物的盐。
值得注意的是杀真菌剂组合物实施例,其中组分(c)包含至少一种杀真菌化合物,所述杀真菌化合物来自选自(c1)至(c46)的两个不同组中的每一组。
“苯并咪唑氨基甲酸甲酯(MBC)杀真菌剂(c1)”(FRAC(杀菌剂抗性行动委员会)编码1)通过在微管组装期间与β-微管蛋白结合来抑制有丝分裂。抑制微管组装可扰乱细胞分裂、在细胞和细胞结构内的传输。苯并咪唑氨基甲酸甲酯杀真菌剂包括苯并咪唑和硫菌灵杀真菌剂。苯并咪唑类包括苯菌灵、多菌灵、麦穗宁和噻苯哒唑。托布津类包括硫菌灵和甲基硫菌灵。
“二酰亚胺杀真菌剂(c2)”(FRAC编码2)旨在通过干扰NADH细胞色素c还原酶来抑制真菌内的类脂过氧化。例子包括乙菌利、异菌脲、腐霉利和乙烯菌核利。
“脱甲基抑制剂(DMI)杀真菌剂(c3)”(FRAC编码3)抑制在甾醇制备中起作用的C14-脱甲基酶。甾醇诸如麦角固醇是薄膜结构和功能所需的,使得它们成为产生功能性细胞壁所必不可少的。因此,暴露于这些杀真菌剂导致致敏真菌异常生长并且最终死亡。DMI杀真菌剂分为多种化学类别:唑类(包括三唑类和咪唑类)、嘧啶类、哌嗪类和吡啶类。三唑类包括戊环唑、联苯三唑醇、糠菌唑、环丙唑醇、醚唑、烯唑醇(包括烯唑醇-M)、氟环唑、乙环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、喹唑、硅氟唑、戊唑醇、氟醚唑、三唑酮、三唑醇、灭菌唑和烯效唑。咪唑类包括克霉唑、益康唑、抑霉唑、异康唑、咪康唑、咪唑、咪鲜安、稻瘟酯和氟菌唑。嘧啶类包括氯苯嘧啶醇、氟苯嘧啶醇和嘧菌醇。哌嗪类包括嗪氨灵。吡啶类包括丁硫啶和啶斑肟。生物化学调查研究已显示所有上述杀真菌剂均为DMI杀真菌剂,如由K.H.Kuck等人在ModernSelective Fungicides-Properties,Applications and Mechanisms of Action,H.Lyr(编辑),Gustav Fischer Verlag:New York,1995,205-258中所述。
“苯基酰胺杀真菌剂(c4)”(FRAC编码4)是卵菌真菌中RNA聚合酶的特定抑制剂。暴露于这些杀真菌剂的致敏真菌示出将尿核苷引入rRNA中的能力下降。通过暴露于该杀真菌剂,可阻止致敏真菌的生长和发展。苯基酰胺杀真菌剂包括酰基丙氨酸、唑烷酮和丁内酯杀真菌剂。所述酰基丙氨酸包括苯霜灵、苯霜灵-M、呋霜灵、甲霜灵、甲霜灵-M(也称为精甲霜灵)。唑烷酮类包括霜灵。丁内酯类包括呋酰胺。
“胺/吗啉杀真菌剂(c5)”(FRAC编码5)抑制甾醇生物合成途径中的两个目标位点,Δ8→Δ7异构酶和Δ14还原酶。甾醇诸如麦角固醇是薄膜结构和功能所需的,使得它们成为产生功能性细胞壁所必不可少的。因此,暴露于这些杀真菌剂导致致敏真菌异常生长并且最终死亡。胺/吗啉杀真菌剂(也称为非-DMI甾醇生物合成抑制剂)包括吗啉、哌啶和螺酮缩醇-胺杀真菌剂。吗啉类包括aldimorph、十二环吗啉、丁苯吗啉、十三吗啉和垂吗酰胺。哌啶类包括苯锈啶和粉病灵。螺酮缩醇-胺类包括螺环菌胺。
“磷脂生物合成抑制剂杀真菌剂(c6)”(FRAC编码6)通过影响磷脂生物合成来抑制真菌的生长。磷脂生物合成杀真菌剂包括硫代磷酸酯和二硫戊环杀真菌剂。硫代磷酸酯类包括敌瘟磷、异稻瘟净和定菌磷。二硫戊环类包括稻瘟灵。
“酰胺杀真菌剂(c7)”(FRAC编码7)通过扰乱克雷伯氏循环(TCA循环)中称为琥珀酸脱氢酶的关键性酶来抑制复合物II(琥珀酸脱氢酶)真菌的呼吸。抑制呼吸可阻止真菌产生ATP,从而抑制生长和繁殖。酰胺杀真菌剂包括苯甲酰胺、呋喃甲酰胺、氧硫杂环己二烯甲酰胺、噻唑甲酰胺、吡唑甲酰胺和吡啶甲酰胺。苯甲酰胺类包括麦锈灵、氟酰胺和灭锈胺。呋喃甲酰胺类包括甲呋酰胺氧硫杂环己二烯羧酰胺类包括萎锈灵和氧化萎锈灵。噻唑甲酰胺类包括噻呋灭。所述吡唑甲酰胺类包括联苯吡菌胺、福拉比、吡唑萘菌胺、氟唑菌酰胺(fluxapyroxad)、吡噻菌胺、sedaxane(N-[2-(1S,2R)-[1,1′-联环丙烷]-2-基苯基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺)和戊苯吡菌胺(penflufen)(N-[2-(1,3-二甲基丁基)苯基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺)(PCT专利公布WO 2003/010149)。吡啶甲酰胺类包括啶酰菌胺。
“羟基(2-氨基-)嘧啶杀真菌剂(c8)”(FRAC编码8)通过干扰腺苷脱氨酶来抑制核酸合成。例子包括乙嘧酚磺酸酯、甲菌定和乙嘧酚。
“苯胺基嘧啶杀真菌剂(c9)”(FRAC编码9)旨在抑制氨基酸甲硫氨酸的生物合成,并且旨在阻断感染期间使植物细胞裂解的水解酶的分泌。例子包括嘧菌环胺、灭派林和嘧霉胺。
“N-苯基氨基甲酸酯杀真菌剂(c10)”(FRAC编码10)通过与β-微管蛋白结合并且扰乱微管组装来抑制有丝分裂。抑制微管组装可扰乱细胞分裂、在细胞和细胞结构内的传输。例子包括乙霉威。
“醌外部抑制剂(QoI)杀真菌剂(c11)”(FRAC编码11)通过影响泛醇氧化酶来抑制真菌内的复合物III线粒体的呼吸。泛醇的氧化在位于真菌线粒体内膜中的细胞色素bc1复合物的“醌外部”(Qo位点处被阻断。抑制线粒体呼吸阻止真菌正常生长和发展。醌外部抑制剂杀真菌剂包括甲氧基丙烯酸酯、甲氧基氨基甲酸酯、肟基乙酸酯、肟基乙酰胺和二氢二嗪杀真菌剂(也统称为甲氧基丙烯酸酯类杀真菌剂)以及唑烷二酮、咪唑啉酮类和苄基氨基甲酸酯杀真菌剂。甲氧基丙烯酸酯类包括嘧菌酯、烯肟菌酯(SYP-Z071)和啶氧菌酯。甲氧基氨基甲酸酯包括唑菌胺酯和唑胺菌酯。肟基乙酸酯包括醚菌酯、唑菌酯和肟菌酯。肟基乙酰胺类包括醚菌胺、苯氧菌胺、肟醚菌胺和α-(甲氧基亚氨基)-N-甲基-2-[[[1-[3-(三氟甲基)苯基]乙氧基]亚氨基]甲基]苯乙酰胺。二氢二嗪杀真菌剂包括氟嘧菌酯。唑烷二酮类包括唑菌酮。咪唑啉酮类包括咪唑菌酮。苄基氨基甲酸酯类包括吡菌苯威(pyribencarb)。
“苯基吡咯杀真菌剂(c12)”(FRAC编码12)抑制真菌内与渗透性信号转导相关的MAP蛋白质激酶。拌种咯和咯菌腈是此杀真菌剂类型的例子。
“喹啉杀真菌剂(c13)”(FRAC编码13)旨在通过影响早期细胞信号G-蛋白来抑制信号转导。已示出它们可干扰引起白粉病的真菌产生和/或附着胞的形成。快诺芬是此类杀真菌剂的例子。
“类脂过氧化抑制剂杀真菌剂(c14)”(FRAC编码14)旨在通过影响真菌内的膜合成来抑制类脂过氧化。此类成员诸如土菌灵还可影响其它生物过程,诸如呼吸和黑素生物合成。类脂过氧化杀真菌剂包括芳烃和1,2,4-噻二唑杀真菌剂。芳烃类包括联苯、地茂散、氯硝胺、五氯硝基苯、四氯硝基苯和甲基立枯磷。1,2,4-噻二唑类包括土菌灵。
“黑素生物合成抑制剂-还原酶(MBI-R)杀真菌剂(c15)”(FRAC编码16.1)抑制黑素生物合成中的萘醛缩还原步骤。黑素是一些真菌感染寄主植物所必需的。黑素生物合成抑制剂-还原酶杀真菌剂包括异苯并呋喃酮、吡咯并喹诺酮和三唑并苯并噻唑杀真菌剂。异苯并呋喃酮类包括四氯苯酞。吡咯并喹诺酮类包括咯喹酮。三唑并苯并噻唑类包括三环唑。
“黑素生物合成抑制剂-脱水酶(MBI-D)杀真菌剂(c16)”(FRAC编码16.2)可抑制黑素生物合成中的小柱孢酮脱水酶。黑素是一些真菌感染寄主植物所必需的。黑素生物合成抑制剂-脱水酶杀真菌剂包括环丙烷甲酰胺、酰胺和丙酰胺杀真菌剂。环丙烷甲酰胺类包括环丙酰菌胺。甲酰胺类包括双氯氰菌胺。丙酰胺类包括氰菌胺。
“羟基苯胺杀真菌剂(c17)”(FRAC编码17)抑制在甾醇制备中起作用的C4-脱甲基酶。例子包括环酰菌胺。
“角鲨烯-环氧酶抑制剂杀真菌剂(c18)”(FRAC编码18)抑制麦角固醇生物合成途径中的角鲨烯-环氧酶。甾醇如麦角固醇是薄膜结构和功能所需的,使得它们成为产生功能性细胞壁必须的。因此,其与这些杀真菌剂接触导致致敏真菌异常生长并且最终死亡。角鲨烯-环氧酶抑制剂杀真菌剂包括硫代氨基甲酸酯和烯丙胺杀真菌剂。硫代氨基甲酸酯类包括稗草畏。烯丙胺类包括萘替芬和特比萘芬。
“多抗霉素杀真菌剂(c19)”(FRAC编码19)抑制甲壳质合酶。例子包括多抗霉素。
“苯基脲杀真菌剂(c20)”(FRAC编码20)旨在影响细胞分株。例子包括戊菌隆。
“醌内部抑制剂(QiI)杀真菌剂(c21)”(FRAC编码21)通过影响泛醇还原酶来抑制真菌内的复合物III线粒体呼吸。泛醇的还原在位于真菌线粒体内膜中的细胞色素bc1复合物的“醌内部”(Qi位点处被阻断。抑制线粒体呼吸阻止真菌正常生长和发展。醌内部抑制剂杀真菌剂包括氰基咪唑和氨磺酰三唑杀真菌剂。氰基咪唑类包括赛座灭。氨磺酰三唑类包括吲唑磺菌胺。
“苯甲酰胺杀真菌剂(c22)”(FRAC编码22)通过与β-微管蛋白结合并且扰乱微管组装来抑制有丝分裂。抑制微管组装可扰乱细胞分裂、在细胞和细胞结构内的传输。例子包括苯酰菌胺。
“烯醇式吡喃糖醛酸抗生素杀真菌剂(c23)”(FRAC编码23)通过影响蛋白质生物合成来抑制真菌生长。例子包括杀稻瘟菌素-S。
“己吡喃糖基抗生素杀真菌剂(c24)”(FRAC编码24)通过影响蛋白质生物合成来抑制真菌生长。例子包括春雷霉素。
“吡喃葡糖基抗生素:蛋白质合成杀真菌剂(c25)”(FRAC编码25)通过影响蛋白质生物合成来抑制真菌生长。例子包括链霉素。
“吡喃葡糖基抗生素:海藻糖酶和肌酶生物合成杀真菌剂(c26)”(FRAC编码26)抑制肌醇生物合成途径中的海藻糖酶。例子包括井冈霉素。
“氰基乙酰胺肟杀真菌剂(c27)”(FRAC编码27)包括霜脲氰。
“氨基甲酸酯杀真菌剂(c28)”(FRAC编码28)被认为是真菌生长多位点抑制剂。它们旨在干扰细胞膜中脂肪酸的合成,从而扰乱细胞膜渗透性。霜霉威、丁基甲氨酸碘代丙炔酯和硫菌威是此类杀真菌剂的例子。
“氧化磷酸化解偶联杀真菌剂(c29)”(FRAC编码29)通过解偶联氧化磷酸化作用于抑制真菌呼吸。抑制呼吸可阻止真菌正常生长和发展。此类包括2,6-二硝基苯胺类诸如氟啶胺、嘧啶酮腙类诸如嘧菌腙、以及巴豆酸二硝基苯酯类诸如敌螨普、消螨多和乐杀螨。
“有机锡杀真菌剂(c30)”(FRAC编码30)抑制氧化磷酸化途径中的腺苷三磷酸腺苷(ATP)合酶。例子包括三苯基乙酸锡、三苯基氯化锡和三苯基氢氧化锡。
“羧酸杀真菌剂(c31)”(FRAC编码31)通过影响脱氧核糖核酸(DNA)II型拓扑异构酶(旋转酶)来抑制真菌生长。例子包括喹酸。
“杂芳族杀真菌剂(c32)”(FRAC编码32)旨在影响DNA/核糖核酸(RNA)的合成。杂芳族杀真菌剂包括异唑和异噻唑啉酮杀真菌剂。异唑类包括霉灵,而异噻唑啉酮类包括辛噻酮。
“膦酸酯杀真菌剂(c33)”(FRAC编码33)包括磷酸及其各种盐,包括三乙膦酸铝。
“邻氨甲酰基苯甲酸杀真菌剂(c34)”(FRAC编码34)包括叶枯酞。
“苯并三嗪杀真菌剂(c35)”(FRAC编码35)包括triazoxide。
“苯-磺酰胺杀真菌剂(c36)”(FRAC编码36)包括磺菌胺。
“哒嗪酮杀真菌剂(c37)”(FRAC编码37)包括哒菌清。
“噻吩-甲酰胺杀真菌剂(c38)”(FRAC编码38)旨在影响ATP生成。例子包括硅噻菌胺。
“嘧啶酰胺杀真菌剂(c39)”(FRAC编码39)通过影响磷脂生物合成来抑制真菌生长,并且包括二氟林。
羧酸酰胺(CAA)杀真菌剂(c40)”(FRAC)编码40)旨在抑制磷脂生物合成和细胞壁沉积。这些过程的抑制作用阻止了目标真菌的生长并且致使其死亡。羧酸酰胺杀真菌剂包括肉桂酰胺、缬胺酰胺氨基甲酸酯和扁桃酰胺杀真菌剂。肉桂酰胺类包括烯酰吗啉和氟吗啉。缬胺酰胺氨基甲酸酯类包括苯噻菌胺、异丙基苯噻菌胺、丙森锌和valifenalate(valiphenal)。扁桃酰胺包括双炔酰菌胺、N-[2-[4-[[3-(4-氯苯基)-2-丙炔-1-基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲基磺酰基)氨基]丁酰胺和N-[2-[4-[[3-(4-氯苯基)-2-丙炔-1-基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(乙基磺酰基)氨基]丁酰胺。
“四环素抗生素杀真菌剂(c41)”(FRAC编码41)通过影响复合物1烟酰胺腺嘌呤二核苷酸(NADH)氧化还原酶来抑制真菌生长。例子包括氧四环素。
“硫代氨基甲酸酯杀真菌剂(c42)”(FRAC编码42)包括磺菌威。
“苯甲酰胺杀真菌剂(c43)”(FRAC编码43)通过使类血影蛋白离域来抑制真菌生长。例子包括氟啶酰菌胺杀真菌剂,诸如氟吡菌胺和氟吡菌酰胺。
“寄主植物防御诱导型杀真菌剂(c44)”(FRAC编码P)诱导寄主植物防御机制。寄主植物防御诱导型杀真菌剂包括阿拉酸式苯、苯并异噻唑和噻二唑-羧酰胺杀真菌剂。阿拉酸式苯类包括阿拉酸式苯-S-甲基。苯并异噻唑类包括噻菌灵。噻二唑-羧酰胺类包括噻酰菌胺和异噻菌胺。
“多位点接触型杀真菌剂(c45)”通过多位点作用抑制真菌生长并且具有接触/预防活性。此类杀真菌剂包括:“铜杀真菌剂(c45.1)(FRAC编码M1)”、“硫杀真菌剂(c45.2)(FRAC编码M2)”、“二硫代氨基甲酸酯杀真菌剂(c45.3)(FRAC编码M3)”、“邻苯二酰亚胺类杀真菌剂(c45.4)(FRAC编码M4)”、“氯腈杀真菌剂(c45.5)(FRAC编码M5)”、“硫酰胺杀真菌剂(c45.6)(FRAC编码M6)”、“胍杀真菌剂(c45.7)(FRAC编码M7)”“三嗪杀真菌剂(c45.8)(FRAC编码M8)”和“醌杀真菌剂(c45.9)(FRAC编码M9)”。“铜杀真菌剂”为包含铜的无机化合物,通常为铜(II)氧化态;例子包括王铜、硫酸铜和氢氧化铜,包括诸如波尔多液(三元硫酸铜)的组合物。“硫杀真菌剂”为包含具有硫原子的环或链的无机化合物;例子包括元素硫。“二硫代氨基甲酸酯杀真菌剂”包含二硫代氨基甲酸酯分子部分;例子包括代森锰锌、代森联、丙森锌、福美铁、代森锰、福美双、代森锌和福美锌。“邻苯二酰亚胺类杀真菌剂”包含邻苯二酰亚胺类分子部分;例子包括灭菌丹、克菌丹和敌菌丹。“氯腈杀真菌剂”包含被氯和氰基取代的芳环;例子包括百菌清。“磺酰胺杀真菌剂”包括抑菌灵和对甲抑菌灵。“胍杀真菌剂”包括多果定、双胍盐和双胍辛胺。“三嗪杀真菌剂”包括敌菌灵。“醌杀真菌剂”包括二噻农。
“杀真菌剂,不是组分(a)和组分(c1)至(c45)的杀真菌剂;(c46)”包括某些它的作用模式可能未知的杀真菌剂。这些包括:(c46.1)“噻唑甲酰胺杀真菌剂”(FRAC编码U5),(c46.2)“苯基-乙酰胺杀真菌剂”(FRAC编码U6),(c46.3)“喹唑啉酮杀真菌剂”(FRAC编码U7),(c46.4)“二苯甲酮杀真菌剂”(FRAC编码U8)和(c46.5)“三唑并嘧啶基胺杀真菌剂”(FRAC编码45)。噻唑甲酰胺类包括噻唑菌胺。苯基-乙酰胺类包括环氟菌胺和N-[[(环丙基甲氧基)氨基][6-(二氟甲氧基)-2,3-二氟苯基]-亚甲基]苯乙酰胺。喹唑啉酮类包括丙氧喹啉和2-丁氧基-6-碘-3-丙基-4H-1-苯并吡喃-4-酮。二苯甲酮类包括苯菌酮和pyriofenone。三唑并嘧啶基胺类包括苯唑嘧菌胺,并且据信通过在泛醌-细胞色素bc1还原酶上结合未阐明的位点来抑制复合体III线粒体呼吸作用。所述(b46)类还包括bethoxazin、甲胂铁铵(甲基胂酸铁)、胺苯吡菌酮(fenpyrazamine)、吡咯尼群、灭螨猛、tebufloquin、2-[[2-氟-5-(三氟甲基)苯基]硫代]-2-[3-(2-甲氧苯基)-2-亚噻唑烷基]乙腈、3-[5-(4-氯苯基)-2,3-二甲基-3-异唑烷基]吡啶、N-[1-[[[1-(4-氰基苯基)乙基]磺酰基]甲基]丙基]氨基甲酸-4-氟苯酯、5-氯-6-(2,4,6-三氟苯基)-7-(4-甲基哌啶-1-基)[1,2,4]三唑并[1,5-a]嘧啶、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、N′-[4-[4-氯-3-(三氟甲基)苯氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒和1-[(2-丙烯硫基)羰基]-2-(1-甲基乙基)-4-(2-甲基苯基)-5-氨基-1H-吡唑-3-酮。
“杀真菌剂,不是组分(a)和组分(c1)至(c45)的杀真菌剂;(c46)”也包括式C1的(c46.5)6-喹啉基氧基乙酰胺化合物及其盐
其中
Rc1为卤素、C1-C4烷氧基或C1-C4炔基;
Rc2为H、卤素或C1-C4烷基;
Rc3为C1-C12烷基、C1-C12卤代烷基、C1-C12烷氧基、C2-C12烷氧基烷基、C2-C12烯基、C2-C12炔基、C4-C12烷氧基烯基、C4-C12烷氧基炔基、C1-C12烷硫基或C2-C12烷硫基烷基;
Rc4为甲基或-ya1-Rc5;
Rc5为C1-C2烷基;并且
yc1为CH2、O或S。
式C1的化合物、它们作为杀真菌剂的用途以及制备的方法一般是已知的;参见,例如PCT专利公布WO 2004/047538、WO 2004/108663、WO 2006/058699、WO 2006/058700、WO2008/110355、WO 2009/030469、WO 2009/049716和WO 2009/087098。式C1的化合物的例子包括:2-[(3-溴代-6-喹啉基)氧基]-N-(1,1-二甲基-2-丁炔-1-基)-2-(甲硫基)乙酰胺、2-[(3-乙炔基-6-喹啉基)氧基]-N-[1-(羟甲基)-1-甲基-2-丙炔-1-基]-2-(甲硫基)乙酰胺、N-(1,1-二甲基-2-丁炔-1-基)-2-[(3-乙炔基-6-喹啉基)氧基]-2-(甲硫基)乙酰胺、2-[(3-溴-8-甲基-6-喹啉基)氧基]-N-(1,1-二甲基-2-丙炔-1-基)-2-(甲硫基)乙酰胺和2-[(3-溴-6-喹啉基)氧基]-N-(1,1-二甲基乙基)丁酰胺。
“杀真菌剂,不是组分(a)和组分(c1)至(c45)的杀真菌剂;“(b46)”也包括(c46.6)N′-[4-[[3-[(4-氯苯基)甲基]-1,2,4-噻二唑-5-基]氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒,据信其抑制甾醇类的生物合成涉及的C24-甲基转移酶。
组分(c)杀真菌化合物的例子包括实施例31,更具体地实施例32,甚至更具体地实施例33中列出的那些。
包含如下组分的组合的组合物可由组分(a)、(b)和(c)的协同作用提供对植物病害的改善的控制(即预防和/或治愈):(a)至少一种化合物,所述化合物选自式1的化合物,包括其N-氧化物和盐,(b)至少一种杀真菌组分,其选自式B1至B13,包括其盐,以及(c)至少一种附加的杀真菌化合物(例如,实施例30的(c1)至(c46),包括上述对应的杀真菌化合物)。改善的植物病害控制可通过更广谱或更长持续时间的植物病害控制,或抗性发展的延迟来显示。组分(a)、(b)和(c)的作用可以互补地累加或甚至大于通过协同作用的累加。加入组分(c)可提供比由组分(a)和(b)的组合所得到的更强的协同作用。
在上述包含如下组分的杀真菌剂组合物中:(a)至少一种化合物,所述化合物选自式1的化合物,包括其N-氧化物和盐,(b)至少一种杀真菌化合物,其选自式B1至B13,包括其盐,以及(c)还包括至少一种附加的化合物和试剂,所述附加化合物和试剂是生物活性的,除了上述杀真菌化合物(c1)至(c46)之外,组分(c)还可选自不是杀真菌剂的具有生物活性的化合物或试剂。此类可与组分(a)和组分(b)的组合物混合(例如,在农用制剂中)的生物活性化合物或试剂的例子为:杀虫剂诸如阿巴美丁、高灭磷、啶虫脒、乙酰虫腈、氟丙菊酯、涕灭威、磺胺螨酯、双甲脒、阿维菌素、印苦楝子素、谷硫磷-甲基、联苯菊酯、联苯肼酯、双三氟虫脲、扑虱灵、克百威、aldimorph、灭螨猛、溴虫腈、定虫隆、氯虫苯甲酰胺、氯蜱硫磷、甲基氯蜱硫磷、克氯苯、可芬诺、可尼丁、氰虫酰胺、丁氟螨酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、γ-三氟氯氰菊酯、λ-三氟氯氰菊酯、三环锡、氯氰菊酯、环丙氨嗪、溴氰菊酯、丁醚脲、敌匹硫磷、三氯杀螨醇、迪厄尔丁、除螨灵、除虫脲、四氟甲醚菊酯、乐果、呋虫胺、二苯丙醚、甲氨基阿维菌素、硫丹、页式氰戊菊酯、乙虫腈、乙螨唑、苯线磷、喹螨醚、苯丁锡、苯硫威、苯氧威、甲氰菊酯、唑螨酯、腈苯苯醚菊酯、氟虫腈、氟啶虫酰胺、氟虫酰胺、氟氰戊菊酯、氟胺氰菊酯、嘧虫胺、氟虫脲、大福松、氯虫酰肼、氟铃脲、噻螨酮、氟蚁腙、新烟碱、吡虫啉、茚虫威、异柳磷、虱螨脲、马拉硫磷、氯氟醚菊酯、氰氟虫腙、蜗牛敌、甲胺磷、杀扑磷、乙肟威、甲氧普烯、甲氧滴滴涕、甲氧虫酰肼、甲氧苄氟菊酯、杀螨菌素肟、久效磷、尼古丁、烯啶虫胺、硝乙脲噻唑、双苯氟脲、多氟脲、草氨酰、对硫磷、甲基对硫磷、扑灭司林、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯、克螨特、硫菌威、protrifenbute、吡蚜酮、吡嗪氟虫腈、除虫菊酯、哒螨酮、啶虫丙醚、pyrifluquinazon、pyriprole、蚊蝇醚、鱼藤酮、利阿诺定、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、砜虫啶、硫丙磷、虫酰肼、吡螨胺、伏虫脲、七氟菊酯、特丁磷、杀虫畏、四氟醚菊酯、噻虫啉、噻虫嗪、硫双灭多威、杀虫双、唑虫酰胺、四溴菊酯、唑蚜威、敌百虫、杀铃脲;杀线虫剂诸如涕灭威、新烟碱、草氨酰和苯线磷;杀细菌剂诸如链霉素;杀螨剂,诸如双甲脒、灭螨猛、克氯苯、杀螨剂(cyenopyrafen)、三环锡、三氯杀螨醇、除螨灵、乙螨唑、喹螨醚、苯丁锡、甲氰菊酯、唑螨酯、噻螨酮、克螨特、哒螨酮和吡螨胺;并且生物试剂包括昆虫病原细菌,诸如苏云金芽孢杆菌鲇泽亚种、苏云金芽孢杆菌库尔斯塔克亚种、以及苏云金芽孢杆菌的包封的δ-内毒素(例如,Cellcap、MPV、MPVII);昆虫病原真菌诸如绿僵菌;和昆虫病原病毒,包括杆状病毒、核多角体病毒(NPV)诸如HzNPV、AfNPV;以及颗粒体病毒(GV),诸如CpGV。
值得注意的是除了组分(a)和(b)之外,还包含至少一种无脊椎害虫控制化合物或试剂的组合物,所述无脊椎害虫控制化合物或试剂选自阿巴美丁、高灭磷、啶虫脒、乙酰虫腈、氟丙菊酯、涕灭威、磺胺螨酯、双甲脒、阿维菌素、印苦楝子素、谷硫磷-甲基、联苯菊酯、联苯肼酯、双三氟虫脲、扑虱灵、克百威、aldimorph、灭螨猛、溴虫腈、定虫隆、氯虫苯甲酰胺、氯蜱硫磷、甲基氯蜱硫磷、克氯苯、可芬诺、可尼丁、氰虫酰胺、丁氟螨酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、γ-三氟氯氰菊酯、λ-三氟氯氰菊酯、三环锡、氯氰菊酯、环丙氨嗪、溴氰菊酯、丁醚脲、敌匹硫磷、三氯杀螨醇、迪厄尔丁、除螨灵、除虫脲、四氟甲醚菊酯、乐果、呋虫胺、二苯丙醚、甲氨基阿维菌素、硫丹、页式氰戊菊酯、乙虫腈、乙螨唑、苯线磷、喹螨醚、苯丁锡、苯硫威、苯氧威、甲氰菊酯、唑螨酯、腈苯苯醚菊酯、氟虫腈、氟啶虫酰胺、氟虫酰胺、氟氰戊菊酯、氟胺氰菊酯、嘧虫胺、氟虫脲、大福松、氯虫酰肼、氟铃脲、噻螨酮、氟蚁腙、新烟碱、吡虫啉、茚虫威、异柳磷、虱螨脲、马拉硫磷、氯氟醚菊酯、氰氟虫腙、蜗牛敌、甲胺磷、杀扑磷、乙肟威、甲氧普烯、甲氧滴滴涕、甲氧虫酰肼、甲氧苄氟菊酯、杀螨菌素肟、久效磷、尼古丁、烯啶虫胺、硝乙脲噻唑、双苯氟脲、多氟脲、草氨酰、对硫磷、甲基对硫磷、扑灭司林、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯、克螨特、硫菌威、protrifenbute、吡蚜酮、吡嗪氟虫腈、除虫菊酯、哒螨酮、啶虫丙醚、pyrifluquinazon、pyriprole、蚊蝇醚、鱼藤酮、利阿诺定、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、砜虫啶、硫丙磷、虫酰肼、吡螨胺、伏虫脲、七氟菊酯、特丁磷、杀虫畏、四氟醚菊酯、噻虫啉、噻虫嗪、硫双灭多威、杀虫双、唑虫酰胺、四溴菊酯、唑蚜威、敌百虫、杀铃脲、苏云金芽孢杆菌鲇泽亚种、、苏云金芽孢杆菌库尔斯塔克亚种、核多角体病毒、苏云金芽孢杆菌的包封的δ内毒素、杆状病毒、昆虫病原细菌、昆虫病原病毒和昆虫病原真菌。
在某些情况下,组分(a)和(b)杀真菌化合物的混合物与无脊椎害虫控制化合物或试剂(即,作为组分(c)的生物活性成分)的组合可导致大于累加(即,协同)效应。减少在环境中释放的活性成分的量,同时确保有效的害虫控制一直是所期望的。当无脊椎害虫防治活性成分在施用量下发生协同作用从而赋予农业上令人满意的无脊椎害虫防治水平时,此类组合可有利地用于减少作物生产成本,并且降低环境荷载。协同作用也可以导致增加的植物病害控制或保护。
在本发明的杀真菌组合物中,组分(a)(即至少一种选自式1的化合物、其N-氧化物和盐的化合物)和组分(b)以杀真菌有效量存在。组分(a)和组分(b)(即,一种或多种附加的杀真菌化合物)的重量比一般介于约1∶3000至约3000∶1之间,更典型地介于约1∶500和约500∶1之间。值得注意的是其中组分(a)和组分(b)的重量比为约125∶1至约1∶125的组合物。由于具有许多组分(b)的杀真菌化合物,这些组合物对控制由真菌植物病原体引起的植物病害特别有效。特别值得注意的是其中组分(a)和组分(b)的重量比为约25∶1至约1∶25,或约5∶1至约1∶5的组合物。通过样品实验,本领域技术人员能够容易地确定杀真菌保护和控制所期望的范围所必要的杀真菌化合物的重量比和施用量。
表A1列出了举例说明本发明混合物、组合物和方法的组分(b)化合物与作为组分(a)的化合物1的具体组合。(化合物编号是指索引表A中的化合物)。表A1的第二栏列出了具体组分(b)化合物(例如,第一行中的“1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮(b1a)”)。表A1的第三栏、第四栏和第五栏列出了在组分(a)通常对大田生长作物所施用的量下,相对于组分(b)的重量比范围。因此,例如,表A1的第一行具体公开了通常以介于400∶1和1∶1之间的化合物1与组分(b1a)的重量比来施加化合物1和组分(b1a)的组合。表A1的其余行可类似地解释。
表A1
表A2至A13每个构造与上表A1中相同,不同的是栏标题下面的条目“组分(a)”被下文所示的相应组分(a)的栏条目替代。因此,例如,表A2中栏标题下面的条目“组分(a)”全列举为“化合物2”,并且表A2中栏标题下面的第一行具体公开了化合物2与1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮的组合。表A3至A13类似构造。
具体的混合物列出在表B1至B13中。(化合物编号涉及在索引表A中的化合物,并且组分(b)在表A1中认定)。在表B1中,在栏标题“组分(a)”和“组分(b)”下面的每行具体地公开了为化合物1的组分(a)与组分(b)杀真菌化合物的混合物。在标题“例证性比率”下的条目公开了关于公开的混合物的组分(a)相对于组分(b)的七个具体的重量比。例如,表B1的第一行公开了化合物1与1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮(b1)的混合物,并列出了化合物1相对于组分(b1)的2∶1、4∶1、8∶1、20∶1、50∶1、100∶1或200∶1的重量比。因此表B1补充了公开于表A1中的组合的一般比率范围的具体比率。
表B1
表B2至B13每个构造与上表B1中相同,不同的是栏标题下面的条目“组分(a)”被下文所示的相应组分(a)的栏条目替代。因此,例如,表B2中栏标题下面的条目“组分(a)”全列举为“化合物2”,并且表A2中栏标题下面的第一行具体公开了化合物2与1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮的组合。表B3至B13类似地构造。因此,表B2至B13补充了分别公开于表A2至A13中的组合的一般比率范围的具体比率。
如已经注意的,本发明包括实施例,其中包含组分(a)和(b)的组合物还包含作为组分(c)的一种或多种生物活性化合物或试剂。因此,本发明的实施例包括表A1至A12中以及表B1至B13中公开的混合物与附加的生物化合物或试剂的组合。作为附加的生物化合物或试剂,值得注意的是选自已经公开的(c1)至(c46)的杀真菌化合物。组分(c)与组分(a)的重量比一般介于约1∶3000和约3000∶1之间,更典型地介于约1∶500和约500∶1之间,介于约125∶1和约1∶125之间,介于约25∶1和1∶25之间,以及最典型地介于约5∶1和约1∶5之间。通过样品实验,本领域技术人员能够容易地确定植物病害保护和控制所期望的范围所必要的杀真菌化合物的重量比和施用量。
表C列出了在包含组分(b)之前(即,不具有组分(b))或之后,包含组分(a)和(c)的组合物中,组分(c)相对于组分(a)的典型的、更典型的和最典型的重量比。
表C
表C中限定重量比范围的具体重量比构成了具体重量比的公开。表C还具体地公开了附加的示例性重量比。本发明的组合物中组分(a)、(b)和(c)的例证性的具体组合为表B1至B13中所列具体组合和重量比的组分(a)和(b)与具体组分(c)杀真菌化合物以表C中公开的具体重量比进一步组合。
制剂/效用
选自式1的化合物、其N-氧化物和盐的化合物,或包含化合物与(b)至少一种如发明内容中所述的选自(b1)至(b13)的杀真菌化合物及其盐的混合物(即,组合物),将一般用于在另外的组合物,即制剂中提供杀真菌活性成分,所述组合物具有至少一种用作载体的附加组分,所述附加组分选自表面活性剂、固体稀释剂和液体稀释剂。选择制剂或组合物成分,使其与活性成分的物理性质、施用方式和环境因素如土壤类型、湿度和温度相符合。
可以多种方式配制组分(a)(即至少一种式1的化合物、其N-氧化物或盐)与组分(b)(例如,选自如上所述的(b1)至(b13)及其盐)和/或一种或多种其它生物学活性化合物或试剂(即,杀虫剂、其它杀真菌剂、杀线虫剂、杀螨剂、除草剂以及其它生物试剂)的混合物,所述多种方式包括:
(i)可单独配制并单独施用或者以适当的重量比同时施用组分(a)、组分(b)和任选地(c)一种或多种其它生物活性化合物或试剂,例如以罐内混合物形式;或者
(ii)以适当的重量比将组分(a)、组分(b)和任选地(c)一种或多种其它生物活性化合物或试剂配制在一起。
可用的制剂包括液体组合物和固体组合物两者。液体组合物包括溶液(包括可乳化的浓缩物)、悬浮液、乳液(包括微乳液和/或悬乳液)等,它们可以任选地被增稠成凝胶。水性液体组合物的一般类型为可溶性浓缩物、悬浮液浓缩物、胶囊悬浮液、浓缩乳液、微乳液和悬乳液。非水性液体组合物的一般类型为可乳化的浓缩物、可微乳化的浓缩物、可分散浓缩物和油分散体。
固体组合物的一般类型为粉剂、粉末、颗粒剂、球剂、小粒、锭剂、片剂、填充膜(包括种子包衣)等,它们可为水分散性的(“可润湿的”)或水溶性的。由成膜溶液或可流动的悬浮液形成的膜和包衣尤其可用于种子处理。活性成分可被(微)包封,并且进一步形成悬浮液或固体制剂;作为另外一种选择,可将活性成分的整个制剂包封(或“包覆”)。包封可控制或延缓活性成分的释放。可乳化的颗粒结合了可乳化的浓缩物制剂和干颗粒制剂两者的优点。高强度组合物主要用作其它制剂的中间体。
值得注意的是组合物实施例,其中使包含式1(或其N-氧化物或盐)的化合物的固体组合物颗粒与包含组分(b)的固体组合物颗粒混合。这些混合物可进一步与包含一种或多种附加的生物活性化合物或试剂,例如附加的农用保护剂的颗粒混合。作为另外一种选择,可将两种或更多种农用保护剂(例如组分(a)(式1)化合物、组分(b)化合物、不是组分(a)或(b)的农用保护剂)混合于一组颗粒固体组合物中,然后与一组或多组包含一种或多种附加农用保护剂的固体组合物颗粒混合。这些颗粒的混合物可以根据PCT专利公布WO94/24861中公开的一般颗粒混合物,或更优选地根据美国专利6,022,552中教导的均匀颗粒混合物。
可喷雾的制剂通常在喷雾前分散在适宜的介质中。将此类液体制剂和固体制剂配制成易于在喷雾介质(通常为水)中稀释的制剂。喷洒体积的范围可以为每公顷约一升至几千升,但更典型为每公顷约十至几百升。可喷雾的制剂可在水槽中与水或另一种适宜的介质混合,以通过空气或地面施用来处理叶,或者施用到植物的生长介质中。液体和干燥制剂可直接定量加入滴灌系统中,或者在种植期间定量加入垄沟中。液体和固体制剂可在种植前的种子处理时施用到作物和其它期望植被的种子上,以通过全身吸收来保护发育中的根部和其它地下植物部分和/或叶。
所述制剂通常将包含有效量的活性成分、稀释剂和表面活性剂,其在如下的近似范围内,总计至多100重量%。
固体稀释剂包括例如粘土诸如膨润土、蒙脱石、绿坡缕石和高岭土、石膏、纤维素、二氧化钛、氧化锌、淀粉、糊精、糖(例如乳糖、蔗糖)、硅石、滑石粉、云母、硅藻土、尿素、碳酸钙、碳酸钠和碳酸氢钠以及硫酸钠。典型的固体稀释剂描述于Watkins等人的Handbook ofInsecticide Dust Diluents and Carriers第2版(Dorland Books,Caldwell,NewJersey)中。
液体稀释剂包括例如水、N,N-二甲基烷酰胺(例如N,N-二甲基甲酰胺)、柠檬烯、二甲基亚砜、N-烷基吡咯烷酮(例如N-甲基吡咯烷酮)、乙二醇、三甘醇、丙二醇、二丙二醇、聚丙二醇、碳酸亚丙酯、碳酸亚丁酯、石蜡(例如白矿物油、正链烷烃、异链烷烃)、烷基苯、烷基萘、甘油、三乙酸甘油酯、山梨醇、甘油三乙酸酯、芳族烃、脱芳脂族化合物、烷基苯、烷基萘、酮(如环己酮、2-庚酮、异佛尔酮和4-羟基-4-甲基-2-戊酮)、乙酸酯(如乙酸异戊酯、乙酸己酯、乙酸庚酯、乙酸辛酯、乙酸壬酯、乙酸十三烷基酯和乙酸异冰片酯)、其它酯(如烷基化乳酸酯、二元酯和γ-丁内酯)、并且可为直链、支链、饱和或不饱和醇(如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、正己醇、2-乙基己醇、正辛醇、癸醇、异癸醇、异十八醇、鲸蜡醇、月桂醇、十三烷醇、油醇、环己醇、四氢糠醇、二丙酮醇和苄醇)。液体稀释剂还包括饱和的和不饱和的脂肪酸(通常为C6-C22)的甘油酯,诸如植物种子和果实的油(例如,橄榄油、蓖麻油、亚麻籽油、芝麻油、玉米油(玉米油)、花生油、葵花籽油、葡萄籽油、红花油、棉籽油、大豆油、油菜籽油、椰子油和棕榈仁油),动物源脂肪(例如,牛脂、猪脂、猪油、鳕鱼肝油、鱼油),以及它们的混合物。液体稀释剂还包括烷基化(例如甲基化、乙基化、丁基化)脂肪酸,其中脂肪酸可通过得自植物和动物源的甘油酯的水解获得,并且可通过蒸馏纯化。典型的液体稀释剂描述于Marsden的Solvents Guide第2版(Interscience,New York,1950)中。
本发明的固体组合物和液体组合物通常包含一种或多种表面活性剂。当加入液体中时,表面活性剂(还被称为“表面活性试剂”)通常修饰、最通常减小液体的表面张力。根据表面活性剂分子中的亲水基团和亲脂基团的性质,表面活性剂可用作润湿剂、分散剂、乳化剂或消泡剂。
表面活性剂可分为非离子的、阴离子的或阳离子的。用于本发明组合物的非离子表面活性剂包括但不限于:醇烷氧基化物诸如基于天然醇和合成醇(其可为支链或直链的)并且由醇和环氧乙烷、环氧丙烷、环氧丁烷或它们混合物制备的醇烷氧基化物;胺乙氧基化物、链烷醇酰胺和乙氧基化链烷醇酰胺;烷氧基化甘油三酯,诸如乙氧基化大豆油、蓖麻油和油菜籽油;烷基苯酚烷氧基化物,诸如辛基苯酚乙氧基化物、壬基苯酚乙氧基化物、二壬基苯酚乙氧基化物和十二烷基苯酚乙氧基化物(由苯酚和环氧乙烷、环氧丙烷、环氧丁烷或它们混合物制得);环氧乙烷或环氧丙烷制备的嵌段聚合物和其中末端嵌段由环氧丙烷制备的反式嵌段聚合物;乙氧基化脂肪酸;乙氧基化脂肪酯和油;乙氧基化甲酯;乙氧基化三苯乙烯基苯酚(包括由环氧乙烷、环氧丙烷、环氧丁烷或它们混合物制备的那些);脂肪酸酯、甘油酯、基于羊毛脂的衍生物、多乙氧基化酯(诸如多乙氧基化脱水山梨糖醇脂肪酸酯、多乙氧基化山梨醇脂肪酸酯和多乙氧基化甘油脂肪酸酯);其它脱水山梨糖醇衍生物,诸如脱水山梨糖醇酯;聚合物表面活性剂,诸如无规共聚物、嵌段共聚物、醇酸peg(聚乙二醇)树脂、接枝或梳型聚合物以及星型聚合物;聚乙二醇(peg);聚乙二醇脂肪酸酯;基于有机硅的表面活性剂;和糖衍生物,诸如蔗糖酯、烷基多苷和烷基多糖。
可用的阴离子表面活性剂包括但不限于:烷基芳基磺酸及其盐;羧化醇或烷基苯酚乙氧基化物;二苯基磺酸酯衍生物;木质素和木质素衍生物,诸如木质素磺酸盐;马来酸或琥珀酸或它们的酸酐;烯烃磺酸酯;磷酸酯,诸如醇烷氧基化物的磷酸酯、烷基苯酚烷氧基化物的磷酸酯和苯乙烯基苯酚乙氧基化物的磷酸酯;基于蛋白质的表面活性剂;肌氨酸衍生物;苯乙烯基苯酚醚硫酸盐;油和脂肪酸的硫酸盐和磺酸盐;乙氧基化烷基苯酚的硫酸盐和磺酸盐;醇的硫酸盐;乙氧基化醇的硫酸盐;胺和酰胺的磺酸盐,诸如N,N-烷基牛磺酸盐;苯、异丙基苯、甲苯、二甲苯以及十二烷基苯和十三烷基苯的磺酸盐;缩聚萘磺酸盐;萘和烷基萘的磺酸盐;石油馏分的磺酸盐;磺基琥珀酰胺酸盐;以及磺基琥珀酸盐和它们的衍生物,诸如二烷基磺基琥珀酸盐。
可用的阳离子表面活性剂包括但不限于:酰胺和乙氧基化酰胺;胺诸如N-烷基丙二胺、三亚丙基三胺和二亚丙基四胺,和乙氧基化胺、乙氧基化二胺以及丙氧基化胺(由胺和环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物制备);胺盐诸如胺乙酸盐和二胺盐;季铵盐,诸如季盐、乙氧基化季盐和二季盐;以及胺氧化物,诸如烷基二甲基胺氧化物和双-(2-羟乙基)-烷基胺氧化物。
还可用于本发明组合物的是非离子表面活性剂和阴离子表面活性剂的混合物,或非离子表面活性剂和阳离子表面活性剂的混合物。非离子、阴离子和阳离子表面活性剂以及它们的推荐用途公开于多个已公布的参考文献中,包括由McCutcheon’s Division,TheManufacturing Confectioner Publishing Co.出版的“McCutcheon’s Emulsifiers andDetergents”(北美和国际年鉴版);Sisely和Wood,Encyclopedia of Surface ActiveAgents,Chemical Publ.Co.,Inc.,New York,1964中描述的那些。以及A.S.Davidson和B.Milwidsky的“SyntheticDetergents”第七版(John Wiley and Sons,New York,1987)。
本发明的组合物还可包含本领域中技术人员已知为辅助制剂的制剂助剂和添加剂(其中的一些也可被认为起到固体稀释剂、液体稀释剂或表面活性剂的作用)。此类制剂助剂和添加剂可控制:pH(缓冲液)、加工过程中的泡沫形成(消泡剂诸如聚有机硅氧烷)、活性成分的沉降(悬浮剂)、粘度(触变增稠剂)、容器内的微生物生长(抗微生物剂)、产品冷冻(防冻剂)、颜色(染料/颜料分散体)、洗脱(成膜剂或粘合剂)、蒸发(防蒸发剂)和其它制剂特性。成膜剂包括例如聚乙酸乙烯酯、聚乙酸乙烯酯共聚物、聚乙烯吡咯烷酮-乙酸乙烯酯共聚物、聚乙烯醇、聚乙烯醇共聚物和蜡。制剂助剂和添加剂的例子包括由McCutcheon’sDivision,TheManufacturing Confectioner Publishing Co.出版的McCutcheon’sVolume2:Functional Materials,北美和国际年鉴版;以及PCT公布WO 03/024222中列出的那些。
通常通过将活性成分溶于溶剂中或通过在液体或干燥稀释剂中研磨,将式1的化合物和其它活性成分掺入本发明的组合物中。可通过简单地混合所述成分来制备溶液,包括可乳化浓缩物。如果用作可乳化浓缩物的液体组合物的溶剂是水不混溶的,则通常加入乳化剂以使含有活性物质的溶剂在用水稀释时乳化。可使用介质磨湿磨具有至多2,000μm粒径的活性成分浆液,以获得具有低于3μm平均直径的颗粒。含水浆液可制成成品悬浮液浓缩物(参见例如U.S.3,060,084)或者通过喷雾干燥进一步加工以形成水分散性颗粒。干燥制剂通常需要干燥研磨加工,其产生2至10μm范围内的平均粒径。粉剂和粉末可通过共混并通常碾磨(如用锤磨机或流能磨)来制备。可通过将活性物质喷雾在预成形的颗粒载体上或通过附聚技术来制备颗粒和粒料。参见,Browning,“Agglomeration”,ChemicalEngineering,1967年12月4日,第147-48页;Perry的Chemical Engineer’s Handbook,第4版,McGraw-Hill,New York,1963,第8-57页及其后页,以及WO 91/13546。粒料可如U.S.4,172,714中所述来制备。水分散性和水溶性颗粒可如U.S.4,144,050、U.S.3,920,442和DE3,246,493中所提出来制备。片剂可如U.S.5,180,587、U.S.5,232,701和U.S.5,208,030中所提出来制备。膜可如GB 2,095,558和U.S.3,299,566中所提出来制备。
关于制剂领域的其它信息,参见T.S.Woods的Pesticide Chemistry andBioscience,The Food-Environment Challenge中的“The Formulator’s Toolbox-Product Forms for Modern Agriculture”,T.Brooks和T.R.Roberts编辑,Proceedingsof the 9th International Congress on Pesticide Chemistry,The Royal Society ofChemistry,Cambridge,1999,第120-133页。还参见U.S.3,235,361,第6栏,第16行至第7栏,第19行和实例10-41;U.S.3,309,192,第5栏,第43行至第7栏,第62行和实例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167和169-182;U.S.2,891,855,第3栏,第66行至第5栏,第17行和实例1-4;Klingman,Weed Control as a Science,John Wiley and Sons,Inc.,New York,1961,第81-96页;Hance等人,“Weed Control Handbook”,第8版,Blackwell Scientific Publications,Oxford,1989;以及Developments in formulationtechnology(PJB Publications,RichmoBd,UK,2000)。
无需进一步详尽说明,据信本领域的技术人员使用上述制剂具体实施方式可将本发明利用至最大限度。因此,以下制剂的实例应理解为仅是例证性的,而不以任何方式限制本发明的公开内容。百分比按重量计,并且所述制剂以常规方式来制备。化合物编号参照索引表A中的化合物。组分标记是指表A1中组分(b)栏中所示的对应的化合物。例如,“组分(b1a)”是指1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮。
实例A
高强度浓缩物
实例B
可润湿粉末
实例C
颗粒剂
实例D
挤出的粒料
实例E
可乳化浓缩物
实例F
微乳液
实例G
高强度浓缩物
实例H
颗粒剂
化合物1、2、3、4、5、6、7、8、9、10、11和12中的任一个 5.0%
组分(b9a) 5.0%
绿坡缕石颗粒剂(低挥发性物质,
0.71/0.30mm;U.S.S.No.25-50筛) 90.0%
实例I
挤出的粒料
实例J
可乳化浓缩物
实例K
种子处理剂
实例L
可润湿粉末
实例M
可乳化浓缩物
如已经提及的,组分(a)、(b)以及任选地(c)的组合可以一起或单独地与表面活性剂、固体稀释剂或液体稀释剂配制中的至少一种配制。因此,可将组分(a)、(b)和(c)中的一种、两种或全部三种可配制在一起以形成预混物组合物,或可将它们单独地配制,然后在施用前将配制的组合物混合在一起(例如,在喷雾罐中),或作为另外一种选择连续施用。在包含组分(a)、(b)或(c)的配制的组合物中,组分(a)、(b)或(c)的含量可以为生物有效量,或更具体地,例如如果它们是杀菌性的则为杀菌有效量,或如果它们是杀虫性的则为杀虫有效量。
在施用前,制剂常常用水稀释以形成含水组合物直接应用于植物或其部分的含水组合物(例如,喷雾罐组合物)通常包含至少约1ppm或更多(例如,1ppm至100ppm)的根据本发明的杀真菌活性化合物。
本发明的组合物可用作植物病害控制剂。因此,本发明还包括用于控制由真菌植物病原体引起的植物病害的方法,其包括向待保护的植物或其部分,或向待保护的植物种子或植物繁殖单元施用有效量的本发明组合物(例如,包含组分(a),或组分(a)和(b),或组分(a)、(b)和(c)的组合物)。本发明的这个方面还可描述为用于保护植物或植物种子免受由真菌病原体引起的病害的方法,所述方法包括向植物(或其部分)或植物种子施用杀真菌有效量的本发明组合物(直接施用到植物或植物种子上,或通过环境(例如生长介质)施用)。
可将组分(a)化合物和/或其与组分(b)化合物和/或(c)一种或多种其它生物活性化合物或试剂的组合施用到基因转化的植物上,以表达对无脊椎害虫有毒的蛋白质(诸如苏云金芽孢杆菌δ-内毒素)。外部单独地施用本发明组分(a)或施用其与组分(b)和任选地组分(c)的组合的效果可与表达的毒素蛋白质协同作用。
通常通过在感染之前或之后,将有效量的本发明组合物(例如包含组分(a),或组分(a)、(b)和任选地(c)的混合物),通常以配制好的组合物的形式,施用到待保护的植物部分如根、杆、叶片、果实、种子、块茎或鳞茎,或施用到待保护植物在其中生长的介质(土壤或沙土),来实现植物病害控制。还可将组分(a)或其混合物施用于种子,以保护种子以及由种子发育的幼苗。还可通过灌溉水来施用所述混合物,以处理植物。感染收割前产品的收割后病原体的控制通常通过现场施用本发明的组合物来实现,并且在其中在收割后发生感染的情况下,可将组合物以浸渍剂、喷雾剂、熏蒸剂、处理包裹物或箱衬垫的形式施用于收割后的作物。
组分(a)(即,至少一种化合物,所述化合物选自式1的化合物、其N-氧化物和其盐)适宜的施用量(例如,杀真菌有效量),以及根据本发明组分(b)和任选地(c)的适宜的施用量(例如生物有效量、杀真菌有效量或杀虫有效量)可受许多环境因素影响并应在实际的使用条件下确定。当以小于约1g/ha至约5,000g/ha活性成分的施用量处理时,叶子通常可受到保护。当以约0.1g至约10g每千克种子的施用量处理种子时,种子和幼苗通常可受到保护;并且当以约0.1至约10g每千克繁殖单元的量处理繁殖单元时,植物的繁殖单元(例如插条和块茎)可通常被保护。本领域技术人员可通过简单的实验容易地确定提供植物保护和植物病害以及任选地其它植物害虫控制所期望的范围所需的,包含根据本发明的活性成分的具体组合的组分(a)及其混合物和组合物的施用量。
式1的化合物、其N-氧化物和盐,对于控制由真菌病原体,尤其是担子菌纲和子囊菌纲引起的植物病害特别有效。将这些化合物与其它杀真菌化合物混合可提供控制由担子菌纲、子囊菌纲、卵菌纲和半知菌纲广谱真菌植物病原体引起的病害。因此,本文所述的混合物和组合物可控制广谱植物病害、作物叶病原体,包括:谷类作物,诸如小麦、大麦、燕麦、裸麦、黑小麦、水稻、玉米、高粱和小米;蔓生作物,诸如鲜食葡萄和酿酒葡萄;大田作物,诸如油菜(卡诺拉)、向日葵;糖用甜菜、甘蔗、大豆、花生(落花生)、烟草属植物、苜蓿草、三叶草、胡枝子、车轴草和野豌豆;仁果类水果,诸如苹果、梨、野苹果、枇杷、山楂和温柏;核果类水果,诸如桃子、樱桃、李子、杏、蜜桃和杏仁;柑橘类水果,诸如柠檬、酸橙、橙、柚子、中国柑桔(橘子)和金橘;根和块茎蔬菜和大田作物(以及它们的叶),诸如洋蓟、根甜菜和糖用甜菜、胡萝卜、木薯、姜、人参、山葵、欧洲防风草、马铃薯、白萝卜、芜菁甘蓝、甘薯、芜菁;萝卜和薯蓣;鳞茎蔬菜,诸如大蒜、韭葱、洋葱和葱;叶菜,诸如芥子苦菜(芝麻菜)、芹菜、芹菜、水芹、菊苣(茅菜)、茴香、莴苣头和莴苣叶、欧芹、红菊苣(红菊苣)、大黄、菠菜和唐莴苣;芸苔属(高丽菜)叶菜,诸如西兰花、花椰菜(西兰花)、芽甘蓝、卷心菜、白菜、菜花、甘蓝、羽衣甘蓝、大头菜、芥菜和绿叶蔬菜;豆类蔬菜(多汁的或无汁的),诸如羽扇豆、菜豆((菜豆属)(包括蚕豆、四季豆、利马豆、菜豆、花豆、红花菜豆、食荚菜豆、宽叶菜豆和黄荚种菜豆)、菜豆(豇豆属)(包括赤豆、长豇豆、眉豆、乌豇豆、豆角、豇豆、豇豆、蛾豆、绿豆、饭豆、豇豆、黑绿豆和特长豇豆)、蚕豆(蚕豆)、鹰嘴豆(埃及豆)、瓜耳、刀豆、鹊豆、兵豆和豌豆(豌豆属)(包括四季豆、食荚豌豆、英国豆、红豌豆、豌豆、青豌豆、雪豆、甜豆、木豆和大豆);果实蔬菜,诸如茄子、地樱桃(酸浆属)、茄瓜和胡椒(包括铃状椒、红辣椒、烹饪胡椒、甘椒树、甜椒;青番茄和番茄);葫芦蔬菜,诸如佛手瓜(果实)、冬瓜(冬瓜)、枸橼西瓜、黄瓜、嫩黄瓜、可食用葫芦(包括葫芦、西葫芦、丝瓜、和葵)、苦瓜属(包括胶苦瓜、山苦瓜、苦瓜和中国黄瓜)、香瓜(包括香瓜和南瓜)、西葫芦和笋瓜(包括胡桃南瓜、南瓜、笋瓜、小青南瓜、面条瓜)和西瓜;浆果类,诸如黑莓(包括红果莓、波伊森莓、露莓、矮灌蓝莓、紫蓝莓、紫草梅和杨氏草莓)、蓝莓、蔓越莓、黑醋栗、接骨木莓、鹅莓、欧越莓、罗甘莓、树莓和草莓;树坚果,诸如杏仁、山毛榉树坚果、巴西果、灰胡桃、腰果、板栗、北美矮栗树果实、榛子(榛果)、山核桃树坚果、夏威夷坚果、美洲山核桃树和胡桃木;热带水果和其它作物,诸如香蕉、大蕉、芒果、椰子、木瓜、番石榴、鳄梨、荔枝、龙舌兰、咖啡、可可、甘蔗、油棕、芝麻、橡胶和香料;纤维作物,诸如棉、亚麻和大麻;草坪草(包括暖季型和凉季型草坪草),诸如本特草、肯塔基兰草、野牛草、高羊茅和百慕大草。
这些病原体包括:卵菌纲,包括疫霉属病原体诸如致病疫霉、大豆疫霉病菌、柑桔脚腐病菌、樟疫霉菌和南瓜疫病菌,草腐霉枯萎属病原体诸如瓜果腐霉菌,以及霜霉族的病原体诸如葡萄霜霉病菌,霜霉属(包括烟草霜霉菌(Peronospora tabacina)和寄生霜霉菌(Peronospora parasitica)、假霜霉属(Pseudoperonospora)(包括黄瓜霜霉病菌(Pseudoperonospora cubensis))和盘梗霉菌病菌(Bremia lactucae);子囊菌纲,包括链格孢属病原体诸如番茄早疫病菌和甘蓝黑斑病菌,球座菌属病原体诸如葡萄球座菌,黑星菌属病原体诸如苹果黑星病菌,壳针孢属病原体诸如颖枯病菌和叶枯病菌,白粉病病害病原体诸如布氏白粉属(包括小麦白粉病菌)和白粉菌属(包括萝白粉病菌)、葡萄白粉病菌、黄瓜白粉病菌和苹果白粉病菌,小麦基腐病菌,灰霉菌属病原体诸如草莓灰霉病菌、桃褐腐病菌,菌核菌属病原体诸如油菜菌核病菌和小菌核菌,稻瘟病菌,葡萄枝枯病菌,蠕形菌属病原体诸如玉米大斑病菌、网纹病菌,炭疽病害病原体诸如黑果病菌或刺盘孢属(诸如粱炭疽病菌和西瓜炭疽病菌),和小麦全蚀病菌;担子菌,包括由锈菌属造成的锈菌病害(诸如隐匿柄锈菌、条锈菌、叶锈菌、杆锈菌和柄锈菌),咖啡锈菌和大豆锈菌;其它病原体包括丝核菌属(诸如立枯丝核菌和赤色菌核病菌);镰孢菌病原体诸如粉红镰孢菌、禾谷镰孢菌和尖孢镰孢菌;大丽轮枝菌(Verticillium dahliae);白绢菌(Sclerotium rolfsii);云纹菌;黑涩病菌、黑斑病菌和褐斑病菌;核盘菌(Rutstroemia floccosum)((还被称为币斑菌(Sclerontina homoeocarpa);根霉属物种;(诸如匍枝根霉);曲霉属物种(诸如黄曲霉和寄生曲霉);以及其它与这些病原体密切相关的属和菌种。一般地,病原体被称为病害,并因此在前述的语句中,词“病原体”也指的是由病原体引起的植物病害。更精确地,植物病害由病原体引起。因此例如,白粉病为由白粉病病原体引起的植物病害,壳针孢属病害为由壳针孢属病原体引起的植物病害,并且锈蜱病害为由锈蜱病害病原体引起的植物病害。某些杀真菌化合物还为杀菌的,并因此除它们的杀真菌活性以外,所述组合物或组合还可具有对抗细菌,诸如梨火疫病菌、野油菜黄单胞菌、丁香假单胞菌和其它相关菌种的活性。此外,根据本发明的式1的化合物及其混合物和组合物可用于处理由真菌和细菌引起的果实和蔬菜的收割后病害。这些感染可在收割之前、期间和之后发生。例如,感染可在收割之前发生然后保持非活性的直至成熟过程中的一些点(例如,宿主以感染能够继续进行的方式开始组织变化);并且感染可从由机械或昆虫损伤产生的表面伤口开始。在这方面,根据本发明的化合物、混合物和组合物的施用可减少由于可能在收割至消费的任何时间下发生的收割后病害的损失(即,数量和质量造成的损失)。用本发明的化合物处理收割后病害可增加易腐可使用植物部分(例如,果实、种子、叶、茎、球茎、块茎)在收割后冷冻或未冷冻储藏的持续时间,并保持可适用性且没有受到真菌或其它微生物的明显或有害的降解或污染。用根据本发明的化合物、混合物或组合物处理收割之前或之后的可食用植物部分还可减少真菌或其它微生物的毒性代谢物的形成,例如霉菌毒素诸如黄曲霉素。
在本发明的杀真菌组合物中,组分(a)的式1化合物可与组分(b)的附加杀真菌化合物协同作用以提供诸如以下的有益效果:扩展所控制的植物病害范围、延长预防性和治疗性保护的持续时间以及抑制耐碱真菌病原体的增殖。在特定实施例中,提供了根据本发明的组合物,所述组合物包含成比例的组分(a)和组分(b),其尤其可用于控制具体的真菌病害(诸如番茄早疫病菌、小麦白粉病菌、草莓灰霉病菌、隐匿柄锈菌、立枯丝核菌、颖枯病菌、叶枯病菌)。
与可基于单独组分的活性预期的相比,杀真菌剂混合物还可提供显著更好的病害控制度。此协同作用被描述为“混合物中两种组分的协同作用可使总效果比的两种(或多种)组分单独获得的效果之和更大或更持久”(参见P.M.L.Tames,Neth.J.PlantPathology1964,70,73-80)。在其中协同由施用到植物或种子的活性成分(如,杀真菌化合物)的组合表现出的,提供植物病害控制的方法中,所述活性成分以协同重量比和协同(即协同有效的)量施用。病害控制、抑制和预防的量度不能超过100%。因此,基本的协同作用的表达通常需要使用活性成分的施用量,其中所述活性成分单独地提供远小于100%的效果,使得它们的累加效应基本上小于100%,从而使效果由于协同作用可能增加。在另一方面,活性成分太低的施用量在混合物中可能不示出很多活性,即使有协同作用的有益效果。本领域的技术员通过简单的实验可容易地识别并优化提供协同作用的杀真菌化合物的重量比和施用量(即,量)。
以下测试包括展示式1的化合物对于控制具体病原体的效果的测试;因此向包含这些化合物的杀真菌混合物提供该效果。然而,由本发明化合物单独或以混合物形式提供的病害控制不限制于所例示的病原性真菌菌种。
对于化合物的描述参见索引表A。对于熔点数据,参见索引表B。缩写“Cmpd.”代表“化合物”,并且缩写“Ex.”代表“实例”并且后面跟随数字表示其中制得所述化合物的合成实例。质谱(M.S.)作为通过向所述分子加成H+(分子量为1)所形成的最高同位素丰度母离子(M+1)的分子量报道,采用大气压化学电离(AP+)通过质谱仪观察。未报道包含一个或多个较低丰度(例如37Cl、81Br)的较高原子量同位素的分子离子的存在。
索引表A
*熔点(MP)数据在索引表B中列出。
索引表B
a熔点数据为℃。
本发明的生物学实例
制备用于测试A-I的测试悬浮液的一般方案:首先将测试化合物溶解于量等于3%最终体积的丙酮中,然后以期望的浓度(以ppm为单位)悬浮在丙酮和纯化水(按体积计50/50混合)中,所述纯化水包含250ppm的表面活性剂014(多元醇酯)。然后将所得的测试悬浮液用于测试A-I中。每个测试以一式三份进行,并且平均所述结果。在测试植物上喷洒200ppm测试悬浮液至流失点,等同于约800g/ha的施用量。除非另外指明,使用表示200ppm测试悬浮液的评定值。(使用紧邻评定值的星号“*”表示40ppm测试悬浮液。)
测试A
在番茄幼苗上喷洒测试悬浮液至流失点。第二天,用草莓灰霉病菌(Botrytiscinerea)(番茄灰霉病的致病原)的孢子悬浮液感染所述幼苗,并且在20℃的饱和气氛中培养48h,然后转移到24℃的生长室中再培养3天,其后进行目视病害评定。
测试B
在番茄幼苗上喷洒测试悬浮液至流失点。第二天,用番茄早疫病菌(Alternariasolani)(番茄早疫病的致病原)的孢子悬浮液感染所述幼苗,并且在27℃的饱和气氛中培养48h,然后转移到20℃的生长室中培养5天,其后进行目视病害评定。
测试C
在番茄幼苗上喷洒测试悬浮液至流失点。第二天,用马铃薯晚疫病菌(Phytophthora infestans)(番茄晚期枯萎病的致病原)的孢子悬浮液感染所述幼苗,孢子悬浮液感染所述幼苗,并且在20℃的饱和气氛中培养24h,然后移入20℃的生长室中保持5天,其后进行目视病害评定。
测试D
在匍匐翦股颖(Agrostis sp.)幼苗上喷洒测试悬浮液至流失点。第二天,用赤色菌核病菌(Rhizoctonia solani)(草皮褐斑病的致病原)的麸皮和菌丝体浆液感染所述幼苗,并且在27℃的饱和气氛中培养48h,然后转移到27℃的生长室中培养3天,其后进行目视病害评定。
测试E
在小麦幼苗上喷洒测试悬浮液至流失点。第二天,用颖枯病菌(Septorianodorum)(壳针孢属颖斑病的致病原)的孢子悬浮液感染所述幼苗,并且在24℃的饱和气氛中培养48h,然后转移到20℃的生长室中培养9天,其后进行目视病害评定。
测试F
在小麦幼苗上喷洒测试悬浮液至流失点。第二天,用叶枯病菌(Septoriatritici)小麦叶斑枯病致病原)的孢子悬浮液感染所述幼苗,并且在24℃的饱和气氛中培养48h,然后所述幼苗被转移到20℃的生长室中再培养19天,其后进行目视病害评定。
测试G
用隐匿柄锈菌(Puccinia recondita f.sp.tritici)(小麦叶锈病的致病原)的孢子悬浮液感染小麦幼苗,并且在20℃的饱和气氛中培养24h,然后转移到20℃的生长室中培养2天。在该时间结束后,用测试悬浮液喷雾至流失点,然后将所述幼苗移入20℃生长室中培养4天,其后进行目视病害评定。
测试H
在小麦幼苗上喷洒测试悬浮液至流失点。第二天,用隐匿柄锈菌(Puccinia recondita f.sp.tritici)(小麦叶锈病的致病原)的孢子悬浮液感染所述幼苗,并且在20℃的饱和气氛中培养24h,然后转移到20℃的生长室中培养6天,其后进行目视病害评定。
测试I
在小麦幼苗上喷洒测试悬浮液至流失点。第二天,用小麦白粉病菌(还已知为小麦白粉病菌,小麦白粉病的致病原)的孢子粉剂感染所述幼苗,并且在20℃的生长室中培养8天,其后进行目视病害评定。
测试A-I的结果示于表A中。在表中,等级100表示100%的病害防治,而等级0表示无病害防治(相对于对照物)。连字符(-)表示无测试结果。
表A
“Cmpd No.”是指化合物编号。
表A中示出的式1化合物的测试结果示出组分(a)的杀真菌活性有利于根据本发明的组合物的植物病害控制实用性,所述组合物包含组分(a)与组分(b)以及任选地组分(c)的组合。
Claims (18)
1.杀真菌组合物,其包含:
(a)至少一种化合物,所述化合物选自式1的化合物和其盐:
其中
R1为Cl,R2为F,R3为Cl;或
R1为Cl,R2为F,R3为Br;或
R1为Br,R2为F,R3为Cl;和
(b)至少一种杀真菌化合物,所述杀真菌化合物选自:
(b1a)
(b2)
其中Rb1为
(b3)
其中Rb2为-CH2OC(O)CH(CH3)2、-C(O)CH3、-CH2OC(O)CH3、-C(O)OCH2CH(CH3)2或
(b4)
其中Rb3为CH3或F;
(b5)
(b6)
其中Rb4为-(CH2)4CH3、-C(CH3)3或-(CH2)2C≡CH;
(b7)
(b8)
(b9)
其中Rb5为H或F,并且Rb6为-CF2CHFCF3或-CF2CF2H;
(b10)
其中
Rb7为
Rb8为H、卤素或C1-C2烷基;
Rb9为C1-C8烷基、C1-C8卤代烷基或C2-C8烷氧基烷基;
Rb10为卤素、C1-C2烷基或C1-C2卤代烷基;
Rb11为卤素、C1-C2烷基或C1-C2卤代烷基;
Rb12为C1-C2烷基;
Rb13为H、卤素或C1-C2烷基;
Rb14为C1-C2烷基或C1-C2卤代烷基;
Rb15为H、C1-C2烷基或C1-C2卤代烷基;
W为CH或N;
Y为CH或N;并且
Z为CH或N;
(b11)
或
(b12)
以及它们的盐。
2.根据权利要求1所述的组合物,其中组分(a)包含式1的化合物或其盐。
3.根据权利要求1所述的组合物,其中组分(a)包含选自以下的化合物:
4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺,和
4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
4.根据权利要求1至3中任一项所述的组合物,其还包含(c)至少一种附加的化合物或试剂,所述化合物或试剂是生物活性的。
5.根据权利要求4所述的组合物,其中所述组分(c)包含至少一种选自以下的杀真菌化合物:
(c1)苯并咪唑氨基甲酸甲酯杀真菌剂;
(c2)二酰亚胺杀真菌剂;
(c3)脱甲基抑制剂杀真菌剂;
(c4)苯基酰胺杀真菌剂;
(c5)胺/吗啉杀真菌剂;
(c6)磷脂生物合成抑制剂杀真菌剂;
(c7)酰胺杀真菌剂;
(c8)羟基(2-氨基-)嘧啶杀真菌剂;
(c9)苯胺基嘧啶杀真菌剂;
(c10)N-苯基氨基甲酸酯杀真菌剂;
(c11)醌外部抑制剂杀真菌剂;
(c12)苯基吡咯杀真菌剂;
(c13)喹啉杀真菌剂;
(c14)类脂过氧化抑制剂杀真菌剂;
(c15)黑素生物合成抑制剂-还原酶杀真菌剂;
(c16)黑素生物合成抑制剂-脱水酶杀真菌剂;
(c17)羟基苯胺杀真菌剂;
(c18)角鲨烯-环氧酶抑制剂杀真菌剂;
(c19)多抗霉素杀真菌剂;
(c20)苯基脲杀真菌剂;
(c21)醌内部抑制剂杀真菌剂;
(c22)苯甲酰胺杀真菌剂;
(c23)烯醇式吡喃糖醛酸抗生素杀真菌剂;
(c24)己吡喃糖基抗生素杀真菌剂;
(c25)吡喃葡糖基抗生素:蛋白质合成杀真菌剂;
(c26)吡喃葡糖基抗生素:海藻糖酶和肌醇生物合成杀真菌剂;
(c27)氰基乙酰胺肟杀真菌剂;
(c28)氨基甲酸酯杀真菌剂;
(c29)氧化磷酸化解偶联杀真菌剂;
(c30)有机锡杀真菌剂;
(c31)羧酸杀真菌剂;
(c32)杂芳族杀真菌剂;
(c33)膦酸酯杀真菌剂;
(c34)邻氨甲酰基苯甲酸杀真菌剂;
(c35)苯并三嗪杀真菌剂;
(c36)苯-磺酰胺杀真菌剂;
(c37)哒嗪酮杀真菌剂;
(c38)噻吩-甲酰胺杀真菌剂;
(c39)嘧啶酰胺杀真菌剂;
(c40)羧酸酰胺杀真菌剂;
(c41)四环素抗生素杀真菌剂;
(c42)硫代氨基甲酸酯杀真菌剂;
(c43)苯甲酰胺杀真菌剂;
(c44)寄主植物防御诱导型杀真菌剂;
(c45)多位点接触活性杀真菌剂;
(c46)杀真菌化合物,所述杀真菌化合物不是组分(a)和组分(c1)至(c45)的杀真菌化合物;以及(c1)至(c46)的化合物的盐。
6.根据权利要求4所述的组合物,其中组分(c)包含至少一种选自以下的化合物:阿拉酸式苯-S-甲基、aldimorph、唑嘧菌胺、吲唑磺菌胺、敌菌灵、戊环唑、嘧菌酯、苯霜灵、苯霜灵-M、麦锈灵、苯菌灵、苯噻菌胺、异丙基苯噻菌胺、bethoxazin、乐杀螨、联苯、联苯三唑醇、联苯吡菌胺、杀稻瘟菌素-S、啶酰菌胺、糠菌唑、乙嘧酚磺酸酯、丁硫啶、萎锈灵、环丙酰菌胺、敌菌丹、克菌丹、多菌灵、地茂散、百菌清、乙菌利、克霉唑、铜盐、赛座灭、环氟菌胺、霜脲氰、环丙唑醇、嘧菌环胺、抑菌灵、双氯氰菌胺、哒菌清、氯硝胺、乙霉威、醚唑、二氟林、甲菌定、烯酰吗啉、醚菌胺、烯唑醇、烯唑醇-M、敌螨普、二噻农、十二环吗啉、多果定、敌瘟磷、烯肟菌酯、氟环唑、乙环唑、噻唑菌胺、乙嘧酚、土菌灵、唑菌酮、咪唑菌酮、氯苯嘧啶醇、腈苯唑、甲呋酰胺、环酰菌胺、氰菌胺、拌种咯、苯锈啶、丁苯吗啉、胺苯吡菌酮、三苯基乙酸锡、三苯基氯化锡、三苯基氢氧化锡、福美铁、嘧菌腙、氟啶胺、咯菌腈、flumetover、氟吗啉、氟吡菌胺、氟吡菌酰胺、氟酰亚胺、氟嘧菌酯、氟喹唑、氟硅唑、磺菌胺、flutianil、氟酰胺、粉唑醇、氟唑菌酰胺、灭菌丹、三乙膦酸铝、麦穗宁、呋霜灵、福拉比、己唑醇、霉灵、双胍盐、抑霉唑、亚胺唑、双胍辛胺、丁基甲氨酸碘代丙炔酯、种菌唑、异稻瘟净、异菌脲、丙森锌、稻瘟灵、吡唑萘菌胺、异噻菌胺、春雷霉素、醚菌酯、代森锰锌、双炔酰菌胺、代森锰、灭锈胺、消螨多、甲霜灵、甲霜灵-M、叶菌唑、磺菌威、代森联、苯氧菌胺、嘧菌胺、苯菌酮、腈菌唑、萘替芬、甲胂铁铵(甲基胂酸铁)、氟苯嘧啶醇、辛噻酮、呋酰胺、肟醚菌胺、霜灵、喹酸、咪唑、氧化萎锈灵、氧四环素、戊菌唑、戊菌隆、戊苯吡菌胺、吡噻菌胺、稻瘟酯、磷酸及其盐、苯酞、啶氧菌酯、粉病灵、多抗霉素、噻菌灵、咪鲜安、腐霉利、霜霉威、霜霉威-盐酸盐、丙环唑、丙森锌、丙氧喹啉、硫菌威、丙硫菌唑、唑菌胺酯、唑胺菌酯、唑菌酯、定菌磷、吡菌苯威、稗草畏、啶斑肟、嘧霉胺、pyriofenone、咯喹酮、吡咯尼群、喹唑、灭螨猛、快诺芬、五氯硝基苯、sedaxane、硅噻菌胺、硅氟唑、螺环菌胺、链霉素、硫、戊唑醇、tebufloquin、克枯烂、四氯硝基苯、特比萘芬、氟醚唑、噻菌灵、噻呋灭、硫菌灵、甲基硫菌灵、福美双、噻酰菌胺、甲基立枯磷、对甲抑菌灵、三唑酮、三唑醇、嘧菌醇、triazoxide、三环唑、十三吗啉、氟菌唑、三环唑、肟菌酯、嗪氨灵、垂吗酰胺、灭菌唑、烯效唑、井冈霉素、valifenalate、乙烯菌核利、代森锌、福美锌、苯酰菌胺、N′-[4-[4-氯-3-(三氟甲基)苯氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒、5-氯-6-(2,4,6-三氟苯基)-7-(4-甲基哌啶-1-基)[1,2,4]三唑并[1,5-a]嘧啶(BAS600)、N-[2-[4-[[3-(4-氯苯基)-2-丙炔-1-基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲基磺酰基)氨基]丁酰胺、N-[2-[4-[[3-(4-氯苯基)-2-丙炔-1-基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(乙基磺酰基)氨基]丁酰胺、2-丁氧基-6-碘-3-丙基-4H-1-苯并吡喃-4-酮、3-[5-(4-氯苯基)-2,3-二甲基-3-异唑烷基]吡啶、N-[1-[[[1-(4-氰基苯基)乙基]磺酰基]甲基]丙基]氨基甲酸4-氟苯酯、N-[[(环丙基甲氧基)氨基][6-(二氟甲氧基)-2,3-二氟苯基]亚甲基]苯乙酰胺、α-(甲氧基亚氨基)-N-甲基-2-[[[1-[3-(三氟甲基)苯基]乙氧基]亚氨基]甲基]苯乙酰胺、N′-[4-[4-氯-3-(三氟甲基)苯氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、2-[[[[3-(2,6-二氯苯基)-1-甲基-2-丙烯-1-叉基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基苯乙酰胺、1-[(2-丙烯硫基)羰基]-2-(1-甲基乙基)-4-(2-甲基苯基)-5-氨基-1H-吡唑-3-酮、乙基-6-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、N-[4-[[[[(1-甲基-1H-四唑-5-基)苯基亚甲基]氨基]氧基]甲基-2-噻唑基]氨基甲酸戊酯、N-[6-[[[[(1-甲基-1H-四唑-5-基)苯基亚甲基]氨基]氧基]甲基-2-吡啶基]氨基甲酸戊酯、2-[(3-溴-6-喹啉基)氧基]-N-(1,1-二甲基-2-丁炔-1-基)-2-(甲硫基)乙酰胺、2-[(3-乙炔基-6-喹啉基)氧基]-N-[1-(羟甲基)-1-甲基-2-丙炔-1-基]-2-(甲硫基)乙酰胺、N-(1,1-二甲基-2-丁炔-1-基)-2-[(3-乙炔基-6-喹啉基)氧基]-2-(甲硫基)乙酰胺以及N′-[4-[[3-[(4-氯苯基)甲基]-1,2,4-噻二唑-5-基]氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒。
7.组合物,其包含权利要求1至6中任一项所述的组合物以及至少一种附加组分,所述附加组分选自表面活性剂、固体稀释剂和液体稀释剂。
8.保护植物或植物种子免受由真菌病原体引起的病害的方法,其包括向所述植物或植物种子施用杀真菌有效量的权利要求1至7中任一项所述的组合物。
9.式14的化合物,其为制备权利要求1中式1化合物的中间体
其中R3为Cl或Br。
10.式17的化合物,
其中
R1为Cl,R2为F和R3为Cl;或
R1为Cl,R2为F和R3为Br;或
R1为Br,R2为F和R3为Cl;并且
R32为H、CH3、CH2CH3或(CH2)2CH3。
11.权利要求10的化合物,其中R1为Cl,R2为F和R3为Br。
12.权利要求11的化合物,其中R32为H、CH3或CH2CH3。
13.式17a的化合物,
其中R1为Cl;R2为F;和R3为Br。
14.式20的化合物,其为制备权利要求1中式1化合物的中间体
其中R1为Br,并且R2为F。
15.式22的化合物,
其中
R1为F、Cl或Br;
R2为H或F;
R3为Cl或Br;并且
M为Na或K。
16.权利要求15的化合物,其中R1为Cl;R2为F;R3为Br;和M为Na或K。
17.权利要求1所述的组合物,其中组分(a)为4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
18.权利要求1或权利要求17的组合物,其中组分(b)为
(b3)
其中Rb2为-CH2OC(O)CH(CH3)2。
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