TW202229241A - Nematocidal compounds and use thereof - Google Patents
Nematocidal compounds and use thereof Download PDFInfo
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- 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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- 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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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- 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
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- 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
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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- 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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- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D249/18—Benzotriazoles
Abstract
Description
本發明係關於新穎的殺線蟲化合物。更特別地，本發明係關於式(I)的N-鏈結的雜環氟烯基化合物 (N-linked heterocyclic fluoroalkenyl compounds)及其製備的方法。本發明進一步關於式(I)化合物作為作物保護劑用於防治害蟲例如植物寄生線蟲的用途。The present invention relates to novel nematicidal compounds. More particularly, the present invention relates to N-linked heterocyclic fluoroalkenyl compounds of formula (I) and processes for their preparation. The present invention further relates to the use of compounds of formula (I) as crop protection agents for controlling pests such as plant parasitic nematodes.
PCT專利公開號WO2019186498、PCT專利公開號WO2020075107、PCT專利公開號WO2003042153以及PCT專利公開號WO9708130揭露氟烯基雜環化合物顯示殺線蟲活性，其中包括雜原子（例如氮、硫及氧）的雜環透過C-鏈結 (C-linker)連接到氟烯基團上。此外，PCT專利公開號WO2020157668揭露咖啡因或茶鹼 (theophylline)衍生物具有殺線蟲的活性。PCT Patent Publication No. WO2019186498, PCT Patent Publication No. WO2020075107, PCT Patent Publication No. WO2003042153, and PCT Patent Publication No. WO9708130 disclose that fluoroalkenyl heterocyclic compounds exhibit nematicidal activity, including heterocycles of heteroatoms such as nitrogen, sulfur and oxygen Attached to the fluoroalkene group through a C-linker. In addition, PCT Patent Publication No. WO2020157668 discloses that caffeine or theophylline derivatives have nematicidal activity.
控制植物病原微生物和害蟲對作物造成的損害對於實現高作物效率十分重要。舉例來說，植物病害對於觀賞植物、蔬菜、農作物、穀類以及水果作物造成的損害會導致生產力顯著下降，從而導致消費者成本增加。即使許多產品可用於控制此類損害，但仍需要更有效、成本更低、毒性更低、環境更安全及/或具有不同作用模式的新化合物。Controlling damage to crops by phytopathogenic microorganisms and pests is important for achieving high crop efficiency. For example, damage to ornamental plants, vegetables, crops, cereals, and fruit crops caused by plant diseases can result in a significant drop in productivity, resulting in increased costs to consumers. Even though many products are available to control such damage, there is still a need for new compounds that are more effective, less expensive, less toxic, environmentally safer and/or have different modes of action.
先前技術中所描述的二氟丁烯、三氟丁烯及其他化合物的有效性在功效、實際條件下的處理成本、植物相容性等各方面都無法令人滿意。因此，尋找新穎的殺蟲化合物以避免及/或控制微生物（例如真菌或細菌病原體或害蟲）在更有利的條件下對已知活性成分具有抗性的發展一直是農業領域的高度關注。因此，特別感興趣的是使用比已知化合物活性更高的新化合物，目的是減少活性化合物的使用量，同時至少以與已知化合物相當的方式保持其有效性及持久活性。The effectiveness of difluorobutene, trifluorobutene and other compounds described in the prior art is unsatisfactory in terms of efficacy, cost of treatment under real conditions, phytocompatibility, etc. Therefore, the development of finding novel pesticidal compounds to avoid and/or control the resistance of microorganisms (eg fungal or bacterial pathogens or pests) to known active ingredients under more favorable conditions has been of great interest in the agricultural field. Therefore, it is of particular interest to use new compounds that are more active than known compounds, with the aim of reducing the amount of active compound used while maintaining its effectiveness and long-lasting activity at least in a manner comparable to known compounds.
本發明係描述式(I)化合物，其具有上述效果或優點。根據本發明的該等式(I)化合物，即其中雜環的環被取代的N-鏈結的雜環氟烯基化合物，對於不想要的害蟲例如植物寄生線蟲，顯示出無法預期且顯著地高的活性。The present invention describes compounds of formula (I) which have the aforementioned effects or advantages. The compounds of the formula (I) according to the present invention, ie N-linked heterocyclic fluoroalkenyl compounds in which the ring of the heterocycle is substituted, exhibit unexpectedly and significantly against unwanted pests such as plant parasitic nematodes high activity.
本發明係關於新穎的式(I)的N-鏈結的雜環氟烯基化合物。
在一實施例中，本發明提供一種製備式(I)化合物的方法。In one embodiment, the present invention provides a method of preparing a compound of formula (I).
在另一實施例中，本發明提供一種式(I)化合物作為作物保護劑用於防治害蟲，特別是植物寄生線蟲，的用途。In another embodiment, the present invention provides the use of a compound of formula (I) as a crop protection agent for controlling pests, especially plant parasitic nematodes.
定義：definition:
本說明書中的定義僅用於說明目的，並且不以任何方式限制本說明書中揭露的本發明的範圍。The definitions in this specification are for illustrative purposes only, and do not limit the scope of the invention disclosed in this specification in any way.
如本文所使用的用語「包括」(comprises, comprising, includes, including)、「有」(has, having)、「含有」(contains, containing)、「以...為特徵」(characterized by)或其任何其他變化，以涵蓋非排他性的包含，但須遵守明確指出的任何限制。例如，由元件清單組成的組成物、混合物、製程或方法不一定只限於這些元件，還可能包括沒有明確列出的元件或這種組合物、混合物、製程或方法所固有的其他元件。As used herein, the terms "comprises, comprising, includes, including," "has, having," "contains, containing," "characterized by," or any other variation thereof, to cover non-exclusive inclusion, subject to any limitations expressly stated. For example, a composition, mixture, process or method consisting of a list of elements is not necessarily limited to only those elements, but may also include elements not expressly listed or other elements inherent to such composition, mixture, process or method.
連接詞「由...組成」(consisting of)排除任何未指明的元件、步驟或成分。如果出現在請求項中，則將使請求項不能包含除了所述材料以外的其他材料，除非是通常與之相關的雜質。當「由...組成」這一片語出現在一請求項的主體 (body)的某一句子中，而不是緊跟在前言 (preamble)之後時，它只限制該句子中規定的元件；其他元件並沒有被排除在整個請求項之外。The conjunction "consisting of" excludes any unspecified element, step or ingredient. If present in a claim, it will make the claim incapable of containing materials other than those stated, except as impurities normally associated with it. When the phrase "consisting of" appears in a sentence in the body of a claim, rather than immediately following the preamble, it restricts only the elements specified in the sentence; other Elements are not excluded from the overall request item.
連接詞片語「基本上由...組成」(consisting essentially of)係用於定義一種組合物或方法，其中所包括的材料、步驟、特徵、成分或元素，除了文義上揭露的以外，這些額外的材料、步驟、特徵、成分或元素不會實質地影響所請求保護的發明的基本和新穎特徵。用語「基本上由...組成」佔據了「包括」與「由...組成」的中間位置。The connective phrase "consisting essentially of" is used to define a composition or method comprising materials, steps, features, ingredients or elements that, unless disclosed by context, are The additional materials, steps, features, ingredients or elements do not materially affect the basic and novel characteristics of the claimed invention. The phrase "consisting essentially of" occupies the middle position between "comprising" and "consisting of."
此外，除非有明確的相反說明，否則「或」指的是包容性的「或」而非排他性的「或」。例如，一個條件A「或」B是由以下任何一種情況滿足的：A是真（或存在），B是假（或不存在），A是假（或不存在），B是真（或存在），以及A及B都是真（或存在）。Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or". For example, a condition A "or" B is satisfied by any of the following: A is true (or exists), B is false (or does not exist), A is false (or does not exist), and B is true (or exists) ), and both A and B are true (or exist).
同樣地，在本發明的元件或組件之前的不定冠詞「一」(a以及an)是為了不限制該元素或組件的實例（即發生次數）。因此，「一」(a或an)應被理解為包括一個或至少一個，並且元素或組件的單數詞形式也包括複數，除非該數字顯然是指單數。Likewise, the indefinite article "a" (a and an) preceding an element or component of the invention is intended not to limit the instance (ie, the number of occurrences) of that element or component. Thus, "a" (a or an) should be read to include one or at least one, and the singular word form of an element or component also includes the plural unless the number clearly refers to the singular.
如本說明書所述，術語「農藥」 (pesticide)在各種情況下係總是包括術語「作物保護劑」 (crop protection agent)。As described in this specification, the term "pesticide" in each case always includes the term "crop protection agent".
術語「無脊椎動物害蟲」 (invertebrate pest)包括具有經濟重要性的節肢動物、腹足動物及線蟲等害蟲。術語「節肢動物」 (arthropod)包括昆蟲、蟎蟲 (mites)、蜘蛛、蠍子、蜈蚣 (centipedes)、千足蟲 (millipedes)、球潮蟲 (pill bugs)及多足類 (symphylans)。術語「腹足動物」 (gastropod)包括 蝸牛、蛞蝓及其他柄眼目動物 (Stylommatophora)。術語「線蟲」(nematode) 是指線蟲門（Phylum Nematoda）的活生物體。術語「蠕蟲」 (helminths)包括蛔蟲、心絲蟲、植食性線蟲 (Nematoda)、吸蟲 (Tematoda)、棘頭蟲以及絛蟲 (Cestoda)。The term "invertebrate pest" includes pests of economic importance such as arthropods, gastropods and nematodes. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term "gastropod" includes snails, slugs, and other Stylommatophoras. The term "nematode" refers to living organisms of the phylum Phylum Nematoda. The term "helminths" includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), echinocephalus, and tapeworms (Cestoda).
術語「不想要的微生物」 (undesired microorganisms)或「植物病原微生物」(phytopathogenic microorganisms)，如真菌或細菌病原體，分別包括瘧原蟲綱 (Plasmodiophoromycetes)、同卵菌綱 (Oomycetes)、壺菌綱 (Chytridiomycetes)、接合菌綱 (Zygomycetes)、子囊菌綱 (Ascomycetes)、擔子菌綱 (Basidiomycetes)以及半知菌綱 (Deuteromycetes)與假單胞菌科 (Pseudomonadaceae)、根瘤菌科 (Rhizobiaceae)、腸桿菌科 (Enterobacteriaceae)、棒狀桿菌科 (Corynebacteriaceae)以及鏈黴菌科 (Streptomycetaceae)。The term "undesired microorganisms" or "phytopathogenic microorganisms", such as fungal or bacterial pathogens, includes the classes Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, respectively. Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
在本說明書的上下文中，「無脊椎動物害蟲防治」 (invertebrate pest control)是指抑制無脊椎動物害蟲發育（包括死亡率、攝食減少及/或交配中斷），並且相關用語被類似地予以定義。In the context of this specification, "invertebrate pest control" refers to the inhibition of invertebrate pest development (including mortality, reduced feeding and/or disruption of mating), and related terms are similarly defined.
術語「農藝學」 (agronomic)是指田間作物的生產，例如用於食品及纖維，以及包括玉米、大豆及其他豆類、稻米、穀物（例如小麥、燕麥、大麥、黑麥、稻米、玉米）、葉類蔬菜（例如生菜、捲心菜及其他油菜作物）、果類蔬菜（例如番茄、胡椒、茄子、十字花科植物及葫蘆科植物）、馬鈴薯、番薯、葡萄、棉花、樹果（例如梨果、核果及柑橘）、小水果（漿果、櫻桃）以及其他特色作物（例如油菜、向日葵、橄欖）的生長。The term "agronomic" refers to the production of field crops, such as for food and fiber, and includes corn, soybeans and other legumes, rice, grains (eg, wheat, oats, barley, rye, rice, corn), Leafy vegetables (such as lettuce, cabbage and other rape crops), fruit vegetables (such as tomatoes, peppers, eggplants, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (such as pome, Stone fruits and citrus), small fruits (berries, cherries) and other specialty crops (eg canola, sunflowers, olives).
術語「非農藝學」 (nonagronomic)是指農作物以外的作物，例如園藝作物（例如，不是在田間種植的溫室、苗圃或是觀賞植物）、住宅、農業、商業及工業結構、草皮（例如草皮農場、牧場、 高爾夫球場、草坪、運動場）、木製品、儲存產品、農林業及植被管理、公共衛生（即人類）及動物健康（例如，馴養動物（如寵物、家畜及家禽）以及未馴化的動物（如野生動物））的應用。The term "nonagronomic" refers to crops other than crops, such as horticultural crops (eg, greenhouses, nurseries, or ornamentals not grown in the field), residential, agricultural, commercial, and industrial structures, turf (eg, turf farms) , pastures, golf courses, lawns, sports fields), wood products, stored products, agroforestry and vegetation management, public health (i.e. humans) and animal health (e.g. domesticated animals (e.g. pets, livestock and poultry) and undomesticated animals (e.g. such as wildlife)) applications.
非農藝學應用包括藉由向要保護的動物施用殺寄生蟲有效（即生物學有效）量的本發明化合物，通常以配製用於獸醫用途的組成物的形式，保護動物免受無脊椎動物寄生害蟲的侵害。如本案說明書及請求項中所提及的，術語「殺寄生蟲的」 (parasiticidal及parasiticidally)是指對無脊椎寄生害蟲提供保護動物免受害蟲侵害的可觀察效果。殺寄生蟲效果通常涉及減少目標無脊椎寄生害蟲的發生或活動。對害蟲的此類影響包括壞死、死亡、生長遲緩、活動性減弱或在宿主動物體內或體內停留的能力減弱、進食減少和繁殖受到抑制。這些對無脊椎動物寄生蟲害蟲的影響提供了對動物寄生蟲感染或感染的控制（包括預防、減少或消除）。Non-agronomic applications include the protection of animals from invertebrate parasitism by administering to the animal to be protected a parasiticidally effective (ie biologically effective) amount of a compound of the invention, usually in the form of a composition formulated for veterinary use Infestation of pests. As referred to in the description and claims of the present case, the terms "parasiticidal" (parasiticidal and parasiticidally) refer to providing an observable effect on invertebrate parasitic pests to protect animals from pests. Parasiticidal effects generally involve reducing the occurrence or activity of target invertebrate parasitic pests. Such effects on pests include necrosis, death, stunted growth, reduced mobility or ability to remain in or within the host animal, reduced feeding and suppressed reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection in animals.
本發明的化合物可以純物質形式或作為不同可能的異構物形式（例如立體異構物或結構異構物）的混合物存在。不同的立體異構物包括鏡像異構物、非鏡像異構物、掌性異構物、阻轉異構物、構象異構物、旋轉異構物、互變異構物、光學異構物、多晶型物以及幾何異構物。這些異構物的任何預期混合物也落入本案的請求項範圍內。所屬領域中具有通常知識者將理解，當相對於其他異構物富集 (enriched)或與其他異構物分離時，一種立體異構物可能更具活性及/或可能表現出有益效果。此外，所屬技術領域中具有通常知識者係了解分離、濃縮及/或選擇性地製備該等異構物的製程或方法或技術。The compounds of the present invention may exist in pure material form or as a mixture of different possible isomeric forms (eg, stereoisomers or structural isomers). Different stereoisomers include enantiomers, diastereoisomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, Polymorphs and geometric isomers. Any contemplated mixtures of these isomers also fall within the scope of the claims in this case. One of ordinary skill in the art will understand that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to or separated from other isomers. Furthermore, those of ordinary skill in the art are aware of processes or methods or techniques for separating, concentrating and/or selectively preparing such isomers.
現在將對說明書中各種術語的定義予以說明：Definitions of various terms in the specification will now be explained:
術語「烷基」 (alkyl)，不管單獨使用或是以複合詞型態使用（例如「烷硫基」 (alkylthio)或「鹵烷基」 (haloalkyl)或-N(烷基)或烷基羰基烷基或烷基磺醯胺基，包括直鏈或支鏈的C 1至C 24烷基，較佳為C 1至C 15烷基，更佳為C 1至C 10烷基，最佳為C 1至C 6烷基。烷基的非限制性實例包括甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1 ,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基及1-乙基-2-甲基丙基或不同的異構物。如果烷基在複合取代基的末端，例如在烷基環烷基中，則複合取代基的起始部分，例如環烷基，可以被烷基相同或不同地且獨立地單取代或多取代。這同樣也適用於複合取代基，其中其他基團，例如烯基、炔基、羥基、鹵素、羰基、羰氧基等位於末端。 The term "alkyl", whether used alone or in a compound form (e.g. "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkane or alkylsulfonamido groups, including linear or branched C 1 to C 24 alkyl groups, preferably C 1 to C 15 alkyl groups, more preferably C 1 to C 10 alkyl groups, most preferably C 1 to C6 alkyl. Non-limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl , 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3 ,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl Alkyl-1-methylpropyl and 1-ethyl-2-methylpropyl or different isomers. If the alkyl group is at the end of the compound substituent, such as in an alkylcycloalkyl, the compound substituent The starting moiety of , such as cycloalkyl, may be mono- or polysubstituted, identically or differently and independently, by alkyl. The same applies to composite substituents, where other groups such as alkenyl, alkynyl, hydroxyl, Halogen, carbonyl, carbonyloxy, etc. are located at the terminals.
術語「烯基」 (alkenyl)，不管單獨使用或是以複合詞型態使用，包括直鏈或支鏈的C 2-C 24烯烴，較佳為C 2-C 15烯烴，更佳為C 2-C 10烯烴，最佳為C 2-C 6烯烴。烯烴的非限制性實例包括乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基，1,1-二甲基-3-丁烯基，1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基及1-乙基-2-甲基-2-丙烯基及不同的異構物。術語「烯基」還包括多烯，例如1,2-丙二烯基及2,4-己二烯基。除非在別處具體定義，否則此定義也適用於作為複合取代基的一部分的烯基，例如烯基等。 The term "alkenyl", whether used alone or in compound form, includes straight or branched C 2 -C 24 alkenes, preferably C 2 -C 15 alkenes, more preferably C 2 -C alkenes. C 10 olefins, most preferably C 2 -C 6 olefins. Non-limiting examples of olefins include vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl- 1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl Alkenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl Alkenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl yl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl yl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl yl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentene base, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl -3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl , 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl , 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl -1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2 ,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butene base, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl and different isomers . The term "alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to an alkenyl group that is part of a composite substituent, eg, alkenyl and the like, unless specifically defined elsewhere.
術語「炔基」 (alkynyl)，不管單獨使用或是以複合詞型態使用，包括直鏈或支鏈的C 2-C 24炔烴，較佳為C 2-C 15炔烴，更佳為C 2-C 10炔烴，最佳為C 2-C 6炔烴。炔烴的非限制性粒子包括乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基以及1-乙基-1-甲基-2-丙炔基以及不同的異構物。除非在別處特別定義，否則此定義也適用於作為複合取代基的一部分的炔基，例如炔基等。術語「炔基」還可包括由多個三鍵組成的部分，例如2,5-己二炔基。 The term "alkynyl", whether used alone or in compound form, includes straight or branched C 2 -C 24 alkynes, preferably C 2 -C 15 alkynes, more preferably C 2 - C10 alkynes, most preferably C2 - C6 alkynes. Non-limiting particles of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl base, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2- Methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl , 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl yl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl base, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl base, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2 -butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and different isomers. This definition also applies to an alkynyl group that is part of a composite substituent, eg, alkynyl, and the like, unless specifically defined elsewhere. The term "alkynyl" may also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl.
術語「環烷基」 (cyclic alkyl或cycloalkyl)是指閉合以形成環的烷基。非限制性的實例包括，但不限於，環丙基、環丁基、環戊基以及環己基。除非在別處特別定義，否則此定義也適用於作為複合取代基的一部分的環烷基，例如環烷基烷基等。The term "cyclic alkyl" (cyclic alkyl or cycloalkyl) refers to an alkyl group that is closed to form a ring. Non-limiting examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Unless specifically defined elsewhere, this definition also applies to a cycloalkyl group that is part of a composite substituent, eg, cycloalkylalkyl, and the like.
術語「環烯基」(cycloalkenyl)是指閉合以形成包括單環、部分不飽和基團的環的烯基。非限制性的實例包括，但不限於，環戊烯基以及環己烯基。除非在別處特別定義，否則此定義也適用於作為複合取代基的一部分的環烯基，例如環烯基烷基等。The term "cycloalkenyl" refers to an alkenyl group that is closed to form a ring that includes a monocyclic, partially unsaturated group. Non-limiting examples include, but are not limited to, cyclopentenyl and cyclohexenyl. This definition also applies to a cycloalkenyl group that is part of a composite substituent, eg, cycloalkenylalkyl, and the like, unless specifically defined elsewhere.
術語「環炔基」 (cycloalkynyl)是指閉合以形成包括單環、部分不飽和基團的環的炔基。除非在別處特別定義，否則此定義也適用於作為複合取代基的一部分的環炔基，例如環炔基烷基等。The term "cycloalkynyl" refers to an alkynyl group that is closed to form a ring that includes a monocyclic, partially unsaturated group. This definition also applies to a cycloalkynyl group that is part of a composite substituent, eg, cycloalkynylalkyl, and the like, unless specifically defined elsewhere.
術語「環烷氧基」 (cycloalkoxy)、「環烯氧基」 (cycloalkenyloxy)等的定義與上述實例類似。非限制性的實例包括，但不限於，環丙烷氧基、環戊烷氧基以及環己烷氧基。除非在別處特別定義，否則此定義也適用於作為複合取代基的一部分的環烷氧基，例如環烷氧基烷基等。The terms "cycloalkoxy", "cycloalkenyloxy" and the like are defined similarly to the above examples. Non-limiting examples include, but are not limited to, cyclopropanoxy, cyclopentanoxy, and cyclohexaneoxy. Unless specifically defined elsewhere, this definition also applies to cycloalkoxy as part of a composite substituent, eg, cycloalkoxyalkyl, and the like.
術語「烷氧基」 (alkoxy)，不管單獨使用或是以複合詞型態使用，包括直鏈或支鏈的C 1-C 15烷氧基，較佳為C 1-C 10烷氧基，更佳為C 1-C 6烷氧基。烷氧基的實例包括甲氧基、乙氧基、丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基、1,1-二甲基乙氧基、戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、2,2-二甲基丙氧基、 1-乙基丙氧基、己氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基以及1-乙基-2-甲基丙氧基以及不同的異構物。除非在別處特別定義，否則此定義也適用於作為複合取代基的一部分的烷氧基，例如鹵烷氧基、炔基烷氧基等。 The term "alkoxy", whether used alone or in the form of a compound word, includes linear or branched C 1 -C 15 alkoxy, preferably C 1 -C 10 alkoxy, more Preferably it is C 1 -C 6 alkoxy. Examples of alkoxy groups include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- Dimethylethoxy, pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethyl Propoxy, hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methyl Pentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-di Methylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2- Trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy and different isomers thing. Unless specifically defined elsewhere, this definition also applies to alkoxy groups that are part of a composite substituent, eg, haloalkoxy, alkynylalkoxy, and the like.
術語「烷硫基」 (alkylthio)包括支鏈或直鏈烷硫基的官能基，例如甲硫基、乙硫基、丙硫基、1-甲乙硫基、丁硫基、1-甲丙硫基、2-甲丙硫基、1,1-二甲乙硫基、戊硫基、1-甲乙硫基、2-甲丁硫基、3-甲基丁硫基、2,2-二甲基丙硫基、1-乙基丙硫基、己硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、1-甲基戊硫基、2-甲基戊硫基、3-甲基戊硫基、4-甲基戊硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,2-二甲基丁硫基、2,3-二甲基丁硫基、3,3-二甲基丁硫基、1-乙基丁硫基、2-乙基丁硫基、1,1,2-三甲基丙硫基、1,2,2-三甲基丙硫基、1-乙基-1-甲基丙硫基以及1-乙基-2-甲基丙硫基等不同的異構物。The term "alkylthio" includes branched or straight chain alkylthio functional groups such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio base, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylethylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylthio Propylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methyl Pentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutyl Thio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methyl Different isomers such as propylthio.
術語「羥基」 (hydroxy)是指-OH，「胺基」是指-NRR，其中R可以是H或者任何可能的取代基，例如烷基。「羰基」是指-C(=O)-，「羰氧基」是指-OC(=O)-，「亞磺醯基」是指SO，「磺醯基」是指S(O) 2。 The term "hydroxy" refers to -OH and "amino" refers to -NRR, where R can be H or any possible substituent such as alkyl. "Carbonyl" means -C(=O)-, "Carbonyloxy" means -OC(=O)-, "Sulfinyl" means SO, "Sulfonyl" means S(O) 2 .
術語「鹵素」 (halogen)，不管單獨使用或是以複合詞型態使用（例如「鹵烷基」 (haloalkyl)），包括氟、氯、溴或碘。此外，當用於複合詞如「鹵烷基」 (haloalkyl)時，所述烷基可以部分或全部被鹵素原子取代，而鹵素原子可以相同或不同。The term "halogen", whether used alone or in compound form (eg "haloalkyl"), includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound words such as "haloalkyl," the alkyl group may be partially or fully substituted with halogen atoms, which may be the same or different.
「鹵烷基」的非限制性實例包括氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、1,1-二氯-2,2,2-三氟乙基以及1,1,1-三氟丙-2-基。除非在別處具體定義，否則此定義也適用於作為複合取代基的一部分的鹵烷基，例如鹵烷基胺基烷基等。Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromethyl Fluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl Fluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl , pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl and 1,1,1-trifluoropropan-2-yl. Unless specifically defined elsewhere, this definition also applies to haloalkyl groups that are part of a composite substituent, eg, haloalkylaminoalkyl, and the like.
術語「鹵烯基」 (haloalkenyl)、「鹵炔基」 (haloalkynyl)的定義類似，不同之處在於烯基和炔基作為取代基的一部分存在而不是烷基。The terms "haloalkenyl", "haloalkynyl" are defined similarly, except that alkenyl and alkynyl are present as part of a substituent rather than an alkyl group.
術語「鹵烷氧基」 (haloalkoxy)是指直鏈或支鏈烷氧基，其中這些基團中的一些或全部氫原子可以被上述鹵素原子取代。鹵烷氧基的非限制性實例包括氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、五氟乙氧基以及1,1,1-三氟丙-2-氧基。除非在別處具體定義，否則此定義也適用於作為複合取代基的一部分的鹵烷氧基，例如鹵烷氧基烷基等。The term "haloalkoxy" refers to a straight or branched chain alkoxy group wherein some or all of the hydrogen atoms in these groups may be replaced by the halogen atoms described above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro Fluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2 -Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro -2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. Unless specifically defined elsewhere, this definition also applies to haloalkoxy as part of a composite substituent, eg, haloalkoxyalkyl, and the like.
術語「鹵烷硫基」 (haloalkylthio)或「鹵烷基氫硫基」 (haloalkylsulfanyl)是指直鏈或支鏈烷硫基，其中這些基團中的一些或全部氫原子可以被上述鹵素原子取代。鹵烷硫基的非限制性實例包括氯甲硫基、溴甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、二氯氟甲硫基、氯二氟甲硫基、1-氯乙硫基、1-溴乙硫基、1-氟乙硫基、2-氟乙硫基、2-二氟乙硫基、2-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、2,2,2-三氯乙硫基、五氟乙硫基以及1,1,1-三氟丙-2-硫基。除非在別處具體定義，否則此定義也適用於作為複合取代基的一部分的鹵烷硫基，例如鹵烷硫基烷基等。The term "haloalkylthio" or "haloalkylsulfanyl" refers to a straight or branched chain alkylthio group in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as described above . Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloro Fluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2-difluoroethylthio Fluoroethylthio, 2-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio group, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1, 1,1-Trifluoropropan-2-sulfanyl. Unless specifically defined elsewhere, this definition also applies to haloalkylthio as part of a composite substituent, eg, haloalkylthioalkyl, and the like.
「鹵烷基亞磺醯基」(haloalkylsulfinyl)的非限制性實例包括CF 3S(O)、CCl 3S(O)、CF 3CH 2S(O)以及CF 3CF 2S(O)。「鹵烷基磺醯基」 (haloalkylsulfonyl)的非限制性實例包括CF 3S(O) 2、CCl 3S(O) 2、CF 3CH 2S(O) 2以及CF 3CF 2S(O) 2。 Non - limiting examples of "haloalkylsulfinyl" include CF3S (O), CCl3S (O), CF3CH2S (O), and CF3CF2S ( O). Non-limiting examples of "haloalkylsulfonyl" include CF3S (O) 2 , CCl3S (O) 2 , CF3CH2S (O) 2 , and CF3CF2S ( O ) ) 2 .
「烷基亞磺醯基」 (alkylsulfinyl)的非限制性實例包括甲基亞磺醯基、乙基亞磺醯基、丙基亞磺醯基、1-甲基乙基亞磺醯基、丁基亞磺醯基、1-甲基丙基亞磺醯基、2-甲基丙基亞磺醯基、1,1-二甲基乙基亞磺醯基、戊基亞磺醯基、1-甲基丁基亞磺醯基、2-甲基丁基亞磺醯基、3-甲基丁基亞磺醯基、2,2-二甲基丙基亞磺醯基、1-乙基丙基亞磺醯基、己基亞磺醯基、1,1-二甲基丙基亞磺醯基、1,2-二甲基丙基亞磺醯基、1-甲基戊基亞磺醯基、2-甲基戊基亞磺醯基、3-甲基戊基亞磺醯基、4-甲基戊基亞磺醯基、1,1-二甲基丁基亞磺醯基、1,2-二甲基丁基亞磺醯基、1,3-二甲基丁基亞磺醯基、2,2-二甲基丁基亞磺醯基、2,3-二甲基丁基亞磺醯基、3,3-二甲基丁基亞磺醯基、1-乙基丁基亞磺醯基、2-乙基丁基亞磺醯基、1,1,2-三甲基丙基亞磺醯基、1,2,2-三甲基丙基亞磺醯基、1-乙基-1甲基丙基亞磺醯基以及1-乙基-2-甲基丙基亞磺醯基以及不同的異構物。Non-limiting examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butyl sulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethyl Propylsulfinyl, hexylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl base, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutyl Sulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethyl Propylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl Sulfonyl and different isomers.
「烷基磺醯基」 (alkylsulfonyl)的非限制性實例包括甲基磺醯基、乙基磺醯基、丙基磺醯基、1-甲基乙基磺醯基、丁基磺醯基、1-甲基丙基磺醯基、2-甲基丙基磺醯基、1,1-二甲基乙基磺醯基、戊基磺醯基、1-甲基丁基磺醯基、2-甲基丁基磺醯基、3-甲基丁基磺醯基、2,2-二甲基丙基磺醯基、1-乙基丙基磺醯基、己基磺醯基、1,1-二甲基丙基磺醯基、1,2-二甲基丙基磺醯基、1-甲基戊基磺醯基、2-甲基戊基磺醯基、3-甲基戊基磺醯基、4-甲基戊基磺醯基、1,1-二甲基丁基磺醯基、1,2-二甲基丁基磺醯基、1,3-二甲基丁基磺醯基、2,2-二甲基丁基磺醯基、2,3-二甲基丁基磺醯基、3,3-二甲基丁基磺醯基、1-乙基丁基磺醯基、2-乙基丁基磺醯基、1,1,2-三甲基丙基磺醯基、1,2,2-三甲基丙基磺醯基、1-乙基-1甲基丙基磺醯基以及1-乙基-2-甲基丙基磺醯基以及不同的異構物。Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-Methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2 -Methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1 -Dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl Sulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl base, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl , 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1methylpropyl Sulfonyl and 1-ethyl-2-methylpropylsulfonyl and different isomers.
術語「芳磺醯基/芳碸基」(arylsulfonyl)包括Ar-S(O) 2，其中Ar可以是任何碳環或雜環。除非在別處具體定義，否則此定義也適用於作為複合取代基的一部分的烷基磺醯基，例如烷基磺醯基烷基等。 The term "arylsulfonyl" includes Ar-S(O) 2 , where Ar can be any carbocyclic or heterocyclic ring. Unless specifically defined elsewhere, this definition also applies to an alkylsulfonyl group as part of a composite substituent, eg, an alkylsulfonylalkyl group, and the like.
術語「環」 (ring)或「環系統」 (ring system)作為式I的組分是碳環或雜環。The term "ring" or "ring system" as a component of formula I is a carbocyclic or heterocyclic ring.
術語「環系統」表示一或多個環。The term "ring system" refers to one or more rings.
術語「芳香的」 (aromatic)表示滿足休克爾定律 (Hueckel rule)，而術語「非芳香的」 (non-aromatic)則表示不滿足休克爾定律。The term "aromatic" means that Hueckel's law is satisfied, while the term "non-aromatic" means that Hueckel's law is not satisfied.
術語「碳環」 (carbocycle)或「碳環的」 (carbocyclic或carbocyclyl)包括「芳香碳環系統」 (aromatic carbocyclic ring system)或者「非芳香碳環系統」 (nonaromatic carbocylic ring system)或者多環或雙環（螺環 (spiro)、稠合環 (fused)、橋接環 (bridged)、非稠合環 (nonfused)）的環化合物，其中該環可以是芳香或非芳香的（其中芳香表示滿足休克爾法則，非芳香表示不滿足休克爾法則）。The term "carbocycle" or "carbocyclic" (carbocyclic or carbocyclyl) includes "aromatic carbocyclic ring system" or "nonaromatic carbocylic ring system" or polycyclic or Bicyclic (spiro, fused, bridged, nonfused) cyclic compounds, where the ring may be aromatic or non-aromatic (wherein aromatic means that satisfies Hückel law, non-aromatic means that Huckel's law is not satisfied).
非芳香碳環系統的非限制性實例為環丙基、環丁基、環戊基、環己基等。Non-limiting examples of non-aromatic carbocyclic ring systems are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
芳香碳環系統的非限制性實例為苯基、萘基等。Non-limiting examples of aromatic carbocyclic systems are phenyl, naphthyl, and the like.
此處的術語「芳基」 (aryl)係指含有任何碳基芳香族的基團，包括但不限於苯基、萘、聯苯、蒽等。芳基可以是經取代的或者是未取代的。此外，芳基可以是單一環結構或者是包括多環結構，多環結構可以是稠合環結構或者是透過碳-碳鍵結所連接的一或多個橋接基團。The term "aryl" as used herein refers to any carbon-based aromatic group including, but not limited to, phenyl, naphthalene, biphenyl, anthracene, and the like. Aryl groups can be substituted or unsubstituted. In addition, aryl groups may be of a single ring structure or include multiple ring structures, which may be fused ring structures or one or more bridging groups attached through carbon-carbon bonds.
與環相關的術語「雜」 (hetero)是指其中至少一個環原子不是碳並且可以包含1至4個獨立地選自N、O及S的雜原子的環，條件是每個環包含不超過4個氮，不超過2個氧以及不超過2個硫。The term "hetero" in relation to rings refers to rings in which at least one ring atom is not carbon and may contain 1 to 4 heteroatoms independently selected from N, O, and S, provided that each ring contains no more than 4 nitrogens, not more than 2 oxygens and not more than 2 sulfurs.
術語「雜環」 (heterocycle或heterocyclic)包括「芳香雜環」 (aromatic heterocycle)或「雜芳環系統」 (heteroaryl ring system)以及「非芳香雜環系統」 (nonaromatic heterocycle ring system)或多環或雙環（螺、稠合、橋接、非稠合）環化合物，其中環可以是芳香的或非芳香的，其中雜環含有至少一個選自N、O及S(O) 0-2的雜原子，及/或雜環的碳環成員可以被C(=O)、C(=S)、C(=CR*R*)及C=NR*取代，*表示整數。 The term "heterocycle" or "heterocyclic" includes "aromatic heterocycle" or "heteroaryl ring system" as well as "nonaromatic heterocycle ring system" or polycyclic or Bicyclic (spiro, fused, bridged, non-fused) ring compounds, wherein the ring may be aromatic or non-aromatic, wherein the heterocyclic ring contains at least one heteroatom selected from N, O and S(O) 0-2 , and/or the carbocyclic ring members of the heterocycle may be substituted by C(=O), C(=S), C(=CR*R*) and C=NR*, * denotes an integer.
術語「非芳族雜環」（non-aromatic heterocycle或non-aromatic heterocyclic）是指含有1至4個選自O、N及S的雜原子的三至十五員，較佳為三至十二員的飽和或部分不飽和雜環：單、雙或三環雜環，除了碳環成員外，還含有一到三個氮原子及/或一個氧或硫原子或一或兩個氧及/或硫原子如果環含有一個以上的氧原子，則它們不直接相鄰；例如（但不限於）：The term "non-aromatic heterocycle" (non-aromatic heterocycle or non-aromatic heterocyclic) refers to three to fifteen members, preferably three to twelve, containing 1 to 4 heteroatoms selected from O, N and S Member saturated or partially unsaturated heterocycles: mono-, bi- or tricyclic heterocycles containing, in addition to carbocyclic members, one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygens and/or Sulfur atoms If the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to):
環氧乙烷基 (oxiranyl)、氧雜環丁烷基 (oxetanyl)、氮丙啶基 (aziridinyl)、氮雜環丁烷基 (azetidinyl)、硫雜環丁烷基 (thietanyl)、四氫呋喃基 (tetrahydrofuranyl)、四氫噻吩基 (tetrahydrothienyl)、吡咯啶基 (pyrrolidinyl)、異噁唑啶基 (isoxazolidinyl)、異噻唑啶基 (isothiazolidinyl)、吡唑啶基 (pyrazolidinyl)、噁唑啶基 (oxazolidinyl)、噻唑啶基 (thiazolidinyl)、咪唑啶基 (imidazolidinyl)、噁二唑啶基 (oxadiazolidinyl)、噻二唑啶基 (thiadiazolidinyl)、***啶基 (triazolidinyl)、二氫呋喃基 (dihydrofuryl)、二氫噻吩基 (dihydrothienyl)、吡咯啉基 (pyrrolinyl)、異噁唑啉基 (isoxazolinyl)、異噻唑啉基 (isothiazolinyl)、二氫吡唑基 (dihydropyrazolyl)、二氫噁唑基 (dihydrooxazolyl)、哌啶基 (piperidinyl)、吡嗪基 (pyrazynyl)、嗎啉基 (morpholinyl)、硫嗎啉基 (thiomorphlinyl)、l,3-二噁基 (dioxany)、四氫吡喃基 (tetrahydropyranyl)、四氫噻吩基 (tetrahydrothienyl)；其中這些環是透過該等環的一個碳原子或氮原子連接主鏈 (skeleton)。除非在別處具體定義，否則此定義也適用於作為複合取代基的一部分的雜環，例如雜環烷基等。oxiranyl, oxetanyl, aziridinyl, azetidinyl, thietanyl, tetrahydrofuranyl ( tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl , thiazolidinyl, imidazolidinyl, oxadiazolidinyl, thiadiazolidinyl, triazolidinyl, dihydrofuryl, two Dihydrothienyl, pyrrolinyl, isoxazolinyl, isothiazolinyl, dihydropyrazolyl, dihydrooxazolyl, piper Piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, l,3-dioxany, tetrahydropyranyl, tetrahydro tetrahydrothienyl; wherein the rings are connected to the skeleton through a carbon or nitrogen atom of the rings. This definition also applies to heterocycles that are part of a composite substituent, eg, heterocycloalkyl, and the like, unless specifically defined elsewhere.
術語「雜芳基」 (heteroaryl)或「芳族雜環」 (aromatic heterocyclic)是指含有1至4個選自O、N及S的雜原子的五或六員、完全不飽和的單環系統；如果環含有一個以上的氧原子，則它們不直接相鄰；五員雜芳基含有1至4個氮原子或1至3個氮原子及1個硫或氧原子；五員雜芳基，除碳原子外，還可含有1到4個氮原子或1到3個氮原子及1個硫或氧原子作為環成員，舉例（但不限於）：呋喃基 (furyl)、噻吩基 (thienyl)、吡咯基 (pyrrolyl)、異噁唑基 (isoxazolyl)、異噻唑基 (isothiazolyl)、吡唑基 (pyrazolyl)、噁唑基 (oxazolyl)、噻唑基 (thiazolyl)、咪唑基 (imidazolyl)、噁二唑基 (oxadiazolyl)、噻二唑基 (thiadiazolyl)、***基 (triazolyl)、四唑基 (tetrazolyl)；其中這些環是透過該等環的一個碳原子或氮原子連接主鏈，The term "heteroaryl" or "aromatic heterocyclic" refers to a five- or six-membered, fully unsaturated monocyclic ring system containing 1 to 4 heteroatoms selected from O, N and S ; if the ring contains more than one oxygen atom, they are not directly adjacent; five-membered heteroaryl groups contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom; five-membered heteroaryl groups, In addition to carbon atoms, it can also contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom as ring members, for example (but not limited to): furyl (furyl), thienyl (thienyl) , pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadi oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl; wherein the rings are connected to the main chain through a carbon or nitrogen atom of the rings,
含有1到4個氮原子的六員雜芳基：除碳原子外，還可分別含有1到3個及1到4個氮原子作為環成員的六員雜芳基，舉例（但不限於）：吡啶基 (pyridinyl)、噠嗪基 (pyridazinyl)、嘧啶基 (pyrimidinyl)以及吡嗪基 (pyrazinyl)。Six-membered heteroaryl groups containing 1 to 4 nitrogen atoms: in addition to carbon atoms, six-membered heteroaryl groups containing 1 to 3 and 1 to 4 nitrogen atoms as ring members, respectively, for example (but not limited to) : pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl.
除非在別處具體定義，否則此定義也適用於作為複合取代基的一部分的雜芳基，例如雜芳基烷基等。Unless specifically defined elsewhere, this definition also applies to heteroaryl groups that are part of a composite substituent, eg, heteroarylalkyl, and the like.
術語「醯胺」是指A-R'C=ONR''-B，其中R'以及R''表示取代基，A及B表示任何基團。The term "amide" refers to A-R'C=ONR''-B, where R' and R'' represent substituents and A and B represent any group.
術語「硫醯胺」是指A-R'C=SNR''-B，其中R'以及R''表示取代基，A及B表示任何基團。The term "thioamide" refers to A-R'C=SNR''-B, where R' and R'' represent substituents and A and B represent any group.
取代基中的碳原子總數由“C i-C j”前綴表示，其中i及j是1到21的數字。舉例來說，C 1-C 3烷氧基表示從甲基至丙基。在以上敘述中，當式(I)化合物由一個或多個雜環組成時，所有取代基透過任何可用的碳或氮藉由取代所述碳或氮上的氫而連接至這些環。 The total number of carbon atoms in a substituent is indicated by the "C i -C j " prefix, where i and j are numbers from 1 to 21. For example, C1 - C3alkoxy represents from methyl to propyl. In the above description, when compounds of formula (I) consist of one or more heterocycles, all substituents are attached to these rings through any available carbon or nitrogen by substituting a hydrogen on said carbon or nitrogen.
當化合物被帶有下標的取代基取代時，且所述取代基指示所述取代基的數目可以超過1時，則所述取代基（當它們超過1時）獨立地選自被定義的取代基組。此外，當下標表示範圍，例如(R) i-j，則取代基的數目可以選自i到j之間的整數，包括i以及j。 When a compound is substituted with a subscripted substituent indicating that the number of such substituents may exceed 1, then the substituents (when they exceed 1) are independently selected from the defined substituents Group. Furthermore, where a subscript indicates a range, eg (R) ij , the number of substituents can be selected from an integer between i and j, inclusive.
當一個基團包含一個可以是氫的取代基時，例如R 1或R 2，那麼，當該取代基被視為氫時，則認為該基團是等同於未取代的。 When a group contains a substituent that may be hydrogen , such as R1 or R2, then the group is considered to be equivalent to unsubstituted when the substituent is considered to be hydrogen.
因此，本發明提供一種式(I)化合物，
在一實施例中，本發明提供一種式(I)化合物，
其中
Y表示O；
環A代表選自A1至A7的環系統，其中A係可選擇地由一或多個R
4取代；
在一實施例中，本發明提供一種式(I)化合物，
其中
環A代表選自A8至A12的環系統，其中A係可選擇地由一或多個R
4取代；
在一實施例中，本發明提供一種式(I)化合物，
其中
較佳地，環A係選自A1、A2、A6以及A7，其中A可選擇地由一或多個R
4取代；
在一實施例中，本發明提供一種式(I)化合物， 其中 Y表示O；環A代表選自A1至A12的環系統，其中A係可選擇地由一或多個R 4取代；且R 4係選自由X、CN、C 1-C 6烷基、C 1-C 6鹵烷基、R 5aC=NOR 5a以及-C 1-C 6-烷基-OR 5所組成的群組。 In one embodiment, the present invention provides a compound of formula (I), wherein Y represents O; Ring A represents a ring system selected from A1 to A12, wherein A is optionally substituted with one or more R 4 ; and R 4 is selected from the group consisting of X, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, R 5a C=NOR 5a and -C 1 -C 6 -alkyl-OR 5 .
在一實施例中，本發明提供一種式(I)化合物，其中較佳的化合物係選自以下所組成的群組：4,4-二氟丁-3-烯-1-基2-(5-甲基-3-(三氟甲基)-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-雙(三氟甲基)-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-二甲基-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(4-甲基-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-雙(二氟甲基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(5-甲基-3-(三氟甲基)-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(5-環丙基-3-(三氟甲基)-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(5-環丙基-3-(三氟甲基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-二甲基-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-甲基-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-雙(三氟甲基)-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(1H-吲唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(1H-吲唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸酯；4,4-二氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-3,5-二甲基-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(4-氯-3,5-二甲基-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-二苯基-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-二苯基-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-甲基-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(4-甲基-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-甲基-2-(4-甲基-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-甲基-2-(4-甲基-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-二苯基-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-二苯基-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-(二氟甲基)-2H-吲唑-2-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-甲基-2H-吲唑-2-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3-甲基-1H-吲唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3-(二氟甲基)-2H-吲唑-2-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-雙(二氟甲基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-(三氟甲基)-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3-(三氟甲基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(5-甲基-3-(三氟甲基)-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(5-甲基-3-(三氟甲基)-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-甲基-2-(5-甲基-3-(三氟甲基)-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-甲基-2-(5-甲基-3-(三氟甲基)-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(2H-吲唑-2-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(2H-吲唑-2-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-二甲基-1H-1,2,4-***-1-基)醋酸酯；2-(4-氯-1H-吡唑-1-基)-N-(3,4,4-三氟丁-3-烯-1-基)乙醯胺；3,4,4-三氟丁-3-烯-1-基2-(5-(三氟甲基)-2H-四唑-2-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4,5-二氯-1H-咪唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-二甲基-1H-1,2,4-***-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-二甲基-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-二甲基-1H-吡唑-1-基)-2-甲基丙酸酯；2-(4-氯-1H-吡唑-1-基)-N-(4,4-二氟丁-3-烯-1-基)乙醯胺；3,4,4-三氟丁-3-烯-1-基2-(1H-苯并[d]咪唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(1H-咪唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(1H-苯并[d]咪唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(1H-咪唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-(三氟甲基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-3,5-二甲基-1H-吡唑-1-基)-2-甲基丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-3,5-二甲基-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(4-氯-3,5-二甲基-1H-吡唑-1-基)-2-甲基丙酸酯；4,4-二氟丁-3-烯-1-基2-(4-氯-3,5-二甲基-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-二甲基-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(2-甲基-1H-咪唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(5-甲基-2H-四唑-2-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(5-甲基-2H-四唑-2-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(4-(三氟甲基)-1H-吡唑-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(2-環丙基-1H-苯并[d]咪唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(1H-苯并[d][1,2,3]***-1-基)醋酸酯；4,4-二氟丁-3-烯-1-基2-(1H-苯并[d][1,2,3]***-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(5-甲基-1H-四唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-雙(三氟甲基)-1H-吡唑-1-基)丙酸酯；4,4-二氟丁-3-烯-1-基2-(3,5-雙(三氟甲基)-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-氯-1H-吲唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-二甲基-1H-吡唑-1-基)-2-甲基丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(2-甲基-1H-咪唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4,5-二氯-2-甲基-1H-咪唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-氯-1H-吲唑-1-基)-2-甲基丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-甲基-2-(1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-(三氟甲基)-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-甲基-2-(3-(三氟甲基)-1H-吡唑-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-苯基-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-3-甲基-5-(三氟甲基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-5-甲基-3-(三氟甲基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-(3,5-二氟苯基)-1H-吡唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(2H-苯并[d][1,2,3]***-2-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(5-甲基-2H-四唑-2-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(1H-苯并[d][1,2,3]***-1-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(2-(三氟甲基)-1H-苯并[d]咪唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(2-甲基-1H-苯并[d]咪唑-1-基)醋酸酯；3,4,4-三氟丁-3-烯-1-基2-(2H-苯并[d][1,2,3]***-2-基)-2-甲基丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(1H-苯并[d][1,2,3]***-1-基)-2-甲基丙酸酯；3,4,4-三氟丁-3-烯-1-基2-甲基-2-(5-甲基-2H-四唑-2-基)丙酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-3,5-甲基-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-(三氟甲基)-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(5-甲基-3-(三氟甲基)-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-雙(三氟甲基)-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-甲基-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(3-甲基-1H-吲唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)-3-甲基丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-雙(三氟甲基)-1H-吡唑-1-基)-3-甲基丁酸酯；3,4,4-三氟丁-3-烯-1-基3-甲基-2-(3-甲基-5-(三氟甲基)-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基3-甲基-2-(3-甲基-5-苯基-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(4-氯-3,5-二甲基-1H-吡唑-1-基)-3-甲基丁酸酯；3,4,4-三氟丁-3-烯-1-基2-(3,5-二苯基-1H-吡唑-1-基)-3-甲基丁酸酯；3,4,4-三氟丁-3-烯-1-基3-甲基-2-(3-甲基-1H-吡唑-1-基)丁酸酯；3,4,4-三氟丁-3-烯-1-基3-甲基-2-(3-(三氟甲基)-1H-吡唑-1-基)丁酸酯以及3,4,4-三氟丁-3-烯-1-基3-甲基-2-(4-甲基-1H-吡唑-1-基)丁酸酯。In one embodiment, the present invention provides a compound of formula (I), wherein the preferred compound is selected from the group consisting of: 4,4-difluorobut-3-en-1-yl 2-(5 -Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(tri Fluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1- yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl) acetate; 4,4-difluorobut-3- En-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl2 -(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(5-cyclopropane) yl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazole- 1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl ) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobutane- 3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 4-Methyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H - Pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-indazol-1-yl)acetate; 3,4,4-trifluorobutane -3-En-1-yl 2-(1H-indazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyridine azol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propionate; 3,4,4 -Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionate; 4,4-difluorobut-3-ene-1 -yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro -3,5-Dimethyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl -1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl) Propionate; 4,4-Difluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propionate; 3,4,4- Trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-( 4-Methyl-1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H- Pyrazol-1-yl)propionate; 4,4-Difluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionic acid ester; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobutane- 3-En-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 3-(Difluoromethyl)-2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-2H-indazole -2-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate; 4,4-difluorobutane -3-En-1-yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2 -(3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-pyrazole -1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobutan-3- En-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-( Trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl) )-1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyridine Azol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H - Pyrazol-1-yl)propionate; 4,4-Difluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H - Pyrazol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(2H-indazol-2-yl)acetate; 4,4-difluoro But-3-en-1-yl 2-(2H-indazol-2-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl yl-1H-1,2,4-triazol-1-yl)acetate; 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobutane- 3-En-1-yl)acetamide; 3,4,4-Trifluorobut-3-en-1-yl 2-(5-(trifluoromethyl)-2H-tetrazol-2-yl) Acetate; 3,4,4-Trifluoro But-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(3, 5-Dimethyl-1H-1,2,4-triazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl- 1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2 - Methylpropionate; 2-(4-Chloro-1H-pyrazol-1-yl)-N-(4,4-difluorobut-3-en-1-yl)acetamide; 3,4 ,4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 4, 4-Difluorobut-3-en-1-yl 2-(1H-imidazol-1-yl) acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-( Trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl- 1H-pyrazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl- 1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1- yl)-2-methylpropionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl) Propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propionate; 4,4-Di Fluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl) 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)acetate ; 4,4-Difluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-Difluorobut-3- En-1-yl 2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 1H-benzo[d][1,2,3]triazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-benzo[d][ 1,2,3]Triazol-1-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-1H-tetrazol-1-yl) Acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 4, 4-Difluoro But-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-ene -1-yl 2-(3-chloro-1H-indazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl -1H-pyrazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1- base) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-2-methyl-1H-imidazol-1-yl) acetate; 3, 4,4-Trifluorobut-3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)-2-methylpropionate; 3,4,4-Trifluorobutane- 3-En-1-yl 2-(1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(1H- Pyrazol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propane 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-phenyl-1H-pyrazol-1-yl)acetate; 3,4,4-Trifluorobut-3-ene -1-yl 2-(4-chloro-3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-ene -1-yl 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-ene -1-yl 2-(4-(3,5-difluorophenyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2 -(2H-benzo[d][1,2,3]triazol-2-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl) yl-2H-tetrazol-2-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]tris azol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1- yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4, 4-Trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)-2-methylpropanoate; 3,4, 4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropionate; 3,4, 4-Trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-2H-tetrazol-2-yl)propionate; 3,4,4-Trifluorobutan-3 -En-1-yl 2-(4-chloro-1H - Pyrazol-1-yl)butyrate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-methyl-1H-pyrazol-1- base) butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3, 4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3,4,4 -Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobutane- 3-en-1-yl 2-(3-methyl-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(3- Methyl-1H-indazol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)- 3-Methylbutyrate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)- 3-Methylbutyrate; 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-(trifluoromethyl)-1H-pyridine oxazol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-phenyl-1H-pyrazole- 1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)- 3-Methylbutyrate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-3-methyl Butyrate; 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-1H-pyrazol-1-yl)butyrate; 3,4 ,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate and 3,4,4- Trifluorobut-3-en-1-yl 3-methyl-2-(4-methyl-1H-pyrazol-1-yl)butyrate.
如果各個組分具有不同的生物學活性，在每種情況下分離或合成生物學上更有效的異構物（例如特定的鏡像異構物或非鏡像異構物，或異構物混合物（例如鏡像異構物混合物或非鏡像異構物混合物））可能是有利的。If the individual components have different biological activities, in each case isolate or synthesize biologically more efficient isomers (e.g. specific enantiomers or non-spiroisomers, or mixtures of isomers (e.g. Enantiomer mixtures or diastereomer mixtures)) may be advantageous.
式(I)化合物及其互變異構物，在任何情況下均呈游離形式或鹽形式，如果合適，也可以水合物形式獲得及/或包括其他溶劑，例如那些可能已用於結晶以固體形式存在的化合物。The compounds of formula (I) and their tautomers, in each case in free form or in salt form, are also available in hydrated form, if appropriate and/or include other solvents such as those which may have been used for crystallization in solid form compounds present.
式(I)及/或表(1)所定義的本發明化合物可以下列流程製備，其中，除非另有說明，否則對於式(I)化合物的每個變數 (variable)的定義如上。Compounds of the invention as defined in Formula (I) and/or Table (1) can be prepared by the following schemes, wherein, unless otherwise stated, each variable for the compounds of Formula (I) is as defined above.
流程：1（Ring A：環A；Base：鹼；Solvent：溶劑）
如流程1所示，在有機或無機鹼（例如碳酸鉀或碳酸銫）以及合適的溶劑（例如乙腈或N,N-二甲基甲醯胺）的存在下，式4化合物可透過式2化合物與式3的鹵乙酸烷基酯化合物的烷基化製備，通常在加熱條件下。之後，式4化合物在合適的酸或鹼的存在下被水解而得到式5化合物。在合適的溶劑（例如四氫呋喃、1,4-二氧陸圜 (dioxane)、甲醇或水）的存在下，可被用來水解的合適的酸係選自鹽酸或三氟乙酸，而可被用來水解的合適的鹼係選自氫氧化鈉或是氫氧化鋰。As shown in Scheme 1, compounds of formula 4 are permeable through compounds of formula 2 in the presence of an organic or inorganic base such as potassium carbonate or cesium carbonate and a suitable solvent such as acetonitrile or N,N-dimethylformamide Alkylation preparation with alkyl haloacetate compounds of formula 3, usually with heating. Afterwards, the compound of formula 4 is hydrolyzed in the presence of a suitable acid or base to obtain the compound of formula 5. Suitable acids that can be used for hydrolysis are selected from hydrochloric acid or trifluoroacetic acid in the presence of a suitable solvent such as tetrahydrofuran, 1,4-dioxane, methanol or water, and can be used with Suitable bases for hydrolysis are selected from sodium hydroxide or lithium hydroxide.
流程：2（Ring A：環A；Base：鹼）
此外，如流程2所示，在有機或無機鹼（例如N,N-二異丙基乙胺、碳酸鉀或碳酸銫）以及合適的溶劑（例如乙腈以及N,N-二甲基甲醯胺）的存在下，式1a化合物可透過式5化合物與式6的氟丁烯基鹵化物的烷基化製備，通常在加熱條件下。In addition, as shown in Scheme 2, in an organic or inorganic base such as N,N-diisopropylethylamine, potassium carbonate or cesium carbonate, and a suitable solvent such as acetonitrile and N,N-dimethylformamide ), compounds of formula 1a can be prepared by alkylation of compounds of formula 5 with fluorobutenyl halides of formula 6, usually with heating.
流程：3（Ring A：環A；Amide Coupling：醯胺偶聯；Base：鹼）
如流程3所示，式1b化合物可透過以不同的偶聯劑（例如N-(3-二甲基胺基丙基)-N'-乙基碳二亞胺鹽酸鹽 (N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI))、1-[雙(二甲基胺基)亞甲基]-1H-1,2,3-***並[4,5-b]吡啶鎓3-氧化六氟磷酸鹽 (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU)或是鹵化劑（例如SOCl 2、SO 2Cl 2、COCl 2、X 2以及甲磺醯氯），較佳地在合適的鹼（例如三乙基胺或二異丙基乙胺）的存在下。此外，在鹼（例如碳酸鉀、碳酸銫以及氫化鈉）以及合適的溶劑（例如乙腈或N,N-二甲基甲醯胺）的存在下，式1c化合物可透過式1b化合物與鹵烷的烷基化製備，通常在室溫及加熱條件下。 As shown in Scheme 3, the compound of formula 1b can be synthesized by different coupling agents such as N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (N-(3 -Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDCI)), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU) or a halogenating agent such as SOCl 2 , SO 2 Cl 2 , COCl 2 , X 2 and methanesulfonyl chloride), preferably in the presence of a suitable base such as triethylamine or diisopropylethylamine. In addition, in the presence of a base such as carbonic acid Compounds of formula 1c can be prepared by alkylation of compounds of formula 1b with haloalkanes in the presence of a suitable solvent such as acetonitrile or N,N-dimethylformamide, usually at Room temperature and heating conditions.
取決於化合物中不對稱中心的數目，根據本發明的任何化合物可以一種或多種光學、幾何或掌性異構物形式存在。因此，本發明同樣關於所有光學異構物以及它們的外消旋或不規則混合物（術語「不規則的 (scalemic)」表示不同比例的鏡像異構物的混合物），以及所有可能的立體異物體的所有比例的混合物。非鏡像異構物及/或光學異構物可以依據所屬技術領域中具有通常知識者所知悉的方法製備。Depending on the number of asymmetric centers in the compound, any compound according to the present invention may exist as one or more optical, geometric or chiral isomers. Accordingly, the present invention also relates to all optical isomers and their racemic or irregular mixtures (the term "scalemic" means mixtures of enantiomers in different proportions), and all possible stereoisomers of all proportions of the mixture. Astereoisomers and/or optical isomers can be prepared according to methods known to those of ordinary skill in the art.
取決於化合物中雙鍵的數目，根據本發明的任何化合物可以一種或多種幾何異構物形式存在。因此，本發明同樣關於所有的幾何異構物以及所有可能的所有比例的混合物。幾何異構物可以依據本領域具有通常知識者所知的方法製備。Depending on the number of double bonds in the compound, any compound according to the present invention may exist as one or more geometric isomers. Accordingly, the present invention also relates to all geometric isomers and all possible mixtures in all ratios. Geometric isomers can be prepared according to methods known to those of ordinary skill in the art.
amorphic取決於化合物的製備、純化儲存以及其他不同的影響因子，根據本發明的任何化合物可以一種或多種非晶態 (amorphic)或同形態 (isomorphic)或多晶態 (polymorphic)的形式存在。因此，本發明也關於所有可能的所有比例的非晶態、同形態以及多晶態的形式。非晶態、同形態以及多晶態形式可依據所屬技術領域中具有通常知識者所知悉的方法製備及/或分離及/或純化。amorphic Depending on the compound's preparation, purification storage, and other various influencing factors, any compound according to the invention may exist in one or more amorphic or isomorphic or polymorphic forms. Accordingly, the present invention also relates to amorphous, isomorphic and polycrystalline forms in all possible proportions. Amorphous, isomorphic and polymorphic forms can be prepared and/or isolated and/or purified according to methods known to those of ordinary skill in the art.
有大量的合適的標準方法，例如烷基化、鹵化、醯化、胺化、肟化 (oximation)、氧化以及還原。適合的製備方法的選擇係取決於中間產物的取代基的性質（反應能力）。這些反應可以在溶劑中被方便地進行。它們也可以在不同的溫度下進行，通常是在惰性環境下。反應物可以鹼的存在下反應。合適的鹼的例子為鹼金屬或鹼土金屬的氫氧化物、鹼金屬或鹼土金屬的氫化物、鹼金屬或鹼土金屬的醯胺、鹼金屬或鹼土金屬的烷氧化物、鹼金屬或鹼土金屬的醋酸酯、鹼金屬或鹼土金屬的碳酸酯、鹼金屬或鹼土金屬的二烷基醯胺或者是鹼金屬或鹼土金屬的烷基矽烷基醯胺、烷基胺、烷基烯二胺 (alkylenediamines)、游離或 N-烷基化的飽和或不飽和環烷基胺、鹼性雜環、氫氧化銨以及碳環胺。可能被提到的例子為，氫氧化鈉、氫化鈉、胺基鈉、甲氧化鈉、乙酸鈉、碳酸鈉、叔丁氧基鉀、氫氧化鉀、碳酸鉀、氫化鉀、二異丙基胺基鋰、雙(三甲基矽烷基)醯胺鉀、氫化鈣、三乙基胺、N,N-二異丙基乙胺、三乙烯基二胺 (triethylenediamine)、環己胺、N-環己基-N,N-二甲基胺、N,N-二乙基苯胺、嘧啶、4-(N,N-二甲基胺基)嘧啶、口昆啶 (quinuclidine)、N-甲基嗎啉、苯甲基三甲基氫氧化銨 (benzyltrimethylammonium hydroxide)以及1,8-二氮雜二環[5.4.0]十一碳-7-烯 (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU))。There are a number of suitable standard methods such as alkylation, halogenation, amidation, amination, oximation, oxidation and reduction. The choice of a suitable preparation method depends on the nature (reactivity) of the substituents of the intermediate product. These reactions can be conveniently carried out in a solvent. They can also be carried out at different temperatures, usually in an inert environment. The reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal amides. Acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines , free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, diisopropylamine Lithium, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, N,N-diisopropylethylamine, triethylenediamine, cyclohexylamine, N-ring Hexyl-N,N-dimethylamine, N,N-diethylaniline, pyrimidine, 4-(N,N-dimethylamino)pyrimidine, quinuclidine, N-methylmorpholine , benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (1,8-diazabicyclo[5.4.0]undec-7 -ene (DBU)).
根據流程-1或流程-3的反應係較佳地於一溶劑中進行，而該溶劑係選自在主要反應條件下呈惰性的標準溶劑。較佳為脂肪族、脂環族或芳香族的烴類（如石油醚、己烷、甲苯）；鹵烴類（如氯苯、二氯甲烷、氯仿、四氯化碳或二氯乙烷）；醚類（如***、二異丙醚、甲基叔丁基醚 (MTBE)、二氧陸圜 (dioxane)、四氫呋喃或1,2-二甲氧基乙烷）；腈類（如乙腈或丙腈）或是醯胺類（如N,N-二甲基甲醯胺 (DMF)、N,N-二甲基乙醯胺、N-甲基甲醯苯胺、N-甲基吡咯烷酮 (NMP) 或六亞甲基磷醯三胺 (hexamethylenephosphoric triamide)）；酯類（如乙酸甲酯或乙酸乙酯）；亞碸類（如二甲亞碸 (DMSO)）；碸類（如環丁碸）；醇類（如甲醇、乙醇、異丙醇、1,1-、異-、仲-或叔丁醇、乙二醇、丙烷-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二乙二醇單甲醚、二乙二醇單***）或這些化合物的混合物。The reaction according to Scheme-1 or Scheme-3 is preferably carried out in a solvent selected from standard solvents which are inert under the main reaction conditions. Preferably aliphatic, cycloaliphatic or aromatic hydrocarbons (such as petroleum ether, hexane, toluene); halogenated hydrocarbons (such as chlorobenzene, dichloromethane, chloroform, carbon tetrachloride or dichloroethane) ; ethers (such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), dioxane, tetrahydrofuran or 1,2-dimethoxyethane); nitriles (such as acetonitrile or propionitrile) or amides (such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methylcarbanilide, N-methylpyrrolidone (NMP) ) or hexamethylenephosphoric triamide); esters (such as methyl acetate or ethyl acetate); sulfites (such as dimethylsulfoxide (DMSO)); sulfites (such as cyclobutane) ); alcohols (e.g. methanol, ethanol, isopropanol, 1,1-, iso-, sec- or tert-butanol, ethylene glycol, propane-1,2-diol, ethoxyethanol, methoxy ethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether) or mixtures of these compounds.
反應物可以這樣相互反應，換句話說，不添加溶劑或稀釋劑。反應有利地在約-80 °C至約+140 °C，較佳地在約-30 °C至約+100 °C的溫度範圍內進行，在許多情況下在環境溫度及約+80 °C之間的範圍內進行。The reactants can react with each other in such a way that no solvent or diluent is added. The reaction is advantageously carried out at a temperature ranging from about -80°C to about +140°C, preferably about -30°C to about +100°C, and in many cases at ambient temperature and about +80°C within the range between.
式(I)化合物可以透過本身已知的方式轉化為另一種式(I)化合物，方法是將式(I)的起始化合物的一個或多個取代基以常規方式替換根據本發明的另一個（其他）取代基。取決於所選擇的反應條件以及每個情況下所適合的起始材料，例如可以在一個反應步驟中僅用本發明的另一取代基替換一個取代基，或者可以在相同步驟中使多個取代基 被根據本發明的其他取代基取代。式(I)化合物的鹽可以根據本身已知的方法被製備。因此，舉例來說，式(I)的酸加成鹽可以藉由以合適的酸或者合適的離子交換試劑處理而獲得，而其帶有鹼的鹽可以藉由以合適的鹼或者合適的離子交換試劑處理而獲得。鹽的選擇取決於其對化合物使用的耐受性，例如農業耐受性或生理耐受性。式(I)化合物的鹽可以常規方式轉換為式I的游離化合物 (free compounds)、酸加成鹽（舉例來說，以合適的酸或者合適的離子交換試劑處理）以及帶有鹼的鹽（例如，以合適的鹼或合適的離子交換試劑處理）。式(I)化合物的鹽可以本身已知的方式轉化為式(I)化合物的其他鹽，例如酸加成鹽，例如轉化為其他酸加成鹽，例如透過在適當的溶劑中處理無機酸的鹽（如鹽酸鹽）與適當的金屬鹽（如酸的鈉、鋇或銀鹽，例如與乙酸銀），其中所形成的無機鹽（例如氯化銀）是不溶 (insoluble)的，因此從反應混合物中析出。A compound of formula (I) can be converted into another compound of formula (I) in a manner known per se by substituting one or more substituents of the starting compound of formula (I) in a conventional manner for another compound according to the invention (Other) Substituents. Depending on the selected reaction conditions and the suitable starting materials in each case, for example, only one substituent can be replaced in one reaction step with another substituent according to the invention, or multiple substitutions can be made in the same step. groups are substituted with other substituents according to the present invention. Salts of compounds of formula (I) can be prepared according to methods known per se. Thus, for example, acid addition salts of formula (I) can be obtained by treatment with suitable acids or suitable ion exchange reagents, and salts thereof with bases can be obtained by treatment with suitable bases or suitable ions obtained by exchanging reagents. The choice of salt depends on its tolerance to the use of the compound, eg agricultural tolerance or physiological tolerance. Salts of compounds of formula (I) can be converted in a conventional manner to free compounds of formula I, acid addition salts (for example, by treatment with a suitable acid or a suitable ion exchange reagent) and salts with bases ( For example, treatment with a suitable base or a suitable ion exchange reagent). Salts of compounds of formula (I) can be converted in a manner known per se to other salts of compounds of formula (I), such as acid addition salts, for example by treatment of mineral acids in suitable solvents. Salts (such as hydrochloride) with suitable metal salts (such as sodium, barium or silver salts of acids, for example with silver acetate), wherein the inorganic salts formed (such as silver chloride) are insoluble, and therefore from Precipitated in the reaction mixture.
在一實施例中，本發明提供式(I)化合物、其立體異構物、農業上可接受的鹽、互變異構物或N-氧化物或其組成物或組合物用於控制或預防農作物及/或園藝作物對抗植物病原真菌、細菌、昆蟲、線蟲或蟎蟲的用途。In one embodiment, the present invention provides compounds of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides or compositions or compositions thereof for use in the control or prevention of crops and/or use of horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes or mites.
在較佳的實施例中，本發明提供式(I)化合物、其立體異構物、農業上可接受的鹽、互變異構物或N-氧化物或其組成物或組合物用於控制或預防農作物及/或園藝作物對抗線蟲和植物病原真菌的用途。In preferred embodiments, the present invention provides compounds of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides or compositions or compositions thereof for use in controlling or Use of crops and/or horticultural crops for prevention against nematodes and phytopathogenic fungi.
農作物係選自穀類、玉米、稻米、大豆及其他豆科植物、水果及果樹、葡萄、堅果及堅果樹、柑橘及柑橘樹、任何園藝植物、 葫蘆科、油料植物、煙草、咖啡、茶、可可、糖用甜菜、甘蔗、棉花、馬鈴薯、蕃茄、洋蔥、胡椒、其他蔬菜或觀賞植物。Crop line is selected from cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa , sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers, other vegetables or ornamental plants.
本發明的化合物可用於防治或消滅害蟲，例如特別存在於植物中的線蟲，尤其是存在於農業、園藝及森林中的實用植物和觀賞植物中，或存在於器官中，例如塊莖、種子或根中，在某些情況下，甚至在較晚的時間點形成的植物器官仍能免受這些害蟲的侵害。The compounds according to the invention can be used for the control or eradication of pests, such as nematodes, which are especially present in plants, especially in practical and ornamental plants in agriculture, horticulture and forests, or in organs such as tubers, seeds or roots In some cases, even plant organs formed at a later point in time are protected from these pests.
根據本發明的式(I)化合物是害蟲防治領域中具有預防及/或治療價值的活性成分，即使在低施用率下，也可用於對抗農藥抗性害蟲，例如線蟲。此外，式(I)化合物具有非常有利的生物殺傷性光譜 (biocidal spectrum)，並且溫血物種、魚類及植物對其具有良好的耐受性。因此，本發明還提供了一種包含本發明化合物（例如式(I)）的殺蟲組成物。現已發現，根據本發明的式(I)化合物具有非常有利的活性譜，可保護動物及實用植物免受線蟲的侵襲和損害。因此，本發明還提供了一種包含本發明化合物（例如式(I)）的殺線蟲組成物。The compounds of formula (I) according to the invention are active ingredients of prophylactic and/or therapeutic value in the field of pest control, even at low application rates, for use against pesticide-resistant pests, such as nematodes. Furthermore, the compounds of formula (I) have a very favourable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. Accordingly, the present invention also provides a pesticidal composition comprising a compound of the present invention (eg formula (I)). It has now been found that the compounds of the formula (I) according to the invention have a very favourable spectrum of activity and protect animals and practical plants from attack and damage by nematodes. Accordingly, the present invention also provides a nematicidal composition comprising a compound of the present invention (eg formula (I)).
式(I)化合物具有有效的殺線蟲活性，可在農業或園藝作物保護以及保護此類材料的面相，用於控制不需要的線蟲和細菌。The compounds of formula (I) have potent nematicidal activity and can be used for controlling unwanted nematodes and bacteria in agricultural or horticultural crop protection and in protecting the face of such materials.
式(I)的化合物可用作作物保護中的殺線蟲劑，例如用於控制墊刃目 (Tylenchida)、桿形目 (Rhabditida)、矛線目 (Dorylaimida)以及Tryplonchida。The compounds of formula (I) are useful as nematicides in crop protection, for example for the control of Tylenchida, Rhabditida, Dorylaimida and Tryplonchida.
式(I)化合物可用於防治或預防農作物及/或園藝作物的植物病原線蟲。The compounds of formula (I) can be used to control or prevent phytopathogenic nematodes of crops and/or horticultural crops.
式(I)的化合物可用於保護作物，其中農作物為穀類、玉米、稻米、大豆及其他豆科植物、水果及果樹、葡萄、堅果及堅果樹、柑橘及柑橘樹、任何園藝植物、葫蘆科、油料植物、煙草、咖啡、茶、可可、糖用甜菜、甘蔗、棉花、馬鈴薯、蕃茄、洋蔥、胡椒、其他蔬菜以及觀賞植物。The compounds of formula (I) can be used to protect crops, wherein the crops are cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, Oil plants, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers, other vegetables and ornamental plants.
式(I)化合物特別適用於控制線蟲。因此，在另一方面，本發明還涉及控制由植物寄生的線蟲(內寄生的-、半內寄生-的以及外寄生的線蟲)對植物或其部分引起損害的方法，尤其是以下植物寄生的線蟲，如根結線蟲 (root knot nematodes)、北方根結線蟲 (Meloidogyne hapla)、南方根結線蟲 (Meloidogyne incognita)、爪哇根結線蟲 (Meloidogyne javanica)、花生根結線蟲 (Meloidogyne arenaria)以及其他根結線蟲屬物種 (Meloidogyne species)；孢囊形成線蟲 (cyst-forming nematodes)、馬鈴薯金線蟲 (Globodera rostochiensis)以及其他球孢囊線蟲屬物種 (Globodera species)；禾穀孢囊線蟲 (Heterodera avenae)、大豆胞囊線蟲 (Heterodera glycines)、甜菜胞囊線蟲 (Heterodera schachtii)、紅三葉異皮線蟲 (Heterodera trifolii)、以及其他異皮線蟲屬物種 (Heterodera species)；種癭線蟲 (Seed gall nematodes)、粒線蟲屬物種 (Anguina species)；莖及葉面線蟲 (Stem and foliar nematodes)、滑刃線蟲屬物種 (Aphelenchoides species)；刺毛線蟲 (Sting nematodes)、長尾刺線蟲 (Eelonolaimus longicaudatus)以及其他刺線蟲屬物種 (Belonolaimus species)；松樹線蟲 (Pine nematodes)、松材線蟲 (Bursaphelenchus xylophilus)以及其他傘滑刃屬物種 (Bursaphelenchus species)；環形線蟲 (Ring nematodes)、環線蟲屬物種 (Criconema species)、小環線蟲屬物種 (Criconemella species)、輪線蟲屬物種 (Criconemoides species)、中環線蟲屬物種 (Mesocriconema species)；莖及鱗球莖線蟲 (Stem and bulb nematodes)、腐爛莖線蟲 (Ditylenchus destructor)、鱗球莖莖線蟲 (Ditylenchus dipsaci)以及其他莖線蟲屬物種 (Ditylenchus species)；錐線蟲 (Awl nematodes)、錐線蟲屬物種 (Dolichodorus species)；螺旋線蟲 (Spiral nematodes)、多頭螺旋線蟲 (Heliocotylenchus multicinctus)以及其他螺旋線蟲屬物種(Helicotylenchus species)；鞘及鞘形線蟲 (Sheath and sheathoid nematodes)、鞘線蟲屬物種 (Hemicycliophora species)以及半輪線蟲屬物種 (Hemicriconemoides species)；潛根線蟲屬物種 (Hirshmanniella species)；支線蟲 (Lance nematodes)、冠線蟲屬物種 (Hoploaimus species)；假根結線蟲 (false rootknot nematodes)、珍珠線蟲屬物種 (Nacobbus species)；針狀線蟲 (Needle nematodes)、橫帶長針線蟲 (Longidorus elongatus)以及其他長針線蟲屬物種 (Longidorus species)；大頭針線蟲 (Pin nematodes)、短體線蟲屬物種 (Pratylenchus species)；腐線蟲 (Lesion nematodes)、花斑短體線蟲 (Pratylenchus neglectus)、穿刺短體線蟲 (Pratylenchus penetrans)、彎曲短體線蟲 (Pratylenchus curvitatus)、古氏短體線蟲 (Pratylenchus goodeyi)以及其他短體線蟲屬物種 (Pratylenchus species)；柑桔穿孔線蟲 (Burrowing nematodes)、香蕉穿孔線蟲 (Radopholus similis)以及其他內侵線蟲屬物種 (Radopholus species)；腎形線蟲 (Reniform nematodes)、羅柏氏盤旋線蟲 (Rotylenchus robustus)、腎形盤旋線蟲 (Rotylenchus reniformis)以及其他盤旋線蟲屬物種 (Rotylenchus species)；盾線蟲屬物種 (Scutellonema species)；短粗根線蟲 (Stubby root nematodes)、原始毛刺線蟲 (Trichodorus primitivus)以及其他毛刺線蟲屬物種 (Trichodorus species)、擬毛刺線蟲屬物種 (Paratrichodorus species)；矮化線蟲 (Stunt nematodes)、馬齒莧矮化線蟲 (Tylenchorhynchus claytoni)、順逆矮化線蟲 (Tylenchorhynchus dubius)以及其他矮化線蟲屬物種 (Tylenchorhynchus species)；柑桔線蟲 (Citrus nematodes)、穿刺線蟲屬物種 (Tylenchulus species)；短劍線蟲 (Dagger nematodes)、劍線蟲屬物種 (Xiphinema species)；以及其他植物寄生的線蟲種類，如亞粒線蟲屬 (Subanguina spp.)、根結線蟲屬 (Hypsoperine spp.)、大刺環線蟲屬 (Macroposthonia spp.)、矮化線蟲屬 (Melinius spp.)、刻點胞囊屬 (Punctodera spp.)、以及五溝線蟲屬 (Quinisulcius spp.)。The compounds of formula (I) are particularly suitable for controlling nematodes. Therefore, in another aspect, the present invention also relates to a method for controlling damage to plants or parts thereof by plant-parasitic nematodes (endo-, semi-endo- and ectoparasitic nematodes), in particular the following plant-parasitic nematodes Nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria, and other root knot nematodes Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Eelonolaimus longicaudatus, and other spiny nematodes Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus, and other Bursaphelenchus species; Ring nematodes, Criconema species, small Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus d estructor), Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus) and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species, and Hemicriconemoides species; Hirshmanniella species); Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, long needle Nematodes (Longidorus elongatus) and other Longidorus species; Pin nematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, banana piercing Nematodes (Radopholus similis) and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus s pecies); Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other stunt nematodes; Citrus nematodes, Stunt nematodes Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant-parasitic nematode species such as Subanguina spp., Hypsoperine spp. ), Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.
特別地，線蟲屬物種，根結線蟲屬 (Meloidogyne spp.)、異皮線蟲屬 (Heterodera spp.)、盤旋線蟲屬 (Rotylenchus spp.)、短體線蟲屬 (Pratylenchus spp.)以及內侵線蟲屬 (Radopholus spp.)可以被本發明的化合物控制。In particular, nematode species, Meloidogyne spp., Heterodera spp., Rotylenchus spp., Pratylenchus spp., and Introgressive nematodes (Radopholus spp.) can be controlled by the compounds of the present invention.
在一實施例中，本發明提供一種用於控制或預防植物病原微生物的組成物，其包含通式(I)化合物、立體異構物、農業上可接受的鹽、互變異構物或N-氧化物以及一或多種惰性載體。In one embodiment, the present invention provides a composition for controlling or preventing phytopathogenic microorganisms, comprising a compound of general formula (I), a stereoisomer, an agriculturally acceptable salt, a tautomer or an N- oxide and one or more inert supports.
在另一實施例中，組成物可進一步包括一或多種活性相容化合物，這些活性相容化合物係選自殺真菌劑、殺蟲劑、殺線蟲劑、殺蟎劑、生物殺蟲劑、除草劑、植物生長調節劑、抗生素、營養劑或肥料。In another embodiment, the composition may further comprise one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides , plant growth regulators, antibiotics, nutrients or fertilizers.
通式(I)的化合物的濃度範圍為相對於組成物總重量的1至90重量%，較佳為相對於組成物的總重量的5至50重量%。The concentration range of the compound of general formula (I) is 1 to 90% by weight relative to the total weight of the composition, preferably 5 to 50% by weight relative to the total weight of the composition.
本發明更關於一種用以控制不想要的微生物的組成物，其包括至少一式(I)化合物以及一或多個惰性載體。惰性載體更近一步包括農業上適合助劑、溶劑、稀釋劑、界面活性劑及/或增充劑 (extender)等。The present invention further relates to a composition for controlling unwanted microorganisms comprising at least one compound of formula (I) and one or more inert carriers. Inert carriers further include agriculturally suitable adjuvants, solvents, diluents, surfactants and/or extenders and the like.
本發明更關於一種用以控制不想要的微生物的組成物，其包括至少一式(I)化合物及/或一或多個活性相容化合物，這些活性相容化合物係選自殺真菌劑、殺蟲劑、殺蟎劑、殺線蟲劑、除草劑、生物殺蟲劑、植物生長調節劑、抗生素、肥料及/或其混合物。The present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one compound of formula (I) and/or one or more active compatible compounds selected from fungicides, insecticides , acaricides, nematicides, herbicides, bioinsecticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.
一般而言，本發明的化合物係以組成物（例如製劑）的形式被使用，其包括一載體。本發明的化合物及其組成物可以不同形式被使用，例如氣霧劑 (aerosol dispenser)、微囊懸浮液 (capsule suspension)、冷霧劑 (cold fogging concentrate)、粉劑 (dustable powder)、乳油 (emulsifiable concentrate)、水乳劑 (emulsion oil in water)、油乳劑 (emulsion water in oil)、膠囊粒劑 (encapsulated granule)、細粒劑 (fine granule)、種子處理流劑 (flowable concentrate for seed treatment)、氣體（在壓力下）、發氣劑 (gas generating product)、顆粒劑 (granule)、熱霧劑 (hot fogging concentrate)、大粒劑 (macrogranule)、微粒劑 (microgranule)、油分散粉劑 (oil dispersible powder)、油混性流劑 (oil miscible flowable concentrate)、油劑 (oil miscible liquid)、膏劑 (paste)、條劑 (plant rodlet)、乾種子處理用粉劑 (powder for dry seed treatment)、塗有農藥的種子 (seed coated with a pesticide)、可溶液劑 (soluble concentrate)、可溶粉劑 (soluble powder)、種子處理用溶液 (solution for seed treatment)、懸浮劑 (suspension concentrate)（流劑 (flowable concentrate)）、超低容量（ulv）液體 (ultra-low volume (ulv) liquid)、超低容量（ulv）懸浮液 (ultra-low volume (ulv) suspension)、水分散粒劑或片劑 (water dispersible granules or tablets)、濕種子處理用水分散粉劑 (water dispersible powder for slurry treatment)、水溶性粒劑或片劑 (water soluble granules or tablets)、種子處理水溶性粉劑 (water soluble powder for seed treatment)以及可濕性粉劑 (wettable powder)。Generally, the compounds of the present invention are used in the form of compositions (eg, formulations) that include a carrier. The compounds of the present invention and their compositions can be used in various forms such as aerosol dispensers, capsule suspensions, cold fogging concentrates, dustable powders, emulsifiable concentrates concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder , oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, pesticide coated Seed (seed coated with a pesticide), soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate) , ultra-low volume (ulv) liquid, ultra-low volume (ulv) suspension, water dispersible granules or tablets tablets), water dispersible powder for slurry treatment, water-soluble granules or tablets (water sol) uble granules or tablets), water soluble powder for seed treatment and wettable powder.
配方通常包括液體或固體載體以及可選地一種慣用的製劑助劑，其可以是固體或液體助劑，舉例而言是未環氧化或環氧化的植物油（例如環氧化的椰子油、菜籽油或大豆油）、消泡劑（例如矽油）、防腐劑、黏土、無機化合物、黏度調節劑、界面活性劑、黏合劑及/或增黏劑。組成物可進一步包括肥料、微量營養素供應體 (micronutrient donor)以及其他影響植物生長的製劑，以及包括含有本發明的化合物與一或多個其他生物活性劑，例如殺菌劑、殺真菌劑、殺線蟲劑、植物活化劑、殺蟎蟲劑以及殺蟲劑。Formulations generally include a liquid or solid carrier and optionally a conventional formulation adjuvant, which may be a solid or liquid adjuvant, for example, an unepoxidized or epoxidized vegetable oil (e.g., epoxidized coconut oil, rapeseed oil) or soybean oil), defoamers (such as silicone oil), preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, binders and/or tackifiers. The composition may further include fertilizers, micronutrient donors, and other agents that affect plant growth, as well as include compounds containing the present invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides agents, plant activators, acaricides and insecticides.
因此，本發明還提供了一種組成物，其包括本發明的化合物及農業載體以及可選第一或多種慣用製劑助劑。Accordingly, the present invention also provides a composition comprising a compound of the present invention and an agricultural carrier and optionally a first or more conventional formulation adjuvants.
在沒有助劑的情況下，例如透過研磨、篩選及/或壓縮本發明的固體化合物，以及在有至少一助劑的情況下，例如透過將本發明的化合物與助劑（多個助劑）緊密地混合及/或研磨，組成物係藉由已知的方法被製備。在發明為固態化合物的情況下，化合物的研磨 (grinding/milling)是為了確保特定的粒徑大小。這些組成物的製備過程以及使用本發明的化合物製備這些組成物的用途也是本發明的主題。In the absence of adjuvants, for example by grinding, screening and/or compressing the solid compounds of the present invention, and in the presence of at least one adjuvant, for example by conflating the compounds of the present invention with adjuvant(s) Mixed and/or milled, the compositions are prepared by known methods. In the case of the invention as a solid compound, the grinding/milling of the compound is to ensure a specific particle size. The preparation of these compositions and the use of the compounds of the present invention to prepare these compositions are also the subject of the present invention.
用於農業的組成物的例子是乳油 (emulsifiable concentrates)、懸浮劑 (suspension concentrates)、微乳劑 (microemulsions)、油分散劑 (oil dispersibles)、可直接噴灑或稀釋的溶液、可塗抹的膏劑 (spreadable pastes)、稀釋的乳劑 (dilute emulsions)、可溶性粉劑 (soluble powders)、可分散的粉劑 (dispersible powders)、可濕性粉劑 (wettable powders)、粉劑 (dusts)、粒劑或多種物質的膠囊 (encapsulations in polymeric substances)，它們至少包括根據本發明的化合物，且組成物的類型應根據預期的目的以及當時的情況選擇。Examples of compositions used in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, sprayable or dilutable solutions, spreadable pastes pastes), dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations of various substances in polymeric substances), which include at least the compounds according to the invention, and the type of composition should be chosen according to the intended purpose and the circumstances at the time.
合適的液體載體的例子是未氫化或部分氫化的芳香烴，最好是烷基苯的C 8至C 12部分，例如二甲苯混合物、烷基萘或四氫萘、脂肪族或環脂肪族烴（如石蠟或環己烷）、醇類（如乙醇、丙醇或丁醇）、乙二醇及其醚與酯（如丙二醇、二丙二醇醚、乙二醇或乙二醇單甲醚或乙二醇單***）、酮類（如環己酮、異佛爾酮 (Isophorone)或二丙酮醇）、強極性溶劑（如N-甲基吡咯烷-2-酮、二甲亞碸或N,N-二甲基甲醯胺、水）、未環氧化或環氧化的植物油（如未環氧化或環氧化的菜籽油、蓖麻油、椰子油或大豆油）以及矽油。例如，用於粉劑和可分散粉劑的固體載體的例子通常是磨碎的天然礦物，如方解石、滑石、高嶺土、蒙脫石或綠坡縷石 (attapulgite)。為了改善物理性質，亦可以添加高分散性的矽石或高分散性的吸收性聚合物。粒劑的合適的微粒吸附性載體為多孔型，例如浮石 (pumice)、磚砂 (brick grit)、海泡石 (sepiolite)或者膨潤土 (bentonite)，且合適的非吸附性載體為方解石或砂。此外，還可以使用大量無機或有機性質的顆粒材料，特別是白雲石 (dolomite)或是粉碎的植物殘留物。根據要配製的活性成分的類型，合適的表面活性化合物是非離子、陽離子及/或陰離子界面活性劑或界面活性劑混合物，其具有良好的乳化、分散以及潤濕特性。以下提到的界面活性劑僅為示例，在相關文獻中還描述了大量一般用於製劑技術並適合本發明的其他界面活性劑。合適的非離子行界面活性劑為，特別是，飽和或不飽和脂肪酸或烷基苯酚的脂肪族或（環）脂肪族醇的聚乙二醇醚衍生物，它們可能含有約3個至約30個乙二醇醚基以及在（環）脂肪族烴基中有約8個至約20個碳原子或者在烷基苯酚基團中含有約6個至約18個碳原子。同樣適合的還有與聚丙二醇、乙二胺聚丙二醇或烷基聚丙二醇的水溶性聚氧乙烯加合物，其烷基鏈上有1個至約10個碳原子，約20個至約250個乙二醇醚基以及約10個至約100個丙二醇醚基。一般來說，上述化合物於每一個丙二醇單元中，包含1個至約5個乙二醇單元。可能提到的例子有壬基苯氧基聚乙氧基乙醇、蓖麻油聚乙二醇醚、聚丙二醇/聚氧化乙烯加合物、三丁基苯氧基聚乙氧基乙醇、聚乙二醇或者辛基苯氧基聚乙氧基乙醇。同樣適合的還有聚氧乙烯山梨糖醇 (polyoxyethylene sorbitan)的脂肪酸酯，例如聚氧乙烯山梨糖醇三油酸酯 (polyoxyethylene sorbitan trioleate)。陽離子界面活性劑尤其是季銨鹽，其通常具有至少一個約8個至約22個碳原子的烷基作為取代基以及作為進一步的取代基（未鹵化或鹵化）的低級烷基或羥基烷基或苯甲基。較佳地以鹵鹽、甲基硫酸鹽或乙基硫酸鹽的形式存在。例子為硬脂基三甲基氯化銨 (stearyltrimethylammonium chloride)以及苯甲基雙(2-氯乙基)乙基溴化銨 (benzylbis(2-chloroethyl)ethylammonium bromide)。 Examples of suitable liquid carriers are unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the C8 to C12 moieties of alkylbenzenes, such as xylene mixtures, alkylnaphthalenes or tetralins, aliphatic or cycloaliphatic hydrocarbons (such as paraffin or cyclohexane), alcohols (such as ethanol, propanol or butanol), ethylene glycol and its ethers and esters (such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol) glycol monoethyl ether), ketones (such as cyclohexanone, isophorone or diacetone alcohol), strongly polar solvents (such as N-methylpyrrolidin-2-one, dimethylsulfoxide or N, N-dimethylformamide, water), unepoxidized or epoxidized vegetable oils (such as unepoxidized or epoxidized canola, castor, coconut, or soybean oil), and silicone oils. For example, examples of solid carriers for dusts and dispersible powders are generally ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. In order to improve the physical properties, high dispersity silica or high dispersity absorbent polymer can also be added. Suitable particulate adsorbent carriers for granules are porous types such as pumice, brick grit, sepiolite or bentonite, and suitable non-absorbent carriers are calcite or sand. Furthermore, it is also possible to use a large number of particulate materials of inorganic or organic nature, in particular dolomite or pulverized plant residues. Depending on the type of active ingredient to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties. The surfactants mentioned below are only examples, and a large number of other surfactants generally used in formulation technology and suitable for the present invention are also described in the relevant literature. Suitable nonionic surfactants are, in particular, polyglycol ether derivatives of saturated or unsaturated fatty acids or aliphatic or (cyclo)aliphatic alcohols of alkylphenols, which may contain from about 3 to about 30 Glycol ether groups and about 8 to about 20 carbon atoms in (cyclo)aliphatic hydrocarbon groups or about 6 to about 18 carbon atoms in alkylphenol groups. Also suitable are water-soluble polyoxyethylene adducts with polypropylene glycol, ethylenediamine polypropylene glycol or alkyl polypropylene glycol having 1 to about 10 carbon atoms in the alkyl chain, about 20 to about 250 carbon atoms in the alkyl chain glycol ether groups and from about 10 to about 100 propylene glycol ether groups. Generally, the above compounds will contain from 1 to about 5 ethylene glycol units per propylene glycol unit. Examples that may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene glycol/polyoxyethylene adduct, tributylphenoxypolyethoxyethanol, polyethylene glycol alcohol or octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate. Cationic surfactants, especially quaternary ammonium salts, which generally have at least one alkyl group of about 8 to about 22 carbon atoms as a substituent and a lower alkyl or hydroxyalkyl group as a further substituent (unhalogenated or halogenated) or benzyl. It is preferably present in the form of a halide, methylsulfate or ethylsulfate. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.
適合的陰離子界面活性劑的例子為水溶性肥皂或者水溶性核成表面活性化合物。適合的肥皂的例子為具有約10個至22個碳原子的脂肪酸的鹼金屬鹽、鹼土金屬鹽或（取代或未取代）銨鹽，例如為油酸或硬脂酸的鈉鹽或鉀鹽，或可從例如椰子油或松油 (tall oil)獲得的天然脂肪酸混合物的鈉鹽或鉀鹽；也須提到脂肪酸甲基牛磺酸鹽 (the fatty acid methyl taurates)。然而，較常使用合成界面活性劑，特別是脂肪磺酸鹽 (fatty sulfonates)、脂肪硫酸鹽 (fatty sulfates)、磺化苯並咪唑衍生物 (sulfonated benzimidazole derivatives)或烷基芳基磺酸鹽 (alkylaryl sulfonates)。通常，脂肪磺酸鹽及脂肪硫酸鹽以鹼金屬鹽、鹼土金屬鹽或（取代或未取代）銨鹽的形式存在，它們通常具有約8個至約22個碳原子的烷基，烷基也應理解為包括醯基的烷基部分；可提及的實例是十二烷基硫酸 (the dodecylsulphuric ester)的木質素磺酸 (lignosulfonic acid)的鈉鹽或鈣鹽或由天然脂肪酸製備的脂肪醇硫酸鹽混合物的木質素磺酸的鈉鹽或鈣鹽。本群組還包括脂肪醇/環氧乙烷加合物的硫酸酯及磺酸鹽。磺化苯並咪唑衍生物較佳地含有兩個磺醯基以及約8個至約22個碳原子的脂肪酸的官能基。烷基芳基磺酸鹽的例子是癸基苯磺酸 (decylbenzenesulfonic acid)、二丁基萘磺酸 (naphthalenesulfonic acid)或萘磺酸/甲醛縮合物 (naphthalenesulfonic acid/formaldehyde condensate)的鈉鹽、鈣鹽或三乙醇銨鹽。此外，合適的磷酸鹽也是可能的，例如對壬基苯酚/(4-14)環氧乙烷加合物 (p-nonylphenol/(4-14)ethylene oxide adduct)的磷酸酯的鹽，或磷脂。Examples of suitable anionic surfactants are water-soluble soaps or water-soluble nucleating surface-active compounds. Examples of suitable soaps are alkali metal, alkaline earth metal or (substituted or unsubstituted) ammonium salts of fatty acids having about 10 to 22 carbon atoms, for example the sodium or potassium salts of oleic or stearic acid, Or the sodium or potassium salts of natural fatty acid mixtures obtainable, for example, from coconut oil or tall oil; mention must also be made of the fatty acid methyl taurates. However, synthetic surfactants are more commonly used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates ( alkylaryl sulfonates). Typically, fatty sulfonates and fatty sulfates exist as alkali metal, alkaline earth metal, or (substituted or unsubstituted) ammonium salts, which typically have alkyl groups of about 8 to about 22 carbon atoms, also alkyl groups is to be understood to include the alkyl moiety of the acyl group; examples that may be mentioned are the sodium or calcium salts of lignosulfonic acid of the dodecylsulphuric ester or fatty alcohols prepared from natural fatty acids Sodium or calcium salt of lignosulfonic acid of sulfate mixture. This group also includes the sulfate and sulfonate salts of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain two sulfonyl groups and functional groups of fatty acids of about 8 to about 22 carbon atoms. Examples of alkylaryl sulfonates are the sodium salts, calcium salts of decylbenzenesulfonic acid, naphthalenesulfonic acid or naphthalenesulfonic acid/formaldehyde condensate salt or triethanolammonium salt. In addition, suitable phosphates are also possible, such as salts of phosphate esters of p-nonylphenol/(4-14)ethylene oxide adduct, or phospholipids .
通常，組成物包含0.1至99%（尤其是0.1至95%）的本發明化合物以及1至99.9%（尤其是5至99.9%）的至少一種固體或液體載體，而通常來說，組成物的0至25%（尤其是0.1至20%）為界面活性劑（%在每種情況下是指重量百分比）。儘管濃縮組成物係傾向於用於市售商品，但最終消費者通常使用活性成分濃度顯著較低的稀釋組成物。Typically, the composition comprises 0.1 to 99% (especially 0.1 to 95%) of a compound of the invention and 1 to 99.9% (especially 5 to 99.9%) of at least one solid or liquid carrier, and generally, the composition of 0 to 25%, especially 0.1 to 20%, are surfactants (% in each case refers to weight percent). While concentrated compositions tend to be used in commercial products, end consumers typically use diluted compositions with significantly lower concentrations of active ingredients.
預混組成物的葉面製劑類型的例子是：
而預混組合物的種子處理製劑類型的例子是：
適用於桶混組成物 (tank-mix compositions)的製劑類型的例子是溶液、稀釋的乳液、懸浮液或其混合物，以及粉劑。Examples of formulation types suitable for use in tank-mix compositions are solutions, diluted emulsions, suspensions or mixtures thereof, and powders.
與製劑的性質一樣，根據預期目標和主要環境選擇施用方法，例如施用於葉面、浸水、噴灑、霧化、撒粉、撒播、塗佈或傾倒的方式。As with the nature of the formulation, the method of application, such as foliar application, flooding, spraying, atomizing, dusting, spreading, spreading or pouring, is selected according to the intended target and the prevailing environment.
桶混組成物通常透過使用溶劑（例如水）稀釋一種或多種含有不同農藥及任選的其他助劑的預混組成物來製備。合適的載體及佐劑可以是固體或液體，並且是製劑技術中通常使用的物質，例如是天然或再生礦物質、溶劑、分散劑、潤濕劑、增黏劑、增稠劑、黏合劑或肥料。Tank mix compositions are typically prepared by diluting one or more premix compositions containing various pesticides and optionally other adjuvants with a solvent such as water. Suitable carriers and adjuvants can be solid or liquid and are substances commonly used in formulation technology, such as natural or regenerated minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizer.
一般而言，施用於葉面或土壤的桶混製劑包含0.1至20%（尤其是0.1至15%）的所需成分以及99.9至80%（尤其是99.9至85%）的固體或液體助劑（包括，例如，如水的溶劑），其中助劑可以是界面活性劑，其用量為桶混製劑的0至20%（尤其是0.1至15%）。通常地，施用於葉面的預混製劑包含0.1至99.9%（尤其是1至95%）的所需成分以及99.9至0.1%（尤其是99至5%）的固體或液體助劑（包括，例如，如水的溶劑），其中助劑可以是界面活性劑，其用量為預混製劑的0至50%（尤其是0.5至40%）。In general, tank mixes for foliar or soil application contain 0.1 to 20% (especially 0.1 to 15%) of the desired ingredients and 99.9 to 80% (especially 99.9 to 85%) of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 20% (especially 0.1 to 15%) of the tank mix formulation. Typically, premix formulations for foliar application comprise 0.1 to 99.9% (especially 1 to 95%) of the desired ingredients and 99.9 to 0.1% (especially 99 to 5%) of solid or liquid adjuvants (including, For example, a solvent such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 50% (especially 0.5 to 40%) of the premix formulation.
通常地，用於種子處理應用的桶混製劑包含0.25至80%（尤其是1至75%）的所需成分以及99.75至20%（尤其是99至25%）的固體或液體助劑（包括，例如，如水的溶劑），其中助劑可以是界面活性劑，其用量為桶混配方的0至40%（尤其是0.5至30%）。Typically, tank mix formulations for seed treatment applications contain 0.25 to 80% (especially 1 to 75%) of the desired ingredients and 99.75 to 20% (especially 99 to 25%) of solid or liquid adjuvants (including , for example, a solvent such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 40% (especially 0.5 to 30%) of the tank-mixed formulation.
通常地，用於種子處理應用的預混製劑包含0.5至99.9%（尤其是1至95%）的所需成分以及99.5至0.1%（尤其是99至5%）的固體或液體助劑（包括，例如，如水的溶劑），其中助劑可以是界面活性劑，其量為預混製劑的0至50%（尤其是0.5至40%），而商業產品將較佳地被配製成濃縮物（例如，預混組成物（製劑）），而最終用戶通常會使用稀釋製劑（例如桶混組成物）。Typically, premix formulations for seed treatment applications contain 0.5 to 99.9% (especially 1 to 95%) of the desired ingredients and 99.5 to 0.1% (especially 99 to 5%) of solid or liquid adjuvants (including , for example, a solvent such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 50% (especially 0.5 to 40%) of the premix formulation, while the commercial product will preferably be formulated as a concentrate (eg, pre-mixed compositions (formulations)), whereas end users typically use diluted formulations (eg, tank-mixed compositions).
較佳的種子處理預混製劑是水性懸浮劑。可以使用一般處理技術及機器將製劑施用於種子，例如流化床技術 (fluidized bed techniques)、輥磨法 (roller mill method)、旋轉靜態種子處理器 (roto static seed treaters)以及滾筒包衣機 (drum coaters)。其他方法，例如噴射床 (spouted beds)也可能有用。種子可在包衣前就先確定大小。在包衣後，種子通常被乾燥並運送至選粒機 (sizing machine)選粒。這些流程係為已知。本發明的化合物特別適合於土壤及種子處理的應用。Preferred seed treatment premix formulations are aqueous suspensions. The formulations can be applied to the seeds using common processing techniques and machines, such as fluidized bed techniques, roller mill methods, roto static seed treaters, and roller coaters ( drum coaters). Other methods, such as spouted beds, may also be useful. Seeds can be sized prior to coating. After coating, the seeds are typically dried and transported to a sizing machine for sizing. These procedures are known. The compounds of the present invention are particularly suitable for soil and seed treatment applications.
一般來說，本發明的預混組成物含有0.5至99.9%，尤其是1至95%，有利地1至50%的所需成分（以質量計）以及99.5至0.1%，尤其是99至5%的固體或液體佐劑（以質量計）（包括，例如，如水的溶劑），其中助劑（或佐劑）可以是界面活性劑，其用量為預混製劑的0至50%（特別是0.5至40%），以質量計。In general, the premix compositions of the present invention contain from 0.5 to 99.9%, especially from 1 to 95%, advantageously from 1 to 50% of the desired ingredients (by mass) and from 99.5 to 0.1%, especially from 99 to 5% % solid or liquid adjuvant (by mass) (including, for example, a solvent such as water), wherein the adjuvant (or adjuvant) may be a surfactant in an amount of 0 to 50% of the premix formulation (especially 0.5 to 40%), by mass.
在獨立於任何其他實施例的較佳實施例中，式(I)化合物係呈植物繁殖材料處理（或保護）組成物的形式，其中所述植物繁殖材料保護組成物可另外地包含著色劑。植物繁殖材料保護組成物也可包括來自水溶性成膜聚合物及水分散性成膜聚合物的至少一種聚合物，其改善活性成分對處理過的植物繁殖材料的黏附，該聚合物通常具有平均分子量為至少10,000至約100,000。In a preferred embodiment independent of any other embodiments, the compound of formula (I) is in the form of a plant propagation material treatment (or protection) composition, wherein the plant propagation material protection composition may additionally comprise colorants. The plant propagation material protection composition may also include at least one polymer from the group consisting of water-soluble film-forming polymers and water-dispersible film-forming polymers, which improves the adhesion of the active ingredient to the treated plant propagation material, the polymer generally having an average The molecular weight is at least 10,000 to about 100,000.
在一實施例中，本發明提供一種控制或預防農作物及/或園藝作物中的植物病原微生物侵擾實用植物的方法，其中通式(I)化合物及/或其立體異構物或農業上可接受的鹽或互變異構物或N-氧化物或組成物或組合物係施用於植物、其部分、或其所在地。In one embodiment, the present invention provides a method for controlling or preventing the infestation of practical plants by phytopathogenic microorganisms in crops and/or horticultural crops, wherein the compound of general formula (I) and/or a stereoisomer thereof or an agriculturally acceptable The salts or tautomers or N-oxides or compositions or compositions are applied to plants, parts thereof, or their locus.
在另一實施例中，本發明提供一種控制或預防農作物及/或園藝作物中的植物病原線蟲侵擾實用植物的方法，其中通式(I)化合物及/或其立體異構物或農業上可接受的鹽或互變異構物或N-氧化物或組成物或組合物係施用於植物種子。In another embodiment, the present invention provides a method of controlling or preventing phytopathogenic nematodes in crops and/or horticultural crops from infesting utility plants, wherein the compound of general formula (I) and/or its stereoisomers or agriculturally acceptable The accepted salt or tautomer or N-oxide or composition or composition is applied to plant seeds.
在又一實施例中，本發明提供一種使用通式(1)化合物及/或其立體異構物或農業上可接受的鹽或互變異構物或N-氧化物或組成物或組合物而控制或預防農作物及/或園藝作物中的植物病原線蟲的方法，其包括步驟：施用有效劑量的化合物或組成物或組合物，用量範圍為每公頃農業及/或園藝作物1 g至5 kg。In yet another embodiment, the present invention provides a compound of formula (1) and/or its stereoisomers or agriculturally acceptable salts or tautomers or N-oxides or compositions or compositions A method for controlling or preventing phytopathogenic nematodes in crops and/or horticultural crops, comprising the steps of: applying an effective dose of a compound or composition or composition ranging from 1 g to 5 kg per hectare of agricultural and/or horticultural crops.
本發明的化合物及其組成物的施用方法的實例，即農業中防治害蟲的方法，是噴霧、霧化、撒粉、刷塗、敷料、撒播或傾倒，它們將被選擇以適合預期目的之情況。Examples of methods of application of the compounds of the invention and their compositions, ie methods of controlling pests in agriculture, are spraying, atomizing, dusting, brushing, dressing, broadcasting or pouring, which will be selected to suit the circumstances of the intended purpose .
農業中的一種施用方法是施用到植物的葉子上（葉面施用），可以選擇施用頻率和施用率以對應匹配相關害蟲或真菌侵染的危險程度。或者，活性成分可以通過根系統（系統作用）到達植物，透過將化合物施用於植物所在地，例如：透過將化合物的液體組成物施用於土壤中（透過浸透），或透過將顆粒形式的固體形式的化合物施用到土壤中（土壤施用）。在水稻植株的情況下，這種粒劑可以計量加入淹沒的稻田中。將本發明的化合物施用於土壤是較佳的施用方法。One method of application in agriculture is to the foliage of plants (foliar application), and the frequency and rate of application can be chosen to match the risk of infestation by the relevant pest or fungus. Alternatively, the active ingredient can reach the plant through the root system (systemic action) by applying the compound to the plant locus, for example, by applying a liquid composition of the compound to the soil (by saturating), or by applying the compound in solid form in granular form The compound is applied to the soil (soil application). In the case of rice plants, the granules can be metered into submerged paddy fields. Application of the compounds of the present invention to soil is the preferred method of application.
每公頃典型的施用率通常為每公頃1至2000 g活性成分，特別是10至1000 g/ha，較佳10至600 g/ha，例如為50至300 g/ha。Typical application rates per hectare are generally 1 to 2000 g active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha, for example 50 to 300 g/ha.
在一實施例中，本發明提供一種子，其包括式(I)化合物及/或其立體異構物、農業上可接受的鹽、互變異構物、N-氧化物或組成物或組合物，其中式(I)化合物或其N-氧化物或農業上可接受的鹽的含量為每100 kg種子0.1 g至10 kg。In one embodiment, the present invention provides a seed comprising a compound of formula (I) and/or its stereoisomers, agriculturally acceptable salts, tautomers, N-oxides or compositions or compositions , wherein the compound of formula (I) or its N-oxide or agriculturally acceptable salt is present in an amount of 0.1 g to 10 kg per 100 kg of seeds.
本發明的化合物及其組成物也適用於保護植物繁殖材料，例如種子，如果實、塊莖或種仁 (kernels)，或苗圃植物，使其免受上述類型害蟲的侵害。植物繁殖材料在種植前以上述化合物處理，例如可以播種之前處理種子。或者，化合物可以應用於種仁（塗層），方法是將種仁浸泡在液體組成物中或施加一層固體組成物。也可以在將繁殖材料種植到施用部位時施用組成物，例如在鑽孔過程中施用於種溝 (seed furrow)。這些植物繁殖材料的處理方法以及經此處理的植物繁殖材料是本發明的進一步發明主題。典型的處理率將取決於要控制的植物和線蟲，通常為1至200 g/每100 kg種子，較佳為5至150 g/每100 kg種子，例如為10至100 g/每100 kg種子。將本發明的化合物施用於種子是較佳的施用方法。The compounds according to the invention and their compositions are also suitable for the protection of plant propagation material, such as seeds, fruit, tubers or kernels, or nursery plants, against pests of the aforementioned types. Plant propagation material is treated with the above-mentioned compounds before planting, eg seeds can be treated before sowing. Alternatively, the compound can be applied to the kernels (coating) by soaking the kernels in a liquid composition or applying a layer of a solid composition. The composition can also be applied when the propagation material is planted to the application site, for example to the seed furrow during drilling. Methods for the treatment of these plant propagation materials and the plant propagation materials thus treated are further inventive subjects of the present invention. Typical treatment rates will depend on the plants and nematodes to be controlled, usually 1 to 200 g/100 kg of seed, preferably 5 to 150 g/100 kg of seed, for example 10 to 100 g/100 kg of seed . Application of the compounds of the present invention to seeds is the preferred method of application.
術語種子 (seed)包括所有種類的種子和植物繁殖體 (plant propagules)，包括但不限於實生種子 (true seeds)、種子碎片、吸根 (sucker)、球莖 (corms)、鱗莖、果實、塊莖、穀粒、根莖、插條、切條等，在較佳實施例中是指實生種子。The term seed includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed fragments, suckers, corms, bulbs, fruits, tubers , grains, rhizomes, cuttings, cut strips, etc., in a preferred embodiment, refers to the seed.
本發明還包括一種子，其係以式I化合物包衣或處理或含有式I化合物。術語「以式I化合物包衣或處理及/或含有」通常表示：儘管根據施藥方法，成分的更多或更少部分可能滲透到種子材料中，在施用當時大部分的活性成分在種子表面。當此種子產品被（再）種植時，其可能吸收活性物質。在一個實施例中，本發明係提供一種附著有式(I)化合物的植物繁殖材料。此外，在此提供一種包含用式(I)化合物處理的植物繁殖材料的組成物。The present invention also includes a seed which is coated or treated with a compound of formula I or contains a compound of formula I. The term "coated or treated and/or contained with a compound of formula I" generally means that most of the active ingredient is on the surface of the seed at the time of application, although more or less of the ingredient may penetrate into the seed material depending on the method of application. . When this seed product is (re)planted, it may absorb active substances. In one embodiment, the present invention provides a plant propagation material to which a compound of formula (I) is attached. Furthermore, there is provided a composition comprising plant propagation material treated with a compound of formula (I).
種子處理包括本領域已知的所有合適的種子處理技術，例如拌種 (seed dressing)、種子包衣 (seed coating)、種子噴粉 (seed dusting)、浸種 (seed soaking)和種子造粒 (seed pelleting)。式I化合物的種子處理施用是較佳的施用方法，其可以透過任何已知方法進行，例如在播種前或播種/種植期間對種子噴灑或撒粉。Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting pelleting). Seed treatment application of a compound of formula I is a preferred method of application, which can be carried out by any known method, such as spraying or dusting the seeds before sowing or during sowing/planting.
合適的標的植物為，特別是，穀類植物（如小麥、黑麥、大麥、燕麥、稻米、玉米或高粱）；甜菜（例如糖用或飼料甜菜）；水果（例如香蕉、梨果、核果或軟果（例如蘋果、梨子、李子、桃子、杏仁、櫻桃、莓果（例如草莓、覆盆子或黑莓））；豆科植物（例如菜豆 (beans)、扁豆、豌豆或大豆）；油料植物（例如油菜、芥菜、罌粟、橄欖、向日葵、椰子、蓖麻、可可或者花生）；葫蘆科植物（例如南瓜、黃瓜或甜瓜）；纖維植物（例如棉花、亞麻、***或黃麻）；柑橘類水果（例如柳橙、檸檬、葡萄柚或橘子）；蔬菜（例如菠菜、萵苣、蘆筍、捲心菜、胡蘿蔔、洋蔥、番茄、馬鈴薯或甜椒）；月桂科植物 (Lauraceae)（例如酪梨、肉桂或樟腦）；以及煙草、堅果、咖啡、茄子、甘蔗、茶、胡椒、葡萄藤、啤酒花、車前草科植物 (the plantain family)、乳膠植物以及觀賞植物（例如花卉、草坪或草皮）。在一實施例中，植物係選自穀類植物、玉米、大豆、稻米、甘蔗、蔬菜以及油類植物。Suitable target plants are, in particular, cereals (such as wheat, rye, barley, oats, rice, maize or sorghum); sugar beets (such as sugar or fodder beets); fruits (such as bananas, pomes, stone fruits or soft drinks). fruits (such as apples, pears, plums, peaches, almonds, cherries, berries (such as strawberries, raspberries, or blackberries)); legumes (such as beans, lentils, peas, or soybeans); oil plants (such as canola , mustard, poppy, olive, sunflower, coconut, castor, cocoa, or peanut); cucurbits (such as pumpkin, cucumber, or melon); fibrous plants (such as cotton, flax, hemp, or jute); citrus fruits (such as willow oranges, lemons, grapefruit, or tangerines); vegetables (such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers); Lauraceae (such as avocado, cinnamon, or camphor); and Tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, the plantain family, latex plants, and ornamental plants (such as flowers, lawns, or turf). In one embodiment, the plant is Selected from cereals, corn, soybeans, rice, sugar cane, vegetables and oily plants.
術語「植物」應理解為還包括已透過使用重組DNA技術轉化的植物，它們能夠合成一種或多種選擇性作用的毒素（例如為已知的，例如從產生毒素的細菌，尤其是芽孢桿菌屬 (genus Bacillus)的那些細菌，以及包括已被選擇或雜交以保持及/或獲得所需特性（例如昆蟲、真菌及/或線蟲抗性）的植物。可由此類轉殖基因植物表現的毒素包括例如：殺蟲蛋白，例如仙人掌芽孢桿菌 (Bacillus cereus)或金龜子芽孢桿菌 (Bacillus popilliae)所產生的殺蟲蛋白，或者蘇雲金芽孢桿菌 (Bacillus thuringiensis)所產生的殺蟲蛋白，如δ-內毒素 (δ-endotoxins)，例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry2A、Cry2Bbl或Cry9c；營養殺蟲蛋白 (vegetative insecticidal proteins, Vip)，例如Vip1、Vip2、Vip3 或Vip3A；或者拓植線蟲 (bacteria colonizing nematodes)的殺蟲蛋白，例如光桿狀菌屬 (Photorhabdus spp.)或是致病桿菌屬 (Xenorhabdus spp.)，例如發光光桿狀菌 ( Photorhabdus luminescens)及嗜線蟲致病桿菌(Xenorhabdus nematophilus)的殺蟲蛋白；動物產生的毒素，例如蠍毒素、蛛形綱 (arachnid)動物毒素、黃蜂毒素或其他昆蟲特異性神經毒素；真菌產生的毒素，例如鍊黴菌 (Streptomycetes)毒素；植物凝集素，例如豆類、大麥凝集素或銀鐘 (snowdrop)凝集素；凝集素 (agglutinins)；蛋白酶抑制劑，例如胰蛋白酶抑制劑、絲胺酸蛋白酶抑制劑、馬鈴薯糖蛋白 (patatin)、胱抑素 (cystatin)或木瓜蛋白酶 (papain)抑制劑；核醣體失活蛋白(ribosome-inactivating proteins, RIP)，例如蓖麻毒素 (ricin)、玉米-RIP (maize-RIP)、相思子素 (abrin)、絲瓜素 (luffin)、皂草素 (saporin)或苔蘚素 (bryodin)；類固醇代謝酶，例如3-羥基類固醇氧化酶 (3-hydroxysteroid oxidase)、蛻皮類固醇-IDP-糖基轉移酶 (ecdysteroid-IDP-glycosyl-transferase)、膽固醇氧化酶 (cholesterol oxidases)、蛻皮激素 (ecdysone)抑制劑或HMG-CoA-還原酶；離子通道阻滯劑，例如鈉或鈣通道阻滯劑；保幼激素酯酶 (juvenile hormone esterase)；利尿激素受體 (diuretic hormone receptors)（螺旋激肽受體 (helicokinin receptors)）；芪合酶 (stilbene synthase)、聯芐合酶 (bibenzyl synthase)、幾丁質酶 (chitinases)或葡聚醣酶 (glucanases)。在本發明之上下文中，應瞭解δ-內毒素（例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C）或營養殺蟲蛋白(Vip)（例如Vip1、Vip2、Vip3或Vip3A）亦特別為雜交毒素 (hybrid toxins)、截短毒素 (truncated toxins)及經修飾之毒素 (modified toxins)。雜交蛋白質的特徵在於蛋白質結構域的新組合(參照，例如PCT專利公開號WO 02/015701)。截短毒素，例如截短的Cry1Ab，係為已知。在經修飾之毒素的狀況下，天然存在之毒素之一或多個胺基酸係被置換。在該等胺基酸置換中，較佳的將非天然存在之蛋白酶識別序列***毒素中，諸如在Cry3A055之狀況下，將組織蛋白酶-G-識別序列***Cry3A毒素中(參見WO 03/018810)。此類毒素或能夠合成此類毒素的遺傳修飾植物的進一步實例也在，例如歐洲專利號EP-A-0 374 753、PCT專利公開號WO 93/007278、PCT專利公開號WO 95/34656、歐洲專利號EP-A-0 427 529、歐洲專利號EP-A-451 878以及PCT專利公開號WO 03/52073當中被揭露。生產此類基因修飾植物的方法通常是所屬技術領域中具有通常知識者已知的，並且被描述，例如，在上述出版物中。CryI類型的去氧核糖核酸及其製備方法已知於例如PCT專利公開號WO 95/34656、歐洲專利號EP-A-0 367 474、歐洲專利號EP-A-0 401 979及PCT專利公開號WO 90/13651之中。轉殖基因植物中所含之毒素賦予植物針對有害昆蟲之耐受性。雖然該等昆蟲可以任何分類群之昆蟲存在，但尤其以甲蟲（鞘翅目 (Coleoptera)）、雙翼昆蟲（雙翅目 (Diptera)）及蝴蝶（鱗翅目 (Lepidoptera)）常見。含有一或多個編碼殺昆蟲劑抗性且表現一或多種毒素之基因的轉殖基因植物為已知的且其中一些可在市場上購得。這些植物的例子為：YieldGard ®（表現Cry1Ab毒素之玉米變種）；YieldGard Rootworm ®（表現Cry3Bb1毒素之玉米變種）；YieldGard Plus ®（表現Cry1Ab及Cry3Bb1毒素之玉米變種）；Starlink ®（表現Cry9C毒素之玉米變種）；HerculexI ®（表現Cry1Fa2毒素及酶膦絲菌素N-乙醯基轉移酶 (phosphinothricine N-acetyltransferase，PAT)以獲得對除草劑草銨膦 (glufosinate-ammonium)之耐受性的玉米變種)；NuCOTN 33B ®（表現Cry1Ac毒素之棉花變種）；Bollgard I ®（表現Cry1Ac毒素之棉花變種）；Bollgard II ®（表現Cry1Ac及Cry2Ab毒素之棉花變種）；VipCoT ®（表現Vip3A及Cry1Ab毒素之棉花變種）；NewLeaf ®（表現Cry3A毒素之馬鈴薯變種）；NatureGard ®、25Agrisure ®GT Advantage（耐GA21草甘膦特性）、Agrisure ®CB Advantage（耐Bt11玉米螟 (CB)特性）以及Protecta ®。該等轉殖基因作物之其他實例為：i) Bt11玉米，獲自Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France，登記編號C/FR/96/05/10。一種已藉由轉殖基因方式表現截短Cry1Ab毒素而可抵抗歐洲玉米螟（玉米螟蛾 (Ostrinia nubi/alis)及西非蛀莖夜蛾 (Sesamia nonagrioides )）侵襲的經遺傳修玉米(Zea mays)。Bt11玉米亦以轉殖基因方式表現酶PAT以獲得對除草劑草銨膦之耐受性；ii) Bt176玉米，獲自Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France，登記編號C/FR/96/05/10。一種已藉由轉殖基因方式表現截短CryIAb毒素而可抵抗歐洲玉米螟（玉米螟蛾及西非蛀莖夜蛾）侵襲的經遺傳修飾玉米。Bt176玉蜀黍亦以轉殖基因方式表現酶PAT以獲得對除草劑草銨膦之耐受性；iii) MIR604玉米，獲自Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France，登記編號C/FR/96/05/10。一種已藉由轉殖基因方式表現經修飾之Cry3A毒素而可抵抗昆蟲的玉米。此毒素為藉由***組織蛋白酶-G-蛋白酶識別序列而修飾之Cry3A055。該等轉殖基因玉米植物之製備方法描述於PCT專利公開號WO 03/018810中；iv) MON 863玉米，獲自Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium，登記編號C/DE/02/9。MON863 表現Cry3Bb1毒素且具有針對某些鞘翅目昆蟲之抗性；v) IPC 531棉花，獲自Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium，登記編號C/ES/96/02；vi) 1507玉米，獲自Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium，登記編號C/NL/00/10。一種經遺傳修飾之玉米，可表現蛋白質Cry1F而獲得針對某些鱗翅目昆蟲之抗性且可表現PAT蛋白質而獲得針對除草劑草銨膦之耐受性；vii) NK603×MON 810玉米，獲自Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium，登記編號C/GB/02/M3/03。其由按習知方法培育之雜交玉米變種組成，該等變種係由遺傳修飾之變種NK603與MON 810雜交而得。NK603×MON 810玉米以轉殖基因方式表現自土壤桿菌屬 (Agrobacterium sp.)菌株CP4獲得之蛋白質CP4 EPSPS，從而獲得針對除草劑Roundup（含有草甘膦）之耐受性，且表現自蘇雲金芽孢桿菌庫斯塔克亞種(Bacillus thuringiensis subsp. kurstaki)獲得之Cry1Ab毒素，從而獲得針對某些鱗翅目（包括歐洲玉米螟）之耐受性。 The term "plant" is to be understood to also include plants that have been transformed by using recombinant DNA techniques, which are capable of synthesizing one or more selectively acting toxins (such as are known, for example, from toxin-producing bacteria, especially Bacillus ( genus Bacillus), as well as plants that have been selected or crossed to maintain and/or acquire desired characteristics such as insect, fungal and/or nematode resistance. Toxins expressible by such transgenic plants include, for example, : Insecticidal proteins, such as those produced by Bacillus cereus or Bacillus popilliae, or those produced by Bacillus thuringiensis, such as delta-endotoxin (delta-endotoxin) -endotoxins) such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry2A, Cry2Bbl or Cry9c; vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3 or Vip3A; or bacterial colonizing nematodes Insecticidal proteins of photorhabdus spp. or Xenorhabdus spp. such as Photorhabdus luminescens and Xenorhabdus nematophilus Toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins; phytohemagglutinins, such as legumes, barley Lectins or snowdrop lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serpins, patatin, cystatin or papain (papain) inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, Saporin or bryodin; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyltransferase -glycosyl-transferase), cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers such as sodium or calcium channel blockers; juvenile hormone esterase ( juvenile hormone esterase); diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention, it should be understood that delta-endotoxins (eg Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C) or nutritional insecticidal proteins (Vip) (eg Vipl, Vip2, Vip3 or Vip3A) are also Especially hybrid toxins, truncated toxins and modified toxins. Hybrid proteins are characterized by novel combinations of protein domains (see, eg, PCT Patent Publication No. WO 02/015701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of a modified toxin, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid substitutions, it is preferred to insert a non-naturally occurring protease recognition sequence into the toxin, such as in the case of Cry3A055, a cathepsin-G-recognition sequence into the Cry3A toxin (see WO 03/018810) . Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are also found in, for example, European Patent No. EP-A-0 374 753, PCT Patent Publication No. WO 93/007278, PCT Patent Publication No. WO 95/34656, European Patent No. EP-A-0 374 753 It is disclosed in Patent No. EP-A-0 427 529, European Patent No. EP-A-451 878 and PCT Patent Publication No. WO 03/52073. Methods of producing such genetically modified plants are generally known to those of ordinary skill in the art and are described, for example, in the aforementioned publications. Deoxyribonucleic acids of the CryI type and methods for their preparation are known, for example, from PCT Patent Publication No. WO 95/34656, European Patent No. EP-A-0 367 474, European Patent No. EP-A-0 401 979 and PCT Patent Publication No. in WO 90/13651. Toxins contained in transgenic plants confer tolerance to harmful insects. While these insects can exist in any taxonomic group of insects, beetles (Coleoptera), bipedal insects (Diptera) and butterflies (Lepidoptera) are particularly common. Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and some are commercially available. Examples of these plants are: YieldGard ® (a maize variant expressing the Cry1Ab toxin); YieldGard Rootworm ® (a maize variant expressing the Cry3Bb1 toxin); YieldGard Plus ® (a maize variant expressing the Cry1Ab and Cry3Bb1 toxins); Starlink ® (a maize variant expressing the Cry9C toxin) maize variety); HerculexI ® (maize expressing Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) for tolerance to the herbicide glufosinate-ammonium cultivar); NuCOTN 33B ® (cotton cultivar expressing Cry1Ac toxin); Bollgard I ® (cotton cultivar expressing Cry1Ac toxin); Bollgard II ® (cotton cultivar expressing Cry1Ac and Cry2Ab toxin ) ; cotton variety); NewLeaf ® (potato variety expressing Cry3A toxin); NatureGard ® , 25Agrisure ® GT Advantage (GA21 glyphosate resistance), Agrisure ® CB Advantage (Bt11 corn borer (CB) resistance) and Protecta ® . Other examples of such transgenic crops are: i) Bt11 maize available from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, accession number C/FR/96/05/10 . A genetically modified maize (Zea mays) that has been transgenic to express a truncated Cry1Ab toxin against attack by European corn borers (Ostrinia nubi/alis and Sesamia nonagrioides) . Bt11 maize was also transgenic to express the enzyme PAT for tolerance to the herbicide glufosinate-ammonium; ii) Bt176 maize, available from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. A genetically modified maize that has been transgenic to express a truncated CryIAb toxin that is resistant to attack by European corn borers (C. Bt176 maize was also transgenic to express the enzyme PAT for tolerance to the herbicide glufosinate-ammonium; iii) MIR604 maize, obtained from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. A corn that has been transgenic to express a modified Cry3A toxin for resistance to insects. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of these transgenic maize plants is described in PCT Patent Publication No. WO 03/018810; iv) MON 863 maize available from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, accession number C /DE/02/9. MON863 expresses the Cry3Bb1 toxin and is resistant to certain coleopteran insects; v) IPC 531 cotton, available from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, accession number C/ES/96/02 ; vi) 1507 Maize available from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. A genetically modified corn expressing the protein Cry1F to obtain resistance against certain Lepidopteran insects and expressing the PAT protein to obtain tolerance to the herbicide glufosinate; vii) NK603×MON 810 corn, obtained from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. It consists of hybrid corn varieties bred according to conventional methods, which are obtained by crossing genetically modified varieties NK603 with MON 810. NK603×MON 810 maize expresses the protein CP4 EPSPS obtained from Agrobacterium sp. strain CP4 by means of transgenic gene, so as to obtain the tolerance to the herbicide Roundup (containing glyphosate), and express from Bacillus thuringiensis Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki to acquire tolerance against certain Lepidoptera, including European corn borer.
在一實施例中，本發明提供一種組合物，其包括式(I)化合物、其立體異構物、農業上可接受的鹽、互變異構物、或N-氧化物以及一或多個活性相容物質，這些活性相容物質係選自殺真菌劑、殺蟲劑、殺線蟲劑、殺蟎劑、生物殺蟲劑、除草劑、植物生長調節劑、抗生素、營養劑或肥料。In one embodiment, the present invention provides a composition comprising a compound of formula (I), a stereoisomer, agriculturally acceptable salt, tautomer, or N-oxide thereof and one or more reactive Compatible substances, these active compatible substances are selected from fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.
本發明的化合物可有效控制生長中的及已收穫的農藝植物的線蟲及/或真菌病原體，當單獨使用時，它們也可以與農業中使用的其他生物活性劑（例如一種或多種殺線蟲劑、殺蟲劑、殺蟎劑、殺真菌劑、殺菌劑、植物活化劑、殺軟體動物劑以及費洛蒙（無論是化學的還是生物的））一起使用。將作為殺蟲劑的使用形式的本發明的化合物或其組成物與其他殺蟲劑混合通常導致更寬的殺蟲作用光譜。舉例來說，本發明的式(I)化合物可與類除蟲菊精 (pyrethroids)、新煙鹼 (neonicotinoids)、大環內酯 (macrolides)、二醯胺 (diamides)、磷酸鹽 (phosphates)、胺基甲酸酯 (carbamates)、環二烯 (cyclodienes)、甲脒 (formamidines)、酚錫化合物 (phenol tin compounds)、氯化烴 (chlorinated hydrocarbons)、苯甲醯苯基脲 (benzoylphenyl ureas)、吡咯等。The compounds of the present invention are effective in controlling nematodes and/or fungal pathogens in growing and harvested agronomic plants, and when used alone, they can also be combined with other biologically active agents used in agriculture (such as one or more nematicides, Insecticides, acaricides, fungicides, fungicides, plant activators, molluscicides, and pheromones (whether chemical or biological) are used together. Combining the compounds of the invention or compositions thereof in use form as insecticides with other insecticides generally results in a broader spectrum of insecticidal action. For example, the compounds of formula (I) of the present invention can be combined with pyrethroids, neonicotinoids, macrolides, diamides, phosphates , carbamates, cyclodienes, formamidines, phenol tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas , pyrrole, etc.
透過加入例如一種或多種殺蟲、殺蟎、殺線蟲及/或殺真菌的活性劑，可以顯著地拓寬本發明組成物的活性，並適應多數情況。式(I)化合物與其他殺蟲、殺蟎、殺線蟲及/或殺真菌活性劑的化合物組合還可具有進一步令人驚奇的優點。舉例來說，更好的植物耐受性、降低的植物毒性、以及害蟲或真菌可以在其不同發育階段被控制，或者在其生產過程中具有更好的行為，例如在研磨或混合過程中、在儲存過程中或在使用過程中。By adding, for example, one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents, the activity of the compositions of the present invention can be significantly broadened and adapted to most situations. Combinations of compounds of formula (I) with other insecticidally, acaricidally, nematicidally and/or fungicidally active compounds may also have further surprising advantages. For example, better plant tolerance, reduced phytotoxicity, and pests or fungi can be controlled at different stages of their development, or have better behavior during their production, such as during grinding or mixing, during storage or during use.
已知及被報導的活性化合物，例如殺真菌劑、殺蟲劑、殺線蟲劑、殺蟎劑、生物殺蟲劑、除草劑、保護劑、植物生長調節劑、抗生素、肥料及營養劑可以與至少一種本發明的式I化合物組合。舉例來說，揭露於PCT專利公開號WO2017076739 (A至O)的殺真菌劑、殺蟲劑、殺線蟲劑、殺蟎劑、生物殺蟲劑、除草劑、保護劑、植物生長調節劑、抗生素、肥料及營養劑可與本發明的式I化合物組合。本發明還關於包含本發明化合物及PCT專利公開號WO2017076739中所報導的活性相容化合物的此類組合。Known and reported active compounds such as fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides, protectants, plant growth regulators, antibiotics, fertilizers and nutrients can be combined with Combination of at least one compound of formula I according to the invention. For example, fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides, protectants, plant growth regulators, antibiotics disclosed in PCT Patent Publication No. WO2017076739 (A to O) , fertilizers and nutrients can be combined with the compounds of formula I of the present invention. The present invention also relates to such combinations comprising compounds of the present invention and active compatible compounds as reported in PCT Patent Publication No. WO2017076739.
本發明的式(I)化合物還可與作用方式未知或不確定的其他殺蟲活性化合物組合，如下：雙丙環蟲酯 (afidopyropen)、阿福拉納 (afoxolaner)、印楝素 (azadirachtin)、磺胺蟎酯 (amidoflumet)、西脫蟎 (benzoximate)、必芬蟎 (bifenazate)、溴蟲氟苯雙醯胺 (broflanilide)、新殺蟎 (bromopropylate)、蟎離丹 (chinomethionat)、冰晶石 (cryolite)、二氯噻吡嘧啶 (dicloromezotiaz)、大克蟎 (dicofol)、氟芬林 (flufenerim)、氟洛美坤 (flometoquin)、氟賽蟲碸 (fluensulfone)、氟赫吩 (fluhexafon)、氟吡蘭 (fluopyram)、氟吡二福隆(flupyradifurone)、氟拉蘭納 (fluralaner)、惡蟲酮 (metoxadiazone)、胡椒基丁氧化物 (piperonyl butoxide)、哌氟布邁 (pyflubumide)、啶蟲丙醚 (pyridalyl)、吡氟喹蟲唑 (pyrifluquinazon)、碸蟲啶 (sulfoxaflor)、敵賽吩 (tioxazafen)、三氟滅蟲胺 (triflumezopyrim)、11-(4-氯-2,6-二甲基苯基)-12-羥基-1,4-二氧-9-氮雜二雙螺並[4.2.4.2]-十四-11-烯-10-酮、3-(4' -氟-2,4-二甲基苯-3-基)-4-羥基-8-氧-1-氮雜螺並[4.5]癸-3-烯-2-酮、1-[2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯基]-3-(三氟甲基)-1 H-1,2,4-***-5-胺、堅強芽孢桿菌 (Bacillus firmus)；(E/Z)-N-[1-[(6-氯-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2,2-三氟-乙醯胺；(E/Z)-N-[1-[(6-氯-5-氟-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2,2-三氟-乙醯胺；(E/Z)-2,2,2-三氟-N-[1-[(6-氟-3-吡啶基)甲基]-2-伸二氫吡啶基]乙醯胺；(E/Z)-N-[1-[(6-溴-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2,2-三氟乙醯胺；(E/Z)-N-[1-[1-(6-氯-3-吡啶基)乙基]-2-伸二氫吡啶基]-2,2,2-三氟乙醯胺；(E/Z)-N-[1-[(6-氯-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2-二氟-乙醯胺；(E/Z)-2-氯-N-[1-[(6-氯-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2-二氟-乙醯胺；(E/Z)-N-[1-[(2-氯嘧啶-5-基)甲基]-2-伸二氫吡啶基]-2,2,2-三氟-乙醯胺；(E/Z)-N-[1-[(6-氯-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2,3,3,3-五氟-丙醯胺)；N-[1-[ (6-氯-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2,2-三氟-硫乙醯胺；N-[1-[(6-氯-3-吡啶基)甲基]-2-伸二氫吡啶基]-2,2,2-三氟-N'-異丙基-乙醯胺；氯氟氰蟲醯胺 (fluazaindolizine)；4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4H-異噁唑-3-基]-2-甲基-N-(1-側氧基硫雜環丁-3-基)苯甲醯胺；氟賽醯胺；5-[3-[2,6-二氯-4-(3,3-二氯烯丙氧基)苯氧基]丙氧基]-1H-吡唑；3-(苯甲醯基甲基胺基)-N-[2-溴-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]-6-(三氟甲基)苯基]-2-氟-苯甲醯胺；3-(苯甲醯基甲基胺基)-2-氟-N-[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]-苯甲醯胺；N-[3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]胺基]羰基]苯基]-N-甲基-苯甲醯胺；N-[3-[[[2-bromo-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]胺基]羰基]-2-氟苯基]-4-氟-N-甲基苯甲醯胺；4-氟-N-[2-氟-3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]胺基]羰基]苯基]-N-甲基-苯甲醯胺；3-氟-N-[2-氟-3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6(三氟甲基)苯基]胺基]羰基]苯基]-N-甲基-苯甲醯胺；2-氯-N-[3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]胺基]羰基]苯基]-3-吡啶羧醯胺；4-腈基-N-[2-腈基-5-[[2,6-二溴-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]胺甲醯基]苯基]-2-甲基-苯甲醯胺；4-腈基-3-[(4-腈基-2-甲基-苯甲基)胺基]-N-[2,6-二氯-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]-2-苯甲醯胺；N-[5-[[2-氯-6-腈基-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]胺甲醯基]-2-腈基-苯基]-4-腈基-2-甲基-苯甲醯胺；N-[5-[[2-溴-6-氯-4-[2,2,2-三氟-1-羥基-1-(三氟甲基)乙基]苯基]胺甲醯基]-2-腈基-苯基]-4-腈基-2-甲基-苯甲醯胺；N-[5-[[2-溴-6-氯-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]胺甲醯基]-2-腈基-苯基]-4-腈基-2-甲基-苯甲醯胺；4-腈基-N-[2-腈基-5-[[2,6-二氯-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]胺甲醯基]苯基]-2-甲基-苯甲醯胺；4-腈基-N-[2-腈基-5-[[2,6-二氯-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]胺甲醯基]苯基]-2-甲基-苯甲醯胺；N-[5-[[2-溴-6-氯-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]胺甲醯基]-2-腈基-苯基]-4-腈基-2-甲基-苯甲醯胺；2-(1,3-二噁-2-基)-6-[2-(3-吡啶基)-5-噻唑基]-吡啶；2-[6-[2-(5-氟-3-吡啶基)-5-噻唑基]-2-吡啶基]-嘧啶；2-[6-[2-(3-吡啶基)-5-噻唑基]-2-吡啶基]-嘧啶；N-甲磺醯基-6-[2-(3-吡啶基)噻唑-5-基]吡啶-2-羧醯胺；甲磺醯基-6-[2-(3-吡啶基)噻唑-5-基]吡啶-2-羧醯胺；N-乙基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基-丙醯胺；N-甲基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基-丙醯胺；N,2-二甲基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基丙醯胺；N-乙基-2-甲基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基-丙醯胺；N-[4-氯-2-(3-吡啶基)噻唑-5-基]-N-乙基-2-甲基-3-甲硫基-丙醯胺；N-[4-氯-2-(3-吡啶基 )噻唑-5-基]-N,2-二甲基-3-甲硫基-丙醯胺；N-[4-氯-2-(3-吡啶基)噻唑-5-基]-N-甲基-3-甲硫基-丙醯胺；N-[4-氯-2-(3-吡啶基)噻唑-5-基]-N-乙基-3-甲硫基-丙醯胺；1-[(6-氯-3-吡啶基)甲基]-1,2,3,5,6,7-六氫-5-甲氧基-7-甲基-8-硝基-咪唑並[1,2-a]吡啶；1-[(6-氯吡啶-3-基)甲基]-7-甲基-8-硝基-1,2,3,5,6,7-六氫咪唑並[1,2-a]吡啶-5-醇；1-異丙基-N,5-二甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；1-(1,2-二甲基丙基)-N-乙基-5-甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；N,5-二甲基-N-噠嗪-4-基-1-(2,2,2-三氟-1-甲基-乙基)吡唑-4-羧醯胺；1-[1-(1-腈基環丙基)乙基]-N-乙基-5-甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；N-乙基-1-(2-氟-1-甲基-丙基)-5-甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；1-(1,2-二甲基丙基)-N,5-二甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；1-[1-(1-腈基環丙基)乙基]-N,5-二甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；N-甲基-1-(2-氟-1-甲基-丙基]-5-甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；1-(4,4-二氟環己基)-N-乙基-5-甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；1-(4,4-二氟環己基)-N,5-二甲基-N-噠嗪-4-基-吡唑-4-羧醯胺；N-(1-甲基乙基)-2-(3-吡啶基)-2H-吲唑-4-羧醯胺；N-環丙基-2-(3-吡啶基)-2H-吲唑-4-羧醯胺；N-環己基-2-(3-吡啶基)- 2H-吲唑-4-羧醯胺；2-(3-吡啶基)-N-(2,2,2-三氟乙基)-2H-吲唑-4-羧醯胺；2-(3-吡啶基)-N-[(四氫-2-呋喃基)甲基]-2H-吲唑-5-羧醯胺；2-[[2-(3-吡啶基)-2H-吲唑-5-yl]羰基]聯胺羧酸甲酯；N-[(2,2-二氟環丙基)甲基]-2-(3-吡啶基)-2H-吲唑-5-羧醯胺；N-(2,2-二氟丙基)-2-(3-吡啶基)-2H-吲唑-5-羧醯胺；2-(3-吡啶基 )N-(2-嘧啶基甲基 )-2H-吲唑-5-羧醯胺；N-[(5-甲基-2-吡嗪基)甲基]-2-(3-吡啶基)-2H-吲唑-5-羧醯胺；N-[3-氯-1-(3-吡啶基)吡唑-4-基]N-乙基-3-(3,3,3-三氟丙磺醯基)丙醯胺；N-[3-氯-1-(3-吡啶基)吡唑-4-基]-N-乙基-3-(3,3,3-三氟丙磺醯基)丙醯胺；N-[3-氯-1-(3-吡啶基)吡唑-4-基]-3-[(2,2-二氟環丙基)甲磺醯基]-N-乙基-丙醯胺；N-[3-氯-1-(3-吡啶基)吡唑-4-yl]-3-[(2,2-二氟環丙基) 甲磺醯基]-N-乙基-丙醯胺；撒洛倫 (sarolaner)、羅替蘭 (lotilaner)。The compounds of formula (I) of the present invention may also be combined with other pesticidally active compounds whose mode of action is unknown or uncertain, such as the following: afidopyropen, afoxolaner, azadirachtin , Amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite ( cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluorine Fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, acetamiprid Pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, 11-(4-chloro-2,6-di) Methylphenyl)-12-hydroxy-1,4-dioxo-9-azabibisspiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4'-fluoro- 2,4-Dimethylben-3-yl)-4-hydroxy-8-oxo-1-azaspiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4- Methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1,2,4-triazole-5- Amine, Bacillus firmus; (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2- Trifluoro-acetamide; (E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2 -Trifluoro-acetamide; (E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-dihydropyridyl] Acetamide; (E/Z)-N-[1-[(6-Bromo-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2-trifluoroacetamide; (E/Z)-N-[1-[1-(6-Chloro-3-pyridyl)ethyl (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2 -dihydropyridyl]-2,2-difluoro-acetamide; (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2- Dihydropyridyl]-2,2-difluoro-acetamide; (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-dihydropyridyl] -2,2,2-Trifluoro-acetamide; (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2, 2,3,3,3-Pentafluoro-propionamide); N-[1-[(6-Chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2- Trifluoro-thioacetamide; N-[1-[(6-Chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2-trifluoro-N'-isopropyl yl-acetamide; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl ]-2-Methyl-N-(1-oxythietan-3-yl)benzamide; Fluoxamide; 5-[3-[2,6-Dichloro-4-( 3,3-Dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; 3-(benzylmethylamino)-N-[2-bromo-4-[1, 2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; 3-(benzene carboxylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl) Fluoromethyl)phenyl]-benzamide; N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] -6-(Trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzylamine; N-[3-[[[2-bromo-4-[1,2, 2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl benzamide; 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl ]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3-fluoro-N-[2-fluoro-3-[[[2- Iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl yl-benzamide; 2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6 -(Trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; 4-nitrile-N-[2-nitrile-5-[[2,6-dibromo- 4 -[1,2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminocarbamoyl]phenyl]-2-methyl-benzylamide; 4-cyano-3-[(4-cyano-2-methyl-benzyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3, 3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-benzamide; N-[5-[[2-chloro-6-cyano-4-[1,2, 2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminocarbamoyl]-2-nitrile-phenyl]-4-nitrile-2-methyl- Benzylamide; N-[5-[[2-Bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl] Aminocarboxy]-2-nitrile-phenyl]-4-nitrile-2-methyl-benzylamine; N-[5-[[2-bromo-6-chloro-4-[1, 2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminocarbamoyl]-2-nitrile-phenyl]-4-nitrile-2-methyl yl-benzamide; 4-nitrile-N-[2-nitrile-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1 -(Trifluoromethyl)propyl]phenyl]aminocarbamoyl]phenyl]-2-methyl-benzylamine; 4-nitrile-N-[2-nitrile-5-[[2 ,6-Dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]aminocarbamoyl]phenyl]-2-methyl-benzyl Amide; N-[5-[[2-Bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]aminocarbamoyl ]-2-nitrile-phenyl]-4-nitrile-2-methyl-benzamide; 2-(1,3-diox-2-yl)-6-[2-(3-pyridine base)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; 2-[6-[ 2-(3-Pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; N-methanesulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2 - Carboxamide; Mesylate-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2- (3-Pyridinyl)thiazol-5-yl]-3-methylthio-propionamide; N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl] -3-Methylthio-propionamide; N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthiopropionamide ; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; N-[4-chloro -2-(3-Pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propionamide; N-[4-Chloro-2-(3-pyridyl] )thiazol-5-yl]-N,2-dimethyl-3-methyl Sulfanyl-propionamide; N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylsulfanyl-propionamide; N-[4-chloro -2-(3-Pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propionamide; 1-[(6-chloro-3-pyridyl)methyl]-1, 2,3,5,6,7-Hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridine-3 -yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; 1-isopropyl yl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1 -Methyl-ethyl)pyrazole-4-carboxyamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazine-4 -yl-pyrazole-4-carboxamide; N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole- 4-Carboxamide; 1-(1,2-Dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-[1 -(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazol-4-carboxamide; N-methyl-1-(2- Fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazol-4-carboxamide; 1-(4,4-difluorocyclohexyl)-N-ethyl 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazine -4-yl-pyrazol-4-carboxamide; N-(1-methylethyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide; N-cyclopropyl -2-(3-pyridyl)-2H-indazole-4-carboxamide; N-cyclohexyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; 2-(3 -Pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridyl)-N-[(tetrahydro-2-furan Methyl)methyl]-2H-indazole-5-carboxamide; 2-[[2-(3-pyridyl)-2H-indazole-5-yl]carbonyl]hydrazinecarboxylate; Methyl 2-[[2-(3-pyridyl)-2H-indazole-5-yl]carbonyl]hydrazinecarboxylate [(2,2-Difluorocyclopropyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide; N-(2,2-difluoropropyl)-2 -(3-Pyridyl)-2H-indazole-5-carboxamide; 2-(3-pyridyl)N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; N -[(5-Methyl-2-pyrazinyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide; N-[3-chloro-1-(3- Pyridyl)pyrazol-4-yl ]N-ethyl-3-(3,3,3-trifluoropropanesulfonyl)propionamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N -Ethyl-3-(3,3,3-trifluoropropanesulfonyl)propionamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[ (2,2-Difluorocyclopropyl)methanesulfonyl]-N-ethyl-propionamide; N-[3-chloro-1-(3-pyridyl)pyrazole-4-yl]-3 -[(2,2-Difluorocyclopropyl)methanesulfonyl]-N-ethyl-propionamide; sarolaner, lotilaner.
上述活性物質、它們的製備和它們的活性（例如對抗有害真菌/昆蟲/線蟲），係為已知（參見：http://www.alanwood.net/pesticides/）；這些物質是可於市面上購得的。以IUPAC命名法所描述的化合物、它們的製備和它們的殺蟲活性也是已知的（參見0366＞Can. J. Plant Sci. 48(6), 587-94, 1968；歐洲專利號EP-A 141 317；歐洲專利號EP-A 152 031；歐洲專利號EP-A 226 917；歐洲專利號EP-A 243 970；歐洲專利號EP-A 256 503；歐洲專利號EP-A 428 941；歐洲專利號EP-A 532 022；歐洲專利號EP-A 1 028 125；歐洲專利號EP-A1 035 122；歐洲專利號EP-A 1 201 648；歐洲專利號EP-A 1 122 244；日本專利號JP 2002316902；德國專利號DE 19650197；德國專利號DE 10021412； 得國專利號DE 102005009458；美國專利號US 3,296,272；美國專利號US 3,325,503；PCT專利公開號WO 98/46608；PCT專利公開號WO 99/14187；PCT專利公開號WO 99/24413；PCT專利公開號WO 99/27783；PCT專利公開號WO 00/29404；PCT專利公開號WO 00/46148；PCT專利公開號WO 00/65913；PCT專利公開號WO 01/54501；PCT專利公開號WO 01/56358；PCT專利公開號WO 02/22583；PCT專利公開號WO 02/40431；PCT專利公開號WO 03/10149；PCT專利公開號WO 03/11853；PCT專利公開號WO 03/14103；PCT專利公開號WO 03/16286；PCT專利公開號WO 03/53145；PCT專利公開號WO 03/61388；PCT專利公開號WO 03/66609；PCT專利公開號WO 03/74491；PCT專利公開號WO 04/49804；PCT專利公開號WO 04/83193；PCT專利公開號WO 05/120234；PCT專利公開號WO 05/123689；PCT專利公開號WO 05/123690；PCT專利公開號WO 05/63721；PCT專利公開號WO 05/87772；PCT專利公開號WO 05/87773；PCT專利公開號WO 06/15866；PCT專利公開號WO 06/87325；PCT專利公開號WO 06/87343；PCT專利公開號WO 07/82098；PCT專利公開號WO 07/90624；PCT專利公開號WO 10/139271；PCT專利公開號WO 11/028657；PCT專利公開號WO 12/168188；PCT專利公開號WO 07/006670；PCT專利公開號WO 11/77514；PCT專利公開號WO 13/047749；PCT專利公開號WO 10/069882；PCT專利公開號WO 13/047441；PCT專利公開號WO 03/16303；PCT專利公開號WO 09/90181；PCT專利公開號WO 13/007767；PCT專利公開號WO 13/010862；PCT專利公開號WO 13/127704；PCT專利公開號WO 13/024009；PCT專利公開號WO 13/24010；PCT專利公開號WO 13/047441；PCT專利公開號WO 13/162072；PCT專利公開號WO 13/092224；PCT專利公開號WO 11/135833；中國專利號CN 1907024；中國專利號CN 1456054；中國專利號CN 103387541；中國專利號CN 1309897；PCT專利公開號WO 12/84812；中國專利號CN 1907024；PCT專利公開號WO 09094442；PCT專利公開號WO 14/60177；PCT專利公開號WO 13/116251；PCT專利公開號WO 08/013622；PCT專利公開號WO 15/65922；PCT專利公開號WO 94/01546；歐洲專利號EP 2865265；PCT專利公開號WO 07/129454；PCT專利公開號WO 12/165511；PCT專利公開號WO 11/081174；PCT專利公開號WO 13/47441）。The above-mentioned active substances, their preparation and their activity (eg against harmful fungi/insects/nematodes) are known (see: http://www.alanwood.net/pesticides/); these substances are commercially available purchased. Compounds described under IUPAC nomenclature, their preparation and their pesticidal activity are also known (see 0366 > Can. J. Plant Sci. 48(6), 587-94, 1968; European Patent No. EP-A 141 317; European Patent No. EP-A 152 031; European Patent No. EP-A 226 917; European Patent No. EP-A 243 970; European Patent No. EP-A 256 503; European Patent No. EP-A 428 941; European Patent No. No. EP-A 532 022; European Patent No. EP-A 1 028 125; European Patent No. EP-A1 035 122; European Patent No. EP-A 1 201 648; European Patent No. EP-A 1 122 244; Japanese Patent No. JP 2002316902; German Patent No. DE 19650197; German Patent No. DE 10021412; National Patent No. DE 102005009458; US Patent No. US 3,296,272; US Patent No. US 3,325,503; ; PCT Patent Publication No. WO 99/24413; PCT Patent Publication No. WO 99/27783; PCT Patent Publication No. WO 00/29404; PCT Patent Publication No. WO 00/46148; PCT Patent Publication No. WO 00/65913; WO 01/54501; PCT Patent Publication No. WO 01/56358; PCT Patent Publication No. WO 02/22583; PCT Patent Publication No. WO 02/40431; PCT Patent Publication No. WO 03/10149; PCT Patent Publication No. WO 03/11853; PCT Patent Publication No. WO 03/14103; PCT Patent Publication No. WO 03/16286; PCT Patent Publication No. WO 03/53145; PCT Patent Publication No. WO 03/61388; PCT Patent Publication No. WO 03/66609; PCT Patent Publication No. WO 03/74491; PCT Patent Publication No. WO 04/49804; PCT Patent Publication No. WO 04/83193; PCT Patent Publication No. WO 05/120234; PCT Patent Publication No. WO 05/123689; PCT Patent Publication No. WO 05/123690; Patent Publication No. WO 05/63721; PCT Patent Publication No. WO 05/87772; PCT Patent Publication No. WO 05/87773; PCT Patent Publication No. WO 06/15866; PCT Patent Publication No. WO 06/87325; PCT Patent Publication No. WO 06 /87343 PCT Patent Publication No. WO 07/82098; PCT Patent Publication No. WO 07/90624; PCT Patent Publication No. WO 10/139271; PCT Patent Publication No. WO 11/028657; PCT Patent Publication No. WO 12/168188; WO 07/006670; PCT Patent Publication No. WO 11/77514; PCT Patent Publication No. WO 13/047749; PCT Patent Publication No. WO 10/069882; PCT Patent Publication No. WO 13/047441; PCT Patent Publication No. WO 03/16303; PCT Patent Publication No. WO 09/90181; PCT Patent Publication No. WO 13/007767; PCT Patent Publication No. WO 13/010862; PCT Patent Publication No. WO 13/127704; PCT Patent Publication No. WO 13/024009; PCT Patent Publication No. WO 13/24010; PCT Patent Publication No. WO 13/047441; PCT Patent Publication No. WO 13/162072; PCT Patent Publication No. WO 13/092224; PCT Patent Publication No. WO 11/135833; Chinese Patent No. CN 1907024; Chinese Patent No. CN 1456054; Chinese Patent No. CN 103387541; Chinese Patent No. CN 1309897; PCT Patent Publication No. WO 12/84812; Chinese Patent No. CN 1907024; PCT Patent Publication No. WO 09094442; PCT Patent Publication No. WO 14/60177; PCT Patent Publication No. WO 13/116251; PCT Patent Publication No. WO 08/013622; PCT Patent Publication No. WO 15/65922; PCT Patent Publication No. WO 94/01546; European Patent No. EP 2865265; PCT Patent Publication No. WO 07/129454; PCT Patent Publication No. WO 12/165511; PCT Patent Publication No. WO 11/081174; PCT Patent Publication No. WO 13/47441).
選擇每種組合中任意兩種成分的質量比以提供所需的效果，例如增強活性。一般而言，通常，質量比將根據特定成分以及組合中存在的成分數量而變化。一般而言，本發明的任意組合中的任意兩種成分之間的質量比彼此獨立地為100:1至1:100，包括從99:1、98:2、97:3、96:4、95:5、94:6、93:7、92:8、91:9、90:10、89:11、88:12、87:13、86:14、85:15、84:16、83:17、82:18、81:19、80:20、79:21、78:22、77:23、76:24、75:25、74:26、73:27、72:28、71:29、70:30、69:31、68:32、67:33、66:34、65:45、64:46、63:47、62:48、61:49、60:40、59:41、58:42、57:43、56:44、55:45、54:46、53:47、52:48、51:49、50:50、49:51、48:52、47:53、46:54、45:55、44:56、43:57、42:58、41:59、40:60、39:61、38:62、37:63、36:64、35:65、34:66、33:67、32:68、31:69、30:70、29:71、28:72、27:73、26:74、25:75、24:76、23:77、22:78、21:79、20:80、19:81、18:82、17:83、16:84、15:85、14:86、13:87、12:88、11:89、10:90、9:91、8:92、7:93、6:94、5:95、4:96、3:97、2:98至1:99。本發明的兩種成分之間的質量比較佳地為從75:1至1:75，特別佳地為50:1至1.50，尤其佳地為25:1至1:25，有利地為10:1至1:10，例如5:1至1:5，例如1:3至3:1。混合比應理解為一方面包括質量比，另一方面還包括莫耳比。The mass ratio of any two ingredients in each combination is chosen to provide the desired effect, such as enhanced activity. In general, mass ratios will vary depending on the particular ingredients and the amount of ingredients present in the combination. In general, the mass ratio between any two components in any combination of the present invention is independently of each other from 100:1 to 1:100, including from 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83: 17, 82:18, 81:19, 80:20, 79:21, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31, 68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41, 58: 42, 57:43, 56:44, 55:45, 54:46, 53:47, 52:48, 51:49, 50:50, 49:51, 48:52, 47:53, 46:54, 45:55, 44:56, 43:57, 42:58, 41:59, 40:60, 39:61, 38:62, 37:63, 36:64, 35:65, 34:66, 33: 67, 32:68, 31:69, 30:70, 29:71, 28:72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78, 21:79, 20:80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91, 8: 92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98 to 1:99. The mass ratio between the two components of the present invention is preferably from 75:1 to 1:75, particularly preferably 50:1 to 1.50, particularly preferably 25:1 to 1:25, advantageously 10:1 1 to 1:10, eg 5:1 to 1:5, eg 1:3 to 3:1. Mixing ratios are understood to include mass ratios on the one hand and molar ratios on the other hand.
本發明的組合（即包含本發明化合物及一種或多種其他生物活性劑的組合）可以同時或依次施用。A combination of the present invention (ie, a combination comprising a compound of the present invention and one or more other biologically active agents) can be administered simultaneously or sequentially.
在組合的成分係依次施用（即一個接一個）的情況下，這些成分在彼此的合理時間內（例如在幾小時或幾天內）依次施用以獲得生物學性能。以組合形式施用成分的順序，亦即是否應首先施用式(I)化合物，對於實施本發明並不重要。Where the components of the combination are administered sequentially (ie, one after the other), the components are administered sequentially within a reasonable time of each other (eg, within hours or days) to achieve biological performance. The order in which the ingredients are administered in combination, ie whether the compound of formula (I) should be administered first, is not critical to the practice of the present invention.
如果組合的成分在本發明中同時施用，它們可以作為包含組成物的組合物施用，在這種情況下：(A) 式(I)化合物及組合中的一種或多種其他成分可以從單獨的製劑來源獲得並混合在一起（稱為桶混 (tank-mix)、即用 (ready-to-apply)、噴霧 (spray broth)或漿液），或(B) 式(I)化合物及一種或多種其他成分可以是作為單一配方混合物來源（稱為預混物 (pre-mix)、預拌物 (ready-mix)、濃縮物或製劑產品）的方式被獲得。If the components of the combination are administered simultaneously in the present invention, they may be administered as a composition comprising the composition, in which case: (A) the compound of formula (I) and one or more other components of the combination may be prepared from separate formulations Sources are obtained and mixed together (called tank-mix, ready-to-apply, spray broth or slurry), or (B) a compound of formula (I) and one or more other The ingredients may be obtained as a source of a single formulation mixture known as a pre-mix, ready-mix, concentrate or formulated product.
在一個實施例中，獨立於其他實施例，根據本發明的化合物係作為組合物應用。據此，本發明也還提供了一種組成物，其包括本發明此處所述的化合物以及一或多種其他的生物活性試劑及可選擇地包括一或多個一般製劑助劑；可以桶混或預拌組成物的形式呈現。In one embodiment, independent of the other embodiments, the compounds according to the present invention are applied as compositions. Accordingly, the present invention also provides a composition comprising the compound of the present invention described herein and one or more other biologically active agents and optionally one or more general formulation adjuvants; it can be tank-mixed or Presented in the form of ready-mixed compositions.
式(I)的化合物特別有用於控制及預防蠕蟲及線蟲內源性 (endo)和外源性 (ecto)寄生蟲對溫血動物的侵擾與感染，例如牛、羊、豬、駱駝、鹿、馬、家禽、魚、兔、山羊、貂、狐狸、絨鼠、狗與貓以及人類。在對於控制和預防溫血動物受侵染和感染，本發明的化合物特別適用於控制蠕蟲和線蟲。蠕蟲的例子是吸蟲綱 (Trematoda)的成員，通常被稱為吸蟲 (flukes)或扁蟲 (flatworms)，尤其是肝片吸蟲屬 (Fasciola)、擬片形吸蟲屬 (Fascioloides)、同端盤吸蟲屬 (Paramphistomu)、雙腔吸蟲屬 (Dicrocoelium)、腸吸蟲屬 (Eurytrema)、後睪吸蟲屬 (Opisthorchis)、薑片蟲屬 (Fasciolopsis)、棘口吸蟲屬 (Echinostoma)以及肺吸蟲屬 (Paragonimus)。可由式(I)化合物防治的線蟲包括血球蟲屬 (Haemonchus)、胃絲蟲屬 (Ostertagia)、古柏線蟲屬 (Cooperia)、腸結節蟲屬 (Oesphagastomu)、細頸線蟲屬 (Nematodirus)、網尾線蟲屬 (Dictyocaulus)、鞭蟲屬 (Trichuris)、犬心絲蟲屬 (Dirofilaria)、鉤蟲線蟲屬 (Ancyclostoma)、蛔蟲屬 (Ascaria)等。對於溫血動物的口服給藥，本發明的化合物可以配製成動物飼料、動物飼料預混物、動物飼料濃縮劑、藥丸、溶液、膏劑、懸浮液、浸液、凝膠、片劑、丸劑及膠囊。此外，本發明的化合物可透過飲用水對動物給藥。就口服給藥而言，所選擇的劑型應為動物提供每天約0.01 mg/kg至100 g/kg動物體重的本發明化合物。或者，本發明的化合物可以腸胃外 (parenterally)方式給藥，例如透過瘤胃內 (intraruminal)、肌肉內、靜脈內或皮下注射。本發明的化合物可以分散或溶解於生理上可接受的載體，以進行皮下注射。或者，本發明的化合物可以配製成用於皮下給藥的植入物。此外，本發明的化合物可以對動物經皮 (transdermally)給藥。就腸胃外給藥而言，所選擇的劑型應為動物提供每天約0.01 mg/kg至100 g/kg動物體重的本發明化合物。The compounds of formula (I) are particularly useful for the control and prevention of infestation and infection of warm-blooded animals such as cattle, sheep, pigs, camels, deer by endogenous (endo) and exogenous (ecto) parasites of helminths and nematodes , horses, poultry, fish, rabbits, goats, minks, foxes, chinchillas, dogs and cats, and humans. For the control and prevention of infestation and infection in warm-blooded animals, the compounds of the present invention are particularly useful for the control of helminths and nematodes. Examples of worms are members of the class Trematoda, commonly known as flukes or flatworms, especially Fasciola, Fascioloides , Paramphistomu, Dicrocoelium, Eurytrema, Opisthorchis, Fasciolopsis, Acanthostomy (Echinostoma) and Paragonimus. Nematodes that can be controlled by compounds of formula (I) include Haemonchus, Ostertagia, Cooperia, Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaria, etc. For oral administration to warm-blooded animals, the compounds of the present invention can be formulated into animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, infusions, gels, tablets, pills and capsules. In addition, the compounds of the present invention can be administered to animals through drinking water. For oral administration, the dosage form selected should provide the animal with about 0.01 mg/kg to 100 g/kg of the animal's body weight per day of the compound of the invention. Alternatively, the compounds of the present invention may be administered parenterally, for example by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention can be formulated into implants for subcutaneous administration. In addition, the compounds of the present invention can be administered transdermally to animals. For parenteral administration, the dosage form selected should provide the animal with about 0.01 mg/kg to 100 g/kg of the animal's body weight per day of a compound of the invention.
本發明的化合物也可以透過浸劑、粉劑、粉末、項圈、獎章、噴霧劑及澆注製劑的形式而以外用方式 (topically)施用於動物。對外用施用的情況而言，浸劑及噴霧劑通常包含0.5 ppm至5,000 ppm的本發明的化合物，且較佳包含約1 ppm至3,000 ppm的本發明的化合物。此外，本發明的化合物可以配製成動物（特別是四足動物 (quadrupeds)，例如牛和羊）的耳標 (ear tags)。The compounds of the present invention can also be administered topically to animals in the form of infusions, dusts, powders, collars, medallions, sprays and pour-on formulations. For topical application, dips and sprays typically contain from 0.5 ppm to 5,000 ppm, and preferably from about 1 ppm to 3,000 ppm, of a compound of the present invention. Furthermore, the compounds of the present invention can be formulated into ear tags for animals, particularly quadrupeds such as cattle and sheep.
在一實施例中，獨立於其他實施例，式(I)化合物是一種抗蠕蟲化合物。In one embodiment, independent of other embodiments, the compound of formula (I) is an antihelminthic compound.
在一實施例中，獨立於其他實施例，式(I)化合物是一種殺蟲化合物，較佳為一種殺線蟲化合物。In one embodiment, independent of other embodiments, the compound of formula (I) is a pesticidal compound, preferably a nematicidal compound.
本發明的化合物不僅有效地控制線蟲害蟲，而且表現出積極的作物反應（例如植物生長促進作用，如增強作物活力、增強根的生長、增強對乾旱、高鹽、高溫、寒冷、霜凍或光輻射的耐受性 ，改善開花，有效的水和養分利用（如改善氮同化 (nitrogen assimilation)），提高植物產品的品質，更多的分蘗，增強對真菌、昆蟲、害蟲等的抵抗力），從而提高產量。The compounds of the present invention are not only effective in controlling nematode pests, but also exhibit positive crop responses (e.g. plant growth promoting effects such as enhanced crop vigor, enhanced root growth, enhanced response to drought, high salt, high temperature, cold, frost or light radiation tolerance, improved flowering, efficient water and nutrient use (e.g. improved nitrogen assimilation), improved plant product quality, more tillers, increased resistance to fungi, insects, pests, etc.), thereby Increase production.
化學實例：Chemical example:
以下實施例闡述了製備本發明化合物的方式及製程，但不限於此，並且包括發明人為實施本發明而設想的最佳模式。The following examples illustrate, but are not limited to, means and procedures for the preparation of the compounds of this invention, and include the best modes contemplated by the inventors for carrying out the invention.
實例 1 ： 4,4- 二氟丁 -3- 烯 -1- 基 2-(4- 氯 -1H- 吡唑 -1- 基 ) 醋酸酯 (4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)acetate) 的製備 
於2-(4-氯-1H-吡唑-1-基)醋酸 (250 mg, 1.56 mmol)的乾的N,N-二甲基甲醯胺 (8 mL)的溶液中，係加入N,N-二異丙基乙基胺 (0.27 ml, 1.56 mmol)以及4-溴-1,1-二氟丁-1-烯 (532 mg, 3.11 mmol)，而反應混合物係於80 ℃攪拌16 h。之後，以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，而有機層係被分離，水溶液層係再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係藉由管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物4,4-二氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)醋酸酯 (270 mg, 1.077 mmol, 產率69.2 %), LCMS (M+1): 251To a solution of 2-(4-chloro-1H-pyrazol-1-yl)acetic acid (250 mg, 1.56 mmol) in dry N,N-dimethylformamide (8 mL) was added N,N-dimethylformamide (8 mL). N-diisopropylethylamine (0.27 ml, 1.56 mmol) and 4-bromo-1,1-difluorobut-1-ene (532 mg, 3.11 mmol), and the reaction mixture was stirred at 80 °C for 16 h . After that, it was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 4,4-difluorobut-3-en-1-yl 2-(4-chloro- 1H-pyrazol-1-yl)acetate (270 mg, 1.077 mmol, 69.2 % yield), LCMS (M+1): 251
實例 2 ： 3,4,4- 三氟丁 -3- 烯 -1- 基 2-(4- 甲基 -1H- 吡唑 -1- 基 ) 醋酸酯 (3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate) 的製備 
於2-(4-甲基-1H-吡唑-1-基)醋酸 (450 mg, 3.21 mmol)的乾的N,N-二甲基甲醯胺 (8 mL)的溶液中，係加入N,N-二異丙基乙基胺 (0.561 ml, 3.21 mmol) and 4-氯-1,1,2-三氟丁-1-烯 (928 mg, 6.42 mmol)，而反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物3,4,4-三氟丁-3-烯-1-基2-(4-甲基-1H-吡唑-1-基)醋酸酯 (375 mg, 1.51 mmol, 產率47.1 %), LCMS (M+1): 249.1To a solution of 2-(4-methyl-1H-pyrazol-1-yl)acetic acid (450 mg, 3.21 mmol) in dry N,N-dimethylformamide (8 mL) was added N , N-diisopropylethylamine (0.561 ml, 3.21 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (928 mg, 6.42 mmol), and the reaction mixture was kept at 80 °C Stir for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl) yl-1H-pyrazol-1-yl)acetate (375 mg, 1.51 mmol, 47.1 % yield), LCMS (M+1): 249.1
實例 3 ： 3,4,4- 三氟丁 -3- 烯 -1- 基 2-(3,5- 二甲基 -1H- 吡唑 -1- 基 ) 醋酸酯 (3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate) 的製備方法 
於2-(3,5-二甲基-1H-吡唑-1-基)醋酸 (450 mg, 2.92 mmol)的乾 N,N-二甲基甲醯胺 (8 mL)的溶液中，係加入N,N-二異丙基乙基胺 (0.510 ml, 2.92 mmol)以及 4-氯-1,1,2-三氟丁-1-烯 (844 mg, 5.84 mmol)，而反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物3,4,4-三氟丁-3-烯-1-基2-(3,5-二甲基-1H-吡唑-1-基)醋酸酯 (340 mg, 1.297 mmol, 產率44.4 %), LCMS (M+1): 263.1In a solution of 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetic acid (450 mg, 2.92 mmol) in dry N,N-dimethylformamide (8 mL) N,N-Diisopropylethylamine (0.510 ml, 2.92 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (844 mg, 5.84 mmol) were added and the reaction mixture was at Stir at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(3,5 -Dimethyl-1H-pyrazol-1-yl)acetate (340 mg, 1.297 mmol, 44.4 % yield), LCMS (M+1): 263.1
實例 4 ： 3,4,4- 三氟丁 -3- 烯 -1- 基 2-(4- 氯 -1H- 吡唑 -1- 基 ) 丙酸酯 (3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate) 的製備 
步驟step 11 ：: 2-(4-2-(4- 氯chlorine -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸乙酯Ethyl propionate (ethyl 2-(4-chloro-1H-pyrazol-1-yl)propanoate)(ethyl 2-(4-chloro-1H-pyrazol-1-yl)propanoate) 的製備preparation
於4-氯-1H-吡唑 (500 mg, 4.88 mmol)的乾的N,N-二甲基甲醯胺 (10 mL)溶液中，係加入碳酸鉀 (1.35 g, 9.75 mmol)以及2-溴丙酸乙酯 (0.9 ml, 6.4 mmol)，且反應混合物係於60 ℃攪拌4 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物2-(4-氯-1H-吡唑-1-基)丙酸乙酯 (600 mg, 2.96 mmol, 產率60.7 %), LCMS (M+1): 203.1To a solution of 4-chloro-1H-pyrazole (500 mg, 4.88 mmol) in dry N,N-dimethylformamide (10 mL) was added potassium carbonate (1.35 g, 9.75 mmol) and 2- Ethyl bromopropionate (0.9 ml, 6.4 mmol), and the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound, ethyl 2-(4-chloro-1H-pyrazol-1-yl)propanoate (600 mg , 2.96 mmol, 60.7% yield), LCMS (M+1): 203.1
步驟step 22 ：: 2-(4-2-(4- 氯chlorine -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸propionic acid (2-(4-chloro-1H-pyrazol-1-yl)propanoic acid)(2-(4-chloro-1H-pyrazol-1-yl)propanoic acid) 的製備preparation
於2-(4-氯-1H-吡唑-1-基)丙酸酯 (1 g, 4.93 mmol)的甲醇-四氫呋喃 (6 ml:3 ml)溶液中，係加入氫氧化鋰 (0.236 g, 9.87 mmol)的水 (1 ml)溶液，而反應混合物係於室溫下攪拌2 h。反應混合物係被濃縮、以水 (5 ml)稀釋並以乙酸乙酯清洗。水溶液層係以濃鹽酸酸化並以乙酸乙酯 (60ml x 2)萃取。合併的有機層係以無水硫酸鈉乾燥、過濾並以減壓濃縮而得到所需產物，2-(4-氯-1H-吡唑-1-基)丙酸 (600 mg, 3.44 mmol, 產率69.6 %), LCMS (M+1): 174.9To a solution of 2-(4-chloro-1H-pyrazol-1-yl)propanoate (1 g, 4.93 mmol) in methanol-tetrahydrofuran (6 ml:3 ml) was added lithium hydroxide (0.236 g, 9.87 mmol) in water (1 ml) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(4-chloro-1H-pyrazol-1-yl)propionic acid (600 mg, 3.44 mmol, yield 69.6 %), LCMS (M+1): 174.9
步驟step 33 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(4-2-(4- 氯chlorine -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸酯propionate (3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate)(3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate) 的製備preparation
於2-(4-氯-1H-吡唑-1-基)丙酸 (400 mg, 2.291 mmol)的乾的N,N-二甲基甲醯胺 (8 mL)的溶液中，係加入N,N-二異丙基乙胺 (0.8 ml, 4.58 mmol)以及4-氯-1,1,2-三氟丁-1-烯 (662 mg, 4.58 mmol)，反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物3,4,4-三氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)丙酸酯 (500 mg, 1.77 mmol, 產率77 %), LCMS (M+1): 282.95To a solution of 2-(4-chloro-1H-pyrazol-1-yl)propionic acid (400 mg, 2.291 mmol) in dry N,N-dimethylformamide (8 mL) was added N , N-diisopropylethylamine (0.8 ml, 4.58 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (662 mg, 4.58 mmol), the reaction mixture was stirred at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro -1H-pyrazol-1-yl)propionate (500 mg, 1.77 mmol, 77 % yield), LCMS (M+1): 282.95
實例 5 ： 3,4,4- 三氟丁 -3- 烯 -1- 基 2-(4- 氯 -1H- 吡唑 -1- 基 )-2- 甲基丙酸酯 (3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate) 的製備 
步驟step 11 ：: 2-(4-2-(4- 氯chlorine -1H--1H- 吡唑Pyrazole -1--1- 基base )-2-)-2- 甲基丙酸乙酯Ethyl methylpropionate (ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate)(ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate) 的製備preparation
在4-氯-1H-吡唑 (500 mg, 4.88 mmol)的乾的N,N-二甲基甲醯胺 (10 mL)的溶液中，係加入碳酸銫 (9.53 g, 29.3 mmol)以及2-溴-2-甲基丙酸乙酯 (2.85 ml, 19.02 mmol)，而反應混合物係於60 ℃攪拌4 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸乙酯 (2.5 g, 11.54 mmol, 產率79 %), LCMS (M+1): 217.1To a solution of 4-chloro-1H-pyrazole (500 mg, 4.88 mmol) in dry N,N-dimethylformamide (10 mL) was added cesium carbonate (9.53 g, 29.3 mmol) and 2 -Bromo-2-methylpropionic acid ethyl ester (2.85 ml, 19.02 mmol), and the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid Ethyl ester (2.5 g, 11.54 mmol, 79 % yield), LCMS (M+1): 217.1
步驟step 22 ：: 2-(4-2-(4- 氯chlorine -1H--1H- 吡唑Pyrazole -1--1- 基base )-2-)-2- 甲基丙酸Methylpropionic acid (2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoic acid)(2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoic acid) 的製備preparation
在2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸乙酯 (3 g, 13.85 mmol)的甲醇-四氫呋喃 (6 ml:3 ml)溶液中，係加入氫氧化鋰 (0.66 g, 27.7 mmol)的水 (1 ml)溶液，且反應混合物係於室溫下攪拌2 h。反應混合物係被濃縮、以水 (5 ml)稀釋並以乙酸乙酯清洗。水溶液層係以濃鹽酸酸化並以乙酸乙酯萃取。合併的有機層係以無水硫酸鈉乾燥、過濾及減壓濃縮而得到所需產物，2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸 (2 g, 10.6 mmol, 產率77 %), LCMS (M+1): 189.1To a solution of 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid ethyl ester (3 g, 13.85 mmol) in methanol-tetrahydrofuran (6 ml:3 ml) was added hydrogen Lithium oxide (0.66 g, 27.7 mmol) in water (1 ml) was dissolved, and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid (2 g, 10.6 mmol, 77% yield), LCMS (M+1): 189.1
步驟step 33 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(4-2-(4- 氯chlorine -1H--1H- 吡唑Pyrazole -1--1- 基base )-2-)-2- 甲基丙酸酯Methylpropionate (3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate)(3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate) 的製備preparation
於2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸 (300 mg, 1.59 mmol)的乾的N,N-二甲基甲醯胺 (8 mL)的溶液中，係加入N,N-二異丙基乙胺 (0.6 ml, 3.2 mmol)以及4-氯-1,1,2-三氟丁-1-烯 (460 mg, 3.18 mmol)，反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥、過濾及減壓濃縮而得到粗產物。粗產物係藉由管柱層析法，利用1-30%乙酸乙酯/己烷，而得到標題化合物3,4,4-三氟丁-3-烯-1-基2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸酯 (420 mg, 1.42 mmol, 產率89 %), LCMS (M+1): 296.95A solution of 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid (300 mg, 1.59 mmol) in dry N,N-dimethylformamide (8 mL) , N,N-diisopropylethylamine (0.6 ml, 3.2 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (460 mg, 3.18 mmol) were added, and the reaction mixture was Stir at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography using 1-30% ethyl acetate/hexane to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro -1H-pyrazol-1-yl)-2-methylpropionate (420 mg, 1.42 mmol, 89 % yield), LCMS (M+1): 296.95
實例 6 ： 3,4,4- 三氟丁 -3- 烯 -1- 基 2-(4- 甲基 -1H- 吡唑 -1- 基 ) 丙酸酯 (3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate) 的製備 
步驟step 11 ：: 2-(4-2-(4- 甲基methyl -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸乙酯Ethyl propionate (ethyl 2-(4-methyl-1H-pyrazol-1-yl)propanoate)(ethyl 2-(4-methyl-1H-pyrazol-1-yl)propanoate) 的製備preparation
在4-甲基-1H-吡唑 (1.5 g, 18.27 mmol)的乾的N,N-二甲基甲醯胺 (10 mL)溶液中，係加入碳酸鉀 (5.05 g, 36.5 mmol)以及2-溴丙酸乙酯 (3.31 ml, 23.75 mmol)，反應混合物係於60 ℃攪拌4 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物2-(4-氯-1H-吡唑-1-基)-2-甲基丙酸乙酯 (2.5 g, 11.54 mmol, 產率79 %), LCMS (M+1): 217.1To a solution of 4-methyl-1H-pyrazole (1.5 g, 18.27 mmol) in dry N,N-dimethylformamide (10 mL) was added potassium carbonate (5.05 g, 36.5 mmol) and 2 - Ethyl bromopropionate (3.31 ml, 23.75 mmol), the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid Ethyl ester (2.5 g, 11.54 mmol, 79 % yield), LCMS (M+1): 217.1
步驟step 22 ：: 2-(4-2-(4- 甲基methyl -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸propionic acid (2-(4-methyl-1H-pyrazol-1-yl)propanoic acid)(2-(4-methyl-1H-pyrazol-1-yl)propanoic acid) 的製備preparation
於2-(4-甲基-1H-吡唑-1-基)丙酸乙酯 (2.2 g, 12.07 mmol)的甲醇-四氫呋喃 (6 ml:3 ml)的溶液中，係加入氫氧化鋰 (0.58 g, 24.2 mmol)的水 (1 ml)溶液，而反應混合物係於室溫下攪拌2 h。反應混合物係被濃縮、以水 (5 ml)稀釋並以乙酸乙酯清洗。水溶液層係以濃鹽酸酸化並以乙酸乙酯 (60ml x 2)萃取。合併的有機層係以無水硫酸鈉乾燥、過濾及減壓濃縮而得到所需產物，2-(4-甲基-1H-吡唑-1-基)丙酸 (1.5 g, 9.73 mmol, 產率81 %), LCMS (M+1): 155.1Lithium hydroxide ( 0.58 g, 24.2 mmol) in water (1 ml), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(4-methyl-1H-pyrazol-1-yl)propionic acid (1.5 g, 9.73 mmol, yield 81 %), LCMS (M+1): 155.1
步驟step 33 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(4-2-(4- 甲基methyl -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸酯propionate (3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate)(3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate) 的製備preparation
於2-(4-甲基-1H-吡唑-1-基)丙酸 (300 mg, 1.95 mmol)的乾的N,N-二甲基甲醯胺 (8 mL)的溶液中，係加入N,N-二異丙基乙胺 (0.68 ml, 3.89 mmol)以及4-氯-1,1,2-三氟丁-1-烯 (366 mg, 2.53 mmol)，且反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物3,4,4-三氟丁-3-烯-1-基2-(4-甲基-1H-吡唑-1-基)丙酸酯 (345 mg, 1.32 mmol, 產率67.6 %), LCMS (M+1): 263.1To a solution of 2-(4-methyl-1H-pyrazol-1-yl)propionic acid (300 mg, 1.95 mmol) in dry N,N-dimethylformamide (8 mL) was added N,N-diisopropylethylamine (0.68 ml, 3.89 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (366 mg, 2.53 mmol), and the reaction mixture was kept at 80 °C Stir for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl) yl-1H-pyrazol-1-yl)propionate (345 mg, 1.32 mmol, 67.6 % yield), LCMS (M+1): 263.1
實例 7 ： 3,4,4- 三氟丁 -3- 烯 -1- 基 2- 甲基 -2-(4- 甲基 -1H- 吡唑 -1- 基 ) 丙酸酯 (3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate) 的製備 
步驟step 11 ：: 2-2- 甲基methyl -2-(4--2-(4- 甲基methyl -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸乙酯Ethyl propionate (ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate)(ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate) 的製備preparation
於4-甲基-1H-吡唑 (1.5 g, 18.27 mmol)的乾的N,N-二甲基甲醯胺 (10 mL)的溶液中，係加入碳酸銫 (8.93 g, 27.4 mmol)以及2-溴-2-甲基丙酸乙酯 (4.63 g, 23.75 mmol)，反應混合物係於60 ℃攪拌4 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物2-甲基-2-(4-甲基-1H-吡唑-1-基)丙酸乙酯 (2.1 g, 10.70 mmol, 產率58.6 %) LCMS (M+1): 197.1To a solution of 4-methyl-1H-pyrazole (1.5 g, 18.27 mmol) in dry N,N-dimethylformamide (10 mL) was added cesium carbonate (8.93 g, 27.4 mmol) and Ethyl 2-bromo-2-methylpropanoate (4.63 g, 23.75 mmol), the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propane Ethyl acid (2.1 g, 10.70 mmol, 58.6 % yield) LCMS (M+1): 197.1
步驟step 22 ：: 2-2- 甲基methyl -2-(4--2-(4- 甲基methyl -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸propionic acid (2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoic acid)(2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoic acid) 的製備preparation
於2-甲基-2-(4-甲基-1H-吡唑-1-基)丙酸乙酯 (2.5 g, 12.74 mmol)的甲醇-四氫呋喃 (6 ml:3 ml)的溶液中，係加入氫氧化鋰 (0.61 g, 25.5 mmol)的水 (1 ml)溶液，且反應混合物係於室溫下攪拌2 h。反應混合物係被濃縮、以水 (5 ml)稀釋並以乙酸乙酯清洗。水溶液層係以濃鹽酸酸化並以乙酸乙酯 (60ml x 2)萃取。合併的有機層係以無水硫酸鈉乾燥、過濾及減壓蒸發而得到所需的產物，2-甲基-2-(4-甲基-1H-吡唑-1-基)丙酸 (1.8 g, 10.7 mmol, 產率84 %), LCMS (M+1): 169.1In a solution of ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate (2.5 g, 12.74 mmol) in methanol-tetrahydrofuran (6 ml:3 ml) A solution of lithium hydroxide (0.61 g, 25.5 mmol) in water (1 ml) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the desired product, 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionic acid (1.8 g , 10.7 mmol, 84% yield), LCMS (M+1): 169.1
步驟step 33 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-2- 甲基methyl -2-(4--2-(4- 甲基methyl -1H--1H- 吡唑Pyrazole -1--1- 基base )) 丙酸酯propionate (3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate)(3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate)
於2-甲基-2-(4-甲基-1H-吡唑-1-基)丙酸 (600 mg, 3.57 mmol)的乾的N,N-二甲基甲醯胺 (8 mL)的溶液中，係加入N,N-二異丙基乙胺 (1.2 ml, 7.13 mmol)以及4-氯-1,1,2-三氟丁-1-烯 (670 mg, 4.64 mmol)，且反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物3,4,4-三氟丁-3-烯-1-基2-甲基-2-(4-甲基-1H-吡唑-1-基)丙酸酯 (350 mg, 1.267 mmol, 產率35.5 %), LCMS (M+1): 277.1A solution of 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionic acid (600 mg, 3.57 mmol) in dry N,N-dimethylformamide (8 mL) To the solution, N,N-diisopropylethylamine (1.2 ml, 7.13 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (670 mg, 4.64 mmol) were added and reacted The mixture was stirred at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl2-methyl-2 -(4-Methyl-1H-pyrazol-1-yl)propionate (350 mg, 1.267 mmol, 35.5 % yield), LCMS (M+1): 277.1
實例Example 88 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(3-2-(3- 甲基methyl -1H--1H- 吲唑Indazole -1--1- 基base )) 醋酸酯Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate)(3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate) 的製備preparation
步驟step 11 ：: 2-(3-2-(3- 甲基methyl -1H--1H- 吲唑Indazole -1--1- 基base )) 乙酸乙酯Ethyl acetate (ethyl 2-(3-methyl-1H-indazol-1-yl)acetate)(ethyl 2-(3-methyl-1H-indazol-1-yl)acetate) 的製備preparation
於3-甲基-2H-吲唑 (400 mg, 3.03 mmol)的乾的丙酮 (8 mL)溶液中，係加入碳酸鉀 (837 mg, 6.05 mmol)以及2-溴乙酸乙酯 (505 mg, 3.03 mmol)，且反應混合物係於60 ℃攪拌4 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物2-(3-甲基-1H-吲唑-1-基)乙酸乙酯 (500 mg, 2.3 mmol, 產率76 %) LCMS (M+1): 219.1To a solution of 3-methyl-2H-indazole (400 mg, 3.03 mmol) in dry acetone (8 mL) was added potassium carbonate (837 mg, 6.05 mmol) and ethyl 2-bromoacetate (505 mg, 3.03 mmol), and the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound, ethyl 2-(3-methyl-1H-indazol-1-yl)acetate (500 mg , 2.3 mmol, 76% yield) LCMS (M+1): 219.1
步驟step 22 ：: 2-(3-2-(3- 甲基methyl -1H--1H- 吲唑Indazole -1--1- 基base )) 醋酸acetic acid (2-(3-methyl-1H-indazol-1-yl)acetic acid)(2-(3-methyl-1H-indazol-1-yl)acetic acid) 的製備preparation
於2-(3-甲基-1H-吲唑-1-基)乙酸乙酯 (590 mg, 2.70 mmol)的甲醇-四氫呋喃 (4 ml:2 ml)溶液中，係加入氫氧化鋰 (129 mg, 5.41 mmol)的水 (0.5 ml)溶液，且反應混合物係於室溫下攪拌2 h。反應混合物係被濃縮、以水 (5 ml)稀釋並以乙酸乙酯清洗。水溶液層係以濃鹽酸酸化並以乙酸乙酯 (60ml x 2)萃取。合併的有機層係以無水硫酸鈉乾燥、過濾並以減壓濃縮而得到所需產物，2-(3-甲基-1H-吲唑-1-基)醋酸 (450 mg, 2.37 mmol, 產率88 %), LCMS (M+1): 191.1To a solution of ethyl 2-(3-methyl-1H-indazol-1-yl)acetate (590 mg, 2.70 mmol) in methanol-tetrahydrofuran (4 ml:2 ml) was added lithium hydroxide (129 mg , 5.41 mmol) in water (0.5 ml), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(3-methyl-1H-indazol-1-yl)acetic acid (450 mg, 2.37 mmol, yield 88 %), LCMS (M+1): 191.1
步驟step 33 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(3-2-(3- 甲基methyl -1H--1H- 吲唑Indazole -1--1- 基base )) 醋酸酯Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate)(3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate) 的製備preparation
於2-(3-甲基-2H-吲唑-2-基)醋酸 (250 mg, 1.314 mmol)的乾的N,N-二甲基甲醯胺 (7 mL)溶液中，係加入N,N-二異丙基乙胺 (0.46 ml, 2.63 mmol)以及4-氯-1,1,2-三氟丁-1-烯 (247 mg, 1.71 mmol)，反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物3,4,4-三氟丁-3-烯-1-基2-(3-甲基-2H-吲唑-2-基)醋酸酯 (160 mg, 0.54 mmol, 產率40 %), LCMS (M+1): 299.3To a solution of 2-(3-methyl-2H-indazol-2-yl)acetic acid (250 mg, 1.314 mmol) in dry N,N-dimethylformamide (7 mL) was added N,N-dimethylformamide (7 mL). N-diisopropylethylamine (0.46 ml, 2.63 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (247 mg, 1.71 mmol), the reaction mixture was stirred at 80 °C for 16 h . The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl) yl-2H-indazol-2-yl)acetate (160 mg, 0.54 mmol, 40 % yield), LCMS (M+1): 299.3
實例Example 99 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(4,5-2-(4,5- 二氯Dichloro -1H--1H- 咪唑imidazole -1--1- 基base )) 醋酸酯Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate)(3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate) 的製備preparation
步驟step 11 ：: 2-(4,5-2-(4,5- 二氯Dichloro -1H--1H- 咪唑imidazole -1--1- 基base )) 醋酸acetic acid (2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid)(2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid) 的製備preparation
於4,5-二氯-1H-咪唑 (1 g, 7.30 mmol)的乾的乙腈 (20 ml)溶液中，係加入碳酸鉀 (1.514 g, 10.95 mmol)以及2-溴醋酸叔丁酯 (1.295 ml, 8.76 mmol)，反應混合物係以室溫攪拌2 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥、過濾及減壓蒸發而得到所需的產物，2-(4,5-二氯-1H-咪唑-1-基)醋酸叔丁酯 (1.8 g, 7.17 mmol, 產率98 %)。於經攪拌的2-(4,5-二氯-1H-咪唑-1-基)醋酸叔丁酯 (1.8 g, 7.17 mmol)的二氯甲烷 (10 ml)，係加入鹽酸 (7.17 ml, 28.7 mmol)且於20-25 °C攪拌16h。反應混合物係蒸發至乾燥而得到所需產物2-(4,5-二氯-1H-咪唑-1-基)醋酸，1.5 克，為米白色固體 （鹽酸鹽）。LCMS (M+1): 194.80; 1HNMR: 1H-NMR (400 MHz, DMSO-d6 ) δ 9.57-9.79 (br s, 1H), 7.78 (s, 1H), 4.87 (s, 2H) To a solution of 4,5-dichloro-1H-imidazole (1 g, 7.30 mmol) in dry acetonitrile (20 ml) was added potassium carbonate (1.514 g, 10.95 mmol) and tert-butyl 2-bromoacetate (1.295 ml, 8.76 mmol), the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the desired product, tert-butyl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.8 g, 7.17 g) mmol, 98% yield). To a stirred solution of tert-butyl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.8 g, 7.17 mmol) in dichloromethane (10 ml) was added hydrochloric acid (7.17 ml, 28.7 mmol) and stirred at 20-25 °C for 16 h. The reaction mixture was evaporated to dryness to give the desired product 2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid, 1.5 g, as an off-white solid (hydrochloride). LCMS (M+1): 194.80; 1 HNMR: 1 H-NMR (400 MHz, DMSO-d6 ) δ 9.57-9.79 (br s, 1H), 7.78 (s, 1H), 4.87 (s, 2H)
步驟step 22 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(4,5-2-(4,5- 二氯Dichloro -1H--1H- 咪唑imidazole -1--1- 基base )) 醋酸酯Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate)(3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate) 的製備preparation
於2-(4,5-二氯-1H-咪唑-1-基)醋酸 (1.5 g, 7.69 mmol)的乾的N,N-二甲基甲醯胺 (10 mL)溶液中，係加入N,N-二異丙基乙胺 (4.03 ml, 23.1 mmol)以及4-氯-1,1,2-三氟丁-1-烯 (247 mg, 1.71 mmol)，反應混合物係於80 ℃攪拌16 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標的化合物3,4,4-三氟丁-3-烯-1-基2-(4,5-二氯-1H-咪唑-1-基)醋酸酯 (1.1 g, 3.63 mmol, 產率47.2 %)，呈深咖啡色油狀，LCMS (M-1): 302.85To a solution of 2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid (1.5 g, 7.69 mmol) in dry N,N-dimethylformamide (10 mL) was added N , N-diisopropylethylamine (4.03 ml, 23.1 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (247 mg, 1.71 mmol), the reaction mixture was stirred at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flushing system to obtain the target compound 3,4,4-trifluorobut-3-en-1-yl 2-(4,5 -Dichloro-1H-imidazol-1-yl)acetate (1.1 g, 3.63 mmol, 47.2 % yield) as dark brown oil, LCMS (M-1): 302.85
實例example 1010 ：: 3,4,4-3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base 2-(3,5-2-(3,5- 二甲基dimethyl -1H-1,2,4--1H-1,2,4- ***triazole -1--1- 基base )) 醋酸酯Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate)(3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate) 的製備preparation
於2-(3,5-二甲基-1H-1,2,4-***-1-基)醋酸 (300 mg, 1.94 mmol)的乾的N,N-二甲基甲醯胺 (05 mL)的溶液中，係加入N,N-二異丙基乙胺 (1.013 ml, 5.80 mmol)以及4-氯-1,1,2-三氟丁-1-烯 (419 mg, 2.90 mmol)，且反應混合物係於80 ℃攪拌12 h。反應混合物係以乙酸乙酯 (30 mL)及水 (30 mL)稀釋，有機層係被分離，而水溶液層則再次以乙酸乙酯 (30 mL)萃取。合併的有機層係以無水硫酸鈉乾燥，過濾並以減壓濃縮而得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物，3,4,4-三氟丁-3-烯-1-基2-(3,5-二甲基-1H-1,2,4-***-1-基)醋酸酯，LCMS (M+1): 263.9Dry N,N-dimethylformamide (05) in 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetic acid (300 mg, 1.94 mmol) mL), was added N,N-diisopropylethylamine (1.013 ml, 5.80 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (419 mg, 2.90 mmol) , and the reaction mixture was stirred at 80 °C for 12 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound, 3,4,4-trifluorobut-3-en-1-yl 2-(3, 5-Dimethyl-1H-1,2,4-triazol-1-yl)acetate, LCMS (M+1): 263.9
實例example 1111 ：: 2-(4-2-(4- 氯chlorine -1H--1H- 吡唑Pyrazole -1--1- 基base )-N-(3,4,4-)-N-(3,4,4- 三氟丁trifluorobutane -3--3- 烯alkene -1--1- 基base )) 乙醯胺Acetamide (2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1-yl)acetamide)(2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1-yl)acetamide) 的製備preparation
於經攪拌的2-(4-氯-1H-吡唑-1-基)醋酸 (0.179 g, 1.114 mmol)的N,N-二甲基甲醯胺 (3 ml)的溶液中，係加入3,4,4-三氟丁-3-烯-1-胺鹽酸鹽 (0.150g, 0.928 mmol)以及N,N-二異丙基乙胺 (0.487 ml, 2.79 mmol) 並接著加入HATU (0.530 g, 1.393 mmol)。所得的反應混合物係於25 °C攪拌3h。反應混合物接著被以水稀釋並以乙酸乙酯 (25ml x 2)萃取。有機層係以無水硫酸鈉乾燥，並以減壓濃縮而乾燥，以得到粗產物。粗產物係以管柱層析法，利用乙酸乙酯/己烷作為沖堤系統純化，而得到標題化合物2-(4-氯-1H-吡唑-1-基)-N-(3,4,4-三氟丁-3-烯-1-基)乙醯胺 (170mg, 0.635 mmol, 產率68.4 %)，呈無色油狀。LCMS (M+1): 267.8To a stirred solution of 2-(4-chloro-1H-pyrazol-1-yl)acetic acid (0.179 g, 1.114 mmol) in N,N-dimethylformamide (3 ml) was added 3 ,4,4-trifluorobut-3-en-1-amine hydrochloride (0.150 g, 0.928 mmol) and N,N-diisopropylethylamine (0.487 ml, 2.79 mmol) and then HATU (0.530 g, 1.393 mmol). The resulting reaction mixture was stirred at 25 °C for 3 h. The reaction mixture was then diluted with water and extracted with ethyl acetate (25ml x 2). The organic layer was dried over anhydrous sodium sulfate, and concentrated and dried under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4 ,4-Trifluorobut-3-en-1-yl)acetamide (170 mg, 0.635 mmol, 68.4 % yield) as a colorless oil. LCMS (M+1): 267.8
表surface 11 係根據流程與實例中所描述的合適方法製備的本發明的代表性化合物Representative compounds of the invention were prepared according to suitable methods described in the Schemes and Examples
表-1：
如此處所述，式(I)的化合物顯示高殺線蟲活性，其對攻擊重要農作物的線蟲發揮作用。以下係評估本發明化合物對以下一種或多種線蟲的活性。As described herein, compounds of formula (I) exhibit high nematicidal activity against nematodes that attack important crops. The following lines evaluate the activity of compounds of the invention against one or more of the following nematodes.
生物實例biological example
對於植物寄生線蟲的生物測試實例Examples of biological tests for plant-parasitic nematodes
實例1：Meloidogyne incognita (Root-knot nematode)：活體外測試Example 1: Meloidogyne incognita (Root-knot nematode): in vitro testing
南方根結線蟲 (Meloidogyne incognita)：將濃度為300 ppm的測試化合物吸入24孔微量滴定板的孔中，每孔含有500 μL蒸餾水以及50隻南方根結線蟲幼蟲。懸浮液被輕微搖晃以均勻地混合化合物。試片以蓋子蓋住，並在溫度25 °C及RH 90%孵育。在顯微鏡下以48、72及96小時的間隔計數死亡/失活的線蟲，並透過將處理結果與未處理對照的結果進行比較來計算死亡率百分比。化合物8、17、25、35、36、37、44、47、55、56、57、58、61、62、63、64、65、66、67、68、69、70、74以及75在300 ppm的測試中顯示超過70%的死亡率，而在未經處理的檢查中沒有死亡率。Meloidogyne incognita: Test compounds at a concentration of 300 ppm were pipetted into wells of a 24-well microtiter plate, each well containing 500 μL of distilled water and 50 M. incognita larvae. The suspension was shaken slightly to mix the compounds evenly. The coupons were covered with lids and incubated at 25 °C and 90% RH. Dead/inactivated nematodes were counted under the microscope at 48, 72 and 96 hour intervals, and percent mortality was calculated by comparing the results of the treatments to those of the untreated controls. Compounds 8, 17, 25, 35, 36, 37, 44, 47, 55, 56, 57, 58, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 74 and 75 at 300 The ppm test showed more than 70% mortality, while there was no mortality in the untreated inspection.
南方根結線蟲：活體內測試Southern root knot nematode: in vivo testing
小黃瓜植株在含有沙子：土壤：厩肥 (FYM)：椰子油的混合物的育苗盤中以1:1:1:1的比例生長。當黃瓜幼苗十天大時，在微量移液管的幫助下將 1 mL 所需測試濃度的測試化合物施用於土壤中。施用後，以大約2000隻剛孵化的南方根結線蟲的第二階段幼苗接種幼苗。處理過的植物被允許於溫室條件下在27 °C的溫度下生長。施用後15天記錄對癭 (gall)等級的觀察。植物被小心地連根拔起並徹底清洗根部。如Zeck (1971)所述，在0-10級上觀察癭等級，如下所述：Gherkin plants were grown in a 1:1:1:1 ratio in nursery trays containing a mixture of sand:soil:manure (FYM):coconut oil. When the cucumber seedlings are ten days old, apply 1 mL of the test compound of the desired test concentration to the soil with the help of a micropipette. After application, seedlings were inoculated with approximately 2000 newly hatched second stage seedlings of R. incognita. Treated plants were allowed to grow under greenhouse conditions at a temperature of 27 °C. Observations of gall grades were recorded 15 days after application. Plants were carefully uprooted and roots washed thoroughly. Gall scales are observed on a scale of 0-10, as described by Zeck (1971), as follows:
0 = 沒有癭0 = no galls
1 = 非常少量的小癭1 = very few small galls
2 = 很多的小癭2 = Lots of small galls
3 = 很多的小癭，其中有的生長在一起3 = Many small galls, some of which grow together
4 = 很多的小癭以及一些大的癭4 = Lots of small galls and some large galls
5 = 根部的25%嚴重地有癭5 = 25% of roots severely gall
6 = 根部的50%嚴重的有癭6 = 50% of roots severely gall
7 = 根部的75%嚴重地有癭7 = 75% of roots severely gall
8 = 根部不健康但植株仍呈現綠色8 = Unhealthy roots but still green plant
9 = 根部腐爛且植株乾枯9 = Root rot and plant withered
10 = 植株與根部死亡10 = Plant and roots die
化合物3、4、5、6、7、8、9、10、11、12、16、17、18、20、24、25、26、35、36、38、44、47、48、54、55、56、61、63、64、66、67、68、69、70以及75在300 ppm的測試中，記錄的癭等級低於3，在未處理的檢查中存在大量癭（高達8）。Compounds 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 16, 17, 18, 20, 24, 25, 26, 35, 36, 38, 44, 47, 48, 54, 55 , 56, 61, 63, 64, 66, 67, 68, 69, 70, and 75 recorded gall ratings below 3 in the 300 ppm test, with a high number of galls (up to 8) present in the untreated inspection.
此外，表A表示本發明的化合物與先前技術中已知的化合物相比的有效性的結果。
已經參照某些較佳態樣描述本發明，從說明書考慮，其他態樣對於熟習該項技術者將變得顯而易見。對於熟習該項技術者來說顯而易見的是：在不脫離本發明的範圍的情況下，可對材料和方法實施許多修改。The present invention has been described with reference to certain preferred aspects, other aspects will become apparent to those skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications can be made to the materials and methods without departing from the scope of the invention.
Claims (18)
Applications Claiming Priority (2)
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2021
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- 2021-09-25 WO PCT/IB2021/058748 patent/WO2022064453A1/en active Application Filing
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| Publication number | Publication date |
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| AR123594A1 (en) | 2022-12-21 |
| WO2022064453A1 (en) | 2022-03-31 |
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