TW202146397A - Azinyl azole compound and pest control agent - Google Patents
Azinyl azole compound and pest control agent Download PDFInfo
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—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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- A—HUMAN NECESSITIES
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- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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Abstract
Description
本發明是有關於一種吖嗪基唑化合物及有害生物防治劑。更詳細而言,本發明是有關於一種具有優異的殺蟲活性及/或殺蟎活性、安全性優異且工業上可有利地合成的吖嗪基唑化合物、以及含有其作為有效成分的有害生物防治劑。 本申請案基於2020年3月4日在日本提出申請的日本專利特願2020-037098號而主張優先權,並將其內容引用至本申請案中。The present invention relates to an azinylazole compound and a pest control agent. More specifically, the present invention relates to an azinylazole compound having excellent insecticidal activity and/or acaricidal activity, excellent safety, and industrially advantageously synthesizable, and harmful organisms containing the same as an active ingredient control agent. This application claims priority based on Japanese Patent Application No. 2020-037098 for which it applied in Japan on March 4, 2020, and the content is incorporated herein by reference.
提出有多種具有殺蟲/殺蟎活性的化合物。為了將此種化合物用作農藥,要求不僅效力足夠高,而且不易產生藥劑抗性、不產生對植物的藥害或土壤污染、對家畜或魚類等的毒性低等。Various compounds have been proposed with insecticidal/acaricidal activity. In order to use such a compound as a pesticide, it is required not only to have a sufficiently high efficacy, but also to be less likely to develop chemical resistance, not to cause phytotoxicity to plants or soil pollution, and to have low toxicity to livestock, fish, and the like.
然而,專利文獻1敘述了式(A)等所表示的化合物可用於抑制動物的外部寄生蟲。However, Patent Document 1 describes that compounds represented by formula (A) and the like can be used to inhibit ectoparasites in animals.
[化1] [現有技術文獻] [專利文獻][hua 1] [Prior Art Document] [Patent Document]
[專利文獻1]WO 2017/192385 A1[Patent Document 1] WO 2017/192385 A1
[發明所欲解決之課題] 本發明的課題在於提供一種有害生物防治活性、其中尤其是殺蟲活性及/或殺蟎活性優異、安全性優異且工業上可有利地合成的吖嗪基唑化合物。本發明的另一課題在於提供一種含有吖嗪基唑化合物作為有效成分的有害生物防治劑、殺蟲或殺蟎劑、外部寄生蟲防治劑、或者內部寄生蟲防治或驅除劑。[The problem to be solved by the invention] An object of the present invention is to provide an azinylazole compound which is excellent in pest control activity, especially insecticidal activity and/or acaricidal activity, and which is excellent in safety and which can be advantageously synthesized industrially. Another subject of the present invention is to provide a pest control agent, an insecticide or acaricide, an external parasite control agent, or an internal parasite control or expelling agent containing an azinylazole compound as an active ingredient.
[解決課題之手段] 為解決所述課題而進行了研究,結果完成了包含以下形態的本發明。[Means of Solving Problems] As a result of studies to solve the above-mentioned problems, the present invention including the following aspects has been completed.
〔1〕 一種化合物或其鹽,所述化合物由式(I)表示。[1] A compound represented by formula (I) or a salt thereof.
[化2] [hua 2]
式(I)中, X表示鹵基、經取代或未經取代的C1~6烷基、羥基、經取代或未經取代的C1~6烷氧基、經取代或未經取代的C1~6烷硫基、經取代或未經取代的C1~6烷基亞磺醯基、經取代或未經取代的C1~6烷基磺醯基、經取代或未經取代的C3~6環烷基、經取代或未經取代的C3~6環烷氧基、經取代或未經取代的C3~6環烷硫基、經取代或未經取代的C3~6環烷基亞磺醯基、經取代或未經取代的C3~6環烷基磺醯基、硝基或氰基; 或者,X表示經取代或未經取代的C2~6炔基; n表示X的數量且為0~5的任一整數,當n為2以上時,X相互可相同,亦可不同, R1 表示氫原子、或者經取代或未經取代的C1~6烷基, R2 表示氫原子、或者經取代或未經取代的C1~6烷基, R3 表示氫原子、經取代或未經取代的C1~6烷基、經取代或未經取代的C1~6烷基羰基、或者經取代或未經取代的C1~6烷氧基羰基, Y1 表示氮原子或CRa 所表示的基, Y2 表示氮原子或CRa 所表示的基, Ra 分別獨立地表示氫原子、鹵基、或者經取代或未經取代的C1~6烷基, Q表示經取代或未經取代的6員雜芳基。In formula (I), X represents halogen, substituted or unsubstituted C1-6 alkyl, hydroxy, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 Alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkylsulfonyl, substituted or unsubstituted C3-6 cycloalkyl , substituted or unsubstituted C3-6 cycloalkoxy, substituted or unsubstituted C3-6 cycloalkylthio, substituted or unsubstituted C3-6 cycloalkylsulfinyl, substituted or unsubstituted C3-6 cycloalkylsulfonyl, nitro or cyano group; or, X represents substituted or unsubstituted C2-6 alkynyl; n represents the number of X and is 0-5 Any integer, when n is 2 or more, X may be the same or different from each other, R 1 represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group, R 2 represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group Unsubstituted C1-6 alkyl, R 3 represents a hydrogen atom, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 alkylcarbonyl, or substituted or unsubstituted C1-6 alkoxycarbonyl group, Y 1 represents a nitrogen atom or a group represented by CR a, Y 2 represents a nitrogen atom or a group represented by CR a, R a independently represents a hydrogen atom, a halogen group, or a substituted group or an unsubstituted C1-6 alkyl group, Q represents a substituted or unsubstituted 6-membered heteroaryl group.
〔2〕 如〔1〕所述的化合物或其鹽,其中,Q為經取代或未經取代的吡啶基、或者經取代或未經取代的嘧啶基。 〔3〕 一種有害生物防治劑,含有選自如〔1〕或〔2〕所述的化合物或其鹽中的至少一種作為有效成分。 〔4〕 一種殺蟲或殺蟎劑,含有選自如〔1〕或〔2〕所述的化合物或其鹽中的至少一種作為有效成分。 〔5〕 一種外部寄生蟲防治劑,含有選自如〔1〕或〔2〕所述的化合物或其鹽中的至少一種作為有效成分。 〔6〕 一種內部寄生蟲防治或驅除劑,含有選自如〔1〕或〔2〕所述的化合物或其鹽中的至少一種作為有效成分。[2] The compound or salt thereof according to [1], wherein Q is a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted pyrimidinyl group. [3] A pest control agent containing, as an active ingredient, at least one selected from the compounds described in [1] or [2] or salts thereof. [4] An insecticide or acaricide containing, as an active ingredient, at least one selected from the compounds described in [1] or [2] or salts thereof. [5] An ectoparasite control agent containing, as an active ingredient, at least one selected from the compounds described in [1] or [2] or salts thereof. [6] An internal parasite control or expelling agent containing as an active ingredient at least one selected from the compounds described in [1] or [2] or salts thereof.
[發明的效果] 本發明的吖嗪基唑化合物具有防治於農作物或衛生方面成為問題的有害生物的功能。含有本發明的吖嗪基唑化合物的防治劑可以更低的濃度有效地防治有害生物、尤其是農業害蟲及蟎類,進而,可有效地防治有時危害人畜的外部寄生蟲及內部寄生蟲。[Effect of invention] The azinylazole compound of the present invention has a function of controlling harmful organisms that are problematic in terms of crops or hygiene. The control agent containing the azinylazole compound of the present invention can effectively control harmful organisms, especially agricultural pests and mites, at a lower concentration, and further, can effectively control external parasites and internal parasites that sometimes harm humans and animals.
本發明的吖嗪基唑化合物為式(I)所表示的化合物或其鹽。The azinylazole compound of the present invention is a compound represented by formula (I) or a salt thereof.
[化3] [hua 3]
此處,「未經取代」這一用語是指僅為成為母核的基。無「經取代」的記載而僅以成為母核的基的名稱記載時,只要無特別說明,則為「未經取代」的含義。 另一方面,「經取代」這一用語是指成為母核的基的任一氫原子被結構與母核相同或不同的基(取代基)取代。因此,「取代基」是與成為母核的基鍵結的其他基。取代基可為一個,亦可為兩個以上。兩個以上的取代基可相同,亦可不同。 「C1~6」等用語表示成為母核的基的碳原子數為1個~6個等。於該碳原子數中不包含取代基中所存在的碳原子的數量。例如,具有乙氧基作為取代基的丁基分類為C2烷氧基C4烷基。Here, the term "unsubstituted" refers to a group that serves only as a parent nucleus. When there is no description of "substituted" and only the name of the group that becomes the parent nucleus is described, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom of the group that becomes the parent nucleus is substituted with a group (substituent) having the same or different structure as that of the parent nucleus. Therefore, the "substituent group" is another group bonded to the group that becomes the parent nucleus. The substituent may be one or two or more. Two or more substituents may be the same or different. Terms such as "C1 to 6" indicate that the number of carbon atoms of the group serving as the parent nucleus is 1 to 6, or the like. The number of carbon atoms present in the substituent is not included in the number of carbon atoms. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
「取代基」只要是化學上容許並具有本發明的效果,則並無特別限制。以下例示可成為「取代基」的基。 甲基、乙基、正丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基等C1~6烷基; 乙烯基、1-丙烯基、2-丙烯基(烯丙基)、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基等C2~6烯基; 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-丙炔基等C2~6炔基;The "substituent" is not particularly limited as long as it is chemically acceptable and has the effects of the present invention. Groups that can be "substituents" are exemplified below. Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl and other C1-6 alkyl groups; vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl -C2-6 alkenyl such as 2-propenyl; C2-6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl;
環丙基、環丁基、環戊基、環己基等C3~6環烷基; 苯基、萘基; 苄基、苯乙基; 3員~6員雜環基; 3員~6員雜環基C1~6烷基;C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; Phenyl, naphthyl; benzyl, phenethyl; 3- to 6-membered heterocyclic group; 3- to 6-membered heterocyclyl C1-6 alkyl;
羥基; 甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基; 乙烯氧基、烯丙氧基、丙烯氧基、丁烯氧基等C2~6烯氧基; 乙炔氧基、炔丙氧基等C2~6炔氧基; 苯氧基、萘氧基; 苄氧基、苯乙氧基等苯基C1~6烷氧基; 噻唑氧基、吡啶氧基等5員~6員雜芳氧基; 噻唑基甲氧基、吡啶基甲氧基等5員~6員雜芳基C1~6烷氧基;hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, third butoxy; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propyleneoxy, butenyloxy; C2-6 alkynyloxy groups such as ethynyloxy, propargyloxy; Phenoxy, naphthoxy; Benzyloxy, phenethoxy and other phenyl C1-6 alkoxy; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy, pyridyloxy; 5- to 6-membered heteroaryl C1-6 alkoxy groups such as thiazolylmethoxy and pyridylmethoxy;
甲醯基; 乙醯基、丙醯基等C1~6烷基羰基; 甲醯氧基; 乙醯氧基、丙醯氧基等C1~6烷基羰氧基; 苯甲醯基; 甲氧基羰基、乙氧基羰基、正丙氧基羰基、異丙氧基羰基、正丁氧基羰基、第三丁氧基羰基等C1~6烷氧基羰基; 甲氧基羰氧基、乙氧基羰氧基、正丙氧基羰氧基、異丙氧基羰氧基、正丁氧基羰氧基、第三丁氧基羰氧基等C1~6烷氧基羰氧基; 羧基;carboxyl; C1-6 alkyl carbonyl groups such as acetyl and propionyl; methyloxy; C1-6 alkylcarbonyloxy groups such as acetyloxy, propionyloxy; benzyl; C1-6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and tert-butoxycarbonyl; Methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, isopropoxycarbonyloxy, n-butoxycarbonyloxy, tert-butoxycarbonyloxy, etc. C1-6 alkoxycarbonyloxy; carboxyl;
氟基、氯基、溴基、碘基等鹵基; 氯甲基、氯乙基、三氟甲基、1,2-二氯正丙基、1-氟正丁基等C1~6鹵代烷基; 2-氯-1-丙烯基、2-氟-1-丁烯基等C2~6鹵代烯基; 4,4-二氯-1-丁炔基、4-氟-1-戊炔基、5-溴-2-戊炔基等C2~6鹵代炔基; 三氟甲氧基、2-氯正丙氧基、2,3-二氯丁氧基等C1~6鹵代烷氧基; 2-氯丙烯氧基、3-溴丁烯氧基等C2~6鹵代烯氧基; 氯乙醯基、三氟乙醯基、三氯乙醯基等C1~6鹵代烷基羰基;Halogen groups such as fluoro, chloro, bromo, iodo, etc.; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl; 2-chloro-1-propenyl, 2-fluoro-1-butenyl and other C2-6 haloalkenyl; 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, 5-bromo-2-pentynyl and other C2-6 haloalkynyl; C1-6 halogenated alkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, 2,3-dichlorobutoxy; C2-6 haloalkenyloxy such as 2-chloropropenyloxy, 3-bromobutenyloxy; C1-6 haloalkylcarbonyl groups such as chloroacetyl, trifluoroacetyl, and trichloroacetyl;
胺基; 甲基胺基、二甲基胺基、二乙基胺基等C1~6烷基取代胺基; 苯胺基等苯基胺基; 苄基胺基、苯乙基胺基等苯基C1~6烷基胺基; 甲醯基胺基; 乙醯基胺基、丙醯基胺基、丁醯基胺基、異丙基羰基胺基等C1~6烷基羰基胺基; 甲氧基羰基胺基、乙氧基羰基胺基、正丙氧基羰基胺基、異丙氧基羰基胺基等C1~6烷氧基羰基胺基; 胺甲醯基、二甲基胺基羰基、苯基胺基羰基、N-苯基-N-甲基胺基羰基等未經取代或具有取代基的胺基羰基; 亞胺基甲基、(1-亞胺基)乙基、(1-亞胺基)正丙基等亞胺基C1~6烷基; N-羥基-亞胺基甲基、(1-(N-羥基)-亞胺基)乙基、(1-(N-羥基)-亞胺基)丙基、N-甲氧基-亞胺基甲基、(1-(N-甲氧基)-亞胺基)乙基等經取代或未經取代的N-羥基亞胺基C1~6烷基; 胺基羰氧基; 乙基胺基羰氧基、二甲基胺基羰氧基等C1~6烷基取代胺基羰氧基;amine group; C1-6 alkyl substituted amino groups such as methylamino, dimethylamino, diethylamino, etc.; Phenylamino such as aniline; Benzylamino, phenethylamino and other phenyl C1-6 alkylamino groups; formylamino; C1-6 alkylcarbonylamino groups such as acetylamino, propionylamino, butylamino, isopropylcarbonylamino, etc.; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, isopropoxycarbonylamino, etc.; Aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, N-phenyl-N-methylaminocarbonyl and other unsubstituted or substituted aminocarbonyl; Imino methyl, (1-imino) ethyl, (1-imino) n-propyl and other imino C1-6 alkyl groups; N-Hydroxy-iminomethyl, (1-(N-hydroxy)-imino)ethyl, (1-(N-hydroxy)-imino)propyl, N-methoxy-imine substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as methyl, (1-(N-methoxy)-imino) ethyl, etc.; aminocarbonyloxy; C1-6 alkyl substituted aminocarbonyloxy such as ethylaminocarbonyloxy and dimethylaminocarbonyloxy;
巰基; 甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、第二丁硫基、第三丁硫基等C1~6烷硫基; 三氟甲硫基、2,2,2-三氟乙硫基等C1~6鹵代烷硫基; 苯硫基、萘硫基; 噻唑硫基、吡啶硫基等5員~6員雜芳硫基;Sulfhydryl; C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, second butylthio, and third butylthio; C1-6 halogenated alkylthio groups such as trifluoromethylthio, 2,2,2-trifluoroethylthio; Phenylthio, naphthylthio; 5- to 6-membered heteroarylthio groups such as thiazolylthio, pyridinethio, etc.;
甲基亞磺醯基、乙基亞磺醯基、第三丁基亞磺醯基等C1~6烷基亞磺醯基; 三氟甲基亞磺醯基、2,2,2-三氟乙基亞磺醯基等C1~6鹵代烷基亞磺醯基; 苯基亞磺醯基; 噻唑基亞磺醯基、吡啶基亞磺醯基等5員~6員雜芳基亞磺醯基;C1-6 alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, and tert-butylsulfinyl; C1-6 haloalkylsulfinyl such as trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl; Phenylsulfinyl; 5- to 6-membered heteroarylsulfinyl groups such as thiazolyl sulfinyl, pyridylsulfinyl, etc.;
甲基磺醯基、乙基磺醯基、第三丁基磺醯基等C1~6烷基磺醯基; 三氟甲基磺醯基、2,2,2-三氟乙基磺醯基等C1~6鹵代烷基磺醯基; 苯基磺醯基; 噻唑基磺醯基、吡啶基磺醯基等5員~6員雜芳基磺醯基; 甲基磺醯氧基、乙基磺醯氧基、第三丁基磺醯氧基等C1~6烷基磺醯氧基; 三氟甲基磺醯氧基、2,2,2-三氟乙基磺醯氧基等C1~6鹵代烷基磺醯氧基;Methylsulfonyl, ethylsulfonyl, tert-butylsulfonyl and other C1-6 alkylsulfonyl groups; C1-6 haloalkylsulfonyl such as trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl; Phenylsulfonyl; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl and pyridylsulfonyl; Methylsulfonyloxy, ethylsulfonyloxy, tert-butylsulfonyloxy and other C1-6 alkylsulfonyloxy groups; C1-6 haloalkylsulfonyloxy such as trifluoromethylsulfonyloxy, 2,2,2-trifluoroethylsulfonyloxy;
三甲基矽烷基、三乙基矽烷基、第三丁基二甲基矽烷基等三C1~6烷基取代矽烷基; 三苯基矽烷基; 五氟氫硫基; 氰基;硝基。Tri-C1-6 alkyl substituted silyl groups such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, etc.; triphenylsilyl; pentafluorohydrosulfanyl; cyano group; nitro group.
另外,關於該些「取代基」,所述取代基中的任一氫原子可被不同結構的基取代。作為該情況下的「取代基」,可列舉:C1~6烷基、C1~6鹵代烷基、C1~6烷氧基、C1~6鹵代烷氧基、鹵基、氰基、硝基等。In addition, regarding these "substituents", any hydrogen atom in the substituents may be substituted by groups of different structures. As a "substituent" in this case, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogen group, a cyano group, a nitro group, etc. are mentioned.
另外,所述「3員~6員雜環基」是包含選自由氮原子、氧原子及硫原子所組成的群組中的1個~4個雜原子作為環構成原子的3員環、4員環、5員環或6員環。雜環基可為單環及多環的任一種。關於多環雜環基,只要至少一個環為雜環,則剩餘的環可為飽和脂環、不飽和脂環或芳香環的任一種。作為「3員~6員雜環基」,可列舉:3員~6員飽和雜環基、5員~6員雜芳基、5員~6員部分不飽和雜環基等。In addition, the "3- to 6-membered heterocyclic group" is a 3-membered ring, 4-membered ring including 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms Ring, 5-member or 6-member ring. The heterocyclic group may be either monocyclic or polycyclic. Regarding the polycyclic heterocyclic group, as long as at least one ring is a heterocyclic ring, the remaining rings may be any of saturated alicyclic, unsaturated alicyclic or aromatic rings. Examples of the "3- to 6-membered heterocyclic group" include a 3- to 6-membered saturated heterocyclic group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclic group.
作為3員~6員飽和雜環基,可列舉:氮丙啶基、環氧基、吡咯啶基、四氫呋喃基、四氫噻唑基、哌啶基、哌嗪基、嗎啉基、二氧雜環戊基、二噁烷基等。Examples of the 3- to 6-membered saturated heterocyclic group include aziridinyl, epoxy, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiazolyl, piperidinyl, piperazinyl, morpholinyl, and dioxa Cyclopentyl, dioxanyl, etc.
作為5員雜芳基,可列舉:吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、噁唑基、異噁唑基、噻唑基、異噻唑基、三唑基、噁二唑基、噻二唑基、四唑基等。 作為6員雜芳基,可列舉:吡啶基、吡嗪基、嘧啶基、噠嗪基、三嗪基等。Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, and oxadiazolyl , thiadiazolyl, tetrazolyl, etc. As a 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, etc. are mentioned.
〔X、n〕 X表示鹵基、經取代或未經取代的C1~6烷基、羥基、經取代或未經取代的C1~6烷氧基、經取代或未經取代的C1~6烷硫基、經取代或未經取代的C1~6烷基亞磺醯基、經取代或未經取代的C1~6烷基磺醯基、經取代或未經取代的C3~6環烷基、經取代或未經取代的C3~6環烷氧基、經取代或未經取代的C3~6環烷硫基、經取代或未經取代的C3~6環烷基亞磺醯基、經取代或未經取代的C3~6環烷基磺醯基、硝基或氰基; 或者,X表示經取代或未經取代的C2~6炔基。 n表示X的數量且為0~5的任一整數。當n為2以上時,X相互可相同,亦可不同。[X, n] X represents halogen, substituted or unsubstituted C1-6 alkyl, hydroxy, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkylsulfonyl, substituted or unsubstituted C3-6 cycloalkyl, substituted or unsubstituted Substituted C3-6 cycloalkoxy, substituted or unsubstituted C3-6 cycloalkylthio, substituted or unsubstituted C3-6 cycloalkylsulfinyl, substituted or unsubstituted C3-6 cycloalkylsulfonyl, nitro or cyano group; Alternatively, X represents a substituted or unsubstituted C2-6 alkynyl group. n represents the number of X and is any integer from 0 to 5. When n is 2 or more, X may be the same or different from each other.
作為X中的「鹵基」,可列舉:氟基、氯基、溴基、碘基等。As a "halogen group" in X, a fluorine group, a chlorine group, a bromine group, an iodine group, etc. are mentioned.
X中的「C1~6烷基」可為直鏈,亦可為分支鏈。作為X中的「C1~6烷基」,可列舉:甲基、乙基、正丙基、正丁基、正戊基、正己基、異丙基、異丁基、第二丁基、第三丁基、異戊基、新戊基、2-甲基丁基、異己基等。The "C1-6 alkyl group" in X may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" in X include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec-butyl, th Tributyl, isopentyl, neopentyl, 2-methylbutyl, isohexyl, etc.
作為X中的「C1~6烷氧基」,可列舉:甲氧基、乙氧基、正丙氧基、正丁氧基、正戊氧基、正己氧基、異丙氧基、異丁氧基、第二丁氧基、第三丁氧基、異己氧基等。Examples of "C1-6 alkoxy" in X include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexyloxy, isopropoxy, isobutoxy oxy, second butoxy, third butoxy, isohexyloxy and the like.
X中的「C1~6烷硫基」可列舉:甲硫基、乙硫基、正丙硫基、正丁硫基、正戊硫基、正己硫基、異丙硫基等。The "C1-6 alkylthio group" in X includes methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, isopropylthio and the like.
作為X中的「C1~6烷基亞磺醯基」,可列舉:甲基亞磺醯基、乙基亞磺醯基、第三丁基亞磺醯基等。As "C1-6 alkylsulfinyl group" in X, methylsulfinyl group, ethylsulfinyl group, tert-butylsulfinyl group, etc. are mentioned.
作為X中的「C1~6烷基磺醯基」,可列舉:甲基磺醯基、乙基磺醯基、第三丁基磺醯基等。As "C1-6 alkylsulfonyl group" in X, methylsulfonyl group, ethylsulfonyl group, tert-butylsulfonyl group, etc. are mentioned.
作為X中的「C1~6烷基」、「C1~6烷氧基」、「C1~6烷硫基」、「C1~6烷基亞磺醯基」或「C1~6烷基磺醯基」上的取代基,較佳為:氟基、氯基、溴基、碘基等鹵基;羥基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基;2-氯正丙氧基、2,3-二氯丁氧基、三氟甲氧基等C1~6鹵代烷氧基;苯基;4-氯苯基、4-三氟甲基苯基、4-三氟甲氧基苯基等「被鹵基、C1~6鹵代烷基或C1~6鹵代烷氧基取代的苯基」;或氰基。As "C1-6 alkyl", "C1-6 alkoxy", "C1-6 alkylthio", "C1-6 alkylsulfinyl" or "C1-6 alkylsulfonyl" in X The substituents on the "group" are preferably: fluoro, chloro, bromo, iodo and other halogen groups; hydroxy; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy , C1-6 alkoxy such as second butoxy, isobutoxy, third butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy and other C1 ~6 haloalkoxy; phenyl; 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. substituted phenyl"; or cyano.
作為X中的「C3~6環烷基」,可列舉:環丙基、環丁基、環戊基、環己基等。 作為X中的「C3~6環烷氧基」,可列舉:環丙氧基、環丁氧基、環戊氧基、環己氧基等。As "C3-6 cycloalkyl group" in X, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned. As "C3-6 cycloalkoxy group" in X, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, etc. are mentioned.
作為X中的「C3~6環烷硫基」,可列舉:環丙硫基、環丁硫基、環戊硫基、環己硫基等。 作為X中的「C3~6環烷基亞磺醯基」,可列舉:環丙基亞磺醯基、環丁基亞磺醯基、環戊基亞磺醯基、環己基亞磺醯基等。 作為X中的「C3~6環烷基磺醯基」,可列舉:環丙基磺醯基、環丁基磺醯基、環戊基磺醯基、環己基磺醯基等。As "C3-6 cycloalkylthio group" in X, a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, etc. are mentioned. Examples of "C3-6 cycloalkylsulfinyl" in X include cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, and cyclohexylsulfinyl Wait. As "C3-6 cycloalkylsulfonyl group" in X, cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group, etc. are mentioned.
作為X中的「C3~6環烷基」、「C3~6環烷氧基」、「C3~6環烷硫基」、「C3~6環烷基亞磺醯基」或「C3~6環烷基磺醯基」上的取代基,較佳為:氟基、氯基、溴基、碘基等鹵基;甲基、乙基、正丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基等C1~6烷基;氯甲基、氯乙基、三氟甲基、1,2-二氯正丙基、1-氟正丁基等C1~6鹵代烷基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基;2-氯正丙氧基、2,3-二氯丁氧基、三氟甲氧基等C1~6鹵代烷氧基;或氰基。As "C3-6cycloalkyl", "C3-6cycloalkoxy", "C3-6cycloalkylthio", "C3-6cycloalkylsulfinyl" or "C3-6cycloalkylsulfinyl" in X The substituents on the cycloalkylsulfonyl group are preferably: fluoro, chloro, bromo, iodo and other halogens; methyl, ethyl, n-propyl, isopropyl, n-butyl, Dibutyl, isobutyl, tert-butyl, n-pentyl, n-hexyl and other C1-6 alkyl groups; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1 -C1-6 haloalkyl such as fluoro-n-butyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, third butoxy C1-6 alkoxy groups such as radicals; C1-6 halogenated alkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy, etc.; or cyano groups.
於本發明中,作為X,較佳為鹵基、鹵基取代或未經取代的C1~6烷基、鹵基取代或未經取代的C1~6烷氧基、或者氰基,較佳為鹵基、鹵基取代C1~6烷基、鹵基取代C1~6烷氧基或氰基。In the present invention, X is preferably a halogen group, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, or a cyano group, preferably Halogen, halogen-substituted C1-6 alkyl, halogen-substituted C1-6 alkoxy or cyano.
作為X中的「鹵基取代的C1~6烷基」,可列舉:二氟甲基、三氟甲基、2,2,2-三氟乙基、2,2,2,1,1-五氟乙基等。 作為X中的「鹵基取代的C1~6烷氧基」,可列舉:二氟甲氧基、三氟甲氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2,2,1,1-四氟乙氧基、2,2,2,1,1-五氟乙氧基等。Examples of the "halo-substituted C1-6 alkyl group" in X include difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2,2,1,1- Pentafluoroethyl, etc. Examples of the "halo-substituted C1-6 alkoxy group" in X include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro Ethoxy, 2,2,1,1-tetrafluoroethoxy, 2,2,2,1,1-pentafluoroethoxy, etc.
作為X中的「C2~6炔基」,可列舉: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-丙炔基等,較佳為乙炔基。Examples of "C2-6 alkynyl" in X include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-butynyl Methyl-2-propynyl and the like, preferably ethynyl.
作為X中的「C2~6炔基」上的取代基,較佳為:氟基、氯基、溴基、碘基等鹵基;羥基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基;2-氯正丙氧基、2,3-二氯丁氧基、三氟甲氧基等C1~6鹵代烷氧基;苯基;4-氯苯基、4-三氟甲基苯基、4-三氟甲氧基苯基等「被鹵基、C1~6鹵代烷基或C1~6鹵代烷氧基取代的苯基」;氰基;或三C1~6烷基取代矽烷基,更佳為三C1~6烷基取代矽烷基,更佳為三甲基取代矽烷基。As the substituent on the "C2-6 alkynyl" in X, preferred are halogen groups such as fluoro, chloro, bromo, iodo, etc.; hydroxy; methoxy, ethoxy, n-propoxy, C1-6 alkoxy such as isopropoxy, n-butoxy, second butoxy, isobutoxy, third butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy C1-6 halogenated alkoxy groups such as phenyl, trifluoromethoxy, etc.; phenyl; 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. 6 haloalkyl or C1-6 haloalkoxy substituted phenyl"; cyano group; or tri-C1-6 alkyl substituted silyl group, more preferably tri-C1-6 alkyl substituted silyl group, more preferably trimethyl substituted Silane group.
〔R1 、R2 、R3 〕 R1 表示氫原子、或者經取代或未經取代的C1~6烷基,R2 表示氫原子、或者經取代或未經取代的C1~6烷基。 R3 表示氫原子、經取代或未經取代的C1~6烷基、經取代或未經取代的C1~6烷基羰基、或者經取代或未經取代的C1~6烷氧基羰基,較佳為表示氫原子、或者經取代或未經取代的C1~6烷基。[R 1 , R 2 , R 3 ] R 1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, and R 2 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R 3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group, more Preferably, it represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group.
R1 、R2 及R3 中的「C1~6烷基」的具體例,可列舉與在X中所例示的基相同的基。 作為R3 中的「C1~6烷基羰基」的具體例,可列舉乙醯基、丙醯基等。 作為R3 中的「C1~6烷氧基羰基」的具體例,可列舉:甲氧基羰基、乙氧基羰基、正丙氧基羰基、異丙氧基羰基、正丁氧基羰基、第三丁氧基羰基等。Specific examples of the "C1-6 alkyl group" in R 1 , R 2 and R 3 include the same groups as those exemplified in X. As a specific example of "C1-6 alkylcarbonyl group" in R<3> , an acetyl group, a propionyl group, etc. are mentioned. Specific examples of "C1-6 alkoxycarbonyl" in R 3 include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, Tributoxycarbonyl, etc.
作為R1 、R2 或R3 中的「C1~6烷基」、「C1~6烷基羰基」或「C1~6烷氧基羰基」上的取代基,較佳為:氟基、氯基、溴基、碘基等鹵基;羥基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基;2-氯正丙氧基、2,3-二氯丁氧基、三氟甲氧基等C1~6鹵代烷氧基;苯基;4-氯苯基、4-三氟甲基苯基、4-三氟甲氧基苯基等「被鹵基、C1~6鹵代烷基或C1~6鹵代烷氧基取代的苯基」;或氰基。As the substituent on the "C1-6 alkyl group", "C1-6 alkylcarbonyl group" or "C1-6 alkoxycarbonyl group" in R 1 , R 2 or R 3 , preferred are: fluorine group, chlorine group halogen, bromo, iodo, etc.; hydroxy; methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, second-butoxy, iso-butoxy, third-butoxy C1-6 alkoxy such as oxy; C1-6 haloalkoxy such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy; phenyl; 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. "phenyl substituted by halo, C1-6 haloalkyl or C1-6 haloalkoxy"; or cyano.
除所述以外,作為R3 中的「C1~6烷基」上的取代基,較佳為環丙基、環丁基、環戊基、環己基等C3~6環烷基;乙烯基等C2~6的烯基;或乙炔基。In addition to the above, as the substituent on the "C1-6 alkyl group" in R 3 , preferably C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; vinyl and the like Alkenyl of C2-6; or ethynyl.
〔Y1 、Y2 、Ra 〕 Y1 表示氮原子或CRa 所表示的基,較佳為表示氮原子。 Y2 表示氮原子或CRa 所表示的基。 Ra 分別獨立地表示氫原子、鹵基、或者經取代或未經取代的C1~6烷基,較佳為表示氫原子或未經取代的C1~6烷基。 Ra 中的「鹵基」或「C1~6烷基」的具體例可列舉與在X中所例示的基相同的基。[Y 1 , Y 2 , R a ] Y 1 represents a nitrogen atom or a group represented by CR a, preferably a nitrogen atom. Y 2 represents a nitrogen atom or a group represented by CR a. R a each independently represents a hydrogen atom, a halogen group, or a substituted or unsubstituted C1-6 alkyl group, preferably a hydrogen atom or an unsubstituted C1-6 alkyl group. Specific examples of the "halo group" or "C1-6 alkyl group" in R a include the same groups as those exemplified in X.
〔Q〕 Q表示經取代或未經取代的6員雜芳基。 Q中的「6員雜芳基」是包含芳香性6員環的一價基,所述芳香性6員環包含選自由氮原子、氧原子及硫原子所組成的群組中的1個、2個、3個或4個雜原子作為環的構成原子。當雜原子為2個以上時,該些可相同,亦可不同。作為6員雜芳基,可列舉:吡啶基、吡嗪基、嘧啶基、噠嗪基、三嗪基等。 該些中,Q較佳為吡啶基、嘧啶基或噠嗪基,更佳為吡啶基或嘧啶基。[Q] Q represents a substituted or unsubstituted 6-membered heteroaryl group. The "6-membered heteroaryl group" in Q is a monovalent group including an aromatic 6-membered ring including one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, 2, 3 or 4 heteroatoms serve as ring constituent atoms. When there are two or more hetero atoms, these may be the same or different. As a 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, etc. are mentioned. Among these, Q is preferably pyridyl, pyrimidinyl or pyridazinyl, more preferably pyridyl or pyrimidinyl.
作為Q中的「6員雜芳基」上的取代基,較佳為:氟基、氯基、溴基、碘基等鹵基;甲基、乙基、正丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基等C1~6烷基;氯甲基、氯乙基、三氟甲基、1,2-二氯正丙基、1-氟正丁基等C1~6鹵代烷基;羥基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基;2-氯正丙氧基、2,3-二氯丁氧基、三氟甲氧基等C1~6鹵代烷氧基;苯基;4-氯苯基、4-三氟甲基苯基、4-三氟甲氧基苯基等「被鹵基、C1~6鹵代烷基或C1~6鹵代烷氧基取代的苯基」;或氰基,更佳為鹵基、C1~6烷基、C1~6鹵代烷基或氰基。As the substituent on the "6-membered heteroaryl group" in Q, preferred are halogen groups such as fluoro, chloro, bromo, iodo; methyl, ethyl, n-propyl, isopropyl, n-propyl, etc. C1-6 alkyl groups such as butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n- Propyl, 1-fluoro-n-butyl and other C1-6 haloalkyl; hydroxyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy C1-6 alkoxy, such as tertiary butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy and other C1-6 haloalkoxy; phenyl; 4 -Chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. "phenyl substituted by halo, C1-6 haloalkyl or C1-6 haloalkoxy"; or cyano , more preferably a halogen group, a C1-6 alkyl group, a C1-6 haloalkyl group or a cyano group.
本發明的吖嗪基唑化合物不受其製造方法特別限定。例如,本發明的吖嗪基唑化合物(以下,有時稱為「本發明化合物」)可使用公知的反應並按照實施例等中所記載的程序來獲得。除實施例等中所記載的方法以外,亦可藉由利用以下所示的反應流程中所記載的反應來獲得。 (反應流程1) 於以下的反應流程1中示出式(I)所表示的化合物的製備方法的概略。The azinylazole compound of the present invention is not particularly limited by its production method. For example, the azinylazole compound of the present invention (hereinafter, sometimes referred to as the "compound of the present invention") can be obtained according to the procedures described in Examples and the like using a known reaction. In addition to the methods described in Examples and the like, it can also be obtained by utilizing the reactions described in the reaction schemes shown below. (Reaction Scheme 1) The outline of the preparation method of the compound represented by Formula (I) is shown in the following Reaction Scheme 1.
[化4] [hua 4]
式(I)中的記號表示與所述該些相同的含義。式(2)中的記號表示與式(I)中的該些相同的含義。式(3)中的X及n表示與式(I)中的該些相同的含義。Z表示鹵基。 藉由使式(2)的化合物與式(3)的化合物於適當的鹼的存在下反應而可製備式(I)的化合物。作為鹼,較佳為三乙基胺、N,N-二異丙基乙基胺等有機鹼。The symbols in the formula (I) have the same meanings as those described above. The symbols in the formula (2) have the same meanings as those in the formula (I). X and n in formula (3) represent the same meanings as those in formula (I). Z represents a halogen group. Compounds of formula (I) can be prepared by reacting compounds of formula (2) with compounds of formula (3) in the presence of a suitable base. As the base, organic bases such as triethylamine and N,N-diisopropylethylamine are preferable.
(反應流程2) 於以下的反應流程2中示出式(2)所表示的化合物的製備方法的概略。(Reaction Scheme 2) The outline of the preparation method of the compound represented by Formula (2) is shown in the following Reaction Scheme 2.
[化5] [hua 5]
式(4)中的記號表示與式(I)中的該些相同的含義。Z'表示鹵基。式(5)中的R3 表示與式(I)中的R3 相同的含義。 藉由使式(4)的化合物與式(5)的胺化合物反應而可製備式(2)的化合物。The symbols in the formula (4) represent the same meanings as those in the formula (I). Z' represents a halogen group. R 3 in formula (5) has the same meaning as R 3 in formula (I). The compound of formula (2) can be prepared by reacting the compound of formula (4) with the amine compound of formula (5).
(反應流程3) 關於式(4)所表示的化合物中Y1 為氮原子且Y2 為CRa 所表示的基的式(4')所表示的化合物,可利用以下的反應流程3所示的方法來製備。(Reaction Scheme 3) The compound represented by the formula (4') in which Y 1 is a nitrogen atom and Y 2 is a group represented by CR a in the compound represented by the formula (4) can be represented by the following reaction scheme 3. method to prepare.
[化6] [hua 6]
式(4')中的記號表示與式(I)中的該些相同的含義,Z'表示鹵基。式(6)中的記號表示與式(I)中的該些相同的含義,Z'表示鹵基。式(7)中的Ra 表示與式(I)中的Ra 相同的含義,Me表示甲基。式(8)中的Q表示與式(I)中的Q相同的含義。 藉由使式(6)的化合物與式(7)所表示的化合物於加熱條件下縮合,然後去除低沸點物(該情況下為甲醇),於乙酸等有機酸的存在下,與式(8)的化合物於加熱條件下縮合,從而可製備式(4')的化合物。 所述情況下,認為式(6)的化合物與式(7)的化合物的縮合物是以下的式(9)的化合物。式(9)中的記號與所述該些相同。The symbols in the formula (4') have the same meanings as those in the formula (I), and Z' represents a halogen group. The symbols in the formula (6) have the same meanings as those in the formula (I), and Z' represents a halogen group. R a in formula (7) has the same meaning as R a in formula (I), and Me represents a methyl group. Q in formula (8) represents the same meaning as Q in formula (I). By condensing the compound represented by the formula (6) and the compound represented by the formula (7) under heating, and then removing the low boiler (methanol in this case), in the presence of an organic acid such as acetic acid, the compound is combined with the formula (8). ) is condensed under heating conditions, so that the compound of formula (4') can be prepared. In this case, the condensate of the compound of the formula (6) and the compound of the formula (7) is considered to be the compound of the following formula (9). The symbols in the formula (9) are the same as those described above.
[化7] [hua 7]
(反應流程4) 關於式(3)所表示的化合物中喹唑啉環的2位為氫的式(3')所表示的化合物,可利用以下的反應流程4所示的方法來製備。(Reaction Scheme 4) The compound represented by the formula (3') in which the 2-position of the quinazoline ring is hydrogen among the compounds represented by the formula (3) can be produced by the method shown in the following reaction scheme 4.
[化8] [hua 8]
式(3')中的X表示與式(I)中的X相同的含義,m表示0~4的任一整數,Z'表示鹵基。式(10)中的X表示與式(I)中的X相同的含義,m表示0~4的任一整數。 藉由使式(10)的化合物與甲醯胺於加熱條件下縮合,然後與亞硫醯氯等鹵化劑反應,從而可製備式(3')的化合物。X in formula (3') represents the same meaning as X in formula (I), m represents any integer of 0 to 4, and Z' represents a halogen group. X in formula (10) has the same meaning as X in formula (I), and m represents any integer of 0 to 4. The compound of formula (3') can be prepared by condensing the compound of formula (10) with carboxamide under heating, and then reacting with a halogenating agent such as thionyl chloride.
本發明化合物防治影響植物生長的各種農業害蟲及蟎類等有害生物的效果優異。 另外,本發明化合物對作物的藥害少、對魚類或恆溫動物的毒性低,因此為安全性高的物質。因此,作為殺蟲劑或殺蟎劑的有效成分有用。 進而,近年來,於小菜蛾、稻飛蝨、葉蟬、蚜蟲等大量害蟲中,發展出對各種已存藥劑的抗性,產生該些藥劑的效力不足的問題,期待對抗性品系的害蟲亦有效的藥劑。本發明化合物不僅對感受性品系的害蟲顯示出優異的防治效果,而且對各種抗性品系的害蟲以及殺蟎劑抗性品系的蟎類亦顯示出優異的防治效果。The compounds of the present invention are excellent in controlling various agricultural pests and mites and other harmful organisms that affect plant growth. In addition, the compound of the present invention has little phytotoxicity to crops and low toxicity to fish or warm-blooded animals, and thus is a highly safe substance. Therefore, it is useful as an active ingredient of an insecticide or acaricide. Furthermore, in recent years, among a large number of pests such as diamondback moth, rice planthopper, leafhopper, aphids, etc., resistance to various existing chemicals has developed, resulting in the problem of insufficient efficacy of these chemicals. It is expected that the pests of resistant strains will also be effective medicine. The compounds of the present invention exhibit excellent control effects not only against pests of susceptible strains, but also against pests of various resistant strains and mites of acaricide-resistant strains.
本發明化合物防治危害人獸的外部寄生蟲及內部寄生蟲的效果優異。另外,對魚類或恆溫動物的毒性低,因此為安全性高的物質。因此,作為外部寄生蟲及內部寄生蟲的防治劑的有效成分有用。The compounds of the present invention are excellent in preventing and controlling external parasites and internal parasites that harm humans and animals. In addition, the toxicity to fish and warm-blooded animals is low, and thus it is a highly safe substance. Therefore, it is useful as an active ingredient of a control agent for external parasites and internal parasites.
另外,本發明化合物於成為防治對象的生物的整個生長階段顯示出效力,例如對蟎、昆蟲等的卵、若蟲、幼蟲、蛹、成蟲顯示出優異的防治效果。In addition, the compound of the present invention exhibits efficacy in the entire growth stage of the organism to be controlled, for example, exhibits an excellent control effect on eggs, nymphs, larvae, pupa, and adults of mites, insects, and the like.
〔有害生物防治劑、殺蟲或殺蟎劑〕 本發明的有害生物防治劑、或者殺蟲或殺蟎劑含有選自本發明化合物中的至少一種作為有效成分。關於本發明的有害生物防治劑、或者殺蟲或殺蟎劑中所含的本發明化合物的量,只要顯示出對有害生物、農業害蟲或蟎類的防治效果,則並無特別限制。[Pest control agents, insecticides or acaricides] The pest control agent, or insecticide or acaricide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the pest control agent of the present invention, or the insecticide or acaricide is not particularly limited as long as it exhibits a control effect against pests, agricultural pests, or mites.
本發明的有害生物防治劑、或者殺蟲或殺蟎劑較佳為用於穀物類;蔬菜類;根菜類;薯類;花卉類;果樹類;賞葉植物、茶、咖啡、可可等樹木類;牧草類;草皮類;棉等植物。 於對植物施用時,本發明的有害生物防治劑、或者殺蟲或殺蟎劑可用於葉、莖、柄、花、蕾、果實、種子、芽、根、塊莖、塊根、枝條、插枝等任一部位。 另外,本發明的有害生物防治劑、或者殺蟲或殺蟎劑不受所施用的植物的品種特別限制。作為植物的品種,例如可列舉:原種、變種、改良品種、栽培品種、突變體、雜交體、基改生物(Genetically Modified Organism,GMO)等。The pest control agent, or insecticide or acaricide of the present invention is preferably used for cereals; vegetables; root vegetables; potatoes; flowers; fruit trees; ; pasture; turf; cotton and other plants. When applied to plants, the pest control agents, or insecticides or acaricides of the present invention can be used on leaves, stems, stalks, flowers, buds, fruits, seeds, shoots, roots, tubers, roots, branches, cuttings, etc. any part. In addition, the pest control agent, or the insecticide or acaricide of the present invention is not particularly limited by the species of plants to be applied. As a plant species, for example, a stock species, a variety, an improved species, a cultivar, a mutant, a hybrid, a Genetically Modified Organism (GMO), etc. are mentioned.
為了防治各種農業害蟲及蟎類,本發明的有害生物防治劑可用於種子處理、莖葉散布、土壤施用、水面施用等。In order to control various agricultural pests and mites, the pest control agent of the present invention can be used for seed treatment, stem and leaf spreading, soil application, water surface application and the like.
以下示出可利用本發明的有害生物防治劑進行防治的各種農業害蟲及蟎類的具體例。Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.
(1)鱗翅目(Lepidoptera)的蝶或蛾 (a)燈蛾科(Arctiidae)的蛾、例如美國白蛾(Hyphantria cunea)、暗點燈蛾(Lemyra imparilis); (b)稜巢蛾科(Bucculatricidae)的蛾、例如梨角折蛾(Bucculatrix pyrivorella); (c)蛀果蛾科(Carposinidae)的蛾、例如桃蛀果蛾(Carposina sasakii); (d)草螟科(Crambidae)的蛾、例如絹野螟屬(Diaphania spp.)的瓜絹野螟(Diaphania indica)、黃瓜絹野螟(Diaphania nitidalis);例如稈野螟屬(Ostrinia spp.)的亞洲玉米螟(Ostrinia furnacalis)、歐洲玉米螟(Ostrinia nubilalis)、麻田豆稈野螟(Ostrinia scapulalis);以及二化螟(Chilo suppressalis)、稻縱捲葉螟(Cnaphalocrocis medinalis)、桃蛀螟(Conogethes punctiferalis)、西南玉米螟(Diatraea grandiosella)、桑絹絲野螟(Glyphodes pyloalis)、菜心螟(Hellula undalis)、早熟禾擬莖草螟(Parapediasia teterrella); (e)麥蛾科(Gelechiidae)的蛾、例如甘薯麥蛾(Helcystogramma triannulella)、棉紅鈴蟲(Pectinophora gossypiella)、馬鈴薯麥蛾(Phthorimaea operculella)、麥蛾(Sitotroga cerealella); (f)尺蛾科(Geometridae)的蛾、例如大造橋蟲(Ascotis selenaria); (g)細蛾科(Gracillariidae)的蛾、例如茶細蛾(Caloptilia theivora)、柑橘潛葉蛾(Phyllocnistis citrella)、金紋細蛾(Phyllonorycter ringoniella); (h)弄蝶科(Hesperiidae)的蝶、例如稻弄蝶(Parnara guttata); (i)枯葉蛾科(Lasiocampidae)的蛾、例如天幕毛蟲(Malacosoma neustria); (j)毒蛾科(Lymantriidae)的蛾、例如毒蛾屬(Lymantria spp.)的舞毒蛾(Lymantria dispar)、松針毒蛾(Lymantria monacha);其他的茶毒蛾(Euproctis pseudoconspersa)、旋古毒蛾(Orgyia thyellina);(1) Butterflies or moths of the order Lepidoptera (a) moths of the family Arctiidae, such as Hyphantria cunea, Lemyra imparilis; (b) Moths of the family Bucculatricidae, such as Bucculatrix pyrivorella; (c) moths of the family Carposinidae, such as the peach fruit moth (Carposina sasakii); (d) Moths of the family Crambidae, such as Diaphania indica, Diaphania nitidalis of the genus Diaphania spp.; for example, Ostrinia spp. ) of the Asian corn borer (Ostrinia furnacalis), the European corn borer (Ostrinia nubilalis), the hemp field bean stem borer (Ostrinia scapulalis); and the Chilo suppressalis, Cnaphalocrocis medinalis, Peach borer (Conogethes punctiferalis), southwest corn borer (Diatraea grandiosella), mulberry silk borer (Glyphodes pyloalis), cabbage borer (Hellula undalis), bluegrass stalk borer (Parapediasia teterrella); (e) moths of the family Gelechiidae, such as the sweet potato wheat moth (Helcystogramma triannulella), the cotton red bollworm (Pectinophora gossypiella), the potato wheat moth (Phthorimaea operculella), the wheat moth (Sitotroga cerealella); (f) moths of the family Geometridae, such as Ascotis selenaria; (g) moths of the family Gracillariidae, such as Caloptilia theivora, Phyllocnistis citrella, Phyllonorycter ringoniella; (h) butterflies of the family Hesperiidae, such as Parnara guttata; (i) moths of the family Lasiocampidae, such as Malacosoma neustria; (j) Moths of the family Lymantriidae, such as Lymantria dispar, Lymantria monacha of the genus Lymantria spp.; other Euproctis pseudoconspersa, Orgyia thyellina ;
(k)潛蛾科(Lyonetiidae)的蛾、例如潛蛾屬(Lyonetia spp.)的桃潛葉蛾(Lyonetia clerkella)、銀紋潛葉蛾(Lyonetia prunifoliella malinella); (l)夜蛾科(Noctuidae)的蛾、例如灰翅夜蛾屬(Spodoptera spp.)的淡劍襲夜蛾(Spodoptera depravata)、南部灰翅夜蛾(Spodoptera eridania)、甜菜夜蛾(Spodoptera exigua)、草地貪夜蛾(Spodoptera frugiperda)、非洲棉葉蟲蛾(Spodoptera littoralis)、斜紋夜蛾(Spodoptera litura);例如丫紋夜蛾屬(Autographa spp.)的漢馬夜蛾(Autographa gamma)、黑點銀紋夜蛾(Autographa nigrisigna);例如地夜蛾屬(Agrotis spp.)的小地老虎(Agrotis ipsilon)、菁夜蛾(Agrotis segetum);例如鈴夜蛾屬(Helicoverpa spp.)的棉鈴蟲(Helicoverpa armigera)、菸夜蛾(Helicoverpa assulta)、穀實夜蛾(Helicoverpa zea);例如實夜蛾屬(Heliothis spp.)的和棉鈴蟲(Heliothis armigera)、菸芽夜蛾(Heliothis virescens);其他的白斑煩夜蛾(Aedia leucomelas)、銀紋夜蛾(Ctenoplusia agnata)、枯葉夜蛾(Eudocima tyrannus)、甘藍夜蛾(Mamestra brassicae)、黏蟲(Mythimna separata)、稻螟蛉(Naranga aenescens)、松小眼夜蛾(Panolis japonica)、疆夜蛾(Peridroma saucia)、大豆尺夜蛾(Pseudoplusia includens)、粉紋夜蛾(Trichoplusia ni); (m)瘤蛾科(Nolidae)的蛾、例如棉斑實蛾(Earias insulana); (n)粉蝶科(Pieridae)的蝶、例如粉蝶屬(Pieris spp.)的大菜粉蝶(Pieris brassicae)、紋白蝶(Pieris rapae crucivora); (o)菜蛾科(Plutellidae)的蛾、例如蔥菜蛾屬(Acrolepiopsis spp.)的蔥菜蛾(Acrolepiopsis sapporensis)、鈴木蔥菜蛾(Acrolepiopsis suzukiella);以及小菜蛾(Plutella xylostella); (p)螟蛾科(Pyralidae)的蛾、例如粉斑螟蛾(Cadra cautella)、南美玉米苗斑螟(Elasmopalpus lignosellus)、豆莢螟(Etiella zinckenella)、大蠟螟(Galleria mellonella); (q)天蛾科(Sphingidae)的蛾、例如菸草天蛾屬(Manduca spp.)的番茄天蛾(Manduca quinquemaculata)、菸草天蛾(Manduca sexta);(k) Moths of the family Lyonetiidae, such as Lyonetia clerkella, Lyonetia prunifoliella malinella of the genus Lyonetia spp.; (l) Moths of the family Noctuidae, such as Spodoptera depravata, Spodoptera eridania, Spodoptera exigua of the genus Spodoptera spp. ), Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; such as Autographa spp. Autographa gamma, Autographa nigrisigna; e.g. Agrotis ipsilon, Agrotis segetum of the genus Agrotis spp.; e.g. cotton bolls of the genus Helicoverpa spp. Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea; e.g. Heliothis spp. and Heliothis armigera, Heliothis virescens ; other Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, armyworm (Mythimna separata), rice borer (Naranga aenescens) , Panolis japonica, Peridroma saucia, Pseudoplusia includens, Trichoplusia ni; (m) moths of the family Nolidae, such as Earias insulana; (n) butterflies of the family Pieridae, such as Pieris brassicae, Pieris rapae crucivora of the genus Pieris spp.; (o) moths of the family Plutellidae, such as Acrolepiopsis sapporensis, Acrolepiopsis suzukiella of the genus Acrolepiopsis spp.; and Plutella xylostella; (p) moths of the family Pyralidae, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella; (q) moths of the family Sphingidae, such as Manduca quinquemaculata, Manduca sexta of the genus Manduca spp.;
(r)展足蛾科(Stathmopodidae)的蛾、例如柿展足蛾(Stathmopoda masinissa); (s)穀蛾科(Tineidae)的蛾、例如衣蛾(Tinea translucens); (t)捲葉蛾科(Tortricidae)的蛾、例如褐帶捲蛾屬(Adoxophyes spp.)的茶小捲葉蛾(Adoxophyes honmai)、蘋果小捲葉蛾(Adoxophyes orana);例如黃捲蛾屬(Archips spp.)的梨黃捲蛾(Archips breviplicanus)、蘋果捲葉蛾(Archips fuscocupreanus);其他的雲杉捲葉蛾(Choristoneura fumiferana)、蘋果小捲蛾(Cydia pomonella)、女貞細捲蛾(Eupoecilia ambiguella)、梨小食心蟲(Grapholitha molesta)、後黃捲葉蛾(Homona magnanima)、大豆食心蟲(Leguminivora glycinivorella)、葡萄花翅小捲蛾(Lobesia botrana)、豆小捲葉蛾(Matsumuraeses phaseoli)、蘋褐捲蛾(Pandemis heparana)、葡萄長須捲葉蛾(Sparganothis pilleriana); (u)巢蛾科(Yponomeutidae)的蛾、例如蘋果銀蛾(Argyresthia conjugella)。(r) moths of the family Stathmopodidae, such as Stathmopoda masinissa; (s) moths of the family Tineidae, for example Tinea translucens; (t) Moths of the family Tortricidae, such as Adoxophyes honmai, Adoxophyes orana of Adoxophyes spp.; for example, of Archips spp. Archips breviplicanus, Archips fuscocupreanus; other Spruce Leaf Rollers (Choristoneura fumiferana), Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta), Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Grape leaf roller (Pandemis heparana) Sparganothis pilleriana); (u) Moths of the family Yponomeutidae, eg Argyresthia conjugella.
(2)纓翅目(Thysanoptera)害蟲 (a)管薊馬科(Phlaeothripidae)的、例如柿管薊馬(Ponticulothrips diospyrosi); (b)薊馬科(Thripidae)的、例如花薊馬屬(Frankliniella spp.)的花薊馬(Frankliniella intonsa)、西花薊馬(Frankliniella occidentalis);例如薊馬屬(Thrips spp.)的棕櫚薊馬(Thrips palmi)、菸薊馬(Thrips tabaci);其他的溫室薊馬(Heliothrips haemorrhoidalis)、茶黃薊馬(Scirtothrips dorsalis)。(2) Thysanoptera pests (a) of the Phlaeothripidae family, such as Ponticulothrips diospyrsi; (b) of the Thripidae family, e.g. Frankliniella intonsa, Frankliniella occidentalis of the genus Frankliniella spp.; e.g. palm of the genus Thrips spp. Thrips palmi, Thrips tabaci; other greenhouse thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis.
(3)半翅目(Hemiptera)的害蟲 (A)古喙亞目(Archaeorrhyncha) (a)飛虱科(Delphacidae)的、例如灰飛虱(Laodelphax striatella)、褐飛虱(Nilaparvata lugens)、甘蔗扁角飛虱(Perkinsiella saccharicida)、白背飛虱(Sogatella furcifera)。(3) Pests of the order Hemiptera (A) Archaeorrhyncha (a) Of the planthopper family (Delphacidae), for example the white-backed planthopper (Laodelphax striatella), the brown planthopper (Nilaparvata lugens), the sugarcane flat-horned planthopper (Perkinsiella saccharicida), the white-backed planthopper (Sogatella furcifera).
(B)盾喙亞目(Clypeorrhyncha) (a)葉蟬科(Cicadellidae)的、例如小綠葉蟬屬(Empoasca spp.)的馬鈴薯小綠葉蟬(Empoasca fabae)、小綠葉蟬(Empoasca nipponica)、小貫小綠葉蟬(Empoasca onukii)、板井小綠葉蟬(Empoasca sakaii);其他的葡萄葉蟬(Arboridia apicalis)、黑胸二室葉蟬(Balclutha saltuella)、二點大葉蟬(Epiacanthus stramineus)、黑額二叉葉蟬(Macrosteles striifrons)、黑尾葉蟬(Nephotettix cinctinceps)。(B) Clypeorrhyncha (a) Potato leafhoppers (Empoasca fabae), Empoasca nipponica, Empoasca onukii, Itai small leafhoppers (Empoasca fabae) of the Cicadellidae family (Empoasca spp.) Green leafhopper (Empoasca sakaii); other grape leafhoppers (Arboridia apicalis), black-breasted leafhoppers (Balclutha saltuella), two-spotted leafhoppers (Epiacanthus stramineus), black-fronted leafhoppers (Macrosteles striifrons), black-tailed leafhoppers Leafhopper (Nephotettix cinctinceps).
(C)異翅亞目(Heteroptera) (a)蛛緣蝽科(Alydidae)的、例如豆緣蝽(Riptortus clavatus); (b)緣蝽科(Coreidae)的、例如稻棘緣蝽(Cletus punctiger)、中稻緣蝽(Leptocorisa chinensis); (c)長蝽科(Lygaeidae)的、例如麥長蝽(Blissus leucopterus)、甘蔗長蝽(Cavelerius saccharivorus)、葫蘆長蝽(Togo hemipterus); (d)盲蝽科(Miridae)的、例如日本跳盲蝽(Halticus insularis)、美洲牧草盲蝽(Lygus lineolaris)、棉盲蝽(Psuedatomoscelis seriatus)、西伯利亞狹盲蝽(Stenodema sibiricum)、赤條纖盲蝽(Stenotus rubrovittatus)、赤須盲蝽(Trigonotylus caelestialium);(C) Heteroptera (a) of the family Alydidae, such as Riptortus clavatus; (b) of the family Coreidae, such as Cletus punctiger, Leptocorisa chinensis; (c) of the Lygaeidae family, such as Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus; (d) of the family Miridae, e.g. Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovitatus, Trigonotylus caelestialium;
(e)蝽科(Pentatomidae)的、例如稻綠蝽屬(Nezara spp.)的黑須稻綠蝽(Nezara antennata)、稻綠蝽(Nezara viridula);例如北二星蝽屬(Eysarcoris spp.)的北二星蝽(Eysarcoris aeneus)、日本二星蝽(Eysarcoris lewisi)、廣二星蝽(Eysarcoris ventralis);其他的斑須蝽(Dolycoris baccarum)、皺紋菜蝽(Eurydema rugosum)、青蝽(Glaucias subpunctatus)、茶翅蝽(Halyomorpha halys)、璧蝽(Piezodorus hybneri)、珀蝽(Plautia crossota)、稻黑蝽(Scotinophora lurida); (f)紅蝽科(Pyrrhocoridae)的、例如棉紅蝽(Dysdercus cingulatus); (g)姬緣蝽科(Rhopalidae)的、例如黃伊緣蝽(Rhopalus msculatus); (h)盾蝽科(Scutelleridae)的、例如麥扁盾蝽(Eurygaster integriceps); (i)網蝽科(Tingidae)的、例如梨冠網蝽(Stephanitis nashi)。(e) of the family Pentatomidae, e.g. Nezara antennata, Nezara viridula of the genus Nezara spp.; e.g. of the genus Eysarcoris spp. Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis; other Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, tea Halyomorpha halys, Piezodorus hybneri, Plautia crossota, Scotinophora lurida; (f) of the family Pyrrhocoridae, for example Dysdercus cingulatus; (g) of the family Rhopalidae, such as Rhopalus msculatus; (h) of the family Scutelleridae, such as Eurygaster integriceps; (i) of the Tingidae family, eg Stephanitis nashi.
(D)胸喙亞目(Sternorrhyncha) (a)球蚜科(Adelgidae)的、例如落葉松球蚜(Adelges laricis); (b)粉虱科(Aleyrodidae)、例如小粉虱屬(Bemisia spp.)的銀葉粉虱(Bemisia argentifolii)、菸粉虱(Bemisia tabaci);其他的黑刺粉虱(Aleurocanthus spiniferus)、柑橘粉虱(Dialeurodes citri)、溫室粉虱(Trialeurodes vaporariorum); (c)蚜科(Aphididae)、例如蚜蟲屬(Aphis spp.)的豆蚜(Aphis craccivora)、甜菜蚜(Aphis fabae)、草螟根蚜(Aphis forbesi)、棉蚜(Aphis gossypii)、蘋蚜(Aphis pomi)、接骨木蚜(Aphis sambuci)、捲葉蟲蚜(Aphis spiraecola);例如縊管蚜屬(Rhopalosiphum spp.)的玉米蚜(Rhopalosiphum maidis)、禾谷縊管蚜(Rhopalosiphum padi);例如西圓尾蚜屬(Dysaphis spp.)的車前圓尾蚜(Dysaphis plantaginea)、居根西圓尾蚜(Dysaphis radicola);例如長管蚜屬(Macrosiphum spp.)的麥長管蚜(Macrosiphum avenae)、馬鈴薯長管蚜(Macrosiphum euphorbiae);例如瘤蚜屬(Myzus spp.)的李瘤蚜(Myzus cerasi)、桃蚜(Myzus persicae)、黃藥子瘤蚜(Myzus varians);其他的豌豆長管蚜(Acyrthosiphon pisum)、茄溝無網蚜(Aulacorthum solani)、李短尾蚜(Brachycaudus helichrysi)、甘藍蚜(Brevicoryne brassicae)、草莓毛管蚜(Chaetosiphon fragaefolii)、桃粉大尾蚜(Hyalopterus pruni)、苦菜超瘤蚜(Hyperomyzus lactucae)、菜縊管蚜(Lipaphis erysimi)、巢菜修尾蚜(Megoura viciae)、麥無網長管蚜(Metopolophium dirhodum)、萵苣蚜(Nasonovia ribis-nigri)、忽布疣蚜(Phorodon humuli)、麥二叉蚜(Schizaphis graminum)、麥長管蚜(Sitobion avenae)、橘二叉蚜(Toxoptera aurantii);(D) Sternorrhyncha (a) of the family Adelgidae, such as Adelges laricis; (b) Aleyrodidae, such as Bemisia argentifolii, Bemisia tabaci of the genus Bemisia spp.; other Aleurocanthus spiniferus, citrus whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum); (c) Aphididae, such as Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis gossypii, Aphis spp. (Aphis pomi), Aphis sambuci, Aphis spiraecola; e.g. Rhopalosiphum maidis, Rhopalosiphum padi of the genus Rhopalosiphum spp.; For example, Dysaphis plantaginea, Dysaphis radicola of the genus Dysaphis spp.; for example, Macrosiphum avenae of the genus Macrosiphum spp., Potato aphid (Macrosiphum euphorbiae); eg Myzus cerasi, Myzus persicae, Myzus varians of the genus Myzus spp.; other Acyrthosiphon pisum), Aulacorthum solani, Brachycaudus helichrysi, Cabbage aphid (Brevicoryne brassicae), Strawberry capillary aphid (Chaetosiphon fragaefolii), Peach powder aphid (Hyalopterus pruni), Bitter cabbage aphid (Hyalopterus pruni) Hyperomyzus lactucae, Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Nasonovia ribis-nigri (Phorodon humuli), Schizaphis graminum, Sitobion avenae, Toxoptera aurantii;
(d)介殼蟲科(Coccidae)的、例如蠟蚧屬(Ceroplastes spp.)的角蠟蚧(Ceroplastes ceriferus)、紅蠟蚧(Ceroplastes rubens); (e)盾蚧科(Diaspididae)的、白盾蚧屬(Pseudaulacaspis spp.)的桑盾蚧(Pseudaulacaspis pentagona)、李白盾蚧(Pseudaulacaspis prunicola);例如矢尖盾蚧屬(Unaspis spp.)的衛矛矢尖盾蚧(Unaspis euonymi)、矢尖盾蚧(Unaspis yanonensis);其他的紅圓蚧(Aonidiella aurantii)、梨圓盾蚧(Comstockaspis perniciosa)、茶單盾蚧(Fiorinia theae)、牡丹網盾蚧(Pseudaonidia paeoniae); (f)綿蚧科(Margarodidae)的、例如草履蚧(Drosicha corpulenta)、吹綿蚧(Icerya purchasi); (g)根瘤蚜科(Phylloxeridae)的、例如葡萄根瘤蚜(Viteus vitifolii); (h)粉蚧科(Pseudococcidae)的、例如臀紋粉蚧屬(Planococcus spp.)的柑橘粉蚧(Planococcus citri)、日本粉蚧(Planococcus kuraunhiae);其他的石蒜綿粉蚧(Phenacoccus solani)、康氏粉蚧(Pseudococcus comstocki); (i)木虱科(Psyllidae)的、例如木虱屬(Psylla spp.)的蘋果木虱(Psylla mali)、梨木虱(Psylla pyrisuga);其他的柑橘木虱(Diaphorina citri)。(d) Ceroplastes ceriferus, Ceroplastes rubens of the family Coccidae, such as Ceroplastes spp.; (e) Pseudaulacaspis pentagona (Pseudaulacaspis pentagona), Pseudaulacaspis prunicola (Pseudaulacaspis prunicola) of the family Diaspididae, Pseudaulacaspis spp.; Unaspis euonymi, Unaspis yanonensis; other Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Peony scale (Pseudaonidia paeoniae); (f) of the family Margarodidae, for example, Drosicha corpulenta, Icerya purchasi; (g) of the Phylloxeridae family, such as Viteus vitifolii; (h) Planococcus citri, Japanese mealybugs (Planococcus kuraunhiae) of the family Pseudococcidae, e.g. Planococcus spp.; other Lycoccus solani , Pseudococcus comstocki; (i) Psyllidae (eg Psylla mali, Psylla pyrisuga) of the genus Psyllidae (Psylla spp.); other citrus psyllids (Diaphorina citri).
(4)多食亞目(Polyphaga)的害蟲 (a)竊蟲科(Anobiidae)的、例如菸草甲蟲(Lasioderma serricorne); (b)捲葉象科(Attelabidae)的、例如金綠捲象(Byctiscus betulae)、梨虎象(Rhynchites heros); (c)長蠢科(Bostrichidae)的、例如褐粉蠹(Lyctus brunneus); (d)錐象鼻蟲科(Brentidae)的、例如甘薯蟻象(Cylas formicarius); (e)吉丁蟲科(Buprestidae)的、例如梨窄吉丁(Agrilus sinuatus); (f)天牛科(Cerambycidae)的、例如星天牛(Anoplophora malasiaca)、松褐天牛(Monochamus alternatus)、黃星天牛(Psacothea hilaris)、葡萄虎天牛(Xylotrechus pyrrhoderus); (g)葉甲科(Chrysomelidae)的、例如豆象屬(Bruchus spp.)的豌豆象(Bruchus pisorum)、蠶豆象(Bruchus rufimanus);例如玉米根蟲屬(Diabrotica spp.)的北方玉米根蟲(Diabrotica barberi)、黃瓜甲蟲(Diabrotica undecimpunctata)、玉米根螢葉甲(Diabrotica virgifera);例如條跳甲屬(Phyllotreta spp.)的菁淡足跳甲(Phyllotreta nemorum)、黃曲條跳甲(Phyllotreta striolata);其他的黃守瓜(Aulacophora femoralis)、綠豆象(Callosobruchus chinensis)、甜菜大龜甲(Cassida nebulosa)、甜菜跳甲(Chaetocnema concinna)、馬鈴薯葉甲(Leptinotarsa decemlineata)、水稻負泥蟲(Oulema oryzae)、茄窄胸跳甲(Psylliodes angusticollis);(4) Pests of polyphaga (Polyphaga) (a) of the family Anobiidae, such as the tobacco beetle (Lasioderma serricorne); (b) of the family Attelabidae, such as Byctiscus betulae, Rhynchites heros; (c) of the Bostrichidae family, such as Lyctus brunneus; (d) of the family Brentidae, such as the sweet potato ant weevil (Cylas formicarius); (e) of the Buprestidae family, such as Agrilus sinuatus; (f) of the family Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus; (g) of the Chrysomelidae family, such as Bruchus pisorum, Bruchus rufimanus; for example, Diabrotica spp. barberi), cucumber beetle (Diabrotica undecimpunctata), corn root beetle (Diabrotica virgifera); e.g. Phyllotreta nemorum, Phyllotreta striolata of the genus Phyllotreta spp. ; other yellow squash (Aulacophora femoralis), mung bean elephant (Callosobruchus chinensis), beet beetle (Cassida nebulosa), beet flea beetle (Chaetocnema concinna), potato leaf beetle (Leptinotarsa decemlineata), rice worm (Oulema oryzae) , Psylliodes angusticollis;
(h)瓢蟲科(Coccinellidae)的、例如食植瓢蟲屬(Epilachna spp.)的墨西哥豆瓢蟲(Epilachna varivestis)、茄二十八星瓢蟲(Epilachna vigintioctopunctata); (i)象鼻蟲科(Curculionidae)的、例如花象屬(Anthonomus spp.)的墨西哥棉鈴象蟲(Anthonomus grandis)、梨花象(Anthonomus pomorum);例如象蟲屬(Sitophilus spp.)的穀象(Sitophilus granarius)、玉米象(Sitophilus zeamais);其他的稻象甲(Echinocnemus squameus)、西印度甘薯象甲(Euscepes postfasciatus)、松樹皮象(Hylobius abietis)、苜蓿葉象甲(Hypera postica)、稻水象甲(Lissohoptrus oryzophilus)、葡萄黑象甲(Otiorhynchus sulcatus)、豌豆根瘤象(Sitona lineatus)、尖隱喙象(Sphenophorus venatus); (j)叩甲科(Elateridae)的、例如梳爪叩甲屬(Melanotus spp.)的褐紋金針蟲(Melanotus fortnumi)、櫛叩頭蟲(Melanotus tamsuyensis); (k)露尾甲科(Nitidulidae)的、例如突露尾甲(Epuraea domina); (l)金龜子科(Scarabaeidae)的、例如異麗金龜屬(Anomala spp.)的古銅異麗金龜(Anomala cuprea)、紅銅麗金龜(Anomala rufocuprea);其他的金花金龜(Cetonia aurata)、小綠花金龜(Gametis jucunda)、小栗鰓金龜(Heptophylla picea)、大栗鰓角金龜(Melolontha melolontha)、日本麗金龜(Popillia japonica); (m)小蠹科(Scolytidae)的、例如雲杉八齒小蠹(Ips typographus); (n)隱翅蟲科(Staphylinidae)的、例如毒隱翅蟲(Paederus fuscipes); (o)擬步甲科(Tenebrionidae)的、例如黃粉蟲(Tenebrio molitor)、赤擬穀盜(Tribolium castaneum); (p)穀盜蟲科(Trogossitidae)的、例如大穀盜(Tenebroides mauritanicus)。(h) of the family Coccinellidae, such as Epilachna varivestis, Epilachna vigintioctopunctata of the genus Epilachna spp.; (i) of the family Curculionidae, such as Anthonomus grandis, Anthonomus pomorum of the genus Anthonomus spp.; (Sitophilus granarius), corn weevil (Sitophilus zeamais); other rice weevil (Echinocnemus squameus), West Indian sweet potato weevil (Euscepes postfasciatus), pine bark weevil (Hylobius abietis), cloverleaf weevil (Hypera postica), rice water weevil Beetle (Lissohoptrus oryzophilus), grape black weevil (Otiorhynchus sulcatus), pea root nodule (Sitona lineatus), sharp beak (Sphenophorus venatus); (j) Melanotus fortnumi, Melanotus tamsuyensis of the family Elateridae, such as Melanotus spp.; (k) of the family Nitidulidae, such as Epuraea domina; (l) of the family Scarabaeidae, such as Anomala cuprea (Anomala cuprea), Anomala rufocuprea (Anomala rufocuprea); other beetles (Cetonia aurata), small Green beetles (Gametis jucunda), small chestnut beetles (Heptophylla picea), large chestnut beetles (Melolontha melolontha), Japanese beetles (Popillia japonica); (m) of the family Scolytidae, such as Ips typographus; (n) of the family Staphylinidae, such as Paederus fuscipes; (o) of the family Tenebrionidae, such as Tenebrio molitor, Tribolium castaneum; (p) of the Trogossitidae family, eg Tenebroides mauritanicus.
(5)雙翅目(Diptera)的害蟲 (A)雙翅亞目(Brachycera) (a)潛蠅科(Agromyzidae)的、例如斑潛蠅屬(Liriomyza spp.)的瓜斑潛蠅(Liriomyza bryoniae)、蔥斑潛蠅(Liriomyza chinensis)、美洲斑潛蠅(Liriomyza sativae)、三葉斑潛蠅(Liriomyza trifolii);其他的豌豆彩潛蠅(Chromatomyia horticola)、日本稻潛蠅(Agromyza oryzae); (b)花蠅科(Anthomyiidae)的、例如地種蠅屬(Delia spp.)的灰地種蠅(Delia platura)、甘藍地種蠅(Delia radicum);其他的肖藜泉蠅(Pegomya cunicularia); (c)果蠅科(Drosophilidae)的、例如果蠅屬(Drosophila spp.)的黑腹果蠅(Drosophila melanogaster)、斑翅果蠅(Drosophila suzukii); (d)水蠅科(Ephydridae)的、例如稻潛葉蠅(Hydrellia griseola); (e)莖蠅科(Psilidae)的、例如蘿蔔莖蠅(Psila rosae); (f)實蠅科(Tephritidae)的、例如果實蠅屬(Bactrocera spp.)的瓜實蠅(Bactrocera cucurbitae)、橘小實蠅(Bactrocera dorsalis);例如繞實蠅屬(Rhagoletis spp.)的櫻桃繞實蠅(Rhagoletis cerasi)、蘋果繞實蠅(Rhagoletis pomonella);其他的地中海果蠅(Ceratitis capitata)、橄欖果蠅(Dacus oleae)。(5) Diptera pests (A) Diptera (Brachycera) (a) Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, three of the family Agromyzidae, such as Liriomyza spp. Leaf miner (Liriomyza trifolii); other pea color miners (Chromatomyia horticola), Japanese rice miner (Agromyza oryzae); (b) Delia platura, Delia radicum of the family Anthomyiidae, such as Delia spp.; other Pegomya cunicularia; (c) Drosophila melanogaster, Drosophila suzukii of the family Drosophilidae, such as Drosophila spp.; (d) of the family Ephydridae, such as Hydrellia griseola; (e) of the family Psilidae, such as Psila rosae; (f) of the family Tephritidae, e.g. Bactrocera cucurbitae, Bactrocera dorsalis of the genus Bactrocera spp.; e.g. cherries of the genus Rhagoletis spp. Rhagoletis cerasi, Rhagoletis pomonella; other Mediterranean fruit flies (Ceratitis capitata), olive fruit fly (Dacus oleae).
(B)長角亞目(Nematocera) (a)癭蚊科(Cecidomyiidae)的、例如大豆癭蚊(Asphondylia yushimai)、高粱癭蚊(Contarinia sorghicola)、黑森癭蚊(Mayetiola destructor)、麥紅吸漿蟲(Sitodiplosis mosellana)。(B) Nematocera (a) Of the Cecidomyiidae family, for example Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, Sitodiplosis mosellana.
(6)直翅目(Orthoptera)的害蟲 (a)蝗科(Acrididae)的、例如沙漠蝗屬(Schistocerca spp.)的美洲沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria);其他的澳大利亞災蝗(Chortoicetes terminifera)、摩洛哥戟紋蝗(Dociostaurus maroccanus)、東亞飛蝗(Locusta migratoria)、褐飛蝗(Locustana pardalina)、紅翅蝗(Nomadacris septemfasciata)、小翅稻蝗(Oxya yezoensis); (b)蟋蟀科(Gryllidae)的、例如家蟋蟀(Acheta domestica)、黃臉油葫蘆(Teleogryllus emma); (c)螻蛄科(Gryllotalpidae)的、例如東方螻蛄(Gryllotalpa orientalis); (d)螽斯科(Tettigoniidae)的、例如溫室灶馬(Tachycines asynamorus)。(6) Pests of the order Orthoptera (a) of the family Acrididae, such as Schistocerca americana, Schistocerca gregaria of the genus Schistocerca spp.; other Australian plague locusts (Chortoicetes terminifera), Moroccan locusts Dociosaurus maroccanus), East Asian locust (Locusta migratoria), brown locust (Locustana pardalina), red-winged locust (Nomadacris septemfasciata), small-winged rice locust (Oxya yezoensis); (b) of the family Gryllidae, such as Acheta domestica, Teleogryllus emma; (c) of the family Gryllotalpidae, such as Gryllotalpa orientalis; (d) of the Tettigoniidae, such as the greenhouse stove horse (Tachycines asynamorus).
(7)蟎類(Acari) (A)無氣門目(Astigmata)的粉蟎亞目類(Acaridida) (a)粉蟎科(Acaridae)的蟎、例如根蟎屬(Rhizoglyphus spp.)的刺足根蟎(Rhizoglyphus echinopus)、羅賓根蟎(Rhizoglyphus robini);例如食酪蟎屬(Tyrophagus spp.)的瓜食酪蟎(Tyrophagus neiswanderi)、塵食酪蟎(Tyrophagus perniciosus)、腐食酪蟎(Tyrophagus putrescentiae)、似食酪蟎(Tyrophagus similis);以及粗腳粉蟎(Acarus siro)、橢圓食粉蟎(Aleuroglyphus ovatus)、菌食嗜菌蟎(Mycetoglyphus fungivorus);(7) Mites (Acari) (A) Suborder Acaridida of the order Astigmata (a) Mites of the family Acaridae, eg Rhizoglyphus echinopus, Rhizoglyphus robini of the genera Rhizoglyphus spp.; eg Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; and Acarus siro, Acarus siro (Aleuroglyphus ovatus), Mycetoglyphus fungivorus;
(B)前氣門目(Prostigmata)的輻蟎亞目類(Actinedida) (a)葉蟎科(Tetranychidae)的蟎、例如苔蟎屬(Bryobia spp.)的苜蓿苔蟎(Bryobia praetiosa)、果苔蟎(Bryobia rubrioculus);例如始葉蟎屬(Eotetranychus spp.)的六點始葉蟎(Eotetranychus asiaticus)、北始葉蟎(Eotetranychus boreus)、樸始葉蟎(Eotetranychus celtis)、膝狀始葉蟎(Eotetranychus geniculatus)、柑橘始葉蟎(Eotetranychus kankitus)、李始葉蟎(Eotetranychus pruni)、木始葉蟎(Eotetranychus shii)、史氏始葉蟎(Eotetranychus smithi)、桑始葉蟎(Eotetranychus suginamensis)、彎鉤始葉蟎(Eotetranychus uncatus);例如小爪蟎屬(Oligonychus spp.)的柳杉小爪蟎(Oligonychus hondoensis)、冬青小爪蟎(Oligonychus ilicis)、落葉松小爪蟎(Oligonychus karamatus)、芒果小爪蟎(Oligonychus mangiferus)、甘蔗小爪蟎(Oligonychus orthius)、鱷梨小爪蟎(Oligonychus perseae)、蝦夷雲杉葉蟎(Oligonychus pustulosus)、真梶小爪蟎(Oligonychus shinkajii)、針葉小爪蟎(Oligonychus ununguis);例如全爪蟎屬(Panonychus spp.)的橘全爪蟎(Panonychus citri)、桑全爪蟎(Panonychus mori)、蘋果全爪蟎(Panonychus ulmi);例如葉蟎屬(Tetranychus spp.)的朱砂葉蟎(Tetranychus cinnabarinus)、伊氏葉蟎(Tetranychus evansi)、神澤氏葉蟎(Tetranychus kanzawai)、盧氏葉蟎(Tetranychus ludeni)、柞木葉蟎(Tetranychus quercivorus)、豆葉蟎(Tetranychus phaselus)、二斑葉蟎(Tetranychus urticae)、山楂葉蟎(Tetranychus viennensis);例如缺爪蟎屬(Aponychus spp.)的竹缺爪蟎(Aponychus corpuzae)、梧桐缺爪蟎(Aponychus firmianae);例如綠葉蟎屬(Sasanychus spp.)的綠葉蟎(Sasanychus akitanus)、姬綠葉蟎(Sasanychus pusillus);例如裂爪蟎屬(Shizotetranychus spp.)的嗜竹裂爪蟎(Shizotetranychus celarius)、長肌裂爪蟎(Shizotetranychus longus)、芒草裂爪蟎(Shizotetranychus miscanthi)、勒氏裂爪蟎(Shizotetranychus recki)、原裂爪蟎(Shizotetranychus schizopus);以及酢漿草如葉蟎(Tetranychina harti)、孔雀杜克葉蟎(Tuckerella pavoniformis)、劄幌葉蟎(Yezonychus sapporensis);(B) Actinedida of the order Prostigmata (a) Mites of the family Tetranychidae, such as Bryobia praetiosa, Bryobia rubrioculus of the genus Bryobia spp.; Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus kankitus Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus suginamensis, Eotetranychus uncatus; e.g. Oligonychus spp.) Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; e.g. Panonychus spp. Panonychus citri, Panonychus mori, Panonychus ulmi; for example, Tetranychus cinnabarinus, Tetranychus spp. (Tetranychus evansi), Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Mt. Tetranychus viennensis; e.g. Aponychus corpuzae of the genus Aponychus spp., Aponychus firmianae; e.g. of the genus Sasanychus spp. ( Sasanychus akitanus), Sasanychus pusillus; eg Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanthi of the genus Shizotetranychus spp. ), Shizotetranychus recki, Shizotetranychus schizopus; and sorrels such as Tetranychina harti, Tuckerella pavoniformis, Yezonychus sapporensis );
(b)細須蟎科(Tenuipalpidae)的蟎、例如短須蟎屬(Brevipalpus spp.)的橘短須蟎(Brevipalpus lewisi)、卵形短須蟎(Brevipalpus obovatus)、紫紅短須蟎(Brevipalpus phoenicis)、仙人掌短須蟎(Brevipalpus russulus)、加州短須蟎(brevipalpus californicus);例如細須蟎屬(Tenuipalpus spp.)的太平洋細須蟎(Tenuipalpus pacificus)、柿細須蟎(Tenuipalpus zhizhilashviliae);以及菠蘿長葉蟎(Dolichotetranychus floridanus); (c)癭蟎科(Eriophyidae)的蟎、例如瘤癭蟎屬(Aceria spp.)的柿癭蟎蟎(Aceria diospyri)、無花果瘤癭蟎(Aceria ficus)、日本瘤癭蟎(Aceria japonica)、枸杞瘤癭蟎(Aceria kuko)、石竹瘤癭蟎(Aceria paradianthi)、枸杞葉潛瘤癭蟎(Aceria tiyingi)、鬱金香瘤癭蟎(Aceria tulipae)、結縷草瘤癭蟎(Aceria zoysiea);例如癭蟎屬(Eriophyes spp.)的千葉癭蟎(Eriophyes chibaensis)、梅癭蟎(Eriophyes emarginatae);例如刺皮癭蟎屬(Aculops spp.)的番茄刺皮癭蟎(Aculops lycopersici)、皮氏刺皮癭蟎(Aculops pelekassi);例如刺癭蟎屬(Aculus spp.)的佛氏刺癭蟎(Aculus fockeui)、蘋果刺鏽蟎(Aculus schlechtendali);以及茶橙癭蟎(Acaphylla theavagrans)、茶葉癭蟎(Calacarus carinatus)、葡萄癭蟎(Colomerus vitis)、葡萄葉鏽蟎(Calepitrimerus vitis)、梨上癭蟎(Epitrimerus pyri)、菊花葉鏽蟎(Paraphytoptus kikus)、羅漢松副剛癭蟎(Paracalacarus podocarpi)、柑橘鏽蟎(Phyllocotruta citri); (d)線蟎科(Transonemidae)的蟎、例如跗線蟎屬(Tarsonemus spp.)的雙葉跗線蟎(Tarsonemus bilobatus)、韋氏跗線蟎(Tarsonemus waitei);以及櫻草植食蟎(Phytonemus pallidus)、側多食跗線蟎(Polyphagotarsonemus latus); (e)葉爪蟎科(Penthaleidae)的蟎、例如葉爪蟎屬(Penthaleus spp.)的紅頭葉爪蟎(Penthaleus erythrocephalus)、麥葉爪蟎(Penthaleus major)。(b) Mites of the family Tenuipalpidae, such as Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis of the genus Brevipalpus spp. ), Brevipalpus russulus, Brevipalpus californicus; for example Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae of Tenuipalpus spp.; and Pineapple spider mite (Dolichotetranychus floridanus); (c) mites of the family Eriophyidae, such as Aceria diospyri, Aceria ficus, Aceria japonica of the genus Aceria spp., Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; e.g. Eriophyes chibaensis, Eriophyes emarginatae of the genus Eriophyes spp.; e.g. Aculops lycopersici, Aculops spp. Aculops pelekassi; e.g. Aculus fockeui, Aculus schlechtendali of Aculus spp.; and Acaphylla theavagrans, tea gall Mite (Calacarus carinatus), grape gall mite (Colomerus vitis), grape leaf rust mite (Calepitrimerus vitis), pear gall mite (Epitrimerus pyri), chrysanthemum leaf rust mite (Paraphytoptus kikus), Paracalacarus podocarpi ), citrus rust mite (Phyllocotruta citri); (d) Mites of the family Transonemidae, such as Tarsonemus bilobatus, Tarsonemus waitei of the genus Tarsonemus spp.; and Phytonemus pallidus), Polyphagotarsonemus latus; (e) Mites of the family Penthaleidae, for example Penthaleus erythrocephalus, Penthaleus major of the genus Penthaleus spp.
本發明的有害生物防治劑可與殺菌劑、殺蟲/殺蟎劑、殺線蟲劑、殺土壤害蟲劑等其他有效成分;植物調節劑、增效劑、肥料、土壤改良劑、動物用飼料等混用或併用。 本發明化合物與其他有效成分的組合可期待與殺蟲/殺蟎/殺線蟲活性有關的協同效應。協同效應可依據規定方法並藉由科爾比式(Colby.S.R.;計算除草劑組合的協同效應與拮抗反應(Calculating Synergistic and Antagonistic Responses of Herbicide Combinations);Weeds 15, 20-22頁, 1967)來確認。The pest control agent of the present invention can be combined with other active ingredients such as fungicides, insecticides/acaricides, nematicides, soil insecticides, etc.; plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. mixed or combined. A synergistic effect related to the insecticidal/acaricidal/nematicidal activity can be expected from the combination of the compound of the present invention and other active ingredients. Synergistic effects can be determined according to prescribed methods and by the Colby formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) confirm.
以下示出可與本發明的有害生物防治劑混用或併用的殺蟲/殺蟎劑、殺線蟲劑、殺土壤害蟲劑、驅蟲劑等的具體例。Specific examples of insecticides/acaricides, nematicides, soil insecticides, insect repellents, etc. that can be mixed or used in combination with the pest control agent of the present invention are shown below.
(1)乙醯膽鹼酯酶抑制劑: (a)胺基甲酸酯系:棉鈴威(alanycarb)、涕滅威(aldicarb)、惡蟲威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮碸威(butoxycarboxim)、西維因(carbaryl)、卡巴呋喃(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐蟲脒(formetanate)、呋線威(furathiocarb)、異丙威(isoprocarb)、甲硫威(methiocarb)、滅多蟲(methomyl)、殺線威(oxamyl)、抗蚜威(pirimicarb)、殘殺威(propoxur)、硫雙威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混殺威(trimethacarb)、一氯代二甲苯(Xylene Monochloride,XMC)、滅殺威(xylylcarb)、苯硫威(fenothiocarb)、滅撲威(MIPC)、滅爾虱(MPMC)、速滅威(MTMC)、碸滅威(aldoxycarb)、除害威(allyxycarb)、滅害威(aminocarb)、合殺威(bufencarb)、除線威(cloethocarb)、威百畝(metam-sodium)、猛殺威(promecarb);(1) Acetylcholinesterase inhibitors: (a) Carbamate series: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butocarboxim Butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furosemide Furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb ), thiofanox, triazamate, trimethacarb, Xylene Monochloride (XMC), xylylcarb, fenothiocarb, Procarb (MIPC), mites (MPMC), swiftcarb (MTMC), aldoxycarb (aldoxycarb), allyxycarb, aminocarb, bufencarb, in addition to line Cloethocarb, metam-sodium, promecarb;
(b)有機磷系:高滅磷(acephate)、甲基吡啶磷(azamethiphos)、乙基穀硫磷(azinphos-ethyl)、甲基穀硫磷(azinphos-methyl)、硫線磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒蟲畏(chlorfenvinphos)、氯甲磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蠅毒磷(coumaphos)、殺螟腈(cyanophos)、甲基內吸磷(demeton-S-methyl)、二嗪農(diazinon)、敵敵畏(dichlorvos)/DDVP、百治磷(dicrotophos)、樂果(dimethoate)、甲基毒蟲畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(ethyl-p-nitrophenyl,EPN)、乙硫磷(ethion)、丙線磷(ethoprophos)、胺磺磷(famphur)、苯線磷(fenamiphos)、殺螟硫磷(fenitrothion)、倍硫磷(fenthion)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、菸鹼硫磷(imicyafos)、異柳磷(isofenphos)、水胺硫磷(isocarbophos)、異噁唑磷(isoxathion)、馬拉硫磷(malathion)、滅蚜磷(mecarbam)、甲胺磷(methamidophos)、殺撲磷(methidathion)、速滅磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化樂果(omethoate)、碸吸磷(oxydemeton-methyl)、對硫磷(parathion)、甲基對硫磷(parathion-methyl)、稻豐散(phenthoate)、甲拌磷(phorate)、伏殺硫磷(phosalone)、亞胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、巴胺磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、噠嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、雙硫磷(temephos)、特丁硫磷(terbufos)、司替羅磷(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敵百蟲(trichlorfon)、蚜滅多(vamidothion)、乙基溴硫磷(bromophos-ethyl)、二溴磷(BRP)、三硫磷(carbophenothion)、苯腈膦(cyanofenphos)、甲基內吸磷碸(demeton-S-methyl sulfone)、氯亞胺硫磷(dialifos)、除線磷(dichlofenthion)、蔬果磷(dioxabenzofos)、乙嘧硫磷(etrimfos)、豐索磷(fensulfothion)、吡氟硫磷(flupyrazofos)、地蟲硫磷(fonofos)、安果(formothion)、丁苯硫磷(fosmethilan)、氯唑磷(isazofos)、碘硫磷(jodfenphos)、丙烯磷(methacrifos)、乙基嘧啶磷(pirimiphos-ethyl)、磷蟲威(phosphocarb)、丙蟲磷(propaphos)、發硫磷(prothoate)、硫丙磷(sulprofos)。(b) Organic phosphorus series: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos , chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, Demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, B Disulfoton, ethyl-p-nitrophenyl (EPN), ethion, ethopropos, famphur, fenamiphos, sulfur borer Phosphorus (fenitrothion), fenthion (fenthion), fosthiazate (fosthiazate), heptenophos (heptenophos), nicotine phosphorus (imicyafos), isofenphos (isofenphos), isocarbophos (isocarbophos) Isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, two naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, Propetaphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, s ulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, Trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, methyl systemophos Demeton-S-methyl sulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, fensulfothion, fensulfothion Phosphorus (flupyrazofos), fonofos (fonofos), formothion, fosmethilan, isazofos, jodfenphos, methacrifos, ethylpyrimidine Phosphorus (pirimiphos-ethyl), phosphocarb, propaphos, prothoate, sulprofos.
(2)γ-胺基丁酸(Gamma Aminobutyric Acid,GABA)-操作性氯離子通道拮抗劑:乙醯蟲腈(acetoprole)、氯丹(chlordane)、硫丹(endosulfan)、乙蟲腈(ethiprole)、氟蟲腈(fipronil)、吡嗪氟蟲腈(pyrafluprole)、吡啶氟蟲腈(pyriprole)、毒殺芬(camphechlor)、七氯(heptachlor)、除蟎靈(dienochlor)。 (3)鈉通道調節劑:氟丙菊酯(acrinathrin)、d-順式-反式丙烯菊酯(d-cis-trans allethrin)、d-反式丙烯菊酯(d-trans allethrin)、聯苯菊酯(bifenthrin)、生物丙烯菊酯(bioallethrin)、生物丙烯菊酯S-環戊基異構物(bioallethrin S-cyclopentyl isomer)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(β-cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、λ-三氟氯氰菊酯(λ-cyhalothrin)、γ-三氟氯氰菊酯(γ-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(α-cypermethrin)、β-氯氰菊酯(β-cypermethrin)、θ-氯氰菊酯(θ-cypermethrin)、ζ-氯氰菊酯(ζ-cypermethrin)、苯氰菊酯[(1R)-反式異構物](cyphenothrin[(1R)-trans isomer])、溴氰菊酯(deltamethrin)、烯炔菊酯[(EZ)-(1R)-異構物](Empenthrin[(EZ)-(1R)-Isomer])、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(τ-fluvalinate)、苄蟎醚(halfenprox)、炔咪菊酯(imiprothrin)、噻恩菊酯(kadethrin)、氯菊酯(permethrin)、苯醚菊酯[(1R)-反式異構物](phenothrin[(1R)-trans isomer])、炔丙菊酯(prallethrin)、除蟲菊(pyrethrum)、苄呋菊酯(resmethrin)、氟矽菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯[(1R)-異構物](tetramethrin[(1R)-isomer])、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)、丙烯菊酯(allethrin)、除蟲菊酯(pyrethrins)、除蟲菊酯I(pyrethrin I)、除蟲菊酯II(pyrethrin II)、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin)、生物環呋菊酯(bioethanomethrin)、生物氯菊酯(biopermethrin)、反式氯菊酯(transpermethrin)、五氟苯菊酯(fenfluthrin)、吡氯氰菊酯(fenpirithrin)、溴氟菊酯(flubrocythrinate)、三氟醚菊酯(flufenprox)、甲氧苄氟菊酯(metofluthrin)、丙三苯醚菊酯(protrifenbute)、反滅蟲菊(pyresmethrin)、環戊烯丙菊酯(terallethrin)。(2) Gamma Aminobutyric Acid (GABA)-operating chloride channel antagonists: acetoprole, chlordane, endosulfan, ethiprole ), fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor. (3) Sodium channel modulators: acrithrin, d-cis-trans allethrin, d-trans allethrin, Bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin ), cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin ), α-cypermethrin (α-cypermethrin), β-cypermethrin (β-cypermethrin), θ-cypermethrin (θ-cypermethrin), ζ-cypermethrin (ζ-cypermethrin), cypermethrin [(1R)-trans-iso [(1R)-trans isomer] (cyphenothrin[(1R)-trans isomer]), deltamethrin, enynthrin [(EZ)-(1R)-isomer] (Empenthrin[(EZ)-(1R) -Isomer]), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, fenvalerate Esters (flumethrin), τ-fluvalinate (τ-fluvalinate), halfenprox (halfenprox), imiprothrin (imiprothrin), kadethrin (kadethrin), permethrin (permethrin), phenyl ether Phenothrin [(1R)-trans isomer] (phenothrin[(1R)-trans isomer]), prallethrin, pyrethrum, resmethrin, fluorosilicone silafluofen, tefluthrin, tetramethrin [(1R)-isomer], tralomethrin, tetrafluthrin (transfluthrin), allethrin, pyrethrin ethrins), pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, Biopermethrin, transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, meth Metofluthrin, protrifenbute, pyresmethrin, terallethrin.
(4)菸鹼性乙醯膽鹼受體促效劑:啶蟲脒(acetamiprid)、噻蟲胺(clothianidin)、呋蟲胺(dinotefuran)、吡蟲啉(imidacloprid)、烯啶蟲胺(nitenpyram)、硝蟲噻嗪(nithiazine)、噻蟲啉(thiacloprid)、噻蟲嗪(thiamethoxam)、氟啶蟲胺腈(sulfoxaflor)、菸鹼(nicotine)、氟吡呋喃酮(flupyradifurone)、氟皮魯亞胺(flupyrimine)。 (5)菸鹼性乙醯膽鹼受體異位調節劑:乙基多殺菌素(spinetoram)、多殺菌素(spinosad)。 (6)氯化物通道活化劑:阿維菌素(abamectin)、甲胺基阿維菌素苯甲酸鹽(emamectin-benzoate)、雷皮菌素(lepimectin)、彌拜菌素(milbemectin)、伊維菌素(ivermectin)、塞拉菌素(selamectin)、多拉菌素(doramectin)、依普菌素(eprinomectin)、莫昔克丁(moxidectin)、美貝黴素(milbemycin)、美貝黴素肟(milbemycin oxime)、奈馬菌素(nemadectin)。 (7)保幼激素類似物:烯蟲乙酯(hydroprene)、烯蟲炔酯(kinoprene)、甲氧普林(methoprene)、苯氧威(fenoxycarb)、吡丙醚(pyriproxyfen)、苯蟲醚(diofenolan)、保幼醚(epofenonane)、烯蟲硫酯(triprene)。 (8)其他非特異性抑制劑:甲基溴(methyl bromide)、氯化苦(chloropicrin)、磺醯氟(sulfuryl fluoride)、硼砂(borax)、吐酒石(tartar emetic)。 (9)同翅目選擇性攝食抑制劑:氟啶蟲醯胺(flonicamid)、吡蚜酮(pymetrozine)、新喹唑啉(pyrifluquinazon)。(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, flupirimide (flupyrimine). (5) Ectopic modulators of nicotinic acetylcholine receptors: spinetoram, spinosad. (6) Chloride channel activators: abamectin, emamectin-benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, mebe Milbemycin oxime, nemadectin. (7) Juvenile hormone analogs: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, benzite (diofenolan), epofenolan (epofenonane), methoprene (triprene). (8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar emetic. (9) Homoptera selective feeding inhibitors: flonicamid, pymetrozine, and pyrifluquinazon.
(10)蟎類生育抑制劑:四蟎嗪(clofentezine)、氟蟎嗪(diflovidazin)、噻蟎酮(hexythiazox)、乙蟎唑(etoxazole)。 (11)源自微生物的昆蟲中腸內膜破壞劑:蘇雲金芽孢桿菌以色列亞種(bacillus thuringiensis subsp. Israelensis)、球形芽孢桿菌(bacillus sphaericus)、蘇雲金芽孢桿菌鯰澤亞種(bacillus thuringiensis subsp. aizawai)、蘇雲金芽孢桿菌庫爾斯塔克亞種(bacillus thuringiensis subsp. kurstaki)、蘇雲金芽孢桿菌擬步行亞種(bacillus thuringiensis subsp. tenebrionis)、Bt作物蛋白質、Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1。 (12)線粒體ATP生物合成酵素抑制劑:丁醚脲(diafenthiuron)、三唑錫(azocyclotin)、三環錫(cyhexatin)、苯丁錫(fenbutatin oxide)、克蟎特(propargite)、四氯殺蟎碸(tetradifon)。 (13)氧化磷酸化解偶聯劑:溴蟲腈(chlorfenapyr)、氟蟲胺(sulfluramid)、二硝甲酚(DNOC)、樂殺蟎(binapacryl)、消蟎通(dinobuton)、消蟎普(dinocap)。 (14)菸鹼性乙醯膽鹼受體通道阻斷劑:殺蟲磺(bensultap)、殺螟丹鹽酸鹽(cartap hydrochloride)、沙蠶毒素(nereistoxin)、殺蟲雙(thiosultap-sodium)、殺蟲環(thiocyclam)。 (15)殼多糖合成抑制劑:雙三氟蟲脲(bistrifluron)、氟啶脲(chlorfluazuron)、伏蟲脲(diflubenzuron)、氟環脲(flucycloxuron)、氟蟲脲(flufenoxuron)、氟鈴脲(hexaflumuron)、虱蟎脲(lufenuron)、雙苯氟脲(novaluron)、多氟脲(noviflumuron)、氟苯隆(teflubenzuron)、殺鈴脲(triflumuron)、噻嗪酮(buprofezin)、吡蟲隆(fluazuron)。 (16)雙翅目蛻皮干擾劑:滅蠅胺(cyromazine)。 (17)蛻皮激素受體促效劑:環蟲醯肼(chromafenozide)、氯蟲醯肼(halofenozide)、甲氧蟲醯肼(methoxyfenozide)、蟲醯肼(tebufenozide)。 (18)章魚胺受體促效劑:雙甲脒(amitraz)、得米地曲(demiditraz)、殺蟲脒(chlordimeform)。 (19)線粒體電子傳遞系統複合體III抑制劑:滅蟎醌(acequinocyl)、嘧蟎酯(fluacrypyrim)、伏蟻腙(hydramethylnon)、聯苯肼酯(bifenazate)。 (20)線粒體電子傳遞系統複合體I抑制劑:喹蟎醚(fenazaquin)、唑蟎酯(fenpyroximate)、嘧蟎醚(pyrimidifen)、噠蟎靈(pyridaben)、吡蟎胺(tebufenpyrad)、唑蟲醯胺(tolfenpyrad)、魚藤酮(rotenone)。(10) Mite fertility inhibitors: clofentezine, diflovidazin, hexythiazox, etoxazole. (11) Microorganism-derived insect midgut lining disruptors: Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai ), Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop protein, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab , Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1. (12) Mitochondrial ATP biosynthesis enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetrachloride Mite (tetradifon). (13) Oxidative phosphorylation uncoupling agents: chlorfenapyr, sulfluramid, dinitrocresol (DNOC), binapacryl, dinobuton, dinocap). (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium , Insecticide ring (thiocyclam). (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron ( hexaflumuron), lufenuron, novaluron, polyflumuron, teflubenzuron, triflumuron, buprofezin, imidacloprid ( fluazuron). (16) Diptera molting interfering agent: cyromazine. (17) Ecdysone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide. (18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform. (19) Mitochondrial electron transport system complex III inhibitors: acequinocyl, fluacrypyrim, hydramethylnon, bifenazate. (20) Mitochondrial electron transport system complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, fenpyroximate Amide (tolfenpyrad), rotenone (rotenone).
(21)電位依存性鈉通道阻斷劑:茚蟲威(indoxacarb)、氰氟蟲腙(metaflumizone)。 (22)乙醯基CoA羧化酶抑制劑:螺蟎酯(spirodiclofen)、螺甲蟎酯(spiromesifen)、螺蟲乙酯(spirotetramat)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-2-氧代-1,8-二氮雜螺[4.5]癸-3-烯-4-基乙基碳酸酯(spiropidion)。 (23)線粒體電子傳遞系統複合體IV抑制劑:磷化鋁(aluminium phosphide)、磷化鈣(calcium phosphide)、膦(phosphine)、磷化鋅(zinc phosphide)、氰化物(cyanide)。 (24)線粒體電子傳遞系統複合體II抑制劑:腈吡蟎酯(cyenopyrafen)、丁氟蟎酯(cyflumetofen)、皮福魯不米德(pyflubumide)。 (25)利阿諾定(Ryanodine)受體調節劑:氯蟲醯胺(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)、氟苯蟲醯胺(flubendiamide)、環溴蟲醯胺(cyclaniliprole)、氟氰蟲醯胺(tetraniliprole)。 (26)混合功能氧化酶抑制劑化合物:增效醚(piperonyl butoxide)。 (27)蛛毒素受體作用劑:縮酚酸肽(depsipeptide)、環狀縮酚酸肽(cyclodepsipeptide)、24員環狀縮酚酸肽(24 membered cyclodepsipeptide)、艾莫德賽(emodepside)。 (28)其他藥劑(作用機制未知):3-內-[2-丙氧基-4-(三氟甲基)苯氧基]-9-[5-(三氟甲基)-2-吡啶氧基]-9-氮雜雙環[3.3.1]壬烷(acynonapyr)、印楝素(azadirachtin)、西脫蟎(benzoximate)、新殺蟎(bromopropylate)、滅蟎猛(quinomethionate)、冰晶石(cryolite)、三氯殺蟎醇(dicofol)、啶蟲丙醚(pyridalyl)、苯氯噻唑(benclothiaz)、硫(sulfur)、磺胺蟎酯(amidoflumet)、1,3-二氯丙烯(1,3-dichloropropene)、二氯異丙醚(DCIP)、溴蟎酯(phenisobromolate)、苯蟎特(benzomate)、四聚乙醛(metaldehyde)、乙酯殺蟎醇(chlorobenzilate)、氯噻苯(clothiazoben)、環蟲腈(dicyclanil)、分薩克林(fenoxacrim)、氟硝二苯胺(fentrifanil)、氟蟎噻(flubenzimine)、氟非那嗪(fluphenazine)、棉紅鈴蟲性誘劑(gossyplure)、金龜子性誘劑(japonilure)、惡蟲酮(metoxadiazone)、石油(oil)、油酸鈉、殺蟎好(tetrasul)、苯蟎噻(triarathene)、阿非多皮羅奮(afidopyropen)、氟麥托醌(flometoquin)、丁烯氟蟲腈(flufiprole)、氟噻蟲碸(fluensulfone)、氯氟醚菊酯(meperfluthrin)、四氟醚菊酯(tetramethylfluthrin)、溴代吡咯腈(tralopyril)、甲基新癸醯胺(methylneodecanamide)、及氟雷拉納(fluralaner)、阿弗拉納(afoxolaner)、福萊克斯阿麥阿米德(fluxametamide)、5-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氫異噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯甲腈(CAS:943137-49-3)(5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitrile(CAS:943137-49-3))、溴蟲氟苯雙醯胺(broflanilide)、三氟苯嘧啶(triflumezopyrim)、敵克美施(dicloromezotiaz)、2-[3-(乙基磺醯基)-2-吡啶基]-5-[(三氟甲基)磺醯基]苯並噁唑(oxazosulfyl)、其他的間二醯胺類、N-[3-氯-1-(3-吡啶基)吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫代]丙醯胺(tyclopyrazoflor)。(21) Potential-dependent sodium channel blockers: indoxacarb, metaflumizone. (22) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, 3-(4-chloro-2,6-dimethyl Phenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (spiropidion). (23) Mitochondrial electron transport system complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide. (24) Mitochondrial electron transport system complex II inhibitors: cyenopyrafen, cyflumetofen, pyflubumide. (25) Rianodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, fluorine Cyaniliprole (tetraniliprole). (26) Mixed-function oxidase inhibitor compounds: piperonyl butoxide. (27) Spider toxin receptor agents: depsipeptide, cyclodepsipeptide, 24-membered cyclodepsipeptide, emodepside. (28) Other agents (mechanism of action unknown): 3-endo-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[5-(trifluoromethyl)-2-pyridine Oxy]-9-azabicyclo[3.3.1]nonane (acynonapyr), azadirachtin, benzoximate, bromopropylate, quinomethionate, cryolite (cryolite), dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene , Dichloroisopropyl ether (DCIP), phenisobromolate, benzomate, metaldehyde, chlorobenzilate, clothiazoben, ringworm Dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossyplure, scarabs japonilure, metoxadiazone, oil, sodium oleate, tetrasul, triarathene, afidopyropen, flumetropone ( flometoquin, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, methyl neodecyl Methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl) -5-Trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49 -3) (5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitril e (CAS: 943137-49-3)), broflanilide, triflumezopyrim, dicloromezotiaz, 2-[3-(ethylsulfonyl) -2-Pyridyl]-5-[(trifluoromethyl)sulfonyl]benzoxazole (oxazosulfyl), other metadiamids, N-[3-chloro-1-(3-pyridyl) ) pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propionamide (tyclopyrazoflor).
(29)驅蟲劑: (a)苯並咪唑系:芬苯達唑(fenbendazole)、阿苯達唑(albendazole)、三氯苯達唑(triclabendazole)、奧苯達唑(oxibendazole)、甲苯達唑(mebendazole)、奧芬達唑(oxfendazole)、帕苯達唑(parbendazole)、氟苯達唑(flubendazole)、苯硫胍(febantel)、奈托比胺(netobimin)、托布津(thiophanate)、噻苯咪唑(thiabendazole)、堪苯達唑(cambendazole); (b)水楊苯胺系:氯氰碘柳胺(closantel)、五氯柳胺(oxyclozanide)、碘醚柳胺(rafoxanide)、氯硝柳胺(niclosamide); (c)取代酚系:硝碘酚腈(nitroxinil)、硝硫氰酯(nitroscanate); (d)嘧啶系:噻嘧啶(pyrantel)、莫侖太爾(morantel); (e)咪唑並噻唑系:左旋咪唑(levamisole)、四咪唑(tetramisole); (f)四氫嘧啶系:吡喹酮(praziquantel)、依西太爾(epsiprantel); (g)其他驅蟲藥:環二烯(cyclodiene)、雷雅尼阿(ryania)、氯舒隆(clorsulon)、甲硝噠唑(metronidazole)、得米地曲(demiditraz)、哌嗪(piperazine)、乙胺嗪(diethylcarbamazine)、雙氯酚(dichlorophen)、莫奈太爾(monepantel)、三苯雙脒(tribendimidine)、阿米太爾(amidantel)、硫乙胂胺(thiacetarsamide)、美拉索明(melarsomine)、砷苯醯胺(arsenamide)。(29) Insect repellent: (a) Benzimidazole series: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, orphen oxfendazole, parbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, Cambendazole; (b) Salicylaniline series: closantel, oxyclozanide, rafoxanide, niclosamide; (c) Substituted phenols: nitroxinil, nitroscanate; (d) Pyrimidine series: pyrantel, morantel; (e) Imidazothiazoles: levamisole, tetramisole; (f) tetrahydropyrimidines: praziquantel, epsiprantel; (g) Other anthelmintics: cyclodiene, ryania, clorsulon, metronidazole, demiditraz, piperazine ), diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melamine Melarsomine, arsenamide.
以下示出可與本發明的有害生物防治劑混用或併用的殺菌劑的具體例。 (A)核酸合成代謝抑制劑 (1)RNA聚合酶I抑制劑 苯霜靈(benalaxyl)、精苯霜靈(benalaxyl-M)、呋霜靈(furalaxyl)、甲霜靈(metalaxyl)、精甲霜靈(metalaxyl-M);惡霜靈(oxadixyl);呋醯胺(ofurace)。 (2)腺苷脫胺酶抑制劑 乙嘧酚磺酸酯(bupirimate)、二甲嘧酚(dimethirimol)、乙嘧酚(ethirimol)。 (3)DNA/RNA生物合成抑制劑 惡黴靈(hymexazol)、辛噻酮(octhilinone)。 (4)DNA拓撲異構酶類型II抑制劑 噁喹酸(oxolinic acid)。Specific examples of fungicides that can be used in combination or in combination with the pest control agent of the present invention are shown below. (A) Nucleic acid anabolic inhibitors (1) RNA polymerase I inhibitor benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; furalaxyl Amine (ofurace). (2) Adenosine deaminase inhibitors Bupirimate, Dimethirimol, Ethirimol. (3) DNA/RNA biosynthesis inhibitors Hymexazol, octhilinone. (4) DNA topoisomerase type II inhibitors oxolinic acid.
(B)細胞骨架與動力蛋白質(motor protein)的抑制劑 (1)β-微管蛋白聚合抑制劑 苯菌靈(benomyl)、多菌靈(carbendazim)、麥穗寧(fuberidazole)、噻苯咪唑(thiabendazole)、硫菌靈(thiophanate)、甲基硫菌靈(thiophanate-methyl)、乙黴威(diethofencarb)、苯醯菌胺(zoxamide)、噻唑菌胺(ethaboxam)。 (2)其他抑制劑 戊菌隆(pencycuron);氟吡菌胺(fluopicolide);氰烯菌酯(phenamacril)、苯菌酮(metrafenone)、派瑞芬酮(pyriofenone)。(B) Inhibitors of cytoskeleton and motor proteins (1) β-tubulin polymerization inhibitor Benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, acetocarb ( diethofencarb), zoxamide, ethaboxam. (2) Other inhibitors Pencycuron; fluopicolide; phenamacril, metrafenone, pyriofenone.
(C)呼吸抑制劑 (1)複合體I:NADH氧化還原酵素的抑制劑 氟嘧菌胺(diflumetorim)、唑蟲醯胺(tolfenpyrad)、喹蟎醚(fenazaquin)。 (2)複合體II:琥珀酸脫氫酵素的抑制劑 麥鏽靈(benodanil)、氟醯胺(flutolanil)、滅鏽胺(mepronil);異丙噻菌胺(isofetamid);氟吡菌醯胺(fluopyram);甲呋醯胺(fenfuram);萎鏽靈(carboxin)、氧化萎鏽靈(oxycarboxin);噻呋醯胺(thifluzamide);苯並烯氟菌唑(benzovindiflupyr)、聯苯吡菌胺(bixafen)、氟茚唑菌胺(fluindapyr)、氟唑菌醯胺(fluxapyroxad)、呋吡菌胺(furametpyr)、音皮福魯愛克薩(inpyrfluxam)、吡唑萘菌胺(isopyrazam)、氟唑菌苯胺(penflufen)、吡噻菌胺(penthiopyrad)、氟唑環菌胺(sedaxane);伊索福魯希皮朗(isoflucypram);氟唑菌醯羥胺(pydiflumetofen);啶醯菌胺(boscalid);皮拉基福魯米德(pyraziflumid)。 (3)複合體III:細胞色素bc1(泛醇氧化酵素)Qo部位(cyt b基因)的抑制劑 嘧菌脂(azoxystrobin)、丁香菌酯(coumoxystrobin)、烯肟菌酯(enoxastrobin)、氟菌蟎酯(flufenoxystrobin)、啶氧菌酯(picoxystrobin)、唑菌酯(pyraoxystrobin);曼德斯特洛賓(mandestrobin);唑菌胺酯(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、氯啶菌酯(triclopyricarb);醚菌酯(kresoxim-methyl)、肟菌酯(trifloxystrobin);醚菌胺(dimoxystrobin)、烯肟菌胺(fenaminstrobin)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin);噁唑菌酮(famoxadone);氟嘧菌酯(fluoxastrobin);咪唑菌酮(fenamidone);吡菌苯威(pyribencarb)。 (4)複合體III:泛醌還原酵素Qi部位的抑制劑 氰霜唑(cyazofamid);吲唑磺菌胺(amisulbrom);酚皮科薩米德(fenpicoxamid)。 (5)氧化磷酸化的解偶聯劑 樂殺蟎(binapacryl)、消蟎普(dinocap)、消蟎多(meptyldinocap);氟啶胺(fluazinam)。 (6)氧化磷酸化、ATP合成酵素的抑制劑 三苯基乙酸錫(fentin acetate)、三苯基氯化錫(fentin chloride)、三苯基氫氧化錫(fentin hydroxide)。 (7)ATP輸送的抑制劑 硫矽菌胺(silthiofam)。 (8)複合體III:泛醌還原酵素(Qo部位、標樁菌素鍵合位點)的抑制劑 唑嘧菌胺(ametoctradin)。(C) Respiratory Depressants (1) Complex I: Inhibitor of NADH oxidoreductase Diflumetorim, tolfenpyrad, fenazaquin. (2) Complex II: an inhibitor of succinate dehydrogenase Benodanil, flutolanil, mepronil; isofetamid; fluopyram; fenfuram; Carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluindapyr, fluazole Fluxapyroxad, furametpyr, inpyrfluxam, isopyrazam, penflufen, penthiopyrad , Fluoxafen (sedaxane); Isoflucypram (isoflucypram); Fluoxamethoxamine (pydiflumetofen); (3) Complex III: Inhibitor of cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene) Azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; Mandestrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin ), fenaminstrobin, metminostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; Pyribencarb (pyribencarb). (4) Complex III: an inhibitor of the Qi site of ubiquinone reductase Cyazofamid; Amisulbrom; Fenpicoxamid. (5) Uncouplers of oxidative phosphorylation Music kills mites (binapacryl), eliminates mites (dinocap), eliminates mites and more (meptyldinocap); fluazinam (fluazinam). (6) Inhibitors of oxidative phosphorylation and ATP synthesis enzymes Triphenyl tin acetate (fentin acetate), triphenyl tin chloride (fentin chloride), triphenyl tin hydroxide (fentin hydroxide). (7) Inhibitors of ATP transport Silthiofam. (8) Complex III: Inhibitor of ubiquinone reductase (Qo site, paxillin binding site) Ametoctradin.
(D)胺基酸及蛋白質合成抑制劑 賽普洛(cyprodinil)、嘧菌胺(mepanipyrim)、嘧黴胺(pyrimethanil);滅瘟素(blasticidin-S);春雷黴素(kasugamycin)、春雷黴素鹽酸鹽(kasugamycin hydrochloride)、鏈黴素(streptomycin);土黴素(oxytetracycline)。(D) Inhibitors of amino acid and protein synthesis Cyprodinil, mepanipyrim, pyrimethanil; blasticidin-S; kasugamycin, kasugamycin hydrochloride, streptomycin Streptomycin; oxytetracycline.
(E)訊號傳導抑制劑 喹氧靈(quinoxyfen)、丙氧喹啉(proquinazid);拌種咯(fenpiclonil)、咯菌腈(fludioxonil);乙菌利(chlozolinate)、菌核淨(dimetachlone)、異菌脲(iprodione)、腐黴利(procymidone)、乙烯菌核利(vinclozolin)。(E) Signaling inhibitors quinoxyfen, proquinazid; fenpiclonil, fludioxonil; chlozolinate, dimetachlone, iprodione, Procymidone, vinclozolin.
(F)抑制脂質生物合成或輸送/細胞膜的結構或功能的藥劑 克瘟散(edifenphos)、異稻瘟淨(iprobenfos)、吡菌磷(pyrazophos);稻瘟靈(isoprothiolane)。 聯苯(biphenyl)、地茂散(chloroneb)、氯硝胺(dichloran)、五氯硝基苯(quintozene)、四氯硝基苯(tecnazene)、甲基立枯磷(tolclofos-methyl);土菌靈(etridiazole);碘代丙炔基丁基甲胺酸酯(iodocarb)、霜黴威(propamocarb)、霜黴威鹽酸鹽(propamocarb-hydrochloride)、硫菌威(prothiocarb);游黴素(natamycin);氟噻唑吡乙酮(oxathiapiprolin)。(F) Agents that inhibit lipid biosynthesis or transport/structure or function of cell membranes Gram blast powder (edifenphos), different rice blast net (iprobenfos), pyrazophos (pyrazophos); rice blast spirit (isoprothiolane). Biphenyl, chloroneb, dichloran, quintozene, tecnazene, tolclofos-methyl; soil Etridiazole; iodocarb, propamocarb, propamocarb-hydrochloride, prothiocarb; natamycin ); oxathiapiprolin.
(G)細胞膜的固醇生物合成(的抑制劑) (1)固醇生物合成的C14位的脫甲基酶(erg11/cyp51)的抑制劑 賽福寧(triforine);啶斑肟(pyrifenox)、啶菌噁唑(pyrisoxazole);氯苯嘧啶醇(fenarimol)、氟苯嘧啶醇(nuarimol);抑黴唑(imazalil)、噁咪唑(oxpoconazole)、稻瘟酯(pefurazoate)、咪鮮胺(prochloraz)、氟菌唑(triflumizole);阿紮康唑(azaconazole)、聯苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、環唑醇(cyproconazole)、苯醚甲環唑(difenoconazole)、烯唑醇(diniconazole)、氟環唑(epoxiconazole)、乙環唑(etaconazole)、腈苯唑(fenbuconazole)、氟喹唑(fluquinconazole)、氟矽唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、亞胺唑(imibenconazole)、種菌唑(ipconazole)、葉菌唑(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙環唑(propiconazole)、矽氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、三唑醇(triadimenol)、滅菌唑(triticonazole)、丙硫菌唑(prothioconazole)。 (2)固醇生物合成中的Δ14還原酵素及Δ8→Δ7-異構酶(erg24、erg2)的抑制劑 十二嗎啉(aldimorph)、嗎菌靈(dodemorph)、嗎菌靈乙酸鹽(dodemorph acetate)、丁苯嗎啉(fenpropimorph)、克啉菌(tridemorph);苯鏽啶(fenpropidin)、粉病靈(piperalin);螺環菌胺(spiroxamine)。 (3)固醇生物合成體系的C4位脫甲基化中的3-酮還原酵素(erg27)的抑制劑 環醯菌胺(fenhexamid)、胺苯吡菌酮(fenpyrazamine)。 (4)固醇生物合成體系的角鯊烯環氧酶(erg1)的抑制劑 稗草丹(pyributicarb)、萘替芬(naftifine)、特比萘芬(terbinafine)。(G) Cell membrane sterol biosynthesis (inhibitor) (1) Inhibitor of sterol biosynthesis C14 demethylase (erg11/cyp51) Triforine; pyrifenox, pyrisoxazole; fenarimol, nuarimol; imazalil, oxpoconazole , pefurazoate, prochloraz, triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole ( cyproconazole), difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole (flusilazole), flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole ), propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, Prothioconazole. (2) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) in sterol biosynthesis aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, powdery mildew (piperalin); spiroxamine. (3) Inhibitor of 3-ketoreductase (erg27) in C4 demethylation of sterol biosynthesis system Cyclofenamide (fenhexamid), fenpyrazamine (fenpyrazamine). (4) Inhibitors of squalene epoxidase (erg1) in the sterol biosynthesis system Barnyard grass Dan (pyributicarb), naftifine (naftifine), terbinafine (terbinafine).
(H)細胞壁生物合成的抑制劑 多抗黴素(polyoxins);烯醯嗎啉(dimethomorph)、氟嗎啉(flumorph)、丁吡嗎啉(pyrimorph);苯噻菌胺(benthiavalicarb)、異丙菌胺(iprovalicarb)、纈菌胺(valifenalate);雙炔醯菌胺(mandipropamid)。(H) Inhibitors of cell wall biosynthesis Polyoxins; dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, valactin (valifenalate); mandipropamid.
(I)細胞壁的黑色素合成的抑制劑 四氯苯酞(fthalide);咯喹酮(pyroquilon);三環唑(tricyclazole);環丙醯菌胺(carpropamid)、雙氯氰菌胺(diclocymet)、氰菌胺(fenoxanil);托普洛卡(tolprocarb)。(I) Inhibitors of cell wall melanin synthesis fthalide; pyroquilon; tricyclazole; carpropamid, diclocymet, fenoxanil; toprol card (tolprocarb).
(P)宿主植物的抗性誘導劑 阿拉酸式苯-S-甲基(acibenzolar-S-methyl);烯丙苯噻唑(probenazole);噻醯菌胺(tiadinil)、異噻菌胺(isotianil);海帶多糖(laminarin);大虎杖萃取物(reynoutria sachalinensis extract);蕈狀芽胞桿菌分離株(Bacillus mycoides isopate J);三乙膦酸(fosetyl)、亞磷酸及鹽、三乙膦酸鈣(fosetyl-calcium)、三乙膦酸鈉(fosetyl-sodium)。(P) Resistance inducers of host plants Acibenzolar-S-methyl; probenazole; tiadinil, isotianil; laminarin; Knotweed extract Reynoutria sachalinensis extract; Bacillus mycoides isopate J; triethylphosphonic acid (fosetyl), phosphorous acid and salts, calcium triethylphosphonate (fosetyl-calcium), sodium triethylphosphonate ( fosetyl-sodium).
(U)作用機構不明的藥劑 霜脲氰(cymoxanil);葉枯酞(tecloftalam);咪唑嗪(triazoxide);磺菌胺(flusulfamide);噠菌清(diclomezine);環氟菌胺(cyflufenamid);多果定(dodine)、多果定游離鹼(dodine free base);氟噻唑菌腈(flutianil);嘧菌腙(ferimzone);異丁乙氧喹啉(tebufloquin);皮卡布西(picarbutrazox);井岡黴素(validamycin)。 氟派保林(fluoxapiprolin)、佛利皮考安米德(florylpicoxamid)、氟醚菌醯胺(fluopimomide)衣破福魯酚金(ipflufenoquin)、甲基四吡唑(metyltetraprole)、噠嗪氯甲基(pyridachlometyl)、皮拉皮羅迫音(pyrapropoyne)、阿米諾皮利酚(aminopyrifen)、二氯苯噻唑(dichlobentiazox)、氯氟醚菌唑(Ipfentrifluconazole)、氯氟醚菌唑(mefentrifluconazole)、基諾福麥林(quinofumelin)、迪派地隆(dipymetitrone)。(U) Agents of unknown mechanism of action Cymoxanil; tecloftalam; triazoxide; flusulfamide; diclomezine; cyflufenamid; dodine, poly Dodine free base; flutianil; ferimzone; tebufloquin; picarbutrazox; validamycin. Fluoxapiprolin, florylpicoxamid, fluopimide, ipflufenoquin, metyltetraprole, pyridazine pyridachlometyl, pyrapropoyne, aminopyrifen, dichlobentiazox, Ipfentrifluconazole, mefentrifluconazole , quinofumelin, dipymetitrone.
(M)顯示出多作用點接觸活性的藥劑 銅(各種鹽)、鹼性硫酸銅、波爾多液(bordeaux mixture)、氫氧化銅(copper hydroxide)、萘二甲酸銅(copper naphthalate)、氧氯化銅(copper oxychloride)、硫酸銅(copper sulfate)、氧化銅(copper oxide)、羥基喹啉銅(oxine copper);硫(sulfur)、石硫合劑;福美鐵(ferbam)、代森錳鋅(Manzeb)、代森錳(maneb)、代森聯(metiram)、甲基代森鋅(propineb)、秋蘭姆(thiuram)、噻唑鋅、代森鋅(zineb)、福美鋅(ziram);克菌丹(captan)、敵菌丹(captafol)、滅菌丹(folpet);百菌清(chlorothalonil);抑菌靈(dichlofluanid)、對甲抑菌靈(tolylfluanid);雙胍鹽(guazatine)、雙胍乙酸鹽(guazatine acetate)、雙胍辛胺(iminoctadine)、雙胍辛胺三乙酸鹽(iminoctadine triacetate)、雙胍三辛烷基苯磺酸鹽(iminoctadine trialbesilate);敵菌靈(anilazine);二噻農(dithianon);滅蟎蜢(quinomethionate);唑呋草(fluoroimide);磺菌威(methasulfocarb)。(M) Agents exhibiting multi-point contact activity Copper (various salts), alkaline copper sulfate, bordeaux mixture, copper hydroxide, copper naphthalate, copper oxychloride, copper sulfate , copper oxide (copper oxide), oxine copper (oxine copper); sulfur (sulfur), lime sulfur mixture; ferbam (ferbam), mancozeb (Manzeb), manganese (maneb), mangosteen (metiram), methyl desen zinc (propineb), thiuram (thiuram), thiazole zinc, desen zinc (zineb), ziram (ziram); Folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; quinomethionate; fluoroimide); sulfocarb (methasulfocarb).
以下示出可與本發明的有害生物防治劑混用或併用的植物調節劑的具體例。 1-甲基環丙烯、2,3,5-三碘苯甲酸、吲哚乙酸(IAA)、吲哚丁酸(IBA)、2-甲基-4-氯苯氧乙酸(MCPA)、二甲四氯丁酸(MCPB)、4-CPA、5-胺基乙醯丙酸鹽酸鹽、6-苄基胺基嘌呤、脫落酸(abscisic acid)、四烯雌酮鹽酸鹽、嘧啶醇(ancymidol)、地樂胺(butralin)、碳酸鈣、氯化鈣、甲酸鈣、過氧化鈣、石灰硫磺、硫酸鈣、矮壯素(Chlormequat Chloride)、氯苯胺靈(Chlorpropham)、氯化膽鹼、調果酸(cloprop)、氰胺(cyanamide)、環丙酸醯胺(Cyclanilide)、丁醯肼(daminozide)、癸醇、2,4-滴丙酸(dichlorprop)、調呋酸(dikegulac)、落長靈(Dimethipin)、敵草快(Diquat)、乙烯磷(ethephon)、吲唑酯(ethychlozate)、氟節胺(Flumetralin)、呋嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤黴素A(gibberellin A)、赤黴素A3(gibberellin A3)、惡黴靈(hymexazol)、抗倒胺(Inabenfide)、稻瘟靈(isoprothiolane)、激動素(kinetin)、馬來酸醯肼、氟磺醯草胺(Mefluidide)、縮節胺(mepiquat chloride)、氧化型麩胱甘肽、多效唑(paclobutrazol)、二甲戊樂靈(Pendimethalin)、調環酸鈣(prohexadione-calcium)、茉莉酮(Prohydrojasmon)、吡草醚(Pyraflufen-ethyl)、殺雄啉(Sintofen)、1-萘乙酸鈉、氰酸鈉、鏈黴素(streptomycin)、噻苯隆(thidiazuron)、抑芽唑(Triapenthenol)、脫葉磷(tribufos)、抗倒酯(Trinexapac-ethyl)、烯效唑(uniconazole)P、1-萘基乙醯胺。Specific examples of plant conditioners that can be used in combination or in combination with the pest control agent of the present invention are shown below. 1-Methylcyclopropene, 2,3,5-Triiodobenzoic acid, Indoleacetic acid (IAA), Indolebutyric acid (IBA), 2-Methyl-4-chlorophenoxyacetic acid (MCPA), Dimethicone Tetrachlorobutyric acid (MCPB), 4-CPA, 5-aminoacetyl propionate hydrochloride, 6-benzylaminopurine, abscisic acid, tetraethrone hydrochloride, pyrimidinol ( ancymidol, butralin, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, lime sulfur, calcium sulfate, Chlormequat Chloride, Chlorpropham, choline chloride, Cloprop, cyanamide, Cyclanilide, daminozide, decyl alcohol, 2,4-propionic acid (dichlorprop), dikegulac, Dimethipin, Diquat, ethephon, ethychlozate, Flumetralin, flurprimidol, forchlorfenuron, gibberellin A (gibberellin A), gibberellin A3 (gibberellin A3), hymexazol, inabenfide, isoprothiolane, kinetin, hydrazine maleate, fluorine Mefluidide, mepiquat chloride, oxidized glutathione, paclobutrazol, pendimethalin, prohexadione-calcium, jasmonone ( Prohydrojasmon), Pyraflufen-ethyl, Sintofen, Sodium 1-naphthalene acetate, Sodium cyanate, Streptomycin, Thidiazuron, Triapenthenol, Trinexapac-ethyl, uniconazole P, 1-naphthylacetamide.
〔外部寄生蟲防治劑〕 本發明的外部寄生蟲防治劑含有選自本發明化合物中的至少一種作為有效成分。只要顯示出外部寄生蟲的防治效果,則本發明的外部寄生蟲防治劑中所含的本發明化合物的量並無特別限制。[External parasite control agent] The ectoparasite control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited as long as the ectoparasite control effect is exhibited.
作為成為本發明的外部寄生蟲防治劑的處理對象的宿主動物,可列舉:犬、貓等寵物動物;寵物鳥;牛、馬、豬、綿羊等家畜;家禽等恆溫動物。除此以外,亦可列舉:蜜蜂、鍬形蟲、獨角仙。Examples of host animals to be treated by the ectoparasite control agent of the present invention include pet animals such as dogs and cats; pet birds; livestock such as cattle, horses, pigs, and sheep; and warm-blooded animals such as poultry. In addition, can also list: bees, stag beetles, unicorns.
本發明的外部寄生蟲防治劑可利用公知的獸醫學方法(局部、口服、非口服或皮下給藥)進行施用。作為該方法,可列舉:藉由片劑、膠囊、飼料混入等而向動物口服給藥的方法;藉由浸漬液、栓劑、注射(肌內、皮下、靜脈內、腹腔內等)等而向動物給藥的方法;藉由噴射、澆潑(pour on)、點塗(spot on)等而將油性或水性液劑局部給藥的方法;於樹脂中混入外部寄生蟲防治劑,將所述混煉物成形為項圈、耳標等合適的形狀,將其佩戴於動物身上,從而局部給藥的方法等。The ectoparasite control agent of the present invention can be administered by a known veterinary method (topical, oral, parenteral or subcutaneous administration). Examples of this method include: a method of oral administration to animals by mixing tablets, capsules, feed, etc.; a method of administering to animals by infusion, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. Methods of animal administration; methods of topical administration of oily or aqueous liquid preparations by spraying, pouring on, spot on, etc.; The kneaded product is formed into a suitable shape such as a collar and an ear tag, and it is worn on an animal, thereby a method of topical administration and the like.
外部寄生蟲寄生於宿主動物、尤其是恆溫動物體內及體表。詳細而言,寄生於宿主動物的後背、腋下、下腹部、大腿內部等而自動物獲得血液或皮屑等營養源,從而得以生息。作為外部寄生蟲,可列舉:蟎類、虱類、蚤類、蚊、廄螫蠅、麻蠅等。以下示出可利用本發明的外部寄生蟲防治劑進行防治的外部寄生蟲的具體例。External parasites live in and on host animals, especially warm-blooded animals. More specifically, it is parasitic on the back, underarm, lower abdomen, inner thigh, etc. of a host animal to obtain a nutrient source such as blood or dander from the animal and live. Examples of external parasites include mites, lice, fleas, mosquitoes, sting flies, hemp flies, and the like. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.
(1)蟎類(Acari) 皮刺蟎科(Dermanyssidae)的蟎、巨刺蟎科(Macronyssidae)的蟎、厲蟎科(Laelapidae)的蟎、瓦蟎科(Varroidae)的蟎、隱喙蜱科(Argasidae)的蟎、硬蜱科(Ixodidae)的蟎、癢蟎科(Psoroptidae)的蟎、疥蟎科(Sarcoptidae)的蟎、膝蟎科(Knemidokoptidae)的蟎、蠕形蟎科(Demodixidae)的蟎、恙蟎科(Trombiculidae)的蟎、鍬形蟲類等昆蟲寄生性蟎。 (2)虱目(Phthiraptera) 血虱科(Haematopinidae)的虱、顎虱科(Linognathidae)的虱、短角鳥虱科(Menoponidae)的鳥虱、長角鳥虱科(Philopteridae)的鳥虱、獸鳥虱科(Trichodectidae)的鳥虱。 (3)蚤目(Siphonaptera) 蚤科(Pulicidae)的蚤、例如犬蚤屬(Ctenocephalides spp.)的犬蚤(Ctenocephalides canis)、貓蚤(Ctenocephalides felis); 潛蚤科(Tungidae)的蚤、角葉蚤科(Ceratophyllidae)的蚤、細蚤科(Leptopsyllidae)的蚤。 (4)半翅目(Hemiptera)。 (5)雙翅目(Diptera)的害蟲 蚊科(Culicidae)的蚊、蚋科(Simuliidae)的蚋、蠓科(Ceratopogonidae)的蠓、虻科(Tabanidae)的虻、家蠅科(Muscidae)的蠅、舌蠅科(Glossinidae)的舌蠅、麻蠅科的麻蠅、虱蠅科(Hippoboscidae)的蠅、麗蠅科(Calliphoridae)的蠅、狂蠅科(Oestridae)的蠅。(1) Mites (Acari) Mites of the family Dermanyssidae, mites of the family Macronyssidae, mites of the family Laelapidae, mites of the family Varroidae, mites of the family Argasidae, mites of the family Argasidae, mites of the family Ixodidae, mites of the family Psoroptidae, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodixidae, mites of the family Trombiculidae , stag beetles and other insect parasitic mites. (2) Phthiraptera lice of the family Haematopinidae, lice of the family Linognathidae, lice of the family Menoponidae, lice of the family Philopteridae, lice of the family Trichodectidae Bird lice. (3) Siphonaptera Fleas of the family Pulicidae, for example Ctenocephalides canis, Ctenocephalides felis of the genus Ctenocephalides spp.; Fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae. (4) Hemiptera. (5) Diptera pests Mosquitoes of the family Culicidae, gnats of the family Simuliidae, midges of the family Ceratopogonidae, flies of the family Tabanidae, flies of the family Muscidae, tsetse flies of the family Glossinidae , Hemp flies of the family Hempfly, flies of the family Hippoboscidae, flies of the family Calliphoridae, flies of the family Oestridae.
〔內部寄生蟲防治或驅除劑〕 本發明的內部寄生蟲防治或驅除劑含有選自本發明化合物中的至少一種作為有效成分。只要顯示出內部寄生蟲的防治效果,則本發明的內部寄生蟲防治或驅除劑中所含的本發明化合物的量並無特別限制。[Internal parasite control or repellent] The internal parasite controlling or expelling agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the internal parasite controlling or expelling agent of the present invention is not particularly limited as long as the control effect of internal parasites is exhibited.
成為本發明的內部寄生蟲防治或驅除劑的對象的寄生蟲於宿主動物、尤其是恆溫動物或魚類的體內寄生(內部寄生蟲)。作為本發明的內部寄生蟲防治或驅除劑有效的宿主動物,可列舉:人類、家畜哺乳動物(例如,牛、馬、豬、綿羊、山羊等)、實驗動物(例如,小鼠、大鼠、沙鼠等)、寵物動物(例如,倉鼠、豚鼠、犬、貓、馬、松鼠、兔、白鼬等)、野生及動物園的哺乳動物(猴子、狐狸、鹿、野牛等)、家禽(火雞、鴨子、雞、鵪鶉、鵝等)、寵物鳥(鴿子、鸚鵡、九官鳥、文鳥、鸚鵡、白腰文鳥、金絲雀等)等恆溫動物;或鮭魚、鱒魚、錦鯉等魚類。藉由防治及驅除寄生蟲,可預防或治療寄生蟲傳播的寄生蟲疾病。The parasite to be the object of the internal parasite control or expelling agent of the present invention is parasitic (internal parasite) in a host animal, especially a warm-blooded animal or a fish. Examples of effective host animals for the internal parasite control or expelling agent of the present invention include humans, livestock mammals (for example, cattle, horses, pigs, sheep, goats, etc.), experimental animals (for example, mice, rats, gerbils, etc.), pet animals (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, bison, etc.), poultry (turkeys, etc.) , ducks, chickens, quails, geese, etc.), pet birds (pigeons, parrots, nine-official birds, birds, parrots, white-backed birds, canaries, etc.) and other warm-blooded animals; or salmon, trout, koi and other fish. Parasitic diseases transmitted by parasites can be prevented or treated by controlling and expelling parasites.
作為防治或驅除對象的寄生蟲,可列舉以下者。 (1)膨結蟲目(Dioctophymatida)的線蟲類 (a)膨結蟲科(Dioctophymatidae)的膨結蟲、例如腎蟲屬(Dioctophyma spp.)的膨結蟲(Dioctophyma renale); (b)紫貂胃蟲科(Soboliphymatidae)的膨結蟲、例如紫貂胃蟲屬(Soboliphyme spp.)的安倍紫貂胃蟲(Soboliphyme abei)、巴魯麗尼紫貂胃蟲(Soboliphyme baturini)。Examples of parasites targeted for control or extermination include the following. (1) Nematodes of the order Dioctophymatida (a) Dioctophyma renale of the family Dioctophymatidae, such as Dioctophyma renale of the genus Dioctophyma spp.; (b) Sable worms of the family Soboliphymatidae, for example Soboliphyme abei, Soboliphyme baturini of the genus Soboliphyme spp.
(2)毛首目(Trichocephalida)的線蟲類 (a)旋毛蟲科(Trichinellidae)的旋毛蟲、例如旋毛蟲屬(Trichinella spp.)的旋毛蟲(Trichinella spiralis); (b)鞭蟲科(Trichuridae)的鞭蟲、例如毛細線蟲屬(Capillaria spp.)的有環毛細線蟲(Capillaria annulata)、撚轉毛細線蟲(Capillaria contorta)、肝毛細線蟲(Capillaria hepatica)、穿孔毛細線蟲(Capillaria perforans)、狐膀胱毛細線蟲(Capillaria plica)、豬毛細線蟲(Capillaria suis);鞭蟲屬(Trichuris spp.)的犬鞭蟲(Trichuris vulpis)、牛鞭蟲(Trichuris discolor)、羊鞭蟲(Trichuris ovis)、斯氏鞭蟲(Trichuris skrjabini)、豬鞭蟲(Trichuris suis)。(2) Nematodes of the order Trichocephalida (a) Trichinella of the family Trichinellidae, such as Trichinella spiralis of the genus Trichinella spp.; (b) Trichuris of the family Trichuridae, such as Capillaria annulata, Capillaria contorta, Capillaria hepatica, perforator of Capillaria spp. Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris vulpis, Trichuris discolor, sheep Trichuris ovis, Trichuris skrjabini, Trichuris suis.
(3)小桿線蟲目(Rhabditida)的線蟲類 類圓線蟲科(Strongyloididae)的類圓線蟲、例如類圓線蟲屬(Strongyloides spp.)的乳頭類圓線蟲(Strongyloides papillosus)、貓糞類圓線蟲(Strongyloides planiceps)、豬蘭氏類圓線蟲(Strongyloides ransomi)、豬糞類圓線蟲(Strongyloides suis)、糞類圓線蟲(Strongyloides stercoralis)、腫脹類圓線蟲(Strongyloides tumefaciens)、鼠糞類圓線蟲(Strongyloides ratti)。(3) Nematodes of the order Rhabditida Strongyloides of the family Strongyloididae, such as Strongyloides papillosus of the genus Strongyloides (Strongyloides spp.), Strongyloides planiceps, Strongyloides ransomi), Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti.
(4)圓線蟲目(Strongylida)的線蟲類 鉤蟲科(Ancylostomatidae)的鉤蟲、例如鉤口線蟲屬(Ancylostoma spp.)的巴西鉤口線蟲(Ancylostoma braziliense)、犬鉤口線蟲(Ancylostoma caninum)、十二指腸鉤口線蟲(Ancylostoma duodenale)、管形鉤口線蟲(Ancylostoma tubaeforme);彎口線蟲屬(Uncinaria stenocephala)的狹首彎口線蟲(Uncinaria stenocephala);仰口線蟲屬(Bunostomum spp.)的牛仰口線蟲(Bunostomum phlebotomum)、羊仰口線蟲(Bunostomum trigonocephalum)。(4) Nematodes of the order Strongylida Hookworms of the family Ancylostomatidae, e.g. Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, Ancylostoma duodenale of the genus Ancylostoma spp. Nematodes (Ancylostoma tubaeforme); Uncinaria stenocephala of the genus Uncinaria stenocephala; Bunostomum phlebotomum and Bunostomum of the genus Bunostomum spp. trigonocephalum).
(5)圓線蟲目(Strongylida)的線蟲類 (a)管圓線蟲科(Angiostrongylidae)的線蟲、例如貓圓線蟲屬(Aelurostrongylus spp.)的貓圓線蟲(Aelurostrongylus abstrusus);管圓線蟲屬(Angiostrongylus spp.)的血管圓線蟲(Angiostrongylus vasorum)、廣州管圓線蟲(Angiostrongylus cantonesis); (b)環體線蟲科(Crenosomatidae)的線蟲、例如環體線蟲屬(Crenosoma spp.)的肺環體線蟲(Crenosoma aerophila)、狐環體線蟲(Crenosoma vulpis); (c)似絲蟲科(Filaroididae)的線蟲、例如似絲蟲屬(Filaroides spp.)的肺似絲蟲(Filaroides hirthi)、奧氏似絲蟲(Filaroides osleri); (d)後圓線蟲科(Metastrongylidae)的後圓線蟲、例如後圓線蟲屬(Metastrongylus spp.)的豬後圓線蟲(Metastrongylus apri)、不對稱後圓線蟲(Metastrongylus asymmetricus)、複陰後圓形線蟲(Metastrongylus pudendotectus)、薩氏後圓線蟲(Metastrongylus salmi); (e)比翼線蟲科(Syngamidae)的比翼線蟲、例如杯口線蟲屬(Cyathostoma spp.)的水鳥杯口線蟲(Cyathostoma bronchialis);比翼線蟲屬(Syngamus spp.)的斯氏比翼線蟲(Syngamus skrjabinomorpha)、氣管比翼線蟲(Syngamus trachea)。(5) Nematodes of the order Strongylida (a) Nematodes of the family Angiostrongylidae, such as Aelurostrongylus abstrusus of the genus Aelurostrongylus spp.; Angiostrongylus vasorum of the genus Angiostrongylus spp., Angiostrongylus cantonesis; (b) nematodes of the family Crenosomatidae, such as Crenosoma aerophila, Crenosoma vulpis of the genus Crenosoma spp.; (c) nematodes of the family Filaroididae, such as Filaroides hirthi, Filaroides osleri of the genus Filaroides spp.; (d) Metastrongylus species of the family Metastrongylidae, such as Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus asymmetricus of the genus Metastrongylus spp. Nematodes (Metastrongylus pudendotectus), Metastrongylus salmi; (e) Syngamus skrjabinomorpha of the family Syngamus spp. , Syngamus trachea.
(6)圓線蟲目(Strongylida)的線蟲類 (a)莫林線蟲科(Molineidae)的線蟲、例如細頸線蟲屬(Nematodirus spp.)的尖刺細頸線蟲(Nematodirus filicollis)、鈍刺細頸線蟲(Nematodirus spathiger); (b)網尾線蟲科(Dictyocaulidae)的線蟲、例如網尾線蟲屬(Dictyocaulus spp.)的絲狀網尾線蟲(Dictyocaulus filaria)、胎生網尾線蟲(Dictyocaulus viviparus); (c)撚轉胃蟲科(Haemonchidae)的線蟲、例如血矛線蟲屬(Haemonchus spp.)的撚轉血矛線蟲(Haemonchus contortus);長刺線蟲屬(Mecistocirrus spp.)的指形長刺線蟲(Mecistocirrus digitatus); (d)撚轉胃蟲科(Haemonchidae)的線蟲、例如奧斯特線蟲屬(Ostertagia spp.)的奧斯特線蟲(Ostertagia ostertagi); (e)似繞線蟲科(Heligmonellidae)的線蟲、例如日圓線蟲屬(Nippostrongylus spp.)的巴西日圓線蟲(Nippostrongylus braziliensis); (f)毛圓線蟲科(Trichostrongylidae)的線蟲、例如毛圓線蟲屬(Trichostrongylus spp.)的艾氏毛圓線蟲(Trichostrongylus axei)、蛇形毛圓線蟲(Trichostrongylus colubriformis)、微細毛圓線蟲(Trichostrongylus tenuis);豬圓線蟲屬(Hyostrongylus spp.)的紅色豬圓線蟲(Hyostrongylus rubidus);尖柱線蟲屬(Obeliscoides spp.)的兔尖柱線蟲(Obeliscoides cuniculi)。(6) Nematodes of the order Strongylida (a) nematodes of the family Molineidae, for example Nematodirus filicollis, Nematodirus spathiger of the genus Nematodirus spp.; (b) nematodes of the family Dictyocaulidae, such as Dictyocaulus filaria, Dictyocaulus viviparus of the genus Dictyocaulus spp.; (c) Nematodes of the family Haemonchidae, such as Haemonchus contortus of the genus Haemonchus spp.; (Mecistocrirus digitatus); (d) nematodes of the family Haemonchidae, such as Ostertagia ostertagi of the genus Ostertagia spp.; (e) Nematodes of the family Heligmonellidae, such as Nippostrongylus braziliensis of the genus Nippostrongylus spp.; (f) Nematodes of the family Trichostrongylidae, such as Trichostrongylus axei, Trichostrongylus colubriformis, Trichostrongylus of the genus Trichostrongylus spp. tenuis); Hyostrongylus rubidus of Hyostrongylus spp.; Obeliscoides cuniculi of Obeliscoides spp.
(7)圓線蟲目(Strongylida)的線蟲類 (a)夏柏特線蟲科(Chabertiidae)的線蟲、例如夏柏特線蟲屬(Chabertia spp.)的綿羊夏柏特線蟲(Chabertia ovina);結節線蟲屬(Oesophagostomum spp.)的豬結節線蟲(Oesophagostomum brevicaudatum)、哥倫比亞結節線蟲(Oesophagostomum columbianum)、有齒結節線蟲(Oesophagostomum dentatum)、喬奇亞結節線蟲(Oesophagostomum georgianum)、梅普爾斯通結節線蟲(Oesophagostomum maplestonei)、長尾結節線蟲(Oesophagostomum quadrispinulatum)、食道口線蟲(Oesophagostomum radiatum)、微管結節線蟲(Oesophagostomum venulosum)、華氏食道口線蟲(Oesophagostomum watanabei); (b)腎線蟲科(Stephanuridae)的線蟲、例如腎線蟲屬(Stephanurus spp.)的有齒腎線蟲(Stephanurus dentatus); (c)圓線蟲科(Strongylidae)的線蟲、例如圓線蟲屬(Strongylus spp.)的驢圓線蟲(Strongylus asini)、無齒圓線蟲(Strongylus edentatus)、馬圓線蟲(Strongylus equinus)、普通圓線蟲(Strongylus vulgaris)。(7) Nematodes of the order Strongylida (a) Nematodes of the family Chabertiidae, such as Chabertia ovina of the genus Chabertia spp.; Oesophagostomum of the genus Oesophagostomum spp. brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, esophagus Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophagostomum watanabei; (b) Nematodes of the family Stephanuridae, such as Stephanurus dentatus of the genus Stephanurus spp.; (c) Nematodes of the family Strongylidae, such as Strongylus asini, Strongylus edentatus, Strongylus equinus, Strongylus equinus of the genus Strongylus spp. (Strongylus vulgaris).
(8)蟯蟲目(Oxyurida)的線蟲類 蟯蟲科(Oxyuridae)的線蟲、例如蟯蟲屬(Enterobius spp.)的黑猩猩蟯蟲(Enterobius anthropopitheci)、蠕形住腸線蟲(Enterobius vermicularis);尖尾線蟲屬(Oxyuris spp.)的馬尖尾線蟲(Oxyuris equi);栓尾線蟲屬(Passalurus spp.)的安比瓜栓尾線蟲(Passalurus ambiguus)。(8) Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, e.g. Enterobius anthropopitheci, Enterobius vermicularis of Enterobius spp.; Nematode (Oxyuris equi); Passalurus ambiguus of the genus Passalurus spp.
(9)蛔蟲目(Ascaridida)的線蟲類 (a)禽蛔蟲科(Ascaridiidae)的線蟲、例如禽蛔蟲屬(Ascaridia spp.)的雞蛔蟲(Ascaridia galli); (b)異刺線蟲科(Heterakidae)的線蟲、例如異刺線蟲屬(Heterakis spp.)的貝拉異刺線蟲(Heterakis beramporia)、短刺異刺線蟲(Heterakis brevispiculum)、雞異刺線蟲(Heterakis gallinarum)、小田雞異刺線蟲(Heterakis pusilla)、南方異刺線蟲(Heterakis putaustralis); (c)異尖線蟲科(Anisakidae)的線蟲、例如異尖線蟲屬(Anisakis spp.)的簡單異尖線蟲(Anisakis simplex); (d)蛔蟲科(Ascarididae)的線蟲、例如蛔蟲屬(Ascaris spp.)的似蚓蛔線蟲(Ascaris lumbricoides)、豬蛔蟲(Ascaris suum);副蛔蟲屬(Parascaris spp.)的馬副蛔蟲(Parascaris equorum); (e)弓首線蟲科(Toxocaridae)的線蟲、例如弓首線蟲屬(Toxocara spp.)的犬弓首線蟲(Toxocara canis)、獅弓首線蟲(Toxocara leonina)、豬弓首線蟲(Toxocarasuum)、牛弓首線蟲(Toxocara vitulorum)、貓弓首線蟲(Toxocara cati)。(9) Nematodes of the order Ascaridida (a) nematodes of the family Ascaridiidae, such as Ascaridia galli of the genus Ascaridia spp.; (b) Nematodes of the family Heterakidae, such as Heterakis beramporia, Heterakis brevispiculum, Heterakis of the genus Heterakis spp. gallinarum), Heterakis pusilla, Heterakis putautralis; (c) nematodes of the family Anisakidae, such as Anisakis simplex of the genus Anisakis spp.; (d) Nematodes of the family Ascarididae, such as Ascaris lumbricoides, Ascaris suum of the genus Ascaris spp.; Parascaris equine of the genus Parascaris spp. equorum); (e) Nematodes of the family Toxocaridae, such as Toxocara canis of the genus Toxocara spp., Toxocara leonina, Toxocarasuum, Toxocara vitulorum, Toxocara cati.
(10)旋尾線蟲目(Spirurida)的線蟲類 (a)盤尾絲蟲科(Onchocercidae)的線蟲、例如布魯絲蟲屬(Brugia spp.)的馬來布魯絲蟲(Brugia malayi)、彭亨布魯絲蟲(Brugia pahangi)、派特布魯絲蟲(Brugia patei);棘唇線蟲屬(Dipetalonema spp.)的隱蔽棘唇絲蟲(Dipetalonema reconditum);惡絲蟲屬(Dirofilaria spp.)的犬惡絲蟲(Dirofilaria immitis);絲蟲屬(Filaria spp.)的羅阿絲蟲(Filaria oculi);盤尾絲蟲屬(Onchocerca spp.)的馬頸盤尾絲蟲(Onchocerca cervicalis)、牛盤尾絲蟲(Onchocerca gibsoni)、喉瘤盤尾絲蟲(Onchocerca gutturosa); (b)絲狀線蟲科(Setariidae)的線蟲、例如絲狀線蟲屬(Setaria spp.)的指狀絲狀線蟲(Setaria digitata)、馬絲狀線蟲(Setaria equina)、牛唇乳絲狀線蟲(Setaria labiatopapillosa)、馬氏絲狀線蟲(Setaria marshalli);吳策線蟲屬(Wuchereria spp.)的班氏吳策線蟲(Wuchereria bancrofti); (c)絲狀線蟲科(Filariidae)的線蟲、例如副絲蟲屬(Parafilaria spp.)的多乳頭絲狀線蟲(Parafilaria multipapillosa);冠絲蟲屬(Stephanofilaria spp.)的艾氏冠絲蟲(Stephanofilaria assamensis)、德氏冠絲蟲(Stephanofilaria dedoesi)、咖氏冠絲蟲(Stephanofilaria kaeli)、沖繩絲狀線蟲(Stephanofilaria okinawaensis)、斯氏冠絲蟲(Stephanofilaria stilesi)。(10) Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, such as Brugia malayi of the genus Brugia spp., Brugia pahangi, Paet Brugia patei; Dipetalonema reconditum of Dipetalonema spp.; Dirofilaria immitis of Dirofilaria spp.; Filaria Filaria oculi of the genus Filaria spp.; Onchocerca cervicalis of the genus Onchocerca spp., Onchocerca gibsoni, laryngeal tumor Onchocerca gutturosa; (b) Nematodes of the family Setariidae, e.g. Setaria digitata, Setaria equina, Papilloma spp. (Setaria spp.) Setaria labiatopapillosa), Setaria marshalli; Wuchereria bancrofti of Wuchereria spp.; (c) Nematodes of the family Filariidae, such as Parafilaria multipapillosa of the genus Parafilaria spp.; Crown worms of the genus Stephanofilaria spp. ( Stephanofilaria assamensis), Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
(11)旋尾線蟲目(Spirurida)的線蟲類 (a)顎口線蟲科(Gnathostomatidae)的線蟲、例如顎口線蟲屬(Gnathostoma spp.)的陶氏顎口線蟲(Gnathostoma doloresi)、刺顎口線蟲(Gnathostoma spinigerum); (b)柔線蟲科(Habronematidae)的線蟲、例如柔線蟲屬(Habronema spp.)的大柔線蟲(Habronema majus)、小口柔線蟲(Habronema microstoma)、蠅柔線蟲(Habronema muscae);德拉希線蟲屬(Draschia spp.)的大口德拉希線蟲(Draschia megastoma); (c)泡翼線蟲科(Physalopteridae)的線蟲、例如泡翼線蟲屬(Physaloptera spp.)的犬泡翼線蟲(Physaloptera canis)、狐狸泡翼線蟲(Physaloptera cesticillata)、艾德吸納泡翼線蟲(Physaloptera erdocyona)、獅泡翼線蟲(Physaloptera felidis)、成雙泡翼線蟲(Physaloptera gemina)、帕匹羅拉基愛特泡翼線蟲(Physaloptera papilloradiata)、貓泡翼線蟲(Physaloptera praeputialis)、派道普瑞阿如天魯斯泡翼線蟲(Physaloptera pseudopraerutialis)、稀泡翼線蟲(Physaloptera rara)、西伯利亞泡翼線蟲(Physaloptera sibirica)、巴魯皮奈斯泡翼線蟲(Physaloptera vulpineus); (d)筒線蟲科(Gongylonematidae)的線蟲、例如筒線蟲屬(Gongylonema spp.)的美麗筒線蟲(Gongylonema pulchrum); (e)尾旋線蟲科(Spirocercidae)的線蟲、例如旋翼線蟲屬(Ascarops spp.)的圓形旋翼線蟲(Ascarops strongylina); (f)吸吮線蟲科(Thelaziidae)的線蟲、例如吸吮線蟲屬(Thelazia spp.)的結膜吸吮線蟲(Thelazia callipaeda)、大口結膜吸吮線蟲(Thelazia gulosa)、淚管吸吮線蟲(Thelazia lacrymalis)、露德西吸吮線蟲(Thelazia rhodesi)、斯克里亞賓氏吸吮線蟲(Thelazia skrjabini)。(11) Nematodes of the order Spirurida (a) nematodes of the family Gnathostomatidae, such as Gnathostoma doloresi, Gnathostoma spinigerum of the genus Gnathostoma spp.; (b) Nematodes of the family Habronematidae, such as Habronema majus, Habronema microstoma, Habronema muscae of the genus Habronema spp.; Draschia megastoma of the genus (Draschia spp.); (c) Nematodes of the family Physalopteridae, such as Physaloptera canis of the genus Physaloptera spp., Physaloptera ceticillata, Physaloptera erdocyona), Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera praeputialis Such as Physaloptera pseudopraerutialis, Physaloptera rara, Physaloptera sibirica, Physaloptera vulpineus; (d) Nematodes of the family Gongylonematidae, such as Gongylonema pulchrum of the genus Gongylonema spp.; (e) nematodes of the family Spirocercidae, such as Ascarops strongylina of the genus Ascarops spp.; (f) Nematodes of the family Thelaziidae, such as Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Lourdes of the genus Thelazia spp. Western sucking nematode (Thelazia rhodesi), Scriabin's sucking nematode (Thelazia skrjabini).
〔與其他有害生物相關的防治劑〕 此外,本發明化合物於具有毒針或毒液且會危害人獸的害蟲、傳播各種病原體/病原菌的害蟲、給人類帶來不快感的害蟲(有毒害蟲/衛生害蟲/令人不快的害蟲等)的防治效果的方面優異。[Controlling agents related to other pests] In addition, the compound of the present invention is used for the pests that have poisonous needles or venoms and can harm humans and animals, pests that spread various pathogens/pathogens, and pests that give unpleasantness to humans (toxic pests/sanitary pests/unpleasant pests, etc.). The control effect is excellent.
以下示出其具體例。 (1)膜翅目(Hymenoptera)的害蟲 三節葉蜂科(Argidae)的蜂、癭蜂科(Cynipidae)的蜂、松葉蜂科(Diprionidae)的蜂、蟻科(Formicidae)的蟻、蟻蜂科(Mutillidae)的蜂、胡蜂科(Vespidae)的蜂。Specific examples thereof are shown below. (1) Pests of the order Hymenoptera Bees of the family Argidae, bees of the family Cynipidae, bees of the family Diprionidae, ants of the family Formicidae, bees of the family Mutillidae, family Vespidae bee.
(2)其他害蟲 蟑螂類(Blattodea)、白蟻類(termite)、蜘蛛類(Araneae)、蜈蚣類(cetipede)、馬陸類(millipede)、甲殼類(crustacea)、臭蟲(Cimex lectularius)。(2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipede (millipede), crustaceans (crustacea), bed bugs (Cimex lectularius).
〔製劑配方〕 示出若干本發明的有害生物防治劑、殺蟲或殺蟎劑、外部寄生蟲防治劑、或者內部寄生蟲防治或驅除劑的製劑實施例,但添加物及添加比例不應限定於該些製劑實施例的配方,可於廣範圍內變化。製劑配方中的「份」及「%」為質量基準。[Preparation formula] Several formulation examples of the pest control agent, insecticide or acaricide, external parasite control agent, or internal parasite control or expelling agent of the present invention are shown, but the additives and the addition ratio should not be limited to these formulations The formulations of the examples can vary widely. The "parts" and "%" in the formulation are the quality standards.
以下示出農園藝用及水稻用的製劑配方。 (製劑1:水合劑) 將本發明化合物40份、矽藻土53份、高級醇硫酸酯4份及烷基萘磺酸鹽3份均勻地混合並粉碎至微細,從而獲得有效成分40%的水合劑。 (製劑2:乳劑) 將本發明化合物30份、二甲苯33份、二甲基甲醯胺30份及聚氧乙烯烷基烯丙基醚7份混合溶解,從而獲得有效成分30%的乳劑。 (製劑3:粒劑) 將本發明化合物5份、滑石40份、黏土38份、膨潤土10份及烷基硫酸鈉7份均勻地混合並粉碎至微細,然後,呈直徑0.5 mm~1.0 mm的粒狀進行造粒,從而獲得有效成分5%的粒劑。 (製劑4:粒劑) 將本發明化合物5份、黏土73份、膨潤土20份、二辛基磺基琥珀酸鈉鹽1份及磷酸鉀1份充分粉碎並加以混合,加入水而充分混煉,然後,進行造粒乾燥,從而獲得有效成分5%的粒劑。 (製劑5:懸濁劑) 將本發明化合物10份、聚氧乙烯烷基烯丙基醚4份、多羧酸鈉鹽2份、甘油10份、黃原膠0.2份及水73.8份混合,並進行濕式粉碎,直至粒度成為3微米以下為止,從而獲得有效成分10%的懸濁劑。The formulation formulations for agriculture and horticulture and rice are shown below. (Formulation 1: Hydrating Agent) 40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate were uniformly mixed and pulverized to fineness to obtain a hydrating agent containing 40% of active ingredients. (Formulation 2: Emulsion) 30 parts of the compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of polyoxyethylene alkyl allyl ether were mixed and dissolved to obtain an emulsion of 30% of active ingredients. (Formulation 3: Granules) 5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and pulverized until fine, and then granulated in the form of granules having a diameter of 0.5 mm to 1.0 mm, thereby Available in 5% active ingredient granules. (Formulation 4: Granules) 5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinic acid sodium salt, and 1 part of potassium phosphate were thoroughly pulverized and mixed, and water was added and thoroughly kneaded, and then granulated and dried. , so as to obtain granules with 5% active ingredients. (Formulation 5: Suspension) Mix 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water, and wet pulverize until particle size A suspension of 10% of the active ingredient was obtained until it became 3 microns or less.
以下示出外部寄生蟲防治劑、或者內部寄生蟲防治或驅除劑的製劑配方。 (製劑6:顆粒劑) 使本發明化合物5份溶解於有機溶媒中而獲得溶液,將所述溶液噴射至高嶺土94份及白碳1份上,繼而,於減壓下使溶媒蒸發。這種顆粒可與動物的餌混合使用。 (製劑7:注入劑) 將本發明化合物0.1份~1份與花生油99份~99.9份均勻地混合,繼而,利用殺菌過濾器進行過濾殺菌。 (製劑8:澆潑劑) 將本發明化合物5份、肉豆蔻酸酯10份及異丙醇85份均勻地混合,從而獲得澆潑劑。 (製劑9:點塗劑) 將本發明化合物10份~15份、棕櫚酸酯10份及異丙醇75份~80份均勻地混合,從而獲得點塗劑。 (製劑10:噴霧劑) 將本發明化合物1份、丙二醇10份及異丙醇89份均勻地混合,從而獲得噴霧劑。The formulation formulation of an external parasite control agent, or an internal parasite control or expelling agent is shown below. (Formulation 6: Granules) A solution obtained by dissolving 5 parts of the compound of the present invention in an organic solvent was sprayed onto 94 parts of kaolin clay and 1 part of white carbon, and then the solvent was evaporated under reduced pressure. The pellets can be mixed with animal baits. (Formulation 7: Injectable) 0.1 part to 1 part of the compound of the present invention and 99 parts to 99.9 parts of peanut oil are uniformly mixed, and then, filtration and sterilization are performed using a sterilizing filter. (Formulation 8: pouring agent) 5 parts of the compound of the present invention, 10 parts of myristate, and 85 parts of isopropyl alcohol were uniformly mixed to obtain a pour-on agent. (Formulation 9: Spot Paint) 10 to 15 parts of the compound of the present invention, 10 parts of palmitate, and 75 to 80 parts of isopropyl alcohol are uniformly mixed to obtain a spot coating agent. (Formulation 10: Spray) 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol were uniformly mixed to obtain a spray.
繼而,示出合成實施例,並對本發明進一步進行具體說明。其中,本發明不受以下合成實施例任何限制。Next, a synthesis example is shown, and the present invention is further described in detail. Wherein, the present invention is not limited in any way by the following synthesis examples.
〔實施例1〕 6-溴-N-(1-(1-(吡啶-2-基)-1H-1,2,4-三唑-5-基)乙基)-8-(三氟甲基)喹唑啉-4-胺〔6-bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazolin-4-amine〕的合成(化合物編號A-2的合成)[Example 1] 6-Bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazoline -4-Amino[6-bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazolin-4 -amine] (synthesis of compound No. A-2)
(步驟1) 2-胺基-5-溴-3-(三氟甲基)苯甲酸〔2-amino-5-bromo-3-(trifluoromethyl)benzoic acid〕的合成(step 1) Synthesis of 2-amino-5-bromo-3-(trifluoromethyl)benzoic acid
[化9] [Chemical 9]
使2-胺基-3-(三氟甲基)苯甲酸(1.5 g)溶解於N,N-二甲基甲醯胺(10 ml)中。將該溶液冷卻至0℃,向其中加入N-溴琥珀醯亞胺(1.4 g)。將所述溶液的溫度提高至室溫,攪拌過夜。繼而,藉由減壓而將溶媒自所獲得的液體中餾去。向其中加入水,並於0℃下攪拌10分鐘。對所獲得的液體進行過濾,依次利用水及己烷對所獲得的固體成分進行清洗,並於減壓下進行乾燥而獲得目標物2.0 g(產率96%)。2-Amino-3-(trifluoromethyl)benzoic acid (1.5 g) was dissolved in N,N-dimethylformamide (10 ml). The solution was cooled to 0°C, and N-bromosuccinimide (1.4 g) was added thereto. The temperature of the solution was raised to room temperature and stirred overnight. Then, the solvent was distilled off from the obtained liquid by reducing pressure. Water was added thereto, followed by stirring at 0°C for 10 minutes. The obtained liquid was filtered, the obtained solid content was washed with water and hexane in this order, and dried under reduced pressure to obtain 2.0 g of the target product (yield: 96%).
(步驟2) 6-溴-8-(三氟甲基)喹唑啉-4-醇〔6-bromo-8-(trifluoromethyl)quinazolin-4-ol〕的合成(step 2) Synthesis of 6-bromo-8-(trifluoromethyl)quinazolin-4-ol [6-bromo-8-(trifluoromethyl)quinazolin-4-ol]
[化10] [Chemical 10]
使2-胺基-5-溴-3-(三氟甲基)苯甲酸(2.0 g)溶解於甲醯胺(5.0 mL)中。將該溶液於150℃下攪拌過夜。 將所獲得的液體冷卻至0℃。然後,進行過濾,依次利用水及己烷對所獲得的固體成分進行清洗,並於減壓下進行乾燥而獲得目標物1.7 g(產率84%)。2-Amino-5-bromo-3-(trifluoromethyl)benzoic acid (2.0 g) was dissolved in carboxamide (5.0 mL). The solution was stirred at 150°C overnight. The obtained liquid was cooled to 0°C. Then, it filtered, the obtained solid content was wash|cleaned with water and hexane in this order, and it dried under reduced pressure, and obtained 1.7 g of target objects (yield 84%).
(步驟3) 6-溴-4-氯-8-(三氟甲基)喹唑啉〔6-bromo-4-chloro-8-(trifluoromethyl)quinazoline〕的合成(step 3) Synthesis of 6-bromo-4-chloro-8-(trifluoromethyl)quinazoline [6-bromo-4-chloro-8-(trifluoromethyl)quinazoline]
[化11] [Chemical 11]
向亞硫醯氯(5.0 mL)中加入6-溴-8-(三氟甲基)喹唑啉-4-醇(1.7 g),繼而,加入數滴N,N-二甲基甲醯胺。將其於加熱回流下攪拌過夜。然後,冷卻至室溫。將所獲得的溶液冰浴冷卻,繼而加入至飽和重碳酸氫鈉水溶液中。利用乙酸乙酯對其進行萃取,利用飽和食鹽水來清洗有機相,利用硫酸鎂進行乾燥並加以過濾。將濾液減壓濃縮。利用矽膠管柱層析法對所獲得的濃縮物進行精製,藉此獲得目標物1.6 g(產率88%)。To thionine chloride (5.0 mL) was added 6-bromo-8-(trifluoromethyl)quinazolin-4-ol (1.7 g), followed by a few drops of N,N-dimethylformamide . It was stirred under reflux with heating overnight. Then, cool to room temperature. The obtained solution was cooled in an ice bath, and then added to a saturated aqueous sodium bicarbonate solution. This was extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 1.6 g of the target compound (yield: 88%).
〔1-(1-(吡啶-2-基)-1H-1,2,4-三唑-5-基)乙烷-1-胺的合成〕[Synthesis of 1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethane-1-amine]
(步驟4) 2-(5-(1-溴乙基)-1H-1,2,4-三唑-1-基)吡啶〔2-(5-(1-bromoethyl)-1H-1,2,4-triazol-1-yl)pyridine〕的合成(step 4) 2-(5-(1-bromoethyl)-1H-1,2,4-triazol-1-yl)pyridine[2-(5-(1-bromoethyl)-1H-1,2,4-triazol Synthesis of -1-yl)pyridine]
[化12] [Chemical 12]
使2-溴丙烷醯胺(5.0 g)溶解於二氯甲烷(165 mL)中。向其中加入N,N-二甲基甲醯胺二甲基縮醛(6.6 mL),於加熱回流下攪拌1.5小時。 將所獲得的液體減壓濃縮。使所獲得的濃縮物溶解於二噁烷(66 mL)與乙酸(66 mL)的混合液中。向其中加入2-肼基吡啶(4.3 g),於加熱回流下攪拌5小時。將所獲得的液體減壓濃縮。然後,加入乙酸乙酯與飽和碳酸氫鈉水溶液,利用乙酸乙酯進行萃取。利用無水硫酸鎂對所獲得的有機相進行乾燥,並進行過濾。將濾液減壓濃縮。利用矽膠管柱層析法對所獲得的濃縮物進行精製,藉此獲得目標物5.4 g(產率65%)。2-Bromopropanamide (5.0 g) was dissolved in dichloromethane (165 mL). N,N-dimethylformamide dimethyl acetal (6.6 mL) was added thereto, and the mixture was stirred with heating under reflux for 1.5 hours. The obtained liquid was concentrated under reduced pressure. The obtained concentrate was dissolved in a mixture of dioxane (66 mL) and acetic acid (66 mL). Thereto was added 2-hydrazinopyridine (4.3 g), and the mixture was stirred under reflux with heating for 5 hours. The obtained liquid was concentrated under reduced pressure. Then, ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added, followed by extraction with ethyl acetate. The obtained organic phase was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 5.4 g of the target compound (yield: 65%).
(步驟5) 1-(1-(吡啶-2-基)-1H-1,2,4-三唑-5-基)乙烷-1-胺〔1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethan-1-amine〕的合成(step 5) 1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethane-1-amine[1-(1-(pyridin-2-yl)-1H- Synthesis of 1,2,4-triazol-5-yl)ethan-1-amine]
[化13] [Chemical 13]
向2-(5-(1-溴乙基)-1H-1,2,4-三唑-1-基)吡啶(1 g)中加入7 N甲醇溶解氨(18.5 mL),於密封管中且於60℃下攪拌4小時。冷卻至室溫,進行減壓濃縮而獲得濃縮物(0.88 g)。To 2-(5-(1-bromoethyl)-1H-1,2,4-triazol-1-yl)pyridine (1 g) was added 7 N methanol to dissolve ammonia (18.5 mL) in a sealed tube and stirred at 60°C for 4 hours. It was cooled to room temperature, and concentrated under reduced pressure to obtain a concentrate (0.88 g).
(步驟6) 6-溴-N-(1-(1-(吡啶-2-基)-1H-1,2,4-三唑-5-基)乙基)-8-(三氟甲基)喹唑啉-4-胺〔6-bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazolin-4-amine〕的合成(step 6) 6-Bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazoline -4-Amino[6-bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazolin-4 -amine] synthesis
[化14] [Chemical 14]
使6-溴-4-氯-8-(三氟甲基)喹唑啉(100 mg)溶解於N,N-二甲基甲醯胺(3 ml)中。向其中加入1-(1-(吡啶-2-基)-1H-1,2,4-三唑-5-基)乙烷-1-胺(87 mg)與N,N-二異丙基乙基胺(124 mg),使用微波裝置於150℃下攪拌0.5小時。 利用矽膠層析法對所獲得的液體進行精製。將包含目標物的餾分濃縮,利用己烷對所獲得的固體成分進行清洗而獲得目標物125 mg(產率84%)。6-Bromo-4-chloro-8-(trifluoromethyl)quinazoline (100 mg) was dissolved in N,N-dimethylformamide (3 ml). To this were added 1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethane-1-amine (87 mg) and N,N-diisopropyl Ethylamine (124 mg), stirred at 150 °C for 0.5 h using a microwave device. The obtained liquid was purified by silica gel chromatography. The fraction containing the target substance was concentrated, and the obtained solid content was washed with hexane to obtain 125 mg of the target substance (yield: 84%).
將利用與所述實施例相同的方法所製造的本發明化合物的例子示於表1中。將化合物的物性資料記入於「物性」一欄。作為物性資料,記載了熔點(m.p.)。Table 1 shows examples of the compounds of the present invention produced by the same method as in the above-mentioned Examples. Enter the physical properties of the compound in the "physical properties" column. As physical property data, melting point (m.p.) is recorded.
[表1]
進而,將本發明化合物的例子示於下述表中。再者,於結構式中,碘基是使用「J」來表述。Furthermore, examples of the compounds of the present invention are shown in the following table. In addition, in the structural formula, an iodo group is represented using "J".
[表2]
[表3]
[表4]
[表5]
[表6]
[表7]
[表8]
[表9]
[表10]
[表11]
[表12]
[表13]
關於表中的化合物中在物性一欄中記載為黏性油(VISCOUS OIL)或非晶質(AMORPHOUS)的化合物,以下示出1 H-核磁共振(Nuclear Magnetic Resonance,NMR)的資料。 化合物編號A-30:1 H-NMR(CDCl3 , δ ppm)8.61 (s, 1H), 8.27 (s, 1H), 8.26 (s, 1H), 8.09 (s, 1H), 8.05 (dd, 1H), 8.00 (dd, 1H), 7.09 (t, 1H), 6.70 (q, 1H), 3.77~3.68 (m, 1H), 3.58~3.49 (m, 1H), 2.06 (d, 3H), 1.07 (t, 3H). 化合物編號A-35:1 H-NMR(CDCl3 , δ ppm)8.97 (d, 1H), 8.60 (d, 1H), 8.48 (d, 1H), 8.32 (s, 1H), 8.24 (d, 2H), 8.15 (dd, 1H), 8.04 (s, 1H), 6.59~6.53 (m, 1H), 1.80 (d, 3H). 化合物編號A-40:1 H-NMR(CDCl3 , δ ppm)8.60 (s, 1H), 8.24 (dd, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.07 (t, 1H), 6.68 (qd, 1H), 3.75~3.65 (m, 1H), 3.56~3.48 (m, 1H), 2.04 (d, 3H), 1.06 (t, 3H). 化合物編號A-52:1 H-NMR(CDCl3 , δ ppm)8.44 (s, 1H), 8.24 (dd, 1H), 8.13 (dd, 1H), 8.09 (dd, 1H), 8.01 (s, 1H), 7.78 (s, 1H), 7.61~7.62 (m, 1H), 6.79 (q, 1H), 3.43 (s, 3H), 1.93 (d, 3H). 化合物編號A-57:1 H-NMR(CDCl3 , δ ppm)8.60 (s, 1H), 8.24 (dd, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.07 (t, 1H), 6.68 (qd, 1H), 3.75~3.65 (m, 1H), 3.56~3.48 (m, 1H), 2.04 (d, 3H), 1.06 (t, 3H). 化合物編號A-58:1 H-NMR(CDCl3 , δ ppm)8.45 (s, 1H), 8.30 (dd, 1H), 8.13 (dd, 1H), 8.09 (dd, 1H), 8.02 (d, 1H), 8.01 (s, 1H), 8.00 (d, 1H), 6.79 (q, 1H), 3.44 (s, 3H), 1.93 (d, 3H). 化合物編號A-63:1 H-NMR(DMSO-d6, δ ppm)8.56 (s, 1H), 8.47 (dd, 1H), 8.29 (s, 1H) , 8.27 (d, 1H), 8.21 (d, 1H), 8.17 (d, 1H), 7.99 (d, 1H), 6.80 (q, 1H), 5.41~5.50 (m, 1H), 5.28~5.35 (m, 1H), 4.27~4.32 (m, 1H), 4.17 (dd, 1H), 1.85 (d, 3H), 1.50 (d, 3H).Regarding the compounds described as viscous oil (VISCOUS OIL) or amorphous (AMORPHOUS) in the physical properties column of the compounds in the table, 1 H-NMR (Nuclear Magnetic Resonance, NMR) data are shown below. Compound No. A-30: 1 H-NMR (CDCl 3 , δ ppm) 8.61 (s, 1H), 8.27 (s, 1H), 8.26 (s, 1H), 8.09 (s, 1H), 8.05 (dd, 1H) ), 8.00 (dd, 1H), 7.09 (t, 1H), 6.70 (q, 1H), 3.77~3.68 (m, 1H), 3.58~3.49 (m, 1H), 2.06 (d, 3H), 1.07 ( t, 3H). Compound No. A-35: 1 H-NMR (CDCl 3 , δ ppm) 8.97 (d, 1H), 8.60 (d, 1H), 8.48 (d, 1H), 8.32 (s, 1H), 8.24 (d, 2H), 8.15 (dd, 1H), 8.04 (s, 1H), 6.59~6.53 (m, 1H), 1.80 (d, 3H). Compound No. A-40: 1 H-NMR (CDCl 3 , δ ppm) 8.60 (s, 1H), 8.24 (dd, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.07 (t, 1H), 6.68 (qd, 1H), 3.75~3.65 (m, 1H), 3.56~3.48 (m, 1H), 2.04 (d, 3H), 1.06 (t, 3H). Compound No. A-52: 1 H-NMR (CDCl 3 , δ ppm) 8.44 (s, 1H), 8.24 (dd, 1H), 8.13 (dd, 1H), 8.09 (dd, 1H), 8.01 (s, 1H), 7.78 (s, 1H), 7.61~7.62 (m, 1H), 6.79 (q, 1H), 3.43 (s, 3H), 1.93 (d, 3H). Compound No. A-57: 1 H-NMR (CDCl 3 , δ ppm) 8.60 (s, 1H), 8.24 ( dd, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.07 (t, 1H), 6.68 (qd, 1H), 3.75~3.65 (m, 1H), 3.56 ~3.48 (m, 1H), 2.04 (d, 3H), 1.06 (t, 3H). Compound No. A-58: 1 H-NMR (CDCl 3 , δ ppm) 8.45 (s, 1H), 8.30 (dd, 1H), 8.13 (dd, 1H), 8.09 (dd, 1H), 8.02 (d, 1H), 8.01 (s, 1H), 8.00 (d, 1H), 6.79 ( q, 1H), 3.44 (s, 3H), 1.93 (d, 3H). Compound No. A-63: 1 H-NMR (DMSO-d6, δ ppm) 8.56 (s, 1H), 8.47 (dd, 1H) , 8.29 (s, 1H) , 8.27 (d, 1H), 8.21 (d, 1H), 8.17 (d, 1H), 7.99 (d, 1H), 6.80 (q, 1H), 5.41~5.50 (m, 1H) ), 5.28~5.35 (m, 1H), 4.27~4.32 (m, 1H), 4.17 (dd, 1H), 1.85 (d, 3H), 1.50 (d, 3H).
〔生物試驗〕 藉由以下試驗例而示出本發明化合物有效用作有害生物防治劑的有效成分。「份」為質量基準。[Biological test] The following test examples show that the compound of the present invention is effective as an active ingredient of a pest control agent. "Part" is the quality standard.
(試驗用乳劑的製備) 將本發明化合物5份、二甲基甲醯胺93.6份及聚氧乙烯烷基芳基醚1.4份混合並加以溶解,獲得有效成分5質量%的乳劑(I)。(Preparation of test emulsion) 5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to obtain an emulsion (I) with 5 mass % of active ingredients.
(對照用乳劑的製備) 將二甲基甲醯胺93.6份及聚氧乙烯烷基芳基醚1.4份混合並加以溶解,獲得乳劑(II)。(Preparation of control emulsion) 93.6 parts of dimethylformamides and 1.4 parts of polyoxyethylene alkyl aryl ethers were mixed and dissolved to obtain Emulsion (II).
(1)對黏蟲(Mythimna separata)的效力試驗(1) 將市售的人工飼料(昆蟲類LFS(insecta LFS),日本農產工業公司製造)0.8 g與乳劑(I)1 μl充分混和,於塑膠製試驗容器(1.4 ml容量)中各處理區分別裝入0.2 g作為試驗用飼料。 將黏蟲2齡幼蟲於各處理區分別接種2只,並利用塑膠製的蓋進行密閉。將其放置於25℃的恆溫室內,於第5天研究殺蟲率與攝食量。試驗反覆進行兩次。 殺蟲率(%)=(死亡蟲數/受試蟲數)×100 另外,除將乳劑(I)取代為乳劑(II)以外,於與所述相同的條件下並行進行試驗。(1) Efficacy test against armyworm (Mythimna separata) (1) 0.8 g of commercially available artificial feed (insect-based LFS (insecta LFS), manufactured by Nippon Agricultural Products Co., Ltd.) was thoroughly mixed with 1 μl of Emulsion (I), and placed in plastic test containers (1.4 ml capacity) for each treatment area. Enter 0.2 g as the test feed. Two armyworm second-instar larvae were inoculated in each treatment area, and sealed with plastic lids. It was placed in a constant temperature room at 25°C, and the insecticidal rate and food intake were studied on the 5th day. The test was repeated twice. Insecticidal rate (%) = (number of dead insects/number of tested insects) × 100 In addition, the test was carried out in parallel under the same conditions as described above, except that the emulsion (I) was replaced by the emulsion (II).
針對化合物編號A-1的化合物,進行對黏蟲的效力試驗(1)。A-1的化合物的殺蟲率為100%而有效。 另一方面,乳劑(II)的殺蟲率為0%。 同樣地,針對化合物編號A-9、A-10、A-11、A-12、A-13、A-16、A-17、A-18、A-19、A-25、A-26、A-28、A-29、A-30、A-32、A-33、A-34、A-35、A-36、A-39、A-41、A-42、A-43、A-44、A-45、A-46、A-47、A-48、A-49、A-50、A-51、A-52、A-53、A-54、A-55、A-56、A-57及A-58的化合物,進行對黏蟲的效力試驗(1)。任一化合物的殺蟲率均為100%而有效。For the compound of compound No. A-1, the efficacy test (1) against armyworm was performed. The compound of A-1 has an insecticidal rate of 100% and is effective. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-9, A-10, A-11, A-12, A-13, A-16, A-17, A-18, A-19, A-25, A-26, A-28, A-29, A-30, A-32, A-33, A-34, A-35, A-36, A-39, A-41, A-42, A-43, A- 44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, The compounds of A-57 and A-58 were tested for their efficacy against armyworms (1). The insecticidal rate of any compound was 100% and effective.
(2)對黏蟲的效力試驗(2) 以本發明化合物的濃度成為125質量ppm的方式利用水對乳劑(I)進行稀釋。將玉米葉片於所述稀釋液中浸漬30秒。將該玉米葉片放入培養皿中,並投放5只黏蟲2齡幼蟲。 於試驗期間中,將所述培養皿放置於溫度25℃、濕度60%的恆溫室內。於投放後經過了6天時,進行死活判定,並算出殺蟲率。試驗反覆進行兩次。(2) Efficacy test against armyworms (2) Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The corn leaves were dipped in the dilution for 30 seconds. The corn leaf was put into a petri dish, and 5 armyworm second instar larvae were placed. During the test period, the petri dish was placed in a constant temperature room with a temperature of 25° C. and a humidity of 60%. When 6 days have passed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.
針對化合物編號A-2及A-3的化合物,進行對黏蟲的效力試驗(2)。對於黏蟲而言,任一化合物均顯示出80%以上的殺蟲率。 另一方面,乳劑(II)的殺蟲率為0%。 同樣地,針對化合物編號A-9、A-10、A-11、A-14、A-16、A-17、A-18、A-19、A-20、A-24、A-25、A-26、A-28、A-29、A-30、A-31、A-32、A-33、A-34、A-35、A-36、A-38、A-39、A-41、A-42、A-43、A-44、A-48、A-50、A-52、A-55、A-56、A-57、A-58、A-60、A-61、A-62及A-63的化合物,進行對黏蟲的效力試驗(2)。任一化合物的殺蟲率均為80%而有效。For the compounds of compound numbers A-2 and A-3, the efficacy test (2) against armyworm was carried out. For armyworms, either compound showed an insecticidal rate of over 80%. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-9, A-10, A-11, A-14, A-16, A-17, A-18, A-19, A-20, A-24, A-25, A-26, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-38, A-39, A- 41, A-42, A-43, A-44, A-48, A-50, A-52, A-55, A-56, A-57, A-58, A-60, A-61, The compounds of A-62 and A-63 were tested for their efficacy against armyworms (2). The insecticidal rate of any compound was 80% and effective.
(3)對小菜蛾(Plutella xylostella)的效力試驗 以本發明化合物的濃度成為125質量ppm的方式利用水對乳劑(I)進行稀釋。將甘藍葉於所述稀釋液中浸漬30秒。將該甘藍葉風乾而放入培養皿中,並投放5只小菜蛾2齡幼蟲。於試驗期間中,將所述培養皿放置於溫度25℃、濕度60%的恆溫室內。於投放後經過了3天時,進行死活判定,並算出殺蟲率。試驗反覆進行兩次。(3) Efficacy test against diamondback moth (Plutella xylostella) Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The cabbage leaves were dipped in the dilution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish, and five second-instar larvae of diamondback moth were put there. During the test period, the petri dish was placed in a constant temperature room with a temperature of 25° C. and a humidity of 60%. When 3 days have elapsed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.
針對化合物編號A-2及A-3的化合物,進行對小菜蛾的效力試驗。對於小菜蛾而言,任一化合物均顯示出80%以上的殺蟲率。 另一方面,乳劑(II)的殺蟲率為0%。 同樣地,針對化合物編號A-9、A-10、A-11、A-14、A-16、A-17、A-18、A-19、A-20、A-24、A-25、A-26、A-28、A-29、A-30、A-31、A-32、A-33、A-34、A-35、A-36、A-38、A-39、A-41、A-44、A-49、A-50、A-52、A-55、A-57、A-58、A-60、A-61、A-62及A-63的化合物,進行對小菜蛾的效力試驗。對於小菜蛾而言,任一化合物均顯示出80%以上的殺蟲率。For the compounds of compound numbers A-2 and A-3, efficacy tests against diamondback moth were conducted. For the diamondback moth, either compound showed an insecticidal rate of over 80%. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-9, A-10, A-11, A-14, A-16, A-17, A-18, A-19, A-20, A-24, A-25, A-26, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-38, A-39, A- 41, the compounds of A-44, A-49, A-50, A-52, A-55, A-57, A-58, A-60, A-61, A-62 and A-63 were compared Efficacy test of diamondback moth. For the diamondback moth, either compound showed an insecticidal rate of over 80%.
(4)對德國蟑螂(Blattella germanica)的效力試驗 使用微型注射器,將本發明化合物10 μg直接注射給德國蟑螂雌成蟲。繼而,將該德國蟑螂雌成蟲3只放入塑膠杯內,並放入市售的人工飼料作為餌料。於試驗期間中,將所述杯放置於溫度25℃、濕度60%的恆溫室內。於投放後經過了2天時,進行死活判定,並算出殺蟲率。試驗反覆進行兩次。(4) Efficacy test against German cockroaches (Blattella germanica) Using a microsyringe, 10 μg of the compound of the present invention was directly injected into the adult female German cockroach. Next, three adult female German cockroaches were placed in a plastic cup, and a commercially available artificial feed was placed as a bait. During the test period, the cup was placed in a constant temperature room with a temperature of 25°C and a humidity of 60%. When 2 days have passed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.
針對化合物編號A-1、A-2、A-3及A-4的化合物,進行對德國蟑螂的注射效力試驗。對於德國蟑螂而言,任一化合物均顯示出100%的殺蟲率。 另一方面,乳劑(II)的殺蟲率為0%。 同樣地,針對化合物編號A-7、A-9、A-10、A-11、A-12、A-13、A-14、A-17、A-18、A-21、A-22、A-23、A-24、A-25、A-26、A-28、A-29、A-30、A-31、A-32、A-33、A-34、A-35、A-36、A-38、A-39、A-44、A-45、A-46、A-47、A-48、A-49、A-50、A-51、A-52、A-53、A-54、A-55、A-56、A-57、A-58及A-59的化合物,進行對德國蟑螂的注射效力試驗。對於德國蟑螂而言,任一化合物均顯示出100%的殺蟲率。For the compounds of compound numbers A-1, A-2, A-3 and A-4, the injection efficacy test against German cockroach was carried out. For German cockroaches, either compound showed a 100% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-7, A-9, A-10, A-11, A-12, A-13, A-14, A-17, A-18, A-21, A-22, A-23, A-24, A-25, A-26, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A- 36, A-38, A-39, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, The compounds of A-54, A-55, A-56, A-57, A-58 and A-59 were tested for injection efficacy against German cockroaches. For German cockroaches, either compound showed a 100 percent insecticidal rate.
(5)對斜紋夜蛾(Spodoptera litura)的效力試驗 以本發明化合物的濃度成為125質量ppm的方式利用水對乳劑(I)進行稀釋。將甘藍葉於所述稀釋液中浸漬30秒。將該甘藍葉風乾而放入培養皿中,並投放5只斜紋夜蛾2齡幼蟲。將培養皿放置於溫度25℃、濕度60%的恆溫室內。於投放後經過了6天時,進行死活判定,並算出殺蟲率。試驗反覆進行兩次。(5) Efficacy test against Spodoptera litura Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The cabbage leaves were dipped in the dilution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish, and five second-instar larvae of Spodoptera litura were put there. The petri dish was placed in a constant temperature room with a temperature of 25°C and a humidity of 60%. When 6 days have passed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.
針對化合物編號A-9、A-17、A-18、A-19、A-20、A-26、A-28、A-29、A-30、A-31、A-32、A-33、A-34、A-35、A-36、A-38、A-39、A-41、A-42、A-43、A-44、A-50、A-52、A-57、A-58、A-60、A-61、A-62及A-63的化合物,進行對斜紋夜蛾的效力試驗。任一化合物均顯示出80%以上的殺蟲率。 另一方面,乳劑(II)的殺蟲率為0%。For compound numbers A-9, A-17, A-18, A-19, A-20, A-26, A-28, A-29, A-30, A-31, A-32, A-33 , A-34, A-35, A-36, A-38, A-39, A-41, A-42, A-43, A-44, A-50, A-52, A-57, A -58, A-60, A-61, A-62 and A-63 compounds were tested for their efficacy against Spodoptera litura. Either compound showed more than 80% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.
(6)對棉蚜(Aphis gossypii)的效力試驗 於3吋盆中播種黃瓜。於發芽後經過了10天的黃瓜上投放棉蚜雌成蟲。第二天,將所產下的1齡幼蟲留下,將雌成蟲去除。以本發明化合物濃度成為125質量ppm的方式利用水對乳劑(I)進行稀釋。對所述黃瓜散布該稀釋液。然後,將黃瓜放置於溫度25℃、濕度60%的恆溫室內,經過5天後,研究棉蚜的死活,並求出殺蟲率。(6) Efficacy test on cotton aphid (Aphis gossypii) Sow cucumbers in 3-inch pots. Cotton aphid female adults were placed on cucumbers 10 days after germination. The next day, the first instar larvae produced were left, and the female adults were removed. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass. This dilution is spread over the cucumbers. Then, the cucumbers were placed in a constant temperature room with a temperature of 25°C and a humidity of 60%, and after 5 days, the life and death of cotton aphids were studied, and the insecticidal rate was obtained.
針對化合物編號A-9、A-14、A-17、A-19、A-25、A-28、A-29、A-30、A-38、A-39、A-41、A-50、A-55及A-57的化合物,進行對棉蚜的效力試驗。任一化合物均顯示出80%以上的殺蟲率。 另一方面,乳劑(II)的殺蟲率為0%。For compound numbers A-9, A-14, A-17, A-19, A-25, A-28, A-29, A-30, A-38, A-39, A-41, A-50 , A-55 and A-57 compounds were tested for efficacy against cotton aphid. Either compound showed more than 80% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.
(7)對棕櫚薊馬(Thrips palmi)的效力試驗 於黃瓜苗上接種8只棕櫚薊馬成蟲。以本發明化合物的濃度成為125質量ppm的方式利用水對乳劑(I)進行稀釋。對黃瓜苗散布該稀釋液並進行風乾。於散布後經過了7天時,計數寄生幼蟲數。化合物的效力是藉由下述所示的防治率來進行評價。 防治率(%)={1-(Nt)/(Nc)}×100 Nt:散布處理區的寄生蟲數 Nc:未處理區的寄生蟲數(7) Efficacy test on Thrips palmi Eight adults of Thrips palmi were inoculated on cucumber seedlings. Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The dilution was spread on cucumber seedlings and air-dried. The number of parasitic larvae was counted when 7 days had passed after dispersal. The efficacy of the compounds was evaluated by the control rates shown below. Control rate (%)={1-(Nt)/(Nc)}×100 Nt: the number of parasites in the scattered treatment area Nc: the number of parasites in the untreated area
針對化合物編號A-17、A-19、A-26、A-28、A-29、A-30、A-31、A-39、A-41、A-50及A-57的化合物,進行對棕櫚薊馬的效力試驗。任一化合物均顯示出80%以上的防治率。 另一方面,乳劑(II)的防治率為0%。For the compounds of compound numbers A-17, A-19, A-26, A-28, A-29, A-30, A-31, A-39, A-41, A-50 and A-57, the Efficacy test on Thrips palmi. Either compound showed a control rate of over 80%. On the other hand, the control rate of Emulsion (II) was 0%.
(8)對褐飛虱(Nilaparvata lugens)的效力試驗 以本發明化合物的濃度成為125質量ppm的方式利用水對乳劑(I)進行稀釋。將稻幼苗於所述稀釋液中浸漬30秒,風乾後,放入塑膠箱中,並投放5只褐飛虱2齡幼蟲。放置於溫度25℃、濕度65%的恆溫室內,自接種起10天後,進行死活判定,並藉由下述式來算出殺蟲率。試驗反覆進行兩次。 殺蟲率(%)=(死亡蟲數/受試蟲數)×100(8) Efficacy test against brown planthopper (Nilaparvata lugens) Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The rice seedlings were immersed in the diluent for 30 seconds, and after air-drying, they were put into a plastic box, and 5 second-instar larvae of N. lugens were placed. It was placed in a constant temperature room with a temperature of 25°C and a humidity of 65%, and 10 days after the inoculation, the dead or alive was judged, and the insecticidal rate was calculated by the following formula. The test was repeated twice. Insecticidal rate (%) = (number of dead insects/number of tested insects) × 100
針對化合物編號A-26、A-29、A-30、A-39及A-57的化合物,進行對褐飛虱的效力試驗。任一化合物均顯示出80%以上的殺蟲率。 另一方面,乳劑(II)的殺蟲率為0%。For the compounds of compound numbers A-26, A-29, A-30, A-39 and A-57, the efficacy test against N. lugens was carried out. Either compound showed more than 80% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.
(9)對家蠅的效力試驗 利用丙酮來稀釋本發明化合物,以成為100質量ppm的方式滴加至1 g的方糖上。將該方糖放入塑膠杯中,投放10只家蠅雌成蟲,蓋上蓋。於25℃下保管,於投放24小時後,進行死活判定,並藉由下式來算出殺蟲率。試驗反覆進行兩次。(9) Efficacy test against housefly The compound of the present invention was diluted with acetone and added dropwise to 1 g of sugar cubes so as to be 100 mass ppm. Put the sugar cube into a plastic cup, put 10 adult female houseflies, and cover it. It was stored at 25 degreeC, and 24 hours after it was put in, the life-and-death determination was performed, and the insecticidal rate was calculated by the following formula. The test was repeated twice.
針對化合物編號A-17、A-18、A-19、A-29及A-30的化合物,進行對家蠅雌成蟲的效力試驗。任一化合物均顯示出100%的殺蟲率。 另一方面,乳劑(II)的殺蟲率為0%。For the compounds of compound numbers A-17, A-18, A-19, A-29 and A-30, the efficacy test on female adult housefly was carried out. Either compound showed 100% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.
自本發明化合物中隨機選擇的化合物起到如上所述的效果,因此可理解為本發明化合物包括未完全於實施例中示出的化合物在內均是具有有害生物防治、殺蟎、尤其是殺蟲等效果的化合物。 [產業上之可利用性]The compounds randomly selected from the compounds of the present invention have the above-mentioned effects, so it can be understood that the compounds of the present invention, including those not completely shown in the examples, have the functions of controlling pests, killing acarids, especially killing compounds with insect effects. [Industrial Availability]
本發明的吖嗪基唑化合物具有防治於農作物或衛生方面成為問題的有害生物。含有本發明的吖嗪基唑化合物的防治劑可以更低的濃度有效地防治有害生物、尤其是農業害蟲及蟎類,進而,可有效地防治有時危害人畜的外部寄生蟲及內部寄生蟲。The azinylazole compound of the present invention has the ability to control harmful organisms that are problematic in terms of crops or sanitation. The control agent containing the azinylazole compound of the present invention can effectively control harmful organisms, especially agricultural pests and mites, at a lower concentration, and further, can effectively control external parasites and internal parasites that sometimes harm humans and animals.
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