TW201336841A - 殺蟲組成物及與其相關之方法(一) - Google Patents
殺蟲組成物及與其相關之方法(一) Download PDFInfo
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- TW201336841A TW201336841A TW102104027A TW102104027A TW201336841A TW 201336841 A TW201336841 A TW 201336841A TW 102104027 A TW102104027 A TW 102104027A TW 102104027 A TW102104027 A TW 102104027A TW 201336841 A TW201336841 A TW 201336841A
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- haloalkyl
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- cycloalkyl
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- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- QERFJLRDDKQIKF-UHFFFAOYSA-L zinc;2-acetyloxybenzoate Chemical compound [Zn+2].CC(=O)OC1=CC=CC=C1C([O-])=O.CC(=O)OC1=CC=CC=C1C([O-])=O QERFJLRDDKQIKF-UHFFFAOYSA-L 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
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- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
本文件揭露具有下列化學式(“化學式1”&”化學式2”及”化學式3”)分子□Ar1、Het、Ar2、R1、R2、R3、R4,及R5係於此處進一步描述。
Description
本申請案主張於2012年2月2日申請之美國臨時申請案第61/594,054號案之優先權,此臨時申請案之完整內容在此併入本申請案以為參考資料。
於本文件揭露之發明係有關於製造可作為殺蟲劑(例如,殺蟎劑、殺昆蟲劑、殺螺劑,及殺線蟲劑)之分子的方法、此等分子,及使用此等分子控制害蟲之領域。
害蟲每年會造成全世界數百萬人死亡。再者,有多於萬種害蟲會造成農業損失。每年全世界農業損失總計數十億美元。
白蟻造成所有種類之私人及公共結構損害。每年全世界白蟻損失總計數十億美元。
貯存食物之害蟲吃掉及混入貯存食物。每年全世界貯存食物損失總計數十億美元,但更重要地,剝奪人類所需食物。
急迫需要新的殺蟲劑。某些害蟲發展出對現今使用殺蟲劑之抗性。數百種害蟲係抵抗一或多種殺蟲劑。對諸如DDT、氨基甲酸酯,及有機磷酸酯之一些較舊殺蟲劑之抗性的發展係已知,但進一步發展出對某些較新殺蟲劑之抗性。
因此,由於包括上述原因之許多原因,存在於新殺蟲劑之需要。
依據本發明之一實施例,係特地提出一種組成物,包含依據化學式2或3之分子,
其中:(a)Ar1係(1)呋喃基、苯基、嗒基、吡啶基、嘧啶基、噻吩基,或(2)經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,或經取代之噻吩基,其中,該經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,及經取代之噻吩基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、
C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基、經取代之苯基,及經取代之苯氧基,其中,該經取代之苯基及經取代之苯氧基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)苯基,及苯氧基;(b)Het係一含有一或多個立地選自氮、硫,或氧之雜原子之5或6員、飽和或不飽和、雜環狀環,且其中,Ar1及Ar2彼此不呈鄰位(但可為間位或對位,諸如,對於一五員環,
其等係1,3,且對於一6員環,其等係1,3或1,4),且其中,該雜環狀環亦可以一或多個獨立地選自下列之取代基取代:H、F、Cl、Br、I、CN、NO2、氧基、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基、經取代之苯基,及經取代之苯氧基,其中,該經取代之苯基及經取代之苯氧基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷
基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,及苯氧基;(c)Ar2係(1)呋喃基、苯基、嗒基、吡啶基、嘧啶基、噻吩基,或(2)經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,或經取代之噻吩基,其中,該經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,及經取代之噻吩基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基、經取代之苯基,及經取代之苯氧基,其中,該經取代之苯基及經取代之苯氧基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環
烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C1-C6鹵烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,及苯氧基;(d)R1係選自H、CN、F、Cl、Br、I、C1-C6烷基、C3-C6環烷基、C3-C6環烷氧基、C1-C6烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、OSO2(C1-C6烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,或苯氧基,其中,每一烷基、環烷基、環烷氧基、烷氧基、烯基、炔基、苯基,及苯氧基係選擇性以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、氧基、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、
S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,及苯氧基;(g)R4係H、C1-C6烷基、C3-C6環烷基、C2-C6烯基、C2-C6炔基、C(=O)H、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、C1-C6烷基苯基、C1-C6烷基-O-苯基、C(=O)Het-1、Het-1、C1-C6烷基Het-1,或C1-C6烷基-O-Het-1,其中,每一烷基、環烷基、烯基、炔基、苯基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、
C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基,及Het-1;(h)R5係一1員之飽和烴基連接,其中,該連接亦可以下列取代:F、Cl、Br、I、CN、NO2、氧基、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)OH、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基,及Het-1,其中,每一烷基、環烷基、環烷氧基、烷氧基、烯基、炔基、苯基、苯氧基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、氧基、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6
烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)OH、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、鹵苯基、苯氧基,及Het-1;(i)n=0、1,或2;(j)Rx及Ry係獨立地選自H、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基),及苯基,其中,每一烷基、環烷基、環烷氧基、烷氧基、烯基、炔基、苯基、苯氧基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、氧基、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷
基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)OH、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、鹵苯基、苯氧基,及Het-1,或Rx及Ry一起可選擇性地形成一可含有一或多個選自氮、硫,及氧之雜原子之5至7員之飽和或不飽和之環狀基團,且其中,該環狀基團可含有>C=O或>C=S,且其中,該環狀基團可以下列取代:F、Cl、Br、I、CN、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、經取代之苯基、苯氧基,及Het-1;且(k)Het-1係一含有一或多個獨立地選自氮、硫或氧之雜原子之5或6員、飽和或不飽和、雜環狀之環。
定義內所提供之範例一般並非詳盡,且不應被作為限制此文件所揭露之發明而闡釋。需瞭解一取代基需遵守與和其附接之特定分子有關之化學鍵結規則及立體相容性限制。
“殺蟎劑組群”係於標題為“殺蟎劑”中定義。
“AI組群”係於此文件中定義“殺蟲劑組群”之位置後定義。
“烯基”意指由碳及氫所組成之非環狀、不飽和(至少一個碳碳雙鍵)、分支或未分支之取代基,例如,乙烯基、丙烯基、丁烯基、戊烯基,及己烯基。
“烯氧基”意指進一步由一碳氧單鍵所組成之烯基,例如,丙烯氧基、丁烯氧基、戊烯氧基、己烯氧基。
“烷氧基”意指進一步由一碳氧單鍵所組成之烷基,例如,甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、異丁氧基,及第三丁氧基。
“烷基”意指由碳及氫組成之非環狀、飽和、分支或未分支之取代基,例如,甲基、乙基、丙基、異丙基、丁基,及第三丁基。
“炔基”意指由碳及氫所組成之非環狀、不飽和(至少一個碳碳三鍵)、分支或未分支之取代基,例如,乙炔基、丙炔基、丁炔基,及戊炔基。
“炔氧基”意指進一步由一碳氧單鍵所組成之炔
基,例如,戊炔氧基、己炔氧基、庚炔氧基,及辛炔氧基。
“芳基”意指由氫及碳所組成之一環狀芳香族取代基,例如,苯基、萘基,及聯苯基。
“環烯基”意指由碳及氫所組成之一單環狀或多環狀、不飽和(至少一個碳碳雙鍵)之取代基,例如,環丁烯基、環戊烯基、環己烯基、降冰片烯基、二環[2.2.2]辛烯基、四氫萘基、六氫萘基,及八氫萘基。
“環烯氧基”意指進一步由一碳氧單鍵所組成之環烯基,例如,環丁烯氧基、環戊烯氧基、降冰片烯氧基,及二環[2.2.2]辛烯氧基。
“環烷基”意指由碳及氫所組成之一單環狀或多環狀、飽和之取代基,例如,環丙基、環丁基、環戊基、降冰片基、二環[2.2.2]辛基,及十氫萘基。
“環烷氧基”意指進一步由一碳氧單鍵所組成之環烷基,例如,環丙氧基、環丁氧基、環戊氧基、降冰片氧基,及二環[2.2.2]辛氧基。
“殺黴菌劑組群”係於標題為“殺黴菌劑”定義。
“鹵基”意指氟、氯、溴,及碘。
“鹵烷氧基”意指進一步由一至最大可能數量之相同或相異之鹵基所組成之烷氧基,例如,氟甲氧基、三氟甲氧基、2,2-二氟丙氧基、氯甲氧基、三氯甲氧基、1,1,2,2-四氟乙氧基,及五氟乙氧基。
“鹵烷基”意指進一步由一至最大可能數量之相同或相異之鹵基所組成之烷基,例如,氟甲基、三氟甲基、
2,2-二氟丙基、氯甲基、三氯甲基,及1,1,2,2-四氟乙基。
“除草劑組群”係於標題為“除草劑”定義。
“雜環基”意指其中環狀結構含有至少一個碳及至少一個雜原子,其中該雜原子係氮、硫,或氧之可為完全飽和、部份不飽和,或完全不飽和之環狀取代基。芳香族雜環基之例子不受限制地包括苯并呋喃基、苯并異噻唑基、苯并異唑基、苯并唑基、苯并噻吩基、苯并噻唑基、啉基、呋喃基、吲唑基、吲哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、呔基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三基,及三唑基。完全飽和之雜環基之例子不受限制地包括哌基、哌啶基、嗎啉基、吡咯啶基、四氫呋喃基,及四氫哌喃基。部份不飽和之雜環基之例子不受限制地包括1,2,3,4-四氫-喹啉基、4,5-二氫-唑基、4,5-二氫-1H-吡唑基、4,5-二氫-異唑基,及2,3-二氫-[1,3,4]-二唑基。
“殺昆蟲劑組群”係於標題為“殺昆蟲劑”定義。
“殺線蟲劑組群”係於標題為“殺線蟲劑”定義。
“增效劑組群”係於標題為“增效劑混合物及增效劑”定義。
本文件揭露具有下列化學式(“化學式1”&“化學式2”及“化學式3”)之分子:(於下列化學式中,氮係編號為
1、2,及3,僅係為了對其等作識別之目的及能於此整份文件中清楚提及)
其中(a)Ar1係(1)呋喃基、苯基、嗒基、吡啶基、嘧啶基、噻吩基,或(2)經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,或經取代之噻吩基,其中,該經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,及經取代之噻吩基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷
基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基、經取代之苯基,及經取代之苯氧基,其中,此經取代之苯基及經取代之苯氧基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)苯基,及苯氧基;(b)Het係一含有一或多個立地選自氮、硫,或氧之雜原子之5或6員、飽和或不飽和、雜環狀環,且其中,Ar1及Ar2彼此不呈鄰位(但可為間位或對位,諸如,對於一五員環,其等可為1,3,且對於一6員環,其等可為1,3或1,4),且其中,雜環狀環亦可以一或多個獨立地選自下列之取代基取代:H、F、Cl、Br、I、CN、NO2、氧基、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6
鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基、經取代之苯基,及經取代之苯氧基,其中,此經取代之苯基及經取代之苯氧基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,及苯氧基;(c)Ar2係(1)呋喃基、苯基、嗒基、吡啶基、嘧啶基、噻吩
基,或(2)經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,或經取代之噻吩基,其中,該經取代之呋喃基、經取代之苯基、經取代之嗒基、經取代之吡啶基、經取代之嘧啶基,及經取代之噻吩基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基、經取代之苯基,及經取代之苯氧基,其中,此經取代之苯基及經取代之苯氧基具有一或多個獨立地選自下列之取代基:H、F、Cl、Br、I、CN、NO2、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6
鹵烷基)、C(=O)H、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C1-C6鹵烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,及苯氧基;(d)R1係選自H、CN、F、Cl、Br、I、C1-C6烷基、C3-C6環烷基、C3-C6環烷氧基、C1-C6烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、OSO2(C1-C6烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,或苯氧基,其中,每一烷基、環烷基、環烷氧基、烷氧基、烯基、炔基、苯基,及苯氧基係選擇性以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、氧基、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6
鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基,及苯氧基;(e)R2係H、C1-C6烷基、C3-C6環烷基、C2-C6烯基、C2-C6炔基、C(=O)H、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、C1-C6烷基苯基、C1-C6烷基-O-苯基、C(=O)Het-1、Het-1、C1-C6烷基Het-1,或C1-C6烷基-O-Het-1,其中,每一烷基、環烷基、烯基、炔基、苯基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6
烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基,及Het-1;(f)R3係C1-C6烷基、C3-C6環烷基、C2-C6烯基、C2-C6炔基、C(=O)H、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、C1-C6烷基苯基、C1-C6烷基-O-苯基、C(=O)Het-1、Het-1、C1-C6烷基Het-1、C1-C6烷基-O-C(=O)C1-C6烷基-O-C1-C6烷基、C1-C6烷基-O-C(=O)C1-C6烷基-O-C1-C6烷基-O-C1-C6烷基、C1-C6烷基-O-C(=O)C1-C6烷基-O-C1-C6鹵烷基、C1-C6烷基-O-C(=O)C1-C6烷基-N(Rx)C(=O)-O-苯基、C1-C6烷基-O-C(=O)C1-C6烷基-N(Rx)C(=O)-O-C1-C6烷基苯基、C1-C6烷基C(=O)N(Rx)C1-C6烷基、C1-C6烷基C(=O)N(Rx)C1-C6烷基Het-1C(=O)-O-C1-C6烷基、C1-C6烷基C(=O)N(Rx)C1-C6烷基Het-1、C1-C6烷基C(=O)Het-1、C1-C6烷基C(=O)N(Rx)C1-C6烷基(N(Rx)(Ry))(C(=O)OH)、C1-C6烷基C(=O)N(Rx)C1-C6烷基N(Rx)(Ry)、C1-C6烷基C(=O)N(Rx)C1-C6烷基N(Rx)C(=O)-O-C1-C6烷基、C1-C6烷基C(=O)N(Rx)C1-C6烷基(N(Rx)C(=O)-O-C1-C6烷基)(C(=O)OH)、C1-C6烷基C(=O)Het-1C(=O)-O-C1-C6烷基、C1-C6烷基-O-C(=O)-O-C1-C6烷基、C1-C6烷基-O-C(=O)C1-C6烷基、C1-C6烷基-O-C(=O)C3-C6環烷基、C1-C6烷基-O-C(=O)Het-1、C1-C6烷基-O-C(=O)C1-C6烷基
-N(Rx)C(=O)-O-C1-C6烷基、C1-C6烷基-NRxRy,或C1-C6烷基-O-Het-1,其中,每一烷基、環烷基、烯基、炔基、苯基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)OH、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基、Si(C1-C6烷基)3、S(=O)nNRxRy,及Het-1;(g)R4係H、C1-C6烷基、C3-C6環烷基、C2-C6烯基、C2-C6炔基、C(=O)H、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、C1-C6烷基苯基、C1-C6烷基-O-苯基、C(=O)Het-1、Het-1、C1-C6烷基Het-1,或C1-C6烷基-O-Het-1,
其中,每一烷基、環烷基、烯基、炔基、苯基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基,及Het-1;(h)R5係一1員之飽和或一2至4員之飽和或不飽和之烴基連接,其中,該連接亦可以下列取代:F、Cl、Br、I、CN、NO2、氧基、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)OH、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6
烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、苯氧基,及Het-1,其中,每一烷基、環烷基、環烷氧基、烷氧基、烯基、炔基、苯基、苯氧基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、氧基、NRxRy、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)OH、C(=O)NRxRy、(C1-C6烷基)NRxRy、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、鹵苯基、苯氧基,及Het-1;(i)n=0、1,或2;(j)Rx及Ry係獨立地選自H、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C2-C6烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷
基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基),及苯基,其中,每一烷基、環烷基、環烷氧基、烷氧基、烯基、炔基、苯基、苯氧基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、I、CN、NO2、氧基、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)H、C(=O)OH、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、鹵苯基、苯氧基,及Het-1,或Rx及Ry一起可選擇性地形成一可含有一或多個選自氮、硫,及氧之雜原子之5至7員之飽和或不飽和之環狀基團,且其中,該環狀基團可含有>C=O或>C=S,且其中,該環狀基團可以下列取代:F、Cl、Br、I、CN、C1-C6烷基、C1-C6鹵烷基、C3-C6環烷基、C3-C6鹵環烷基、C3-C6環烷氧基、C3-C6鹵環烷氧基、C1-C6烷氧基、C1-C6鹵烷氧基、C2-C6烯基、C3-C6環烯基、C2-C6炔基、S(=O)n(C1-C6烷基)、S(=O)n(C1-C6鹵烷基)、OSO2(C1-C6烷基)、OSO2(C1-C6鹵烷基)、C(=O)(C1-C6烷基)、C(=O)O(C1-C6烷基)、
C(=O)(C1-C6鹵烷基)、C(=O)O(C1-C6鹵烷基)、C(=O)(C3-C6環烷基)、C(=O)O(C3-C6環烷基)、C(=O)(C2-C6烯基)、C(=O)O(C2-C6烯基)、(C1-C6烷基)O(C1-C6烷基)、(C1-C6烷基)S(C1-C6烷基)、C(=O)(C1-C6烷基)C(=O)O(C1-C6烷基)、苯基、經取代之苯基、苯氧基,及Het-1;且(k)Het-1係一含有一或多個獨立地選自氮、硫或氧之雜原子之5或6員、飽和或不飽和、雜環狀之環。
需瞭解於化學式1中,當R2係H,化合物可以多於一種互變異構物或異構物型式存在,其中,氫係附接至任一氮原子;再者,E及Z異構物二者皆可存在。本發明之此等化合物之任何及所有異構物型式被請求。
於另一實施例,Ar1係一經取代之苯基,其中,該經取代之苯基具有一或多個獨立地選自C1-C6鹵烷基及C1-C6鹵烷氧基之取代基。
於另一實施例,Ar1係一經取代之苯基,其中,該經取代之苯基具有一或多個獨立地選自CF3、OCF3,及OCF2CF3之取代基。
於另一實施例,Het係選自三唑基、咪唑基,或吡唑基,其等可經取代或未經取代。
於另一實施例,Het係1,2,4-三唑基
於另一實施例,Het係1,4-咪唑基
於另一實施例,Het係1,3-吡唑基
於另一實施例,Het係經取代之1,3-吡唑基。
於另一實施例,Het係1,4-吡唑基
於另一實施例,Ar2係苯基。
於另一實施例,R1係H或C1-C6烷基。
於另一實施例,R1係H或CH3。
於另一實施例,R2係H。
於另一實施例,R3係選自C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷基苯基、C1-C6烷基Het-1、C1-C6烷基-O-C(=O)C1-C6烷基-O-C1-C6烷基、C1-C6烷基-O-C(=O)C1-C6烷基-O-C1-C6烷基-O-C1-C6烷基、C1-C6烷基-O-C(=O)C1-C6烷基-O-C1-C6鹵烷基、C1-C6烷基-O-C(=O)C1-C6烷基-N(Rx)C(=O)-O-苯基、C1-C6烷基-O-C(=O)C1-C6烷基-N(Rx)C(=O)-O-C1-C6烷基苯基、C1-C6烷基C(=O)N(Rx)C1-C6烷基、C1-C6烷基C(=O)N(Rx)C1-C6烷
基Het-1C(=O)-O-C1-C6烷基、C1-C6烷基C(=O)N(Rx)C1-C6烷基Het-1、C1-C6烷基C(=O)Het-1、C1-C6烷基C(=O)N(Rx)C1-C6烷基(N(Rx)(Ry))(C(=O)OH)、C1-C6烷基C(=O)N(Rx)C1-C6烷基N(Rx)(Ry)、C1-C6烷基C(=O)N(Rx)C1-C6烷基N(Rx)C(=O)-O-C1-C6烷基、C1-C6烷基C(=O)N(Rx)C1-C6烷基(N(Rx)C(=O)-O-C1-C6烷基)(C(=O)OH)、C1-C6烷基C(=O)Het-1C(=O)-O-C1-C6烷基、C1-C6烷基-O-C(=O)-O-C1-C6烷基、C1-C6烷基-O-C(=O)C1-C6烷基、C1-C6烷基-O-C(=O)C3-C6環烷基、C1-C6烷基-O-C(=O)Het-1,或C1-C6烷基-O-C(=O)C1-C6烷基-N(Rx)C(=O)-O-C1-C6烷基,其中,每一烷基、烯基、炔基、苯基,及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、C1-C6烷基、C1-C6鹵烷基、C1-C6鹵烷氧基、S(=O)n(C1-C6烷基)、C(=O)OH、C(=O)O(C1-C6烷基)、苯基、Si(C1-C6烷基)3,及S(=O)nNRxRy。
於另一實施例,R4係苯基、C1-C6烷基苯基、Het-1,或C1-C6烷基-O-苯基,其中,每一烷基、Het-1,及苯基係選擇性地以一或多個選自下列之取代基取代:F、Cl、NRxRy、C1-C6烷基、C3-C6環烷基、C1-C6鹵烷氧基、C(=O)OC1-C6烷基,或C1-C6烷氧基。
於另一實施例,R5係以氧基、C(=O)OH、苯基,及Het-1取代,其中,每一苯基及Het-1可選擇性地以一或多個獨立地選自下列之取代基取代:氧基、C1-C6鹵烷基、C1-C6鹵烷氧基、C(=O)OH,及鹵苯基。
於另一實施例,Rx及Ry係獨立地選自H及苯基,其中,該苯基可選擇性地以一或多個獨立地選自F及Cl之取代基取代。
於另一實施例:Ar1係一經取代之苯基,其中,該經取代之苯基具有一或多個C1-C6鹵烷氧基;Het係三唑基;Ar2係苯基;R1係H;R2係H;R3係C1-C6烷基Het-1,其中,該烷基及Het-1係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、Br、C1-C6烷基、C1-C6鹵烷基、C1-C6鹵烷氧基、S(=O)n(C1-C6烷基)、C(=O)OH、C(=O)O(C1-C6烷基)、苯基、Si(C1-C6烷基)3,及S(=O)nNRxRy;R4係苯基,其中,該苯基係選擇性地以一或多個獨立地選自下列之取代基取代:F、Cl、NRxRy、C1-C6烷基,或C1-C6烷氧基;且n=0、1,或2;Rx及Ry係獨立地選自H及苯基,其中,該苯基可選擇性地以一或多個獨立地選自F及Cl之取代基取代;且Het-1係一含有一或多個獨立地選自氮、硫,或氧之雜原子之5或6員、飽和或不飽和、雜環狀之環。
於另一實施例,Het-1係選自苯并呋喃基、苯并
異噻唑基、苯并異唑基、苯并唑基、苯并噻吩基、苯并噻唑基、啉基、呋喃基、吲唑基、吲哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、酞基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹唑啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三基、三唑基、哌基、哌啶基、嗎啉基、吡咯啶基、四氫呋喃基、四氫吡喃基、1,2,3,4-四氫喹啉基、4,5-二氫唑基、4,5-二氫-1H-吡唑基、4,5-二氫異唑基,及2,3-二氫-[1,3,4]-二唑基。
於另一實施例,Het係選自苯并呋喃基、苯并異噻唑基、苯并異唑基、苯并唑基、苯并噻吩基、苯并噻唑基、啉基、呋喃基、吲唑基、吲哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、酞基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三基、三唑基、哌基、哌啶基、嗎啉基、吡咯啶基、四氫呋喃基、四氫吡喃基、1,2,3,4-四氫喹啉基、4,5-二氫唑基、4,5-二氫-1H-吡唑基、4,5-二氫異唑基,及2,3-二氫-[1,3,4]-二唑基。
於另一實施例,Het-1係選自苯并呋喃基、苯并異噻唑基、苯并異唑基、苯并唑基、苯并噻吩基、苯并噻唑基、苯并噻二唑基、啉基、呋喃基、吲唑基、吲
哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、酞基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹啉基、四唑基、噻唑啉基、噻唑基、噻吩基、噻吩基吡唑基、三基、三唑基、哌基、哌啶基、嗎啉基、吡咯啶基、四氫呋喃基、四氫吡喃基、1,2,3,4-四氫喹啉基、4,5-二氫唑基、4,5-二氫-1H-吡唑基、4,5-二氫-異唑基,及2,3-二氫-[1,3,4]-二唑基。
於另一實施例,Het-1係選自苯并噻二唑基、呋喃基、唑基,及噻吩基吡唑基。
雖然此等實施例已被表示,但其它實施例及此等表示實施例及其它實施例之組合係可能。
具化學式1、2及3之分子一般會具有約100道爾頓(Dalton)至約1200道爾頓之分子質量。但是,若分子質量係從約120道爾頓至約900道爾頓,一般係較佳,且若分子質量係從約400道爾頓至約800道爾頓,一般係更佳。
本發明之化合物可藉由製造三芳基中間物,Ar1-Het-Ar2,然後,將其與所欲中間物連接形成所欲化合物而製備。廣泛之各種三芳基中間物可用以製備本發明之化合物,只要此等三芳基中間物於可與所欲中間物之剩餘者附接之Ar2上含有一適合官能基團。適合之官能基團包含氧烷基或甲醯基基團。此等三芳基中間物可藉由先前於化學文獻中描述之方法製備,包括Crouse等人,PCT Int.Appl.
Publ.WO2009/102736 A1。
經腙連接之化合物可藉由三種方法之一自相對應之芳基醛或酮製備:(1)藉由與肼反應,其後與芳基異硫氰酸酯於四氫呋喃(THF)中,於0與100℃間之溫度反應(反應A);(2)藉由與甲基肼二硫代甲酸酯反應,其後藉由與苯胺於極性非質子性溶劑(諸如,N,N-二甲基甲醯胺(DMF))中,於25與150℃間之溫度反應(反應B);或(3)藉由與芳基硫半卡肼(其係可購得或可由熟習此項技藝者製備)於極性質子性溶劑(諸如,乙醇(EtOH))中,於0與100℃間之溫度反應(反應C)。
經烷化之經腙連接之化合物可藉由二方法之一自相對應之經腙連接之化合物製備:(1)藉由與烷化劑於EtOH或丙酮中,於0與100℃間之溫度反應1至24小時,或(2)藉由與烷化劑於氯仿(CHCl3)、二氯甲烷(CH2Cl2),或其它鹵碳化合物溶劑中,具有或不具有鹼(諸如,碳酸氫鈉),於
20至60℃反應。
具有其中R5與N3形成一環之化學式2(見以下之流程)或具有其中R5與N2形成一環之化學式3之化合物可自適合之非環狀先質,藉由使用α-鹵酸、酸鹵化物、酯,或酮(F或G或H)製備。例如,於極性溶劑(諸如,EtOH或甲醇(CH3OH))中,以些微過量之α-鹵酯處理硫半卡腙,造成S-烷化及其後排它地於N3上之閉環(反應F;見,例如,J.Indian Chemical Society 1966,43,275-276,或J.Heterocycl.Chem.1978,15,335-336)。當諸如CH2Cl2或二氯乙烷(ClCH2CH2Cl)之非質子性溶劑於30℃至80℃之溫度使用時,α鹵酮之加成方向亦有利於N3上之閉合,及其後之脫水形成亞胺基噻唑啉(反應G)。以於鹵碳化合物溶劑(諸如,CH2Cl2或ClCH2CH2Cl)中之α-鹵酸或酸鹵化物或酯,觀察到於N2(反應H)及N3上之閉環。雖然此等反應通常於無添加鹼而進行,但可添加諸如碳酸氫鈉、碳酸鈉或乙酸鈉之鹼,或諸如吡啶或三乙基胺之胺鹼。
另外,3-芳啶亞胺基-2-芳基亞胺基噻唑啉-4-酮可藉由如下流程(I)所示般,於乙酸中,於30至70℃,以3-胺基-2-(芳基亞胺基)四氫噻唑-4-酮處理醛或酮而製備,其中,R1係如前所述。中間物1-胺基-2-芳基亞胺基噻唑啉-5-酮,其中,R4係苯基,已被描述(見,例如,J.Org.Chem.1962,27,2878);藉由於熱EtOH中以2-氯乙酸乙酯及乙酸鈉處理4-苯基硫半卡肼以80%產率製備。
另外,具化學式2及化學式3之化合物可藉由丙酮或2-丁酮或其它適合溶劑中,使用諸如碳酸鉀或三乙基胺之鹼,於環境與100℃間之溫度,使硫半卡腙先質與二鹵基
團Hal1-R5-Hal2(諸如,1-溴-2-氯乙烷或二碘甲烷)加熱1至72小時而形成。S-烷化中間物於N2或N3進行環化產生具有化學式2或化學式2之化合物(反應J)。於某些情況,需要添加KI以加速中間物S-烷化衍生物之環化成閉環產物。
製備本發明化合物之一另外方法係藉由以不飽和之酯或酸氯化物處理硫半卡腙先質(反應L)。
經取代之肼硫代甲醯胺中間物,諸如,於如上之方法C中使用者,可藉由化學文獻中所知之數種方法製備。另外,其中Ra、Rb,及Rc非衍生自一可購得苯胺之化合物可依據下列流程製備。例如,以一或多個Rc取代基取代之2-鹵硝基苯,諸如,2-溴硝基苯,其中,Rc可為H、烷基、烷氧基,或鹵(諸如,氟),可於鹼(例如,碳酸鈉)及鈀催化劑(諸如,雙(三苯基膦)鈀(II)氯化物)存在中,於水性溶劑
系統(諸如,4:1二烷/水),於高溫(例如,80℃),與硼酸或硼酸酯(諸如,經取代之4,4,5,5-四甲基-1,3,2-二氧硼戊環反應,其中,Ra及Rb係H,提供經烯烴取代之硝基苯化合物。另外,Ra及Rb可一起形成一環,諸如,環戊烯,產生相對應之2-(環戊-1-烯-1-基)-4,4,5,5-四甲基-1,3,2-二氧硼戊環,其於上述條件下提供經環狀烯取代之硝基苯。於催化劑(例如,於碳上之鈀(Pd/C))存在中,以氫氣處理於非質子性溶劑(諸如,乙酸乙酯)中之烯烴硝基苯溶液,其中,Ra、Rb,及Rc係如上定義,提供相對應之經烷基或環烷基取代之苯胺。以鹼(諸如,碳酸氫鈉)處理於鹵化溶劑及水之混合物(諸如,2:1之二氯甲烷/水)中之苯胺的二相溶液,其中,Ra、Rb,及Rc係如所定義,其後以硫光氣處理提供中間物異硫氰基苯。分離此等相,其後乾燥及蒸發有機溶劑提供粗製中間物,使其溶於醇(諸如,乙醇),且以肼水合物處理,產生肼硫代甲醯胺中間物,其中,Ra、Rb,及Rc係如所定義。
此等範例係用於例示目的,且不能闡釋為將此文件揭露之本發明僅限於此等範例中揭露之實施例。
自商業來源獲得之起始材料、試劑,及溶劑係於未進一步純化而使用。無水溶劑係購自Aldrich之Sure/SealTM,且以收到者使用。熔點係於Thomas Hoover Unimelt毛細管熔點裝置或Stanford Research Systems之OptiMelt自動化熔點系統上獲得,且未經校正。分子係以其已知名稱提供,依據MDL ISISTM/Draw 2.5、ChemBioDraw Ultra 12.0或ACD Name Pro內之命名程式命名。若此等程式不能將分子命名,此分子係使用傳統命名規則命名。除非其它表示外,1H NMR光譜數據係以ppm(δ),且係於300、400或600 MHz記錄,且13C NMR光譜數據係以ppm(δ),且係於75、100或150 MHz記錄。
步驟1. (E)-3-(4-(亞肼基甲基)苯基)-1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑. 對含有肼水合物(64%水(aq)溶液;7.27毫升,15.0毫莫耳(mmol)),於EtOH(100毫升)內)之250毫升(mL)圓底燒瓶,於80℃,於5分鐘(min)期間一部份一部份地添加4-[1-(4-三氟甲氧基苯基)-1H-[1,2,4]三唑-3-基]-苯甲醛(5.00克(g),1.50毫莫耳)。溶液迴流攪拌另外3小時(h),其後以(H2O;300毫升)稀釋,且冷卻至0℃。沉澱產物藉由真空過濾收集,呈白色固體(4.89克,93%):mp
222-226℃;1H NMR(400 MHz,DMSO-d6)δ 8.59(s,1H),8.22(d,J=8.2 Hz,2H),7.84-7.79(m,3H),7.66(d,J=8.3 Hz,2H),7.41(d,J=8.2 Hz,2H),7.29(s,1H),5.63(br s,2H);ESIMS m/z 348(M+H)。
步驟2. 對含有於THF(10毫升)內之於THF(10毫升)內之(E)-3-(4-(亞肼基甲基)-苯基)-1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑(250毫克,0.720毫莫耳)之25毫升圓底燒瓶,添加4-異硫氰基-N,N-二甲基苯胺(385毫克,2.16毫莫耳)。內容物於65℃加熱並攪拌2小時,其後溶劑於減壓下移除。殘質於CH2Cl2(10毫升)形成漿料,造成產物材料沉澱。所欲產物經由真空過濾以黃色固體獲得(350毫克,93%):mp 205-208℃;1H NMR(400 MHz,DMSO-d6)δ 11.78(s,1H),10.02(s,1H),9.42(s,1H),8.19-7.99(m,6H),7.64(d,J=8.3 Hz,2H),7.28(d,J=8.3 Hz,2H),7.73(d,J=8.3 Hz,2H),2.92(s,6H);ESIMS m/z 526(M+H)。
步驟1. (E)-甲基2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼二硫代甲酸酯. 對含有於EtOH(100毫升)內之肼二硫代羧酸甲酯(2.38克,1.95毫莫耳)之250毫升圓底燒瓶,添加4-[1-(4-三氟甲氧基苯
基)-1H-[1,2,4]三唑-3-基]-苯甲醛(5.00克,1.50毫莫耳)。容器於80℃加熱小時,其後以H2O(300毫升)稀釋,且冷卻至0℃。沉澱產物藉由真空過濾收集,呈灰白色固體(6.13克,93%):mp 204-206℃;1H NMR(400 MHz,DMSO-d6)δ 13.39(s,1H),9.43(s,1H),8.38(s,1H),8.21(d,J=8.3 Hz,2H),8.09(d,J=8.4 Hz,2H),7.88(d,J=8.4 Hz,2H),7.62(d,J=8.3 Hz,2H),2.57(s,3H);ESIMS m/z 438(M+H)。
步驟2. 對含有於DMF(3毫升)內之(E)-甲基2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼二硫代甲酸酯(250毫克,0.571毫莫耳)之50毫升圓底燒瓶,添加N1,N1-二甲基苯-1,3-二胺(195毫克,1.43毫莫耳)。內容物於150℃加熱,並攪拌5小時,其後,溶液冷卻隔夜。混合物被過濾,且濾液經由RP-HPLC純化提供所欲材料(235毫克,78%),呈灰白色固體:mp 192-194℃;1H NMR(400 MHz,DMSO-d6)δ 11.82(s,1H),10.04(s,1H),9.41(s,1H),8.19(s,1H),8.16-7.99(m,6H),7.61(d,J=8.3 Hz,2H),7.16(t,J=7.2 Hz,1H),7.01(m,1H),6.87(m,1H),6.58(m,1H),2.88(s,6H);ESIMS m/z 526([M+H]+)。
對含有於EtOH(3毫升)內之4-[1-[4-(三氟甲氧基)
苯基]-1,2,4-三唑-3-基]苯甲醛(500毫克,1.5毫莫耳)之50毫升圓底燒瓶,添加4-苄基硫半卡肼(650毫克,3.6毫莫耳)。反應混合物於80℃加熱隔夜。於反應完全後添加H2O,且粗製產物材料藉由真空過濾隔離。標題化合物經由RP-HPLC隔離,呈白色固體(390毫克,52%):mp 220-224℃;1H NMR(400 MHz,CDCl3)δ 9.29(s,1H),8.59(s,1H),8.21(d,J=8.4 Hz,2H),7.85-7.79(m,3H),7.71(d,J=8.4 Hz,2H),7.46-7.30(m,8H),5.01(d,J=5.8 Hz,2H);ESIMS m/z 497.2(M+H)。
表1中之化合物I-4至I-31係依據如上範例合成。用於製備本發明化合物之其它中間物係依據Brown等人之WO 2011017504 A1中所述程序或其它已知路徑製備。
於EtOH(5毫升)內之含有(E)-N-(4-(二甲基胺基)苯基)-2-(4-(1-(4-(三氟甲氧基)-苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(150毫克,0.285毫莫耳)及碘甲烷(0.054毫升,0.856毫莫耳)之溶液於80℃加熱3小時,其後,溶劑於減壓下移除。殘質經由正向快速層析術純化(以己烷/EtOAc梯度洗提),提供標題化合物,呈橙色發泡體(93毫克
(mg),60%):1H NMR(400 MHz,DMSO-d6)δ 8.61(s,1H),8.48(s,1H),8.22(d,J=8.24 Hz,2H),8.17(s,1H),7.89(d,J=8.24 Hz,2H),7.80(d,J=8.28 Hz,2H),7.41(d,J=8.28 Hz,2H),7.19(d,J=8.24 Hz,2H),6.71(d,J=8.24 Hz,2H),2.99(s,6H),2.42(s,3H);EIMS m/z 540(M+)。
於CH2Cl2或氯仿(CHCl3)內之硫半卡腙及烷化劑之攪拌溶液於35至50℃加熱10至24小時。冷卻溶液於減壓下濃縮。殘質一般係經由層析術使用氯仿/甲醇(CHCl3/CH3OH)或EtOAc-己烷溶液作為洗提液純化,提供S-烷化產物。
對於二氯乙烷(3毫升)內之溴乙醯基溴化物(26微升(μL),0.299毫莫耳)之溶液以滴液方式添加於二氯甲烷(1毫升)內之(S)-第三丁基3-(胺基甲基)哌啶-1-羧酸酯(63.9毫克,0.298毫莫耳)之溶液,其後,添加N-乙基-N-異丙基丙-2-胺(76毫克,0.588毫莫耳)。此混合物於室溫攪拌30分鐘,
然後,(E)-N-(2,6-二甲基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼-硫代甲醯胺(100毫克,0.196毫莫耳)以固體添加,且混合物加熱至40℃持續90分鐘。然後,冷卻至室溫,且於減壓下蒸發,產生淡黃色玻璃,使其溶於乙腈(2毫升),且於室溫靜置。形成之沉澱物藉由離心及傾析而隔離,以新的乙腈清洗。固體於氮氣流下乾燥,然後,於高度真空下乾燥。粗製產物自丙酮-異丙醇再結晶。標題化合物以白色固體隔離(36.5毫克,24%):mp 148-151℃;1H NMR(400 MHz,甲醇-d4)δ 9.18(s,1H),8.59(s,1H),8.30(d,J=8.1 Hz,2H),8.12(m,2H),8.07-8.00(m,2H),7.58-7.43(m,2H),7.33(dd,J=8.6,6.5 Hz,1H),7.25(d,J=7.6 Hz,2H),4.02(m,2H),3.97-3.75(m,2H),3.21(d,J=6.9 Hz,2H),2.90(m,1H),2.59(m,1H),2.35(s,6H),1.84(m,2H),1.78-1.63(m,2H),1.44(s,9H),1.29(m,3H);ESIMS m/z 765(M+H)。
於TFA(250 μL,3.24毫莫耳)內之(S)-第三丁基
3-((2-((Z)-(2,6-二甲基苯基亞胺基)-((E)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼基)甲基硫基)-乙醯胺基)甲基)哌啶-1-羧酸酯(32.0毫克,0.042毫莫耳)之溶液於室溫攪拌10分鐘。然後,添加Et2O(10毫升),產生白色沉澱物,其藉由離心及傾析而隔離,然後,以新的Et2O(5毫升)沖洗。固體於氮氣流下乾燥,然後,於高度真空下乾燥,產生標題化合物,呈白色固體(19.8毫克,60%):mp 110-120℃;1H NMR(400 MHz,甲醇-d4)δ 9.18(s,1H),8.56(m,1H),8.26(m,2H),8.16-7.84(m,4H),7.52(m,2H),7.27(m,1H),7.22(m,2H),4.00(s,2H),3.28(m,3H),3.06-2.83(m,1H),2.75(t,J=12.2 Hz,1H),2.34(s,6H),2.21-1.83(m,4H),1.72(m,1H),1.47-1.19(m,2H);ESIMS m/z 665(M+H)。
對於THF(10毫升)內之2-((Z)-(4-甲氧基-2,6-二甲基苯基亞胺基)((E)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼基)甲基硫基)乙酸(77.7毫克,0.130毫莫耳)之溶液緩慢添加甲醇鈉(0.5 M,於甲醇內;260 μL,0.130毫莫耳)。混合物立即變較暗黃色,然後,於室溫於真
空下蒸發,產生淡橙色固體。此材料以Et2O(2X)研製,且藉由使用離心傾析而隔離,且於氮氣流下乾燥,然後,於高度真空下乾燥。標題化合物係以淡橙色固體隔離(32毫克,39%)。mp 146-154℃;1H NMR(400 MHz,甲醇-d4)δ 9.11(s,1H),8.64-7.68(m,7H),7.51(m,2H),6.70(s,2H),3.85-3.70(m,4H),3.61(m,1H),2.29(s,6H);ESIMS m/z 599(M+H)。
對於EtOH(5毫升)內之(E)-N-(4-甲氧基-2,6-二甲基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼-硫代甲醯胺(250毫克,0.462毫莫耳)之溶液,添加溴乙酸甲酯(100毫克,0.65毫莫耳),且混合物加熱至70℃持續4小時。混合物冷卻至室溫,且以水(1毫升)稀釋。沉澱物經真空過濾,產生標題化合物,呈白色固體(204毫克,76%):mp 188-190℃;1H NMR(400 MHz,CDCl3)δ 8.56(s,1H),8.33(s,1H),8.22(d,J=8.1 Hz,2H),7.90-7.70(m,4H),7.39(d,J=8.7 Hz,2H),6.72(s,2H),4.01(s,2H),3.87-3.73(s,3H),2.18(s,6H);ESIMS m/z 581(M+H)。
對於二氯乙烷(5毫升)內之(E)-N-(2,6-二甲基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼-硫代甲醯胺(74.7毫克,0.144毫莫耳)之溶液,添加δ-溴-4-二乙基胺基)苯乙酮(53.9毫克,0.199毫莫耳),且混合物加熱至40℃持續4小時。然後,混合物冷卻至室溫,且於真空下蒸發。粗製材料以乙腈研製,並且傾析(2X)。形成固體於氮氣流下乾燥,產生標題化合物,呈淡黃色固體(25毫克,25%):mp 190-193℃;1H NMR(400 MHz,甲醇-d4)δ 9.20(s,1H),8.38(s,1H),8.31-8.24(m,2H),8.08-8.00(m,2H),7.95-7.88(m,2H),7.55-7.48(m,3H),7.48-7.36(m,5H),7.31(d,J=7.7 Hz,2H),3.60(q,J=7.2 Hz,4H),2.20(s,6H),1.07(t,J=7.2 Hz,6H);ESIMS m/z 682(M+H)。
對於EtOH(10毫升)內之1-(2,6-二甲基苯基)硫脲(1.0克,5.55毫莫耳)之溶液,添加2-溴乙酸甲酯(1.0克,6.5毫莫耳)及乙酸鈉(1.0克,12.2毫莫耳)。溶液被攪拌及加熱迴流1小時,使其冷卻,且液體自一小量之固體材料傾析,然後,液體以水(10毫升)稀釋。沉澱物藉由過濾隔離,產生(1.1克,83%)之(Z)-3-胺基-2-(2,6-二甲基苯基亞胺基)四氫噻唑-4-酮:mp 149-152℃;1H NMR(400 MHz,CDCl3)δ 7.06(d,J=7.2 Hz,2H),6.98(m,1H),4.75(s,2H),3.80(s,2H),2.12(s,6H);ESIMS m/z 236(M+H)。
一部份之此材料(0.07克,0.3毫莫耳)溶於冰醋酸(3毫升),且以4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)苯甲醛(0.10克,0.30毫莫耳)處理,且溶液加熱至60℃持續2小時。然後,使溶液冷卻,且以水(1毫升)稀釋,且形成固體被過濾,且以空氣乾燥產生標題化合物(0.12克,67%):mp 209-213℃;1H NMR(400 MHz,CDCl3)δ 9.42(s,1H),8.59(s,1H),8.28(d,J=8.4 Hz,2H),8.01(d,J=8.3 Hz,2H),7.80-7.77(m,2H),7.43-7.34(m,2H),7.07(d,J=7.5 Hz,2H),6.98(dd,J=8.2,6.7 Hz,1H),3.90(s,2H),2.17(s,6H);ESIMS m/z 551(M+H)。
對於裝設一攪拌棒及維格羅分餾柱(vigruex column)之25毫升玻璃瓶內之於丁酮(10毫升)內之(E)-N-(2-異丙基苯基)-2-(4-(1-(4-(三氟甲基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(200毫克,0.393毫莫耳)及碳酸鉀(217毫克,1.57毫莫耳),添加1-溴-3-氯丙烷(0.047毫升,0.472毫莫耳)。反應加熱至60℃隔夜。反應藉由LCMS判定完全。反應混合物以DCM稀釋,且以水清洗。水性層以DCM萃取。有機層經倒經一相分離器,並且濃縮。藉由快速管柱層析術純化提供二化合物。微量之化合物於吸塵系統(house vacuum)下乾燥隔夜,提供標題化合物87C(2Z,NE)-2-((2-異丙基苯基)亞胺基)-N-(4-(1-(4-(三氟甲基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)-1,3-噻烷-3-胺(28.毫克,13%)呈黃色固體:mp 187-189℃;1H NMR(400 MHz,CDCl3)δ 8.81(s,1H),8.66(s,1H),8.21(d,J=8.3 Hz,2H),7.92(d,J=8.4 Hz,2H),7.81(t,J=10.2 Hz,4H),7.30-7.26(m,2H),7.17-7.04(m,1H),6.83(d,J=6.4 Hz,1H),3.96(t,
J=6.1 Hz,2H),3.13(七重峰,J=6.9 Hz,1H),2.97-2.90(m,2H),2.47-2.38(m,2H),1.25(d,J=7.5 Hz,6H);ESIMS m/z 550(M+H)。主要化合物自MeOH再結晶。固體被過濾,以MeOH清洗,且於50℃真空下乾燥。然後,固體與丙酮(3x)共沸,且形成之固體於50℃真空下乾燥,提供標題化合物179C(Z)-3-(2-異丙基苯基)-2-((E)-(4-(1-(4-(三氟甲基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)亞肼基)-1,3-噻烷,呈黃色固體(92.3毫克,0.168毫莫耳,43%):mp 212-213℃;1H NMR(400 MHz,CDCl3)δ 8.64(s,1H),8.15(d,J=8.4 Hz,2H),8.06(s,1H),7.91(d,J=8.5 Hz,2H),7.79(d,J=8.6 Hz,2H),7.75(d,J=8.4 Hz,2H),7.38(dd,J=7.8,1.6 Hz,1H),7.33(td,J=7.5,1.4 Hz,1H),7.29-7.23(m,1H),7.18(dd,J=7.8,1.4 Hz,1H),3.78-3.72(m,1H),3.59-3.48(m,1H),3.18-3.04(m,3H),2.40-2.30(m,2H),1.26-1.20(m,6H);ESIMS m/z 550(M+H)。
對於EtOH(4毫升)內之(E)-N-(2-環丙基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄
基)肼硫代甲醯胺(100毫克,0.191毫莫耳)及乙酸鈉(63.0毫克,0.765毫莫耳),添加2-溴丙酸甲酯(0.026毫升,0.230毫莫耳)。反應加熱至60℃隔夜。然後,反應加熱至85℃持續72小時。反應混合物以DCM稀釋,且以水清洗。水性層以DCM萃取。有機層倒經一相分離器,並且濃縮。藉由快速管柱層析術純化,提供標題化合物,呈白色固體(32.5毫克,0.056毫莫耳,30%):mp 112-115℃;1H NMR(400 MHz,CDCl3)δ 8.58(s,1H),8.32(s,1H),8.22(d,J=8.3 Hz,2H),7.87-7.75(m,4H),7.43-7.32(m,4H),7.26-7.24(m,2H),4.23(q,J=7.3 Hz,1H),1.85-1.78(m,4H),0.90-0.78(m,2H),0.78-0.69(m,1H),0.65-0.55(m,1H);ESIMS m/z 578(M+H)。
對於丁酮(4毫升)內之(E)-N-(2-異丙基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(214毫克,0.407毫莫耳)及碳酸鉀(225毫克,1.63毫莫耳),添加1-溴-2-氯乙烷(70.0毫克,0.489毫莫耳)。反應加熱至90℃隔夜。反應藉由LCMS判定完全。反
應混合物被冷卻,以DCM稀釋,且以水清洗。水性層以DCM萃取。有機層經由一相分離器過濾,並且濃縮。藉由快速管柱層析術分離,及於55℃於真空下乾燥回收之固體,提供標題化合物,呈白色固體(137毫克,0.249毫莫耳,61%):mp 193-196℃;1H NMR(400 MHz,CDCl3)δ 8.56(s,1H),8.22(s,1H),8.17(d,J=8.4 Hz,2H),7.80(ddd,J=9.5,6.9,4.9 Hz,4H),7.43-7.33(m,4H),7.31-7.21(m,2H),4.05(td,J=9.4,7.1 Hz,1H),3.97-3.87(m,1H),3.42-3.33(m,1H),3.33-3.24(m,1H),3.12(七重峰,J=6.8 Hz,1H),1.27(d,J=6.8 Hz,3H),1.22(d,J=6.9 Hz,3H);ESIMS m/z 552(M+H)。
對於丁酮(4毫升)內之(E)-N-(2-異丙基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(300毫克,0.572毫莫耳)及碳酸鉀(316毫克,2.29毫莫耳),添加1,2-二溴丙烷(0.072毫升,0.686毫莫耳)。反應加熱至85℃隔夜。反應藉由LCMS判定完全。反應混合物以DCM稀釋,且以水清洗。水性層以DCM萃取。
有機層倒經一相分離器,並且濃縮。藉由決速管柱層析術純化,提供黃色固體。固體自MeOH再結晶。固體被過濾,以MeOH清洗,及乾燥,提供標題化合物,呈黃色固體,使其溶於丙酮並且濃縮(3x)。淡黃色固體被收集且乾燥,提供標題化合物,呈旋轉非鏡像異構物之1:1混合物(75.1毫克,0.133毫莫耳,23%):mp 201-204℃;混合物之1H NMR(400 MHz,CDCl3)δ 8.56(s,2H),8.18(dd,J=10.8,7.4 Hz,6H),7.84-7.73(m,8H),7.45-7.30(m,8H),7.30-7.23(m,2H),7.20(d,J=6.7 Hz,1H),7.12(dd,J=7.8,1.2 Hz,1H),4.43-4.33(m,1H),4.16(dd,J=12.6,6.3 Hz,1H),3.48(dt,J=13.3,6.7 Hz,1H),3.37(dd,J=10.8,6.2 Hz,1H),3.24(dt,J=13.7,6.9 Hz,1H),3.08-2.92(m,3H),1.33-1.16(m,18H);ESIMS m/z 566(M+H)。
對於丁酮(5毫升)內之(E)-N-(鄰-甲苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(257毫克,0.520毫莫耳)之溶液,添加三乙基胺(0.14毫升,1.0毫莫耳)及氯丙酮(0.06毫升,0.73毫莫耳),且於75℃迴流15小時。使混合物冷卻至室溫,然後,
轉移至一含有水(5毫升)之分液漏斗,且以二氯甲烷萃取兩次。有機層經由一相分離器過濾,吸附於矽石凝膠上,且藉由快速管柱層析術純化,提供標題化合物,呈黃色固體(229毫克,83%):mp 87℃(度);1H NMR(400 MHz,CDCl3)δ 8.56(s,1H),8.19-8.15(m,3H),7.82-7.75(m,4H),7.43-7.30(m,5H),7.24(d,J=7.3 Hz,1H),5.88(d,J=1.3 Hz,1H),2.21(s,3H),1.80(d,J=1.2 Hz,3H);ESIMS m/z 536(M+H)。
對於丁酮(4毫升)內之(E)-N-(2-異丙基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(100毫克,0.191毫莫耳)及碳酸鉀(105毫克,0.763毫莫耳),添加1-溴-3-氯-2-甲基丙烷(39.0毫克,0.229毫莫耳)。反應加熱至80℃隔夜。然後,反應混合物以DCM稀釋,且以水清洗。水性層以DCM萃取。有機層倒經一相分離器,並且濃縮。藉由快速管柱層析術純化,提供標題化合物,呈淡黃色固體,為旋轉非鏡像異構物之混合物:mp 186-190℃;1H NMR(400 MHz,CDCl3)δ 8.55(d,
J=3.6 Hz,1H),8.14(d,J=8.4 Hz,2H),8.06(s,1H),7.84-7.77(m,2H),7.74(d,J=8.4 Hz,2H),7.38(d,J=9.0 Hz,3H),7.32(td,J=7.5,1.4 Hz,1H),7.26(s,1H),7.17(t,J=7.1 Hz,1H),3.69-3.26(m,1H),3.55-3.37(m,1H),3.18-2.98(m,2H),2.93-2.80(m,1H),2.47(d,J=35.9 Hz,1H),1.31-1.12(m,9H);ESIMS m/z 580(M+H)。
對於丙酮(4毫升)內之(E)-N-(2,6-二甲基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(500毫克,0.979毫莫耳)及碳酸鉀(541毫克,3.92毫莫耳),添加1-溴-4-氯丁烷(0.135毫升,1.18毫莫耳)。反應加熱至60℃隔夜。烷化藉由超效能液相層析術(“UPLC”)判定係完全。反應混合物以DCM稀釋,且以水清洗。水性層以DCM萃取。有機層倒至一相分離器,並且濃縮。藉由快速管柱層析術純化,提供(1Z,N'E)-4-氯丁基N-(2,6-二甲基苯基)-N'-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)氨基甲醯基硫代亞肼酯(427毫克,0.710毫莫耳,73%),呈黃色膠,其係於未進一
步純化下使用。對(1Z,N'E)-4-氯丁基N-(2,6-二甲基苯基)-N'-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)-氨基甲醯基硫代亞肼酯(427毫克,0.710毫莫耳)、碘化鉀(236毫克,1.42毫莫耳),及碳酸鉀(393毫克,2.84毫莫耳),添加丙酮(7毫升)。反應加熱至65℃持續72小時。反應冷卻至室溫,以DCM稀釋,且以水清洗。水性層以DCM萃取。有機層倒經一相分離器,並且濃縮。藉由快速管柱層析術純化,提供黃色油。黃色油自MeOH再結晶,過濾,以MeOH清洗,並且乾燥,提供標題化合物,呈黃色固體(100毫克,0.177毫莫耳,25%):mp 100-106℃;1H NMR(400 MHz,CDCl3)δ 8.55(s,1H),8.15(d,J=8.4 Hz,2H),8.10(s,1H),7.79(dt,J=10.4,5.8 Hz,4H),7.38(d,J=8.3 Hz,2H),7.11(s,3H),3.85-3.78(m,2H),3.20-3.12(m,2H),2.30(s,6H),2.13-2.07(m,2H),1.87-1.82(m,2H);ESIMS m/z 566(M+H)。
對於丁酮(9.5毫升)內之(E)-N-(2-異丙基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄
基)肼硫代甲醯胺(500毫克,0.953毫莫耳)添加丙烯醯氯(0.077毫升,0.953毫莫耳)。反應於環境溫度攪拌10分鐘,其後於50℃持續2小時。反應冷卻至40℃隔夜。反應藉由LCMS判定係完全。反應混合物以DCM稀釋,且以飽和碳酸氫鈉清洗。水性層以DCM萃取。有機層倒經一相分離器,並且濃縮。藉由快速管柱層析術純化,提供黃色油。油以二乙基醚/己烷再結晶,提供標題化合物,呈淡黃色固體(125毫克,0.217毫莫耳,23%):mp 118℃(度);1H NMR(400 MHz,CDCl3)δ 8.57(s,1H),8.21(d,J=8.4 Hz,2H),8.16(s,1H),7.85-7.75(m,4H),7.46-7.36(m,4H),7.33-7.26(m,1H),7.10(d,J=7.6 Hz,1H),3.26-3.14(m,4H),2.81(七重峰,J=6.9 Hz,1H),1.21(t,J=7.2 Hz,6H);ESIMS m/z 580(M+H)。
對於裝設一磁性攪拌棒之25毫升玻璃瓶內之於丁酮(10毫升)內之(E)-N-(2,6-二氟苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(0.50克,0.96毫莫耳)及碳酸鉀(0.53克,3.9毫莫耳)之混合物,添加二碘甲烷(0.093毫升,1.2毫莫耳)。反應加熱至55℃,
且攪拌二天。反應混合物以DCM稀釋,以水清洗,且相被分離。水性相以DCM萃取,且混合之有機相藉由通過一相分離器匣,然後濃縮而乾燥。藉由快速管柱層析術純化,提供黃色油,於靜置時結晶化。固體於二乙基醚及己烷內形成漿料,且藉由真空過濾收集。固體以己烷清洗,及乾燥提供標題化合物(0.086克,0.16毫莫耳,17%),呈淡黃色固體:mp 144-146℃;1H NMR(400 MHz,CDCl3)δ 8.58(s,1H),8.34(s,1H),8.20(d,J=8.3 Hz,2H),7.81(d,J=8.8 Hz,4H),7.40(d,J=8.3 Hz,2H),7.31-7.23(m,1H),7.03-6.97(m,2H),5.05(s,2H);ESIMS m/z 532(M+H)。
表3所示之化合物240-244及246-261係依據範例20所述之方法自表1揭露之經適當取代之中間物製備。此等化合物之特徵化數據係於表4中報導。
自外消旋混合物分離成份異構物可使用下列手性HPLC方法之一實行。
分離方法A:用於分離之管柱係Chiral Technologies INC Chiral Pak 1A 5 μm,4.6 X 250 mm管柱(零件編號80325)。此方法係由1.0毫升/分鐘之流速,從0至30分鐘,於此操作期間於25% B之等度維持所組成。A洗提液係正己烷,B洗提液係異丙醇。
分離方法B:用於分離之管柱係Chiral Technologies INC Chiral Pak 1B 5 μm,4.6 X 250 mm管柱(零件編號81325)。此方法係由1.0毫升/分鐘之流速,從0至30
分鐘,於此操作期間於15% B之等度維持所組成。A洗提液係正戊烷,B洗提液係正丁醇。
步驟1:製備1-氟-2-硝基-3-(丙-1-烯-2-基)苯(I-37,方法M). 對於裝設一磁性攪拌棒及氮氣入口之100毫升圓底燒瓶內之1-溴-3-氟-2-硝基苯(0.953克,4.33毫莫耳)之混合物,添加二烷(17.3毫升)、碳酸鈉(0.551克,5.20毫莫耳)、水(4.33毫升),及4,4,5,5-四甲基-2-(丙-1-烯-2-基)-1,3,2-二氧硼戊環(0.977毫升,5.20毫莫耳)。對此混合物,添加雙(三苯基-膦)鈀(II)氯化物(0.243克,0.347毫莫耳)。燒對被排氣且以氮氣吹掃(3 x),然後,加熱至80℃,且攪拌隔夜。反應冷卻至室溫,經由Celite ®過濾,且墊材以乙酸乙酯清洗。相被分離,且有機相被濃縮。藉由快速管柱層析術純化,提供標題化合物(0.590克,3.26毫莫耳,75%產率),呈淡黃色油:1H NMR(400 MHz,CDCl3)δ 7.48-7.36(m,1H),7.21-7.06(m,2H),5.23(p,J=1.5 Hz,1H),5.05(q,J=1.1 Hz,1H),2.09(s,3H);13C NMR(101 MHz,
CDCl3)δ 153.56(d,JCF=257.5 Hz),139.62,139.60,138.83,131.48(d,JCF=8.6 Hz),124.47(d,JCF=3.6 Hz),117.60,115.51(d,JCF=19.1 Hz),23.18。
步驟2:製備2-氟-6-異丙基苯胺(I-38,方法M). 對於裝設一磁性攪拌棒及氮氣入口之250毫升圓底燒瓶內之於乙酸乙酯(32.6毫升)內之1-氟-2-硝基-3-(丙-1-烯-2-基)苯(0.590克,3.26毫莫耳)之溶液,添加於碳上之鈀(5% Pd/C,0.693克,0.326毫莫耳)。反應燒瓶被排氣,且以氫氣吹掃(2 x),然後,置於1大氣壓(atm)之氫氣下,且於室溫攪拌隔夜。反應經由Celite®過濾,且墊材以乙酸乙酯清洗。濾液被濃縮產生標題化合物(0.423克,2.76毫莫耳,85%產率),呈澄清且無色之油:IR(淨)3476(m),3392(m),2966(m),2872(m),1628(s),1474(s),1270(m)cm-1;1H NMR(400 MHz,CDCl3)δ 6.92(dt,J=7.7,1.2 Hz,1H),6.86(ddd,J=10.8,8.1,1.4 Hz,1H),6.69(td,J=8.0,5.6 Hz,1H),3.71(bs,2H),2.92(七重峰,J=6.8 Hz,1H),1.26(d,J=6.8 Hz,6H);13C NMR(101 MHz,CDCl3)δ 151.91(d,J=237.6 Hz),135.10(d,J=2.3 Hz),131.60(d,J=11.8 Hz),120.52(d,J=3.0 Hz),117.99(d,J=8.0 Hz),112.28(d,J=19.6 Hz),27.77(d,J=2.9 Hz),22.22。
步驟3:製備N-(2-氟-6-異丙基苯基)肼硫代甲醯胺(I-39,方法M). 對裝設一攪拌棒及氮氣入口之100毫升圓底燒瓶,添加2-氟-6-異丙基苯胺(0.415克,2.71毫莫耳)、二氯甲烷(13.6毫升)、水(6.78毫升),及碳酸氫鈉(0.683克,
8.13毫莫耳)。對此二相混合物,添加硫光氣(0.199毫升,2.60毫莫耳),且反應劇烈攪拌2小時。懸浮液經一相分離器匣過濾,且有機相於100毫升圓底燒瓶內濃縮。燒瓶係裝設一磁性攪拌棒及氮氣入口,且殘質溶於乙醇(6.78毫升)。對形成之溶液,添加肼水合物(0.131毫升,2.71毫莫耳),且反應於室溫攪拌2天。溶液被濃縮,且形成之殘質懸浮於二乙基醚與己烷之混合物內,且再次濃縮產生固體。固體懸浮於最小量之二乙基醚內,且混合物以己烷稀釋。大部份之二乙基醚被蒸發,且形成之固體藉由真空過濾收集,以己烷清洗,然後,於於吸塵系統下乾燥,提供標題化合物(0.518克,2.28毫莫耳,84%產率),呈白色固體:mp 122-124℃;1H NMR(400 MHz,CDCl3)δ 8.56(bs,1H),7.52(bs,1H),7.32(td,J=8.1,5.6 Hz,1H),7.17-7.12(m,1H),7.00(ddd,J=9.5,8.2,1.4 Hz,1H),4.07(bs,2H),3.15(七重峰,J=7.0 Hz,1H),1.24(d,J=6.9 Hz,6H);ESIMS m/z 229([M+H]+)。
步驟4:製備(E)-N-(2-氟-6-異丙基苯基)-2-(4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)亞苄基)肼硫代甲醯胺(I-40,方法C). 對於裝設一磁性攪拌棒及迴流冷凝器之100毫升圓底燒瓶內之於甲醇(22.8毫升)內之4-(1-(4-(三氟甲氧基)苯基)-1H-1,2,4-三唑-3-基)苯甲醛(0.760克,2.28毫莫耳)之溶液,添加N-(2-氟-6-異丙基苯基)肼硫代甲醯胺(0.518克,2.28毫莫耳),且反應加熱至65℃,且攪拌6小時。溫度降低至50℃,且反應攪拌隔夜。反應冷卻至至溫,且形成之固體被過濾,以甲醇清洗,且於真空
下(25,以Hg計)於55℃乾燥,產生標題化合物(0.907克,1.67毫莫耳,73%產率),呈白色固體:mp 210-212℃;1H NMR(400 MHz,CDCl3)δ 9.54(s,1H),8.60(s,1H),8.56(s,1H),8.30-8.22(m,2H),7.92(s,1H),7.86-7.76(m,4H),7.44-7.38(m,2H),7.35(dd,J=8.1,5.6 Hz,1H),7.18(d,J=7.9 Hz,1H),7.04(ddd,J=9.4,8.2,1.3 Hz,1H),3.22(p,J=6.9 Hz,1H),1.29(d,J=6.9 Hz,6H);ESIMS m/z 544([M+H]+)。
表1所示之中間化合物I-32-I-36及I-41-I-65係依據範例22,步驟1-4概述之方法製備。此等中間物之特徵化數據係顯示於表2。
BAW具有很少之有效的寄生蟲、疾病,或捕食者降低其數量。BAW寄生於許多雜草、樹木、小草、豆類,及農場作物。於各種不同場所,對蘆筍、棉花、玉米、黃豆、菸草、苜蓿芽、甜菜、胡椒、蕃茄、馬鈴薯、洋蔥、豆子、葵花,及柑橘,各種其它植物有經濟上影響。CEW已知會攻擊玉米及蕃茄,但其亦攻擊朝鮮薊、蘆葦、甘藍菜、香瓜、芥藍、豇豆、小黃瓜、茄子、萵苣、利馬豆、洋香瓜、秋葵、豌豆、胡椒、馬鈴薯、南瓜、四季豆、菠菜、栗南瓜、地瓜,及西瓜,與其它植物。CEW亦已知能需某些殺昆蟲劑。因此,由為上述因素,控制此等害蟲係重要。再者,控制此等害蟲之分子可用於控制其它害蟲。
此文件中揭露之某些分子係使用於下列範例中所述之程序對BAW及CEW作測試。於報導此等結果,係使用“BAW及CEW分級表”(見表格段落)。
對BAW之生物分析係使用128-孔之食物盤分析進行。一至五個二齡BAW幼蟲被置於食物盤之每一孔(3毫升),此食物盤已事先填充1毫升之人工食物,50 μg/cm2之測試化合物(溶於50 μL之90:10丙酮-水之混合物)已施加(至八個孔之每一者),然後,乾燥。盤係以一透明自黏性覆蓋物覆蓋,且於25℃,14:10亮-暗保持五至七天。每一孔之幼蟲死亡率被記錄;然後,八個孔之活性被平均。結果係於標題為“表5:生物結果”之表中指示(見表格段落)。
對CEW之生物分析係使用128-孔之食物盤分析進行。一至五個二齡CEW幼蟲被置於食物盤之每一孔(3毫升),此食物盤已事先填充1毫升之人工食物,50 μg/cm2之測試化合物(溶於50 μL之90:10丙酮-水之混合物)已施加(至八個孔之每一者),然後,乾燥。盤係以一透明自黏性覆蓋物覆蓋,且於25℃,14:10亮-暗保持五至七天。每一孔之幼蟲死亡率被記錄;然後,八個孔之活性被平均。結果係於標題為“表5:生物結果”之表中指示(見表格段落)。
GPA係桃樹之最顯著之蚜蟲,造成減少之生長,葉子枯萎,及各種組織死亡。其亦係危險,因為其作為將
植物病毒(諸如,馬鈴薯病毒Y及馬鈴薯卷葉病毒)運送至龍葵/馬鈴薯家族茄科之成員,及將各種馬賽克病毒運送至許多食物作物之媒介。GPA攻擊諸如青花菜、牛蒡、甘藍菜、胡蘿蔔、花椰菜、白蘿蔔、茄子、綠豆、萵苣、夏威夷豆、木瓜、胡椒、地瓜、番茄、西洋菜及鬼瓜之植物與其它植物。GPA亦攻擊諸如康乃馨、菊花、白菜心、聖誕紅,及玫瑰之許多觀賞作物。GPA已發展出對許多殺蟲劑之抗性。
本文件揭露之某些分子係使用於下列範例中描述之程序對GPA作測試。於報導此等結果,係使用“GPA分級表”(見表格段落)。
於3-英吋盆內生長具有2-3個小(3-5 cm)真葉之甘藍菜苗被作為測試基材。於施加化學品前,以20-50 GPA(無翼成蟲及蛹階段)寄生於此等苗。四個具有個別苗之盆被用於每一處理。測試化合物(2毫克)溶於2毫升之丙酮/甲醇(1:1)溶劑,形成1000 ppm測試化合物之原料溶液。原料溶液以於H2O內之0.025% Tween 20稀釋5X,獲得200 ppm測試化合物之溶液。手持吸引器型之噴灑器用於將溶液噴灑至甘藍菜葉之二側至溢流為止。參考植物(溶劑檢查)以僅含有20體積%之丙酮/甲醇(1:1)溶劑之稀釋劑噴灑。於分級前,經處理之植物於約25℃及環境相對濕度(RH)之貯存室貯存三天。評估係以於顯微鏡下計算每一植物活蚜蟲數量進行。控制百分率係使用如下之Abbott校正公式測試(W.S.Abbott,“A Method of Computing the Effectiveness of an Insecticide”J.Econ.Entomol.18(1925),265-267頁)。
經校正之控制%=100 *(X-Y)/X其中,X=於溶劑檢查植物上之活蚜蟲數量,且Y=經處理之植物上之活蚜蟲數量
結果係於標題為“表5:生物結果”之表中指示(見表格段落)。
具化學式1、2及3之分子可配製成殺蟲可接受之酸加成鹽。作為非限制性例子,胺官能基可與氫氯酸、氫溴酸、硫酸、磷酸、乙酸、苯甲酸、檸檬酸、丙二酸、水楊酸、蘋果酸、福馬酸、草酸、琥珀酸、酒石酸、乳酸、葡萄糖酸、抗壞血酸、馬來酸、天冬門酸、苯磺酸、甲磺酸、乙磺酸、羥甲磺酸,及羥乙磺酸形成鹽。另外,作為非限制性例子,酸官能基可形成包括自鹼金屬或鹼土金屬衍生及自氨及胺衍生之鹽。較佳陽離子之例子包括鈉、鉀,及鎂。
具化學式1、2及3之分子可配製成鹽衍生物。作為非限制性例子,鹽衍生物可藉由可藉由使自由鹼與足夠量之所欲酸接觸產生鹽而製備。自由鹼可藉由將此鹽以諸如稀氫氧化鈉(NaOH)、碳酸鉀、氨,及碳酸氫鈉水溶液之適合的稀鹼水溶液處理而再生。舉例而言,於許多情況,諸如2,4-D之殺蟲劑係藉由將其轉化成其二甲基胺鹽而變得更具水溶性。
具化學式1、2及3之分子可與溶劑配製成安定錯合物,使得錯合物於未錯合溶劑被移除後保持完整。此等錯合物通常稱為"溶劑合物”。但是,特別所欲者係與作為溶劑之水形成安定水合物。
具化學式1、2及3之分子可製成酯衍生物。然後,此等酯衍生物可以與本文件揭露之本發明被應用之相同方式應用。
具化學式1、2及3之分子可以各種不同結晶多形體製造。多形體於發展農用化學品係重要,因為相同分子之不同結晶多形體或結構具有大為不同之物理性質及生物性能。
具有化學式1、2及3之分子可以不同同位素製造。特別重要者係具有替代1H之2H(亦稱為氘)之分子。
具化學式1、2及3之分子可以不同放射性核種製造。特別重要係具有14C之分子。
具化學式1、2及3之分子可以一或多種立體異構物存在。因此,某些分子可以外消旋混合物製造。熟習此項技藝者會瞭解一立體異構物可能比其它立體異構物更具活性。個別之立體異構物可藉由已知之選擇性合成程序,藉由使用溶解起始物料之傳統合成程序,或藉由傳統溶解程序獲得。
具化學式1、2及3之分子亦可與一或多種下列殺
昆蟲劑結合使用(諸如,以一組成混合物,或同時或依序施加)-1,2-二氯丙烷、阿巴汀、毆殺松、亞滅培、家蠅磷、乙醯蟲腈、阿納寧、丙烯腈、棉寧威、涕滅威、得烕克、奧爾德林、丙烯菊酯、阿洛氨菌素、除害威、α-賽滅寧、α-蛻皮激素、α-安殺番、賽硫磷、滅害威、安利通、安利通草酸鹽、雙甲脒、阿那巴辛、乙基殺扑磷、印楝素、亞滅松、乙基谷速松、甲基谷速松、偶氮磷、六氟矽酸鋇、除蟲菊精、免敵克、免扶克、免速達、β-賽扶寧、β-亞滅寧、畢芬寧、百亞烈寧、戊環苄呋菊酯、生物氯菊酯、雙三氟蟲脲、硼砂、硼酸、溴苯烯磷、溴殺烯、溴-DDT、溴磷松、乙基溴磷松、必克蝨、布芬淨、畜蟲烕、丁嘧硫磷、丁酮威、丁酸酯、丁酮碸威、硫線磷、砷酸鈣、多硫化鈣、毒殺芬、氯滅殺威、加保利、加保扶、二硫化碳、四氯化碳、加芬松、丁基加保扶、培丹、培丹氫氯酸鹽、氯蟲苯甲醯胺、冰片丹、可氯丹、十氯酮、殺蟲脒、殺蟲脒氫氯酸鹽、氯氧磷、克凡派、毒蟲畏、克福隆、氯甲硫砏、氯仿、氯化苦、氯腈肟磷、滅蟲吡啶、陶斯松、甲基陶斯松、克硫松、可芬諾、瓜菊脂I、瓜菊脂II、瓜菊脂類、順式苄呋菊酯、除線烕、氯氰碘柳胺、可尼丁、醋酸亞磷酸銅、砷酸銅、環烷酸銅、油酸銅、牛璧逃、畜蟲磷、克羅米通、巴毒磷、育畜磷、冰晶石、施力松、氰乃松、果蟲磷、氰蟲醯胺、環蟲菊、乙氰菊酯、賽扶寧、賽洛寧、賽滅寧、賽酚寧、賽滅淨、賽滅磷、DDT、加保扶、第滅寧、甲基滅賜松、甲基滅賜松-O、甲基滅賜松-S、滅賜松、滅賜松-甲
基、滅賜松-O、滅賜松-O-甲基、滅賜松-S、滅賜松-S-甲基、滅賜松-S-甲基碸、汰芬隆、得拉松、矽藻土、大利松、異氯磷、除線磷、二氯松、對甲苯、雙特松、地昔尼爾、地特靈、二福隆、滴露、四氟甲醚菊酯、甲氟磷、地麥烕、大滅松、苄菊酯、二甲基亞硝胺、敵蠅威、消蟎酚、消蟎酚-地克林辛、硝丙酚、戊硝酚、達特南、二苯丙醚、蔬果磷、二氧烕、敵殺磷、乙拌磷、苯噻乙雙硫磷、d-檸檬烯、DNOC、DNOC-銨、DNOC-鉀、DNOC-鈉、多拉菌素、蛻皮激素、因滅汀、因滅汀苯甲酸鹽、EMPC、烯炔菊酯、硫丹、內毒磷、異狄氏劑、EPN、保幼醚、依普菌素、生物丙烯菊酯、益化利、丙硫磷、乙硫苯威、愛殺松、乙蟲腈、益硫磷、普伏松、甲酸乙酯、乙基-DDD、二溴乙烷、二氯乙烷、環氧乙烷、依芬寧、益多松、EXD、氨磺磷、芬滅松、抗蟎唑、皮蠅磷、二乙基苯酚甲基氨基甲酸酯、芬氟次林、撲滅松、丁基滅必蝨、嘧醯蟲胺、芬諾克、吡氯氰菊酯、芬普寧、繁福松、芬殺松、乙基芬殺松、芬化利、芬普尼、弗諾米托昆、氟尼胺、氟蟲醯胺(其另外溶解異構物)、弗康夫南、氟環脲、氟氰戊菊酯、嘧蟲胺、氟蟲脲、三氟醚菊酯、丁蟲腈、氟比拉弟弗隆(flupyradifurone)、氟胺氰菊酯、大福松、覆滅蟎、覆滅蟎氫氯酸鹽、福木松、藻蟎威、藻蟎威氫氯酸鹽、丁苯硫磷、福司吡酯、丁硫環磷、呋喃蟲醯肼、呋線威、糠醛菊酯、γ-賽洛寧、γ-HCH、合芬寧、合芬隆、HCH、HEOD、七氯、庚烯磷、速殺硫磷、六伏隆、HHDN、愛美松、氰化氫、烯蟲乙酯、海昆卡、
益達胺、氯噻啉、炔咪菊酯、因得克、碘甲烷、IPSP、依殺松、碳氯靈、水胺硫磷、異艾氏劑、亞芬松、甲基亞芬松、異丙威、亞賜圃、獲賜松、加福松、樂去蟲、茉莉菊酯I、茉莉菊酯II、阿發松、保幼激素I、保幼激素II、保幼激素III、氯戊環、烯蟲炔酯、λ-賽洛寧、砷酸鉛、拉皮米汀、福賜松、靈丹、丙嘧硫磷、祿芬隆、噻唑磷、馬拉硫磷、特蟎腈、疊氮磷、ME-5343、MEB-5343、滅蚜磷、甲基滅蚜磷、滅蚜松、氯氯醚菊酯、地安磷、氯化亞汞、倍硫磷亞碸、氰氟蟲腙、蟲蟎畏、達馬松、滅大松、滅蟲威、殺蟲乙烯磷、滅多威、烯蟲酯、甲醚菊酯、甲氧氯、甲氧蟲醯肼、溴甲烷、異硫氰酸甲酯、甲基氯仿、二氯甲烷、美特寧、速滅威、蟲酮、美文松、茲克威、密滅汀、殺蟎菌素肟、丙胺氟磷、滅蟻靈、殺蟲單、亞素靈、殺蟲單(monomehypo)、殺蟲單(monosultap)、茂果、莫昔克汀、萘酞磷、二溴磷、萘、尼古丁、氟蟻靈、烯啶蟲胺、尼噻、戊氰威、諾伐隆、諾福隆、毆滅松、殺線威、碸吸磷、異亞碸磷、碸拌磷、對-二氯苯、巴拉松、甲基巴拉松、氟幼脲、五氯酚、百滅寧、芬硫磷、苯醚菊酯、賽達松、福瑞松、伏殺硫磷、硫環磷、益滅松、雙氯硫磷、福賜米松、膦、辛硫磷、甲基辛硫磷、甲胺基嘧啶磷、比加普、乙基嘧啶磷、甲基嘧啶磷、亞砷酸鉀、硫代氰酸鉀、pp'-DDT、炔丙菊酯、早熟素I、早熟素II、早熟素III、乙醯嘧啶磷、佈飛松、環丙氟靈、丙氟菊酯、蜱虱威、猛殺威、丙蟲磷、胺丙畏、安丹、乙噻唑磷、普硫松、發果、普若泰利芬比、
派滅淨、白克松、吡氟蟲腈、定菌磷、百滅磷、除蟲菊酯I、除蟲菊酯II、除蟲菊酯類、噠蟎靈、啶蟲丙醚、噠硫磷、比拉弗路喹唑啉、畢汰芬、嘧啶磷、吡啶氟蟲腈、百利普芬、苦木、喹硫磷、甲基喹硫磷、畜寧磷、雷復尼特、苄呋菊酯、毒魚藤素、魚尼丁、沙巴藜蘆、八甲磷、司拉克丁、矽醚菊酯、矽石凝膠、砷亞酸鈉、氟化鈉、六氟矽酸鈉、硫代氰酸鈉、蘇硫磷、賜諾特、賜諾殺、螺殺蟎酯、螺蟲乙酯、蘇克呋喃、蘇克呋喃鈉、氟蟲胺、硫特普、氟啶蟲胺腈、硫醯氟、硫丙磷、塔士門酮(tasmanone)、氟胺氰菊酯、噻蟎威、TDE、得芬諾、吡蟎胺、丁基嘧啶磷、伏蟲隆、七氟菊酯、亞培松、TEPP、甲烯菊酯、托福松、四氯乙烷、殺蟲畏、胺菊酯、四氟醚菊酯、θ-賽滅寧、噻蟲啉、賽速安、苯噻乙硫磷、抗蟲威、殺蟲環、殺蟲環草酸鹽、硫敵克、久效威碸、甲基乙拌磷、噻蘇塔、噻蘇塔二鈉、噻蘇塔單鈉、蘇雲金素、脫芬瑞、四溴菊酯、四氟苯菊酯、反式百滅寧、苯蟎噻、唑蚜威、三落松、三氯松、皮蠅磷-3、壤蟲磷、佈飛松、殺鈴脲、三甲威、烯蟲硫酯、繁米松、甲烯氟蟲腈、XMC、滅殺威、ζ-賽滅寧,及丙硫唑磷(集體地,此等通常稱作殺昆蟲劑係定義為“殺昆蟲劑組群”)。
具化學式1、2及3之分子亦可與一或多種下列殺蟎劑混合使用(諸如,以組成物混合物,或同時或依序施加)-亞醌蟎、醯胺夫蟎、三氧化二砷、偶氮苯、三唑錫、苯菌
靈、苯諾沙磷、苯蟎特、苯甲酸苯甲酯、聯苯肼酯、樂殺蟎、溴蟎酯、滅蟎猛、氯殺蟎、殺蟎醇、殺蟎酯、敵殺特、乙酯殺蟎醇、滅蟎脒、滅蟲脲、氯蟎酯、克芬蟎、唑蟎腈、賽芬蟎、三環錫、益發靈、大克蟎、得氯蟎、氟蟎四、大脫蟎、白粉克、白粉克-4、白粉克-6、鄰敵蟎消、硝戊酯、硝辛酯、硝丁酯、二苯基碸、四乙秋蘭姆化二硫、多芬奈品、依殺蟎、芬殺蟎、芬佈賜、芬硫克、唑蟎酯、除蟎酯、芳氟胺、嘧蟎酯、吡蟲隆、氟奔絕胺、聯氟蟎、氟氯苯菊酯、氟殺蟎、合賽多、甲硫酚、MNAF、尼可黴素、丙氯醇、炔蟎特、喹硫啉、螺蟎酯、舒非侖、硫磺、三氯殺蟎碸、四抗菌素、殺蟎硫醚,及克殺蟎(集體地,此等通常稱作殺蟎劑係定義為“殺蟎劑組群”)。
具化學式1、2及3之分子亦可與一或多種下列殺線蟲劑結合使用(諸如,以一組成混合物,或同時或依序施加)-1,3-二氯丙烯、異噻蟲唑、棉隆、棉隆鈉、DBCP、DCIP、除線特、氟噻蟲碸、福賽絕、糠醛、新煙鹼類、依沙米多夫、依殺松、威百畝、威百畝銨、威百畝鉀、威百畝鈉、磷克,及硫磷(集體地,此等通常稱作殺線蟲劑係定義為“殺線蟲劑組群”)。
具化學式1、2及3之分子亦可與一或多種下列殺黴菌劑結合使用(諸如,以一組成混合物,或同時或依序施加)-(3-乙氧基丙基)溴化汞、2-甲氧基乙基氯化汞、2-苯基
酚、8-羥基喹啉硫酸鹽、8-苯基汞氧基喹啉、阿拉酸式苯、阿位酸式苯-S-甲基、阿西皮塔斯、阿西皮塔斯銅、阿西皮塔斯鋅、阿地嗎、丙烯醇、辛唑嘧菌胺、安美速、1-氨基丙基磷酸、敵菌靈、金色制黴素、戊環唑、氧化福美雙殺菌劑、亞托敏、多硫化鋇、本達樂、本達樂-M、麥鏽靈、苯菌靈、醌肟腙、滅草特、苯噻菌胺、異丙基苯噻菌胺、氯化苯二甲烴銨、苄馬克力、異丁基苄馬克力、抑菌啉、苯并羥肟酸、比托沙、樂殺蟎、聯苯基、比多農、硫氯酚、聯苯吡菌胺、保米黴素-S、波爾多混合物、白克列、糠菌唑、乙嘧酚磺酸酯、勃根地混合物、得滅多、丁胺、多硫化鈣、敵菌丹、蓋普丹、嗎菌威、貝芬替、萎鏽靈、加普胺、香芹酮、柴斯罕特混合物、蟎離丹、克氯綜、粉淨胺、四氯苯醌、2-(2-氯苯基)-1H-苯并咪唑、氯二硝基萘、地茂散、氯化苦、百菌清、目氯喹啉、乙菌利、甘寶素、克霉唑、乙酸銅、鹼性碳酸銅、氫氧化銅、環烷酸銅、油酸酮、氧氯化銅、矽酸銅、硫酸銅、鉻酸銅鋅、間甲酚、硫雜靈、福美銅氯、氧化亞銅、氰霜唑、環菌胺、環己醯亞胺、環氟菌胺、克絕、青菌靈、環丙唑醇、賽普洛、棉隆、棉隆鈉、DBCP、咪菌威、癸磷錫、脫氫乙酸、益發靈、二氯萘醌、二氯芬、菌核利、苄氯三唑醇、雙氯氰菌胺、噠菌酮、噠菌酮鈉、氯硝胺、乙黴威、焦碳酸二乙酯、苯醚甲環唑、二氟林、二甲嘧酚、烯醯嗎啉、醚菌胺、烯唑醇、烯唑醇-M、辛硝蟎通、白粉克、白粉克-4、白粉克-6、敵蟎消、硝戊酯、硝辛酯、硝丁酯、二苯胺、雙硫氧吡啶、四乙秋
蘭姆化二硫、滅菌磷、腈硫醌、DNOC、DNOC-銨、DNOC-鉀、DNOC-鈉、嗎菌靈、嗎菌靈乙酸鹽、十二環嗎啉苯甲酸鹽、多地辛、多地辛鈉、乙酸十二烷胍、肼菌酮、護粒松、氟環唑、乙環唑、伊特姆、唑菌胺、乙嘧酚、乙氧基喹啉、乙基汞2,3-二羥丙基硫醇鹽、乙基乙酸汞、乙基溴化汞、乙基氯化汞、乙基磷酸汞、依得利、唑菌酮、咪唑菌酮、敵磺鈉、咪菌腈、芬瑞莫、腈苯唑、甲呋醯胺、環醯菌胺、種衣酯、氰菌胺、拌種咯、苯鏽啶、芬普福、三苯錫、三苯錫氯、三苯錫氫氧化物、福美鐵、嘧菌腙、氟啶胺、咯菌酯、氟醯菌胺、氟嗎啉、氟吡菌胺、氟吡菌醯胺、氟醯亞胺、三氟苯唑、氟嘧菌酯、氟喹唑、氟矽唑、磺菌胺、氟噻菌淨、福多寧、護汰芬、氟苯吡菌胺、滅菌丹、甲醛、三乙膦酸、三乙膦酸鋁、麥穗寧、呋霜靈、福拉比、二甲呋醯胺、呋菌唑、順式呋菌唑、糠醛、拌種胺、呋甲硫菌靈、果綠啶、灰黃黴素、克熱淨、丙烯酸喹啉酯、六氯苯、六氯丁二烯、己唑醇、己噻福司、雙苯汞亞甲基二萘磺酸酯、殺紋寧、依滅列、依滅列硝酸鹽、依滅列硫酸鹽、易胺唑、克達淨、克熱淨三乙酸鹽、克熱淨三烷苯磺酸鹽、碘甲烷、種菌唑、丙基喜樂松、異菌脲、丙森鋅、亞賜圃、吡唑萘菌胺、異噻菌胺、異醯菌酮、嘉賜黴素、甲基醚菌酯、代森錳銅、代森錳鋅、雙炔醯菌胺、代森錳、鄰醯胺、苯并威、滅派林、滅普寧、敵蟎普、氯化汞、氧化汞、氯化亞汞、甲霜靈、甲霜靈-M、威百畝、威百畝銨、威百畝鉀、威百畝鈉、間氯敵菌酮、滅特唑、磺菌威、呋
菌胺、溴甲烷、異硫氰酸甲酯、苯甲酸甲汞、雙氰胺甲汞、五氯苯氧化甲汞、代森聯、苯氧菌胺、滅芬農、噻菌胺、代森環、腈菌唑、甲菌利、N-(乙基汞)-對-甲苯磺醯苯胺、代森鈉、納他黴素、硝基苯乙烯、酞菌酯、尼瑞莫、OCH、辛噻酮、呋醯胺、醚菌胺、惡霜靈、羥基喹啉銅、嚼咪唑、嚼咪唑福馬酸鹽、嘉保信、稻瘟酯、平克唑、戊菌隆、戊苯吡菌胺、五氯酚、吡噻菌胺、苯基汞尿素、乙酸苯汞、氯化苯汞、兒茶酚之苯基汞衍生物、硝酸苯汞、水楊酸苯汞、氯瘟磷、熱必斯、啶氧菌酯、哌丙靈、聚氨基甲酸酯、聚肟、保粒黴素、保粒黴素鋅、疊氮化鉀、聚硫化鉀、硫代氰酸鉀、撲殺熱、撲克熱、撲滅寧、霜黴威、霜黴威氫氯酸鹽、普克利、甲基代森鋅、丙氧噻唑、硫菌威、硫菌威氫氯酸鹽、丙硫菌唑、賜加落、百克威、百克威、唑胺菌酯、唑菌酯、定菌磷、吡菌苯威、定菌腈、啶斑肟、嘧黴胺、甲氧苯啶菌、咯喹酮、氯甲氧吡啶、氯吡呋醚、喹烯酮、喹烯酮硫酸鹽、醌菌腙、氯苯喹唑、快諾芬、五氯硝基苯、吡咪唑、水楊醯苯胺、噻達新、矽噻菌胺、矽氟唑、疊氮化鈉、鄰苯基苯氧化鈉、五氯苯氧化鈉、多硫化鈉、螺環菌胺、鏈黴素、硫磺、戊苯碸、TCMTB、戊唑醇、異丁乙氧喹啉、克枯欄、四氯硝基苯、福美雙聯、氟醚唑、噻菌靈、氟噻亞菌胺、噻菌腈、噻氟菌胺、硫氯苯亞胺、硫柳汞、硫菌靈、甲基硫菌靈、克殺蟎、得恩地、噻醯菌胺、提惡米得、甲基立枯磷、甲苯氟磺胺、乙酸甲苯汞、三唑酮、三唑醇、威菌磷、嘧菌醇、丁三唑、咪唑、三
丁基氧化錫、水楊菌胺、三環唑、十三嗎啉、肟菌酯、氟菌唑、賽福寧、滅菌唑、烯效唑、烯效唑-P、有效黴素、霜黴滅、乙烯菌核利、氰菌胺、環烷酸鈉、代森鋅、福美鋅、苯醯菌胺(集體地,此等通常稱作殺黴菌劑係定義為“殺黴菌劑組群”)。
具有化學式1、2及3之分子亦可與一或多種下列除草劑組合使用(諸如,以組成物混合物,或同時或依序施加)-2,3,6-TBA、2,3,6-TBA-二甲基銨、2,3,6-TBA-鈉、2,4,5-T、2,4,5-T-2-丁氧基丙基、2,4,5-T-2-乙基己基、2,4,5-T-3-丁氧基丙基、2,4,5-TB、2,4,5-T-比托米提、2,4,5-T-丁氧基乙酯、2,4,5-T-丁基、2,4,5-T-異丁基、2,4,5-T-異辛基、2,4,5-T-異丙基、2,4,5-T-甲基、2,4,5-T-戊基、2,4,5-T-鈉、2,4,5-T-三乙基銨、2,4,5-T-三乙醇胺、2,4-D、2,4-D-2-丁氧基丙基、2,4-D-2-乙基己基、2,4-D-3-丁氧基丙基、2,4-D-銨、2,4-DB、2,4-DB-丁基、2,4-DB-二甲基銨、2,4-DB-異辛基、2,4-DB-鉀、2,4-DB-鈉、2,4-D-丁氧基乙酯、2,4-D-丁基、2,4-D-二乙基銨、2,4-D-二甲基銨、2,4-D-二乙醇胺,2,4-D-十二烷基銨、2,4-DEB、2,4-DEP、2,4-D-乙基、2,4-D-庚基銨、2,4-D-異丁基、2,4-D-異辛基、2,4-D-異丙基、2,4-D-異丙基銨、2,4-D-鋰、2,4-D-米比、2,4-D-甲基、2,4-D-辛基、2,4-D-戊基、2,4-D-鉀、2,4-D-丙基、2,4-D-鈉、2,4-D-替夫、2,4-D-十四烷基銨、2,4-D-三乙基銨、2,4-D-三(2-羥基丙基)銨、2,4-D-三乙醇胺、3,4-DA、3,4-DB、3,4-DP、4-CPA、
4-CPB、4-CPP、乙草胺、三氟羧甲醚、甲基三氟羧甲醚、三氟羧甲醚鈉、苯草醚、丙烯醛、甲草胺、二丙烯草胺、亞汰草、亞汰草鈉、丙烯醇、阿羅拉、胺酮、草殺淨、胺草酮、胺唑草酮、醯嘧磺隆、環丙嘧啶酸、甲基環丙嘧啶酸、環丙嘧啶酸鉀、氯氨吡啶酸、氯氨吡啶酸鉀、氯氨吡啶酸-三(2-羥丙基)銨、甲基胺草磷、氨基三唑、氨基磺酸銨、莎裨磷、安尼蘇隆、磺草靈、磺草靈鉀、磺草靈鈉、莠去通、草脫淨、唑啶草酮、四唑嘧磺隆、疊氮津、燕麥靈、BCPC、氟丁醯草胺、草除靈、草除靈二甲銨、草除靈乙酯、草除靈鉀、醯苯草酮、氟草胺、三氮雜苯、苄嘧磺隆、苄嘧磺隆甲酯、地散磷、本達隆、本達隆鈉、胺酸殺、胺酸殺銨、雙苯嘧草酮、苄草胺、苯并雙環酮、吡草酮、氟草黃、新燕靈、新燕靈乙酯、苯噻隆、二環吡草酮、必芬諾、雙丙氨膦、雙丙氨膦鈉、雙草醚、雙草醚鈉、硼沙、除草定、除草定鋰、除草定鈉、溴苯肼、溴丁醯草胺、溴酚肟、溴苯腈、溴苯腈丁酸酯、溴苯腈庚酸酯、溴苯腈辛酸酯、溴苯腈鉀、溴殺草敏、丁草胺、氟丙嘧草酯、丁胺磷、丁草胺、丁噻咪草酮、丁噻隆、比達寧、丁氧環酮、炔草隆、丁酸酯、二甲胂酸、唑草胺、氯酸鈣、氰胺化鈣、肯本地洛、除草隆、卡草胺、咔唑、唑酮草、唑酮草乙酯、CDEA、CEPC、甲氧除草醚、草滅平、草滅平銨、草滅平二乙醇胺、草滅平甲酯、草滅平甲基銨、草滅平鈉、地快樂、炔禾靈、炔禾靈丙炔酯、可樂津、氯溴隆、氯草靈、乙氧隆、伐草克、伐草克鈉、除蟎靈、除蟎靈甲
酯、氟咪殺、整型醇、整型醇甲酯、氯草敏、氯嘧磺隆、氯嘧磺隆乙酯、草枯醚、三氯丙酸、綠麥隆、枯草隆、羥敵草腈、克洛普卡、氯苯胺靈、氯磺隆、敵草索、敵草索二甲酯、敵草索單甲酯、賽草青、吲哚酮草酯、環庚草醚、醚黃隆、咯草隆、烯草酮、一氯吡啶酯、炔草、炔草丙炔酯、克洛法、克洛法異丁酯、可滅蹤、氯甲醯草胺、調果酸、洛普丁、二氯吡啶酸、二氯吡啶酸甲酯、二氯吡啶酸乙醇胺、二氯吡啶酸鉀、二氯吡啶酸-三(2-羥丙基)銨、氯酯磺草胺酸、氯酯磺草胺酸甲酯、CMA、硫酸銅、CPMF、CPPC、醚草敏、甲酚、苄草隆、氨基氰、氰草淨、氰乙醯腈、草滅特、環磺隆、噻草酮、環莠隆、賽伏草、賽伏草丁酯、牧草快、牧草快氯化物、環丙津、三環噻草胺、環醯草胺、香草隆、茅草枯、茅草枯鈣、茅草枯鎂、茅草枯鈉、棉隆、棉隆鈉、異丁草胺、甜菜胺、敵草淨、燕麥敵、麥草畏、麥草畏二甲基銨、麥草畏二乙醇胺、麥草畏異丙基銨、麥草畏甲酯、麥草畏乙醇胺、麥草畏鉀、麥草畏鈉、麥草畏三乙醇胺、敵草腈、氯全隆、苄胺靈、滴丙酸、滴丙酸-2-乙基己酯、滴丙酸-丁氧基乙酯、滴丙酸二甲基銨、滴丙酸乙基銨、滴丙酸異辛酯、滴丙酸甲酯、滴丙酸-P、滴丙酸-P-二甲基銨、滴丙酸鉀、滴丙酸鈉、二氯苯氧基苯氧基丙酸、二氯苯氧基苯氧基丙酸甲酯、雙氯磺草胺、地依塞奎、地依塞奎二氯化物、乙醯草酸胺、乙醯草酸胺乙酯、戊味禾草靈、戊味禾草靈乙酯、枯莠隆、野燕枯、野燕枯甲硫酸鹽、吡氟醯草胺、氟吡草腙、氟吡草腙鈉、惡
唑隆、哌草丹、二甲草胺、戊草津、汰草滅、汰草滅-P、草滅散、草噠酮、撻乃安、地樂特、硝丙酚、戊硝酚、地樂酚、地樂酚乙酸酯、地樂酚銨、地樂酚二乙醇胺、地樂酚鈉、地樂酚三乙醇胺、特樂酚、特樂酚乙酸酯、二苯茚酮鈉、草乃敵、異丙淨、敵草炔、敵草炔二溴化物、賽松、賽松鈉、氟氯草定、敵草隆、DMPA、DNOC、DNOC銨、DNOC鉀、DNOC鈉、DSMA、EBEP、甘草津、甘草津乙酯、草多索、草多索二銨、草多索二鉀、草多索二鈉、三唑磺、EPTC、抑草蓬、戊草丹、乙丁烯氟靈、胺苯磺隆、胺苯磺隆甲酯、磺噻隆、硫草敵、醚菊酯、氟乳醚、氟乳醚乙酯、乙氧嘧磺隆、硝草酚、安尼普米、乙氧苯草胺、EXD、芬納穌蘭、涕丙酸、涕丙酸-3-丁氧基丙酯、涕丙酸丁氧基丙酯、涕丙酸丁氧基乙酯、涕丙酸丁酯、涕丙酸異辛酯、涕丙酸甲酯、涕丙酸鉀、唑菌胺、唑菌胺乙酯、唑菌胺-P、唑菌胺-P-乙酯、異苯碸、非諾特羅、噻唑禾草靈、噻唑禾草靈乙酯、四唑草胺、非草隆、非草隆TCA、硫酸亞鐵、麥草氟、麥草氟異丙酯、麥草氟-M、麥草氟甲酯、麥草氟-M-異丙酯、麥草氟-M-甲酯、啶嘧磺隆、雙氟磺草胺、吡氟夫草靈、吡氟夫草靈丁酯、吡氟夫草靈甲酯、吡氟夫草靈-P、吡氟夫草靈-P-丁酯、異丙吡草酯、氟酮磺隆、氟酮磺隆鈉、氟吡磺隆、氟消草、氟噻草胺、三吡氟草胺、氟噠草酯、氟噠草酯乙酯、氟唑嘧磺草胺、氟奮乃靜、氟胺草酯、氟胺草酯戊酯、丙炔氟草胺、炔草胺、伏草隆、三氟硝草醚、乙羧氟草醚、乙羧氟草醚乙酯、唑
啶草、氟除草醚、氟硫隆、氟胺草唑、氟單丙唑草酯、四氟丙酸、四氟丙酸鈉、氟啶嘧磺隆、氟啶嘧磺隆甲基鈉、氟啶酮、氟咯草酮、氟氯比、氟氯比丁氧基丙酯、氟氯比甲基庚酯、呋草酮、噠草酸、噠草酸甲酯、氟磺胺草醚、氟磺胺草醚鈉、甲醯胺磺隆、調節膦、調節膦銨、呋氧草醚、草丁膦、草丁膦銨、草丁膦-P、草丁膦-P-銨、草丁膦-P-鈉、嘉磷塞、嘉磷塞二銨、嘉磷塞二甲基銨、嘉磷塞異丙基銨、嘉磷塞單銨、嘉磷塞鉀、嘉磷塞倍半鈉、嘉磷塞三甲基硫、鹵沙芬、鹵蘇福隆、鹵蘇福隆甲酯、氟啶草、吡氟氯禾靈、吡氟氯禾靈乙氧基乙酯、吡氟氯禾靈甲酯、吡氟氯禾靈-P、吡氟氯禾靈-P-乙氧基乙酯、吡氟氯禾靈-P-甲酯、吡氟氯禾靈鈉、六氯丙酮、六氟鹽、環酮、咪唑酸、咪唑酸甲酯、甲基咪唑酸、甲基咪唑酸銨、甲基咪草烟、甲基咪草烟銨、依滅草、依滅草異丙基銨、滅草喹、滅草喹銨、滅草喹甲酯、滅草喹鈉、咪草烟、咪草烟銨、咪唑磺隆、茚草酮、吲弗萊、吲多波尼、碘甲烷、碘磺隆、甲基碘磺隆鈉、碘苯腈、碘苯腈辛酸酯、碘苯腈鋰、碘苯腈鈉、抑草津、鹵苯胺唑、氯胺草啶鹼、丁脒胺、異草定、丁草酮、異草完隆、異普林納、異丙樂靈、異丙隆、異隆、異草胺、異氯草酮、異氟草、草醚、卡靈草、酮螺達、乳氟夫草靈、環草定、利谷隆、MAA、MAMA、MCPA、MCPA-2-乙基己酯、MCPA-丁氧基乙酯、MCPA-丁酯、MCPA-二甲基銨、MCPA-二乙醇胺、MCPA-乙酯、MCPA-異丁酯、MCPA-異辛酯、MCPA-異丙酯、MCPA-
甲酯、MCPA-乙醇胺、MCPA-鉀、MCPA-鈉、MCPA-硫代乙酯、MCPA-三乙醇胺、MCPB、MCPB-乙酯、MCPB-甲酯、MCPB-鈉、甲氯丙酸、甲氯丙酸-2-乙基己酯、甲氯丙酸二甲基銨、甲氯丙酸二乙醇胺、甲氯丙酸-三氯乙酯、甲氯丙酸異辛酯、甲氯丙酸甲酯、甲氯丙酸-P、甲氯丙酸-P-二甲基銨、甲氯丙酸-P-異丁酯、甲氯丙酸鉀、甲氯丙酸-P-鉀、甲氯丙酸鈉、甲氯丙酸-三乙醇胺、米特樂酚、米特樂酚乙酸酯、苯噻草胺、氯磺醯草胺、氯磺醯草胺二乙醇胺、氯磺醯草胺鉀、滅莠津、甲磺胺磺隆、甲磺胺磺隆甲酯、甲基磺草酮、威百畝、威百畝銨、唑醯草胺、苯草酮、威百畝鉀、威百畝鈉、吡草胺、雙醚氯吡嘧磺隆、二甲噠草伏、甲基苯噻隆、甲普帕林、滅草唑、殺丹、甲硫咪唑、滅草恆、醚草通、枯草淨、溴甲烷、異硫氰酸甲酯、甲基殺草隆、甲氧苯草隆、異丙甲草胺、磺草唑胺、甲氧隆、滅必淨、甲磺隆、甲磺隆甲酯、禾草特、庚醯草胺、單甲異隆、單氯乙酸、綠谷隆、滅草隆、滅草隆TCA、伐草快、伐草快二氯化物、MSMA、萘丙胺、敵草胺、萘草胺、萘草胺鈉、草不隆、烟嘧磺隆、吡氯草胺、甲磺樂靈、除草醚、三氟甲草醚、氟草敏、草完隆、OCH、坪草丹、鄰-二氯苯、嘧苯胺磺隆、氯磺樂靈、草酮、樂滅草、草達松、草達松-三乙醇胺、草達松鈉、環氧嘧磺隆、去裨胺、乙氧氟草醚、雙氟隆、巴拉刈、巴拉刈二氯化物、巴拉刈二甲硫酸鹽、丁乙硫代氨甲酸丙酯、正壬酸、二甲戊樂靈、五氟磺草胺、五氯酚、蔬草滅、環戊草酮、黃草伏、烯
草胺、棉胺寧、甜菜寧、甜菜寧乙酯、醯草隆、乙酸苯汞、毒莠定、毒莠定-2-乙基己酯、毒莠定異辛酯、毒莠定甲酯、毒莠定乙醇胺、毒莠定鉀、毒莠定三乙基銨、毒莠定三(2-羥丙基)銨、氟吡醯草胺、唑啉草酯、哌草磷、亞砷酸鉀、疊氮化鉀、氰酸鉀、普拉草、氟嘧磺隆、氟嘧磺隆甲酯、環丙腈津、氨基丙氟靈、氟唑草胺、環丙氟靈、環苯甲酮、甘撲津、甘撲津乙酯、撲滅通、撲草淨胺、毒草胺、敵裨、喔草酯、撲滅津、苯胺靈、異丙草胺、丙苯磺隆、丙苯磺隆鈉、咪唑嘧磺隆、戊炔草胺、甲硫磺樂靈、苄草丹、氟磺隆、異丙黃原酸、異丙黃原酸鈉、丙炔草胺、噠酮乙酸、雙唑草腈、吡草醚、吡草醚乙酯、塵無忌、吡唑特、吡嘧磺隆、吡嘧磺隆乙酯、苄草唑、嘧啶肟草醚、裨草畏、三氯吡啶酚、噠草醇、必汰草、環酯草醚、嘧草醚、嘧草醚甲酯、嘧啶硫番、嘧草硫醚、嘧草硫醚鈉、派羅克殺草碸、甲氧磺草胺、二氯喹啉酸、氯甲喹啉酸、莫克草、克藻胺、喹禾靈、喹禾靈乙酯、喹禾靈-P、喹禾靈-P-乙酯、喹禾靈-P-糠酯、硫氰苯胺、碸嘧磺隆、苯嘧磺草胺、另丁津、仲丁通、稀禾定、環草隆、西瑪津、西瑪通、西草淨、SMA、S-莫多草、亞砷酸鈉、疊氮化鈉、氯酸鈉、磺草酮、草克死、磺醯唑草酮、嘧磺隆、嘧磺隆甲酯、磺醯磺隆、硫酸、沙格里卡平、滅草靈、TCA、TCA-銨、TCA-鈣、TCA-三氯乙酯、TCA-鎂、TCA-鈉、牧草胺、特丁噻草隆、塵無忌、但波三酮、得殺草、特草定、特草靈、特丁草胺、特丁通、草淨津、去草淨、四氟隆、甲氧噻草胺、噻氟隆、
噻草定、噻二唑草胺、噻苯隆、酮脲磺草酚、酮脲磺草酚甲酯、噻吩磺隆、噻吩磺隆甲酯、殺丹、丁草威、替洛林、苯唑草酮、肟草酮、野麥畏、醚苯磺隆、三氟草胺、苯磺隆、苯磺隆甲酯、殺草畏、定草酯、定草酯丁氧基乙酯、定草酯乙酯、定草酯三乙基銨、滅草環、草達津、三氟啶磺隆、三氟啶磺隆鈉、三福林、氟胺磺隆、氟胺磺隆甲酯、特力弗、特力弗甲酯、三氟禾草肟、三羥三、三甲隆、三普平丹、三塔克、三氟甲磺隆、滅草猛、二甲苯草胺(集體地,此等一般稱為除草劑係定義為“除草劑組群”)。
具有化學式1、2及3之分子亦可與一或多種生物殺蟲劑組合使用(諸如,以組成物混合物,或同時或依序施加)。“生物殺蟲劑”一辭係用於微生物生物害蟲控制劑,其係以與化學殺蟲劑相似之方式施加。一般,此等係細菌性,但亦有黴菌控制劑之例子,包括木黴菌(Trichoderma spp)及白粉寄生菌(Ampelomyces quisqualis)(葡萄白粉病之控制劑)。枯草芽孢桿菌(Bacillus subtilis)係用於控制植物病原體。雜草及嚙齒動物亦已以微生物劑控制。一已知之殺昆蟲劑例子係蘇力菌(Bacillus thuringiensis),鱗翅目(Lepidoptera)、鞘翅目(Coleoptera),及雙翅目(Diptera)之一細菌疾病。因為其對於其它生物具有極小作用,被認為係比合成殺蟲劑對環境更友善。生物殺昆蟲劑包括以如下為主之產物:1.昆蟲病原性真菌(例如,黑殭菌(Metarhizium anisopliae));2.蟲生線蟲(例如,夜蛾斯氏線蟲(Steinernema feltiae));及3.昆蟲病毒(例如,蘋果蠹蛾顆粒體病毒(Cydia pomonella granulovirus))。
昆蟲病原生物之其它例子不受限制地包括桿狀病毒、細菌,及其它原核生物、真菌、原蟲,及微孢子蟲。生物衍生之殺昆蟲劑不受限制地包括魚藤酮、藜蘆定,與微生物毒素;耐蟲性或抗蟲性植物品種;及藉由重組DNA技術而產生殺昆蟲劑或將抗蟲性運送至基因改造生物而改造之生物。於一實施例,具化學式1、2及3之分子可與一或多種生物殺蟲劑使用於種籽處理及土壤改良領域。生物控制劑手冊(The Manual of Biocontrol Agents)提供可利用之生物殺昆蟲劑(及其它以生物學為主之控制)產物之評介。Copping L.G.(ed.)(2004).The Manual of Biocontrol Agents(見前係the Biopesticide Manual)第3版.British Crop Production Council(BCPC),Farnham,Surrey UK。
具化學式1、2及3之分子亦可與下列之一或多種組合使用(諸如,以組成物混合物,或同時或依序施用):1. 3-(4-氯-2,6-二甲基苯基)-4-羥基-8-氧-1-氮雜螺[4,5]癸-3-烯-2-酮;2. 3-(4’-氯-2,4-二甲基[1,1’-聯苯基]-3-基)-4-羥基-8-氧-1-氮雜螺[4,5]癸-3-烯-2-酮;
3. 4-[[(6-氯-3-吡啶基)甲基]甲基胺基]-2(5H)-呋喃酮;4. 4-[[(6-氯-3-吡啶基)甲基]環丙基胺基]-2(5H)-呋喃酮;5. 3-氯-N2-[(1S)-1-甲基-2-(甲基磺醯基)乙基]-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二羧醯胺;6. 2-氰基-N-乙基-4-氟-3-甲氧基-苯磺醯胺;7. 2-氰基-N-乙基-3-甲氧基-苯磺醯胺;8. 2-氰基-3-二氟甲氧基-N-乙基-4-氟-苯磺醯胺;9. 2-氰基-3-氟甲氧基-N-乙基-苯磺醯胺;10. 2-氰基-6-氟-3-甲氧基-N,N-二甲基-苯磺醯胺;11. 2-氰基-N-乙基-6-氟-3-甲氧基-N-甲基-苯磺醯胺;12. 2-氰基-3-二氟甲氧基-N,N-二甲基苯磺醯胺;13. 3-(二氟甲基)-N-[2-(3,3-二甲基丁基)苯基]-1-甲基-1H-吡唑-4-羧醯胺;14. N-乙基-2,2-二甲基丙醯胺-2-(2,6-二氯-α,α,α-三氟-對-甲苯基)腙;15. N-乙基-2,2-二氯-1-甲基環丙烷-羧醯胺-2-(2,6-二氯-α,α,α-三氟-對-甲苯基)腙尼古丁;16. O-{(E-)-[2-(4-氯-苯基)-2-氰基-1-(2-三氟甲基苯基)-乙烯基]}S-甲基硫代碳酸酯;17. (E)-N1-[(2-氯-1,3-噻唑-5-基甲基)]-N2-氰基-N1-甲基乙脒;18. 1-(6-氯吡啶-3-基甲基)-7-甲基-8-硝基-1,2,3,5,6,7-
六氫-咪唑并[1,2-a]吡啶-5-醇;19. 4-[4-氯苯基-(2-亞丁基-亞肼基)甲基]]苯基甲磺酸酯;及20. N-乙基-2,2-二氯-1-甲基環丙烷羧醯胺-2-(2,6-二氯-α,α,α-三氟-對-甲苯基)腙。
具化學式1、2及3之分子亦可與下列組群中之一或多種化合物組合使用(諸如,以組成物混合物,或同時或依序施用):除藻劑、抗食劑、殺鳥劑、殺細菌劑、驅鳥劑、化學不育劑、除草劑安全劑、昆蟲引誘劑、驅昆蟲劑、哺乳動物忌避劑、交配干擾劑、殺螺劑、植物活化劑、植物生長調節劑、滅鼠劑及/或殺病毒劑(集體地,此等一般指稱之組群係定義為“AI組群”)。需注意落於AI組群、殺昆蟲劑組群、殺黴菌劑組群、除草劑組群、殺蟎劑組群,或殺線蟲劑組群內之化合物可能因為此化合物具有數種活性而係於多於一組群內。對於更多資訊,查閱位於http://www.alanwood.net/pesticides/index.html之“COMPENDIUM OF PESTICIDE COMMON NAMES”。亦可查閱“THE PESTICIDE MANUAL”第14版,C D S Tomlin編輯,British Crop Production Council 2006版權,或其先前或更近版本。
具化學式1、2及3之分子可與殺昆蟲劑組群之化合物使用形成增效混合物,其中,此等化合物之作用模徑與具化學式1及2之分子之作用模式相比係相同、相似,或不同。作用模式之例子不受限制地包括:乙醯膽鹼酯酶抑
制劑;鈉通道調節劑;幾丁生物合成抑制劑;GABA調控之氯化物通道拮抗劑;GABA及谷氨酸鹽調控之氯化物通道激動劑;乙醯膽鹼受體激動劑;MET I抑制劑;Mg-刺激之ATP酶抑制劑;尼古丁乙醯膽鹼受體;中腸膜干擾素;氧化磷酸化干擾素;及雷諾定受體(RyRs)。另外,具化學式1及2之分子可與殺黴菌劑組群、殺蟎劑組群、除草劑組群,或殺線蟲劑組群中之化合物使用形成增效混合物。再者,具化學式1、2及3之分子可與諸如於標題為“其它活性化合物”中之其它活性化合物、殺藻劑、殺鳥劑、殺細菌劑、殺螺劑、滅鼠劑、殺病毒劑、除草劑安全劑、佐劑,及/或界面活性劑使用形成增效混合物。一般,增效混合物內之具化學式1、2及3之分子與另外化合物之重量比率係約10:1至約1:10,較佳係約5:1至約1:5,且更佳係約3:1,且更佳係約1:1。另外,下列化合物係稱為增效劑,且可與化學式1揭露之分子使用:胡椒基丁醚、增效醛、增效酯、增效菊、芝麻林、亞碸,及脫葉磷(集體地,此等增效劑係定義為“增效劑組群”)。
殺蟲劑係很少適於以其純型式應用。通常需添加其它物質,使得殺蟲劑可以允許輕易施加、處理、運送、貯存,及最大殺蟲劑活性之需要濃度及適當型式使用。因此,殺蟲劑係配製成,例如,誘餌、濃縮乳化液、塵粉、可乳化之濃縮物、燻劑、凝膠、顆粒、微膠囊.種子處理劑、懸浮濃縮物、懸乳劑、錠劑、水溶性液體、水可分散
之顆粒或乾燥動流劑、可濕性粉末,及超低體積溶液。有關配製物型式之進一步資訊,見“Catalogue of Pesticide Formulation Types and International Coding System”Technical Monograph n°2,第5版,CropLife International(2002)。
殺蟲劑最普遍係以自此等殺蟲劑之濃縮配製物製得之水性懸浮液或乳化液施用。此等水溶性、水可懸浮,或可乳化之配製物係固體,通常稱為可濕性粉末,或水可分散之顆粒,或通常稱為可乳化濃縮物或水性懸浮液之液體。可經壓實形成水可分散顆粒之可濕性粉末包含殺蟲劑、載劑及界面活性劑之密實混合物。殺蟲劑之濃度通常係約10重量%至約90重量%。載劑通常係選自鎂鋁海泡石黏土、蒙脫土黏土、矽藻土,或經純化之矽酸鹽。包含約0.5%至約10%之可濕性粉末之有效界面活性劑係於磺化木質素、濃縮萘磺酸鹽、萘磺酸鹽、烷基苯磺酸鹽、烷基硫酸鹽,及諸如烷基酚之環氧乙烷加成物之非離子界面活性劑發現。
殺蟲劑之可乳化濃縮物包含一方便濃度之殺蟲劑,諸如,溶於載劑(其係水可溶混溶劑或水不可溶混有機溶劑及乳化劑之混合物)內之每公升液體為約50至約500克。有用之有機溶劑包括芳香族,特別是二甲苯類及石油分餾物,特別是石油之高沸點萘及烯烴部份,諸如,重芳香族石油腦。其它有機溶劑亦可被使用,諸如,包括松脂衍生物之萜烯溶劑,諸如環己酮之脂族酮,及諸如2-乙氧
基乙醇之錯合醇。可乳化之濃縮物之適合乳化劑係選自傳統陰離子及非離子之界面活性劑。
水性懸浮液包含以約5重量%至約50重量%範圍之濃度分散於水性載劑之水不可溶殺蟲劑之懸浮液。懸浮液係藉由將殺蟲劑細微研磨及將其劇烈混合於包含水及界面活性劑之載劑內而製備。諸如無機鹽及合成或天然膠之成份亦可被添加,以增加水性載劑之密度及黏度。通常最有效係藉由於諸如砂磨機、球磨機,或活塞型均質機內製備水性混合物及將其均質化而將殺蟲劑同時研磨及混合。
殺蟲劑亦可以特別可用於施加至土壤之顆粒狀組成物施加。顆粒狀組成物通常含有約0.5重量%至約10重量%之殺蟲劑,其係分散於包含黏土或相似物質之載劑內。此等組成物通常係藉由將殺蟲劑溶於一適合溶劑,及將其施加至已預先形成於約0.5至約3 mm範圍之適當顆粒尺寸之顆粒狀載劑而製備。此等組成物亦可藉由製成載劑及化合物之糰狀物或糊料及粉碎與乾燥獲得所欲顆粒狀粒子尺寸而配製。
含有殺蟲劑之塵粉係藉由將粉末型式之殺蟲劑與一適合粉狀之農業載劑(諸如,高嶺黏土、經研磨之火山岩等)緻密混合而製備。塵粉可適合地含有約1%至約10%之殺蟲劑。其可以一噴粉機以種子拌藥或以葉子施加而施加。
相等實際地以於廣泛用於農業化學之適當有機溶劑(通常係石油潤滑油,諸如,噴灑油)內之溶液型式施加殺蟲劑。
殺蟲劑亦可以氣溶膠組成物型式施加。於此等組成物,殺蟲劑係溶於為產生壓力之推進劑混合物之載劑。氣溶膠組成物係裝填於一容器內,混合物係自此容器經由一霧化閥分配。
殺蟲劑誘餌係於殺蟲劑與食物或引誘劑或二者混合時形成。當害蟲食用誘餌時,其亦消耗殺蟲劑。誘餌可採用顆粒、凝膠、可流動粉末、液體,或固體之型式。其亦可用於害蟲藏身處。
燻劑具有相對較高蒸氣壓且因此可以足夠濃度之氣體存在而殺死土壤或封閉空間內之害蟲的殺蟲劑。燻劑之毒性係與其濃度及曝露時間成比例。其特徵在於良好擴散能力,且係藉由滲透害蟲呼吸系統或經由害蟲表皮吸收而作用。燻劑係應用於控制氣密式片材下、氣密室或建築內或特別腔室內之貯存產物之害蟲。
殺蟲劑可藉由將殺蟲劑顆粒或滴液懸浮於各種型式之塑膠聚合物內而製成微膠囊。藉由改變聚合物之化學或藉由改變加工處理因素,可形成具有各種尺寸、溶解性、壁厚度,及滲透度之微膠囊。此等因素主控其內活性成份釋放之速度,因而影響產物之殘餘性能、作用速度,及氣味。
油溶液濃縮物係藉由將殺蟲劑溶於會使殺蟲劑維持於溶液之溶劑內而製造。由於溶劑本身具有殺蟲作用且外皮之蠟質覆蓋物之溶解增加殺蟲劑攝取速度,殺蟲劑之油溶液通常提供比其它配製物更快速地擊敗及殺死害
蟲。油溶液之其它優點包括較佳貯存安定性、較佳裂縫滲透性,及與油質表面較佳黏著性。
另一實施例係水包油之乳化液,其中,乳化液包含油質小球體,其每一者係具有層狀液晶塗覆物且係分散於一水性相,其中,每一油質小球體包含至少一具農業活性之化合物,且係個別以包含下述之一單層狀或寡層狀之層狀物塗覆:(1)至少一非離子親酯性表面活性劑,(2)至少一非離子親水性表面活性劑;及(3)至少一離子表面活性劑,其中,小球體具有少於800奈米之平均顆粒直徑。對於此實施例之進一步資訊係揭示於2007年2月1日公告之美國專利公告第20070027034號案,其具有專利申請序號第11/495,228號案。為了輕易使用,此實施例會稱為“OIWE”。
對於進一步資訊,查看“Insect Pest Management”,第2版,D.Dent,版權CAB International(2000)。另外,對於更詳細資訊,查看“Handbook of Pest Control-The Behavior,Life History,and Control of Household Pests”,Arnold Mallis,第9版,2004版權GIE Media Inc。
一般,當化學式1、2及3揭露之分子用於一配製物,此配製物亦可含有其它組份。此等組份不受限制地包括(此係非詳盡及非相互排它之列示)濕潤劑、展著劑、黏著劑、滲透劑、緩衝劑、螯合劑、漂浮降低劑、相容劑、抗發泡劑、清潔劑,及乳化劑。一些組份係即刻被說明。
濕潤劑係當添加至液體時藉由降低液體與其展開之表面間的界面張力而增加液體之展開或滲透力之物質。濕潤劑係因二主要功能而用於農用化學配製物:於加工及製造期間,增加粉末於水中之濕潤速率,以製成用於可溶性液體之濃縮物或懸浮濃物;及於產物與水於噴灑槽內混合期間,降低可濕潤粉末之濕潤時間及改良水於水可分散顆粒內之滲透。用於可濕潤粉末、懸浮濃縮物,及水可分散顆粒配製物之濕潤劑之例子係:月桂基硫酸鈉;二辛基磺基琥珀酸鈉;烷基酚乙氧化物;及脂族醇乙氧化物。
分散劑係吸附於顆粒表面上且助於保存顆粒分散狀態及避免再聚結之物質。分散劑係添加至農用化學配製物,以於製造期間促進分散及懸浮,及確保顆粒於噴灑槽內再次分散於水中。其係廣泛用於可濕潤顆粒、懸浮濃縮物,及水可分散顆粒。可作為分散劑之界面活性劑具有強烈吸附於顆粒表面上且對顆粒再聚結提供電荷或立體障壁之能力。最普遍使用之界面活性劑係陰離子、非離子,或此二種之混合物。對於可濕潤粉末配製物,最普遍之分散劑係木質素磺酸鈉。對於懸浮濃縮物,極佳吸附性及安定性係使用聚電解質獲得,諸如,萘磺酸鈉甲醛濃縮物。三苯乙烯基苯酚乙氧化物磷酸酯亦被使用。諸如烷基芳基乙烯化氧濃縮物及EO-PO嵌段共聚物之非離子物有時與陰離子物組合作為懸浮濃縮物之分散劑。近年,新型式之極高分子量聚合物界面活性劑已發展作為分散劑。此等具有極長之疏水性‘主鏈’及大數量之乙烯化氧鏈,其形成”梳狀”
界面活性劑之‘齒’。此等高分子量聚合物可對懸浮濃縮物產生極長期安定性,因為疏水性主鏈對顆粒表面具有許多固定點。用於農用化學配製物之分散劑之例子係:木質素磺酸鈉;萘磺酸鈉甲醛濃縮物;三苯乙烯基苯酚乙氧化物磷酸酯;脂族醇乙氧化物;烷基乙氧化物;EO-PO嵌段共聚物;及接枝共聚物。
乳化劑係使一液相滴液於另一液相內之懸浮液安定化之物質。無乳化劑,此二相會分成二不可溶混之液相。最普遍使用之乳化劑摻合物包含具有十二或更多個乙烯化氧單位之烷基酚或脂族醇,及十二烷基苯磺酸之油可溶性鈣鹽。8至18之範圍的親水親脂平衡(“HLB”)值一般會提供良好安定之乳化液。乳化安定性有時可藉由添加一小量之EO-PO嵌段共聚物界面活性劑而改良。
助溶劑係會以高於臨界微胞濃度之濃度於水中形成微胞之界面活性劑。然後,微胞能使水不溶之材料溶解或助溶於微胞之疏水部份內。通常用於助溶之界面活性劑型式係非離子物、山梨醇酐單油酸酯、山梨醇酐單油酸酯乙氧化物,及油酸甲酯。
界面活性劑有時係單獨或與其它添加劑(諸如,作為佐劑之礦物油或蔬菜油)用於噴灑槽混合物,以改良殺蟲劑對目標物之生物性能。用於生物增強之界面活性劑型式一般係依殺蟲劑之性質及作用模式而定。但是,其通常係非離子物,諸:烷基乙氧化物;線性脂族醇乙氧化物;脂族胺乙氧化物。
農用配製物中之載劑或稀釋劑係添加至殺蟲劑產生具所需強度之產品的材料。載劑通常係具高吸收能力之材料,而稀釋劑通常係具低吸收能力之材料。載劑及稀釋劑係用於塵粉、濕潤性粉末、顆粒,及水可分散顆粒之配製物。
有機溶劑主要係用於可乳化濃縮物、水包油之乳化液、懸乳液,及超低體積配製物之配製物,及較少程度之顆粒配製物。有時,係使用溶劑混合物。第一主要組群之溶劑係脂族石蠟油,諸如,煤油或精製石蠟。第二主要組群(且最普遍)包含芳香族溶劑,諸如,二甲苯及較高分子量之C9及C10芳香族溶劑分餾物。當配製物於水中乳化時,氯化烴可作為用以避免殺蟲劑結晶化之共溶劑。醇有時係作為用以增加溶劑力之共溶劑。其它溶劑可包括蔬菜油、籽油,及蔬菜油及籽油之酯。
增稠劑或膠凝劑主要用於懸浮濃縮物、乳化液及懸浮液之配製物,以改良液體之流變學或流動性質及避免分散顆粒或滴液分離及沉降。增稠劑、膠凝劑,及抗沉降劑一般係落於二類,即,水不可溶顆粒及水可溶聚合物。可使用黏土及矽石製造懸浮濃縮配製物。此等型式之材料的例子不受限制地包括蒙脫土、皂土、矽酸鎂鋁,及鎂鋁海泡石。水可溶多醣多年來已被作增稠膠凝劑。最普遍使用之多醣型式係種籽及海藻之天然萃取物或纖維素之合成衍生物。此等型式之物料的例子不受限制地包括瓜耳膠;刺塊豆膠;角叉菜膠;海藻酸鹽;甲基纖維素;羧甲基纖
維素鈉(SCMC);羥基乙基纖維素(HEC)。其它型式之抗沉降劑係以改質澱粉、多醣、聚乙烯醇,及聚乙烯化氧為主。另外之良好抗沉降劑係三仙膠。
微生物會造成配製產物損壞。因此,防腐劑被用
以去除或降低此等作用。此等試劑之例子不受限制地包括:丙酸及其鈉鹽;山梨酸及其鈉或鉀鹽;苯甲酸及其鈉鹽;對-羥基苯甲酸鈉鹽;對-羥基苯甲酸甲酯;及1,2-苯并異噻唑-3-酮(BIT)。
界面活性劑之存在通常造成以水為主之配製物於製造及於經由噴灑槽施用之混合操作期間發泡。為降低發泡趨勢,抗發泡劑通常係於製造階段期間或填充於瓶子內之前添加。一般,有二種抗發泡劑,即,聚矽氧及非聚矽氧。聚矽氧通常係二甲基聚矽氧烷之水性乳化液,而非聚矽氧抗發泡劑係水不可溶油,諸如,辛醇及壬醇,或矽石。於二情況,抗發泡劑之功能係替換空氣-水界面之界面活性劑。
“綠色”劑(例如,佐劑、界面活性劑、溶劑)可降低作物保護配製物之整體環境足跡。綠色劑係生物可降解,且一般係衍生自天然及/或永續之來源,例如,植勿及動物來源。特別例子係:蔬菜油、籽油,及其等之酯,與烷氧化之烷基多醣。
對於進一步資訊,見“Chemistry and Technology of Agrochemical Formulations”,D.A. Knowles編輯,1998版權Kluwer Academic Publishers。亦見“Insecticides in
Agriculture and Environment-Retrospects and Prospects”,A.S. Perry、I. Yamamoto、I. Ishaaya,及R. Perry,1998版權Springer-Verlag。
一般,具化學式1、2及3之分子可用於控制害蟲,例如,甲蟲、蠳螋、蟑螂、蒼蠅、蚜蟲、介殼蟲、粉蝨、葉蟬、螞蟻、黃蜂、白蟻、蛾、蝴蝶、虱、草蜢、蝗蟲、蟋蟀、跳蚤、薊馬、衣魚、小蜘蛛、壁虱、線蟲,及綜合蟲。
於另一實施例,具化學式1、2及3之分子可用以控制線蟲動物(Phyla Nematoda)及/或節肢動物門(Arthropoda)之害蟲。
於另一實施例,具化學式1、2及3之分子可用以控制螯肢(Subphyla Chelicerata)、多足(Myriapoda)及/或六足亞門(Hexapoda)之害蟲。
於另一實施例,具化學式1、2及3之分子可用以控制蛛形(Arachnida)綱、綜合(Symphyla)綱及/或昆蟲(Insecta)綱之害蟲。
於另一實施例,具化學式1、2及3之分子可用以控制半翅目(Order Anoplura)之害蟲。特別屬之非詳盡列示不受限制地包括肺蟲(Haematopinus spp.)、甲脅虱(Hoplopleura spp.)、壁虱(Linognathus spp.)、體虱(Pediculus spp.),及彎多板虱(Polyplax spp.)。特別種類之非詳盡列示不受限制地包括馬虱(Haematopinus asini)、豬虱
(Haematopinus suis)、棘顎虱(Linognathus setosus)、綿羊顎虱(Linognathus ovillus)、頭虱(Pediculus humanus capitis)、人類體虱(Pediculus humanus humanus),及陰虱(Pthirus pubis)。
於另一實施例,具化學式1、2及3之分子可用以控制鞘翅目(Order Coleoptera)之害蟲。特別屬之非詳盡列示不受限制地包括菜豆象屬(Acanthoscelides spp.)、叩頭蟲屬(Agriotes spp.)、象鼻蟲屬(Anthonomus spp.)、種籽象甲蟲屬(Apion spp.)、金龜屬(Apogonia spp.)、黃守瓜屬(Aulacophora spp.)、豆象蟲屬(Bruchus spp.)、天牛屬(Cerosterna spp.)、豆葉甲蟲屬(Cerotoma spp.)、象鼻蟲屬(Ceutorhynchus spp.)、凹脛跳甲蟲屬(Chaetocnema spp.)、肖葉甲蟲屬(Colaspis spp.)、梳瓜扣頭蟲屬(Ctenicera spp.)、栗實象蟲屬(Curculio spp.)、獨角仙屬(Cyclocephala spp.)、玉米根蟲屬(Diabrotica spp.)、象甲蟲屬(Hypera spp.)、齒小蠹屬(Ips spp.)、粉蠹蟲屬(Lyctus spp.)、Megascelis spp.、菜花露尾甲蟲屬(Meligethes spp.)、蛀象鼻蟲屬(Otiorhynchus spp.)、玫瑰短喙象蟲屬(Pantomorus spp.)、金龜子屬(Phyllophaga spp.)、黃條跳甲蟲屬(Phyllotreta spp.)、歐洲金龜子屬(Rhizotrogus spp.)、梨象蟲屬(Rhynchites spp.)、棕櫚象蟲屬(Rhynchophorus spp.)、小蠹蟲屬(Scolytus spp.)、禾象鼻蟲屬(Sphenophorus spp.)、米象蟲屬(Sitophilus spp.),及擬穀盗蟲屬(Tribolium spp.)。特別種類之非詳盡列示不受限制地包括菜豆象蟲
(Acanthoscelides obtectus)、白蠟窄吉丁蟲(Agrilus planipennis)、光肩星天牛(Anoplophora glabripennis)、棉鈴象甲蟲(Anthonomus grandis)、黑絨金龜(Ataenius spretulus)、甜菜隱食甲蟲(Atomaria linearis)、甜菜象蟲(Bothynoderes punctiventris)、豌豆象蟲(Bruchus pisorum)、四紋豆象蟲(Callosobruchus maculatus)、黃斑露尾甲蟲(Carpophilus hemipterus)、甜菜龜甲蟲(Cassida vittata)、豆葉甲蟲(Cerotoma trifurcata)、甘藍莢象甲蟲(Ceutorhynchus assimilis)、白菜象鼻蟲(Ceutorhynchus napi)、梯斑叩頭蟲(Conoderus scalaris)、多斑叩頭蟲(Conoderus stigmosus)、李象鼻蟲(Conotrachelus nenuphar)、綠花金龜(Cotinis nitida)、天冬門葉甲蟲(Crioceris asparagi)、角胸粉扁蟲(Cryptolestes ferrugineus)、長角扁穀盗蟲(Cryptolestes pusillus)、土耳其扁穀盗蟲(Cryptolestes turcicus)、密點細枝象蟲(Cylindrocopturus adspersus)、芒果切葉象蟲(Deporaus marginatus)、火腿皮蠹(Dermestes lardarius)、白復皮蠹(Dermestes maculatus)、墨西哥豆瓢蟲(Epilachna varivestis)、煙草鉆孔蟲(Faustinus cubae)、樹皮象蟲(Hylobius pales)、苜蓿葉象甲蟲(Hypera postica)、咖啡果小蠹(Hypothenemus hampei)、煙草甲蟲(Lasioderma serricorne)、馬鈴薯甲蟲(Leptinotarsa decemlineata)、白蠐螬(Liogenys fuscus)、Liogenys suturalis、水稻水象鼻蟲(Lissorhoptrus oryzophilus)、Maecolaspis joliveti、玉米叩甲蟲(Melanotus communis)、油菜花露尾甲蟲(Meligethes aeneus)、大栗鰓角金龜(Melolontha melolontha)、梯頂天牛(Oberea brevis)、線狀天牛(Oberea linearis)、椰子犀角金龜(Oryctes rhinoceros)、大眼鋸殼盗蟲(Oryzaephilus mercator)、鋸胸粉扁蟲(Oryzaephilus surinamensis)、殼物葉子甲蟲(Oulema melanopus)、稻負泥蟲(Oulema oryzae)、金龜子(Phyllophaga cuyabana)、日本麗金龜(Popillia japonica)、大穀蠹(Prostephanus truncatus)、穀蠹(Rhyzopertha dominica)、條紋根瘤象蟲(Sitona lineatus)、穀象蟲(Sitophilus granarius)、米象蟲(Sitophilus oryzae)、玉米象蟲(Sitophilus zeamais)、藥材甲蟲(Stegobium paniceum)、赤擬穀盗蟲(Tribolium castaneum)、雜擬穀盗蟲(Tribolium confusum)、花斑皮蠹(Trogoderma variabile),及玉米距步甲蟲(Zabrus tenebrioides)。
於另一實施例,具化學式1、2及3之分子可用以控制革翅目(Order Dermaptera)之害蟲。
於另一實施例,具化學式1、2及3之分子可用以控制蜚蠊目(Order Blattaria)之害蟲。特別種類之非詳盡列示不受限制地包括德國蟑螂(Blattella germanica)、東方蜚蠊(Blatta orientalis)、賓西法尼亞木蠊(Parcoblatta pennsylvanica)、美洲蟑螂(Periplaneta americana)、澳洲蜚蠊(Periplaneta australasiae)、棕色家蠊(Periplaneta brunnea)、煙褐蟑螂(Periplaneta fuliginosa)、潛伏蟑螂(Pycnoscelus surinamensis),及棕帶蜚蠊(Supella longipalpa)。
於另一實施例,具化學式1、2及3之分子可用以控制雙翅目(Order Diptera)之害蟲。特別屬之非詳盡列示不受限制地包括斑蚊屬(Aedes spp.)、潛蠅屬(Agromyza spp.)、按實蠅屬(Anastrepha spp.)、瘧蚊屬(Anopheles spp.)、果實蠅屬(Bactrocera spp.)、地中海實蠅屬(Ceratitis spp.)、斑虻屬(Chrysops spp.)、螺旅蠅屬(Cochliomyia spp.)、癭蚊屬(Contarinia spp.)、家蚊屬(Culex spp.)、癭蠅屬(Dasineura spp.)、種蠅屬(Delia spp.)、果蠅屬(Drosophila spp.)、廁蠅屬(Fannia spp.)、黑蠅屬(Hylemyia spp.)、斑潛蠅屬(Liriomyza spp.)、家蠅屬(Musca spp.)、草種蠅屬(Phorbia spp.)、虻蟲屬(Tabanus spp.),及大蚊屬(Tipula spp.)。特別種類之非詳盡列示不受限制地包括苜蓿斑潛蠅(Agromyza frontella)、加勒比海果實蠅(Anastrepha suspensa)、墨西哥果實蠅(Anastrepha ludens)、西印度果實蠅(Anastrepha obliqa)、瓜實蠅(Bactrocera cucurbitae)、東方果實蠅(Bactrocera dorsalis)、入侵果實蠅(Bactrocera invadens)、桃果實蠅(Bactrocera zonata)、地中海果實蠅(Ceratitis capitata)、油菜莢葉癭蚊(Dasineura brassicae)、灰地種蠅(Delia platura)、夏廁蠅(Fannia canicularis)、灰腹廁蠅(Fannia scalaris)、腸胃蠅(Gasterophilus intestinalis)、Gracillia perseae、角蠅(Haematobia irritans)、牛蠅(Hypoderma lineatum)、菜斑潛蠅(Liriomyza brassicae)、綿羊虱蠅(Melophagus ovinus)、秋家蠅(Musca autumnalis)、肉蠅(Musca domestica)、羊狂蠅(Oestrus ovis)、黑麥稈蠅
(Oscinella frit)、甜菜蠅(Pegomya betae)、胡蘿蔔蠅(Psila rosae)、實桃實蠅(Rhagoletis cerasi)、蘋果果實蠅(Rhagoletis pomonella)、越橘果實蠅(Rhagoletis mendax)、麥紅吸漿蟲(Sitodiplosis mosellana),及廄螯蠅(Stomoxys calcitrans)。
於另一實施例,具化學式1、2及3之分子可用以控制半翅目(Order Hemiptera)之害蟲。特別屬之非詳盡列示不受限制地包括球蚜屬(Adelges spp.)、介殼蟲屬(Aulacaspis spp.)、沫蟬屬(Aphrophora spp.)、蚜蟲屬(Aphis spp.)、粉虱屬(Bemisia spp.)、蠟蚧屬(Ceroplastes spp.)、盾蚧屬(Chionaspis spp.)、褐圓盾介殼蟲屬(Chrysomphalus spp.)、胭脂蟲屬(Coccus spp.)、葉蟬屬(Empoasca spp.)、蠣盾介殼蟲屬(Lepidosaphes spp.)、稻椿象屬(Lagynotomus spp.)、棉盲椿屬(Lygus spp.)、長管蚜屬(Macrosiphum spp.)、葉蟬屬(Nephotettix spp.)、綠椿屬(Nezara spp.)、沫蟬屬(Philaenus spp.)、植盲椿屬(Phytocoris spp.)、璧椿屬(Piezodorus spp.)、粉介殼蟲屬(Planococcus spp.)、粉蚧蟲屬(Pseudococcus spp.)、縊管蚜屬(Rhopalosiphum spp.)、硬介殼蟲屬(Saissetia spp.)、斑蚜屬(Therioaphis spp.)、蠟蚧蟲屬(Toumeyella spp.)、桔蚜屬(Toxoptera spp.)、粉虱屬(Trialeurodes spp.)、錐椿屬(Triatoma spp.),及矢尖蚧屬(Unaspis spp.)。特別種類之非詳盡列示不受限制地包括擬綠椿(Acrosternum hilare)、豌豆蚜(Acyrthosiphon pisum)、甘藍粉虱(Aleyrodes proletella)、螺旋粉虱(Aleurodicus dispersus)、絲絨粉虱(Aleurothrixus floccosus)、二點小綠葉蟬(Amrasca biguttula biguttula)、紅圓蚧(Aonidiella aurantii)、棉蚜(Aphis gossypii)、大豆呀(Aphis glycines)、蘋果蚜蟲(Aphis pomi)、馬鈴薯蚜(Aulacorthum solani)、銀葉粉虱(Bemisia argentifolii)、煙草粉虱(Bemisia tabaci)、麥長椿象蟲(Blissus leucopterus)、天冬門小管蚜(Brachycorynella asparagi)、稻粉介殼蟲(Brevennia rehi)、甘藍蚜(Brevicoryne brassicae)、草莓椿(Calocoris norvegicus)、紅蠟介殼蟲(Ceroplastes rubens)、床蝨(Cimex hemipterus)、溫帶臭蟲(Cimex lectularius)、Dagbertus fasciatus、Dichelops furcatus、麥雙尾蚜(Diuraphis noxia)、柑桔木蝨(Diaphorina citri)、玫瑰蘋果蚜(Dysaphis plantaginea)、棉黑翅紅椿(Dysdercus suturellus)、Edessa meditabunda、蘋果棉蚜(Eriosoma lanigerum)、歐扁盾椿(Eurygaster maura)、大豆褐椿(Euschistus heros)、褐臭椿(Euschistus servus)、安妥角盲椿(Helopeltis antonii)、茶角盲椿(Helopeltis theivora)、吹棉介殼蟲(Icerya purchasi)、檸果褐葉蟬(Idioscopus nitidulus)、斑飛蝨(Laodelphax striatellus)、大稻緣椿(Leptocorisa oratorius)、稻緣椿象(Leptocorisa varicornis)、豆莢盲椿(Lygus hesperus)、桑粉介殼蟲(Maconellicoccus hirsutus)、馬鈴薯長管蚜(Macrosiphum euphorbiae)、麥長管蚜(Macrosiphum granarium)、薔薇長管蚜(Macrosiphum rosae)、翠菊葉蟬(Macrosteles quadrilineatus)、沬蟬(Mahanarva frimbiolata)、麥無網長管蚜(Metopolophium dirhodum)、長角椿象(Mictis longicornis)、桃蚜(Myzus persicae)、葉蟬(Nephotettix cinctipes)、Neurocolpus longirostris、南方綠椿(Nezara viridula)、褐灰蝨(Nilaparvata lugens)、糠片盾蚧(Parlatoria pergandii)、黑點介殼蟲(Parlatoria ziziphi)、玉米飛蝨(Peregrinus maidis)、葡萄根瘤蚜(Phylloxera vitifoliae)、去杉球蚧(Physokermes piceae)、加州盲椿(Phytocoris californicus)、植盲椿(Phytocoris relativus)、紅肩綠椿(Piezodorus guildinii)、四線盲椿(Poecilocapsus lineatus)、Psallus vaccinicola、Pseudacysta perseae、菠蘿粉介殼蟲(Pseudococcus brevipes)、梨笠圓盾蚧(Quadraspidiotus perniciosus)、玉米蚜(Rhopalosiphum maidis)、稻麥蚜(Rhopalosiphum padi)、橄欖黑盾蚧(Saissetia oleae)、Scaptocoris castanea、麥二叉蚜(Schizaphis graminum)、麥長管蚜(Sitobion avenae)、白背飛虱(Sogatella furcifera)、溫室粉虱(Trialeurodes vaporariorum)、煙粉虱(Trialeurodes abutiloneus)、箭頭介殼蟲(Unaspis yanonensis,),及Zulia entrerriana。
於另一實施例,具化學式1、2及3之分子可用以控制膜翅目(Order Hymenoptera)之害蟲。特別屬之非詳盡列示不受限制地包括切葉蟻屬(Acromyrmex spp.)、切葉蟻屬(Atta spp.)、巨山蟻屬(Camponotus spp)、松葉蜂屬(Diprion spp.)、螞蟻屬(Formica spp.)、單家蟻屬(Monomorium spp.)、松葉蜂屬(Neodiprion spp.)、收割蟻屬(Pogonomyrmex spp.)、長腳蜂屬(Polistes spp.)、紅火蟻屬(Solenopsis spp.)、黃斑胡蜂屬(Vespula spp.),及黃領花蜂屬(Xylocopa spp.)。
特別種類之非詳盡列示不受限制地包括菜葉蜂(Athalia rosae)、德克塞斯切葉蟻(Atta texana)、阿根廷蟻(Iridomyrmex humilis)、小黑家蟻(Monomorium minimum)、法老蟻(Monomorium pharaonis)、入侵火紅蟻(Solenopsis invicta)、熱帶火蟻(Solenopsis geminata,)、竊葉蟻(Solenopsis molesta)、黑火蟻(Solenopsis richtery)、南方火蟻(Solenopsis xyloni),及酸臭蟻(Tapinoma sessile)。
於另一實施例,具化學式1、2及3之分子可用以控制等翅目(Order Isoptera)之害蟲。特別屬之非詳盡列示不受限制地包括乳白蟻屬(Coptotermes spp.)、白蟻屬(Cornitermes spp)、堆砂白蟻屬(Cryptotermes spp.)、寬唇異白蟻屬(Heterotermes spp.)、木白蟻屬(Kalotermes spp)、楹白蟻屬(Incisitermes spp.)、大白蟻屬(Macrotermes spp.)、緣木白蟻屬(Marginitermes spp.)、鋸白蟻屬(Microcerotermes spp.)、Procornitermes spp.、散白蟻屬(Reticulitermes spp.)、長鼻白蟻屬(Schedorhinotermes spp.),及古白蟻屬(Zootermopsis spp)。特別種類之非詳盡列示不受限制地包括橡膠白蟻(Coptotermes curvignathus)、法國乳白蟻(Coptotermes frenchi)、台灣乳白蟻(Coptotermes formosanus)、金黃色異白蟻(Heterotermes aureus)、小白蟻(Microtermes obesi)、散白蟻(Reticulitermes banyulensis)、格氏散白蟻(Reticulitermes grassei)、黃肢散白蟻(Reticulitermes flavipes)、哈氏散白蟻(Reticulitermes hageni)、地底白蟻(Reticulitermes hesperus)、地下散白蟻
(Reticulitermes santonensis)、黃胸散白蟻(Reticulitermes speratus)、黑胸散白蟻(Reticulitermes tibialis),及南方散白蟻(Reticulitermes virginicus.)。
於另一實施例,具化學式1、2及3之分子可用以控制鱗翅目(Order Lepidoptera)之害蟲。特別屬之非詳盡列示不受限制地包括卷葉蛾屬(Adoxophyes spp.)、切根蟲屬(Agrotis spp.)、卷蛾屬(Argyrotaenia spp.)、卷葉蛾屬(Cacoecia spp.)、麗細蛾屬(Caloptilia spp.)、水稻螟蟲屬(Chilo spp.)、夜蛾屬(Chrysodeixis spp.)、豆粉蝶屬(Colias spp.)、草螟屬(Crambus spp.)、絹野螟屬(Diaphania spp.)、螟蟲屬(Diatraea spp.)、鉆夜蛾屬(Earias spp.)、粉斑螟屬(Ephestia spp.)、尺護蛾屬(Epimecis spp.)、斑點夜蛾屬(Feltia spp.)、夜蛾屬(Gortyna spp.)、棉鈴蟲屬(Helicoverpa spp.)、實夜蛾屬(Heliothis spp.)、Indarbela spp.、潛夜細蛾屬(Lithocolletis spp.)、切根蟲屬(Loxagrotis spp.)、天幕毛蟲屬(Malacosoma spp.)、疆夜蛾屬(Peridroma spp.)、潛葉蛾屬(Phyllonorycter spp.)、黏夜蛾屬(Pseudaletia spp.)、大螟屬(Sesamia spp.)、灰翅夜蛾屬(Spodoptera spp.)、透翅蛾屬(Synanthedon spp.),及巢蛾屬(Yponomeuta spp.)。特別種類之非詳盡列示不受限制地包括飛揚阿夜蛾(Achaea janata)、棉褐帶卷蛾(Adoxophyes orana)、球菜夜蛾(Agrotis ipsilon)、棉樹葉蟲(Alabama argillacea)、鰐梨卷葉蟲(Amorbia cuneana)、臍橙螟蛾(Amyelois transitella)、棕灰蛾(Anacamptodes defectaria)、桃芽蛾(Anarsia lineatella)、
黃麻夜蛾(Anomis sabulifera)、黎豆夜蛾(Anticarsia gemmatalis)、果樹黃卷蛾(Archips argyrospila)、玫瑰黃卷蛾(Archips rosana)、桔帶卷蛾(Argyrotaenia citrana)、γ紋葉蛾(Autographa gamma)、卷葉蛾(Bonagota cranaodes)、禾弄蝶(Borbo cinnara)、棉潛蛾(Bucculatrix thurberiella)、桔橘卷蛾(Capua reticulana)、桃蛀果蛾(Carposina niponensis)、檸果螟蛾(Chlumetia transversa)、玫瑰色卷蛾(Choristoneura rosaceana)、稻縱卷葉蛾(Cnaphalocrocis medinalis)、荔枝細蛾(Conopomorpha cramerella)、芳香木蠹蛾(Cossus cossus)、石核桃卷蛾(Cydia caryana)、桃蛀野螟(Cydia funebrana)、梨小食心蟲(Cydia molesta)、豌豆小卷蛾(Cydia nigricana)、蘋果蠹蛾(Cydia pomonella)、茶刺蛾(Darna diducta)、蔗螟(Diatraea saccharalis)、西南玉米螟(Diatraea grandiosella)、埃及鉆夜蛾(Earias insulana)、翠紋鉛夜蛾(Earias vittella)、對小卷蛾(Ecdytolopha aurantianum)、小玉米莖蛀蟲(Elasmopalpus lignosellus)、粉斑螟蛾(Ephestia cautella)、煙草粉斑螟(Ephestia elutella)、地中海粉斑螟(Ephestia kuehniella)、大豆田小卷蛾(Epinotia aporema)、蘋淺褐卷蛾(Epiphyas postvittana)、香蕉弄蝶(Erionota thrax)、環針單紋卷蛾(Eupoecilia ambiguella)、原切根蟲(Euxoa auxiliaris)、桃折心蟲(Grapholita molesta)、三紋螟蛾(Hedylepta indicata)、番茄夜蛾(Helicoverpa armigera)、美洲棉鈴蟲(Helicoverpa zea)、綠棉鈴蟲(Heliothis virescens)、菜心野螟蛾(Hellula undalis)、番茄蠹
蛾(Keiferia lycopersicella)、茄白翅野螟(Leucinodes orbonalis)、咖啡潛葉蛾(Leucoptera coffeella)、旋紋潛蛾(Leucoptera malifoliella)、葡萄花翅小卷蛾(Lobesia botrana)、豆白緣切根蟲(Loxagrotis albicosta)、舞毒蛾(Lymantria dispar)、桃潛葉蛾(Lyonetia clerkella)、簑蛾(Mahasena corbetti)、甘藍夜蛾(Mamestra brassicae)、豆莢螟(Maruca testulalis)、碎葉蓑蛾(Metisa plana)、栗夜盗蟲(Mythimna unipuncta)、番茄蛀蟲(Neoleucinodes elegantalis)、白水螟蛾(Nymphula depunctalis)、冬尺蛾(Operophtera brumata)、玉米螟(Ostrinia nubilalis)、Oxydia vesulia、疆褐卷蛾(Pandemis cerasana)、蘋褐卷蛾(Pandemis heparana)、非洲達摩鳳蝶(Papilio demodocus)、棉紅鈴蟲(Pectinophora gossypiella)、疆夜蛾(Peridroma saucia)、咖啡潛葉蛾(Perileucoptera coffeella)、馬鈴薯蠹蛾(Phthorimaea operculella)、柑橘潛夜蛾(Phyllocnistis citrella)、紋白蝶(Pieris rapae)、苜蓿盲椿(Plathypena scabra)、印度谷螟(Plodia interpunctella)、小菜蛾(Plutella xylostella)、卷蛾(Polychrosis viteana)、桔果巢蛾(Prays endocarpa)、油橄欖巢蛾(Prays oleae)、一星黏蟲(Pseudaletia unipuncta)、大豆尺夜蛾(Pseudoplusia includens)、向日葵尺蠖(Rachiplusia nu)、三化螟(Scirpophaga incertulas)、大螟(Sesamia inferens)、四非蛀莖夜蛾(Sesamia nonagrioides)、荨麻毛蟲(Setora nitens)、麥蛾(Sitotroga cerealella)、葡萄長卷葉蛾(Sparganothis pilleriana)、甜菜葉蛾(Spodoptera exigua)、草地貪夜蛾(Spodoptera frugiperda)、南方灰翅夜蛾(Spodoptera eridania)、菠蘿褐灰蝶(Thecla basilides)、衣蛾(Tineola bisselliella)、粉紋夜蛾(Trichoplusia ni)、斑潛蠅(Tuta absoluta)、咖啡蠹蛾(Zeuzera coffeae),及梨豹蠹蛾(Zeuzera pyrina)。
於另一實施例,具化學式1、2及3之分子可用以控制食毛目(Order Mallophaga)之害蟲。特別屬之非詳盡列示不受限制地包括細鵝虱屬(Anaticola spp.)、牛毛虱屬(Bovicola spp.)、大火雞虱屬(Chelopistes spp.)、雞角羽虱(Goniodes spp.)、雞虱屬(Menacanthus spp.),及犬食毛虱(Trichodectes spp.)。特別種類之非詳盡列示不受限制地包括牛羽虱(Bovicola bovis)、山羊住牛虱(Bovicola caprae)、綿羊虱(Bovicola ovis)、大火雞虱(Chelopistes meleagridis)、雞角羽虱(Goniodes dissimilis)、大角羽虱(Goniodes gigas)、雞黃體虱子(Menacanthus stramineus)、雞短角羽虱(Menopon gallinae),及犬嚙毛虱(Trichodectes canis)。
於另一實施例,具化學式1、2及3之分子可用以控制支翅目(Order Orthoptera)之害蟲。特別屬之非詳盡列示不受限制地包括黑蝗屬(Melanoplus spp.)及側羽葉屬(Pterophylla spp.)。特別種類之非詳盡列示不受限制地包括摩門蟋蟀(Anabrus simplex)、非洲螻蛄(Gryllotalpa africana)、南方螻蛄(Gryllotalpa australis)、黑短螻蛄(Gryllotalpa brachyptera)、歐洲痣蟋蟀(Gryllotalpa hexadactyla)、東亞飛蝗(Locusta migratoria)、小角翅蟈蟈(Microcentrum retinerve)、沙漠蝗蟲(Schistocerca gregaria),及叉尾灌叢樹蟲(Scudderia furcata)。
於另一實施例,具化學式1、2及3之分子可用以控制蚤目(Order Siphonaptera)之害蟲。特別種類之非詳盡列示不受限制地包括禽蚤(Ceratophyllus gallinae)、雞角葉蚤(Ceratophyllus niger)、狗蚤(Ctenocephalides canis)、貓蚤(Ctenocephalides felis),及人蚤(Pulex irritans)。
於另一實施例,具化學式1、2及3之分子可用以控制纓翅目(Order Thysanoptera)之害蟲。特別屬之非詳盡列示不受限制地包括巢針薊馬屬(Caliothrips spp.)、花薊馬屬(Frankliniella spp.)、黃薊馬屬(Scirtothrips spp.),及薊馬屬(Thrips spp.)。特別種類之非詳盡列示不受限制地包括褐花薊馬(Frankliniella fusca)、西方花薊馬(Frankliniella occidentalis)、梳缺花薊馬(Frankliniella schultzei)、威廉期花薊馬(Frankliniella williamsi)、溫室薊馬(Heliothrips haemorrhoidalis)、腹鉤薊馬(Rhipiphorothrips cruentatus)、桔梗薊馬(Scirtothrips citri)、小黃薊馬(Scirtothrips dorsalis),及薊馬(Taeniothrips rhopalantennalis)、黃胸薊馬(Thrips hawaiiensis)、豆黃薊馬(Thrips nigropilosus)、東方薊馬(Thrips orientalis)、煙薊馬(Thrips tabaci)。
於另一實施例,具化學式1、2及3之分子可用以控制衣角目(Order Thysanura)之害蟲。特別屬之非詳盡列示不受限制地包括衣魚屬(Lepisma spp.)及衣角屬(Thermobia spp.)。
於另一實施例,具化學式1、2及3之分子可用以控制蟎目(Order Acarina)之害蟲。特別屬之非詳盡列示不受限制地包括粉蟎屬(Acarus spp.)、刺皮癭蟎屬(Aculops spp.)、牛壁虱屬(Boophilus spp.)、皮膚蟎屬(Demodex spp.)、革蜱屬(Dermacentor spp.)、銹蜱屬(Epitrimerus spp.)、氈蟎屬(Eriophyes spp.)、硬蜱屬(Ixodes spp.)、葉蟎屬(Oligonychus spp.)、全爪蟎屬(Panonychus spp.)、根蟎屬(Rhizoglyphus spp.),及葉蟎屬(Tetranychus spp.)。特別種類之非詳盡列示不受限制地包括伍德氏蟎(Acarapis woodi)、粗腳粉蟎(Acarus siro)、瘤癭蟎(Aceria mangiferae)、番茄刺皮癭蟎(Aculops lycopersici)、皮氏刺皮癭蟎(Aculus pelekassi)、蘋果銹蜱(Aculus schlechtendali)、美洲鈍眼蜱(Amblyomma americanum)、卵形短鬚蟎(Brevipalpus obovatus)、紫紅短鬚蟎(Brevipalpus phoenicis)、變異革蜱(Dermacentor variabilis)、塵蟎(Dermatophagoides pteronyssinus)、鵝耳櫪台葉蟎(Eotetranychus carpini)、貓耳蟎(Notoedres cati)、茶樹茶紅蟎(Oligonychus coffeae)、冬青木爪蟎(Oligonychus ilicis)、柑桔全爪蟎(Panonychus citri)、蘋果全爪蟎(Panonychus ulmi)、柑橘銹壁虱(Phyllocoptruta oleivora)、茶黃蟎(Polyphagotarsonemus latus)、血紅扇頭蜱(Rhipicephalus sanguineus)、人疥蟎(Sarcoptes scabiei)、冠頂癭蟎(Tegolophus perseaflorae)、二斑葉蟎(Tetranychus urticae),及蜂蟹蟎(Varroa destructor)。
於另一實施例,具化學式1、2及3之分子可用以控制綜合目(Order Symphyla)之害蟲。特別屬之非詳盡列示不受限制地包括庭院蜈蚣(Scutigerella immaculata)。
於另一實施例,具化學式1、2及3之分子可用以控制線蟲動物門(Phylum Nematoda)之害蟲。特別屬之非詳盡列示不受限制地包括葉芽線蟲屬(Aphelenchoides spp.)、刺線蟲屬(Belonolaimus spp.)、環紋線蟲屬(Criconemella spp.)、莖線蟲屬(Ditylenchus spp.)、包囊線蟲屬(Heterodera spp.)、潛根線蟲屬(Hirschmanniella spp.)、冠線蟲屬(Hoplolaimus spp.)、根瘤線蟲屬(Meloidogyne spp.)、根腐線蟲屬(Pratylenchus spp.),及穿孔線蟲屬(Radopholus spp.)。特別種類之非詳盡列示不受限制地包括心絲蟲(Dirofilaria immitis)、玉米胞囊線蟲(Heterodera zeae)、南方根結線蟲(Meloidogyne incognita)、爪哇根結線蟲(Meloidogyne javanica)、旋盤尾絲蟲(Onchocerca volvulus)、香蕉穿孔線蟲(Radopholus similis),及腎形線蟲(Rotylenchulus reniformis)。
對於另外資訊,查閱“HANDBOOK OF PEST CONTROL-THE BEHAVIOR,LIFE HISTORY,AND CONTROL OF HOUSEHOLD PESTS”,Arnold Mallis,第9版,2004版權GIE Media Inc.。
具化學式1、2及3之分子一般係以每公頃約0.01克至每公頃約5000克之量使用以提供控制。每公頃約0.1克
至每公頃約500克之量一般係較佳,且每公頃約1克至每公頃約50克之量係更佳。
具化學式1、2或3之分子施用之區域可為害蟲居住住(或可能居住,或經過)之任何區域,例如:作物、樹木、水果、穀物、飼料物種、藤木、草皮,及觀賞植物生長處;家畜居住處;建築物之室內或室外表面(諸如,穀物貯存位置)、建築用之建構材料(諸如,浸漬木材),及建築周圍之土壤。使用具化學式1之分子之特別作物區域包括蘋果、玉米、葵花、棉花、黃豆、芥花、小麥、稻米、高梁、大麥、燕麥、馬鈴薯、柑橘、苜蓿芽、萵苣、草莓、番茄、胡椒、十字花科植物、梨、煙草、杏仁、甜菜、豆子,及其它有價植之作物生長或其種籽將種植之區域。當生長各種植物時,亦有利地係使用鋁酸鹽及具化學式1之分子。
控制害蟲一般意指害蟲組群、害蟲活性,或二者於一區域內被降低。此可於害蟲組群自一區域逐退時;害蟲於一區域或其附近喪失能力時;或害蟲於一區域或附近整體或部份被滅絕時發生。當然,此等結果之組合一般會發生。一般,害族之組群、活性,或二者所欲地係降低多於50%,較佳係多於90%。一般,此區域並非於人類;因此,位置一般係無人類區域。
具化學式1、2及3之分子可單獨或與其它化合物以混合物使用,同時或依序施加,以增強植物活力(例如,生長較佳根部系統,較佳地耐有壓力之生長條件)。此等其它化合物係,例如,調節植物乙烯受體之化合物,最顯著
係1-甲基環丙烯(亦稱為1-MCP)。
具化學式1、2及3之分子可施用至植物之葉上及果實部份以控制害蟲。此等分子會與害蟲直接接觸,或害蟲於食用含有殺蟲劑之葉子、果質或萃取汁液時會消耗殺蟲劑。具化學式1、2及3之分子亦可施用至土壤,且當以此方式施加時,食用根部及莖部之害蟲可被控制。根部亦會吸收分子,將其吸收至植物之葉子部,以控制地面上咬食及食用汁液之害蟲。
一般,使用誘餌,誘餌係置於,例如,白蟻與誘餌接觸及/或受其吸引之地面。誘餌可施用於建築物表面(水平、垂直或傾斜表面),例如,螞蟻、白蟻、蟑螂,及蒼蠅會與誘餌接觸及/或受其吸引處。誘餌可包含具化學式1、2或3之分子。
具化學式1、2及3之分子可包封於膠囊內部,或置於其表面上。膠囊尺寸範圍可為奈米尺寸(直徑約100-900奈米)至微米尺寸(直徑約10-900微米)。
因為某些害蟲之卵耐某些殺蟲劑之獨特能力,重複施用化學式1、2或3可所欲地控制新長出之幼蟲。
將殺蟲劑系統式移至植物內可藉由將具化學式1、2或3之分子施用(例如,藉由噴灑一區域)至植物之不同部份而控制植物之一部份。例如,食用葉子之害蟲之控制可藉由滴灌或犁溝施用,藉由以例如種植前或種植後之土壤澆灌而處理土壤,或藉由於種植前處理植物種籽而達成。
種籽處理可應用於所有種類之種籽,包括被基因
改質以表現特定化特性之植物會發芽者。代表性例子包括對無脊椎害蟲(諸如,蘇力菌)表現蛋白毒性或其它殺蟲毒性者,表現耐除草劑者,諸如,“轉基因大豆(Roundup Ready)”種籽,或具有表現殺蟲毒性、耐除草劑、營養強化、耐旱性,或任何其它有利特性之“堆疊式”外源基因者。再者,此等以具化學式1、2或3之分子之種籽處理可進一步增強植物較佳耐壓力生長條件之能力。此造成更健康、更有活力之植物,此可導致於收割期較高產量。一般,每100,000個種籽約1克之具化學式1、2或3之分子至約500克被預期提供良好益處,每100,000個種籽約10克至約100克之量被預期提供更佳益處,且每100,000個種籽約25克至約75克之量被預期提供更佳益處。
顯然地,具化學式1、2及3之分子可用於經基因改良表示特定特性(諸如蘇力菌或其它殺蟲毒性)之植物上、其它或周圍,或表現耐除草劑者,或具有表現殺蟲毒性、耐除草劑、營養強化、耐旱性,或任何其它有利特性之“堆疊式”外源基因者。
具化學式1、2及3之分子可用以控制獸醫業或非人類之動物護理領域之內寄生蟲及皮外寄生蟲。具化學式1、2及3之分子可藉由以,例如,錠劑、膠囊、飲料、顆粒之型式口服投藥,藉由以,例如,浸泡、噴灑、傾倒、點藥,及噴粉之型式經皮膚施用,及藉由以,例如,注射之型式腸胃外投藥而施用。
具化學式1、2及3之分子亦可有利地用於禽畜飼
養,例如,牛、羊、豬、雞,及鵝。亦可有利地用於寵物,諸如,馬、狗,及貓。欲控制之特別害蟲會係會對此等動物造成麻煩之跳蚤及蜱。適合配製物係藉由飲水或餵食而口服投用至此等動物。適合之劑量及配製物係依種類而定。
具化學式1、2及3之分子亦可用於控制於上示動物中之管圓線蟲,特別是腸內。
具化學式1、2及3之分子亦可用於人類健康照護之治療方法。此等方法不受限制地包括以,例如,錠劑、膠囊、飲料、顆粒型式口服投藥,及藉由皮膚塗敷。
全世界之害蟲正遷移至(對此害蟲係)新的環境,且其後於此新環境變成新侵入物種。具化學式1及2之分子亦可用於此等新侵入物種,而對其等於此新環境中作控制。
具化學式1、2及3之分子亦可用於諸如作物之植物生長(例如,種植前、種植中、採收前)之區域,及會對此等植物造成商業上損害之低程度(甚至無實際存在)害蟲之區域。於此區域使用此等分子會對於此區域生長之植物造成益處。此等益處可不受限制地包括改良植物健康,改良植物產量(例如,增加生物質量及/或增加有價值成份之含量),改良植物活力(例如,改良植物生長及/或更綠之葉子),改良植物品質(例如,改良某些成份之含量或組成),及改良植物對非生物及/或生物壓力之容忍性。
於殺蟲劑可被使用或商業販售前,此殺蟲劑係由各種政府機構(地方、區域、州立、國家,及國際)進行長時
間之評估程序。大量資料要求係由法規機構特定,且需由產品註冊者或代表產品註冊者之第三方經由資料產生及提交而處理,通當係使用與全球資訊網連接之電腦。然後,此等政府機構查核此資料,且若安全性決定結束,提供可能使用者或販售者產品註冊許可。其後,於產品註冊被授予及支持之地方,此使用者或販售者可使用或販售此殺蟲劑。
依據化學式1、2及34之分子可被測試而決定其對抗害蟲之效率。再者,作用模式研究可被進行以決定該分子是否具有不同於其它殺蟲劑之作用模式。其後,此獲得資料可藉由,諸如,網際網路傳播給第三方。
此文件中之標題僅係為了方便,且不應被用於闡釋其任何部份。
表格段落
Claims (32)
- 一種組成物,包含依據化學式2或3之分子,
- 如申請專利範圍第1項之分子,其中,Ar1係一經取代之苯基,其中,該經取代之苯基具有一或多個獨立地選自C1-C6鹵烷基及C1-C6鹵烷氧基之取代基。
- 如申請專利範圍第1項之分子,其中,Ar1係一經取代之苯基,其中,該經取代之苯基具有一或多個獨立地選自CF3、OCF3,及OCF2CF3之取代基。
- 如申請專利範圍第1項之分子,其中,Het係選自三唑基、咪唑基,或吡唑基,其等可經取代或未經取代。
- 如申請專利範圍第1項之分子,其中,Het係1,2,4-三唑基
- 如申請專利範圍第1項之分子,其中,Het係1,4-咪唑基
- 如申請專利範圍第1項之分子,其中,Het係1,3-吡唑基
- 如申請專利範圍第1項之分子,其中,Het係經取代之1,3-吡唑基。
- 如申請專利範圍第1項之分子,其中,Het係1,4-吡唑基
- 如申請專利範圍第1項之分子,其中,Ar2係苯基。
- 如申請專利範圍第1項之分子,其中,R1係H或C1-C6烷基。
- 如申請專利範圍第1項之分子,其中,R1係H或CH3。
- 如申請專利範圍第1項之分子,其中,R4係苯基、C1-C6烷基苯基,或C1-C6烷基-O-苯基,其中,每一烷基及苯基係選擇性地以一或多個選自下列之取代基取代:F、Cl、NRxRy、C1-C6烷基,或C1-C6烷氧基。
- 如申請專利範圍第1項之分子,其中,R5係未經取代。
- 如申請專利範圍第1項之分子,其中,Rx及Ry係獨立地選自H及苯基,其中,該苯基可選擇性地以一或多個獨 立地選自F及Cl之取代基取代。
- 如申請專利範圍第1項之分子,其中,Het-1係選自苯并呋喃基、苯并異噻唑基、苯并異唑基、苯并唑基、苯并噻吩基、苯并噻唑基、啉基、呋喃基、吲唑基、吲哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、酞基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹唑啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三基、三唑基、哌基、哌啶基、嗎啉基、吡咯啶基、四氫呋喃基、四氫吡喃基、1,2,3,4-四氫喹啉基、4,5-二氫唑基、4,5-二氫-1H-吡唑基、4,5-二氫異唑基,及2,3-二氫-[1,3,4]-二唑基。
- 如申請專利範圍第1項之分子,其中,Het係選自苯并呋喃基、苯并異噻唑基、苯并異唑基、苯并唑基、苯并噻吩基、苯并噻唑基、啉基、呋喃基、吲唑基、吲哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、酞基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三基、三唑基、哌基、哌啶基、嗎啉基、吡咯啶基、四氫呋喃基、四氫吡喃基、1,2,3,4-四氫喹啉基、4,5-二氫唑基、4,5-二氫-1H-吡唑基、4,5-二氫異唑基,及2,3-二氫-[1,3,4]-二唑基。
- 如申請專利範圍第1項之分子,其中,Het-1係選自苯并 呋喃基、苯并異噻唑基、苯并異唑基、苯并唑基、苯并噻吩基、苯并噻唑基、苯并噻二唑基、啉基、呋喃基、吲唑基、吲哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異唑基、二唑基、唑啉基、唑基、酞基、吡基、吡唑啉基、吡唑基、嗒基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹啉基、四唑基、噻唑啉基、噻唑基、噻吩基、噻吩基吡唑基、三基、三唑基、哌基、哌啶基、嗎啉基、吡咯啶基、四氫呋喃基、四氫吡喃基、1,2,3,4-四氫喹啉基、4,5-二氫唑基、4,5-二氫-1H-吡唑基、4,5-二氫-異唑基,及2,3-二氫-[1,3,4]-二唑基。
- 如申請專利範圍第1項之分子,其中,Het-1係選自苯并噻二唑基、呋喃基、唑基,及噻吩基吡唑基。
- 如申請專利範圍第1項之分子,其中,該分子係選自
- 一種施用如申請專利範圍第1項之組成物之方法,該方法包含使如申請專利範圍第1項之組成物以一足以控制 害蟲之量施用至一區域以控制該害蟲。
- 如申請專利範圍第21項之方法,其中,該分子係選自
- 如申請專利範圍第21項之方法,其中,該區域係蘋果、玉米、棉花、黃豆、芥花、小麥、稻米、高梁、大麥、燕麥、馬鈴薯、柑橘、苜蓿芽、萵苣、草莓、番茄、胡椒、十字花科植物、梨、煙草、杏仁、甜菜,或豆子正在生長或其等之種籽將種植之區域。
- 如申請專利範圍第1項之組成物,包含如申請專利範圍第1項之分子之一殺蟲可接受之酸加成鹽、一鹽衍生物、一溶劑合物,或一酯衍生物。
- 如申請專利範圍第1項之組成物,包含如申請專利範圍第1項之分子之一多形體。
- 如申請專利範圍第1項之組成物,包含如申請專利範圍第1項之分子,其中,至少一H係2H或至少一C係14C。
- 一種組成物,包含如申請專利範圍第1項之分子,及至少一選自殺昆蟲劑組群、殺蟎劑組群、殺線蟲劑組群、殺黴菌劑組群、除草劑組群、AI組群,或增效劑組群之其它化合物。
- 一種組成物,包含如申請專利範圍第1項之組成物,及一種籽。
- 如申請專利範圍第28項之組成物,其中,該種籽已經基因改造而表現一或多種特定化之特性。
- 如申請專利範圍第1項之組成物,及至少一化合物,其具有選自乙醯膽鹼酯酶抑制劑、鈉通道調節劑、幾丁生物合成抑制劑、GABA調控之氯化物通道拮抗劑、GABA 及谷氨酸鹽調控之氯化物通道激動劑、乙醯膽鹼受體激動劑、MET I抑制劑、Mg-刺激之ATP酶抑制劑、尼古丁乙醯膽鹼受體、中腸膜干擾素、氧化磷酸化干擾素,及雷諾定受體(RyRs)之一作用模式。
- 一種方法,包含使如申請專利範圍第1項之組成物施用至經基因改造而表現一或多種特定化之特性之一經基因改造之植物。
- 一種方法,包含使如申請專利範圍第1項之組成物口服投用或局部施用至至一非人類之動物以控制內寄生蟲、皮外寄生蟲,或二者。
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BR112014018943A8 (pt) | 2012-02-02 | 2017-07-11 | Dow Agrosciences Llc | Composições pesticidas e processos relacionados as mesmas |
US8916183B2 (en) * | 2012-02-02 | 2014-12-23 | Dow Agrosciences, Llc. | Pesticidal compositions and processes related thereto |
BR112017015505B1 (pt) | 2015-01-23 | 2021-09-14 | Syngenta Participations Ag | Composto, composição pesticida, método para controle de pragas, método para a proteção de material de propagação de plantas do ataque por pragas e material de propagação revestido |
JP6807876B2 (ja) | 2015-06-05 | 2021-01-06 | シンジェンタ パーティシペーションズ アーゲー | 殺有害生物的に活性なオキシムおよびヒドラゾン誘導体 |
JP6970176B2 (ja) | 2016-07-22 | 2021-11-24 | シンジェンタ パーティシペーションズ アーゲー | 有害生物防除剤としての尿素およびチオ尿素置換二環式誘導体 |
CN107935961B (zh) * | 2017-12-01 | 2019-10-29 | 赣南师范大学 | 一种2-亚氨基噻唑烷-4-酮类化合物的制备方法 |
US20220002284A1 (en) | 2018-11-28 | 2022-01-06 | Basf Se | Pesticidal compounds |
CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
WO2020229398A1 (de) | 2019-05-14 | 2020-11-19 | Bayer Aktiengesellschaft | (1-alkenyl)-substituierte pyrazole und triazole als schädlingsbekämpfungsmittel |
KR20220035939A (ko) | 2019-07-22 | 2022-03-22 | 바이엘 악티엔게젤샤프트 | 살충제로서의 5-아미노-치환된 피라졸 및 트리아졸 |
WO2021219513A1 (en) | 2020-04-28 | 2021-11-04 | Basf Se | Pesticidal compounds |
WO2022033991A1 (de) | 2020-08-13 | 2022-02-17 | Bayer Aktiengesellschaft | 5-amino substituierte triazole als schädlingsbekämpfungsmittel |
WO2022053453A1 (de) | 2020-09-09 | 2022-03-17 | Bayer Aktiengesellschaft | Azolcarboxamide als schädlingsbekämpfungsmittel |
EP3974414A1 (de) | 2020-09-25 | 2022-03-30 | Bayer AG | 5-amino substituierte pyrazole und triazole als schädlingsbekämpfungsmittel |
EP4036083A1 (de) | 2021-02-02 | 2022-08-03 | Bayer Aktiengesellschaft | 5-oxy substituierte hetereozyklen, als schädlingsbekämpfungsmittel |
EP4144739A1 (de) | 2021-09-02 | 2023-03-08 | Bayer Aktiengesellschaft | Anellierte pyrazole als schädlingsbekämpfungsmittel |
EP4198023A1 (en) | 2021-12-16 | 2023-06-21 | Basf Se | Pesticidally active thiosemicarbazone compounds |
WO2023156402A1 (en) | 2022-02-17 | 2023-08-24 | Basf Se | Pesticidally active thiosemicarbazone compounds |
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AU1555797A (en) * | 1996-01-30 | 1997-08-22 | Takeda Chemical Industries Ltd. | Arylpyrazole insecticides |
US6413992B1 (en) * | 1998-10-23 | 2002-07-02 | Dow Agrosciences Llc | 3-(substituted pyridyl)-1,2,4-triazole compounds |
PT1328275E (pt) * | 2000-10-27 | 2008-07-14 | Dow Agrosciences Llc | 4,5-di-hidro-1,2,4-triazina-3-onas, 1,2,4-triazina-3-onas substituidas e suas utilizações como fungicidas e insecticidas |
TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
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EP2019095A1 (en) * | 2007-07-06 | 2009-01-28 | Bayer CropScience AG | Iminooxazole and iminothiazole compounds as pesticides |
CN101998963B (zh) * | 2008-02-12 | 2014-09-24 | 陶氏益农公司 | 杀虫组合物 |
UA108619C2 (xx) * | 2009-08-07 | 2015-05-25 | Пестицидні композиції | |
BR112012002677A2 (pt) * | 2009-08-07 | 2021-03-09 | Dow Agrosciences Llc | Moléculas de heteroaril-n-aril carbamatos, e composição pesticida |
EP2585443B1 (en) * | 2010-06-23 | 2015-02-18 | Basf Se | Process for producing imine compounds for combating invertebrate pests |
MX2013009129A (es) | 2011-02-07 | 2013-10-01 | Dow Agrosciences Llc | Composiciones pesticidas y procesos relacionados. |
BR112014018943A8 (pt) | 2012-02-02 | 2017-07-11 | Dow Agrosciences Llc | Composições pesticidas e processos relacionados as mesmas |
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AP2014007823A0 (en) | 2014-07-31 |
EP2809159A4 (en) | 2015-08-12 |
EP2809159A1 (en) | 2014-12-10 |
CN104202986A (zh) | 2014-12-10 |
CL2014002051A1 (es) | 2014-11-21 |
US20140235440A1 (en) | 2014-08-21 |
IL233704B (en) | 2018-03-29 |
CA2861353A1 (en) | 2013-08-08 |
CN104202986B (zh) | 2016-08-24 |
PH12014501744A1 (en) | 2014-11-10 |
PH12014501744B1 (en) | 2014-11-10 |
BR112014018943A8 (pt) | 2017-07-11 |
ZA201405157B (en) | 2015-11-25 |
JP2015506959A (ja) | 2015-03-05 |
US20130203593A1 (en) | 2013-08-08 |
UA114313C2 (uk) | 2017-05-25 |
MX338200B (es) | 2016-04-07 |
KR20140119789A (ko) | 2014-10-10 |
WO2013116052A1 (en) | 2013-08-08 |
RU2616808C2 (ru) | 2017-04-18 |
AR089875A1 (es) | 2014-09-24 |
RU2014135519A (ru) | 2016-03-20 |
CO7020932A2 (es) | 2014-08-11 |
AU2013215536A1 (en) | 2014-07-31 |
TWI571464B (zh) | 2017-02-21 |
US9018388B2 (en) | 2015-04-28 |
HK1204752A1 (zh) | 2015-12-04 |
NZ627331A (en) | 2016-03-31 |
AU2013215536B2 (en) | 2016-03-17 |
JP6117825B2 (ja) | 2017-04-19 |
MX2014009346A (es) | 2014-09-01 |
BR112014018943A2 (zh) | 2017-06-20 |
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