CN1761654A - 吡唑化合物 - Google Patents
吡唑化合物 Download PDFInfo
- Publication number
- CN1761654A CN1761654A CNA2004800076819A CN200480007681A CN1761654A CN 1761654 A CN1761654 A CN 1761654A CN A2004800076819 A CNA2004800076819 A CN A2004800076819A CN 200480007681 A CN200480007681 A CN 200480007681A CN 1761654 A CN1761654 A CN 1761654A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- chch
- formula
- pyrazole compound
- benzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 Pyrazole compound Chemical class 0.000 title claims abstract description 193
- 150000001875 compounds Chemical class 0.000 claims abstract description 211
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 89
- 239000001257 hydrogen Substances 0.000 claims abstract description 89
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 79
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 66
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 63
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 48
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 46
- 241000238421 Arthropoda Species 0.000 claims abstract description 34
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 82
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 73
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 57
- 239000000460 chlorine Substances 0.000 claims description 47
- 229910052801 chlorine Inorganic materials 0.000 claims description 47
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 46
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 37
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 37
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 37
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 37
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 36
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 abstract 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 194
- 101150065749 Churc1 gene Proteins 0.000 description 194
- 102100038239 Protein Churchill Human genes 0.000 description 194
- 238000004519 manufacturing process Methods 0.000 description 80
- 238000005160 1H NMR spectroscopy Methods 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 239000012044 organic layer Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 27
- 239000003513 alkali Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000003810 ethyl acetate extraction Methods 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- 238000010898 silica gel chromatography Methods 0.000 description 22
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
- 238000005406 washing Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 235000015320 potassium carbonate Nutrition 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 150000001342 alkaline earth metals Chemical class 0.000 description 11
- 229910052728 basic metal Inorganic materials 0.000 description 11
- 150000003818 basic metals Chemical class 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 6
- 229910000105 potassium hydride Inorganic materials 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 238000000638 solvent extraction Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
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- KHMZDLNSWZGRDB-OWOJBTEDSA-N (e)-1,3,3-trichloroprop-1-ene Chemical compound Cl\C=C\C(Cl)Cl KHMZDLNSWZGRDB-OWOJBTEDSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
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- 241000256118 Aedes aegypti Species 0.000 description 4
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Abstract
一种由式(a)表示的吡唑化合物:其中R1表示C1-4烷基或三氟甲基,R2表示C1-4烷基,R3表示氢或C1-6烷基;R4表示卤素等,m表示0-4的整数;R5表示卤素等,n表示0-4的整数;R6和R7相同或者不同,并且各自表示氢、卤素或甲基;X表示氧或由R8O-N表示的基团;R8表示氢、C1-6烷基等。该化合物在防治有害节肢动物方面有高活性。
Description
技术领域
本发明涉及吡唑化合物、其中间体化合物以及用它们防治有害节肢动物的方法。
背景技术
某些类型吡唑化合物被认为是杀虫剂和杀螨剂的有效成分。参见美国专利4,843,068。
然而,在有些情况下,这些吡唑化合物的有害节肢动物防治活性不足够,因此需要具有有害节肢动物防治活性的新型化合物。
发明内容
本发明提供式(a)的吡唑化合物(在下文简称本发明化合物):
其中R1表示C1-C4烷基或三氟甲基,R2表示C1-C4烷基,R3表示氢或C1-C6烷基;R4表示卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基,m表示0-4的整数,当m为2-4的整数时,每个R4相同或者不同;R5表示卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基,n表示0-4的整数,当n为2-4的整数时,每个R5相同或者不同;R6和R7相同或者不同,并且表示氢、卤素或甲基,X表示氧或R8O-N;R8表示氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
包含本发明化合物的防治有害节肢动物的组合物;和防治有害节肢动物的方法,其特征在于把有效量的本发明化合物应用于有害节肢动物或有害节肢动物栖息地。
此外,本发明也提供式(b)的化合物:
其中R1表示C1-C4烷基或三氟甲基,R2表示C1-C4烷基,R3表示氢或C1-C6烷基;R4表示卤素、C1-C3烷基、C1-C3烷氧基或三氟甲基,m表示0-4的整数,当m为2-4的整数时,每个R4相同或者不同;R5表示卤素、C1-C3烷基、C1-C3烷氧基或三氟甲基,n表示0-4的整数,当n为2-4的整数时,每个R5相同或者不同;X表示氧或R8O-N;R8表示氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);所述化合物可用作本发明化合物的中间体。
在本发明化合物中,每个由R1、R2、R3、R4、R5、R6、R7或R8表示的取代基以下述取代基为例具体说明。
由R1表示的C1-C4烷基为甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基和叔丁基。
由R2表示的C1-C4烷基为甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基和叔丁基。
由R3表示的C1-C6烷基包括甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、3-甲基丁基、2,2-二甲基丙基、1,1-二甲基丙基、1-乙基丙基、己基、5-甲基戊基、2-乙基丁基、3-甲基戊基和1,3-二甲基丁基。
由R4和R5表示的卤素为氟、氯、溴和碘;
C1-C3烷基包括甲基、乙基、丙基和异丙基;
C1-C3烷氧基包括甲氧基、乙氧基、丙氧基和异丙氧基;
C1-C3卤代烷基包括三氟甲基、2-氟乙基、2,2,2-三氟乙基、3,3,3-三氟丙基、2-氯乙基和3-溴丙基;
C1-C3卤代烷氧基包括三氟烷氧基、2,2,2-三氟乙氧基、3,3,3-三氟丙氧基。
由R6表示的卤素为氟、氯、溴和碘。
由R7表示的卤素为氟、氯、溴和碘。
由R8表示的C1-C6烷基包括甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、新戊基、叔戊基、1-甲基丁基、1,2-二甲基丙基和己基;
C1-C6卤代烷基包括氟甲基、2-氟乙基、2,2,2-三氟乙基、3,3,3-三氟丙基、4,4,4-三氟丁基、5,5,5-三氟戊基、2-氯乙基、3-氯丙基、3-溴丙基、4-氯丁基、4-溴丁基、4-氯戊基和4-溴戊基;
C3-C6烯基包括烯丙基、2-甲基-2-丙烯基、3-甲基-2-丁烯基、2-丁烯基、3-丁烯基、2-戊烯基、3-戊烯基、2-己烯基和3-己烯基;
C3-C6卤代烯基包括3-氯-2-丙烯基、3,3-二氯-2-丙烯基、3-溴-2-丙烯基、3,3-二溴-2-丙烯基、2-氯-2-丙烯基、2-溴-2-丙烯基、2-氟-2-丙烯基、2,3-二氯-2-丙烯基、2,3-二溴-2-丙烯基、3-氯-2-丁烯基、3-氯-4,4,4-三氟-2-丁烯基、4-氯-2-丁烯基、4-溴-2-丁烯基和2,3,3-三氟-2-丙烯基;
C3-C6炔基包括2-丙炔基、2-丁炔基、2-戊炔基、3-丁炔基和1-甲基-2-丙炔基;
C3-C6卤代炔基包括3-氯-2-丙炔基、4-氯-3-丁炔基、5-氯-4-戊炔基、6-氯-5-己炔基、3-溴-2-丙炔基、4-溴-3-丁炔基、5-溴-4-戊炔基和6-溴-5-己炔基;
C2-C5氰基烷基包括氰基甲基、2-氰基乙基、3-氰基丙基和4-氰基丁基;
任选被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代的苄基包括苄基、2-氟苄基、3-氟苄基、4-氟苄基、2-氯苄基、3-氯苄基、4-氯苄基、2-溴苄基、3-溴苄基、4-溴苄基、2,3-二氯苄基、3,5-二氯苄基、2,4-二氯苄基、2-甲基苄基、3-甲基苄基、4-甲基苄基、2,3-二甲基苄基、3,5-二甲基苄基、2,4-甲基苄基、2-甲氧基苄基、3-甲氧基苄基、4-甲氧基苄基、2,3-二甲氧基苄基、3,5-二甲氧基苄基、2,4-二甲氧基苄基、4-甲氧基羰基苄基、4-乙氧基羰基苄基、4-丙氧基羰基苄基、4-三氟甲基苄基和4-三氟甲氧基苄基。
本发明化合物的实施方案举例说明如下:
1)吡唑化合物,其中在式(a)中,R1为甲基;
2)吡唑化合物,其中在式(a)中,R1为乙基;
3)吡唑化合物,其中在式(a)中,R1为三氟甲基;
4)吡唑化合物,其中在式(a)中,R2为甲基;
5)吡唑化合物,其中在式(a)中,R3为氢;
6)吡唑化合物,其中在式(a)中,R3为甲基;
7)吡唑化合物,其中在式(a)中,m为0;
8)吡唑化合物,其中在式(a)中,n为0;
9)吡唑化合物,其中在式(a)中,R6为氯;
10)吡唑化合物,其中在式(a)中,R6和R7为氯;
11)吡唑化合物,其中在式(a)中,R1为甲基,R2为甲基;
12)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基;
13)吡唑化合物,其中在式(a)中,R1为三氟甲基,R2为甲基;
14)吡唑化合物,其中在式(a)中,R1为甲基,R6为氯;
15)吡唑化合物,其中在式(a)中,R1为乙基,R6为氯;
16)吡唑化合物,其中在式(a)中,R1为三氟甲基,R6为氯;
17)吡唑化合物,其中在式(a)中,R1为甲基,R6和R7为氯;
18)吡唑化合物,其中在式(a)中,R1为乙基,R6和R7为氯;
19)吡唑化合物,其中在式(a)中,R1为三氟甲基,R6和R7为氯;
20)吡唑化合物,其中在式(a)中,R1为甲基,R2为甲基,R6为氯;
21)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,R6为氯;
22)吡唑化合物,其中在式(a)中,R1为三氟甲基,R2为甲基,R6为氯;
23)吡唑化合物,其中在式(a)中,R1为甲基,R2为甲基,R6和R7为氯;
24)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,R6和R7为氯;
25)吡唑化合物,其中在式(a)中,R1为三氟甲基,R2为甲基,R6和R7为氯;
26)吡唑化合物,其中在式(a)中,R1为甲基,R2为甲基,R3为氢,R6和R7为氯;
27)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,R3为氢原子,R6和R7为氯;
28)吡唑化合物,其中在式(a)中,R1为三氟甲基,R2为甲基,R3为氢原子,R6和R7为氯;
29)吡唑化合物,其中在式(a)中,R1为甲基,R2为甲基,R3为甲基,R6和R7为氯;
30)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,R3为甲基,R6和R7为氯;
31)吡唑化合物,其中在式(a)中,R1为三氟甲基,R2为甲基,R3为甲基,R6和R7为氯;
32)吡唑化合物,其中在式(a)中,R1为甲基,R2为甲基,m为0,n为0;
33)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,m为0,n为0;
34)吡唑化合物,其中在式(a)中,R1为三氟甲基,R2为甲基,m为0,n为0;
35)吡唑化合物,其中在式(a)中,R1为甲基,R2为甲基,m为0,n为0,R6为氯;
36)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,m为0,n为0,R6为氯;
37)吡唑化合物,其中在式(a)中,R1为三氟甲基,R2为甲基,m为0,n为0,R6为氯;
38)吡唑化合物,其中在式(a)中,R2为甲基,R6为氯;
39)吡唑化合物,其中在式(a)中,R2为甲基,R6和R7为氯;
40)吡唑化合物,其中在式(a)中,R2为甲基,m为0,n为0;
41)吡唑化合物,其中在式(a)中,R2为甲基,m为0,n为0,R6为氯;
42)吡唑化合物,其中在式(a)中,R2为甲基,m为0,n为0,R6和R7为氯;
43)吡唑化合物,其中在式(a)中,m为0,n为0;
44)吡唑化合物,其中在式(a)中,m为0,n为0,R6为氯;
45)吡唑化合物,其中在式(a)中,m为0,n为0,R6和R7为氯;
46)吡唑化合物,其中在式(a)中,R3为氢;
47)吡唑化合物,其中在式(a)中,R3为C1-C6烷基;
48)吡唑化合物,其中在式(a)中,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
49)吡唑化合物,其中在式(a)中,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C2-C5氰基烷基;
50)吡唑化合物,其中在式(a)中,X为R8O-N,R8为苄基(其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
51)吡唑化合物,其中在式(a)中,X为氧;
52)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
53)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C2-C5氰基烷基;
54)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为苄基(其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
55)吡唑化合物,其中在式(a)中,R3为氢,X为氧;
56)吡唑化合物,其中在式(a)中,R3为氢原子,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R4和R5为卤素、C1-C3烷基、C1-C3烷氧基或三氟甲基,m和n为0-2的整数;
57)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C2-C5氰基烷基,R4和R5为卤素、C1-C3烷基、C1-C3烷氧基或三氟甲基,m和n为0-2的整数;
58)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R4和R5为卤素、C1-C3烷基、C1-C3烷氧基或三氟甲基,m和n为0-2的整数;
59)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C2-C5氰基烷基,R4和R5为氢;
60)吡唑化合物,其中在式(a)中,R3为氢,X为氧,R4和R5为卤素、C1-C3烷基、C1-C3烷氧基或三氟甲基,m和n为0-2的整数;
61)吡唑化合物,其中在式(a)中,R3为氢,R6为卤素,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
62)吡唑化合物,其中在式(a)中,R3为氢,R6为卤素,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C2-C5氰基烷基;
63)吡唑化合物,其中在式(a)中,R3为氢,R6为卤素,X为R8O-N,R8为苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
64)吡唑化合物,其中在式(a)中,R3为氢,R6为卤素,X为氧;
65)吡唑化合物,其中在式(a)中,R3为氢,R6为和R7卤素,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
66)吡唑化合物,其中在式(a)中,R3为氢,R6为和R7卤素,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C2-C5氰基烷基;
67)吡唑化合物,其中在式(a)中,R3为氢,R6为和R7卤素,X为R8O-N,R8为苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代);
68)吡唑化合物,其中在式(a)中,R3为氢,R6为和R7卤素,X为氧;
69)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为甲基;
70)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为乙基;
71)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为三氟甲基;
72)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R2为甲基;
73)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R3为氢;
74)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R3为甲基;
75)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),m为0;
76)吡唑化合物,其中在式(a)中,n为0;
77)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R6为氯;
78)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R6和R7为氯;
79)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为甲基,R2为甲基;
80)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为乙基,R2为甲基;
81)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为三氟甲基,R2为甲基;
82)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为甲基,R2为甲基,R3为氢,R6和R7为氯;
83)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,R3为氢,R6和R7为氯;
84)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为三氟甲基,R2为乙基,R3为氢,R6和R7为氯;
85)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为甲基,R2为甲基,R3为甲基,R6和R7为氯;
86)吡唑化合物,其中在式(a)中,R1为乙基,R2为甲基,R3为甲基,R6和R7为氯;
87)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),R1为三氟甲基,R2为甲基,R3为甲基,R6和R7为氯;
88)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),m为0,n为0;
89)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),m为0,n为0,R6为氯;
90)吡唑化合物,其中在式(a)中,R3为氢,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基(所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代),m为0,n为0,R6和R7为氯。
本发明化合物可以通过以下方法例如生产方法1至生产方法4制得。
生产方法1
可以通过使式(b)的化合物:
其中R1、R2、R3、R4、R5、X、m和n的含义同上;
与式(e)的化合物反应来生产本发明化合物:
L-CH2CH=C(R6)(R7) (e)
其中R6和R7的含义同上,L表示卤素(例如氯或溴)、甲磺酰氧基、苯磺酰氧基或甲苯磺酰氧基。
反应通常在碱存在下在溶剂中进行。反应温度通常为-78℃至150℃,反应时间为0.1-24小时。
用于反应的溶剂的实例包括酮类例如丙酮、甲乙酮等;芳香烃例如甲苯、二甲苯等;脂肪烃例如己烷、庚烷等;醚例如二乙醚、四氢呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等;卤代烃例如二氯甲烷、氯仿、1,2-二氯乙烷、氯苯、二氯苯等;酰胺例如N,N-二甲基甲酰胺、N,N-二乙基乙酰胺等;腈例如乙腈等;二甲亚砜;及其混合物。
用于反应的碱的实例包括无机碱例如碱金属或碱土金属的氢氧化物(例如氢氧化钠、氢氧化钾、氢氧化钙等)、碱金属或碱土金属的氢化物(例如氢化钠、氢化钾、氢化钙等)、碳酸钠、碳酸钾等;和有机碱例如三乙胺等。
根据1摩尔式(b)化合物,通常使用1-3摩尔式(a)化合物和1-3摩尔所述碱。
反应后,将反应混合物倾入水中,用有机溶剂萃取,干燥并浓缩有机层,得到本发明化合物。此外,可通过色谱、重结晶等方法纯化所获得的本发明化合物。
生产方法2
通过使式(c)的化合物:
其中R1、R2、R3、R4、R5、R6、R7、X、m和n的含义同上;
与式(d)的羟胺化合物本身或其盐例如盐酸盐、硫酸盐、硝酸盐等反应来生产式(a)中X为R8O-N的本发明化合物:
R8O-NH2 (d)
其中R8的含义同上。
反应通常在碱存在下在溶剂中进行。反应温度通常为-78℃至150℃,反应时间为0.1-24小时。
用于反应的溶剂的实例包括醇类例如甲醇、乙醇等;芳香烃例如苯、甲苯、二甲苯等;脂肪烃例如己烷、庚烷等;醚例如二乙醚、四氢呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等;卤代烃例如二氯甲烷、氯仿、1,2-二氯乙烷、氯苯、二氯苯等;酰胺例如N,N-二甲基甲酰胺、N,N-二乙基乙酰胺等;二甲亚砜;水;及其混合物。
用于反应的碱的实例包括无机碱例如碱金属或碱土金属的氢化物(例如氢化钠、氢化钾、氢化钙等)、碳酸钠、碳酸钾等;和有机碱例如三乙胺、吡啶等。
当使用过量的式(d)的羟胺化合物本身时,所述碱可不需要。
根据1摩尔式(c)化合物,通常使用1-3摩尔式(d)的羟胺化合物本身或其酸和1-3摩尔所述碱。
反应后,将反应混合物倾入水中,用有机溶剂萃取,干燥并浓缩有机层,得到本发明化合物,其中在式(a)中,X为R8O-N。此外,可通过色谱、重结晶等方法纯化所获得的本发明化合物。
生产方法3
通过使式(f)的化合物:
其中R1、R2、R3、R4、R5、R6、R7、m和n的含义同上;
与式(g)的化合物反应来生产式(a)中X为R8O-N的本发明化合物:
L-R8 (g)
其中R8的含义同上,L表示卤素(例如氯或溴)、甲磺酰氧基、苯磺酰氧基或甲苯磺酰氧基。
反应通常在碱存在下在溶剂中进行。反应温度通常为-78℃至150℃,反应时间为0.1-24小时。
用于反应的溶剂的实例包括酮类例如丙酮、甲乙酮等;芳香烃例如甲苯、二甲苯等;脂肪烃例如己烷、庚烷等;醚例如二乙醚、四氢呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等;卤代烃例如氯苯、二氯苯等;酰胺例如N,N-二甲基甲酰胺、N,N-二乙基乙酰胺等;腈例如乙腈等;二甲亚砜;及其混合物。
用于反应的碱的实例包括无机碱例如碱金属或碱土金属的氢氧化物(例如氢氧化钠、氢氧化钾、氢氧化钙等)、碱金属或碱土金属的氢化物(例如氢化钠、氢化钾、氢化钙等)、碳酸钠、碳酸钾等;和有机碱例如三乙胺等。
根据1摩尔式(f)化合物,通常使用1-1.5摩尔式(g)化合物和1-1.2摩尔所述碱。
反应后,将反应混合物倾入水中,用有机溶剂萃取,干燥并浓缩有机层,得到目标化合物,其中在式(a)中,X为R8O-N。此外,可通过色谱、重结晶等方法纯化所获得的本发明化合物。
生产方法4
通过使式(h)的化合物:
其中R1、R2和R3的含义同上;
与式(k)的化合物反应来生产式(a)中X为氧的本发明化合物:
其中R4、R5、R6、R7、m和n的含义同上。
反应通常在碱存在下在溶剂中进行。反应温度通常为-78℃至150℃,反应时间为0.1-24小时。
用于反应的溶剂的实例包括芳香烃例如甲苯、二甲苯等;脂肪烃例如己烷、庚烷等;醚例如二乙醚、四氢呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等;酰胺例如N,N-二甲基甲酰胺、N,N-二乙基乙酰胺等;二甲亚砜;及其混合物。
用于反应的碱的实例包括无机碱例如碱金属或碱土金属的氢氧化物(例如氢氧化钠、氢氧化钾、氢氧化钙等)、碱金属或碱土金属的氢化物(例如氢化钠、氢化钾、氢化钙等)、碳酸钠、碳酸钾等;和有机碱例如三乙胺等。
根据1摩尔式(h)化合物,通常使用0.5-3摩尔式(k)化合物和1-3摩尔所述碱。
反应后,将反应混合物倾入水中,用有机溶剂萃取,干燥并浓缩有机层,得到本发明化合物,其中在式(a)中,X为氧。此外,可通过色谱、重结晶等方法纯化所获得的本发明化合物。
接下来,在下文中描述本发明中间体的生产方法。
式(b-2)的化合物:
其中R1、R2、R3、R4、R5、R8、m和n的含义同上;
例如,可以通过使式(b-1)的化合物:
其中R1、R2、R3、R4、R5、m和n的含义同上;
与式(d)的羟胺化合物本身或其盐例如盐酸盐、硫酸盐、硝酸盐等反应来生产。
反应通常在碱存在下在溶剂中进行。反应温度通常为-78℃至150℃,反应时间为0.1-24小时。
用于反应的溶剂的实例包括醇类例如甲醇、乙醇等;芳香烃例如甲苯、二甲苯等;脂肪烃例如己烷、庚烷等;醚例如二乙醚、四氢呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等;卤代烃例如二氯甲烷、氯仿、1,2-二氯乙烷、氯苯、二氯苯等;酰胺例如N,N-二甲基甲酰胺、N,N-二乙基乙酰胺等;二甲亚砜;水;及其混合物。
用于反应的碱的实例包括无机碱例如碱金属或碱土金属的氢氧化物(例如氢氧化钠、氢氧化钾、氢氧化钙等)、碱金属或碱土金属的氢化物(例如氢化钠、氢化钾、氢化钙等)、碳酸钠、碳酸钾等;和有机碱例如三乙胺等。当使用过量的式(d)的羟胺化合物本身时,所述碱可不需要。根据1摩尔式(b-1)化合物,通常使用1-3摩尔式(d)羟胺化合物本身或其盐和1-10摩尔所述碱。
反应后,将反应混合物倾入水中,用有机溶剂萃取,干燥并浓缩有机层,得到式(b-2)化合物。此外,可通过色谱、重结晶等纯化所获式(b-2)化合物。
例如,可以通过使式(h)的化合物与式(i)的化合物反应来生产式(b-1)的化合物:
其中R4、R5、m和n的含义同上。
反应通常在碱存在下在溶剂中进行。反应温度通常为-78℃至150℃,反应时间为0.1-24小时。
用于反应的溶剂的实例包括芳香烃例如甲苯、二甲苯等;脂肪烃例如己烷、庚烷等;醚例如二乙醚、四氢呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等;酰胺例如N,N-二甲基甲酰胺、N,N-二乙基乙酰胺等;二甲亚砜;及其混合物。
用于反应的碱的实例包括无机碱例如碱金属或碱土金属的氢氧化物(例如氢氧化钠、氢氧化钾、氢氧化钙等)、碱金属或碱土金属的氢化物(例如氢化钠、氢化钾、氢化钙等)、碳酸钠、碳酸钾等;和有机碱例如三乙胺等。
根据1摩尔式(h)化合物,通常使用0.5-3摩尔式(i)化合物和1-3摩尔所述碱。
反应后,将反应混合物倾入水中,用有机溶剂萃取,干燥并浓缩有机层,得到式(b-1)化合物。此外,可通过色谱、重结晶等纯化所获式(b-1)化合物。
可以通过用适当的保护基(例如苄基、叔丁基二甲基甲硅烷基和甲氧基甲基)保护式(i)化合物中的两个酚羟基之一,进行上述反应后,除去所述保护基,从而得到式(b-1)的化合物。
本发明化合物举例说明如下。
在式(I)至式(XXXXXIII)中,R1、R2和X中每个为描述于表1或表2中的组合中任何一种。
表1(X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CH-CH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CH-CH2CH2(CH3)3C-CH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2-CH=CHCH2CBrH2-CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2-CH=CHCH2CBrH2-CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2CH=CHCH2CBrH2CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2ClCH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2CH=CHCH2CBrH2CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2CH=CHCH2CBrH2CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
Ch3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2CH=CHCH2CBrH2CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R3O-N)
R1 | R2 | R3 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2CH=CHCH2CBrH2CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2CH=CHCH2CBrH2CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2FCH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2ClCH2CH2CH2BrCH2CH2CH2ClCH2CH2CH2CH2BrCH2CH2CH2CH2ClCH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH2BrCH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2-CH=CHCH2CBrH2-CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2-CH=CHCH2CBrH2-CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2 | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH2Br-CH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2-CH=CHCH2CBrH2-CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHO C(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH3CH3CH2CH3CH2CH2(CH3)2CHCH3CH2CH2CH2CH3CH2-(CH3)CH(CH3)2CHCH2(CH3)3CCH3CH2CH2CH2CH2(CH3)2CHCH2CH2(CH3)3CCH2CH3CH2CH2-(CH3)CH(CH3)2CH-(CH3)CHCH3CH2CH2CH2CH2CH2CH2FCH2F-CH2CF3CH2CF3CH2CH2CF3CH2CH2CH2CF3CH2CH2CH2CH2CH2Cl-CH2CH2CH2Br-CH2CH2CH2Cl-CH2CH2CH2CH2Br-CH2CH2CH2CH2Cl-CH2CH2CH2CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH2BrCH2CH2CH2CH2CH2=CHCH2CH2=C(CH3)-CH2(CH3)2C=CHCH2CH3CH=CHCH2CH2=CHCH2CH2CH3CH2CH=CHCH2CH3CH=CHCH2CH2CH3CH2CH2CH=CHCH2CH3CH2CH=CHCH2CH2CHCl=CHCH2CCl2=CHCH2CHBr=CHCH2CBr2=CHCH2CH2=CClCH2CH2=CBrCH2CH2=CFCH2CHCl=CClCH2CHBr=CBrCH2CH3CCl=CHCH2CF3CCl=CHCH2CClH2CH=CHCH2CBrH2CH=CHCH2CF2=CFCH2CH≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH3C≡CCH2CH3CH2C≡CCH2CH3C≡CCH2CH2CH≡C-(CH3)CHN≡CCH2N≡CCH2CH2N≡CCH2CH2CH2N≡CCH2CH2CH2CH2HC6H5-CH22-F-C6H4-CH23-F-C6H4-CH24-F-C6H4-CH22-Cl-C6H4-CH23-Cl-C6H4-CH24-Cl-C6H4-CH22-Br-C6H4-CH23-Br-C6H4-CH24-Br-C6H4-CH24-I-C6H4-CH22-CH3-C6H4-CH23-CH3-C6H4-CH24-CH3-C6H4-CH24-CF3-C6H4-CH24-CH3CH2-C6H4-CH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | (CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | 4-(CH3)2CH-C6H4-CH24-CH3CH2CH2-C6H4-CH24-(CH3)3C-C6H4-CH22,4-(CH3)2-C6H3-CH22,4,6-(CH3)3-C6H2-CH22,4-Cl2-C6H3-CH23,4-Cl2-C6H3-CH22,5-Cl2-C6H3-CH23,5-Cl2-C6H3-CH22,6-Cl2-C6H3-CH24-CH3O-C6H4-CH24-CF3O-C6H4-CH24-CH3CH2O-C6H4-CH24-(CH3)2CHO-C6H4-CH24-(CH3)3CO-C6H4-CH24-CH3OC(=O)-C6H4-CH24-CH3CH2OC(=O)-C6H4-CH24-CH3CH2CH2OC(=O)-C6H4-CH24-(CH3)2CHOC(=O)-C6H4-CH24-(CH3)3COC(=O)-C6H4-CH2CH2Cl-CH2CCl≡CCH2CBr≡CCH2 |
(表1续:X表示R8O-N)
R1 | R2 | R8 |
(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)3C | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HCH3CH3CH2CH3CH2CH2CH2FCF3CH2CF3CH2CH2CH2ClCH2CH2=CHCH2CH≡CCH2CH3C≡CCH2N≡CCH2HCH3CH3CH2CH3CH2CH2CH2FCF3CH2CF3CH2CH2CH2Cl-CH2CH2=CHCH2CH≡CCH2CH3C≡CCH2N≡CCH2 |
表2(X表示氧原子)
R1 | R2 |
CH3CH3CH3CH3CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2CH3CH2(CH3)3C(CH3)3C(CH3)3C(CH3)3C(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2CHCF3CF3CF3CF3 | CH3CH3CH2(CH3)2CH(CH3)3CCH3CH3CH2(CH3)2CH(CH3)3CCH3CH3CH2(CH3)2CH(CH3)3CCH3CH3CH2(CH3)2CH(CH3)3CCH3CH3CH2(CH3)2CH(CH3)3CCH3CH3CH2(CH3)2CH(CH3)3C |
本发明化合物对其有活性的有害节肢动物,包括昆虫害虫和螨虫害虫,并具体描述如下:
半翅目(Hemiptera):
飞虱科(Delphacidae),例如灰飞虱(Laodelphax striatellus)、褐飞虱(Nilaparvata lugens)、白背飞虱(Sogatella furcifera)等,
角顶叶蝉科(Deltocephalidae),例如黑尾叶蝉(Nephotettixcincticeps)、二点黑尾叶蝉(Nephotettix virescens)等,
蚜科(Aphididae),例如棉蚜(Aphis gossypii)、桃蚜(Myzus persicae)等,
蝽科(Pentatomidae),例如花角绿蝽Nezara antennata)、豆蜂缘蝽(Riptortus clavetus)等,
粉虱科(Aleyrodidae),例如温室粉虱(Trialeurodes vaporariorum)、银叶粉虱(Bemisia argentifolii)等,
蚧科(Coccidae),例如红肾圆盾蚧(Aonidiella aurantii)、圣琼斯康盾蚧(Comstockaspis perniciosa)、柑桔尖盾蚧(Unaspis citri)、红龟蜡蚧(Ceroplastes rubens)、澳洲吹绵蚧(Icerya purchasi)等,
网蝽科(Tingidae),
木虱科(Psyllidae)等;
鳞翅目(Lepidoptera):
螟蛾科(Pyralidae),例如二化螟(Chilo suppressalis)、稻纵卷叶野螟(Cnaphalocrocis medinalis)、棉卷叶野螟(Notarcha derogata)、印度谷斑螟(Plodia interpunctella)等,
夜蛾科(Noctuidae),例如斜纹夜蛾(Spodoptera litura)、粘虫(Pseudaletia separata)、Thoricoplusia spp.、实夜蛾(Heliothis spp.)、夜蛾(Helicoverpa spp.)等,
粉蝶科(Pieridae),例如菜粉蝶(Pieris rapae)等,
卷蛾科(Tortricidae),例如卷蛾(Adoxophyes spp.)、梨小食心虫(Grapholita molesta)、苹果皮小卷蛾(Cydia pomonella)等,
蛀果蛾科(Carposinidae),例如桃蛀果蛾(Carposina niponensis)等,
潜蛾科(Lyonetiidae),例如潜蛾(Lyonetia spp.)等,
毒蛾科(Lymantriidae),例如毒蛾(Lymantria spp.)、黄毒蛾(Euproctis spp.)等,
巢蛾科(Yponomeutidae),例如小菜蛾(Plutella xylostella)等,
麦蛾科(Gelechiidae),例如红铃麦蛾(Pectinophora gossypiella)等,
灯蛾科(Arctiidae),例如美国白蛾(Hyphantria cunea)等,
谷蛾科(Tineidae),例如Tinea translucens、幕谷蛾(Tineolabisselliella)等;
双翅目(Diptera):
Calicedae,例如淡色库蚊(Culex pipiens pallens)、三带喙库蚊(Culex tritaeniorhynchus)、致倦库蚊(Culex quinquefasciatus)等,
伊蚊(Aedes spp.),例如埃及伊蚊(Aedes aegypti)、白文伊蚊(Aedesalbopictus)等,
按蚊属(Anopheles),例如中华按蚊(Anopheles sinensis)等,
摇蚊科(Chironomidae),
蝇科(Muscidae),例如家蝇(Musca domestica)、厩腐蝇(Muscinastabulans)等,
丽蝇科(Calliphoridae),
麻蝇科(Sarcophagidae),
厕蝇科(Fanniidae),
花蝇科(Anthomyiidae),例如灰地种蝇(Delia platura)、葱地种蝇(Delia antigua)等,
实蝇科(Tephritidae),
果蝇科(Drosophilidae),
毛蠓科(Psychodidae),
虻科(Tabanidae),
蚋科(Simuliidae),
蛰蝇科(Stomoxyidae),
潜蝇科(Agromyzidae)等;
鞘翅目(Coleoptera):
南美叶甲(Diabrotica spp.),例如玉米根叶甲(Diabroticavirgifera)、Diabrotica undecimpunctata howardi等,
金龟科(Scarabaeidae),例如古铜异丽金龟(Anomala cuprea)、多色异丽金龟(Anomala rufocuprea)等,
象虫科(Curculionidae),例如玉米象(Sitophilus zeamais)、稻水象(Lissorhoptrus oryzophilus)、绿豆象(Callosobruchus chinesis)等,
拟步甲科(Tenebrionidae),例如黄粉甲(Tenebrio molitor)、赤拟谷盗(Tribolium castaneum)等,
叶甲科(Chrysomelidae),例如黄守瓜(Aulacophora femoralis)、黄曲条菜跳甲(Phyllotreta striolata)、马铃薯叶甲(Leptinotarsadecemlineata)等,
窃蠹科(Anobiidae),
瓢虫(Epilachna spp.),例如二十八星瓢虫(Epilachnavigintioctopunctata)等,
粉蠹科(Lyctidae),
长蠹科(Bostrychidae),
天牛科(Cerambycidae),
毒隐翅虫(Paederus fuscipes);
蜚蠊目(Blattodea):
德国小蠊(Blattella germanica)、黑胸大蠊(Periplaneta fuliginosa)、美洲大蠊(Periplaneta americana)、褐斑大蠊(Periplaneta brunnea)、东方蜚蠊(Blatta orientalis)等;
缨翅目(Thysanoptera):
棕榈蓟马(Thrips palmi)、烟蓟马(Thrips tabaci)、西花蓟马(Frankliniella occidentalis)等;
膜翅目(Hymenoptera):
蚁科(Formicidae),例如小家蚁(Monomorium pharaonis)、胡蜂科(Vespidae)、肿腿蜂科(bethylid wasps)、叶蜂科(Tenthredinidae),例如日本菜叶蜂(Athalia japonica)等;
直翅目(Orthoptera):
蝼蛄科(Gryllotalpidae)、剑角蝗科(Acrididae)等;
蚤目(Aphaniptera):
猫蚤(Ctenocephalides felis)、狗蚤(Ctenocephalides canis)、人蚤(Pulex irritans)、鼠蚤(Xenopsylla cheopis);
虱目(Anoplura):
头虱(Pediculus humanus capitis)、阴虱(Phthirus pubis)、牛血虱(Haematopinus eurysternus)、Dalmalinia ovis等;
等翅目(Isoptera):
黄胸散白蚁(Reticulitermes speratus)、台湾乳白蚁(Coptotermesformosanus)等;
螨目(Acarina):
叶螨科(Tetranychidae),例如二斑叶螨(Tetranychus urticae)、柑桔全爪螨(Panonychus citri)、小爪螨(Oligonychus spp.)等,
瘿螨科(Eriophyidae),例如橘刺皮瘿螨(Aculops pelekassi)等,
跗线螨科(Tarsonemidae),例如侧多食跗线螨(Polyphagotarsonemus latus)等,
细须螨科(Tenuipalpidae),
杜克螨科(Tuckerellidae),
硬蜱科(Ixodidae),例如长角血蜱(Haemaphysalis longicornis)、褐黄血蜱(Haemaphysalis flava)、台湾革蜱(Dermacentor taiwanicus)、卵形硬蜱(Ixodes ovatus)、全沟硬蜱(Ixodes persulcatus)、微小牛蜱(Boophilus microplus)、血红扇头蜱(Rhipicephalus sanguineus)等,
粉螨科(Acaridae),例如腐食酪螨(Tyrophagus putrescentiae)等,
表皮螨科(Epidermoptidae),例如粉尘螨(Dermatophagoidesfarinae)、屋尘螨(Dermatophagoides ptrenyssnus)等,
肉食螨科(Cheyletidae),例如普通肉食螨(Cheyletus eruditus)、马六甲肉食螨(Cheyletus malaccensis)、Cheyletus moorei等,
皮刺螨科(Dermanyssidae)。
本发明的有害节肢动物防治组合物含有本发明化合物和惰性载体。一般而言,其为通过混合本发明化合物和固体载体、液体载体、气体载体和/或毒杀诱饵,必要时,添加表面活性剂和其它制剂用辅料。所述制剂包括油溶液剂、乳剂、可流动制剂、可湿性制剂、颗粒剂、粉剂、微胶囊制剂等。这些制剂可转换成用于片状的毒饵中。在本发明的有害节肢动物防治组合物中,本发明化合物含量通常为0.01-95%重量。
制剂用固体载体,例如粘土细粉或颗粒(例如高岭土、硅藻土、膨润土、Fubasami土、酸性粘土等)、合成水合氧化硅、滑石粉、陶土、其它无机材料(例如绢云母、石英、硫磺、活性炭、碳酸钙和水合二氧化硅)或化肥(例如硫酸铵、磷酸铵、硝酸铵、尿素和氯化铵)。
制剂用液体载体包括,例如水、醇(例如甲醇、乙醇、异丙醇、丁醇、己醇、苯甲醇、乙二醇、丙二醇、苯氧基乙醇)、酮(例如丙酮、甲乙酮、环己酮)、芳香烃(例如甲苯、二甲苯、乙苯、十二烷基苯、苯基二甲苯基乙烷、甲基萘)、脂肪烃(例如己烷、环己烷、煤油、轻油)、酯(例如乙酸乙酯、乙酸丁酯、十四烷酸异丙酯、油酸乙酯、己二酸二异丙酯、己二酸二异丁酯、乙酸丙二醇单甲酯)、腈(例如乙腈和异丁腈)、醚(例如二异丙基醚、1,4-二噁烷、乙二醇二甲醚、二乙二醇二甲醚、二乙二醇单甲醚、丙二醇单甲醚、二丙二醇单甲醚、3-甲氧基-3-甲基-1-丁醇)、酰胺(例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺)、卤代烃(例如二氯甲烷、三氯乙烷、四氯化碳)、亚砜(例如二甲亚砜)和植物油(例如大豆油、棉子油)。
制剂用气体载体包括,例如碳氟化合物、丁烷气、液化石油气(LPG)、二甲醚和二氧化碳。
制剂用表面活性剂包括,例如,非离子型表面活性剂如聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚乙二醇脂肪酸酯;阴离子型表面活性剂如烷基磺酸盐、烷基苯磺酸盐、烷基硫酸(surfic acid)盐。
其它制剂用辅料包括粘合剂、分散剂和稳定剂,具体如酪蛋白、明胶、多糖(例如淀粉、阿拉伯胶、纤维素衍生物、海藻酸)、木质素衍生物、膨润土、合成水溶性多聚物(例如聚乙烯醇、聚乙烯吡咯烷酮、聚丙烯酸)、PAP(异丙基酸磷酸盐)、BHT(2,6-二叔丁基-4-甲基苯酚)、BHA(2-叔丁基-4-甲氧基苯酚和3-叔丁基-4-甲氧基苯酚混合物)。
本发明有害节肢动物防治方法为,直接将本发明化合物应用于节肢动物和/或节肢动物栖息地(例如植物、土壤、室内、动物体内等)。本发明化合物通常用作有害节肢动物防治组合物。
当本发明的有害节肢动物防治组合物用于防治农业和林业的节肢动物时,使用量通常为1-10,000g本发明化合物/10,000m2。本发明的有害节肢动物防治组合物的乳剂、可湿性粉剂和可流动制剂,通常在用水稀释成有效成分浓度为0.01-10,000ppm后使用,而粉剂和颗粒剂也通常如此应用。
这些制剂和所述制剂稀释剂可直接向节肢动物或节肢动物藏身的植物喷雾。栖息于土壤中的节肢动物可以通过用这些制剂处理土壤进行防治。
此外,制成片状或条状的局部制剂可以通过缠绕植物、伸展在植物附近及放置在植物根部土壤表面而应用。
当本发明的有害节肢动物防治组合物用于防治室内的有害节肢动物(例如苍蝇、蚊子、蟑螂)时,在施用于平面的情况下,其用量通常为0.01-1,000mg本发明化合物/1m2,在用于立体空间的情况下,用量通常为0.01-500mg本发明化合物/1m3。本发明的有害节肢动物防治组合物的乳剂、可湿性粉剂和可流动制剂,通常在用水稀释成有效成分浓度为0.01-1,000ppm后使用,而溶液剂、气雾剂、烟雾剂和毒饵也通常如此应用。
本发明的有害节肢动物防治组合物可含有其它有害节肢动物防治组合物、杀线虫剂、杀真菌剂、除草剂、植物生长调节剂、增效剂、肥料、土壤调节剂、动物饲料等。
所述有害节肢动物防治组合物和杀线虫剂的有效成分包括,例如有机膦化合物例如杀螟硫磷、倍硫磷、哒嗪硫磷、二嗪磷、毒死蜱、甲基毒死蜱、高灭磷、杀扑磷、乙拌磷、DDVP、乙丙硫磷、杀螟腈、蔬果磷、乐果、稻丰散、马拉硫磷、敌百虫、谷硫磷、久效磷乙硫磷丙溴磷、甲基对硫磷和异噁唑磷;氨基甲酸酯化合物例如BPMC、丙硫克百威、残杀威、丁硫克百威、甲萘威(Carbaril)、灭多虫、乙硫苯威、涕灭威、草胺酰、苯硫威、硫双威和棉铃威;拟除虫菊酯化合物例如醚菊酯、杀灭菊酯、S-氰戊菊酯、甲氰菊酯、氯氰菊酯、α-氯氰菊酯、ζ-氯氰菊酯、氯菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、δ-氯氟氰菊酯、氟氯氰菊酯、β-氟氯氰菊酯、乙氰菊酯、氟胺氰菊酯、氟氰戊菊酯、联苯菊酯、氟丙菊酯、四溴菊酯(Traromethrin)和氟硅菊酯;新烟碱样化合物例如吡虫清、烯啶虫胺、噻虫嗪和噻虫啉;沙蚕毒素衍生物例如杀螟丹、杀虫环和杀虫磺;氯代烃例如硫丹、γ-BHC和1,1-双(氯苯基)-2,2,2-三氯乙醇;苯甲酰基苯基脲化合物例如氟啶脲、氟苯脲、Fulphenoxron和虱螨脲;苯基酰肼化合物例如虫酰肼、环虫酰胺、甲氧苯酰肼和氯虫酰肼;甲脒衍生物例如虫螨脒和杀虫脒;硫脲衍生物例如杀螨硫隆;扑虱灵;氟唑虫清、多杀菌素及其衍生物;甲氨基阿维菌素苯甲酸盐;噁二唑虫;拒嗪酮;苯基吡唑衍生物;溴螨酯;三氯杀螨砜;灭螨猛;克螨特;克螨锡;三环锡;噻螨酮(Hexathiazox);四螨嗪;哒螨酮;唑螨酯;吡螨胺;嘧胺苯醚;喹螨醚;联苯肼酯;灭螨醌;spirodiclofen;spiromesifen;复合杀螨霉素[例如杀螨霉素、二甲杀螨霉素、一甲杀螨霉素];米尔螨素;齐墩螨素;azadilactin。
本发明通过下面的生产实施例、制剂实施例和试验实施例进一步说明;然而,本发明并不限于这些实施例。
下面描述本发明的生产实施例。
生产实施例1
取200mg式(i)化合物:
溶于3ml N,N-二甲基甲酰胺中,向所得混合物中加入100mg碳酸钾和100mg 1,1,3-三氯丙烯,并将所得混合物于70℃搅拌1小时。将反应混合物冷却至室温,加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到190mg式(1)化合物:
(在下文简称本发明化合物(1))。
1H-NMR(CDCl3,TMS)δ(ppm):9.51(1H,s),6.83-6.97(8H,m),6.16(1H,t),4.64(2H,d),3.66(3H,s),2.45(3H,s)
生产实施例2
取440mg式(ii)化合物:
溶于5ml N,N-二甲基甲酰胺中,向所得混合物中加入220mg碳酸钾和210mg 1,1,3-三氯丙烯,并将所得混合物于70℃搅拌1小时。将反应混合物冷却至室温,加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到480mg式(2)化合物:
(在下文简称本发明化合物(2))。
1H-NMR(CDCl3,TMS)δ(ppm):9.53(1H,s),6.86-6.98(8H,m),6.16(1H,t),3.66(3H,s),2.85(2H,q),1.26(3H,t)
生产实施例3
取200mg本发明化合物(1)溶于5ml吡啶中,在冰冷却下,向所得混合物中加入45mg甲氧基胺盐酸盐,并将所得混合物在室温下搅拌2小时。减压浓缩反应混合物。向残留物中加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到200mg式(3)化合物:
(在下文简称本发明化合物(3))。
1H-NMR(CDCl3,TMS)δ(ppm):7.74(1H,s),6.16-6.96(8H,m),6.16(1H,t),4.64(2H,d),3.81(3H,s),3.62(3H,s),2.38(3H,s)
生产实施例4
通过用50mg乙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到170mg式(4)化合物:
(在下文简称本发明化合物(4))。
1H-NMR(CDCl3,TMS)δ(ppm):7.75(1H,s),6.83-6.95(8H,m),6.15(1H,t),4.63(2H,d),4.04(2H,q),3.61(3H,s),2.37(3H,s),1.21(3H,t)
生产实施例5
通过用62mg异丙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到140mg式(5)化合物:
(在下文简称本发明化合物(5))。
1H-NMR(CDCl3,TMS)δ(ppm):7.77(1H,s),6.82-6.98(8H,m),6.15(1H,t),5.37(1H,q),4.63(2H,d),3.61(3H,s),2.37(3H,s),1.73(6H,d)
生产实施例6
通过用248mg本发明化合物(1)和80mg叔丁氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到270mg式(6)化合物:
(在下文简称本发明化合物(6))。
1H-NMR(CDCl3,TMS)δ(ppm):7.76(1H,s),6.82-6.99(8H,m),6.16(1H,t),4.63(2H,d),3.62(3H,s),2.38(3H,s),1.21(9H,s)
生产实施例7
通过用77mg戊氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到130mg式(7)化合物:
(在下文简称本发明化合物(7))。
1H-NMR(CDCl3,TMS)δ(ppm):7.76(1H,s),6.83-6.95(8H,m),6.16(1H,t),4.64(2H,d),3.98(2H,t),3.61(3H,s),2.37(3H,s),1.58(2H,br),1.30-1.32(5H,m),0.89(3H,t)
生产实施例8
通过用60mg 2-丙炔氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到140mg式(8)化合物:
(在下文简称本发明化合物(8))。
1H-NMR(CDCl3,TMS)δ(ppm):7.80(1H,s),6.84-6.96(8H,m),6.16(1H,t),4.64(2H,d),4.60(1H,s),3.62(3H,s),2.44(3H,s)
生产实施例9
通过用55mg烯丙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到200mg式(9)化合物:
(在下文简称本发明化合物(9))。
1H-NMR(CDCl3,TMS)δ(ppm):7.79(1H,s),6.83-6.95(8H,m),6.15(1H,t),5.90-5.97(1H,m),5.16-5.28(2H,m),4.64(2H,d),4.50(2H,d),3.61(3H,s)
生产实施例10
通过用100mg 3,3-二氯-2-丙烯氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到130mg式(10)化合物:
(在下文简称本发明化合物(10))。
1H-NMR(CDCl3,TMS)δ(ppm):7.75(1H,s),6.83-6.95(8H,m),6.15(1H,t),6.03(1H,t),4.64(2H,d),4.57(2H,d),3.62(3H,s),2.36(3H,s)
生产实施例11
通过用75mg苄氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到165mg式(11)化合物:
(在下文简称本发明化合物(11))。
1H-NMR(CDCl3,TMS)δ(ppm):7.80(1H,s),7.28-7.32(5H,m),6.81-6.95(8H,m),6.16(1H,t),5.02(2H,s),4.63(2H,d),3.60(3H,s),2.35(3H,s)
生产实施例12
通过用55mg(E)-2-丁烯氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到90mg式(12)化合物:
(在下文简称本发明化合物(12))。
1H-NMR(CDCl3,TMS)δ(ppm):7.77(1H,s),6.83-6.96(8H,m),6.16(1H,t),5.60-6.17(2H,m),4.64(2H,d),4.42(2H,d),3.62(3H,s),2.37(3H,q),1.71(3H,d)
生产实施例13
取190mg本发明化合物(2)溶于5ml吡啶中,在冰冷却下,向所得混合物中加入43mg甲氧基胺盐酸盐,并将所得混合物在室温下搅拌2小时。减压浓缩反应混合物。向残留物中加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到150mg式(13)化合物:
(在下文简称本发明化合物(13))。
1H-NMR(CDCl3,TMS)δ(ppm):7.74(1H,s),6.83-6.95(8H,m),6.16(1H,t),4.64(2H,d),3.80(3H,s),3.62(3H,s),2.78(2H,q),1.27(3H,t)
生产实施例14
通过用180mg本发明化合物(2)和50mg乙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到160mg式(14)化合物:
(在下文简称本发明化合物(14))。
1H-NMR(CDCl3,TMS)δ(ppm):7.77(1H,s),6.83-6.95(8H,m),6.16(1H,t),4.64(2H,d),4.04(2H,q),3.62(3H,s),2.77(2H,q),1.19-1.28(6H,m)
生产实施例15
取190mg式(iii)化合物:
溶于2ml N,N-二甲基甲酰胺中,向所得混合物中加入80mg碳酸钾和80mg 1,1,3-三氯丙烯,并将所得混合物于80℃搅拌1小时。将反应混合物冷却至室温,加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到150mg式(15)化合物:
(在下文简称本发明化合物(15))。
1H-NMR(CDCl3,TMS)δ(ppm):7.84(1H,s),6.85-6.95(8H,m),6.16(1H,t),4.64(2H,d),3.78(3H,s),3.71(3H,s)
生产实施例16
取170mg式(iv)化合物:
溶于3ml N,N-二甲基甲酰胺中,向所得混合物中加入80mg碳酸钾和70mg 1,3-二氯-2-丁烯,并将所得混合物于80℃搅拌1小时。将反应混合物冷却至室温,加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到160mg式(16)化合物:
(在下文简称本发明化合物(16))。
1H-NMR(CDCl3,TMS)δ(ppm):7.73(1H,s),6.82-6.96(8H,m),5.76(1H,t),4.66(2H,d),4.48(3H,s),3.61(3H,s),2.38(3H,s),2.17(3H,s)
生产实施例17
通过用60mg 1,3-二氯丙烯替代生产实施例16中的1,3-二氯-2-丁烯,得到130mg式(17)化合物:
(在下文简称本发明化合物(17))。
1H-NMR(CDCl3,TMS)δ(ppm):7.74(1H,s),6.83-6.95(8H,m),6.37-6.40(1H,m),6.13-6.19(1H,m),4.50(2H,d),3.80(3H,s),3.61(3H,s),2.38(3H,s)
生产实施例18
取114mg本发明化合物(1)溶于3ml吡啶中,在冰冷却下,向所得混合物中加入25mg羟胺盐酸盐,并将所得混合物在室温下搅拌30分钟。减压浓缩反应混合物。向残留物中加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到80mg式(18)化合物:
(在下文简称本发明化合物(18))。
1H-NMR(CDCl3,TMS)δ(ppm):7.83(1H,s),7.08(1H,s),6.84-6.96(8H,m),6.16(1H,t),4.64(2H,d),3.61(3H,s),2.36(3H,s)
生产实施例19
通过用370mg本发明化合物(1)和110mg丙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到400mg式(19)化合物:
(在下文简称本发明化合物(19))。
1H-NMR(CDCl3,TMS)δ(ppm):0.90(3H,t),1.61(2H,m),2.37(3H,s),3.62(3H,s),3.94(2H,t),4.64(2H,d),6.16(1H,t),6.83-6.96(8H,m),7.77(1H,s)
生产实施例20
通过用150mg本发明化合物(1)和60mg新戊氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到130mg式(20)化合物:
(在下文简称本发明化合物(20))。
1H-NMR(CDCl3,TMS)δ(ppm):0.90(6H,d),1.46-1.70(3H,m),2.37(3H,s),3.61(3H,s),4.02(2H,t),4.64(2H,d),6.16(1H,t),6.82-6.96(8H,m),7.75(1H,s)
生产实施例21
通过用150mg本发明化合物(1)和60mg 3-甲基-2-丁烯氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到150mg式(21)化合物:
(在下文简称本发明化合物(21))。
1H-NMR(CDCl3,TMS)δ(ppm):1.70(3H,s),1.75(3H,s),2.37(3H,s),3.61(3H,s),4.50(2H,d),4.63(2H,d),5.38(1H,m),6.16(1H,t),6.82-6.96(8H,m),7.77(1H,s)
生产实施例22
通过用150mg本发明化合物(1)和50mg 1-甲基-2-丙炔氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到110mg式(22)化合物:
(在下文简称本发明化合物(22))。
1H-NMR(CDCl3,TMS)δ(ppm):1.46(3H,d),2.38(3H,s),2.43(1H,d),3.62(3H,s),4.63(2H,d),4.79(1H,m),6.16(1H,t),6.83-6.96(8H,m),7.79(1H,s)
生产实施例23
通过用150mg本发明化合物(1)和50mg 1-甲基丙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到170mg式(23)化合物:
(在下文简称本发明化合物(23))。
1H-NMR(CDCl3,TMS)δ(ppm):0.88(3H,t),1.15(3H,d),1.41-1.64(2H,m),2.37(3H,s),3.62(3H,s),4.04(1H,m),4.63(2H,d),6.16(1H,t),6.83-6.96(8H,m),7.76(1H,s)
生产实施例24
通过用150mg本发明化合物(1)和70mg 1,2-二甲基丙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到160mg式(24)化合物:
(在下文简称本发明化合物(24))。
1H-NMR(CDCl3,TMS)δ(ppm):0.83(3H,d),0.88(3H,d),1.11(3H,d),1.82(1H,m),2.37(3H,s),3.62(3H,s),3.89(1H,m),4.64(2H,d),6.16(1H,t),6.82-6.96(8H,m),7.76(1H,s)
生产实施例25
通过用150mg本发明化合物(1)和50mg 2-氟乙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到130mg式(25)化合物:
(在下文简称本发明化合物(25))。
1H-NMR(CDCl3,TMS)δ(ppm):2.36(3H,s),3.62(3H,s),4.21(2H,dt),4.56(2H,dt),4.64(2H,d),6.16(1H,t),6.82-6.97(8H,m),7.83(1H,s)
生产实施例26
通过用150mg本发明化合物(1)和70mg 3,3,3-三氟丙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到140mg式(26)化合物:
(在下文简称本发明化合物(26))。
1H-NMR(CDCl3,TMS)δ(ppm):2.36(5H,m),3.63(3H,s),4.19(2H,t),4.64(2H,d),6.16(1H,t),6.83-6.96(8H,m),7.77(1H,s)
生产实施例27
通过用150mg本发明化合物(1)和70mg 4,4,4-三氟丙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到120mg式(27)化合物:
(在下文简称本发明化合物(27))。
1H-NMR(CDCl3,TMS)δ(ppm):1.86(2H,m),2.12(2H,m),2.36(3H,s),3.62(3H,s),4.03(2H,t),4.64(2H,d),6.16(1H,t),6.82-6.96(8H,m),7.77(1H,s)
生产实施例28
通过用150mg本发明化合物(1)和70mg 3-氯-2-丙烯氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到160mg式(28)化合物的非对映体混合物:
(在下文简称本发明化合物(28))。
1H-NMR(CDCl3,TMS)δ(ppm):2.36(1.5H,s),2.36(1.5H,s),3.62(3H,s),4.45(1H,dd),4.64(2H,d),4.70(1H,dd),5.94(0.5H,m),6.04(0.5H,m),6.16(2H,m),6.83-6.96(8H,m),7.76(0.5H,s),7.77(0.5H,s)
生产实施例29
通过用150mg本发明化合物(1)和110mg 3,3-二溴-2-丙烯氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到220mg式(29)化合物:
(在下文简称本发明化合物(29))。
1H-NMR(CDCl3,TMS)δ(ppm):2.36(3H,s),3.62(3H,s),4.48(2H,d),4.64(2H,d),6.16(1H,t),6.59(1H,t),6.83-6.97(8H,m),7.76(1H,s)
生产实施例30
通过用150mg本发明化合物(1)和60mg丁氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到160mg式(30)化合物:
(在下文简称本发明化合物(30))。
1H-NMR(CDCl3,TMS)δ(ppm):0.91(3H,t),1.35(2H,m),1.56(2H,m),2.37(3H,s),3.62(3H,s),4.00(2H,t),4.64(2H,d),6.16(1H,t),6.82-6.96(8H,m),7.76(1H,s)
生产实施例31
取200mg本发明化合物(18),溶于2ml N,N-二甲基甲酰胺中,向所得混合物中加入120mg碳酸钾和110mg溴乙腈,并将所得混合物于40℃搅拌5小时。将反应混合物冷却至室温,加入稀盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到80mg式(31)化合物:
(在下文简称本发明化合物(31))。
1H-NMR(CDCl3,TMS)δ(ppm):2.38(3H,s),3.63(3H,s),4.63(4H,m),6.16(1H,t),6.85-6.98(8H,m),7.82(1H,s)
生产实施例32
通过用3.50g本发明化合物(1)和1.35g 2,2,2-三氟乙氧基胺盐酸盐替代生产实施例3中的甲氧基胺盐酸盐,得到3.85g式(32)化合物:
(在下文简称本发明化合物(32))。
1H-NMR(CDCl3,TMS)δ(ppm):2.36(3H,s),3.62(3H,s),4.34(2H,q),4.64(2H,d),6.16(1H,t),6.82-6.97(8H,m),7.83(1H,s)
生产实施例33
取150mg本发明化合物(18),溶于2ml N,N-二甲基甲酰胺中,向所得混合物中加入90mg碳酸钾和1-溴-2-甲基丙烷,并将所得混合物于70℃搅拌10小时。将反应混合物冷却至室温,加入稀盐酸中,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到40mg式(33)化合物:
(在下文简称本发明化合物(33))。
1H-NMR(CDCl3,TMS)δ(ppm):0.88(6H,d),1.90(1H,m),2.37(3H,s),3.62(3H,s),3.76(2H,d),4.64(2H,d),6.16(1H,t),6.83-6.96(8H,m),7.77(1H,s)
生产实施例34
在室温下,将90mg氢化钠(60%油悬液)悬浮于5ml己烷中,并向所得混合物中加入460mg 5-氯-1,3-二甲基-1H-吡唑-4-甲醛。然后将500mg式(v)化合物:
在回流条件下,滴加到所得混合物中,并将所得混合物在回流条件下搅拌5小时。向反应混合物中加入饱和氯化铵水溶液,用乙酸乙酯萃取。有机层用稀盐酸、水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到260mg式(34)化合物:
(在下文简称本发明化合物(34))。
1H-NMR(CDCl3,TMS)δ(ppm):2.45(3H,s),3.65(3H,s),4.64(2H,d),6.15(1H,t),6.78-7.01(7H,m),9.51(1H,s)
生产实施例35
取150mg本发明化合物(34),溶于2ml吡啶中,在冰冷却条件下,向所得混合物中加入40mg 2-丙炔氧基胺盐酸盐,并将所得混合物在室温下搅拌5小时。减压浓缩反应混合物。稀盐酸加入到残留物中,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到150mg式(35)化合物:
(在下文简称本发明化合物(35))。
1H-NMR(CDCl3,TMS)δ(ppm):2.36(3H,s),2.43(1H,t),3.62(3H,s),4.59(2H,d),4.63(2H,d),6.15(1H,t),6.76-7.01(7H,m),7.80(1H,s)
生产实施例36
取200mg本发明化合物(18),溶于2ml N,N-二甲基甲酰胺中,于室温向所得混合物中加入80mg碳酸钾和60mg 2,3-二氯丙烯,并将所得混合物于70℃搅拌10小时。将反应混合物冷却至室温,加入稀盐酸中,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到130mg式(36)化合物:
(在下文简称本发明化合物(36))。
1H-NMR(CDCl3,TMS)δ(ppm):2.35(3H,s),3.62(3H,s),4.52(2H,s),4.64(2H,d),5.33(1H,s),5,35(1H,s),6.16(1H,t),6.82-6.97(8H,m),7.84(1H,s)
生产实施例37
取200mg本发明化合物(18),溶于2ml N,N-二甲基甲酰胺中,于室温向所得混合物中加入90mg碳酸钾和110mg甲磺酸2-氯乙酯,并将所得混合物于70℃搅拌10小时。将反应混合物冷却至室温,加入稀盐酸中,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到90mg式(37)化合物:
(在下文简称本发明化合物(37))。
1H-NMR(CDCl3,TMS)δ(ppm):2.35(3H,s),3.60(2H,t),3.63(3H,s),4.18(2H,t),4.64(2H,d),6.16(1H,t),6.83-6.98(8H,m),7.82(1H,s)
生产实施例38
取270mg本发明化合物(vi):
溶于2ml N,N-二甲基甲酰胺中,向所得混合物中加入150mg碳酸钾和140mg 1,1,3-三氯丙烯,并将所得混合物在室温下搅拌10小时。将反应混合物冷却,加入稀盐酸中,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到350mg式(38)化合物:
(在下文简称本发明化合物(38))。
1H-NMR(CDCl3,TMS)δ(ppm):2.25(3H,s),2.47(3H,s),3.57(3H,s),4.64(2H,d),6.16(1H,t),6.81-6.97(8H,m)
生产实施例39
取160mg本发明化合物(38),溶于2ml吡啶中,于室温向所得混合物中加入50mg 2-丙炔氧基胺盐酸盐,并将所得混合物在室温下搅拌10小时。减压浓缩反应混合物。稀盐酸加入残留物中,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到170mg式(39)化合物:
(在下文简称本发明化合物(39))。
1H-NMR(CDCl3,TMS)δ(ppm):2.00(3H,s),2.39(3H,s),2.43(1H,t),3.58(3H,s),4.64(2H,d),4.65(2H,d),6.16(1H,t),6.77-6.97(8H,m)
生产实施例40
取300mg本发明化合物(18),溶于3ml N,N-二甲基甲酰胺中,于室温向所得混合物中加入100mg碳酸钾和110mg 1-溴-2-丁炔,并将所得混合物于40℃搅拌10小时。将反应混合物冷却至室温,加入稀盐酸中,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到250mg式(40)化合物:
(在下文简称本发明化合物(40))。
1H-NMR(CDCl3,TMS)δ(ppm):1.85(3H,t),2.37(3H,s),3.62(3H,s),4.57(2H,q),4.64(2H,d),6.16(1H,t),6.83-6.97(8H,m),7.79(1H,s)
接着,下面描述本发明中间体的参考生产实施例。
参考生产实施例1
取330mg本发明化合物(i),溶于3ml吡啶中,在冰冷却条件下,向其中加入100mg甲氧基胺盐酸盐,并将所得混合物在室温下搅拌2小时。减压浓缩反应混合物。向残留物中加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到290mg式(iv)化合物。
1H-NMR(CDCl3,TMS)δ(ppm):7.74(1H,s),6.80-6.90(8H,m),5.97(1H,s),3.81(3H,s),3.61(3H,s),2.39(3H,s)
参考生产实施例2
取240mg本发明化合物(vii)
溶于3ml吡啶中,在冰冷却条件下,加入64mg甲氧基胺盐酸盐,并将所得混合物在室温下搅拌2小时。减压浓缩反应混合物。向残留物中加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到260mg式(iii)化合物。
1H-NMR(CDCl3,TMS)δ(ppm):7.83(1H,s),6.79-7.11(8H,m),5.28(1H,br),3.78(3H,s),3.70(3H,s)
参考生产实施例3
取300mg 4,4’-二羟基二苯醚,溶于5ml N,N’-二甲基甲酰胺中,在冰冷却条件下,向其中加入120mg氢化钠(60%油悬液),并将所得混合物在室温下搅拌10分钟。然后,于70℃,在10分钟内边搅拌边滴加3ml N,N’-二甲基甲酰胺中的230mg 5-氯-1,3-二甲基-1H-吡唑-4-甲醛,于70℃搅拌2小时。将反应混合物冷却至室温,加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到260mg式(i)化合物。
1H-NMR(CDCl3,TMS)δ(ppm):9.50(1H,s),6.76-6.99(8H,m),5.44(1H,br),3.66(3H,s),2.45(3H,s)
参考生产实施例4
取500mg 4,4’-二羟基二苯醚,溶于5ml N,N’-二甲基甲酰胺中,在冰冷却条件下,向其中加入200mg氢化钠(60%油悬液),并将所得混合物在室温下搅拌10分钟。然后,于70℃,在10分钟内边搅拌边滴加5ml N,N’-二甲基甲酰胺中的410mg 5-氯-3-乙基-1-甲基-1H-吡唑-4-甲醛,于70℃搅拌2小时。将反应混合物冷却至室温,加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到460mg式(ii)化合物。
1H-NMR(CDCl3,TMS)δ(ppm):9.51(1H,s),6.79-6.94(8H,m),5.44(1H,s),3.66(3H,s),2.86(2H,q),1.27(3H,t)
参考生产实施例5
取570mg 4,4’-二羟基二苯醚,溶于5ml N,N’-二甲基甲酰胺中,在冰冷却条件下,向其中加入170mg氢化钠(60%油悬液),并将所得混合物在室温下搅拌10分钟。然后,于70℃,在10分钟内边搅拌边滴加5ml N,N’-二甲基甲酰胺中的570mg 5-氯-1-甲基-3-三氟甲基-1H-吡唑-4-甲醛,于70℃搅拌2小时。将反应混合物冷却至室温,加入水和10%盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到440mg式(vii)化合物。
1H-NMR(CDCl3,TMS)δ(ppm):9.66(1H,s),6.79-6.93(8H,m),4.95(1H,s),3.81(3H,s)
参考生产实施例6
取560mg 4,4’-二羟基二苯基醚,溶于10ml N,N’-二甲基甲酰胺中,在冰冷却条件下,向其中加入140mg氢化钠(60%油悬液),并将所得混合物于70℃搅拌1小时。然后,于70℃,在15分钟内边搅拌边滴加5ml N,N’-二甲基甲酰胺中的400mg 1-(5-氯-1,3-二甲基-1H-吡唑-4-基)乙酮,于70℃搅拌6小时。将反应混合物冷却至室温,加入稀盐酸,用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,经硫酸镁干燥并减压浓缩。残留物用硅胶柱色谱法进行纯化,得到340mg式(vi)化合物。
1H-NMR(CDCl3,TMS)δ(ppm):2.26(3H,s),2.47(3H,s),3.57(3H,s),5.22(1H,s),6.79-6.95(8H,m)
下面描述制剂实施例,其中份表示重量份。
制剂实施例1
取本发明化合物(1)-(40),每种10份,溶于35份二甲苯和35份N,N-二甲基甲酰胺的混合物中,向其中加入14份聚氧乙烯苯乙烯基苯基醚和6份十二烷基苯磺酸钙,然后充分搅拌并混合,得到每种化合物的10%乳剂。
制剂实施例2
取本发明化合物(1)-(40),每种20份,加入到含有4份十二烷基硫酸钠、2份木质素磺酸钙、20份合成水合氧化硅细粉和54份硅藻土的混合物中,然后充分搅拌并混合,得到每种化合物的20%可湿性粉剂。
制剂实施例3
取本发明化合物(1)-(40),每种2份,向其中加入1份合成水合氧化硅细粉、2份木质素磺酸钙、30份膨润土和65份高岭土,然后然后充分搅拌并混合,向该混合物中加入适量的水,然后进一步搅拌,用制粒机制粒,风干,得到每种化合物的2%颗粒剂。
制剂实施例4
取本发明化合物(1)-(40),每种1份,溶于适量的丙酮中,将5份合成水合氧化硅细粉、0.3份PAP和93.7份Fubasami粘土充分搅拌并混合,蒸发除去混合物中的丙酮,得到每种化合物的1%粉剂。
制剂实施例5
取本发明化合物(1)-(40),每种10份,使其与35份含有50份聚氧乙烯烷基醚硫酸铵的白碳墨和55份水混合,并用湿研磨法研磨,得到每种化合物的10%可流动制剂。
制剂实施例6
取本发明化合物(1)-(40),每种0.1份,溶于5份二甲苯和5份三氯乙烷的混合物中,并将所得溶液与89.9份脱臭煤油混合,得到每种化合物的0.1%油溶液剂。
制剂实施例7
取本发明化合物(1)-(40),每种10mg,溶于0.5ml丙酮中,将溶液施用于5g粉状固体动物食物(出血用粉状固体动物食物EC-2;日本CLEA公司的产品),并混合均匀,蒸发除去混合物中的丙酮,得到每种化合物的毒饵。
下述试验实施例用于证明本发明化合物的有害节肢动物防治活性。
试验实施例1
下述每一种本发明化合物(2)-(15)、(17)-(33)、(36)-(40)和对比化合物,根据制剂实施例5配制,每种制剂用水稀释,以使本发明化合物或对比化合物的浓度达到500ppm。
让约20只雌性成体二斑叶螨(Tetranychus urticae)自由生活在初生叶期的菜豆(Phaseolus vulgaris)上,该植物在播种后已置于塑料杯中生长7天。1天后,将30ml上述稀释制剂喷在上述植物上。在施药后第8天和第13天,检查菜豆叶上二斑叶螨的活体数,并通过以下方案计算防治率。
防治率=100×{1-(经处理的二斑叶螨活体数)/(未经处理的二斑叶螨活体数)}
结果,在本发明化合物(2)-(15)、(17)-(33)、(36)-(40)的处理中,在施药后第8天和第13天,所有防治率都不低于90%。在对比化合物的处理中,在施药后第8天和第13天,防治率低于30%。
对比化合物
其作为第189号化合物,公开于日本公开特许公报S63-183564,第21页。
试验实施例2
下述每一种本发明化合物(3)、(4)、(6)-(10)、(12)-(33)、(36)、(37)、(39)和(40),根据制剂实施例5配制,每种制剂用水稀释,以使本发明化合物的浓度达到500ppm。
在直径5.5cm的聚乙烯杯杯底,放置9g人工饵料(Silkmate 2S;Nosan公司生产),在人工饵料上滴加1ml上述稀释制剂。让30条棉褐带卷蛾(Adoxophyes orana)第一龄期幼虫自由生活在聚乙烯杯中。7天后,检查棉褐带卷蛾的活体数,以获得害虫死亡率。
结果,在本发明化合物(3)、(4)、(6)-(10)、(12)-(33)、(36)、(37)、(39)和(40)的处理中,所有的害虫死亡率都不低于90%。
工业实用性
用本发明化合物,可以防治有害节肢动物。
Claims (15)
1.一种以下式(a)的吡唑化合物:
其中R1表示C1-C4烷基或三氟甲基,R2表示C1-C4烷基,R3表示氢或C1-C6烷基;R4表示卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基,m表示0-4的整数,当m为2-4的整数时,每个R4相同或者不同;R5表示卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基,n表示0-4的整数,当n为2-4的整数时,每个R5相同或者不同;R6和R7相同或者不同,并且表示氢、卤素或甲基,X表示氧或R8O-N;R8表示氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基,其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代。
2.权利要求1的吡唑化合物,其中在式(a)中,R3为氢。
3.权利要求1的吡唑化合物,其中在式(a)中,R3为C1-C6烷基。
4.权利要求1-3中任一项的吡唑化合物,其中在式(a)中,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基,其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代。
5.权利要求1-3中任一项的吡唑化合物,其中在式(a)中,X为R8O-N,R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C2-C5氰基烷基。
6.权利要求1-3中任一项的吡唑化合物,其中在式(a)中,X为R8O-N,R8为苄基,其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代。
7.权利要求1-3中任一项的吡唑化合物,其中在式(a)中,X为氧。
8.权利要求1的吡唑化合物,其中在式(a)中,R6为卤素。
9.权利要求1的吡唑化合物,其中在式(a)中,R6和R7为卤素。
10.权利要求1的吡唑化合物,其中在式(a)中,R6和R7为氯。
11.权利要求1的吡唑化合物,其中在式(a)中,R4和R5为卤素、C1-C3烷基、C1-C3烷氧基或三氟甲基,m和n为0-2的整数。
12.一种有害节肢动物防治组合物,所述组合物包含有效量的权利要求1的吡唑化合物。
13.一种防治有害节肢动物的方法,所述方法包括把有效量的权利要求1的吡唑化合物应用于有害节肢动物或有害节肢动物栖息地。
14.权利要求1的吡唑化合物作为有害节肢动物防治组合物的有效成分的用途。
15.一种以下式(b)的化合物:
其中R1表示C1-C4烷基或三氟甲基,R2表示C1-C4烷基,R3表示氢或C1-C6烷基;R4表示卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基,m表示0-4的整数,当m为2-4的整数时,每个R4相同或者不同;R5表示卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基,n表示0-4的整数,当n为2-4的整数时,每个R5相同或者不同;X表示氧或R8O-N;R8表示氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基、C2-C5氰基烷基或苄基,其中所述苄基可以被卤素、C1-C4烷基、C1-C4烷氧基、C2-C5烷氧基羰基、三氟甲基或三氟甲氧基取代。
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WO2010060379A1 (zh) * | 2008-11-28 | 2010-06-03 | 中国中化集团公司 | 具有含氮五元杂环的醚类化合物及其应用 |
Families Citing this family (2)
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TWI344340B (en) | 2004-02-05 | 2011-07-01 | Sumitomo Chemical Co | Pyrazole compounds and use thereof |
PE20231209A1 (es) | 2020-09-25 | 2023-08-17 | Neuropore Therapies Inc | Compuestos y composiciones como moduladores de senalizacion tlr |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS6253970A (ja) | 1985-09-03 | 1987-03-09 | Nippon Nohyaku Co Ltd | ピラゾ−ル誘導体及びその製法 |
US4843068A (en) | 1985-12-27 | 1989-06-27 | Nihon Nohyaku Co., Ltd. | Pyrazole oxime derivatives and compositions |
TW306864B (zh) * | 1993-10-19 | 1997-06-01 | Sumitomo Chemical Co | |
JPH08208551A (ja) * | 1995-02-01 | 1996-08-13 | Sumitomo Chem Co Ltd | ジハロプロペン化合物およびそれを有効成分とする殺虫、殺ダニ剤 |
CN1072211C (zh) | 1997-01-23 | 2001-10-03 | 化学工业部沈阳化工研究院 | 作为农用杀菌剂和杀虫杀螨的吡唑类化合物及其制剂 |
WO2000071536A1 (en) | 1999-05-20 | 2000-11-30 | E.I. Du Pont De Nemours And Company | Heteroaryloxypyrimidine insecticides and acaricides |
JP2001354659A (ja) * | 2000-06-13 | 2001-12-25 | Kureha Chem Ind Co Ltd | 新規ピラゾリン誘導体、その製造方法、及び有害生物防除剤 |
DE10063865A1 (de) * | 2000-12-21 | 2002-06-27 | Bayer Ag | Verwendung von Pyrazoloximen als Parasitizide |
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2004
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- 2004-02-03 DE DE602004029143T patent/DE602004029143D1/de not_active Expired - Lifetime
- 2004-02-03 ES ES04707666T patent/ES2349635T3/es not_active Expired - Lifetime
- 2004-02-03 US US10/545,066 patent/US7442801B2/en not_active Expired - Fee Related
- 2004-02-03 CN CN2009101414107A patent/CN101701010B/zh not_active Expired - Fee Related
- 2004-02-03 CN CNA2004800076819A patent/CN1761654A/zh active Pending
- 2004-02-03 WO PCT/JP2004/001071 patent/WO2004085405A1/ja active Application Filing
- 2004-02-03 ZA ZA200506245A patent/ZA200506245B/en unknown
- 2004-02-03 PT PT04707666T patent/PT1607390E/pt unknown
- 2004-02-03 AU AU2004224033A patent/AU2004224033B2/en not_active Ceased
- 2004-02-03 CN CN200910141408A patent/CN101704784A/zh active Pending
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010060379A1 (zh) * | 2008-11-28 | 2010-06-03 | 中国中化集团公司 | 具有含氮五元杂环的醚类化合物及其应用 |
CN102216294A (zh) * | 2008-11-28 | 2011-10-12 | 中国中化股份有限公司 | 具有含氮五元杂环的醚类化合物及其应用 |
US8222280B2 (en) | 2008-11-28 | 2012-07-17 | Sinochem Corporation | Ether compounds with nitrogen-containing 5-member heterocycle and uses thereof |
CN102216294B (zh) * | 2008-11-28 | 2013-08-28 | 中国中化股份有限公司 | 具有含氮五元杂环的醚类化合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
WO2004085405A1 (ja) | 2004-10-07 |
CN101704784A (zh) | 2010-05-12 |
TW200505338A (en) | 2005-02-16 |
PT1607390E (pt) | 2010-10-12 |
EP1607390B1 (en) | 2010-09-15 |
CN101712651A (zh) | 2010-05-26 |
MXPA05010144A (es) | 2005-11-16 |
EP1607390A4 (en) | 2008-03-26 |
CN101701010A (zh) | 2010-05-05 |
BRPI0408755A (pt) | 2006-03-28 |
CN101701010B (zh) | 2012-06-13 |
KR101021452B1 (ko) | 2011-03-16 |
US20060142367A1 (en) | 2006-06-29 |
IL170056A (en) | 2010-11-30 |
US7442801B2 (en) | 2008-10-28 |
DE602004029143D1 (en) | 2010-10-28 |
ZA200506245B (en) | 2007-09-26 |
KR20050111609A (ko) | 2005-11-25 |
TWI321036B (zh) | 2010-03-01 |
EG24798A (en) | 2010-09-15 |
AU2004224033A1 (en) | 2004-10-07 |
AU2004224033B2 (en) | 2009-10-22 |
ES2349635T3 (es) | 2011-01-07 |
EP1607390A1 (en) | 2005-12-21 |
ATE481390T1 (de) | 2010-10-15 |
CO5611064A2 (es) | 2006-02-28 |
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