CN100339352C - 2-和2,5-取代的苯基酮烯醇 - Google Patents
2-和2,5-取代的苯基酮烯醇 Download PDFInfo
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- CN100339352C CN100339352C CN200410100062.6A CN200410100062A CN100339352C CN 100339352 C CN100339352 C CN 100339352C CN 200410100062 A CN200410100062 A CN 200410100062A CN 100339352 C CN100339352 C CN 100339352C
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- 150000001875 compounds Chemical class 0.000 claims description 212
- 239000000460 chlorine Substances 0.000 claims description 69
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 abstract description 117
- 230000008569 process Effects 0.000 abstract description 14
- 125000004122 cyclic group Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- -1 phenyl ketone enol Chemical class 0.000 description 253
- 239000000203 mixture Substances 0.000 description 84
- 238000006243 chemical reaction Methods 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- 239000001301 oxygen Substances 0.000 description 56
- 229910052760 oxygen Inorganic materials 0.000 description 56
- 238000002360 preparation method Methods 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
- 239000002253 acid Substances 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 45
- 239000005864 Sulphur Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000002585 base Substances 0.000 description 36
- 239000003921 oil Substances 0.000 description 36
- 239000003795 chemical substances by application Substances 0.000 description 35
- 125000004093 cyano group Chemical group *C#N 0.000 description 35
- 125000003545 alkoxy group Chemical group 0.000 description 33
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- 239000001257 hydrogen Substances 0.000 description 27
- 229910052739 hydrogen Inorganic materials 0.000 description 27
- 239000003999 initiator Substances 0.000 description 27
- 239000000463 material Substances 0.000 description 25
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000011230 binding agent Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000003995 emulsifying agent Substances 0.000 description 22
- 230000000694 effects Effects 0.000 description 19
- 125000005843 halogen group Chemical group 0.000 description 19
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 239000003513 alkali Substances 0.000 description 15
- 150000003851 azoles Chemical class 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 125000001544 thienyl group Chemical group 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 241000238631 Hexapoda Species 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 11
- 150000002170 ethers Chemical class 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 238000006073 displacement reaction Methods 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 125000004076 pyridyl group Chemical group 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- 239000000370 acceptor Substances 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000002541 furyl group Chemical group 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229920000151 polyglycol Polymers 0.000 description 9
- 239000010695 polyglycol Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 240000007124 Brassica oleracea Species 0.000 description 8
- 241000209094 Oryza Species 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 150000003818 basic metals Chemical group 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 7
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- 241001674048 Phthiraptera Species 0.000 description 7
- 241000500437 Plutella xylostella Species 0.000 description 7
- 150000001266 acyl halides Chemical class 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000013459 approach Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 150000001733 carboxylic acid esters Chemical class 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
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- 239000004215 Carbon black (E152) Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
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- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D405/00—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
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Abstract
本发明涉及式(I)的新的苯基取代的环酮烯醇,其中Het代表下面基团之一,A,B,D,G,X和Z各自如说明书定义。本发明还涉及多种制备这些化合物的方法和中间体,及其作为杀虫剂的用途。
Description
本申请是申请号为CN97198554.5(国际申请日为1997年7月23日)的进入国家阶段的PCT申请的分案申请。
本发明涉及新的苯基取代的环酮烯醇,其多种制备方法和中间体,以及其作为杀虫剂的用途。
已经公开过一些苯基取代的环酮烯醇作为杀昆虫剂,杀螨剂和/或除草剂是有活性的。
也已知1H-芳基吡咯烷二酮衍生物
(EP-A-456 063,EP-A-521 334,EP-A-596 298,EP-A-613 884,EP-A-613 885,DE 44 40 594,WO 94/01 997,WO 95/01 358,WO 95/26 954,WO 95/20 572,EP-A-0 668 267,WO 96/25 395,WO 96/35 664,WO 97/01 535和WO 97/02 243)
已知一些取代的Δ3-二氢呋喃-2-酮衍生物具有除草性能(参见DE-A-4014420)。用作起始物的季酮酸衍生物(例如3-(2-甲基-苯基)-4-羟基-5-(4-氟代苯基)-Δ3-二氢呋喃-2-酮)的合成同样描述于DE-A-4014420。从公开物Campbell等,J.Chem.Soc.,PerkinTran.1,
1985,(8)1567-76得知没有详细描述杀昆虫和/或杀螨活性的类似结构的化合物。此外,具有除草,杀螨和杀昆虫性能的3-芳基-Δ3-二氢呋喃酮衍生物公开于EP-A528156,EP-A0647637,WO95/26345,WO96/20196,WO96/25395,WO96/35664,WO97/01535和WO97/02243中。
一些苯环没有被取代的苯基-吡喃酮衍生物已经被公开(参见A.M.Chirazi,T.Kappe和E.Ziegler,Arch.Pharm.309,558(1976)和K.-H.Boltze和K.Heidenbluth,Chem.Ber.
91,2849),没有指明这些化合物作为杀虫剂的可能的实用性。苯环被取代并且具有除草,杀螨和杀虫性能的苯基-吡喃酮衍生物公开于EP-A-588137,WO96/25395,WO96/35664,WO97/01535和WO97/02243中。
但是杀螨活性和杀虫活性和/或作用范围,和/或植物,特别是作物对已知化合物的耐受性并不总是令人满意。
因此,本发明提供式(I)化合物
其中
X代表卤素,烷基,链烯基,炔烃基,烷氧基,苄基氧基,卤代烷基,卤代烷氧基,氰基或硝基,
Z代表氢,氨基,卤素,烷基,烷氧基,卤代烷基,卤代烷氧基,羟基,氰基,硝基或者各自任选被取代的苯氧基,苯硫基,5-或6-元杂芳基氧基,5-或6-元杂芳基硫基,苯基烷氧基或苯基烷硫基,和
Het代表下面的基团之一
其中
A代表各自任选被取代的选自烷基,链烯基,烷氧基烷基,多烷氧基烷基和烷硫基烷基的基团,代表各自饱和的或不饱和的和任选被取代的环烷基或杂环基或者代表各自任选被卤素-,烷基-,卤代烷基-,烷氧基-,卤代烷氧基-,氰基-或硝基-取代的芳基,芳基烷基或杂芳基,
B代表烷基或烷氧基烷基,或者
A和B与它们所连接的碳原子一起代表饱和的或不饱和的,任选被取代的碳环或杂环,
D代表氢或者代表任选被取代的选自烷基,链烯基,炔烃基,烷氧基烷基,多烷氧基烷基,烷硫基烷基,饱和的或不饱和的环烷基,饱和的或不饱和的杂环基,芳基烷基,芳基,杂芳基烷基或杂芳基的基团,或者
A和D与它们所连接的原子一起代表各自任选被取代的碳环或杂环,
G代表氢(a)或者代表下面的基团之一
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,
M代表氧或硫,
R1代表各自任选被卤素-取代的烷基,链烯基,烷氧基烷基,烷硫基烷基或多烷氧基烷基或者代表各自任选被卤素-,烷基-或烷氧基-取代的环烷基或杂环基或者代表各自任选被取代的苯基,苯基烷基,杂芳基,苯氧基烷基或杂芳基氧基烷基,
R2代表各自任选被卤素-取代的烷基,链烯基,烷氧基烷基或多烷氧基烷基或者代表各自任选被取代的环烷基,苯基或苄基,
R3,R4和R5各自独立地代表各自任选被卤素-取代的烷基,烷氧基,烷基氨基,二烷基氨基,烷基硫基,链烯基硫基或环烷基硫基或者代表各自任选被取代的苯基,苄基,苯氧基或苯硫基,
R6和R7各自独立地代表氢,代表各自任选被卤素-取代的烷基,环烷基,链烯基,烷氧基,烷氧基烷基,代表各自任选被取代的苯基或苄基,或者与它们所连接的氮原子一起形成任选含有氧或硫的任选被取代的环。
根据取代基的性质,式(I)化合物也可以以几何异构体和/或旋光异构体和不同组成的异构体混合物存在,如果适当,异构体混合物可以用常规方法分离。纯的异构体和异构体混合物,其制备和应用,含有它们的组合物都是本发明主题的一部分。下面为了简化起见,总是提到式(I)化合物,但是它意指纯的化合物和如果适当,具有不同比例异构体化合物的混合物。
包括基团Het定义(1)至(4),得到下面的主结构(I-1)至(I-4):
其中
A,B,D,G,X和Z各自如上定义。
如果Het代表基团(1),则得到包括基团G不同定义(a),(b),(c),(d),(e),(f)和(g)的下面主结构(I-1-a)至(I-1-g)
其中
A,B,E,L,M,X,Z,R1,R2,R3,R4,R5,R6和R7各自如上定义。
如果Het代表基团(2),则得到包括基团G不同定义(a),(b),(c),(d),(e),(f)和(g)的下面主结构(I-2-a)至(I-2-g)
其中
A,B,E,L,M,X,Z,R1,R2,R3,R4,R5,R6和R7各自如上定义。
如果Het代表基团(3),则得到包括基团G不同定义(a),(b),(c),(d),(e),(f)和(g)的下面主结构(I-3-a)至(I-3-g)
其中
A,B,E,L,M,X,Z,R1,R2,R3,R4,R5,R6和R7各自如上定义。
根据取代基G的位置,式(I-4)化合物可以以两种异构体形式式(I-4)a和(I-4)b存在
其以式(I-4)中的虚线表示。
式(I-4)a和(I-4)b化合物可以以混合物和其纯的异构体的形式存在。如果需要,式(I-4)a和(I-4)b化合物的混合物可以以本身已知的方式,通过物理方法来分离,例如通过色谱方法。
为了更清楚,下面各种情况下只给出了可能的异构体之一。但这并不排除化合物可以任选以异构体混合物形式或者以各异构体形式存在的可能性。
如果Het代表基团(4),则得到包括基团G不同定义(a),(b),(c),(d),(e),(f)和(g)的下面主结构(I-4-a)至(I-4-g)
其中
A,D,E,L,M,X,Z,R1,R2,R3,R4,R5,R6和R7各自如上定义。
此外,发现通过下面描述的方法之一得到了式(I)新的化合物:
(A)在稀释剂存在下和在碱存在下,通过式(II)化合物的分子内缩合,得到式(I-1-a)化合物
其中
A,B,X和Z各自如上定义,
其中
A,B,X和Z各自如上定义,
和
R8代表烷基(优选C1-C6烷基)。
(B)此外发现在稀释剂存在下和在碱存在下,通过式(III)化合物的分子内缩合,得到式(I-2-a)化合物
其中
A,B,X和Z各自如上定义,
其中
A,B,X,Z和R8各自如上定义。
(C)此外发现如果适当在稀释剂存在下和在酸存在下,通过式(IV)化合物的分子内环化,得到式(I-3-a)化合物
其中
A,B,X和Z各自如上定义,
其中
A,B,X,Z和R8各自如上定义,和
W代表氢,卤素,烷基(优选C1-C6-烷基)或烷氧基(优选C1-C8-烷氧基)。
(D)此外发现,如果适当在稀释剂存在下和如果适当在酸受体存在下,通过使式(V)化合物或其式(Va)甲硅烷基烯醇醚与式(VI)化合物反应,得到式(I-4-a)化合物
其中
A,D,X和Z各自如上定义,
其中
A和D各自如上定义,
其中
A和D各自如上定义,和
R8’代表烷基(优选甲基),
其中
X和Z各自如上定义,和
Hal代表卤素(优选氯或溴)。
此外发现,
(E)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,通过使其中A,B,D,X和Z各自如上定义的上述式(I-1-a)至(I-4-a)化合物进行下面的反应,得到其中A,B,D,R1,X和Z各自如上定义的上述式(I-1-b)至(I-4-b)化合物
α)与式(VII)酰卤反应
其中
R1如上定义,和
Hal代表卤素(特别是氯或溴),
或者
β)与式(VIII)酸酐反应
R1-CO-O-CO-R1 (VIII)
其中
R1如上定义;
(F)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,通过使其中A,B,D,X和Z各自如上定义的上述式(I-1-a)至(I-4-a)化合物各自与式(IX)的氯甲酸酯或氯甲酸硫酯反应,得到其中A,B,D,R2,M,X和Z各自如上定义并且L代表氧的上述式(I-1-c)至(I-4-c)化合物
R2-M-CO-Cl (IX)
其中
R2和M各自如上定义;
(G)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,通过使其中A,B,D,X和Z各自如上定义的上述式(I-1-a)至(I-4-a)化合物各自与式(X)的氯一硫代甲酸酯或氯二硫代甲酸酯反应,得到其中A,B,D,R2,M,X和Z各自如上定义并且L代表硫的上述式(I-1-c)至(I-4-c)化合物
其中
R2和M各自如上定义;
(H)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,通过使其中A,B,D,X和Z各自如上定义的上述式(I-1-a)至(I-4-a)化合物各自与式(XII)的磺酰氯反应,得到其中A,B,D,R3,X和Z各自如上定义的上述式(I-1-d)至(I-4-d)化合物
R3-SO2-Cl (XII)
其中
R3如上定义;
(I)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,通过使其中A,B,D,X和Z各自如上定义的上述式(I-1-a)至(I-4-a)化合物各自与式(XIII)的磷化合物反应,得到其中A,B,D,L,R4,R5,X和Z各自如上定义的上述式(I-1-e)至(I-4-e)化合物
其中
L,R4和R5各自如上定义,和
Hal代表卤素(特别是氯或溴);
(J)如果适当在稀释剂存在下,通过使其中A,B,D,X和Z各自如上定义的式(I-1-a)至(I-4-a)化合物各自与式(XIV)或(XV)的金属化合物或胺反应,得到其中A,B,D,E,X和Z各自如上定义的上述式(I-1-f)至(I-4-f)化合物
Me(OR10)t (XIV)
其中
Me代表一价或二价金属(优选碱金属或碱土金属,例如锂,钠,钾,镁或钙),
t代表数1或2,和
R10,R11,R12各自独立地代表氢或烷基(优选C1-C8-烷基);(K)通过使其中A,B,D,X和Z各自如上定义的上述式(I-1-a)至(I-4-a)化合物在下面各情况下反应,得到其中A,B,D,L,R6,R7,X和Z各自如上定义的上述式(I-1-g)至(I-4-g)化合物:
α)如果适当在稀释剂存在下和如果适当在催化剂存在下,与式(XVI)的异氰酸酯或异硫代氰酸酯反应
R6-N=C=L (XVI)
其中
R6和L各自如上定义,
或者
β)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,与式(XVII)的氨基甲酰氯或硫代氨基甲酰氯反应
其中
L,R6和R7各自如上定义。
此外发现,式(I)新的化合物作为杀虫剂,优选作为杀昆虫剂和杀螨剂具有特别好的活性,另外,植物,特别是农作物对其有非常好的耐受性。
式(I)提供本发明化合物的一般定义。下面详细描述上文和下文提到的结构式中所示基团的优选取代基或范围:
X优选代表卤素,C1-C6-烷基,C2-C6-链烯基,C2-C6-炔烃基,C1-C6-烷氧基,苄基氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,氰基或硝基,
Z优选代表氢,氨基,卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,羟基,氰基,硝基,或者各自任选被卤素-,C1-C4-烷基-,C1-C4-烷氧基-,C1-C4-卤代烷基-,C1-C4-卤代烷氧基-,硝基-或氰基-取代的苯氧基,苯硫基,噻唑基氧基,吡啶基氧基,嘧啶基氧基,吡唑基氧基,苯基-C1-C4-烷基氧基或苯基-C1-C7-烷基硫基。
Het优选代表下面的基团之一
其中
A优选代表各自任选被卤素-取代的C1-C12-烷基,C2-C8-链烯基,C1-C10-烷氧基-C1-C8-烷基,多-C1-C8-烷氧基-C1-C8-烷基或C1-C10-烷硫基-C1-C6-烷基,优选代表任选被卤素-,C1-C6-烷基-或C1-C6-烷氧基-取代的C3-C8-环烷基,其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换,或者优选代表各自任选被卤素-,C1-C6-烷基-,C1-C6-卤代烷基-,C1-C6-烷氧基-,C1-C6-卤代烷氧基-,氰基-或硝基-取代的苯基,萘基,苯基-C1-C6-烷基,萘基-C1-C6-烷基或者具有5或6个成环原子和1-3个选自氧,硫和氮的杂原子的杂芳基(特别是选自呋喃基,吡啶基,咪唑基,三唑基,吡唑基,吲哚基,噻唑基和噻吩基)。
B优选代表C1-C12-烷基或C1-C8-烷氧基-C1-C6-烷基,或者
A,B与它们所连接的碳原子一起优选代表其中各种情况下一个亚甲基任选被氧或硫置换,并且其任选被C1-C8-烷基,C3-C10-环烷基,C1-C8-卤代烷基,C1-C8-烷氧基,C1-C8-烷硫基,卤素或苯基取代的C3-C10-环烷基或C5-C10-环烯基,或者
A,B与它们所连接的碳原子一起优选代表C5-C6-环烷基,其被任选含有一个或两个不直接相邻的氧和/或硫原子的亚烷基二基取代,或者被亚烷基二氧基或亚烷基二硫基取代,其与所连接的碳原子形成另外一个5-或8-员环,或者
A,B与它们所连接的碳原子一起优选代表C3-C8-环烷基或C5-C8-环烯基,其中两个碳原子通过各自任选被C1-C6-烷基-,C1-C6-烷氧基-或卤素-取代的C3-C6-链烷二基,C3-C6-链烯烃二基或C4-C6-链烷二烯二基相互连接,在各种情况下一个亚甲基任选被氧或硫置换。
D优选代表氢,优选代表各自任选被卤素-取代的C1-C12-烷基,C3-C8-链烯基,C3-C8-炔烃基,C1-C10-烷氧基-C2-C8-烷基,多-C1-C8-烷氧基-C2-C8-烷基或C1-C10-烷硫基-C2-C8-烷基,优选代表任选被卤素-,C1-C4-烷基,C1-C4-烷氧基或C1-C4-卤代烷基-取代的、其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换的C3-C8-环烷基,或者优选代表各自任选被卤素-,C1-C6-烷基-,C1-C6-卤代烷基-,C1-C6-烷氧基-,C1-C6-卤代烷氧基-,氰基-或硝基-取代的苯基,具有5或6个成环原子和1或2个选自氧,硫和氮的杂原子的杂芳基(特别是选自呋喃基,咪唑基,吡啶基,噻唑基,吡唑基,嘧啶基,吡咯基,噻吩基和三唑基),苯基-C1-C6-烷基或者具有5或6个成环原子和1或2个选自氧,硫和氮的杂原子的杂芳基-C1-C6-烷基(特别选自呋喃基-,咪唑基-,吡啶基-,噻唑基-,吡唑基-,嘧啶基-,吡咯基-,噻吩基-和三唑基-C1-C6-烷基),或者
A和D一起优选代表C3-C6-链烷二基,C3-C6-链烯烃二基或C4-C6-链烷二烯二基,其中各自任选地一个亚甲基被氧或硫置换,并且其各自任选被卤素或者被各自任选地被卤素-取代的C1-C10-烷基,C1-C6-烷氧基,C1-C6-烷硫基,C3-C7-环烷基,苯基或苄基氧基取代,或者各自任选被另外一个形成稠合环的C3-C6-链烷二基,C3-C6-链烯烃二基或C4-C6-链烷二烯二基取代,其中各自任选地一个亚甲基被氧或硫取代,而且其任选被C1-C6-烷基取代,或者
A和D一起代表各种情况下任选包含下面基团之一的C3-C6-链烷二基或C3-C6-链烯烃二基
G优选代表氢(a)或者代表下面的基团之一
E(f)或
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫,
R1优选代表各自任选被卤素-取代的C1-C20-烷基,C2-C20-链烯基,C1-C8-烷氧基-C1-C8-烷基,C1-C8-烷硫基-C1-C8-烷基或多-C1-C8-烷氧基-C1-C8-烷基或者优选代表其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换的任选被卤素,C1-C6-烷基或C1-C6-烷氧基取代的C3-C8环烷基,
优选代表任选被卤素-,氰基-,硝基-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C6-卤代烷基-,C1-C6-卤代烷氧基-,C1-C6-烷硫基-或C1-C6-烷基磺酰基-取代的苯基,
优选代表任选被卤素-,硝基-,氰基-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C6-卤代烷基-或C1-C6-卤代烷氧基-取代的苯基-C1-C6-烷基,优选代表任选被卤素-或C1-C6-烷基-取代的5-或6-元具有1或2个选自氧,硫和氮的杂原子的杂芳基(特别是选自吡唑基,噻唑基,吡啶基,嘧啶基,呋喃基和噻吩基),
优选代表任选被卤素-或C1-C6-烷基-取代的苯氧基-C1-C6-烷基,或者
优选代表任选被卤素-,氨基-或C1-C6-烷基-取代的具有1或2个选自氧,硫和氮的杂原子的5-或6-元杂芳基氧基-C1-C6-烷基(特别选自吡啶基氧基-C1-C6-烷基,嘧啶基氧基-C1-C6-烷基和噻唑基氧基-C1-C6-烷基)。
R2优选代表各自任选被卤素-取代的C1-C20-烷基,C2-C20-链烯基,C1-C8-烷氧基-C2-C8-烷基或多C1-C8-烷氧基-C2-C8-烷基,优选代表任选被卤素-,C1-C6-烷基或C1-C6-烷氧基取代的C3-C8环烷基,或者
优选代表各自任选被卤素-,氰基-,硝基-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C6-卤代烷基-或C1-C6-卤代烷氧基-取代的苯基或苄基。R3优选代表任选被卤素-取代的C1-C8-烷基或者各自任选被卤素-,C1-C6-烷基-,C1-C6-烷氧基~,C1-C4-卤代烷基-,C1-C4-卤代烷氧基-,氰基-或硝基取代的苯基或苄基。
R4和R5各自独立地优选代表任选被卤素-取代的C1-C8-烷基,C1-C8-烷氧基,C1-C8-烷基氨基,二(C1-C8-烷基)氨基,C1-C8-烷基硫基或C3-C8-链烯基硫基,或者优选代表各自任选被卤素-,硝基-,氰基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,C1-C4-烷硫基-,C1-C4-卤代烷硫基-,C1-C4-烷基-或C1-C4-卤代烷基-取代的苯基,苯氧基或苯硫基。
R6和R7各自独立地优选代表氢,优选代表各自任选被卤素-取代的C1-C8-烷基,C3-C8-环烷基,C1-C8-烷氧基,C3-C8-链烯基或C1-C8-烷氧基C2-C8-烷基,优选代表各自任选被卤素-,C1-C8-烷基-,C1-C8-卤代烷基-或C1-C8-烷氧基-取代的苯基或苄基,或者一起优选代表其中任选地一个亚甲基被氧或硫置换的任选被C1-C6-烷基取代的C3-C6-亚烷基。
R13优选代表氢或各自任选被卤素-取代的C1-C8-烷基或C1-C8-烷氧基,优选代表其中任选地一个亚甲基被氧或硫置换的任选被卤素-,C1-C4-烷基-或C1-C4-烷氧基-取代的C3-C8-环烷基,或者优选代表各自任选被卤素-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C4-卤代烷基-,C1-C4-卤代烷氧基-,氰基-或硝基-取代的苯基,苯基-C1-C4-烷基或苯基-C1-C4-烷氧基。
R14优选代表氢或C1-C8-烷基,或者
R13和R14一起优选代表C4-C6-链烷二基。
R15和R16是相同或不同的,并且各自代表C1-C6-烷基,或者
R15和R16一起优选代表C2-C4-链烷二基,其任选被C1-C6-烷基或者被任选被卤素-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,硝基-或氰基-取代的苯基取代。
R17和R18各自独立地优选代表氢,优选代表任选被卤素-取代的C1-C8-烷基,或者优选代表任选被卤素-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C4-卤代烷基-,C1-C4-卤代烷氧基-,硝基-或氰基-取代的苯基,
或者
R17和R18与它们所连接的碳原子一起优选代表其中任选地一个亚甲基被氧或硫置换的任选被C1-C4-烷基-取代的C5-C7-环烷基。
R19和R20各自独立地优选代表C1-C10-烷基,C2-C10-链烯基,C1-C10-烷氧基,C1-C10-烷基氨基,C3-C10-链烯基氨基,二-(C1-C10-烷基)-氨基或二-(C3-C10-链烯基)-氨基。
X特别优选代表氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,苄基氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,氰基或硝基。
Z特别优选代表氢,氨基,氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,羟基,氰基,硝基,或者各自任选被氟-,氯-,溴-,C1-C4-烷基-,C1-C4-烷氧基-,C1-C2-卤代烷基-,C1-C2-卤代烷氧基-,硝基-或氰基-取代的苯氧基或苄氧基。
Het特别优选代表下面的基团之一
A特别优选代表各自任选被氟-或氯-取代的C1-C10-烷基,C2-C6-链烯基,C1-C8-烷氧基-C1-C6-烷基,多-C1-C6-烷氧基-C1-C6-烷基或C1-C8-烷硫基-C1-C6-烷基或者特别优选代表任选被氟-,氯-,C1-C4-烷基-或C1-C4-烷氧基-取代的其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换的C3-C7-环烷基,或者特别优选代表各自任选被氟-,氯-,溴-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,氰基-或硝基-取代的苯基,呋喃基,吡啶基,咪唑基,三唑基,吡唑基,吲哚基,噻唑基,噻吩基或苯基-C1-C4-烷基。
B特别优选代表C1-C10-烷基或C1-C6-烷氧基-C1-C4-烷基,或者A,B与它们所连接的碳原子一起特别优选代表其中各种情况下一个亚甲基任选被氧或硫置换,并且其任选被C1-C6-烷基,C3-C8-环烷基,C1-C3-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,氟,氯或苯基取代的C3-C8-环烷基或C5-C8-环烯基,或者
A,B与它们所连接的碳原子一起特别优选代表C5-C6-环烷基,其被任选含有一个或两个不直接相邻的氧或硫原子的亚烷基二基取代,或者被亚烷基二氧基或亚烷基二硫醇基取代,其与所连接的碳原子一起形成另一个5-至7-元环,或者
A,B与它们所连接的碳原子一起特别优选代表C3-C6-环烷基或C5-C6-环烯基,其中两个碳原子通过各自任选被C1-C4-烷基-,C1-C4-烷氧基-,氟-,氯-或溴-取代的C3-C5-链烷二基或C3-C5-链烯烃二基相互连接,其中在每种情况下一个亚甲基任选被氧或硫置换,或者通过丁二烯二基相互连接。
D特别优选代表氢,特别优选代表各自任选被氟-或氯-取代的C1-C6-烷基或C1-C6-烷氧基,特别优选代表各自任选被氟-,氯-,C1-C4-烷基,C1-C4-烷氧基或C1-C2-卤代烷基-取代的,其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换的C3-C7-环烷基,或者特别优选代表各自任选被氟-,氯-,溴-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,氰基-或硝基-取代的苯基,呋喃基,咪唑基,吡啶基,噻唑基,吡唑基,嘧啶基,吡咯基,噻吩基,三唑基或苯基-C1-C4-烷基,或者
A和D一起特别优选代表C3-C5-链烷二基或C3-C5-链烯烃二基,其中各种情况下任选地一个亚甲基被氧或硫置换,并且其任选被氟,氯或者被各自任选地被氟-或氯-取代的C1-C6-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C3-C6-环烷基,苯基或苄基氧基取代,或者其中各种情况下任选地含有下面基团之一:
G特别优选代表氢(a)或者代表下面的基团之一
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫,
R1特别优选代表各自任选被氟-或氯-取代的C1-C16-烷基,C2-C16-链烯基,C1-C6-烷氧基-C1-C6-烷基,C1-C6-烷硫基-C1-C6-烷基或多-C1-C6-烷氧基-C1-C6-烷基,或者特别优选代表其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换的任选被氟-,氯-,C1-C5-烷基-或C1-C5-烷氧基-取代的C3-C7-环烷基,
特别优选代表任选被氟-,氯-,溴-,氰基-,硝基-,C1-C4-烷基-,C1-C4-烷氧基-,C1-C3-卤代烷基-,C1-C3-卤代烷氧基-,C1-C4-烷硫基-或C1-C4-烷基磺酰基-取代的苯基,
特别优选代表任选被氟-,氯-,溴-,C1-C4-烷基-,C1-C4-烷氧基-,C1-C3-卤代烷基-或C1-C3-卤代烷氧基-取代的苯基-C1-C4-烷基,特别优选代表各自任选被氟-,氯-,溴-或C1-C4-烷基-取代的吡唑基,噻唑基,吡啶基,嘧啶基,呋喃基或噻吩基,
特别优选代表任选被氟-,氯-,溴-或C1-C4-烷基-取代的苯氧基-C1-C5-烷基,或者
特别优选代表各自任选被氟-,氯-,溴-,氨基-或C1-C4-烷基-取代的吡啶基氧基-C1-C5-烷基,嘧啶基氧基-C1-C5-烷基或噻唑基氧基-C1-C5-烷基。
R2特别优选代表各自任选被氟-或氯-取代的C1-C16-烷基,C2-C16-链烯基,C1-C6-烷氧基-C2-C6-烷基或多C1-C6-烷氧基-C2-C6-烷基,
特别优选代表任选被氟-,氯-,C1-C4-烷基-或C1-C4-烷氧基-取代的C3-C7-环烷基,或者
特别优选代表各自任选被氟-,氯-,溴-,氰基-,硝基-,C1-C4-烷基-,C1-C3-烷氧基-,C1-C3-卤代烷基-或C1-C3-卤代烷氧基-取代的苯基或苄基。
R3特别优选代表任选被氟-或氯-取代的C1-C6-烷基或者各自任选被氟-,氯-,溴-,C1-C4-烷基-,C1-C4-烷氧基-,C1-C2-卤代烷基-,C1-C2-卤代烷氧基-,氰基-或硝基-取代的苯基或苄基。
R4和R5各自独立地特别优选代表各自任选被氟-或氯-取代的C1-C6-烷基,C1-C6-烷氧基,C1-C6-烷基氨基,二-(C1-C6-烷基)-氨基,C1-C6-烷硫基或C3-C4-链烯基硫基,或者特别优选代表各自任选被氟-,氯-,溴-,硝基-,氰基-,C1-C3-烷氧基-,C1-C3-卤代烷氧基-,C1-C3-烷硫基-,C1-C3-卤代烷硫基-,C1-C3-烷基-或C1-C3-卤代烷基-取代的苯基,苯氧基或苯硫基。
R6和R7各自独立地特别优选代表氢,特别优选代表各自任选被氟-或氯-取代的C1-C6-烷基,C3-C6-环烷基,C1-C6-烷氧基,C3-C6-链烯基或C1-C6-烷氧基C2-C6-烷基,特别优选代表各自任选被氟-,氯-,溴-,C1-C5-烷基-,C1-C5-卤代烷基-或C1-C5-烷氧基-取代的苯基或苄基,或者一起特别优选代表其中任选地一个亚甲基被氧-或硫-置换的任选被C1-C4-烷基取代的C3-C6-亚烷基。
R13特别优选代表氢或各自任选被氟-或氯-取代的C1-C6-烷基或C1-C6-烷氧基,特别优选代表其中任选地一个亚甲基被氧或硫置换的任选被氟-,C1-C2-烷基-或C1-C2-烷氧基-取代的C3-C7-环烷基,或者特别优选代表各自任选被氟-,氯-,溴-,C1-C5-烷基-,C1-C5-烷氧基-,C1-C2-卤代烷基-,C1-C2-卤代烷氧基-,氰基-或硝基-取代的苯基,苯基-C1-C3-烷基或苯基-C1-C2-烷氧基。
R14特别优选代表氢或C1-C6-烷基,或者
R13和R14一起特别优选代表C4-C6-链烷二基。
R15和R16是相同或不同的,并且各自特别优选代表C1-C4-烷基,或者
R15和R16一起特别优选代表C2-C3-链烷二基,其任选被C1-C4-烷基或者被任选被氟-,氯-,溴-,C1-C2-烷基-,C1-C2-卤代烷基-,C1-C2-烷氧基-,C1-C2-卤代烷氧基-,硝基-或氰基-取代的苯基取代。
X非常特别优选代表氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,异丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基,三氟甲基,三氟甲氧基,二氟甲氧基,氰基或硝基,
Z非常特别优选代表氢,氨基,氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,异丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基,三氟甲基,三氟甲氧基,二氟甲氧基,氰基或硝基。
Het非常特别优选代表下面的基团之一
A非常特别优选代表各自任选被氟-或氯-取代的C1-C8-烷基,C2-C4-链烯基,C1-C6-烷氧基-C1-C4-烷基,多-C1-C4-烷氧基-C1-C4-烷基或C1-C6-烷硫基-C1-C4-烷基,或者非常特别优选代表任选被氟-,氯-,甲基-或甲氧基-取代的其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换的C3-C6-环烷基,或者非常特别优选代表各自任选被氟-,氯-,溴-,甲基-,乙基-,正丙基-,异丙基-,甲氧基-,乙氧基-,三氟甲基-,三氟甲氧基-,氰基-或硝基-取代的苯基,吡啶基或苄基。
B非常特别优选代表C1-C8-烷基或C1-C4-烷氧基-C1-C2-烷基或A,B和它们所连接的碳原子一起非常特别优选代表C3-C8-环烷基或C5-C8-环烯基,其中各种情况下任选地一个亚甲基被氧或硫置换,并且其任选地被甲基,乙基,正丙基,异丙基,丁基,异丁基,仲丁基,叔丁基,环己基,三氟甲基,甲氧基,乙氧基,正丙氧基,异丙氧基,丁氧基,异丁氧基,仲丁氧基,叔丁氧基,甲硫基,乙硫基,氟,氯或苯基取代,或A,B和它们所连接的碳原子一起非常特别优选代表C3-C6-环烷基或C5-C6-环烯基,其中两个碳原子通过其中各种情况下任选地一个亚甲基被氧或硫置换的C3-C4-链烷二基或C3-C4-链烯二基连接在一起,或者通过丁二烯二基连接在一起。
D非常特别优选代表氢,非常特别优选代表各自任选被氟-取代的C1-C4-烷基或C1-C4-烷氧基或C3-C6-环烷基,其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换,或者非常特别优选代表各自任选地被氟-,氯-,溴-,甲基-,乙基-,正丙基-,异丙基-,甲氧基-,乙氧基-,三氟甲基-,三氟甲氧基-,氰基-或硝基-取代的苯基,呋喃基,吡啶基,噻吩基或苄基,
或者
A和D一起非常特别优选代表C3-C5-链烷二基或C3-C5-链烯烃二基,其中各种情况下任选地一个亚甲基被氧或硫置换,并且其任选被氟,氯或者被各自任选地被氟-或氯-取代的C1-C6-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C3-C6-环烷基,苯基或苄基氧基取代。
G非常特别优选代表氢(a)或者代表下面的基团之一
E(f)或
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫。
R1非常特别优选代表各自任选被氟-或氯-取代的C1-C14-烷基,C2-C14-链烯基,C1-C4-烷氧基-C1-C6-烷基,C1-C4-烷硫基-C1-C6-烷基,多-C1-C4-烷氧基-C1-C4-烷基或者非常特别优选代表任选被氟-,氯-,甲基-,乙基-,正丙基-,异丙基-,正丁基-,异丁基-,叔丁基-,甲氧基-,乙氧基-,正丙氧基-或异丙氧基-取代的其中任选地一个或两个不直接相邻的亚甲基被氧和/或硫置换的C3-C6-环烷基,非常特别优选代表任选被氟-,氯-,溴-,氰基-,硝基-,甲基-,乙基-,正丙基-,异丙基-,甲氧基-,乙氧基-,三氟甲基-,三氟甲氧基-,甲硫基-,乙硫基-,甲基磺酰基-或乙基磺酰基-取代的苯基,
非常特别优选代表任选被氟-,氯-,溴-,甲基-,乙基-,正丙基-,异丙基-,甲氧基-,乙氧基-,三氟甲基-或三氟甲氧基-取代的苄基,
非常特别优选代表各自任选被氟-,氯-,溴-,甲基-或乙基-取代的呋喃基,噻吩基或吡啶基,
非常特别优选代表任选被氟-,氯-,甲基-或乙基-取代的苯氧基-C1-C4-烷基,或者
非常特别优选代表各自任选被氟-,氯-,氨基-,甲基-或乙基-取代的吡啶基氧基-C1-C4-烷基,嘧啶基氧基-C1-C4-烷基或噻唑基氧基-C1-C4-烷基。
R2非常特别优选代表各自任选被氟-或氯-取代的C1-C14-烷基,C2-C14-链烯基,C1-C4-烷氧基-C2-C6-烷基或多-C1-C4-烷氧基-C2-C6-烷基,
非常特别优选代表任选被氟-,氯-,甲基-,乙基-,正丙基-,异丙基-或甲氧基-取代的C3-C6-环烷基,
或者非常特别优选代表各自任选被氟-,氯-,氰基-,硝基-,甲基-,乙基-,正丙基-,异丙基-,甲氧基-,乙氧基-,三氟甲基-或三氟甲氧基-取代的苯基或苄基。
R3非常特别优选代表任选被氟-或氯-取代的甲基,乙基,丙基,异丙基,正丁基,叔丁基或者各自任选被氟-,氯-,溴-,甲基-,乙基-,异丙基-,叔丁基-,甲氧基-,乙氧基-,异丙氧基,三氟甲基-,三氟甲氧基-,氰基-或硝基-取代的苯基或苄基。
R4和R5各自独立地非常特别优选代表各自任选被氟-或氯-取代的C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷基氨基,二-(C1-C4-烷基)-氨基或C1-C4-烷硫基,或者非常特别优选代表各自任选被氟-,氯-,溴-,硝基-,氰基-,甲基-,甲氧基-,三氟甲基-或三氟甲氧基-取代的苯基,苯氧基或苯硫基。
R6和R7各自独立地非常特别优选代表氢,非常特别优选代表各自任选被氟-或氯-取代的C1-C4-烷基,C3-C6-环烷基,C1-C4-烷氧基,C3-C4-链烯基或C1-C4-烷氧基-C2-C4-烷基,非常特别优选代表各自任选被氟-,氯-,溴-,甲基-,甲氧基-或三氟甲基-取代的苯基或苄基,或者一起非常特别优选代表其中任选地一个亚甲基被氧或硫置换的任选被甲基-或乙基-取代的C5-C6-亚烷基。
特别优选的是其中Z不代表氢的式(I)化合物。
优选的还有其中D不代表甲基的那些化合物。
上述一般或优选范围提到的基团的定义或说明可以根据需要相互组合,即也可以是各范围和优选范围之间的组合。它们相应地适用于终产物及母体和中间体。
为了本发明目的,优选的是其中存在作为优选的(优选地)上述提到的定义的组合的式(I)化合物。
为了本发明目的,特别优选的是其中存在作为特别优选的上述提到的定义的组合的式(I)化合物。
为了本发明目的,非常特别优选的是其中存在作为非常特别优选的上述提到的定义的组合的式(I)化合物。
饱和的或不饱和的烃基,例如烷基或链烯基,也包括与杂原子的组合情况,例如在烷氧基中,只要有可能,在各种情况下可以是直链或支链的。
任选被取代的基团可以是一取代或多取代的,多取代情况下取代基可以是相同或不同的。
除了制备实施例中提到的化合物外,可以具体提到下面的式(I-1-a)化合物:
表1 X=CH3;Z=CH3
表1(续):
表1(续):
表2:A和B各自如表1中定义,
X=CH3;Z=Cl
表3:A和B各自如表1中定义,
X=Cl;Z=CH3
除制备实施例中提到的化合物外,可以具体提到下面式(I-2-a)化合物:
表4 X=CH3;Z=CH3
表4(续):
表4(续):
表5:A和B各自如表4中定义,
X=CH3;Z=Cl
表6:A和B各自如表4中定义,
X=Cl;Z=CH3
除制备实施例中提到的化合物外,可以具体提到下面式(I-3-a)化合物:
表7 X=CH3;Z=CH3
A | B |
CH3 | CH3 |
C2H5 | CH3 |
C3H7 | CH3 |
i-C3H7 | CH3 |
C4H9 | CH3 |
i-C4H9 | CH3 |
表7(续):
表7(续):
表8:A和B各自如表7中定义,
X=CH3;Z=Cl
表9:A和B各自如表7中定义,
X=Cl;Z=CH3
除制备实施例中提到的化合物外,可以具体提到下面式(I-4-a)化合物:
表10X=CH3;Z=CH3
表10(续):
表11:A和D各自如表10中所定义,
X=CH3;Z=Cl
表12:A和D各自如表10中所定义,
X=Cl;Z=CH3
如果根据方法(A),用N-[(3-氯-6-甲基)-苯基乙酰基]-1-氨基-4-乙基-环己烷-羧酸乙酯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(B),用0-[(2,5-二氯)-苯基乙酰基]-2-羟基-异丁酸乙酯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(C),用2-[(2-氯-5-甲基)-苯基]-4-(4-甲氧基)-苄基巯基-4-甲基-3-氧代-戊酸乙酯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果,例如,根据方法(D),用(氯代羰基)-2-[(3-氯-6-甲基)-苯基]-乙烯酮和4-氟-苯基·乙基甲酮为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(Eα),用3-[(2,5-二氯)-苯基]-5,5-二甲基-吡咯烷-2,4-二酮和新戊酰氯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(E)(变化方法β),用3-[(2,5-二氯)-苯基]-4-羟基-5-甲基-5-苯基-Δ3-二氢呋喃-2-酮和乙酸酐为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(F),用8-[(2-氯-5-甲基)-苯基]-5,5-五亚甲基-吡咯烷-2,4-二酮和氯甲酸乙氧乙酯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(G),用3-[(2-溴-5-甲基)-苯基]-4-羟基-5-甲基-6-(3-吡啶基)-吡喃酮和氯一硫代甲酸甲酯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(H),用2-[(2,5-二甲基)-苯基]-5,5-[(3-甲基)-五亚甲基]吡咯烷-2,4-二酮和甲磺酰氯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(I),用2-[(2-氯-5-甲基)-苯基]-4-羟基-5-甲基-6-(2-吡啶基)-吡喃酮和硫代甲膦酸酰氯2,2,2-三氟乙酯为起始物,则本发明方法的过程可以通过下面的反应式代表:
如果,根据方法(J),用3-[(2,5-二氯)-苯基]-5-环丙基-5-甲基-吡咯烷-2,4-二酮和氢氧化钠为反应组分,则本发明方法的过程可以通过下面的反应式代表:
如果根据方法(K)(变化方法α),用3-[(2-氯-5-甲基)-苯基]-4-羟基-5,5-四亚甲基-Δ3-二氢-呋喃-2-酮和异氰酸乙酯为起始物,则反应过程可以通过下面的反应式代表:
如果根据方法(K)(变化方法β),用3-[(2-氯-5-甲基)-苯基]-5,5-二甲基-吡咯烷-2,4-二酮和二甲基氨基甲酰氯为起始物,则反应
过程可以通过下面的反应式代表:
用作本发明方法(A)中的起始物需要的式(II)化合物是新的,
其中A,B,X,Z和R8各自如上定义。
例如,当用式(XIX)的取代的苯基乙酰卤酰化式(XVIII)的氨基酸衍生物时,
其中
A,B和R8如上定义,
其中
X和Z各自如上定义,和
Hal代表氯或溴,
(化学综述(Chem.Reviews)
52,237-416(1953);Bhattacharya,印度化学杂志(Indian J.Chem.)
6,341-5,1968)
或者
当式(XX)的乙酰基氨基酸被酯化时(Chem.Ind,(London)1568(1968)),
其中
A,B,X和Z各自如上定义,
得到式(II)的乙酰基氨基酸酯。
式(XX)化合物是新的
其中A,B,X和Z各自如上定义。
当根据Schotten-Baumann(Organikum,VEB Deutscher Verlagder Wissen-schaften,柏林1977,p.505)用式(XIX)的取代的苯基乙酰卤酰化式(XXI)氨基酸时,得到式(XX)化合物
其中
A和B各自如上定义,
其中
X和Z各自如上定义,和
Hal代表氯或溴。
一些式(XIX)化合物是新的。它们可以通过已知的方法制备。
例如,通过在-20℃至150℃,优选-10℃至100℃的温度下,如果适当在稀释剂(例如任选氯化的脂肪烃或芳香烃例如甲苯或二氯甲烷)存在下,用卤化剂(例如亚硫酰氯,亚硫酰溴,草酰氯,光气,三氯化磷,三溴化磷或五氯化磷)与式(XXII)的取代的苯基乙酸反应,得到式(XIX)化合物,
其中
X和Z各自如上定义。
除了2,5-二氯苯基乙酸(CAS5398-79-8),5-氯-2-甲氧基苯基乙酸(CAS7569-62-2),2-氯-5-甲基苯基乙酸(CAS81682-39-5),2,5-二氟苯基乙酸(CAS85068-27-5),2-溴-5-甲基苯基乙酸(BRN3249577)和2-氯-5-三氟甲基苯基乙酸(CAS22893-39-6)外,式(XXII)化合物是新的,它们可以通过文献已知的方法制备(Organikum,15版,p.533,VEB Deutscher Verlag der Wissen-schaften,柏林1977)。例如,通过在0℃和150℃之间,优选20℃和100℃之间的温度下,在酸(例如无机酸,如盐酸)存在下,或者在碱(例如碱金属氢氧化物,如氢氧化钠或氢氧化钾)存在下,并且如果适当,在稀释剂(例如醇水溶液,如甲醇或乙醇)存在下,水解式(XXIII)的取代的苯基乙酸酯,得到式(XXII)化合物,
其中
X,Z和R8各自如上定义。
除了2,5-二氯苯基乙酸甲酯(CAS96129-66-7)和5-氯-2-甲氧基-苯基乙酸甲酯(CAS26939-01-5)外,式(XXIII)化合物是新的,它们可以通过原则上已知的方法制备。
例如,通过式(XXIV)的取代的1,1,1-三氯-2-苯基乙烷首先在0℃和150℃之间,优选20℃和120℃之间的温度下,在稀释剂(例如从烷氧化物衍生的醇)存在下与烷氧化物(例如碱金属烷氧化物,如甲醇钠或乙醇钠)反应,然后在-20℃和150℃之间,优选0℃和100℃之间的温度下与酸(优选无机酸,例如硫酸)反应,得到式(XXIII)化合物(参见DE3314249),
其中
X和Z各自如上定义。
式(XXIV)化合物是新的,它们可以通过原则上已知的方法制备。
例如,当在式(XXVI)亚硝酸烷基酯存在下,在氯化铜(II)存在下,和,如果适当,在稀释剂(例如脂族腈如乙腈)存在下,在-20℃至80℃之间,优选0℃至60℃之间的温度下,式(XXV)苯胺与1,1-二氯乙烯(CH2=CCl2)反应,得到式(XXIV)化合物,
其中
X和Z各自如上定义,
R21-ONO (XXVI)
其中
R21代表烷基,优选C1-C6-烷基。
式(XXV)和(XXVI)化合物是有机化学已知化合物。氯化铜(II)和1,1,-二氯乙烯很早就是已知的了,并且可以购得。
一些式(XVIII)和(XXI)化合物是已知的和/或其可以通过已知的方法制备(参见,例如,Compagnon,Miocque Ann.Chim.(巴黎)[14]
5,p.11-22,23-27(1970))。
其中A和B形成环的式(XXIa)的取代的环氨基羧酸一般通过Bucherer-Bergs合成或者通过Strecher合成而获得,并且这里在每种情况下以不同异构体形式得到。因此,根据Bucherer-Bergs合成的条件,主要获得其中基团R和羧基是平伏位置的异构体(为简化起见下文指定为β),而根据Strecher合成的条件,主要获得其中氨基和基团R是平伏位置的异构体(为简化起见下文指定为α)。
Bucherer-Bergs Strecker
合成(β-异构体) 合成(α-异构体)
(L.Munday,J.Chem.Soc.4372(1961);J.T.Eward,C.Jitrangeri,Can.J.Chem.
53,3339(1975))。
此外,上述方法(A)中使用的式(II)起始物可以通过使式(XXVII)的氨基腈与式(XIX)的取代的苯基乙酰基卤反应,得到式(XXVIII)化合物,并且然后使这些化合物进行酸性醇解来制备,
其中
A,B,X,Z和R8各自如上定义,
其中
A和B各自如上定义,
其中
X,Z和Hal各自如上定义,
其中
A,B,X和Z各自如上定义。
式(XXVIII)化合物也是新的。
用作本发明方法(B)中的起始物需要的式(III)化合物也是新的,
其中
A,B,X,Z和R8各自如上定义。
它们可以通过原则上已知的方法以简单的方式制备。
例如,当用式(XIX)的取代的苯基乙酰基卤酰化式(XXIX)的2-羟基羧酸酯时,得到式(III)化合物,
其中
A,B和R8各自如上定义,
其中
X,Z和Hal各自如上定义(化学综述
52,237-416(1953))。
用作方法(C)中的起始物需要的式(IV)化合物是新的,
其中
A,B,W,X,Z和R8各自如上定义。
它们可以通过原则上已知的方法制备。
例如,当在强碱存在下,用式(XXX)的2-苄硫基酰卤酰化式(XXIII).的取代的苯基乙酸酯时,得到式(IV)化合物,
其中
X,R8和Z各自如上定义,
其中
A,B和W各自如上定义,并且
Hal代表卤素(特别是氯或溴)(参见,例如,M.S.Chambers,E.J.Thomas,D.J.Williams,J.Chem.Soc.Chem.Commun,(1987),1228)。
式(XXX)的苄硫基-酰卤在某些情况下是已知的和/或可以通过已知的方法制备(抗生素杂志(J.Antibiotics)(1983),
26,1589)。
用作方法(D)中的起始物需要的其中Z不代表氢的式(VI)的卤代羰基烯酮是新的。它们可以通过原则上已知的方法以简单的方式制备(参见,例如,有机制备方法(Org.Prep.Proced.Int.),
7,(4),155-158,1975和DE1945703)。
如果适当在催化剂例如二乙基甲酰胺,甲基十八烷基甲酰胺或三苯基膦存在下和如果适当在碱例如吡啶或三乙胺存在下,在-20℃和200℃之间,优选在0℃和150℃之间的温度下,当式(XXXI)的取代的苯基丙二酸与酰卤例如亚硫酰氯,氯化磷(V),氯化磷(III),草酰氯,光气或亚硫酰溴反应时,得到式(VI)化合物,
其中
X和Z各自如上定义,和
Hal代表氯或溴,
其中
X和Z各自如上定义。
其中Z不代表氢的式(XXXI)的取代的苯基丙二酸是新的。但是,它们可以通过已知的方法以简单的方式制备(参见,例如,Organikum,VEB Deutscher Verlag der Wissenschaften,柏林1977,p.517ff),例如,通过水解式(XXXII)取代的苯基丙二酸酯而得到,
其中
X,Z和R8各自如上定义。
用作本发明方法(D)中的起始物需要的式(V)的羰基化合物或其式(Va)的甲硅烷基烯醇醚是可以购得的化合物,一般是已知的,或者通过已知的方法易得的,
其中
A,D和R8’各自如上定义。
式(XXXII)的丙二酸酯是新的,
其中
R8,X和Z各自如上定义,并且Z不是氢。
它们一般通过已知的有机化学方法来制备(参见,例如四面体通讯(Tetrahedron Lett.)
27,2763(1986)和Organikum,VEB DeutscherVerlag der Wisaenschaften,柏林1977,p.587ff)。
另外,进行本发明方法(F),(G),(H),(I),(J)和(K)所需要用作起始物的式(VII)酰卤,式(VIII)酸酐,式(IX)氯甲酸酯或氯甲酸硫酯,式(X)氯一硫代甲酸酯或氯二硫代甲酸酯,式(XII)磺酰氯,式(XIII)磷化合物和式(XIV)和(XV)金属氢氧化物,金属烷氧化物或胺和式(XVI)异氰酸酯和式(XVII)氨基甲酰氯一般是已知的有机化学或无机化学化合物。
式(V),(VII)至(XVII),(XVIII),(XXI),(XXII),(XXIX),(XXX)和(XXXI)化合物还公开于开篇所引用的专利申请中和/或可以通过所给出的方法制备。
方法(A)的特征在于,使其中A,B,X,Z和R8各自如上定义的式(II)化合物在稀释剂存在下和在碱存在下进行分子内缩合。
进行本发明方法(A)合适的稀释剂是对反应参与者呈惰性的所有的有机溶剂。优选使用的是烃,例如甲苯和二甲苯,还有醚类,例如二丁基醚,四氢呋喃,二_烷,乙二醇二甲基醚和二甘醇二甲基醚,还有极性溶剂,例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基吡咯烷酮,还有醇类,例如甲醇,乙醇,丙醇,异-丙醇,丁醇,异丁醇和叔丁醇。
进行本发明方法(A)的合适的碱(去质子剂)是所有常规质子受体。优选使用的是碱金属和碱土金属氧化物,氢氧化物和碳酸盐,例如,氢氧化钠,氢氧化钾,氧化镁,氧化钙,碳酸钠,碳酸钾和碳酸钙,它们也可以在相转移催化剂例如三乙基苄基氯化铵,四丁基溴化铵,Adogen464(=甲基三烷基(C8-C10)氯化铵)或TDA 1(=三-(甲氧基乙氧基-乙基)胺)存在下使用。也可以使用碱金属,例如钠或钾。此外,可以使用碱金属和碱土金属氨基化物和氢化物,例如氨基钠,氢化钠和氢化钙,此外还有碱金属烷氧化物,例如甲醇钠,乙醇钠和叔丁醇钾。
进行本发明方法(A)时,反应温度可以在较宽的范围内变化。一般情况下,在0℃和250℃之间的温度下进行该反应,优选在50℃和150℃之间。
本发明方法(A)一般在大气压下进行。
进行本发明方法(A)时,一般以等摩尔至大约两倍摩尔的量使用式(II)反应组分和去质子碱。但是,也可以以较大的过量(最多3mol)使用一种组分或另一种组分。
方法(B)的特征在于,使其中A,B,X,Z和R8各自如上定义的式(III)化合物在稀释剂存在下和在碱存在下进行分子内缩合。
进行本发明方法(B)合适的稀释剂是对反应参与者呈惰性的所有的有机溶剂。优选使用的是烃,例如甲苯和二甲苯,还有醚类,例如二丁基醚,四氢呋喃,二_烷,乙二醇二甲基醚和二甘醇二甲基醚,还有极性溶剂,例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基吡咯烷酮,还可以使用醇类,例如甲醇,乙醇,丙醇,异丙醇,丁醇,异丁醇和叔丁醇。
进行本发明方法(B)的合适的碱(去质于剂)是所有常规质子受体。优选使用的是碱金属和碱土金属氧化物,氢氧化物和碳酸盐,例如,氢氧化钠,氢氧化钾,氧化镁,氧化钙,碳酸钠,碳酸钾和碳酸钙,它们也可以在相转移催化剂例如三乙基苄基氯化铵,四丁基溴化铵,Adogen464(=甲基三烷基(C8-C10)-氯化铵)或TDA 1(=三-(甲氧基乙氧基-乙基)-胺)存在下使用。也可以使用碱金属例如钠或钾。合适的还有碱金属和碱土金属氨基化物和氢化物,例如氨基钠,氢化钠和氢化钙,和碱金属烷氧化物,例如甲醇钠,乙醇钠和叔丁醇钾。
进行本发明方法(B)时,反应温度可以在较宽的范围内变化。一般情况下,在0℃和250℃之间的温度下进行该反应,优选在50℃和150℃之间。
本发明方法(B)一般在大气压下进行。
进行本发明方法(B)时,一般以大约等摩尔量使用式(III)反应组分和去质子碱。但是,也可以以较大的过量(最多3mol)使用一种组分或另一种组分。
方法(C)的特征在于,使其中A,B,W,X,Z和R8各自如上定义的式(IV)化合物在酸存在下和如果适当在稀释剂存在下进行分子内环化。
进行本发明方法(C)合适的稀释剂是对反应参与者呈惰性的所有的有机溶剂。优选使用的是烃,例如甲苯和二甲苯,还有卤代烃,例如二氯甲烷,氯仿,二氯乙烷,氯苯,二氯苯,还有极性溶剂,例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基吡咯烷酮,还可以使用醇类,例如甲醇,乙醇,丙醇,异丙醇,丁醇,异丁醇和叔丁醇。
如果适当,使用的酸也可以用作稀释剂。
本发明方法(C)中使用的酸是所有常规无机酸和有机酸,例如氢卤酸,硫酸,烷基-、芳基-和卤代烷基磺酸,尤其是卤代烷基羧酸如三氟乙酸。
进行本发明方法(C)时,反应温度可以在较宽的范围内变化。一般情况下,在0℃和250℃之间的温度下进行该反应,优选在50℃和150℃之间。
本发明方法(C)一般在大气压下进行。
进行本发明方法(C)时,例如以等摩尔量使用式(IV)反应组分和酸。但是,如果适当,也可以以催化剂量使用酸。
本发明方法(D)的特征在于,如果适当在稀释剂存在下和如果适当在酸受体存在下,使式(V)羰基化合物或式(Va)其甲硅烷基烯醇醚与式(VI)烯酮酰基卤反应。
进行本发明方法(D)合适的稀释剂是对反应参与者呈惰性的所有的有机溶剂。优选使用的是烃,例如邻二氯苯,四氢化萘,甲苯和二甲苯,还有醚类,例如二丁基醚,乙二醇二甲基醚和二甘醇二甲基醚,还有极性溶剂,例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基-吡咯烷酮。
进行本发明方法(D)所使用的酸受体是所有常规酸受体。
优选使用的是叔胺,例如三乙胺,吡啶,二氮杂双环辛烷(DABCO),二氮杂双环十一烯(DBU),二氮杂双环壬烯(DBN),Hünig碱或N,N-二甲基苯胺。
进行本发明方法(D)时,反应温度可以在较宽的范围内变化。有利地,在0℃和250℃之间的温度下进行该反应,优选在50℃和220℃之间。
本发明方法(D)优选在大气压下进行。
进行本发明方法(D)时,一般以大约等摩尔量使用式(V)和(VI)反应组分和,如果适当,酸受体。但是,也可以以较大的过量(最多5mol)使用一种组分或另一种组分。
方法(Eα)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(I-1-a)至(I-4-a)化合物在各种情况下与式(VII)酰基卤反应。
进行本发明方法(Eα)合适的稀释剂是对酰基卤呈惰性的所有溶剂。优选使用的是烃,例如汽油,苯,甲苯,二甲苯和四氢化萘,还有卤代烃,例如二氯甲烷,氯仿,四氯化碳,氯苯和邻二氯苯,还有酮类,例如丙酮和甲基异丙基酮,还有醚类,例如乙醚,四氢呋喃和二_烷,还有羧酸酯,例如乙酸乙酯,还有强极性溶剂,例如二甲基甲酰胺,二甲亚砜和环丁砜。如果酰基卤对水解的稳定性允许,则也可以在水存在下进行该反应。
进行本发明方法(Eα)的合适的酸结合剂是所有常规酸受体。优选使用的是叔胺,例如三乙胺,吡啶,二氮杂双环辛烷(DABCO),二氮杂双环十一烯(DBU),二氮杂双环壬烯(DBN),Hunig碱和N,N-二甲基苯胺,还有碱土金属氧化物,例如氧化镁和氧化钙,还有碱金属和碱土金属碳酸盐,例如碳酸钠,碳酸钾和碳酸钙,还有碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
进行本发明方法(Eα)的反应温度可以在较宽的范围内变化。一般情况下,在-20℃和+150℃之间的温度下进行该反应,优选在0℃和100℃之间。
进行本发明方法(Eα)时,一般各自以大约等摩尔量使用式(I-1-a)至(I-4-a)起始物和式(VII)酰基卤。但是,也可以以较大的过量(最多5mol)使用酰基卤。根据常规方法进行后处理。
方法(Eβ)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(VIII)酸酐反应。
进行本发明方法(Eβ)优选的稀释剂是使用酰基卤时也优选的那些稀释剂。另外,过量使用的酸酐也可以同时作为稀释剂起作用。
方法(Eβ)中可能加入的酸结合剂优选是使用酰基卤时也优选的那些酸结合剂。
进行本发明方法(Eβ)的反应温度可以在较宽的范围内变化。一般情况下,在-20℃和+150℃之间的温度下进行该反应,优选在0℃和100℃之间。
进行本发明方法(Eβ)时,一般各自以大约等摩尔量使用式(I-1-a)至(I-4-a)起始物和式(VIII)酸酐。但是,也可以以较大的过量(最多5mol)使用酸酐。根据常规方法进行后处理。
一般情况下,进行一个步骤,其中通过蒸馏或者通过用有机溶剂或用水洗涤来去除稀释剂和过量的酸酐以及产生的羧酸。
方法(F)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(IX)氯甲酸酯或氯甲酸硫酯反应。
进行本发明方法(F)的合适的酸结合剂是所有常规酸受体。优选使用的是叔胺例如三乙胺,吡啶,DABCO,DBU,DBA,Hünig碱和N,N-二甲基苯胺,还有碱土金属氧化物,例如氧化镁和氧化钙,还有碱金属和碱土金属碳酸盐,例如碳酸钠,碳酸钾和碳酸钙,还有碱金属氢氧化物例如氢氧化钠和氢氧化钾。
进行本发明方法(F)合适的稀释剂是对氯甲酸酯或氯甲酸硫酯呈惰性的所有溶剂。优选使用的是烃例如汽油,苯,甲苯,二甲苯和四氢化萘,还有卤代烃,例如二氯甲烷,氯仿,四氯化碳,氯苯和邻二氯苯,还有酮类例如丙酮和甲基异丙基酮,还有醚类例如乙醚,四氢呋喃和二_烷,还有羧酸酯例如乙酸乙酯,还有腈类例如乙腈,还有强极性溶剂例如二甲基甲酰胺,二甲亚砜和环丁砜。
进行本发明方法(F)时,反应温度可以在较宽的范围内变化。一般情况下,在-20℃和+100℃之间的温度下进行该反应,优选在0℃和50℃之间。
本发明方法(F)一般在大气压下进行。
进行本发明方法(F)时,一般各自以大约等摩尔量使用式(I-1-a)至(I-4-a)起始物和式(IX)合适的氯甲酸酯或氯甲酸硫酯。但是,也可以以较失的过量(最多2mol)使用一种组分或另一种组分。根据常规方法进行后处理。一般情况下,进行一个步骤,其中去除沉淀的盐并且通过汽提出稀释剂来浓缩残留的反应混合物。
本发明方法(G)的特征在于,在稀释剂存在下和如果适当在酸结合剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(X)化合物反应。
在制备方法(G)中,在0-120℃,优选在20-60℃下,使每摩尔式(I-1-a)至(I-4-a)起始物与大约1mol式(X)氯代一硫代甲酸酯或氯代二硫代甲酸酯反应。
如果适当,加入的稀释剂是所有的惰性极性有机溶剂,例如醚类,酰胺类,砜类,亚砜类,还有卤代烷类。
优选使用二甲亚砜,四氢呋喃,二甲基甲酰胺或二氯甲烷。
在一个优选实施方案中,如果通过加入强去质子剂例如氢化钠或叔丁醇钾来制备(I-1-a)至(I-4-a)化合物的烯醇盐,则可以省去另外加入酸结合剂。
如果使用酸结合剂,常规的无机或有机碱是合适的;作为例子可以提到的是氢氧化钠,碳酸钠,碳酸钾,吡啶和三乙胺。
反应可以在常压或高压下进行;优选在大气压下进行,根据常规方法进行后处理。
本发明方法(H)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(XII)磺酰氯反应。
在制备方法(H)中,在-20-150℃,优选在0-70℃下,使每摩尔式(I-1-a)至(I-4-a)起始物与大约1mol式(XII)磺酰氯反应。
方法(H)优选在稀释剂存在下进行。
合适的稀释剂是所有惰性极性有机溶剂例如醚类,酰胺类,酮类,羧酸酯类,腈类,砜类,亚砜类或卤代烃类例如二氯甲烷。
优选使用二甲亚砜,四氢呋喃,二甲基甲酰胺和二氯甲烷。
在一个优选实施方案中,如果通过加入强去质子剂(例如氢化钠或叔丁醇钾)来制备(I-1-a)至(I-4-a)化合物的烯醇盐,则可以省去进一步加入酸结合剂,
如果使用酸结合剂,常规的无机或有机碱是合适的;作为例子可以提到的是氢氧化钠,碳酸钠,碳酸钾,吡啶和三乙胺。
反应可以在常压或高压下进行,优选在大气压下进行,根据常规方法进行后处理。
本发明方法(I)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(XIII)磷化合物反应。
在制备方法(I)中,在-40℃和150℃之间,优选在-10℃和110℃之间的温度下,使每1摩尔式(I-1-a)至(I-4-a)化合物与1-2,优选1-1.3mol式(XIII)磷化合物反应,得到式(I-1-e)至(I-4-e)化合物。
方法(I)优选在稀释剂存在下进行。
合适的稀释剂是所有惰性极性有机溶剂,例如醚类,羧酸酯类,卤代烃类,酮类,酰胺类,腈类,砜类,亚砜类等。
优选使用乙腈,二甲亚砜,四氢呋喃,二甲基甲酰胺或二氯甲烷。
如果适当,可以加入的酸结合剂是常规无机或有机碱,例如氢氧化物,碳酸盐或胺类。作为例子可以提到的是氢氧化钠,碳酸钠,碳酸钾,吡啶和三乙胺。
反应可以在常压或高压下进行;优选在大气压下进行。根据有机化学常规方法进行后处理。终产物优选通过结晶,色谱纯化或者通过称之为“初期蒸馏”,即真空去除挥发成分来纯化。
本发明方法(J)的特征在于,如果适当在稀释剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(XIV)金属氢氧化物或金属烷氧化物或式(XV)胺反应。
用于本发明方法(J)的优选稀释剂是醚类例如四氢呋喃,二_烷和乙醚,还有醇类例如甲醇,乙醇和异丙醇,还有水。本发明方法(J)一般在大气压下进行。反应温度一般在-20℃和100℃之间,优选在0℃和50℃之间。
本发明方法(K)的特征在于,(Kα)如果适当在稀释剂存在下和如果适当在催化剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(XVI)化合物反应,或者(Kβ)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(I-1-a)至(I-4-a)化合物各自与式(XVII)化合物反应。
在制备方法(Kα)中,在0℃-100℃,优选在20℃-50℃温度下,使每摩尔式(I-1-a)至(I-4-a)起始物与大约1mol式(XVI)异氰酸酯反应。
方法(Kα)优选在稀释剂存在下进行。
合适的稀释剂是所有惰性有机溶剂,例如芳香烃类,卤代烃类,醚类,酰胺类,腈类,砜类或亚砜类等。
如果需要,可以加入催化剂来促进反应。使用的催化剂非常有利地是有机锡化合物,例如二月桂酸二丁基锡。
反应优选在大气压下进行。
在制备方法(Kβ)中,在0℃-150℃,优选在20℃-70℃温度下,使每摩尔式(I-1-a)至(I-4-a)起始物与大约1mol式(XVII)氨基甲酰氯反应。
任选加入的可能的稀释剂是所有惰性极性有机溶剂,例如醚类,羧酸酯类,腈类,酮类,酰胺类,砜类,亚砜类或卤代烃类。
优选使用二甲亚砜,四氢呋喃,二甲基甲酰胺或二氯甲烷。
在一个优选实施方案中,如果通过加入强去质子剂(例如氢化钠或叔丁醇钾)来制备(I-1-a)至(I-4-a)化合物的烯醇盐,则可以省去进一步加入酸结合剂。
如果使用酸结合剂,常规的无机或有机碱是合适的;作为例子可以提到的是氢氧化钠,碳酸钠,碳酸钾,吡啶或三乙胺。
反应可以在常压或高压下进行,优选在大气压下进行。根据常规方法进行后处理。
本发明活性化合物适于防治动物害虫,优选节肢动物和线虫,特别是农业,林业,储藏品保护和材料保护,以及卫生领域所遇到的昆虫,和蛛形纲。这些化合物对于一般敏感性和抗性物种都是有活性的,并且在害虫发育的所有阶段或部分阶段有效。上述害虫包括:等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber。
多足纲目(Diplopoda),例如Blaniulus gutttulatus。
唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。
综合纲目(Symphyla),例如Scutigerella immaculata。缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。弹尾目(Collembola),例如Onychiurus armatus。直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoriamigratorioides),长额负蝗(Melanoplus differentialis)和Schistocerca gregaria。
革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia)。等翅目(Isoptera),例如白蚁属(Reticulitermes spp.)。虱目(Anoplura),例如Phylloxera vastatrix,瘿绵蚜属(Pemphigusspp.),头虱(Pediculus humanus corporis),盲虱属(Haematopinusspp.)和长额虱(Linognathus spp.)。
食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalinea spp.。
缨翅目(Thysanoptera),例如温室条蓟马(Hercinothripsfemoralis)和棉蓟马(Thrips tabaci)。
异翅亚目(Heteroptera),例如褐盾蝽属(Eurygasterspp.),Dysdercus intermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimex lectularius),Rhodnius prolixus和吸血猎蝽属(Triatoma spp.)。
同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphisgossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Doralis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodonhumuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelis bilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotus hederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletis blancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutella maculipennis),天幕毛虫(Malacosomaneustria),Euproctis chrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrix thurberiella),Phyllocnisticitrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Earias insulana),夜蛾属(Heliothisspp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestrabrassicae),Panolis flammea,斜纹夜蛾(Prodenia litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilospp.),Pyrausta nubilalis,Ephestia kuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineola bisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophilapseudospretella),Cacoecia podana,Capua reticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysiaambiguella),茶黄卷叶蛾(Homona magnanima)和栎绿卷叶蛾(Tortrix viridana)。
鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,大豆象(Acanthoscelides obtectus),家天牛(Hylotrupes bajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemlineata),Phaedon cochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachna varivestis),Atomaria spp.,锯胸谷盗(Oryzaephilus surinamens),象甲属(Anthonomus spp.),米象属(Sitophilus spp.),Otiorrhynchus sulcatus,香蕉蛛基象甲(Cosmopolites sordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hypera posttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenuespp.),粉蠹(Lyctus spp.),Meligethes aeneus,蛛甲属(Ptinusspp.),金黄蛛甲(Niptus hdoleucus),麦蛛甲(Gibbiumpsylliodes),拟谷稻属(Tribollum spp.),黄粉甲(Tenebriomolitor),扣甲属(Agriotes spp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis)和Costelytra zealandica.
膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomoriumpharaonis),和胡蜂(Vespa spp.)。
双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydodermaspp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyia hyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipula paludosa).
蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis),和角叶蚤属(Ceratophyllus spp.)。
蛛形纲(Arachnida),例如Sciopio maurus,黑寡妇球腹蛛(Latrodectus mactans)。
蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssusgallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptesspp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.)。
本发明活性化合物的特征在于有高杀昆虫和杀螨活性。
它们被用来特别好地有效防治对植物有害的害虫,例如杀辣根猿叶甲(Phaedon cochleariae)幼虫,杀黑尾叶蝉(Nephotettixcincticeps)幼虫或者杀小菜蛾(Plutella maculipennis)毛虫(参见应用实施例)。
活性化合物可以转变成常规制剂,例如溶液、乳液、可湿性粉末、悬浮液、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、浸有活性化合物的天然的和合成的材料,和包裹在聚合物中的细微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与扩充剂即液体溶剂和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
用水作扩充剂的情况下,也可以用例如有机溶剂作助溶剂。作为液体溶剂合适的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物和氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂肪烃如环己烷或石蜡,例如矿物油馏份,矿物油和植物油,醇类如丁醇或乙二醇以及其醚和酯,酮类如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲亚砜,以及水。
作为固体载体合适的是:
例如铵盐,磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎;作为乳化剂和/或起泡剂适合的有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;作为分散剂适合的有:例如,木素亚硫酸废液和甲基纤维素。
制剂中,可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可以使用染料,如无机顔料例如氧化铁、氧化钛和普鲁士蓝,和有机染料如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
本发明活性化合物可以以其商售制剂和由这些制剂制备的使用形式作为与其它活性化合物的混合物存在,例如杀虫剂、引诱剂、杀菌剂、杀螨剂、杀线虫剂、杀真菌剂,生长调节剂或除草剂。杀虫剂包括例如磷酸酯,氨基甲酸酯,羧酸酯,氯代烃,苯基脲和由微生物产生的物质。
特别有利的混合物成分的例子如下:
杀真菌剂:
2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚胺基-N-甲基-2-(2-苯氧基苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧基]-苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚胺基[α-(邻甲苯基氧基)-邻-甲苯基]乙酸甲酯;2-苯基苯酚(OPP),aldimorph,氨丙磷酸,敌菌灵,戊环唑,
苯霜灵,邻碘酰苯胺,苯菌灵,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌消,乙菌利,代森锰,霜尿氰,环唑醇,酯菌胺,
双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,_醚唑,二甲嘧吩,烯酸吗啉,烯唑醇,二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,多果定,氨_唑酮,
克瘟散,epoxyconazole,乙嘧酚,土菌灵,
氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,fludioxonil,氟氯菌核利,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋霜灵,拌种胺,
谷种定,
六氯苯,己唑醇,_霉灵,
抑霉唑,酰胺唑,双瓣醋酸盐,异稻瘟净(IBP),异菌脲,稻瘟灵,
春雷霉素,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,噻菌胺,腈菌唑,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,_霜灵,oxamocarb,氧化萎锈灵,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,
五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,氟嘧唑,噻菌灵,噻菌腈,甲基硫菌灵,福美双,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
稻纹散,乙烯菌核利,
代森锌,福美锌。
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,阿凡曼菌素,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,_虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben、
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,CGA157419,CGA184699,chloethocarb,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌_磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,_唑磷,异阿凡曼菌素,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NC184,NI25,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
RH5292,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,YI5301/5302,zetamethrin。
除草剂:
例如N-酰苯胺类,例如吡氟草胺和敌稗;芳基羧酸类,例如二氯吡啶甲酸,麦草畏和毒莠定;芳基氧基链烷酸类,例如2,4-滴,2,4-滴丁酸,2,4-滴丙酸,氟草烟,2甲4氯,2甲4氯丙酸和绿草定;芳基氧基-苯氧基-链烷酸酯类,例如禾草灵,_唑禾草灵,吡氟禾草灵,吡氟氯禾灵和喹禾灵;吖嗪酮类,例如杀草敏和哒草伏;氨基甲酸酯类,例如氯苯胺灵,甜菜安,甜菜宁和苯胺灵;氯代N-乙酰苯胺类,例如甲草胺,乙草安,丁草安,吡草安,异丙甲草胺,丙草安和毒草安;二硝基苯胺类,例如安磺灵,二甲戊乐灵和氟乐灵;二苯基醚类,例如三氟羧草醚,甲羧除草醚,乙羧氟草醚,氟磺胺草醚,halosafen,乳氟禾草灵和乙氧氟草醚;脲类,例如氯麦隆,敌草隆,伏草隆,异丙隆,利谷隆和甲基苯噻隆;羟胺类,例如禾草灭,烯草酮,噻草隆,稀禾定和肟草酮;咪唑啉酮类,例如咪草烟,咪草酯,灭草烟和灭草喹;腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如苯噻草胺;磺酰脲类,例如amidosulfuron,苄嘧黄隆,氯嘧黄隆,氯黄隆,醚黄隆,甲黄隆,烟嘧黄隆,氟嘧黄隆,吡嘧黄隆,噻黄隆,醚苯黄隆和苯黄隆;硫代氨基甲酸酯类,例如克草猛,灭草特,燕麦畏,菌达灭,禾草畏,草达灭,苄草丹,杀草丹和野燕畏;三嗪类,例如莠去津,氰草津,西玛津,西草净,特丁净和terbutylazine;三嗪酮类,例如环嗪酮,苯嗪草酮和嗪草酮;其它类,例如氨基三唑,呋草黄,灭草松,环庚草醚,异_草酮,二氯吡啶酸,双苯唑快,氟硫草定,乙呋草黄,氟咯草酮,草铵膦,草甘膦,isoxaben,哒草特,二氯喹啉酸,喹草酸,草硫磷和灭草环。
本发明活性化合物还可以以其商售制剂和由这些制剂制备的使用形式作为与增效剂的混合物存在。增效剂是提高活性化合物的作用而其自身不必是活性的化合物。
由商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。使用形式活性化合物的浓度是0.0000001-95%重量活性化合物,优选0.0001-1%重量。
以适于这些使用形式的常规方式应用这些化合物。
当用来杀卫生领域害虫和储存产品害虫时,这些活性化合物的特征在于对木材和粘土的极好的残留作用,以及对用石灰处理过的物质上的碱的好的稳定性。
本发明活性化合物不仅对杀植物,卫生领域和储存产品害虫有活性,而且还用于兽药领域,杀动物寄生虫(内寄生虫),例如硬蜱,软蜱,马痒螨,恙螨,蝇(叮和吮),寄生蝇幼虫,虱,头虱,鸟虱和蚤。这样的寄生虫包括:
虱目(Anolpurida),例如,血虱属(Haematopinus spp.),长
虱(Linognathus spp.),虱属(Pediculus spp.),阴虱属(Phtirusspp.),管虱属(Solenopotes spp.)。
食毛目咬虱(Mallophagida)和Amblycerina及Ischnocerina亚目,例如毛羽虱属(Trimenopon spp.),Menopon spp.,巨羽虱属(Trinoton spp.),牛羽虱属(Bovicola spp.),Werneckiella spp.,Lepikentron spp.,Damalina spp.,Trichodectes spp.,Felcolaspp.。
双翅目(Diptera)和长角亚目(Nematocerina)和Brachycorina亚目,例如伊蚊(Aedes spp.),斑按蚊属(Anopheles spp.),库蚊(Culex spp.),蚋属(Simulium spp.),全毛真蚋(Eusimulium spp.),白蛉(Phlebotomus spp.),罗蛉属(Lutzomyia spp.),库蠓(Culicoides spp.),斑虻(Chrysops spp.),瘤虻(Hybomitra spp),Atylotus spp.,虻属(Tabanus spp.),麻虻属(Haematopotaspp.),Philipomyia spp.,Braula spp.,Musca spp.,齿股蝇属(Hydrotuea spp.),螫蝇(Stomoxys spp.),Haematobia spp.,Morellia spp.,厕蝇(Fannia spp.),Glossinaspp.,Calliphoraspp.,Lucilia spp.,Chrysomyia spp.,Wohlfahrtia spp.,别麻蝇(Sareophaga spp.),Oestrus spp.,皮蝇(Hypoderma spp.),Gasterophilus spp.,虱蝇(Hippobosca spp.),Lipoptena spp.,和Melophagus spp,.
蚤目(Siphonapterida),例如,蚤属(Pulex spp.),Ctenocephalides spp.,鼠蚤(Xenopsylla spp.),和角叶蚤(Ceratophyllus spp.).
异翅亚目(Heteropterida),例如,臭虫属(Cimex spp.),吸血猎蝽属(Triatoma spp.),Rhodnius spp.,和全圆蝽属(Panstrongylusspp.)。
非蠊目(Blattarida),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),德国小蠊(Blattela germanica),非蠊属(Supella spp.)。
螨亚类(Acarida),和后胸气门目(Metastigmata)和中胸气门目(Mesostigmata),例如,隐喙蜱属(Argas spp.),喙蜱属(Ornithodorus spp.),耳残喙蜱(Otabius spp.),硬蜱(Ixodesspp.),花蜱属(Amblyonma spp.),牛蜱属(Boophilus spp.),矩头蜱(Dermacentor spp.),Haemophysalis spp.,璃眼蜱(Hyalommaspp.),头蜱属(Rhipicephalus spp.),鸡皮刺螨(Dermanyssusspp.),瑞立绦虫(Raillietia spp.),Pneumonyssus spp.,Sternostoma spp.,和Varroa spp.。
Actinedida(恙螨亚目,Prostigmata)和Acaridida(Astigmata),例如Acarapis spp.,姬螯螨属(Cheyletiella spp.),Ornithocheyletia spp.,Myobia spp.,疥螨(Psorergates spp.),蠕形螨(Demodex spp.),恙螨(Trombiculaspp.),Listrophorus spp.,粗脚粉螨(Acarus spp.),酪螨(Tyrophagus spp.),嗜木螨(Caloglyphus spp.),Hypodectes spp.,翼衣螨属(Pterolichus spp.),恙螨(Psoroptes spp.),恙螨(Chorioptes spp.),Octodectes spp.,疥螨(Sarcoptes spp.),Notoedres spp.,足螨(Knemidocoptes spp.,),Cytodites spp.,和Laminosioptes spp.。
例如它们具有杀丝光绿蝇(Lucilla cuprina)和Boophilusmicroplus的出色的活性。
本发明式(I)活性化合物也适于杀死侵染农业生产家畜的节肢动物,所述家畜是例如牛,绵羊,山羊,马,猪,驴,骆驼,水牛,兔子,鸡,火鸡,鸭,鹅,蜜蜂,其它宠物,例如狗,猫,笼养的鸟和鱼缸养殖鱼,和称之为实验室动物的动物,例如仓鼠,豚鼠,大鼠和小鼠。通过杀死这些节肢动物,可以避免家畜死亡并且提高产量(例如肉,奶,毛,皮,蛋,蜂蜜等产量),因此通过使用本发明活性化合物可以实现更经济更简单的动物的喂养。
在兽药领域,本发明活性化合物以已知方式经肠给药使用,例如以片剂,胶囊,顿服水剂,顿服药,颗粒剂,糊剂,巨丸剂,送食方法栓剂,通过肠胃外给药,例如通过注射(肌内,皮下,静脉内,腹膜内等),埋入,通过鼻给药,通过以例如浸渍或浸浴,喷洒,倒施和点施,洗用和撒粉的形式皮肤给药,也可以借助于含有活性化合物的成型物品,例如颈圈,耳饰,尾饰,腿带,笼头,标记物等而使用。
当对牲畜,家禽,宠物等施用时,本发明式(I)活性化合物可以作为以1-80%重量比的量含有活性化合物的制剂(例如粉末剂,乳剂,可流动剂)而被使用,直接使用或者稀释100-10000倍后使用,或者可以以化学浴形式使用。
另外,还发现本发明式(I)化合物还具有杀破坏工业物质的昆虫的有效能的杀虫作用。
作为例子,优选可以提到下面的昆虫,但是不受此限制:
甲虫,例如
家天牛(Hylotrupes bajulus),Chlorophorus pilosis,家具窃蠹(Anobium punctatum),Xestobium rufovillosum,Ptilinuspecticornis,Dendrobium pertinex,Ernobius mollis,Priobiumcarpini,欧洲竹粉蠹(Lyctus brunneus),Lyctus africanus,平颈粉蠹(Lyctus planicollis),Lyctus linearis,Lyctuspubescens,Trogoxylon aequale,Minthes rugicollis,小蠹虫种(Xyleborus spec.),Tryptodendron spec.,Apate monachus,Bostrychus capucins,Heterobostrychus branneus,Simoxylonspec.,和竹长蠹(Dinoderus minutus)。
膜翅目(Dermapterans),例如
钢青小树蜂(Sirex juvencus),枞大树蜂(Urocerus gigas),Urocerus gigas taignus和Urocerus augur。
白蚁,例如
Kalotermes flavicollis,Cryptotermes brevis,Heterotermes indicola,Reticulitermes flavipes,Reticulitermes santonensis,Reticulitermes lucifugus,澳洲白蚁(Mastotermes darwiniensis),Zootermopsis nevadensis和台湾家白蚁(Coptotermes formosanus)。
Bristle-tail,例如西洋衣鱼(Lepisma saccharina)。
本发明中所涉及的工业材料理解为非生命材料,例如,优选合成材料,粘合剂,胶料,纸和纸板,皮革,木材和木材加工产品以及涂料。
要非常特别保护使不受昆虫侵染的材料是木材和木材加工产品。
可以用本发明组合物或含有这样一种组合物的混合物保护的木材和木材加工产品理解为是,例如建筑木材加工品,木梁,铁轨枕木,建桥木料,码头,木制运载工具,箱子,制模板,容器,电线杆,木桶,木窗,木门,胶合板,颗粒板,接合物,或者在房屋建筑或细木工行业很普通使用的木产品。
本发明活性化合物可以以其自身,以浓缩物形式或者一般的常规制剂例如粉末剂,颗粒剂,溶液,混悬剂,乳剂或糊剂使用。
提到的制剂可以以本身已知的方法制备,例如通过混合活性化合物和至少一种溶剂或稀释剂,乳化剂,悬浮剂和/或粘合剂或固定剂,防水剂,如果合适,干燥剂和UV稳定剂和,如果合适,着色剂和颜料和其它加工助剂。
用于保护木料和木制品的杀虫剂组合物或浓缩物以0.0001-95%重量浓度含有本发明活性化合物,特别是0.001-60%重量。
使用的组合物或浓缩物的量取决于害虫的物种和发生情况,并取决于介质。施用的最佳比例每种情况下可以通过试验系列来决定。但是,一般情况下,使用以要保护的材料为基础的0.0001-20%重量,优选0.001-10%重量的活性化合物足够了。
使用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油或油型有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水和,如果合适,乳化剂和/或湿润剂。
优选使用的有机化学溶剂是具有大于35的挥发数和高于30℃,优选高于45℃的闪点的油或油型溶剂。作为这样的具有低挥发性并且在水中不溶解的油和油型溶剂的物质有合适的矿物油或其芳香烃级分,或者含有矿物油的溶剂混合物,优选石油溶剂,石油和/或烷基苯。
有利地使用的物质是沸点范围是170-220℃的矿物油,沸点范围是170-220℃的石油溶剂,沸点范围是250-350℃的锭子油,沸点范围是160-280℃的石油或芳香烃,松节精油等。
在一个优选的实施方案中,使用的物质是沸点范围是180-210℃的液体脂肪烃或者沸点范围是180-220℃的芳香烃和脂肪烃的高沸点混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
具有大于35的挥发数和高于30℃,优选高于45℃闪点的低挥发性有机油或油型溶剂可以部分替换成低挥发性或中等挥发性的有机化学溶剂,前提是该溶剂混合物也具有大于35的挥发数和高于30℃,优选高于45℃的闪点,并且杀虫剂/杀真菌剂混合物在该溶剂混合物中是可溶解的或可乳化的。
在一个优选的实施方案中,部分有机化学溶剂或溶剂混合物替换成脂肪族极性有机化学溶剂或溶剂混合物。优选使用的物质是具有羟基和/或酯基和/或醚基的脂肪族有机化学溶剂,例如二醇醚,酯等。
本发明范围内使用的有机化学粘合剂是本身已知的合成树脂和/或粘合干燥油,并且可以用水稀释和/或在使用的有机化学溶剂中是可溶解的,可分散的或可乳化的,特别是粘合剂由下面的物质组成或者含有下面的物质:丙烯酸树脂,乙烯树脂,例如聚乙酸乙烯酯,聚酯树脂,缩聚物或加聚物树脂,聚氨酯树脂,醇酸树脂或改性的醇酸树脂,苯酚树脂,烃类树脂,例如茚/苯并呋喃树脂,硅氧烷树脂,干燥植物油和/或干燥油和/或以天然和/或合成树脂为基础的物理干燥粘合剂。
作为粘合剂使用的合成树脂可以以乳液,分散液或溶液的形式使用。最多10%重量的沥青或沥青状物质也可以作为粘合剂使用。另外,可以使用本身已知的着色剂,颜料,防水剂,气味掩蔽物质和抑制剂或防腐蚀剂等。
根据本发明,组合物或浓缩物优选含有至少一种醇酸树脂或改性的醇酸树脂和/或干燥植物油作为有机化学粘合剂。根据本发明,优选使用的物质是油含量大于45%重量,优选50-68%重量的醇酸树脂。
上面提到的粘合剂的所有或部分粘合剂可以替换成固定剂(混合物)或增塑剂(混合物)。这些添加剂是为了防止活性化合物的挥发和结晶或沉淀。优选替换0.01-30%的粘合剂(以使用的100%粘合剂为基础)。
增塑剂来自邻苯二甲酸酯类,例如邻苯二甲酸二丁酯,邻苯二甲酸二辛酯或邻苯二甲酸苄酯丁酯,磷酸酯,例如磷酸三丁酯,己二酸酯例如己二酸二-(2-乙基己基)酯,硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯,油酸酯,例如油酸丁酯,甘油醚或较高分子量的乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂的化学基础是聚乙烯基烷基醚,例如,聚乙烯基甲基醚,或酮类,例如二苯酮或亚乙基二苯酮。
作为溶剂或稀释剂特别合适的是水,如果合适,以与一种或多种上述有机化学溶剂或稀释剂,乳化剂和分散剂的混合物存在。
特别有效的木材保护作用是通过大量的工业化浸入方法实现的,例如真空,双真空或加压方法。
如果合适,即用型组合物可以另外含有一种或几种其它的杀虫剂和,如果合适,另外一种或几种杀真菌剂。
可以混合的合适的附加成分优选是WO94/29268中提到的杀虫剂和杀真菌剂。该文献中提到的化合物明确地引入本申请作为参考。
可以混合的非常特别优选的成分是杀虫剂例如毒死稗,辛硫磷,silafluofin,甲体氯氰菊酯,氟氯氰菊酯,氯氰菊酯,溴氰菊酯,氯菊酯,吡虫啉,NI-25,氟虫脲,氟铃脲和杀虫隆,和杀真菌剂例如epoxyconazole,己唑醇,戊环唑,环丙唑,戊唑醇,环唑醇,metconazole,抑霉唑,苯氟磺胺,甲苯氟磺胺,氨基甲酸3-碘代-2-丙炔基丁酯,N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明活性化合物的制备和应用可以用下面的实施例说明。
制备实施例
实施例(I-1-a-1)
80℃下,向51ml无水二甲基甲酰胺(DMF)中的14.94g(0.128mol)叔丁醇钾中滴加36ml无水DMF中的17.9g实施例II-1的化合物,并且将该混合物在室温下搅拌1.5小时。然后加入440ml冰水并且在0-20℃用浓盐酸将混合物酸化至pH1,吸滤沉淀并干燥。粗产物与甲基叔丁基醚(MTBE)/正己烷搅拌,吸滤并干燥。
产率:10g(理论量的62%);mp.:>220℃。
类似于实施例(I-1-a-1)和/或根据一般制备说明,得到下面式(I-1-a)化合物:
实施例序号 | X | Z | A | B | 异构体 | mp.℃ |
I-1-a-2 | CH3 | H | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-3 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | β | >220 | |
I-1-a-4 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-5 | OCH3 | H | -(CH2)2-CHCH3-(CH2)2- | β | 181 |
式(I-1-a);续
实施例序号 | X | Z | A | B | 异构体 | mp.℃ |
I-1-a-6 | i-C3H7 | H | -(CH2)2-CHCH3-(CH2)2- | β | 193 | |
I-1-a-7 | Cl | NO2 | -(CH2)2-CHCH3-(CH2)2- | β | >220 | |
I-1-a-8 | CH3 | CH3 | -(CH2)2-CHOC2H5-(CH2)2- | β | 128 | |
I-1-a-9 | OCH2-C6H5 | H | -(CH2)2-CHCH3-(CH2)2- | β | 188 | |
I-1-a-10 | CH3 | CH3 | i-C3H7 | CH3 | - | 117 |
I-1-a-11 | CH3 | CH3 | CH3 | CH3 | - | 210 |
I-1-a-12 | Br | OCH3 | -(CH2)2-CHCH3-(CH2)2- | β | >220 | |
I-1-a-13 | Cl | NH2 | -(CH2)2-CHCH3-(CH2)2- | β | ||
I-1-a-14 | OCH3 | Cl | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-15 | Br | OCH3 | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-16 | Cl | CH3 | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-17 | F | OCH3 | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-18 | CH3 | CH3 | -(CH2)2-O-(CH2)2- | - | 215 | |
I-1-a-19 | Cl | Cl | -(CH2)2-CHOCH3-(CH2)2- | β | 218 | |
I-1-a-20 | F | F | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-21 | Br | Br | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-22 | Cl | H | -(CH2)2-CHOCH3-(CH2)2- | β | 218 | |
I-1-a-23 | Cl | NO2 | -(CH2)2-CHOCH3-(CH2)2- | β | >220 | |
I-1-a-24 | F | CH3 | -(CH2)2-CHOCH3-(CH2)2- | β | 200-201 |
实施例(I-1-b-1)
首先将2.3g(8mmol)实施例(I-1-a-2)的化合物加入到50ml无水乙酸乙酯中,并且与1.34ml(9.6mmol)三乙胺混合,并且回流下滴加5ml无水乙酸乙酯中的1.01ml(9.6mmol)异丁酰氯。回流16小时后浓缩混合物,并且将残余物溶解于二氯甲烷,每次用50ml的0.5N氢氧化钠洗涤,洗涤两次。残余物从甲基叔丁基醚(MTB醚)/正己烷中重结晶。
产率:1.8g(Δ理论量的62%);mp.:163℃。
类似于实施例(I-1-b-1)和/或根据一般制备说明,得到下面式(I-b-1)化合物:
实施例序号 | X | Z | A | B | R1 | mp.℃ | 异构体 |
I-1-b-2 | i-C3H7 | H | -(CH2)2-CHCH3-(CH2)2- | i-C3H7- | 183 | β | |
I-1-b-3 | i-C3H7 | H | -(CH2)2-CHCH3-(CH2)2- | t-C4H9- | 198 | β | |
I-1-b-4 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | i-C3H7- | 170 | β | |
I-1-b-5 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | t-C4H9-CH2- | 198 | β | |
I-1-b-6 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | 4-Cl-C6H4- | 213 | β | |
I-1-b-7 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | i-C3H7- | 145 | β | |
I-1-b-8 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | t-C4H9-CH2- | 194 | β | |
I-1-b-9 | CH3 | CH3 | CH3 | CH3 | i-C3H7- | 188 | - |
I-1-b-10 | CH3 | CH3 | -(CH2)2-CHOC2H5-(CH2)2- | i-C3H7- | 143 | β | |
I-1-b-11 | Br | OCH3 | -(CH2)2-CHCH3-(CH2)2- | i-C3H7- | 151 | β | |
I-1-b-12 | Cl | NO2 | -(CH2)2-CHCH3-(CH2)2- | i-C3H7- | >220 | β | |
I-1-b-13 | O-CH2-C6H5 | H | -(CH2)2-CHCH3-(CH2)2- | i-C3H7- | 161 | β | |
I-1-b-14 | CH3 | CH3 | i-C3H7 | CH3 | C2H5-O-CH2- | 103 | - |
I-1-b-15 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | i-C4H9- | 157 | β | |
I-1-b-16 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | 环己基 | 171 | β | |
I-1-b-17 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | C2H5O-CH2- | 131 | β | |
I-1-b-18 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | 4-Cl-C6H4- | 164 | β |
式(I-1-b)续
实施例(I-1-c-1)
首先将2.3g(8mmol)实施例(I-1-a-2)的化合物加入到50ml无水二氯甲烷中,并且与1.12ml(8mmol)三乙胺混合,并且在0-10℃下滴加在5ml无水二氯甲烷中的0.8ml(8mmol)氯甲酸乙酯。继续在室温下搅拌,并且通过TLC监测反应,然后每次用50ml的0.5N氢氧化钠洗涤混合物两次,干燥并蒸发。残余物从MTB醚/正己烷中重结晶。产率:1.7g(Δ理论量的59%);mp.:135℃。
类似于实施例(I-1-c-1)和/或根据一般制备说明,得到下面式(I-1-c)化合物:
实施例序号 | X | Z | A | B | M | R2 | mp.℃ | 异构体 |
I-1-c-2 | i-C3H7 | H | -(CH2)2-CHCH3-(CH2)2- | O | C2H5 | 198 | β | |
I-1-c-3 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | O | C2H5 | 146 | β | |
I-1-c-4 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | O | C2H5 | 128 | β | |
I-1-c-5 | CH3 | CH3 | CH3 | CH3 | O | C2H5 | 139 | - |
I-1-c-6 | CH3 | CH3 | -(CH2)2-CHOC2H5-(CH2)2- | O | C2H5 | 126 | β | |
I-1-c-7 | Br | OCH3 | -(CH2)2-CHCH3-(CH2)2- | O | C2H5 | 175 | β | |
I-1-c-8 | Cl | NO2 | -(CH2)2-CHCH3-(CH2)2- | O | C2H5 | 236 | β | |
I-1-c-9 | O-CH2-C6H5 | H | -(CH2)2-CHCH3-(CH2)2- | O | C2H5 | 131 | β | |
I-1-c-10 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | O | i-C4H9- | 122 | β | |
I-1-c-11 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | O | C6H5-CH2 | 139 | β | |
I-1-c-12 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | O | C6H5- | 193 | β | |
I-1-c-13 | OCH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | O | C2H5- | 208-211 | β | |
I-1-c-14 | Br | OCH3 | -(CH2)2-CHOCH3-(CH2)2- | O | C2H5- | 180-182 | β | |
I-1-c-15 | Cl | CH3 | -(CH2)2-CHOCH3-(CH2)2- | O | C2H5- | 153-155 | β | |
I-1-c-16 | Br | Br | -(CH2)2-CHOCH3-(CH2)2- | O | C2H5- | >230 | β |
式(I-1-c):续
实施例序号 | X | Z | A | B | M | R2 | mp.℃ | 异构体 |
I-1-c-17 | CH3 | CH3 | -(CH2)2-CHOC2H5-(CH2)2- | O | i-C4H9- | 137-139 | β | |
I-1-c-18 | CH3 | CH3 | -(CH2)2-CHOC2H5-(CH2)2- | O | C6H5-CH2 | 135-137 | β | |
I-1-c-19 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | S | i-C3H7- | 152-154 | β | |
I-1-c-20 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | S | t-C4H9- | 200-201 | β | |
I-1-c-21 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | S | C6H5-CH2- | 148-149 | β |
实施例(I-1-g-1)
将1.8g(6mmol)实施例(I-1-a-4)的化合物和1.2ml(1.5当量)三乙胺先加在50ml乙酸甲酯中,并且在回流下加热。加入5ml乙酸甲酯中0.91ml(1.1g;1.3当量)吗啉-N-甲酰氯。混合物在回流下加热过夜,浓缩,残余物溶解于二氯甲烷。每次用40ml N氢氧化钠将有机相洗涤两次,干燥并浓缩。残余物(2.7g)与石油醚搅拌,吸滤并干燥。产率:0.90g(理论量的36%);mp.:132℃。
实施例I-1-g-2
类似于和/或根据一般制备说明,得到下面油状化合物:
实施例(II-1)
0-10℃下,向200ml无水THF中的20.8g 1-氨基-4-甲基环己烷羧酸甲酯和29.4ml(0.21mol)三乙胺中滴加20ml无水四氢呋喃(THF)中的16.9g2-甲基苯基乙酰氯,在室温下搅拌混合物。反应完后(通过薄层色谱(TLC)控制),浓缩混合物,溶解于0.5N HCl/二氯甲烷的混合物中,并且干燥有机相并浓缩。残余物从MTB醚/正己烷中重结晶。产率:17.9g(理论量的59%);mp.:107℃。
类似于实施例(II-1)和/或根据一般制备说明,得到下面式(II)化合物:
实施例序号 | X | Z | A | B | R8 | 异构体 | mp.℃ |
II-2 | CH3 | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 98 | |
II-3 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | CH3 | β | 120 | |
II-4 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 90 | |
II-5 | CH3 | CH3 | CH3 | CH3 | CH3 | - | |
II-6 | OCH3 | H | -(CH2)2-CHCH3-(CH2)2- | CH3 | β | 138 | |
II-7 | O-CH2-C6H5 | H | -(CH2)2-CHCH3-(CH2)2- | CH3 | β | 85 | |
II-8 | OCH3 | Cl | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 149 | |
II-9 | CH3 | CH3 | -(CH2)2-CHOC2H5-(CH2)2- | CH3 | β | 108 | |
II-10 | CH3 | CH3 | i-C3H7 | CH3 | CH3 | - | 75 |
II-11 | CH3 | CH3 | -(CH2)2-O-(CH2)2- | CH3 | - | 153 | |
II-12 | Cl | NO2 | -(CH2)2-CHCH3-(CH2)2- | CH3 | β | 158 | |
II-13 | Cl | Cl | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 112 | |
II-14 | Cl | CH3 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 171 | |
II-15 | Cl | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 68 | |
II-16 | Br | OCH3 | -(CH2)2-CHCH3-(CH2)2- | CH3 | β | 131 | |
II-17 | Br | OCH3 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 158 |
实施例序号 | X | Z | A | B | R8 | 异构体 | mp.℃ |
II-18 | Br | Br | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 132 | |
II-19 | F | CH3 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 74-76 | |
II-20 | F | OCH3 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 169 | |
II-21 | F | F | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 91 | |
II-22 | Cl | NH2 | -(CH2)2-CHCH3-(CH2)2- | CH3 | β | 94 | |
II-23 | Cl | NO2 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 127 | |
II-24 | Cl | Br | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 126-128 | |
II-25 | Cl | CF3 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 109-111 | |
II-26 | Br | CH3 | -(CH2)2-CHOCH3-(CH2)2- | CH3 | β | 100-102 |
实施例(II-10)
在30-40℃内部温度下,向32.2g(0.326mol)浓硫酸中滴加200ml二氯甲烷中16.7g实施例(XXVIII-1)的化合物,并且在该温度下将该混合物再搅拌2小时。然后以一种方式滴加42ml无水甲醇使得保持40℃内部温度。混合物在40-70℃下再搅拌6小时,倒入0.35kg冰中,并且用二氯甲烷萃取,用碳酸氢钠水溶液洗涤有机相,干燥并浓缩,残余物从MTB醚/正己烷中结晶。
产率:7.40g(理论量的39%);mp.:75℃。
实施例(II-22)
370ml乙醇中37g实施例(II-12)的化合物与阮内镍混合并氢化。过滤出催化剂,浓缩滤液,残余物从MTB醚/正己烷中重结晶。得到10.3g固体,mp.:94℃。浓缩母液,又得到20g产物,为油状物。总产率:理论量的89%。
实施例(I-2-a-1)
0-10℃下,向50ml无水THF中8.42g(75mmol)叔丁醇钾中滴加50ml四氢呋喃(THF)中16.6g(50mmol)实施例(III-1)2-氯苯基乙酸1-乙氧羰基-环己基酯的溶液,并且混合物在室温下搅拌16小时。
后处理时,将反应混合物滴加到500ml冰冷的1N盐酸中,并且吸滤沉淀的产物,用水洗涤,并在真空干燥箱中干燥。
产率:10.19g(理论量的80%);mp.:231℃。
类似地和/或根据一般制备说明,得到下面式(I-2-a)化合物:
实施例序号 | X | Z | A | B | mp.℃ |
I-2-a-2 | CH3 | H | -(CH2)5- | 233 | |
I-2-a-3 | OCH3 | H | -(CH2)5- | 177 | |
I-2-a-4 | F | H | -(CH2)5- | 233 | |
I-2-a-5 | i-C3H7 | H | -(CH2)5- | 200 | |
I-2-a-6 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | 180 | |
I-2-a-7 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | 240 |
实施例(I-2-b-1)
先将2.79g(10mmol)实施例(I-2-a-1)的化合物加入到50ml无水THF中,加入1.21g(12mmol)三乙胺,冰冷却下滴加1.33g(11mmol)新戊酰氯溶液,混合物在室温下搅拌16小时。后处理时,混合物搅拌下倒入200ml水中,并且吸滤产物,并干燥。
产率:3.5g(理论量的98%);mp.:128℃-
类似地和/或根据一般制备说明,得到下面式(I-2-b)化合物:
实施例序号 | X | Z | A | B | R1 | mp.℃ |
I-2-b-2 | CH3 | H | -(CH2)5- | t-C4H9 | 101 | |
I-2-b-3 | Cl | H | -(CH2)5- | H5C2-C(CH3)2- | 90-92 | |
I-2-b-4 | OCH3 | H | -(CH2)5- | t-C4H9 | oil | |
I-2-b-5 | F | H | -(CH2)5- | t-C4H9 | 88 | |
I-2-b-6 | i-C3H7 | H | -(CH2)5- | t-C4H9 | 98 | |
I-2-b-7 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | i-C3H7 | 91 | |
I-2-b-8 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | i-C3H7 | 104-106 |
实施例(I-2-c-1)
0-10℃下,30ml二氯甲烷中1.43g实施例(I-2-a-7)的化合物与0.55g三乙胺和0.75g氯甲酸异丁酯混合。
根据实施例(I-1-c-1)所述进行后处理。
产率:0.94g;mp.:70℃。
实施例(I-2-c-2)
以类似方法从实施例(I-2-a-6)的化合物得到该化合物。
产率:1.7g,半晶体。
实施例(III-1)
8.6g(50mmol)2-氯苯基乙酰氯与8.6g(50mmol)1-羟基-环己烷羧酸乙酯一起在120℃下搅拌5小时,并且用油泵脱气。
产率:15.26g作为无色油状物的2-氯苯基乙酸1-乙氧羰基-环己基酯。
1H NMR(300MHz,CDCl3):δ=1.1δ(t,3H,CH2 CH 3),1.2-1.82(m,8H,c-Hcx),2.12(m,2H,c-Hcx),3.81(s,2H,
CH 2-CO),4.14(q,2H,O-
CH 2-CH3),7.15-7.4(m,4H,Ar-
H)
以类似方法和/或根据一般制备说明,得到下面式(III)化合物:
实施例序号 | X | Z | A | B | R8 | mp.℃ |
III-2 | CH3 | H | -(CH2)5- | C2H5 | 油 | |
III-3 | OCH3 | H | -(CH2)5- | C2H5 | 油 | |
III-4 | F | H | -(CH2)5- | C2H5 | 油 | |
III-5 | i-C3H7 | H | -(CH2)5- | C2H5 | 油 | |
III-6 | CH3 | CH3 | -(CH2)2-CHOCH3-(CH2)2- | C2H5 | 油 | |
III-7 | CH3 | CH3 | -(CH2)2-CHCH3-(CH2)2- | C2H5 | 油 |
实施例(I-3-a-1)
86ml甲苯中的19g实施例(IV-1)的化合物和43ml三氟乙酸在回流下加热过夜。减压去除过量的三氟乙酸,残余物溶解于400ml水和120ml MTBE中,并且通过加入氢氧化钠而将pH调节到14值。用MTBE萃取混合物两次,并且用盐酸酸化水相,用MTBE萃取三次、干燥有机相并蒸发。
产率:7.8g(理论量的63%);mp.:185-187℃。
实施例(I-3-b-1)
20ml二氯甲烷中1.5g实施例(I-3-a-1)的化合物与1.08ml三乙胺混合。冰冷却下,滴加3ml二氯甲烷中0.96ml新戊酰氯的溶液,并且在室温下再搅拌2小时。混合物用10%强度柠檬酸洗涤两次并用二氯甲烷萃取。合并的有机相用1N氢氧化钠洗涤两次,并且用二氯甲烷萃取碱水相。干燥合并的有机相并浓缩。
产率:1.90g(理论量的98%);mp.:79-83℃。
实施例(I-3-b-2)
类似于实施例(I-3-b-1),当使用异丁酰氯代替新戊酰氯时,定量得到熔点是149-152℃的下面化合物:
实施例(I-3-c-1)
类似于实施例(I-3-b-1),当使用氯甲酸异丁酯代替新戊酰氯时,以理论量的98%的产率得到熔点是101-103℃的下面化合物:
实施例(IV-1)
A:40ml甲苯中10g化合物(1)与1滴DMF和6.4g亚硫酰氯混合,并在室温下搅拌5分钟,然后在100℃下搅拌,直到生成的气体逸出。去除过量的亚硫酰氯(高真空),并且将酰基氯溶解于20ml THF(四氢呋喃)中:溶液A.
B:0℃下,向50ml THF中二异丙基氨基锂(LDA)(65.8mmol)的溶液32ml中滴加20ml THF中10.7g化合物(2),混合物在0℃下搅拌30分钟。然后在该温度下滴加溶液A,不加冷却下将混合物再搅拌1小时。
混合物与175ml MTBE和几滴水混合。然后用10%强度氯化铵水溶液将混合物洗涤两次,干燥有机相并浓缩。
产率:19g(油状物)
1H NMR(400MHz,CDCl3):1.2-2.0(m,10H,CH2);2.32,2.38(2s,2×3H;CH3),3.22(dd,2H,CH2);3.71,3.76(2s,2×3H,OCH3);6.7-7.4(m,7H,苯基-H)
实施例(I-4-a-1)
先将1.9g(10mmol)2-(2-甲基-苯基)-氯羰基烯酮加入到20ml无水甲苯中。加入1.4g(10mmol)乙基2-吡啶基酮后,回流下加热混合物8小时。冷却后,吸滤沉淀,并用环己烷洗涤两次。
产率:2.1g(理论量的71%);mp.:105-107℃。
以类似方法和/或根据一般制备说明,得到下面式(I-4-a)化合物:
实施例序号 | X | Z | A | D | mp.℃ |
I-4-a-2 | CH3 | H | CH3 | 4-F-苯基 | 187-190 |
I-4-a-3 | Cl | H | CH3 | CH3 | 97-100 |
I-4-a-4 | Cl | H | -[C(CH3)2]-O-[C(CH3)2]- | 194-196 | |
I-4-a-5 | CHx3 | CH3 | -[C(CH3)2]-O-[C(CH3)2]- | 174-175 | |
I-4-a-6 | CH3 | CH3 | -(CH2)4- | 198-200 | |
I-4-a-7 | CH3 | CH3 | CH3 | 2-吡啶基 | 99-102 |
I-4-a-8 | CH3 | CH3 | CH3 | 4-吡啶基 | 273-275 |
I-4-a-9 | CH3 | CH3 | CH3 | CH3 | 57-59 |
实施例(I-4-b-1)
10ml乙酸乙酯中1.2g(4mmol)实施例(I-4-a-7)的化合物与0.4g(4mmol)三乙胺混合,并且在0℃滴加溶解于4ml乙酸乙酯的0.7g(4mmol)6-氯代吡啶-3-基-羰基氯。混合物在室温下保持20小时,并吸滤沉淀,并用乙酸乙酯洗涤,每次用20ml半浓氯化钠水溶液将有机相洗涤两次,干燥并浓缩。
产率:2g(理论量的91%);mp.:70-73℃。
类似于(I-4-b-1)和/或根据一般制备说明,得到下面式(I-4-b)化合物:
实施例(I-4-c-1)
20ml乙酸乙酯中1.5g(5mmol)实施例(I-4-a-7)的化合物与0.5g(5mmol)三乙胺混合,并且在0℃滴加溶解于5ml乙酸乙酯的0.47g(5mmol)氯甲酸甲酯。混合物在室温下搅拌20小时,分离沉淀并用乙酸乙酯洗涤,每次用25ml半浓氯化钠水溶液将有机相洗涤两次,干燥并浓缩。
产率:1.7g(理论量的93%);mp.:136-137℃。
实施例(XXXII-1)
先将236g(2.8mol)碳酸二甲酯加入到814ml无水甲苯中,加入27.3g(0.91mol)氢化钠(80%)。80℃下,滴加133g(0.7mol)2-氯苯基乙酸甲酯,混合物在80-90℃搅拌16小时。混合物倒入2L冰水中,并用半浓盐酸酸化至pH4,分离有机相,用150ml甲苯萃取水相。干燥合并的有机相,蒸馏出溶剂,残余物用高真空蒸馏。
产率:122.9g(理论量的72%),bp(0.6-0.7mbar)129-131℃。
以类似方法和/或根据一般制备说明,得到下面式(XXXII)化合物:
实施例序号 | X | Z | R8 | bp. |
XXXII-2 | CH3 | H | CH3 | 作为粗产物使用 |
XXXII-3 | CH3 | CH3 | CH3 | 1H NMR(400MHz,CDCl3)δ=2.25(s,3H,CH3),1,28(3H,s,CH3);3.78(s,6-H,2×CO2CH3);4,88(s,1H,CH) |
实施例(XXXI-1)
将93.3g(1.67mol)氢氧化钾溶解到125ml水中,并且与250ml甲醇混合。然后,滴加121.3g(0.5mol)实施例(XXXII-1)的化合物。回流5小时后,蒸发混合物,且残余物溶解于乙酸乙酯,在0℃下,小心地用浓盐酸酸化。吸滤沉淀,减压下用氯化钙干燥。
产率:29.2g(理论量的27%),mp.:135-136℃(分解)。
以类似方法和/或根据一般制备说明,得到下面式(XXXI)化合物:
实施例序号 | X | Z | mp.℃ |
XXXI-2 | CH3 | H | 149-150(分解) |
XXXI-3 | CH3 | CH3 | 150 |
实施例(VI-1)
先将27.9g(0.13mol)2-(2-氯-苯基)-丙二酸加入到32ml无水甲苯中,滴加59g(0.391mol)亚硫酰氯,混合物在回流下加热5小时。浓缩和蒸馏后得到20.7g(理论量的74%)2-(2-氯苯基)-2-氯羰基烯酮,bp(1mbar)102℃。
以类似方法和/或根据一般制备说明,得到下面式(VI)化合物:
实施例序号 | X | Y | bp.℃ |
VI-2 | CH3 | H | 92-94(0.6mbar) |
VI-3 | CH3 | CH3 | 1H NMR(400MHz,CDCl3)δ=2.20,221(2s.6H,2CH3),705(m,3H,Ph- H) |
实施例(XXII-1)
向220mlTHF中上述实施例(XXIII-1)的55g羧酸酯滴加220ml水中5.10g 98%强度氢氧化锂的溶液,混合物在室温下搅拌过夜。然后蒸发混合物,残余物与水混合并且用MTBE萃取,水相用浓盐酸酸化,并且吸滤沉淀。
类似于实施例(XXII-1)和/或根据一般制备说明,得到下面式(XXII)化合物:
实施例 序号 | X | Z | mp.℃ |
XXII-2 | OCH3 | Cl | 128-130 |
XXII-3 | Cl | CH3 | 116-120 |
XXII-4 | F | CH3 | 89 |
XXII-5 | Br | Br | 95 |
XXII-6 | F | F | 118 |
XXII-7 | Cl | Br | 115 |
XXII-8 | Cl | CF3 | 110 |
XXII-9 | Br | CH3 | 117 |
实施例(XXIII-1)
冷却下,向220ml甲醇中实施例(XXIV-1)的653g(1.26mol)(68%)化合物中滴加1020ml 30%强度甲醇钠水溶液(5.67mol),混合物在回流下搅拌5小时。然后在冷却下,滴加200ml浓硫酸后,混合物在回流下再搅拌1小时。浓缩混合物,与水混合并且用二氯甲烷萃取,干燥并浓缩萃取液。
粗产率:355g(81%纯度)。
类似于实施例(XXIII-1)和/或根据一般制备说明,得到下面式(XXIII)化合物:
实施例序号 | X | Z | R8 | bpmbar℃ |
XXIII-2 | OCH3 | Cl | CH3 | 1200.09 |
XXIII-3 | Cl | CH3 | CH3 | 1250.1 |
XXIII-4 | F | CH3 | CH3 | 600.05 |
XXIII-5 | Br | Br | CH3 | GC/MS308(M+,4%)249(42%)227(77%) |
XXIII-6 | F | F | CH3 | 1000.03 |
XXIII-7 | Cl | Br | CH3 | 101℃/0,25mbar |
XXIII-8 | Cl | CF3 | CH3 | Kp 110℃/0,35mbar |
XXIII-9 | Br | CH3 | CH3 | GC/MS183(29%)163(100%) |
实施例(XXIV-1)
氩气下,向750ml无水乙腈中229g亚硝酸异戊酯中加入202.9g无水氯化铜(II)后加1890g 1,1-二氯乙烷。低于30℃下,分批加204g2,5-二氯苯胺,混合物在室温下搅拌过夜,直到生成的气体逸出。将混合物倒入3600ml冰冷的20%强度盐酸中,搅拌10分钟,用MTBE反复萃取。有机相用20%强度盐酸洗涤,干燥并浓缩。
MS与该结构吻合。
类似于实施例(XXIV-1)和/或根据一般制备说明,得到下面式(XXIV)化合物:
实施例序号 | X | Z | GC/MS |
XXIV-2 | OCH3 | Cl | 274(12%,M-)155(100%) |
XXIV-3 | Cl | CH3 | 256(5%,M+)185(7%)139(100%) |
XXIV-4 | F | CH3 | 242(7%,M+)123(100%) |
XXIV-5 | Br | Br | 366(13%,M+)249(100%) |
XXIV-6 | F | F | 246(5%,M+)127(100%) |
XXIV-7 | Cl | Br | M+322(17%)205(100%) |
XXIV-8 | Cl | CF3 | M+312(4%)193(100%) |
XXIV-9 | Br | CH3 | M+302(22%)185(100%) |
实施例(XXVIII-1)
0-10℃下,向160mlTHF和12.3ml三乙胺中9g(0.08mol)上述氨基腈中滴加20mlTHF中14.9g 2,5-二甲基苯基乙酰氯。
反应完全后,浓缩混合物,残余物溶解于0.5N盐酸/二氯甲烷,干燥并浓缩有机相。残余物经硅胶用正己烷/乙酸乙酯进行色谱。产率:16.70g(理论量的80%);mp.:89℃。
实施例(XXVIII-2)
以类似方法,定量得到下式化合物
mp.:198℃。
应用实施例
实施例A
猿叶虫(Phaedon)幼虫试验
溶剂:7份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用辣根猿叶甲(Phaedon cochleariae)幼虫侵染。
一定时间后,测定损害百分率。100%表示所有的甲虫幼虫都已经被杀死;0%表示没有杀死一只甲虫幼虫。
在该试验中,例如制备实施例(I-1-a-1)和(I-4-a-1)的化合物在例示的0.1%活性化合物浓度下,7天后,各种情况下均引起100%的破坏。
实施例B
菜蛾(Plutella)试验
溶剂:7份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用小菜蛾(Plutellamaculipennis)毛虫侵染。
一定时间后,测定损害百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该试验中,例如制备实施例(I-4-a-1)和(I-4-a-2)的化合物在例示的0.1%活性化合物浓度下,7天后,各种情况下均引起100%的破坏。
实施例C
夜蛾(Spodoptera)试验
溶剂:7份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用甜菜夜蛾(Spodoptera frugiperda)毛虫侵染。
一定时间后,测定杀伤百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该试验中,例如制备实施例(I-1-a-1)和(I-4-a-1)的化合物在例示的0.1%活性化合物浓度下,7天后,各种情况下引起85%的破坏。
实施例G
瘤额蚜(Myzus)试验
溶剂:7份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理被桃蚜(Myzus persicae)严重侵染的甘蓝叶(Brassica oleracea)。
一定时间后,测定损害百分率。100%表示所有的蚜虫都已经被杀死;0%表示没有杀死一只蚜虫。
在该试验中,例如制备实施例(I-2-a-1),(I-2-b-1),(I-2-b-2),(I-1-a-1)和(I-4-a-1)的化合物在例示的0.1%活性化合物浓度下,6天后,各种情况下引起90%的破坏。
实施例E
叶蝉(Nephotettix)试验
溶剂:7份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理稻苗(Oryzaesativa),并在籽苗还湿润的时候用黑尾叶蝉(Nephotettixcincticeps)幼虫侵染。
一定时间后,测定损害百分率。100%表示所有的幼虫都已经被杀死;0%表示没有杀死一只幼虫。
在该试验中,例如制备实施例(I-2-a-2),(I-2-b-3),(I-1-a-1),(I-4-a-1)和(I-4-a-2)的化合物在例示的0.1%活性化合物浓度下,6天后,各种情况下引起100%的破坏。
实施例F
叶螨(Tetranychus)试验(OP抗性)
溶剂:7份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理被所有发育期红叶螨(Tetranychus urticae)严重侵染的豆类植物(Phaseolusvulgaris)。
一定时间后,测定损害百分率。100%表示所有的叶螨都已经被杀死;0%表示没有杀死一只叶螨。
在该试验中,例如制备实施例(I-2-a-1),(I-2-a-2),(I-2-b-1)和(I-2-b-2)的化合物在例示的0.1%活性化合物浓度下,9天后,各种情况下达到至少98%的药效。
实施例G
叶螨(Tetranychus)试验(OP抗性/浸入处理)
溶剂:3份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理被所有发育期红叶螨(Tetranychus urticae)严重侵染的豆类植物(Phaseolusvulgaris)。
一定时间后,测定损害百分率。100%表示所有的叶螨都已经被杀死;0%表示没有杀死一只叶螨。
在该试验中,例如制备实施例(I-2-a-1),(I-2-a-2),(I-2-b-1)和(I-2-b-2)的化合物在例示的0.01%活性化合物浓度下,13天后,各种情况下达到至少95%的药效。
实施例H
红蜘蛛(Panonychus)试验
溶剂:3份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
用期望浓度的活性化合物制剂喷雾被所有发育期苹果红蜘蛛(Panonychus ulmi)严重侵染的大约30cm高的李树(Prunusdomestica)。
一定时间后,测定损害百分率。100%表示所有的红蜘蛛都已经被杀死;0%表示没有杀死一只红蜘蛛。
在该试验中,例如制备实施例(I-2-b-1)和(I-2-b-2)的化合物在例示的0.004%活性化合物浓度下,7天后,各种情况下具有100%的药效。
实施例I
蝇幼虫试验/发育抑制作用
试验动物:所有幼虫阶段的铜绿蝇(Lucilia cuprina)(OP抗性)
[蛹和成虫(没有与活性化合物接触)]
溶剂:35份重量乙二醇一甲醚
35份重量壬基苯酚聚乙二醇醚
为了制备合适的制剂,将3份重量活性化合物与7份重量上述溶剂-乳化剂混合物混合,并在各种情况下用水将得到的乳油稀释到需要的浓度。
对于各浓度,向含有1cm3马肉的试管中加入30-50只幼虫。将500μl待试验的稀释液用移液管加到马肉上。将试验试管放置在底部覆盖沙子的塑料杯中,保持在气候化实验室(26℃±1.5℃,70%±10%相对湿度)中。24小时和48小时后测定活性(杀幼虫作用)。当幼虫羽化后(大约72小时),取出试管,并且将穿孔的塑料盖盖在烧杯上。发育时间(对照蝇的孵化)的1.5倍时间后,计数孵化的蝇和蛹/茧。
活性标准是处理幼虫48小时后死亡发生率(杀幼虫效果),或者对从蛹孵化成成虫的抑制作用或者对蛹生成的抑制作用。对于物质体外活性评判的标准是对蝇发育的抑制作用,或者成虫期之前发育停止。100%杀幼虫作用指48小时后所有的幼虫都已经被杀死。100%发育抑制作用指没有发育成成虫蝇。
在该试验中,例如制备实施例(I-2-b-3)的化合物在例示的1000ppm活性化合物浓度时表现出100%发育抑制作用。
实施例K
微小牛蜱(Boophilus microplus)抗性试验/SP抗性Parkhurst品系
试验动物:已经吮饱的雌成虫
溶剂:二甲亚砜
20mg活性物质溶解于1ml二甲亚砜中,通过用相同溶剂稀释来制备较小浓度。
重复5次试验。将1μl溶液注入腹部,并且将动物转移到盘中并保持在控制环境的室中。通过抑制产卵测定活性。100%表示没有蜱产卵。
在该试验中,例如制备实施例(I-1-a-2)的化合物在例示的20μg/动物活性化合物浓度时表现出100%活性。
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