CN1192123A - N-芳基-1,2,4-三唑啉-5-酮 - Google Patents
N-芳基-1,2,4-三唑啉-5-酮 Download PDFInfo
- Publication number
- CN1192123A CN1192123A CN96195972A CN96195972A CN1192123A CN 1192123 A CN1192123 A CN 1192123A CN 96195972 A CN96195972 A CN 96195972A CN 96195972 A CN96195972 A CN 96195972A CN 1192123 A CN1192123 A CN 1192123A
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- CN
- China
- Prior art keywords
- alkyl
- optional
- represent
- group
- alkoxyl
- Prior art date
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- 241001465754 Metazoa Species 0.000 claims abstract description 19
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 10
- -1 nitro- Chemical class 0.000 claims description 436
- 150000001875 compounds Chemical class 0.000 claims description 238
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 149
- 239000000460 chlorine Chemical group 0.000 claims description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 80
- 125000003545 alkoxy group Chemical group 0.000 claims description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 150000002431 hydrogen Chemical group 0.000 claims description 67
- 229910052731 fluorine Inorganic materials 0.000 claims description 62
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
- 239000011737 fluorine Chemical group 0.000 claims description 58
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical group 0.000 claims description 48
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 47
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 43
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- 125000005843 halogen group Chemical group 0.000 claims description 42
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
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- 238000006243 chemical reaction Methods 0.000 claims description 25
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
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- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 108010067167 thuricin Proteins 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及部分已知的式(Ⅰ)N-芳基-1,2,4-三唑啉-5-酮用于防治动物害虫的用途,其中A、R1、R2、R3、R4和R5各如说明书中所定义。
Description
本发明涉及新的和已知的N-芳基-1,2,4-三唑啉-5-酮防治动物害虫,特别是防治出现在农业、森林、贮藏产品和材料保护以及卫生方面上的昆虫、蜱螨和线虫的应用。
业已知道,某些取代的N-芳基-1,2,4-三唑啉-5-酮衍生物(参见例如EP-A0610733和EP-A0617026)具有除草性能。但并不知道由EP-A-0617026已知的化合物具有杀虫活性。由EP-A-0610733已知的化合物据称在适宜的施用量下对叶面昆虫和蜱螨具有活性。然而,这些化合物的杀虫活性,特别是在低施用量和浓度下的杀虫活性并不总是令人满意。
因此,本发明提供新的和已知的式(I)N-芳基-1,2,4-三唑啉-5-酮,它们非常适合用于防治动物害虫,特别是昆虫、蜱螨和线虫,
其中
A代表氮或基团CR,
R代表氢、卤素、硝基、氰基、羟基,任选卤素-、氰基-、硝基-、烷氧基-或氨基取代的烷基,任选取代的环烷基或基团-CX-NY1Y2,
R1代表卤素、硝基、氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基取代的烷基或烷氧基,任选取代的环烷基或基团-CX-NY1Y2,
R2代表氢、卤素,任选卤素-、氰基-、硝基-、烷氧基-或氨基取代的烷基或任选取代的环烷基,
R3代表硝基、卤代烷基、卤代烷氧基或基团-S(O)nR6,
R4代表卤素、硝基、氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、羟基、巯基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基、芳氧基烷基或芳烷基或基团-S(O)nR6,
R5代表氢、氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、炔氧基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基或芳烷基或基团-S(O)nR6、-NR7R8或-N=CR9R10,
R6代表任选卤素-、氰基-、硝基-、烷氧基或氨基取代的烷基,代表链烯基、链二烯基、炔基,任选取代的环烷基或任选取代的芳基,
R7代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基取代的烷基,代表链烯基、炔基、烷氧基,任选取代的环烷基或任选取代的芳基,
R8代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基取代的烷基,代表链烯基、炔基、烷氧基,任选取代的环烷基或任选取代的芳基,或
R7和R8与连接氮原子一起代表任选取代杂环,该杂环可任选含有一或多个另外的杂原子,
R9代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,
R10代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,
X代表氧或硫,
Y1代表氢或烷基,
Y2代表氢或烷基,且
n代表数字0、1或2之一。
取决于取代基的性质,式(I)化合物可以作为不同组分的几何和/或光学异构体或异构体混合物存在。本发明涉及纯异构体和异构体混合物两者。
出人意外的是,根据本发明使用的N-芳基-1,2,4-三唑啉-5-酮具有比结构上最相似的现有技术化合物对动物害虫明显更好的活性。
式(I)提供可根据本发明使用的N-芳基-1,2,4-三唑啉-5-酮的一般定义。
列举于上下文中提到的化学式中基团的优选取代基和范围说明如下。
A优选代表氮或基团CR,
R优选代表氢、氟、氯、溴、硝基、氰基、羟基,任选氟-、氯-、溴-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基取代的C3-C6-环烷基,或代表下列基团之一:-CONH2、-CSNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2或-CS-N(C1-C4-烷基)2,
R1优选代表氟、氯、溴、硝基、氰基,各任选氟-、氯-、溴-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基或C1-C4-烷氧基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基取代的C3-C6-环烷基,或代表下列基团之一:-CONH2、-CSNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2或-CS-N(C1-C4-烷基)2,
R2优选代表氢、氟、氯、C1-C4-烷基或C1-C4-卤代烷基,
R3优选代表硝基、C1-C4-卤代烷基、C1-C4-卤代烷氧基或下列基团之一:-S-C1-C4-卤代烷基、-SO-C1-C4-卤代烷基或-SO2-C1-C4-卤代烷基,
R4优选代表卤素、硝基、氰基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-、或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、羟基、巯基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基、苯氧基-C1-C4-烷基或苯基-C1-C4-烷基,它们各任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,或代表基团-S(O)nR6,
R5优选代表氢、氰基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、C3-C6-炔氧基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或C3-C6-环烷基-C1-C4-烷基,任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,或代表C1-C4-烷基取代的苄基或下列基团之一:-S(O)nR6、-NR7R8或-N=CR9R10,
R6优选代表任选氟-、氯-、氰基-、硝基-取代的C1-C4-烷基,代表C3-C6-链烯基、C3-C6-链二烯基、C3-C6-炔基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,
n优选代表数字0、1或2之一,
R7特别优选代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基-取代的C1-C4-烷基,代表C3-C6-链烯基、C3-C6-炔基或C1-C4-烷氧基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,
R8优选代表氢,任选氟-、氯-、氰基-、硝基-、氨基或C1-C4烷氧基取代的C1-C4烷基,代表C3-C6-链烯基、C3-C6-炔基或C1-C4-烷氧基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,
R7和R8优选与连接氮原子一起代表任选卤素-、C1-C4-烷基、C1-C4-烷氧基或C1-C4-烷硫基取代的5至7元饱和杂环,该杂环除了氮原子外,具有2或3个相同或不同的选自氮、氧或硫的杂原子,
R9优选代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基,
R10优选代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基。
A特别优选代表氮或基团CR,
R特别优选代表氢、氟、氯、溴、硝基、氰基、羟基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基或代表下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2或-CSN(CH3)2,
R1特别优选代表氟、氯、溴、硝基、氰基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、三氟乙氧基或代表下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2或-CSN(CH3)2,
R2特别优选代表氢、氟、氯、甲基或三氟甲基,
R3特别优选代表三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、三氟甲基亚磺酰基、三氟甲基亚硫酰基或三氟甲基磺酰基,
R4特别优选代表氯、溴、硝基、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、三氟乙氧基、四氟乙氧基、五氟乙氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、羟基、巯基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表苯基、苯氧基甲基或苄基,它们各任选被氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、硝基或任选氟-、氯-或甲基取代的苯基取代或代表基团-S(O)nR6,
R5特别优选代表氢、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、氟丙基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、炔丙氧基、丁炔氧基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表任选被氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基或任选氟-、氯-或甲基取代的苯基取代的苯基,代表任选甲基-、乙基-、正或异丙基-、正、异、仲或叔丁基取代的苄基,或代表下列基团之一:-S(O)nR6、-NR7R8或-N=CR9R10,
R6特别优选代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、烯丙基、丙二烯基、炔丙基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环戊基或环己基,或任选被氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基或任选氟-、氯-或甲基取代的苯基取代的苯基,
n特别优选代表数字0、1或2之一,
R7特别优选代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基或环丙基,
R8特别优选代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基或环丙基,或
R7和R8与连接的氮原子一起代表各任选甲基-、乙基-、甲氧基-或乙氧基-取代的哌啶基、哌嗪基或吗啉基,
R9特别优选代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基,
R10特别优选代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基。
一些式(I)化合物是已知的(参见例如EP-A0617026)。
在上面的一般性或在优选范围中提到的基团的定义或说明适用于终产物,且相应地适用于原料和中间体。这些基团的定义可以按需要相互间组合,即各自优选范围间的组合也是可以的。
根据本发明,优选的是使用那些存在上述优选含意组合的式(I)化合物。
根据本发明,特别优选的是使用那些存在上述特别优选含意组合的式(I)化合物。
在上下文所提到的基团的定义中,烃基基团如烷基或链烯基,包括与杂原子相连的烃基如烷氧基或烷硫基,在每种情况下,尽可能是直链或支链。
其中
A1代表氮或基团CR0,
R0代表氢、卤素、硝基、氰基、羟基,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,任选取代的环烷基或基团-CX1-NY11Y12,
R11代表卤素、硝基、氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,任选取代的环烷基或基团-CX1-NY11Y12,
R12代表氢、卤素,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,任选取代的环烷基,
R13代表硝基、卤代烷基、卤代烷氧基或基团-S(O)n 1R16,
R14代表卤素、氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、羟基、巯基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基、芳氧基烷基或芳烷基或基团-S(O)1 nR16,
R15代表氢、氰基、氨基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、炔氧基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基或芳烷基或基团-S(O)1 nR16、-NR17R18或-N=CR19R20之一,
R16代表任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表链烯基、链二烯基、炔基,任选取代的环烷基或任选取代的芳基,
R17和R18与连接的氮原子一起代表任选取代杂环,该杂环可任选含有一或多个另外的杂原子,
R19代表氢,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,
R20代表氢,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,
X1代表氧或硫,
Y11代表氢或烷基,
Y12代表氢或烷基,且
n代表数字0、1或2之一。
取决于取代基的性质,式(I)化合物可以作为不同组分的几何和/或光学异构体或异构体混合物存在。本发明涉及纯异构体和异构体混合物两者。
其中
R11、R12、R13、R14、R15和A1各如上所定义,
如果适宜,在稀释剂存在下,和如果适宜在反应辅助剂存在下,使式(II)的1H-三唑啉酮与式(III)的卤素衍生物反应其中R14和R15各如上所定义,
其中
R11、R12、R13和A1各如上所定义,且
Ha1代表卤素;
或
其中
R11、R12、R13和A1各如上所定义,且
R14-1代表氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基,各任选取代的环烷基或环烷基烷基或各任选取代的芳基、芳氧基烷基或芳烷基,
在稀释剂存在下,使式(IV)的肼衍生物与式(V)的亚氨基羧酸酯反应
其中
R11、R12、R13和A1各如上所定义,
其中
R14-1如上所定义,且
R21和R22相互独立地各代表烷基(优选C1-C8-烷基);
或
c)如下获得式(Ic)的N-芳基-1,2,4-三唑啉-5-酮
其中
R11、R12、R13、R14和A1各如上所定义,且
R15-1代表氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表链烯基、炔基、各任选取代的环烷基和环烷基烷基或任选取代的芳基,
如果适宜,在稀释剂存在下,且如果适宜在反应辅助剂存在下,使式(Id)的N-芳基-1,2,4-三唑啉-5-酮与式(VI)的烷基化试剂反应
其中
R11、R12、R13、R14和A1各如上所定义,
E-R15-1 (VI)
其中
R15-1如上所定义,且
E代表吸电子离去基团。
新颖的本发明N-芳基-1,2,4-三唑啉-5-酮的一般定义由式(Ia)给出。
列举于上下文中提到的化学式中基团的优选取代基和范围说明于下列。
A1优选代表氮或基团CR0,
R0优选代表氢、氟、氯、溴、硝基、氰基、羟基,任选氟-、氯-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-氧基-、C1-C4-代烷基-或C1-C4-代烷氧基取代的C3-C6-烷基,或代表下列基团之一:-ONH2、-SNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2或-CS-N(C1-C4-烷基)2,
R11优选代表氟、氯、溴、硝基、氰基,各任选氟-、氯-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基或C1-C4-烷氧基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基取代的C3-C6-环烷基,或代表下列基团之一:-CONH2、-CSNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2或-CS-N(C1-C4-烷基)2,
R12优选代表氢、氟、氯、C1-C4-烷基或C1-C4-卤代烷基,
R13优选代表硝基、C1-C4-卤代烷基、C1-C4-卤代烷氧基或下列基团之一:-S-C1-C4-卤代烷基、-SO-C1-C4-卤代烷基或-SO2-C1-C4-卤代烷基,
R14优选代表卤素、氰基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、羟基、巯基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基、苯氧基-C1-C4-烷基或苯基-C1-C4-烷基,它们各任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,或代表基团-S(O)1 nR16,
R15优选代表氢、氰基,氨基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、C3-C6-炔氧基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基,该苯基任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,代表任选C1-C4-烷基取代的苄基或下列基团之一:-S(O)1 nR16、-NR17R18或-N=CR19R20,
R16优选代表任选氟-、氯-、氰基-或硝基-取代的C1-C4-烷基,代表C3-C6-链烯基、C3-C6-链二烯基、C3-C6-炔基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或苯基,该苯基任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,
n1优选代表数字0、1或2之一,
R17和R18与连接的氮原子一起代表任选卤素-、C1-C4-烷基、C1-C4-烷氧基或C1-C4-烷硫基取代的饱和5至7元杂环,该杂环除了氮原子外,具有2或3个相同或不同的选自氮、氧和硫的杂原子,
R19优选代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基,
R20优选代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基。
A1特别优选代表氮或基团CR0,
R0特别优选代表氢、氟、氯、溴、硝基、氰基、羟基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基或代表下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2或-CSN(CH3)2,
R11特别优选代表氟、氯、溴、硝基、氰基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、三氟乙氧基或代表下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2和-CSN(CH3)2,
R12特别优选代表氢、氟、氯、甲基或三氟甲基,
R13特别优选代表三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、三氟甲基亚磺酰基、三氟甲基亚硫酰基或三氟甲基磺酰基,
R14特别优选代表氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、三氟乙氧基、四氟乙氧基、五氟乙氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、羟基、巯基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表苯基、苯氧基甲基或苄基,它们各任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、硝基或任选氟-、氯-或甲基-取代的苯基取代,或代表基团-S(O)1 nR16,
R15特别优选代表氢、氰基、氨基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、氟丙基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、炔丙氧基、丁炔氧基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表苯基,该苯基任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基或任选氟-、氯-或甲基取代的苯基取代,代表任选甲基-、乙基-、正或异丙基-、正、异、仲或叔丁基-取代的苄基,或代表下列基团之一:-S(O)1 nR16、-NR17R18或-N=CR19R20,
R16特别优选代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、烯丙基、丙二烯基、炔丙基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环戊基或环己基,或苯基,该苯基任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基或任选氟-、氯-或甲基取代的苯基取代,
n1特别优选代表数字0、1或2之一,
R17和R18与连接的氮原子一起代表各任选甲基-、乙基-、甲氧基-或乙氧基-取代的哌啶基、哌嗪基或吗啉基,
R19特别优选代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基,
R20特别优选代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基。
在上面的一般性或在优选范围中提到的基团的定义或说明适用于终产物,且相应地适用于原料和中间体。这些基团的定义可以按需要相互间组合,即各自优选范围间的组合也是可以的。
根据本发明,优选那些存在上述优选含意组合的式(I)化合物。
根据本发明,特别优选那些存在上述特别优选含意组合的式(I)化合物。
在上下文基团的定义中所提到的烃基基团如烷基或链烯基,包括与杂原子相连的烃基如烷氧基或烷硫基,在每种情况下,尽可能是直链或支链。
根据本发明的新化合物的实例列于表1a至80d中:表1a表1a中的化合物相应于通式(I),其中R14=CH3R15=CH3和Ar=下列:
表1b表1b含有通式(IA)化合物,其中R14=CH3R15=CH3和At=下列:
表1c表1c含有通式(IA)化合物,其中R14=CH3R15=CH3和Ar=下列:
表1d表1d含有通式(IA)化合物,其中R14=CH3R15=CH3和Ar=下列:
表2a至2d表2a至2d含有通式(IA)化合物,其中R14=C2H5R15=CH3和Ar=如表1a至1d中所列。表3a至3d表3a至3d含有通式(IA)化合物,其中R14=C3H7-iR15=CH3和Ar=如表1a至1d中所列。表4a至4d表4a至4d含有通式(IA)化合物,其中R14=C3H7-nR15=CH3和Ar=如表1a至1d中所列。表5a至5d表5a至5d含有通式(IA)化合物,其中R14=C4H9-nR15=CH3和Ar=如表1a至1d中所列。表6a至6d表6a至6d含有通式(IA)化合物,其中R14=环丙基R15=CH3和Ar=如表1a至1d中所列。表7a至7d表7a至7d含有通式(IA)化合物,其中R14=环丙基R15=C2H5和Ar=如表1a至1d中所列。表8a至8d表8a至8d含有通式(IA)化合物,其中R14=环丙基R15=C3H7-i和Ar=如表1a至1d中所列。表9a至9d表9a至9d含有通式(IA)化合物,其中R14=环丙基R15=环丙基和Ar=如表1a至1d中所列。表10a至10d表10a至10d含有通式(IA)化合物,其中R14=C3H7-iR15=环丙基和Ar=如表1a至1d中所列。表11a至11d表11a至11d含有通式(IA)化合物,其中R14=C4H9-tR15=环丙基和Ar=如表1a至1d中所列。表12a至12d表12a至12d含有通式(IA)化合物,其中R14=环丙基R15=-CH2CH2OCH3和Ar=如表1a至1d中所列。表13a至13d表13a至13d含有通式(IA)化合物,其中R14=CF3R15=H和Ar=如表1a至1d中所列。表14a至14d表14a至14d含有通式(IA)化合物,其中R14=CF3R15=-SCFCl2和Ar=如表1a至1d中所列。表15a至15d表15a至15d含有通式(IA)化合物,其中R14=环丙基R15=-OCH3和Ar=如表1a至1d中所列。表16a至16d表16a至16d含有通式(IA)化合物,其中R14=环丙基R15=-OC3H5和Ar=如表1a至1d中所列。表17a至17d表17a至17d含有通式(IA)化合物,其中R14=环丙基R15=-OCH2C=CH2和Ar=如表1a至1d中所列。表18a至18d表18a至18d含有通式(IA)化合物,其中R14=环丙基R15=-NH2和Ar=如表1a至1d中所列。表19a至19d表19a至19d含有通式(IA)化合物,其中R14=环丙基R15=-CHF2和Ar=如表1a至1d中所列。表20a至20d表20a至20d含有通式(IA)化合物,其中R14=CF3R15=C3H7-i和Ar=如表1a至1d中所列。表21a至21d表21a至21d含有通式(IA)化合物,其中R14=CHF3R15=CH3和Ar=如表1a至1d中所列。表22a至22d表22a至22d含有通式(IA)化合物,其中R14=CF3R15=C2H5和Ar=如表1a至1d中所列。表23a至23d表23a至23d含有通式(IA)化合物,其中R14=CF3R15=C4H9-t和Ar=如表1a至1d中所列。表24a至24d表24a至24d含有通式(IA)化合物,其中R14=CF3R15=环丙基和Ar=如表1a至1d中所列。表25a至25d表25a至25d含有通式(IA)化合物,其中R14=CF3 Ar=如表1a至1d中所列。表26a至26d表26a至26d含有通式(IA)化合物,其中R14=CHF2R15=环丙基和Ar=如表1a至1d中所列。表27a至27d表27a至27d含有通式(IA)化合物,其中R14=CHF2R15=CN和Ar=如表1a至1d中所列。表28a至28d表28a至28d含有通式(IA)化合物,其中R14=CF3R15=CN和Ar=如表1a至1d中所列。表29a至29d表29a至29d含有通式(IA)化合物,其中R14=SCHF2R15=-C3H7-i和Ar=如表1a至1d中所列。表30a至30d表30a至30d含有通式(IA)化合物,其中R14=CF3R15=-OCH3和Ar=如表1a至1d中所列。表31a至31d表31a至31d含有通式(IA)化合物,其中R14=CF3R15=-CH2CH2OCH3和Ar=如表1a至1d中所列。表32a至32d表32a至32d含有通式(IA)化合物,其中R14=CF3R15=苯基和Ar=如表1a至1d中所列。表33a至33d表33a至33d含有通式(IA)化合物,其中R14=CF3 Ar=如表1a至1d中所列。表34a至34d表34a至34d含有通式(IA)化合物,其中R14=CF3 Ar=如表1a至1d中所列。表35a至35d表35a至35d含有通式(IA)化合物,其中R14=-OCH2CF3 Ar=如表1a至1d中所列。表36a至36d表36a至36d含有通式(IA)化合物,其中R14=苯基R15=环丙基和Ar=如表1a至1d中所列。表37a至37d表37a至37d含有通式(IA)化合物,其中R14=-CF2CF3R15=环丙基和Ar=如表1a至1d中所列。表38a至38d表38a至38d含有通式(IA)化合物,其中R14=CF2CF3R15=C4H9-t和Ar=如表1a至1d中所列。表39a至39d表39a至39d含有通式(IA)化合物,其中R14=CF2CF3R15=C3H7-i和Ar=如表1a至1d中所列。表40a至40d表40a至40d含有通式(IA)化合物,其中R14=-CF2CF3R15=C2H5和Ar=如表1a至1d中所列。表41a至41d表41a至41d含有通式(IA)化合物,其中R14=-CF2CF3R15=CH3和Ar=如表1a至1d中所列。表42a至42d表42a至42d含有通式(IA)化合物,其中R14=-CF2CHF2R15=CH3和Ar=如表1a至1d中所列。表43a至43d表43a至43d含有通式(IA)化合物,其中R14=-CF2CHF2R15=C2H5和Ar=如表1a至1d中所列。表44a至44d表44a至44d含有通式(IA)化合物,其中R14=-CF2CHF2R15=C3H7-i和Ar=如表1a至1d中所列。表45a至45d表45a至45d含有通式(IA)化合物,其中R14=-CF2CHF2R15=C4H9-t和Ar=如表1a至1d中所列。表46a至46d表46a至46d含有通式(IA)化合物,其中R14=-CF2CHF2R15=C3H7-n和Ar=如表1a至1d中所列。表47a至47d表47a至47d含有通式(IA)化合物,其中R14=-CF2CHF2R15=环丙基和Ar=如表1a至1d中所列。表48a至48d表48a至48d含有通式(IA)化合物,其中R14=-CF3R15=-CH2CH2CH2F和Ar=如表1a至1d中所列。表49a至49d表49a至49d含有通式(IA)化合物,其中R14=C3H7-iR15=-CH2CH2CH2F和Ar=如表1a至1d中所列。表50a至50d表50a至50d含有通式(IA)化合物,其中R14=环丙基R15=-CH2CH2CH2F和Ar=如表1a至1d中所列。表51a至51d表51a至51d含有通式(IA)化合物,其中R14=CNR15=-CH2CH2CH2F和Ar=如表1a至1d中所列。表52a至52d表52a至52d含有通式(IA)化合物,其中R14=CNR15=-CHF2和Ar=如表1a至1d中所列。表53a至53d表53a至53d含有通式(IA)化合物,其中R14=CNR15=环丙基和Ar=如表1a至1d中所列。表54a至54d表54a至54d含有通式(IA)化合物,其中R14=BrR15=环丙基和Ar=如表1a至1d中所列。表55a至55d表55a至55d含有通式(IA)化合物,其中R14=ClR15=环丙基和Ar=如表1a至1d中所列。表56a至56d表56a至56d含有通式(IA)化合物,其中R14=ClR15=-CHF2和Ar=如表1a至1d中所列。表57a至57d表57a至57d含有通式(IA)化合物,其中R14=ClR15=-CH3和Ar=如表1a至1d中所列。表58a至58d表58a至58d含有通式(IA)化合物,其中R14=ClR15=-C2H5和Ar=如表1a至1d中所列。表59a至59d表59a至59d含有通式(IA)化合物,其中R14=ClR15=-C3H7-i和Ar=如表1a至1d中所列。表60a至60d表60a至60d含有通式(IA)化合物,其中R14=BrR15=-C3H7-i和Ar=如表1a至1d中所列。表61a至61d表61a至61d含有通式(IA)化合物,其中R14=BrR15=-C4H9-t和Ar=如表1a至1d中所列。表62a至62d表62a至62d含有通式(IA)化合物,其中R14=SCHF2R15=环丙基和Ar=如表1a至1d中所列。表63a至63d表63a至63d含有通式(IA)化合物,其中R14=OCF2HR15=环丙基和Ar=如表1a至1d中所列。表64a至64d表64a至64d含有通式(IA)化合物,其中R14=OCHF2R15=C4H9-t和Ar=如表1a至1d中所列。表65a至65d表65a至65d含有通式(IA)化合物,其中R14=-OCH3R15=环丙基和Ar=如表1a至1d中所列。表66a至66d表66a至66d含有通式(IA)化合物,其中R14=-OC2H5R15=环丙基和Ar=如表1a至1d中所列。表67a至67d表67a至67d含有通式(IA)化合物,其中R14=-OC3H7-iR15=环丙基和Ar=如表1a至1d中所列。表68a至68d表68a至68d含有通式(IA)化合物,其中R14=-SCH3R15=环丙基和Ar=如表1a至1d中所列。表69a至69d表69a至69d含有通式(IA)化合物,其中R14=-SO2CH3R15=环丙基和Ar=如表1a至1d中所列。表70a至70d表70a至70d含有通式(IA)化合物,其中R14=-SC3H7-iR15=环丙基和Ar=如表1a至1d中所列。表71a至71d表71a至71d含有通式(IA)化合物,其中R14=C4H9-tR15=CN和Ar=如表1a至1d中所列。表72a至72d表72a至72d含有通式(IA)化合物,其中R14=-SC2H5R15=-CN和Ar=如表1a至1d中所列。表73a至73d表73a至73d含有通式(IA)化合物,其中R14=CF3R15=-CHF2和Ar=如表1a至1d中所列。表74a至74d表74a至74d含有通式(IA)化合物,其中R14=CF3R15=-CH2CN和Ar=如表1a至1d中所列。表75a至75d表75a至75d含有通式(IA)化合物,其中R14=CF3R15=间三氟甲基苯基和Ar=如表1a至1d中所列。表76a至76d表76a至76d含有通式(IA)化合物,其中R14=CF3R15=对氯苯基和Ar=如表1a至1d中所列。表77a至77d表77a至77d含有通式(IA)化合物,其中R14=CF3R15=-N=CHOC2H5和Ar=如表1a至1d中所列。表78a至78d表78a至78d含有通式(IA)化合物,其中R14=CF3R15=-N=C(CH3)OC2H5和Ar=如表1a至1d中所列。表79a至79d表79a至79d含有通式(IA)化合物,其中R14=CF3 Ar=如表1a至1d中所列。表80a至80d表80a至80d含有通式(IA)化合物,其中R14=CF3R15=-SO2CF2CH3和Ar=如表1a至1d中所列。
R11 | R13 | Ro |
ClFBrFBrClBrFNO2NO2NO2NO2 | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClFFCNCNCNCNNO2ClBr |
R11 | R13 | Ro |
NO2CF3CF3CNClClClFClClFBrClCl-CONH2FClBrBrFFBrCN-CONHCH3-CON(CH3)2FFFFF | CF3CF3CF3CF3CF3CF3-OCF3-OCF3-OCHF2CF3CF3CF3CF3CF3CF3-OCHF2-OCF3-OCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3-OCF3-OCF3 | FCF3ClCNCH3C2H5ClClCl-CSNH2-CSNH2-CSNH2-CSNHCH3-CSN(CH3)2Cl-CSNH2-CSNH2-CSNH2-CSNHCH3-CSNHCH3-CSN(CH3)2-CSN(CH3)2-CSN(CH3)2ClCl-CONH2-CONHCH3-CON(CH3)2-CSNH2-CONH2 |
R11 | R13 | Ro |
ClClClClClClClClClClClCl | -SO2CF3-SO2CF3-SO2CF3-SO2CF3-SO2CF3-SO2CF3-SO2CF3-SO2CF3-SO2CF3-SO2CF3-SCF3-SOCF3 | FClNO2CN-CONH2-CSNH2-CSNHCH3-CSN(CH3)2-CONHCH3-CON(CH3)2ClCl |
R11 | R13 |
CNClClCl | CF3CF3-OCF3-OCClF2 |
R11 | R12 | R13 | Ro |
ClCl | FF | CF3CF3 | ClF |
R11 | R13 |
ClF | CF3CF3 |
式(II)提供进行本发明方法(a)所需起始原料1H-三唑啉的一般定义。在此式(II)中,R14和R15各优选且特别是代表这样的基团,即与本发明式(Ia)化合物的相关的描述中业已提到的对于这些取代基而言是优选或特别优选的基团。
式(II)的1H-三唑啉是已知的或可以通过已知的方法获得(参见例如EP283876;EP305844;EP341489;EP415196;EP422469;EP425948;EP431291;EP507171;EP513621;EP534266;Chem.Ber.102,755-766[1969];Liebigs Ann.Chem.343,24[1905])。它们中的一些也构成共同转让的迄今未公开的专利申请主题的一部分(参见1994年10月5日的德国专利申请P4435547)。
式(II)1H-三唑啉酮的实例列于表(II-1)至(II-49)中:
表(II-1)表(II-1)化合物相应于通式(II),其中R14=CH3R15=下列:H,CH3,C2H5,n-C3H7,i-C3H7,n-C4H9,i-C4H9,s-C4H9,t-C4H9,CHF2,CClF2,CHClF,CH2CH2CH2F,CH2CF3,CHF=CClF,CH2CH2-O-CH3,CH2CH2-O-CH2CH3,CH2CH=CH2,CH2CH2CH2-O-CH3,CH2CN,CN,CH2C=CH,O-CH3,O-C2H5,O-CH2CH=CH2,O-CH(CH3)C≡CH,SCFCl2,SO2CF2CH3,N=CHOC2H5,N=C(CH3)OC2H5,NH2, 表(II-2)表(II-2)含有通式(II)的化合物,其中R14=C2H5和R15=如表(II-1)中所列。表(II-3)表(II-3)含有通式(II)的化合物,其中R14=C3H7-i和R15=如表(II-1)中所列。表(II-4)表(II-4)含有通式(II)的化合物,其中R14=C3H7-n和R15=如表(II-1)中所列。表(II-5)表(II-5)含有通式(II)的化合物,其中R14=C4H9-t和R15=如表(II-1)中所列。表(II-6)表(II-6)含有通式(II)的化合物,其中R14=C4H9-n和R15=如表(II-1)中所列。表(II-7)表(II-7)含有通式(II)的化合物,其中R14=C4H9-t和R15=如表(II-1)中所列。表(II-8)表(II-8)含有通式(II)的化合物,其中R14=C4H9-s和R15=如表(II-1)中所列。表(II-9)表(II-9)含有通式(II)的化合物,其中R14=环丙基和R15=如表(II-1)中所列。表(II-10)表(II-10)含有通式(II)的化合物,其中R14=CF3和R15=如表(II-1)中所列。表(II-11)表(II-11)含有通式(II)的化合物,其中R14=CHF2和R15=如表(II-1)中所列。表(II-12)表(II-12)含有通式(II)的化合物,其中R14=CClF2和R15=如表(II-1)中所列。表(II-13)表(II-13)含有通式(II)的化合物,其中R14=CF2CF3和R15=如表(II-1)中所列。表(II-14)表(II-14)含有通式(II)的化合物,其中R14=CF2CHF2和R15=如表(II-1)中所列。表(II-15)表(II-15)含有通式(II)的化合物,其中R14=苯基和R15=如表(II-1)中所列。表(II-16)表(II-16)含有通式(II)的化合物,其中R14=CN和R15=如表(II-1)中所列。表(II-17)表(II-17)含有通式(II)的化合物,其中R14=-OCH2CF3和R15=如表(II-1)中所列。表(II-18)表(II-18)含有通式(II)的化合物,其中R14=-OCHF2和R15=如表(II-1)中所列。表(II-19)表(II-19)含有通式(II)的化合物,其中R14=Br和R15=如表(II-1)中所列。表(II-20)表(II-20)含有通式(II)的化合物,其中R15=如表(II-1)中所列。表(II-21)表(II-21)含有通式(II)的化合物,其中R14=Cl和R15=如表(II-1)中所列。表(II-22)表(II-22)含有通式(II)的化合物,其中R14=OCH3和R15=如表(II-1)中所列。表(II-23)表(II-23)含有通式(II)的化合物,其中R14=-OC2H5和R15=如表(II-1)中所列。表(II-24)表(II-24)含有通式(II)的化合物,其中R14=-OC3H7-i和R15=如表(II-1)中所列。表(II-25)表(II-25)含有通式(II)的化合物,其中R14=-SCH3和R15=如表(II-1)中所列。表(II-26)表(II-26)含有通式(II)的化合物,其中R14=-SO2CH3和R15=如表(II-1)中所列。表(II-27)表(II-27)含有通式(II)的化合物,其中R14=-SO2C2H5和R15=如表(II-1)中所列。表(II-28)表(II-28)含有通式(II)的化合物,其中R14=-SC2H5和R15=如表(II-1)中所列。表(II-29)表(II-29)含有通式(II)的化合物,其中R14=-SC3H7-i和R15=如表(II-1)中所列。表(II-30)表(II-30)含有通式(II)的化合物,其中R14=-SCHF2和R15=如表(II-1)中所列。表(II-31)表(II-31)含有通式(II)的化合物,其中R14=-SCH2CH2CH2F和R15=如表(II-1)中所列。表(II-32)表(II-32)含有通式(II)的化合物,其中R14=-OCH2CH2CH2F和R15=如表(II-1)中所列。表(II-33)表(II-33)含有通式(II)的化合物,其中R14=苄基和R15=如表(II-1)中所列。表(II-34)表(II-34)含有通式(II)的化合物,其中R14=-CH2CF3和R15=如表(II-1)中所列。表(II-35)表(II-35)含有通式(II)的化合物,其中R14=3,4-二氯苯基和R15=如表(II-1)中所列。表(II-36)表(II-36)含有通式(II)的化合物,其中R14=间三氟甲基苯基和R15=如表(II-1)中所列。表(II-37)表(II-37)含有通式(II)的化合物,其中R14=-OCH2CCl3和R15=如表(II-1)中所列。表(II-38)表(II-38)含有通式(II)的化合物,其中R14=-SCH2Cl和R15=如表(II-1)中所列。表(II-39)表(II-39)含有通式(II)的化合物,其中R14=-SCH2F和R15=如表(II-1)中所列。表(II-40)表(II-40)含有通式(II)的化合物,其中R14=-SCH2CH2F和R15=如表(II-1)中所列。表(II-41)表(II-41)含有通式(II)的化合物,其中R14=-SCH2CHF2和R15=如表(II-1)中所列。表(II-42)表(II-42)含有通式(II)的化合物,其中R14=-SCH2CF3和R15=如表(II-1)中所列。表(II-43)表(II-43)含有通式(II)的化合物,其中R14=-SCH2CH2CF3和R15=如表(II-1)中所列。表(II-44)表(II-44)含有通式(II)的化合物,其中R14=-SCH2CH=CH2和R15=如表(II-1)中所列。表(II-45)表(II-45)含有通式(II)的化合物,其中R14=-SCH2C≡CH和R15=如表(II-1)中所列。表(II-46)表(II-46)含有通式(II)的化合物,其中R14=-SCH=C=CH2和R15=如表(II-1)中所列。表(II-47)表(II-47)含有通式(II)的化合物,其中R14=-OCH2CF2CHF2和R15=如表(II-1)中所列。表(II-48)表(II-48)含有通式(II)的化合物,其中R14=苯硫基和R15=如表(II-1)中所列。表(II-49)表(II-49)含有通式(II)的化合物,其中R15=如表(II-1)中所列。
式(III)提供进行本发明方法(a)进一步需要的起始原料卤素衍生物的一般定义。在此式(III)中,R11、R12、R13和A1各优选且特别是代表这样的基团,即与本发明式(Ia)化合物的相关的描述中业已提到的对于这些取代基而言是优选或特别优选的基团。Hal优选代表氟、氯或溴,特别是氟或氯。
式(III)的卤素衍生物是通常已知的有机化学化合物或可以用通常已知的方法获得。
式(IV)提供进行本发明方法(b)需要的起始原料肼衍生物的一般定义。在此式(IV)中,R11、R12、R13和A1各优选且特别是代表这样的基团,即与本发明式(Ia)化合物的相关的描述中业已提到的对于这些取代基而言是优选或特别优选的基团。
式(IV)的肼衍生物是已知的(参见例如US-PS4127575;US-PS3609158;DE-A-2558399;J.Chem.Soc.C;1971,167-174)或可以通过已知的方法用简单的方式获得(参见例如Houben-Weyl“Methodender orgnischen Chemie”Vol.X/2,p203,Thieme Verlag,Stuttgart,1967)。
式(V)提供进行本发明方法(b)进一步需要的起始原料亚氨基羧酸酯衍生物的一般定义。在此式(V)中,R21和R22相互独立地各优选代表C1-C4-烷基,特别是甲基或乙基。Rl4-1优选或特别是具有这样的含意,即与本发明式(Ia)化合物相关的描述中,在R14中业已提到的对于相应的取代基而言是优选或特别优选的含意。
式(V)的氨基羧酸酯是已知的或可以通过已知的方法获得(参见例如Ber.119,2444-2457[1986];Bull.Chem.Soc.Jpn.55,3943-3944[1982];Chem.Lett.1982,1015-1016;Chem.Lett.1987,1403-1404;J.Amer.Chem.Soc.95,3957-3963[1973];J.Org.Chem.36,3251-3252[1971]。
进行本发明方法(c)所需的起始原料式(Id)N-芳基-1,2,4-三唑啉-5-酮是根据本发明的化合物。
式(VI)提供进行本发明方法(c)进一步需要的起始原料烷基化剂的一般定义。在此式(VI)中,R15-1优选或特别是具有这样的含意,即与本发明式(Ia)化合物相关的描述中,在R15中业已提到的对于相应的取代基而言是优选或特别优选的含意。E代表常规的吸电子离去基团,例如卤素,特别是氯、溴或碘;或代表各任选取代的烷基磺酰氧基、烷氧基磺酰氧基或芳基磺酰氧基,特别是甲磺酰氧基、三氟甲磺酰氧基、甲氧基磺酰氧基、乙氧基磺酰氧基或对甲苯磺酰氧基。
式(VI)的烷基化剂是通常已知的有机化学化合物。
适合于进行本发明方法(a)的稀释剂是惰性有机溶剂。这些溶剂包括:特别是脂族、脂环族或芳族的、任选卤代的烃类,如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿或四氯化碳;醚类,如乙醚、二异丙醚、二噁烷、四氢呋喃或乙二醇二甲基醚和乙二醇二乙基醚;醚类如丙酮、丁酮或甲基异丁基酮;腈类如乙腈、丙腈或苄腈;酰胺类如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;或酯类如乙酸甲酯或乙酸乙酯。
本发明方法(a)优选在适合的反应辅助剂存在下进行。适合的反应辅助剂是所有的常规无机或有机碱。这些碱包括例如:碱土金属或碱金属氢氧化物,如氢氧化钠、氢氧化钙或氢氧化钾,氢氧化铵,碱金属碳酸盐如碳酸钠、碳酸钾、碳酸氢钾或碳酸氢钠,碳酸铵,碱金属或碱土金属乙酸盐如乙酸钠、乙酸钾、乙酸钙或乙酸铵,和叔胺如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU)以及哌啶。
实施本发明方法(a)时,反应温度可以在相对宽的范围内变化。通常,反应是在0℃至+180℃间,优选在+20℃至+120℃间的温度下进行的。
本发明方法(a)通常在常压下进行。然而,也可以在高压或低压下进行。
实施本发明方法(a)时,对于每摩尔的式(II)1H-三唑啉酮,通常采用1.0至3.0摩尔,优选1.0至1.5摩尔的式(III)卤素衍生物,且如果适宜,采用1.0至3.0摩尔,优选1.0至1.5摩尔的碱(作为反应辅助剂)。
反应、反应产物的后处理和分离是用常规已知的方法来进行的(同样参见制备实施例)。
适合于进行本发明方法(b)的稀释剂是惰性有机溶剂。优选使用实施本发明方法(a)的描述中列出的溶剂。
实施本发明方法(b)时,反应温度可以在相对宽的范围内变化。通常,反应是在-20℃至+150℃间,优选在0℃至+120℃间的温度下进行的。
本发明方法(b)通常在常压下进行。然而,也可以在高压或低压下进行。
实施本发明方法(b)时,对于每摩尔的式(IV)肼衍生物,通常采用1.0至3.0摩尔,优选1.0至1.5摩尔的式(V)氨基羧酸酯。
反应、反应产物的后处理和分离是用常规已知的方法来进行的。
适合于实施本发明方法(c)的稀释剂是惰性有机溶剂。这些溶剂包括:特别是脂族、脂环族或芳族,任选卤代的烃类,如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿或四氯化碳;醚类,如乙醚、二异丙醚、二噁烷、四氢呋喃或乙二醇二甲基醚和乙二醇二乙基醚;腈类如乙腈、丙腈或苄腈;酰胺类如N,N-二甲基甲酰胺、N,N-二乙基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类如乙酸甲酯或乙酸乙酯;或亚砜类如二甲基亚砜。
如果适宜,本发明方法(c)也可以在两相体系中进行,例如水/甲苯或水/二氯甲烷,如果适宜,在适合的相转移催化剂存在下进行。这些催化剂的实例包括:碘化四丁基铵、溴化四丁基铵、氯化四丁基铵、溴化三丁基甲基鏻、氯化三甲基-C13/C15-烷基铵、溴化三甲基-C13/C15-烷基铵、二苄基二甲基铵甲基硫酸盐、氯化二甲基-C12/C14-烷基苄基铵、溴化二甲基-C12/C14-烷基苄基铵、四丁基氢氧化铵、氯化三乙基苄基铵、氯化甲基三辛基铵、氯化三甲基苄基铵、15-冠-5、18-冠-6或三-[2-(2-甲氧基乙氧基)-乙基]-胺。
本发明方法(c)优选在适合的反应辅助剂存在下进行。适合的反应辅助剂是所有的常规无机或有机碱。这些碱包括例如:碱土金属或碱金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、乙酸钠、乙酸钾、乙酸钙、碳酸钠、碳酸钾、碳酸氢钾或碳酸氢钠、氢氧化铵、乙酸铵或碳酸铵,和叔胺如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU)。
实施本发明方法(c)时,反应温度可以在相对宽的范围内变化。通常,反应是在-20℃至+150℃间,优选在0℃至+120℃间的温度下进行的。
本发明方法(c)通常在常压下进行。然而,也可以在高压或低压下进行。
实施本发明方法(c)时,对于每摩尔的式(Id)N-芳基-1,2,4-三唑啉-5-酮,通常采用1.0至3.0摩尔,优选1.0至2.0摩尔的式(VI)烷基化剂,且如果适宜,采用1.0至3.0摩尔,优选1.0至2.0摩尔的碱(作为反应辅助剂)。
反应、反应产物的后处理和分离是用常规已知的方法来进行的。
可用于本发明的式(I)活性化合物具有好的作物耐受性和有利的同热安全性,它们适合于防治动物害虫,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面上的昆虫、蜱螨和线虫。它们可优选用作作物保护剂。它们对正常的敏感和抗性种类和对所有或某些生长发育阶段有活性。上述害虫包括:
等足纲,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidium vulgare)和斑鼠妇(Porcellio scaber)。
倍足纲,例如,Blaniulus guttulatus。
唇足纲,例如,地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigeraspec)。
综合纲,例如,洁幺蚰(Scutigerella immaculata)。
缨尾目,例如,西洋衣鱼(Lepisma saccharina)。
弹尾目,例如,棘跳虫(Onychiurus armatus)。
直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattellagermanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoria migratorioids)、殊种蚱蜢(Melanoplusdifferentialis)、沙漠蝗(Schistocerca gregaria)和Supella spp.。
革翅目,例如,欧洲球螋(Forfcula auricularia)。
等翅目,例如,犀白蚁属(Reticulitermes spp.)。
虱目,例如,美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigusspp.)、阴虱属(Phthiru spp.)、虱属(Pediculus spp.)、血虱属(Haematopinus spp.)、颚虱属(Linognathus spp.)和盲虱属(Solenopotesspp.)。
食毛目,例如,啮毛虱属(Trichodectes spp.)、Damalinea spp.、毛鸟虱属(Trimenopon spp.)、Monopon spp.、Trioton spp.、羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.和猫虱属(Felicola spp.)。
缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thripstabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、臭蝽属(Cimex spp.)、猎蝽属(Rhodnius spp.)、锥蝽属(Triatoma spp.)和全圆蝽属(Panstrongylus spp.)。
同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisiatabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Doralis pomi)、苹果绵蚜(Eriosomalanigerum)、桃大尾蚜(Hyalopterus arundinis)、麦长管蚜(Macrosiphumavenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodon humili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoasca spp.)、Euscelisbilobatus、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecaniumcorni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvata lugens)、红园蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotus hederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psyllaspp.)。
鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupaluspiniarius)、冬尺蛾(Cheimatobia brumata)、Lithocolletis blancardella、苹果巢蛾(Hyponomeuta padella)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜叶蛾(Phyllocnistis citrella)、Agrotis spp.、Euxoa spp.、Feltia spp.、棉斑实蛾(Earias insulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾((Spodopteraexigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolis flammea)、斜纹夜蛾(Prodenia litura)、粘虫属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pierisspp.)、禾草螟属(Chilo spp.)、Pyrausta nubilalis、Ephestiakuehniella、蜡螟(Galleria mellonella)、幕衣蛾(Tineola bisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、Cacoecia podana、Capua reticulana、枞色卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupesbajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶甲(Phaedon cochleariae)、条叶甲属(Diabroticaspp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachnavarive stis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilussurinamensis)、花象甲属(Antho nomus spp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopolitessordidus)、甘蓝荚象甲(Ceuthorrhynchus assimilis)、苜蓿叶象虫(Hyperapostica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptus hololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、Agriotes spp.、Cono derus spp、鳃角金龟(Melolontha melolontha)、六月金龟(Amphimallon sosti tialis)和Costelytra zealandica。
膜翅目,例如,Diprion spp.、Hoplocampa spp.、田蚁属(Lasiusspp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。
双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、蝇属(Muscaspp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、Cuterebraspp.、Tannia spp.、Bibio hortulanus、瑞典麦杆蝇(Oscinella frit)、Phorbia spp.、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitiscapitata)、油榄实蝇(Dacus oleae)、沼泽大蚊(Tipula paludosa)、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomusspp.)、卢蚊属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、Hybomitra spp.、Atylotus spp.、虻属(Tabanusspp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、Hydrotaea spp.、螫蝇属(Stomoxys spp.)、血蝇属(Haematobia spp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphora spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophagaspp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp)、Lipoptena spp.、Melophagus spp.、Muscina spp.。
蚤目,例如,印鼠客蚤(Xenopsylla cheopis)、毛列蚤属(Ceratophyllusspp.)、蚤属(Pulex spp.)和栉头蚤属(Ctenocephalides spp.)。
蛛形纲,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectus mactans)。
蜱螨目,例如,Myocoptes spp.、粗脚粉螨(Acarus siro)、隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodoros spp.)、Ornithonyssus spp.、皮刺螨属(Dermanyssus spp.)、茶藨瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalommaspp.)、硬蜱属(Ixodes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)、叶螨属(Tetranychusspp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、Raillietia spp.、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostormaspp.)、瓦螨属(Varroa spp.)和Otobius spp.。
Actinedida(后气孔亚目)和Acaridida(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、绵羊疥螨属(Psorergatesspp.)、脂螨属(Demodex spp.)、恙螨属(Trombicula spp.)、嫠螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、 Hypodectes spp.、翼衣属(Pterolichusspp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、Otodectesspp.、疥螨属(Sarcoptes spp.)、Notoedres spp.、鸟疥螨属(Knemidocoptesspp.)、鸡螨属(Cytodites spp.)和鸡雏螨属(Laminosioptes spp.)。
植物寄生线虫包括例如草地垫刃线虫属(Pratylenchus spp.)、毕肖穿孔线虫(Radopholus similis)、Ditylenchus dipsaci、Tylenchulussemipenetrans、异皮线虫属(Heterodera spp.)、囊线虫属(Globoderaspp.)、Meloidogyne spp.、滑刃线虫属(Aphelechoides spp.)、Longidorusspp.、剑线虫属(Xiphinema spp.)和髦根线虫属(Trichodorus spp.)。
本发明活性化合物具有高的杀虫活性。
它们可以用来特别有效地防治对植物有害的叶居和土壤居昆虫,例如防治辣根猿叶甲(Phaedon cochleariae)幼虫、黑尾叶蝉(Nephotettixcincticeps)幼虫或防治小菜蛾(Plutella maculipennis)幼虫,以及防治草地贪夜蛾(Spodoptera frugiperda)和烟芽夜蛾(Heliothis Virescens)幼虫。
此外,可能根据本发明使用的式(I)活性化合物也具有杀螨和杀真菌活性,例如对稻瘟病有活性。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、水溶性粉剂、颗粒剂、悬浮-乳剂、用活性化合物浸渍的天然和合成材料,以及包在聚合物中的微细胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂,即液体溶剂和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
在用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有: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,脂族烃,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。
适合的固体载体是:
例如铵盐和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:例如压碎并分级的原生岩如方解石、大理石、浮石、海泡石和白云石,以及无机和有机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是: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;适合的分散剂是:例如,木素亚硫酸盐废液和甲基纤维素。
制剂中可以使用粘合剂如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,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。其它的粘合剂可以是矿物油和植物油。
也可能使用着色剂如无机颜料,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。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
本发明活性化合物可以其商业上可行的制剂和由这些制剂制备的使用形式存在,所述的制剂为与如下的其它活性化合物的混合物:杀虫剂、引诱剂、杀菌剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯、羧酸酯类、氯代烃类、苯基脲类、由微生物产生的物质等。
特别有利的混合物组分是下列化合物: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-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)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)-甲氧基亚氨基[α-(邻甲苯氧基)-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、碘萎灵、苯菌灵、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、恶醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、一甲呋萎灵、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、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、双胍辛、六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、铜制剂如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物、双代混剂、代森锰锌、代森锰、嘧菌胺、邻酰胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、恶酰胺、oxamocarb、氧化萎锈灵、pefurazoate、戊菌唑、戊菌隆、稻病磷、四氯苯酞、匹马菌素、哌啶宁、福代锌、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环吗啉、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:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。杀虫剂/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、双甲脒、阿维螨素(avermectin)、AZ60541、azadirachtin、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、苯恶威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA157419、CGA184699、除线威、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、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二恶硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、锐劲特(fipronil)、氟啶胺、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fbfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、吡虫啉、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC184、NI25、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH5992、水杨硫磷、硫线磷、silafluofen、治螟磷、甲丙硫磷、tebufenozide、tebufenpyrad、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、YI5301/5302、zetamethrin。除草剂:
例如酰苯胺类如吡氟草胺和敌稗;芳基羧酸类如二氯吡啶甲酸、麦草畏和毒草定;芳氧羧酸类如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;芳氧基苯氧羧酸类如禾草灵、噁唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵;连氮酮类如杀草敏和哒草伏;氨基甲酸酯类如氯苯胺灵、甜菜安、甜菜宁和苯胺灵;氯乙酰苯胺类如甲草胺、乙草胺、丁草胺、吡草胺、异丙草胺、丙草胺和毒草胺;二硝基苯胺类如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类如三氟羧草醚、甲羧除草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和甲基苯噻隆;羟胺类如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类如咪草烟、咪草酯、灭草烟和灭草喹;腈类如溴苯腈、敌草腈和碘苯腈;氧乙酰胺类如苯噻草胺;磺酰脲类如amidosufuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、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;硫代氨基甲酸酯类如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹和野麦畏;三嗪类如莠去津、氰草津、西玛津、西草净、特丁净和特丁津;三嗪酮类如环嗪酮、苯嗪草酮和嗪草酮;其它除草剂如杀草强、呋草黄、灭草松、环庚草醚、异恶草酮、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、草硫膦和灭草环。
此外,本发明活性化合物可以以其商业上可行的制剂和以由这些制剂制备的使用形式存在。这些制剂可以是与增效剂的混合物。增效剂是可以增加活性化合物活性,而所添加的增效剂本身无需有活性的化合物。
由商业上可行的制剂制备的使用形式中的活性化合物的含量可以在宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
使用形式是以适合之的常规形式采用的。
当防治卫生和贮藏产品害虫时,活性化合物的突出之处在于其在木材和粘土上的显著残留作用和对石灰处理过的底物上的碱的良好的稳定性。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如硬蜱、隐喙蜱、疥螨、恙螨科、(叮咬和吸吮)蝇、寄生蝇幼虫、虱、毛虱、鸟虱和蚤有活性。例如它们对蜱如微小牛蜱有显著的活性。
本发明式(I)活性化合物也适合防治侵害如下动物的节肢动物:牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。防治这些节肢动物时,旨在降低死亡率和性能(与肉、奶、羊毛、皮、蛋、蜜等等相关)损耗。这样,采用本发明活性化合物使更经济和更简单的动物管理成为可能。
本发明活性化合物可以已知的方式用在兽医方面,通过外部施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过沐浴或浸蘸、喷雾、浇泼、点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当用于家畜、家禽、家养动物等时,式(I)的活性化合物可以以制剂的形式(例如粉剂、乳剂、流动剂)的使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10,000倍后施用,或者它们可以以化学浴的形式使用。
而且,现已发现,本发明式(I)化合物对破坏工业材料的昆虫具有强的杀虫作用。
可以列举且是优选的昆虫是下列,但不限于这些昆虫:甲虫如
家天牛(Hylotrupes bajulus)、Chlorophorus pilosis、具斑窃蠹(Anobium punctatum)、Xestobium rufovillosum、Ptilinuspecticornis、Dendrobium pertinex、Ernobium mollis、Priobiumcarpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(L.afrcanus、平颈粉蠹(L.planicollis)、桴粉蠹(L.linesris)、L.pubescens、Trogoxylonaequale、鳞毛粉蠹(Minthes rugicollis)、小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostyrchuscapucins)、Heterobostrychus brunneus、Sinoxylon spec.、竹长蠹(Dinoderus minutus)。革翅目,如
小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigastaignus、U.augur。白蚁,如
木白蚁(Kalotermes flavicollis)、隐白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermes flavipes)、R.santonecsis、R.lucifugus、澳洲白蚁(Mastotermes darwiniensis)、Zootermopsis nevadensis、家白蚁(Coptotermes formosanus)。
衣鱼如西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为无生命的材料如优选的是合成材料、胶水、粘性材料、纸和板、皮革、木材和木制品、和漆。
非常特别优选的受保护而使之不被昆虫侵害的材料是木材和木制品。
可以用本发明的组合物或含有这种组合物的混合物保护的木材和木制品应理解为有下列含意,例如,建筑木料、木梁、铁道枕木、桥梁组件、突堤、木车、盒、箱、容器、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
本发明活性化合物可以以其原样、以其浓缩物或通常的常规制剂形式使用。所述的常规制剂是例如粉剂、颗粒剂、溶液、悬浮剂、乳剂或膏剂。
上述制剂可以以本身已知的方式制备,例如通过将活性化合物与至少一种下列物质混合:溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂、如果需要的话,脱水剂和UV稳定剂和如果需要的话,着色剂和染料和其它加工辅助剂。
用于保护木材和木制品的杀虫组合物或浓缩物包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
所采用的组合物或浓缩物的量取决于昆虫的种类和密度,以及介质。所用最佳量可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足矣。
所用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油型有机化学溶剂或溶剂混合物和/或极性有机溶剂或溶剂混合物和/或水,且如果适宜,是乳化剂和/或润湿剂。
优选采用的有机化学溶剂是油性或油型溶剂,所述的溶剂具有大于35的蒸发值和高于30℃的闪点,优选高于45℃。以原样使用的油性或油型溶剂的物质是低挥发性的,且不溶于水,这类物质适合的有矿物油或其芳族馏份或含有矿物油的溶剂混合物,优选是石油溶剂、石油和/或烷基苯。
有利地采用的物质是沸程为170到220℃的矿物油、沸程为170到220℃的石油溶剂、沸程为250到350℃的锭子油、沸程为160到280℃的石油或芳族化合物、松脂精等是有利的。
在优选的实施方案中,使用沸程为180至210℃的液体脂族烃或芳族和沸程为180至220℃的脂族烃的高沸点混合物和/或锭子油和/或单氯萘,优选-单氯萘。
蒸发值高于35且闪点高于30℃,优选高于45℃的低挥发性有机油性或油型溶剂,可以部分地由高或中挥发性的有机化学溶剂置换,其前提条件是,溶剂混合物也具有高于35的蒸发值且闪点高于30℃,优选高于45℃,且杀虫剂/杀真菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物由脂族极性有机化学溶剂或溶剂混合物置换。优选采用的物质是含有羟基和/或酯和/或醚基团的脂族有机化学溶剂,如例如乙二醇醚、酯等。
在本发明范围内使用的有机化学粘合剂是合成树脂和/或本身已知的粘合干性油,它们可以用水稀释和/或在所采用的有机化学溶剂中是可溶的、可分散的或可乳化的,特别是那些由如下组成,或包含如下成分的粘合剂:丙烯酸酯树脂、乙烯树脂,例如聚乙酸乙烯酯、聚酯树酯、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、苯酚树脂、烃类树脂如茚-香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
用作粘合剂的合成树脂可以以乳液、分散液或溶液的形式使用。沥青或沥青状物质也可以用作粘合剂的物质,其量至多为按重量计10%。此外,可以采用本身已知的着色剂、染料、防水剂、气味掩蔽剂和抑制剂或抗腐蚀剂等。
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醇酸树脂和/或干性植物油作为有机化学粘合剂。本发明优选采用的物质是油含量超过按重量计45%,优选50至68%的醇酸树脂。
所有的或部分上述粘合剂可以由固定剂(混合物)或增塑剂(混合物)置换。这些添加剂是旨在防止活性化合物的挥发和结晶或沉淀。它们优选替换0.01至30%的粘合剂(以所用粘合剂的100%为基准)。
增塑剂来自属于下列化学分类的物质:邻苯二甲酸酯类,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯类,如磷酸三丁酯,己二酸酯类,如二(2-乙基己基)己二酸酯,硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,如油酸丁酯,甘油醚类或较高分子量乙二醇醚类、甘油酯类和对甲苯磺酸酯类。
固定剂化学上基于聚乙烯烷基酯类如聚乙烯甲基酯,或酮类如二苯甲酮或亚乙基二苯甲酮。
特别适合的溶剂或稀释剂也可以是水,如果适宜,是水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。
特别有效的木材保护通过大规模的工业浸渍工艺,例如真空、双真空或加压工艺的方式获得。
如果适宜,直接可用的组合物可以包含其它杀虫剂和如果适宜,也可以有一种或多种杀真菌剂。
可能混合于其中的另外的适宜组分优选是WO 94/29268中提到的杀虫剂和杀真菌剂。在上述文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、silafluofin、氟氯氰菊酯、甲体氯氰菊酯、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,以及杀真菌剂如环氧唑(epoxyconazole)、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、metconazole、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
在室温下,将于100毫升二甲基亚砜中的3.86克(0.02摩尔)3-三氟甲基-4-丙烯基-1H-1,2,4-三唑啉-5-酮和2.76克(0.02摩尔)碳酸钾与5.41克(0.02摩尔)2,6-二硝基-4-三氟甲基氯苯混合,并在80℃下搅拌4小时,和在120℃下搅拌1小时。后处理时,将反应混合物与冰水搅拌,沉淀的产物抽吸过滤,并由异丙醇重结晶。
获得4.4克(理论值的52%)的1-(2,6-二硝基-4-三氟甲基苯基)-3-三氟甲基-4-丙烯基-1,2,4-三唑啉-5-酮,熔点136℃。
通过实施例1的方法和根据本发明制备方法的一般说明,可以制备出表1中所列的式(Ia)化合物:表1表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)应用实施例在下面的应用实施例中,采用下列化合物作为对比物质:
1-(2,6-二氯-4-三氟甲基苯基)-3-环丙基-4-甲基氨基-1,2,4-三唑啉-5-酮
(所有上述化合物由EP-A0617026公开,(A)=实施例44、(B)=实施例45、(C)=实施例72)实施例A辣根猿叶甲幼虫试验
溶剂:7重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备活性化合物的合适制剂,将1重量份的活性化合物与所述量的溶剂和所述量的乳化剂混合,并将该浓缩物用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,用辣根猿叶甲(Phaedon cochleariae)幼虫侵害。
经过所需的一段时间后,测定杀死%。100%是指所有的甲虫幼虫均被杀死;0%是指没有甲虫幼虫被杀死。
在此试验中,在实施活性化合物浓度为0.1%的条件下,7天后,杀死100%的有制备实施例5、8、11、12、13、15、21、27、36、42、45、50、57和83的化合物,而已知的化合物(B)和(C)分别显示无杀死和10%的死亡率。实施例B小菜蛾试验
溶剂:7重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备活性化合物的合适制剂,将1重量份的活性化合物与所述量的溶剂和所述量的乳化剂混合,并将该浓缩物用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,用小菜蛾(Plutella maculipennis)幼虫侵害。
经过所需的一段时间后,测定杀死%。100%是指所有的幼虫均被杀死;0%是指没有幼虫被杀死。
在此试验中,在实施活性化合物浓度为0.1%的条件下,7天后,杀死100%的有制备实施例4、5、12、21、22、32、49和81的化合物,而已知的化合物(C)显示10%的死亡率。实施例C草地贪夜蛾试验
溶剂:7重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备活性化合物的合适制剂,将1重量份的活性化合物与所述量的溶剂和所述量的乳化剂混合,并将该浓缩用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,用草地贪夜蛾(Spodoptera frugiperda)幼虫侵害。
经过所需的一段 时间后,测定活性%。100%是指所有的幼虫均被杀死;0%是指没有幼虫被杀死。
在此试验中,在实施活性化合物浓度为0.1%的条件下,7天后,杀死100%的有制备实施例10、12、21、49和50的化合物,而已知的化合物(C)未显示出活性。实施例D烟芽夜蛾试验
溶剂:7重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备活性化合物的合适制剂,将1重量份的活性化合物与所述量的溶剂和所述量的乳化剂混合,并将该浓缩用水稀释至所需浓度。
将大豆苗(Glycine max)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,用草地贪夜蛾(Heliothis virescens)幼虫侵害。
经过所需的一段时间后,测定杀死%。100%是指所有的幼虫均被杀死;0%是指没有幼虫被杀死。
在此试验中,在实施活性化合物浓度为0.1%的条件下,7天后,杀死100%的有制备实施例4和5的化合物,而已知的化合物(A)和(B)未显示出活性。实施例E黑尾叶蝉试验
溶剂:7重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备活性化合物的合适制剂,将1重量份的活性化合物与所述量的溶剂和所述量的乳化剂混合,并将该浓缩物用水稀释至所需浓度。
将稻秧(Oryza sativa)通过浸入所需浓度的活性化合物制剂中来处理,当秧苗仍润湿时,用黑尾叶蝉(Nephotettix cincticeps)侵害。
经过了所需的一段时间后,测定杀死%。100%是指所有的黑尾叶蝉均被杀死;0%是指没有黑尾叶蝉被杀死。
在此试验中,在实施活性化合物浓度为0.1%的条件下,7天后,杀死100%的有制备实施例12、31、41、45和58的化合物,而已知的化合物(A)、(B)和(C)未显示出活性。实施例F
微小牛蜱(SP-抗性Parkurst品系)抗性试验
试验动物:自己吸足血的雌成虫
溶剂:二甲基亚砜
将20mg活性化合物溶于1毫升二甲基亚砜中,并用相同的溶剂稀释,制成低浓度液。
重复进行试验5次。将1微升溶液注射入腹部,并将动物转移到培养皿中,保持在空调室中。由抑制产卵来确定活性。100%是指没有蜱产卵。
在此试验中,在实施活性化合物浓度为20微克的条件下,杀死100%的有制备实施例5、21、32、33、34和36的本发明化合物,而已知的化合物(A)、(B)和(C)未显示出活性。实施例G蜚蠊试验
试验动物:美洲大蠊
溶剂:35重量份的乙二醇单甲基醚
乳化剂:35重量份的壬基苯酚聚乙二醇醚
为制备合适的制剂,将3重量份的活性化合物与7重量份的上述溶剂-乳化剂混合物混合,并将所得乳液浓缩物用水稀释至各自所需浓度。
将2毫升此活性化合物制剂移到放在相应大小的培养皿中的过滤纸圆盘上( 9.5厘米)。过滤纸圆盘干燥后,移入5只美洲大蠊,并盖好。
3天后测定活性化合物制剂的活性。100%是指所有的蠊均被杀死;0%是指没有蠊被杀死。
在此试验中,在实施活性化合物浓度为1000ppm的条件下,显示出100%活性的有制备实施例4、5、12、21、27、28、32、36、41和50的本发明化合物,而已知的化合物(A)、(B)和(C)未显示出活性。实施例H家蝇试验
试验动物:成家蝇,Reichswald品系(OP、SP、氨基甲酸酯抗性)
溶剂:35重量份的乙二醇单甲基醚
乳化剂:35重量份的壬基苯酚聚乙二醇醚
为制备合适的制剂时,将3重量份的活性化合物与7重量份的上述溶剂-乳化剂混合物混合,并将所得乳液浓缩物用水稀释至各自所需浓度。
将2毫升此活性化合物制剂移到放在相应大小的培养皿中的过滤纸圆盘上( 9.5厘米)。过滤纸圆盘干燥后,将25只试验动物移入培养皿中,并盖好。
1、3、5和24小时后测定活性化合物制剂的活性。100%是指所有的家蝇均被杀死;0%是指没有家蝇被杀死。
在此试验中,在实施活性化合物浓度为100ppm的条件下,显示出100%活性的有例如制备实施例4、5、8、12、21、22、23、24、28、32、33和36的本发明化合物,而已知的化合物(A)、(B)和(C)未显示出活性。实施例I
蝇幼虫的发育抑制作用试验
试验动物:Lucilia cuprina(OP-抗性)所有的幼虫期
[蛹和成虫(不与活性化合物接触)]
溶剂:35重量份的乙二醇单甲基醚
乳化剂:35重量份的壬基苯酚聚乙二醇醚
为制备适合的制剂,将3重量份的活性化合物与7重量份的上述溶剂-乳化剂混合物混合,且所得的乳液浓缩物各用水稀释至各自所需浓度。
对于每一浓缩液,将30至50只幼虫转移到内含1cm3马肉的玻璃试管中。向此马肉上用吸管移500微升试验稀释液。将试管放入底部盖有一层海沙的塑料烧杯中,并保持在空调室中(26℃±1.5℃,70%±10%相对湿度)。24和48小时后检查活性(杀幼虫作用)。在幼虫留在玻璃试管中(大约72小时)后,将试管移出,且在烧杯上盖上打了孔的塑料盖。在1.5倍于发育期(对照蝇孵化)后,计数孵化的蝇和蛹/围蛹数。
活性标准是幼虫处理后48小时死亡(杀虫效果)或抑制由蛹孵化出成虫或抑制化蛹。物质的体外活性标准是抑制蝇的发育或将发育阻止在成虫期前。100%杀幼虫作用是指所有幼虫在48小时后被杀死。100%发育抑制作用是指没孵化出成蝇。
在此试验中,在1000ppm活性化合物浓度下,显示出100%活性的有例如制备实施例4、5、8、12、21、33、42和50的本发明化合物,而已知化合物(A)、(B)和(C)未显示出活性。
Claims (11)
1.防治动物害虫的组合物,其特征在于,含有至少一种式(I)化合物其中A代表氮或基团CR,R代表氢、卤素、硝基、氰基、羟基,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,任选取代的环烷基或基团-CX-NY1Y2,R1代表卤素、硝基、氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,任选取代的环烷基或基团-CX-NY1Y2,R2代表氢、卤素,任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基或任选取代的环烷基,R3代表硝基、卤代烷基、卤代烷氧基或基团-S(O)nR6,R4代表卤素、硝基、氰基,各任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、羟基、巯基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基、芳氧基烷基或芳烷基或基团-S(O)nR6,R5代表氢、氰基,各任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、炔氧基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基或芳烷基或基团-S(O)nR6、-NR7R8或-N=CR9R10之一,R6代表任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基,代表链烯基、链二烯基、炔基,任选取代的环烷基或任选取代的芳基,R7代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基,代表链烯基、炔基、烷氧基,任选取代的环烷基或任选取代的芳基,R8代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基,代表链烯基、炔基、烷氧基,任选取代的环烷基或任选取代的芳基,或R7和R8与连接的氮原子一起代表任选取代杂环,该杂环可任选含有一个或多个另外的杂原子,R9代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,R10代表氢,任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,X代表氧或硫,Y1代表氢或烷基,Y2代表氢或烷基,且n代表数字0、1或2之一。
2.防治动物害虫的组合物,其特征在于,含有至少一种根据权利要求1的式(I)化合物其中A代表氮或基团CR,R代表氢、氟、氯、溴、硝基、氰基、羟基,任选氟-、氯-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基取代的C3-C6-环烷基,或代表下列基团之一:-CONH2、-CSNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2或-CS-N(C1-C4-烷基)2,R1代表氟、氯、溴、硝基、氰基,各任选氟-、氯-、溴-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基或C1-C4-烷氧基,任选氟-、氯-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基取代的C3-C6-环烷基,或代表下列基团之一:-CONH2、-CSNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2和-CS-N(C1-C4-烷基)2,R2代表氢、氟、氯、C1-C4-烷基或C1-C4-卤代烷基,R3代表硝基、C1-C4-卤代烷基、C1-C4-卤代烷氧基或下列基团之一:-S-C1-C4-卤代烷基、-SO-C1-C4-卤代烷基或-SO2-C1-C4-卤代烷基,R4代表卤素、硝基、氰基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、羟基、巯基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基、苯氧基-C1-C4-烷基或苯基-C1-C4-烷基,它们各任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,或代表基团-S(O)nR6,R5代表氢、氰基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、C3-C6-炔氧基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或C3-C6-环烷基-C1-C4-烷基,任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,代表C1-C4-烷基取代的苄基或下列基团之一:-S(O)nR6、-NR7R8或-N=CR9R10,R6代表任选氟-、氯-、氰基-或硝基-取代的C1-C4-烷基,代表C3-C6-链烯基、C3-C6-链二烯基、C3-C6-炔基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,n代表数字0、1或2之一,R7代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基-取代的C1-C4-烷基,代表C3-C6-链烯基、C3-C6-炔基或C1-C4-烷氧基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,R8代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4烷基,代表C3-C6-链烯基、C3-C6-炔基或C1-C4-烷氧基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代的苯基,R7和R8与连接的氮原子一起代表任选卤素-、C1-C4-烷基、C1-C4-烷氧基或C1-C4-烷硫基取代的饱和5至7元杂环,该杂环除了氮原子外,具有2或3个相同或不同的选自氮、氧和硫的杂原子,R9代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基,和R10代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基。
3.防治动物害虫的组合物,其特征在于,含有至少一种根据权利要求1的式(I)化合物其中A代表氮或基团CR,R代表氢、氟、氯、溴、硝基、氰基、羟基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基或代表下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2或-CSN(CH3)2,R1代表氟、氯、溴、硝基、氰基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、三氟乙氧基或下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2和-CSN(CH3)2,R2代表氢、氟、氯、甲基或三氟甲基,R3代表三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、三氟甲基亚磺酰基、三氟甲基亚硫酰基或三氟甲基磺酰基,R4代表氯、溴、硝基、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、三氟乙氧基、四氟乙氧基、五氟乙氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、羟基、巯基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表苯基、苯氧基甲基或苄基,它们各任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、硝基或任选氟-、氯-或甲基取代的苯基取代,或代表基团-S(O)nR6,R5代表氢、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、氟丙基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、炔丙氧基、丁炔氧基,各任选氟-、氯-、溴、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表苯基,该苯基任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基,或任选氟-、氯-或甲基取代的苯基取代,代表任选甲基-、乙基-、正或异丙基-、正、异、仲或叔丁基取代的苄基,或代表下列基团之一:-S(O)nR6、-NR7R8或-N=CR9R10,R6代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、烯丙基、丙二烯基、炔丙基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环戊基或环己基,或苯基,该苯基任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基或任选氟-、氯-或甲基取代的苯基取代,n代表数字0、1或2之一,R7代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基或环丙基,R8代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基或环丙基,或R7和R8与连接的氮原子一起代表各任选甲基-、乙基-、甲氧基-或乙氧基-取代的哌啶基、哌嗪基或吗啉基,R9代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基,和R10代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基。
4.防治动物害虫的方法,其特征在于,使根据权利要求1的式(I)化合物作用于害虫和/或其栖生地。
5.根据权利要求1的式(I)化合物用于防治动物害虫的用途。
6.制备农药的方法,其特征在于,将根据权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
7.根据权利要求1的式(I)化合物制备农药的用途。
8.式(Ia)化合物其中A1代表氮或基团CR0,R0代表氢、卤素、硝基、氰基、羟基,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,任选取代的环烷基或基团-CX1-NY11Y12,R11代表卤素、硝基、氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,任选取代的环烷基或基团-CX1-NY11Y12,R12代表氢、卤素,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,任选取代的环烷基,R13代表硝基、卤代烷基、卤代烷氧基或基团-S(O)n 1R16,R14代表卤素、氰基,各任选卤素-、氰基-、硝基-、烷氧基或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、羟基、巯基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基、芳氧基烷基或芳烷基或基团-S(O)1 nR16,R15代表氢、氰基、氨基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基、炔氧基,各任选取代的环烷基或环烷基烷基,各任选取代的芳基或芳烷基或基团-S(O)1 nR16、-NR17R18或-N=CR19R20之一,R16代表任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表链烯基、链二烯基、炔基,任选取代的环烷基或任选取代的芳基,R17和R18与连接的氮原子一起代表任选取代杂环,该杂环可任选含有一个或多个另外的杂原子,R19代表氢,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,R20代表氢,任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表烷氧基、任选取代的环烷基或各任选取代的芳基或杂环基,X1代表氧或硫,Y11代表氢或烷基,Y12代表氢或烷基,且n代表数字0、1或2之一。
9.制备根据权利要求6的式(Ia)化合物的方法,其特征在于a)如下获得式(Ia)化合物其中R11、R12、R13、R14、R15和A1各如上所定义,如果适宜,在稀释剂存在下,和如果适宜,在反应辅助剂存在下,使式(II)的1H-三唑啉酮与式(III)的卤素衍生物反应其中R14和R15各如上所定义,其中R11、R12、R13和A1各如上所定义,和Hal代表卤素;b)如下获得式(Ib)化合物其中R11、R12、R13和A1各如上所定义,且R14-1代表氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基或烷氧基,代表链烯基、链烯氧基、炔基,各任选取代的环烷基或环烷基烷基或各任选取代的芳基、芳氧基烷基或芳烷基,在稀释剂存在下,使式(IV)的肼衍生物与式(V)的亚氨基羧酸酯反应其中R11、R12、R13和A1各如上所定义,其中R14-1如上所定义,且R21和R22相互独立地各代表烷基(优选C1-C8烷基);c)如下获得式(Ic)化合物其中R11、R12、R13、R14和A1各如上所定义,且R15-1代表氰基,各任选卤素-、氰基-、硝基-、烷氧基-或氨基-取代的烷基,代表链烯基、炔基、各任选取代的环烷基和环烷基烷基或任选取代的芳基,如果适宜,在稀释剂存在下,且如果适宜在反应辅助剂存在下,使式(Id)的N-芳基-1,2,4-三唑啉-5-酮与式(VI)的烷基化剂反应其中R11、R12、R13、R14和A1各如上所定义,
E-R15-1 (VI)其中R15-1如上所定义,且E代表吸电子离去基团。
10.根据权利要求8的式(Ia)化合物,其中A1代表氮或基团CR0,R0代表氢、氟、氯、溴、硝基、氰基、羟基,任选氟-、氯-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基取代的C3-C6-环烷基,或代表下列基团之一:-CONH2、-CSNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2和-CS-N(C1-C4-烷基)2,R11代表氟、氯、溴、硝基、氰基,各任选氟-、氯-、氰基-、硝基-或C1-C2-烷氧基取代的C1-C4-烷基或C1-C4-烷氧基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基取代的C3-C6-环烷基,或代表下列基团之一:-CONH2、-CSNH2、-CO-NH-C1-C4-烷基、-CS-NH-C1-C4-烷基、-CO-N(C1-C4-烷基)2或-CS-N(C1-C4-烷基)2,R12代表氢、氟、氯、C1-C4-烷基或C1-C4-卤代烷基,R13代表硝基、C1-C4-卤代烷基、C1-C4-卤代烷氧基或下列基团之一:-S-C1-C4-卤代烷基、-SO-C1-C4-卤代烷基或-SO2-C1-C4-卤代烷基,R14代表卤素、氰基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、羟基、巯基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基、苯氧基-C1-C4-烷基或苯基-C1-C4-烷基,它们各任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,或代表基团-S(O)1 nR16,R15代表氢、氰基、氨基,各任选氟-、氯-、氰基-、硝基-、C1-C4-烷氧基-或氨基-取代的C1-C4-烷基或C1-C4-烷氧基,代表C3-C6-链烯基、C3-C6-链烯氧基、C3-C6-炔基、C3-C6-炔氧基,各任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或C3-C6-环烷基-C1-C4-烷基,代表苯基,该苯基任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,代表任选C1-C4-烷基取代的苄基或下列基团之一:-S(O)1 nR16、-NR17R18或-N=CR19R20,R16代表任选氟-、氯-、氰基-或硝基-取代的C1-C4-烷基,代表C3-C6-链烯基、C3-C6-链二烯基、C3-C6-炔基,任选氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-卤代烷基-或C1-C4-卤代烷氧基-取代的C3-C6-环烷基,或苯基,该苯基任选由卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基或任选卤素-或C1-C4-烷基取代的苯基取代,n1代表数字0、1或2之一,R17和R18与连接的氮原子一起代表任选卤素-、C1-C4-烷基、C1-C4-烷氧基或C1-C4-烷硫基取代的饱和5至7元杂环,该杂环除了氮原子外,具有2或3个相同或不同的选自氮、氧和硫的杂原子,R19代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基,和R20代表氢,任选氟-、氯-、氰基-、硝基-、氨基-或C1-C4-烷氧基取代的C1-C4-烷基或代表C1-C4-烷氧基。
11.根据权利要求8的式(Ia)化合物,其中A1代表氮或基团CR0,R0代表氢、氟、氯、溴、硝基、氰基、羟基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基或代表下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2或-CSN(CH3)2,R11代表氟、氯、溴、硝基、氰基、甲基、乙基、正或异丙基、甲氧基甲基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、三氟乙氧基或代表下列基团之一:-CONH2、-CSNH2、-CONHCH3、-CSNHCH3、-CON(CH3)2或-CSN(CH3)2,R12代表氢、氟、氯、甲基或三氟甲基,R13代表三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、三氟甲基亚磺酰基、三氟甲基亚硫酰基或三氟甲基磺酰基,R14代表氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、三氟甲氧基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、三氟乙氧基、四氟乙氧基、五氟乙氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、羟基、巯基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表苯基、苯氧基甲基或苄基,它们各任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、硝基或任选氟-、氯-或甲基取代的苯基取代,或代表基团-S(O)1 nR16,R15代表氢、氰基、氨基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、氟丙基、二氟甲氧基、氯二氟甲氧基、二氯氟甲氧基、氰基甲基、烯丙基、烯丙氧基、炔丙基、炔丙氧基、丁炔氧基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环丙基甲基、环戊基、环戊基甲基、环己基或环己基甲基,代表苯基,该苯基任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基或任选氟-、氯-或甲基取代的苯基取代,代表任选甲基-、乙基-、正或异丙基-、正、异、仲或叔丁基取代的苄基,或代表下列基团之一:-S(O)1 nR16、-NR17R18或-N=CR19R20,R16代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氟乙基、四氟乙基、五氟乙基、氟丙基、烯丙基、丙二烯基、炔丙基,各任选氟-、氯-、溴-、甲基-、乙基-、甲氧基-、三氟甲基-或三氟甲氧基-取代的环丙基、环戊基或环己基,或苯基,该苯基任选由氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基、甲硫基、三氟甲硫基、氰基、硝基或任选氟-、氯-或甲基取代的苯基取代,n1代表数字0、1或2之一,R17和R18与连接的氮原子一起代表各任选甲基-、乙基-、甲氧基-或乙氧基-取代的哌啶基、哌嗪基或吗啉基,R19代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基,和R20代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基、甲氧基或乙氧基。
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DE19521162.6 | 1995-06-09 | ||
DE19521162A DE19521162A1 (de) | 1995-06-09 | 1995-06-09 | N-Aryl-1,2,4-triazolin-5-one |
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EP (1) | EP0831705B1 (zh) |
JP (1) | JPH11507651A (zh) |
KR (1) | KR100413330B1 (zh) |
CN (1) | CN1094725C (zh) |
AU (1) | AU703364B2 (zh) |
BR (1) | BR9609884A (zh) |
DE (2) | DE19521162A1 (zh) |
ES (1) | ES2162070T3 (zh) |
HU (1) | HUP9900365A3 (zh) |
MX (1) | MX9709398A (zh) |
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US6492527B1 (en) * | 1999-10-13 | 2002-12-10 | Fmc Corporation | Process to prepare aryltriazolinones and novel intermediates thereto |
US20020103233A1 (en) * | 2000-11-30 | 2002-08-01 | Arther Robert G. | Compositions for enhanced acaricidal activity |
CA2586612C (en) * | 2004-11-18 | 2016-10-11 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
WO2007094819A2 (en) * | 2005-08-18 | 2007-08-23 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
WO2007133820A2 (en) * | 2006-01-19 | 2007-11-22 | Neurogen Corporation | Diaryl triazolones as cb1 antagonists |
WO2007139968A2 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
EP2032545A2 (en) * | 2006-05-25 | 2009-03-11 | Synta Pharmaceuticals Corporation | Compounds that modulate hsp90 activity and methods for identifying same |
ES2484042T3 (es) * | 2006-05-25 | 2014-08-08 | Synta Pharmaceuticals Corporation | Compuestos de triazol que modulan la actividad de HSP90 |
EP2034996A2 (en) * | 2006-05-25 | 2009-03-18 | Synta Pharmaceuticals Corporation | Triazole compounds that modulate hsp90 activity |
WO2011133520A1 (en) | 2010-04-19 | 2011-10-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
EP2776025A1 (en) | 2011-11-02 | 2014-09-17 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with platinum-containing agents |
AU2012332421A1 (en) | 2011-11-02 | 2014-06-05 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of Hsp90 inhibitors with topoisomerase I inhibitors |
EP2780010A1 (en) | 2011-11-14 | 2014-09-24 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
EP2822931B1 (en) | 2012-03-09 | 2017-05-03 | Inception 2, Inc. | Triazolone compounds and uses thereof |
SG11201504622PA (en) | 2012-12-20 | 2015-07-30 | Inception 2 Inc | Triazolone compounds and uses thereof |
EA201690230A1 (ru) | 2013-09-06 | 2016-07-29 | Инсепшн 2, Инк. | Соединения триазолона и их применения |
CN104610177B (zh) * | 2015-02-02 | 2017-12-19 | 浙江树人大学 | 一种三唑酮类化合物的制备与应用 |
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DE2724819A1 (de) * | 1977-06-02 | 1978-12-07 | Hoechst Ag | Bis-phenyl-triazolone und verfahren zu ihrer herstellung |
DE2725148A1 (de) * | 1977-06-03 | 1978-12-14 | Hoechst Ag | 1-aryl-4-alkyl-1,2,4-triazol-5-one und verfahren zu ihrer herstellung |
CN85106905A (zh) | 1985-08-08 | 1987-02-04 | Fmc公司 | 含有1-芳基-δ2-1,2,4,-三唑啉-5-酮类的除草剂及其制备方法 |
US5174809A (en) | 1985-12-20 | 1992-12-29 | Fmc Corporation | Herbicidal aryl triazolinones |
US5294595A (en) | 1985-12-20 | 1994-03-15 | Fmc Corporation | Herbicidal aryl triazolinones |
US5214154A (en) | 1985-12-20 | 1993-05-25 | Fmc Corporation | Herbicidal aryl triazolinones |
US5041155A (en) | 1989-04-03 | 1991-08-20 | Fmc Corporation | Herbicidal aryl triazolinones |
DE4238125A1 (de) * | 1992-11-12 | 1994-05-19 | Bayer Ag | Substituierte Triazolinone |
EP0586513A1 (en) * | 1991-05-10 | 1994-03-16 | Merck & Co. Inc. | Acidic aralkyl triazole derivatives active as angiotensin ii antagonists |
US5256793A (en) | 1992-05-13 | 1993-10-26 | Fmc Corporation | Triazolinone ring formation in tert-butanol |
US5440045A (en) | 1992-05-13 | 1995-08-08 | Fmc Corporation | Triazolinone ring formation in tert-butanol |
US5262390A (en) * | 1992-08-26 | 1993-11-16 | Fmc Corporation | Herbicical 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates |
DE4239269A1 (de) * | 1992-11-23 | 1994-05-26 | Huesker Synthetic Gmbh & Co | Verfahren und Schirm zum Fixieren großflächiger Schlammablagerungen |
DE4303676A1 (de) * | 1993-02-09 | 1994-08-11 | Bayer Ag | 1-Aryltriazolin(thi)one |
DE4309966A1 (de) * | 1993-03-26 | 1994-09-29 | Bayer Ag | Substituierte 1-Aryltriazolinone |
-
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- 1995-06-09 DE DE19521162A patent/DE19521162A1/de not_active Withdrawn
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1996
- 1996-05-28 AU AU61231/96A patent/AU703364B2/en not_active Ceased
- 1996-05-28 ES ES96918634T patent/ES2162070T3/es not_active Expired - Lifetime
- 1996-05-28 HU HU9900365A patent/HUP9900365A3/hu unknown
- 1996-05-28 EP EP96918634A patent/EP0831705B1/de not_active Expired - Lifetime
- 1996-05-28 KR KR1019970708928A patent/KR100413330B1/ko not_active IP Right Cessation
- 1996-05-28 WO PCT/EP1996/002287 patent/WO1996041535A1/de active IP Right Grant
- 1996-05-28 BR BR9609884A patent/BR9609884A/pt not_active Application Discontinuation
- 1996-05-28 CN CN96195972A patent/CN1094725C/zh not_active Expired - Fee Related
- 1996-05-28 TR TR97/01576T patent/TR199701576T1/xx unknown
- 1996-05-28 US US08/973,538 patent/US6258957B1/en not_active Expired - Fee Related
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- 1996-05-28 DE DE59607589T patent/DE59607589D1/de not_active Expired - Fee Related
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DE19521162A1 (de) | 1996-12-12 |
KR19990022447A (ko) | 1999-03-25 |
US6258957B1 (en) | 2001-07-10 |
CN1094725C (zh) | 2002-11-27 |
JPH11507651A (ja) | 1999-07-06 |
DE59607589D1 (de) | 2001-10-04 |
HUP9900365A3 (en) | 1999-11-29 |
EP0831705B1 (de) | 2001-08-29 |
AU703364B2 (en) | 1999-03-25 |
MX9709398A (es) | 1998-07-31 |
AU6123196A (en) | 1997-01-09 |
EP0831705A1 (de) | 1998-04-01 |
HUP9900365A2 (hu) | 1999-05-28 |
WO1996041535A1 (de) | 1996-12-27 |
BR9609884A (pt) | 1999-03-23 |
ES2162070T3 (es) | 2001-12-16 |
KR100413330B1 (ko) | 2004-05-31 |
TR199701576T1 (xx) | 1998-05-21 |
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