CN1240449A - 取代的苯基酮-烯醇及其作为杀虫剂的应用 - Google Patents
取代的苯基酮-烯醇及其作为杀虫剂的应用 Download PDFInfo
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- CN1240449A CN1240449A CN97180627A CN97180627A CN1240449A CN 1240449 A CN1240449 A CN 1240449A CN 97180627 A CN97180627 A CN 97180627A CN 97180627 A CN97180627 A CN 97180627A CN 1240449 A CN1240449 A CN 1240449A
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- Prior art keywords
- alkyl
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- arbitrarily
- chlorine
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- 239000004009 herbicide Substances 0.000 title abstract description 3
- 239000000575 pesticide Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 110
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 56
- -1 octadecyloxy phenyl sulfenyl Chemical group 0.000 claims description 202
- 150000001875 compounds Chemical class 0.000 claims description 187
- 239000000460 chlorine Substances 0.000 claims description 184
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 115
- 229910052801 chlorine Inorganic materials 0.000 claims description 115
- 239000011737 fluorine Substances 0.000 claims description 103
- 229910052731 fluorine Inorganic materials 0.000 claims description 103
- 125000003545 alkoxy group Chemical group 0.000 claims description 95
- 238000006243 chemical reaction Methods 0.000 claims description 91
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 83
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 81
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 65
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 65
- 229910052794 bromium Inorganic materials 0.000 claims description 65
- 238000002360 preparation method Methods 0.000 claims description 64
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 150000002431 hydrogen Chemical class 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 47
- 239000001301 oxygen Substances 0.000 claims description 47
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 46
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 239000005864 Sulphur Substances 0.000 claims description 34
- 239000011230 binding agent Substances 0.000 claims description 33
- 239000002585 base Substances 0.000 claims description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 125000001544 thienyl group Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 241000238631 Hexapoda Species 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 15
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- 150000001412 amines Chemical class 0.000 claims description 12
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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- 239000013543 active substance Substances 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- RHJFWPOOZFAPEB-UHFFFAOYSA-N [O].C1=CSC=N1 Chemical compound [O].C1=CSC=N1 RHJFWPOOZFAPEB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 238000009333 weeding Methods 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- VKDHJTWRUAFVCO-UHFFFAOYSA-N N1=C(N=CC=C1)ON1N=CC=C1 Chemical class N1=C(N=CC=C1)ON1N=CC=C1 VKDHJTWRUAFVCO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 230000002508 compound effect Effects 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 47
- 150000001721 carbon Chemical group 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
- 229940126142 compound 16 Drugs 0.000 claims 1
- 125000004122 cyclic group Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
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- 239000000203 mixture Substances 0.000 description 54
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 52
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- 239000002904 solvent Substances 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
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- 239000000243 solution Substances 0.000 description 18
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- 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
- 229930192474 thiophene Natural products 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
- 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
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- 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
- 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
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
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Abstract
本发明涉及新的式(Ⅰ)的环状的苯基取代的酮-烯醇,其中Het表示下列基团之一,并且G、V、W、X、Y和Z分别如说明书中所定义,本发明还涉及它们的制备方法和制备中间体以及它们作为杀虫剂和除草剂的用途。
Description
本发明涉及新的苯基取代的环状酮-烯醇、其多种制备方法和制备中间体以及它们用作杀虫剂和除草剂的用途。
某些苯基取代的环状酮-烯醇有作为杀昆虫剂、杀螨剂和/或除草剂是公知的。
具有杀昆虫、杀螨虫活性和在某些情况下具有除草活性的1H-芳基吡咯烷-二酮衍生物是公知的(EP-A-456063、EP-A-521334、EP-A-596298、EP-A-613884、EP-A-613885、DE 4440594、WO94/01997、WO 95/01358、/WO 95/20572、EP-A-668267、WO95/26954、WO 96/25395和WO 96/35664)。
还公知某些取代的Δ3-二氢呋喃-2-酮衍生物具有除草特性(参见DE-A-4014420)。DE-A-4014420中还描述了用原料进行的季酮酸衍生物(例如,3-(2-甲基苯基)-4-羟基-5-(4-氟苯基)-Δ3-二氢呋喃-(2)-酮)的合成。类似结构的化物还公开于出版物Campbell等,J.Chem.Soc..Perkin Trans.1.1985,(8)1567-76,但其中未提及杀昆虫和/或杀螨虫活性。此外,具有除草、杀螨虫和/或杀昆虫特性的3-芳基-Δ3-二氢呋喃酮衍生物还公知于EP-A-528156、EP-A-0647637、WO 96/25395、WO 96/20196和上述迄今未公开的专利申请中。3-芳基-Δ3-二氢噻吩酮衍生物也是公知的(WO95/26345、WO 96/25395和WO 96/35664)。
但是,这些化合物的杀螨虫和杀昆虫活性和/或杀虫谱以及作物,尤其是农作物的耐受性不总是令人满意。
其中
V表示氢、卤素、烷基或烷氧基,
W表示氢、氰基、硝基、卤素、烷基、链烯基、炔基、烷氧基、卤代烷基、卤代烷氧基或者分别是可任意取代的苯基、苯氧基、苯硫基、苯基烷氧基或苯基烷硫基,
X表示卤素、烷基、链烯基、炔基、烷氧基、卤代烷基、卤代烷氧基、氰基、硝基或者分别是可任意取代的苯基、苯氧基、苯硫基、苯基烷氧基或苯基烷硫基,
Y表示氢、卤素、烷基、烷氧基、卤代烷基、卤代烷氧基、氰基或硝基,
Z表示氢、卤素、烷基、烷氧基、卤代烷基、卤代烷氧基、羟基、氰基、硝基或者分别是可任意取代的苯氧基、苯硫基、5-或6-元杂芳基氧基、5-或6-元杂芳硫基、苯基烷氧基或苯基烷氧基,或者
Y和Z与相连的碳原子一起表示可任意取代的环,该环可任意地被一个或多个杂原子间隔,或者
W和Z与相连的碳原子一起表示可任意取代的环,该环可任意地被一个或多个杂原子间隔,
其中
E表示金属离子等价物(Metallionaquivalent)或铵离子,
L表示氧或硫,
M表示氧或硫,
R1表示可任意被卤素或氰基取代的烷基、链烯基、烷氧基烷基、烷硫基烷基或多烷氧基烷基,或者表示可任意被卤素、烷基或烷氧基取代的环烷基或杂环基,或者表示可任意取代的苯基、苯基烷基、杂芳基、苯氧基烷基或杂芳氧基烷基,
R2表示可任意被卤素或氰基取代的烷基、链烯基、烷氧基烷基或多烷氧基烷基,或者表示可任意取代的环烷基、苯基或苄基,
R3、R4和R5各自彼此独立地表示可任意被卤素取代的烷基、烷氧基、烷基氨基、二烷基氨基、烷硫基、链烯硫基或环烷硫基,或者表示可任意取代的苯基、苄基、苯氧基或苯硫基,
R6和R7各自彼此独立地表示氢,表示可任意被卤素或氰基取代的烷基、环烷基、链烯基、烷氧基、烷氧基烷基,或者表示可任意取代的苯基、苄基,或者与相连的氮原子一起形成可任意含有氧或硫并可任意地被取代的环。
根据(特别是)取代基的性质,式(I)化合物可以旋光异构体或不同组成的异构体混合物形式存在,如果合适,可采用常规方法将混合物分离。纯净异构体或异构体混合物,它们的制备方法和用途以及含有它们的组合物均是本发明主题的一部分。为简便起见,下文中的式(I)化合物总是指纯净化合物,如果合适,也指含不同比例异构体化合物的混合物。包括含义(1)-(3)的Het基团,得出下面的基本结构(I-1)-(I-3):
其中
G、V、W、X、Y和Z分别如上所定义。
其中
E、L、M、V、W、X、Y、Z、R1、R2、R3、R4、R5、R6和R7各自如上所定义。
其中
E、L、M、V、W、X、Y、Z、R1、R2、R3、R4、R5、R6和R7各自如上所定义。
其中
E、L、M、V、W、X、Y、Z、R1、R2、R3、R4、R5、R6和R7各自如上所定义。
另外,发现新的式(I)化合物可通过下面描述的方法获得:
(A)式(I-1-a)化合物其中V、W、X、Y和Z如上所定义,可通过将式(II)化合物其中V、W、X、Y和Z如上所定义并且R8表示烷基(优选C1-C6烷基),在稀释剂和碱的存在下进行分子内缩合获得。(B)并且,发现式(I-2-a)化合物其中V、W、X、Y和Z如上所定义,可通过将式(III)化合物其中V、W、X、Y、Z和R8如上所定义在稀释剂和碱的存在下进行分子内缩合获得。(C)并且,发现式(I-3-a)化合物其中V、W、X、Y和Z如上所定义,可通过将式(IV)化合物
其中V、W、X、Y、Z和R8如上所定义
T表示氢、卤素、烷基(优选C1-C6烷基)或烷氧基(优选C1-C8烷氧基),
进行分子内环化获得,如果合适,环化反应可在稀释剂和酸的存在下进行。
并且发现
(D)如上所示的其中R1、V、W、X、Y和Z各自如上所定义的式(I-1-b)-(I-3-b)化合物可通过下面描述的方法获得:
将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别
其中
R1如上所定义
Hal表示卤素(尤其是氯或溴)
或β)与式(VI)的羧酸酐
R1-CO-O-CO-R1 (VI)
其中
R1如上所定义,
反应,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行;
(E)如上所示的其中R2、V、W、X、Y和Z各自如上所定义并且L表示氧的式(I-1-c)-(I-3-c)化合物可通过将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别
与式(VII)的氯甲酸酯或氯甲酸硫酯
R2-M-CO-Cl (VII)
其中
R2和M各自如上所定义,
反应获得,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行;
(F)如上所示的其中R2、V、W、X、Y和Z各自如上所定义并且L表示硫的式(I-1-c)-(I-3-c)化合物可通过将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别与式(VIII)的氯单硫代甲酸酯或氯二硫代甲酸酯
其中
M和R2各自如上所定义,
反应获得,如果合适反应可在有稀释剂的存在下和如果合适可在有酸结合剂的存在下进行;
(G)如上所示的其中R3、V、W、X、Y和Z各自如上所定义的式(I-1-d)-(I-3-d)化合物可通过将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别
与式(IX)的磺酰氯
R3-S2O-Cl (IX)
其中
R3如上所定义,
反应获得,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行;
(H)如上所示的其中L、R4、R5、V、W、X、Y和Z各自如上所定义的式(I-1-e)-(I-3-e)化合物可通过将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别
L、R4和R5各自如上所定义和
Hal表示卤素(尤其是氯或溴),
反应获得,如果合适反应可在有稀释剂的存在下和如果合适可在有酸结合剂的存在下进行;
(I)如上所示的其中E、V、W、X、Y和Z各自如上所定义的式(I-1-f)-(I-3-f)化合物可通过在将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别
其中
Me表示一价或二价金属(优选碱金属或碱土金属,如锂、钠、钾、镁或钙),
t表示1或2的数,并且
R10、R11和R12各自独立地表示氢或烷基(优选C1-C8烷基),
反应获得,如果合适反应可在有稀释剂的存在下进行;
(J)如上所示的其中L、R6、R7、V、W、X、Y和Z各自如上所定义的式(I-1-g)-(I-3-g)化合物可通过下面描述的方法获得:
将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别
α)与式(XIII)的异氰酸酯或异硫氰酸酯
R6-N=C=L (XIII)
其中
R6和L如上所定义,反应,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行。或β)与式(XIV)的氨基甲酰氯或硫代氨基甲酰氯
其中
L、R6和R7如上所定义,
反应,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行。
此外,发现新的式(I)化合物具有极好的杀虫活性,优选用作杀昆虫剂、杀螨虫剂和除草剂,并且它们还极易于为作物,尤其是农作物所频繁地耐受。
式(I)给出了本发明化合物的通式定义。优选取代基和/或本文中提及的该式中列出的基团如下所示:
V优选表示氢、卤素、C1-C6烷基或C1-C6烷氧基,
W优选表示氢、硝基、氰基、卤素、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基或者优选表示可任意被卤素、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、苯氧基、苯硫基、苯基-C1-C4烷氧基或苯基-C1-C4烷硫基,
X优选表示卤素、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、氰基、硝基或者优选表示可任意被卤素、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、苯氧基、苯硫基、苯基-C1-C4烷氧基或苯基-C1-C4烷硫基,
Y优选表示氢、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,
Z优选表示氢、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、硝基或者优选表示可任意被卤素、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、噻唑氧基、吡啶氧基、嘧啶氧基、吡唑氧基、苯基-C1-C4烷氧基或苯基-C1-C4烷氧基,或者
Y和Z与相连的碳原子一起优选表示可任意被卤素、C1-C6烷基、C1-C6烷氧基或C1-C4卤代烷基取代的C3-C5烷二基或C3-C5链烯二基,其中一至三个单元可任意地彼此独立地被氧、硫、氮或羰基代替,
W和Z与相连的碳原子一起优选表示可任意被卤素、C1-C6烷基、C1-C6烷氧基或C1-C4卤代烷基取代的C3-C5烷二基或C3-C5链烯二基,其中一至三个单元可任意地彼此独立地被氧、硫、氮或羰基代替,
(特别是(a)、(b)或(c))
其中
E表示金属离子等价物或铵离子,
L表示氧或硫,
M表示氧或硫,
R1优选表示可任意被卤素或氰基取代的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,或者优选表示可任意被卤素、C1-C6烷基或C1-C6烷氧基取代的C3-C8环烷基,其中的一个或两个不直接相邻的亚甲基可任意地被氧和/或硫代替,
优选表示可任意被卤素、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,
优选表示可任意被卤素、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,
优选表示可任意地被卤素或C1-C6烷基取代的5或6元含一或两个选自氧、硫和氮的杂原子的杂芳基,例如吡唑基、噻唑基、吡啶基、嘧啶基、呋喃基或噻吩基,
优选表示可任意地被卤素或C1-C6烷基取代的苯氧基-C1-C6烷基或者
优选表示可任意地被卤素、氨基或C1-C6烷基取代的5或6元含一或两个选自氧、硫和氮的杂原子的杂芳氧基-C1-C6烷基,例如吡啶氧基-C1-C6烷基、嘧啶基-C1-C6烷基或噻唑氧基-C1-C6烷基。
R2优选表示可任意被卤素或氰基取代的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,
优选表示可任意被卤素、C1-C6烷基或C1-C6烷氧基取代的C3-C8环烷基或者
优选表示可任意地被卤素、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优选表示可任意地被卤素取代的C1-C8烷基或优选表示可任意地被卤素、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各自彼此独立地优选表示可任意被卤素取代的C1-C8烷基、C1-C8烷氧基、C1-C8烷基氨基、二-(C1-C8烷基)氨基、C1-C8烷硫基或C3-C8链烯硫基,或者优选表示任意地被卤素、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各自彼此独立地优选表示氢,分别优选表示可任意被卤素或氰基取代的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,或者分别优选表示可任意被卤素、C1-C8烷基、C1-C8卤代烷基或C1-C8烷氧基取代的苯基或苄基,或者二者一起优选表示可任意被C1-C6烷基取代的C3-C6亚烷基,其中的一个亚甲基可任意地被氧或硫代替。
V特别优选表示氢、氟、氯、溴、C1-C4烷基或C1-C4烷氧基,
W特别优选表示氢、硝基、氰基、氟、氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基或者分别特别优选表示可任意被氟、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基、苯氧基或苄氧基。
X特别优选表示氟、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、硝基或者特别优选表示可任意被氟、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基、苯氧基或苄氧基。
Y特别优选表示氢、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,
Z特别优选表示氢、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、硝基或者优选表示可任意被氟、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,或者
Y和Z与相连的碳原子一起特别优选表示可任意被氟、氯、溴、C1-C4烷基、C1-C4烷氧基或C1-C2卤代烷基取代的C3-C4烷二基或C3-C4链烯二基,其中一至两个不直接相邻的单元可任意地彼此独立地被氧、硫或氮代替,或者
W和Z与相连的碳原子一起特别优选表示可任意被氟、氯、溴、C1-C4烷基、C1-C4烷氧基或C1-C2卤代烷基取代的C3-C4烷二基或C3-C4链烯二基,其中一至两个不直接相邻的单元可任意地彼此独立地被氧、硫或氮代替,
其中
E表示金属离子等价物或铵离子,
L表示氧或硫,
M表示氧或硫,
R1特别优选表示可任意被氟或氯取代的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,或者特别优选表示可任意被氟、氯、C1-C5烷基或C1-C5烷氧基取代的C3-C7环烷基,其中的一个或两个不直接相邻的亚甲基可任意地被氧和/或硫代替,
特别优选表示可任意被氟、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,
特别优选表示可任意被氟、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,
特别优选表示可任意地被氟、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,
特别优选表示可任意地被氟、氯、溴或C1-C4烷基取代的苯氧基-C1-C5烷基或者
特别优选表示可任意地被氟、氯、溴、氨基或C1-C4烷基取代的吡啶氧基-C1-C5烷基、嘧啶基-C1-C5烷基或噻唑氧基-C1-C5烷基。
R2特别优选表示可任意被氟或氯取代的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,
特别优选表示可任意被氟、氯、C1-C4烷基或C1-C4烷氧基取代的C3-C7环烷基或者
特别优选表示可任意地被氟、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特别优选表示可任意地被氟或氯取代的C1-C6烷基或特别优选表示可任意地被氟、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各自彼此独立地特别优选表示可任意被氟或氯取代的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链烯硫基,或者特别优选表示任意地被氟、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各自彼此独立地特别优选表示氢,分别特别优选表示可任意被氟或氯取代的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,或者分别特别优选表示可任意被氟、氯、溴、C1-C5卤代烷基、C1-C5烷基或C1-C5烷氧基取代的苯基或苄基,或者二者一起特别优选表示可任意被C1-C4烷基取代的C3-C6亚烷基,其中的一个亚甲基可任意地被氧或硫代替。
V最优选表示氢、氟、氯、溴、甲基、乙基、丙基、异丙基、叔丁基、甲氧基、乙氧基、丙氧基或异丙氧基。
W最优选表示氢、硝基、氰基、氟、氯、溴、甲基、乙基、丙基、正丁基、异丙基、异丁基、甲氧基、乙氧基、丙氧基、异丙氧基、三氟甲基、二氟甲氧基、三氟甲氧基、苯基或苄氧基。
X最优选表示氟、氯、溴、甲基、乙基、丙基、丁基、异丁基、异丙基、甲氧基、乙氧基、丙氧基、异丙氧基、三氟甲基、三氟甲氧基、二氟甲氧基、氰基、硝基、苯基或苄氧基。
Y最优选表示氢、氟、氯、溴、甲基、乙基、丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、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最优选表示氢、氟、氯、溴、甲基、乙基、丙基、丁基、异丁基、异丙基、叔丁基、甲氧基、乙氧基、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,或者
Y和Z与相连的碳原子一起最优选表示可任意被氟、氯、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、丙氧基、异丙氧基或三氟甲基取代的C3-C4烷二基,其中两个不直接相邻的单元可任意地被氧代替,或者
W和Z与相连的碳原子一起最优选表示可任意被氟、氯、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、丙氧基、异丙氧基或三氟甲基取代的C3-C4烷二基,其中两个不直接相邻的单元可任意地被氧代替,
(尤其是表示(a),(b)或(c))其中
E表示金属离子等价物或铵离子,
L表示氧或硫,
M表示氧或硫,
R1最优选表示可任意被氟或氯取代的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烷基或多-C1-C4烷氧基-C1-C4烷基,或者最优选表示可任意被氟、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C3-C6环烷基,其中的一个或两个不直接相邻的亚甲基可任意地被氧和/或硫代替,
最优选表示可任意被氟、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、甲磺酰基或乙磺酰基取代的苯基,
最优选表示可任意被氟、氯、溴、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基取代的苄基,
最优选表示可任意地被氟、氯、溴、甲基或乙基取代的呋喃基、噻吩基或吡啶基,
最优选表示可任意地被氟、氯、甲基或乙基取代的苯氧基-C1-C4烷基或者
最优选表示可任意地被氟、氯、氨基、甲基或乙基取代的吡啶氧基-C1-C4烷基、嘧啶基-C1-C4烷基或噻唑氧基-C1-C4烷基。
R2最优选表示可任意被氟或氯取代的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,
最优选表示可任意被氟、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
最优选表示可任意地被氟、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最优选表示可任意地被氟或氯取代的甲基、乙基、丙基、异丙基、正丁基、叔丁基或最优选表示可任意地被氟、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各自彼此独立地最优选表示可任意被氟或氯取代的C1-C4烷基、C1-C4烷氧基、C1-C4烷基氨基、二-(C1-C4烷基)氨基、C1-C4烷硫基,或者最优选表示任意地被氟、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各自彼此独立地最优选表示氢,分别最优选表示可任意被氟或氯取代的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,或者分别最优选表示可任意被氟、氯、溴、甲基、甲氧基或三氟甲基取代的苯基或苄基,或者二者一起最优选表示可任意被甲基或乙基取代的C5-C6亚烷基,其中的一个亚甲基可任意地被氧或硫代替。
上述基团的一般的或优选的定义或说明可按需彼此结合,也就是说所讨论的范围和优选范围之间可以相结合。它们不仅适用于终产物,也相应地适用于原料和中间体。
本发明优选那些包含如上优选给出的定义结合的式(I)化合物。
本发明特别优选那些包含如上特别优选给出的定义结合的式(I)化合物。
本发明最优选那些包含如上最优选给出的定义结合的式(I)化合物。
饱和或不饱和的烃基,如烷基或链烯基也可与杂原子结合,如在各种直链或支链烃基的情况下可结合形成烷氧基。
可任意取代的基团可以是单或多取代的,在多取代的情况下,取代基可以相同或不同。
除制备实施例中的化合物外,可特别列举下面的式(I-1-a)化合物:
表1V X W Y ZH Br H Cl HH Cl H Br HH Cl H Cl HH Cl H F HH F H Cl HH Cl H OCH3 HH Cl H CH3 HH OCH3 H Cl HH OCH3 H OCH3 HH CH3 H Cl HH CH3 H F HH CH3 H OCH3 HH CH3 H t-C4H9HH CH3 H CH3 HH Cl Cl H HH Cl F H HH Cl OCH3 H HH Cl CH3 H HH Cl OC2H5H HH OCH3 OCH3 H HH CH3 CH3 H HH Br CH3 Br HH Cl Cl CH3 HV X W Y ZH CH3 Br CH3 HH CH3 Cl CH3 HH CH3 OCHF2 CH3 HH CH3 OCH2CF3CH3 HH CH3 OC2H5 CH3 HH CH3 OCH3 CH3 HH CH3 CH3 CH3 HH Br Br CH3 HH Cl Cl CH3 HH C2H5 C2H5 Br HH CH3 CH3 Br HH CH3 CH3 OCH3 HH Br Cl CH3 HH Br CH3 Cl HH Cl CH3 Br HH C2H5 Br CH3 HH CH3 O-C3H7 CH3 HH CH3 O-Bz* CH3 HH CH3 CH3 Cl HH CH3 Ph* CH3 HH Cl H Cl ClH CH3 H CH3 CH3H CH3 H Cl CH3H Br H Cl CH3H Br H CH3 CH3H Cl H Br CH3H Cl H Cl CH3H CH3 H Br CH3H Cl H Cl FH Cl H -O-CF2-O- V X W Y ZH Br H -(CH2)3-H Cl H CH3 ClH CH3 H H HH Cl H H HH Br H H HH O-Bz H H HH CF3 H H HH OCH3 H H HH CH3 CH3 CH3 CH3CH3 CH3 H CH3 CH3CH3 CH3 CH3 H CH3H Br Br -(CH2)3-H CH3 CH3 CH3 FH CH3 CH3 CH3 ClH CH3 CH3 CH3 BrH CH3 CH3 H ClH CH3 CH3 H BrH Cl Cl H BrCH3 CH3 CH3 CH3 CH3
*Bz=苄基;Ph=苯基
除制备实施例中的化合物外,可特别列举下面的式(I-2-a)化合物:
其中
V、W、X、Y和Z如表1中所定义。
除制备实施例中的化合物外,可特别列举下面的式(I-3-a)化合物:
表3
其中
V、W、X、Y和Z如表1中所定义。
采用方法(Dα),以3-[(2-氯-4-甲基)-苯基]-5,5-亚甲氧基丙基-吡咯烷-2,4-二酮和新戊酰氯为原料,本发明方法的反应过程可用下式表示:
采用方法(H),以2-[(4-溴-2-氯-6-甲基)-苯基]-4-羟基-5,5-亚甲氧基丙基-Δ3-二氢呋喃-2-酮和(2,2,2-三氟乙基)-甲基硫代膦酰氯为原料,本发明方法的反应过程可用下式表示:
采用方法(J)(α法),以3-[(2-氯-4-溴-5-甲基)-苯基]-4-羟基-5,5-亚甲氧基丙基-Δ3-二氢呋喃-2-酮和异氰酸乙酯为原料,本发明方法的反应过程可用下式表示:
其中V、W、X、Y和Z分别定义如上,并且
Hal表示氯或溴(Chem.Review 52,237-416(1953);Bhattacharya,Indian J.Chem.6,341-5,1968);
式(XVII)化合物可通过例如按照Schotten-Baumann(Organkum,VEB Deutscher Verlag der Wissenschaften,Berlin 1977,p.505)将式(XVIII)的3-氨基四氢吡喃-3-羧酸用式(XVI)的取代的苯乙酰基卤酰化获得,
其中V、W、X、Y和Z分别定义如上,并且
Hal表示氯或溴。
某些式(XVI)化合物是新化合物,可采用公知的方法制备(参见,例如WO 97/02243、WO 97/01535和DE-196 13 171)。
式(XVI)化合物可通过例如将其中V、W、X、Y和Z分别定义如上的式(XIX)的取代的苯基乙酸
与卤化试剂(例如硫酰氯、硫酰溴、草酰氯、光气、三氯化磷、三溴化磷或五氯化磷)反应获得,如果合适反应可在有稀释剂(例如任选的氯代脂族或芳族烃,如甲苯和氯甲烷)的存在下,在-20℃-150℃,优选在-10℃-100℃的温度下进行。
某些式(XIX)化合物是新化合物,它们可通过文献公知的方法(Organikum 15th edition,p.533,VEB Deutscher Verlag DerWissenschaften,Berlin 1977,参见例如WO 97/02243、WO 97/01535和DE-19613171)制备。式(XIX)化合物可通过例如在酸(例如无机酸,如盐酸)或碱(例如碱金属氢氧化物,如氢氧化钠或氢氧化钾)的存在下,如果合适可在有稀释剂(例如醇,如甲醇或乙醇的水溶液)的存在下,在0℃-150℃,优选20℃-100℃的温度下水解其中V、W、X、Y、Z和R8分别定义如上的式(XX)的取代的苯基乙酸获得。
某些式(XX)化合物是新化合物,它们基本上可采用公知的方法制备。
与醇化物(如碱金属醇化物,如甲醇钠或乙醇钠)在稀释剂(例如由醇化物衍生的醇)在0℃-150℃,优选在20℃-120℃下反应,然后再与酸(优选无机酸,如硫酸)在-20℃-150℃,优选在0℃-100℃下反应(参见DE 3314249)。
某些式(XXI)化合物是新化合物,它们基本上可通过公知的方法制备。
与二氯乙烯(CH=CCl2)在其中R13表示烷基、优选C1-C6烷基的式(XXIII)的烷基亚硝酸酯的存在下,
R13-ONO (XXIII)
在氯化铜(II)的存在下,如果合适可在有稀释剂(例如脂族腈,如乙腈)的存在下,在-20℃-80℃,优选0℃-60℃的温度下反应。
某些式(XXII)化合物是已知化合物,它们可采用文献公知的方法制备,例如通过还原相应的硝基化合物或通过卤化苄胺或乙酰苄胺,然后裂解制备。
式(XXIII)化合物是已知的有机化合物。氯化铜(II)和二氯乙烯也是很早就公知的化合物,并且都有市售。
式(XV)和(XVIII)化合物是新化合物。它们可采用公知的方法制备(参见,例如Compagnon,Ann.Chim.(Paris)[14]5,p.11-22,23-27(1970),L.Munday,J.Chem.Soc.4372(1961);J.T.Eward,C.Jitrangeri,Can.J.Chem.53,3339(1975)。
或者,在方法(A)中被用作原料的其中V、W、X、Y、Z和R8分别定义如上的式(II)化合物可通过如下的方法制备:
将式(XXIV)的3-氨基-四氢吡喃-3-甲腈
随后进行酸醇解。
式(XXV)的化合物也是新化合物。式(XXIV)化合物也是新的(参见制备实施例)。
它们基本上可采用公知的方法简便地制备。
式(XXVI)的3-羟基-四氢吡喃-3-羧酸酯是新化合物。它们了通过例如按照Pinner的方法(参见制备实施例),在酸的存在下,醇化式(XXVI-a)的3-羟基-四氢吡喃-3-甲腈获得。该氰醇可通过例如将四氢吡喃-3-酮与氢氰酸反应获得。
它们基本上可采用公知的方法制备。
用其中T定义如上并且Hal表示卤素(尤其是氯或溴)的式(XXVII)的2-苄硫基-甲酰卤在强碱存在下酰化(参见,如M.S.Chambers,E.J.Thomas,D.J.Williams,J.Chem.Soc.Chem.Commun.,(1987),1228)。
式(XXVII)的苄硫基甲酰卤是新化合物。它们可采用公知的方法制备(J.Antibiotics(1983),26,1589)。
在方法(D)、(E)、(F)、(G)、(H)、(I)和(J)中被用作原料的式(V)的酰卤、式(VI)的酸酐、式(VII)的氯甲酸酯或氯甲酸硫酯、式(VIII)的氯单硫代甲酸酯或氯二硫代甲酸酯、式(IX)的磺酰氯、式(X)的磷化合物、式(XI)和(XII)的金属氢氧化钠、金属醇化物或胺以及式(XIII)的异氰酸酯和式(XIV)的氨基甲酰氯通常是已知的有机或无机化合物。
式(XVI)、(XIX)、(XX)、(XXI)和(XXII)化合物也可从所引述的专利申请中获知并且/或者可采用其中给出的方法制备(参见WO96/35664、WO 97/01535、WO 97/02243和DE 19613171)。
方法(A)的特征在于将其中V、W、X、Y、Z和R8分别定义如上的式(II)化合物在有稀释剂和碱的存在下进行分子内缩合。
用于本发明方法(A)的适宜稀释剂是所有对反应物呈惰性的有机溶剂。优选使用烃,如甲苯和二甲苯;醚,如二丁基醚、四氢呋喃、二氧六环、甘醇二甲醚和二甘醇二甲醚;极性溶剂,如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基吡咯烷酮以及醇类,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
适用于本发明方法(A)的适宜的碱(去质子剂)是所有各种常用的质子接受剂。优选使用碱金属和碱土金属氧化物、氢氧化物和碳酸盐,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,它们也可在相转移催化剂,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TDA1(=三-(甲氧基乙氧基乙基)胺)的存在下使用。也可使用碱金属,如钠或钾。此外,可使用碱金属或碱土金属氨基化物和氢化物,如氨基钠、氢化钠或氢化钙,还可使用碱金属醇化物,如甲醇钠、乙醇钠和叔丁醇钾。
当采用本发明的方法(A)时,反应温度可在相当宽的范围内变化。通常反应在-75℃-200℃,优选在-50℃-150℃下进行。
本发明的方法(A)通常在大气压下进行。
当采用本发明的方法(A)时,反应物式(II)和去质子剂通常以等摩尔的量至约两倍摩尔的量使用。但一者或另一者的用量也可相对大大过量(多达3摩尔)。
方法(B)的特征在于将其中V、W、X、Y、Z和R8分别定义如上的式(III)化合物在稀释剂和碱的存在下进行分子内缩合。
用于本发明方法(B)的适宜稀释剂是所有对反应物呈惰性的有机溶剂。优选使用烃,如甲苯和二甲苯;醚,如二丁基醚、四氢呋喃、二氧六环、甘醇二甲醚和二甘醇二甲醚;极性溶剂,如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基吡咯烷酮以及醇类,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
适用于本发明方法(B)的适宜的碱(去质子剂)是所有各种常用的质子接受剂。优选使用碱金属和碱土金属氧化物、氢氧化物和碳酸盐,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,它们也可在相转移催化剂,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)的存在下使用。也可使用碱金属,如钠或钾。此外,可使用碱金属或碱土金属氨基化物和氢化物,如氨基钠、氢化钠或氢化钙,还可使用碱金属醇化物,如甲醇钠、乙醇钠和叔丁醇钾。
当采用本发明的方法(B)时,反应温度可在相当宽的范围内变化。通常反应在-75℃-200℃,优选在-50℃-150℃下进行。
本发明的方法(B)通常在大气压下进行。
当采用本发明的方法(B)时,反应物式(III)和去质子剂通常以约等摩尔的量使用。但一者或另一者的用量也可相对大大过量(多达3摩尔)。
方法(C)的特征在于将其中T、V、W、X、Y、Z和R8分别定义如上的式(IV)化合物在酸,和如果合适可在有稀释剂的存在下进行分子内环化。
用于本发明方法(C)的适宜稀释剂是所有对反应物呈惰性的有机溶剂。优选使用烃,如甲苯和二甲苯;卤代烃,如二氯甲烷、氯仿、二氯乙烷、氯苯、二氯苯;极性溶剂,如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基吡咯烷酮。或者,也可使用醇类,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
如果合适,也可使用酸作为稀释剂。
适用于本发明方法(C)的适宜酸是所有常用的无机和有机酸,如氢卤酸、硫酸、烷基磺酸、芳基磺酸和卤代烷基磺酸,尤其适用的是卤代烷基羧酸,如三氟乙酸。
当采用本发明的方法(C)时,反应温度可在相当宽的范围内变化。通常反应在0℃-250℃,优选在50℃-150℃下进行。
本发明的方法(C)通常在大气压下进行。
当采用本发明的方法(C)时,反应物式(IV)和酸通常以约等摩尔的量使用。但如果合适,也可使用催化量的酸。
方法(Dα)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(V)的甲酰卤反应,如果合适该反应可在有稀释剂的存在下和如果合适可在酸结合剂的存在下进行。
用于本发明方法(Dα)的适宜稀释剂是所有对酰卤呈情性的溶剂。优选使用烃类,如汽油、苯、甲苯、二甲苯、1,2,3,4-四氢化萘;卤代烃,如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;酮类,如丙酮、甲基异丙基酮;醚类,如乙醚、四氢呋喃和二氧六环;还有羧酸酯,如乙酸乙酯和强极性溶剂,如二甲基甲酰胺、二甲亚砜和环丁砜。只要酰卤的水解稳定性,反应也可在水的存在下进行。
适于本发明方法(Dα)的适宜的酸结合剂是常用的酸结合剂。优选使用叔胺,如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一碳烯(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,如氧化镁和氧化钙;碱金属和碱土金属碳酸盐,如碳酸钠、碳酸钾和碳酸钙以及碱金属氢氧化物,如氢氧化钠和氢氧化钾。
当采用本发明的方法(Dα)时,反应温度可在相当宽的范围内变化。通常反应在-20℃-+150℃,优选在0℃-100℃下进行。
当采用本发明的方法(Dα)时,原料式(I-1-a)-(I-3-a)化合物与式(V)的甲酰卤通常以约等摩尔的量使用。但也可使用相对大大过量(多达5摩尔)的甲酰卤。并用常规方法进行后处理。
方法(Dβ)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(VI)的酸酐反应,如果合适该反应可在有稀释剂的存在下和如果合适可在酸结合剂的存在下进行。
用于本发明方法(Dβ)的适宜稀释剂优选是那些在酰卤情况下使用的稀释剂。另外,过量使用的酸酐也可同时被用作稀释剂。
如果合适,加到方法(Dβ)中的酸结合剂优选那些在采用酰卤的情况下优选使用的酸结合剂。
当采用本发明的方法(Dβ)时,反应温度可在相当宽的范围内变化。通常反应在-20℃-+150℃,优选在0℃-100℃下进行。
当采用本发明的方法(Dβ)时,式(I-1-a)-(I-3-a)化合物的原料与式(VI)的酸酐通常以约等摩尔的量使用。但也可使用相对大大过量(多达5摩尔)的酸酐。并用常规方法进行后处理。
通常,通过蒸馏或者用有机溶剂或用水洗涤除去稀释剂和过量的酸酐以及形成的羧酸。
方法(E)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(VII)的氯甲酸酯或氯甲酸硫酯反应,如果合适该反应可在有稀释剂和如果合适可在酸结合剂的存在下进行。
适于本发明方法(E)的适宜的酸结合剂是常用的酸结合剂。优选使用叔胺,如三乙胺、吡啶、DABCO、DBU、DBN、Hunig碱和N,N-二甲基苯胺;还有碱土金属氧化物,如氧化镁和氧化钙;碱金属和碱土金属碳酸盐,如碳酸钠、碳酸钾和碳酸钙以及碱金属氢氧化物,如氢氧化钠和氢氧化钾。
用于本发明方法(E)的适宜稀释剂是所有对氯甲酸酯或氯甲酸硫酯呈惰性的溶剂。优选使用烃类,如汽油、苯、甲苯、二甲苯、1,2,3,4-四氢化萘;卤代烃,如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;酮类,如丙酮、甲基异丙基酮;醚类,如乙醚、四氢呋喃和二氧六环;还有羧酸酯,如乙酸乙酯和腈类,如乙腈以及强极性溶剂,如二甲基甲酰胺、二甲亚砜和环丁砜。
当采用本发明的方法(E)时,反应温度可在相当宽的范围内变化。通常反应在-20℃-+100℃,优选在0℃-50℃下进行。
本发明的方法(E)通常在大气压下进行。
当采用本发明的方法(E)时,原料式(I-1-a)-(I-3-a)化合物与式(VII)的氯甲酸酯或氯甲酸硫酯通常以约等摩尔的量使用。但也可使用相对大大过量的一者或另一者(多达2摩尔)。并用常规方法进行后处理。通常,除去沉淀的盐,将剩余反应混合物在减压下除去稀释剂浓缩。
方法(F)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(VIII)化合物在稀释剂的存在下反应,如果合适该反应可在酸结合剂的存在下进行。
在制备方法(F)中,将每摩尔式(I-1-a)-(I-3-a)的原料化合物分别与约1摩尔式(VIII)的氯单硫代甲酸酯或氯二硫代甲酸酯于0-120℃,优选在20-60℃下反应。
如果合适,可加入稀释剂,它们是所有惰性的极性有机溶剂,如醚、酰胺、砜、亚砜和硫代烷。
优选使用二甲基亚砜、四氢呋喃、二甲基甲酰胺、乙酸乙酯和二氯甲烷。
在优选的实施方案中,式(I-1-a)-(I-3-a)的烯醇盐通过加入强去质子剂,如氢化钠或叔丁醇钾制备,也可不加入酸结合剂。
用于方法(F)的适宜碱是所有常用的质子接受剂。优选使用碱金属氢化物、碱金属或碱土金属碳酸盐或碳酸氢盐或者含氮的碱。例如氢化钠、甲醇钠、氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄基胺、二异丙基胺、吡啶、喹啉、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)和二氮杂双环十一碳烯(DBU)。
反应可在大气压或在升高的压力下进行,但优选在大气压下进行。并用常规方法进行后处理。
方法(G)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(IX)的磺酰氯反应,如果合适该反应可在稀释剂的存在下和如果合适可在酸结合剂的存在下进行。
在制备方法(G)中,将每摩尔式(I-1-a)-(I-3-a)的原料化合物分别与约1摩尔式(IX)的磺酰氯于-20-150℃,优选在0-70℃下反应。
方法(G)优选在有稀释剂的存在下进行。
适宜的稀释剂是所有惰性的极性有机溶剂,如醚、酰胺、酮、羧酸酯、腈类、砜、亚砜或卤代烃,如二氯甲烷。
优选使用二甲基亚砜、四氢呋喃、二甲基甲酰胺、乙酸乙酯和二氯甲烷。
在优选的实施方案中,式(I-1-a)-(I-3-a)的烯醇盐的制备通过加入强去质子剂,如氢化钠或叔丁醇钾进行,也可不加入酸结合剂。
如果采用酸结合剂,适用的有常用的无机或有机碱,如氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在大气压或在升高的压力下进行,但优选在大气压下进行。并用常规方法进行后处理。
方法(H)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(X)的磷化合物反应,如果合适该反应可在稀释剂的存在下和如果合适可在酸结合剂的存在下进行。
在制备方法(H)中,将1-2,优选1-1.3摩尔的式(X)的磷化合物与每摩尔的式(I-1-a)-(I-3-a)原料化合物分别在于-40-150℃,优选在-10-110℃下反应,获得式(I-1-e)-(I-3-e)化合物。
方法(H)优选在有稀释剂的存在下进行。
适宜的稀释剂是是所有惰性的极性有机溶剂,如醚、羧酸酯、卤代烃、酮、酰胺、腈类、砜或亚砜等。
优选使用乙腈、二甲基亚砜、四氢呋喃、二甲基甲酰胺、二氯甲烷。
如果合适可加入酸结合剂,它们是常用的无机或有机碱,如氢氧化物、碳酸盐或胺。实例包括氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在大气压或在升高的压力下进行,但优选在大气压下进行。并用常规方法进行后处理。终产物优选通过结晶、色谱纯化或通过所谓的“赋形剂蒸馏(Andestillieren)”,即减压除去挥发性成分进行纯化。
方法(I)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(XI)的金属氢氧化物或金属醇化物或者式(XII)的胺反应,如果合适该反应可在稀释剂的存在下进行。
优选用于本发明方法(I)的稀释剂是醚,如四氢呋喃、二氧六环、乙醚或醇,如甲醇、乙醇、异丙醇,但也可使用水。本发明方法(I)通常在大气压下进行。反应温度通常为-20-100℃,优选0-50℃。
方法(J)的特征在于将式(I-1-a)-(I-3-a)的化合物分别与式(XIII)的化合物反应(Jα)或者与式(XIV)的化合物反应(Jβ),前者的反应如果合适可在稀释剂的存在下和如果合适可在催化剂的存在下进行;后者的反应如果合适可在稀释剂的存在下和如果合适可在酸结合剂的存在下进行。
在制备方法(Jα)中,将每摩尔式(I-1-a)-(I-3-a)的原料化合物分别与约1摩尔式(XIII)的异氰酸酯于0-100℃,优选在20-50℃下反应。
方法(Jα)优选在有稀释剂的存在下进行。
适宜的稀释剂是是所有惰性的有机溶剂,如芳族烃、卤代烃、醚、酰胺、腈类、砜或亚砜。
如果合适,可加入催化剂促进反应。可使用的非常有益的催化剂是有机锡化合物,如二月桂酸二丁基锡。
该方法优选在大气压下进行。
在制备方法(Jβ)中,将每摩尔式(I-1-a)-(I-3-a)的原料化合物分别与约1摩尔式(XIV)的氨基甲酰氯于0-150℃,优选在20-70℃下反应。
如果合适可加入稀释剂,它们是所有惰性的极性有机溶剂,如醚、羧酸酯、腈类、酮、酰胺、砜、亚砜或卤代烃类。
优选使用二甲基亚砜、四氢呋喃、二甲基甲酰胺和二氯甲烷。
在优选的实施方案中,式(I-1-a)-(I-3-a)的烯醇盐通过加入强去质子剂(如氢化钠或叔丁醇钾)制备,也可不加入酸结合剂。
如果采用酸结合剂,适用的有常用的无机或有机碱,实例包括氢氧化钠、碳酸钠、碳酸钾、三乙胺和吡啶。
反应可在大气压或在升高的压力下进行,但优选在大气压下进行。并用常规方法进行后处理。
本发明活性化合物适合防治动物害虫,优选节肢动物和线虫,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。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:
等足目,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidium vulgare)和斑鼠妇(Porcellio scaber)。
倍足目,例如,具斑马陆(Blaniulus guttulatus)。
唇足目,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigera spec)。
综合目,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)和沙漠蝗(Schistocerca gregaria)。
革翅目,例如,欧洲球螋(Forficula 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(Pemphigus spp.)、体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。
食毛目,例如,啮毛虱属(Trichodectes spp.)和畜属虱(Damalineaspp.)。
缨翅目,例如,Frankliniella occidentalis、温室条蓟马(Hercinothripsfemoralis)、Thrips palmi和棉蓟马(Thrips tabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimexlectularius)、长红猎蝽(Rhodnius prolixus)和锥蝽属(Triatoma 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.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphaxstriatellus)、稻褐飞虱(Nilaparvata lugens)、红肾园盾蚧(Aonidiellaaurantii)、夹竹桃园蚧(Aspidiotus hederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupaluspiniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithocolletisblancardella)、苹果巢蛾(Hyponomeuta padella)、小菜蛾(Plutellamaculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctischrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrixthurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Eariasinsulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾(Spodoptera exigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolis flammea)、斜纹夜蛾(Prodenia litura)、灰翅夜蛾属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pierisspp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestia kuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineola bisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoecia podana)、Capua reticulana、枞色卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homona magnanima)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(Epilachnavarivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilussurinamensis)、花象甲属(Anthonomus 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(Lyctusspp.)、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(Tribolium spp.)、黄粉虫(Tenebrio molitor)、叩头虫属(Agriotesspp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)和褐新西兰肋翅鳃角金龟(Costelytra zealandica)。
膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampaspp.)、田蚁属(Lasius spp.)、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(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophoraerythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanus spp.)、螗蜩属(Tanniaspp.)、花园毛蚊(Bibio hortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbia spp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitis capitara)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipulapaludosa)。
蚤目,例如,印鼠客蚤(Xenopsylla cheopis)、毛列蚤属(Ceratophyllus spp.)。
蛛形目,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectusmactans)。
蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、茶瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyommaspp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychus spp.)。
本发明活性化合物的突出之处在于其强的杀虫和杀螨活性。
它们可以特别成功地采用来防治对植物有害的昆虫,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。
本发明的活性化合物还可作为脱叶剂、干燥剂、除草剂,尤其是除草剂使用。从广义上说,草应理解为生长在不应生长的地方的所有植物。本发明的物质是否被用作非选择性和选择性除草剂则取决于所使用的量。
本发明的活性化合物的防治杂草的剂量为0.001-10kg/ha,优选0.005-5kg/ha。
本发明的活性化合物可应用于下列植物:
双子叶属草:芸苔属(Sinapis)、独行菜属(Lepidium)、猪殃殃属(Galium)、繁缕属(Stellaria)、母菊属(Matricaria)、春黄菊属(Anthemis)、galinsoga、美洲土荆芥(Chenopodium)、荨麻属(Urtica)、美狗舌草(Senecio)、苋属(Amaranthus)、马齿苋属(Portulaca)、苍耳属(Xanthium)、旋花属(Convolvulus)、药薯(Ipomoea)、蓼属(Polygonum)、Sesbania、豕草属(Ambrosia)、蓟属(Cirsium)、飞廉属(Carduus)、苦苣菜属(Sonchus)、茄属(Solanum)、焊菜(Roripa)、Rotola、Lindernia、夜芝麻属(Lamium)、婆婆纳属(Veronica)、苘麻属(Abutilon)、曼陀罗属(Datura)、堇菜属(Viola)、Galeopsis、罂粟属(Papaver)、矢车菊属(Centaurea)、Trifolium、毛茛属(Ranunculus)和蒲公英(Taraxacum)。
双子叶属作物:棉花(Gossypium)、大豆属(Glycine)、甜菜属(Beta)、胡萝卜属(Daucus)、菜豆属(Phaseolus)、豌豆(Pisum)、茄属(Solanum)、Linum、药薯(Ipomoea)、蚕豆属(Vicia)、烟草属(Nicotiana)、番茄(Lycopersicum)、落花生属(Arachis)、芸苔属(Brassica)、莴苣属(Lactuca)、黄瓜属(Cucumis)和南瓜属(Cucurbita)。
单子叶属草:Echinochloa、狗尾草属(Setaria)、黍属(Panicum)、马唐属(Digitaria)、猫尾草(Phleum)、Poa、Festuca、Eleusine、Brachiaria、毒麦(Lolium)、雀麦(Bromus)、燕麦属(Avena)、莎草属(Cyperus)、高粱(Sorghum)、偃麦草(Agropyron)、Cycnodon、雨久花属(Monochoria)、Fimbristylis、慈菇属(Sagittaria)、Eleocharis、威草属(Scirpus)、Paspalum、Ischaemum、Sphenoclea、Dactyloctenium、Agrostis、Alopecurus和Apera。
单子叶属作物:稻属(Oryza)、玉米属(Zea)、小麦属(Triticum)、大麦(Hordeum)、燕麦属(Avena)、黑麦属(Secale)、Sorghum、黍属(Panicum)、甘蔗属(Saccharum)、菠罗(Ananas)、芦笋(Asparagus)和葱属(Allium)。
但是,本发明活性化合物的应用不仅限于这些植物,同样可以相同方式应用于其它植物。
根据浓度,可使化合物适用于完全除去杂草,例如用于有或没有树木种植的工业地区和铁道区、道路和广场。同样地,活性化合物可用于防治多年生作物中的杂草,如用于森林、装饰性树木种植园、果园、葡萄园、柑橘种植园、坚果园、香蕉种植园、咖啡种植园、茶种植园、橡胶种植园、油棕榈种植园、可可种植园、软果(soft fruit)种植园和啤酒花地、草坪、草皮和草原,以及用于选择性除去一年生作物中的杂草。
本发明化合物特别适合于以芽前或芽后的方法选择性地防治双子叶作物中的单子叶杂草。例如它们可以采用来非常成功地在棉花或甘蔗中防治杂草。
活性化合物可以转化成常规剂型,如溶液、乳剂、悬浮剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳浓缩物、用活性化合物浸渍的天然和合成材料和聚合物微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与增量剂,即液体和/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。
如果允许,在用水作增量剂的情况下,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,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份、矿物和植物油,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,如二甲基甲酰胺或二甲基亚砜,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:例如压碎并分级的天然岩石,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: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,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,亚硫酸木素废液和甲基纤维素。
制剂中可以使用增稠剂如粉状、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。其它的添加剂是矿物油和植物油。
也可使用着色剂,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%,并还优选含有增量剂和表面活性剂。
本发明活性化合物可以其市售制剂和由这些制剂制备的使用形式存在,作为其与其它如下的活性化合物的混合物形式:杀虫剂、引诱剂、不育剂、杀细菌剂、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类、氨基甲酸酯、羧酸酯类、氯代烃类、苯基脲类和由微生物生产的物质。
特别有益的混合成分实例是下列化合物: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-2′-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-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、呋菌胺、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、甲羟异恶唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净(IBP)、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、灭锈胺、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、稻瘟酯、戊菌唑、戊菌隆、稻病磷、稻瘟酞、匹马菌素、哌啶宁、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(PCNB)、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、AC 303 630、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)、AZ 60541、苦楝素、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、丁酮成、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA 157 419、CGA 184 699、除线威、氯氧磷、毒虫畏、定虫隆、氯甲硫磷、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰葡酯、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(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、异丙威、恶唑磷、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、NC 184、定虫脒、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、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH 5992、水杨硫磷、硫线磷、硅氟菊酯、治螟磷、甲丙硫磷、虫酰肼、吡螨胺、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、YI 5301/5302、zetamethrin。
除草剂:
苯胺类,如吡氟酰草胺和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸类,如2,4-D,2,4-滴丁酸(2,4-DB)、2,4-DP、氯氟吡氧乙酸、2甲4氯(MCPA)、MCPP、定草酯;芳氧基苯氧基链烷酸酯类,如禾草灵、精恶唑禾草灵、精吡氟禾草灵、氟吡禾草灵和精喹禾灵;嗪酮类(azinones),如氯草敏和氟草敏;氨基甲酸酯类,如氯普芬、甜菜安、苯敌草和苯胺灵;氯代乙酰苯胺类,如甲草胺、乙草胺、丁草胺、吡唑草胺、异丙甲草胺、丙草胺和毒草胺;二硝基苯胺类,如胺磺乐灵、喷达曼萨林和氟乐灵;二苯基醚类,如氟锁草醚、治草醚、乙羧氟草醚、氟磺胺草醚、halosafen、乳氟禾草灵和氧氟吩;脲类,如chlortoluron、敌草隆、伏草隆、异丙隆、利农伦和唑隆;羟胺类,如禾草灭、烯草酮、噻草酮、稀禾定和三甲苯草酮;咪唑啉酮类,如咪唑乙烟酸、咪草酸、咪唑烟酸和咪唑喹啉酸;腈类,如溴草腈、敌草腈和碘苯腈;氧乙酰胺类,如苯噻酰草胺;磺酰脲类,如酰嘧磺隆、苄嘧磺隆、氯嘧磺隆、氯磺隆、醚磺隆、甲磺隆、烟嘧磺隆、氟嘧磺隆、吡嘧磺隆、噻吩磺隆、醚苯磺隆和苯磺隆;硫代氨基甲酸酯类,如丁草敌、环草敌、燕麦敌、茵草敌、戊草丹、禾草敌、苄草丹、禾草丹、野麦畏;三嗪类,如莠去津、氰乙酰肼、西玛津、西草净、特丁净和特丁津;三嗪酮类,如环嗪酮、苯嗪草酮和草克净;其它类,如杀草强、呋草黄、bentazone、环庚草醚、异恶草松、二氯吡啶酸、野燕枯、氟硫草定、灭草呋喃、氟咯草酮、草安膦、草甘膦、异恶酰草胺、哒草特、二氯喹啉酸、氯甲喹啉酸、草硫膦和灭草环。
本发明活性化合物可以其市售制剂和由这些制剂制备的使用形式存在,作为其与协同剂的混合物形式。协同剂是增强活性化合物作用的化合物,而加入的协同剂本身并不需要具备活性。
由市售制剂制备的使用形式中的活性化合物含量可在较宽的范围内变化。使用形式中的活性化合物浓度可在0.0000001-95%(重量),优选在0.0001-1%(重量)。
活性化合物可以适于使用形式的常规方式使用。
当用于对抗卫生方面的害虫和贮存制品的害虫时,活性化合物在木材和粘土中具有显著的残留作用,并对石灰物质中的碱具有良好稳定性。
本发明的活性化合物不仅在植物、卫生方面和贮存制品具有杀虫活性,但也可应用于兽医对抗动物寄生虫(体外寄生虫),如硬蜱、隐喙蜱、痒螨、恙螨、苍蝇(叮咬和吸吮)、寄生的苍蝇幼虫、虱、发虱、禽虱和蚤。这些寄生虫包括:
虱目(Anoplurida):例如血虱属(Haematopinus spp.)、长颚虱属(Linognathus spp.)、虱(Pediculus)、阴虱属(Phtirus spp.)、盲虱属(Solenopotes spp.)。
食毛目(Mallophagida)及Amblycerina亚目和Ischnocerina亚目,例如Trimenopon spp.、Menopon spp.、Trinoton spp.、Bovicola spp.、Werneckiella spp.、Lepikentron spp.、啮虱目(Damalina spp.)、啮毛虱目(Trichodectes spp.)、猫虱目(Felicola spp.)。
双翅目及长角亚目和短角亚目(brachycerina),例如伊蚊属(Aedesspp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simuliumspp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、Hybomitra spp.、Atylotus spp.、虻属(Tabanus spp.)、麻虻属(Haematopotaspp.)、Philipomyia spp.、Braula spp.、蝇属(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、血蝇属(Haematobia spp.)、Morellia spp.、厕蝇属(Fanniaspp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphora spp.)、绿蝇属(Luciliaspp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮下蝇属(Hypoderma spp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、Lipoptena spp.、蜱蝇属(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉头蚤属(Ctenocephalides spp.)、客蚤属(Xenopsylla spp.)、角叶蚤属(Ceratophyllusspp.)
异翅亚目(Heteropterida),例如臭虫属(Cimex spp.)、锥蝽属(Triatomaspp.)、长红猎蝽(Rhodnius spp.)、锥蝽属(Panstrongylus spp.)、
蠊目(Blattarida),例如东方蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、德国小蠊(Blattela germanica)和Supella spp。
螨亚纲(Acaridae)及Meta-和Mesostigmata亚目,例如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、Otabius spp.、硬蜱属(Ixodesspp.)、钝眼蜱属(Amblyomma spp.)、方头蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、璃眼蜱属(Hyalommaspp.)、扇头蜱属(Rhipicephalus spp.)、皮刺螨属(Dermanyssus spp.)、瑞立绦虫属(Raillietia spp.)、肺刺螨(Pneumonyssus spp.)、Sternostoma spp.和Varroa spp。
Actinedida(Prostigmata)和螨科(Astigmata),例如,伍氏螨(Acarapisspp.)、姬螯螨属(Cheyletiella spp.)、Ornithocheyletia spp.、Myobia spp.、Psorergates spp.、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、Listrophorus spp.、螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、Caloglyphus spp.、Hypodectes spp.、Pterolichus spp.、痒螨属(Psoroptesspp.)、皮螨属(Chorioptes spp.)、Octodectes spp.、疥螨属(Sarcoptes spp.)、耳螨属(Notoedres spp.)、鸟疥螨属(Knemidocoptes spp.)、Cytodites spp.和Laminosioptes spp.
本发明的式(I)活性化合物还适于防治攻击农业牲畜,例如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水族馆鱼和所谓的试验动物,例如仓鼠、豚鼠、大鼠和小鼠的节支动物。防治这些节支动物的目的在于降低死亡率和减少活动性(在肉、奶、毛、兽皮、蛋和蜂蜜等中的),因此使用本发明的活性化合物可以使动物的喂养更经济和简便。
在兽医方面,本发明的活性化合物可以公知的方式通过胃肠施用(如以片剂、胶囊、饮用水、顿服药、颗粒剂、糊剂、大丸剂、饲喂方法、栓剂方式);通过非胃肠施用,如通过注射(肌内、皮下、静脉内和腹膜内等)和植入剂方式;经鼻施用和经皮施用(如以浸渍、洗浴、喷雾、涂敷和点涂、清洗、喷粉和借助包含活性化合物的成型物品,如领、耳签、尾标、肢带、笼头和标记设备等形式)。
当对牲畜、家禽和家养动物施用时,式(I)的化合物可以制剂(如粉剂、乳剂和可流动物)形式施用,所述制剂中活性化合物的含量为1-80%(重量),其可直接或经稀释100-10000倍后施用;它们也可以化学浴形式施用。
此外,发现本发明的式(I)化合物对毁坏工业材料的昆虫有很强的杀虫作用。
下列以实例方式列举的昆虫是优选的,但不是限定性的:
甲虫,例如Hylotrupes bajulus、多毛天牛(Chlorophorus pilosis)、家具窃蠹(Anobium punctatum)、Xestobium rufovillosum、栉角窃蠹(Ptilinus pecticornis)、石槲(Dendrobium pertinex)、Ernobius mollis、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、平颈粉蠹(Lyctus planicollis)、桴粉蠹(Lyctus linearis)、软毛粉蠹(Lyctuspubescens)、Trogoxylon aequale、Minthes rugicollis、Xyleborus spec.、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、Bostrychuscapucins、Heterobostrychus brunneus、长蠹(Sinoxylon spex)、竹长蠹(Dinoderus minutus)。
革翅目,例如,小钢青树蜂(Sirex juvencus)、大树蜂(Urocerusgigas)、针叶大树蜂(Urocerus gigas taignus)和Urocerus augur。
白蚁,例如,木白蚁(Kalotermes flavicollis)、Cryptotermes brevisheterotermes indicola黄胸散白蚁(Reticulitermes flavipes)、Reticulitermessantonensis、避光犀白蚁(Reticulitermes lucifugus)、澳洲白蚁(Mastotermesdarwiniensis)、古白蚁(Zootermopasis nevadensis)、家白蚁(Coptotermesformosanus)。
石虫丙(Bristletails),例如,西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为非生命的材料,例如,优选是合成材料、胶、浆料、纸和纸板、皮革、木材和木制品以及油漆。
特别优选的免受昆虫侵害的是木材和木制品。
可受本发明的组合物或含有这类组合物的混合物保护的木材和木制品应理解为,例如,建筑木料、木条、铁道枕木、桥梁构件、码头、木制运输工具、夹板、木制容器、电话台、木制隔热层、木制门窗、夹板、碎板、木匠物品或木制品,它们都是房屋建筑和细木工行业中常用的。
活性化合物可以浓缩物或常规制剂形式使用,例如粉剂、颗粒剂、溶液、悬浮液、乳液或糊剂。
所述的制剂可按照先前已知的方式配制,例如通过将活性成分与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、驱避剂混合,如果适当可加入干燥剂和UV稳定剂,并且如果适当可加入着色剂、颜料和其它加工助剂。
用于保护木制品或木材的杀昆虫组合物和浓缩物包括浓度为0.0001-95%(重量),尤其是0.001-60%(重量)的本发明活性化合物。
组合物和浓缩物的用量取决于昆虫的种类和发生情况以及介质。最佳施用率可取决于各种系列试验。通常,基于所保护的材料,施用0.0001-20%重量,优选0.001-10%重量的活性化合物就足以。
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性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,如果合适,还可使用乳化剂和/或润湿剂。
优选使用的有机化学溶剂是蒸发数高于35和闪点高于30℃,优选高于45℃的油或油性溶剂。被用作这类油或油性溶剂的物质具有低挥发性并且不溶于水,适宜的是矿物油或它们的芳香馏分,或者含矿物油溶剂的混合物,优选油漆溶剂油、石油和/或烷基苯。
可使用的有益矿物油是沸点在170-220℃之间的矿物油,沸点在170-220℃之间的油漆溶剂油,沸点为250-350℃的锭子油、沸点为160-280℃的石油或芳香成分和松节油香精等。
在优选的实施方案中,使用沸点为180-210℃的液态脂族烃或沸点为180-220℃的高沸点芳族和脂族烃混合物和/或一氯萘,优选α-一氯萘。
挥发数高于35并且闪点高于30℃,优选高于45℃的低挥发性有机油或油性溶剂可部分地被高度或中度挥发性的有机化学溶剂替代,前提是溶剂混合物的挥发数高于35,闪点高于30℃,优选高于45℃,并且杀昆虫/杀真菌混合物可溶于或乳化于该溶剂混合物中。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物可被脂族极性有机化学溶剂或溶剂混合物替代。优选使用的物质是带有羟基和/或酯和/或醚基的脂族有机化学溶剂,例如甘醇醚和酯等。
在本发明范围中使用的有机化学粘合剂是先前公知的合成树脂和/或无水的粘合油,它们可用水稀释和/或溶于、分散于或乳化于所使用的有机化学溶剂中,具体地说,粘合剂包括丙烯酸酯树脂、乙烯树脂,例如聚乙酸乙烯酯、聚酯树脂、聚缩合或聚甲醇树脂、聚脲树脂、醇酸树脂或改性的醇酸树脂、苯酚树脂、烃树脂,如茚/香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或物理干性粘合剂(基于天然或合成树脂的)。
用作粘合剂的合成树脂可以乳液、分散液或溶液形式使用。至多10%(重量)的沥青或沥青类物质也可用作粘合剂。此外,可使用着色剂、颜料、防水剂、臭味掩蔽剂和先前公知的抑制剂或防腐剂等。
本发明的组合物或浓缩物优选包含至少一种醇酸树脂或改性的醇酸树脂和/或干性植物油作为有机化学粘合剂。本发明优选使用的醇酸树脂占油的含量超过45%(重量),优选为50-68%(重量)。
所有的或某些上述的粘合剂可被固定剂(混合物)或增塑剂(混合物)替代。这些添加剂的目的是防止活性化合物的挥发和结晶或沉淀。它们优选替代0.01-30%的粘合剂(基于使用的粘合剂为100%)。
增塑剂在化学上是邻苯二甲酸酯类(如邻苯二甲酸二丁基酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯)、磷酸酯(如磷酸三丁酯)、脂肪酸酯(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基酯)、油酸酯(如油酸丁酯)、甘油醚或相对高分子量的甘醇醚、甘油酯和对甲苯磺酸酯。
固定剂是聚乙烯烷基醚类(如聚乙烯甲基醚)或酮类(如二苯酮或亚乙基二苯酮)。
特别适于作为溶剂或稀释剂的还有水,如果合适,可使用水与一种或多种上述的有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别优选保护的木材是通过大规模工业浸渍方法,例如真空、两次真空或加压方法获得的。
如果合适,现成的组合物还可含有其它杀昆虫剂,并且如果合适还可含有一种或多种杀真菌剂。
可混入的适宜的其它成分优选是WO 94/29269中提及的杀昆虫剂和杀真菌剂。显然,该文献中提及的化合物也构成了本申请的一部分。
可混入的特别优选的成分是杀昆虫剂,如毒死蜱(chlorpyriphos)、辛硫磷(phoxim)、氟硅菊酯(silafluofin)、顺式氯氰菊酯(alphamethrin)、氟氯氰菊酯(cyfluthrin)、氯氰菊酯(cypermethrin)、溴氰菊酯(deltamethrin)、苄氯菊酯、氯菊酯(permethrin)、吡虫啉(imidacloprid)、啶虫脒(NI-25)、氟虫脲(flufenoxuron)、epoxyconazole、氟铃脲(hexaflumuron)、环氧唑(azaconazole)、丙环唑(propiconazole)、戊唑醇(tebuconazole)、环丙唑醇(cyproconazole)、metconazole、抑霉唑(imazalil)、二氯氟磺胺(dichlorofluanide)、甲苯氟磺胺(tolylfluanide)、3-碘-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。
下列实施例可说明本发明活性化合物的制备和应用。
实施例
实施例I-1-a-1
在回流温度下,将17.3g实施II-1的化合物在160ml无水甲苯中的溶液滴加到14.05g(0.125mol)叔丁醇钾在54ml无水四氢呋喃(THF)中的溶液中,将该混合物在该温度下再搅拌1.5小时。冷却后,加入160ml水,分层,甲苯相用80ml水萃取,在0-20℃下,将合并的水相用浓盐酸酸化。吸滤出产物、洗涤、干燥,然后进一步纯化,与甲基叔丁基(MTB)醚/N-己烷搅拌,吸滤并干燥。收率:12.1g(理论收率的77%),熔点:200℃。
类似地,和/或按照通用制备方法,制得下列式(I-1-a)的化合物:表4实施例号 V W X Y Z 熔点℃I-1-a-2 H CH3 CH3 CH3 CH3 219I-1-a-3 H CH3 CH3 Br H >220I-1-a-4 H H CH3 CH3 H 226I-1-a-5 H H Cl Cl H >220I-1-a-6 H H CH3 CH3 CH3 130I-1-a-7 H H CH3 H CH3 187I-1-a-8 H Br Cl CH3 H >220I-1-a-9 H H CH3 Br CH3 >220I-1-a-10 H Cl CH3 Cl H >220I-1-a-11 H H Br CH3 CH3 145I-1-a-12 H CH3 CH3 H Br 194I-1-a-13 H CH3 CH3 CH3 Br
在回流下,将2.88g(0.0010mol)实施例(I-1-a-1)的化合物和2.1ml(15mmol)三乙胺在50ml无水乙酸乙酯中的溶液与1.85ml(0.15mol)新戊酰氯在5ml无水乙酸乙酯中的溶液混合。将该混合物在回流下搅拌直至反应结束(根据薄层色谱分析)。为进行后处理,将反应混合物浓缩,加到二氯甲烷中,用50ml 0.5N氢氧化钠水溶液洗涤两次,经硫酸镁干燥并浓缩。粗产物在MTB醚/N-己烷中重结晶。收率:2.0g(理论收率的53%),熔点:193℃。
类似地,和/或按照通用制备方法,制得下列式(I-b-1)的化合物:
表5实施例号 V W X Y Z R1 熔点℃I-1-b-2 H CH3 CH3 CH3 H i-C3H7 163I-1-b-3 H CH3 CH3 CH3 CH3 i-C3H7 153I-1-b-4 H CH3 CH3 CH3 CH3 2-噻吩基 >220I-1-b-5 H CH3 CH3 Br H i-C3H7 190I-1-b-6 H CH3 CH3 Br H 2-噻吩基 >220I-1-b-7 H CH3 CH3 Br H 4-Cl-氯苯基 209I-1-b-8 H CH3 H H CH3 i-C3H7 178I-1-b-9 H CH3 H CH3 CH3 i-C3H7 173I-1-b-10 H CH3 H CH3 CH3 s-C4H9 193I-1-b-11 H CH3 H CH3 H i-C3H7 183I-1-b-12 H Cl H Cl H i-C3H7 108
实施例(I-1-c-1)
在0-10℃下,将1.0ml(0.010mol)氯甲酸乙酯的5ml无水二氯甲烷溶液滴加到2.88g(0.010mol)实施例(I-1-a-1)的化合物和1.4ml(0.010mol)三乙胺在50ml无水二氯甲烷中的溶液中,将该混合物在室温搅拌直至反应结束(根据薄层色谱分析)。为进行后处理,将混合物用50ml 0.5N氢氧化钠溶液洗涤两次,经硫酸镁干燥并浓缩。收率:2.8g(理论收率的77%),熔点:157℃。
类似地,和/或按照通用制备方法,制得下列式(I-1-c)的化合物:
表6实施例号 V W X Y Z L M R2 熔点℃No.I-1-c-2 H CH3 CH3 CH3 CH3O O C2H5 163I-1-c-3 H CH3 CH3 Br H O O C2H5 184I-1-c-4 H H Cl Cl H O O C2H5 131
在30-40℃下,将29.1g(0.1016mol)实施例(XXV-1)混合物在310ml无水二氯甲烷中的溶液小心地滴加到51.3g(0.513mol)浓硫酸中,将该混合物在该温度下搅拌2小时。然后以使反应物内部温度保持在约40℃的速率滴加69ml无水甲醇,并继续在40-70℃下再搅拌6小时。为进行后处理,将混合物倾入0.51kg冰中,用二氯甲烷萃取,用碳酸氢钠水溶液洗涤,干燥并浓缩。残余物用甲基叔丁基醚/N-己烷重结晶。收率:17.3g(理论收率的53%),熔点:168℃。
以类似于实施例(II-1)和按照通用制备方法,制备下列式(II)化合物:
表7实施例号 V W X Y Z R8 熔点℃II-2 H CH3 CH3 CH3 CH3 CH3 78II-3 H CH3 CH3 Br H CH3 110II-4 H H CH3 CH3 H CH3 68II-5 H H Cl Cl H CH3 103II-6 H H CH3 CH3 CH3 CH3 92II-7 H Br Cl CH3 H CH3 114II-8 H Cl CH3 Cl H CH3 204II-9 H H CH3 H CH3 CH3 74II-10 H H CH3 H H CH3 85II-11 H H Br CH3 CH3 CH3 81II-12 H H CH3 Br CH3 CH3 110II-13 H CH3 CH3 H Br CH3 134II-14 H H Cl -O-CF2-O- CH3 121II-15 H CH3 CH3 CH3 Br CH3 97
在0-10℃下,将25g 2,4,6-三甲基苯乙酰氯的30ml无水THF溶液滴加到15.8g 3-氨基四氢吡喃-3-甲腈(按照实施例XXIV)和17.6ml三乙胺在250ml无水THF中的溶液中,将该混合物搅拌直至反应结束。将该混合物在500ml冰水和200ml 1N HCl的混合液中搅拌。吸滤出产物,残余物加到二氯甲烷中,干燥并浓缩。收率:29.1g(理论收率的81%),熔点:153℃。
类似于实施例(XXV-1),和/或按照通用制备方法,制备下列式(XXV)化合物:
表8实施例号 V W X Y Z 熔点℃XXV-2 H CH3 CH3 CH3 CH3 182XXV-3 H CH3 CH3 Br H 187XXV-4 H H CH3 CH3 H 137XXV-5 H H Cl Cl H 162XXV-6 H H CH3 CH3 CH3 159XXV-7 H Br Cl CH3 H 158XXV-8 H Cl CH3 Cl H 141XXV-9 H H CH3 H CH3 148XXV-10 H H CH3 H H 149XXV-11 H CH3 CH3 H Br 176XXV-12 H H Br CH3 CH3 135XXV-13 H H CH3 Br CH3 166XXV-14 H H Cl -O-CF2O- 115XXV-15 H CH3 CH3 CH3 Br 212
在10℃下,将18.1g(0.057mol)实施例III-1化合物在30ml无水二甲基甲酰胺(DMF)溶液缓慢地滴加到9.58g(0.085mol)叔丁醇钾在10ml无水DMF中的溶液中,将该混合物在室温搅拌过夜。蒸除DMF,残余物加到1L水中并用浓盐酸缓慢地酸化。吸滤出产物,用水洗涤并在50℃下加压干燥,熔点:261℃。
以类似于实施例(1-2-a-1)和按照通用制备方法,制得下列式(I-2-a)的化合物:实施例号 V W X Y Z 熔点℃I-2-a-2 H CH3 CH3 Cl H 266-269I-2-a-3 H H CH3 CH3 CH3 213-214I-2-a-4 H CH3 Br CH3 H 245I-2-a-5 H CH3 CH3 Br H 270I-2-a-6 H CH3 Cl CH3 H 248-250I-2-a-7 H CH3 CH3 CH3 CH3 218
将1.45g(0.012mol)新戊酰氯滴加到2.88g(0.01mol)实施例I-2-a-1的混合物和1.2g(0.012mol)三乙胺在30ml无水二氯甲烷中的溶液中,并搅拌该混合物直至反应结束。然后进行常规后处理,收率:3.47g,熔点:108℃。
以类似于实施例(1-2-b-1)和按照通用制备方法,制得下列式(I-2-b)的化合物:实施例号 V W X Y Z R1 熔点℃I-2-b-2 H H CH3 CH3 CH3 i-C3H7 106-107I-2-b-3 H CH3 CH3 CH3 H i-C3H7 115I-2-b-4 H CH3 CH3 Cl H i-C3H7 109-110I-2-b-5 H CH3 Br CH3 H i-C3H7 94I-2-b-6 H CH3 CH3 Br H i-C3H7 118I-2-b-7 H CH3 Cl CH3 H i-C3H7 96-98I-2-b-8 H CH3 CH3 CH3 CH3 i-C3H7 115
实施例(I-2-c-1)
将1.64g(0.012mol)氯甲酸异丁酯滴加到2.88g(0.01mol)实施例I-2-a-1的混合物和1.2g(0.012mol)三乙胺在30ml无水二氯甲烷中的溶液中,并搅拌该混合物直至反应结束。然后进行常规后处理,收率:3.8g,熔点:107℃。
以类似于实施例(1-2-c-1)和按照通用制备方法,制得下列式(I-2-c)的化合物:实施例号 V W X Y Z M R2 熔点℃I-2-c-2 H H CH3 CH3 CH3 O i-C4H9 102-103I-2-c-3 H CH3 CH3 CH3 H S i-C3H7 105-106I-2-c-4 H CH3 CH3 Cl H O i-C4H9 143I-2-c-5 H CH3 Br CH3 H O i-C4H9 89I-2-c-6 H CH3 CH3 Br H O i-C4H9 138I-2-c-7 H CH3 Cl CH3 H O i-C4H9 90-92I-2-c-8 H CH3 CH3 CH3 CH3 O i-C4H9 95
实施例(I-2-a-2)
将10g(0.057mol)实施例(XXVI)化合物和11.3g 2,4,6-三甲基苯基乙酰氯在140℃下加热6小时,然后脱气。收率:18.1g油状物,质谱(m/e):334(M+,36%),160(38%),133(100%)。
以类似于实施例(III-1),和/或按照通用制备方法,制得下列式(III)的化合物:实施例号 V W X Y Z 熔点℃III-2 H CH3 CH3 Cl H oilIII-3 H H CH3 CH3 CH3 oilIII-4 H CH3 Br CH3 H oilIII-5 H CH3 CH3 Br H oilIII-6 H CH3 Cl CH3 H oilIII-7 H CH3 CH3 CH3 CH3 oil
在室温下,将116.8g(1.17mol)3-氧杂环己-1-酮(参见Bull.Soc.Chim,Fr.(1970),(10),3521-3)滴加到222.4g(3.27mol)强度为25%的氨水溶液、75g(1.4mol)氯化铵、68.7g(1.4mol)氰化钠和210ml水的混合物中,将该混合物在45℃搅拌过夜。用二氯甲烷萃取,得到95.2g(理论收率的64%)上述化合物,该化合物无需纯化即可用于制备式XXV化合物。
在0~-20℃下,将89.3g(0.7mol)实施例(XXVIa)化合物的420ml甲醇溶液用盐酸饱和。将该混合物在0℃再搅拌1小时,然后使其在3小时里温热到室温。减压除去过量盐酸,浓缩。将残余物与400ml冷却的水混合并搅拌1小时。该混合物用二氯甲烷萃取两次,将萃取液干燥并浓缩。
收率:90g,沸点0.06:66℃。
在室温下,将24.3g(0.9mol)氢氰酸滴加到85.0g(0.85mol)3-氧杂环己-1-酮(Bull.Soc.Chim.Fr.(1970)(10),3521-3)和0.72ml三乙胺的混合物中,将该混合物在室温再搅拌1.5小时。该混合物用0.12ml正磷酸稳定并减压脱气。
收率:102g(理论收率的94%)。
应用实施例
实施例A
蚜虫试验
溶剂:7份重的二甲基甲酰胺
乳化剂:1份重的聚乙二醇烷基芳基醚
为生产适宜的活性化合物的制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,该浓缩物用水稀释至所需浓度。
将严重感染了桃蚜(Myzus persicae)的甘蓝菜叶(Brassica ileracea)用所需浓度的活性化合物制剂浸渍处理。
经过所需时间后,测定杀灭率。100%表示所有的蚜虫都被杀灭;0%表示没有蚜虫被杀灭。
在该试验中,制备实施例(I-1-a-2)、(I-1-a-3)、(I-1-b-2)和(I-1-c-1)的化合物的实验浓度为0.1%,6天后的杀灭率为100%。
实施例B
黑尾叶蝉试验
溶剂:20份重的二甲基甲酰胺
乳化剂:1份重的聚乙二醇烷基芳基醚
为生产适宜的活性化合物的制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,该浓缩物用水稀释至所需浓度。
将聚集有绿黑尾叶蝉(Nephotettix cincticeps)的潮湿稻种(Oryzeasativa)用所需浓度的活性化合物制剂浸渍处理。
经过所需时间后,测定杀灭率。100%表示所有的叶蝉都被杀灭;0%表示没有叶蝉被杀灭。
在该试验中,制备实施例(I-1-a-1)、(I-1-a-2)、(I-1-a-3)、(I-1-b-1)、(I-1-b-2)、(I-1-b-3)、(I-1-b-4)、(I-1-b-5)和(I-1-c-3)化合物的实验浓度为0.1%,6天后的杀灭率为100%。
实施例C
猿叶虫幼虫试验
溶剂:7份重的二甲基甲酰胺
乳化剂:1份重的聚乙二醇烷基芳基醚
为生产适宜的活性化合物的制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,该浓缩物用水稀释至所需浓度。
将聚集有辣根猿叶虫(phaedon cochleariae)幼虫的湿润的甘蓝叶(Brassica oleracea)用所需浓度的活性化合物制剂浸渍处理。
经过所需时间后,测定杀灭率。100%表示所有的猿叶虫幼虫都被杀灭;0%表示没有猿叶虫幼虫被杀灭。
在该试验中,制备实施例(I-1-a-1)、(I-1-a-2)、(I-1-a-3)、(I-1-b-1)、(I-1-b-2)、(I-1-b-3)、(I-1-b-4)、(I-1-b-5)和(I-1-c-1)化合物的实验浓度为0.1%,7天后的杀灭率为100%。
实施例D
草地贪夜蛾试验
溶剂:7份重的二甲基甲酰胺
乳化剂:1份重的聚乙二醇烷基芳基醚
为生产适宜的活性化合物的制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,该浓缩物用水稀释至所需浓度。
将聚集有枭蛾(草地贪夜蛾,Spodoptera frugiperda)毛虫的湿润的甘蓝叶(Brassica oleracea)用所需浓度的活性化合物制剂浸渍处理。
经过所需时间后,测定杀灭率。100%表示所有的毛虫都被杀灭;0%表示没有毛虫被杀灭。
在该试验中,制备实施例(I-1-b-4)和(I-1-c-1)化合物的实验浓度为0.1%,7天后的杀灭率为100%。
实施例E
红叶螨试验
溶剂:3份重的二甲基甲酰胺
乳化剂:1份重的聚乙二醇烷基芳基醚
为生产适宜的活性化合物的制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,该浓缩物用水稀释至所需浓度。
将严重感染有各阶段棉红蜘蛛(二点叶螨,Tetranychus urticae)的大豆植物(菜豆,Phaseolus vulgaris)用所需浓度的活性化合物制剂浸渍处理。
经过所需时间后,测定杀灭率。100%表示所有的蜘蛛螨都被杀灭;0%表示没有蜘蛛螨被杀灭。
在该试验中,制备实施例(I-1-a-1)、(I-1-b-1)、(I-1-b-2)和(I-1-c-1)化合物的实验浓度为0.1%,13天后的杀灭率为100%。
Claims (19)
其中
V表示氢、卤素、烷基或烷氧基,
W表示氢、氰基、硝基、卤素、烷基、链烯基、炔基、烷氧基、卤代烷基、卤代烷氧基或者分别是可任意取代的苯基、苯氧基、苯硫基、苯基烷氧基或苯基烷硫基,
X表示卤素、烷基、链烯基、炔基、烷氧基、卤代烷基、卤代烷氧基、氰基、硝基或者分别是可任意取代的苯基、苯氧基、苯硫基、苯基烷氧基或苯基烷硫基,
Y表示氢、卤素、烷基、烷氧基、卤代烷基、卤代烷氧基、氰基或硝基,
Z表示氢、卤素、烷基、烷氧基、卤代烷基、卤代烷氧基、羟基、氰基、硝基或者分别是可任意取代的苯氧基、苯硫基、5-或6-元杂芳基氧基、5-或6-元杂芳硫基、苯基烷氧基或苯基烷硫基,或者
Y和Z与相连的碳原子一起表示可任意取代的环,该环可任意地被一个或多个杂原子间插,或者
W和Z与相连的碳原子一起表示可任意取代的环,该环可任意地被一个或多个杂原子间插,
其中
G表示氢(a)或表示下式的基团
其中
E表示金属离子等价物或铵离子,
L表示氧或硫,
M表示氧或硫,
R1表示可任意被卤素或氰基取代的烷基、链烯基、烷氧基烷基、烷硫基烷基或多烷氧基烷基,或者表示可任意被卤素、烷基或烷氧基取代的环烷基或杂环基,或者表示可任意取代的苯基、苯基烷基、杂芳基、苯氧基烷基或杂芳氧基烷基,
R2表示可任意被卤素或氰基取代的烷基、链烯基、烷氧基烷基或多烷氧基烷基,或者表示可任意取代的环烷基、苯基或苄基,
R3、R4和R5各自彼此独立地表示可任意被卤素取代的烷基、烷氧基、烷基氨基、二烷基氨基、烷硫基、链烯硫基或环烷硫基,或者表示可任意取代的苯基、苄基、苯氧基或苯硫基,
R6和R7各自彼此独立地表示氢,或表示可任意被卤素或氰基取代的烷基、环烷基、链烯基、烷氧基、烷氧基烷基,或者表示可任意取代的苯基、苄基,或者与相连的氮原子一起形成可任意含有氧或硫并可任意地被取代的环。
2、权利要求1的式(I)化合物,其中
V表示氢、卤素、C1-C6烷基或C1-C6烷氧基,
W表示氢、硝基、氰基、卤素、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基或者表示可任意被卤素、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、苯氧基、苯硫基、苯基-C1-C4烷氧基或苯基-C1-C4烷硫基,
X表示卤素、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、氰基、硝基或者表示可任意被卤素、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、苯氧基、苯硫基、苯基-C1-C4烷氧基或苯基-C1-C4烷硫基,
Y表示氢、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,
Z表示氢、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、硝基或者表示可任意被卤素、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、噻唑氧基、吡啶氧基、嘧啶氧基、吡唑氧基、苯基-C1-C4烷氧基或苯基-C1-C4烷氧基,或者
Y和Z与相连的碳原子一起表示可任意被卤素、C1-C6烷基、C1-C6烷氧基或C1-C4卤代烷基取代的C3-C5烷二基或C3-C5链烯二基,其中一至三个单元可任意地彼此独立地被氧、硫、氮或羰基代替,
W和Z与相连的碳原子一起表示可任意被卤素、C1-C6烷基、C1-C6烷氧基或C1-C4卤代烷基取代的C3-C5烷二基或C3-C5链烯二基,其中一至三个单元可任意地彼此独立地被氧、硫、氮或羰基代替,
其中
G表示氢(a)或表示下式的基团
其中
E表示金属离子等价物或铵离子,
L表示氧或硫,
M表示氧或硫,
R1 表示可任意被卤素或氰基取代的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,或者表示可任意被卤素、C1-C6烷基或C1-C6烷氧基取代的C3-C8环烷基,其中的一个或两个不直接相邻的亚甲基可任意地被氧和/或硫代替,
表示可任意被卤素、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,
表示可任意被卤素、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,
表示可任意地被卤素或C1-C6烷基取代的5或6元含一或两个选自氧、硫和氮的杂原子的杂芳基,
表示可任意地被卤素或C1-C6烷基取代的苯氧基-C1-C6烷基或者
表示可任意地被卤素、氨基或C1-C6烷基取代的5或6元含一或两个选自氧、硫和氮的杂原子的杂芳氧基-C1-C6烷基;
R2表示可任意被卤素或氰基取代的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,
表示可任意被卤素、C1-C6烷基或C1-C6烷氧基取代的C3-C8环烷基或者
表示可任意地被卤素、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表示可任意地被卤素取代的C1-C8烷基或优选表示可任意地被卤素、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各自彼此独立地表示可任意被卤素取代的C1-C8烷基、C1-C8烷氧基、C1-C8烷基氨基、二-(C1-C8烷基)氨基、C1-C8烷硫基或C3-C8链烯硫基,或者表示任意地被卤素、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各自彼此独立地表示氢,或分别表示可任意被卤素或氰基取代的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,或者分别表示可任意被卤素、C1-C8烷基、C1-C8卤代烷基或C1-C8烷氧基取代的苯基或苄基,或者二者一起表示可任意被C1-C6烷基取代的C3-C6亚烷基,其中的一个亚甲基可任意地被氧或硫代替。
3、权利要求1的式(I)化合物,其中
V表示氢、氟、氯、溴、C1-C4烷基或C1-C4烷氧基,
W表示氢、硝基、氰基、氟、氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基或者表示可任意被氟、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基、苯氧基或苄氧基;
X表示氟、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、硝基或者表示可任意被氟、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基、苯氧基或苄氧基;
Y表示氢、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,
Z表示氢、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、硝基或者表示可任意被氟、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,或者
Y和Z与相连的碳原子一起表示可任意被氟、氯、溴、C1-C4烷基、C1-C4烷氧基或C1-C2卤代烷基取代的C3-C4烷二基或C3-C4链烯二基,其中一至两个不直接相邻的单元可任意地彼此独立地被氧、硫或氮代替,或者
W和Z与相连的碳原子一起表示可任意被氟、氯、溴、C1-C4烷基、C1-C4烷氧基或C1-C2卤代烷基取代的C3-C4烷二基或C3-C4链烯二基,其中一至两个不直接相邻的单元可任意地彼此独立地被氧、硫或氮代替,
其中
G表示氢(a)或表示下式的基团
其中
E表示金属离子等价物或铵离子,
L表示氧或硫,
M表示氧或硫,
R1表示可任意被氟或氯取代的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,或者表示可任意被氟、氯、C1-C5烷基或C1-C5烷氧基取代的C3-C7环烷基,其中的一个或两个不直接相邻的亚甲基可任意地被氧和/或硫代替,
表示可任意被氟、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,
表示可任意被氟、氯、溴、氰基、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,
表示可任意地被氟、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,
表示可任意地被氟、氯、溴或C1-C4烷基取代的苯氧基-C1-C5烷基或者
表示可任意地被氟、氯、溴、氨基或C1-C4烷基取代的吡啶氧基-C1-C5烷基、嘧啶基-C1-C5烷基或噻唑氧基-C1-C5烷基。
R2表示可任意被氟或氯取代的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,
表示可任意被氟、氯、C1-C4烷基或C1-C4烷氧基取代的C3-C7环烷基或者
表示可任意地被氟、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表示可任意地被氟或氯取代的C1-C6烷基或表示可任意地被氟、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各自彼此独立地表示可任意被氟或氯取代的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链烯硫基,或者表示任意地被氟、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各自彼此独立地表示氢,或分别表示可任意被氟或氯取代的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,或者分别表示可任意被氟、氯、溴、C1-C5卤代烷基、C1-C5烷基或C1-C5烷氧基取代的苯基或苄基,或者二者一起表示可任意被C1-C4烷基取代的C3-C6亚烷基,其中的一个亚甲基可任意地被氧或硫代替。
4、权利要求1的式(I)化合物,其中
V表示氢、氟、氯、溴、甲基、乙基、丙基、异丙基、叔丁基、甲氧基、乙氧基、丙氧基或异丙氧基;
W表示氢、硝基、氰基、氟、氯、溴、甲基、乙基、丙基、正丁基、异丙基、异丁基、甲氧基、乙氧基、丙氧基、异丙氧基、三氟甲基、二氟甲氧基、三氟甲氧基、苯基或苄氧基;
X表示氟、氯、溴、甲基、乙基、丙基、丁基、异丁基、异丙基、甲氧基、乙氧基、丙氧基、异丙氧基、三氟甲基、三氟甲氧基、二氟甲氧基、氰基、硝基、苯基或苄氧基;
Y表示氢、氟、氯、溴、甲基、乙基、丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、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表示氢、氟、氯、溴、甲基、乙基、丙基、丁基、异丁基、异丙基、叔丁基、甲氧基、乙氧基、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,或者
Y和Z与相连的碳原子一起表示可任意被氟、氯、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、丙氧基、异丙氧基或三氟甲基取代的C3-C4烷二基,其中两个不直接相邻的单元可任意地被氧代替,或者
W和Z与相连的碳原子一起表示可任意被氟、氯、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、丙氧基、异丙氧基或三氟甲基取代的C3-C4烷二基,其中两个不直接相邻的单元可任意地被氧代替,
其中
其中
E表示金属离子等价物或铵离子,
L表示氧或硫,
M表示氧或硫,
R1表示可任意被氟或氯取代的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烷基或多-C1-C4烷氧基-C1-C4烷基,或者表示可任意被氟、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C3-C6环烷基,其中的一个或两个不直接相邻的亚甲基可任意地被氧和/或硫代替,
表示可任意被氟、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、甲磺酰基或乙磺酰基取代的苯基,
表示可任意被氟、氯、溴、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基取代的苄基,
表示可任意地被氟、氯、溴、甲基或乙基取代的呋喃基、噻吩基或吡啶基,
表示可任意地被氟、氯、甲基或乙基取代的苯氧基-C1-C4烷基或者
表示可任意地被氟、氯、氨基、甲基或乙基取代的吡啶氧基-C1-C4烷基、嘧啶基-C1-C4烷基或噻唑氧基-C1-C4烷基;
R2表示可任意被氟或氯取代的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,
表示可任意被氟、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
表示可任意地被氟、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表示可任意地被氟或氯取代的甲基、乙基、丙基、异丙基、正丁基、叔丁基或表示可任意地被氟、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各自彼此独立地表示可任意被氟或氯取代的C1-C4烷基、C1-C4烷氧基、C1-C4烷基氨基、二-(C1-C4烷基)氨基、C1-C4烷硫基,或者表示任意地被氟、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各自彼此独立地表示氢,或分别表示可任意被氟或氯取代的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,或者分别表示可任意被氟、氯、溴、甲基、甲氧基或三氟甲基取代的苯基或苄基,或者二者一起表示可任意被甲基或乙基取代的C5-C6亚烷基,其中的一个亚甲基可任意地被氧或硫代替。
5、权利要求1的式(I)化合物的制备方法,特征在于
(A)式(I-1-a)化合物
其中V、W、X、Y和Z如权利要求1所定义,
其中V、W、X、Y和Z如上所定义
并且R8表示烷基,
在稀释剂和碱的存在下进行分子内缩合获得;
其中V、W、X、Y和Z如上所定义,
其中V、W、X、Y、Z和R8如上所定义
在稀释剂和碱的存在下进行分子内缩合获得;
(C)式(I-3-a)化合物
其中V、W、X、Y和Z如上所定义,
可通过将式(IV)化合物
其中V、W、X、Y、Z和R8如上所定义
T表示氢、卤素、烷基或烷氧基,
进行分子内环化获得,如果合适,环化反应可在稀释剂和酸的存在下进行;
将其中V、W、X、Y和Z各自如上所定义的式(I-1-a)-(I-3-a)化合物分别
其中
R1如权利要求1所定义
Hal表示卤素或
β)与式(VI)的羧酸酐
R1-CO-O-CO-R1 (VI)
其中
R1如上所定义,
反应,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行;
(E)与式(VII)的氯甲酸酯或氯甲酸硫酯
R2-M-CO-Cl (VII)
其中
R2和M各自如上所定义,
反应获得,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行;或者
其中
M和R2各自如上所定义,
反应获得,如果合适反应可在有稀释剂的存在下和如果合适可在有酸结合剂的存在下进行;
或者
(G)与式(IX)的磺酰氯
R3-SO2-Cl (IX)
其中
R3如上所定义,
反应获得,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行;
或者
其中
L、R4和R5各自如权利要求1所定义和
Hal表示卤素,
反应获得,如果合适反应可在有稀释剂的存在下和如果合适可在有酸结合剂的存在下进行;或者
(I)与式(XI)或(XII)金属化合物或胺
Me(OR10)t (XI)
其中
Me表示一价或二价金属,
t表示1或2的数,并且
R10、R11和R12各自独立地表示氢或烷基,
反应获得,如果合适反应可在有稀释剂的存在下进行;或者
(J)α)与式(XIII)的异氰酸酯或异硫氰酸酯
R6-N=C=L (XIII)
其中
R6和L如权利要求1所定义,
反应,如果合适反应可在稀释剂和如果合适可在酸结合剂的存在下进行,
或
其中
L、R6和R7如权利要求1所定义,
反应,如果合适反应可在有稀释剂和如果合适可在有酸结合剂的存在下进行。
7、式(XVII)的化合物
其中V、W、X、Y和Z分别如权利要求1所定义。
10、式(XXVI)的化合物
其中R8表示烷基。
13、式(XXIV)的化合物
16、一种杀虫剂或除草剂,特征在于它们含有权利要求1的式(I)化合物。
17、权利要求1的式(I)化合物用于防治昆虫和除草的用途。
18、一种防治昆虫和除草的方法,特征在于使权利要求1的式(I)化合物作用于昆虫或杂草和/或它们的寄居处。
19、一种制备杀虫剂和除草剂的方法,特征在于将权利要求1的式(I)化合物与增量剂和/或表面活性剂混合。
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1996
- 1996-12-12 DE DE19651686A patent/DE19651686A1/de not_active Withdrawn
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1997
- 1997-12-01 EP EP97952026A patent/EP0944633B1/de not_active Expired - Lifetime
- 1997-12-01 BR BRPI9714470-3A patent/BR9714470B1/pt not_active IP Right Cessation
- 1997-12-01 KR KR10-1999-7004521A patent/KR100506486B1/ko not_active IP Right Cessation
- 1997-12-01 CN CN97180627A patent/CN1130366C/zh not_active Expired - Fee Related
- 1997-12-01 DE DE59712887T patent/DE59712887D1/de not_active Expired - Lifetime
- 1997-12-01 AU AU55595/98A patent/AU5559598A/en not_active Abandoned
- 1997-12-01 JP JP52616198A patent/JP4767372B2/ja not_active Expired - Fee Related
- 1997-12-01 WO PCT/EP1997/006708 patent/WO1998025928A1/de active IP Right Grant
- 1997-12-01 US US09/319,489 patent/US6288102B1/en not_active Expired - Fee Related
- 1997-12-01 ES ES97952026T patent/ES2296316T3/es not_active Expired - Lifetime
Cited By (7)
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CN1837194B (zh) * | 2001-09-24 | 2010-06-16 | 拜尔农作物科学股份公司 | 螺环3-苯基-3-取代的4-酮基内酰胺类和4-酮基内酯类化合物 |
CN100457729C (zh) * | 2003-01-20 | 2009-02-04 | 拜尔农作物科学股份公司 | 2,4-二卤素-6-(C2-C3-烷基)苯基取代的tetramic acid衍生物 |
CN101195599B (zh) * | 2003-03-14 | 2013-04-10 | 拜尔农作物科学股份公司 | 2,4,6-苯基取代的环酮-烯醇 |
CN101495448B (zh) * | 2006-06-02 | 2014-02-19 | 拜尔农作物科学股份公司 | 烷氧基烷基取代的环状酮烯醇 |
CN101565416B (zh) * | 2009-06-02 | 2012-05-30 | 华南农业大学 | 一种炔基噻吩酮类化合物及其制备方法和应用 |
CN103402979A (zh) * | 2011-01-05 | 2013-11-20 | 先正达参股股份有限公司 | 化学化合物 |
CN114409664A (zh) * | 2021-12-24 | 2022-04-29 | 河北威远生物化工有限公司 | 一种螺杂环四氢吡喃化合物及其制备方法和应用 |
Also Published As
Publication number | Publication date |
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JP2001505892A (ja) | 2001-05-08 |
BR9714470B1 (pt) | 2009-05-05 |
BR9714470A (pt) | 2000-05-16 |
EP0944633B1 (de) | 2007-10-10 |
AU5559598A (en) | 1998-07-03 |
DE59712887D1 (de) | 2007-11-22 |
WO1998025928A1 (de) | 1998-06-18 |
ES2296316T3 (es) | 2008-04-16 |
KR100506486B1 (ko) | 2005-08-08 |
CN1130366C (zh) | 2003-12-10 |
US6288102B1 (en) | 2001-09-11 |
KR20000069079A (ko) | 2000-11-25 |
JP4767372B2 (ja) | 2011-09-07 |
EP0944633A1 (de) | 1999-09-29 |
DE19651686A1 (de) | 1998-06-18 |
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