CN103596923A - 作为在植物中抵抗非生物胁迫的活性剂的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔 - Google Patents
作为在植物中抵抗非生物胁迫的活性剂的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔 Download PDFInfo
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- CN103596923A CN103596923A CN201280028961.2A CN201280028961A CN103596923A CN 103596923 A CN103596923 A CN 103596923A CN 201280028961 A CN201280028961 A CN 201280028961A CN 103596923 A CN103596923 A CN 103596923A
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- Prior art keywords
- alkyl
- cycloalkyl
- carbonyl
- aryl
- base
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- 230000036579 abiotic stress Effects 0.000 title claims abstract description 32
- MYMYTIFYNJRKLE-UHFFFAOYSA-N CC=CC=CC1CCCC=C1 Chemical class CC=CC=CC1CCCC=C1 MYMYTIFYNJRKLE-UHFFFAOYSA-N 0.000 title abstract 2
- 239000013543 active substance Substances 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 31
- 230000035882 stress Effects 0.000 claims abstract description 17
- -1 thiazolinyl alkyl Chemical group 0.000 claims description 304
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 256
- 125000003545 alkoxy group Chemical group 0.000 claims description 158
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 150000001875 compounds Chemical class 0.000 claims description 100
- 229910052760 oxygen Inorganic materials 0.000 claims description 95
- 239000001301 oxygen Substances 0.000 claims description 79
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 47
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 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
- 125000004414 alkyl thio group Chemical group 0.000 claims description 34
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
- 239000011737 fluorine Substances 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 24
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 23
- 239000003337 fertilizer Substances 0.000 claims description 23
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 17
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000007921 spray Substances 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 13
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 239000004411 aluminium Substances 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 10
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052732 germanium Inorganic materials 0.000 claims description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000003899 bactericide agent Substances 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 7
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 7
- 238000005728 strengthening Methods 0.000 claims description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 6
- 239000000642 acaricide Substances 0.000 claims description 6
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000005038 alkynylalkyl group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 229910000085 borane Inorganic materials 0.000 claims description 6
- 230000008641 drought stress Effects 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
- 235000016709 nutrition Nutrition 0.000 claims description 6
- 230000035764 nutrition Effects 0.000 claims description 6
- 230000008635 plant growth Effects 0.000 claims description 6
- 125000000382 plumbyl group Chemical group [H][Pb]([H])([H])* 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 6
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 5
- 241000534944 Thia Species 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 5
- 244000038559 crop plants Species 0.000 claims description 5
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000002917 insecticide Substances 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 229940031815 mycocide Drugs 0.000 claims description 5
- 230000001069 nematicidal effect Effects 0.000 claims description 5
- 239000005645 nematicide Substances 0.000 claims description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000000707 boryl group Chemical group B* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 238000012239 gene modification Methods 0.000 claims description 4
- 230000005017 genetic modification Effects 0.000 claims description 4
- 235000013617 genetically modified food Nutrition 0.000 claims description 4
- 239000003630 growth substance Substances 0.000 claims description 4
- 230000035800 maturation Effects 0.000 claims description 4
- 230000008723 osmotic stress Effects 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- BNZLTPCWOLWBNJ-UHFFFAOYSA-M Br[Mg] Chemical compound Br[Mg] BNZLTPCWOLWBNJ-UHFFFAOYSA-M 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- FOSCDBCOYQJHPN-UHFFFAOYSA-M Cl[Mg] Chemical compound Cl[Mg] FOSCDBCOYQJHPN-UHFFFAOYSA-M 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 2
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000000320 amidine group Chemical group 0.000 claims description 2
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
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- 230000000875 corresponding effect Effects 0.000 claims 2
- 231100000956 nontoxicity Toxicity 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- 230000035040 seed growth Effects 0.000 claims 1
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical compound S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 abstract description 6
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- 239000002585 base Substances 0.000 description 493
- 241000196324 Embryophyta Species 0.000 description 234
- 238000005160 1H NMR spectroscopy Methods 0.000 description 128
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 73
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
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- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 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
- KKEOZWYTZSNYLJ-UHFFFAOYSA-O triazanium;nitrate;sulfate Chemical compound [NH4+].[NH4+].[NH4+].[O-][N+]([O-])=O.[O-]S([O-])(=O)=O KKEOZWYTZSNYLJ-UHFFFAOYSA-O 0.000 description 1
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- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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- 229940088594 vitamin Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000000664 voltage gated sodium channel blocking agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- PCMOZDDGXKIOLL-UHFFFAOYSA-K yttrium chloride Chemical compound [Cl-].[Cl-].[Cl-].[Y+3] PCMOZDDGXKIOLL-UHFFFAOYSA-K 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds only one oxygen atom attached to the nitrogen atom
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
本发明涉及取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔、其制备方法及其用于提高植物对非生物胁迫的胁迫耐受性的用途,和/或提高植物产量的用途。
已知特定的5-(1,2-环氧基-2,6,6-三甲基环己基)-3-甲基戊-2,4-二烯酸及其衍生物具有影响植物生长的特性(参见NL6811769)。脱落酸的某些1,2-环氧基类似物对稻秧的生长调节效果也记载于Agr.Biol.Chem.1969,33,1357和Agr.Biol.Chem.1970,34,1393。US2010/0160166记载了取代的5-环己-2-烯-1-基戊-2,4-二烯基醇和5-环己-2-烯-1-基戊-2-烯-4-炔基醇、5-环己-2-烯-1-基戊-2,4-二烯基硫醚和5-环己-2-烯-1-基戊-2-烯-4-炔基硫醚和5-环己-2-烯-1-基戊-2,4-二烯基胺和5-环己-2-烯-1-基戊-2-烯-4-炔基胺作为环氧类胡萝卜素双加氧酶抑制剂的用途和作为萌芽抑制剂的用途。US5518995和EP0371882记载了在2,4-戊二烯酸单元中具有3-甲基取代基的特定脱落酸衍生物的制备及其用于影响萌芽和植物生长的用途。另外已知具有3-甲基取代基的特定脱落酸衍生物可用于提高植物对低温的耐受性(参见WO94/15467)。US4581057记载了通过使用脱落酸和合适的肥料而提高大豆种子的产量。
同样已知的是在5-环己-2-烯-1-基单元的C6位具有不饱和取代基的5-(环己-2-烯-1-基)-3-甲基戊-2,4-二烯酸衍生物可影响植物的水平衡和萌芽(参见WO97/23441)。此外还记载了在5-(环己-2-烯-1-基)-3-甲基戊-2,4-二烯酸的5-环己-2-烯-1-基单元的C6位为三氟甲基、烷基和甲氧基甲基取代基(参见Biosci.Biotech.Biochem.1994,58,707;Biosci.Biotech.Biochem.1995,59,699;Phytochem.1995,38,561;Bioorg.Med.Chem.Lett.1995,5,275)。WO2005108345记载了双环四氢萘酮基的3-甲基戊-2,4-二烯酸衍生物。
还已知脱落酸及其衍生物可用作调节钙转运的药物活性化合物(参见EP240257)。
具有3-羟甲基侧链的脱落酸衍生物,(2E,4E)-3-(羟甲基)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)戊-2,4-二烯酸的制备记载于Org.Biomol.Chem.2006,4,4186。
已知植物可以特定或非特定的防御机制对自然胁迫条件例如冷、热、干旱胁迫(由干燥和/或缺水引起的胁迫)、损伤、病原体攻击(病毒、细菌、真菌、昆虫)等做出响应,而且对除草剂也会做出响应[Pflanzenbiochemie[Plant Biochemistry],第393-462页,SpektrumAkademischer Verlag,Heidelberg,Berlin,Oxford,Hans W.Heldt,1996.;Biochemistry and Molecular Biology of Plants,S.1102-1203,American Society of Plant Physiologists,Rockville,Maryland,eds.Buchanan,Gruissem,Jones,2000]。
已知植物中存在大量蛋白质以及编码其的基因,所述基因参与对非生物胁迫(例如冷、热、干旱胁迫、盐、涝)的防御反应。其中的一些形成信号传导链的部分(例如转录因子、激酶、磷酸酯酶)或者引起植物细胞的生理响应(例如离子运输、活性氧簇的失活)。非生物胁迫反应的信号链基因尤其包括DREB和CBF类转录因子(Jaglo-Ottosen等人,1998,Science280:104-106)。对盐胁迫的反应涉及ATPK和MP2C类磷酸酯酶。
此外,在盐胁迫的情况下,通常激活渗透物如脯氨酸或蔗糖的生物合成。
这包括例如蔗糖合酶和脯氨酸转运蛋白(Hasegawa等人,2000,Annu RevPlant Physiol Plant Mol Biol51:463-499)。植物对冷和干旱的胁迫防御利用某些相同的分子机制。已知存在被称为晚期胚胎富集蛋白(LEA蛋白质)的物质累积,其包括作为一个重要类别的脱水蛋白(Ingram and Bartels,1996,Annu Rev Plant Physiol Plant Mol Biol47:277-403,Close,1997,Physiol Plant100:291-296)。这些是在胁迫植物中稳定囊泡、蛋白质和膜结构的伴侣蛋白(Bray,1993,Plant Physiol103:1035-1040)。此外,经常引入醛脱氢酶,其使在氧化胁迫的情况下形成的活性氧簇(ROS)失活(Kirch等人,2005,Plant Mol Biol57:315-332)。热休克因子(HSF)和热休克蛋白(HSP)在热胁迫的情况下被激活并且在此作为伴侣蛋白在冷和干旱胁迫的情况下起与脱水蛋白类似的作用(Yu等人,2005,Mol Cells19:328-333)。
已知许多参与胁迫耐受或病原体防御的植物内源信号物质。此处的实例包括水杨酸、苯甲酸、茉莉酮酸或乙烯[Biochemistry and MolecularBiology of Plants,第850-929页,American Society of Plant Physiologists,Rockville,Maryland,eds.Buchanan,Gruissem,Jones,2000]。这些物质中的一些或其稳定的合成衍生物及其衍生结构在植物的外部施用或拌种中也是有效的,并且激活了引发植物的胁迫耐受性或病原体耐受性提高的防御反应[Sembdner,and Parthier,1993,Ann.Rev.Plant Physiol.Plant Mol.Biol.44:569-589)。
另外已知化学物质可提高植物对非生物胁迫的耐受性。这类物质通过拌种、通过叶面喷洒或通过土壤处理施用。例如,记载了通过用系统获得性抗性(SAR)激发子或脱落酸衍生物处理来提高作物植物的非生物胁迫耐受性(Schading and Wei,WO-200028055,Churchill等人,1998,PlantGrowth Regul25:35-45)。此外,生长调节剂对作物植物的胁迫耐受性的效果已有记载(Morrison and Andrews,1992,J Plant Growth Regul11:113-117,RD-259027)。在本文中,同样已知生长调节性的萘基磺酰胺(4-溴代-N-(吡啶-2-基甲基)萘-1-磺酰胺)以与脱落酸相同的方式影响植物种子的萌芽(Park等人,Science2009,324,1068-1071)。还已知另一萘基磺酰胺,N-(6-氨己基)-5-氯萘-1-磺酰胺影响暴露于冷休克的植物中的钙水平(Cholewa等人,Can.J.Botany1997,75,375-382)。
类似的效应同样可见于施用杀菌剂,特别是使用嗜球果伞素(Strobilurin)类杀菌剂或琥珀酸脱氢酶抑制剂类杀菌剂时,并且其通常还伴随产量的增加(Draber等人,DE3534948,Bartlett等人,2002,Pest Manag Sci60:309)。还已知低剂量的除草剂草甘膦刺激一些植物物种的生长(Cedergreen,Env.Pollution2008,156,1099)。
在渗透胁迫的情况中,由于施用渗透物(例如甘氨酸甜菜碱或其生化前体,例如胆碱衍生物)而观察到了保护效应(Chen等人,2000,Plant Cell Environ23:609-618,Bergmann等人,DE4103253)。抗氧化剂例如萘酚和黄嘌呤(xanthine)提高植物非生物胁迫耐受性的效应同样已有记载(Bergmann等人,DD277832,Bergmann等人,DD277835)。然而,这些物质抗胁迫作用的分子原因基本未知。
还已知植物对非生物胁迫的耐受性可通过对内源性聚-ADP-核糖聚合酶(PARP)或聚-(ADP-核糖)糖基水解酶(PARG)的活性进行修饰来提高(de Block等人,The Plant Journal,2005,41,95;Levine等人,FEBSLett.1998,440,1;WO0004173;WO04090140)。
因此已知植物具有多种内源性反应机制,其引起对多种不同的有害微生物和/或自然非生物胁迫的有效防御。
由于对于现代作物处理组合物的生态上和经济上的需求不断提高,例如关于毒性、选择性、施用率、残留物形成和有利的制造,因此需要不断开发至少在某些方面优于那些已知组合物的新的植物处理组合物。
因此,本发明的目的在于提供提高植物对非生物胁迫的耐受性,特别是使植物茁壮成长和/或有助于提高植物产量的其他化合物。
因此,本发明提供式(I)的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔或其盐。
其中
[X-Y]代表部分:
Q代表部分Q-1至Q-4
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表烷基、烯基、炔基、烯基烷基、炔基烷基、烷氧基烷基、羟基烷基、卤代烷基、卤代烯基、卤代炔基、卤代烷氧基烷基、烷氧基卤代烷基、卤代烷氧基卤代烷基、烷硫基烷基,
R2代表氢、烷基、烯基、烯基烷基、烷氧基烷基、烷基羰基、芳基羰基、杂芳基羰基、环烷基羰基、烷氧基羰基、烯氧基羰基、芳氧基烷基、芳基烷氧基羰基、芳基烷氧基烷基、芳基烷基、烷氧基烷氧基烷基、烷硫基烷基、三烷基甲硅烷基、烷基(二烷基)甲硅烷基、烷基(二芳基)甲硅烷基、芳基(二烷基)甲硅烷基、环烷基(二烷基)甲硅烷基、卤代(二烷基)甲硅烷基、三烷基甲硅烷基烷氧基烷基、三烷基甲硅烷基烷基,
R3和R4彼此独立地代表烷氧基、烷氧基烷氧基、环烷基烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、芳基烷氧基、芳基烷硫基或与其所连接的原子一起形成氧代基团(oxo group)、羟基亚氨基、烷氧基亚氨基、环烷氧基亚氨基、环烷基烷氧基亚氨基、芳基烷氧基亚氨基或任选可被进一步取代的5元至7元杂环,
R5和R6彼此独立地代表氢、卤素、烷基、卤代烷基,
R7代表卤素、烷基、卤代烷基、卤代烷氧基、卤代烷氧基烷基、卤代烷氧基卤代烷基、烷氧基卤代烷基、炔氧基卤代烷基、烯氧基卤代烷基、烷硫基、卤代烷硫基、芳基、芳基烷基、杂芳基、杂芳基烷基,
R6和R7与其所键合的原子形成完全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代,
R8代表氢、烷基、烷氧基烷基、环烷基、环烷基烷基、芳基、芳基烷基、杂芳基烷基、二芳基烷基、三芳基烷基、烯基、烯基烷基、环烯基烷基、炔基烷基、三烷基甲硅烷基烷氧基烷基、烷氧基烷氧基烷基、烷硫基烷基、卤代烷基、芳基磺酰基烷基、三烷基甲硅烷基、烷基(二芳基)甲硅烷基、烷基(二烷基)甲硅烷基、二烷基氨基烷基,
R9代表氢、烷基、环烷基、卤素、烯基烷基、炔基烷基、卤代烷基、炔基、烯基、氰基烷基、环烷基烷基、芳基烷基、杂芳基烷基、烷基羰基、烷氧基羰基、烯氧基羰基、烯基烷氧基羰基、芳基烷氧基羰基、环烷氧基羰基、环烷基烷氧基羰基、烷基磺酰基、芳基磺酰基、环烷基磺酰基、烷基亚磺酰基、芳基亚磺酰基、环烷基亚磺酰基、烷氧基羰基烷基、羟基羰基烷基、芳基烷氧基羰基烷基、环烷基烷氧基羰基烷基、烷氧基羰基环烷基、羟基羰基环烷基、芳基烷氧基羰基环烷基、烯氧基羰基环烷基、氨基羰基环烷基、烷基氨基羰基环烷基、环烷基氨基羰基环烷基、烷氧基羰基环烯基、羟基羰基环烯基、二烷基氨基烷基、羟基羰基杂环基、烷氧基羰基杂环基、烯氧基羰基杂环基、烯基烷氧基羰基杂环基、芳基烷氧基羰基杂环基、环烷氧基羰基杂环基、环烷基烷氧基羰基杂环基、氨基羰基杂环基、烷基氨基羰基杂环基、二烷基氨基羰基杂环基、环烷基氨基羰基杂环基、芳基烷基氨基羰基杂环基、烯基氨基羰基杂环基、羟基羰基杂环基烷基、烷氧基羰基杂环基烷基、羟基羰基环烷基烷基、烷氧基羰基环烷基烷基、羟基、烷氧基,
R10代表氢、烷基、环烷基、卤素、烷基烯基、卤代烷基(halogenalkyl)、炔基、烯基、氰基烷基、芳基烷基、杂芳基烷基、烷基羰基、烷氧基羰基、烷基磺酰基、芳基磺酰基、环烷基磺酰基、烷基亚磺酰基、芳基亚磺酰基、环烷基亚磺酰基、烷氧基羰基烷基
或
R9和R10与其所连接的氮形成任选被卤素、烷基、卤代烷基、烷氧基、烷氧基羰基、环烷氧基羰基、环烷基烷氧基羰基、烯氧基羰基、羟基羰基、氨基羰基、烷基氨基羰基、环烷基氨基羰基、芳基烷基氨基羰基取代的三至八元环,其任选被O、S或N间隔
或
R9和R10一起为任选取代的硫亚胺或脒基团的部分或一起形成亚氨基正磷(iminophosphorane)。
式(I)的化合物能够形成盐。盐可通过使碱作用于那些带有酸性氢原子的式(I)的化合物——例如R1含有COOH基团或磺酰胺基团-NHSO2-的化合物——来形成。合适的碱为例如有机胺如三烷基胺、吗啉、哌啶或吡啶,以及铵、碱金属或碱土金属氢氧化物、碱金属或碱土金属碳酸盐和碱金属或碱土金属碳酸氢盐,特别是氢氧化钠和氢氧化钾、碳酸钠和碳酸钾和碳酸氢钠和碳酸氢钾。这些盐是其中的酸性氢被农业适用的阳离子替代的化合物,例如金属盐,特别是碱金属盐或碱土金属盐,特别是钠盐和钾盐、或铵盐、含有机胺的盐或季铵盐,例如具有式[NRR′R′′R′′′]+的阳离子的盐,其中R至R′′′各自彼此独立地为有机基团,特别是烷基、芳基、芳烷基或烷芳基。合适的还有烷基锍和烷基氧化锍盐,如(C1-C4)三烷基锍和(C1-C4)三烷基氧化锍盐。
本发明式(I)的化合物及其盐和/或根据本发明使用的化合物在下文中还简称为“式(I)的化合物”。
优选式(I)的化合物,其中
[X-Y]代表部分:
Q代表Q-1至Q-4部分
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表(C1-C8)烷基、(C2-C8)烯基、(C2-C8)炔基、(C2-C8)烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、羟基-(C1-C8)烷基、(C1-C8)卤代烷基、(C2-C8)卤代烯基、(C2-C8)卤代炔基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C3-C8)环烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷硫基-(C1-C8)烷基,
R2代表氢、(C1-C8)烷基、(C2-C8)烯基、(C2-C8)烯基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷基羰基、芳基羰基、杂芳基羰基、(C3-C8)环烷基羰基、(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、芳基-(C1-C8)烷氧基羰基、芳基-(C1-C8)烷氧基-(C1-C8)烷基、芳氧基-(C1-C8)烷基、芳基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷硫基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基、(C1-C8)烷基-(二-(C1-C8)烷基)甲硅烷基、(C1-C8)烷基(二芳基)甲硅烷基、芳基(二-(C1-C8)烷基)甲硅烷基、(C3-C8)环烷基(二-(C1-C6)烷基)甲硅烷基、卤代(二-(C1-C8)烷基)甲硅烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷氧基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷基,
R3和R4彼此独立地代表(C1-C8)烷氧基、(C1-C8)烷氧基-(C1-C8)烷氧基、(C3-C8)环烷基-(C1-C8)烷氧基、(C1-C8)卤代烷氧基、(C1-C8)烷硫基、(C1-C8)卤代烷硫基、芳基-(C1-C8)烷氧基、芳基-(C1-C8)烷硫基或与其所连接的原子一起形成氧代基团、羟基亚氨基、(C1-C8)烷氧基亚氨基、(C3-C8)环烷氧基亚氨基、(C3-C8)环烷基-(C1-C8)烷氧基亚氨基、芳基-(C1-C8)烷氧基亚氨基或任选被进一步取代的5元至7元杂环,
R5和R6彼此独立地代表氢、卤素、(C1-C8)烷基、(C1-C8)卤代烷基,
R7代表卤素、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C8)卤代烷氧基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)炔氧基-(C1-C8)卤代烷基、(C1-C8)烯氧基-(C1-C8)卤代烷基、(C1-C8)烷硫基、(C1-C8)卤代烷硫基、任选取代的苯基、芳基-(C1-C8)烷基、杂芳基、杂芳基-(C1-C8)烷基,
R6和R7与其所键合的原子形成完全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代,
R8代表氢、(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、(C3-C8)环烷基、(C3-C8)环烷基-(C1-C8)烷基、任选取代的苯基、芳基-(C1-C8)烷基、杂芳基-(C1-C8)烷基、二芳基-(C1-C8)烷基、三芳基-(C1-C8)烷基、(C2-C8)烯基、(C2-C8)烯基-(C1-C8)烷基、(C4-C8)环烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷硫基-(C1-C8)烷基、(C1-C8)卤代烷基、芳基磺酰基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基、(C1-C8)烷基-(二芳基)甲硅烷基、(C1-C8)烷基-(二-(C1-C8)烷基)甲硅烷基、二-(C1-C8)烷基氨基-(C1-C8)烷基,
R9代表氢、(C1-C8)烷基、(C3-C8)环烷基、卤素、(C2-C8)烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、(C1-C8)卤代烷基、(C2-C8)炔基、(C2-C8)烯基、氰基(C1-C8)烷基、(C3-C8)环烷基-(C1-C8)烷基、芳基-(C1-C8)烷基、杂芳基-(C1-C8)烷基、(C1-C8)烷基羰基、(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、(C2-C8)烯基-(C1-C8)烷氧基羰基、芳基-(C1-C8)烷氧基羰基、(C3-C8)环烷氧基羰基、(C3-C8)环烷基-(C1-C8)烷氧基羰基、(C1-C8)烷基磺酰基、芳基磺酰基、(C3-C8)环烷基磺酰基、(C1-C8)烷基亚磺酰基、芳基亚磺酰基、(C3-C8)环烷基亚磺酰基、(C1-C8)烷氧基羰基-(C1-C8)烷基、羟基羰基-(C1-C8)烷基、芳基-(C1-C8)烷氧基羰基-(C1-C8)烷基、(C3-C8)环烷基-(C1-C8)烷氧基羰基-(C1-C8)烷基、(C1-C8)烷氧基羰基-(C3-C8)环烷基、羟基羰基-(C3-C8)环烷基、芳基-(C1-C8)烷氧基羰基-(C3-C8)环烷基、(C2-C8)烯氧基羰基-(C3-C8)环烷基、氨基羰基-(C3-C8)环烷基、(C1-C8)烷基氨基羰基-(C3-C8)环烷基、(C3-C8)环烷基氨基羰基-(C3-C8)环烷基、(C1-C8)烷氧基羰基-(C4-C8)环烯基、羟基羰基-(C4-C8)环烯基、二-(C1-C8)烷基氨基-(C1-C8)烷基、羟基羰基杂环基、(C1-C8)烷氧基羰基杂环基、(C2-C8)烯氧基羰基杂环基、(C2-C8)烯基-(C1-C8)烷氧基羰基杂环基、芳基-(C1-C8)烷氧基羰基杂环基、(C3-C8)环烷氧基羰基杂环基、(C3-C8)环烷基-(C1-C8)烷氧基羰基杂环基、氨基羰基杂环基、(C1-C8)烷基氨基羰基杂环基、二-(C1-C8)烷基氨基羰基杂环基、(C3-C8)环烷基氨基羰基杂环基、芳基-(C1-C8)烷基氨基羰基杂环基、(C2-C8)烯基氨基羰基杂环基、羟基羰基杂环基-(C1-C8)烷基、(C1-C8)烷氧基羰基杂环基-(C1-C8)烷基、羟基羰基-(C3-C8)环烷基-(C1-C8)烷基、(C1-C8)烷氧基羰基-(C3-C8)环烷基-(C1-C8)烷基、羟基、(C1-C8)烷氧基,
R10代表氢、(C1-C8)烷基、(C3-C8)环烷基、卤素、(C1-C8)烷基-(C1-C8)烯基、(C1-C8)卤代烷基、(C2-C8)炔基、(C2-C8)烯基、氰基-(C1-C8)烷基、芳基-(C1-C8)烷基、杂芳基-(C1-C8)烷基、(C1-C8)烷基羰基、(C1-C8)烷氧基羰基、(C1-C8)烷基磺酰基、芳基磺酰基、(C3-C8)环烷基磺酰基、(C1-C8)烷基亚磺酰基、芳基亚磺酰基、(C3-C8)环烷基亚磺酰基、(C1-C8)烷氧基羰基-(C1-C8)烷基,
或
R9和R10与其所连接的氮形成任选被卤素、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C8)烷氧基、(C1-C8)烷氧基羰基、(C3-C8)环烷氧基羰基、(C3-C8)环烷基-(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、羟基羰基、氨基羰基、(C1-C8)烷基氨基羰基、(C3-C8)环烷基氨基羰基、芳基-(C1-C8)烷基氨基羰基取代的三至八元环,其任选被O、S或N间隔,
或
R9和R10一起形成N-(二-(C1-C6)烷基)亚硫烷基(sulfanylidene)、N-(芳基-(C1-C6)烷基)亚硫烷基、N-(二-(C3-C7)环烷基)亚硫烷基、N-((C1-C6)烷基-(C3-C7)环烷基)亚硫烷基或N,N-二-(C1-C6)烷基亚甲酰基(alkylformylidene group)。
特别优选式(I)的化合物,其中
[X-Y]代表部分:
Q代表部分Q-1至Q-3
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C2-C6)烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、羟基-(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)卤代烯基、(C2-C6)卤代炔基、(C1-C6)卤代烷氧基-(C1-C6)烷基、(C3-C7)环烷基、(C1-C6)烷氧基-(C1-C6)卤代烷基、(C1-C6)卤代烷氧基-(C1-C6)卤代烷基、(C1-C6)烷硫基-(C1-C6)烷基,
R2代表氢、三-(C1-C6)烷基甲硅烷基、(C1-C6)烷基-(二-(C1-C6)烷基)甲硅烷基、(C1-C6)烷基(二芳基)甲硅烷基、芳基(二-(C1-C6)烷基)甲硅烷基、(C3-C7)环烷基(二-(C1-C6)烷基)甲硅烷基、卤代(二-(C1-C6)烷基)甲硅烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷氧基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷基,
R3和R4彼此独立地代表(C1-C6)烷氧基、(C1-C6)烷硫基或与其所连接的原子一起形成氧代基团、羟基亚氨基、(C1-C6)烷氧基亚氨基、(C3-C6)环烷氧基亚氨基、(C3-C6)环烷基-(C1-C6)烷氧基亚氨基、芳基-(C1-C6)烷氧基亚氨基或任选可被进一步取代的5元至7元杂环,
R5和R6彼此独立地代表氢、卤素、(C1-C8)烷基、(C1-C6)卤代烷基,
R7代表卤素、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C8)卤代烷氧基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)炔氧基-(C1-C8)卤代烷基、(C1-C8)烯氧基-(C1-C8)卤代烷基、(C1-C6)烷硫基、(C1-C6)卤代烷硫基、任选取代的苯基、芳基-(C1-C6)烷基、杂芳基、杂芳基-(C1-C6)烷基,
R6和R7与其所键合的原子形成完全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代,
R8代表氢、(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、(C3-C7)环烷基、(C3-C7)环烷基-(C1-C6)烷基、任选取代的苯基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、二芳基-(C1-C6)烷基、三芳基-(C1-C6)烷基、(C2-C6)烯基、(C2-C6)烯基-(C1-C6)烷基、(C4-C7)环烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷氧基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷氧基-(C1-C6)烷基、(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)卤代烷基、芳基磺酰基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基、(C1-C6)烷基-(二芳基)甲硅烷基、(C1-C6)烷基-(二-(C1-C6)烷基)甲硅烷基、二-(C1-C6)烷基氨基-(C1-C6)烷基,
R9代表氢、(C1-C6)烷基、(C3-C7)环烷基、卤素、(C2-C6)烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)炔基、(C2-C6)烯基、氰基-(C1-C6)烷基、(C3-C7)环烷基-(C1-C6)烷基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、(C1-C6)烷基羰基、(C1-C6)烷氧基羰基、(C2-C6)烯氧基羰基、(C2-C6)烯基-(C1-C6)烷氧基羰基、芳基-(C1-C6)烷氧基羰基、(C3-C7)环烷氧基羰基、(C3-C6)环烷基-(C1-C6)烷氧基羰基、(C1-C6)烷基磺酰基、芳基磺酰基、(C3-C7)环烷基磺酰基、(C1-C6)烷基亚磺酰基、芳基亚磺酰基、(C3-C7)环烷基亚磺酰基、(C1-C6)烷氧基羰基-(C1-C6)烷基、羟基羰基-(C1-C6)烷基、芳基-(C1-C6)烷氧基羰基-(C1-C6)烷基、(C3-C7)环烷基-(C1-C6)烷氧基羰基-(C1-C6)烷基、(C1-C6)烷氧基羰基-(C3-C6)环烷基、羟基羰基-(C3-C6)环烷基、芳基-(C1-C6)烷氧基羰基-(C1-C6)环烷基、(C2-C6)烯氧基羰基-(C3-C6)环烷基、氨基羰基-(C3-C7)环烷基、(C1-C6)烷基氨基羰基-(C3-C7)环烷基、(C3-C7)环烷基氨基羰基-(C3-C7)环烷基、(C1-C6)烷氧基羰基-(C4-C7)环烯基、羟基羰基-(C4-C7)环烯基、二-(C1-C6)烷基氨基-(C1-C6)烷基、羟基羰基杂环基、(C1-C6)烷氧基羰基杂环基、(C2-C6)烯氧基羰基杂环基、(C2-C6)烯基-(C1-C6)烷氧基羰基杂环基、芳基-(C1-C6)烷氧基羰基杂环基、(C3-C7)环烷氧基羰基杂环基、(C3-C7)环烷基-(C1-C6)烷氧基羰基杂环基、氨基羰基杂环基、(C1-C6)烷基氨基羰基杂环基、二-(C1-C6)烷基氨基羰基杂环基、(C3-C7)环烷基氨基羰基杂环基、芳基-(C1-C6)烷基氨基羰基杂环基、(C2-C6)烯基氨基羰基杂环基、羟基羰基杂环基-(C1-C6)烷基、(C1-C6)烷氧基羰基杂环基-(C1-C6)烷基、羟基羰基-(C3-C7)环烷基-(C1-C6)烷基、(C1-C6)烷氧基羰基-(C3-C7)环烷基-(C1-C6)烷基、羟基、(C1-C6)烷氧基,
R10代表氢、(C1-C6)烷基、(C3-C7)环烷基、(C1-C6)烷基-(C1-C6)烯基、(C1-C6)卤代烷基、(C2-C6)炔基、(C2-C6)烯基、氰基-(C1-C6)烷基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、(C1-C6)烷基羰基、(C1-C6)烷氧基羰基、(C1-C6)烷基磺酰基、芳基磺酰基、(C3-C7)环烷基磺酰基、(C1-C6)烷基亚磺酰基、芳基亚磺酰基、(C3-C7)环烷基亚磺酰基、(C1-C6)烷氧基羰基-(C1-C6)烷基,
R9和R10与其所连接的氮形成任选被氟、氯、溴、碘、(C1-C6)烷基、(C1-C6)卤代烷基、(C1-C6)烷氧基、(C1-C6)烷氧基羰基、(C3-C7)环烷氧基羰基、(C3-C7)环烷基-(C1-C6)烷氧基羰基、(C2-C6)烯氧基羰基、羟基羰基、氨基羰基、(C1-C6)烷基氨基羰基、(C3-C7)环烷基氨基羰基、芳基-(C1-C6)烷基氨基羰基所取代的三至八元环,其任选被O、S或N间隔,
或
R9和R10一起形成N-(二-(C1-C6)烷基)亚硫烷基、N-(芳基-(C1-C6)烷基)亚硫烷基、N-(二-(C3-C7)环烷基)亚硫烷基、N-((C1-C6)烷基-(C3-C7)环烷基)亚硫烷基或N,N-二-(C1-C6)烷基亚甲酰基。
非常特别优选式(I)的化合物,其中
[X-Y]代表部分:
Q代表部分Q-1至Q-3
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表甲基、乙基、正丙基、正丁基、异丁基、异丙基、正戊基、正己基、异戊基、环丙基、环丁基、环戊基、丙-1-炔-3-基、丙-1-炔-1-基、丁-2-炔-3-基、丁-1-炔-1-基、乙炔基、1-甲基丙-2-炔-1-基、2-丁炔基、2-戊炔基、1-甲基丁-3-炔-1-基、乙烯基、丙-1-烯-1-基、丁-1-烯-1-基、烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、1-甲基丁-3-烯-1-基和1-甲基丁-2-烯-1-基、2-甲基丙-1-烯-1-基、1-甲基丙-1-烯-1-基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基丁-3-烯-1-基或1-甲基丁-2-烯-1-基、戊烯基、2-甲基戊烯基或己烯基、2-溴乙炔-1-基、2-氯乙炔-1-基、2-碘乙炔-1-基、2,2,3,3,3-五氟丙基、3,3,2,2-四氟丙基、4,4,4-三氟丁基、1-氟乙基、2-氟乙基、氟甲基、二氟甲基、三氟甲基、五氟乙基、七氟正丙基、七氟异丙基、氯二氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、2,2-二氯-2-氟乙基、2-氯-2,2-二氟乙基、二氟叔丁基、2-溴-1,1,2-三氟乙基、1,1,2,2-四氟乙基、1,2,2,2-四氟乙基、2-氯-1,1,2-三氟乙基、2-氯-1,1,2,2-四氟乙基、1,2,2,3,3,3-六氟丙基、1-甲基-2,2,2-三氟乙基、1-氯-2,2,2-三氟乙基、1,2,2,3,3,4,4,4-八氟丁基、1-氟-1-甲基乙基、正丙氧基二氟甲基、甲氧基二氟甲基、乙氧基二氟甲基、甲硫基甲基、乙硫基甲基、正丙硫基甲基、氯甲基、溴甲基,
R2代表氢、叔丁基二甲基甲硅烷基、三甲基甲硅烷基、三乙基甲硅烷基、三(异丙基)甲硅烷基、三-(正丙基)甲硅烷基、叔丁基二苯基甲硅烷基、二乙基异丙基甲硅烷基、异丙基二甲基甲硅烷基、叔己基二甲基甲硅烷基、2-(三甲基甲硅烷基)乙氧基甲基、2-(三甲基甲硅烷基)乙基、二甲基(苯基)甲硅烷基,
R3和R4彼此独立地代表甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基或与其所连接的原子形成氧代基团、羟基亚氨基、(C1-C6)烷氧基亚氨基、(C3-C6)环烷氧基亚氨基、(C3-C6)环烷基-(C1-C6)烷氧基亚氨基、芳基-(C1-C6)烷氧基亚氨基或5元至7元杂环,例如1,3-二氧杂环戊基、1,3-二氧杂环己基、1,3-二硫杂环戊基、1,3-二噻烷基、1,3-氧硫杂环己基、5-烷基-1,3,5-二噻嗪基、1,3-噁唑烷基环,该杂环可任选被(C1-C6)烷基、(C1-C6)烷氧基羰基、(C3-C6)环烷基、螺-(C3-C6)环烷基、螺-氧杂环丁基进一步取代,
R5和R6彼此独立地代表氢、氟、氯、溴、碘、甲基、乙基、正丙基、正丁基、异丁基、异丙基、正戊基、正己基、异戊基、三氟甲基、五氟乙基、七氟丙基、九氟丁基、氯二氟甲基、溴二氟甲基、二氯氟甲基、溴氟甲基、1-氟乙基、2-氟乙基、氟甲基、二氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、2,2-二氯-2-氟乙基、2-氯-2,2-二氟乙基、二氟叔丁基,
R7代表氟、氯、溴、碘、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)炔氧基-(C1-C8)卤代烷基、(C1-C8)烯氧基-(C1-C8)卤代烷基、(C1-C6)烷硫基、(C1-C6)卤代烷硫基、任选取代的苯基、芳基-(C1-C6)烷基、杂芳基、杂芳基-(C1-C6)烷基、(C3-C7)环烷基、(C3-C7)环卤代烷基,
R6和R7与其所键合的原子形成完全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代,
R8代表氢、(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、(C3-C7)环烷基、(C3-C7)环烷基-(C1-C6)烷基、任选取代的苯基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、二芳基-(C1-C6)烷基、三芳基-(C1-C6)烷基、(C2-C6)烯基、(C2-C6)烯基-(C1-C6)烷基、(C4-C6)环烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷氧基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷氧基-(C1-C6)烷基、(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)卤代烷基、芳基磺酰基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基、(C1-C6)烷基-(二芳基)甲硅烷基、(C1-C6)烷基-(二-(C1-C6)烷基)甲硅烷基、二-(C1-C6)烷基氨基-(C1-C6)烷基,
R9代表氢、(C1-C6)烷基、(C3-C6)环烷基、氯、溴、(C2-C6)烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)炔基、(C2-C6)烯基、氰基-(C1-C6)烷基、(C3-C7)环烷基-(C1-C6)烷基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、(C1-C6)烷基羰基、(C1-C6)烷氧基羰基、(C2-C6)烯氧基羰基、(C2-C6)烯基-(C1-C6)烷氧基羰基、芳基-(C1-C6)烷氧基羰基、(C3-C7)环烷氧基羰基、(C3-C6)环烷基-(C1-C6)烷氧基羰基、(C1-C6)烷基磺酰基、芳基磺酰基、(C3-C7)环烷基磺酰基、(C1-C6)烷基亚磺酰基、芳基亚磺酰基、(C3-C7)环烷基亚磺酰基、(C1-C6)烷氧基羰基-(C1-C6)烷基、羟基羰基-(C1-C6)烷基、芳基-(C1-C6)烷氧基羰基-(C1-C6)烷基、(C3-C7)环烷基-(C1-C6)烷氧基羰基-(C1-C6)烷基、(C1-C6)烷氧基羰基-(C3-C6)环烷基、羟基羰基-(C3-C6)环烷基、芳基-(C1-C6)烷氧基羰基-(C3-C6)环烷基、(C2-C6)烯氧基羰基-(C3-C6)环烷基、氨基羰基-(C3-C6)环烷基、(C1-C6)烷基氨基羰基-(C3-C6)环烷基、(C3-C6)环烷基氨基羰基-(C3-C6)环烷基、(C1-C6)烷氧基羰基-(C4-C6)环烯基、羟基羰基-(C4-C7)环烯基、二-(C1-C6)烷基氨基-(C1-C6)烷基、羟基羰基杂环基、(C1-C6)烷氧基羰基杂环基、(C2-C6)烯氧基羰基杂环基、(C2-C6)烯基-(C1-C6)烷氧基羰基杂环基、芳基-(C1-C6)烷氧基羰基杂环基、(C3-C6)环烷氧基羰基杂环基、(C3-C6)环烷基-(C1-C6)烷氧基羰基杂环基、氨基羰基杂环基、(C1-C6)烷基氨基羰基杂环基、二-(C1-C6)烷基氨基羰基杂环基、(C3-C6)环烷基氨基羰基杂环基、芳基-(C1-C6)烷基氨基羰基杂环基、(C2-C6)烯基氨基羰基杂环基、羟基羰基杂环基-(C1-C6)烷基、(C1-C6)烷氧基羰基杂环基-(C1-C6)烷基、羟基羰基-(C3-C6)环烷基-(C1-C6)烷基、(C1-C6)烷氧基羰基-(C3-C7)环烷基-(C1-C6)烷基、羟基、(C1-C6)烷氧基,
R10代表氢、(C1-C6)烷基、(C3-C7)环烷基、(C1-C6)烷基-(C1-C6)烯基、(C1-C6)卤代烷基、(C2-C6)炔基、(C2-C6)烯基、氰基-(C1-C6)烷基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、(C1-C6)烷基羰基、(C1-C6)烷氧基羰基、(C1-C6)烷基磺酰基、芳基磺酰基、(C3-C7)环烷基磺酰基、(C1-C6)烷基亚磺酰基、芳基亚磺酰基、(C3-C6)环烷基亚磺酰基、(C1-C6)烷氧基羰基-(C1-C6)烷基,
R9和R10与其所连接的氮形成任选被氟、氯、溴、碘、(C1-C6)烷基、(C1-C6)卤代烷基、(C1-C6)烷氧基、(C1-C6)烷氧基羰基、(C3-C7)环烷氧基羰基、(C3-C6)环烷基-(C1-C6)烷氧基羰基、(C2-C6)烯氧基羰基、羟基羰基、氨基羰基、(C1-C6)烷基氨基羰基、(C3-C7)环烷基氨基羰基、芳基-(C1-C6)烷基氨基羰基取代的三至七元环,其任选被O、S或N间隔,
或
R9和R10一起代表N-(二-正丁基亚硫烷基)、N-(二-异丙基亚硫烷基)、N-(二-正丙基亚硫烷基)、N-(二-正戊基亚硫烷基)、N-(二异丁基亚硫烷基)、N-(环丁基异丙基亚硫烷基)、N-(正丙基异丙基亚硫烷基)、N-(环丙基异丙基亚硫烷基)、N-(异丁基异丙基亚硫烷基)、N,N-二甲基亚甲酰基,
此外Q为下表中记载的Q-1.1至Q-3.45部分之一。
具体优选式(I)的化合物,其中
[X-Y]代表部分:
Q代表部分Q-1至Q-3
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表甲基、乙基、正丙基、正丁基、异丁基、异丙基、正戊基、正己基、异戊基、环丙基、环丁基、环戊基、2,2,3,3,3-五氟丙基、3,3,2,2-四氟丙基、4,4,4-三氟丁基、1-氟乙基、2-氟乙基、氟甲基、二氟甲基、三氟甲基、五氟乙基、七氟正丙基、七氟异丙基、氯二氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、1,1,2,2-四氟乙基、1,2,2,2-四氟乙基、1,2,2,3,3,3-六氟丙基、1-甲基-2,2,2-三氟乙基、1-氯-2,2,2-三氟乙基、1,2,2,3,3,4,4,4-八氟丁基、1-氟-1-甲基乙基、正丙氧基二氟甲基、甲氧基二氟甲基、乙氧基二氟甲基,
R2代表氢、叔丁基二甲基甲硅烷基、三甲基甲硅烷基、三乙基甲硅烷基、三(异丙基)甲硅烷基、三-(正丙基)甲硅烷基、叔丁基二苯基甲硅烷基、二乙基异丙基甲硅烷基、异丙基二甲基甲硅烷基、叔己基二甲基甲硅烷基、2-(三甲基甲硅烷基)乙氧基甲基、2-(三甲基甲硅烷基)乙基、二甲基(苯基)甲硅烷基,
R3和R4彼此独立地代表甲氧基、乙氧基、正丙氧基、正丁氧基、甲硫基、乙硫基、正丙硫基、正丁硫基或与其所连接的原子一起形成氧代基团、羟基亚氨基;甲氧基亚氨基、乙氧基亚氨基、正丙氧基亚氨基、异丙氧基亚氨基、正丁氧基亚氨基、异丁氧基亚氨基、环丙氧基亚氨基、环丁氧基亚氨基、环丙基甲氧基亚氨基、苯甲氧基亚氨基、对-氯苯基甲氧基亚氨基、对-甲基苯基甲氧基亚氨基、对-甲氧基苯基甲氧基亚氨基、邻-氯苯基甲氧基亚氨基、间-氯苯基甲氧基亚氨基或5元至7元杂环,例如1,3-二氧杂环戊基、1,3-二氧杂环己基、1,3-二硫杂环戊基、1,3-二噻烷基、1,3-氧硫杂环己基、5-烷基-1,3,5-二噻嗪基、1,3-噁唑烷基环,该杂环可任选被(C1-C6)烷基、(C1-C6)烷氧基羰基、(C3-C6)环烷基、螺-(C3-C6)环烷基、螺-氧杂环丁基进一步取代,
R5和R6彼此独立地代表氢、氟、氯、溴、碘、甲基、乙基、正丙基、正丁基、异丁基、异丙基、正戊基、正己基、异戊基、三氟甲基、五氟乙基、七氟丙基、九氟丁基、氯二氟甲基、1-氟乙基、2-氟乙基、氟甲基、二氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、2,2-二氯-2-氟乙基、2-氯-2,2-二氟乙基、二氟-叔-丁基,
R7代表氟、氯、溴、碘、(C1-C8)烷基、(C1-C7)卤代烷基、(C1-C7)卤代烷氧基-(C1-C7)烷基、(C1-C7)卤代烷氧基-(C1-C7)卤代烷基、(C1-C6)烷氧基-(C1-C6)卤代烷基、(C3-C6)环烷基、(C3-C6)环卤代烷基,
R6和R7与其所键合的原子形成全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代。
R8代表氢、(C1-C4)烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C3-C6)环烷基、(C3-C6)环烷基-(C1-C4)烷基、任选取代的苯基、芳基-(C1-C4)烷基、杂芳基-(C1-C4)烷基、(C2-C6)烯基、(C2-C4)炔基-(C1-C4)烷基、(C1-C4)卤代烷基,
R9代表氢、(C1-C4)烷基、(C3-C6)环烷基、氯、(C2-C6)烯基-(C1-C4)烷基、(C2-C6)炔基-(C1-C4)烷基、(C1-C4)卤代烷基、(C2-C6)炔基、(C2-C6)烯基、氰基-(C1-C4)烷基、(C3-C6)环烷基-(C1-C4)烷基、芳基-(C1-C4)烷基、杂芳基-(C1-C4)烷基、(C1-C4)烷基羰基、(C1-C4)烷氧基羰基、(C1-C4)烷氧基羰基-(C1-C4)烷基、羟基羰基-(C1-C4)烷基、芳基-(C1-C4)烷氧基羰基-(C1-C4)烷基、(C3-C6)环烷基-(C1-C4)烷氧基羰基-(C1-C4)烷基、(C1-C4)烷氧基羰基-(C3-C6)环烷基、羟基羰基-(C3-C6)环烷基、芳基-(C1-C4)烷氧基羰基-(C3-C6)环烷基、(C2-C6)烯氧基羰基-(C3-C6)环烷基、(C1-C6)烷氧基羰基-(C4-C6)环烯基、羟基羰基-(C4-C6)环烯基、羟基羰基杂环基、(C1-C4)烷氧基羰基杂环基、羟基羰基杂环基-(C1-C4)烷基、(C1-C4)烷氧基羰基杂环基-(C1-C4)烷基、羟基羰基-(C3-C6)环烷基-(C1-C4)烷基、(C1-C4)烷氧基羰基-(C3-C6)环烷基-(C1-C6)烷基、羟基、(C1-C6)烷氧基,
R10代表氢、(C1-C6)烷基、(C3-C6)环烷基,
R9和R10与其所连接的氮原子形成任选被氟、氯、溴、碘、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)烷氧基羰基、(C3-C6)环烷氧基羰基、(C3-C6)环烷基-(C1-C4)烷氧基羰基、(C2-C6)烯氧基羰基、羟基羰基、氨基羰基、(C1-C4)烷基氨基羰基、(C3-C6)环烷基氨基羰基、芳基-(C1-C4)烷基氨基羰基取代的三元至七元环,其任选被O、S或N间隔
或
R9和R10一起代表N-(二正丁基亚硫烷基)、N-(二异丙基亚硫烷基)、N-(二正丙基亚硫烷基)、N-(二正戊基亚硫烷基)、N-(二异丁基亚硫烷基)、N-(环丁基异丙基亚硫烷基)、N-(正丙基异丙基亚硫烷基)、N-(环丙基异丙基亚硫烷基)、N-(异丁基异丙基亚硫烷基)、N,N-二甲基亚甲酰基,
并且Q另外代表上文提及的表中记载的Q-1.1至Q-3.45部分之一。
上述一般的基团定义或优选部分的基团定义适用于式(I)的最终产物并且相应地适用于在其各个制备情况下所需的原料或中间体。
这些基团定义可视需要彼此结合,即包括给定的优选范围的结合。
同样目前未知并且因此构成本发明又一部分的为式(II)的化合物或其盐
其作为用于制备本发明式(I)的化合物的中间体,
其中
R1代表(C1-C8)烷基、(C2-C8)烯基、(C2-C8)炔基、(C2-C8)烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、羟基-(C1-C8)烷基、(C1-C8)卤代烷基、(C2-C8)卤代烯基、(C2-C8)卤代炔基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C3-C8)环烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷硫基-(C1-C8)烷基,
R2代表氢、(C1-C8)烷基、(C2-C8)烯基、(C2-C8)烯基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷基羰基、芳基羰基、杂芳基羰基、(C3-C8)环烷基羰基、(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、芳基-(C1-C8)烷氧基羰基、芳基-(C1-C8)烷氧基-(C1-C8)烷基、芳氧基-(C1-C8)烷基、芳基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷硫基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基、(C1-C8)烷基-(二-(C1-C8)烷基)甲硅烷基、(C1-C8)烷基(二芳基)甲硅烷基、芳基(二-(C1-C8)烷基)甲硅烷基、(C3-C8)环烷基(二-(C1-C6)烷基)甲硅烷基、卤代(二-(C1-C8)烷基)甲硅烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷氧基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷基,
R3和R4彼此独立地代表(C1-C8)烷氧基、(C1-C8)烷氧基-(C1-C8)烷氧基、(C3-C8)环烷基-(C1-C8)烷氧基、(C1-C8)卤代烷氧基、(C1-C8)烷硫基、(C1-C8)卤代烷硫基、芳基-(C1-C8)烷氧基、芳基-(C1-C8)烷硫基或与其所连接的原子一起形成氧代基团或5元至7元杂环,例如1,3-二氧杂环戊基、1,3-二氧杂环己基、1,3-二硫杂环戊基、1,3-二噻烷基、1,3-氧硫杂环己基、5-烷基-1,3,5-二噻嗪基、1,3-噁唑烷基环,该杂环可任选被(C1-C6)烷基、(C1-C6)烷氧基羰基、(C3-C6)环烷基、螺-(C3-C6)环烷基、螺-氧杂环丁基进一步取代,和
[M]代表三-[(C1-C6)烷基]甲锡烷基、三-[(C3-C8)环烷基]甲锡烷基、三-[(C1-C6)烷基]锗基、三-[(C3-C8)环烷基]锗基、二-(环戊二烯基)氧锆基、二-(1,2,3,4,5-五甲基环戊二烯基)氧锆基、二-(环戊二烯基)铪氧基、二-(1,2,3,4,5-五甲基环戊二烯基)铪氧基、二-(羟基)硼基、二-[(C1-C6)烷氧基]-硼基、(C1-C6)烷基-1,3,2-二氧杂环戊硼烷-2-基、二-[(C1-C6)烷基]-1,3,2-二氧杂环戊硼烷-2-基、四-[(C1-C6)烷基]-1,3,2-二氧杂环戊硼烷-2-基、1,3,2-二氧杂环己硼烷-2-基、二-[(C1-C6)烷基]-1,3,2-二氧杂环己硼烷-2-基、(C1-C6)烷基-1,3,2-二氧杂环己硼烷-2-基、三-[(C1-C6)烷基]-1,3,2-二氧杂环己硼烷-2-基、2,6,7-三氧杂-1-甲硼烷负离子杂(boranuida)双环[2.2.2]辛烷基、(C1-C6)烷基-2,6,7-三氧杂-1-甲硼烷负离子杂双环[2.2.2]辛烷基、三-[(C1-C6)烷基]铅烷基(plumbanyl)、三-[(C1-C6)烷基羰基氧基]铅烷基、三-芳基-铅烷基、二-[(C1-C6)烷基羰基氧基]-芳基铅烷基、二-[(C1-C6)烷基]-铝基、二-[(C1-C6)环烷基]-铝基、二氯铝基、氯代镁基、溴代镁基、氯代锌基(chlorozincyl)、氯代汞基(chlorohydrargyl)、溴代汞基(bromohydrargyl)、(C1-C6)烷基汞基、(C3-C6)环烷基汞基、三-[(C1-C6)烷基]甲硅烷基、(C1-C6)烷基-[二-(C1-C6)烷基]甲硅烷基、(C1-C6)烷基-二-(芳基)甲硅烷基、芳基-二-[(C1-C6)烷基)]甲硅烷基、(C3-C7)环烷基-二-[(C1-C6)烷基]甲硅烷基。
优选式(II)的化合物,其中
R1代表(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、(C1-C6)卤代烷基、(C1-C6)卤代烷氧基-(C1-C6)烷基、(C3-C6)环烷基、(C1-C6)烷氧基-(C1-C6)卤代烷基、(C1-C6)卤代烷氧基-(C1-C6)卤代烷基、(C1-C6)烷硫基-(C1-C6)烷基,
R2代表氢、三-(C1-C6)烷基甲硅烷基、(C1-C6)烷基-(二-(C1-C6)烷基)甲硅烷基、(C1-C6)烷基(二-芳基)甲硅烷基、芳基(二-(C1-C6)烷基)甲硅烷基、(C3-C6)环烷基(二-(C1-C6)烷基)甲硅烷基、卤代(二-(C1-C6)烷基)甲硅烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷氧基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷基,
R3和R4彼此独立地代表(C1-C8)烷氧基、(C1-C8)烷硫基、芳基-(C1-C8)烷氧基、芳基-(C1-C8)烷硫基或与其所连接的原子一起形成氧代基团或5元至7元杂环,例如1,3-二氧杂环戊基、1,3-二氧杂环己基、1,3-二硫杂环戊基、1,3-二噻烷基、1,3-氧硫杂环己基、5-烷基-1,3,5-二噻嗪基、1,3-噁唑烷基环,该杂环可任选被(C1-C6)烷基、(C1-C6)烷氧基羰基、(C3-C6)环烷基、螺-(C3-C6)环烷基、螺-氧杂环丁基进一步取代,和
[M]代表三-[(C1-C6)烷基]甲锡烷基、三-[(C3-C6)环烷基]甲锡烷基、三-[(C1-C6)烷基]锗基、三-[(C3-C6)环烷基]锗基、二-(环戊二烯基)氧锆基、二-(1,2,3,4,5-五甲基环戊二烯基)氧锆基、二-(环戊二烯基)铪氧基、二-(1,2,3,4,5-五甲基环戊二烯基)铪氧基、二-(羟基)硼基、二-[(C1-C6)烷氧基]-硼基、(C1-C6)烷基-1,3,2-二氧杂环戊硼烷-2-基、二-[(C1-C6)烷基]-1,3,2-二氧杂环戊硼烷-2-基、四-[(C1-C6)烷基]-1,3,2-二氧杂环戊硼烷-2-基、1,3,2-二氧杂环己硼烷-2-基、二-[(C1-C6)烷基]-1,3,2-二氧杂环己硼烷-2-基、(C1-C6)烷基-1,3,2-二氧杂环己硼烷-2-基、三-[(C1-C6)烷基]-1,3,2-二氧杂环己硼烷-2-基、2,6,7-三氧杂-1-甲硼烷负离子杂双环[2.2.2]辛烷基、(C1-C6)烷基-2,6,7-三氧杂-1-甲硼烷负离子杂双环[2.2.2]辛烷基、三-[(C1-C6)烷基]铅烷基、三-[(C1-C6)烷基羰基氧基]铅烷基、三-芳基-铅烷基、二-[(C1-C6)烷基羰基氧基]-芳基铅烷基、二-[(C1-C6)烷基]-铝基、二-[(C1-C6)环烷基]-铝基、二氯铝基、氯代镁基、溴代镁基、氯代锌基、氯代汞基、溴代汞基、(C1-C6)烷基汞基、(C3-C6)环烷基汞基、三-[(C1-C6)烷基]甲硅烷基、(C1-C6)烷基-[二-(C1-C6)烷基]甲硅烷基、(C1-C6)烷基-二-(芳基)甲硅烷基、芳基-二-[(C1-C6)烷基)]甲硅烷基、(C3-C7)环烷基-二-[(C1-C6)烷基]甲硅烷基。
关于本发明的化合物,将说明上文和下文使用的术语。这些术语是本领域技术人员所熟知的并且特别具有下文所阐明的定义:
根据本发明,“芳基磺酰基”代表任选取代的苯基磺酰基或任选取代的多环芳基磺酰基,在此特别是任选取代的萘基磺酰基,例如被氟、氯、溴、碘、氰基、硝基、烷基、卤代烷基、卤代烷氧基、氨基、烷基氨基、烷基羰基氨基、二烷基氨基或烷氧基取代。
根据本发明,“环烷基磺酰基”——单独或作为化学基团的一部分——代表任选取代的环烷基磺酰基,优选具有3至6个碳原子的环烷基磺酰基,例如环丙基磺酰基、环丁基磺酰基、环戊基磺酰基或环己基磺酰基。
根据本发明,“烷基磺酰基”——单独或作为化学基团的一部分——代表直链或支链的烷基磺酰基,优选具有1至8个,或具有1至6个碳原子的烷基磺酰基,例如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基和叔丁基磺酰基。
根据本发明,“杂芳基磺酰基”代表任选取代的吡啶基磺酰基、嘧啶基磺酰基、吡嗪基磺酰基或任选取代的多环杂芳基磺酰基,在此特别是任选取代的喹啉基磺酰基,例如被氟、氯、溴、碘、氰基、硝基、烷基、卤代烷基、卤代烷氧基、氨基、烷基氨基、烷基羰基氨基、二烷基氨基或烷氧基取代。
根据本发明,“烷硫基”——单独或作为化学基团的一部分——代表直链或支链的S-烷基,优选具有1至8个或具有1至6个碳原子,例如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基和叔丁硫基。烯硫基是通过硫原子连接的烯基,炔硫基是通过硫原子连接的炔基,环烷硫基是通过硫原子连接的环烷基,并且环烯硫基是通过硫原子连接的环烯基。
“烷氧基”是通过氧原子连接的烷基,烯氧基是通过氧原子连接的烯基,炔氧基是通过氧原子连接的炔基,环烷氧基是通过氧原子连接的环烷基,并且环烯氧基是通过氧原子连接的环烯基。
术语“芳基”是指优选具有6至14个,特别是6至10个环碳原子的任选取代的单环、二环或多环芳族体系,例如苯基、萘基、蒽基、菲基等,优选苯基。
术语“任选取代的芳基”还包括多环体系,如四氢萘基、茚基、茚满基、芴基、联苯基,其中键合点在芳族体系上。就系统术语而言,“芳基”通常还被囊括在术语“任选取代的苯基”中。
杂环基团(杂环基)包括至少一个杂环(=其中至少一个碳原子被杂原子,优选被选自N、O、S、P的杂原子取代的碳环),所述杂环可为饱和、不饱和、部分饱和或杂芳族的且其可为未取代或取代的,其中键合点位于环原子上。当杂环基团或杂环任选被取代时,则所述杂环基团或杂环可稠合至其他碳环或杂环。对于任选取代的杂环基,还包括多环体系,例如8-氮杂二环[3.2.1]辛烷基、8-氮杂二环[2.2.2]辛烷基或1-氮杂二环[2.2.1]庚基。对于任选取代的杂环基,还包括螺环体系,例如1-氧杂-5-氮杂螺[2.3]己基。除非另有定义,所述杂环包括优选包括3至9个环原子且特别是3至6个环原子,并且在杂环中包含一个或多个,优选1至4个且特别是1个、2个或3个优选选自N、O和S的杂原子,但两个氧原子不可直接相邻,例如,含有一个选自N、O和S的杂原子:1-或2-或3-吡咯烷基、3,4-二氢-2H-吡咯-2-或3-基、2,3-二氢-1H-吡咯-1-或2-或3-或4-或5-基、2,5-二氢-1H-吡咯-1-或2-或3-基、1-或2-或3-或4-哌啶基、2,3,4,5-四氢吡啶-2-或3-或4-或5-基或6-基、1,2,3,6-四氢吡啶-1-或2-或3-或4-或5-或6-基、1,2,3,4-四氢吡啶-1-或2-或3-或4-或5-或6-基、1,4-二氢吡啶-1-或2-或3-或4-基、2,3-二氢吡啶-2-或3-或4-或5-或6-基、2,5-二氢吡啶-2-或3-或4-或5-或6-基、1-或2-或3-或4-氮杂环庚基、2,3,4,5-四氢-1H-氮杂卓(azepin)-1-或2-或3-或4-或5-或6-或7-基、2,3,4,7-四氢-1H-氮杂卓-1-或2-或3-或4-或5-或6-或7-基、2,3,6,7-四氢-1H-氮杂卓-1-或2-或3-或4-基、3,4,5,6-四氢-2H-氮杂卓-2-或3-或4-或5-或6-或7-基、4,5-二氢-1H-氮杂卓-1-或2-或3-或4-基、2,5-二氢-1H-氮杂卓-1-或-2-或3-或4-或5-或6-或7-基、2,7-二氢-1H-氮杂卓-1-或-2-或3-或4-基、2,3-二氢-1H-氮杂卓-1-或-2-或3-或4-或5-或6-或7-基、3,4-二氢-2H-氮杂卓-2-或3-或4-或5-或6-或7-基、3,6-二氢-2H-氮杂卓-2-或3-或4-或5-或6-或7-基、5,6-二氢-2H-氮杂卓-2-或3-或4-或5-或6-或7-基、4,5-二氢-3H-氮杂卓-2-或3-或4-或5-或6-或7-基、1H-氮杂卓-1-或-2-或3-或4-或5-或6-或7-基、2H-氮杂卓-2-或3-或4-或5-或6-或7-基、3H-氮杂卓-2-或3-或4-或5-或6-或7-基、4H-氮杂卓-2-或3-或4-或5-或6-或7-基、2-或3-氧杂环戊基(oxolanyl)(=2-或3-四氢呋喃基)、2,3-二氢呋喃-2-或3-或4-或5-基、2,5-二氢呋喃-2-或3-基、2-或3-或4-氧杂环己基(=2-或3-或4-四氢吡喃基)、3,4-二氢-2H-吡喃-2-或3-或4-或5-或6-基、3,6-二氢-2H-吡喃-2-或3-或4-或5-或6-基、2H-吡喃-2-或3-或4-或5-或6-基、4H-吡喃-2-或3-或4-基、2-或3-或4-氧杂环庚基(oxepanyl)、2,3,4,5-四氢氧杂卓(oxepin)-2-或3-或4-或5-或6-或7-基、2,3,4,7-四氢氧杂卓-2-或3-或4-或5-或6-或7-基、2,3,6,7-四氢氧杂卓-2-或3-或4-基、2,3-二氢氧杂卓-2-或3-或4-或5-或6-或7-基、4,5-二氢氧杂卓-2-或3-或4-基、2,5-二氢氧杂卓-2-或3-或4-或5-或6-或7-基、氧杂卓-2-或3-或4-或5-或6-或7-基、2-或3-四氢苯硫基、2,3-二氢噻吩基-2-或3-或4-或5-基、2,5-二氢噻吩基-2-或3-基、四氢-2H-噻喃-2-或3-或4-基、3,4-二氢-2H-噻喃-2-或3-或4-或5-或6-基、3,6-二氢-2H-噻喃-2-或3-或4-或5-或6-基、2H-噻喃-2-或3-或4-或5-或6-基、4H-噻喃-2-或3-或4-基。优选的3元和4元杂环为,例如1-或2-吖丙啶基、环氧乙烷基(oxiranyl)、硫杂丙环基(thiiranyl)、1-或2-或3-氮杂环丁基、2-或3-氧杂环丁基、2-或3-硫杂环丁基(thietanyl)、1,3-二氧杂环丁-2-基。“杂环基”的其他实例为具有两个选自N、O和S的杂原子的部分氢化或完全氢化的杂环基,例如1-或2-或3-或4-吡唑烷基、4,5-二氢-3H-吡唑-3-或4-或5-基、4,5-二氢-1H-吡唑-1-或3-或4-或5-基、2,3-二氢-1H-吡唑-1-或2-或3-或4-或5-基、1-或2-或3-或4-咪唑烷基、2,3-二氢-1H-咪唑-1-或2-或3-或4-基、2,5-二氢-1H-咪唑-1-或2-或4-或5-基、4,5-二氢-1H-咪唑-1-或2-或4-或5-基、六氢哒嗪-1-或2-或3-或4-基、1,2,3,4-四氢哒嗪-1-或2-或3-或4-或5-或6-基、1,2,3,6-四氢哒嗪-1-或2-或3-或4-或5-或6-基、1,4,5,6-四氢哒嗪-1-或3-或4-或5-或6-基、3,4,5,6-四氢哒嗪-3-或4-或5-基、4,5-二氢哒嗪-3-或4-基、3,4-二氢哒嗪-3-或4-或5-或6-基、3,6-二氢哒嗪-3-或4-基、1,6-二氢哒嗪-1-或3-或4-或5-或6-基、六氢嘧啶-1-或2-或3-或4-基、1,4,5,6-四氢嘧啶-1-或2-或4-或5-或6-基、1,2,5,6-四氢嘧啶-1-或2-或4-或5-或6-基、1,2,3,4-四氢嘧啶-1-或2-或3-或4-或5-或6-基、1,6-二氢嘧啶-1-或2-或4-或5-或6-基、1,2-二氢嘧啶-1-或2-或4-或5-或6-基、2,5-二氢嘧啶-2-或4-或5-基、4,5-二氢嘧啶-4-或5-或6-基、1,4-二氢嘧啶-1-或2-或4-或5-或6-基、1-或2-或3-哌嗪基、1,2,3,6-四氢吡嗪-1-或2-或3-或5-或6-基、1,2,3,4-四氢吡嗪-1-或2-或3-或4-或5-或6-基、1,2-二氢吡嗪-1-或2-或3-或5-或6-基、1,4-二氢吡嗪-1-或2-或3-基、2,3-二氢吡嗪-2-或3-或5-或6-基、2,5-二氢吡嗪-2-或3-基、1,3-二氧戊环-2-或4-或5-基、1,3-间二氧杂环戊烯(dioxol)-2-或4-基、1,3-二噁烷-2-或4-或5-基、4H-1,3-二噁英-2-或4-或5-或6-基、1,4-二噁烷-2-或3-或5-或6-基、2,3-二氢-1,4-二噁英-2-或3-或5-或6-基、1,4-二噁英-2-或3-基、1,2-二硫戊环-3-或4-基、3H-1,2-二硫杂环戊二烯-3-或4-或5-基、1,3-二硫戊环-2-或4-基、1,3-二硫杂环戊二烯-2-或4-基、1,2-二噻烷-3-或4-基、3,4-二氢-1,2-二噻英(dithiin)-3-或4-或5-或6-基、3,6-二氢-1,2-二噻英-3-或4-基、1,2-二噻英-3-或4-基、1,3-二噻烷-2-或4-或5-基、4H-1,3-二噻英-2-或4-或5-或6-基、异噁唑烷-2-或3-或4-或5-基、2,3-二氢异噁唑-2-或3-或4-或5-基、2,5-二氢异噁唑-2-或3-或4-或5-基、4,5-二氢异噁唑-3-或4-或5-基、1,3-噁唑烷-2-或3-或4-或5-基、2,3-二氢-1,3-噁唑-2-或3-或4-或5-基、2,5-二氢-1,3-噁唑-2-或4-或5-基、4,5-二氢-1,3-噁唑-2-或4-或5-基、1,2-氧氮杂环己(oxazinan)-2-或3-或4-或5-或6-基、3,4-二氢-2H-1,2-噁嗪-2-或3-或4-或5-或6-基、3,6-二氢-2H-1,2-噁嗪-2-或3-或4-或5-或6-基、5,6-二氢-2H-1,2-噁嗪-2-或3-或4-或5-或6-基、5,6-二氢-4H-1,2-噁嗪-3-或4-或5-或6-基、2H-1,2-噁嗪-2-或3-或4-或5-或6-基、6H-1,2-噁嗪-3-或4-或5-或6-基、4H-1,2-噁嗪-3-或4-或5-或6-基、1,3-氧氮杂环己-2-或3-或4-或5-或6-基、3,4-二氢-2H-1,3-噁嗪-2-或3-或4-或5-或6-基、3,6-二氢-2H-1,3-噁嗪-2-或3-或4-或5-或6-基、5,6-二氢-2H-1,3-噁嗪-2-或4-或5-或6-基、5,6-二氢-4H-1,3-噁嗪-2-或4-或5-或6-基、2H-1,3-噁嗪-2-或4-或5-或6-基、6H-1,3-噁嗪-2-或4-或5-或6-基、4H-1,3-噁嗪-2-或4-或5-或6-基、吗啉-2-或3-或4-基、3,4-二氢-2H-1,4-噁嗪-2-或3-或4-或5-或6-基、3,6-二氢-2H-1,4-噁嗪-2-或3-或5-或6-基、2H-1,4-噁嗪-2-或3-或5-或6-基、4H-1,4-噁嗪-2-或3-基、1,2-氧氮杂环庚(oxazepan)-2-或3-或4-或5-或6-或7-基、2,3,4,5-四氢-1,2-氧氮杂卓(oxazepin)-2-或3-或4-或5-或6-或7-基、2,3,4,7-四氢-1,2-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,3,6,7-四氢-1,2-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,5,6,7-四氢-1,2-氧氮杂卓-2-或3-或4-或5-或6-或7-基、4,5,6,7-四氢-1,2-氧氮杂卓-3-或4-或5-或6-或7-基、2,3-二氢-1,2-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,5-二氢-1,2-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,7-二氢-1,2-氧氮杂卓-2-或3-或4-或5-或6-或7-基、4,5-二氢-1,2-氧氮杂卓-3-或4-或5-或6-或7-基、4,7-二氢-1,2-氧氮杂卓-3-或4-或5-或6-或7-基、6,7-二氢-1,2-氧氮杂卓-3-或4-或5-或6-或7-基、1,2-氧氮杂卓-3-或4-或5-或6-或7-基、1,3-氧氮杂环庚-2-或3-或4-或5-或6-或7-基、2,3,4,5-四氢-1,3-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,3,4,7-四氢-1,3-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,3,6,7-四氢-1,3-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,5,6,7-四氢-1,3-氧氮杂卓-2-或4-或5-或6-或7-基、4,5,6,7-四氢-1,3-氧氮杂卓-2-或4-或5-或6-或7-基、2,3-二氢-1,3-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,5-二氢-1,3-氧氮杂卓-2-或4-或5-或6-或7-基、2,7-二氢-1,3-氧氮杂卓-2-或4-或5-或6-或7-基、4,5-二氢-1,3-氧氮杂卓-2-或4-或5-或6-或7-基、4,7-二氢-1,3-氧氮杂卓-2-或4-或5-或6-或7-基、6,7-二氢-1,3-氧氮杂卓-2-或4-或5-或6-或7-基、1,3-氧氮杂卓-2-或4-或5-或6-或7-基、1,4-氧氮杂环庚-2-或3-或5-或6-或7-基、2,3,4,5-四氢-1,4-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,3,4,7-四氢-1,4-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,3,6,7-四氢-1,4-氧氮杂卓-2-或3-或5-或6-或7-基、2,5,6,7-四氢-1,4-氧氮杂卓-2-或3-或5-或6-或7-基、4,5,6,7-四氢-1,4-氧氮杂卓-2-或3-或4-或5-或6-或7-基、2,3-二氢-1,4-氧氮杂卓-2-或3-或5-或6-或7-基、2,5-二氢-1,4-氧氮杂卓-2-或3-或5-或6-或7-基、2,7-二氢-1,4-氧氮杂卓-2-或3-或5-或6-或7-基、4,5-二氢-1,4-氧氮杂卓-2-或3-或4-或5-或6-或7-基、4,7-二氢-1,4-氧氮杂卓-2-或3-或4-或5-或6-或7-基、6,7-二氢-1,4-氧氮杂卓-2-或3-或5-或6-或7-基、1,4-氧氮杂卓-2-或3-或5-或6-或7-基、异噻唑烷-2-或3-或4-或5-基、2,3-二氢异噻唑-2-或3-或4-或5-基、2,5-二氢异噻唑-2-或3-或4-或5-基、4,5-二氢异噻唑-3-或4-或5-基、1,3-噻唑烷-2-或3-或4-或5-基、2,3-二氢-1,3-噻唑-2-或3-或4-或5-基、2,5-二氢-1,3-噻唑-2-或4-或5-基、4,5-二氢-1,3-噻唑-2-或4-或5-基、1,3-噻嗪烷(thiazinan)-2-或3-或4-或5-或6-基、3,4-二氢-2H-1,3-噻嗪-2-或3-或4-或5-或6-基、3,6-二氢-2H-1,3-噻嗪-2-或3-或4-或5-或6-基、5,6-二氢-2H-1,3-噻嗪-2-或4-或5-或6-基、5,6-二氢-4H-1,3-噻嗪-2-或4-或5-或6-基、2H-1,3-噻嗪-2-或4-或5-或6-基、6H-1,3-噻嗪-2-或4-或5-或6-基、4H-1,3-噻嗪-2-或4-或5-或6-基。“杂环基”另外的实例为具有3个选自N、O和S的杂原子的部分氢化或完全氢化的杂环基团,例如1,4,2-二噁唑烷-2-或3-或5-基、1,4,2-二噁唑-3-或5-基、1,4,2-二噁嗪烷-2-或-3-或5-或6-基、5,6-二氢-1,4,2-二噁嗪-3-或5-或6-基、1,4,2-二噁嗪-3-或5-或6-基、1,4,2-二氧氮杂环庚-2-或3-或5-或6-或7-基、6,7-二氢-5H-1,4,2-二氧氮杂卓-3-或5-或6-或7-基、2,3-二氢-7H-1,4,2-二氧氮杂卓-2-或3-或5-或6-或7-基、2,3-二氢-5H-1,4,2-二氧氮杂卓-2-或3-或5-或6-或7-基、5H-1,4,2-二氧氮杂卓-3-或5-或6-或7-基、7H-1,4,2-二氧氮杂卓-3-或5-或6-或7-基。
当基础结构被来自基团列表或基团的一般定义的“一个或多个基团”取代时,其在每种情况下包括同时被多个相同和/或结构不同的基团取代。
对于部分饱和或完全饱和的氮杂环,其可以通过碳或通过氮与分子剩余部分连接。
用于取代的杂环基团的合适的取代基为以下具体指定的取代基,并且还包括氧基和硫代氧基。作为环碳原子上取代基的氧代基团于是为例如杂环中的羰基。因此,还优选包括内酯和内酰胺。所述氧代基团还可存在于环杂原子(例如N和S)上,所述环杂原子可以各种氧化态存在,在该情况下其在杂环中形成例如二价基团N(O)、S(O)(还简写为SO)和S(O)2(还简写为SO2)。在–N(O)-和–S(O)-基团的情况下,包括各自的两种对映异构体。
根据本发明,表达式―杂芳基‖代表杂芳族化合物,即完全不饱和的芳族杂环化合物,优选具有1至4、优选1或2个相同或不同杂原子(优选O、S或N)的5元至7元环。本发明的杂芳基为例如1H-吡咯-1-基、1H-吡咯-2-基、1H-吡咯-3-基、呋喃-2-基、呋喃-3-基、噻吩-2-基、噻吩-3-基、1H-咪唑-1-基、1H-咪唑-2-基、1H-咪唑-4-基、1H-咪唑-5-基、1H-吡唑-1-基、1H-吡唑-3-基、1H-吡唑-4-基、1H-吡唑-5-基、1H-1,2,3-三唑-1-基、1H-1,2,3-三唑-4-基、1H-1,2,3-三唑-5-基、2H-1,2,3-三唑-2-基、2H-1,2,3-三唑-4-基、1H-1,2,4-三唑-1-基、1H-1,2,4-三唑-3-基、4H-1,2,4-三唑-4-基、1,2,4-噁二唑-3-基、1,2,4-噁二唑-5-基、1,3,4-噁二唑-2-基、1,2,3-噁二唑-4-基、1,2,3-噁二唑-5-基、1,2,5-噁二唑-3-基、氮杂卓基(azepinyl)、吡啶-2-基、吡啶-3-基、吡啶-4-基、吡嗪-2-基、吡嗪-3-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、哒嗪-3-基、哒嗪-4-基、1,3,5-三嗪-2-基、1,2,4-三嗪-3-基、1,2,4-三嗪-5-基、1,2,4-三嗪-6-基、1,2,3-三嗪-4-基、1,2,3-三嗪-5-基、1,2,4-、1,3,2-、1,3,6-和1,2,6-噁嗪基-、异噁唑-3-基、异噁唑-4-基、异噁唑-5-基、1,3-噁唑-2-基、1,3-噁唑-4-基、1,3-噁唑-5-基、异噻唑-3-基、异噻唑-4-基、异噻唑-5-基、1,3-噻唑-2-基、1,3-噻唑-4-基、1,3-噻唑-5-基、氧杂卓基(oxepinyl)、硫杂卓基(thiepinyl)、1,2,4-三唑酮基(triazolonyl),和1,2,4-二氮杂卓基(diazepinyl)、2H-1,2,3,4-四唑-5-基、1H-1,2,3,4-四唑-5-基、1,2,3,4-噁三唑-5-基、1,2,3,4-噻三唑-5-基、1,2,3,5-噁三唑-4-基、1,2,3,5-噻三唑-4-基。本发明的杂芳基也可被一个或多个相同或不同的基团取代。当两个相邻碳原子为又一个芳环的部分时,此体系为稠合杂芳族体系,例如苯并稠合杂芳族化合物或多环杂芳族化合物。优选的实例为喹啉(例如喹啉-2-基、喹啉-3-基、喹啉-4-基、喹啉-5-基、喹啉-6-基、喹啉-7-基、喹啉-8-基);异喹啉(例如异喹啉-1-基、异喹啉-3-基、异喹啉-4-基、异喹啉-5-基、异喹啉-6-基、异喹啉-7-基、异喹啉-8-基);喹喔啉、喹唑啉、噌啉、1,5-萘啶、1,6-萘啶、1,7-萘啶、1,8-萘啶、2,6-萘啶、2,7-萘啶、酞嗪、吡啶并吡嗪、吡啶并嘧啶、吡啶并哒嗪、蝶啶、嘧啶并嘧啶。杂芳基的实例还包括选自以下的5元或6元苯并稠环:1H-吲哚-1-基、1H-吲哚-2-基、1H-吲哚-3-基、1H-吲哚-4-基、1H-吲哚-5-基、1H-吲哚-6-基、1H-吲哚-7-基、1-苯并呋喃-2-基、1-苯并呋喃-3-基、1-苯并呋喃-4-基、1-苯并呋喃-5-基、1-苯并呋喃-6-基、1-苯并呋喃-7-基、1-苯并噻吩-2-基、1-苯并噻吩-3-基、1-苯并噻吩-4-基、1-苯并噻吩-5-基、1-苯并噻吩-6-基、1-苯并噻吩-7-基、1H-吲唑-1-基、1H-吲唑-3-基、1H-吲唑-4-基、1H-吲唑-5-基、1H-吲唑-6-基、1H-吲唑-7-基、2H-吲唑-2-基、2H-吲唑-3-基、2H-吲唑-4-基、2H-吲唑-5-基、2H-吲唑-6-基、2H-吲唑-7-基、2H-异吲哚-2-基、2H-异吲哚-1-基、2H-异吲哚-3-基、2H-异吲哚-4-基、2H-异吲哚-5-基、2H-异吲哚-6-基、2H-异吲哚-7-基、1H-苯并咪唑-1-基、1H-苯并咪唑-2-基、1H-苯并咪唑-4-基、1H-苯并咪唑-5-基、1H-苯并咪唑-6-基、1H-苯并咪唑-7-基、1,3-苯并噁唑-2-基、1,3-苯并噁唑-4-基、1,3-苯并噁唑-5-基、1,3-苯并噁唑-6-基、1,3-苯并噁唑-7-基、1,3-苯并噻唑-2-基、1,3-苯并噻唑-4-基、1,3-苯并噻唑-5-基、1,3-苯并噻唑-6-基、1,3-苯并噻唑-7-基、1,2-苯并异噁唑-3-基、1,2-苯并异噁唑-4-基、1,2-苯并异噁唑-5-基、1,2-苯并异噁唑-6-基、1,2-苯并异噁唑-7-基、1,2-苯并异噻唑-3-基、1,2-苯并异噻唑-4-基、1,2-苯并异噻唑-5-基、1,2-苯并异噻唑-6-基、1,2-苯并异噻唑-7-基。
术语“卤素”是指例如氟、氯、溴或碘。当该术语用于基团时,“卤素”是指例如氟原子、氯原子、溴原子或碘原子。
根据本发明,“烷基”是指任选被单取代或多取代的直链或支链的开链饱和烃基基团。优选的取代基为卤素原子、烷氧基、卤代烷氧基、氰基、烷硫基、卤代烷硫基、氨基或硝基,特别优选甲氧基、甲基、氟烷基、氰基、硝基、氟、氯、溴或碘。
“卤代烷基”、“卤代烯基”和“卤代炔基”分别指被相同或不同的卤素原子部分取代或完全取代的烷基、烯基和炔基,例如单卤代烷基,例如CH2CH2Cl、CH2CH2Br、CHClCH3、CH2Cl、CH2F;全卤代烷基,例如CCl3、CClF2、CFCl2、CF2CClF2、CF2CClFCF3;多卤代烷基,例如CH2CHFCl、CF2CClFH、CF2CBrFH、CH2CF3;术语“全卤代烷基”也包括术语“全氟烷基”。
“部分氟化烷基”是指被氟单取代或多取代的直链或支链饱和烃,其中所述氟原子可以作为直链或支链烃基链的一个或多个不同的碳原子上的取代基而存在,例如CHFCH3、CH2CH2F、CH2CH2CF3、CHF2,CH2F、CHFCF2CF3。
“部分氟化卤代烷基”是指被包括至少一个氟原子的不同卤素原子取代的直链或支链饱和烃,其中任选存在的任何其他卤素原子选自氟、氯或溴、碘。所述卤素原子可以作为直链或支链烃基链的一个或多个不同的碳原子上的取代基而存在。部分氟化的卤代烷基也包括经包括至少一个氟原子的卤素完全取代的直链或支链。
卤代烷氧基为,例如,OCF3、OCHF2、OCH2F、OCF2CF3、OCH2CF3和OCH2CH2Cl;情况与卤代烯基和其他卤素取代的基团等同。
本文所提及的表述“(C1-C4)烷基”为对应于碳原子所述范围的具有1至4个碳原子的直链或支链烷基的简称,即包括甲基、乙基、1-丙基、2-丙基、1-丁基、2-丁基、2-甲基丙基或叔丁基基团。具有更大指定碳原子范围的一般烷基,例如“(C1-C6)烷基”,相应地也包括具有更多碳原子数的直链或支链烷基,即根据实例也包括具有5个和6个碳原子的烷基。
除非具体说明,优选低级碳骨架,例如对于烃基基团例如烷基、烯基和炔基,包括在结合基团中的烃基,具有1至6个碳原子,或在不饱和基团的情况下具有2至6个碳原子。烷基——包括在复合基团例如烷氧基、卤代烷基等中的烷基——为例如甲基、乙基、正丙基或异丙基、正丁基、异丁基或叔丁基或2-丁基、戊基、己基(例如正己基、异己基和1,3-二甲基丁基)、庚基(例如正庚基、1-甲基己基和1,4-二甲基戊基),烯基和炔基定义为对应于烷基的可能的不饱和基团,其中存在至少一个双键或三键。优选具有一个双键或三键的基团。
术语“烯基”还特别包括具有多于一个双键的直链或支链开链烃基,例如1,3-丁二烯基和1,4-戊二烯基,还包括具有一个或多个累积双键的丙二烯基或累积多烯基,例如丙二烯基(1,2-丙二烯基)、1,2-丁二烯基和1,2,3-戊三烯基。烯基为例如可任选被其他烷基取代的乙烯基,例如丙-1-烯-1-基、丁-1-烯-1-基、烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、1-甲基丁-3-烯-1-基和1-甲基丁-2-烯-1-基、2-甲基丙-1-烯-1-基、1-甲基丙-1-烯-1-基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基丁-3-烯-1-基或1-甲基丁-2-烯-1-基、戊烯基、2-甲基戊烯基或己烯基。
术语“炔基”还特别包括具有多于一个三键,或者具有一个或多个三键和一个或多个双键的直链或支链开链烃基,例如1,3-丁三烯基或3-戊烯-1-炔-1-基。(C2-C6)炔基为例如乙炔基、炔丙基、1-甲基丙-2-炔-1-基、2-丁炔基、2-戊炔基或2-己炔基,优选炔丙基、丁-2-炔-1-基、丁-3-炔-1-基或1-甲基丁-3-炔-1-基。
术语“环烷基”是指具有优选3至8个环碳原子的碳环饱和环体系,例如环丙基、环丁基、环戊基或环己基。在任选取代的环烷基的情况下,包括具有取代基的环状体系,还包括在环烷基上具有双键的取代基,例如亚烷基如亚甲基。在任选取代的环烷基的情况下,还包括多环脂族体系,例如二环[1.1.0]丁-1-基、二环[1.1.0]丁-2-基、二环[2.1.0]戊-1-基、二环[2.1.0]戊-2-基、二环[2.1.0]戊-5-基、二环[2.2.1]庚-2-基(降冰片基)、二环[2.2.2]辛-2-基、金刚烷-1-基和金刚烷-2-基。表述“(C3-C7)环烷基”为对应于碳原子的指定范围具有3至7个碳原子的环烷基的简称。
在取代的环烷基的情况下,还包括螺环脂族体系,例如螺[2.2]戊-1-基、螺[2.3]己-1-基、螺[2.3]己-4-基、3-螺[2.3]己-5-基。
“环烯基”是指具有优选4-8个碳原子的碳环、非芳族、部分不饱和环体系,例如1-环丁烯基、2-环丁烯基、1-环戊烯基、2-环戊烯基、3-环戊烯基或1-环己烯基、2-环己烯基、3-环己烯基、1,3-环己二烯基或1,4-环己二烯基,还包括在环烯基上具有双键的取代基,例如亚烷基如亚甲基。在任选取代的环烯基的情况下,相应适用对于取代的环烷基的解释。
术语“亚烷基”(例如包括(C1-C10)亚烷基形式)是指通过双键连接的直链或支链开链烃基基团。对于亚烷基的可能键合点仅存在于两个氢原子可被双键取代的基础结构上;基团为例如=CH2、=CH-CH3、=C(CH3)-CH3、=C(CH3)-C2H5或=C(C2H5)-C2H5。环亚烷基是通过双键连接的碳环基。
术语“甲锡烷基”代表含有锡原子的被另外取代的基团;“锗基”类似地代表含有锗原子的被另外取代的基团。“氧锆基”代表含有锆原子的被另外取代的基团。“铪氧基”代表含有铪原子的被另外取代的基团。“硼基”、“环戊硼烷基”和“环己硼烷基”代表各自含有硼原子的被另外取代的并且任选的环状基团。“铅基(Plumbanyl)”代表含有铅原子的被另外取代的基团。“汞基(Hydrargyl)”代表含有汞原子的被另外取代的基团。“铝基(Alanyl)”代表含有铝原子的被另外取代的基团。“镁基”代表含有镁原子的被另外取代的基团。“锌基(Zincyl)”代表含有锌原子的被另外取代的基团。
根据取代基的性质和连接,式(I)化合物可以立体异构体存在。式(I)包括由其具体的三维形式定义的所有可能的立体异构体,例如对映异构体、非对映异构体、Z和E异构体。例如,当存在一个或多个烯基时,可出现非对映异构体(Z和E异构体)。例如,当存在一个或多个不对称碳原子时,可出现对映异构体和非对映异构体。立体异构体可通过常规分离方法从制备中获得的混合物中获得。色谱分离可以分析规模进行以找出对映异构体过量或非对映异构体过量,或以制备规模进行以制备用于生物测试的试验样品。也可以通过使用光学活性原料和/或助剂的立体选择反应来选择性地制备立体异构体。因此本发明还涉及所有由式(I)涵盖但是没有以其具体的立体异构体形式示出的立体异构体,并且涉及其混合物。
取代的5-(环己-2-烯-1-基)戊-2,4-二烯和5-(环己-2-烯-1-基)戊-2-烯-4-炔及其类似物的合成
本发明式(I)的取代的5-(环己-2-烯-1-基)戊-2,4-二烯和5-(环己-2-烯-1-基)戊-2-烯-4-炔可通过已知方法制备。已知的和结构相关的天然植物化合物脱落酸可通过多种合成路径获得(参见Hanson等人J.Chem.Res.(S),2003,426;Constantino等人J.Org.Chem.1986,51,253;Constantino等人1989,54,681;Marsh等人Org.Biomol.Chem.2006,4,4186;WO94/15467)。一些其中记载的用于合成脱落酸骨架的方法已被优化并且被其他合成步骤所替代。所使用和检验的合成路线由市售可得的或易于制备的环己酮和炔醇酸(alkynoic acid)衍生物开始进行。
作为用于合成本发明式(I)化合物的第一个关键的中间体,制备相应地被取代的且任选经保护的8-乙炔基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇。为此,用催化剂用量的对甲基苯磺酸或溶于二氧六环和三甲氧基甲酸原酸酯混合物中的对甲基苯磺酸以及任选取代的乙二醇使相应的被另外取代的环己-2-烯-1,4-二酮转化为相应的被另外取代的1,4-二氧杂螺[4.5]癸-6-烯-8-酮(参见J.Org.Chem.2009,74,2425;Org.Lett.2001,3,1649;J.Label Compd.Radiopharm.2003,46,273)。从文献已知被适当取代的环己-2-烯-1,4-二酮的构建单元(building block)的制备(参见US5101032,Can.J.Chem.1987,65,69;Org.Lett.2006,8,3149)。还可使用其他醇和烷二醇。然后所述被另外取代的1,4-二氧杂螺[4.5]癸-6-烯-8-酮可以在合适的极性非质子溶剂(例如四氢呋喃)中与乙炔锂/乙二胺络合物反应直接转化为相应被取代的8-乙炔基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇,或在两步中在合适的极性非质子溶剂(例如四氢呋喃)中、在-78℃至0℃的温度范围内与三甲基甲硅烷基乙炔和LDA(二异丙基氨基锂)反应并且随后在极性非质子溶剂中借助合适的三烷基氟化铵(例如四丁基氟化铵)或者在极性质子溶剂中(例如甲醇)与合适的碳酸盐碱(例如碳酸钾)反应(参见J.Chem.Res.(S)2003,426)来除去三甲基甲硅烷基团以转化为相应被取代的8-乙炔基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(方案1)。
方案1
所述取代的8-乙炔基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇可在含有合适的碱(例如2,6-二甲基吡啶)的合适的极性非质子溶剂(例如二氯甲烷)中与合适的三氟甲基磺酸甲硅烷基酯试剂反应而转化为取代的(8-乙炔基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)氧基硅烷。通过使用第一步中任选被取代的丙二醇,相应的取代的9-乙炔基-1,5-二氧杂螺[5.5]十一-7-烯-9-醇可用作类似反应中的关键中间体用于下文所述的反应,以得到本发明式(I)化合物。方案1示出上述合成顺序,例如使用2,3-丁二醇和2,2-二甲基丙二醇以及三氟甲烷磺酸三乙基甲硅烷基酯。
方案2
始自合适的取代的1-乙炔基-甲基环己烯-1-醇,本发明被另外取代的(Z)-5-(环己-2-烯-1-基)戊-2-烯-4-炔酸I(a)可通过与合适的取代的碘代链烯酸或炔酸衍生物的过渡金属催化的偶联来制备(参见Chem.Res.(S),2003,426;J.Chem.Soc.,Perkin Trans.12001,47;Adv.Synth.Catal.2005,347,872),所述制备使用在胺和极性非质子溶剂的合适的溶剂混合物(例如二异丙基胺和甲苯或三乙胺和四氢呋喃)中的合适的过渡金属催化剂体系(例如二-(三苯基膦)二氯化钯、乙酸钯(II)与三苯基膦或二-(环戊-1,5-二烯基)氯化钇结合二齿配体例如2,2′-双(二苯基膦)-1,1′-联萘或1,4-双(二苯基膦)丁烷)和合适的卤化亚铜(I)(例如碘化亚铜(I)))(方案3)。
方案3
相应的(Z)-碘代链烯酸衍生物可通过例如使用合适的碱(例如正丁基锂)使端炔与氯代甲酸酯反应并且随后与碘化钠反应来制备(参见J.Fluorine Chem.1981,17,249;Org.Lett.2000,2,3407;TetrahedronLett.2008,49,794;Tetrahedron Lett.1997,38,6729)(方案2)。或者,本发明的取代的(Z)-5-(环己-2-烯-1-基)戊-2-烯-4-炔酸I(a)还可使用含有合适的碱(例如二异丙基氨基锂或正丁基锂)的合适的极性非质子溶剂(例如四氢呋喃)而使合适的取代的环己烯酮与合适的取代的(Z)-戊-2-烯-4-炔酸衍生物反应来制备(方案3)。相应的(Z)-戊-2-烯-4-炔酸衍生物可通过以下方法获得:使用含有合适的钯催化剂(例如二(三苯基膦)二氯化钯)和合适的卤化亚铜(I)(例如碘化亚铜(I))在胺和极性非质子溶剂的合适的溶剂混合物(例如二异丙胺和甲苯或三乙胺和四氢呋喃)中使三烷基甲硅烷基炔与(Z)-碘代链烯酸衍生物进行过渡金属催化偶联(参见J.Chem.Res.(S),2003,426;J.Chem.Soc.,Perkin Trans.12001,47)并且随后用合适的四烷基氟化铵处理(方案2)。取代的(Z)-碘代烯酰胺可由(Z)-碘代链烯酸通过与亚硫酰氯反应并且随后加入相应的氨基组分或通过由EDC和HOBt介导的与胺组分的偶联来得到(方案2)。
在此,EDC是指1-乙基-3-(3-二甲基氨基丙基)碳二亚胺,且在本文中HOBt是指羟基苯并三唑。
方案4
因此,本发明的取代的(Z)-5-(环己-2-烯-1-基)戊-2-烯-4-炔酸酰胺I(b)可通过两种可行的合成路线得到(方案4),a)本发明的取代的(Z)-5-(环己-2-烯-1-基)-戊-2-烯-4-炔酸I(a)通过与亚硫酰氯反应并且随后加入相关的胺组分或通过胺组分的EDC和HOBt介导的偶联而转化或b)使用合适的钯催化剂(例如二(三苯基膦)二氯化钯)和合适的卤化亚铜(I)(例如碘化亚铜(I))在胺和极性非质子溶剂的合适的溶剂混合物(例如二异丙胺和甲苯或三乙胺和四氢呋喃)中使合适的取代的1-乙炔基甲基环己烯-1-醇和(Z)-碘代烯酰胺进行过渡金属催化偶联(参见J.Chem.Res.(S),2003,426;J.Chem.Soc.,Perkin Trans.12001,47)。
本发明的取代的(E,Z)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酸衍生物I(c)可通过使用以下试剂将本发明化合物I(a)的炔基还原来制备:使用含有合适的氢化铝试剂(例如二-(2-甲氧基乙氧基)氢化铝钠)或氢化铝锂的合适的极性-非质子溶剂(例如四氢呋喃)(参见Org.Biomol.Chem.2006,4,4186;Bioorg.Med.Chem.2004,12,363-370;Tetrahedron2003,59,9091-9100;Org.Biomol.Chem.2006,4,1400-1412;Synthesis1977,561;Tetrahedron Letters1992,33,3477andTetrahedron Letters1974,1593)、使用含有硼氢化试剂(例如硼氢化钠)的合适的极性质子溶剂(例如甲醇)(参见Lett.2004,6,1785)、使用溶于乙胺和叔丁醇混合物的锂(例如Helvetica Chimica Acta1986,69,368)或使用在合适的过渡金属催化剂(例如三-(乙腈)钌-1,2,3,4,5-五甲基环戊二烯基六氟磷酸盐或三-(乙腈)钌环戊二烯基六氟磷酸盐;参见J.Am.Chem.Soc.2002,124,7622;J.Am.Chem.Soc.2005,127,17645)的存在下的合适的三烷氧基硅烷(方案5)。取决于反应条件,三键的氢化还可提供作为又一反应产物的本发明的相应的(E,E)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酸衍生物I(d)。
方案5
另一种得到本发明的取代的(E,Z)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酸衍生物I(c)的方法为在合适的极性非质子溶剂(例如四氢呋喃或二氯甲烷)中由金属氢化物或半金属氢化物介导而将上述取代的1-乙炔基甲基环己烯-1-醇转化为相应的取代的(E)-[M]-1-乙烯基甲基环己烯-1-醇(参见Org.Lett.2002,4,703;Angew.Int.Ed.2006,45,2916),
其中[M]代表,例如,其他选自锡、锗、铅、硼、铝和锆的取代金属或半金属组分(例如[M]=三正丁基甲锡烷基或双环戊二烯基氯代氧锆基)(还参见Org.Lett.2010,12,1056;Org.Lett2005,7,5191,J.Am.Chem.Soc.2010,132,10961;Tetrahedron1994,50,5189;Angew.Chem.Int.Ed.2000,39,1930)。由此获得的取代的(E)-[M]-1-乙烯基甲基环己烯-1-醇可通过在合适的溶剂(例如四氢呋喃或N,N-二甲基甲酰胺)中使用合适的过渡金属催化剂(例如二(三苯基膦)二氰化钯、四(三苯基膦)钯或二(三苯基膦)二氯化钯)与合适的取代的(Z)-卤代链烯酸衍生物偶联以得到本发明的取代的(E,Z)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酸衍生物I(c)(方案6)。
方案6
本发明的相应的取代的(E,Z)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酰胺I(e)可通过本发明式I(c)的化合物与亚硫酰氯反应并且随后加入所述氨基组分而制备或通过由EDC-和HOBt-介导的胺组分的偶联来制备(方案7)。
方案7
又一种得到本发明的取代的(E,Z)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酰胺I(e)的路线为在合适的溶剂(例如四氢呋喃或N,N-二甲基甲酰胺)中使用合适的过渡金属催化剂(例如二(三苯基膦)二氰化钯、四(三苯基膦)钯或二(三苯基膦)二氯化钯)而使取代的(E)-[M]-1-乙烯基甲基环己烯-1-醇与合适的取代的(Z)-卤代烷烯酰胺偶联来制备(方案7)。
方案8
本发明的取代的(E)-5-(环己-2-烯-1-基)戊-2-烯-4-炔酸衍生物I(f)、其相应的酰胺类似物I(g)和(E,E)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酸衍生物I(d)及其类似的酰胺I(h)可使用相应的(E)-卤代链烯酸衍生物并使用上述合成方法来制备(方案8)。
方案9
还原本发明取代的(Z)-5-(环己-2-烯-1-基)戊-2-烯-4-炔酸衍生物I(a)以得到本发明的取代的(Z,Z)-构形的5-(环己-2-烯-1-基)戊-2,4-二烯酸衍生物I(i)可在合适的极性质子溶剂(例如正丁醇)中在过渡金属催化剂如林德拉催化剂以及氢气的存在下进行(参见Tetrahedron1987,43,4107;Tetrahedron1983,39,2315;J.Org.Synth.1983,48,4436和J.Am.Chem.Soc.1984,106,2735)(方案9)。
以下给出所选择的本发明式(I)化合物的详细合成实施例。提及的实施例号对应于以下表1至表5中编号。以下段落中记载的所述化学实例的1H NMR、13C NMR和19F NMR光谱数据(对于1H NMR而言是400MHz并且对于13C NMR而言是150MHz并且对于19F NMR而言是375MHz,溶剂:CDCl3、CD3OD或d6-DMSO,内标物:四甲基硅烷δ=0.00ppm)使用Bruker仪器获得,并且所列信号具有以下给出的含义:
br=宽峰;s=单峰、d=双峰、t=三重峰、dd=双二重峰、ddd=双重双二重峰、m=多重峰、q=四重峰、quint=五重峰、sext=六重峰、sept=七重峰、dq=双四重峰、dt=双三重峰。对于化学基团使用的缩写定义如下:Me=CH3、Et=CH2CH3、t-Hex=C(CH3)2CH(CH3)2、t-Bu=C(CH3)3、n-Bu=非支链丁基、n-Pr=非支链丙基、c-Hex=环己基。在非对映异构体混合物的情况下,记录两个非对映异构体各自的显著信号或主要非对映异构体的特征信号。
合成实施例:
编号I.1-1:(2Z)-3-[(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)乙炔基]己-2-烯酸乙酯
在圆底烧瓶中于氩气下,将2,2,6-三甲基-1,4-环己二酮(15.40g,101.19mmol)溶于2,3-丁二醇(90ml)和无水甲苯(90ml)中,并且加入原甲酸三甲酯(33.21ml,303.56mmol)和对甲基苯磺酸(1.22g,7.08mmol)。将得到的反应混合物在50℃下搅拌7小时。冷却至室温后,加入水和甲苯并且用甲苯反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度)得到2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-酮(20.01g,理论值的88%)。在圆底烧瓶中于氩气下,将2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-酮(10.00g,44.58mmol)溶于无水四氢呋喃(50ml)并且将其逐滴加入至乙炔锂/乙二胺络合物(6.28g,57.96mmol,85%纯度)的无水四氢呋喃(70ml)溶液中。加入完成后,将反应混合物在室温下搅拌4小时,然后加入水并将混合物在减压下浓缩。剩余的残留物与水和二氯甲烷混合,并且用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所获粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),分离到呈无色固体的8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(10.02g,理论值的85%)。随后,在氩气下在烘过的圆底烧瓶中首先装入碘化亚铜(I)(46mg,0.24mmol)和二(三苯基膦)氯化钯(II)(126mg,0.18mmol),然后加入无水甲苯(8ml)和(2Z)-3-碘代己-2-烯酸乙酯(321mg,1.19mmol)。在室温下搅拌10分钟后逐滴加入8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(300mg,1.19mmol)的无水甲苯(2ml)溶液和二异丙胺(0.34ml,2.39mmol)。将得到的反应混合物在室温下搅拌3小时,然后加入水。用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所获粗产物的最终柱色谱纯化(使用乙酸乙酯/庚烷梯度),分离到无色油状物形式的(2Z)-3-[(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)乙炔基]己-2-烯酸乙酯(440mg,理论值的94%)。1H-NMR(400MHz,CDCl3δ,ppm)5.97(s,1H),5.49(s,1H),4.18(m,3H),3.59(m,1H),2.22(m,2H),2.02(m,1H),1.92(m,4H),1.58(m,3H),1.24(t,3H),1.20-1.12(m,12H),0.91(t,3H)。
编号I.1-2:(2Z)-3-[(1-羟基-2,6,6,-三甲基-4-氧代环己-2-烯-1-基)-乙炔基]己-2-烯酸乙酯
在氩气下在圆底烧瓶中,将(2Z)-3-[(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)乙炔基]己-2-烯酸乙酯(100mg,0.26mmol)溶于丙酮(5ml)中,并且加入5滴浓盐酸。将得到的反应溶液在室温下搅拌3小时,然后加入水。在减压下移除丙酮之后,用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),分离到无色油状物形式的(2Z)-3-[(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)乙炔基]己-2-烯酸乙酯(62mg,理论值的72%)。1H-NMR(400MHz,CDCl3δ,ppm)6.04(s,1H),5.87(s,1H),4.17(q,2H),2.99(br.s,1H,OH),2.59(d,1H),2.42(d,1H),2.23(t,2H),2.15(s,3H),1.59(m,2H),1.29(t,3H),1.25(s,3H),1.13(s,3H),0.93(t,3H)。
编号I.1-3:(2Z)-3-[(E)-2-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)乙烯基]己-2-烯酸乙酯
在氩气下在圆底烧瓶中,将(2Z)-3-[(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)乙炔基]-己-2-烯酸乙酯(340mg,0.87mmol)溶于无水二氯甲烷(4ml),并且加入三乙氧基硅烷(172mg,1.05mmol)。然后将反应溶液冷却至0℃,加入三(乙腈)环戊二烯基钌(II)六氟磷酸盐(18mg,0.04mmol)并且将混合物在室温下搅拌2小时。然后加入二乙醚,并且将反应混合物在减压下浓缩。将剩余的残留物溶于无水四氢呋喃(4ml)中,加入碘化亚铜(I)(16mg,0.09mmol)和四正丁基氟化铵(289mg,1.11mmol),将混合物在室温下搅拌4小时,然后加入水。用二氯甲烷彻底地反复萃取水相。然后将合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度)得到无色油状物形式的(2Z)-3-[(E)-2-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)乙烯基]己-2-烯酸乙酯(140mg,理论值的41%)。1H-NMR(400MHz,CDCl3δ,ppm)7.68(d,1H),6.09(d,1H),5.97(s,1H),5.48(s,1H),4.19(m,3H),3.61(m,1H),2.29(m,1H),2.22(m,2H),2.02(m,1H),1.92(m,3H),1.67(m,2H),1.62(m,1H),1.28(m,6H),1.20-1.08(m,9H),0.91(t,3H)。
编号I.1-4:(2Z)-3-[(E)-2-(1-羟基-2,6,6,-三甲基-4-氧代环己-2-烯-1-基)乙烯基]己-2-烯酸乙酯
在圆底烧瓶中于氩气下,将(2Z)-3-[(E)-2-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)乙烯基]己-2-烯酸乙酯(180mg,0.46mmol)溶于丙酮(5ml)中,并且加入3滴浓盐酸。将得到的反应溶液在室温下搅拌30分钟,然后加入水。在减压下移除丙酮,用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度),得到无色油状物形式的(2Z)-3-[(E)-2-(1-羟基-2,6,6,-三甲基-4-氧代环己-2-烯-1-基)乙烯基]己-2-烯酸乙酯(114mg,理论值的74%)。1H-NMR(400MHz,CDCl3δ,ppm)7.77(d,1H),6.15(d,1H),6.05(s,1H),5.93(s,1H),4.19(q,2H),2.96(br.s,1H,OH),2.47(d,1H),2.31(d,1H),2.24(t,2H),1.92(s,3H),1.58(m,2H),1.27(t,3H),1.24(s,3H),1.12(s,3H),0.92(t,3H)。
编号I.1-11:(2Z,4E)-3-乙基-5-{2,3,7,9,9-五甲基-8-[(三乙基甲硅烷基)氧基]-1,4-二氧杂螺[4.5]癸-6-烯-8-基}戊-2,4-二烯酸乙酯
将二环戊二烯基二甲基[(E)-2-{2,3,7,9,9-五甲基-8-[(三乙基甲硅烷基)氧基]-1,4-二氧杂螺[4.5]癸-6-烯-8-基}乙烯基]锆的无水四氢呋喃溶液冷却至0℃,并且逐滴加入已预先搅拌10分钟的二(三苯基膦)氯化钯(II)(39mg,0.06mmol),二异丁基氢化铝(16mg,0.11mmol)和(2Z)-3-碘代戊-2-烯酸乙酯(260mg,1.15mmol)的无水四氢呋喃溶液。然后直接加入氯化锌(II)(149mg,1.09mmol)的无水四氢呋喃(3ml)溶液。将得到的反应混合物在室温下搅拌7小时,然后加入水。在减压下移除四氢呋喃之后,用二氯甲烷反复萃取水相。然后将合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所获粗产物的最终柱色谱纯化(使用乙酸乙酯/庚烷梯度)分离得到无色油状物形式的(2Z,4E)-3-乙基-5-{2,3,7,9,9-五甲基-8-[(三乙基甲硅烷基)氧基]-1,4-二氧杂螺[4.5]癸-6-烯-8-基}戊-2,4-二烯酸乙酯(21mg,理论值的3%)。1H-NMR(400MHz,CDCl3δ,ppm)7.52(d,1H),6.38(d,1H),6.04(s,1H),5.39(s,1H),4.28(q,1H),4.23(m,1H),3.59(m,1H),2.29(q,2H),2.20(br.s,1H,OH),2.04(d,1H),1.93(s,3H),1.88(d,1H),1.23(m,3H),1.19-1.12(m,12H),0.92(t,3H)。
编号I.1-13:(2E)-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-3-(三氟甲基)戊-2-烯-4-炔酸乙酯
在氩气下首先将碘化亚铜(I)(46mg,0.24mmol)和二(三苯基膦)氯化钯(II)(126mg,0.18mmol)装入经加热干燥的圆底烧瓶中,加入无水甲苯(9ml)和(2Z)-4,4,4,-三氟-3-碘代丁-2-烯酸乙酯(388mg,1.32mmol)。在室温下搅拌10分钟后逐滴加入8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(300mg,1.19mmol)的无水甲苯(3ml)溶液和二异丙胺(0.34ml,2.39mmol)。将得到的反应混合物在室温下搅拌3小时,然后加入水。用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所获粗产物的最终柱色谱纯化(使用乙酸乙酯/庚烷梯度),分离得到无色油状物形式的(2E)-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(300mg,理论值的57%)。1H-NMR(400MHz,CDCl3δ,ppm)6.61(s,1H),5.56(s,1H),4.22(m,3H),3.58(m,1H),2.21(br.s,1H,OH),1.99(m,1H),1.92(m,4H),1.31(t,3H),1.22-1.13(m,12H)。
编号I.1-14:(2E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2-烯-4-炔酸乙酯
在氩气下在圆底烧瓶中,将(2E)-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(200mg,0.48mmol)溶于丙酮(5ml),并加入10%浓度的盐酸。将得到的反应溶液在室温下搅拌45分钟,然后加入水。在减压下移除丙酮后,用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度)得到无色油状物形式的(2E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(130mg,理论值的79%)。1H-NMR(400MHz,CDCl3δ,ppm)6.68(s,1H),5.90(s,1H),4.26(q,2H),2.58(m,2H),2.44(d,1H),2.15(s,3H),1.31(t,3H),1.25(s,3H),1.15(s,3H)。
编号I.1-15:(2E,4E)-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-3-(三氟甲基)戊-2,4-二烯酸乙酯
在氩气下在经加热干燥的圆底烧瓶中,将2,3,7,9,9-五甲基-8-[(E)-2-(三丁基甲锡烷基)乙烯基]-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(300mg,0.55mmol)和(2Z)-4,4,4-三氟-3-碘代丁-2-烯酸乙酯(163mg,0.55mmol)溶于无水N,N-二甲基甲酰胺(4ml),加入二氯二(乙腈)钯(II)(7mg,0.03mmol),并将混合物在室温下搅拌3小时。加入氟化钾溶液后,将反应混合物进一步在室温下搅拌过夜。然后用二乙醚彻底地反复萃取水相,然后将合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度)得到无色油状物形式的(2E,4E)-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-3-(三氟甲基)戊-2,4-二烯酸乙酯(150mg,理论值的61%)。1H-NMR(400MHz,CDCl3δ,ppm)7.47(d,1H),6.29(d,1H),6.25(s,1H),5.48(s,1H),4.26(q,2H),3.68(m,1H),3.59(m,1H),1.93(d,1H),1.83(br.m,1H,OH),1.77(d,1H),1.69(s,3H),1.32(t,3H),1.25(m,3H),1.18(m,3H),1.10(s,3H),0.91(s,3H)。
编号I.1-16:(2E,4E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2,4-二烯酸乙酯
在氩气下在圆底烧瓶中,将(2E,4E)-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-3-(三氟甲基)戊-2,4-二烯酸乙酯(150mg,0.36mmol)溶于丙酮(5ml),加入10%浓度的盐酸。将得到的反应溶液在室温下搅拌40分钟,然后加入水。在减压下移除丙酮后,用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度)得到无色油状物形式的(2E,4E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2,4-二烯酸乙酯(80mg,理论值的61%)。1H-NMR(400MHz,CDCl3δ,ppm)7.55(d,1H),6.37(d,1H),6.33(s,1H),5.97(s,1H),4.25(q,2H),2.47(d,1H),2.34(d,1H),1.92(s,3H),1.90(br.s,1H,OH),1.33(t,3H),1.11(s,3H),1.02(s,3H)。
编号I.1-23:(2E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2-烯-4-炔酸
在圆底烧瓶中,将(2E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(130mg,0.38mmol)溶于水和四氢呋喃的混合物中,然后加入氢氧化钠(38mg,0.94mmol)。将得到的反应混合物回流搅拌2小时,冷却至室温后,用盐酸水溶液酸化。用二氯甲烷彻底地反复萃取水相,然后将合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度)得到无色固体形式的(2E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2-烯-4-炔酸(40mg,理论值的32%)。1H-NMR(400MHz,CDCl3δ,ppm)10.14(br.s,1H,OH),6.70(s,1H),5.92(s,1H),2.61(d,1H),2.43(d,1H),2.30(br.s,1H,OH),2.16(s,3H),1.28(s,3H),1.13(s,3H)。
编码I.1-401:(2E)-5-[1-羟基-4-(甲氧基亚氨基)-2,6,6-三甲基环己-2-烯-1-基]-3-(三氟甲基)戊-2-烯-4-炔酸乙酯
将(2E)-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(60mg,0.17mmol)、O-甲基羟胺盐酸盐(17mg,0.21)和乙酸钠(30mg,0.37mmol)溶于乙醇和水的1:1混合物(4ml)中,然后在60℃的温度下搅拌4小时。冷却至室温后,在减压下移除乙醇并用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度)得到无色固体形式的(2E)-5-[1-羟基-4-(甲氧基亚氨基)-2,6,6-三甲基环己-2-烯-1-基]-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(40mg,理论值的58%)。1H-NMR(400MHz,CDCl3δ,ppm)6.65/6.63(s,1H),6.00/5.94(s,1H),4.27(q,2H),3.89/3.86(s,3H),2.62/2.56(br.s,1H,OH),2.46(d,1H),2.39(m,1H),2.08/2.05(s,3H),1.31(t,3H),1.18(s,3H),1.11(s,3H)。
编号I.1-521:(2E)-5-[8-羟基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂-螺[4.5]癸-6-烯-8-基]-3-(三氟甲基)戊-2-烯-4-炔酸乙酯
将乙酰基亚甲基三苯基正膦(12.91g,40.57mmol)溶解于二乙醚(30ml)和二氯甲烷(10ml)的混合物中并搅拌5分钟,然后加入1,1,1-三氟丙酮(5.00g,44.62mmol)并将混合物在室温下搅拌40小时。滤出形成的沉淀物,用二乙醚洗涤滤饼,合并的有机相在小幅减压下小心地浓缩。将如此获得的(3Z)-5,5,5-三氟-4-甲基戊-3-烯-2-酮的粗溶液不经进一步纯化用于下一个反应步骤,并溶解于甲苯(25ml)中。在加入乙酰乙酸乙酯(3.42g,26.29mmol)和叔-丁醇钾(0.88g,7.89mmol)后,将得到的反应混合物在回流条件下搅拌5小时。冷却至室温后,加入水,将混合物剧烈搅拌5分钟,然后用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度),可获得无色油状物形式的3,5-二甲基-5-(三氟甲基)环己-2-烯-1-酮(1.9g,理论值的38%)。然后将3,5-二甲基-5-(三氟甲基)环己-2-烯-1-酮(1.60g,8.33mmol)溶于无水甲苯,加入钼磷酸水合物(30mg,0.02mmol)、五水硫酸铜(II)(4mg,0.02mmol)和氧化钼(VI)(5mg,0.03mmol)。将得到的反应混合物在回流条件下引入空气搅拌4天。冷却至室温后,加入水,将混合物剧烈搅拌5分钟然后用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化,可获得无色油状物形式的2,6-二甲基-6-(三氟甲基)环己-2-烯-1,4-二酮(300mg,理论值的17%)。在氩气下,将2,6-二甲基-6-(三氟甲基)环己-2-烯-1,4-二酮(520mg,2.52mmol)溶解于2,3-丁二醇(4ml)中,加入原甲酸三甲酯(0.83ml,7.57mmol)和对-甲苯磺酸(30mg,0.18mmol)。将得到的反应混合物在50℃下搅拌6小时。冷却至室温后,加入水和甲苯并用甲苯反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤和浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),获得了2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-酮(700mg,理论值的98%)。然后在氩气下在圆底烧瓶中,将2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-酮(700mg,2.52mmol)溶于无水四氢呋喃(3ml)中并将其逐滴加入至乙炔锂/乙二胺络合物(376mg,3.27mmol,80%纯度)的无水四氢呋喃(5ml)溶液中。加入完成后,将反应混合物在室温下搅拌4小时,然后加入水并且在减压下浓缩混合物。将剩余的残留物与水和二氯甲烷混合,并且用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所获粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),分离得到呈无色固体的8-乙炔基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(550mg,理论值的68%)。随后,在氩气下在烘过的圆底烧瓶中首先装入碘化亚铜(I)(16mg,0.09mmol)和二(三苯基膦)氯化钯(II)(45mg,0.06mmol),并加入无水甲苯(3ml)和(2Z)-4,4,4-三氟-3-碘代丁-2-烯酸乙酯(126mg,0.43mmol)。在室温下搅拌10分钟后,逐滴加入8-乙炔基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(130mg,0.43mmol)的无水甲苯(1ml)的溶液和二异丙胺(0.12ml,0.85mmol)。将得到的反应混合物在室温下搅拌3小时,然后加入水。用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所获粗产物的最终柱色谱纯化(使用乙酸乙酯/庚烷梯度),分离得到无色油状物形式的(2E)-5-[8-羟基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂-螺[4.5]癸-6-烯-8-基]-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(110mg,理论值的52%)。1H-NMR(400MHz,CDCl3δ,ppm)6.65/6.63(s,1H),5.54/5.51/5.29(s,1H),4.28/3.96(q,2H),4.27/3.60(m,2H),2.62(br.s,1H,OH),2.47/2.34(d,1H),2.01/1.99(s,3H),1.98/1.91(d,1H),1.42(s,3H),1.31(t,3H),1.28(m,3H),1.17(m,3H)。
编号I.1-522:(2E)-5-[1-羟基-2,6-二甲基-4-氧-6-(三氟甲基)环己-2-烯-1-基]-3-(三氟甲基)戊-2-烯-4-炔酸乙酯
15
在氩气下在圆底烧瓶中,将(2E)-5-[8-羟基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-基]-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(110mg,0.23mmol)溶于丙酮(5ml)中,加入5滴浓盐酸。将得到的反应溶液在室温下搅拌4小时,然后加入水。在减压下移除丙酮后,用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),分离得到无色粘稠油状物形式的(2E)-5-[1-羟基-2,6-二甲基-4-氧-6-(三氟甲基)环己-2-烯-1-基]-3-(三氟甲基)戊-2-烯-4-炔酸乙酯(70mg,理论值的71%)。1H-NMR(400MHz,CDCl3δ,ppm)6.72/6.71(s,1H),5.98/5.97(s,1H),4.28/3.93(q,2H),3.28(br.s,1H,OH),3.00(d,1H),2.66(d,1H),2.21/2.18(s,3H),1.49/1.37(s,3H),1.32/1.09(t,3H)。
编号I.1-531:(2Z,4E)-3-环丙基-5-[8-羟基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-基]戊-2,4-二烯酸乙酯
在氩气下在经加热干燥的圆底烧瓶中,将2,3,7,9-四甲基-8-[(E)-2-(三丁基甲锡烷基)乙烯基]-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(150mg,0.25mmol)和(2Z)-3-环丙基-3-碘代丙烯酸乙酯(67mg,0.25mmol)溶于无水四氢呋喃(4ml)中,加入二氯二(乙腈)钯(II)(3mg,0.01mmol)并将混合物在室温下搅拌3小时。加入氟化钾溶液后,将反应混合物进一步在室温下搅拌过夜。然后用二乙醚彻底地反复萃取水相,然后将合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度),得到无色油状物形式的(2Z,4E)-3-环丙基-5-[8-羟基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-基]戊-2,4-二烯酸乙酯(40mg,理论值的36%)。1H-NMR(400MHz,CDCl3δ,ppm)7.80/7.78(d,1H),6.40/6.38(d,1H),5.62/5.60(s,1H),5.52/5.44(s,1H),4.28/3.63(m,2H),4.18(q,2H),2.52/2.41(d,1H),2.03/1.94(d,1H),2.00(br.s,1H,OH),1.72/1.69(s,3H),1.62/1.55(m,1H),1.40-1.34(m,3H),1.29-1.17(m,6H),0.92(t,3H),0.83(m,2H),0.58(m,2H)。
编号I.1-532:(2Z,4E)-3-环丙基-5-[1-羟基-2,6-二甲基-4-氧-6-(三氟甲基)环己-2-烯-1-基]戊-2,4-二烯酸乙酯
在氩气下在圆底烧瓶中,将(2Z,4E)-3-环丙基-5-[8-羟基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-基]戊-2,4-二烯酸乙酯(40mg,0.09mmol)溶于丙酮(4ml)中,加入几滴浓盐酸。将得到的反应溶液在室温下搅拌4小时,然后加入水。在减压下移除丙酮后,用二氯甲烷反复萃取水相。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),得到无色油状物形式的(2Z,4E)-3-环丙基-5-[1-羟基-2,6-二甲基-4-氧-6-(三氟甲基)环己-2-烯-1-基]戊-2,4-二烯酸乙酯(15mg,理论值的45%)。1H-NMR(400MHz,CDCl3δ,ppm)7.88(d,1H),6.37(d,1H),6.01(s,1H),5.64(s,1H),4.17(q,2H),2.92(d,1H),2.52(d,1H),2.39(br.s,1H,OH),1.98(s,3H),1.59(m,1H),1.30(t,3H),1.28(s,3H),0.88(m,2H),0.59(m,2H)。
编号I.2-69:(2Z)-3-乙基-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-N-丙基戊-2-烯-4-炔酰胺
将戊-2-炔酸(1.50g,15.29mmol)溶解于浓乙酸(15ml)中,加入细粉末的碘化钠(6.88g,45.87mmol)并将混合物在110℃的温度下搅拌3小时。冷却至室温后,加入甲基-叔丁醚(MTBE)和饱和的硫代硫酸钠溶液。水相用MTBE反复萃取,合并的有机相用硫酸镁干燥,减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),可得到无色固体形式的(2Z)-3-碘代戊-2-烯酸(2.10g,理论值的61%)。然后在氩气下在圆底烧瓶中,将(2Z)-3-碘代戊-2-烯酸(500mg,2.21mmol)溶于无水二氯甲烷,逐滴加入乙二酰氯(0.16ml,1.88mmol)。加入催化剂量的N,N-二甲基酰胺后,将反应溶液在60℃的温度下搅拌3小时,并且冷却至室温后逐滴加入正丙胺(78mg,1.33mmol)和三乙胺(0.19ml,1.33mmol)。加入水和二氯甲烷后,用二氯甲烷反复萃取水相,合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的柱色谱纯化(乙酸乙酯/庚烷梯度),可得到无色固体形式的(2Z)-3-碘-N-丙基戊-2-烯酰胺(230mg,理论值的74%)。1H-NMR(400MHz,CDCl3δ,ppm)6.27(s,1H),5.73(br.t,1H,NH),3.34(m,2H),2.65(q,2H),1.60(m,2H),1.12(t,3H),0.97(t,3H)。随后,在氩气下在烘过的圆底烧瓶中首先装入碘化亚铜(I)(30mg,0.16mmol)和二(三苯基膦)氯化钯(II)(84mg,0.12mmol),并加入无水甲苯(4ml)和(2Z)-3-碘-N-丙基戊-2-烯酰胺(214mg,0.80mmol)。在室温下搅拌10分钟后,逐滴加入8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(200mg,0.80mmol)的无水甲苯(1ml)的溶液和二异丙胺(0.22ml,1.60mmol)。将得到的反应混合物在室温下搅拌4小时,然后加入水。水相用二氯甲烷反复萃取。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所获粗产物的最终柱色谱纯化(使用乙酸乙酯/庚烷梯度),分离得到无色高度粘稠的油状物形式的(2Z)-3-乙基-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-N-丙基戊-2-烯-4-炔酰胺(280mg,理论值的85%)。1H-NMR(400MHz,CDCl3δ,ppm)6.83(br.t,1H,NH),5.99(s,1H),5.42(s,1H),4.23(m,1H),3.59(m,1H),3.29(m,2H),2.29(q,2H),2.21(br.s,1H,OH),2.02(d,1H),1.92(s,3H),1.85(d,1H),1.57(m,2H),1.23(m,3H),1.19-1.12(m,12H),0.92(t,3H)。
编号I.2-70:(2Z)-3-乙基-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-N-丙基戊-2-烯-4-炔酰胺
在氩气下在圆底烧瓶中,将(2Z)-3-乙基-5-(8-羟基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)-N-丙基戊-2-烯-4-炔酰胺(280mg,0.72mmol)溶于丙酮(4ml)中,加入10%浓度的盐酸。将得到的反应溶液在室温下搅拌50分钟,然后加入水。在减压下移除丙酮后,水相用二氯甲烷反复萃取。合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度),可得到无色固体形式的(2Z)-3-乙基-5-(1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基)-N-丙基戊-2-烯-4-炔酰胺(200mg,理论值的88%)。1H-NMR(400MHz,CDCl3δ,ppm)6.08(br.t,1H,NH),6.00(s,1H),5.87(s,1H),3.54(br.s,1H,OH),3.27(m,2H),2.53(d,1H),2.42(d,1H),2.27(q,2H),2.17(s,3H),1.56(sext,2H),1.22(s,3H),1.13(s,3H),1.11(t,3H),0.93(t,3H)。
编号II.1:2,3,7,9,9-五甲基-8-[(E)-2-(三丁基甲锡烷基)乙烯基]-1,4-二氧杂螺[4.5]癸-6-烯-8-醇
在氩气下在经加热干燥的圆底烧瓶中,首先装入四(三苯基膦)钯(0)(231mg,0.20mmol),并加入无水四氢呋喃(25ml)和8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(1.0g,3.99mmol)。在室温下搅拌5分钟后,加入三丁基氢化锡(1.29ml,4.79mmol)。将得到的反应混合物在室温下搅拌1小时,然后加入水。水相用二氯甲烷反复萃取,然后合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度),可得到无色油状物形式的2,3,7,9,9-五甲基-8-[(E)-2-(三丁基甲锡烷基)乙烯基]-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(1.50g,理论值的66%)。1H-NMR(400MHz,CDCl3δ,ppm)6.13(d,1H),5.93(d,1H),5.42(s,1H),4.22/3.63(m,2H),1.61(s,3H),1.59(d,1H),1.52(d,1H),1.49(m,6H),1.32-1.24(m,12H),1.09(s,3H),0.89(m,18H)。
编号II.25:二环戊二烯基二甲基[(E)-2-{2,3,7,9,9-五甲基-8-[(三乙基甲硅烷基)氧]-1,4-二氧杂螺[4.5]癸-6-烯-8-基}乙烯基]锆
在氩气下在圆底烧瓶中,将8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(500mg,1.99mmol)溶解于无水二氯甲烷(15ml)中,并冷却至0℃,逐滴加入二甲基吡啶(0.58ml,4.99mmol)和三乙基甲硅烷基三氟甲磺酸酯(0.68ml,2.99mmol)。将得到的反应混合物在0℃下搅拌1小时,在室温下进一步搅拌1小时,反应结束后加入水。水相用二氯甲烷反复彻底萃取,然后合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度),得到无色油状物形式的[(8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)氧](三乙基)硅烷(400mg,理论值的55%)。1H-NMR(400MHz,CDCl3δ,ppm)5.30(s,1H),4.20(m,1H),3.58(m,1H),2.48(s,1H),2.02(d,1H),1.86(s,3H),1.79(d,1H),1.22(m,3H),1.14-0.93(m,9H),0.75(m,6H),0.53(t,9H)。将经加热彻底干燥的多颈圆底烧瓶用氩气吹扫并反复抽真空,然后在恒定的氩气流下加入氢氯二茂锆(311mg,1.21mmol)和脱气的无水四氢呋喃(3ml)。将反应溶液冷却至0℃,逐滴加入[(8-乙炔基-2,3,7,9,9-五甲基-1,4-二氧杂螺[4.5]癸-6-烯-8-基)氧](三乙基)硅烷的无水四氢呋喃(2ml)溶液。将得到的反应溶液在室温下搅拌1小时,其NMR光谱分析显示全部转化成所需的二环戊二烯基二甲基[(E)-2-{2,3,7,9,9-五甲基-8-[(三乙基甲硅烷基)氧]-1,4-二氧杂螺[4.5]癸-6-烯-8-基}乙烯基]锆。1H-NMR(400MHz,CDCl3δ,ppm)7.75(m,4H),7.36(m,6H),7.27(d,1H),5.39(d,1H),5.31(s,1H),3.69(m,1H),3.62(m,1H),2.10-2.06(m,2H),1.61(s,3H),1.32-1.22(m,12H),0.89(m,6H),0.83(t,9H)。以该方式获得的合成中间体II.25不经进一步纯化就用于随后的反应中。
编号II.83:2,3,7,9-四甲基-8-[(E)-2-(三丁基甲锡烷基)乙烯基]-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-醇
在氩气下在经加热干燥的圆底烧瓶中,首先装入四(三苯基膦)钯(0)(19mg,0.02mmol),并加入无水四氢呋喃(5ml)和8-乙炔基-2,3,7,9-四甲基-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(100mg,0.33mmol)。在室温下搅拌5分钟后,加入三丁基氢化锡(0.11ml,0.39mmol)。将得到的反应混合物在55℃下搅拌1小时,冷却至室温后,加入水。水相用二氯甲烷反复彻底萃取,然后合并的有机相用硫酸镁干燥,在减压下过滤并浓缩。通过所得粗产物的最终柱色谱纯化(乙酸乙酯/庚烷梯度),
可得到无色油状物形式的2,3,7,9-四甲基-8-[(E)-2-(三丁基甲锡烷基)乙烯基]-9-(三氟甲基)-1,4-二氧杂螺[4.5]癸-6-烯-8-醇(160mg,理论值的82%)。1H-NMR(400MHz,CDCl3δ,ppm)6.33/6.31(d,1H),5.97/5.92(d,1H),5.51/5.42(s,1H),4.24/3.64(m,2H),2.46/2.35(d,1H),1.92(br.s,1H,OH),1.91/1.87(d,1H),1.64/1.62(s,3H),1.49(m,6H),1.32-1.26(m,9H),1.18(m,3H),0.89(m,18H)。
类似于以上给出的制备实施例并考虑关于制备式(I)的取代的5-(环己-2-烯-1-基)戊-2,4-二烯和5-(环己-2-烯-1-基)戊-2-烯-4-炔的通用描述,可获得表1至4中具体提及以下化合物:
表1:
表2:
表3:
表4:
所选择的表中实施例的光谱数据:
实施例编号I.1-7:
1H-NMR(400MHz,CDCl3δ,ppm)5.98(s,1H),5.51(s,1H),4.21(m,1H),4.17(q,2H),3.60(m,1H),2.48(br.s,1H,OH),2.29(q,2H),2.06(d,1H),1.93(s,3H),1.90(d,1H),1.24(m,6H),1.19-1.12(m,12H)。
实施例编号I.1-8:
1H-NMR(400MHz,CDCl3δ,ppm)6.05(s,1H),5.87(s,1H),4.19(q,2H),3.10(br.s,1H,OH),2.61(d,1H),2.42(d,1H),2.29(t,2H),2.16(s,3H),1.27(t,3H),1.25(s,3H),1.15(t,3H),1.12(s,3H)。
实施例编号I.1-9:
1H-NMR(400MHz,CDCl3δ,ppm)7.70(d,1H),6.10(d,1H),5.68(s,1H),5.51(s,1H),4.22(m,1H),4.18(q,2H),3.58(m,1H),2.29(q,2H),2.05(d,1H),1.93(s,3H),1.84(d,1H),1.31-1.22(m,6H),1.17-1.09(m,12H)。
实施例编号I.1-10:
1H-NMR(400MHz,CDCl3δ,ppm)7.79(d,1H),6.12(d,1H),5.93(s,1H),5.72(s,1H),4.17(q,2H),2.58(d,1H),2.39(d,1H),2.29(q,2H),1.92(s,3H),1.28(t,3H),1.25(s,3H),1.13(t,3H),1.11(s,3H)。
实施例编号I.1-20:
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.17(d,1H),5.96(s,1H),5.77(s,1H),2.48(d,1H),2.41(q,2H),2.29(d,1H),1.91(s,3H),1.12(t,3H),1.10(s,3H),1.04(s,3H)。
实施例编号I.1-22:
1H-NMR(400MHz,CDCl3δ,ppm)7.72(d,1H),6.18(d,1H),5.96(s,1H),5.75(s,1H),2.49(d,1H),2.32(q,2H),2.29(d,1H),1.92(s,3H),1.53(sext,2H),1.12(s,3H),1.04(s,3H),0.92(t,3H)。
实施例编号I.1-26:
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.16(d,1H),5.97(s,1H),5.74(s,1H),2.50(d,1H),2.37(m,2H),2.31(d,1H),1.93(s,3H),1.50(quint,2H),1.34(sext,2H),1.12(s,3H),1.05(s,3H),0.92(t,3H)。
实施例编号I.1-30:
1H-NMR(400MHz,CDCl3δ,ppm)7.69(d,1H),6.17(d,1H),5.96(s,1H),5.75(s,1H),2.50(d,1H),2.35(m,2H),2.32(d,1H),1.92(s,3H),1.58(m,2H),1.49(m,2H),1.30(m,4H),1.13(s,3H),1.03(s,3H),0.89(t,3H)。
实施例编号I.1-46:
1H-NMR(400MHz,CDCl3δ,ppm)7.70(d,1H),6.50(d,1H),5.97(s,1H),5.58(s,1H),2.52(d,1H),2.31(d,1H),1.94(s,3H),1.63(m,1H),1.13(s,3H),1.07(s,3H),0.90(m,2H),0.62(m,2H).
实施例编号I.1-59:
1H-NMR(400MHz,CDCl3δ,ppm)5.96(s,1H),5.89(s,1H),4.20(m,1H),4.18(q,2H),3.58(m,1H),2.52(br.s,1H,OH),2.24(m,2H),2.05(d,1H),1.93(s,3H),1.84(d,1H),1.55(quint,2H),1.31(sext,2H),1.27(t,3H),1.20(s,3H),1.16(d,6H),1.12(s,3H),0.89(t,3H)。
实施例编号I.1-60:
1H-NMR(400MHz,CDCl3δ,ppm)6.05(s,1H),5.88(s,1H),4.17(q,2H),3.03(br.s,1H,OH),2.59(d,1H),2.41(d,1H),2.27(t,2H),2.15(s,3H),1.54(quint,2H),1.33(sext,2H),1.28(t,3H),1.25(s,3H),1.13(s,3H),0.91(t,3H)。
实施例编号I.1-61:
1H-NMR(400MHz,CDCl3δ,ppm)7.67(d,1H),6.09(d,1H),5.66(s,1H),5.43(s,1H),4.21(m,1H),4.17(q,2H),3.59(m,1H),2.30(m,2H),1.93(d,1H),1.69(s,3H),1.66(d,1H),1.49(m,2H),1.31-1.23(m,11H),1.11(s,3H),1.09(s,3H),0.89(t,3H)。
实施例编号I.1-62:
1H-NMR(400MHz,CDCl3δ,ppm)7.78(d,1H),6.16(d,1H),5.94(s,1H),5.72(s,1H),4.18(q,2H),2.47(d,1H),2.32(m,2H),2.28(d,1H),1.93(s,3H),1.46(quint,2H),1.33(sext,2H),1.29(t,3H),1.11(s,3H),1.02(s,3H),0.90(t,3H)。
实施例编号I.1-65:
1H-NMR(400MHz,CDCl3δ,ppm)5.97(s,1H),5.89(s,1H),4.20(m,1H),4.18(q,2H),3.59(m,1H),2.53(br.s,1H,OH),2.22(m,2H),2.04(d,1H),1.92(s,3H),1.83(d,1H),1.57(quint,2H),1.30-1.22(m,10H),1.17(d,6H),1.12(s,3H),0.89(t,3H)。
实施例编号I.1-66:
1H-NMR(400MHz,CDCl3δ,ppm)6.04(s,1H),5.87(s,1H),4.19(q,2H),3.01(br.s,1H,OH),2.61(d,1H),2.42(d,1H),2.26(t,2H),2.16(s,3H),1.56(quint,2H),1.29(m,7H),1.24(s,3H),1.13(s,3H),0.89(t,3H)。
实施例编号I.1-67:
1H-NMR(400MHz,CDCl3δ,ppm)7.69(d,1H),6.08(d,1H),5.67(s,1H),5.42(s,1H),4.20(m,1H),4.16(q,2H),3.59(m,1H),2.32(m,2H),1.92(d,1H),1.67(s,3H),1.65(d,1H),1.48(m,2H),1.32-1.23(m,9H),1.17(m,2H),1.10(s,3H),1.07(s,3H),0.91(m,5H)。
实施例编号I.1-68:
1H-NMR(400MHz,CDCl3δ,ppm)7.75(d,1H),6.12(d,1H),5.93(s,1H),5.73(s,1H),4.17(q,2H),2.45(d,1H),2.31(m,2H),2.29(d,1H),1.92(s,3H),1.49(m,2H),1.30(m,7H),1.11(s,3H),1.01(s,3H),0.87(t,3H)。
实施例编号I.1-71:
1H-NMR(400MHz,CDCl3δ,ppm)5.96(s,1H),5.39(s,1H),4.20(m,1H),4.18(q,2H),3.60(m,1H),2.58(br.s,1H,OH),2.24(m,2H),2.04(d,1H),1.92(s,3H),1.83(d,1H),1.57(m,2H),1.30-1.22(m,16H),1.18(d,6H),1.11(s,3H),0.87(t,3H)。
实施例编号I.1-72:
1H-NMR(400MHz,CDCl3δ,ppm)6.04(s,1H),5.87(s,1H),4.18(q,2H),3.08(br.s,1H,OH),2.59(d,1H),2.41(d,1H),2.27(t,2H),2.15(s,3H),1.53(m,2H),1.29(m,12H),1.13(s,3H),0.88(t,3H)。
实施例编号I.1-73:
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.10(d,1H),5.66(s,1H),5.43(s,1H),4.21(m,1H),4.18(q,2H),3.58(m,1H),2.31(m,2H),1.94(d,1H),1.76(d,1H),1.68(s,3H),1.48(m,2H),1.31-1.22(m,18H),1.18(m,2H),1.11(s,3H),0.92(t,3H),0.87(t,3H)。
实施例编号I.1-74:
1H-NMR(400MHz,CDCl3δ,ppm)7.76(d,1H),6.13(d,1H),5.94(s,1H),5.72(s,1H),4.18(q,2H),2.47(d,1H),2.33(m,2H),2.31(d,1H),1.92(s,3H),1.48(m,2H),1.34-1.25(m,9H),1.11(s,3H),1.02(s,3H),0.88(t,3H)。
实施例编号I.1-77:
1H-NMR(400MHz,CDCl3δ,ppm)5.96(s,1H),5.39(s,1H),4.21(m,1H),4.17(q,2H),3.58(m,1H),2.55(br.s,1H,OH),2.23(m,2H),2.03(d,1H),1.93(s,3H),1.86(d,1H),1.55(m,2H),1.30-1.22(m,14H),1.15(m,6H),1.12(s,3H),0.88(t,3H)。
实施例编号I.1-78:
1H-NMR(400MHz,CDCl3δ,ppm)6.03(s,1H),5.86(s,1H),4.17(q,2H),3.11(br.s,1H,OH),2.61(d,1H),2.43(d,1H),2.26(t,2H),2.15(s,3H),1.55(m,2H),1.29(m,16H),1.13(s,3H),0.87(t,3H)。
实施例编号I.1-79:
1H-NMR(400MHz,CDCl3δ,ppm)7.68(d,1H),6.09(d,1H),5.66(s,1H),5.43(s,1H),4.21(m,1H),4.18(q,2H),3.58(m,1H),2.31(m,2H),1.93(d,1H),1.74(d,1H),1.67(s,3H),1.48(m,2H),1.31-1.21(m,17H),1.14(m,2H),1.10(s,3H),0.92(t,3H),0.88(t,3H)。
实施例编号I.1-80:
1H-NMR(400MHz,CDCl3δ,ppm)7.77(d,1H),6.12(d,1H),5.94(s,1H),5.71(s,1H),4.18(q,2H),2.45(d,1H),2.31(m,2H),2.29(d,1H),1.93(s,3H),1.48(m,2H),1.33-1.23(m,13H),1.11(s,3H),1.03(s,3H),0.87(t,3H)。
实施例编号I.1-83:
1H-NMR(400MHz,CDCl3δ,ppm)6.00(s,1H),5.52/5.41(s,1H),4.21/3.59(m,2H),4.17(q,2H),2.55/2.38(br.s,1H,OH),2.50(m,1H),2.05(d,1H),1.95/1.92(s,3H),1.88(d,1H),1.30-1.22(m,9H),1.19(s,3H),1.14(m,9H)。
实施例编号I.1-84:
1H-NMR(400MHz,CDCl3δ,ppm)6.06(s,1H),5.87(s,1H),4.17(q,2H),3.09(br.s,1H,OH),2.60(d,1H),2.52(sept,1H),2.43(d,1H),2.16(s,3H),1.28(t,3H),1.26(s,3H),1.14(s,3H),1.12(d,6H)。
实施例编号I.1-85:
1H-NMR(400MHz,CDCl3δ,ppm)7.66/7.65(d,1H),6.10(d,1H),5.66/5.65(s,1H),5.55/5.43(s,1H),4.23/3.59(m,2H),4.18(q,2H),2.82(m,1H),2.09/1.98(d,1H),1.82/1.73(d,1H),1.69/1.68(s,3H),1.28(m,6H),1.19-1.10(m,12H),0.93(m,3H)。
实施例编号I.1-86:
1H-NMR(400MHz,CDCl3δ,ppm)7.70(d,1H),6.15(d,1H),5.94(s,1H),5.73(s,1H),4.18(q,2H),2.80(sept,1H),2.50(d,1H),2.30(d,1H),1.99(br.s,1H,OH),1.94(s,3H),1.29(t,3H),1.15-1.10(m,9H),1.03(s,3H)。
实施例编号I.1-89:
1H-NMR(400MHz,CDCl3δ,ppm)6.03(s,1H),5.58/5.40(s,1H),4.19(q,2H),4.05/3.59(m,2H),2.72(br.s,1H,OH),2.07/2.05(d,1H),1.96/1.94(s,3H),1.88/1.86(d,1H),1.29-1.22(m,6H),1.19-1.10(m,15H),1.03(s,3H)。
实施例编号I.1-90:
1H-NMR(400MHz,CDCl3δ,ppm)6.09(s,1H),5.87(s,1H),4.19(q,2H),3.22(br.s,1H,OH),2.59(d,1H),2.43(d,1H),2.16(s,3H),1.29(t,3H),1.26(s,3H),1.17(s,9H),1.13(s,3H)。
实施例编号I.1-91:
1H-NMR(400MHz,CDCl3δ,ppm)6.42/6.38(d,1H),5.72/5.67(s,1H),5.62(d,1H),5.53/5.41(s,1H),4.22/3.58(m,2H),4.11(q,2H),2.08/1.99(d,1H),1.92/1.84(d,1H),1.74/1.72(s,3H),1.24(m,6H),1.19-1.10(m,15H),0.94(m,3H)。
实施例编号I.1-92:
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.45(d,1H),5.93(s,1H),5.76(s,1H),4.10(q,2H),2.52(d,1H),2.25(d,1H),2.01(br.s,1H,OH),2.00(s,3H),1.26(t,3H),1.11(s,9H),1.10(s,3H),1.06(s,3H)。
实施例编号I.1-113:
1H-NMR(400MHz,CDCl3δ,ppm)6.11(s,1H),5.39(s,1H),4.20(m,1H),4.16(q,2H),3.59(m,1H),2.58(br.s,1H,OH),2.01(d,1H),1.91(s,3H),1.86(d,1H),1.62(m,1H),1.24(t,3H),1.21(m,3H),1.13(m,6H),1.11(m,3H),0.88(m,2H),0.81(m,2H)。
实施例编号I.1-114:
1H-NMR(400MHz,CDCl3δ,ppm)6.18(s,1H),5.86(s,1H),4.18(q,2H),3.08(br.s,1H,OH),2.54(d,1H),2.42(d,1H),2.14(s,3H),1.67(m,1H),1.28(t,3H),1.24(s,3H),1.11(s,3H),0.83(m,4H)。
实施例编号I.1-115:
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.43(d,1H),5.51(s,1H),5.44(s,1H),4.21(m,1H),4.17(q,2H),3.58(m,1H),1.98(d,1H),1.83(d,1H),1.71(s,3H),1.63(m,1H),1.25-1.21(m,6H),1.13(m,3H),1.09(m,3H),0.94(m,3H),0.82(m,2H),0.56(m,2H)。
实施例编号I.1-116:
1H-NMR(400MHz,CDCl3δ,ppm)7.81(d,1H),6.52(d,1H),5.95(s,1H),5.59(s,1H),4.17(q,2H),2.51(d,1H),2.32(d,1H),1.94(s,3H),1.61(m,1H),1.28(t,3H),1.12(s,3H),1.03(s,3H),0.85(m,2H),0.58(m,2H)。
实施例编号I.1-121:
1H-NMR(400MHz,CDCl3δ,ppm)6.02(s,1H),5.51/5.39(s,1H),4.21/3.59(m,2H),4.18(q,2H),2.69/2.63(m,1H),2.55/2.53(br.s,1H,OH),2.04(d,1H),1.94/1.92(s,3H),1.89-1.77(m,3H),1.71(m,2H),1.62(m,4H),1.28-1.22(m,9H),1.18(s,3H),1.14(m,3H)。
实施例编号I.1-122:
1H-NMR(400MHz,CDCl3δ,ppm)6.08(s,1H),5.87(s,1H),4.19(q,2H),3.15(br.s,1H,OH),2.66(quint,1H),2.58(d,1H),2.42(d,1H),2.16(s,3H),1.87(m,2H),1.69(m,2H),1.59(m,4H),1.27(t,3H),1.25(s,3H),1.13(s,3H)。
实施例编号I.1-123:
1H-NMR(400MHz,CDCl3δ,ppm)7.71/7.70(d,1H),6.10(d,1H),5.69/5.68(s,1H),5.55/5.43(s,1H),4.22/3.59(m,2H),4.18(q,2H),2.91(m,1H),2.08/1.96(d,1H),1.91-1.82(m,3H),1.69/1.68(s,3H),1.68-1.60(m,4H),1.51-1.43(m,2H),1.28(m,6H),1.19-1.09(m,6H),0.92(m,3H)。
实施例编号I.1-124:
1H-NMR(400MHz,CDCl3δ,ppm)7.76(d,1H),6.16(d,1H),5.94(s,1H),5.75(s,1H),4.18(q,2H),2.89(pent,1H),2.49(d,1H),2.30(d,1H),2.00(br.s,1H,OH),1.94(s,3H),1.90(m,2H),1.72(m,2H),1.66(m,2H),1.49(m,2H),1.29(t,3H),1.11(s,3H),1.03(s,3H)。
实施例编号I.1-125:
1H-NMR(400MHz,CDCl3δ,ppm)5.97(s,1H),5.39(s,1H),4.21(m,1H),4.19(q,2H),3.60(m,1H),2.56(br,s,1H,OH),2.15(m,1H),2.03(d,1H),1.94(s,3H),1.90(d,1H),1.78(m,4H),1.69(m,2H),1.37(m,2H),1.30-1.21(m,6H),1.20-1.12(m,5H),1.10(m,3H),0.88(m,3H)。
实施例编号I.1-126:
1H-NMR(400MHz,CDCl3δ,ppm)6.04(s,1H),5.87(s,1H),4.18(q,2H),3.07(br.s,1H,OH),2.61(d,1H),2.44(d,1H),2.18(m,1H),2.16(s,3H),1.79(m,3H),1.70(m,1H),1.32-1.24(m,12H),1.13(s,3H)。
实施例编号I.1-127:
1H-NMR(400MHz,CDCl3δ,ppm)7.58(d,1H),6.06(d,1H),5.63(s,1H),5.45(s,1H),4.21(m,1H),4.18(q,2H),3.59(m,1H),2.41(m,1H),1.94(d,1H),1.81-1.73(m,5H),1.70(s,3H),1.64(m,2H),1.32-1.21(m,8H),1.20-1.12(m,5H),1.10(m,3H),0.92(m,3H)。
实施例编号I.1-128:
1H-NMR(400MHz,CDCl3δ,ppm)7.67(d,1H),6.11(d,1H),5.94(s,1H),5.70(s,1H),4.15(q,2H),2.48(d,1H),2.38(m,1H),2.29(d,1H),1.95(s,3H),1.83-1.74(m,4H),1.37-1.19(m,6H),1.28(t,3H),1.12(s,3H),1.03(s,3H)。
实施例编号I.1-141:
1H-NMR(400MHz,CDCl3δ,ppm)5.98(s,1H),5.43/5.40(s,1H),4.16/3.59(m,2H),3.72(s,3H),2.50(br.s,1H,OH),2.29(q,2H),2.08(d,1H),1.96/1.95(s,3H),1.84(d,1H),1.24(m,6H),1.20(s,3H),1.14(m,9H)。
实施例编号I.1-142:
1H-NMR(400MHz,CDCl3δ,ppm)6.06(s,1H),5.87(s,1H),3.72(s,3H),2.99(br.s,1H,OH),2.61(d,1H),2.42(d,1H),2.30(q,2H),2.16(s,3H),1.26(s,3H),1.14(t,3H),1.13(s,3H)。
实施例编号I.1-143:
1H-NMR(400MHz,CDCl3δ,ppm)7.70(d,1H),6.11(d,1H),5.68/5.67(s,1H),5.56/5.43(s,1H),4.23/3.59(m,2H),3.71(s,3H),2.38(q,2H),2.08/1.97(d,1H),1.83/1.73(d,1H),1.69/1.68(s,3H),1.26(m,3H),1.17(m,3H),1.11(m,6H),0.91(t,3H)。
实施例编号I.1-144:
1H-NMR(400MHz,CDCl3δ,ppm)7.80(d,1H),6.18(d,1H),5.95(s,1H),5.75(s,1H),3.71(s,3H),2.82(br.s,1H,OH),2.49(d,1H),2.38(q,2H),2.31(d,1H),1.93(s,3H),1.13(t,3H),1.11(s,3H),1.02(s,3H)。
实施例编号I.1-147:
1H-NMR(400MHz,CDCl3δ,ppm)7.73/7.71(d,1H),6.12(d,1H),5.93/5.90(s,1H),5.56/5.42(s,1H),4.17/3.59(m,2H),3.71(s,3H),2.29(m,2H),2.08/1.99(d,1H),1.84(d,1H),1.81/1.78(s,3H),1.53(m,2H),1.26(m,6H),1.11(m,6H),0.96(m,3H)。
实施例编号I.1-148:
1H-NMR(400MHz,CDCl3δ,ppm)7.78(d,1H),6.16(d,1H),5.95(s,1H),5.72(s,1H),3.71(s,3H),2.48(d,1H),2.30(m,3H),1.97(br.s,1H,OH),1.93(s,3H),1.53(m,2H),1.11(s,3H),1.02(s,3H),0.96(t,3H)。
实施例编号I.1-230:
1H-NMR(400MHz,CDCl3δ,ppm)6.07(s,1H),5.87(s,1H),4.08(t,2H),3.02(br.s,1H,OH),2.60(d,1H),2.45(q,2H),2.42(d,1H),2.16(s,3H),1.68(sext,2H),1.25(s,3H),1.15(t,3H),1.10(s,3H),0.95(t,3H)。
实施例编号I.1-231:
1H-NMR(400MHz,CDCl3δ,ppm)7.73/7.71(d,1H),6.11(d,1H),5.69/5.68(s,1H),5.56/5.43(s,1H),4.25/3.59(m,2H),4.09(t,2H),2.37(q,2H),2.08/1.96(d,1H),1.83/1.74(d,1H),1.69(m,5H),1.26(m,6H),1.18-1.10(m,6H),0.97(m,3H),0.92(m,3H)。
实施例编号I.1-232:
1H-NMR(400MHz,CDCl3δ,ppm)7.81(d,1H),6.17(d,1H),5.94(s,1H),5.75(s,1H),4.08(t,2H),2.49(d,1H),2.39(q,2H),2.32(d,1H),1.95(br.s,1H,OH),1.93(s,3H),1.69(sext,2H),1.13(m,6H),1.02(s,3H),0.97(t,3H)。
实施例编号I.1-279:
1H-NMR(400MHz,CDCl3δ,ppm)7.71/7.69(d,1H),6.12(d,1H),5.68/5.67(s,1H),5.56/5.42(s,1H),4.21/3.59(m,2H),4.13(t,2H),2.31(m,2H),2.08/1.96(d,1H),1.83/1.74(d,1H),1.81-1.69(m,5H),1.50(m,2H),1.26(m,6H),1.18-1.10(m,9H),0.97(m,3H)。
实施例编号I.1-280:
1H-NMR(400MHz,CDCl3δ,ppm)7.80(d,1H),6.15(d,1H),5.94(s,1H),5.73(s,1H),4.11(t,2H),2.49(d,1H),2.30(m,3H),1.98(br.s,1H,OH),1.95(s,3H),1.85(m,2H),1.55(m,2H),1.13(s,3H),1.02(m,6H),0.97(t,3H)。
实施例编号I.1-317:
1H-NMR(400MHz,CDCl3δ,ppm)5.97(s,1H),5.40(s,1H),4.21(m,1H),4.14(t,2H),3.58(m,1H),2.57(br.s,1H,OH),2.23(t,2H),2.04(d,1H),1.93(s,3H),1.88(d,1H),1.68(m,1H),1.53(quint,2H),1.29(m,4H),1.23(t,3H),1.19(m,6H),1.14(m,5H),0.90(d,6H),0.78(t,3H)。
实施例编号I.1-318:
1H-NMR(400MHz,CDCl3δ,ppm)6.04(s,1H),5.87(s,1H),4.15(t,2H),3.04(br.s,1H,OH),2.59(d,1H),2.41(d,1H),2.26(t,2H),2.15(s,3H),1.69(m,1H),1.56(m,2H),1.54(m,2H),1.29(m,4H),1.24(s,3H),1.12(s,3H),0.93(d,6H),0.88(t,3H)。
实施例编号I.1-319:
1H-NMR(400MHz,CDCl3δ,ppm)7.69(d,1H),6.09(d,1H),5.66(s,1H),5.43(s,1H),4.21(m,1H),4.13(t,2H),3.58(m,1H),2.30(m,2H),1.94(d,1H),1.74(d,1H),1.69(s,3H),1.58(s,3H),1.49(quint,2H),1.29(m,4H),1.26(m,4H),1.18(m,3H),1.09(m,4H),0.91(m,9H),0.88(m,3H)。
实施例编号I.1-320:
1H-NMR(400MHz,CDCl3δ,ppm)7.80(d,1H),6.15(d,1H),5.94(s,1H),5.72(s,1H),4.16(t,2H),2.47(d,1H),2.32(d,1H),2.29(m,2H),1.93(s,3H),1.72(m,1H),1.54(m,2H),1.49(m,2H),1.31(m,4H),1.12(s,3H),1.03(s,3H),0.91(d,6H),0.88(t,3H)。
实施例编号I.1-394:
1H-NMR(400MHz,CDCl3δ,ppm)7.68(d,1H),6.46(d,1H),5.52(s,1H),5.44(s,1H),4.22(m,1H),3.58(m,1H),2.45(br.s,1H,OH),1.94(d,1H),1.91(m,1H),1.85(d,1H),1.68(s,3H),1.31(m,3H),1.22(m,3H),1.18(m,3H),1.10(m,3H),0.90(m,2H),0.59(m,2H)。
实施例编号I.1-395:
1H-NMR(400MHz,CDCl3δ,ppm)7.63(d,1H),6.14(d,1H),5.68(s,1H),5.44(s,1H),4.22(m,1H),3.58(m,1H),2.34(m,2H),1.93(d,1H),1.76(d,1H),1.68-1.63(m,5H),1.49(m,2H),1.34-1.22(m,11H),1.18-1.13(m,2H),1.10(m,3H),0.90(m,6H)。
实施例编号I.1-396:
1H-NMR(400MHz,CDCl3δ,ppm)7.66(d,1H),6.12(d,1H),5.68(s,1H),5.42(s,1H),4.21(m,1H),3.59(m,1H),2.32(m,2H),1.92(d,1H),1.82(d,1H),1.67(s,3H),1.61(m,2H),1.33(m,2H),1.28(m,6H),1.14(m,3H),1.10(m,3H),0.91(t,3H)。
实施例编号I.1-403
1H-NMR(400MHz,CDCl3δ,ppm)6.67/6.64(s,1H),6.63/6.01(s,1H),4.28(q,2H),4.11(m,2H),2.62/2.56(br.s,1H,OH),2.44-2.35(m,2H),2.08/2.05(s,3H),1.30(t,3H),1.27(t,3H),1.18(s,3H),1.10(s,3H)。
实施例编号I.1-413
1H-NMR(400MHz,CDCl3δ,ppm)6.59/6.58(s,1H),6.02/5.95(s,1H),4.19(q,2H),3.89/3.86(s,3H),2.74/2.66(br.s,1H,OH),2.47(d,1H),2.33(m,1H),2.29(q,2H),2.08/2.05(s,3H),1.28(t,3H),1.19(s,3H),1.12(t,3H),1.10(s,3H)。
实施例编号I.1-414
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.64/5.99(s,1H),6.11/6.09(d,1H),5.71/5.70(s,1H),4.18(q,2H),3.90/3.87(s,3H),2.77/2.73(br.s,1H,OH),2.42(d,1H),2.38(m,2H),2.22(m,1H),1.84/1.81(s,3H),1.29(t,3H),1.11(m,3H),1.02(s,3H),0.99(s,3H)。
实施例编号I.1-415
1H-NMR(400MHz,CDCl3δ,ppm)6.62/6.02(s,1H),6.01/5.97(s,1H),4.18(q,2H),4.11(m,2H),2.71/2.62(br.s,1H,OH),2.47(d,1H),2.35(m,1H),2.29(q,2H),2.09/2.05(s,3H),1.28(m,6H),1.20(s,3H),1.14(t,3H),1.08(s,3H)。
实施例编号I.1-416
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.67/5.98(s,1H),6.12/6.08(d,1H),5.71/5.69(s,1H),4.18(q,2H),4.12(m,2H),2.80/2.76(br.s,1H,OH),2.43(d,1H),2.38(q,2H),2.23(m,1H),1.83/1.81(s,3H),1.29(m,6H),1.12(m,3H),1.02(s,3H),0.99(s,3H)。
实施例编号I.1-439:
1H-NMR(400MHz,CDCl3δ,ppm)7.61/7.58(d,1H),6.11/6.10(d,1H),5.68/5.65(s,1H),5.56/5.43(s,1H),4.22/3.58(m,2H),2.59(m,1H),2.08/1.93(d,1H),1.92/1.91(br.s,1H,OH),1.83/1.76(d,1H),1.69/1.68(s,3H),1.43(m,1H),1.34(m,1H),1.23(m,6H),1.14-1.10(m,9H),0.89(m,3H)。
实施例编号I.1-440:
1H-NMR(400MHz,CDCl3δ,ppm)7.62/7.61(d,1H),6.15(d,1H),5.97(s,1H),5.72(s,1H),2.58(m,1H),2.49(d,1H),2.31(d,1H),1.98(br.s,1H,OH),1.93(s,3H),1.54(m,1H),1.47(m,1H),1.12(m,6H),1.04(m,3H),0.89(m,3H)。
实施例编号I.1-441:
1H-NMR(400MHz,CDCl3δ,ppm)5.98(s,1H),5.51/5.40(s,1H),4.21/3.59(m,2H),3.72(s,3H),2.53(br.s,1H,OH),2.23/2.00(m,1H),2.04(m,1H),1.96/1.94(s,3H),1.91-1.84(m,1H),1.42(m,2H),1.23(m,4H),1.19(s,3H),1.14-1.11(m,9H),0.89/0.82(t,3H)。
实施例编号I.1-442:
1H-NMR(400MHz,CDCl3δ,ppm)6.05(s,1H),5.87(s,1H),3.72(s,3H),3.06(br.s,1H,OH),2.58(d,1H),2.43(d,1H),2.28(m,1H),2.16(s,3H),1.51(m,1H),1.53(m,1H),1.26(s,3H),1.13(s,3H),1.12/1.10(d,3H),0.85(t,3H)。
实施例编号I.1-443:
1H-NMR(400MHz,CDCl3δ,ppm)7.62/7.60(d,1H),6.10/6.07(d,1H),5.64(s,1H),5.56/5.43(s,1H),4.23/3.58(m,2H),3.71(s,3H),2.59(m,1H),2.08/1.93(d,1H),1.92(br.s,1H,OH),1.84/1.78(d,1H),1.69/1.68(s,3H),1.51(m,1H),1.42(m,1H),1.26(m,6H),1.14-1.10(m,6H),0.92-0.85(m,6H)。
实施例编号I.1-444:
1H-NMR(400MHz,CDCl3δ,ppm)7.71/7.66(d,1H),6.14(d,1H),5.95(s,1H),5.70(s,1H),3.71(s,3H),2.56(m,1H),2.49(d,1H),2.31(d,1H),1.94(s,3H),1.54(m,1H),1.43(m,1H),1.11(s,3H),1.09(s,3H),1.03(m,3H),0.88(m,3H)。
实施例编号I.1-457:
1H-NMR(400MHz,CDCl3δ,ppm)6.43/5.98(s,1H),5.51/5.39(s,1H),4.22/3.59(m,2H),4.19(q,2H),2.51(br.s,1H,OH),2.33/2.16(m,1H),2.02(m,1H),1.94/1.91/1.89(s,3H),1.88-1.78(m,1H),1.53(m,2H),1.29-1.21(m,12H),1.20-1.17(m,3H),1.15-1.08(m,5H),0.89/0.82(t,3H)。
实施例编号I.1-458:
1H-NMR(400MHz,CDCl3δ,ppm)6.04(s,1H),5.87(s,1H),4.19(q,2H),3.11(br.s,1H,OH),2.58(d,1H),2.43(d,1H),2.38(m,1H),2.16(s,3H),1.49(m,1H),1.35(m,1H),1.31-1.23(m,8H),1.13(s,3H),1.11/1.09(d,3H),0.88(t,3H)。
实施例编号I.1-459:
1H-NMR(400MHz,CDCl3δ,ppm)7.68/7.63(d,1H),6.10/6.08(d,1H),5.64/5.61(s,1H),5.56/5.43(s,1H),4.22/3.58(m,2H),4.18(q,2H),2.68(m,1H),2.08/1.97(d,1H),1.93/1.91(br.s,1H,OH),1.84/1.77(d,1H),1.69/1.68(s,3H),1.49(m,1H),1.37(m,1H),1.28(m,9H),1.18(m,2H),1.12(m,6H),0.93(m,3H),0.89(m,3H)。
实施例编号I.1-460:
1H-NMR(400MHz,CDCl3δ,ppm)7.71/7.68(d,1H),6.14/6.11(d,1H),5.95/5.93(s,1H),5.70(s,1H),4.18(q,2H),2.62(m,1H),2.48(d,1H),2.30(d,1H),1.98(br.s,1H,OH),1.95/1.90(s,3H),1.49(m,1H),1.38(m,1H),1.30(m,5H),1.11(m,6H),1.02(s,3H),0.88(m,3H)。
实施例编号I.1-489:
1H-NMR(400MHz,CDCl3δ,ppm)6.01(s,1H),5.52/5.41(s,1H),4.24/3.63(m,2H),4.19(q,2H),2.95(br.s,1H,OH),2.58/2.48(d,1H),2.38/1.92(d,1H),2.29(q,2H),2.02/2.00(s,3H),1.43(s,3H),1.28-1.24(m,6H),1.18-1.04(m,6H)。
实施例编号I.1-490:
1H-NMR(400MHz,CDCl3δ,ppm)6.09(s,1H),5.94(s,1H),4.19(q,2H),3.67(br.s,1H,OH),2.97(d,1H),2.70(d,1H),2.32(q,2H),2.21(s,3H),1.50(s,3H),1.29(t,3H),1.15(t,3H)。
实施例编号I.1-497:
1H-NMR(400MHz,CDCl3δ,ppm)6.00(s,1H),5.50/5.47/5.41(s,1H),4.24/3.63(m,2H),4.18(q,2H),2.86/2.80(br.s,1H,OH),2.48/2.37(d,1H),2.23(t,2H),2.01/1.92(d,1H),2.00/1.99(s,3H),1.60(m,2H),1.42(s,3H),1.28(m,6H),1.18(m,3H),0.92(t,3H)。
实施例编号I.1-498:
1H-NMR(400MHz,CDCl3δ,ppm)6.08(s,1H),5.94(s,1H),4.19(q,2H),3.41(br.s,1H,OH),2.96(d,1H),2.70(d,1H),2.25(t,2H),2.20(s,3H),1.58(m,2H),1.50(s,3H),1.28(t,3H),0.94(t,3H)。
实施例编号I.1-505:
1H-NMR(400MHz,CDCl3δ,ppm)6.02(s,1H),5.50/5.47/5.41(s,1H),4.24/3.64(m,2H),4.17(q,2H),2.89/2.87(br.s,1H,OH),2.52(sept,2H),2.49/2.38(d,1H),2.03/1.91(d,1H),2.02/2.00(s,3H),1.43(s,3H),1.28(m,6H),1.18(m,3H),1.14(m,6H)。
实施例编号I.1-506:
1H-NMR(400MHz,CDCl3δ,ppm)6.10(s,1H),5.94(s,1H),4.18(q,2H),3.41(br.s,1H,OH),2.97(d,1H),2.70(d,1H),2.54(sept,2H),2.21(s,3H),1.51(s,3H),1.28(t,3H),1.15(d,6H)。
实施例编号I.1-529:
1H-NMR(400MHz,CDCl3δ,ppm)6.15(s,1H),5.49/5.46/5.40(s,1H),4.24/3.64(m,2H),4.17(q,2H),2.97/2.92(br.s,1H,OH),2.47/2.36(d,1H),2.02/1.91(d,1H),1.99/1.97(s,3H),1.67(m,1H),1.40(s,3H),1.27(m,6H),1.18(m,3H),0.84(m,4H)。
实施例编号I.1-530:
1H-NMR(400MHz,CDCl3δ,ppm)6.21(s,1H),5.93(s,1H),4.18(q,2H),3.50(br.s,1H,OH),2.96(d,1H),2.66(d,1H),2.18(s,3H),1.69(m,1H),1.48(s,3H),1.28(t,3H),0.90(m,2H),0.82(m,2H)。
实施例编号I.1-549
1H-NMR(400MHz,CDCl3δ,ppm)6.70/5.97(s,1H),6.02/6.01(s,1H),4.20(q,2H),2.93/2.88(br.s,1H,OH),2.59/2.49(br.s,1H,OH),2.43(d,1H),2.36(m,1H),2.29(q,2H),2.11/2.06(s,3H),1.28(t,3H),1.22(s,3H),1.16(t,3H),1.10(s,3H)。
实施例编号I.1-551
1H-NMR(400MHz,CDCl3δ,ppm)6.74/6.01(s,1H),6.65/5.64(s,1H),4.28(q,2H),2.70/2.60(br.s,1H,OH),2.58/2.49(br.s,1H,OH),2.42(d,1H),2.39(m,1H),2.11/2.06(s,3H),1.31/1.26(t,3H),1.19(s,3H),1.13/1.10(s,3H)。
实施例编号I.1-553:
1H-NMR(400MHz,CDCl3δ,ppm)5.98(s,1H),5.52/5.39(s,1H),4.21/3.59(m,2H),4.19(q,2H),2.76(br.s,1H,OH),2.02(m,1H),1.93/1.89(s,3H),1.79(d,1H),1.29(t,3H),1.27-1.21(m,6H),1.20-1.08(m,14H),0.77(t,3H)。
实施例编号I.1-554:
1H-NMR(400MHz,CDCl3δ,ppm)6.05(s,1H),5.87(s,1H),4.20(q,2H),3.27(br.s,1H,OH),2.57(d,1H),2.42(d,1H),2.16(s,3H),1.52(q,2H),1.29(t,1H),1.23(s,6H),1.12(s,3H),1.11(s,3H),0.77(t,3H)。
实施例编号I.1-555:
1H-NMR(400MHz,CDCl3δ,ppm)7.60/7.57(d,1H),6.18/6.16(d,1H),5.99/5.68(s,1H),5.56/5.44(s,1H),4.23/3.58(m,2H),4.11(q,2H),2.08/1.96(d,1H),1.91/1.86(d,1H),1.64/1.62(s,3H),1.49(m,2H),1.28(m,9H),1.19-1.09(m,9H),0.93-0.88(m,6H)。
实施例编号I.1-556:
1H-NMR(400MHz,CDCl3δ,ppm)7.71(d,1H),6.00(d,1H),5.93(s,1H),5.38(s,1H),4.10(q,2H),2.48(d,1H),2.27(d,1H),1.99(br.s,1H,OH),1.90(s,3H),1.43(q,2H),1.28(t,3H),1.11(s,6H),1.09(s,3H),1.04(s,3H),0.78(t,3H)。
实施例编号I.1-560:
1H-NMR(400MHz,CDCl3δ,ppm)7.80(d,1H),6.18(d,1H),5.94(s,1H),5.74(s,1H),4.15(t,2H),3.59(t,2H),2.49(d,1H),2.39(q,2H),2.32(d,1H),2.01(br.s,1H,OH),1.93(s,3H),1.89(m,2H),1.84(m,2H),1.14(t,3H),1.13(s,3H),1.02(s,3H)。
实施例编号I.1-564:
1H-NMR(400MHz,CDCl3δ,ppm)7.79(d,1H),6.17(d,1H),5.94(s,1H),5.72(s,1H),4.15(t,2H),3.60(t,2H),2.48(d,1H),2.31(m,1H),1.98(br.s,1H,OH),1.93(s,3H),1.88(m,2H),1.84(m,2H),1.53(m,2H),1.11(s,3H),1.02(s,3H),0.98(t,3H)。
实施例编号I.1-565:
1H-NMR(400MHz,CDCl3δ,ppm)7.60/7.57(d,1H),5.73(d,1H),5.69/5.68(s,1H),5.66/5.43(s,1H),4.19/3.58(m,2H),2.59(m,1H),1.98/1.95(d,1H),1.91/1.88(d,1H),1.72/1.71(s,3H),1.44(m,2H),1.26(m,6H),1.12-1.09(m,9H),0.96(s,3H),0.88(m,3H)。
实施例编号I.1-566:
1H-NMR(400MHz,CDCl3δ,ppm)7.61(d,1H),6.43(d,1H),5.94(s,1H),5.73(s,1H),2.53(d,1H),2.27(d,1H),1.97(s,3H),1.44(q,2H),1.10(s,3H),1.09(s,6H),1.05(s,3H),0.78(t,3H)。
实施例编号I.2-5:
1H-NMR(400MHz,CDCl3δ,ppm)6.83(br.s,1H,NH),6.02(s,1H),5.42(s,1H),4.21(m,1H),3.58(m,1H),2.87(d,3H),2.28(q,2H),2.17(br.s,1H,OH),2.00(d,1H),1.91(s,3H),1.83(d,1H),1.24(m,6H),1.19-1.12(m,9H)。
实施例编号I.2-6:
1H-NMR(400MHz,CDCl3δ,ppm)6.15(br.s,1H,NH),6.01(s,1H),5.88(s,1H),3.44(br.s,1H,OH),2.86(d,3H),2.53(d,1H),2.42(d,1H),2.28(q,2H),2.16(s,3H),1.25(s,3H),1.13(s,3H),1.11(t,3H)。
实施例编号I.2-13:
1H-NMR(400MHz,CDCl3δ,ppm)6.68(br.s,1H,NH),5.97(s,1H),5.42(s,1H),4.21(m,1H),4.16(m,1H),3.59(m,1H),2.27(q,2H),2.14(br.s,1H,OH),1.99(d,1H),1.93(s,3H),1.88(d,1H),1.23(m,3H),1.18(m,6H),1.15-1.12(m,12H)。
实施例编号I.2-14:
1H-NMR(400MHz,CDCl3δ,ppm)5.96(s,1H),5.88(s,1H),5.84(br.s,1H,NH),4.15(m,1H),3.29(br.s,1H,OH),2.55(d,1H),2.42(d,1H),2.26(q,2H),2.16(s,3H),1.25(s,3H),1.18(d,6H),1.12(s,3H),1.10(t,3H)。
实施例编号I.2-17:
1H-NMR(400MHz,CDCl3δ,ppm)6.97(br.s,1H,NH),5.99(s,1H),5.44(s,1H),4.21(m,1H),3.59(m,1H),2.79(m,1H),2.28(q,2H),2.16(br.s,1H,OH),2.01(d,1H),1.92(s,3H),1.86(d,1H),1.23(m,3H),1.18(m,3H),1.14-1.10(m,9H),0.78(m,2H),0.59(m,2H)。
实施例编号I.2-18:
1H-NMR(400MHz,CDCl3δ,ppm)6.31(br.s,1H,NH),5.97(s,1H),5.88(s,1H),3.24(br.s,1H,OH),2.78(m,1H),2.52(d,1H),2.43(d,1H),2.26(q,2H),2.16(s,3H),1.25(s,3H),1.12(s,3H),1.10(t,3H),0.81(m,2H),0.53(m,2H)。
实施例编号I.2-25:
1H-NMR(400MHz,CDCl3δ,ppm)6.74(br.s,1H,NH),5.99(s,1H),5.41(s,1H),4.20(m,1H),3.58(m,1H),3.04(d,2H),2.29(q,2H),2.16(s,1H),2.12(br.s,1H,OH),1.94(d,1H),1.90(s,3H),1.87(d,1H),1.23(m,3H),1.12(m,6H),1.09(m,6H)。
实施例编号I.2-41:
1H-NMR(400MHz,CDCl3δ,ppm)8.74(d,2H),8.08(br.t,1H,NH),7.22(t,1H),6.09(s,1H),5.42(s,1H),4.88(d,2H),4.21(m,1H),3.59(m,1H),2.32(q,2H),2.01(d,1H),1.89(s,3H),1.87(d,1H),1.22(m,6H),1.17-1.12(m,9H)。
实施例编号I.3-1:
1H-NMR(400MHz,CDCl3δ,ppm)6.38(d,1H),6.21(d,1H),5.92(s,1H),5.84(s,1H),2.45(d,1H),2.28(d,1H),1.95(q,2H),1.90(s,3H),1.10(s,3H),1.08(t,3H),1.03(s,3H)。
实施例编号II.19:
1H-NMR(400MHz,CDCl3δ,ppm)5.42(d,1H),5.31(d,1H),5.30(s,1H),3.60(m,2H),2.08(d,1H),1.90(s,3H),1.82(d,1H),1.24(t,9H),1.19(q,6H),1.14(d,6H),1.11(s,3H),1.09(s,3H)。
本发明还提供使用一种选自式(I)的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔的化合物,以及这些本发明式(I)的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔与下面定义的活性农用化学化合物的任何所需的混合物,用于提高植物对非生物胁迫因素(优选干旱胁迫)的抗性,以及用于促进植物生长和/或提高植物产量的用途。
本发明还提供用于处理植物的喷雾溶液,所述喷雾溶液包含对于增强植物对非生物胁迫因素的抗性而言有效量的至少一种选自式(I)的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔的化合物。相关的非生物胁迫条件可包括例如热、干旱、冷和干燥胁迫(由干燥和/或缺水造成的胁迫)、渗透胁迫、水涝、高土壤盐度、高矿物暴露、臭氧条件、强光条件、有限的氮营养素利用度、有限的磷营养素利用度。
在一个实施方案中,例如,可将本发明的化合物——即式(I)的合适的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔——通过喷雾施加至待处理的合适的植物或植物部位。本发明的式(I)化合物或其盐的使用剂量优选为0.00005至3kg/ha,更优选为0.0001至2kg/ha,特别优选为0.0005至1kg/ha,特别优选0.001至0.25kg/ha。
在本发明的上下文中,术语“对非生物胁迫的抗性”应理解为对植物的多种益处。这些有益性质表现为例如以下的改进的植物特性:改善表面积和深度方面的根系生长、增加匍匐茎或分蘖枝的形成、使匍匐茎和分蘖枝更强和更多产、改善芽生长、提高抗倒伏性、提高芽基部直径、增大叶面积、提高营养物质和成分(例如碳水化合物、脂肪、油、蛋白质、维生素、矿物质、精油、染料、纤维)的收率、使纤维品质更好、开花更早、增加花的数量、降低有毒产物如真菌毒素的含量、降低残余物或任意种类不利成分的含量、或者提高可消化性、提高采收物的储存稳定性、提高对不利温度的耐受性、提高对干旱和干燥的耐受性、以及提高对水涝造成的缺氧的耐受性、提高对土壤和水中高含盐量的耐受性、增强对臭氧胁迫的耐受性、改善与除草剂和其他作物处理组合物的相容性、改善吸水和光合作用性能、有利的植物性质例如加速成熟、成熟更均匀、对有益动物的吸引更强、改善授粉、或本领域技术人员熟知的其他优势。
更具体而言,根据本发明使用一种或多种式(I)化合物在喷雾施加至植物和植物部位时表现出所述优势。式(I)的合适的取代的5-(环己-2-烯-1-基)戊-2,4-二烯和5-(环己-2-烯-1-基)戊-2-烯-4-炔与包括杀昆虫剂、引诱剂、杀螨剂、杀真菌剂、杀线虫剂、除草剂、生长调节剂、安全剂、影响植物成熟的物质、以及杀细菌剂的物质的结合物也可用于防治本发明上下文的植物病害。另外,式(I)的合适的取代的5-(环己-2-烯-1-基)戊-2,4-二烯和5-(环己-2-烯-1-基)戊-2-烯-4-炔与基因修饰栽培品种的结合使用以提高对非生物胁迫的耐受性同样是可行的。
如所已知的,上面所提及的对植物的各种益处可部分结合,并且可使用通用术语描述它们。所述术语为例如以下的名称:植物毒性效应、对胁迫因素的抗性、更少的植物胁迫、植物健康(health)、健康的植物、植物健康度(fitness)、植物健康状况(wellness)、植物概念、茁壮效应、胁迫防护、保护性防护、作物健康、作物健康特性、作物健康产品、作物健康管理、作物健康疗法、植物健康、植物健康特性、植物健康产品、植物健康管理、植物健康疗法、绿化效应或返青效应(regreening effect)、鲜度或本领域技术人员熟知的其他术语。
在本发明的上下文中,对非生物胁迫抗性的良好效应应理解为以下含义,但不受其限制:
·出苗率提高至少为通常3%,特别是高于5%,更优选高于10%,
·产量提高至少为通常3%,特别是高于5%,更优选高于10%,
·根发育提高至少为通常3%,特别是高于5%,更优选高于10%,
·芽尺寸增加至少为通常3%,特别是高于5%,更优选高于10%,
·叶面积增加至少为通常3%,特别是高于5%,更优选高于10%,
·光合作用提高至少为通常3%,特别是高于5%,更优选高于10%,和/或
·花形成提高至少为通常3%,特别是高于5%,更优选高于10%,
并且所述效应可以单独出现,或者以两个或多个效应的任意结合出现。
本发明还提供用于处理植物的喷雾溶液,所述喷雾溶液包含对于增强植物对非生物胁迫因素的抗性而言有效量的至少一种式(I)的化合物。所述喷雾溶液可包含其他常规组分,例如溶剂、制剂助剂,特别是水。其他组分可包括下文进一步描述的活性农用化学化合物。
本发明还提供相应的喷雾溶液用于提高植物对非生物胁迫因素的抗性的用途。下面的说明同时适用于本发明的式(I)化合物本身和相应的喷雾溶液的用途。
根据本发明,另外发现将式(I)化合物与至少一种下文进一步定义的肥料结合施用至植物或其环境是可行的。
根据本发明,可与上文详细说明的式(I)化合物一起使用的肥料通常为有机和无机含氮化合物,例如尿素、尿素/甲醛缩合产物、氨基酸、铵盐和硝酸铵、钾盐(优选氯化钾、硫酸钾、硝酸钾)、磷酸盐和/或亚磷酸盐(优选钾盐和铵盐)。在本文中,特别应提及NPK肥料,即含氮、磷和钾的肥料;硝酸铵钙,即,还包含钙的肥料;或硝硫酸铵(式为(NH4)2SO4NH4NO3)、磷酸铵和硫酸铵。这些肥料对于本领域内技术人员而言是公知常识;还参见例如Ullmann's Encyclopedia ofIndustrial Chemistry,第5版,A10卷,第323页至431页,Verlagsgesellschaft,Weinheim,1987。
所述肥料还可包含微量营养物(优选钙、硫、硼、锰、镁、铁、硼、铜、锌、钼和钴)的盐和植物激素(例如维生素B1和吲哚-3-乙酸)或它们的混合物。根据本发明使用的肥料还可包含其他盐,例如磷酸一铵(MAP)、磷酸二铵(DAP)、硫酸钾、氯化钾、硫酸镁。二级营养素或微量元素的合适用量为0.5至5重量%,基于总肥料计。其他可能的成分有作物保护组合物、杀虫剂或杀菌剂、生长调节剂或其混合物。这在下文将进一步详细说明。
所述肥料可以例如粉末剂(powder)、颗粒剂、小球剂(prill)或密实剂(compactate)形式使用。然而,所述肥料也可溶于含水介质中以液体形式使用。在该情况下,稀释的氨水溶液也可用作氮肥。其他可能的肥料成分记载于例如Ullmann's Encyclopedia of Industrial Chemistry,第5版,1987,A10卷,第363页至401页、DE-A4128828、DE-A1905834和DE-A19631764。在本发明的上下文中,肥料的常规组成可采用单一肥料和/或复合肥料的形式,例如由氮、钾或磷组成,其可以在宽的范围内变化。一般而言,氮含量为1至30重量%(优选5至20重量%),钾含量为1至20重量%(优选3至15重量%)且磷含量为1至20重量%(优选3至10重量%)是有利的。微量元素含量通常在ppm范围内,优选为1至1000ppm范围。
在本发明的上下文中,肥料和式(I)化合物可同时施用。然而,也可先施用肥料然后施用式(I)的化合物,或先施用式(I)的化合物然后施用肥料。然而,在不同时施用式(I)的化合物与肥料的情况下,本发明上下文的施用以功能关系进行,特别是在通常24小时内,优选18小时,更优选12小时,特别是6小时,更特别是4小时,甚至更特别是2小时的时间内。在本发明非常具体的实施方案中,本发明式(I)的化合物和肥料在小于1小时,优选小于30分钟,更优选小于15分钟的时间内施用。
优选将式(I)化合物用于经济植物、观赏植物、草皮类,在公共区域和家用区域作为观赏植物的常用树木、和林业树木。林业树木包括用于生产木材、纤维素、纸和由树木的部位制成的产品的树木。在此使用的术语“经济植物”是指如下的作物植物,其用于获得食物、动物饲料、燃料或用于工业目的。
所述经济植物包括例如以下类型的植物:黑小麦、硬质小麦(硬小麦)、草皮、藤本植物、谷物(例如小麦、大麦、黑麦、燕麦、稻、玉米和粟/高粱);甜菜例如糖用甜菜和饲料甜菜;水果例如仁果、核果和无核水果,例如苹果、梨、李、桃、杏、樱桃和浆果,例如草莓、覆盆子、黑莓;豆类,例如菜豆、小扁豆、豌豆和大豆;油料作物,例如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻油植物、可可豆和花生;葫芦科植物,例如南瓜(pumpkin/squash))、黄瓜和甜瓜;纤维植物,例如棉花、亚麻、大麻和黄麻;柑橘类水果,例如橙、柠檬、葡萄柚和柑橘;蔬菜,例如菠菜、莴苣、芦笋、甘蓝类、胡萝卜、洋葱、番茄、马铃薯和甜椒;樟科,例如鳄梨、樟属、樟脑,或者植物例如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄藤、葎草、香蕉、橡胶植物和观赏植物,例如花、灌木、落叶树和针叶树。这些列举并非限制。
下列植物被认为是特别适于应用本发明方法的目标作物:燕麦、黑麦、黑小麦、硬质小麦、棉花、茄子、草皮、仁果、核果、无核水果、玉米、小麦、大麦、黄瓜、烟草、藤本植物、稻、谷物、梨、胡椒、菜豆、大豆、油菜、番茄、甜椒、甜瓜、甘蓝、马铃薯和苹果。
根据本发明方法可以改进的树的实例包括:冷杉属(Abies sp.)、桉树属(Eucalyptus sp.)、云杉属(Picea sp.)、松属(Pinus sp.)、七叶树属(Aesculus sp.)、悬铃木属(Platanus sp.)、椴树属(Tilia sp.)、槭树属(Acer sp.)、铁杉属(Tsuga sp.)、白蜡树属(Fraxinus sp.)、花楸属(Sorbus sp.)、桦木属(Betula sp.)、山楂树属(Crataegus sp.)、榆树属(Ulmus sp.)、橡树属(Quercus sp.)、山毛榉属(Fagus sp.)、柳属(Salix sp.)、杨属(Populus sp.)。
可以根据本发明方法改进的优选的树木包括:七叶树属树种:欧洲七叶树(A.hippocastanum)、小花七叶树(A.pariflora)、红花七叶树(A.carnea);悬铃木属树种:英国梧桐(P.acerifolia)、美国梧桐(P.occidentali)、P.racemosa;云杉属树种:云杉(P.abies);松属树种:辐射松(P.radiate)、西黄松(P.ponderosa)、小干松(P.contorta)、P.sylvestre、湿地松(P.elliottii)、松白松(P.montecola)、白皮松(P.albicaulis)、美国赤松(P.resinosa)、长叶松(P.palustris)、火炬松(P.taeda)、柔枝松(P.flexilis)、黑材松(P.jeffregi)、短叶松(P.baksiana)、白松(P.strobes);桉树属树种:巨桉(E.grandis)、蓝桉(E.globulus)、E.camadentis、亮果桉(E.nitens)、斜叶桉(E.obliqua)、王桉(E.regnans)、弹丸桉(E.pilularus)。
根据本发明方法改进的特别优选的树木包括:松属树种:辐射松(P.radiate)、西黄松(P.ponderosa)、小干松(P.contorta)、P.sylvestre、白松(P.strobes);桉树属树种:巨桉(E.grandis)、蓝桉(E.globulus)、E.camadentis。
根据本发明方法改进的特别优选的树木包括:七叶树(horsechestnut)、悬铃木科(Platanaceae)、椴树(linden tree)、枫树(mapletree)。
本发明还可应用于任何草皮草类,包括冷季草皮草(cool-seasonturfgrass)和暖季草皮草(warm-season turfgrass)。冷季草皮草的实例为蓝草(早熟禾属(Poa spp.)),例如肯塔基蓝草(Kentucky bluegrass)(草地早熟禾(Poa pratensis L.))、粗茎苗系草(Poa trivialis L.)、加拿大蓝草(Poa compressa L.)、一年生蓝草(Poa annua L.)、高地早熟禾(Poa glaucantha Gaudin)、林地早熟禾(Poa nemoralis L.)和鳞茎早熟禾(Poa bulbosa L.);高羊茅属(Agrostis spp.)例如匍匐剪股颖(Agrostis palustris Huds.)、细纪翦股颖(Agrostis tenuis Sibth.)、绒毛翦股颖(Agrostis canina L.)、剪股颖属草类(Agrostis spp.包括细弱剪股颖(Agrostis tenius Sibth.)、普通剪股颖(Agrostis canina L.)和Agrostis palustris Hud)和小糠草(Agrostis alba L.);
羊茅属(Festuca spp.)例如例如紫羊茅(Festuca rubra L.spp.rubra)、邱氏羊茅(Festuca rubra L.)、紫羊茅(Festuca rubra commutataGaud.)、羊茅(Festuca ovina L.)、长叶羊茅(Festuca longifolia Thuill.)、牛毛草(Festucu capillata Lam.)、苇状羊茅(Festuca arundinaceaSchreb.)、高狐茅(Festuca elantor L.);
黑麦草属(Lolium L.),例如一年生黑麦草(Lolium multiflorumLam.)、多年生黑麦草(Lolium perenne L.)和多花黑麦草(Loliummultiflorum Lam.);
和冰草属(wheatgrasses(Agropyron spp.)),例如冰草(FairwayWheatgrass(Agropyron cristatum(L.)Gaertn.))、扁穗冰草(crestedwheatgrass(Agropyron desertorum(Fisch.)Schult.))和蓝茎冰草(Western Wheatgrass(Agropyron smithii Rydb.))。
其他冷季草皮草的实例为海滩草(Ammophila breviligulata Fern.)、无芒雀麦(Bromus inermis Leyss.)、香蒲属例如猫尾草(Phleumpratense L.)、sand cattail(Phleum subulatum L.)、野茅(Dactylisglomerata L.)、碱茅(Puccinellia distans(L.)Parl.)和洋狗尾草(Cynosurus cristatus L.)。
暖季草皮草的实例有:百慕达草(Bermudagrasses(Cynodon L.C.Rich))、结缕草属(Zoysia grasses(Zoysia spp.Willd.))、森特钝叶草(St.Augustine grass(Stenotaphrum secundatum Walt Kuntze))、假俭草(Centipede grass(Eremochloa ophiuroides Munro Hack.))、地毯草属(Carpet grass(Axonopus affinis Chase))、百喜草(Bahia grass(Paspalumnotatum Flugge.))、铺地狼尾草(Kikuyu grass(Pennisetum clandestinumHochst.ex Chiov.))、野牛草(Buffalo grass(Buchloe dactyloides(Nutt.)Engelm.))、格兰马草(Bouteloua gracilis(H.B.K.)Lag.ex Griffiths)、海雀稗(Seashore paspalum(Paspalum vaginatum swartz))和垂穗草(Bouteloua curtipendula(Michx.)Torr.)。根据本发明,通常优选使用冷季草皮草。特别优选为蓝草、翦股颖属和小糠草、羊茅和黑麦草。尤其优选翦股颖属。
特别优选使用本发明式(I)的化合物处理单独市售的植物或常用的植物栽培品种的植物。植物栽培品种应理解为是指具有新性质(“特征”)并且通过常规育种、通过突变或借助于重组DNA技术而获得的植物。因此作物植物可为可通过常规育种和最优化方法或通过生物技术和基因工程方法或这些方法的结合而获得的植物,包括转基因植物并且包括可被植物育种者权利保护和不受植物育种者权利保护的植物品种。
因此本发明的处理方法还可用于处理基因修饰有机体(GMO)例如植物或种子。基因修饰植物(或转基因植物)为异源基因(heterologousgene)被稳定地整合至基因组中的植物。表述“异源基因”主要是指提供或组装于植物外的基因,并且当它们被引入至核基因组、叶绿体基因组或hypochondrial基因组时,通过表达所关注的蛋白质或多肽或下调或关闭其他存在于植物中的基因(使用例如反义技术、共抑制技术或RNAi技术[RNA干涉]),而给予这些被转变的植物新的或改进的农艺性质或其他性质。存在于基因组中的异源基因也被称作转基因。通过其在植物基因组中的具体位置所定义的转基因称作转化株系或转基因株系(transgenic event)。
优选用本发明式(I)化合物处理的植物和植物品种包括所有具有赋予这些植物特别有利的、有用的特征的基因材料的所有植物(不论是通过育种方法和/或通过生物技术方法获得)。
也可用本发明式(I)化合物处理的植物和植物品种为对一种或多种非生物胁迫因素具有抗性的植物。非生物胁迫条件可以包括例如,热、干旱、冷和干旱胁迫、渗透胁迫、水涝、增加的土壤盐度、增加的矿物暴露、臭氧条件暴露、强光条件暴露、有限的氮营养素利用度、有限的磷营养素利用度或荫避。
还可用本发明式(I)化合物处理的植物和植物品种是以提高的产量特性为特征的那些植物。所述植物的产量提高可以是以下因素的结果:例如,改善的植物生理机能、生长和发育,例如水分利用率、水分保留率、改进的氮利用、提高的碳素同化作用、增强的光合作用、提高的发芽率和加速成熟。产量还可通过改进的植物构造来实现(在胁迫和非胁迫条件下),包括提早开花、对杂交种子生产的开花控制、秧苗活力、植株大小、节间数和节间距、根系生长、种子大小、果实大小、荚果大小、荚数或穗数、每个荚或穗的种子数量、种子质量、增强种子填充、减少种子散播、减少荚裂开以及抗倒伏。其他产量性状包括种子成分,如碳水化合物含量、蛋白质含量、油含量和组成、营养价值、减少抗营养化合物、改善的可加工性和更好的贮存稳定性。
可用本发明式(I)化合物处理的植物为已经表达出杂交特性和或杂交效应的杂交植物,杂交通常导致较高的产量、更加茁壮、更加健康和对生物和非生物胁迫因素的更好的抗性。这种植物通常是将一种先天自交雄性不育亲系(母本)与另一种先天自交雄性能育亲系(父本)杂交而制得。杂交种子通常收获自雄性不育植物然后出售给种植者。雄性不育植物有时(例如在玉米中)可以通过去雄(即机械地移除雄性生殖器官或雄花)而制得,但是,更通常地,雄性不育性是植物基因组中遗传定子的结果。在这种情况下,尤其是当从杂交植物上收获的种子是所需产品时,通常有用的是确保充分恢复含有负责雄性不育性的遗传决定因子的杂交植物的雄性能育性。这可以通过保证父本具有适当的育性恢复基因而达到,该基因能够恢复含有造成负责雄性不育性的遗传定子的杂交植物的雄性可育性。造成雄性不育的遗传定子可以位于细胞质中。细胞质雄性不育(CMS)例如芸苔属种(Brassica species)的细胞质雄性不育已被描述(WO92/005251、WO95/009910、WO98/27806、WO05/002324、WO06/021972和US6,229,072)。然而,负责雄性不育的遗传定子也可以位于细胞核基因组中。雄性不育植物也可通过植物生物技术方法例如基因工程获得。一种特别有用的获取雄性不育植物的方法记载于WO89/10396中,其中,例如,在雄蕊中的绒毡层细胞中选择性地表达一种核糖核酸酶例如芽孢杆菌RNA酶(barnase)。可以通过在绒毡层细胞中表达核糖核酸酶抑制剂如芽孢杆菌RNA酶抑制剂(bastar)来恢复能育性(例如WO91/002069)。
同样可以用本发明式(I)化合物处理的植物或植物品种(通过植物生物技术方法例如基因工程获得)为耐除草剂植物,即对一种或多种给定的除草剂耐受的植物。这些植物可以通过遗传转化或通过选择含有赋予该除草剂耐受性的突变的植物而获得。
耐除草剂的植物为例如,耐草甘膦植物,即对除草剂草甘膦或其盐具有耐受性的植物。例如,耐草甘膦植物可以通过用编码5-烯醇丙酮莽草酸-3-磷酸合酶(EPSPS)的基因转化植物获得。所述EPSPS基因的实例有鼠伤寒沙门氏菌(Salmonella typhimurium)的AroA基因(突变体CT7)(Comai等人,Science(1983),221,370-371)、细菌土壤杆菌属(Agrobacterium sp.)的CP4基因(Barry等,Curr.Topics PlantPhysiol.(1992),7,139-145)、编码矮牵牛(petunia)EPSPS的基因(Shah等人,Science(1986),233,478-481)、编码番茄EPSPS的基因(Gasser等人,J.Biol.Chem.(1988),263,4280-4289)或编码穇属(Eleusine)EPSPS的基因(WO01/66704)。所述基因也可以为突变的EPSPS,例如EP-A0837944、WO00/066746、WO00/066747或WO02/026995中所记载的。耐草甘膦植物还可以通过表达编码草甘膦氧化还原酶的基因而获得,如US5,776,760和US5,463,175所记载的。耐草甘膦植物还可以通过表达编码草甘膦乙酰基转移酶的基因而获得,描述于例如WO02/036782、WO03/092360、WO05/012515和WO07/024782。耐草甘膦植物还可以通过选择含有上述基因的天然突变体的植物而获得,例如WO01/024615或WO03/013226所记载的。
其他耐除草剂植物为例如对抑制谷氨酰胺合酶的除草剂例如双丙氨膦(bialaphos)、草丁膦(phosphinothricin)或草铵膦(glufosinate)具有耐受性的植物。该植物可以通过表达一种使除草剂解毒的酶或通过表达一种对抑制作用具有抗性的突变谷氨酰胺合酶而获得。一种这类有效的解毒酶为例如编码草丁膦乙酰转移酶的酶(例如链霉菌(Streptomyces)的bar蛋白或pat蛋白)。表达异源草丁膦乙酰基转移酶的植物记载于例如US5,561,236、US5,648,477、US5,646,024、US5,273,894、US5,637,489、US5,276,268、US5,739,082、US5,908,810和US7,112,665。
其他耐除草剂植物还可为对抑制羟苯基丙酮酸双加氧酶(HPPD)的除草剂有耐受性的植物。羟苯基丙酮酸双加氧酶为催化将对羟苯基丙酮酸盐(HPP)转化为尿黑酸的反应的酶。对HPPD抑制剂具有耐受性的植物可以用编码天然存在的抗性HPPD酶的基因,或用编码突变HPPD酶的基因进行转化,如WO96/038567、WO99/024585和WO99/024586所述。对HPPD抑制剂的耐受性也可通过用编码某些尽管天然HPPD酶被HPPD抑制剂抑制也能够形成尿黑酸的酶的基因对植物进行转化而获得。这种植物和基因在WO99/034008和WO2002/36787中有描述。植物对HPPD抑制剂的耐受性除用编码HPPD耐受酶的基因外,也可通过用编码预苯酸脱氢酶的基因转化植物而改进,如WO2004/024928中所述。
其他除草剂抗性植物有耐受乙酰乳酸合成酶(ALS)抑制剂的植物。已知的ALS抑制剂包括,例如,磺酰脲、咪唑啉酮、三唑并嘧啶类、嘧啶氧基(硫代)苯甲酸酯和/或磺酰基氨基羰基三唑啉酮除草剂。已知ALS酶(也被称为乙酰羟酸合成酶,AHAS)的不同突变赋予了对不同除草剂和除草剂类的耐受性,例如在Tranel and Wright,Weed Science(2002),50,700-712,以及在US5,605,011、US5,378,824、US5,141,870和US5,013,659中所述。磺酰脲耐受性植物和咪唑啉酮耐受性植物的生产描述于US5,605,011、US5,013,659、US5,141,870、US5,767,361、US5,731,180、US5,304,732、US4,761,373、US5,331,107、US5,928,937、和US5,378,824;以及国际公布文本WO96/033270。其他咪唑啉酮耐受性植物还描述于例如WO2004/040012、WO2004/106529、WO2005/020673、WO2005/093093、WO2006/007373、WO2006/015376、WO2006/024351和WO2006/060634。其他磺酰脲耐受植物和咪唑啉酮耐受性植物还描述于例如WO2007/024782。
其他耐受ALS抑制剂——特别是咪唑啉酮,磺酰脲和/或氨磺酰基羰基三唑啉酮——的植物可通过诱变、在除草剂存在的情况下进行细胞培养选择、或者诱变育种而获得,例如,US5,084,082中对大豆、WO97/41218中对稻、US5,773,702和WO99/057965中对甜菜、US5,198,599中对莴苣或WO2001/065922中对向日葵进行的描述。
还可以用本发明式(I)化合物处理的植物或植物栽培种(由植物生物技术方法如基因工程获得)是抗昆虫的转基因植物,即可抵抗某些目标昆虫侵害的植物。这些植物可通过遗传转化或通过选择含赋予所述昆虫抗性的突变的植物而获得。
在本文中,术语―抗昆虫转基因植物‖包括含有至少一种含编码以下蛋白的编码序列的转基因的任何植物:
1)一种源自苏云金杆菌(Bacillus thuringiensis)的杀昆虫晶体蛋白1是其杀虫部分,例如由Crickmore等人,Microbiology and MolecularBiology Reviews(1998),62,807-813所汇编的,由Crickmore等人(2005)在Bacillus thuringiensis toxin nomenclature(http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/)上更新的杀昆虫晶体蛋白质或其杀虫部分,例如Cry蛋白质类中的蛋白质Cry1Ab、Cry1Ac、Cry1F、Cry2Ab、Cry3Ae或Cry3Bb或其杀虫部分;或者
2)一种在第二种苏云金杆菌晶体蛋白或其部分的存在下具有杀虫活性的来自苏云金杆菌的晶体蛋白或其部分,例如由Cy34和Cy35晶体蛋白组成的二元毒素(Moellenbeck等人,Nat.Biotechnol.(2001),19,668-72;Schnepf等人,Applied Environm.Microb.(2006),71,1765-1774);或者
3)一种包含来自苏云金杆菌两种不同杀虫晶体蛋白部分的杀虫杂合蛋白质,例如上述1)的蛋白质的杂合体,或是上述2)的蛋白质的杂合体,如由玉米株系MON98034(WO2007/027777)产生的Cry1A.105蛋白;或者
4)上面1)到3)中任一项的蛋白质,其中由于一些,特别是1-10个氨基酸被另一个氨基酸所替代和/或由于在克隆或转化过程中引入编码DNA的改变,从而获得对于目标昆虫更高的杀虫活性,和/或扩大受影响的目标昆虫品种的范围,如玉米株系MON863或MON88017中的Cry3Bb1蛋白,或在玉米株系MIR604中的Cry3A蛋白;或者
5)一种来自苏云金杆菌或蜡样芽胞杆菌(Bacillus cereus)的杀昆虫分泌性蛋白质,或其杀虫成分,例如在http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html所列的营养期杀虫蛋白(VIP),例如来自VIP3Aa蛋白类的蛋白质;或者
6)一种在来自苏云金杆菌或蜡样芽胞杆菌的第二分泌性蛋白质的存在下具有杀虫活性的来自苏云金杆菌或蜡样芽胞杆菌的分泌性蛋白质,例如由VIP1A和VIP2A蛋白质组成的二元毒素(WO94/21795);或者
7)一种包含来自苏云金杆菌或蜡样芽胞杆菌的不同分泌性蛋白质的部分的杀虫杂合蛋白质,例如上述1)的蛋白质杂合体,或上述2)的蛋白质的杂合体;或者
8)一种上述1)到3)任一项的蛋白质,其中由于一些,特别是1-10个氨基酸被另一个氨基酸替代和/或由于在克隆或转化过程中引入编码DNA的变化(但仍编码一种杀虫蛋白)从而获得更高的对于目标昆虫的杀虫活性、和/或扩大受影响目标昆虫种类的范围,例如棉花株系COT102中的VIP3Aa蛋白。
当然,本文使用的抗昆虫转基因植物还包括含有编码上述1-8任一类蛋白质的基因的结合物的任何植物。在一个实施方案中,抗昆虫植物含有多于一种编码上述1-8任一类蛋白质的转基因,通过使用对同一目标昆虫种属具有杀虫性但作用模式不同(例如结合昆虫中不同受体结合位点)的不同蛋白,来扩大受影响的目标昆虫种类的范围或延迟植物的昆虫抗性的发展。
还可根据本发明方法处理的植物或植物品种(通过植物生物技术方法如遗传工程而获得)对非生物胁迫因素具有耐受性。这些植物可通过遗传转化或通过选择含有赋予所述胁迫耐受性的突变的植物而获得。特别有用的胁迫耐受性植物包括:
a.含有能够降低植物细胞或植物中多(ADP-核糖)聚合酶(PARP)基因的表达和/或活性的转基因植物,如在WO2000/004173或EP04077984.5或EP06009836.5中所述。
b.含有能够降低植物或植物细胞的PARG编码基因的表达和/或活性的胁迫耐受性增强转基因的植物,例如在WO2004/090140中所述。
c.含有编码烟酰胺腺嘌呤二核苷酸生物合成补救途径的植物功能酶的胁迫耐受性增强转基因的植物,所述植物功能性酶包括烟酰胺酶、烟酸酯磷酸核糖基转移酶、烟酸单核苷酸腺嘌呤基转移酶、烟酰胺腺嘌呤二核苷酸合成酶或烟酰胺磷酸核糖基转移酶,例如在EP04077624.7或WO2006/133827或PCT/EP07/002433中所述。
也可用本发明的式(I)化合物处理的植物或植物品种(通过植物生物技术方法如遗传工程而获得)显示出改变的收获产品的数量、质量和/或贮藏稳定性,和/或改变的收获产品的具体成分的性质,例如:
1)合成改性淀粉的转基因植物,该改性淀粉的物理化学特性——特别是直链淀粉的含量或是直链淀粉/支链淀粉比、支链程度、平均链长、侧链分布、粘度特性、凝胶化强度、淀粉粒大小和/或淀粉粒形态——与野生型植物细胞或植物中的合成淀粉相比发生了改变,从而使得其能更适于特定应用。合成改性淀粉的这些转基因植物描述于,例如EP0571427、WO95/004826、EP0719338、WO96/15248、WO96/19581、WO96/27674、WO97/11188、WO97/26362、WO97/32985、WO97/42328、WO97/44472、WO97/45545、WO98/27212、WO98/40503、WO99/58688、WO99/58690、WO99/58654、WO2000/008184、WO2000/008185、WO2000/28052、WO2000/77229、WO2001/12782、WO2001/12826、WO2002/101059、WO2003/071860、WO2004/056999、WO2005/030942、WO2005/030941、WO2005/095632、WO2005/095617、WO2005/095619、WO2005/095618、WO2005/123927、WO2006/018319、WO2006/103107、WO2006/108702、WO2007/009823、WO2000/22140、WO2006/063862、WO2006/072603、WO2002/034923、EP06090134.5、EP06090228.5、EP06090227.7、EP07090007.1、EP07090009.7、WO2001/14569、WO2002/79410、WO2003/33540、WO2004/078983、WO2001/19975、WO95/26407、WO96/34968、WO98/20145、WO99/12950、WO99/66050、WO99/53072、US6,734,341、WO2000/11192、WO98/22604、WO98/32326、WO2001/98509、WO2001/98509、WO2005/002359、US5,824,790、US6,013,861、WO94/004693、WO94/009144、WO94/11520、WO95/35026和WO97/20936。
2)合成非淀粉碳水化合物聚合物的转基因植物,或合成与未进行遗传修饰的野生型植物相比具有改变性质的非淀粉碳水化合物聚合物的转基因植物。实例有产生多聚果糖,尤其是产生菊粉型和果聚糖型多聚果糖的植物,如EP0663956、WO96/001904、WO96/021023、WO98/039460和WO99/024593中所述;产生α-1,4-葡聚糖的植物,如WO95/031553、US2002/031826、US6,284,479、US5,712,107、WO97/047806、WO97/047807、WO97/047808以及WO2000/14249中所述;产生α-1,6-支链α-1,4-葡聚糖的植物,如WO2000/73422中所述;以及产生交替糖(alternan)的植物,如WO2000/047727、EP06077301.7、US5,908,975和EP0728213中所述。
3)产生透明质酸(hyaluronan)的转基因植物,例如,在WO06/032538、WO2007/039314、WO2007/039315、WO2007/039316、JP2006/304779和WO2005/012529中所述。
也可使用本发明的式(I)化合物处理的植物或植物品种(通过植物生物技术方法如遗传工程而获得)是具有改变的纤维特性的植物,例如棉花植物。这些植物可通过遗传转化或通过选择含有赋予所述改变的纤维特性的突变的植物而获得,其包括:
a)包含纤维素合成酶基因的改变形式的植物,如棉花植物,如WO98/000549中所述;
b)包含rsw2或rsw3同源核酸的改变形式的植物,如棉花植物,如WO2004/053219中所述;
c)具有蔗糖磷酸酯合成酶的增强表达的植物,如棉花植物,如WO2001/017333中所述;
d)具有蔗糖合酶的增强表达的植物,如棉花植物,如WO02/45485中所述;
e)其中纤维细胞基部胞间连丝门控的时机(timing)通过例如纤维选择性β-1,3-葡聚糖酶的下调被改变的植物,如棉花植物,如WO2005/017157中所述;
f)具有反应性改变的——通过例如含nodC的N-乙酰葡糖胺转移酶基因和几丁质合成酶基因的表达而改变——纤维的植物,如棉花植物,如WO2006/136351中所述。
也可使用本发明的式(I)化合物处理的植物或植物栽培种(通过植物生物技术方法如遗传工程而获得)是具有改变的油分布特性的植物,例如油菜和相关的芸苔属(Brassica)植物。这些植物可通过遗传转化或通过选择含有赋予所述改变的油特性的突变的植物而获得,其包括:
a)产生具有高油酸含量的油的植物,例如油菜植物,例如US5,969,169、US5,840,946或US6,323,392或US6,063,947中所述;
b)产生具有低亚麻酸含量的油的植物,例如油菜植物,例如US6,270,828、US6,169,190或US5,965,755中所述;
c)产生具有低水平的饱和脂肪酸的油的植物,例如油菜植物,例如US5,434,283中所述。
可用本发明式(I)化合物进行处理的特别有用的转基因植物是含有转化株系或转化株系组合的植物,其列于例如多个国家或地区管理机构的数据库中。
可以用本发明式(I)化合物进行处理的特别有用的转基因植物是含有一种或多种编码一种或多种毒素的基因的植物,这些转基因植物是市售的,商品名为:(例如玉米、棉花、大豆)、(例如玉米)、(例如玉米)、(例如玉米)、(例如玉米)、(棉花)、(棉花)、 (棉花)、(例如玉米)、和(马铃薯)。可提及的除草剂耐受植物的实例为玉米品种、棉花品种和大豆品种,其市售商品名为:(对草甘膦耐受,例如玉米、棉花、大豆)、(对草丁膦耐受,例如油菜)、(对咪唑啉酮耐受)和(对磺酰脲耐受),例如玉米。可提及的除草剂耐受植物(用常规除草剂耐受性方式培育的植物)包括商品名为(例如玉米)的市售品种。
根据本发明使用的式(I)化合物可以转化为常规制剂,例如溶液剂、乳剂、可湿性粉末剂、水基和油基悬浮剂、粉剂、粉末剂(dust)、糊剂、可溶性粉剂、可溶性颗粒剂、撒播颗粒剂、悬乳浓缩剂、经活性成分浸渍的天然物质、经活性成分浸渍的合成物质、肥料以及聚合物中的微胶囊剂。
在本发明中,尤其优选以喷雾制剂形式施用式(I)化合物。
因此,本发明另外还涉及用于增强植物对非生物胁迫抗性的喷雾制剂。一种喷雾制剂详细记载于下文:
用于喷雾施用的制剂以已知的方式制备,例如将本发明所用的式(I)化合物与填充剂(即液体溶剂和/或固体载体)混合,任选使用表面活性剂(即乳化剂和/或分散剂和/或成泡剂)。也可任选使用其他常规添加剂例如常规填充剂和溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、粘合剂、赤霉素以及水。所述制剂可以在合适的设备中制备或者在施用前或施用中制备。
所用的助剂可为适于赋予组合物自身和/或由其得到的制剂(例如喷雾液)特定性质(例如特殊的技术性质和/或特定生物学性质)的物质。常规助剂包括:填充剂、溶剂和载体。
合适的填充剂为,例如水、极性和非极性有机化学液体,如芳烃类和非芳烃类(例如石蜡、烷基苯、烷基萘、氯苯)、醇类和多元醇类(如果合适,其还可任选被取代、醚化和/或酯化)、酮类(例如丙酮、环己酮)、酯类(包括脂肪和油)以及(聚)醚类、未被取代和被取代的胺类、酰胺类、内酰胺类(例如N-烷基吡咯烷酮)以及内酯类、砜类和亚砜类(例如二甲基亚砜)。
如果所用的填充剂为水,则还可使用例如有机溶剂作为助溶剂。合适的液体溶剂基本上有:芳族化合物,例如二甲苯、甲苯或烷基萘;氯代芳烃和氯代脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷或石蜡,如矿物油馏分、矿物油和植物油;醇,例如丁醇或乙二醇,及其醚和酯;酮,例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲亚砜;以及水。
可以使用着色剂例如无机颜料,例如氧化铁、氧化钛和普鲁士蓝;以及有机着色剂,例如茜素着色剂、偶氮着色剂和金属酞菁着色剂;和微量营养素,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
可存在于根据本发明使用的制剂中的合适的润湿剂为所有促进润湿并且通常用于农用化学活性化合物制剂中的物质。优选使用烷基萘磺酸盐例如二异丙基萘磺酸盐或二异丁基萘磺酸盐。
可存在于可根据本发明使用的制剂中的合适的分散剂和/或乳化剂为所有的常用于农用化学活性化合物制剂中的非离子分散剂、阴离子分散剂和阳离子分散剂。优选使用非离子或阴离子分散剂或非离子或阴离子分散剂的混合物。合适的非离子分散剂特别为环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基苯酚聚乙二醇醚,及其磷酸化或硫酸化衍生物。合适的阴离子分散剂特别为木素磺酸盐、聚丙烯酸盐和芳基磺酸盐/甲醛缩合物。
可存在于可根据本发明使用的制剂中的合适的消泡剂为所有常规用于农用化学活性化合物制剂中的泡沫抑制物质。优选可使用硅酮消泡剂和硬脂酸镁。
可存在于可根据本发明使用的制剂中的合适的防腐剂为所有可为此目的用于农用化学组合物中的物质。可以提及的实例为二氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的制剂中的合适的二次增稠剂为所有可为此目的用于农用化学组合物中的物质。优选为纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土和细分散的二氧化硅。
可存在于可根据本发明使用的制剂中的合适的粘合剂包括所有可用于拌种产品的常规粘合剂。优选提及聚乙烯基吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素。可存在于可根据本发明使用的制剂中的合适的赤霉素优选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。这些赤霉素为已知的(参见R.Wegler"Chemie derPflanzenschutz-and "[Chemistry of theCrop Protection Compositions and Pesticides]第2卷,Springer Verlag,1970,第401页-412页)。
其他可能的添加剂可为香料、任选改性的矿物油或植物油、蜡和营养素(包括微量营养素),例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。另外可存在稳定剂,例如冷稳定剂、抗氧化剂、光稳定剂或其他改进化学和/或物理稳定性的试剂。
所述制剂通常包含0.01至98重量%,优选0.5至90重量%的式(I)化合物。
本发明式(I)化合物可以其市售制剂存在和以由这些制剂制备的使用形式作为与其他活性化合物的混合物存在,所述其他活性化合物为例如杀昆虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质、除草剂、安全剂、肥料或化学信息素。
此外,式(I)化合物对于植物自身防御而言的积极效应可以用杀虫、杀真菌或杀细菌活性化合物另外处理而得以支持。
为增强对非生物胁迫的抗性,施加式(I)化合物的优选次数为用经证明有效的施用率处理土壤、茎和/或叶。
式(I)的活性化合物通常也可以额外地以其市售制剂形式存在和以由这些制剂与其他活性化合物混合制备的使用形式存在,所述其他活性化合物为例如杀昆虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、杀细菌剂、生长调节物质、影响植物成熟的物质、安全剂或除草剂。特别有益的混合成分(mixing partner)为例如下面各组列出的不同类的活性化合物,不以其顺序做任何优选:
杀真菌剂:
F1)核酸合成抑制剂:例如苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、乙嘧酚磺酸酯(bupirimate)、chiralaxyl、clozylacon、二甲嘧酚(dimethirimol)、乙嘧酚(ethirimol)、呋霜灵(furalaxyl)、恶霉灵(hymexazole)、甲霜灵(metalaxyl)、高效甲霜灵(metalaxyl-M)、呋酰胺(ofurace)、噁霜灵(oxadixyl)、喹菌酮(oxolinic acid);
F2)有丝分裂和细胞分裂抑制剂:例如苯菌灵(benomyl)、多菌灵(carbendazim)、乙霉威(diethofencarb)、麦穗宁(fuberidazole)、氟吡菌胺(fluopicolid)、戊菌隆(pencycuron)、噻菌灵(thiabendazole)、甲基硫菌灵(thiophanate-methyl)、苯酰菌胺(zoxamide)和氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶;
F3)呼吸链复合体I/II抑制剂:例如氟嘧菌胺(diflumetorim)、异噻菌胺(bixafen)、啶酰菌胺(boscalid)、萎锈灵(carboxin)、二氟林(diflumethorim)、甲呋酰胺(fenfuram)、氟吡菌酰胺(fluopyram)、氟酰胺(flutolanil)、呋吡菌胺(furametpyr)、灭锈胺(mepronil)、氧化萎锈灵(oxycarboxin)、戊苯吡菌胺(penflufen)、吡噻菌胺(penthiopyrad)、溴氟唑菌(thifluzamide)、N-[2-(1,3-二甲基丁基)苯基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、氟环唑(isopyrazam)、环丙吡菌胺(sedaxan)、3-(二氟甲基)-1-甲基-N-(3',4',5'-三氟联苯基-2-基)-1H-吡唑-4-甲酰胺、3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺、3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺、N-[1-(2,4-二氯苯基)-1-甲氧基丙烷-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺及其相应的盐;
F4)呼吸链复合体III抑制剂:例如吲唑磺菌胺(amisulbrom)、嘧菌酯(azoxystrobin)、氰霜唑(cyazofamid)、醚菌胺(dimoxystrobin)、烯肟菌(enestrobin)、噁唑菌酮(famoxadone)、咪唑菌酮(fenamidone)、氟嘧菌酯(fluoxastrobin)、醚菌酯(kresoxim-methyl)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、唑菌胺酯(pyraclostrobin)、pyribencarb、啶氧菌酯(picoxystrobin)、肟菌酯(trifloxystrobin)、(2E)-2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺、(2E)-2-(乙氧基亚氨基)-N-甲基-2-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)乙酰胺及其相应的盐、(2E)-2-(甲氧基亚氨基)-N-甲基-2-{2-[(E)-({1-[3-(三氟甲基)苯基]乙氧基}亚氨基)甲基]苯基}乙酰胺、(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(2E)-2-{2-[({[(2E,3E)-4-(2,6-二氯苯基)亚丁-3-烯-2-基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、2-氯-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)吡啶-3-甲酰胺、5-甲氧基-2-甲基-4-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)-2,4-二氢-3H-1,2,4-三唑-3-酮、{2-[({环丙基[(4-甲氧基苯基)亚氨基]甲基}硫烷基)甲基]苯基}-3-甲氧基丙烯酸2-甲酯、N-(3-乙基-3,5,5-三甲基环己基)-3-(甲酰基氨基)-2-羟基苯甲酰胺及其相应的盐;
F5)解偶剂(decoupler):例如敌螨普(dinocap)、氟啶胺(fluazinam);
F6)ATP产生抑制剂:例如三苯基乙酸锡(fentin acetate)、三苯基氯化锡(fentin chloride)、毒菌锡(fentin hydroxide)、硅噻菌胺(silthiofam);
F7)氨基酸和蛋白质生物合成抑制剂:例如胺扑灭(andoprim)、灭瘟素(blasticidin-S)、嘧菌环胺(cyprodinil)、春雷霉素(kasugamycin)、春雷霉素一水合盐酸盐(kasugamycin hydrochloride hydrate)、嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil);
F8)信号转导抑制剂:例如拌种咯(fenpiclonil)、咯菌腈(fludioxonil)、苯氧喹啉(quinoxyfen);
F9)脂类和膜合成抑制剂:例如乙菌利(chlozolinate)、异菌脲(iprodione)、腐霉利(procymidone)、乙烯菌核利(vinclozolin)、氨丙膦酸(ampropylfos)、氨丙膦酸钾(potassium-ampropylfos)、敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)(IBP)、稻瘟灵(isoprothiolane)、吡菌磷(pyrazophos)、甲基立枯磷(tolclofos-methyl)、联苯、iodocarb、霜霉威(propamocarb)、霜霉威盐酸盐(propamocarb hydrochloride);
F10)麦角固醇生物合成抑制剂:例如环酰菌胺(fenhexamid)、氧环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、苄氯三唑醇(diclobutrazole)、苯醚甲环唑(difenoconazole)、烯唑醇(diniconazole)、高效烯唑醇(diniconazole-M)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、丁氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、己唑醇(hexaconazole)、亚胺唑(imibenconazole)、种菌唑(ipconazole)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazol)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、螺环菌胺(spiroxamine)、戊唑醇(tebuconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、灭菌唑(triticonazole)、烯效唑(uniconazole)、伏立康唑(voriconazole)、抑霉唑(imazalil)、烯菌灵(imazalil sulfate)、恶咪唑(oxpoconazole)、氯苯嘧啶醇(fenarimol)、呋嘧醇(flurprimidol)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine)、稻瘟酯(pefurazoate)、咪鲜胺(prochloraz)、氟菌唑(triflumizole)、烯霜苄唑(viniconazole)、杀螟丹(aldimorph)、十二环吗啉(dodemorph)、十二环吗啉乙酸盐(dodemorph acetate)、丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph)、苯锈啶(fenpropidin)、萘替芬(naftifine)、稗草丹(pyributicarb)、特比萘芬(terbinafine)、1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、1-(2,2-二甲基-2,3-二氢-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、N'-{5-(二氟甲基)-2-甲基-4-[3-(三甲基甲硅烷基)丙氧基]苯基}-N-乙基-N-甲基酰亚胺基甲酰胺、N-乙基-N-甲基-N'-{2-甲基-5-(三氟甲基)-4-[3-(三甲基甲硅烷基)丙氧基]苯基}酰亚胺基甲酰胺和O-{1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基}-1H-咪唑-1-硫代甲酸酯;
F11)细胞壁合成抑制剂:例如苯噻菌胺(benthiavalicarb)、双丙氨膦(bialaphos)、烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、异丙菌胺(iprovalicarb)、多抗霉素(polyoxins)、多氧霉素(polyoxorim)、有效霉素A(validamycin A);
F12)黑色素生物合成抑制剂:例如环丙酰菌胺(capropamid)、双氯氰菌胺(diclocymet)、氰菌胺(fenoxanil)、四氯苯酞(phthalide)、咯喹酮(pyroquilon)、三环唑(tricyclazole);
F13)抗性诱导剂:例如苯并噻二唑(acibenzolar-S-methyl)、烯丙苯噻唑(probenazole)、噻酰菌胺(tiadinil);
F14)多位点物质:例如敌菌丹(captafol)、克菌丹(captan)、百菌清(chlorothalonil)、铜盐如氢氧化铜、环烷酸铜(coppernaphthenate)、氯氧化铜(copper oxychloride)、硫酸铜、氧化铜、喹啉铜(oxine-copper)和波尔多液混合物(Bordeaux mixture)、苯氟磺胺(dichlofluanid)、二氰蒽醌(dithianon)、多果定(dodine)、多果定游离碱(dodine free base)、福美铁(ferbam)、灭菌丹(folpet)、氟灭菌丹(fluorofolpet)、双胍盐(guazatine)、双胍辛乙酸盐(guazatineacetate)、双胍辛胺(iminoctadine)、双胍辛烷基苯磺酸盐(iminoctadinealbesilate)、双胍辛胺乙酸盐(iminoctadine triacetate)、代森锰铜(mancopper)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram)、代森联锌(metiram zinc)、丙森锌(propineb)、硫和含有多硫化钙的硫制剂、福美双(thiram)、甲苯氟磺胺(tolylfluanid)、代森锌(zineb)、福美锌(ziram);
F15)未知机理化合物:例如amibromdol、苯噻硫氰(benthiazole)、bethoxazin、卡巴西霉素(capsimycin)、香芹酮(carvone)、灭螨猛(chinomethionat)、氯化苦(chloropicrin)、硫杂灵(cufraneb)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌酮(diclomezine)、双氯酚(dichlorophen)、氯硝胺(dicloran)、野燕枯(difenzoquat)、苯敌快(difenzoquat methylsulphate)、二苯胺(diphenylamine)、噻唑菌胺(ethaboxam)、嘧菌腙(ferimzone)、氟酰菌胺(flumetover)、磺菌胺(flusulfamide)、氟啶酰菌胺(fluopicolide)、氟氯菌核利(fluoroimide)、三乙膦酸铝(fosatyl-Al)、六氯苯(hexachlorobenzene)、8-羟基喹啉硫酸盐(8-hydroxyquinoline sulphate)、异菌脲(iprodione)、人间霉素(irumamycin)、异噻菌胺(isotianil)、磺菌威(methasulphocarb)、苯菌酮(metrafenone)、氰土灵(methyl isothiocyanate)、米多霉素(mildiomycin)、多马霉素(natamycin)、福美镍(nickel dimethyldithiocarbamate)、酞菌酯(nitrothal-isopropyl)、辛噻酮(octhilinone)、oxamocarb、oxyfenthiin、五氯苯酚(pentachlorophenol)及其盐、2-苯基苯酚及其盐、病花灵(piperalin)、propanosine-sodium、丙氧喹啉(proquinazid)、吡咯菌素(pyrrolnitrin)、五氯硝基苯(quintozene)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、咪唑嗪(triazoxide)、水杨菌胺(trichlamide)、氰菌胺(zarilamid)和2,3,5,6-四氯-4-(甲基磺酰基)吡啶、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、2,4-二氢-5-甲氧基-2-甲基-4-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]苯基]-3H-1,2,3-三唑-3-酮(185336-79-2)、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、3,4,5-三氯-2,6-吡啶二腈、2-[[[环丙基[(4-甲氧基苯基)亚氨基]甲基]硫基]甲基]-α-(甲氧基亚甲基)苯乙酸甲酯、4-氯-α-炔丙氧基-N-[2-[3-甲氧基-4-(2-炔丙氧基)苯基]乙基]苯乙酰胺、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲基磺酰基)氨基]丁酰胺、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶、5-氯-6-(2,4,6-三氟苯基)-N-[(1R)-1,2,2-三甲基丙基][1,2,4]三唑并[1,5-a]嘧啶-7-胺、5-氯-N-[(1R)-1,2-二甲基丙基]-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶-7-胺、N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯烟酰胺、N-(5-溴-3-氯吡啶-2-基)甲基-2,4-二氯烟酰胺、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯乙酰胺、N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰氨基-2-羟基苯甲酰胺、2-[[[[1-[3(1-氟-2-苯基乙基)氧基]苯基]亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-αE-苯乙酰胺、N-{2-[3-氯-5-(三氟甲基)吡啶-2-基]乙基}-2-(三氟甲基)苯甲酰胺、N-(3',4'-二氯-5-氟联苯基-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、N-(6-甲氧基-3-吡啶基)环丙烷甲酰胺、1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基-1H-咪唑-1-羧酸、O-[1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基]-1H-咪唑-1-硫代羟酸、2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺。
杀细菌剂:
溴硝丙二醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、福镁镍(nickel dimethyldithiocarbamate)、春雷霉素(kasugamycin)、辛噻酮(octhilinone)、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracycline)、噻菌灵(probenazole)、链霉素(streptomycin)、叶枯酞(tecloftalam)、硫酸铜及其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
I1)乙酰胆碱酯酶(AChE)抑制剂:例如氨基甲酸酯类,例如棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、灭除威(XMC)和灭杀威(xylylcarb);或有机磷酸酯类,例如乙酰甲胺磷(acephate)、甲基吡恶磷(azamethiphos)、保棉磷/益棉磷(aziphos(-methyl,-ethyl))、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、倍硫磷(fenthion)、噻唑酮磷(fosthiazate)、庚烯磷(heptenophos)、碘硫磷(isodofenphos)、O-(甲氧基氨基硫磷酰)水杨酸异丙酯(isopropylO-(methoxyaminothiophosphoryl)salicylate)、噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、亚砜磷(oxydemeton(-methyl))、甲基对硫磷(parathion(-methyl))、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、腈肟磷(phoxim)、虫螨磷(pirimiphos(-methyl))、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹噁磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)和蚜灭磷(vamidothion)
I2)GABA门控氯离子通道拮抗剂:例如有机氯类,例如氯丹(chlordane)和硫丹(endosulfan(α-));或菲普鲁来斯(fiproles(苯基吡唑类)):例如乙虫腈(ethiprole)、氟虫腈(fipronil)、pyrafluprole和pyriprole。
I3)钠通道调节剂/电位门控(voltage-gated)钠通道阻断剂:例如拟除虫菊酯类,例如氟丙菊酯(acrinathrin)、烯丙菊酯(d-顺-反,d-反)(allethrin(d-cis-trans,d-trans))、联苯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯-S-环戊基异构体、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(β-)(cyfluthrin(beta-))、氯氟氰菊酯(γ-、λ-)(cyhalothrin(gamma-、lambda-))、氯氰菊酯(α-、β-、θ-、ζ-)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氯菊酯(cyphenothrin[(1R)-反式异构体])、溴氰菊酯(deltamethrin)、四氟甲醚菊酯(dimefluthrin)、右旋烯炔菊酯((EZ)-1R异构体)(empenthrin([(EZ)-1R-isomer]))、S-氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate(tau-))、苄螨醚(halfenprox)、咪炔菊酯(imiprothrin)、甲氧苄氟菊酯(metofluthrin)、百灭宁(permethrin)、苯醚菊酯(1R反式异构体)(phenothrin(1R trans-isomer)、右旋炔丙菊酯(prallethrin)、丙氟菊酯(profluthrin)、pyrethrins(pyrethrum)、苄呋菊酯(resmethrin)、RU15525、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(1R异构体)(tetramethrin(1R isomer))、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)和溴氟菊酯(ZXI8901);或DDT;或甲氧滴滴涕(methoxychlor)。
I4)烟碱乙酰胆碱受体激动剂,例如新烟碱类(neonicotinoid),例如啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)或烟碱(nicotine)。
I5)变构乙酰胆碱受体调节剂(激动剂),例如多杀霉素类(spinosyn)例如乙基多杀菌素(spinetoram)和多杀菌素(spinosad)。
I6)氯离子通道活化剂类:例如除虫菌素(avermectin)/米尔倍霉素类(milbemycin),例如阿维菌素(abamectin)、埃玛菌素(emamectin)、埃玛菌素苯甲酸盐(emamectin benzoate)、lepimectin和米尔倍霉素(milbemycin)。
I7)保幼激素模拟物类:例如烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)、烯虫酯(methoprene);或苯氧威(fenoxycarb);吡丙醚(pyriproxyfen)。
I8)具有未知或未确定作用机理的活性成分,例如熏蒸剂类,例如溴甲烷和其他烷基卤化物;或氯化苦(chloropicrin);磺酰氟;硼砂;吐酒石。
I9)选择性拒食剂类:例如吡蚜酮(pymetrozine);或氟啶虫酰胺(flonicamid)。
I10)螨生长抑制剂类:例如四螨嗪(clofentezine)、氟螨嗪(diflovidazin)、噻螨酮(hexythiazox)、乙螨唑(etoxazole)。
I11)昆虫肠道膜微生物干扰剂类:例如苏云金杆菌以色列亚种(Bacillus thuringiensis subspecies israelensis)、球形芽孢杆菌(Bacillussphaericus)、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis subspeciesaizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensissubspecies kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillusthuringiensis subspecies tenebrionis)和BT植物蛋白:例如Cry1Ab、Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Ab1。
I12)氧化磷酸化抑制剂,a)ATP干扰剂类,例如丁醚脲(diafenthiuron);或有机锡化合物,例如三唑锡(azocyclotin)、三环锡(cyhexatin)、苯丁锡(fenbutatin oxide);或炔螨特(propargite);三氯杀螨砜(tetradifon)。
I13)通过间断H-质子梯度而起作用的氧化磷酸化解偶联剂类:例如虫螨腈(chlorfenapyr)和二硝甲酚(DNOC)。
I14)乙酰胆碱受体拮抗剂,例如杀虫磺(bensultap)、杀螟丹(cartap(-hydrochloride))、杀虫环(thiocyclam)和杀虫双(thiosultapsodium)
I15)几丁质生物合成抑制剂,0型,例如苯甲酰脲类,例如双三氟虫脲(bistrifluron)、氟啶脲(chlofluazuron)、除虫脲(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)和杀铃脲(triflumuron)。
I16)几丁质生物合成抑制剂,1型,例如噻嗪酮(buprofezin)。
I17)蜕皮干扰剂,例如灭蝇胺(cyromazine)。
I18)蜕皮激素激动剂/干扰剂类,例如双酰肼类,例如环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)和虫酰肼(tebufenozide)。
I19)章鱼胺能激动剂类,例如虫螨脒(amitraz)。
I20)复合物Ⅲ电子转移抑制剂类:例如伏蚁腙(hydramethylnone);灭螨醌(acequinocyl);嘧螨酯(fluacrypyrim)。
I21)复合物I电子转移抑制剂类,例如METI杀螨剂类,例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)或鱼藤酮(rotenone(Derris))。
I22)电压门控钠通道阻断剂,例如茚虫威(indoxacarb)、氰氟虫胺(metaflumizone)。
I23)乙酰-CoA羧化酶抑制剂,例如特窗酸衍生物类:例如螺螨酯(spirodiclofen)和螺甲螨酯(spiromesifen);和特特拉姆酸衍生物类(tetramic acids):例如螺虫乙酯(spirotetramat)。
I24)复合物IV电子转移抑制剂类,例如膦类,例如磷化铝、磷化钙、膦、磷化锌;或氰化物。
I25)复合物II电子转移抑制剂,例如腈吡螨酯(cyenopyrafen)。
I26)兰诺定(ryanodin)受体效应物类,例如二酰胺类,例如氟虫酰胺(flubendiamide)、氯虫酰胺(Chlorantraniliprole(Rynaxypyr))、溴氰虫酰胺(cyantraniliprole(Cyazypyr))和3-溴-N-{2-溴-4-氯-6-[(1-环丙基乙基)氨甲酰基]苯基}-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺(已知于WO2005/077934)或2-[3,5-二溴-2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)苯甲酰基]-1,2-二甲基肼羧酸甲酯(已知于WO2007/043677)。
具有未知或未确定作用机理的活性化合物类:例如印楝素(azadirachtin)、amidoflumet、苯螨特(benzoximate)、联苯肼酯(bifenazate)、灭螨锰(chinomethionat)、冰晶石(cryolite)、丁氟螨酯(cyflumetofen)、三氯杀螨醇(dicofol)、5-氯-2-[(3,4,4-三氟丁-3-烯-1-基)磺酰基]-1,3-噻唑、flufenerim、啶虫丙醚(pyridalyl)和敌磺酸(pyrifluquinazon);还有基于坚强芽孢杆菌(Bacillus firmus)(I-1582,BioNeem,Votivo)的制剂和以下已知的活性化合物4-{[(6-溴吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(已知于WO2007/115644)、4-{[(6-氟吡啶-3-基)甲基](2,2-二氟乙基)氨基}呋喃-2(5H)-酮(已知于WO2007/115644)、4-{[(2-氯-1,3-噻唑-5-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(已知于WO2007/115644)、4-{[(6-氯吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(已知于WO2007/115644)、4-{[(6-氯吡啶-3-基)甲基](2,2-二氟乙基)氨基}呋喃-2(5H)-酮(已知于WO2007/115644)、4-{[(6-氯-5-氟吡啶-3-基)甲基](甲基)氨基}呋喃-2(5H)-酮(已知于WO2007/115643)、4-{[(5,6-二氯吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(已知于WO2007/115646)、4-{[(6-氯-5-氟吡啶-3-基)甲基](环丙基)氨基}呋喃-2(5H)-酮(已知于WO2007/115643)、4-{[(6-氯吡啶-3-基)甲基](环丙基)氨基}呋喃-2(5H)-酮(已知于EP0539588)、4-{[(6-氯吡啶-3-基)甲基](甲基)氨基}呋喃-2(5H)-酮(已知于EP0539588)、[1-(6-氯吡啶-3-基)乙基](甲基)氧代-λ4-亚硫烷基氨腈(已知于WO2007/149134)和其非对映体{[(1R)-1-(6-氯吡啶-3-基)乙基](甲基)氧代-λ6-亚硫烷基}氨腈和{[(1S)-1-(6-氯吡啶-3-基)乙基](甲基)氧代-λ6-亚硫烷基}氨腈(同样已知于WO2007/149134)和氟啶虫胺腈(sulfoxaflor)(同样已知于WO2007/149134)、1-[2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基]-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(已知于WO2006/043635)、[(3S,4αR,12R,12αS,12βS)-3-[(环丙基羰基)氧]-6,12-二羟基-4,12β-二甲基-11-氧代-9-(吡啶-3-基)-1,3,4,4α,5,6,6α,12,12α,12β-十氢-2H,11H-苯并[f]吡喃并[4,3-b]苯并二氢吡喃-4-基]甲基环丙烷羧酸酯(已知于WO2006/129714)、2-氰基-3-(二氟甲氧基)-N,N-二甲基苯磺酰胺(WO2006/056433)、2-氰基-3-(二氟甲氧基)-N-甲基苯磺酰胺(已知于WO2006/100288)、2-氰基-3-(二氟甲氧基)-N-乙苯磺酰胺(已知于WO2005/035486)、4-(二氟甲氧基)-N-乙基-N-甲基-1,2-苯并噻唑-3-胺1,1-二氧化物(已知于WO2007/057407)、N-[1-(2,3-二甲基苯基)-2-(3,5-二甲基苯基)乙基]-4,5-二氢-1,3-噻唑-2-胺(已知于WO2008/104503)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(已知于WO2003/106457)、3-(2,5-二甲基苯基)-4-羟基-8-甲氧基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(已知于WO2009/049851)、3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(已知于WO2009/049851)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(已知于WO2004/099160)、(2,2,3,3,4,4,5,5-八氟戊基)(3,3,3-三氟丙基)丙二腈(已知于WO2005/063094)、(2,2,3,3,4,4,5,5-八氟戊基)(3,3,4,4,4-五氟丁基)丙二腈(已知于WO2005/063094)、8-[2-(环丙基甲氧基)-4-(三氟甲基)苯氧基]-3-[6-(三氟甲基)哒嗪-3-基]-3-氮杂二环[3.2.1]辛烷(已知于WO2007/040280/282)、2-乙基-7-甲氧基-3-甲基-6-[(2,2,3,3-四氟-2,3-二氢-1,4-苯并二噁英-6-基)氧基]喹啉-4-基甲基碳酸酯(已知于JP2008110953)、2-乙基-7-甲氧基-3-甲基-6-[(2,2,3,3-四氟-2,3-二氢-1,4-苯并二噁英-6-基)氧基]喹啉-4-基乙酸酯(已知于JP2008110953)、PF1364(化学注册号1204776-60-2,已知于JP2010018586)、5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢-1,2-噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯甲腈(已知于WO2007075459)、5-[5-(2-氯吡啶-4-基)-5-(三氟甲基)-4,5-二氢-1,2-噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯甲腈(已知于WO2007/075459)、4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢-1,2-噁唑-3-基]-2-甲基-N-{2-氧代-2-[(2,2,2-三氟乙基)氨基]乙基}苯甲酰胺(已知于WO2005/085216)。
安全剂优选选自:
S1)式(S1)的化合物
其中符号和指数具有如下含义:
nA为0至5,优选0至3的自然数;
RA 1为卤素、(C1-C4)烷基、(C1-C4)烷氧基、硝基或(C1-C4)卤代烷基;
WA为未取代或取代的二价杂环基团,其选自具有1至3个选自N和O的杂原子的部分不饱和或芳族五元杂环,其中至少一个氮原子和至多一个氧原子存在于环中,优选为选自(WA 1)至(WA 4)的基团
mA为0或1;
RA 2为ORA 3、SRA 3或NRA 3RA 4或饱和或不饱和的3至7元杂环,其具有至少一个氮原子和最高达3个优选选自O和S的杂原子,所述杂环通过氮原子连接至(S1)中的羰基并且为未取代的或被选自(C1-C4)烷基、(C1-C4)烷氧基或任选取代的苯基取代,优选为式ORA 3、NHRA 4或N(CH3)2基团,特别为式ORA 3;
RA 3为氢或未取代或取代的脂族烃基,其优选具有总共1至18个碳原子;
RA 4为氢、(C1-C6)烷基、(C1-C6)烷氧基或取代的或未取代的苯基;
RA 5为氢、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C4)烷氧基(C1-C8)烷基、氰基或COORA 9,其中RA 9为氢、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C6)羟基烷基、(C3-C12)环烷基或三-(C1-C4)-烷基甲硅烷基;
RA 6、RA 7、RA 8相同或不同并且各自为氢、(C1-C8)烷基、(C1-C8)卤代烷基、(C3-C12)环烷基或取代或未取代的苯基;
优选为:
a)二氯苯基吡唑啉-3-羧酸(S1a)类化合物,优选的化合物为例如1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-羧酸、1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-羧酸乙酯(S1-1)(“吡唑解草酯(mefenpyr-diethyl)”),和记载于WO-A-91/07874中的相关化合物;
b)二氯苯基吡唑羧酸衍生物(S1b),优选的化合物为例如1-(2,4-二氯苯基)-5-甲基吡唑-3-羧酸乙酯(S1-2)、1-(2,4-二氯苯基)-5-异丙基吡唑-3-羧酸乙酯(S1-3)、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)吡唑-3-羧酸乙酯(S1-4)以及记载于EP-A-333131和EP-A-269806中的相关化合物;
c)1,5-联苯基吡唑-3-羧酸衍生物(S1c),优选的化合物为例如1-(2,4-二氯苯基)-5-苯基吡唑-3-羧酸乙酯(S1-5)、1-(2-氯苯基)-5-苯基吡唑-3-羧酸甲酯(S1-6)以及记载于例如EP-A-268554中的相关化合物;
d)三唑羧酸类化合物(S1d),优选的化合物为例如解草唑(fenchlorazole)(-乙酯),即1-(2,4-二氯苯基)-5-三氯甲基-(1H)-1,2,4-三唑-3-羧酸乙酯(S1-7),以及记载于EP-A-174562和EP-A-346620中的相关化合物;
e)5-苄基-或5-苯基-2-异噁唑啉-3-羧酸或5,5-联苯基-2-异噁唑啉-3-羧酸类化合物(S1e),优选的化合物为例如5-(2,4-二氯苄基)-2-异噁唑啉-3-羧酸乙酯(S1-8)或5-苯基-2-异噁唑啉-3-羧酸乙酯(S1-9)以及记载于WO-A-91/08202中的相关化合物,或5,5-联苯基-2-异噁唑啉-3-羧酸(S1-10)或5,5-联苯基-2-异噁唑啉-3-羧酸乙酯(S1-11)(“双苯噁唑酸(isoxadifen-ethyl)”)或5,5-联苯基-2-异噁唑啉-3-羧酸正丙酯(S1-12)或5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-羧酸乙酯(S1-13),如专利申请WO-A-95/07897中所记载。
S2)式(S2)的喹啉衍生物
其中符号和指数具有如下含义:
RB 1为卤素、(C1-C4)烷基、(C1-C4)烷氧基、硝基或(C1-C4)卤代烷基;
nB为0至5、优选0至3的自然数;
RB 2为ORB 3、SRB 3或NRB 3RB 4或饱和或不饱和的3至7元杂环,其具有至少一个氮原子和最高达3个优选选自O和S的杂原子,所述杂环通过氮原子连接至(S2)中的羰基并且为未取代的或被选自(C1-C4)烷基、(C1-C4)烷氧基或任选取代苯基的基团所取代,优选为式O RB 3、NH RB 4或N(CH3)2的基团,特别为式ORB 3;
RB 3为氢或优选总共具有1至18个碳原子的未取代或取代的脂族烃;
RB 4为氢、(C1-C6)烷基、(C1-C6)烷氧基或取代或未取代的苯基;
TB为未取代的或被一个或两个(C1-C4)烷基或被[(C1-C3)-烷氧基]羰基取代的(C1或C2)-烷二基链;
优选为:
a)8-喹啉氧基乙酸类化合物(S2a),优选(5-氯-8-喹啉氧基)乙酸1-甲基己酯(“解毒喹(cloquintocet-mexyl)”)(S2-1)、(5-氯-8-喹啉氧基)乙酸1,3-二甲基丁-1-酯(S2-2)、(5-氯-8-喹啉氧基)乙酸4-烯丙氧基丁酯(S2-3)、(5-氯-8-喹啉氧基)乙酸1-烯丙氧基丙-2-酯(S2-4)、(5-氯-8-喹啉氧基)乙酸乙酯(S2-5)、(5-氯-8-喹啉氧基)乙酸甲酯(S2-6)、(5-氯-8-喹啉氧基)乙酸烯丙酯(S2-7)、(5-氯-8-喹啉氧基)乙酸2-(2-亚丙基亚氨基氧基)-1-乙酯(S2-8)、(5-氯-8-喹啉氧基)乙酸2-氧代丙-1-酯(S2-9)以及相关化合物,例如记载于EP-A-86750、EP-A-94349和EP-A-191736或EP-A-0492366,以及(5-氯-8-喹啉氧基)乙酸(S2-10),及其水合物和盐,例如锂盐、钠盐、钾盐、钙盐、镁盐、铝盐、铁盐、铵盐、季铵盐、锍盐或鏻盐,如WO-A-2002/34048中所记载;
b)(5-氯-8-喹啉氧基)丙二酸类化合物(S2b),优选的化合物为例如(5-氯-8-喹啉氧基)丙二酸二乙酯、(5-氯-8-喹啉氧基)丙二酸二烯丙酯、(5-氯-8-喹啉氧基)丙二酸甲基乙酯以及相关的化合物,如EP-A-0582198中所记载。
S3)式(S3)的化合物
其中符号和指数具有如下含义:
RC 1为(C1-C4)烷基、(C1-C4)卤代烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C3-C7)环烷基,优选二氯甲基;
RC 2、RC 3相同或不同,并且各自为氢、(C1-C4)烷基、(C2-C4)烯基、(C2-C4)炔基、(C1-C4)卤代烷基、(C2-C4)卤代烯基、(C1-C4)烷基氨基甲酰基-(C1-C4)烷基、(C2-C4)烯基氨基甲酰基-(C1-C4)烷基、(C1-C4)烷氧基-(C1-C4)烷基、二氧戊环基-(C1-C4)烷基、噻唑基、呋喃基、呋喃基烷基、噻吩基、哌啶基、取代或未取代的苯基、或RC 2和RC 3一起形成一个取代的或未取代的杂环,优选噁唑烷、噻唑烷、哌啶、吗啉、六氢嘧啶或苯并噁嗪环;优选:二氯乙酰胺类活性化合物,其通常用作萌芽前安全剂(土壤作用安全剂),例如“烯丙酰草胺(dichlormid)”(N,N-二烯丙基-2,2-二氯乙酰胺)(S3-1)、Stauffer的"R-29148"(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)(S3-2)、Stauffer的"R-28725"(3-二氯乙酰基-2,2-二甲基-1,3-噁唑烷)(S3-3)、“解草酮(benoxacor)”(4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪)(S3-4)、PPG Industries的“PPG-1292”(N-烯丙基-N-[(1,3-二氧戊环-2-基)甲基]二氯乙酰胺)(S3-5)、Sagro-Chem的“DKA-24”(N-烯丙基-N-[(烯丙基氨基羰基)甲基]二氯乙酰胺)(S3-6)、Nitrokemia或Monsanto的“AD-67”或“MON4660”(3-二氯乙酰基-1-氧杂-3-氮杂螺[4,5]癸烷)(S3-7)、TRI-ChemicalRT的“TI-35”(1-二氯乙酰基氮杂环庚烷)(S3-8)、BASF的“diclonon”(dicyclonone)或“BAS145138”或BASF的“LAB145138”(S3-9)((RS)-1-二氯乙酰基-3,3,8a-三甲基全氢吡咯[1,2-a]嘧啶-6-酮)、“解草噁唑(furilazole)”或者“MON13900”((RS)-3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷(S3-10);及其(R)异构体(S3-11)。
S4)式(S4)的N-酰基磺酰胺及其盐,
其中符号和指数具有如下含义:
XD为CH或N;
RD 1为CO-NRD 5RD 6或NHCO-RD 7;
RD 2为卤素、(C1-C4)卤代烷基、(C1-C4)卤代烷氧基、硝基、(C1-C4)烷基、(C1-C4)烷氧基、(C1-C4)烷基磺酰基、(C1-C4)烷氧基羰基或(C1-C4)烷基羰基;
RD 3为氢、(C1-C4)烷基、(C2-C4)烯基或(C2-C4)炔基;
RD 4为卤素、硝基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)卤代烷氧基、(C3-C6)环烷基、苯基、(C1-C4)烷氧基、氰基、(C1-C4)烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)烷氧基羰基或(C1-C4)烷基羰基;
RD 5为氢、(C1-C6)烷基、(C3-C6)环烷基、(C2-C6)烯基、(C2-C6)炔基、(C5-C6)环烯基、苯基或3至6元杂环基,所述杂环基含有vD个选自氮、氧和硫的杂原子,其中(C1-C6)烷基、(C3-C6)环烷基、(C2-C6)烯基、(C2-C6)炔基、(C5-C6)环烯基、苯基或3至6元杂环基被vD个选自以下的取代基取代:卤素、(C1-C6)烷氧基、(C1-C6)卤代烷氧基、(C1-C2)烷基亚磺酰基、(C1-C2)烷基磺酰基、(C3-C6)环烷基、(C1-C4)烷氧基羰基、(C1-C4)烷基羰基和苯基,并且在环状基团的情况下,还可以为(C1-C4)烷基和(C1-C4)卤代烷基;
RD 6为氢、(C1-C6)烷基、(C2-C6)烯基或(C2-C6)炔基,其中(C1-C6)烷基、(C2-C6)烯基或(C2-C6)炔基被vD个取代基取代,所述取代基选自卤素、羟基、(C1-C4)烷基、(C1-C4)烷氧基和(C1-C4)烷硫基,或者
RD 5和RD 6与它们所连的氮原子一起形成吡咯烷基或哌啶基;
RD 7为氢、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、(C1-C6)烷基、(C3-C6)环烷基,其中(C1-C6)烷基、(C3-C6)环烷基被vD个取代基取代,所述取代基选自卤素、(C1-C4)烷氧基、(C1-C6)卤代烷氧基和(C1-C4)烷硫基,并且在环状基团的情况下,还可以为(C1-C4)烷基和(C1-C4)卤代烷基;
nD为0、1或2;
mD为1或2;
vD为0、1、2或3;
其中,优选N-酰基磺酰胺类化合物,例如下面的式(S4a),所述化合物已知于例如WO-A-97/45016
其中
RD 7为(C1-C6)烷基、(C3-C6)环烷基,其中(C1-C6)烷基、(C3-C6)环烷基被vD个取代基取代,所述取代基选自卤素、(C1-C4)烷氧基、(C1-C6)卤代烷氧基和(C1-C4)烷硫基,并且在环状基团的情况下,还可以为(C1-C4)烷基和(C1-C4)卤代烷基;
RD 4为卤素、(C1-C4)烷基、(C1-C4)烷氧基、CF3;
mD为1或2;
vD为0、1、2或3;
还优选酰基氨磺酰基苯甲酰胺,例如下面的式(S4b),其已知于例如WO-A-99/16744,
例如下述化合物,其中
RD 5=环丙基且(RD 4)=2-OMe(“N-[[4-[(环丙基氨基)羰基]苯基]磺酰基]-2-甲氧基苯甲酰胺(cyprosulfamide)”,S4-1),
RD 5=环丙基且(RD 4)=5-Cl-2-OMe(S4-2),
RD 5=乙基且(RD 4)=2-OMe(S4-3),
RD 5=异丙基且(RD 4)=5-Cl-2-OMe(S4-4)且
RD 5=异丙基且(RD 4)=2-OMe(S4-5)
并且优选式(S4c)的N-酰基氨磺酰基苯基脲类化合物,所述化合物已知于例如EP-A-365484,
其中
RD 8和RD 9各自独立地为氢、(C1-C8)烷基、(C3-C8)环烷基、(C3-C6)烯基、(C3-C6)炔基,
RD 4为卤素、(C1-C4)烷基、(C1-C4)烷氧基、CF3
mD为1或2;
例如
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲、1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲、1-[4-(N-4,5-二甲基苯甲酰基氨磺酰基)苯基]-3-甲基脲。
S5)羟基芳族化合物类以及芳族-脂族羧酸衍生物类的活性化合物(S5),例如3,4,5-三乙酰氧基苯甲酸乙酯、3,5-二甲氧基-4-羟基苯甲酸、3,5-二羟基苯甲酸、4-羟基水杨酸、4-氟水杨酸、2-羟基肉桂酸、2,4-二氯肉桂酸,如WO-A-2004/084631、WO-A-2005/015994、WO-A-2005/016001所记载。
S6)1,2-二氢喹喔啉-2-酮类活性化合物(S6),例如1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮、1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-硫酮、1-(2-氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮氢氯化物、1-(2-甲基磺酰基氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮,如WO-A-2005/112630所记载。
S7)式(S7)的化合物,如WO-A-1998/38856所记载,
其中符号和指数具有如下含义:
RE 1、RE 2各自独立地为卤素、(C1-C4)烷基、(C1-C4)烷氧基、(C1-C4)卤代烷基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、硝基;
AE为COORE 3或COSRE 4
RE 3、RE 4各自独立地为氢、(C1-C4)烷基、(C2-C6)烯基、(C2-C4)炔基、氰基烷基、(C1-C4)卤代烷基、苯基、硝基苯基、苄基、卤代苄基、吡啶基烷基和烷基铵,
nE 1为0或1
nE 2、nE 3各自独立地为0、1或2,
优选联苯基甲氧基乙酸、联苯基甲氧基乙酸乙酯、联苯基甲氧基乙酸甲酯(CAS注册号41858-19-9)(S7-1)。
S8)式(S8)的化合物,记载于WO-A-98/27049,
其中
XF为CH或N,
在XF=N的情况下nF为0至4的整数且
在XF=CH的情况下nF为0至5的整数,
RF 1为卤素、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、硝基、(C1-C4)烷硫基、(C1-C4)-烷基磺酰基、(C1-C4)烷氧基羰基、任选取代的苯基、任选取代的苯氧基,
RF 2为氢或(C1-C4)烷基
RF 3为氢、(C1-C8)烷基、(C2-C4)烯基、(C2-C4)炔基、或芳基,其中每个前述含碳基团为未取代的或被一个或多个、优选最高达三个相同或不同的选自卤素和烷氧基的基团取代;或其盐,
优选下述化合物,其中
XF为CH,
nF为0至2的整数,
RF 1为卤素、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基,
RF 2为氢或(C1-C4)烷基,
RF 3为氢、(C1-C8)烷基、(C2-C4)烯基、(C2-C4)炔基、或芳基,其中每个前述含碳基团为未取代的或被一个或多个、优选最高达三个相同或不同的选自卤素和烷氧基的基团取代;或其盐。
S9)3-(5-四唑基羰基)-2-喹诺酮类活性化合物(S9),例如
1,2-二氢-4-羟基-1-乙基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号:219479-18-2)、1,2-二氢-4-羟基-1-甲基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号:95855-00-8),记载于WO-A-1999/000020。
S10)式(S10a)或式(S10b)的化合物
记载于WO-A-2007/023719和WO-A-2007/023764
其中
RG 1为卤素、(C1-C4)烷基、甲氧基、硝基、氰基、CF3、OCF3,
YG、ZG彼此独立地为O或S,
nG为0至4的整数
RG 2为(C1-C16)烷基、(C2-C6)烯基、(C3-C6)环烷基、芳基、苄基、卤代苄基、
RG 3为氢或(C1-C6)烷基。
S11)氧基亚氨基化合物类活性化合物(S11),其已知作为拌种组合物,例如“解草腈(oxabetrinil)”((Z)-1,3-二氧戊环-2-基-甲氧基亚氨基(苯基)乙腈)(S11-1),其已知作为黍/高粱的拌种安全剂,用于抵抗异丙甲草胺(metolachlor)的损害,“氟草肟(fluxofenim)”(1-(4-氯苯基)-2,2,2-三氟-1-乙酮O-(1,3-二氧戊环-2-基甲基)肟)(S11-2),其已知作为黍/高粱的拌种安全剂用于抵抗异丙甲草胺的损害,以及“解草胺腈(cyometrinil)”或“CGA-43089”((Z)-氰基甲氧基亚氨基(苯基)乙腈)(S11-3),其已知作为黍/高粱的拌种安全剂用于抵抗异丙甲草胺的损害。
S12)异硫代苯并二氢吡喃酮类活性化合物(S12),例如[(3-氧代-1H-2-苯并硫基吡喃-4(3H)-亚基)甲氧基]乙酸甲酯(CAS注册号205121-04-6)(S12-1)及WO-A-1998/13361中的相关化合物。
S13)(S13)类的一种或多种化合物:“萘二甲酸酐”(1,8-萘二甲酸酐)(S13-1),其已知为玉米的拌种安全剂用于抵抗硫代氨基甲酸盐除草剂的损害,“解草啶(fenclorim)”(4,6-二氯-2-苯基嘧啶)(S13-2),其已知为用于已播种水稻抵抗丙草胺(pretilachlor)的安全剂,“解草胺(flurazole)”(2-氯-4-三氟甲基-1,3-噻唑-5-羧酸苯甲酯)(S13-3),其已知作为黍/高粱的拌种安全剂,用于抵抗甲草胺(alachlor)和异丙甲草胺(metolachlor)的损害,American Cyanamid的“CL304415”(CAS登记号31541-57-8)(4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸)(S13-4),其已知作为玉米抗咪唑啉酮损害的安全剂,Nitrokemia的“MG191”(CAS登记号96420-72-3)(2-二氯甲基-2-甲基-1,3-二氧戊环)(S13-5),其已知作为玉米的安全剂,Nitrokemia的“MG-838”(CAS注册号133993-74-5)(1-氧杂-4-氮杂螺[4.5]癸烷-4-二硫代羟酸2-丙烯酯)(S13-6),“乙拌磷(disulfoton)”(S-2-乙硫基乙基二硫代磷酸O,O-二乙酯)(S13-7),“增效磷(dietholate)”(O-苯基硫代磷酸O,O-二乙酯)(S13-8),“mephenate”(甲基氨基甲酸4-氯苯酯)(S13-9)。
S14)除对有害植物具有除草作用外,还对作物植物例如稻具有安全剂作用的活性化合物,例如“哌草丹(dimepiperate)”或“MY-93”(S-1-甲基-1-苯基乙基哌啶-1-硫代碳酸酯),其已知作为稻的安全剂,抵抗除草剂禾草敌(molinate),“杀草隆(daimuron)”或“SK23”(1-(1-甲基-1-苯基乙基)-3-对甲苯基脲),其已知作为稻的安全剂,抵抗除草剂唑吡嘧磺隆(imazosulfuron),“苄草隆(cumyluron)”=“JC-940”(3-(2-氯苯基甲基)-1-(1-甲基-1-苯基乙基)脲,见JP-A-60087254),其已知作为稻的安全剂抵抗某些除草剂损害,“苯草酮(methoxyphenone)”或“NK049”(3,3'-二甲基-4-甲氧基苯甲酮),其已知作为稻的安全剂抵抗某些除草剂损害,Kumiai的“CSB”(1-溴-4-(氯甲基磺酰基)苯),(CAS登记号54091-06-4),其已知作为稻的安全剂抗某些除草剂造成的损害。
S15)式(S15)的化合物或其互变异构体
如WO-A-2008/131861和WO-A-2008/131860中所记载
其中
RH 1为(C1-C6)卤代烷基并且
RH 2为氢或卤素并且
RH 3、RH 4各自彼此独立地为氢、(C1-C16)烷基、(C2-C16)烯基或(C2-C16)炔基,其中(C1-C16)烷基、(C2-C16)烯基或(C2-C16)炔基各自为未取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)烷硫基、(C1-C4)烷基氨基、二[(C1-C4)烷基]氨基、[(C1-C4)烷氧基]羰基、[(C1-C4)卤代烷氧基]羰基、未取代的或取代的(C3-C6)环烷基、未取代或取代的苯基、以及未取代或取代的杂环基、或(C3-C6)环烷基、(C4-C6)环烯基、在环一侧稠合至4元至6元饱和或不饱和碳环的(C3-C6)环烷基,或在环一侧稠合至4元至6元饱和或不饱和碳环的(C4-C6)环烯基,其中最后4个基团各自为未取代的或被一个或多个选自下面的基团取代:卤素、羟基、氰基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)烷硫基、(C1-C4)烷基氨基、二[(C1-C4)烷基]氨基、[(C1-C4)烷氧基]羰基、[(C1-C4)卤代烷氧基]-羰基、未取代的或取代的(C3-C6)环烷基、未取代的或取代的苯基,以及未取代的或取代的杂环基,
或者
RH 3为(C1-C4)-烷氧基、(C2-C4)烯氧基、(C2-C6)炔氧基或(C2-C4)卤代烷氧基
并且
RH 4为氢或(C1-C4)-烷基或
RH 3和RH 4与其直接相连的氮原子一起为四至八元杂环,其中除氮原子外还可包含其他环杂原子,优选最多两个选自N、O和S的其他环杂原子,并且其为未取代的或被一个或多个选自以下的基团取代:卤素、氰基、硝基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基和(C1-C4)烷硫基。
S16)主要用作除草剂但是对作物植物也具有安全作用的活性化合物,例如(2,4-二氯苯氧基)乙酸(2,4-D)、(4-氯苯氧基)乙酸、(R,S)-2-(4-氯-邻甲苯氧基)丙酸(2甲4氯丙酸(mecoprop))、4-(2,4-二氯苯氧基)丁酸(2,4-DB)、(4-氯-邻甲苯氧基)乙酸(MCPA)、4-(4-氯-邻甲苯氧基)丁酸、4-(4-氯苯氧基)丁酸、3,6-二氯-2-甲氧基苯甲酸(麦草畏(dicamba))、3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor-ethyl)。
影响植物成熟的物质:
在混合物制剂或在桶混制剂(tank mix)中可用于式(I)化合物的配伍成分(Combination partner)为,例如基于抑制以下物质的已知活性成分:例如1-氨基环丙烷-1-羧酸盐合酶、1-氨基环丙烷-1-羧酸盐氧化酶和乙烯受体,例如ETR1、ETR2、ERS1、ERS2或EIN4,例如记载于Biotechn.Adv.2006,24,357-367;Bot.Bull.Acad.Sin.199,40,1-7或Plant Growth Reg.1993,13,41-46以及其中所引用的文献。
影响植物成熟并且可以与式(I)化合物结合的已知物质的实例包括以下的活性化合物(所述化合物根据国际标准化组织(ISO)指定的通用名称或根据化学名或根据编号命名)并且总是包括所有使用形式,例如酸、盐、酯和异构体,例如立体异构体和旋光异构体。在该名单中,提及一种或者在某些情况下多于一种的应用形式:
根瘤菌毒素、2-氨基乙氧基乙烯基甘氨酸(AVG)、甲氧基乙烯基甘氨酸(MVG)、乙烯基甘氨酸、氨基氧基乙酸、西奈芬净(sinefungin)、s-腺苷高半胱氨酸(S-adenosylhomocysteine)、硫代丁酸2-酮基-4-甲酯、(异亚丙基)氨基氧基乙酸2-(甲氧基)-2-氧代乙酯、(异亚丙基)氨基氧基乙酸2-(己氧基)-2-氧代乙酯、(环亚己基)氨基氧基乙酸2-(异亚丙基)-2-氧代乙酯、腐胺(putrescine)、亚精胺(spermidine)、精胺(spermine)、1,8-二氨基-4-氨基乙基辛烷、L-刀豆酸(L-canaline)、丁酰肼、1-氨基环丙基-1-羧酸甲酯、N-甲基-1-氨基环丙基-1-羧酸、1-氨基环丙基-1-甲酰胺、取代的1-氨基环丙基-1-羧酸衍生物,记载于DE3335514、EP30287、DE2906507或US5123951中;1-氨基环丙基-1-羟肟酸、1-甲基环丙烯、3-甲基环丙烯、1-乙基环丙烯、1-正丙基环丙烯、1-环丙烯基甲醇、香芹酮、丁香油酚、环丙-1-烯-1-基乙酸钠、环丙-2-烯-1-基乙酸钠、3-(环丙-2-烯-1-基)丙酸钠、3-(环丙-1-烯-1-基)丙酸钠、茉莉酸、茉莉酮酸甲酯、茉莉酮酸乙酯。
影响植物健康和萌芽的物质:
在混合物制剂或在桶混制剂中可用于式(I)化合物的配伍成分的实例包括已知的影响植物健康的活性成分(所述成分根据国际标准化组织(ISO)指定的通用名称或根据化学名称或根据编号命名并且总是包括所有使用形式,如酸、盐、酯和异构体,如立体异构体和旋光异构体):肌氨酸、苯基丙氨酸、色氨酸、N'-甲基-1-苯基-1-N,N-二乙基氨基甲烷磺酰胺、胡萝卜-半乳醛聚糖,如WO2010017956所记载,4-氧代-4-[(2-苯乙基)氨基]丁酸、4-{[2-(1H-吲哚-3-基)乙基]氨基}-4-氧代丁酸、4-[(3-甲基吡啶-2-基)氨基]-4-氧代丁酸、尿囊素、5-氨基乙酰丙酸、(2S,3R)-2-(3,4-二羟基苯基)-3,4-二氢-2H-色烯-3,5,7-三醇以及记载于WO2010122956中的结构相关的儿茶酚、2-羟基-4-(甲基硫烷基)丁酸、(3E,3αR,8βS)-3-({[(2R)-4-甲基-5-氧代-2,5-二氢呋喃-2-基]氧代}亚甲基)-3,3α,4,8β-四氢-2H-茚基[1,2-b]呋喃-2-酮以及记载于EP2248421的同系内酯、脱落酸、(2Z,4E)-5-[6-乙炔基-1-羟基-2,6-二甲基-4-氧代环己-2-烯-1-基]-3-甲基戊-2,4-二烯酸、(2Z,4E)-5-[6-乙炔基-1-羟基-2,6-二甲基-4-氧代环己-2-烯-1-基]-3-甲基戊-2,4-二烯酸甲酯、4-苯基丁酸、4-苯基丁酸钠、4-苯基丁酸钾。
除草剂或植物生长调节剂:
在混合物制剂或在桶混制剂中可用于式(I)化合物的配伍组分为,例如基于抑制以下物质的已知活性化合物:例如乙酰乳酸合酶、乙酰基-CoA羧化酶、纤维素合酶、烯醇式丙酮酰莽草酸-3-磷酸合酶、谷氨酰胺合酶、对羟基苯基丙酮酸盐加双氧酶、八氢番茄红素脱氢酶(phytoendesaturase)、光合体系I、光合体系II、原卟啉原氧化酶(protoporphyrinogen oxidase),记载于例如Weed Research26(1986)441-445或“The Pesticide Manual”,第14版,The British CropProtection Council and the Royal Soc.of Chemistry,2006以及其中所引用的文献。
可与式(I)化合物结合的已知除草剂或植物生长调节剂的实例包括以下活性化合物(所述化合物根据国际标准化组织(ISO)指定的通用名称或根据化学名称或根据编号命名)并且总是包括所有使用形式,例如酸、盐、酯和异构体,例如立体异构体和旋光异构体。在该名单中,提及一种或者在某些情况下多于一种的应用形式:
乙草胺(acetochlor)、活化酯(acibenzolar)、苯并噻二唑(acibenzolar-S-methyl)、三氟羧草醚(acifluorfen)、三氟羧草醚钠(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、禾草灭钠(alloxydim-sodium)、莠灭净(ametryne)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、氨草啶(aminopyralid)、杀草强(amitrole)、氨基磺酸铵、环丙嘧啶醇(ancymidol)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、叠氮津(aziprotryn)、氟丁酰草胺(beflubutamid)、草除灵(benazolin、benazolin-ethyl)、bencarbazone、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、地散磷(bensulide)、苄嘧磺隆(bensulfuron、bensulfuron-methyl)、灭草松(bentazone)、双苯嘧草酮(benzfendizone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟磺胺草(benzofluor)、新燕灵(benzoylprop)、bicyclopyrone、甲羧除草醚(bifenox)、双丙氨酰膦(bilanafos)、双丙氨酰膦钠(bilanafos-sodium)、双草醚(bispyribac)、双草醚钠(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、氯溴隆(bromuron)、特克草(buminafos)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁苯草酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑草酯(carfentrazone)、唑草乙酯(carfentrazone-ethyl)、甲氧除草醚(chlomethoxyfen)、草灭畏(chloramben)、炔禾灵(chlorazifop)、炔禾灵丁酯(chlorazifop-butyl)、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam)、伐草克(chlorfenac、chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯甲丹(chlorflurenol)、氯甲丹甲酯(chlorflurenol-methyl))、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron、chlorimuron-ethyl)、矮壮素(chlormequat-chloride)、草枯醚(chlornitrofen)、氯酞酰亚胺(chlorophthalim)、氯酞酸甲酯(chlorthal-dimethyl)、绿麦隆(chlorotoluron)、氯磺隆(chlorsulfuron)、吲哚酮草酯(cinidon、cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、烯草酮(clethodim)、炔草酸(clodinafop、clodinafop-propargyl)、杀雄嗪酸(clofencet)、异恶草松(clomazone)、氯甲酰草胺(clomeprop)、调果酸(cloprop)、二氯吡啶酸(clopyralid)、氯酯磺草酸(cloransulam、cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环丙酰胺酸(cyclanilide)、环草敌(cycloate)、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron)、氰氟草酯(cyhalofop、cyhalofop-butyl)、莎草快(cyperquat)、环丙津(cyprazine)、环唑草胺(cyprazole)、2,4-D、2,4-DB、杀草隆(daimuron/dymron)、茅草枯(dalapon)、丁酰肼(daminozide)、棉隆(dazomet)、正癸醇、甜菜安(desmedipham)、敌草净(desmetryn)、脱甲苯磺酰基吡唑特(detosyl-pyrazolate(DTP))、燕麦敌(diallate)、麦草畏(dicamba)、敌草腈(dichlobenil)、2,4-滴丙酸(dichlorprop)、高2,4-滴丙酸(dichlorprop-P)、氯甲草(diclofop)、禾草灵(diclofop-methyl)、精禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、乙酰甲草胺(diethatyl、diethatyl-ethyl)、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、氟吡草腙(diflufenzopyr、diflufenzopyr-sodium)、恶唑隆(dimefuron)、调呋酸(dikegulac-sodium)、恶唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、噻节因(dimethipin)、醚磺隆(dimetrasulfuron)、氨氟灵(dinitramine)、地乐酚(dinoseb)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、异丙净(dipropetryn)、敌草快(diquat、diquat-dibromide)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、草止津(eglinazine-ethyl)、茵多酸(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron、ethametsulfuron-methyl)、乙烯利(ethephon)、磺噻隆(ethidimuron)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氯氟草醚(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F5331,即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧-1H-四唑-1-基]苯基]乙磺酰胺、F-7967,即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮、2,4,5-涕丙酸(fenoprop)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、精噁唑禾草灵(fenoxaprop-P-ethyl)、fenoxasulfone、四唑酰草胺(fentrazamide)、非草隆(fenuron)、麦草氟(flamprop)、麦草氟-M-异丙酯(flamprop-M-isopropyl)、麦草氟-M-甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、异丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone、flucarbazone-sodium))、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet、thiafluamide)、氟哒嗪草酯(flufenpyr、flufenpyr-ethyl)、氟节胺(flumetralin)、唑嘧磺草胺(flumetsulam)、酰亚胺苯氧乙酸(flumiclorac)、酰亚胺苯氧乙酸戊酯(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、氟草隆(fluometuron)、三氟硝草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen、fluoroglycofen-ethyl)、氟胺草唑(flupoxam)、flupropacil、四氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron、flupyrsulfuron-methyl-sodium)、芴丁酯(flurenol、flurenol-butyl)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、氟氯胺啶(fluroxypyr-meptyl)、呋嘧醇(flurprimidol)、呋草酮(flurtamone)、氟噻乙草酯(fluthiacet、fluthiacet-methyl)、噻唑草酰胺(fluthiamide)、氟磺胺草醚(fomesafen)、甲酰氨磺隆(foramsulfuron)、氯吡脲(forchlorfenuron)、杀木膦(fosamine)、呋氧草醚(furyloxyfen)、赤霉素(gibberillic acid)、草铵膦(glufosinate、glufosinate-ammonium)、精草铵膦(glufosinate-P)、精草铵膦(glufosinate-P-ammonium)、精草铵膦钠(glufosinate-P-sodium)、草甘膦(glyphosate)、草甘膦异丙铵(glyphosate-isopropylammonium)、H-9201,即O-(2,4-二甲基-6-硝基苯基)O-乙基异丙基磷酰氨基硫酸酯、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron、halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氟吡乙禾灵(haloxyfop-ethoxyethyl)、精氟吡乙禾灵(haloxyfop-P-ethoxyethyl)、氟吡甲禾灵(haloxyfop-methyl)、精氟吡甲禾灵(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02,即(2,4-二氯苯氧基)乙酸1-(二甲氧基磷酰基)乙酯、咪草酸(imazamethabenz、imazamethabenz-methyl)、甲氧咪草烟(imazamox、imazamox-ammonium)、甲咪唑烟酸(imazapic)、咪唑烟酸(imazapyr、imazapyr-isopropylammonium)、咪唑喹啉酸(imazaquin、imazaquin-ammonium)、咪唑乙烟酸(imazethapyr、imazethapyr-ammonium)、唑吡嘧磺隆(imazosulfuron)、抗倒胺(inabenfide)、茚草酮(indanofan)、indaziflam、吲哚乙酸(IAA)、4-吲哚-3-基丁酸(IBA)、碘磺隆(iodosulfuron)、碘甲磺隆钠盐(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、ipfencarbazone、丁脒酰胺(isocarbamid)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异恶酰草胺(isoxaben)、异恶氯草酮(isoxachlortole)、异噁唑草酮(isoxaflutole)、异恶草醚(isoxapyrifop)、KUH-043,即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-噁唑、特胺灵(karbutilate)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、马来酰肼(maleic hydrazide)、MCPA、MCPB、2甲4氯丁酸甲酯(MCPB-methyl)、2甲4氯丁酸乙酯(MCPB-ethyl)和2甲4氯丁酸钠(MCPB-sodium)、2甲4氯丙酸(mecoprop)、2甲4氯丙酸钠(mecoprop-sodium)、2甲4氯丙酸丁氧酯(mecoprop-butotyl)、高2甲4氯丙酸丁氧酯(mecoprop-P-butotyl)、高2甲4氯丙酸二甲铵(mecoprop-P-dimethylammonium)、高2甲4氯丙酸2-乙基己酯(mecoprop-P-2-ethylhexyl)、高2甲4氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidide)、甲哌啶(mepiquat-chloride)、甲磺胺磺隆(mesosulfuron、mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、恶唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、metazasulfuron、灭草唑(methazole)、methiopyrsulfuron、methiozolin、苯草酮(methoxyphenone)、甲基杀草隆(methyldymron)、1-甲基环丙烯、异硫氰酸甲酯、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆甲酯(metsulfuron-methyl)、禾草敌(molinate)、庚酰草胺(monalide)、monocarbamide、甲酰胺硫酸盐(monocarbamide dihydrogen sulfate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron、monosulfuron ester)、灭草隆(monuron)、MT128,即6-氯-N-[(2E)-3-氯丙-2-烯-1-基]-5-甲基-N-苯基吡嗪-3-胺、MT-5950,即N-[3-氯-4-(1-甲基乙基)苯基]-2-甲基戊酰胺、NGGC-011、萘丙胺(naproanilide)、敌草胺(napropamide)、萘草胺(naptalam),NC310,即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen)、硝基苯酚钠(异构体混合物)、硝氟草醚(nitrofluorfen)、壬酸、氟草敏(norflurazon)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔恶草酮(oxadiargyl)、恶草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、恶嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、多效唑(paclobutrazole)、百草枯(paraquat)、二氯百草枯(paraquatdichloride)、壬酸、二甲戊灵(pendimethalin)、pendralin、五氟磺草胺(penoxsulam)、甲氯酰草胺(pentanochlor)、环戊恶草酮(pentoxazone)、黄草伏(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、苯敌草(phenmedipham)、乙苯敌草(phenmedipham-ethyl)、氨氯吡啶酸(picloram)、氟吡草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、pirifenop、pirifenop-butyl、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron、primisulfuron-methyl)、烯丙苯噻唑(probenazole)、氟唑草胺(profluazol)、环丙氰津(procyazine)、氨氟乐灵(prodiamine)、环丙氟灵(profluraline)、环苯草酮(profoxydim)、调环酸(prohexadione、prohexadione-calcium)、茉莉酮(prohydrojasmone)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、恶草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone、propoxycarbazone-sodium)、propyrisulfuron、炔苯酰草胺(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、丙炔草胺(prynachlor)、双唑草腈(pyraclonil)、吡草醚(pyraflufen、pyraflufen-ethyl)、pyrasulfotole、吡唑特(pyrazolynate,pyrazolate)、吡嘧磺隆(pyrazosulfuron、pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、丙酯草醚(pyribambenz、pyribambenz-propyl)、异丙酯草醚(pyribambenz-isopropyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、pyridafol、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac、pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac、pyrithiobac-sodium)、pyroxasulfone、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop、quizalofop-ethyl)、精喹禾灵(quizalofop-P、quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、saflufenacil、仲丁通(secbumeton)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SN-106279,即(2R)-2-({7-[2-氯-4-(三氟甲基)苯氧基]-2-萘基}氧代)丙酸甲酯、磺草酮(sulcotrione)、菜草畏(sulfallate,CDEC)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron、sulfometuron-methyl)、草硫膦(sulfosate,glyphosate-trimesium)、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249,即1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸酯、SYP-300,即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫代氧代咪唑啉-4,5-二酮、牧草胺(tebutam)、丁噻隆(tebuthiuron)、四氯硝基苯(tecnacene)、tefuryltrione、tembotrione、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、特丁通(terbumeton)、特丁津(terbuthylazine)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、thiafluamide、噻氟隆(thiazafluron)、噻唑烟酸(thiazopyr)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、thiencarbazone、thiencarbazone-methyl、噻吩磺隆(thifensulfuron)、噻吩磺隆甲酯(thifensulfuron-methyl)、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、topramezone、三甲苯草酮(tralkoxydim)、野燕畏(triallate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、triazofenamide、苯磺隆(tribenuron)、苯磺隆甲酯(tribenuron-methyl)、三氯乙酸(TCA)、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠(trifloxysulfuron-sodium)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron、triflusulfuron-methyl)、三甲隆(trimeturon)、抗倒酯(trinexapac、trinexapac-ethyl)、三氟甲磺隆(tritosulfuron)、tsitodef、烯效唑(uniconazole)、高烯效唑(uniconazole-P)、灭草敌(vernolate)、ZJ-0862,即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苯甲基}苯胺,以及下列化合物:
本发明将通过下面生物实施例进行阐述,但不限制于此。
生物实施例
将单子叶和双子叶作物植物的种子置于木质纤维盆中的砂壤土中,覆以土壤,并在温室中于良好的生长条件下培育。在早叶期(BBCH10–BBCH13)处理测试植物。为了确保在胁迫开始之前均匀的水供给,事先通过堤坝灌溉(dam irrigation)供给所述盆栽植物最大量的水,并且在施用后,将其转移至塑料嵌入物(plastic insert)中以防止随后过快地干燥。将配制成可湿性粉剂(WP)、可湿性颗粒剂(WG)、悬浮浓缩剂(SC)或乳化浓缩剂(EC)的本发明的化合物的含水悬浮液喷洒至植物的绿色部位,其相当于水施用率600l/ha,并添加0.2%润湿剂(agrotin)。施用物质后立即对植物进行胁迫处理(冷或干旱胁迫)。对于冷胁迫处理,将植物保持在以下的控制条件下:
“白天”:在8℃下光照12小时
“夜晚”:在1℃下无光照12小时
干旱胁迫通过在以下条件下缓慢干燥而引起:
“白天”:在26℃下光照14小时
“夜晚”:在18℃下无光照10小时
各个胁迫阶段的持续时间主要由未处理的(=用不含试验化合物的空白制剂处理)胁迫对照植物的状态确定并且因此随作物而变化。在未处理的胁迫对照植物中观察到不可逆的损害时立刻停止(通过重新灌溉或将其转移至具有良好生长条件的温室)。对于双子叶作物,例如油菜和大豆,干旱胁迫阶段的持续时间在3天至5天之间,对于单子叶作物例如小麦、大麦或玉米,在6天至10天之间变化。冷胁迫阶段的持续时间在12天至14天之间。
胁迫阶段结束后为大约5-7天的恢复阶段,在恢复阶段中将植物再次保持在温室中的良好生长条件下。为了排除因测试化合物的任何杀真菌作用而观察到的对效果的任何影响,还确保测试在没有真菌感染和没有感染压力下进行。
在恢复阶段终止后,损害强度以与相同生长期(age)(在干旱胁迫的情况下)或相同的生长阶段(在冷胁迫的情况下)的未处理的、未受胁迫的对照组的目测对比进行评定。损害强度首先以百分比记录(100%=植物已经死亡,0%=与对照植物相同)。然后用这些数值通过下面式子计算测试化合物的功效(=由于施用物质使损害强度降低的百分比):
EF:功效(%)
DVus:未处理的受胁迫的对照组的损害值
DVts:经测试化合物处理的植物的损害值
下表列出在每种情况下相同测试的三次结果的平均值。
在干旱胁迫下所选择的式(I)化合物的功效:
表A1:
表A2:
表A3:
在上表中:
BRSNS=芸苔(Brassica napus)
TRZAS=小麦(Triticum aestivum)
ZEAMX=玉米(Zea mays)
使用其他式(I)的化合物施用于不同植物品种也获得了类似的结果。
Claims (14)
1.式(I)的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯或5-(环己-2-烯-1-基)戊-2-烯-4-炔或其盐,
其中
[X-Y]代表部分:
Q代表部分Q-1至Q-4
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表烷基、烯基、炔基、烯基烷基、炔基烷基、烷氧基烷基、羟基烷基、卤代烷基、卤代烯基、卤代炔基、卤代烷氧基烷基、烷氧基卤代烷基、卤代烷氧基卤代烷基、烷硫基烷基,
R2代表氢、烷基、烯基、烯基烷基、烷氧基烷基、烷基羰基、芳基羰基、杂芳基羰基、环烷基羰基、烷氧基羰基、烯氧基羰基、芳氧基烷基、芳基烷氧基羰基、芳基烷氧基烷基、芳基烷基、烷氧基烷氧基烷基、烷硫基烷基、三烷基甲硅烷基、烷基(二烷基)甲硅烷基、烷基(二芳基)甲硅烷基、芳基(二烷基)甲硅烷基、环烷基(二烷基)甲硅烷基、卤代(二烷基)甲硅烷基、三烷基甲硅烷基烷氧基烷基、三烷基甲硅烷基烷基,
R3和R4彼此独立地代表烷氧基、烷氧基烷氧基、环烷基烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、芳基烷氧基、芳基烷硫基或与其所连接的原子一起形成氧代基团、羟基亚氨基、烷氧基亚氨基、环烷氧基亚氨基、环烷基烷氧基亚氨基、芳基烷氧基亚氨基或任选可被进一步取代的5元至7元杂环,
R5和R6彼此独立地代表氢、卤素、烷基、卤代烷基,
R7代表卤素、烷基、卤代烷基、卤代烷氧基、卤代烷氧基烷基、卤代烷氧基卤代烷基、烷氧基卤代烷基、炔氧基卤代烷基、烯氧基卤代烷基、烷硫基、卤代烷硫基、芳基、芳基烷基、杂芳基、杂芳基烷基,
R6和R7与其所键合的原子形成完全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代,
R8代表氢、烷基、烷氧基烷基、环烷基、环烷基烷基、芳基、芳基烷基、杂芳基烷基、二芳基烷基、三芳基烷基、烯基、烯基烷基、环烯基烷基、炔基烷基、三烷基甲硅烷基烷氧基烷基、烷氧基烷氧基烷基、烷硫基烷基、卤代烷基、芳基磺酰基烷基、三烷基甲硅烷基、烷基(二芳基)甲硅烷基、烷基(二烷基)甲硅烷基、二烷基氨基烷基,
R9代表氢、烷基、环烷基、卤素、烯基烷基、炔基烷基、卤代烷基、炔基、烯基、氰基烷基、环烷基烷基、芳基烷基、杂芳基烷基、烷基羰基、烷氧基羰基、烯氧基羰基、烯基烷氧基羰基、芳基烷氧基羰基、环烷氧基羰基、环烷基烷氧基羰基、烷基磺酰基、芳基磺酰基、环烷基磺酰基、烷基亚磺酰基、芳基亚磺酰基、环烷基亚磺酰基、烷氧基羰基烷基、羟基羰基烷基、芳基烷氧基羰基烷基、环烷基烷氧基羰基烷基、烷氧基羰基环烷基、羟基羰基环烷基、芳基烷氧基羰基环烷基、烯氧基羰基环烷基、氨基羰基环烷基、烷基氨基羰基环烷基、环烷基氨基羰基环烷基、烷氧基羰基环烯基、羟基羰基环烯基、二烷基氨基烷基、羟基羰基杂环基、烷氧基羰基杂环基、烯氧基羰基杂环基、烯基烷氧基羰基杂环基、芳基烷氧基羰基杂环基、环烷氧基羰基杂环基、环烷基烷氧基羰基杂环基、氨基羰基杂环基、烷基氨基羰基杂环基、二烷基氨基羰基杂环基、环烷基氨基羰基杂环基、芳基烷基氨基羰基杂环基、烯基氨基羰基杂环基、羟基羰基杂环基烷基、烷氧基羰基杂环基烷基、羟基羰基环烷基烷基、烷氧基羰基环烷基烷基、羟基、烷氧基,
R10代表氢、烷基、环烷基、卤素、烷基烯基、卤代烷基、炔基、烯基、氰基烷基、芳基烷基、杂芳基烷基、烷基羰基、烷氧基羰基、烷基磺酰基、芳基磺酰基、环烷基磺酰基、烷基亚磺酰基、芳基亚磺酰基、环烷基亚磺酰基、烷氧基羰基烷基
或
R9和R10与其所连接的氮形成任选被卤素、烷基、卤代烷基、烷氧基、烷氧基羰基、环烷氧基羰基、环烷基烷氧基羰基、烯氧基羰基、羟基羰基、氨基羰基、烷基氨基羰基、环烷基氨基羰基、芳基烷基氨基羰基取代的三至八元环,其任选被O、S或N间隔
或
R9和R10一起为任选取代的硫亚胺或脒基团的部分或一起形成亚氨基正磷。
2.权利要求1的式(I)的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯或5-(环己-2-烯-1-基)戊-2-烯-4-炔或其盐,其中
[X-Y]代表部分:
Q代表Q-1至Q-4部分
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表(C1-C8)烷基、(C2-C8)烯基、(C2-C8)炔基、(C2-C8)烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、羟基-(C1-C8)烷基、(C1-C8)卤代烷基、(C2-C8)卤代烯基、(C2-C8)卤代炔基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C3-C8)环烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷硫基-(C1-C8)烷基,
R2代表氢、(C1-C8)烷基、(C2-C8)烯基、(C2-C8)烯基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷基羰基、芳基羰基、杂芳基羰基、(C3-C8)环烷基羰基、(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、芳基-(C1-C8)烷氧基羰基、芳基-(C1-C8)烷氧基-(C1-C8)烷基、芳氧基-(C1-C8)烷基、芳基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷硫基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基、(C1-C8)烷基-(二-(C1-C8)烷基)甲硅烷基、(C1-C8)烷基(二芳基)甲硅烷基、芳基(二-(C1-C8)烷基)甲硅烷基、(C3-C8)环烷基(二-(C1-C6)烷基)甲硅烷基、卤代(二-(C1-C8)烷基)甲硅烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷氧基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷基,
R3和R4彼此独立地代表(C1-C8)烷氧基、(C1-C8)烷氧基-(C1-C8)烷氧基、(C3-C8)环烷基-(C1-C8)烷氧基、(C1-C8)卤代烷氧基、(C1-C8)烷硫基、(C1-C8)卤代烷硫基、芳基-(C1-C8)烷氧基、芳基-(C1-C8)烷硫基或与其所连接的原子一起形成氧代基团、羟基亚氨基、(C1-C8)烷氧基亚氨基、(C3-C8)环烷氧基亚氨基、(C3-C8)环烷基-(C1-C8)烷氧基亚氨基、芳基-(C1-C8)烷氧基亚氨基或任选被进一步取代的5元至7元杂环,
R5和R6彼此独立地代表氢、卤素、(C1-C8)烷基、(C1-C8)卤代烷基,
R7代表卤素、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C8)卤代烷氧基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)炔氧基-(C1-C8)卤代烷基、(C1-C8)烯氧基-(C1-C8)卤代烷基、(C1-C8)烷硫基、(C1-C8)卤代烷硫基、任选取代的苯基、芳基-(C1-C8)烷基、杂芳基、杂芳基-(C1-C8)烷基,
R6和R7与其所键合的原子形成完全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代,
R8代表氢、(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、(C3-C8)环烷基、(C3-C8)环烷基-(C1-C8)烷基、任选取代的苯基、芳基-(C1-C8)烷基、杂芳基-(C1-C8)烷基、二芳基-(C1-C8)烷基、三芳基-(C1-C8)烷基、(C2-C8)烯基、(C2-C8)烯基-(C1-C8)烷基、(C4-C8)环烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷硫基-(C1-C8)烷基、(C1-C8)卤代烷基、芳基磺酰基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基、(C1-C8)烷基-(二芳基)甲硅烷基、(C1-C8)烷基-(二-(C1-C8)烷基)甲硅烷基、二-(C1-C8)烷基氨基-(C1-C8)烷基,
R9代表氢、(C1-C8)烷基、(C3-C8)环烷基、卤素、(C2-C8)烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、(C1-C8)卤代烷基、(C2-C8)炔基、(C2-C8)烯基、氰基-(C1-C8)烷基、(C3-C8)环烷基-(C1-C8)烷基、芳基-(C1-C8)烷基、杂芳基-(C1-C8)烷基、(C1-C8)烷基羰基、(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、(C2-C8)烯基-(C1-C8)烷氧基羰基、芳基-(C1-C8)烷氧基羰基、(C3-C8)环烷氧基羰基、(C3-C8)环烷基-(C1-C8)烷氧基羰基、(C1-C8)烷基磺酰基、芳基磺酰基、(C3-C8)环烷基磺酰基、(C1-C8)烷基亚磺酰基、芳基亚磺酰基、(C3-C8)环烷基亚磺酰基、(C1-C8)烷氧基羰基-(C1-C8)烷基、羟基羰基-(C1-C8)烷基、芳基-(C1-C8)烷氧基羰基-(C1-C8)烷基、(C3-C8)环烷基-(C1-C8)烷氧基羰基-(C1-C8)烷基、(C1-C8)烷氧基羰基-(C3-C8)环烷基、羟基羰基-(C3-C8)环烷基、芳基-(C1-C8)烷氧基羰基-(C3-C8)环烷基、(C2-C8)烯氧基羰基-(C3-C8)环烷基、氨基羰基-(C3-C8)环烷基、(C1-C8)烷基氨基羰基-(C3-C8)环烷基、(C3-C8)环烷基氨基羰基-(C3-C8)环烷基、(C1-C8)烷氧基羰基-(C4-C8)环烯基、羟基羰基-(C4-C8)环烯基、二-(C1-C8)烷基氨基-(C1-C8)烷基、羟基羰基杂环基、(C1-C8)烷氧基羰基杂环基、(C2-C8)烯氧基羰基杂环基、(C2-C8)烯基-(C1-C8)烷氧基羰基杂环基、芳基-(C1-C8)烷氧基羰基杂环基、(C3-C8)环烷氧基羰基杂环基、(C3-C8)环烷基-(C1-C8)烷氧基羰基杂环基、氨基羰基杂环基、(C1-C8)烷基氨基羰基杂环基、二-(C1-C8)烷基氨基羰基杂环基、(C3-C8)环烷基氨基羰基杂环基、芳基-(C1-C8)烷基氨基羰基杂环基、(C2-C8)烯基氨基羰基杂环基、羟基羰基杂环基-(C1-C8)烷基、(C1-C8)烷氧基羰基杂环基-(C1-C8)烷基、羟基羰基-(C3-C8)环烷基-(C1-C8)烷基、(C1-C8)烷氧基羰基-(C3-C8)环烷基-(C1-C8)烷基、羟基、(C1-C8)烷氧基,
R10代表氢、(C1-C8)烷基、(C3-C8)环烷基、卤素、(C1-C8)烷基-(C1-C8)烯基、(C1-C8)卤代烷基、(C2-C8)炔基、(C2-C8)烯基、氰基-(C1-C8)烷基、芳基-(C1-C8)烷基、杂芳基-(C1-C8)烷基、(C1-C8)烷基羰基、(C1-C8)烷氧基羰基、(C1-C8)烷基磺酰基、芳基磺酰基、(C3-C8)环烷基磺酰基、(C1-C8)烷基亚磺酰基、芳基亚磺酰基、(C3-C8)环烷基亚磺酰基、(C1-C8)烷氧基羰基-(C1-C8)烷基,
或
R9和R10与其所连接的氮形成任选被卤素、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C8)烷氧基、(C1-C8)烷氧基羰基、(C3-C8)环烷氧基羰基、(C3-C8)环烷基-(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、羟基羰基、氨基羰基、(C1-C8)烷基氨基羰基、(C3-C8)环烷基氨基羰基、芳基-(C1-C8)烷基氨基羰基取代的三至八元环,其任选被O、S或N间隔,
或
R9和R10一起形成N-(二-(C1-C6)烷基)亚硫烷基、N-(芳基-(C1-C6)烷基)亚硫烷基、N-(二-(C3-C7)环烷基)亚硫烷基、N-((C1-C6)烷基-(C3-C7)环烷基)亚硫烷基或N,N-二-(C1-C6)烷基亚甲酰基。
3.权利要求1的式(I)的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯或5-(环己-2-烯-1-基)戊-2-烯-4-炔或其盐,其中
[X-Y]代表部分:
Q代表部分Q-1至Q-3
其中R5、R6、R7、R8、R9和R10各自如下定义并且其中箭头代表连接至各个[X-Y]部分的键;
R1代表(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C2-C6)烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、羟基-(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)卤代烯基、(C2-C6)卤代炔基、(C1-C6)卤代烷氧基-(C1-C6)烷基、(C3-C7)环烷基、(C1-C6)烷氧基-(C1-C6)卤代烷基、(C1-C6)卤代烷氧基-(C1-C6)卤代烷基、(C1-C6)烷硫基-(C1-C6)烷基,
R2代表氢、三-(C1-C6)烷基甲硅烷基、(C1-C6)烷基-(二-(C1-C6)烷基)甲硅烷基、(C1-C6)烷基(二芳基)甲硅烷基、芳基(二-(C1-C6)烷基)甲硅烷基、(C3-C7)环烷基(二-(C1-C6)烷基)甲硅烷基、卤代(二-(C1-C6)烷基)甲硅烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷氧基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷基,
R3和R4彼此独立地代表(C1-C6)烷氧基、(C1-C6)烷硫基或与其所连接的原子一起形成氧代基团、羟基亚氨基、(C1-C6)烷氧基亚氨基、(C3-C6)环烷氧基亚氨基、(C3-C6)环烷基-(C1-C6)烷氧基亚氨基、芳基-(C1-C6)烷氧基亚氨基或任选可被进一步取代的5元至7元杂环,
R5和R6彼此独立地代表氢、卤素、(C1-C8)烷基、(C1-C6)卤代烷基,
R7代表卤素、(C1-C8)烷基、(C1-C8)卤代烷基、(C1-C8)卤代烷氧基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)炔氧基-(C1-C8)卤代烷基、(C1-C8)烯氧基-(C1-C8)卤代烷基、(C1-C6)烷硫基、(C1-C6)卤代烷硫基、任选取代的苯基、芳基(C1-C6)烷基、杂芳基、杂芳基-(C1-C6)烷基,
R6和R7与其所键合的原子形成完全饱和的3元至6元环,所述环任选被杂原子间隔并且任选被进一步取代,
R8代表氢、(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、(C3-C7)环烷基、(C3-C7)环烷基-(C1-C6)烷基、任选取代的苯基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、二芳基-(C1-C6)烷基、三芳基-(C1-C6)烷基、(C2-C6)烯基、(C2-C6)烯基-(C1-C6)烷基、(C4-C7)环烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基-(C1-C6)烷氧基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷氧基-(C1-C6)烷基、(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)卤代烷基、芳基磺酰基-(C1-C6)烷基、三-(C1-C6)烷基甲硅烷基、(C1-C6)烷基-(二芳基)甲硅烷基、(C1-C6)烷基-(二-(C1-C6)烷基)甲硅烷基、二-(C1-C6)烷基氨基-(C1-C6)烷基,
R9代表氢、(C1-C6)烷基、(C3-C7)环烷基、卤素、(C2-C6)烯基-(C1-C6)烷基、(C2-C6)炔基-(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)炔基、(C2-C6)烯基、氰基-(C1-C6)烷基、(C3-C7)环烷基-(C1-C6)烷基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、(C1-C6)烷基羰基、(C1-C6)烷氧基羰基、(C2-C6)烯氧基羰基、(C2-C6)烯基-(C1-C6)烷氧基羰基、芳基-(C1-C6)烷氧基羰基、(C3-C7)环烷氧基羰基、(C3-C6)环烷基-(C1-C6)烷氧基羰基、(C1-C6)烷基磺酰基、芳基磺酰基、(C3-C7)环烷基磺酰基、(C1-C6)烷基亚磺酰基、芳基亚磺酰基、(C3-C7)环烷基亚磺酰基、(C1-C6)烷氧基羰基-(C1-C6)烷基、羟基羰基-(C1-C6)烷基、芳基-(C1-C6)烷氧基羰基-(C1-C6)烷基、(C3-C7)环烷基-(C1-C6)烷氧基羰基-(C1-C6)烷基、(C1-C6)烷氧基羰基-(C3-C6)环烷基、羟基羰基-(C3-C6)环烷基、芳基-(C1-C6)烷氧基羰基-(C1-C6)环烷基、(C2-C6)烯氧基羰基-(C3-C6)环烷基、氨基羰基-(C3-C7)环烷基、(C1-C6)烷基氨基羰基-(C3-C7)环烷基、(C3-C7)环烷基氨基羰基-(C3-C7)环烷基、(C1-C6)烷氧基羰基-(C4-C7)环烯基、羟基羰基-(C4-C7)环烯基、二-(C1-C6)烷基氨基-(C1-C6)烷基、羟基羰基杂环基、(C1-C6)烷氧基羰基杂环基、(C2-C6)烯氧基羰基杂环基、(C2-C6)烯基-(C1-C6)烷氧基羰基杂环基、芳基-(C1-C6)烷氧基羰基杂环基、(C3-C7)环烷氧基羰基杂环基、(C3-C7)环烷基-(C1-C6)烷氧基羰基杂环基、氨基羰基杂环基、(C1-C6)烷基氨基羰基杂环基、二-(C1-C6)烷基氨基羰基杂环基、(C3-C7)环烷基氨基羰基杂环基、芳基-(C1-C6)烷基氨基羰基杂环基、(C2-C6)烯基氨基羰基杂环基、羟基羰基杂环基-(C1-C6)烷基、(C1-C6)烷氧基羰基杂环基-(C1-C6)烷基、羟基羰基-(C3-C7)环烷基-(C1-C6)烷基、(C1-C6)烷氧基羰基-(C3-C7)环烷基-(C1-C6)烷基、羟基、(C1-C6)烷氧基,
R10代表氢、(C1-C6)烷基、(C3-C7)环烷基、(C1-C6)烷基-(C1-C6)烯基、(C1-C6)卤代烷基、(C2-C6)炔基、(C2-C6)烯基、氰基-(C1-C6)烷基、芳基-(C1-C6)烷基、杂芳基-(C1-C6)烷基、(C1-C6)烷基羰基、(C1-C6)烷氧基羰基、(C1-C6)烷基磺酰基、芳基磺酰基、(C3-C7)环烷基磺酰基、(C1-C6)烷基亚磺酰基、芳基亚磺酰基、(C3-C7)环烷基亚磺酰基、(C1-C6)烷氧基羰基-(C1-C6)烷基,
R9和R10与其所连接的氮形成任选被氟、氯、溴、碘、(C1-C6)烷基、(C1-C6)卤代烷基、(C1-C6)烷氧基、(C1-C6)烷氧基羰基、(C3-C7)环烷氧基羰基、(C3-C7)环烷基-(C1-C6)烷氧基羰基、(C2-C6)烯氧基羰基、羟基羰基、氨基羰基、(C1-C6)烷基氨基羰基、(C3-C7)环烷基氨基羰基、芳基-(C1-C6)烷基氨基羰基所取代的三至八元环,其任选被O、S或N间隔
或
R9和R10一起形成N-(二-(C1-C6)烷基)亚硫烷基、N-(芳基-(C1-C6)烷基)亚硫烷基、N-(二-(C3-C7)环烷基)亚硫烷基、N-((C1-C6)烷基-(C3-C7)环烷基)亚硫烷基或N,N-二-(C1-C6)烷基亚甲酰基。
4.一种或多种权利要求1至3中任一项的式(I)化合物或其盐用于提高植物中对非生物胁迫耐受性的用途。
5.一种对植物的处理,包括以对增强植物对非生物胁迫因素的抗性有效的无毒性用量施用一种或多种权利要求1至3中任一项的式(I)化合物或其盐。
6.权利要求5的处理,其中所述非生物胁迫条件对应于一种或多种选自以下的条件:热、干旱、冷和干旱胁迫、渗透胁迫、水涝、高的土壤盐度、高的矿物质暴露、臭氧条件、强光条件、有限的氮营养素利用度、有限的磷营养素利用度。
7.一种或多种权利要求1至3中任一项的式(I)化合物或其盐与一种或多种选自杀昆虫剂、引诱剂、杀螨剂、杀真菌剂、杀线虫剂、除草剂、生长调节剂、安全剂、影响植物成熟的物质以及杀细菌剂的活性成分结合喷雾施用于植物和植物部位的用途。
8.一种或多种权利要求1至3中任一项的式(I)化合物或其盐与肥料结合喷雾施用于植物和植物部位的用途。
9.一种或多种权利要求1至3中任一项的式(I)化合物或其盐施用于基因修饰品种、其种子、或施用于这些品种生长的栽培区域的用途。
10.一种用于处理植物的喷雾溶液,其包含对增强植物对非生物胁迫因素的抗性有效的用量的一种或多种权利要求1至3中任一项的式(I)化合物或其盐。
11.包含一种或多种权利要求1至3中任一项的式(I)化合物或其盐的喷雾溶液用于增强植物对非生物胁迫因素抗性的用途。
12.提高选自有用植物、观赏植物、草皮类或树木的植物的胁迫耐受性的方法,所述方法包括将足量的、无毒性用量的一种或多种权利要求1至3中任一项的式(I)化合物或其盐施用至需要相应效果的区域,包括施用至植物、其种子或植物生长的区域。
13.权利要求12的方法,其中在原本相同的生理条件下与未处理植物相比,经如此处理的植物对非生物胁迫的抗性提高至少3%。
14.式(II)的化合物
其中
R1代表(C1-C8)烷基、(C2-C8)烯基、(C2-C8)炔基、(C2-C8)烯基-(C1-C8)烷基、(C2-C8)炔基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、羟基-(C1-C8)烷基、(C1-C8)卤代烷基、(C2-C8)卤代烯基、(C2-C8)卤代炔基、(C1-C8)卤代烷氧基-(C1-C8)烷基、(C3-C8)环烷基、(C1-C8)烷氧基-(C1-C8)卤代烷基、(C1-C8)卤代烷氧基-(C1-C8)卤代烷基、(C1-C8)烷硫基-(C1-C8)烷基,
R2代表氢、(C1-C8)烷基、(C2-C8)烯基、(C2-C8)烯基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷基羰基、芳基羰基、杂芳基羰基、(C3-C8)环烷基羰基、(C1-C8)烷氧基羰基、(C2-C8)烯氧基羰基、芳基-(C1-C8)烷氧基羰基、芳基-(C1-C8)烷氧基-(C1-C8)烷基、芳氧基-(C1-C8)烷基、芳基-(C1-C8)烷基、(C1-C8)烷氧基-(C1-C8)烷氧基-(C1-C8)烷基、(C1-C8)烷硫基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基、(C1-C8)烷基-(二-(C1-C8)烷基)甲硅烷基、(C1-C8)烷基(二芳基)甲硅烷基、芳基(二-(C1-C8)烷基)甲硅烷基、(C3-C8)环烷基(二-(C1-C6)烷基)甲硅烷基、卤代(二-(C1-C8)烷基)甲硅烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷氧基-(C1-C8)烷基、三-(C1-C8)烷基甲硅烷基-(C1-C8)烷基,
R3和R4彼此独立地代表(C1-C8)烷氧基、(C1-C8)烷氧基-(C1-C8)烷氧基、(C3-C8)环烷基-(C1-C8)烷氧基、(C1-C8)卤代烷氧基、(C1-C8)烷硫基、(C1-C8)卤代烷硫基、芳基-(C1-C8)烷氧基、芳基-(C1-C8)烷硫基或与其所连接的原子一起形成氧代基团或5元至7元杂环,例如1,3-二氧杂环戊基、1,3-二氧杂环己基、1,3-二硫杂环戊基、1,3-二噻烷基、1,3-氧硫杂环己基、5-烷基-1,3,5-二噻嗪基、1,3-噁唑烷基环,该杂环可任选被(C1-C6)烷基、(C1-C6)烷氧基羰基、(C3-C6)环烷基、螺-(C3-C6)环烷基、螺-氧杂环丁基进一步取代,和
[M]代表三-[(C1-C6)烷基]甲锡烷基、三-[(C3-C8)环烷基]甲锡烷基、三-[(C1-C6)烷基]锗基、三-[(C3-C8)环烷基]锗基、二-(环戊二烯基)氧锆基、二-(1,2,3,4,5-五甲基环戊二烯基)氧锆基、二-(环戊二烯基)铪氧基、二-(1,2,3,4,5-五甲基环戊二烯基)铪氧基、二-(羟基)硼基、二-[(C1-C6)烷氧基]-硼基、(C1-C6)烷基-1,3,2-二氧杂环戊硼烷-2-基、二-[(C1-C6)烷基]-1,3,2-二氧杂环戊硼烷-2-基、四-[(C1-C6)烷基]-1,3,2-二氧杂环戊硼烷-2-基、1,3,2-二氧杂环己硼烷-2-基、二-[(C1-C6)烷基]-1,3,2-二氧杂环己硼烷-2-基、(C1-C6)烷基-1,3,2-二氧杂环己硼烷-2-基、三-[(C1-C6)烷基]-1,3,2-二氧杂环己硼烷-2-基、2,6,7-三氧杂-1-甲硼烷负离子杂双环[2.2.2]辛烷基、(C1-C6)烷基-2,6,7-三氧杂-1-甲硼烷负离子杂双环[2.2.2]辛烷基、三-[(C1-C6)烷基]铅烷基、三-[(C1-C6)烷基羰基氧基]铅烷基、三-芳基-铅烷基、二-[(C1-C6)烷基羰基氧基]-芳基铅烷基、二-[(C1-C6)烷基]-铝基、二-[(C1-C6)环烷基]-铝基、二氯铝基、氯代镁基、溴代镁基、氯代锌基、氯代汞基、溴代汞基、(C1-C6)烷基汞基、(C3-C6)环烷基汞基、三-[(C1-C6)烷基]甲硅烷基、(C1-C6)烷基-[二-(C1-C6)烷基]甲硅烷基、(C1-C6)烷基-二-(芳基)甲硅烷基、芳基-二-[(C1-C6)烷基)]甲硅烷基、(C3-C7)环烷基-二-[(C1-C6)烷基]甲硅烷基。
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- 2012-03-28 BR BR112013026592A patent/BR112013026592A2/pt not_active Application Discontinuation
- 2012-03-28 US US14/111,741 patent/US9185914B2/en not_active Expired - Fee Related
- 2012-03-28 JP JP2014504242A patent/JP6059203B2/ja not_active Expired - Fee Related
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- 2012-03-28 EA EA201391529A patent/EA201391529A1/ru unknown
- 2012-03-28 ES ES12710747.2T patent/ES2593809T3/es active Active
- 2012-03-28 CN CN201280028961.2A patent/CN103596923A/zh active Pending
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CN111087375A (zh) * | 2019-12-24 | 2020-05-01 | 温州大学新材料与产业技术研究院 | 一种2h-色烯衍生物的制备方法 |
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BR112013026592A2 (pt) | 2016-09-13 |
JP2014511868A (ja) | 2014-05-19 |
EP2697193A1 (de) | 2014-02-19 |
AR090010A1 (es) | 2014-10-15 |
EA201391529A1 (ru) | 2014-08-29 |
EP2697193B1 (de) | 2016-07-06 |
US9185914B2 (en) | 2015-11-17 |
ZA201307418B (en) | 2015-05-27 |
HUE031102T2 (en) | 2017-06-28 |
US20140087949A1 (en) | 2014-03-27 |
AU2012242124A1 (en) | 2013-10-31 |
AU2012242124B2 (en) | 2017-05-25 |
JP6059203B2 (ja) | 2017-01-11 |
WO2012139890A1 (de) | 2012-10-18 |
PL2697193T3 (pl) | 2016-12-30 |
CA2833036A1 (en) | 2012-10-18 |
ES2593809T3 (es) | 2016-12-13 |
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