CN116348456A - 植物生长调节剂化合物 - Google Patents
植物生长调节剂化合物 Download PDFInfo
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- CN116348456A CN116348456A CN202180072272.0A CN202180072272A CN116348456A CN 116348456 A CN116348456 A CN 116348456A CN 202180072272 A CN202180072272 A CN 202180072272A CN 116348456 A CN116348456 A CN 116348456A
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- Prior art keywords
- alkyl
- methyl
- hydrogen
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- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 215
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- 230000007226 seed germination Effects 0.000 claims abstract description 20
- -1 amino-oxycarbonyl Chemical group 0.000 claims description 226
- 239000000203 mixture Substances 0.000 claims description 131
- 239000001257 hydrogen Substances 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 129
- 150000002431 hydrogen Chemical class 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 238000009472 formulation Methods 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000004043 oxo group Chemical group O=* 0.000 claims description 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
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- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 11
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 65
- GITITJADGZYSRL-UHFFFAOYSA-N methyl but-3-enoate Chemical compound COC(=O)CC=C GITITJADGZYSRL-UHFFFAOYSA-N 0.000 description 36
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- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 19
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
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- 235000009973 maize Nutrition 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
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- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 7
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 7
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- XEAIHUDTEINXFG-SNAWJCMRSA-N methyl (e)-hex-3-enoate Chemical compound CC\C=C\CC(=O)OC XEAIHUDTEINXFG-SNAWJCMRSA-N 0.000 description 7
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- 239000005944 Chlorpyrifos Substances 0.000 description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 6
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 6
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- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 6
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- 231100000765 toxin Toxicity 0.000 description 6
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000005820 Prochloraz Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 5
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- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 4
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- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- JGFYQVQAXANWJU-UHFFFAOYSA-M sodium fluoroacetate Chemical compound [Na+].[O-]C(=O)CF JGFYQVQAXANWJU-UHFFFAOYSA-M 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 239000011655 sodium selenate Substances 0.000 description 1
- 235000018716 sodium selenate Nutrition 0.000 description 1
- 229960001881 sodium selenate Drugs 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- NHQVTOYJPBRYNG-UHFFFAOYSA-M sodium;2,4,7-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C2=CC(C(C)C)=CC=C21 NHQVTOYJPBRYNG-UHFFFAOYSA-M 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- NMGNJWORLGLLHQ-UHFFFAOYSA-M sulcofuron-sodium Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 NMGNJWORLGLLHQ-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YJINQJFQLQIYHX-UHFFFAOYSA-N tetradec-11-enyl acetate Chemical compound CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- OUOJIFQQBPKAMU-UHFFFAOYSA-N tetrazol-5-one Chemical compound O=C1N=NN=N1 OUOJIFQQBPKAMU-UHFFFAOYSA-N 0.000 description 1
- YTQVHRVITVLIRD-UHFFFAOYSA-L thallium sulfate Chemical compound [Tl+].[Tl+].[O-]S([O-])(=O)=O YTQVHRVITVLIRD-UHFFFAOYSA-L 0.000 description 1
- 229940119523 thallium sulfate Drugs 0.000 description 1
- 229910000374 thallium(I) sulfate Inorganic materials 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 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
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229950001577 trimetozine Drugs 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-M valinate Chemical compound CC(C)C(N)C([O-])=O KZSNJWFQEVHDMF-UHFFFAOYSA-M 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229940023877 zeatin Drugs 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
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- 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
- A01N43/04—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 one hetero atom
- A01N43/06—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 one hetero atom five-membered rings
- A01N43/08—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 one hetero atom five-membered rings with oxygen as the ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cultivation Of Plants (AREA)
Abstract
披露了具有式(I)的化合物,其中取代基是如权利要求1中所定义的,所述化合物可用作植物生长调节剂和/或种子萌发促进剂。
Description
本发明涉及新的玉米内酯(zealactone)衍生物,涉及用于制备这些衍生物(包括中间体化合物)的方法,涉及包含这些衍生物的种子,涉及包含这些衍生物的植物生长调节剂或种子萌发促进组合物,并且涉及使用这些衍生物控制植物生长、改进植物养分利用效率和/或促进种子萌发的方法。
玉米内酯自身从以下获知:Xiaonan Xie,Takaya Kisugi,Kaori Yoneyama等人,‘Methyl zealactonoate,a novel germination stimulant for root parasitic weedsproduced by maize[甲基玉米内酯,一种由玉蜀黍产生的用于根寄生杂草的新的萌发刺激剂]’,Journal of Pesticide Science[农药科学杂志]2017,42,58-61以及T.V.Charnikhova,K.Gaus,A.Lumbroso等人,‘Zealactones.Novel naturalstrigolactones from maize[玉米内酯,来自玉蜀黍的新的天然独脚金内酯]’,Phytochemistry[植物化学]2017,137,123-131;并且玉米内酯的合成方法从以下获知:M.Yoshimura,M.Dieckmann,P-Y.Dakas等人,‘Total Synthesis and BiologicalEvaluation of Zealactone 1a/b[玉米内酯1a/b的全合成和生物学评价]’,Helv.Chim.Acta[瑞士化学学报]2020,103,e2000017。
根据本发明,提供了一种具有式(I)的化合物:
其中
R1是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C6环烷基;
R2是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C6环烷基;
R3是氢或C1-C3烷基;
R4是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基羰基-N(C1-C3烷基)氨基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基;
R5是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基或C2-C6炔基;
R6是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基羰基-N(C1-C3烷基)氨基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基;或者
R4和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,其任选地被1、2、3或4个选自R9的基团取代;或者
R5和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,其任选地被1、2、3或4个选自R9的基团取代;或者
R4、R5和R6与它们所附接的碳原子一起形成8元至12元碳三环体系,其任选地被1、2、3或4个选自R9的基团取代;
R7是氢、C1-C6烷基、C1-C6卤代烷基或C3-C6环烷基;
R8是氢或C1-C3烷基;
R9是卤素、C1-C3烷基、C1-C3烷氧基、氰基或氧代基(=O);
或其盐。
在本发明的第二方面,提供了一种植物生长调节或种子萌发促进组合物,其包含根据本发明的化合物和任选的农业上可接受的配制辅助剂。
在本发明的第三方面,提供了一种用于在场所调节植物生长的方法,其中该方法包括向该场所施用植物生长调节量的根据本发明第二方面的组合物。
在本发明的第四方面,提供了一种用于促进种子萌发的方法,该方法包括向这些种子、或者含有种子的场所施用种子萌发促进量的根据本发明第二方面的组合物。
在本发明的第五方面,提供了一种用于控制杂草的方法,该方法包括向含有杂草种子的场所施用种子萌发促进量的根据本发明第二方面的组合物,从而允许这些种子萌发,并且然后向该场所施用苗后除草剂。
在本发明的第六方面,提供了根据本发明的具有式(I)的化合物作为植物生长调节剂或种子萌发促进剂的用途。
在本发明的第七方面,提供了一种处理植物繁殖材料的方法,该方法包括以对于促进萌发和/或调节植物生长有效的量向该植物繁殖材料施用根据本发明的化合物或组合物。
在本发明的第八方面,提供了一种用于改进作物养分吸收的方法,该方法包括以对于促进养分吸收有效的量向植物或其场所施用根据本发明的具有式(I)的化合物或组合物。
在本发明的第九方面,提供了一种用根据本发明的具有式(I)的化合物或根据本发明的组合物处理的植物繁殖材料。
在本发明的第十方面,提供了一种包含根据本发明的具有式(I)的化合物的种子。
当取代基被表示为“被任选地取代”时,这意指它们可以带有或可以不带有一个或多个相同或不同的取代基,例如一个、两个或三个R9取代基。例如,被1、2或3个卤素取代的C1-C6烷基可以包括但不限于-CH2Cl、-CHCl2、-CCl3、-CH2F、-CHF2、-CF3、-CH2CF3或-CF2CH3基团。作为另一个实例,被1、2或3个卤素取代的C1-C6烷氧基可以包括但不限于CH2ClO-、CHCl2O-、CCl3O-、CH2FO-、CHF2O-、CF3O-、CF3CH2O-或CH3CF2O-基团。
如本文使用的,术语“氰基”意指-CN基团。
如本文使用的,术语“卤素”是指氟(fluorine,fluoro)、氯(chlorine,chloro)、溴(bromine,bromo)或碘(iodine,iodo)。
如本文中所使用的,=O表示氧代基(oxo),例如如在羰基(-C(=O)-)基团中所见。
如本文使用的,术语“C1-C6烷基”是指仅由碳原子和氢原子组成的直链的或支链的烃链基团,所述烃链基团不含不饱和度、具有从一至六个碳原子、并且通过单键附接至分子的其余部分。“C1-C4烷基”和“C1-C3烷基”应相应地解释。C1-C6烷基的实例包括但不限于甲基、乙基、正丙基、及其异构体,例如异丙基。“C1-C6亚烷基”基团是指C1-C6烷基的相应定义,不同之处在于此种基团是通过两个单键附接至分子的其余部分。术语“C1-C2亚烷基”应相应地解释。C1-C6亚烷基的实例包括但不限于-CH2-、-CH2CH2-和-(CH2)3-。
如本文使用的,术语“C1-C6卤代烷基”是指如以上一般定义的C1-C6烷基,其被一个或多个相同的或不同的卤素原子取代。术语“C1-C4卤代烷基”和“C1-C3卤代烷基”应相应地解释。C1-C6卤代烷基的实例包括但不限于三氟甲基。
如本文使用的,术语“氰基C1-C6烷基”是指如上一般定义的C1-C6烷基基团,该基团被一个或多个如上定义的氰基基团取代。
如本文使用的,术语“C1-C6烷氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C1-C6烷基。术语“C1-C4烷氧基”和“C1-C3烷氧基”应相应地解释。C1-C6烷氧基的实例包括但不限于甲氧基、乙氧基、1-甲基乙氧基(异丙氧基)、和丙氧基。
如本文使用的,术语“C1-C4卤代烷氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C1-C4烷基基团,该基团被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C2-C6烯基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团含有至少一个可以具有(E)-或(Z)-构型的双键,具有从二至六个碳原子,通过单键附接至分子的其余部分。“C2-C4烯基”和“C2-C3烯基”应相应地解释。C2-C6烯基的实例包括但不限于乙烯基(ethenyl)(乙烯基(vinyl))、丙-1-烯基、丙-2-烯基(烯丙基)和丁-1-烯基。
如本文使用的,术语“C2-C6炔基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,所述烃链基团包含至少一个三键,具有从二至六个碳原子,并且通过单键附接至分子的其余部分。“C2-C4炔基”和“C2-C3炔基”应相应地解释。C2-C6炔基的实例包括但不限于乙炔基、丙-1-炔基、丁-1-炔基。
如本文使用的,术语“N,N-二(C1-C3烷基)氨基氧基羰基”是指具有式(Ra)(Rb)NCO(O)-的基团,其中Ra和Rb各自独立地是如上一般定义的C1-C3烷基基团。
如本文使用的,术语“N,N-二(C1-C3烷基)氨基羰基”是指具有式(Ra)(Rb)NC(O)-的基团,其中Ra和Rb各自独立地是如上一般定义的C1-C3烷基基团。“N,N-二(C1-C3烷基)氨基羰基”的实例包括但不限于N,N-二(甲基)氨基羰基。
如本文使用的,术语“C1-C6烷基羰基-N(C1-C3烷基)氨基”是指具有式RaC(O)NH(Rb)-的基团,其中Ra是如以上一般定义的C1-C6烷基基团,并且Rb是如以上一般定义的C1-C3烷基基团。“C1-C6烷基羰基-N(C1-C3烷基)氨基”的实例包括但不限于甲基羰基-N(甲基)氨基。
如本文使用的,术语“C3-C6环烷基”是指为单环饱和环体系并含有3至6个碳原子的基团。“C3-C5环烷基”和“C3-C4环烷基”应相应地解释。C3-C6环烷基的实例包括但不限于环丙基、1-甲基环丙基、2-甲基环丙基、环丁基、1-甲基环丁基、1,1-二甲基环丁基、2-甲基环丁基、和2,2-二甲基环丁基。
如本文使用的,术语“C1-C3烷氧基羰基”是指具有式-C(O)ORa的基团,其中Ra是如上一般定义的C1-C3烷基基团。
如本文使用的,术语“C1-C6烷基硫烷基”是指具有式-SRa的基团,其中Ra是如上一般定义的C1-C6烷基基团。术语“C1-C4烷基硫烷基”和“C1-C3烷基硫烷基”应相应地解释。C1-C6烷基硫烷基的实例包括但不限于甲基硫烷基。
如本文使用的,术语“C1-C6烷基亚磺酰基”是指具有式-S(O)Ra的基团,其中Ra是如上一般定义的C1-C6烷基基团。术语“C1-C4烷基亚磺酰基”和“C1-C3烷基亚磺酰基”应相应地解释。C1-C6烷基亚磺酰基的实例包括但不限于甲基亚磺酰基。
如本文使用的,术语“C1-C6烷基磺酰基”是指具有式-S(O)2Ra的基团,其中Ra是如上一般定义的C1-C6烷基基团。术语“C1-C4烷基磺酰基”和“C1-C3烷基磺酰基”应相应地解释。C1-C6烷基磺酰基的实例包括但不限于甲基磺酰基。
如本文使用的,“碳三环”是指非芳香族三环体系,其包含三个在一个碳原子上连接在一起的环,即共享一个碳原子。碳三环体系的实例包括但不限于金刚烷基。
在具有式(I)的化合物中存在一个或多个可能的立构元素意指化合物可以呈光学异构体形式(即,对映异构体或非对映异构体形式)存在。作为围绕单键的受限旋转的结果,还可能存在阻转异构体。式(I)旨在包括所有那些可能的异构体形式及其混合物。本发明包括具有式(I)的化合物的所有那些可能的异构体形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体。本发明包括具有式(I)的化合物的所有可能的互变异构体形式。
在每种情况下,根据本发明的具有式(I)的化合物呈游离形式或呈盐形式(例如,农艺学上可用的盐形式)。
以下清单提供了关于具有式(I)的化合物的取代基R1、R2、R3、R4、R5、R6、R7、R8和R9的定义,包括优选的定义。对于这些取代基中的任何一个,以下给出的任何定义都可以结合以下或在本文件中的其他地方给出的任何其他取代基的任何定义。
R1是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C6环烷基。优选地,R1是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C4环烷基。更优选地,R1是氢、卤素、C1-C3烷基或C1-C3烷氧基。甚至更优选地,R1是氢、C1-C3烷基或C1-C3烷氧基。还更优选地,R1是氢、甲基或甲氧基。甚至还更优选地,R1是氢或甲基。在一个实施例中,R1是氢。
R2是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C6环烷基。优选地,R2是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C4环烷基。更优选地,R2是氢、卤素、C1-C3烷基或C1-C3烷氧基。甚至更优选地,R2是氢、C1-C3烷基或C1-C3烷氧基。还更优选地,R2是氢或C1-C3烷基。甚至还更优选地,R2是氢或甲基。在一个实施例中,R2是C1-C3烷基,优选是甲基。在另一个实施例中,R2是C1-C3烷基或C1-C3烷氧基,优选是甲基或甲氧基。
在一组实施例中,当R1是氢时,R2是甲基。在另一组实施例中,R1和R2都是甲基。
R3是氢或C1-C3烷基。优选地,R3是氢、甲基、乙基或异丙基。还更优选地,R3是氢或甲基。在一个实施例中,R3是氢。
R4是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基羰基-N(C1-C3烷基)氨基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基。
优选地,R4是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C3烷基羰基-N(C1-C3烷基)氨基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基或C1-C3烷基硫烷基。
更优选地,R4是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C2-C4烯基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、C1-C3烷基羰基-N(C1-C3烷基)氨基或C1-C3烷基磺酰基。
还更优选地,R4是氢、氰基、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、正丙氧基、异丙氧基、三氟甲基、二氟甲基、2,2,2-三氟乙基、乙烯基、丙烯基、1-异丙烯基、甲氧基羰基、乙氧基羰基、异丙氧基羰基、N,N-二(甲基)氨基羰基、甲基羰基-N(甲基)氨基或甲基磺酰基、乙基磺酰基或异丙基磺酰基。
在一组实施例中,R4是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3烷氧基羰基、N,N-二(C1-C2烷基)氨基羰基、C1-C2烷基羰基-N(C1-C2烷基)氨基或C1-C3烷基磺酰基
更优选地,R4是氢、氰基、甲基、甲氧基、甲氧基羰基、N,N-二(甲基)氨基羰基、甲基羰基-N(甲基)氨基或甲基磺酰基。
在一组实施例中,R4是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C2-C4烯基、C1-C3烷氧基羰基、N,N-二(甲基)氨基羰基、N,N-二(甲基)氨基氧基羰基、C1-C3烷基羰基-N(甲基)氨基或C1-C3烷基磺酰基。
在另一组实施例中,R4是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基。优选地,R4是氢、氰基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基或C1-C4烷基硫烷基。更优选地,R4是氢、氰基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C4烷基磺酰基或C1-C4烷基硫烷基。更优选地,R4是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3烷基磺酰基或C1-C3烷基硫烷基。还更优选地,R4是氢、氰基、甲基、乙基、甲氧基、甲基硫烷基或甲基磺酰基。甚至还更优选地,R4是氢或甲基。
R5是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基或C2-C6炔基。优选地,R5是氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C2-C5烯基或C2-C5炔基。更优选地,R5是氢、C1-C3烷基或C1-C3烷氧基。还更优选地,R5是氢、甲基或甲氧基。甚至还更优选地,R5是氢或甲基。
在一组实施例中,R5是氢、C1-C6烷基或C2-C6烯基,优选地,氢、C1-C3烷基或C2-C4烯基,更优选地,氢、C1-C3烷基或C2-C3烯基,并且甚至更优选地,氢、甲基或异丙烯基。
R6是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基羰基-N(C1-C3烷基)氨基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基。
优选地,R6是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C3烷基羰基-N(C1-C3烷基)氨基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基或C1-C3烷基硫烷基。
更优选地,R6是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C2-C4烯基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、C1-C3烷基羰基-N(C1-C3烷基)氨基或C1-C3烷基磺酰基。
还更优选地,R6是氢、氰基、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、正丙氧基、异丙氧基、三氟甲基、二氟甲基、2,2,2-三氟乙基、乙烯基、丙烯基、1-异丙烯基、甲氧基羰基、乙氧基羰基、异丙氧基羰基、N,N-二(甲基)氨基羰基、甲基羰基-N(甲基)氨基或甲基磺酰基、乙基磺酰基或异丙基磺酰基。
在一组实施例中,R6是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3烷氧基羰基、N,N-二(C1-C2烷基)氨基羰基、C1-C2烷基羰基-N(C1-C2烷基)氨基或C1-C3烷基磺酰基。
更优选地,R6是氢、氰基、甲基、甲氧基、甲氧基羰基、N,N-二(甲基)氨基羰基、甲基羰基-N(甲基)氨基或甲基磺酰基
在另一组实施例中,R6是氢或C1-C6烷基,优选地,氢或C1-C3烷基,并且更优选地,氢或甲基。
在一组实施例中,R6是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基;优选地,R6是氢、氰基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基或C1-C4烷基硫烷基。更优选地,R6是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C3烷基磺酰基或C1-C3烷基硫烷基。甚至更优选地,R6是氢、氰基、甲基、甲氧基、甲氧基羰基、N,N-二(甲基)氨基氧基羰基或甲基磺酰基。
或者R4和R6与它们所附接的碳原子一起形成氧代(=O)基团或3元至6元环烷基环,任选地被1、2、3或4个选自R9的基团取代。优选地,R4和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,任选地被1、2或3个选自R9的基团取代。更优选地,R4和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,任选地被1个或2个选自R9的基团取代。
在一组实施例中,R4和R6与它们所附接的碳原子一起形成3元至6元环烷基环,任选地被1、2、3或4个选自R9的基团取代;更优选地,R4和R6与它们所附接的碳原子一起形成4元至6元环烷基环,任选地被1、2、3或4个选自R9的基团取代;甚至更优选地,R4和R6与它们所附接的碳原子一起形成4元至6元环烷基环,任选地被1、2或3个选自R9的基团取代;还更优选地,R4和R6与它们所附接的碳原子一起形成4元至6元环烷基环,或被2个或3个选自R9的基团取代的4元或6元环烷基环。
在一组特别优选的实施例中,R4和R6与它们所附接的碳原子一起形成环丁基、环戊基或环己基环,其中环丁基环任选地被3个选自R9的基团取代,并且其中环己基环任选地被2个选自R9的基团取代。
或者R5和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,任选地被1、2、3或4个选自R9的基团取代。
或者R4、R5和R6与它们所附接的碳原子一起形成8元至12元碳三环体系,任选地被1、2、3或4个选自R9的基团取代。优选地,R4、R5和R6与它们所附接的碳原子一起形成8元至10元碳三环体系,任选地被1、2或3个选自R9的基团取代。更优选地,R4、R5和R6与它们所附接的碳原子一起形成8元至10元碳三环体系,任选地被1个或2个选自R9的基团取代。还更优选地,R4、R5和R6与它们所附接的碳原子一起形成8元至10元碳三环体系。甚至更优选地,R4、R5和R6与它们所附接的碳原子一起形成金刚烷基环。
R7是氢、C1-C6烷基、C1-C6卤代烷基或C3-C6环烷基。优选地,R7是氢、C1-C3烷基、C1-C3卤代烷基或C3-C6环烷基。更优选地,R7是氢或C1-C3烷基,甚至更优选地,R7是C1-C3烷基,并且最优选地,R7是甲基。
R8是氢或C1-C3烷基。优选地,R8是氢、甲基或乙基。更优选地,R8是氢或甲基。还更优选地,R8是氢。
R9是卤素、C1-C3烷基、C1-C3烷氧基、氰基或氧代基(=O)。优选地,R9是氯、氟、甲基、甲氧基、氰基或氧代基(=O)。在一组实施例中,R9是氢、C1-C3烷基或氧代基(=O),优选地,卤素、甲基或氧代基(=O),更优选地,氟、甲基或氧代基(=O)。在另一组实施例中,R9是卤素,优选是氟。
在根据本发明的具有式(I)的化合物中,优选地:
R1是氢、C1-C3烷基或C1-C3烷氧基;
R2是氢、C1-C3烷基或C1-C3烷氧基;
R3是氢或C1-C3烷基;
R4是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3烷基磺酰基或C1-C3烷基硫烷基;
R5是氢、C1-C3烷基、C1-C3烷氧基或C2-C4烯基;
R6是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C3烷基磺酰基或C1-C3烷基硫烷基;或者
R4和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,任选地被1、2或3个选自R9的基团取代;或者
R4、R5和R6与它们所附接的碳原子一起形成8元至10元碳三环体系,其任选地被1个或2个选自R9的基团取代;
R7是C1-C3烷基;
R8是氢或C1-C3烷基;并且
R9是卤素。
在另一组实施例中,R1是氢、甲基或甲氧基;
R2是氢或甲基;
R3是氢或甲基;
R4是氢、氰基、甲基、乙基、甲氧基、甲基硫烷基或甲基磺酰基;
R5是氢、甲基或甲氧基;
R6是氢、氰基、甲基、甲氧基、甲氧基羰基、N,N-二(甲基)氨基氧基羰基或甲基磺酰基;或者
R4和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,任选地被1个或2个选自R9的基团取代;或者
R4、R5和R6与它们所附接的碳原子一起形成8元至10元碳三环体系;
R7是C1-C3烷基;
R8是氢或C1-C3烷基;并且
R9是卤素。
在另一组实施例中,R1是氢或C1-C3烷基;
R2是C1-C3烷基;
R3是氢或C1-C3烷基;
R4是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、C1-C3烷基羰基-N(C1-C3烷基)氨基或C1-C3烷基磺酰基;
R5是氢、C1-C3烷基或C2-C4烯基;
R6是氢或C1-C3烷基;或者
R4和R6与它们所附接的碳原子一起形成4元至6元环烷基环,任选地被1、2或3个选自R9的基团取代;或者
R4、R5和R6与它们所附接的碳原子一起形成金刚烷基基团;
R7是甲基;
R8是氢;并且
R9是氟、甲基或氧代基(=O)。
在另一组实施例中,R1是氢或C1-C3烷基;
R2是C1-C3烷基;
R3是氢或C1-C3烷基;
R4是氢、氰基、甲基、甲氧基、甲氧基羰基、甲基羰基-N-(甲基)氨基、N,N-二(甲基)-氨基羰基或甲基磺酰基;
R5是氢、甲基或异丙烯基;
R6是氢或甲基;或者
R4和R6与它们所附接的碳原子一起形成环丁基、环戊基或环己基环,任选地被1、2或3个选自氟、甲基和氧代基(=O)的基团取代;或者
R4、R5和R6与它们所附接的碳原子一起形成金刚烷基基团;
R7是C1-C3烷基;并且
R8是氢。
在还另一组实施例中,R1是氢或甲基;
R2是甲基;
R3是氢或甲基;
R4是氢、氰基、甲基、甲氧基、甲氧基羰基、甲基羰基-N-(甲基)氨基、N,N-二(甲基)-氨基羰基或甲基磺酰基;
R5是氢、甲基或异丙烯基;
R6是氢或甲基;或者
R4和R6与它们所附接的碳原子一起形成环丁基、环戊基或环己基环,任选地被1、2或3个选自氟、甲基和氧代基(=O)的基团取代;或者
R4、R5和R6与它们所附接的碳原子一起形成金刚烷基基团;
R7是甲基;并且
R8是氢。
在一组特别优选的实施例中,具有式(I)的化合物选自:
(E,2E)-4-(1-甲基环己基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-1);
(E,2E)-4-(4,4-二氟环己基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-2);
(E,2E)-4-环己基-2-[(3,4-二甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-3);
(E,2E)-4-(1-金刚烷基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-4);
(E,2E)-4-环丁基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-5);
(E,2E)-4-(1-甲基环戊基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-6);
(E,2E)-4-(1-甲基环丙基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-7);
(E,4E)-4-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]戊-2-烯二酸二甲酯(P-8);
(2E)-4-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]戊-3-烯酸甲酯(P-9);
(E,2E)-2-[(3,4-二甲基-5-氧代-2H-呋喃-2-基)甲醛]-5,5-二甲基-己-3-烯酸甲酯(P-10);
(2E,3E)-4-环戊基-2-(((4-甲基-5-氧代-2,5-二氢呋喃-2-基)氧基)亚甲基)丁-3-烯酸甲酯(P-11);
(E,2E)-5-甲氧基-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(P-12);
(E,2E)-4-环己基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-13);
(E,2E)-5,5-二甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(P-14);
(E,2E)-4-(1-异丙烯基-2,2-二甲基-4-氧代-环丁基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-15);
(E,2E)-5-氰基-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(P-16);
(E,2E)-5-[乙酰基(甲基)氨基]-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(P-17);
(E,2E)-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]-5-甲基磺酰基-己-3-烯酸甲酯(P-18);
(E,5E)-2,2-二甲基-5-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯二酸二甲酯(P-19);以及
(E,2E)-6-(二甲基氨基)-5,5-二甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]-6-氧代-己-3-烯酸甲酯(P-20)。
在另一组特别优选的实施例中,具有式(I)的化合物选自:
(E,2E)-4-(4,4-二氟环己基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-2);
(E,2E)-4-环己基-2-[(3,4-二甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-3);
(E,2E)-4-(1-金刚烷基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-4);
(E,2E)-4-(1-甲基环戊基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-6);
(E,4E)-4-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]戊-2-烯二酸二甲酯(P-8);
(2E)-4-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]戊-3-烯酸甲酯(P-9);
(E,2E)-2-[(3,4-二甲基-5-氧代-2H-呋喃-2-基)甲醛]-5,5-二甲基-己-3-烯酸甲酯(P-10);
(E,2E)-4-(1-异丙烯基-2,2-二甲基-4-氧代-环丁基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-15);以及
(E,5E)-2,2-二甲基-5-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯二酸二甲酯(P-19)。
在另一组特别优选的实施例中,具有式(I)的化合物选自:
(E,2E)-4-(4,4-二氟环己基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-2);
(E,2E)-4-(1-金刚烷基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-4);
(E,2E)-4-(1-甲基环戊基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-6);
(E,2E)-4-(1-甲基环丙基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-7);
(E,4E)-4-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]戊-2-烯二酸二甲酯(P-8);
(E,2E)-5-甲氧基-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(P-12);
(E,2E)-4-(1-异丙烯基-2,2-二甲基-4-氧代-环丁基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(P-15);
(E,2E)-5-氰基-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(P-16);
(E,2E)-5-[乙酰基(甲基)氨基]-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(P-17);
(E,5E)-2,2-二甲基-5-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯二酸二甲酯(P-19);以及
(E,2E)-6-(二甲基氨基)-5,5-二甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]-6-氧代-己-3-烯酸甲酯(P-20)。
本发明的化合物可以如在以下方案中所示来制备,其中(除非另外说明)每一变量的定义是如以上针对具有式(I)的化合物所定义的。
具有式(I)的化合物可以通过在催化剂诸如钯(0)的存在下,将具有式(II)的化合物(其中X是卤素)与具有式(III)的化合物(其中R是C3-C6烷基并且R3和R8是氢)进行偶联来制备。该反应可能被本领域技术人员称为施蒂勒(Stille)偶联。这示于以下方案1中。
方案1
可替代地,具有式(I)的化合物可以通过在催化剂诸如钯(0)的存在下,将具有式(IV)的化合物(其中R是C3-C6烷基并且R3和R8是氢)与具有式(V)的化合物(其中X是卤素)进行偶联来制备。该反应可能被本领域技术人员称为施蒂勒偶联。这示于以下方案2中。
方案2
具有式(III)的化合物(其中R是C3-C6烷基并且R3和R8是氢)可商购获得或者可通过在催化剂诸如Pd(0)的存在下与R3SnH反应由具有式(VI)的化合物制备。具有式(VI)的化合物可以从化学品供应商处购买。这示于以下方案3中。
方案3
具有式(V)的化合物(其中X是卤素)可以通过具有式(III)的化合物与X2或任何其他亲电卤化试剂的反应来制备。这示于以下方案4中。
方案4
具有式(IV)的化合物可以通过在催化剂诸如Pd(0)的存在下,将具有式(II)的化合物(其中X是卤素)与具有式R3Sn-SnR3的化合物进行偶联来制备。这示于以下方案5中。具有式(II)的化合物可以如M.Dieckmann等人,J.Org.Chem.[有机化学杂志],2018,125-135中所述来制备。
方案5
下表示出了根据本发明的具有式(I)的单独的化合物的实例。
表1:根据本发明的具有式(I)的单独的化合物的取代基R1、R2、R3、R5、R7和R8的定
义:
索引 | R1 | R2 | R3 | R5 | R7 | R8 |
001 | H | H | H | H | CH3 | H |
002 | H | H | H | CH3 | CH3 | H |
003 | H | H | CH3 | H | CH3 | H |
004 | H | H | CH3 | CH3 | CH3 | H |
005 | H | H | H | H | CH3 | CH3 |
006 | H | H | H | CH3 | CH3 | CH3 |
007 | H | H | CH3 | H | CH3 | CH3 |
008 | H | H | CH3 | CH3 | CH3 | CH3 |
009 | CH3 | H | H | H | CH3 | H |
010 | CH3 | H | H | CH3 | CH3 | H |
011 | CH3 | H | CH3 | H | CH3 | H |
012 | CH3 | H | CH3 | CH3 | CH3 | H |
013 | CH3 | H | H | H | CH3 | CH3 |
014 | CH3 | H | H | CH3 | CH3 | CH3 |
015 | CH3 | H | CH3 | H | CH3 | CH3 |
016 | CH3 | H | CH3 | CH3 | CH3 | CH3 |
017 | OCH3 | H | H | H | CH3 | H |
018 | OCH3 | H | H | CH3 | CH3 | H |
019 | OCH3 | H | CH3 | H | CH3 | H |
020 | OCH3 | H | CH3 | CH3 | CH3 | H |
021 | OCH3 | H | H | H | CH3 | CH3 |
022 | OCH3 | H | H | CH3 | CH3 | CH3 |
023 | OCH3 | H | CH3 | H | CH3 | CH3 |
024 | OCH3 | H | CH3 | CH3 | CH3 | CH3 |
025 | H | CH3 | H | H | CH3 | H |
026 | H | CH3 | H | CH3 | CH3 | H |
027 | H | CH3 | CH3 | H | CH3 | H |
索引 | R1 | R2 | R3 | R5 | R7 | R8 |
028 | H | CH3 | CH3 | CH3 | CH3 | H |
029 | H | CH3 | H | H | CH3 | CH3 |
030 | H | CH3 | H | CH3 | CH3 | CH3 |
031 | H | CH3 | CH3 | H | CH3 | CH3 |
032 | H | CH3 | CH3 | CH3 | CH3 | CH3 |
033 | CH3 | CH3 | H | H | CH3 | H |
034 | CH3 | CH3 | H | CH3 | CH3 | H |
035 | CH3 | CH3 | CH3 | H | CH3 | H |
036 | CH3 | CH3 | CH3 | CH3 | CH3 | H |
037 | CH3 | CH3 | H | H | CH3 | CH3 |
038 | CH3 | CH3 | H | CH3 | CH3 | CH3 |
039 | CH3 | CH3 | CH3 | H | CH3 | CH3 |
040 | CH3 | CH3 | CH3 | CH3 | CH3 | CH3 |
041 | OCH3 | CH3 | H | H | CH3 | H |
042 | OCH3 | CH3 | H | CH3 | CH3 | H |
043 | OCH3 | CH3 | CH3 | H | CH3 | H |
044 | OCH3 | CH3 | CH3 | CH3 | CH3 | H |
045 | OCH3 | CH3 | H | H | CH3 | CH3 |
046 | OCH3 | CH3 | H | CH3 | CH3 | CH3 |
047 | OCH3 | CH3 | CH3 | H | CH3 | CH3 |
048 | OCH3 | CH3 | CH3 | CH3 | CH3 | CH3 |
049 | H | H | H | H | CH2CH3 | H |
050 | H | H | H | CH3 | CH2CH3 | H |
051 | H | H | CH3 | H | CH2CH3 | H |
052 | H | H | CH3 | CH3 | CH2CH3 | H |
053 | H | H | H | H | CH2CH3 | CH3 |
054 | H | H | H | CH3 | CH2CH3 | CH3 |
索引 | R1 | R2 | R3 | R5 | R7 | R8 |
055 | H | H | CH3 | H | CH2CH3 | CH3 |
056 | H | H | CH3 | CH3 | CH2CH3 | CH3 |
057 | CH3 | H | H | H | CH2CH3 | H |
058 | CH3 | H | H | CH3 | CH2CH3 | H |
059 | CH3 | H | CH3 | H | CH2CH3 | H |
060 | CH3 | H | CH3 | CH3 | CH2CH3 | H |
061 | CH3 | H | H | H | CH2CH3 | CH3 |
062 | CH3 | H | H | CH3 | CH2CH3 | CH3 |
063 | CH3 | H | CH3 | H | CH2CH3 | CH3 |
064 | CH3 | H | CH3 | CH3 | CH2CH3 | CH3 |
065 | OCH3 | H | H | H | CH2CH3 | H |
066 | OCH3 | H | H | CH3 | CH2CH3 | H |
067 | OCH3 | H | CH3 | H | CH2CH3 | H |
068 | OCH3 | H | CH3 | CH3 | CH2CH3 | H |
069 | OCH3 | H | H | H | CH2CH3 | CH3 |
070 | OCH3 | H | H | CH3 | CH2CH3 | CH3 |
071 | OCH3 | H | CH3 | H | CH2CH3 | CH3 |
072 | OCH3 | H | CH3 | CH3 | CH2CH3 | CH3 |
073 | H | CH3 | H | H | CH2CH3 | H |
074 | H | CH3 | H | CH3 | CH2CH3 | H |
075 | H | CH3 | CH3 | H | CH2CH3 | H |
076 | H | CH3 | CH3 | CH3 | CH2CH3 | H |
077 | H | CH3 | H | H | CH2CH3 | CH3 |
078 | H | CH3 | H | CH3 | CH2CH3 | CH3 |
079 | H | CH3 | CH3 | H | CH2CH3 | CH3 |
080 | H | CH3 | CH3 | CH3 | CH2CH3 | CH3 |
081 | CH3 | CH3 | H | H | CH2CH3 | H |
索引 | R1 | R2 | R3 | R5 | R7 | R8 |
082 | CH3 | CH3 | H | CH3 | CH2CH3 | H |
083 | CH3 | CH3 | CH3 | H | CH2CH3 | H |
084 | CH3 | CH3 | CH3 | CH3 | CH2CH3 | H |
085 | CH3 | CH3 | H | H | CH2CH3 | CH3 |
086 | CH3 | CH3 | H | CH3 | CH2CH3 | CH3 |
087 | CH3 | CH3 | CH3 | H | CH2CH3 | CH3 |
088 | CH3 | CH3 | CH3 | CH3 | CH2CH3 | CH3 |
089 | OCH3 | CH3 | H | H | CH2CH3 | H |
090 | OCH3 | CH3 | H | CH3 | CH2CH3 | H |
091 | OCH3 | CH3 | CH3 | H | CH2CH3 | H |
092 | OCH3 | CH3 | CH3 | CH3 | CH2CH3 | H |
093 | OCH3 | CH3 | H | H | CH2CH3 | CH3 |
094 | OCH3 | CH3 | H | CH3 | CH2CH3 | CH3 |
095 | OCH3 | CH3 | CH3 | H | CH2CH3 | CH3 |
096 | OCH3 | CH3 | CH3 | CH3 | CH2CH3 | CH3 |
表A-1提供了96种具有式(I)的化合物A-1.001至A-1.096,其中R4和R6两者均是氢,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-2提供了96种具有式(I)的化合物A-2.001至A-2.096,其中R4是甲基,R6是氢,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-3提供了96种具有式(I)的化合物A-3.001至A-3.096,其中R4是乙基,R6是氢,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-4提供了96种具有式(I)的化合物A-4.001至A-4.096,其中R4是甲氧基,R6是氢,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-5提供了96种具有式(I)的化合物A-5.001至A-5.096,其中R4是甲基硫烷基,R6是氢,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-6提供了96种具有式(I)的化合物A-6.001至A-6.096,其中R4是甲基磺酰基,R6是氢,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-7提供了96种具有式(I)的化合物A-7.001至A-7.096,其中R4是氢,R6是甲基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-8提供了96种具有式(I)的化合物A-8.001至A-8.096,其中R4和R6两者均是甲基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-9提供了96种具有式(I)的化合物A-9.001至A-9.096,其中R4是乙基,R6是甲基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-10提供了96种具有式(I)的化合物A-10.001至A-10.096,其中R4是甲氧基,R6是甲基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-11提供了96种具有式(I)的化合物A-11.001至A-11.096,其中R4是甲基硫烷基,R6是甲基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-12提供了96种具有式(I)的化合物A-12.001至A-12.096,其中R4是甲基磺酰基,R6是甲基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-13提供了96种具有式(I)的化合物A-13.001至A-13.096,其中R4是氢,R6是-CO2CH3,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-14提供了96种具有式(I)的化合物A-14.001至A-14.096,其中R4是甲基,R6是-CO2CH3,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-15提供了96种具有式(I)的化合物A-15.001至A-15.096,其中R4是乙基,R6是-CO2CH3,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-16提供了96种具有式(I)的化合物A-16.001至A-16.096,其中R4是甲氧基,R6是-CO2CH3,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-17提供了96种具有式(I)的化合物A-17.001至A-17.096,其中R4是甲基硫烷基,R6是-CO2CH3,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-18提供了96种具有式(I)的化合物A-18.001至A-18.096,其中R4是甲基磺酰基,R6是-CO2CH3,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-19提供了96种具有式(I)的化合物A-19.001至A-19.096,其中R4是氢,R6是-CO2N(CH3)2,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-20提供了96种具有式(I)的化合物A-20.001至A-20.096,其中R4是甲基,R6是-CO2N(CH3)2,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-21提供了96种具有式(I)的化合物A-21.001至A-21.096,其中R4是乙基,R6是-CO2N(CH3)2,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-22提供了96种具有式(I)的化合物A-22.001至A-22.096,其中R4是甲氧基,R6是-CO2N(CH3)2,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-23提供了96种具有式(I)的化合物A-23.001至A-23.096,其中R4是甲基硫烷基,R6是-CO2N(CH3)2,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-24提供了96种具有式(I)的化合物A-24.001至A-24.096,其中R4是甲基磺酰基,R6是-CO2N(CH3)2,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-25提供了96种具有式(I)的化合物A-25.001至A-25.096,其中R4是氢,R6是甲基磺酰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-26提供了96种具有式(I)的化合物A-26.001至A-26.096,其中R4是甲基,R6是甲基磺酰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-27提供了96种具有式(I)的化合物A-27.001至A-27.096,其中R4是乙基,R6是甲基磺酰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-28提供了96种具有式(I)的化合物A-28.001至A-28.096,其中R4是甲氧基,R6是甲基磺酰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-29提供了96种具有式(I)的化合物A-29.001至A-29.096,其中R4是甲基硫烷基,R6是甲基磺酰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-30提供了96种具有式(I)的化合物A-30.001至A-30.096,其中R4是甲基磺酰基,R6是氢,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-31提供了96种具有式(I)的化合物A-31.001至A-31.096,其中R4是氢,R6是甲氧基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-32提供了96种具有式(I)的化合物A-32.001至A-32.096,其中R4是甲基,R6是甲氧基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-33提供了96种具有式(I)的化合物A-33.001至A-33.096,其中R4是乙基,R6是甲氧基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-34提供了96种具有式(I)的化合物A-34.001至A-34.096,其中R4是甲氧基,R6是甲氧基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-35提供了96种具有式(I)的化合物A-35.001至A-35.096,其中R4是甲基硫烷基,R6是甲氧基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-36提供了96种具有式(I)的化合物A-36.001至A-36.096,其中R4是甲基磺酰基,R6是甲氧基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-37提供了96种具有式(I)的化合物A-37.001至A-37.096,其中R4是氢,R6是氰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-38提供了96种具有式(I)的化合物A-38.001至A-38.096,其中R4是甲基,R6是氰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-39提供了96种具有式(I)的化合物A-39.001至A-39.096,其中R4是乙基,R6是氰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-40提供了96种具有式(I)的化合物A-40.001至A-40.096,其中R4是甲氧基,R6是氰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-41提供了96种具有式(I)的化合物A-41.001至A-41.096,其中R4是甲基硫烷基,R6是氰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表A-42提供了96种具有式(I)的化合物A-42.001至A-42.096,其中R4是甲基磺酰基,R6是氰基,并且R1、R2、R3、R5、R7和R8如表1中所定义。
表B-1提供了96种具有式(Ia)的化合物B-1.001至B-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
表C-1提供了96种具有式(Ib)的化合物C-1.001至C-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
表D-1提供了96种具有式(Ic)的化合物D-1.001至D-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
表E-1提供了96种具有式(Id)的化合物E-1.001至E-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
表F-1提供了96种具有式(Ie)的化合物F-1.001至F-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
表G-1提供了96种具有式(If)的化合物G-1.001至G-1.096,其中R1、R2、R3、R7和R8如表1中所定义:
表H-1提供了96种具有式(Ig)的化合物H-1.001至H-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
表J-1提供了96种具有式(Ih)的化合物J-1.001至J-1.096,其中R1、R2、R3、R7和R8如表1中所定义:
表K-1提供了96种具有式(Ii)的化合物K-1.001至K-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
表L-1提供了96种具有式(Ij)的化合物L-1.001至L-1.096,其中R1、R2、R3、R5、R7和R8如表1中所定义:
本发明提供了一种改进植物对非生物胁迫的耐受性的方法,其中该方法包括向该植物、植物部分、植物繁殖材料或植物生长场所施用根据本发明的化合物、组合物或混合物。
本发明提供了一种用于调节或改进植物的生长的方法,其中该方法包括向该植物、植物部分、植物繁殖材料或植物生长场所施用根据本发明的化合物、组合物或混合物。在一个实施例中,当植物经受非生物胁迫条件时,植物生长被调节或改进。
本发明还提供了一种用于改进植物种子萌发的方法,并且特别地本发明提供了一种用于在冷胁迫条件下改进植物种子萌发的方法,该方法包括向该种子或含有种子的场所施用根据本发明的化合物、组合物或混合物。
本发明还提供了一种用于针对化学药品的植物毒性效应将植物安全化的方法,该方法包括向该植物、植物部分、植物繁殖材料、或植物生长场所施用根据本发明的化合物、组合物或混合物。
本发明还提供了一种用于诱导/增加有用植物作物的叶衰老的方法,所述方法包括向该植物、植物部分、植物繁殖材料、或植物生长场所施用根据本发明的化合物、组合物或混合物。特别地,还提供了一种用于诱导/增加作物的叶衰老的方法,所述方法包括向该作物植物、植物部分、植物繁殖材料、或植物生长场所施用根据本发明的化合物、组合物或混合物。
根据本发明,“调节或改进作物的生长”意指植物活力的改进、植物品质的改进、对胁迫因素的改进的耐受性、和/或改进的投入使用效率。
‘植物活力的改进’意指与生长在缺少本发明方法的相同条件下的对照植物的相同性状相比时,定性或定量地改进某些性状。这样的性状包括,但并不局限于,早的和/或改进的发芽,改进的出苗,使用更少种子的能力,增加的根的生长,更发达的根系,增加的根的结瘤,增加的芽的生长,增加的分蘖,更强的分蘖,更有效的分蘖,增加的或改进的植株站立,更少的植物颠倒(plant verse)(倒伏),植物高度的增加和/或改进,植物重量(鲜重或干重)的增加,更大的叶片,更绿的叶子颜色,增加的色素含量,增加的光合活性,更早的开花,更长的圆锥花序,早的谷物成熟期,增加的种子、果实或荚果大小,增加的荚果或穗的数量,增加的每荚果或穗的种子数量,增加的种子品质,增强的种子填充,更少的死的基生叶,延缓枯萎,改进的植物生命力,在储存组织的提高的氨基酸类化合物水平和/或需要更少的投入(例如更少的所需肥料、水和/或劳作)。活力改进的植物可以具有在任何上述性状或任意组合或两个或更多个上述性状方面的增加。
‘植物品质的改进’意指与生长在缺少本发明方法的相同条件下的对照植物的相同性状相比时,定性或定量地改进某些性状。这样的性状包括,但并不局限于,改进的植物视觉外观,减少的乙烯(减少产生和/或抑制接收),所收获材料(例如种子、果实、叶、蔬菜)的改进的品质,这样改进的品质可以表现为所收获材料的改进的视觉外观,改进的碳水化合物含量(例如增加的糖和/或淀粉的量值、改进的糖酸比、还原糖的减少、增加的糖形成速度),改进的蛋白质含量,改进的油含量和组成,改进的营养价值,抗营养化合物的减少,改进的感官特性(例如改进的味道)和/或改进的消费者健康益处(例如增加的维生素和抗氧化剂水平),改进的收获后特征(例如增强的贮存期和/或贮存稳定性,更容易的可加工性,更容易的化合物提取),更同质的作物发育(例如植物的同时萌发、开花和/或结果)和/或改进的种子品质(例如在随后的季节中使用)。品质改进的植物可以具有在任何上述这些性状或任意组合或两个或更多个上述性状方面的增加。
‘对于胁迫因素的改进的耐受性’意指与生长在缺少本发明方法的相同条件下的对照植物的相同性状相比时,定性或定量地改进了某些性状。这样的性状包括但并不局限于对多种非生物胁迫因素的耐受力和/或抗性增加,这些因素引发次优生长条件,如干旱(例如导致植物水含量缺乏、水吸收潜力缺乏或向植物供水减少的任何胁迫)、受冷、受热、渗透胁迫、UV胁迫、漫灌、盐度增加(例如土壤中的盐度)、增加的矿物暴露、臭氧暴露、高度的光暴露和/或养分(例如氮和/或磷养分)利用受限。对胁迫因素的耐受性改进的植物可以具有在任何上述性状或任意组合或两个或更多个上述性状方面的增加。在干旱和养分胁迫的情况下,这些耐受性改进可以归因于,例如,更高效率的吸收、利用或者保有水分和养分。特别地,本发明的这些化合物或组合物可用于改进对干旱胁迫的耐受性。
‘改进的投入利用效率’是指当与在相同条件下生长但未使用本发明的方法的对照植物的生长相比时,植物能够更有效地使用给定的投入水平而生长。具体而言,这些投入包括,但并不局限于肥料(例如氮、磷、钾、以及微量营养素)、光和水。具有改进的投入利用效率的植物可以具有对任何上述投入、或两种或更多种上述投入的任何组合的改进的使用。
调节或改进作物生长的其他效果包括减少植物高度,或减少分蘖,这在作物中或在希望具有更少的生物质和更少分蘖的条件下是有益的特征。
任何或全部以上的作物增强可以通过改进例如植物生理、植物生长与发育和/或植物株型而导致改进的产量。在本发明的上下文中,‘产量’包括,但并不局限于:(i)生物质生产、谷物产量、淀粉含量、油含量和/或蛋白质含量的增加,这可以起因于:(a)由植物自身生产的量的增加或(b)改进的收获植物物质的能力,(ii)收获材料的组成上的改进(例如改进的糖酸比、改进的油组成,增加的营养价值,抗营养化合物的减少,增加的消费者健康益处)和/或(iii)增加的/易化的收获作物的能力、改进的作物可加工性和/或更好的贮存稳定性/贮存期。农业植物的产量增加意指,在可能采取定量测量的情况下,各个植物的某一产物的产量比该植物在相同条件下(但没有应用本发明)生产的这种相同产物的产量提高可测量的数量。根据本发明,优选的是,产量增加了至少0.5%、更优选至少1%、甚至更优选至少2%、还更优选至少4%、优选5%或甚至更多。
任何或全部以上的作物增强也可以导致土地利用改进,即先前对于种植不可用或次优的土地可以变得可用。例如,在干旱条件下显示出生存能力增强的植物能够在次优降雨地区(例如可能在沙漠边缘或者甚至沙漠里)种植。
在本发明的一个方面,作物增强是在来自有害生物和/或病害和/或非生物胁迫的压力大体上不存在下得到的。在本发明的另一个方面,植物活力、胁迫耐受力、品质和/或产量的改进是在来自有害生物和/或病害的压力大体上不存在下得到的。例如,有害生物和/或病害可以通过在本发明的方法之前或者同时施用杀有害生物处理来控制。在本发明的还另一个方面,植物活力、胁迫耐受力、品质和/或产量的改进是在有害生物和/或病害压力不存在下得到的。在另外的实施例中,植物活力、品质和/或产量的改进是在非生物胁迫不存在或者大体上不存在下得到的。
具有式(I)的化合物可以是组合物的唯一活性成分,或者适当时它可以与一种或多种额外的活性成分(诸如杀有害生物剂、杀真菌剂、增效剂、除草剂或植物生长调节剂)混合。在一些情况下,额外的活性成分可以产生出乎意料的协同活性。
合适的另外的活性成分的实例还包括以下:矿物油、1,1-双(4-氯-苯基)-2-乙氧基乙醇、2,4-二氯苯基苯磺酸盐、2-氟-N-甲基-N-1-萘乙酰胺、4-氯苯基苯基砜、乙酰虫腈、氧涕灭威、赛硫磷、果满磷、胺吸磷、胺吸磷草酸氢盐、双甲脒、杀螨特、三氧化二砷、溴灭菊酯、偶氮磷、苯菌灵、苯噁磷、苯甲酸苯甲酯、联苯吡菌胺、溴灭菊酯、溴-大环多胺、溴硫磷、溴螨酯、噻嗪酮、丁酮威、丁酮砜威、丁哒螨灵、多硫化钙、毒杀芬、氯灭杀威、三硫磷、螨蜱胺、灭螨猛、氯杀螨、杀虫脒、杀虫脒盐酸盐、杀螨醇、杀螨酯、敌螨丹、乙酯杀螨醇、chloromebuform、螟铃畏、丙酯杀螨醇、虫螨磷、瓜菊酯I、瓜菊酯II、瓜菊酯、氯氰碘柳胺、蝇毒磷、克罗米通、巴毒磷、硫杂灵、果虫磷、DCPM、DDT、田乐磷、田乐磷-O、田乐磷-S、内吸磷-甲基、内吸磷-O、内吸磷-O-甲基、内吸磷-S、内吸磷-S-甲基、内吸磷-S-甲基砜、抑菌灵、敌敌畏、dicliphos、除螨灵、甲氟磷、消螨酚(dinex)、消螨酚(dinex-diclexine)、敌螨普-4、敌螨普-6、邻敌螨消、硝戊酯、硝辛酯、硝丁酯、敌杀磷、二苯基砜、双硫仑、DNOC、dofenapyn、多拉菌素、因毒磷、依普菌素、益果、乙嘧硫磷、抗螨唑、苯丁锡氧化物、苯硫威、吡螨胺、唑螨酯、胺苯吡菌酮、除螨酯、fentrifanil、氟螨噻、氟螨脲、联氟螨、氟杀螨、FMC 1137、伐虫脒、伐虫脒盐酸盐、formparanate、γ-HCH、果绿啶、苄螨醚、十六基环丙烷羧酸盐、水胺硫磷、茉莉菊酯I、茉莉菊酯II、碘硫磷、林丹、丙螨氰、灭蚜磷、二噻磷、甲硫酚、虫螨畏、甲基溴、速灭威、自克威、贝霉素肟、丙胺氟、久效磷、茂硫磷、莫西菌素、二溴磷、4-氯-2-(2-氯-2-甲基-丙基)-5-[(6-碘-3-吡啶基)甲氧基]哒嗪-3-酮、氟蚁灵、尼可霉素、戊氰威、戊氰威1:1氯化锌复合物、氧乐果、异亚砜磷、砜拌磷、pp'-DDT、对硫磷、苄氯菊酯、芬硫磷、伏杀硫磷、硫环磷、磷胺、聚氯萜烯(polychloroterpenes)、浏阳霉素、丙氯醇、蜱虱威、残杀威、乙噻唑磷、发果、除虫菊酯I、除虫菊酯II、除虫菊酯、哒嗪硫磷、嘧硫磷、奎硫磷、喹硫磷、R-1492、甘氨硫磷、鱼藤酮、八甲磷、克线丹、司拉克丁、苏硫磷、SSI-121、舒非仑、氟虫胺、治螟磷、硫磺、氟螨嗪、氟胺氰菊酯、TEPP、叔丁威、四氯杀螨砜、杀螨好、thiafenox、抗虫威、久效威、甲基乙拌磷、克杀螨、苏云金素、威菌磷、苯螨噻、***磷、唑蚜威、三氯丙氧磷、三活菌素、蚜灭多、vaniliprole、贝斯氧杂嗪、辛酸铜、硫酸铜、cybutryne、二氯萘醌、二氯酚、茵多酸、三苯锡、熟石灰、代森钠、灭藻醌、克藻胺、西玛津、三苯基锡乙酸盐、三苯基锡氢氧化物、育畜磷、哌嗪、托布津、氯醛糖、倍硫磷、吡啶-4-胺、毒鼠碱、1-羟基-1H-吡啶-2-硫酮、4-(喹喔啉-2-基氨基)苯磺酰胺、8-羟基喹啉硫酸盐、溴硝丙二醇、氢氧化铜、甲酚、双硫氧吡啶、多地辛、地克松、甲醛、汞加芬、春雷霉素、春雷霉素盐酸盐水合物、双(二甲基二硫代氨基甲酸酯)镍、三氯甲基吡啶、辛噻酮、奥索利酸、土霉素、羟基喹啉硫酸钾、噻菌灵、链霉素、链霉素倍半硫酸盐、叶枯酞、硫柳汞钠、棉褐带卷蛾GV、放射性土壤杆菌、钝绥螨属种、芹菜夜蛾NPV、缨翅缨小蜂属原子微粒、短距虫牙小蜂(Aphelinus abdominalis)、科列马·阿布拉小蜂、食蚜瘿蚊、苜蓿银纹夜蛾NPV、球形芽孢杆菌、白僵菌、普通草蛉、孟氏隐唇瓢虫、苹果蠹蛾GV、番茄潜蝇离额茧蜂、豌豆潜叶蝇姬小蜂、丽蚜小蜂、浆角蚜小峰、异小杆线虫和大异小杆线虫、斑长足瓢虫、丽扑跳小蜂、暗黑长脊盲蝽(Macrolophus caliginosus)、甘蓝夜蛾NPV、阔柄跳小蜂、绿僵菌属绿僵菌变体蝗绿僵菌、绿僵菌属绿僵菌变体绿僵菌、欧洲松叶蜂NPV和红头新松叶蜂(N.lecontei)NPV、小花椿属种、烟色拟青霉、智利小植绥螨、毛蚊虫斯氏线虫、小卷蛾斯氏线虫、夜蛾斯氏线虫、格氏斯氏线虫、斯氏线虫riobrave、斯氏线虫riobravis、斯氏线虫scapterisci、斯氏线虫属种、赤眼蜂种、西方盲走螨、蜡蚧轮枝菌、唑磷嗪、bisazir、白消安、dimatif、六甲嘧胺、六甲磷、甲基涕巴、甲硫涕巴、甲基唑磷嗪、morzid、氟幼脲、涕巴、thiohempa、三胺硫磷、三胺嗪、乌瑞替派、(E)-十-5-烯-1-基乙酸盐与(E)-十-5-烯-1-醇、(E)-十三-4-烯-1-基乙酸盐、(E)-6-甲基庚-2-烯-4-醇、(E,Z)-十四-4,10-二烯-1-基乙酸盐、(Z)-十二-7-烯-1-基乙酸盐、(Z)-十六-11-醛、(Z)-十六-11-烯-1-基乙酸盐、(Z)-十六-13-烯-11-炔-1-基乙酸盐、(Z)-icos-13-烯-10-酮、(Z)-十四-7-烯-1-醛、(Z)-十四-9-烯-1-醇、(Z)-十四-9-烯-1-基乙酸盐、(7E,9Z)-十二-7,9-二烯-1-基乙酸盐、(9Z,11E)-十四-9,11-二烯-1-基乙酸盐、(9Z,12E)-十四-9,12-二烯-1-基乙酸盐、14-甲基十八-1-烯、4-甲基壬酸-5-醇与4-甲基壬酸-5-酮、α-multistriatin、小蠹性信息素、苹果蠹蛾性信息素、苹果小卷蛾性诱剂、瓜实蝇性诱剂、环氧十九烷、十二-8-烯-1-基乙酸盐、十二-9-烯-1-基乙酸盐、十二-8、10-二烯-1-基乙酸盐、dominicalure、4-辛酸甲酯乙酯、丁子香酚、南部松小蠹诱剂、诱杀烯混剂、诱杀烯混剂I、诱杀烯混剂II、诱杀烯混剂III、诱杀烯混剂IV、棉红蛉虫性诱剂、齿小蠹二烯醇、齿小蠹烯醇、japonilure、三甲基二氧三环壬烷、litlure、粉纹夜蛾性诱剂、诱杀酯、megatomoic acid、甲基丁香油酚、诱虫烯、十八-2,13-二烯-1-基乙酸盐、十八-3,13-二烯-1-基乙酸盐、梨小食心虫信息素、二疣犀甲聚集信息素、ostramone、诱虫环、索迪叮、食菌甲诱醇、十四-11-烯-1-基乙酸盐、地中海实蝇性诱剂、地中海实蝇性诱剂A、地中海实蝇性诱剂B1、地中海实蝇性诱剂B2、地中海实蝇性诱剂C、trunc-call、2-(辛基硫)-乙醇、避蚊酮、丁氧基(聚丙烯乙二醇)、己二酸二丁酯、邻苯二甲酸二丁酯、琥珀酸二丁酯、二乙基甲苯酰胺、二甲基碳酸盐、邻苯二甲酸二甲酯、乙基己二醇、已酰胺、methoquin-butyl、甲基新癸酰胺(methyl neodecanamide)、草氨酸盐、派卡瑞丁、1-二氯-1-硝基乙烷、1,1-二氯-2,2-双(4-乙基苯基)-乙烷、1,2-二氯丙烷与1,3-二氯丙烯、1-溴-2-氯乙烷、2,2,2-三氯-1-(3,4-二氯-苯基)乙酸乙酯、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸盐、2-(1,3-二硫戊环-2-基)苯基二甲基氨基甲酸酯、2-(2-丁氧基乙氧基)乙基硫氰酸盐、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯、2-(4-氯-3,5-甲苄基氧基)乙醇、2-氯乙烯基二乙基磷酸盐、2-咪唑烷酮、2-异戊酰基茚-1,3-二酮、2-甲基(丙-2-炔)氨基苯基甲基氨基甲酸酯、2-氰硫基乙基月硅酸盐、3-溴-1-氯丙-1-烯、3-甲基-1-苯基吡唑-5-基二甲基-氨基甲酸酯、4-甲基(丙-2-炔)氨基-3,5-甲苄基甲基氨基甲酸酯、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯、家蝇磷、丙烯腈、阿耳德林、阿洛氨菌素、除害威、α-蜕皮激素、磷化铝、灭害威、新烟碱、乙基杀扑磷、甲基吡啶磷、苏云金芽孢杆菌δ内毒素、六氟硅酸钡、多硫化钡、熏虫菊、拜耳22/190、拜耳22408、β-氟氯氰菊酯、β-氯氰菊酯、bioethanomethrin、生物氯菊酯、双(2-氯乙基)***、硼砂、溴苯烯磷、溴-DDT、合杀威、畜虫威、butathiofos、丁酯膦、砷酸钙、氰化钙、二硫化碳、四氯化碳、杀螟丹盐酸盐、西法丁、冰片丹、氯丹、十氯酮、氯仿、三氯硝基甲烷、氯腈肟磷、氯批唑磷(chlorprazophos)、顺式-灭虫菊、顺式苄呋菊酯、氯氟氰菊酯、亚砷酸铜、砷酸铜、油酸酮、畜虫磷、冰晶石、CS 708、苯腈膦、杀螟腈、环虫菊、畜蜱磷、d-胺菊酯、DAEP、棉隆、decarbofuran、除线特、异氯硫磷、除线磷、甲基碳酸酯、地昔尼尔、狄氏剂、二乙基5-甲基吡唑-3-基磷酸盐、喘定、四氟甲醚菊酯、地麦威、苄菊酯、二甲基毒虫威、敌蝇威、硝丙酚、戊硝酚、地乐酚、苯虫醚、蔬果磷、dithicrofos、DSP、脱皮甾酮、EI 1642、EMPC、EPBP、牛津郡丙硫磷、杀虫丹、甲酸乙酯、二溴化乙烯、二氯化乙烯、氧化乙烯、EXD、皮蝇磷、双乙威、杀螟硫磷、fenoxacrim、吡氯氰菊酯、线虫磷、乙基倍硫磷、索拉菲尼杂质I(flucofuron)、丁苯硫磷、福司吡酯、丁硫环磷、呋线威、抗虫菊、双胍盐、双胍盐乙酸盐、四硫代碳酸钠、苄螨醚、HCH、HEOD、七氯、速杀硫磷、HHDN、氰化氢、hyquincarb、IPSP、氯唑磷、碳氯灵、异艾氏剂、异柳磷、异索威、稻瘟灵、异噁唑磷、保幼激素I、保幼激素II、保幼激素III、氯戊环、烯虫炔酯、砷酸铅、溴苯磷、lirimfos、噻唑磷、间异丙苯基甲基氨基甲酸酯、磷化镁、叠氮磷、四甲磷、灭蚜硫磷、氯化亚汞、倍硫磷亚砜、威百亩、威百亩-钾、威百亩-钠、甲烷磺酰基氟化物、methocrotophos、甲氧普林、甲醚菊酯、甲氧基氯、异硫氰酸甲酯、甲基氯仿、亚甲基氯化物、恶虫酮、灭蚁灵、萘肽磷、精萘、NC-170、尼古丁、尼古丁硫酸盐、噻虫醛、降烟碱、O-5-二氯-4-碘苯基O-乙基乙基硫代膦酸酯、O,O-二乙基O-4-甲基-2-氧代-2H-色满-7-基硫代磷酸酯、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代磷酸酯、O,O,O',O'-二硫焦磷酸四丙酯、十八烯酸、对二氯苯、甲基对硫磷、戊氯苯酚、戊氯苯基月硅酸盐、PH 60-38、芬硫磷、对氯硫磷、磷化氢、甲基辛硫磷、甲胺嘧磷、聚氯二环戊二烯异构物、***、硫氰酸钾、早熟素I、早熟素II、早熟素III、primidophos、丙氟菊酯、猛杀威、丙硫磷、定菌磷、反灭虫菊(pyresmethrin)、苦木、甲基喹硫磷、quinothion、碘醚柳胺、灭虫菊、鱼藤酮、噻嗯菊酯、鱼尼汀、利阿诺定、沙巴藜芦、八甲磷、克线丹、SI-0009、噻丙腈、***、***、氟化钠、六氟硅酸钠、戊氯酚钠、硒酸钠、硫氰酸钠、米丁FF(sulcofuron)、米丁FF(sulcofuron-sodium)、硫酰氟、硫丙磷、焦油、噻螨威、TDE、丁基嘧啶磷、双硫磷、环戊烯丙菊酯、四氯乙烷、thicrofos、杀虫环、杀虫环草酸氢盐、硫磷嗪、杀虫单(thiosultap)、杀虫单(thiosultap-sodium)、四溴菊酯、反式苄氯菊二丙酯、唑蚜威、三氯甲基对硫磷-3、毒壤膦、混杀威、tolprocarb、氯啶菌酯、烯虫硫酯、藜芦定、藜芦碱、XMC、zetamethrin、磷化锌、zolaprofos、氯氟醚菊酯、四氟醚菊酯、双(三丁基锡)氧化物、溴乙酰胺、磷酸铁、灭绦灵-乙醇胺、三丁基锡氧化物、吡吗啉、杀螺吗啉、1,2-二溴-3-氯丙烷、1,3-二氯丙烯、3,4-二氯四氢噻吩1,1-二氧化物、3-(4-氯苯基)-5-甲基罗丹宁、5-甲基-6-硫基-1,3,5-噻二嗪烷-3-基乙酸、6-异戊烯基氨基嘌呤、anisiflupurin、benclothiaz、细胞***素、DCIP、糠醛、isamidofos、激动素、疣孢漆斑菌组合物、四氯噻吩、二甲苯酚、玉米素、乙基黄酸钾、活化酯、活化酯-S-甲基、大虎杖提取物、α-氯醇、安妥、碳酸钡、双鼠脲、溴鼠灵、溴敌隆、溴鼠胺、氯鼠酮、胆钙化醇、氯杀鼠灵、克鼠灵、杀鼠醚、杀鼠嘧啶、鼠得克、噻鼠灵、敌鼠、钙化醇、氟鼠灵、氟乙酰胺、氟鼠啶、氟鼠啶盐酸盐、鼠特灵、毒鼠磷、总磷、杀鼠酮、灭鼠优、红海葱苷、氟-乙酸钠、硫酸铊、华法林、2-(2-丁氧基乙氧基)-乙基胡椒酸盐、5-(1,3-苯并二唑-5-基)-3-己基环己-2-烯酮、法尼醇与橙花叔醇、增效炔醚、MGK 264、增效醚、增效醛、丙基异构物、S421、增效菊、芝麻林素(sesasmolin)、亚砜、蒽醌、环烷酸铜、氯氧化铜、二环戊二烯、福美双、环烷酸锌、福美锌、衣马宁、病毒唑、氯吲哚酰肼(chloroinconazide)、***、甲基托布津、氮康唑、联苯***醇、溴菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、呋吡菌胺、己唑醇、抑霉唑、亚胺唑、种菌唑、叶菌唑、腈菌唑、多效唑、稻瘟酯、戊菌唑、丙硫菌唑、啶斑肟、咪鲜胺、丙环唑、啶菌噁唑、硅氟唑、戊唑醇、氟醚唑、***酮、***醇、氟菌唑、灭菌唑、嘧啶醇、氯苯嘧啶醇、氟苯嘧啶醇、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、吗菌灵、苯锈定、丁苯吗啉、螺环菌胺、克啉菌、环丙嘧啶、嘧菌胺、嘧霉胺、拌种咯、咯菌腈、苯霜灵、呋霜灵、甲霜灵、R-甲霜灵、呋酰胺、恶霜灵、多菌灵、咪菌威、麦穗宁、噻苯咪唑、乙菌利、菌核利、myclozoline、腐霉利、乙烯菌核利、啶酰菌胺、萎锈灵、甲呋酰胺、氟酰胺、灭锈胺、氧化萎锈灵、吡噻菌胺、噻呋酰胺、多果定、双胍辛胺、嘧菌酯、醚菌胺、烯肟菌酯、烯肟菌胺、氟菌螨酯、氟嘧菌酯、甲基醚菌酯、(E)-苯氧菌胺、肟菌酯、肟醚菌胺、啶氧菌酯、唑菌胺酯、唑胺菌酯、唑菌酯、福美铁、代森锰锌、代森锰、代森联、丙森锌、代森锌、敌菌丹、克菌丹、氟酰亚胺、灭菌丹、甲苯氟磺胺、波尔多混合剂、氧化铜、代森锰铜、喹啉铜、酞菌酯、克瘟散、异稻瘟净、氯瘟磷、甲基立枯磷、敌菌灵、苯噻菌胺、灭瘟素-S、地茂散、百菌清、环氟菌胺、霜脲氰、三氟吡啶胺(cyclobutrifluram)、双氯氰菌胺、哒菌酮、氯硝胺、乙霉威、烯酰吗啉、氟吗啉、二噻农、噻唑菌胺、土菌灵、噁唑菌酮、咪唑菌酮、稻瘟酰胺、嘧菌腙、氟啶胺、flumetylsulforim、氟吡菌胺、fluoxytioconazole、磺菌胺、氟唑菌酰胺、环酰菌胺、乙膦酸铝、恶霉灵、异丙菌胺、氰霜唑、磺菌威、苯菌酮、戊菌隆、四氯苯酞、多抗霉素、霜霉威、吡菌苯威、丙氧喹啉、咯喹酮、焦苯酮(pyriofenone)、喹氧灵、五氯硝基苯、噻酰菌胺、唑菌嗪、三环唑、嗪氨灵、有效霉素、缬菌胺、苯酰菌胺、双炔酰菌胺、氟苯醚酰胺(flubeneteram)、吡唑萘菌胺、氟唑环菌胺、苯并烯氟菌唑、氟唑菌酰羟胺、3-二氟甲基-1-甲基-1H-吡唑-4-羧酸(3',4',5'-三氟-联苯基-2-基)-酰胺、isoflucypram、异噻菌胺中间体(isotianil)、dipymetitrone、6-乙基-5,7-二氧代-吡咯并[4,5][1,4]二噻烯(dithiino)[1,2-c]异噻唑-3-甲腈、2-(二氟甲基)-N-[3-乙基-1,1-二甲基-茚-4-基]吡啶-3-甲酰胺、4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪-3-甲腈、(R)-3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚-4-基]吡唑-4-甲酰胺、4-(2-溴-4-氟-苯基)-N-(2-氯-6-氟-苯基)-2,5-二甲基-吡唑-3-胺、4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1、3-二甲基-1H-吡唑-5-胺、氟茚唑菌胺、甲香菌酯(jiaxiangjunzhi)、利本米昔安/氯苯醚酰胺(lvbenmixianan)、dichlobentiazox、mandestrobin、3-(4,4-二氟-3,4-二氢-3,3-二甲基异喹啉-1-基)喹诺酮、2-[2-氟-6-[(8-氟-2-甲基-3-喹啉基)氧基]苯基]丙烷-2-醇、氟噻唑吡乙酮、N-[6-[[[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸叔丁酯、联苯吡嗪菌胺、inpyrfluxam、trolprocarb、氯氟醚菌唑、ipfentrifluconazole、2-(二氟甲基)-N-[(3R)-3-乙基-1,1-二甲基-茚-4-基]吡啶-3-甲酰胺、N'-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒、N'-[4-(4,5-二氯噻唑-2-基)氧基-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒、[2-[3-[2-[1-[2-[3,5-双(二氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]噻唑-4-基]-4,5-二氢异噁唑-5-基]-3-氯-苯基]甲烷磺酸盐、丁-3-炔N-[6-[[(Z)-[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸酯、N-[[5-[4-(2,4-二甲基苯基)***-2-基]-2-甲基-苯基]甲基]氨基甲酸甲酯、3-氯-6-甲基-5-苯基-4-(2,4,6-三氟苯基)哒嗪、pyridachlometyl、3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚-4-基]吡唑-4-甲酰胺、1-[2-[[1-(4-氯苯基)吡唑-3-基]氧基甲基]-3-甲基-苯基]-4-甲基-四唑-5-酮、1-甲基-4-[3-甲基-2-[[2-甲基-4-(3,4,5-三甲基吡唑-1-基)苯氧基]甲基]苯基]四唑-5-酮、aminopyrifen、唑嘧菌胺、安美速、戊苯吡菌胺、(Z,2E)-5-[1-(4-氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺、florylpicoxamid、fenpicoxamid、metarylpicoxamid、tebufloquin、ipflufenoquin、quinofumelin、异丙噻菌胺、N-[2-[2,4-二氯-苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺、N-[2-[2-氯-4-(三氟甲基)苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺、苯噻菌酯、氰烯菌酯、5-氨基-1,3,4-噻二唑-2-硫醇锌盐(2:1)、氟吡菌酰胺、flufenoxadiazam、flutianil、氟醚菌酰胺、pyrapropoyne、picarbutrazox、2-(二氟甲基)-N-(3-乙基-1,1-二甲基-茚-4-基)吡啶-3-甲酰胺、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚-4-基)吡啶-3-甲酰胺、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-***-1-基)丙基]-3-吡啶基]氧基]苯甲腈、metyltetraprole、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚-4-基)吡啶-3-甲酰胺、α-(1,1-二甲基乙基)-α-[4'-(三氟甲氧基)[1,1'-联苯基]-4-基]-5-嘧啶甲醇、fluoxapiprolin、烯肟菌酯、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-***-1-基)丙基]-3-吡啶基]氧基]苯甲腈、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫烷基-1,2,4-***-1-基)丙基]-3-吡啶基]氧基]苯甲腈、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫基-4H-1,2,4-***-1-基)丙基]-3-吡啶基]氧基]苯甲腈、抗倒酯、丁香菌酯、中生菌素、噻菌铜、噻唑锌、amectotractin、异菌脲、辛菌胺(seboctylamine)、N'-[5-溴-2-甲基-6-[(1S)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-[(1R)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-氯-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-异丙基-N-甲基-甲脒(这些化合物可由WO 2015/155075中所述的方法来制备);N'-[5-溴-2-甲基-6-(2-丙氧基丙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒(此化合物可以由IPCOM000249876D中描述的方法制备);N-异丙基-N’-[5-甲氧基-2-甲基-4-(2,2,2-三氟-1-羟基-1-苯基-乙基)苯基]-N-甲基-甲脒、N’-[4-(1-环丙基-2,2,2-三氟-1-羟基-乙基)-5-甲氧基-2-甲基-苯基]-N-异丙基-N-甲基-甲脒(这些化合物可以由WO 2018/228896中描述的方法制备);N-乙基-N’-[5-甲氧基-2-甲基-4-[(2-三氟甲基)氧杂环丁烷-2-基]苯基]-N-甲基-甲脒、N-乙基-N’-[5-甲氧基-2-甲基-4-[(2-三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒(这些化合物可以由WO 2019/110427中描述的方法制备);N-[(1R)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺、N-[(1R)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺、N-[(1R)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺、8-氟-N-[(1R)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺、8-氟-N-[(1S)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺、N-[(1R)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺、N-((1R)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺、N-((1S)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺(这些化合物可以由WO 2017/153380中描述的方法制备);1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,5-三氟-3,3-二甲基-异喹啉、1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,6-三氟-3,3-二甲基-异喹啉、4,4-二氟-3,3-二甲基-1-(6-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉、4,4-二氟-3,3-二甲基-1-(7-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉、1-(6-氯-7-甲基-吡唑并[1,5-a]吡啶-3-基)-4,4-二氟-3,3-二甲基-异喹啉(这些化合物可以由WO 2017/025510中描述的方法制备);1-(4,5-二甲基苯并咪唑-1-基)-4,4,5-三氟-3,3-二甲基-异喹啉、1-(4,5-二甲基苯并咪唑-1-基)-4,4-二氟-3,3-二甲基-异喹啉、6-氯-4,4-二氟-3,3-二甲基-1-(4-甲基苯并咪唑-1-基)异喹啉、4,4-二氟-1-(5-氟-4-甲基-苯并咪唑-1-基)-3,3-二甲基-异喹啉、3-(4,4-二氟-3,3-二甲基-1-异喹啉基)-7,8-二氢-6H-环戊二烯并[e]苯并咪唑(这些化合物可以由WO 2016/156085中描述的方法制备);N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙烷甲酰胺、N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡唑-4-甲酸乙酯、N,N-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-1,2,4-***-3-胺(这些化合物可以由WO 2017/055473、WO 2017/055469、WO 2017/093348和WO2017/118689中描述的方法制备);2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-***-1-基)丙-2-醇(此化合物可以由WO 2017/029179中描述的方法制备);2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-***-1-基)丙-2-醇(此化合物可以由WO2017/029179中描述的方法制备);3-[2-(1-氯环丙基)-3-(2-氟苯基)-2-羟基-丙基]咪唑-4-甲腈(此化合物可以由WO 2016/156290中描述的方法制备);3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-甲腈(此化合物可以由WO 2016/156290中描述的方法制备);2-氨基-6-甲基-吡啶-3-甲酸(4-苯氧基苯基)甲酯(此化合物可以由WO 2014/006945中描述的方法制备);2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮(此化合物可以由WO 2011/138281中描述的方法制备)、N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯硫代甲酰胺;N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺;(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺(此化合物可以由WO 2018/153707中描述的方法制备);N'-(2-氯-5-甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒;N'-[2-氯-4-(2-氟苯氧基)-5-甲基-苯基]-N-乙基-N-甲基-甲脒(此化合物可以由WO 2016/202742中描述的方法制备);2-(二氟甲基)-N-[(3S)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺(此化合物可以由WO 2014/095675中描述的方法制备);(5-甲基-2-吡啶基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮、(3-甲基异噁唑-5-基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮(这些化合物可以由WO 2017/220485中描述的方法制备);2-氧代-N-丙基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺(此化合物可以由WO 2018/065414中描述的方法制备);1-[[5-[5-(三氟甲基)-1,2,4-噁二唑-3-基]-2-噻吩基]甲基]吡唑-4-甲酸乙酯(此化合物可以由WO 2018/158365中描述的方法制备);2,2-二氟-N-甲基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺、N-[(E)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、N-[(Z)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、N-[N-甲氧基-C-甲基-碳酰亚胺基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺(这些化合物可以由WO 2018/202428中描述的方法制备)。
本发明的这些化合物可以单独使用,但通常使用配制辅助剂,诸如载体、溶剂和表面活性剂(SFA)被配制成组合物。因此,本发明进一步提供了一种组合物,其包含本发明的化合物以及农业上可接受的配制辅助剂。还提供了一种组合物,其主要由本发明的化合物以及农业上可接受的配制辅助剂组成。还提供了一种组合物,其由本发明的化合物以及农业上可接受的配制辅助剂组成。
本发明进一步提供了一种植物生长调节剂组合物,其包含本发明的化合物以及农业上可接受的配制辅助剂。还提供了一种植物生长调节剂组合物,其基本上由本发明的化合物以及农业上可接受的配制辅助剂组成。还提供了一种植物生长调节剂组合物,其由本发明的化合物以及农业上可接受的配制辅助剂组成。
本发明进一步提供了一种植物非生物胁迫管理组合物,其包含本发明的化合物以及农业上可接受的配制辅助剂。还提供了一种植物非生物胁迫管理组合物,其主要由本发明的化合物以及农业上可接受的配制辅助剂组成。还提供了一种植物非生物胁迫管理组合物,其由本发明的化合物、以及农业上可接受的配制辅助剂组成。
本发明进一步提供了一种种子萌发促进剂组合物,其包含本发明的化合物和农业上可接受的配制辅助剂。还提供了一种种子萌发促进剂组合物,其主要由本发明的化合物和农业上可接受的配制辅助剂组成。还提供了一种种子萌发促进剂组合物,其由本发明的化合物和农业上可接受的配制辅助剂组成。
组合物可以呈浓缩物的形式,在使用前稀释这些浓缩物,尽管也可以制成即用型组合物。最终稀释通常用水进行,但是可以替代水或除了水之外使用例如液体肥料、微量营养素、生物有机体、油或溶剂进行。
这些组合物通常包括按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制辅助剂,该配制辅助剂优选地包括按重量计从0至25%的表面活性物质。
这些组合物可以选自多种配制品类型,这些配制品类型中的很多是从Manual onDevelopment and Use of FAO Specifications for Plant Protection Products[关于植物保护产物的FAO标准的发展和使用手册],第5版,1999中得知。这些包括可尘化粉剂(DP)、可溶性粉剂(SP)、水溶性颗粒剂(SG)、水可分散性颗粒剂(WG)、可湿性粉剂(WP)、颗粒剂(GR)(缓释或快释的)、可溶的浓缩物(SL)、油易混合的液体(OL)、超低体积液体(UL)、可乳化的浓缩物(EC)、可分散性浓缩物(DC)、乳液(水包油(EW)和油包水(EO)两者)、微乳液(ME)、悬浮液浓缩物(SC)、气溶胶、胶囊悬浮液(CS)以及种子处理配制品。在任何情况下,所选择的配制品类型将取决于所设想的具体目的以及本发明的化合物的物理、化学和生物学特性。
可粉尘化的粉剂(DP)可以通过将本发明的化合物与一种或多种固体稀释剂(例如,天然粘土、高岭土、叶蜡石、膨润土、氧化铝、蒙脱石、硅藻土(kieselguhr)、白垩土、硅藻土(diatomaceous earths)、磷酸钙、碳酸钙和碳酸镁、硫、石灰、面粉、滑石和其他有机和无机的固体载体)混合并将该混合物机械地碾磨成细粉末来制备。
可溶性粉剂(SP)可以通过将本发明的化合物与一种或多种水溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖)以及任选地一种或多种湿润剂、一种或多种分散剂或所述试剂的混合物进行混合来制备以改进水分散性/水溶性。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水溶性颗粒剂(SG)。
可湿性粉剂(WP)可以通过如下进行制备,即将本发明的化合物与一种或多种固体稀释剂或载体、一种或多种润湿剂以及优选地一种或多种分散剂以及可任选地一种或多种悬浮剂混合,以促进在液体中的分散。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水可分散性颗粒剂(WG)。
可以这样形成颗粒剂(GR):通过将本发明的化合物与一种或多种粉状固体稀释剂或载体的混合物造粒来形成,或者通过将本发明的化合物(或其在一种合适的试剂中的溶液)吸收进多孔颗粒材料(例如浮石、凹凸棒石粘土、漂白土、砂藻土(kieselguhr)、硅藻土(diatomaceous earths)或玉米芯粉)、或通过将本发明的化合物(或其在合适的试剂中的溶液)吸附到硬芯材料(例如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话进行干燥,来由预成型的空白颗粒形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。一种或多种其他添加剂也可以包含在颗粒剂中(例如乳化剂、湿润剂或分散剂)。
可分散的浓缩物(DC)可以通过将本发明的化合物溶解于水或有机溶剂(如酮、醇或乙二醇醚)中进行制备。这些溶液可以含有表面活性剂(例如以改善水稀释或防止喷雾罐中的结晶)。
可乳化的浓缩物(EC)或水包油乳液(EW)可以通过将本发明的化合物溶解于有机溶剂(可任选地包含一种或多种润湿剂、一种或多种乳化剂或所述试剂的混合物)进行制备。在EC中使用的合适有机溶剂包括芳香族烃(如烷基苯或烷基萘,以SOLVESSO 100、SOLVESSO 150和SOLVESSO 200为例;SOLVESSO是注册商标)、酮(如环己酮或甲基环己酮)和醇(如苯甲醇、糠醇或丁醇)、N-烷基吡咯烷酮(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃。EC产品可以在添加到水中时自发地乳化,从而产生具有足够稳定性的乳液,以允许通过适当设备进行喷洒施用。
EW的制备涉及获得作为液体(如果它在室温下不是液体,则它可以在典型地低于70℃的合理温度下被熔化)或处于溶液中(通过将它溶于适当的溶剂中)的本发明的化合物,然后在高剪切下将所得液体或溶液乳化进包含一种或多种SFA的水中,以产生乳液。在EW中使用的合适溶剂包括植物油、氯化烃(如氯苯)、芳香族溶剂(如烷基苯或烷基萘)以及在水中具有低溶解度的其他适当的有机溶剂。
微乳液(ME)可以通过以下方式制备:将水与一种或多种溶剂和一种或多种SFA的共混物混合,以自发地产生热力学稳定的各向同性的液体配制品。本发明的化合物起初存在于水或溶剂/SFA共混物中。适用于ME的溶剂包括以上所述用于EC或EW中的那些。ME可以是水包油体系或油包水体系(存在哪种体系可以通过电导率测量来测定)并且可以适用于在同一配制品中混合水溶性的杀有害生物剂和油溶性的杀有害生物剂。ME适用于稀释到水中,保持为微乳液或形成常规的水包油乳液。
悬浮液浓缩物(SC)可以包括本发明的化合物的精细分散的不溶固体颗粒的含水或无水悬浮液。SC可以任选地使用一种或多种分散剂通过在合适的介质中球磨或珠磨本发明的固体化合物来制备,以产生该化合物的细颗粒悬浮液。在组合物中可以包含一种或多种湿润剂,并且可以包含悬浮剂以降低颗粒沉降的速率。可替代地,可以干磨本发明的化合物并添加至包含此前所述的试剂的水中,以产生所希望的最终产品。
气溶胶配制品包含本发明的化合物以及合适的推进剂(例如正丁烷)。也可将本发明的化合物溶解于或分散于合适的介质(例如水或可与水混溶的液体,如正丙醇)中以提供在非加压的手动喷雾泵中使用的组合物。
胶囊悬浮液(CS)可以通过类似于EW配制品的制备的方法进行制备,但是具有额外的聚合反应阶段,因而获得油滴的水性分散液,其中每个油滴被聚合物壳包封并且包含本发明的化合物以及可任选地该化合物的载体或稀释剂。聚合物壳可以通过界面缩聚反应或通过凝聚程序产生。这些组合物可以提供本发明的化合物的受控释放并且它们可以用于种子处理。本发明的化合物还可以配制在生物可降解的聚合物基质中以提供该化合物的缓慢的、受控的释放。
组合物可以包含一种或多种添加剂以改进该组合物的生物性能,例如通过改进在表面上的湿润性、保持力或分布;被处理表面上的抗雨水性;或本发明的化合物的吸收或流动。这样的添加剂包括表面活性剂(SFA)、基于油的喷雾添加剂,例如某些矿物油或天然植物油(如大豆和油菜籽油),以及这些与其他生物增强助剂(可以帮助或修饰本发明的化合物的作用的成分)的共混物。
湿润剂、分散剂和乳化剂可以是阳离子类型、阴离子类型、两性类型或非离子类型的SFA。
合适的阳离子类型的SFA包括季铵化合物(例如十六烷基三甲基溴化铵)、咪唑啉以及胺盐。
合适的阴离子SFA包括脂肪酸的碱金属盐、硫酸的脂肪族单酯的盐(例如月桂硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷(主要是二酯)之间反应的产物,例如月桂醇与四磷酸之间的反应;另外这些产物可以是乙氧基化的)、硫代琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐以及木质磺酸盐。
合适的两性类型的SFA包括甜菜碱、丙酸盐和甘氨酸盐。
合适的非离子类型的SFA包括环氧烷(如环氧乙烷、环氧丙烷、环氧丁烷或其混合物)与脂肪醇(如油醇或鲸蜡醇)或与烷基酚(如辛基酚、壬基酚或辛基甲酚)的缩合产物;衍生自长链脂肪酸或己糖醇酐的偏酯;所述偏酯与环氧乙烷的缩合产物;嵌段聚合物(包含环氧乙烷和环氧丙烷);烷醇酰胺;单酯(例如脂肪酸聚乙二醇酯);胺氧化物(例如月桂基二甲基氧化胺);和卵磷脂。
合适的悬浮剂包括亲水性胶体(如多糖、聚乙烯吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(如膨润土或凹凸棒石)。
本发明的化合物或组合物可以施用到植物、植物的一部分、植物器官、植物繁殖材料或植物生长场所。
术语“植物”是指植物的所有有形部分,包括种子、幼苗、幼树、根、块茎、茎、秆、叶子和果实。
如本文使用的,术语“场所”意指植物在其中或其上生长的地方,或栽培植物的种子被播种的地方,或者种子将要被置于土壤中的地方。它包括土壤、种子以及幼苗,连同建立的植被。
术语“植物繁殖材料”表示植物的所有生殖部分,例如植物的种子或营养性部分如插条以及块茎。它包括严格意义上的种子、以及根、果实、块茎、球茎、根茎和植物各部分。
通常通过喷洒该组合物进行施用,典型地是通过用于大面积的装在拖拉机上的喷洒机,但是还可以使用其他方法如撒粉(针对粉末)、滴加或浸灌。可替代地,该组合物可以在犁沟中施用,或者在种植前或种植时直接施用于种子。
本发明的化合物或组合物可以在出苗前或出苗后施用。适当地,当组合物被用于调节作物植物的生长或增强对非生物胁迫的耐受性时,其可以在作物出苗后施用。当该组合物被用于促进种子萌发时,可以出苗前施用。
本发明设想了在种植之前、种植期间、或种植之后,向植物繁殖材料施用本发明的化合物或组合物或其任何组合。
虽然可以将活性成分施用于处于任何生理状态下的植物繁殖材料,但通常的方法是在足够耐用的状态下使用种子,以在处理过程中不产生损伤。典型地,该种子是已从田间收获;从植物取下;并且与任何玉米穗轴、茎、外壳以及周围果肉或其他非种子植物材料分离。种子还优选地是生物稳定的,其程度为该处理不会引起对该种子的生物损害。据信可在种子收获和种子播种之间的任何时间(包括在种子播种过程中)随时处理种子。
将活性成分施用或处理于植物繁殖材料上或种植场所中的方法是本领域已知的,并且包括敷裹、包衣、造粒、和浸渍、以及水稻钵盘施用、犁沟施用、土壤湿透、土壤注入、滴灌、通过喷洒器或中枢(central pivot)施用、结合到土壤中(撒施或带施用(band))。可替代地或另外地,活性成分可以被施用到与植物繁殖材料一起播种的合适的基质上。
本发明化合物的施用率可以在宽的限度内变化并且取决于土壤的性质、施用的方法(出苗前或出苗后;种子拌种;施用于种子沟;免耕法施用等)、作物、盛行的气候条件以及其他受施用方法、施用时间以及目标作物支配的因素。用于叶或浸湿施用时,根据本发明的本发明的化合物通常以从1g/ha至2000g/ha,尤其是从5g/ha至1000g/ha的比率施用。对于种子处理,该施用率通常是在每100kg种子0.0005g与150g之间。
本发明的这些化合物和组合物可以在双子叶植物或单子叶作物上施用。根据本发明的组合物可以用于其中的有用植物作物包括多年生和一年生作物,例如浆果植物,例如黑莓、蓝莓、蔓越莓、树莓以及草莓;谷物,例如大麦、玉蜀黍(玉米)、粟、燕麦、水稻、黑麦、高粱、黑小麦以及小麦;纤维植物,例如棉花、***、黄麻和剑麻;大田作物,例如糖甜菜和饲料甜菜、咖啡豆、啤酒花、芥菜、油菜(卡诺拉)、罂粟、甘蔗、向日葵、茶以及烟草;果树,例如苹果、杏、鳄梨、香蕉、樱桃、柑橘、油桃、桃、梨以及李子;草,例如百慕达草、蓝草、本特草、蜈蚣草、牛毛草、黑麦草、圣奥古斯丁草以及结缕草;药草,如罗勒、琉璃苣、细香葱、胡荽、薰衣草、独活草、薄荷、牛至、荷兰芹、迷迭香、鼠尾草以及百里香;豆类,例如菜豆、小扁豆、豌豆以及大豆;坚果,例如杏仁、腰果、落花生、榛子、花生、山核桃、开心果以及核桃;棕榈植物,例如油棕榈;观赏植物,例如花、灌木以及树;其他树木,例如可可树、椰子树、橄榄树以及橡胶树;蔬菜,例如芦笋、茄子、西兰花、卷心菜、胡萝卜、黄瓜、大蒜、莴苣、西葫芦、甜瓜、秋葵、洋葱、胡椒、马铃薯、南瓜、大黄、菠菜以及番茄;和葡萄藤,例如葡萄。
作物应当被理解为是天然存在的、通过常规的育种方法获得或通过基因工程获得的那些。它们包括含有所谓的输出型(output)性状(例如改进的储存稳定性、更高的营养价值以及改进的风味)的作物。
作物应被理解为还包括已经被赋予对除草剂(像溴草腈)或多种类别的除草剂(如ALS-、EPSPS-、GS-、HPPD-和PPO-抑制剂)的耐受性的那些作物。通过常规的育种方法已经被赋予了对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是夏季卡诺拉。通过遗传工程方法而被赋予了对除草剂的耐受性的作物的实例包括例如草甘膦和草铵膦抗性玉米品种,这些玉米品种以商标名/>和/>是可商购的。
作物还应被理解为天然地是或已经赋予对害虫的抗性的那些作物。这包括通过使用重组DNA技术转化从而例如能够合成一种或多种选择性作用毒素的植物,这些毒素是如从例如产毒素的细菌已知的。可以被表达的毒素的实例包括δ-内毒素,营养期杀昆虫蛋白(Vip),细菌定殖线虫的杀昆虫蛋白,以及由蝎子、蛛形纲动物、黄蜂和真菌产生的毒素。
已经被修饰为表达苏云金芽孢杆菌(Bacillus thuringiensis)毒素的作物的实例是Bt maize(先正达种子公司(Syngenta Seeds))。包括编码杀昆虫抗性并且由此表达多于一种毒素的多于一种基因的作物的实例是/>(先正达种子公司)。作物或其种子材料还可以是对多种类型的有害生物具有抗性(当通过遗传修饰产生时的所谓的叠加转基因事件)。例如,植物可以具有表达杀昆虫蛋白同时耐受除草剂的能力,例如/>(陶氏益农公司(Dow AgroSciences),先锋良种国际公司(PioneerHi-Bred International))。
本发明的化合物还可以用于促进非作物植物种子的萌发,例如作为一体式杂草控制程序的一部分。通过减少与杂草的竞争,杂草种子萌发的延缓可以为作物幼苗提供更强的开始。可替代地,本发明的化合物可用于延缓作物植物种子的萌发,例如对于种植者增加了种植时间的灵活性。
通常,在作物的管理中,除了本发明的化合物或组合物之外,种植者将使用一种或多种其他的农用化学或生物药品。还提供了一种混合物,其包含本发明的化合物或组合物以及另外的活性成分。
农用化学或生物药品的实例包括杀有害生物剂如杀螨剂、杀细菌剂、杀真菌剂、除草剂、杀昆虫剂、杀线虫剂、植物生长调节剂、作物增强剂、安全剂、以及植物营养素与植物肥料。合适的混合配伍物的实例可以在Pesticide Manual[杀有害生物剂手册],第15版(英国农作物保护委员会(British Crop Protection Council)出版))中找到。此类混合物可以同时地(例如,作为预配制混合物或以桶混制剂(tank mix))亦或在合适的时间范围内连续地施用到植物、植物繁殖材料或植物生长场所上。多种杀有害生物剂与本发明共同施用具有使向作物施用产品所费农民的时间最小化的额外益处。该组合还可包括使用任何手段,例如常规育种或基因修饰结合到植物中的特定植物性状。
本发明提供了具有式(I)的化合物,或包含根据式(I)的化合物和农业上可接受的配制辅助剂的组合物,用于改进植物对非生物胁迫的耐受性、调节或改进植物的生长、促进种子萌发、和/或针对化学药品的植物毒性效应将植物安全化的用途。
本发明还提供了本发明的化合物、组合物、或混合物,用于改进植物对非生物胁迫的耐受性、调节或改进植物的生长、促进种子萌发、和/或针对化学药品对植物毒性效应将植物安全化的用途。
配制品实例
将该活性成分与辅助剂充分混合并且将混合物在适合的研磨机中充分研磨,从而提供可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
将该活性成分与辅助剂充分混合并且将混合物在合适的研磨机中充分研磨,从而提供可以直接用于种子处理的粉剂。
可乳化浓缩物
在植物保护中可以使用的具有任何所要求的稀释的乳液可以通过用水稀释由这种浓缩物中获得。
通过将该活性成分与载体混合并且将混合物在适合的研磨机中研磨而获得即用型粉尘剂。此类粉剂还可以用于种子的干拌种。
挤出机颗粒剂
将该活性成分与辅助剂混合并且研磨,并且将该混合物用水润湿。将混合物挤出并且然后在空气流中干燥。
包衣颗粒剂
活性成分[具有式(I)的化合物] 8%
聚乙二醇(分子量200) 3%
高岭土 89%
将精细研磨的活性成分在混合器中均匀地施用到用聚乙二醇湿润的高岭土上。以此方式获得无尘的包衣颗粒剂。
悬浮液浓缩物
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且通过喷洒、倾倒或浸渍保护其对抗微生物的侵染。
种子处理用的可流动性浓缩物
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且通过喷洒、倾倒或浸渍保护其对抗微生物的侵染。
缓释的胶囊悬浮液
将28份的具有式(I)的化合物的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8:1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的粒度。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将混合物搅拌直至聚合反应完成。
将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮液配制品包含28%的活性成分。该介质胶囊的直径是8-15微米。
将所得配制品作为在适合于此目的的装置中的水性悬浮液施用至种子上。
实例
接下来的实例用来说明本发明。
化合物的合成与表征
贯穿本部分使用了以下缩写:br s=宽单峰,℃=摄氏度,CDCl3=氯仿-d,d=二重峰,dd=双二重峰,m=多重峰,M=摩尔,MHz=兆赫兹,s=单峰,sext=六重峰,THF=四氢呋喃
LC-MS记录在来自沃特斯公司(Waters)的质谱仪(SQD、SQDII单四极杆质谱仪)上,其装备有电喷射源(极性:正离子和负离子,毛细管:3.00kV,锥孔范围:30V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h,质量范围:100至900Da)和来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500。
方案A:运行时间:1.5min;溶剂:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;流量(ml/min)0.85,梯度:10%B等度持续0.2min,然后在1.0min内10%-100%B,100%B等度持续0.2min,在0.05min内100%-10%B,10%B等度持续0.05min。
方案B:运行时间:3.0min;溶剂:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;流量(ml/min)0.85,梯度:10%B等度持续0.2min,然后在2.5min内10%-100%B,100%B等度持续0.3min。Rt代表保留时间。
一般程序A:该实例说明具有式(VI-a)的锡烷化合物的一般合成制备
在室温在氩气下,向具有式(VI-a)的末端炔烃底物(1.0当量)和Pd(PPh3)4(0.05当量)在THF(0.2M)中的溶液中加入三丁基氢化锡(1.2当量)。将混合物搅拌90min后,将溶液经硅藻土过滤。在真空中浓缩所得溶液。粗物质通过快速柱色谱法(SiO2,环己烷)纯化以得到呈无色油状物的相应的具有式(III-a)的锡烷化合物(80%-90%纯度)。具有式(III-a)的粗锡烷材料不经进一步纯化用于下一步反应。
一般程序B:该实例说明了经由施蒂勒偶联的具有式(I-a)的化合物的一般合成制备
在氩气气氛下向碘化乙烯(II-a)(1.0当量)的溶液中加入在1,4-二噁烷(0.1M)中的三呋喃基膦(0.40当量),然后加入具有式(III-a)的锡烷化合物(3.0当量)。通过使氩气鼓泡通过溶液持续10min使溶液脱气。添加Pd2(dba)3(0.10当量),然后密封反应小瓶并加热至120℃持续30min。使混合物溶液冷却至室温并经硅藻土过滤。在真空中除去溶剂,并将粗物质通过快速柱色谱法(SiO2,环己烷/乙酸乙酯)纯化以提供呈油状物质的相应的偶联产物(I-a)。
除非下文另有说明,否则所有反应均根据一般程序A和B进行。
实例1:(E,2E)-4-(1-甲基环己基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(化合物P-1):
1H NMR(400MHz,CDCl3)δppm:7.46(s,1H),6.98(quin,J=1.6Hz,1H),6.42(d,J=16.9Hz,1H),6.13-6.16(m,1H),6.07(d,J=16.5Hz,1H),3.76(s,3H),2.04(t,J=1.5Hz,3H),1.45-1.58(m,6H),1.37-1.43(m,2H),1.33(m,2H),1.02(s,3H);
13C NMR(101MHz,CDCl3)δppm:170.5,167.1,150.8,145.8,141.3,135.5,114.8,113.0,100.3,51.6,37.8(2C),36.6,27.2,26.3,22.4(2C),10.7。
实例2:(E,2E)-4-(4,4-二氟环己基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(化合物P-2):
需要通过反相柱色谱法纯化;
1H NMR(400MHz,CDCl3)δppm:7.50(s,1H),6.98(quin,J=1.6Hz,1H),6.36(dd,J=16.1,7.3Hz,1H),6.18(dd,J=16.1,1.1Hz,1H),6.15(quin,J=1.4Hz,1H),3.76(s,3H),2.07-2.18(m,3H),2.05(t,J=1.5Hz,3H),1.67-1.86(m,4H),1.49-1.57(m,2H);
13C NMR(101MHz,CDCl3)δppm:170.4,166.8,151.7,141.2,138.4,135.7,123.3(t,J=240Hz),117.8,112.1,100.4,51.6,40.0,33.2(t,J=24Hz),28.7(d,J=9,3Hz),10.7;
19F NMR(377MHz,CDCl3)δppm:-92.05(d,J=235.7Hz,1F),-101.42(d,J=236.0Hz,1F)。
实例3:(E,2E)-4-(1-甲基环戊基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(化合物P-6):
条件:使用三苯基胂代替三呋喃基膦。将反应在100℃下搅拌60min。
1H NMR(400MHz,CD2Cl2)δppm:7.46(s,1H),7.06-6.93(m,1H),6.50(d,J=16.5Hz,1H),6.18-6.14(m,1H),6.09(d,J=16.5Hz,1H),3.73(s,3H),2.00(s,2H),2.04-1.96(m,1H),1.77-1.34(m,8H),1.09(s,3H);
13C NMR(101MHz,CD2Cl2)δppm:170.5,166.9,151.0,145.2,141.4,135.4,114.1,112.6,100.6,51.4,45.3,39.5,25.2,24.1,10.4。
实例4:(E,2E)-4-(1-甲基环丙基)-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(化合物P-7):
将反应在100℃下搅拌30min;需要通过反相柱色谱法纯化;
1H NMR(400MHz,CDCl3)δppm:7.43(s,1H),6.97(quin,J=1.6Hz,1H),6.13-6.16(m,1H),6.09(d,J=16.2Hz,1H),6.04(d,J=16.2Hz,1H),3.75(s,3H),2.04(t,J=1.5Hz,3H),1.22(s,3H),0.64-0.68(m,4H);
13C NMR(101MHz,CDCl3)δppm:170.5,167.1,150.3,143.5,141.3,135.6,114.1,112.6,100.4,51.6,21.0,18.3,15.9(2C),10.7。
实例5:(E,2E)-2-[(3,4-二甲基-5-氧代-2H-呋喃-2-基)甲醛]-5,5-二甲基-己-3-烯酸甲酯(化合物P-10):
1H NMR(400MHz,CD2Cl2))δppm:7.50(s,1H),6.47(d,J=16.5Hz,1H),6.10(d,J=16.5Hz,1H),6.02-5.95(m,1H),3.75(s,3H),2.07-2.03(m,3H),1.91(t,J=1.1Hz,3H),1.08(s,9H);
13C NMR(101MHz,CD2Cl2)δppm:170.9,166.9,152.9,151.1,146.2,127.8,113.8,112.6,102.1,51.4,33.6,29.1,11.1,8.30。
实例6:(E,2E)-4-环戊基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(化合物P-11):
条件:需要通过反相柱色谱法纯化。
1H NMR(400MHz,CDCl3)δppm:7.46(s,1H),7.00-6.96(m,1H),6.39(dd,J=8.1,16.1Hz,1H),6.18-6.11(m,2H),3.76(s,3H),2.49(sext,J=8.1Hz,1H),2.06-2.02(m,3H),1.86-1.77(m,2H),1.71-1.63(m,2H),1.62-1.55(m,2H),1.40-1.31(m,2H);
13C NMR(101MHz,CDCl3)δppm:170.5,167.0,151.0,141.3,140.6,135.6,116.7,112.6,100.4,51.6,44.9,33.2,25.3,10.7。
实例7:(E,2E)-5-甲氧基-5-甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(化合物P-12):
1H NMR(400MHz,CDCl3)δppm:7.56(s,1H),7.04-6.93(m,1H),6.41(d,J=16.9Hz,1H),6.26(d,J=16.9Hz,1H),6.20-6.09(m,1H),3.78(s,3H),3.19(s,3H),2.05(s,3H),1.32(s,6H);
13C NMR(101MHz,CDCl3)δppm:170.4,166.9,152.3,141.2,139.9,135.7,117.8,111.8,100.4,75.5,51.7,50.5,25.8,10.7。
实例8:(E,2E)-4-环己基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]丁-3-烯酸甲酯(化合物P-13):
1H NMR(400MHz,CDCl3)δppm:7.45(s,1H),7.00-6.90(m,1H),6.35(dd,J=7.2,16.3Hz,1H),6.14-6.06(m,2H),3.75(s,3H),2.01(br s,4H),1.77-1.62(m,5H),1.31-1.08(m,5H);
13C NMR(101MHz,CDCl3)δppm:170.5,167.0,151.1,141.7,141.3,135.6,116.2,112.7,100.4,51.6,42.2,32.8,26.1,26.0,10.7。
实例9:(E,2E)-5,5-二甲基-2-[(4-甲基-5-氧代-2H-呋喃-2-基)甲醛]己-3-烯酸甲酯(化合物P-14):
1H NMR(400MHz,CD2Cl2)δppm:7.49(s,1H),7.06-6.95(m,1H),6.48(d,J=16.5Hz,1H),6.19(s,1H),6.09(d,J=16.5Hz,1H),3.75(s,3H),2.05-2.00(m,3H),1.08(s,9H);
13C NMR(101MHz,CD2Cl2)δppm:170.5,166.9,151.2,146.2,141.4,135.4,113.6,112.5,100.6,51.4,33.7,29.1,10.4。
表2:表1中选定化合物的LC/MS数据(Rt=保留时间)。
生物学实例
实例B1:冷胁迫条件下玉米种子萌发
方法:玉米种子(var.NK Falkone,Syngenta Seeds SAS,St.Sauveur,France[var.NK Falkone,先正达种子公司,圣苏维尔,法国])使用筛子按大小分类以剔除圆形种子。将这些玉米种子置于24孔板中(每孔1粒种子,每个板被视为一个实验单位或实验重复)。通过每孔添加250μL的含有0.5%DMSO的蒸馏水(以及在给定浓度下的测试物质),从而起始萌发。将8个重复(即,8个板)用于每次处理的表征。使用来自HJ-BIOANALYTIK的密封箔(聚烯烃Art.Nr.900320)将平板进行密封。所有板均置于15℃和60%相对湿度的气候室中。该实验采用完全随机设计。
随着时间推移,通过在不同的时间点拍摄照片来跟踪萌发。使用Image J软件以显影大图像自动进行图像分析。通过拟合趋势曲线来进行萌发的动力学分析。从趋势曲线上计算三个参数:T50(50%萌发所需时间;萌发速度);曲线的斜率(萌发的均匀性)和平台(萌发种子的总百分比)。
使用给定化合物的处理在4个浓度(2、10、50和250μM)下进行。
在最高速率(250μM)下,化合物P-2、P-3、P-4、P-6、P-8、P-9、P-10、P-15和P-19与未处理的对照相比,会降低T50值超过5%。此外,在相同速率(250μM)下,化合物P-2、P-3、P-6、P-8、P-9、P-10、P-12、P-15和P-19与未处理的对照相比,T50处的曲线斜率增加超过50%。
实例B2:玉米叶的暗诱导衰老
已知的是独脚金内酯调节(加速)叶衰老,可能地通过D14受体信号。还已知衰老是允许养分重新分配的重要过程。在玉米叶暗诱导的衰老测定中测试了具有式(I)的化合物并与未处理的对照进行比较。
品种Multitop的玉米植物在相对湿度为75%且23℃-25℃的温室中生长6周。将1.4cm直径的叶圆片放置于24孔板中,该板以0.5%DMSO的最终浓度的浓度梯度(100μM-0.0001μM)含有测试化合物。以12次重复测试每个浓度。用密封箔密封板。刺破箔以提供在每个孔中的气体交换。将该板放置于完全黑暗的气候室中。将板在湿度为75%且23℃的室中温育8天。在第0、5、6、7和8天拍摄每个板的照片,并使用ImageJ软件开发的宏进行图像分析。使用图像分析确定在其下达到50%衰老的浓度(IC50)。该值越低,衰老诱导效力越高。化合物P-2、P-4、P-6、P-7、P-8、P-12、P-15、P-16、P-17、P-19和P-20显示IC50低于3μM。
Claims (15)
1.一种具有式(I)的化合物:
其中
R1是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C6环烷基;
R2是氢、卤素、C1-C3烷基、C1-C3烷氧基或C3-C6环烷基;
R3是氢或C1-C3烷基;
R4是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基羰基-N(C1-C3烷基)氨基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基;
R5是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基或C2-C6炔基;
R6是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C6烷基羰基-N(C1-C3烷基)氨基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6烷基硫烷基;或者
R4和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,其任选地被1、2、3或4个选自R9的基团取代;或者
R5和R6与它们所附接的碳原子一起形成氧代基团或3元至6元环烷基环,其任选地被1、2、3或4个选自R9的基团取代;或者
R4、R5和R6与它们所附接的碳原子一起形成8元至12元碳三环体系,其任选地被1、2、3或4个选自R9的基团取代;
R7是氢、C1-C6烷基、C1-C6卤代烷基或C3-C6环烷基;
R8是氢或C1-C3烷基;
R9是卤素、C1-C3烷基、C1-C3烷氧基、氰基或氧代基(=O);
或其盐。
2.根据权利要求1所述的化合物,其中,R1是氢、C1-C3烷基或C1-C3烷氧基。
3.根据权利要求1或权利要求2所述的化合物,其中,R2是C1-C3烷基或C1-C3烷氧基。
4.根据权利要求1至3中任一项所述的化合物,其中,R5是氢、C1-C3烷基或C2-C4烯基。
5.根据权利要求1至4中任一项所述的化合物,其中,R4是氢、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C3烷基羰基-N(C1-C3烷基)氨基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基或C1-C3烷基硫烷基。
6.根据权利要求1至5中任一项所述的化合物,其中,R6是氢、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3烷氧基羰基、N,N-二(C1-C3烷基)氨基氧基羰基、C1-C3烷基磺酰基或C1-C3烷基硫烷基。
7.根据权利要求1至4中任一项所述的化合物,其中,R4和R6与它们所附接的碳原子一起形成4元至6元环烷基环,其任选地被1、2或3个选自R9的基团取代。
8.根据权利要求1至4中任一项所述的化合物,其中,R4、R5和R6与它们所附接的碳原子一起形成8元至10元碳三环体系,其任选地被1个或2个选自R9的基团取代。
9.根据权利要求1至8中任一项所述的化合物,其中,R7是C1-C3烷基。
10.一种植物生长调节或种子萌发促进组合物,其包含根据权利要求1至9中任一项所述的化合物,以及农业上可接受的配制辅助剂。
11.一种用于在场所调节植物生长的方法,所述方法包括向所述场所施用根据权利要求1至9中任一项所述的化合物或调节植物生长量的根据权利要求10所述的组合物。
12.一种用于促进种子萌发的方法,所述方法包括向所述种子或包含所述种子的场所施用根据权利要求1至9中任一项所述的化合物或促进种子萌发量的根据权利要求10所述的组合物。
13.一种用于改进作物养分吸收的方法,所述方法包括向所述植物或其场所施用根据权利要求1至9中任一项所述的化合物或根据权利要求10所述的植物生长调节或种子萌发促进组合物。
14.根据权利要求1至9中任一项所述的具有式(I)的化合物或如权利要求10中所定义的组合物用于促进种子萌发和/或用于调节植物生长的用途。
15.一种种子,其包含根据权利要求1至9中任一项所述的具有式(I)的化合物或根据权利要求10所述的组合物。
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