CN102112439B - 作为除草剂的5-杂环基烷基-3-羟基-2-苯基环戊-2-烯酮 - Google Patents
作为除草剂的5-杂环基烷基-3-羟基-2-苯基环戊-2-烯酮 Download PDFInfo
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- CN102112439B CN102112439B CN2009801294512A CN200980129451A CN102112439B CN 102112439 B CN102112439 B CN 102112439B CN 2009801294512 A CN2009801294512 A CN 2009801294512A CN 200980129451 A CN200980129451 A CN 200980129451A CN 102112439 B CN102112439 B CN 102112439B
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- alkyl
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- compound
- alkoxyl
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- 239000004009 herbicide Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 730
- -1 hydrogen Chemical class 0.000 claims description 445
- 125000003545 alkoxy group Chemical group 0.000 claims description 163
- 229910052736 halogen Inorganic materials 0.000 claims description 162
- 239000001257 hydrogen Substances 0.000 claims description 161
- 229910052739 hydrogen Inorganic materials 0.000 claims description 161
- 150000002367 halogens Chemical class 0.000 claims description 159
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 144
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 136
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 82
- 125000001072 heteroaryl group Chemical group 0.000 claims description 73
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 54
- 229910052760 oxygen Inorganic materials 0.000 claims description 53
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 46
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 46
- 239000001301 oxygen Substances 0.000 claims description 46
- 150000002431 hydrogen Chemical group 0.000 claims description 44
- 239000000460 chlorine Substances 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 241000196324 Embryophyta Species 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 24
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000003368 amide group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 239000005864 Sulphur Substances 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims description 12
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 244000025254 Cannabis sativa Species 0.000 claims description 10
- 244000038559 crop plants Species 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 8
- 240000008042 Zea mays Species 0.000 claims description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
- 235000005822 corn Nutrition 0.000 claims description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 229920000742 Cotton Polymers 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
- 229910052728 basic metal Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 150000003818 basic metals Chemical class 0.000 claims description 3
- 235000013339 cereals Nutrition 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 2
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000018262 Arachis monticola Nutrition 0.000 claims description 2
- 241000219146 Gossypium Species 0.000 claims description 2
- 244000020551 Helianthus annuus Species 0.000 claims description 2
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 240000000111 Saccharum officinarum Species 0.000 claims description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
- 235000020232 peanut Nutrition 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims 1
- 235000021536 Sugar beet Nutrition 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 114
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- 239000000243 solution Substances 0.000 description 64
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 64
- 239000002585 base Substances 0.000 description 53
- 238000002360 preparation method Methods 0.000 description 44
- 239000002904 solvent Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 37
- 239000003513 alkali Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- 238000003756 stirring Methods 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 0 CC(*)(**)*C(*)(C(*)(*)C(O)=C1c2c(*)cc(*)c(*)c2P)C1=O Chemical compound CC(*)(**)*C(*)(C(*)(*)C(O)=C1c2c(*)cc(*)c(*)c2P)C1=O 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 10
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- 239000011630 iodine Substances 0.000 description 9
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
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- 239000013543 active substance Substances 0.000 description 7
- 150000001502 aryl halides Chemical class 0.000 description 7
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- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 description 5
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- 239000004563 wettable powder Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
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- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
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Abstract
适于用作除草剂的式(I)化合物,其中取代基如权利要求1中所定义。
Description
本发明涉及新的除草活性的环二酮类及其衍生物,涉及它们的制备方法,涉及包括这些化合物的组合物,还涉及它们在防治杂草,特别是在有用植物作物中的杂草,或者抑制不希望的植物生长中的用途。
具有除草作用的环状二酮化合物描述于例如WO01/74770和WO96/03366。
目前已发现具有除草和生长抑制特性的新环戊烷二酮化合物及其衍生物。
因此,本发明涉及式(I)化合物
其中
R1是氢,甲基,乙基,正丙基,异丙基,卤代甲基,卤代乙基,卤素,乙烯基,乙炔基,甲氧基,乙氧基,卤代甲氧基,卤代乙氧基,环丙基或卤代环丙基,
R2和R3独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C2-C6卤代炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基,氰基,硝基,苯基,被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基,或者杂芳基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的杂芳基,
R4是氢,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基或氰基,
R5,R6,R7,R8和R9独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6卤代烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基,氰基,硝基,苯基,被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基,或者杂芳基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基取代的杂芳基,或者苄基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苄基,或者其中环或链亚甲基任选用氧或硫原子替换的C3-C6环烷基C1-C3烷基,或者
R6和R7或者R8和R9与它们连接至的碳原子一起形成任选经取代的3-至8-元环,任选含有氧、硫或氮原子,或者
R5和R6一起形成键,
Q是C3-C8饱和的或一不饱和的含有至少一个选自O、N和S的杂原子的杂环基,其是未经取代的或被下述基团取代:式=O、=N-R10残基或C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基C1-C2烷基,C3-C6环烷基,苯基,被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基,其中R10是C1-C6烷基,C1-C6卤代烷基,C3-C7环烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷基羰基,C1-C6卤代烷基羰基,C1-C6烷氧羰基,C1-C6烷基氨基羰基,C2-C8二烷基氨基羰基,C1-C6卤代烷基亚磺酰基或C1-C6卤代烷基磺酰基,
m是1、2或3,
其中当m是2或3时R6或R7可以具有不同的含义,和
G是氢或农业上可接受的金属,锍,铵或潜伏(latentiating)基团。
在式I化合物的取代基定义中,各烷基部分无论单独的或作为更大基团(比如烷氧基、烷硫基、烷基羰基、烷基氨基羰基和二烷基氨基羰基)的一部分是直链或支化的链并且是例如甲基、乙基、正丙基、正丁基、正戊基、正己基、异丙基、正丁基、仲丁基、异丁基、叔丁基或新戊基。烷基适宜地是C1-C6烷基,但是优选是C1-C4烷基,更优选C1-C2烷基。
烯基和炔基部分可以是直链或支化的链的形式,且所述烯基部分,在合适的情况下,可以是(E)-或(Z)-构型。实例是乙烯基、烯丙基和炔丙基。烯基和炔基部分可以含有一个或多个任意组合的双键和/或三键。应理解,这些术语中包括丙二烯基和炔基(alkylinyl)烯基。
卤素是氟、氯、溴或碘。
卤代烷基是用一个或多个相同或不同卤素原子取代的烷基,并且是例如CF3、CF2Cl、CF2H、CCl2H、FCH2、ClCH2、BrCH2、CH3CHF、(CH3)2CF、CF3CH2或CHF2CH2。
术语“杂芳基”优选表示包含至少一个杂原子并且由单环或者两个或两个以上稠环组成的芳族环系。优选地,单环含有多至三个杂原子而双环系含有多至四个杂原子,所述杂原子优选选自氮、氧和硫。上述基团的实例包括呋喃基,噻吩基,吡咯基,吡唑基,咪唑基,1,2,3-三唑基,1,2,4-三唑基,噁唑基,异噁唑基,噻唑基,异噻唑基,1,2,4-噁二唑基,1,3,4-噁二唑基,1,2,5-噁二唑基,1,2,3-噻二唑基,1,2,4-噻二唑基,1,3,4-噻二唑基,1,2,5-噻二唑基,吡啶基,嘧啶基,哒嗪基,吡嗪基,1,2,3-三嗪基,1,2,4-三嗪基,1,3,5-三嗪基,苯并呋喃基,苯并异呋喃基,苯并噻吩基,苯并异噻吩基,吲哚基,异吲哚基,吲唑基,苯并噻唑基,苯并异噻唑基,苯并噁唑基,苯并异噁唑基,苯并咪唑基,2,1,3-苯并噁二唑,喹啉基,异喹啉基,噌啉基,酞嗪基,喹唑啉基,喹喔啉基,萘啶基,苯并三嗪基,嘌呤基,蝶啶基和吲嗪基。
杂芳族基团的优选实例包括吡啶基、嘧啶基、三嗪基、噻吩基、呋喃基、噁唑基、异噁唑基、2,1,3-苯并噁二唑基和噻唑基。
另一组优选杂芳基包含呋喃基、噻吩基、吡唑基、1,2,3-三唑基、1,2,4-三唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、喹啉基、异喹啉基、噌啉基、喹唑啉基或喹喔啉基。
术语“杂环基”优选是指非芳族优选单环或双环的含有多至8个原子的环系,其包括至少一个(优选一个或两个)选自O、S和N的杂原子。这种环的实例包括1,3-二硫杂环己烷,1,3-二噁烷,1,4-二噁烷,吗啉,硫吗啉,哌嗪,四氢吡喃,哌啶,硫杂环己烷,1,3-二氧杂环戊烷,四氢呋喃,四氢噻吩,吡咯烷(pirolidine),咪唑啉,氮杂环丁烷,氧杂环丁烷,硫杂环丁烷,氮丙啶,环氧乙烷(epoxide)和硫杂环丙烷。
杂环残基的优选实例包括1,3-二噁烷,吗啉,硫吗啉,四氢吡喃,1,3-二氧杂环戊烷,四氢呋喃和四氢噻吩。
环烷基优选包括环丙基、环丁基、环戊基和环己基。
对于取代的杂环基比如分别由R6和R7以及R8和R9形成的环,优选一个或多个取代基独立地选自卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,硝基和氰基。应理解二烷基氨基取代基包括其中所述二烷基和它们与之连接的N原子一起形成五、六或七元杂环的那些,其还可以含有一个或两个选自O、N或S的其它杂原子并且其任选由一个或两个独立选择的C1-C6烷基取代。当通过联接N原子上的两个基团来形成杂环时,所成环适宜地是吡咯烷,哌啶,硫代吗啉和吗啉,其各自可以由一个或两个独立地选择的C1-C6烷基取代。
本发明还涉及式I化合物可与胺、碱金属和碱土金属碱或季铵碱形成的盐。
在作为成盐物质的碱金属和碱土金属氢氧化物中应特别提及锂、钠、钾、镁和钙的氢氧化物,更尤其是钠和钾的氢氧化物。根据本发明的式I化合物还包括可以在成盐期间形成的水合物。
适于形成铵盐的胺的实例包括氨以及伯、仲和叔C1-C18烷基胺,C1-C4羟基烷基胺和C2-C4烷氧基烷基胺,例如甲胺,乙胺,正丙胺,异丙胺,四种丁胺异构体,正戊基胺,异戊基胺,己基胺,庚基胺,辛基胺,壬基胺,癸基胺,十五烷基胺,十六烷基胺,十七烷基胺,十八烷基胺,甲基乙胺,甲基异丙胺,甲基己基胺,甲基壬基胺,甲基十五烷基胺,甲基十八烷基胺,乙基丁胺,乙基庚基胺,乙基辛基胺,己基庚基胺,己基辛基胺,二甲胺,二乙胺,二正丙胺,二异丙胺,二正丁胺,二正戊基胺,二异戊基胺,二己基胺,二庚基胺,二辛基胺,乙醇胺,正丙醇胺,异丙醇胺,N,N-二乙醇胺,N-乙基丙醇胺,N-丁基乙醇胺,烯丙基胺,正丁-2-烯基胺,正戊-2-烯基胺,2,3-二甲基丁-2-烯基胺,二丁-2-烯基胺,正己-2-烯基胺,丙二胺,三甲胺,三乙胺,三正丙胺,三异丙胺,三正丁胺,三异丁胺,三仲丁胺,三正戊基胺,甲氧基乙胺和乙氧基乙胺;杂环胺,例如吡啶,喹啉,异喹啉,吗啉,哌啶,吡咯烷,吲哚啉,奎宁环和氮杂伯芳基胺,例如苯胺,甲氧基苯胺,乙氧基苯胺,邻-,间-和对-甲苯胺,亚苯基二胺,联苯胺,萘胺和邻-,间-和对-氯苯胺;但尤其是三乙胺,异丙胺和二异丙胺。
优选适于成盐的季铵碱对应于例如式[N(Ra Rb Rc Rd)]OH,其中Ra、Rb、Rc和Rd各自彼此独立地是C1-C4烷基。可以例如通过阴离子交换反应来获得其它的适宜四烷基铵与其它阴离子所成的碱。
农业上可接受的金属是碱金属或碱土金属离子,例如钠、钾、镁和钙离子,和过渡金属离子,例如铜和铁原子。适宜的铵离子是NH4 +,烷基铵,二烷基铵,三烷基铵和四烷基铵离子。适宜的锍离子是三烷基锍离子,例如三甲基锍离子。
应理解在G是如上文所提及的金属、铵或锍并由此代表阳离子的那些式I化合物中,相应负电荷大体上在O-C=C-C=O单元上离域化。
选择潜伏基团G使其在施用至经处理的区域或植物之前、期间或之后,可以通过生化、化学或物理学方法中的一种或其组合将之除去以产生其中G是H的式I化合物。上述方法的实例包括酶解、化学水解和光解。带有这种基团G的化合物可以提供一些优势,比如经处理植物的改进的表皮穿透,作物增加的耐受性,包含其它除草剂、除草剂安全剂、植物生长调节剂、杀真菌剂或杀虫剂的制剂混合物中改进的相容性或稳定性,或者减少的土壤淋溶。
所述潜伏基团G优选选自C1-C8烷基,C2-C8卤代烷基,苯基C1-C8烷基(其中该苯基可任选被C1-C3烷基,C1-C3卤代烷基,C1-C3烷氧基,C1-C3卤代烷氧基,C1-C3烷硫基,C1-C3烷基亚磺酰基,C1-C3烷基磺酰基,卤素,氰基或硝基取代),杂芳基C1-C8烷基(其中该杂芳基可任选被C1-C3烷基,C1-C3卤代烷基,C1-C3烷氧基,C1-C3卤代烷氧基,C1-C3烷硫基,C1-C3烷基亚磺酰基,C1-C3烷基磺酰基,卤素,氰基或硝基取代),C3-C8烯基,C3-C8卤代烯基,C3-C8炔基,C(Xa)-Ra,C(Xb)-Xc-Rb,C(Xd)-N(Rc)-Rd,-SO2-Re,-P(Xe)(Rf)-Rg或CH2-Xf-Rh其中Xa,Xb,Xc,Xd,Xe和Xf彼此独立是氧或硫;
Ra是H,C1-C18烷基,C2-C18烯基,C2-C18炔基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔基C1-C5氧基烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基,苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基,杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基,
Rb是C1-C18烷基,C3-C18烯基,C3-C18炔基,C2-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C2-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基,(其中该杂芳基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C3-C5卤代烯基,C3-C8环烷基,苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基,杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基,
Rc和Rd各自彼此独立是氢,C1-C10烷基,C3-C10烯基,C3-C10炔基,C2-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C2-C5烷基氨基烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基,苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基,杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基,杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基氨基,二杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二杂芳基氨基,苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基氨基,二苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二苯基氨基,或者C3-C7环烷基氨基,二-C3-C7环烷基氨基或C3-C7环烷氧基;或者Rc和Rd可以一起联接形成3-7元环,任选含有一个选自O或S的杂原子,
Re是C1-C10烷基,C2-C10烯基,C2-C10炔基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基,苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基,杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基,杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基氨基,二杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二杂芳基氨基,苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基氨基,二苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二苯基氨基,或者C3-C7环烷基氨基,二C3-C7环烷基氨基或C3-C7环烷氧基,C1-C10烷氧基,C1-C10卤代烷氧基,C1-C5烷基氨基或C2-C8二烷基氨基,
Rf和Rg各自彼此独立是C1-C10烷基,C2-C10烯基,C2-C10炔基,C1-C10烷氧基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C2-C5烷基氨基烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基,苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基,杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基,杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基氨基,二杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二杂芳基氨基,苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基氨基,二苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二苯基氨基,或者C3-C7环烷基氨基,二C3-C7环烷基氨基或C3-C7环烷氧基,C1-C10卤代烷氧基,C1-C5烷基氨基或C2-C8二烷基氨基,苄氧基或苯氧基,其中该苄基和苯基可以又被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代,并且
Rh是C1-C10烷基,C3-C10烯基,C3-C10炔基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C2-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),苯氧基C1-C5烷基(其中该苯基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳氧基C1-C5烷基(其中该杂芳基可任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C3-C5卤代烯基,C3-C8环烷基,苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素或硝基取代的苯基,或杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基。
尤其是,潜伏基团G是基团-C(Xa)-Ra或-C(Xb)-Xc-Rb,而Xa、Ra、Xb、Xc和Rb的含义如前文所定义。
优选G是氢、碱金属或碱土金属,其中特别优选氢。
根据取代基的性质,式(I)化合物可以以不同异构体形式存在。例如,当G是氢时式(I)化合物可以以不同互变异构体形式存在。
本发明涵盖全部比例的全部这些异构体和互变异构体及其混合物。另外,当取代基包含双键时,可以存在顺式和反式异构体。同样地,这些异构体也在要求保护的式(I)化合物的范围之内。
在式(I)化合物的优选组中,R1是甲基,乙基或甲氧基。
优选,R2和R3独立地是氢,卤素,C1-C6烷基,C1-C6烷氧基,C2-C6烯基,C2-C6炔基,C2-C6卤代炔基,苯基或被C1-C4烷基、C1-C3卤代烷基、氰基、硝基、卤素或C1-C3烷基磺酰基取代的苯基;更优选地,R2和R3独立地是氢,氯,溴,甲基,甲氧基,乙基,乙氧基,乙烯基,乙炔基,苯基或被甲基、三氟甲基、氰基、硝基、氟、氯或甲磺酰基取代的苯基。
在又一组优选的式(I)化合物中,R2和R3独立地是噻吩基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噻吩基,呋喃基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的呋喃基,吡唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的吡唑基,噻唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噻唑基,噁唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噁唑基,异噻唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的异噻唑基,异噁唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的异噁唑基,三唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的三唑基,噁二唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噁二唑基,噻二唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噻二唑基,四唑基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的四唑基,吡啶基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的吡啶基,嘧啶基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的嘧啶基,哒嗪基,被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的哒嗪基,吡嗪基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的吡嗪基,三嗪基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的三嗪基。
优选,R3是氢。
优选,R4是氢,甲基,乙基,正丙基,异丙基,卤代甲基,卤代乙基,卤素,乙烯基,乙炔基,甲氧基,乙氧基,卤代甲氧基或卤代乙氧基,和更优选R4是氢,甲基,乙基,氯,溴,乙烯基,乙炔基,甲氧基或乙氧基。
优选,R1,R2和R4是甲基而R3是氢。
在式(I)化合物的又一优选组中,R5是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基或C1-C6卤代烷氧基,而更优选,R5是氢或甲基。
优选,在式(I)化合物中,R6和R7独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基或C1-C6卤代烷氧基,而更优选,R6和R7独立地是氢或甲基。
在式(I)化合物的又一优选组中,R8和R9独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基或C1-C6卤代烷氧基,而更优选,R8和R9独立地是氢或甲基。
优选的饱和的或一不饱和的环Q是下式那些
其中
R是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C2-C6卤代炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基,氰基,硝基,苯基,被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基,或杂芳基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的杂芳基,
R’是氢,C1-C6烷基,C1-C6卤代烷基,C3-C7环烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷基羰基,C1-C6卤代烷基羰基,C1-C6烷氧羰基,C1-C6烷基氨基羰基,C2-C8二烷基氨基羰基,C6-C10芳基磺酰基,C6-C10芳基羰基,C6-C10芳基氨基羰基,C7-C16芳基烷基氨基羰基,C1-C9杂芳基磺酰基,C1-C9杂芳基羰基,C1-C9杂芳基氨基羰基,C2-C15杂芳基烷基氨基羰基,
R”是氢,C1-C6烷基,C1-C6卤代烷基,C3-C7环烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷基羰基,C1-C6卤代烷基羰基,C1-C6烷氧羰基,C1-C6烷基氨基羰基,C2-C8二烷基氨基羰基,C1-C6卤代烷基亚磺酰基或C1-C6卤代烷基磺酰基,
n是0、1、2、3或4和
A表示连接至-(CR6R7)m-部分的位置。
基团Q1,Q2,Q3,Q4,Q5,Q6,Q7,Q25,Q26,Q27,Q28,Q29,Q86,Q87,Q88,Q89,Q90是更加优选的,而基团Q1至Q7是特别优选的。
优选,R和R’独立地是氢,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基或C1-C4卤代烷氧基,而R”是氢,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基或C1-C6卤代烷基羰基。
优选,n是0、1和2。
在式(I)化合物中优选m是1或2,而最优选m是1。
某些式(I)化合物是烯烃,其本身按照已知方法进行其它的烯烃类普通反应提供其它式(I)化合物。上述反应的实例包括但不限于卤化或氢化
式(I)化合物,其中R5和R6形成键而R7是卤素(优选氯或溴)或R7是C1-C6烷基磺酸酯(优选甲磺酸酯)或C1-C6卤代烷基磺酸酯(优选三氟甲磺酸酯)或芳基磺酸酯(优选甲苯磺酸酯),可以在Suzuki-Miyaura、Sonogashira和有关交联反应的文献中描述的条件下与适宜的偶联伴侣发生交联反应以提供额外的式(I)化合物(参见例如,O’Brien,C.J.和Organ,M.G.Angew.Chem.Int.Ed.(2007),46,2768-2813;Suzuki,A.Journal of Organometallic Chemistry(2002),653,83;Miyaura N.和Suzuki,A.Chem.Rev.(1995),95,2457-2483)。
本领域技术人员应理解式(I)化合物可以含有带有一个或多个取代基的杂芳族部分,该取代基能够在已知条件下转化为另选的取代基,并且这些化合物本身可以充当制备其它式(I)化合物的中间体。
例如,其中R1、R2、R3或R4是烯基或炔基的式(I)化合物可以在已知条件下被还原为其中R1、R2、R3或R4是烷基的式(I)化合物,而其中R1、R2、R3或R4是卤素优选溴或碘的式(I)化合物可以在Suzuki-Miyaura、Sonogashira和有关交联反应的文献中描述的条件下与适宜的偶联伴侣发生交联反应以提供额外的式(I)化合物(参见例如,O’Brien,C.J.和Organ,M.G.Angew.Chem.Int.Ed.(2007),46,2768-2813;Suzuki,A.Journal of Organometallic Chemistry(2002),653,83;Miyaura N.和Suzuki,A.Chem.Rev.(1995),95,2457-2483)。
式(I)化合物,其中G是C1-C8烷基,C2-C8卤代烷基,苯基C1-C8烷基(其中该苯基可以任选被C1-C3烷基,C1-C3卤代烷基,C1-C3烷氧基,C1-C3卤代烷氧基,C1-C3烷硫基,C1-C3烷基亚磺酰基,C1-C3烷基磺酰基,卤素,氰基或硝基取代),杂芳基C1-C8烷基(其中该杂芳基可以任选被C1-C3烷基,C1-C3卤代烷基,C1-C3烷氧基,C1-C3卤代烷氧基,C1-C3烷硫基,C1-C3烷基亚磺酰基,C1-C3烷基磺酰基,卤素,氰基或硝基取代),C3-C8烯基,C3-C8卤代烯基,C3-C8炔基,C(Xa)-Ra,C(Xb)-Xc-Rb,C(Xd)-N(Rc)-Rd,-SO2-Re,-P(Xe)(Rf)-Rg或CH2-Xf-Rh,其中Xa,Xb,Xc,Xd,Xe,Xf,Ra,Rb,Rc,Rd,Re,Rf,Rg和Rh如前文所定义,可以优选在至少一当量碱存在下通过用下述试剂处理式(A)化合物(其为G是H的式(I)化合物)来制备:试剂G-Z,其中G-Z是烷基化试剂比如烷基卤化物(烷基卤化物的定义包括简单的C1-C8烷基卤化物比如碘甲烷和碘乙烷,取代的烷基卤化物比如氯甲基烷基醚Cl-CH2-Xf-Rh,其中Xf是氧,和氯甲基烷基硫化物Cl-CH2-Xf-Rh,其中Xf是硫),C1-C8烷基磺酸酯,或二-C1-C8烷基硫酸酯;或C3-C8烯基卤化物;或C3-C8炔基卤化物;或酰化剂比如羧酸HO-C(Xa)Ra,其中Xa是氧,酰氯Cl-C(Xa)Ra,其中Xa是氧,或酸酐[RaC(Xa)]2O,其中Xa是氧,或异氰酸酯RcN=C=O,或氨基甲酰基氯化物Cl-C(Xd)-N(Rc)-Rd(其中Xd是氧且条件是Rc和Rd都不是氢),或硫代氨基甲酰基氯化物Cl-C(Xd)-N(Rc)-Rd(其中Xd是硫且条件是Rc和Rd都不是氢)或氯甲酸酯Cl-C(Xb)-Xc-Rb(其中Xb和Xc是氧),或氯硫代甲酸酯Cl-C(Xb)-Xc-Rb(其中Xb是氧和Xc是硫),或氯二硫代甲酸酯Cl-C(Xb)-Xc-Rb(其中Xb和Xc是硫),或异硫氰酸酯RcN=C=S,或用二硫化碳和烷基化试剂依次处理;或磷酰化剂比如磷酰氯Cl-P(Xe)(Rf)-Rg或磺酰化试剂比如磺酰氯Cl-SO2-Re。
可以形成异构的式(I)化合物。比如说,式(A)化合物可以产生两种异构的式(I)化合物,或产生式(I)化合物的异构混合物。本发明涵盖两种异构的式(I)化合物,以及这些化合物任意比率的混合物。
环1,3-二酮的O-烷基化是已知的;适宜方法描述于例如US4436666。备择程序已报告于Pizzorno,M.T.和Albonico,S.M.Chem.Ind.(London)(1972),425;Born,H.等人J.Chem.Soc.(1953),1779;Constantino,M.G.等人Synth.Commun.(1992),22(19),2859;Tian,Y.等人Synth.Commun.(1997),27(9),1577;Chandra Roy,S.等人,Chem.Lett.(2006),35(1),16;Zubaidha,P.K.等人Tetrahedron Lett.(2004),45,7187和Zwanenburg,B.等人Tetrahedron(2005),45(22),7109。
环1,3-二酮的酰基化可以由与例如US4551547,US4175135,US4422870,US4659372和US4436666所描述那些的相似方法来进行。式(A)二酮通常可以在至少1当量适宜碱存在下,任选地在适宜溶剂存在下,用酰化试剂进行处理。所述碱可以是无机碱比如碱金属碳酸盐或氢氧化物,或金属氢化物,或者有机碱比如叔胺或金属醇盐。适宜无机碱的实例包括碳酸钠、氢氧化钠或氢氧化钾、氢化钠,适宜的有机碱包括三烷基胺,比如三甲胺和三乙胺,吡啶或其它胺类碱比如1,4-二氮杂二环[2.2.2]-辛烷和1,8-二氮杂二环[5.4.0]十一-7-烯。优选的碱包括三乙胺和吡啶。选择适宜该反应的溶剂从而与反应试剂相容,并且包括醚类比如四氢呋喃和1,2-二甲氧基乙烷和卤化溶剂比如二氯甲烷和氯仿。某些碱,比如吡啶和三乙胺,可以成功地同时用作碱和溶剂。在酰化试剂是羧酸的情况下,优选在偶联剂比如碘化2-氯-1-甲基吡啶鎓、N,N’-二环己基碳二亚胺、1-(3-二甲基氨基丙基)-3-乙基碳二亚胺和N,N’-羰基二咪唑,和任选的碱如三乙胺或吡啶存在下,在适宜溶剂比如四氢呋喃、二氯甲烷或乙腈中,进行酰化。适宜的程序描述于例如Zhang,W.和Pugh,G.Tetrahedron Lett.(1999),40(43),7595和Isobe,T.和Ishikawa,T.J.Org.Chem.(1999),64(19)6984。
环1,3-二酮的磷酰化可以使用磷酰卤或硫代磷酰卤和碱由与US4409153所描述那些的相似方法来进行。
式(A)化合物的磺酰化可以例如通过Kowalski,C.J.和Fields,K.W.J.Org.Chem.(1981),46,197的程序优选在至少一当量碱存在下用烷基卤化物或芳基磺酰卤来实现。
式(A)化合物可以这样制备自式(I)化合物:在常规加热下或在微波辐射下,优选25℃至150℃,优选在酸催化剂比如盐酸存在下和任选在适宜的溶剂比如四氢呋喃或丙酮存在下,进行水解。
在又一方法中,式(A)化合物可以这样制备:通过与T.N.Wheeler,US4209532描述的那些相类似的方法,优选在酸或碱存在下,和任选在适宜溶剂存在下,环化其中R”’是氢或烷基的式(B)化合物或式(C)化合物。其中R”’是氢的式(B)化合物或式(C)化合物可以在酸性条件下,优选在强酸比如硫酸、多磷酸或Eaton试剂存在下,任选地在适宜溶剂比如乙酸、甲苯或二氯甲烷存在下,进行环化。
其中R”’是烷基(优选甲基或乙基)的式(B)化合物或式(C)化合物,可以在酸性或碱性条件下,优选在至少一当量强碱比如叔丁醇钾、二异丙基氨基锂或氢化钠存在下和在溶剂比如四氢呋喃、甲苯、二甲亚砜或N,N-二甲基甲酰胺中,进行环化。
其中R”’是H的式(B)化合物和式(C)化合物可以在标准条件下分别酯化为其中R”’是烷基的式(B)化合物和式(C)化合物,例如通过在酸催化剂存在下与烷基醇ROH一起加热。
其中R”’是H的式(B)化合物和式(C)化合物可以分别这样制备:通过与例如T.N.Wheeler,US4209532描述的那些相类似的过程,在标准条件下皂化其中R””’是烷基(优选甲基或乙基)的式(D)化合物和式(E)化合物,随后酸化反应混合物引起脱羧。
其中R””是烷基的式(D)化合物和式(E)化合物可以这样制备:在碱性条件下,分别用适宜的式(G)羧酰氯或适宜的式(H)羧酰氯处理式(F)化合物。适宜的碱包括叔丁醇钾,二(三甲基甲硅烷基)氨基钠和二异丙基氨基锂,而上述反应优选在-80℃至30℃的温度下在适宜溶剂(比如四氢呋喃或甲苯)中进行。另选地,其中R””是H的式(D)化合物和式(E)化合物可以这样制备:在适宜温度(-80℃至30℃)下,在适宜的溶剂(比如四氢呋喃或甲苯)中,用适宜的碱(比如叔丁醇钾,二(三甲基甲硅烷基)氨基钠和二异丙基氨基锂)处理式(F)化合物,并将所得阴离子与式(J)的适宜酸酐进行反应:
式(F)化合物是已知化合物,或可以通过已知方法制备自已知化合物。
式(J)化合物可以例如通过与Ballini,R.等人Synthesis(2002),(5),681-685;Bergmeier,S.C.和Ismail,K.A.Synthesis(2000),(10),1369-1371;Groutas,W.C.等人J.Med.Chem.(1989),32(7),1607-11和Bernhard,K.和Lincke,H.Helv.Chim.Acta(1946),29,1457-1466描述的那些相类似的方法来制备。
式(G)化合物或式(H)化合物可以这样制备自式(J)化合物:在碱比如二甲基氨基吡啶或碱性金属醇盐存在下用烷基醇R”’-OH处理(参见例如,Buser,S.和Vasella,A.Helv.Chim.Acta,(2005),88,3151和M.Hart等人Bioorg.Med.Chem.Letters,(2004),14,1969),随后在已知条件下将所得酸用氯化试剂比如草酰氯或亚硫酰氯进行处理(参见例如,Santelli-Rouvier.C.Tetrahedron Lett.(1984),25(39),4371;Walba D.和Wand,M.Tetrahedron Lett.(1982),23(48),4995;Cason,J.Org.Synth.Coll.Vol.III,(169),1955)。
式(G)化合物和式(H)化合物可以通过已知方法制备自已知化合物。例如,获得式(G)化合物和式(H)化合物的类似方法描述于Bergmeier,S.C.和Ismail,K.A.Synthesis(2000),(10),1369-1371。
在又一方法中,式(I)化合物可以这样制备:在碱性条件下,用其中LG是离去基团比如卤素(优选碘或溴)或活化的醇(优选甲磺酸酯或甲苯磺酸酯)的式(L)化合物处理式(K)化合物。适宜的碱包括二异丙基氨基锂,六甲基二硅基氨基钠,叔丁醇钾,而该反应优选在-80℃至30℃的温度下在适宜的溶剂(比如四氢呋喃)中进行。
式(L)化合物是已知的,或可以通过已知方法制备自已知化合物(参见例如:WO2006016178;Ueno,H.等人J.Med.Chem.(2005),48(10),3586-3604;Kanoh,S.等人Tetrahedron(2002),58(35),7049-7064;Strachan,J.-P.等人J.Org.Chem.(2006),71(26),9909-9911)。
式(K)化合物是已知化合物或可以通过已知方法制备自已知化合物(参见例如,Song,Y.S.S.等人Tetrahedron Lett.(2005),46(46),5987-5990;Kuethe,J.T.等人J.Org.Chem.(2002),67(17),5993-6000)。
另选地,其中G是C1-C6烷基的式(K)化合物可以这样制备:在已知条件下或通过已知方法(参见例如,Eberhardt,U.等人Chem.Ber.(1983),116(1),119-135)烷基化其中G是氢的式(K)化合物。
其中G是氢的式(K)化合物是已知的,或可以通过已知方法制备自已知化合物(参见例如,Nguyen,H.N.等人J.Am.Chem.Soc.(2003),125(39),11818-11819;Bonjoch,J.等人Tetrahedron(2001),57(28),6011-6017;Fox,J.M.等人J.Am.Chem.Soc.(2000),122(7),1360-1370;US4338122;US4283348)。
另选地,其中R5和R6形成键的式(I)化合物可以通过已知方法制备自式(M)化合物(参见例如Nagaoka,H.等人Tetrahedron Letters(1985),26(41),5053-5056;Nagaoka,H.等人J.Am.Chem.Soc.(1986),108(16),5019-5021;Zuki,M.等人Bull.Chem.Soc.Japan(1988),61(4),1299-1312;Enholm,E.J.等人J.Org.Chem.(1996),61(16),5384-5390;Clive,D.L.J.等人Tetrahedron(2001),57(18),3845-3858;Bartoli,G.等人J.Org.Chem.(2002),67(25),9111-9114.Jung,M.E.等人Chem.Comm.(2003),(2),196-197;EP1433772;JP2004203844;IN194295)。
式(M)化合物可以这样制备:在碱性条件下用式(N)化合物处理式(K)化合物(其中R5是氢)。适宜的碱包括二异丙基氨基锂、六甲基二硅基氨基钠、叔丁醇钾,而上述反应优选在-80℃至30℃的温度下在适宜的溶剂(比如四氢呋喃)中进行。
式(N)化合物已知的,或者可以通过已知方法制备自已知化合物。
式(I)化合物(其中G是C1-C4烷基)可以这样制备:在常规加热下或在微波辐射下,优选25℃至200℃,在适宜的钯催化剂(例如相对化合物(O)0.001-50%乙酸钯(II))和碱(例如相对化合物(O)1至10当量磷酸钾)存在下和优选在适宜配体(例如相对化合物(O)0.001-50%(2-二环己基膦基)-2’,6’-二甲氧基联苯)存在下,和在适宜的溶剂(例如甲苯或1,2-二甲氧基乙烷)中,将式(O)化合物(其中G是C1-C4烷基,而Hal是卤素,优选溴或碘),与式(P)芳基取代硼酸Ar-B(OH)2或芳基取代硼酸酯,进行反应(参见例如,Song,Y.S.S.等人Tetrahedron Lett.(2005),46(46),5987-5990;Kuethe,J.T.等人J.Org.Chem.(2002),67(17),5993-6000)。
式(O)化合物可以这样制备:在已知条件下,卤化式(Q)化合物,随后用C1-C4烷基卤化物或原甲酸三-C1-C4烷基酯烷基化所得式(R)卤化物,例如通过Shepherd R.G.等人J.Chem.Soc.Perkin Trans.1(1987),2153-2155和Lin Y.-L.等人Bioorg.Med.Chem.(2002),10,685-690的程序。另选地,式(O)化合物可以这样制备:在已知条件下,用C1-4烷基卤化物或原甲酸三-C1-4-烷基酯烷基化式(Q)化合物,并卤化所得式(S)烯酮(参见例如Song,Y.S.等人Tetrahedron Lett.(2005),46(36),5987-5990;Kuethe,J.T.等人J.Org.Chem.(2002),67(17),5993-6000;Belmont,D.T.等人J.Org.Chem.1985,50(21),4102-4107)。
式(S)化合物可以这样制备:在碱性条件下,用其中LG是离去基团比如卤素(优选碘或溴)或活化的醇(优选甲磺酸酯或甲苯磺酸酯)的式(L)化合物处理式(T)化合物。适宜的碱包括二异丙基氨基锂,六甲基二硅基氨基钠,叔丁醇钾,而上述反应优选在-80℃至30℃的温度下在适宜溶剂(比如四氢呋喃)中进行(参见例如,Gulias,M.等人Org.Lett.(2003),5(11),1975-1977;Altenbach,R.J.等人J.Med.Chem.(2006),49(23),6869-6887;Snowden,R.L.Tetrahedron(1986),42(12),3277-90;Oppolzer,W.等人Helv.Chim.Acta(1980),63(4),788-92;Mellor,M.等人Synth.Commun.1979,9(1),1-4)。
式(T)化合物是已知的,或者可以通过已知方法制备自已知化合物。
另选地,其中R5和R6形成键的式(S)化合物可以通过已知方法制备自式(U)化合物(参见例如,Nagaoka,H.等人Tetrahedron Letters(1985),26(41),5053-5056;Nagaoka,H.等人J.Am.Chem.Soc.(1986),108(16),5019-5021;Zuki,M.等人Bull.Chem.Soc.Japan(1988),61(4),1299-1312;Enholm,E.J.等人J.Org.Chem.(1996),61(16),5384-5390;Clive,D.L.J.等人Tetrahedron(2001),57(18),3845-3858;Bartoli,G.等人J.Org.Chem.(2002),67(25),9111-9114.Jung,M.E.等人Chem.Comm.(2003),(2),196-197;EP1433772;JP2004203844;IN194295)。
式(U)化合物可以这样制备:在碱性条件下用式(N)化合物处理式(T)化合物。适宜的碱包括二异丙基氨基锂、六甲基二硅基氨基钠、叔丁醇钾,而上述反应优选在-80℃至30℃的温度下在适宜的溶剂(比如四氢呋喃)中进行(参见例如,Aleman,J.等人Chem.Comm.(2007),(38),3921-3923)。
式(P)化合物可以通过已知方法制备自其中Hal是溴或碘的式(V)芳基卤化物(参见例如,Thompson W.等人J.Org.Chem.(1984),49,5237和R.Hawkins等人J.Am.Chem.Soc.(1960),82,3053)。例如,式(V)芳基卤化物可以在-80℃至30℃的温度下,在适宜溶剂优选二乙基醚或四氢呋喃中用烷基锂或烷基镁的卤化物处理,而所获得的芳基镁或芳基锂试剂然后可以与硼酸三烷基酯(优选硼酸三甲酯)反应,提供芳基取代硼酸二烷基酯,其在酸性条件下可被水解提供式(P)取代硼酸。
另选地,式(V)化合物可以在已知条件下与衍生自1,2-或1,3-烷二醇(比如频哪醇、2,2-二甲基-1,3-丙二醇和2-甲基-2,4-戊二醇)的环状取代硼酸酯反应(参见例如,Miyaura N.等人J.Org.Chem.(1995),60,7508,和Zhu W.等人Org.Lett.(2006),8(2),261),而所得取代硼酸酯可以在酸性条件下水解提供式(P)取代硼酸。
式(V)芳基卤化物是已知的,或可以通过已知方法制备自已知化合物。例如,式(V)芳基卤化物可以通过已知方法例如Sandmeyer反应经由相应重氮盐制备自式(W)苯胺。
式(W)苯胺是已知化合物,或可以通过已知方法制备自已知化合物。
另选地,式(V)化合物能够通过已知方法经由卤化相应已知化合物来制备。
式(Q)化合物可以这样制备自式(S)化合物:在常规加热下或在微波辐射下,优选25℃至150℃,优选在酸催化剂比如盐酸存在下和任选在适宜的溶剂比如四氢呋喃或丙酮存在下,进行水解。
另选地,式(Q)化合物能够通过已知方法制备自已知化合物(参见例如Manukina,T.A.等人Zhurnal Organicheskoi Khimii(1986),22(4),873-4;Mellor,M.等人Synth.Commun.1979,9(1),1-4)。
在又一方法中,式(A)化合物可以这样制备:优选在25℃至200℃,在适宜的溶剂(例如二噁烷或1,2-二甲氧基乙烷)中,在适宜的钯催化剂(例如相对式(Q)化合物0.001-50%乙酸钯(II))和碱(例如相对式(Q)化合物1至10当量磷酸钾)存在下和优选在适宜的配体(例如相对式(Q)化合物0.001-50%(2-二环己基膦基)-2’,4’,6’-三异丙基联苯)存在下,将式(Q)化合物与适宜的芳基卤化物(比如芳基-碘化物,芳基-溴化物或芳基-氯化物)式(V)Ar-Hal,或适宜的C1-C6烷基磺酸酯(优选甲磺酸酯)或C1-C6卤代烷基磺酸酯(优选三氟甲磺酸酯)或芳基磺酸酯(优选甲苯磺酸酯),进行反应。相似的偶联已知于文献中(参见例如,Belmont,D.T.等人J.Org.Chem.1985,50(21),4102-4107;Fox,J.M.等人J.Am.Chem.Soc.(2000),122(7),1360-1370;B.Hong等人WO 2005/000233)。另选地,式(A)化合物可以这样制备:优选在25℃至200℃,在适宜的溶剂(例如二甲亚砜)中,在适宜的铜催化剂(例如相对式(Q)化合物0.001.50%铜(I)碘化物)和碱(例如相对式(Q)化合物1至10当量碳酸钾)存在下和优选在适宜的配体(例如相对式(Q)化合物0.001-50%L-脯氨酸)存在下,将式(Q)化合物与适宜的芳基卤化物(比如芳基-碘化物)式(V)Ar-Hal,进行反应。相似的偶联已知于有关芳基卤化物的文献中(参见例如,Jiang,Y.等人Synlett(2005),18,2731-2734)。
额外的式(A)化合物可以这样制备:将式(Q)化合物与式(x)有机铅试剂在例如Pinhey,J.Pure and Appl.Chem.(1996),68(4),819和MoloneyM.等人Tetrahedron Lett.(2002),43,3407描述的条件下进行反应。
式(x)有机铅试剂可以根据已知程序制备自式(P)取代硼酸、R””’是C1-C4烷基的式(Y)锡烷或者通过用四乙酸铅直接高铅酸化式(Z)化合物制得。
其它式(A)化合物可以这样制备:在例如Fedorov,A.U.等人Russ.Chem.Bull.Int.Ed.(2005),54(11),2602和Koech P.等人J.Am.Chem.Soc.(2004),126(17),5350及其参考文献描述的条件下将式(Q)化合物与适宜的三芳基铋化合物反应。
额外的式(A)化合物可以这样制备:在适宜的钯催化剂、碱存在下和在适宜的溶剂中,将Ar是任选经取代的苯基的式(AA)碘鎓内鎓盐与式(P)芳基取代硼酸进行反应。
适宜的钯催化剂通常是钯(II)或钯(0)配合物,例如二卤化钯(II)、乙酸钯(II)、硫酸钯(II)、二氯化二(三苯基膦)钯(II)、二氯化二(三环戊基膦)钯(II)、二氯化二(三环己基膦)钯(II)、二(二苯亚甲基丙酮)钯(0)或四(三苯基膦)钯(0)。所述钯催化剂也可以通过与希望的配体配合从钯(II)或钯(0)化合物“原位”制得,例如将待配合的钯(II)盐如二氯化钯(II)(PdCl2)或乙酸钯(II)(Pd(OAc)2)与希望的配体如三苯基膦(PPh3)、三环戊基膦、三环己基膦、2-二环己基膦基-2’,6’-二甲氧基联苯或2-二环己基膦基-2’,4’,6’-三异丙基联苯以及所选溶剂一起,与式(AA)化合物、式(P)芳基取代硼酸和碱进行组合。还适宜的二齿配体是,例如1,1′-二(二苯基膦基)二茂铁或1,2-二(二苯基膦基)乙烷。加热反应介质,对C-C偶联反应所希望的钯(II)配合物或钯(0)配合物由此“原位”形成,接着引发所述C-C偶联反应。
所述钯催化剂的用量是0.001-50mol%,优选量是0.1-15mol%,按式(AA)化合物计。该反应还可以在其他添加剂比如四烷基铵盐如溴化四丁基铵存在下进行。优选钯催化剂是乙酸钯,碱是氢氧化锂而溶剂是1,2-二甲氧基乙烷水溶液。
式(AA)化合物可以这样制备自式(Q)化合物:根据Schank K.等人Synthesis(1983),392,Moriarty R.M.等人J.Am.Chem.Soc.(1985),107,1375或Yang Z.等人Org.Lett.(2002),4(19),3333的程序,用超化合价碘试剂比如二乙酸碘苯或亚碘酰苯和碱比如碳酸钠水溶液、氢氧化锂或氢氧化钠在溶剂比如水或含水醇比如含水乙醇中的溶液,进行处理。
额外的式(A)化合物可以这样制备:在酸性条件下,其中R”””’是C1-C4烷基(优选甲基)的式(AB)化合物或式(AC)化合物进行频哪醇重排(参见例如,Eberhardt,U.等人Chem.Ber.(1983),116(1),119-35和Wheeler,T.N.US4283348)。
式(AB)化合物和式(AC)化合物可以这样制备:在-80℃至30℃的温度下,在酸(比如四氯化钛或碘化镁)存在下任选在适宜的溶剂(比如二氯甲烷)中,用式(AE)化合物处理式(AD)化合物(参见例如,Li,W.-D.Z.和Zhang,X.-X.Org.Lett.(2002),4(20),3485-3488;Shimada,J.等人J.Am.Chem.Soc.(1984),106(6),1759-73;Eberhardt,U.等人Chem.Ber.(1983),116(1),119-35和Wheeler,T.N.US4283348)。
式(AD)化合物是已知的或者可以通过已知方法制备自式(V)化合物或式(Z)化合物。
式(AE)化合物可以于温度20℃至150℃下,在三-C1-C4烷基甲硅烷基氯和金属(优选钠)存在下,在适宜的溶剂(比如甲苯或二乙基醚)中,制备自其中R”’是烷基(优选甲基)的式(AF)化合物(参见例如,Blanchard,A.N.和Burnell,D.J.Tetrahedron Lett.(2001),42(29),4779-4781和Salaun,J.等人Tetrahedron(1989),45(10),3151-62)。
式(AF)化合物类似于式(H)化合物和式(G)化合物并可以通过类似于对式(H)化合物和式(G)化合物所描述那些的已知方法制备。
额外的式(I)化合物,其中R5和R6形成键而R7是C1-C6烷基磺酸酯(优选甲磺酸酯)或C1-C6卤代烷基磺酸酯(优选三氟甲磺酸酯)或芳基磺酸酯(优选的甲苯磺酸酯),可以按照已知程序(Specklin等人J.Org.Chem.2008,73(19),7845-7848)制备自式(AG)化合物。
式(AG)化合物可以在碱性或酸性条件下制备自式(AH)化合物。其程序例如参见G.Quinkert等人Helv.Chim.Acta,1986,69(3),469-537。
式(AH)化合物可以这样制备:在碱存在下将其中R5是氢的式(K)化合物与式(AJ)酰氯进行反应。
式(AJ)化合物是已知的或可以通过已知方法制备自已知化合物。
另选地,式(AG)化合物能够用已知氧化程序(参见例如D.B.Dess和J.C.Martin J.Org.Chem.1983,48(22),4155-4156)制备自式(M)化合物。
本发明式(I)化合物可以如合成所得以未修饰的形式用作除草剂,但是通常使用如载体、溶剂和表面活性物质的配制助剂以各种方式将它们配制为除草组合物。所述配制剂可以呈各种物理形式,例如粉剂、凝胶剂、可湿性粉剂、水分散性粒剂、水分散性片剂、泡腾压缩片剂、乳油、可微乳化浓剂、水乳剂、可流动油剂、水分散剂、油分散剂、悬乳剂、微胶囊悬浮剂、乳粒剂、可溶液剂、水溶性浓剂(具有作为载体的水或可与水混合的有机溶剂)、浸渍的聚合物膜的形式或已知自例如the Manualon Development and Use of FAO Specifications for Plant ProtectionProducts,第5版,1999的其它形式。这些制剂可以直接使用或在使用前稀释。稀释的配制剂可以用例如水、液体肥料、微量营养素、生物体、油或溶剂来制备。
这些配制剂可以这样制备:例如将活性成分与配制助剂混合而得到细分的固体、颗粒、溶液、分散液或乳液形式的组合物。活性成分还可以与其它助剂一起配制,例如细分的固体、矿物油、植物油、改性的植物油、有机溶剂、水、表面活性物质或其组合。活性成分还可以包含在聚合物构成的非常细小的微胶囊中。微胶囊在多孔载体中含有活性成分。这使得活性成分能够以受控量被释放入其环境(例如缓释)。微胶囊通常具有0.1到500微米的直径。它们含有按胶囊重量计约25到95%的量的活性成分。活性成分可以以整块固体形式、固体或液体分散体中的微粒形式或者适宜的溶液形式存在。包封膜包含,例如,天然或合成树胶、纤维素、苯乙烯-丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯或化学改性的聚合物和淀粉黄原酸酯或者其它本领域技术人员已知的相关聚合物。另选地,可以形成很细的微胶囊,其中活性成分以基础物质固体基体中的细分颗粒形式存在,但在此情况下微胶囊未被包封。
适于制备本发明组合物的配制助剂本身是已知的。可以用作液体载体的是:水,甲苯,二甲苯,石油醚,植物油,丙酮,甲基乙基酮,环己酮,酸酐,乙腈,苯乙酮,乙酸戊酯,2-丁酮,碳酸亚丁酯,氯苯,环己烷,环己醇,乙酸烷基酯,二丙酮醇,1,2-二氯丙烷,二乙醇胺,对-二乙基苯,二甘醇,二甘醇松香酸酯,二甘醇丁基醚,二甘醇乙基醚,二甘醇甲基醚,N,N-二甲基甲酰胺,二甲亚枫,1,4-二氧六环,一缩二丙二醇,一缩二丙二醇甲基醚,一缩二丙二醇二苯甲酸酯,diproxitol,烷基吡咯烷酮,乙酸乙酯,2-乙基己醇,碳酸亚乙酯,1,1,1-三氯乙烷,2-庚酮,α-蒎烯,d-柠檬烯,乳酸乙酯,乙二醇,乙二醇丁基醚,乙二醇甲基醚,γ-丁内酯,甘油,乙酸甘油酯,二乙酸甘油酯,三乙酸甘油酯,十六烷,己二醇,乙酸异戊酯,乙酸异冰片酯,异辛烷,异佛尔酮,异丙基苯,肉豆蔻酸异丙酯,乳酸,月桂基胺,异亚丙基丙酮,甲氧基丙醇,甲基异戊基酮,甲基异丁基酮,月桂酸甲酯,辛酸甲酯,油酸甲酯,二氯甲烷,间-二甲苯,正己烷,正辛胺,十八烷酸,辛胺乙酸盐,油酸,油烯基胺,邻-二甲苯,苯酚,聚乙二醇(PEG 400),丙酸,乳酸丙酯,碳酸亚丙酯,丙二醇,丙二醇甲基醚,对-二甲苯,甲苯,磷酸三乙酯,三甘醇,二甲苯磺酸,烷烃,矿物油,三氯乙烯,全氯乙烯,乙酸乙酯,乙酸戊酯,乙酸丁酯,丙二醇甲基醚,二甘醇甲基醚,甲醇,乙醇,异丙醇和更高分子量的醇,比如异戊醇,四氢糠醇,己醇,辛醇的,乙二醇,丙二醇,甘油,N-甲基-2-吡咯烷酮等。为稀释浓缩物,一般选择水作载体。适宜的固体载体是,例如,滑石、二氧化钛、叶蜡石粘土、硅土、凹凸棒石粘土、硅藻土、石灰石、碳酸钙、膨润土、蒙脱石钙、棉籽壳、粗麦粉、大豆面粉、浮石、木屑、核桃(ground walnut)壳、木质素以及例如CFR 180.1001.(c)&(d)中描述的类似物质。
大量表面活性物质可以被有利地用在固体和液体制剂中,特别是在使用前可用载体稀释的那些制剂中。表面活性物质可以是阴离子、阳离子、非离子或聚合物型,它们还可用作乳化剂、湿润剂或助悬剂或用于其他目的。典型的表面活性物质包括,例如,硫酸烷基酯的盐,比如月桂基硫酸酯二乙醇铵;烷基芳基磺酸盐,比如十二烷基苯磺酸钙;烷基苯酚-环氧烷烃的加成产物,比如乙氧基化壬基苯酚;醇-环氧烷烃的加成产物,比如乙氧基化十三烷醇;皂,比如硬脂酸钠;烷基萘磺酸盐,比如二丁基萘磺酸钠;磺基琥珀酸盐的二烷基酯,比如磺基琥珀酸钠二(2-乙基己基)酯;山梨糖醇酯,比如山梨糖醇油酸酯;季铵,比如月桂基三甲基氯化铵,脂肪酸聚乙二醇酯,比如硬脂酸聚乙二醇酯;环氧乙烷和环氧丙烷的嵌段共聚物;单-和二-烷基磷酸酯的盐;还有在例如″McCutcheon′s Detergents and Emulsifiers Annual″,MC PublishingCorp.,Ridgewood,New Jersey,1981中描述的其它物质。
通常可以用在农药制剂中的其它助剂可以包括结晶抑制剂、粘度调节物质、助悬剂、染料、抗氧化剂、起泡剂、光吸收剂、混合助剂、消泡剂、配位剂、中和或pH-调节物质以及缓冲剂、腐蚀抑制剂、香料、湿润剂、吸收改善剂、微量营养素、增塑剂、助流剂、润滑剂、分散剂、增稠剂、防冻剂、杀微生物剂以及液体和固体肥料。
所述制剂还可以包含额外的活性物质,例如其它除草剂、除草剂安全剂、植物生长调节剂、杀真菌剂或杀虫剂。
本发明组合物还可以包括添加剂,其包含植物或动物来源的油、矿物油、这种油的烷基酯或者这种油和油衍生物的混合物。用于本发明组合物中的油添加剂的量一般是从0.01到10%,基于喷雾混合物。例如,可以在制备出喷雾混合物后可将油添加剂以希望的浓度加至喷雾槽。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或向日葵油,乳化植物油,比如(Canada Inc.),植物来源油的烷基酯,例如甲基衍生物,或者动物来源的油,比如鱼油或牛脂。优选的添加剂含有,例如作为活性成分的基本上80%重量的鱼油烷基酯和15%重量的甲基化菜籽油,还有5%重量的惯用乳化剂和pH调节剂。特别优选的油添加剂包含C8-C22脂肪酸的烷基酯,特别是C12-C18脂肪酸的甲基衍生物,例如重要的月桂酸、棕榈酸和油酸的甲酯。这些酯已知为月桂酸甲酯(CAS-111-82-0)、棕榈酸甲酯(CAS-112-39-0)和油酸甲酯(CAS-112-62-9)。优选的脂肪酸甲酯衍生物是和2231(Cognis GmbH)。这些油衍生物和其它油衍生物也已知自theCompendium of Herbicide Adjuvants,第5版,Southern IllinoisUniversity,2000。
油添加剂的施用和作用还可以通过将其与表面活性物质如非离子、阴离子或阳离子表面活性剂组合来改善。适宜的阴离子、非离子和阳离子表面活性剂的实例见于WO 97/34485的第7页和第8页。优选的表面活性物质是十二烷基苄磺酸酯的盐类的阴离子表面活性剂,特别是其钙盐,以及乙氧基化脂肪醇类的非离子表面活性剂。特别优选具有5-40的乙氧基化度的乙氧基化C12-C22脂肪醇。可商购表面活性剂的实例是Genapol型(Clariant AG)。还优选的是有机硅表面活性剂,特别是可作为例如Silwet购得的聚烷基氧化物改性的七甲基三硅氧烷,以及全氟化表面活性剂。相对全部添加剂的表面活性物质浓度一般从1到30%重量。包含油或矿物油或其衍生物与表面活性剂的混合物的油添加剂实例是Edenor ME(Syngenta AG,CH)和(BP Oil UK Limited,GB)。
所述表面活性物质还可以单独用于配制剂中,也即不加油添加剂。
此外,向油添加剂/表面活性剂混合物中添加有机溶剂可以有助于进一步增强作用。适宜溶剂是例如(ESSO)和Aromatic(Exxon公司)。这些溶剂的浓度可以是总重量的10-80%重量。这种可以与溶剂混合的油添加剂描述于例如US-A-4 834 908中,其中公开的可商购油添加剂称为(BASF公司)。根据本发明优选的其他油添加剂是(Syngenta Crop Protection Canada)和(Syngenta Crop Protection Canada)。
除了上面列出的油添加剂,为了增强本发明组合物的作用,还可以将烷基吡咯烷酮类配制剂(例如)加入喷雾混合物。还可以使用合成的网络结构(latices)配制剂例如聚丙烯酰胺、聚乙烯化合物或聚-1-p-薄荷烯(例如或)。包含丙酸的溶液,例如Eurogkem也可以混入喷雾混合物中作为活性增强剂。
除草制剂通常包含从0.1到99%重量、特别是从0.1到95%重量的式I化合物以及从1到99.9%重量的配制助剂,其优选包括从0到25%重量的表面活性物质。尽管商业产品优选配制为浓缩物,但终端用户仍通常采用稀释的配制剂。
式I化合物的施用率可以在宽范围内变化并且取决于土壤性质、施用方法(出苗前或出苗后;拌种;向种畦中施用;免耕施用等)、作物植物、待防治的杂草或禾本科草、主要气候条件和受施用方法、施用时间和靶标作物控制的其它因素。根据本发明的式I化合物通常以1-2000g/公顷,优选1-1000g/公顷,最优选1-500g/公顷的用量施用。
优选的配制剂特别地具有下述组成:
(%=重量百分比)
乳油:
活性成分: 1至95%,优选60至90%
表面活性剂:1至30%,优选5至20%
液态载体: 1至80%,优选1至35%
粉剂:
活性成分: 0.1至10%,优选0.1至5%
固态载体: 99.9至90%,优选99.9至99%
浓悬浮剂:
活性成分: 5至75%,优选10至50%
水: 94至24%,优选88至30%
表面活性剂: 1至40%,优选2至30%
可湿性粉剂:
活性成分: 0.5至90%,优选1至80%
表面活性剂: 0.5至20%,优选1至15%
固态载体: 5至95%,优选15至90%
颗粒剂:
活性成分: 0.1至30%,优选0.1至15%
固态载体: 99.5至70%,优选97至85%
下述实例进一步举例说明本发明,但并非对其进行限制。
F1.乳油 a) b) c) d)
活性成分 5% 10% 25% 50%
十二烷基苯磺酸钙 6% 8% 6% 8%
蓖麻油聚乙二醇醚 4% - 4% 4%
(36mol环氧乙烷)
辛基苯酚聚乙二醇醚 - 4% - 2%
(7-8mol环氧乙烷)
NMP - - 10% 20%
芳族烃 85% 78% 55% 16%
混合物C9-C12
可用水稀释该浓缩物以配制任意希望浓度的乳液。
F2.溶液剂 a) b) c) d)
活性成分 5% 10% 50% 90%
1-甲氧基-3-(3-甲氧基-
丙氧基)-丙烷 - 20% 20% -
聚乙二醇MW 400 20% 10% - -
NMP - - 30% 10%
芳族烃 75% 60% - -
混合物C9-C12
该溶液适于以微滴剂形式施用。
F3.可湿性粉剂 a) b) c) d)
活性成分 5% 25% 50% 80%
木质素磺酸钠 4% - 3% -
月桂基硫酸钠 2% 3% - 4%
二异丁基萘磺酸钠 - 6% 5% 6%
辛基苯酚聚乙二醇醚 - 1% 2% -
(7-8mol环氧乙烷)
高分散硅酸 1% 3% 5% 10%
高岭土 88% 62% 35% -
将活性成分与助剂充分地混合,将所得混合物在合适的磨机中充分研磨,得到可湿性粉剂,可加水将其稀释给出任意希望浓度的悬浮剂。
F4.包衣颗粒剂 a) b) c)
活性成分 0.1% 5% 15%
高分散硅酸 0.9% 2% 2%
无机载体 99.0% 93% 83%
(直径0.1-1mm)
例如CaCO3或SiO2
将活性成分溶于二氯甲烷,将所得溶液喷涂于载体上,接着在真空中蒸除溶剂。
F5.包衣颗粒剂 a) b) c)
活性成分 0.1% 5% 15%
聚乙二醇MW 200 1.0% 2% 3%
高分散硅酸 0.9% 1% 2%
无机载体 98.0% 92% 80%
(直径0.1-1mm)
例如CaCO3或SiO2
在搅拌机中,将充分研磨的活性成分均匀地涂布至用聚乙二醇湿润的载体。通过这种方式获得不起尘的包覆颗粒剂。
F6.挤出颗粒剂 a) b) c) d)
活性成分 0.1% 3% 5% 15%
木质素磺酸钠 1.5% 2% 3% 4%
羧甲基纤维素 1.4% 2% 2% 2%
高岭土 97.0% 93% 90% 79%
将活性成分与助剂混合并研磨,用水润湿此混合物。将所获混合物挤出,然后在空气流中干燥。
F7.粉剂 a) b) c)
活性成分 0.1% 1% 5%
滑石 39.9% 49% 35%
高岭土 60.0% 50% 60%
通过混合活性成分和载体并在合适的研磨机中研磨所述混合物获得即用粉剂。
F8.浓悬浮剂 a) b) c) d)
活性成分 3% 10% 25% 50%
乙二醇 5% 5% 5% 5%
壬基苯酚聚乙二醇醚 - 1% 2% -
(15mol环氧乙烷)
木质素磺酸钠 3% 3% 4% 5%
羧甲基纤维素 1% 1% 1% 1%
37%甲醛水溶液 0.2% 0.2% 0.2% 0.2%
溶液
硅油乳液 0.8% 0.8% 0.8% 0.8%
水 87% 79% 62% 38%
将充分研磨的活性成分与助剂密切混合,得到浓悬浮剂,将其用水稀释可制备任意希望浓度的悬浮剂。
本发明也涉及选择性防治有用植物作物中的禾本科草和杂草以及用于非选择性杂草防治的方法,其包括用式I化合物处理所述有用植物或其栽培区域或处所。
其中可以使用根据本发明的组合物的有用植物作物特别地包括谷物,尤其是小麦和大麦,稻,玉米,油菜,甜菜,甘蔗,大豆,棉花,向日葵,花生和种植园作物。
术语“作物”应被理解为还包括通过常规育种法或基因工程使其耐受除草剂或除草剂类(例如ALS、GS、EPSPS、PPO和HPPD抑制剂)的作物。通过常规育种法使其耐受例如咪唑啉酮类如甲氧咪草烟的作物的实例是夏季油菜(Canola)。通过基因工程方法使之耐受除草剂的作物实例包括抗草甘膦和抗草铵膦的玉米品种,该品种可根据商品名Roundup和Liberty购得。待防治的杂草可以是单子叶和双子叶杂草,比如,例如,繁缕属(Stellaria)、旱金莲属(Nasturtium)、剪股颖属(Agrostis)、马唐属(Digitaria)、燕麦属(Avena)、狗尾草属(Setaria)、白芥属(Sinapis)、黑麦草属(Lolium)、茄属(Solanum)、稗属(Echinochloa)、莞草属(Scirpus)、雨久花属(Monochoria)、慈姑属(Sagittaria)、雀麦属(Bromus)、看麦娘属(Alopecurus)、蜀黍属(Sorghum)、筒轴茅属(Rottboellia)、莎草属(Cyperus)、苘麻属(Abutilon)、黄花捻属(Sida)、苍耳属(xanthium)、苋属(Amaranthus)、藜属(Chenopodium)、番薯属(Ipomoea)、菊属(Chrysanthemum)、猪殃殃属(Galium)、堇菜属(Viola)和婆婆纳属(Veronica)。对单子叶杂草尤其是剪股颖属(Agrostis)、燕麦属(Avena)、狗尾草属(Setaria)、黑麦草属(Lolium)、稗属(Echinochloa)、雀麦属(Bromus)、看麦娘属(Alopecurus)和蜀黍属(Sorghum)的防治是非常广泛的。
作物还被理解为通过基因工程方法使其对有害昆虫有抗性的那些,例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象有抗性)以及Bt马铃薯(对马铃薯叶甲有抗性)。Bt玉米的实例是(Syngenta Seeds)的Bt-176玉米杂交种。该Bt毒素是由苏云金杆菌(Bacillus thuringiensis)土壤细菌天然形成的蛋白。毒素和能合成这种毒素的转基因植物的实例描述于EP-A-451 878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073和EP-A-427 529中。包含一种或多种编码杀虫抗性和表达一种或多种毒素的基因的转基因植物实例是(玉米)、Yield(玉米)、(棉花)、(棉花)、(马铃薯)、和植物作物和其种子材料可以对除草剂有抗性,而且同时对昆虫摄食有抗性(“叠加的”转基因事件)。种子例如可以具有表达杀虫活性Cry3蛋白并在同时有草甘膦耐受性的能力。术语“作物”应被理解为还包括通过常规育种法或基因工程获得的作物,其包含所谓的输出特性(例如改进的味道、贮藏稳定性、营养成分)。
栽培区域应被理解为包括其中已经生长了作物植物的土地以及计划用于这些作物植物的栽培的土地。
根据本发明的式I化合物还可以与其它除草剂组合使用。优选地,在这些混合物中,式I化合物是下表1-102所列出的那些化合物之一:式I化合物的下述混合物特别重要:
式I化合物+乙草胺,式I化合物+三氟羧草醚,式I化合物+三氟羧草醚-钠盐,式I化合物+苯草醚,式I化合物+丙烯醛,式I化合物+甲草胺,式I化合物+禾草灭,式I化合物+烯丙醇,式I化合物+莠灭净,式I化合物+氨唑草酮,式I化合物+酰嘧磺隆,式I化合物+氯氨吡啶酸(aminopyralid),式I化合物+杀草强,式I化合物+氨基磺酸铵,式I化合物+莎稗磷,式I化合物+磺草灵,式I化合物+atraton,式I化合物+莠去津,式I化合物+四唑嘧磺隆,式I化合物+BCPC,式I化合物+氟丁酰草胺,式I化合物+草除灵,式I化合物+乙丁氟灵,式I化合物+呋草黄,式I化合物+苄嘧磺隆,式I化合物+苄嘧磺隆-甲酯,式I化合物+地散磷,式I化合物+灭草松,式I化合物+双苯嘧草酮,式I化合物+双环磺草酮,式I化合物+吡草酮,式I化合物+甲羧除草醚,式I化合物+双丙氨膦,式I化合物+双草醚,式I化合物+双草醚-钠盐,式I化合物+硼砂,式I化合物+除草定,式I化合物+溴丁酰草胺,式I化合物+溴苯腈,式I化合物+丁草胺,式I化合物+氟丙嘧草酯,式I化合物+抑草磷,式I化合物+仲丁灵,式I化合物+丁苯草酮,式I化合物+丁草敌,式I化合物+二甲胂酸,式I化合物+氯酸钙,式I化合物+唑草胺,式I化合物+双酰草胺,式I化合物+唑草酸(carfentrazone),式I化合物+唑草酯,式I化合物+CDEA,式I化合物+CEPC,式I化合物+整形醇,式I化合物+整形醇-甲酯,式I化合物+氯草敏,式I化合物+氯嘧磺隆,式I化合物+氯嘧磺隆-乙酯,式I化合物+氯乙酸,式I化合物+绿麦隆,式I化合物+氯苯胺灵,式I化合物+氯磺隆,式I化合物+氯酞酸,式I化合物+氯酞酸-二甲酯,式I化合物+吲哚酮草酯,式I化合物+环庚草醚,式I化合物+醚磺隆,式I化合物+咯草隆,式I化合物+烯草酮,式I化合物+炔草酸(clodinafop),式I化合物+炔草酯,式I化合物+异噁草酮,式I化合物+氯甲酰草胺,式I化合物+二氯吡啶酸,式I化合物+氯酯磺草酸(cloransulam),式I化合物+氯酯磺草胺,式I化合物+CMA,式I化合物+4-CPB,式I化合物+CPMF,式I化合物+4-CPP,式I化合物+CPPC,式I化合物+甲酚,式I化合物+苄草隆,式I化合物+单氰胺,式I化合物+氰草津,式I化合物+环草敌,式I化合物+环丙嘧磺隆,式I化合物+噻草酮,式I化合物+氰氟草酯(cyhalofop),式I化合物+氰氟草酯,式I化合物+2,4-滴,式I化合物+3,4-DA,式I化合物+杀草隆,式I化合物+茅草枯,式I化合物+棉隆,式I化合物+2,4-DB,式I化合物+3,4-DB,式I化合物+2,4-DEB,式I化合物+甜菜安,式I化合物+麦草畏,式I化合物+敌草腈,式I化合物+邻二氯苯,式I化合物+对二氯苯,式I化合物+2,4-滴丙酸,式I化合物+精2,4-滴丙酸,式I化合物+禾草灵(diclofop),式I化合物+禾草灵,式I化合物+双氯磺草胺,式I化合物+野燕枯,式I化合物+野燕枯硫酸甲酯盐,式I化合物+吡氟酰草胺,式I化合物+氟吡草腙,式I化合物+噁唑隆,式I化合物+哌草丹,式I化合物+二甲草胺,式I化合物+异戊乙净,式I化合物+二甲吩草胺,式I化合物+二甲吩草胺-P,式I化合物+噻节因,式I化合物+二甲基次胂酸,式I化合物+氨氟灵,式I化合物+特乐酚,式I化合物+双苯酰草胺,式I化合物+敌草快,式I化合物+二溴化敌草快,式I化合物+氟硫草定,式I化合物+敌草隆,式I化合物+二硝酚,式I化合物+3,4-DP,式I化合物+DSMA,式I化合物+EBEP,式I化合物+茵多酸,式I化合物+茵草敌,式I化合物+戊草丹,式I化合物+乙丁烯氟灵,式I化合物+胺苯磺隆,式I化合物+胺苯磺隆-甲酯,式I化合物+乙氧呋草黄,式I化合物+氟乳醚(ethoxyfen),式I化合物+乙氧磺隆,式I化合物+乙氧苯草胺,式I化合物+精噁唑禾草灵,式I化合物+精噁唑禾草灵-乙酯,式I化合物+四唑酰草胺,式I化合物+硫酸亚铁,式I化合物+高效麦草氟,式I化合物+啶嘧磺隆,式I化合物+双氟磺草胺,式I化合物+吡氟禾草灵,式I化合物+吡氟禾草灵-丁酯,式I化合物+精吡氟禾草灵,式I化合物+精吡氟禾草灵-丁酯,式I化合物+氟唑磺隆,式I化合物+氟唑磺隆-钠盐,式I化合物+氟吡磺隆,式I化合物+氯乙氟灵,式I化合物+氟噻草胺,式I化合物+氟哒嗪草酸(flufenpyr),式I化合物+氟哒嗪草酯,式I化合物+唑嘧磺草胺,式I化合物+氟烯草酸,式I化合物+氟烯草酸-戊酯,式I化合物+丙炔氟草胺,式I化合物+氟草隆,式I化合物+乙羧氟草醚,式I化合物+乙羧氟草醚-乙酯,式I化合物+四氟丙酸,式I化合物+氟啶嘧磺隆(flupyrsulfuron),式I化合物+氟啶嘧磺隆-甲酯-钠盐,式I化合物+芴丁酯,式I化合物+氟啶草酮,式I化合物+氟咯草酮,式I化合物+氯氟吡氧乙酸,式I化合物+呋草酮,式I化合物+嗪草酸,式I化合物+嗪草酸甲酯,式I化合物+氟磺胺草醚,式I化合物+甲酰氨基嘧磺隆,式I化合物+杀木膦,式I化合物+草铵膦酸(glufosinate),式I化合物+草铵膦,式I化合物+草甘膦,式I化合物+氯吡嘧磺隆,式I化合物+氯吡嘧磺隆-甲酯,式I化合物+氟吡禾灵,式I化合物+高效氟吡禾灵,式I化合物+HC-252,式I化合物+环嗪酮,式I化合物+咪草酸,式I化合物+咪草酸-甲酯,式I化合物+甲氧咪草烟,式I化合物+甲咪唑烟酸,式I化合物+咪唑烟酸,式I化合物+咪唑喹啉酸,式I化合物+咪唑乙烟酸,式I化合物+唑吡嘧磺隆,式I化合物+茚草酮,式I化合物+碘甲烷,式I化合物+碘磺隆(iodosulfuron),式I化合物+碘磺隆甲酯钠盐,式I化合物+碘苯腈,式I化合物+异丙隆,式I化合物+异噁隆,式I化合物+异噁酰草胺,式I化合物+异噁氯草酮,式I化合物+异噁唑草酮,式I化合物+特胺灵,式I化合物+乳氟禾草灵,式I化合物+环草定,式I化合物+利谷隆,式I化合物+MAA,式I化合物+MAMA,式I化合物+2甲4氯,式I化合物+2甲4氯乙硫酯,式I化合物+2甲4氯丁酸,式I化合物+2甲4氯丙酸,式I化合物+精2甲4氯丙酸,式I化合物+苯噻酰草胺,式I化合物+氟磺酰草胺,式I化合物+mesosulfuron,式I化合物+甲基二磺隆,式I化合物+硝磺草酮,式I化合物+百亩酸(metam),式I化合物+噁唑酰草胺,式I化合物+苯嗪草酮,式I化合物+吡唑草胺,式I化合物+甲基苯噻隆,式I化合物+甲基胂酸,式I化合物+甲基杀草隆,式I化合物+异硫氰酸甲酯,式I化合物+吡喃隆,式I化合物+异丙甲草胺,式I化合物+精异丙甲草胺,式I化合物+磺草唑胺,式I化合物+甲氧隆,式I化合物+嗪草酮,式I化合物+甲磺隆,式I化合物+甲磺隆-甲酯,式I化合物+MK-616,式I化合物+禾草敌,式I化合物+绿谷隆,式I化合物+甲基砷酸钠,式I化合物+萘丙胺,式I化合物+敌草胺,式I化合物+萘草胺,式I化合物+草不隆,式I化合物+烟嘧磺隆,式I化合物+壬酸,式I化合物+氟草敏,式I化合物+油酸(脂肪酸),式I化合物+坪草丹,式I化合物+嘧苯胺磺隆(orthosulfamuron),式I化合物+氨磺乐灵,式I化合物+丙炔噁草酮,式I化合物+噁草酮,式I化合物+环氧嘧磺隆,式I化合物+噁嗪草酮,式I化合物+乙氧氟草醚,式I化合物+百草枯,式I化合物+百草枯二氯化物,式I化合物+克草敌,式I化合物+二甲戊灵,式I化合物+五氟磺草胺,式I化合物+五氯苯酚,式I化合物+甲氯酰草胺,式I化合物+环戊噁草酮,式I化合物+pethoxamid,式I化合物+矿物油,式I化合物+甜菜宁,式I化合物+甜菜宁-乙酯,式I化合物+氨氯吡啶酸,式I化合物+氯吡酰草胺,式I化合物+唑啉草酯,式I化合物+哌草磷,式I化合物+亚砷酸钾,式I化合物+叠氮化钾,式I化合物+丙草胺,式I化合物+氟嘧磺隆,式I化合物+氟嘧磺隆-甲酯,式I化合物+氨氟乐灵,式I化合物+氟唑草胺,式I化合物+环苯草酮,式I化合物+扑灭通,式I化合物+扑草净,式I化合物+毒草胺,式I化合物+敌稗,式I化合物+噁草酸,式I化合物+扑灭津,式I化合物+苯胺灵,式I化合物+异丙草胺,式I化合物+丙氧基缩二氨基脲,式I化合物+丙氧基缩二氨基脲-钠盐,式I化合物+炔苯酰草胺,式I化合物+苄草丹,式I化合物+氟磺隆,式I化合物+pyraclonil,式I化合物+吡草醚(pyraflufen),式I化合物+吡草醚-乙酯,式I化合物+吡唑特,式I化合物+吡嘧磺隆,式I化合物+吡嘧磺隆-乙酯,式I化合物+苄草唑,式I化合物+嘧啶肟草醚,式I化合物+稗草丹,式I化合物+pyridafol,式I化合物+哒草特,式I化合物+环酯草醚,式I化合物+嘧草醚,式I化合物+嘧草醚-甲酯,式I化合物+pyrimisulfan,式I化合物+嘧草硫醚(pyrithiobac),式I化合物+嘧草硫醚-钠盐,式I化合物+二氯喹啉酸,式I化合物+氯甲喹啉酸,式I化合物+灭藻醌,式I化合物+喹禾灵,式I化合物+精喹禾灵,式I化合物+砜嘧磺隆,式I化合物+烯禾啶,式I化合物+环草隆,式I化合物+西玛津,式I化合物+西草净,式I化合物+氯乙酸钠(SMA),式I化合物+亚砷酸钠,式I化合物+叠氮化钠,式I化合物+氯酸钠,式I化合物+磺草酮,式I化合物+甲磺草胺,式I化合物+甲嘧磺隆,式I化合物+甲嘧磺隆-甲酯,式I化合物+sulfosate,式I化合物+磺酰磺隆,式I化合物+硫酸,式I化合物+焦油,式I化合物+2,3,6-TBA,式I化合物+三氯乙酸,式I化合物+三氯乙酸钠,式I化合物+丁噻隆,式I化合物+吡喃草酮,式I化合物+特草定,式I化合物+特丁通,式I化合物+特丁津,式I化合物+特丁净,式I化合物+噻吩草胺,式I化合物+噻唑烟酸,式I化合物+噻吩磺隆,式I化合物+噻吩磺隆-甲酯,式I化合物+禾草丹,式I化合物+仲草丹,式I化合物+苯唑草酮(topramezone),式I化合物+三甲苯草酮,式I化合物+野麦畏,式I化合物+醚苯磺隆,式I化合物+三嗪氟草胺,式I化合物+苯磺隆,式I化合物+苯磺隆-甲酯,式I化合物+杀草畏,式I化合物+三氯吡氧乙酸,式I化合物+草达津,式I化合物+三氟啶磺隆(trifloxysulfuron),式I化合物+三氟啶磺隆钠盐,式I化合物+氟乐灵,式I化合物+氟胺磺隆,式I化合物+氟胺磺隆-甲酯,式I化合物+三羟基三嗪,式I化合物+三氟甲磺隆,式I化合物+[3-[2-氯-4-氟-5-(1-甲基-6-三氟甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-3-基)苯氧基]-2-吡啶基氧基]乙酸乙基酯(CAS RN 353292-31-6),式I化合物+4-[(4,5-二氢-3-甲氧基-4-甲基-5-氧代)-1H-1,2,4-三唑-1-基羰基氨磺酰基]-5-甲基噻吩-3-羧酸(BAY636),式I化合物+BAY747(CAS RN 335104-84-2),式I化合物+苯唑草酮(topramezone)(CAS RN 210631-68-8),式I化合物+4-羟基-3-[[2-[(2-甲氧基乙氧基)甲基]-6-(三氟甲基)-3-吡啶基]羰基]-二环[3.2.1]辛-3-烯-2-酮(CAS RN 352010-68-5),和式I化合物+4-羟基-3-[[2-(3-甲氧基丙基)-6-(二氟甲基)-3-吡啶基]羰基]-二环[3.2.1]辛-3-烯-2-酮。
参照例如The Pesticide Manual,第12版(BCPC),2000中的内容,式I化合物的混配物还可以是酯或盐的形式。
根据本发明的式I化合物还可以与安全剂组合使用。优选地,在这些混合物中,式I化合物是下表1-102所列出的那些化合物之一。特别考虑与安全剂的下述混合物:
式I化合物+解草酯,式I化合物+解草酸(cloquintocet)及其盐,式I化合物+解草唑-乙酯,式I化合物+解草唑及其盐,式I化合物+吡唑解草酯,式I化合物+吡唑解草酸(mefenpyr),式I化合物+双苯噁唑酸-乙酯,式I化合物+双苯噁唑酸,式I化合物+解草噁唑,式I化合物+解草噁唑R异构体,式(I)化合物+N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺,式I化合物+解草嗪,式I化合物+烯丙酰草胺,式I化合物+AD-67,式I化合物+解草腈,式I化合物+解草胺腈,式I化合物+解草胺腈Z-异构体,式I化合物+解草啶,式I化合物+cyprosulfamide,式I化合物+邻苯二甲酸酐,式I化合物+解草胺,式I化合物+CL304,415,式I化合物+dicyclonon,式I化合物+氟草肟,式I化合物+DKA-24,式I化合物+R-29148和式I化合物+PPG-1292。还能够观察到安全效果的是下述混合物:式I化合物+dymron,式I化合物+2甲4氯,式I化合物+2甲4氯丙酸和式I化合物+精2甲4氯丙酸。
上述提及的安全剂和除草剂描述于,例如the Pesticide Manual,第12版,British Crop Protection Council,2000。R-29148描述于例如P.B.Goldsbrough等人,Plant Physiology,(2002),第130卷第1497-1505页及其中的参考文献,PPG-1292已知于WO09211761且N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺已知于EP365484。
解草嗪,解草酯,cyprosulfamide,吡唑解草酯和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺是特别优选的,其中解草酯尤其有价值。
相对除草剂的安全剂施用率通常取决于施用模式。在田间处理的情况下所施用的是:通常0.001至5.0kg安全剂/公顷,优选0.001至0.5kg安全剂/公顷,和通常0.001至2kg除草剂/公顷,但优选0.005至1kg除草剂/公顷。
本发明的除草组合物适于农业中惯用的全部施用方法,比如出苗前施用、出苗后施用和种子处理。根据预期用途,可以用安全剂来预先处理作物植物的种子材料(拌种种子或幼苗)或者在播种之前或之后将其引入土壤,随后施用(未安全化的)式(I)化合物,任选与共除草剂组合。然而,它还可以在植物出苗之前或之后单独施用或与除草剂一起施用。因此,用安全剂处理植物或种子材料可以原则上独立于除草剂的施用时间而进行。通常优选通过同时施用除草剂和安全剂(例如桶混形式)来处理植物。相对除草剂的安全剂施用率通常取决于施用模式。在田间处理的情况下所施用的是:通常0.001至5.0kg安全剂/公顷,优选0.001至0.5kg安全剂/公顷。在种子处理情况下所施用的是:通常0.001至10g安全剂/kg种子,优选0.05至2g安全剂/kg种子。当安全剂在播种前不久用浸种以液体形式施用时,有利地使用安全剂溶液,其含有浓度为1-10000ppm、优选100-1000ppm的活性成分。
优选将另外的除草剂与上述安全剂之一共同施用。
下述实施例进一步举例说明本发明但并非限制本发明。
制备实施例:
本领域技术人员将理解下文描述的一些化合物是β-酮烯醇,其本身可作为单一互变异构体或作为酮烯醇与二酮互变异构体的混合物存在,正如例如J.March,Advanced Organic Chemistry,第三版,John Wileyand Sons中所描述。化合物在表T1中表示为单一烯醇互变异构体,但还应推断出这种描述包括可通过互变异构形成的二酮和任何可能的烯醇。另外,表T1和表P1中的一些化合物出于简化目的画作单一对映异构体,但是除非特别指定为单一对映异构体,这些结构应理解为代表对映异构体的混合物。
在详细实验部分即使主要的互变异构体是烯醇形式,出于命名目的仍选择二酮互变异构体。
在质子NMR中观察到多于一种互变异构体的情况下,所示数据对应互变异构体的混合物。
实施例1:
制备2,2-二甲基-丙酸3-氧代-4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊-1-烯基酯
步骤1:
制备2-(2,4,6-三甲基苯基)-3-甲氧基-环戊-2-烯酮
在氮下,向2-溴-3-甲氧基-环戊-2-烯酮(6.75g,35.3mmol),2,4,6-三甲基苯基取代硼酸(6.99g,42.6mmol)和新磨碎的磷酸钾(15g,70.6mmol)的脱气甲苯(180ml)悬浮液加入Pd(OAc)2(159mg,0.71mmol)和S-Phos(579mg,1.41mmol),将反应加热至90℃并在N2下搅拌4小时。将反应混合物在乙酸乙酯(150ml)与水(150ml)间分配,除去有机层,将硅胶加至有机层,减压蒸发溶剂,残余物通过硅胶上的快速色谱法纯化,提供2-(2,4,6-三甲基苯基)-3-甲氧基-环戊-2-烯酮(6.2g)。
步骤2:
制备5-[羟基-(四氢-吡喃-4-基)-甲基]-3-甲氧基-2-(2,4,6-三甲基-苯基)-环戊-2-烯酮
在N2下于-78℃,向N-乙基-N,N-二异丙胺(527μl,3.76mmol)的THF(5ml)溶液逐滴加入2.5M的丁基锂的己烷(1.32ml,3.3mmol)溶液,让反应在-78℃搅拌20分钟。然后,于在N2下在10分钟期间内将该淡黄色溶液滴加至预冷却至-78℃的2-(2,4,6-三甲基苯基)-3-甲氧基-环戊-2-烯酮(691ml,3mmol)的THF(5ml)溶液。让所得溶液在-78℃搅拌40分钟。然后一批加入四氢吡喃-4-甲醛(377mg,3.3mmol)的THF(1ml)溶液,在-78℃搅拌反应混合物30分钟,随后在60分钟期间内让其温热至室温。加入饱和氯化铵水溶液(50ml)猝灭反应,用乙酸乙酯(2x 50ml)萃取。通过快速色谱法纯化经合并的有机物,提供5-[羟基-(四氢-吡喃-4-基)-甲基]-3-甲氧基-2-(2,4,6-三甲基-苯基)-环戊-2-烯酮(648mg)。
步骤3:
制备4-[1-(四氢-吡喃-4-基)-亚甲-(E)-基]-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮
向5-[羟基-(四氢-吡喃-4-基)-甲基]-3-甲氧基-2-(2,4,6-三甲基-苯基)-环戊-2-烯酮(408mg,1.18mmol)的丙酮(2ml)溶液加入2N盐酸(2ml)溶液,通过微波辐射将所得溶液加热至130℃持续90分钟。反应混合物用2N盐酸(25ml)稀释,用乙酸乙酯(2x 25ml)萃取。经合并的有机物用盐水洗涤(25ml),在硫酸镁上干燥,过滤,真空浓缩,提供4-[1-(四氢-吡喃-4-基)-亚甲-(E)-基]-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮(302mg)。
步骤4:
制备4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮
向4-[1-(四氢-吡喃-4-基)-亚甲-(E)-基]-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮(270mg,0.86mmol)的乙醇(10ml)溶液加入10%钯碳(27mg),在室温下在氢(3巴)下搅拌所得溶液5小时。然后将反应混合物过滤通过C盐垫,用甲醇洗涤,真空浓缩滤液,提供4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮(258mg)。
步骤5:
制备2,2-二甲基-丙酸3-氧代-4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊-1-烯基酯
在室温下,向4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮(100mg,0.25mmol)的二氯甲烷(5ml)和三乙胺(140μl,1mmol)溶液加入新戊酰氯(91μl,1mmol)。反应混合物在室温下搅拌过夜。将硅胶加至粗制反应混合物,减压蒸发溶剂,残余物通过硅胶上的快速色谱法纯化,提供2,2-二甲基-丙酸3-氧代-4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊-1-烯基酯(102mg)。
实施例2:
制备2-(3,5-二甲基联苯-4-基)-4-(四氢呋喃-3-基甲基)环戊烷-1,3-二酮
步骤1:
制备2-(3,5-二甲基联苯-4-基)-3-甲氧基环戊-2-烯酮
向2-(4-溴-2,6-二甲基苯基)-3-甲氧基-环戊-2-烯酮(1g,3.4mmol)、氟化铯(1.5g,9.87mmol)、苯基取代硼酸(0.5g,4.1mmol)和[1,1’-二(二苯基膦基)二茂铁]二氯-钯(II)(0.44g,0.54mmol)的混合物加入脱气的二甲氧基乙烷(10ml),在氮下搅拌所得悬浮液45分钟,然后在80℃加热4小时。在冷却至室温后用1N盐酸水溶液酸化反应混合物。用乙酸乙酯(3x100ml)进一步萃取水相,然后合并全部有机级分,在无水硫酸钠上干燥,真空浓缩。所得物质通过柱色谱法在硅胶上纯化,提供2-(3,5-二甲基联苯-4-基)-3-甲氧基环戊-2-烯酮(0.7g),是白色固体。
步骤2:
制备2-(3,5-二甲基联苯-4-基)-5-[羟基-(四氢呋喃-3-基)-甲基]-3-甲氧基-环戊-2-烯酮
在氮气氛下于-75℃,向2-(3,5-二甲基联苯-4-基)-3-甲氧基环戊-2-烯酮(0.6g,2.05mmol)的四氢呋喃(12ml)溶液加入1摩尔每升的二(三甲基甲硅烷基)氨基锂的THF(2.5ml,2.5mmol)溶液。在-75℃搅拌所得溶液40分钟并在20分钟内向该混合物加入3-四氢呋喃甲醛(0.42g,4.1mmol)的THF溶液。在-75℃搅拌所得溶液2小时。除去冷却浴,使混合物达到室温,然后搅拌2小时。反应混合物用冰冷的水(100ml)淬灭用乙酸乙酯(3x75ml)萃取,在无水硫酸钠上干燥,过滤,真空浓缩滤液,提供残余物(1.1g),将其原样用于后续步骤。
步骤3:
制备2-(3,5-二甲基联苯-4-基)-4-[1-(四氢呋喃-3-基)亚甲基]-环戊烷-1,3-二酮
在微波条件下于130℃,加热2-(3,5-二甲基联苯-4-基)-5-[羟基-(四氢呋喃-3-基)-甲基]-3-甲氧基-环戊-2-烯酮(1.1g,2.8mmol)、丙酮(21ml)和2N盐酸(10ml)的混合物40分钟。在真空下蒸发有机溶剂,用水稀释(100ml),用乙酸乙酯(3x100ml)萃取。合并经合并的有机萃取物,用水和盐水洗涤,在无水硫酸钠上干燥,过滤,真空浓缩滤液。残余物通过柱色谱法在硅胶上纯化,提供2-(3,5-二甲基联苯-4-基)-4-[1-(四氢呋喃-3-基)亚甲基]-环戊烷-1,3-二酮(0.29g)。
步骤4:
制备2-(3,5-二甲基联苯-4-基)-4-(四氢呋喃-3基甲基)-环戊烷-1,3-二酮
向2-(3,5-二甲基联苯-4-基)-4-[1-(四氢呋喃-3-基)亚甲基]-环戊烷-1,3-二酮(0.29g,0.8mmol)的甲醇(10ml)溶液加入10%钯碳(0.06g),随后在1巴氢气氛下搅拌8小时。然后将反应混合物过滤通过硅藻土,浓缩,提供粗制产品,将其通过快速色谱法(己烷/乙酸乙酯)纯化,提供2-(3,5-二甲基联苯-4-基)-4-(四氢呋喃-3基甲基)-环戊烷-1,3-二酮(0.12g)。
实施例3:
制备2-(4-氟-2,6-二甲基苯基)-4-(四氢吡喃-4-基甲基)环戊烷-1,3-二酮
步骤1:
制备(4-氟-2,6-二甲基苯基)呋喃-2-基甲醇
在氮气氛下于-75℃,向5-氟-2-碘-1,3-二甲苯(11g,44mmol)的四氢呋喃(110ml)溶液加入1.6摩尔每升的正丁基锂的己烷(33ml,52mmol)溶液。在-75℃搅拌所得溶液60分钟并在20分钟内向该混合物加入糠醛(6.3g,65.6mmol)的THF(20ml)溶液。在-75℃搅拌所得溶液2小时。除去冷却浴,让混合物达到室温,然后搅拌5小时。反应混合物用冰冷的水(1000ml)淬灭,用乙酸乙酯(3x250ml)萃取,在无水硫酸钠上干燥,过滤,真空浓缩滤液,提供残余物,将其通过快速色谱法(己烷/乙酸乙酯)纯化,提供(4-氟-2,6-二甲基苯基)呋喃-2-基甲醇(6g)。
步骤2:
制备5-(4-氟-2,6-二甲基苯基)-4-羟基环戊-2-烯酮
在微波条件下于120℃,加热(4-氟-2,6-二甲基苯基)呋喃-2-基甲醇(6g,27mmol)、丙酮(150ml)、水(24ml)和正磷酸(0.6ml)的混合物50分钟。在真空下蒸发有机溶剂,用水(150ml)稀释,用乙酸乙酯(3x100ml)萃取。合并经合并的有机萃取物,用水和盐水洗涤,在无水硫酸钠上干燥,过滤,真空浓缩滤液。残余物通过柱色谱法在硅胶上纯化,提供5-(4-氟-2,6-二甲基苯基)-4-羟基环戊-2-烯酮(3g)。
步骤3:
制备2-(4-氟-2,6-二甲基苯基)环戊-4-烯-1,3-二酮
在0℃,向5-(4-氟-2,6-二甲基苯基)-4-羟基环戊-2-烯酮(3g,13.6mmol)的丙酮(36ml)溶液加入新制备的Jones试剂(24ml)。在0℃搅拌所得溶液60分钟。反应混合物用冰冷的异丙醇(25ml)淬灭,搅拌一小时。在真空下蒸发有机物,用乙酸乙酯萃取,在无水硫酸钠上干燥,过滤,真空浓缩滤液,提供残余物,将其通过快速色谱法(己烷/乙酸乙酯)纯化,提供2-(4-氟-2,6-二甲基苯基)环戊-4-烯-1,3-二酮(2.9g)。
步骤4:
制备2-(4-氟-2,6-二甲基苯基)-环戊烷-1,3-二酮
于25-30℃,向2-(4-氟-2,6-二甲基苯基)环戊-4-烯-1,3-二酮(2.9g,13.3mmol)的乙酸(116ml)溶液加入锌粉(6g,91.7mmol)。于25-30℃搅拌所得溶液16小时。然后将反应混合物过滤通过硅藻土,浓缩,提供粗制产品(2.9g),将其用于后续步骤。
步骤5:
制备2-(4-氟-2,6-二甲基苯基)-3-甲氧基-环戊-2-烯酮
向2-(4-氟-2,6-二甲基苯基)-环戊烷-1,3-二酮(2.9g,13.3mmol)的四氢呋喃(290ml)溶液加入无水碳酸钾(22g,159mmol)和碘甲烷(22.6g,159mmol。于25-30℃搅拌所得混合物16小时。蒸发有机层,反应混合物用水(150ml)淬灭,用乙酸乙酯(3x100ml)萃取。合并经合并的有机萃取物,用水和盐水洗涤,在无水硫酸钠上干燥,过滤,真空浓缩滤液。残余物通过柱色谱法在硅胶上纯化,提供2-(4-氟-2,6-二甲基苯基)-3-甲氧基-环戊-2-烯酮(2g)。
步骤6:
制备2-(4-氟-2,6-二甲基苯基)-3-甲氧基-5-[1-四氢吡喃-4-基)-乙基]-环戊-2-烯酮
在氮气氛下于-75℃,向2-(4-氟-2,6-二甲基苯基)-3-甲氧基-环戊-2-烯酮(0.5g,2.1mmol)的四氢呋喃(10ml)溶液加入1摩尔每升的二(三甲基甲硅烷基)氨基锂的THF(2.7ml)溶液。在-75℃搅拌所得溶液40分钟并在20分钟内向该混合物加入3-四氢呋喃甲醛(0.5g,4.38mmol)的THF溶液。在-75℃搅拌所得溶液2小时。除去冷却浴,让混合物达到室温,然后搅拌2小时。反应混合物用冰冷的水(100ml)淬灭,用乙酸乙酯(3x75ml)萃取,在无水硫酸钠上干燥,过滤,真空浓缩滤液,提供残余物(0.7g),将其原样用于后续步骤。
步骤7:
制备2-(4-氟-2,6-二甲基苯基)-4-[1-(四氢吡喃-4-基)-亚甲基]-环戊烷-1,3-二酮
在微波条件下于130℃,加热2-(4-氟-2,6-二甲基苯基)-3-甲氧基-5-[1-四氢吡喃-4-基)-乙基]-环戊-2-烯酮(0.7g,2mmol)、丙酮(10ml)和2N盐酸(10ml)的混合物40分钟。在真空下蒸发有机溶剂,用水(100ml)稀释,用乙酸乙酯(3x75ml)萃取。合并经合并的有机萃取物,用水和盐水洗涤,在无水硫酸钠上干燥,过滤,真空浓缩滤液。残余物通过柱色谱法在硅胶上纯化,提供2-(4-氟-2,6-二甲基苯基)-4-[1-(四氢吡喃-4-基)-亚甲基]-环戊烷-1,3-二酮(0.23g)。
步骤8:
制备2-(4-氟-2,6-二甲基苯基)-4-[四氢吡喃-4-基甲基)-环戊烷-1,3-二酮
向2-(4-氟-2,6-二甲基苯基)-4-[1-(四氢吡喃-4-基)-亚甲基]-环戊烷-1,3-二酮(0.14g,0.44mmol)的甲醇(3ml)溶液加入10%钯碳(1.5mg),随后在1巴氢气氛下搅拌8小时。然后,将反应混合物过滤通过硅藻土,浓缩,提供粗制产品,将其通过快速色谱法(己烷/乙酸乙酯)纯化,提供2-(4-氟-2,6-二甲基苯基)-4-[四氢吡喃-4-基甲基)-环戊烷-1,3-二酮(0.13g)。
实施例3:
制备2-(4-溴-2,6-二甲基苯基)-4-(四氢吡喃-4-基甲基)环戊烷-1,3-二酮
用10%铂碳在20巴氢气氛下对2-(4-溴-2,6-二甲基苯基)-4-[1-(四氢吡喃-4-基)-亚甲基]-环戊烷-1,3-二酮(0.1g,0.26mmol)的甲醇(100ml)溶液进行H-Cube条件下的氢化。然后浓缩反应混合物,提供粗制产品,将其通过快速色谱法(己烷/乙酸乙酯)纯化,提供2-(4-溴-2,6-二甲基苯基)-4-(四氢吡喃-4-基甲基)环戊烷-1,3-二酮(0.09g)。
实施例4:
制备2-(2,6-二甲基苯基)-4-(四氢吡喃-4-基甲基)环戊烷-1,3-二酮
向2-(4-溴-2,6-二甲基苯基)-4-[1-(四氢吡喃-4-基)-亚甲基]-环戊烷-1,3-二酮(0.3g,0.8mmol)的甲醇(5ml)溶液加入10%钯碳(0.06g),随后在1巴氢气氛下搅拌8小时。然后,将反应混合物过滤通过硅藻土,浓缩,提供粗制产品,将其通过快速色谱法(己烷/乙酸乙酯)纯化,提供2-(2,6-二甲基苯基)-4-(四氢吡喃-4-基甲基)环戊烷-1,3-二酮(0.12g)。
实施例5:
制备2-(4-环丙基-2,6-二甲基-苯基)-4-(四氢吡喃-4-基甲基)-环戊烷-1,3-二酮
在微波条件下于130℃,加热2-(4-溴-2,6-二甲基苯基)-4-(四氢吡喃-4-基甲基)环戊烷-1,3-二酮(0.1g,0.26mmol)、磷酸钾(0.11g,0.53mmol)、环丙基取代硼酸(0.09g,1.05mmol)和四(三苯基膦)钯(0)(0.06g,0.053mmol)、甲苯(2ml)、二甲氧基乙烷(0.5ml)和水(0.5ml)的混合物22分钟。在真空下蒸发有机溶剂,用水稀释,用乙酸乙酯(3x25ml)萃取。合并经合并的有机萃取物,用水和盐水洗涤,在无水硫酸钠上干燥,过滤,真空浓缩滤液。残余物通过柱色谱法在硅胶上纯化,随后用制备型HPLC纯化,提供2-(4-环丙基-2,6-二甲基-苯基)-4-(四氢吡喃-4-基甲基)-环戊烷-1,3-二酮(0.012g)。
实施例6:
制备(4-(1-环丙烷羰基-哌啶-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮
步骤1:
制备4-[4-甲氧基-2-氧代-3-(2,4,6-三甲基-苯基)-环戊-3-烯-(E)-亚基甲基]-哌啶-1-羧酸叔丁基酯
在N2下于-78℃,在30分钟期间内向2-(2,4,6-三甲基苯基)-3-甲氧基-环戊-2-烯酮(9.05g,39.21mmol)的THF(150ml)溶液逐滴加入二异丙基氨基锂溶液(24ml,43.24mmol,1.8M的己烷/THF/乙基苯溶液),让反应在该温度下再搅拌30分钟。然后,一批加入4-甲酰基-哌啶-1-羧酸叔丁基酯(10g,43.24mmol),将反应保持在-78℃持续30分钟,随后在60分钟期间内让其逐渐温热至室温。然后,一批加入叔丁醇钾(7.28g,64.86mmol),在室温下再搅拌反应2小时。
加入氯化铵饱和水溶液(500ml)猝灭反应,用乙酸乙酯(500ml)萃取。除去有机层,将硅胶加至有机层,减压蒸发溶剂,残余物通过快速色谱法在硅胶上纯化,提供4-[4-甲氧基-2-氧代-3-(2,4,6-三甲基-苯基)-环戊-3-烯-(E)-亚基甲基]-哌啶-1-羧酸叔丁基酯(15.33g)
步骤2:
制备4-[4-甲氧基-2-氧代-3-(2,4,6-三甲基-苯基)-环戊-3-烯基甲基]-哌啶-1-羧酸叔丁基酯
向4-[4-甲氧基-2-氧代-3-(2,4,6-三甲基-苯基)-环戊-3-烯-(E)-亚基甲基]-哌啶-1-羧酸叔丁基酯(15.33g,36.02mmol)的乙醇(150ml)溶液加入10%钯活性碳(1.53g),在氢(4巴)下搅拌反应小时。将反应过滤通过C盐垫,减压除去溶剂,提供4-[4-甲氧基-2-氧代-3-(2,4,6-三甲基-苯基)-环戊-3-烯基甲基]-哌啶-1-羧酸叔丁基酯(15.4g)
步骤3:
制备4-[2,4-二氧代-3-(2,4,6-三甲基-苯基)-环戊基甲基]-哌啶鎓盐酸盐
向4-[4-甲氧基-2-氧代-3-(2,4,6-三甲基-苯基)-环戊-3-烯基甲基]-哌啶-1-羧酸叔丁基酯(15.4g,36mmol)的丙酮(100ml)溶液加入2N HCl(100ml),将反应加热至回流4小时。减压除去溶剂,提供4-[2,4-二氧代-3-(2,4,6-三甲基-苯基)-环戊基甲基]-哌啶鎓盐酸盐(12.58g)。
步骤4:
制备环丙烷羧酸4-(1-环丙烷羰基-哌啶-4-基甲基)-3-氧代-2-(2,4,6-三甲基-苯基)-环戊-1-烯基酯
向4-[2,4-二氧代-3-(2,4,6-三甲基-苯基)-环戊基甲基]-哌啶鎓盐酸盐(175mg,0.5mmol)的DCM(5ml)悬浮液加入三乙胺(697μl,5mmol),随后加入环丙基碳酰氯(608μl,4.5mmol),在室温下搅拌反应5小时。将硅胶加至粗制反应物,减压蒸发溶剂,残余物通过硅胶上的快速色谱法纯化,提供环丙烷羧酸4-(1-环丙烷羰基-哌啶-4-基甲基)-3-氧代-2-(2,4,6-三甲基-苯基)-环戊-1-烯基酯(162mg)
步骤5:
制备4-(1-环丙烷羰基-哌啶-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮
向4-(1-环丙烷羰基-哌啶-4-基甲基)-3-氧代-2-(2,4,6-三甲基-苯基)-环戊-1-烯基酯(162mg,0.36mmol)的甲醇悬浮液加入碳酸钾(149mg,1.08mmol),在室温下搅拌反应4小时。减压除去溶剂,将残余物溶于水(2ml)。然后加入2N HCl(3ml),滤去所得沉淀,用己烷洗涤,进行空气干燥,提供4-(1-环丙烷羰基-哌啶-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮(72mg)。
实施例7:
制备4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮的钠盐
在室温下于氮下,将0.5M甲醇钠的甲醇(2ml,1mmol)溶液加入4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮(314mg,1mmol)。反应混合物在室温下搅拌15分钟。减压蒸发反应混合物,提供4-(四氢-吡喃-4-基甲基)-2-(2,4,6-三甲基-苯基)-环戊烷-1,3-二酮的钠盐(336mg)。
在质子NMR谱中观察到多于一个互变异构体或旋转构象异构体的情况下,下述数据对应异构体和构象异构体的混合物。
除非另有说明,在环境温度记录质子NMR谱图。
化合物通过HPLC-MS进行表征,用下述三种方法之一进行分析。
方法A
化合物通过HPLC-MS进行表征:分析使用Waters 2795HPLC,其配有Waters Atlantis dC18柱(柱长20mm,柱内径3mm,粒径3微米,温度40℃),Waters光电二极管阵列和Micromass ZQ2000。根据下述梯度表,使用3分钟的运行时间来进行分析:
时间(分) | 溶剂A(%) | 溶剂B(%) | 流速(ml/分) |
0.00 | 90.0 | 10.0 | 2.00 |
0.25 | 90.0 | 10.0 | 2.00 |
2.00 | 10.0 | 90.0 | 2.00 |
2.50 | 10.0 | 90.0 | 2.00 |
2.60 | 90.0 | 10.0 | 2.00 |
3.0 | 90.0 | 10.0 | 2.00 |
溶剂A:H2O,含0.1%HCOOH
溶剂B:CH3CN,含0.1%HCOOH
方法B
化合物通过HPLC-MS进行表征,分析使用Waters 2777注射器和1525微泵HPLC,其配有Waters Atlantis dC18 IS柱(柱长20mm,柱内径3mm,粒径3微米)、Waters 2996光电二极管阵列、Waters 2420ELSD和Micromass ZQ2000。根据下述梯度表,使用3分钟的运行时间来进行分析:
溶剂A:H2O,含0.05%TFA
溶剂B:CH3CN,含0.05%TFA
方法C:
化合物通过HPLC-MS进行表征,分析使用Finnigan Surveyor MSQPlus,配有Waters Xterra柱(柱长50mm,柱内径4.6mm,粒径3.5微米,温度40℃)、Waters光电二极管阵列和Micromass ZQ2000。根据下述梯度表,使用6分钟的运行时间来进行分析:
时间(分) | 溶剂A(%) | 溶剂B(%) | 流速(ml/分) |
0.00 | 90.0 | 10.0 | 1.30 |
3.80 | 0.00 | 100 | 1.30 |
4.80 | 0.00 | 100 | 1.30 |
5.00 | 90.0 | 10.0 | 1.30 |
6.00 | 90.0 | 10.0 | 1.30 |
溶剂A:H2O,含0.05%HCOOH
溶剂B:CH3CN,含0.05%HCOOH
表T1
表P1
下文表1-102的化合物可以以类似方式获得。
表1涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如下表1所述:
化合物编号 | R1 | R2 | R3 | R4 |
1.001 | CH3 | H | H | H |
1.002 | CH3 | CH3 | H | H |
1.003 | CH3 | H | CH3 | H |
1.004 | CH3 | H | H | CH3 |
1.005 | CH3 | CH3 | CH3 | H |
1.006 | CH3 | CH3 | H | CH3 |
1.007 | CH3 | CH3 | CH3 | CH3 |
1.008 | CH3 | Cl | H | H |
1.009 | CH3 | Cl | H | CH3 |
1.010 | CH3 | Cl | H | OCH3 |
1.011 | CH3 | H | Cl | H |
1.012 | CH3 | H | H | Cl |
1.013 | CH3 | CH3 | Cl | H |
1.014 | CH3 | CH3 | H | Cl |
1.015 | CH3 | H | Cl | CH3 |
1.016 | CH3 | CH3 | Cl | CH3 |
1.017 | CH3 | Br | H | H |
1.018 | CH3 | Br | H | CH3 |
1.019 | CH3 | Br | H | OCH3 |
1.020 | CH3 | H | Br | H |
1.021 | CH3 | H | H | Br |
1.022 | CH3 | CH3 | Br | H |
1.023 | CH3 | CH3 | H | Br |
1.024 | CH3 | H | Br | CH3 |
1.025 | CH3 | CH3 | Br | CH3 |
1.026 | CH3 | CH3O | H | H |
1.027 | CH3 | CH3O | H | CH3 |
1.028 | CH3 | CH3O | H | Cl |
1.029 | CH3 | CH3O | H | Br |
1.030 | CH3 | CH3CH2O | H | H |
1.031 | CH3 | CH3CH2O | H | CH3 |
1.032 | CH3 | CH3CH2O | H | Cl |
1.033 | CH3 | CH3CH2O | H | Br |
1.034 | CH3 | H | CH3O | H |
1.035 | CH3 | H | H | CH3O |
1.036 | CH3 | CH3 | CH3O | H |
1.037 | CH3 | CH3 | H | CH3O |
1.038 | CH3 | H | CH3O | CH3 |
1.039 | CH3 | CH3 | CH3O | CH3 |
1.040 | CH3 | -CH=CH2 | H | CH3 |
1.041 | CH3 | CH3 | H | -CH=CH2 |
1.042 | CH3 | -C.CH | H | CH3 |
1.043 | CH3 | CH3 | H | -C.CH |
1.044 | CH3 | -CH=CH2 | H | -CH=CH2 |
1.045 | CH3 | CH2CH3 | H | CH3 |
1.046 | CH3 | 苯基 | H | CH3 |
1.047 | CH3 | 2-氟苯基 | H | CH3 |
1.048 | CH3 | 2-氯苯基 | H | CH3 |
1.049 | CH3 | 2-三氟甲基苯基 | H | CH3 |
1.050 | CH3 | 2-硝基苯基 | H | CH3 |
1.051 | CH3 | 2-甲基苯基 | H | CH3 |
1.052 | CH3 | 2-甲磺酰基苯基 | H | CH3 |
1.053 | CH3 | 2-氰基苯基 | H | CH3 |
1.054 | CH3 | 3-氟苯基 | H | CH3 |
1.055 | CH3 | 3-氯苯基 | H | CH3 |
1.056 | CH3 | 3-三氟甲基苯基 | H | CH3 |
1.057 | CH3 | 3-硝基苯基 | H | CH3 |
1.058 | CH3 | 3-甲基苯基 | H | CH3 |
1.059 | CH3 | 3-甲磺酰基苯基 | H | CH3 |
1.060 | CH3 | 3-氰基苯基 | H | CH3 |
1.061 | CH3 | 4-氟苯基 | H | CH3 |
1.062 | CH3 | 4-氯苯基 | H | CH3 |
1.063 | CH3 | 4-溴苯基 | H | CH3 |
1.064 | CH3 | 4-二氟甲氧基苯基 | H | CH3 |
1.065 | CH3 | 2-氟-4-氯苯基 | H | CH3 |
1.066 | CH3 | 2-氯-4-氯苯基 | H | CH3 |
1.067 | CH3 | 2-甲基-4-氯苯基 | H | CH3 |
1.068 | CH3 | 4-三氟甲基苯基 | H | CH3 |
1.069 | CH3 | 4-硝基苯基 | H | CH3 |
1.070 | CH3 | 4-甲基苯基 | H | CH3 |
1.071 | CH3 | 4-甲磺酰基苯基 | H | CH3 |
1.072 | CH3 | 4-氰基苯基 | H | CH3 |
1.073 | CH3 | H | 苯基 | H |
1.074 | CH3 | H | 2-氟苯基 | H |
1.075 | CH3 | H | 2-氯苯基 | H |
1.076 | CH3 | H | 2-三氟甲基苯基 | H |
1.077 | CH3 | H | 2-硝基苯基 | H |
1.078 | CH3 | H | 2-甲基苯基 | H |
1.079 | CH3 | H | 2-甲磺酰基苯基 | H |
1.080 | CH3 | H | 2-氰基苯基 | H |
1.081 | CH3 | H | 3-氟苯基 | H |
1.082 | CH3 | H | 3-氯苯基 | H |
1.083 | CH3 | H | 3-三氟甲基苯基 | H |
1.084 | CH3 | H | 3-硝基苯基 | H |
1.085 | CH3 | H | 3-甲基苯基 | H |
1.086 | CH3 | H | 3-甲磺酰基苯基 | H |
1.087 | CH3 | H | 3-氰基苯基 | H |
1.088 | CH3 | H | 4-氟苯基 | H |
1.089 | CH3 | H | 4-氯苯基 | H |
1.090 | CH3 | H | 4-溴苯基 | H |
1.091 | CH3 | H | 4-二氟甲氧基苯基 | H |
1.092 | CH3 | H | 2-氟-4-氯苯基 | H |
1.093 | CH3 | H | 2-氯-4-氯苯基 | H |
1.094 | CH3 | H | 2-甲基-4-氯苯基 | H |
1.095 | CH3 | H | 4-三氟甲基苯基 | H |
1.096 | CH3 | H | 4-硝基苯基 | H |
1.097 | CH3 | H | 4-甲基苯基 | H |
1.098 | CH3 | H | 4-甲磺酰基苯基 | H |
1.099 | CH3 | H | 4-氰基苯基 | H |
1.100 | CH2CH3 | H | H | H |
1.101 | CH2CH3 | CH3 | H | H |
1.102 | CH2CH3 | H | CH3 | H |
1.103 | CH2CH3 | H | H | CH3 |
1.104 | CH2CH3 | CH3 | CH3 | H |
1.105 | CH2CH3 | CH3 | H | CH3 |
1.106 | CH2CH3 | CH3 | CH3 | CH3 |
1.107 | CH2CH3 | Cl | H | H |
1.108 | CH2CH3 | Cl | H | CH3 |
1.109 | CH2CH3 | Cl | H | OCH3 |
1.110 | CH2CH3 | H | Cl | H |
1.111 | CH2CH3 | H | H | Cl |
1.112 | CH2CH3 | CH3 | Cl | H |
1.113 | CH2CH3 | CH3 | H | Cl |
1.114 | CH2CH3 | H | Cl | CH3 |
1.115 | CH2CH3 | CH3 | Cl | CH3 |
1.116 | CH2CH3 | Br | H | H |
1.117 | CH2CH3 | Br | H | CH3 |
1.118 | CH2CH3 | Br | H | OCH3 |
1.119 | CH2CH3 | H | Br | H |
1.120 | CH2CH3 | H | H | Br |
1.121 | CH2CH3 | CH3 | Br | H |
1.122 | CH2CH3 | CH3 | H | Br |
1.123 | CH2CH3 | H | Br | CH3 |
1.124 | CH2CH3 | CH3 | Br | CH3 |
1.125 | CH2CH3 | CH3O | H | H |
1.126 | CH2CH3 | CH3O | H | CH3 |
1.127 | CH2CH3 | CH3O | H | Cl |
1.128 | CH2CH3 | CH3O | H | Br |
1.129 | CH2CH3 | CH3CH2O | H | H |
1.130 | CH2CH3 | CH3CH2O | H | CH3 |
1.131 | CH2CH3 | CH3CH2O | H | Cl |
1.132 | CH2CH3 | CH3CH2O | H | Br |
1.133 | CH2CH3 | H | CH3O | H |
1.134 | CH2CH3 | H | H | CH3O |
1.135 | CH2CH3 | CH3 | CH3O | H |
1.136 | CH2CH3 | CH3 | H | CH3O |
1.137 | CH2CH3 | H | CH3O | CH3 |
1.138 | CH2CH3 | CH3 | CH3O | CH3 |
1.139 | CH2CH3 | -CH=CH2 | H | CH3 |
1.140 | CH2CH3 | CH3 | H | -CH=CH2 |
1.141 | CH2CH3 | -C.CH | H | CH3 |
1.142 | CH2CH3 | CH3 | H | -C.CH |
1.143 | CH2CH3 | -CH=CH2 | H | -CH=CH2 |
1.144 | CH2CH3 | CH2CH3 | H | CH3 |
1.145 | CH2CH3 | 苯基 | H | CH3 |
1.146 | CH2CH3 | 2-氟苯基 | H | CH3 |
1.147 | CH2CH3 | 2-氯苯基 | H | CH3 |
1.148 | CH2CH3 | 2-三氟甲基苯基 | H | CH3 |
1.149 | CH2CH3 | 2-硝基苯基 | H | CH3 |
1.150 | CH2CH3 | 2-甲基苯基 | H | CH3 |
1.151 | CH2CH3 | 2-甲磺酰基苯基 | H | CH3 |
1.152 | CH2CH3 | 2-氰基苯基 | H | CH3 |
1.153 | CH2CH3 | 3-氟苯基 | H | CH3 |
1.154 | CH2CH3 | 3-氯苯基 | H | CH3 |
1.155 | CH2CH3 | 3-三氟甲基苯基 | H | CH3 |
1.156 | CH2CH3 | 3-硝基苯基 | H | CH3 |
1.157 | CH2CH3 | 3-甲基苯基 | H | CH3 |
1.158 | CH2CH3 | 3-甲磺酰基苯基 | H | CH3 |
1.159 | CH2CH3 | 3-氰基苯基 | H | CHx |
1.160 | CH2CH3 | 4-氟苯基 | H | CH3 |
1.161 | CH2CH3 | 4-氯苯基 | H | CH3 |
1.162 | CH2CH3 | 4-溴苯基 | H | CH3 |
1.163 | CH2CH3 | 4-二氟甲氧基苯基 | H | CH3 |
1.164 | CH2CH3 | 2-氟-4-氯苯基 | H | CH3 |
1.165 | CH2CH3 | 2-氯-4-氯苯基 | H | CH3 |
1.166 | CH2CH3 | 2-甲基-4-氯苯基 | H | CH3 |
1.167 | CH2CH3 | 4-三氟甲基苯基 | H | CH3 |
1.168 | CH2CH3 | 4-硝基苯基 | H | CH3 |
1.169 | CH2CH3 | 4-甲基苯基 | H | CH3 |
1.170 | CH2CH3 | 4-甲磺酰基苯基 | H | CH3 |
1.171 | CH2CH3 | 4-氰基苯基 | H | CH3 |
1.172 | CH2CH3 | H | 苯基 | H |
1.173 | CH2CH3 | H | 2-氟苯基 | H |
1.174 | CH2CH3 | H | 2-氯苯基 | H |
1.175 | CH2CH3 | H | 2-三氟甲基苯基 | H |
1.176 | CH2CH3 | H | 2-硝基苯基 | H |
1.177 | CH2CH3 | H | 2-甲基苯基 | H |
1.178 | CH2CH3 | H | 2-甲磺酰基苯基 | H |
1.179 | CH2CH3 | H | 2-氰基苯基 | H |
1.180 | CH2CH3 | H | 3-氟苯基 | H |
1.181 | CH2CH3 | H | 3-氯苯基 | H |
1.182 | CH2CH3 | H | 3-三氟甲基苯基 | H |
1.183 | CH2CH3 | H | 3-硝基苯基 | H |
1.184 | CH2CH3 | H | 3-甲基苯基 | H |
1.185 | CH2CH3 | H | 3-甲磺酰基苯基 | H |
1.186 | CH2CH3 | H | 3-氰基苯基 | H |
1.187 | CH2CH3 | H | 4-氟苯基 | H |
1.188 | CH2CH3 | H | 4-氯苯基 | H |
1.189 | CH2CH3 | H | 4-溴苯基 | H |
1.190 | CH2CH3 | H | 4-二氟甲氧基苯基 | H |
1.191 | CH2CH3 | H | 2-氟-4-氯苯基 | H |
1.192 | CH2CH3 | H | 2-氯-4-氯苯基 | H |
1.193 | CH2CH3 | H | 2-甲基-4-氯苯基 | H |
1.194 | CH2CH3 | H | 4-三氟甲基苯基 | H |
1.195 | CH2CH3 | H | 4-硝基苯基 | H |
1.196 | CH2CH3 | H | 4-甲基苯基 | H |
1.197 | CH2CH3 | H | 4-甲磺酰基苯基 | H |
1.198 | CH2CH3 | H | 4-氰基苯基 | H |
1.199 | CH2CH3 | CH3 | H | CH2CH3 |
1.200 | CH2CH3 | CH2CH3 | H | CH2CH3 |
1.201 | CH2CH3 | Cl | H | CH2CH3 |
1.202 | CH2CH3 | Br | H | CH2CH3 |
1.203 | CH2CH3 | NO2 | H | CH2CH3 |
1.204 | CH2CH3 | CH3O | H | CH2CH3 |
1.205 | CH2CH3 | CH3S | H | CH2CH3 |
1.206 | CH2CH3 | CH3SO2 | H | CH2CH3 |
1.207 | CH2CH3 | CH2=CH | H | CH2CH3 |
1.208 | CH2CH3 | -C.CH | H | CH2CH3 |
1.209 | CH2CH3 | 苯基 | H | CH2CH3 |
1.210 | CH2CH3 | 2-氟苯基 | H | CH2CH3 |
1.211 | CH2CH3 | 2-氯苯基 | H | CH2CH3 |
1.212 | CH2CH3 | 2-三氟甲基苯基 | H | CH2CH3 |
1.213 | CH2CH3 | 2-硝基苯基 | H | CH2CH3 |
1.214 | CH2CH3 | 2-甲基苯基 | H | CH2CH3 |
1.215 | CH2CH3 | 2-甲磺酰基苯基 | H | CH2CH3 |
1.216 | CH2CH3 | 2-氰基苯基 | H | CH2CH3 |
1.217 | CH2CH3 | 3-氟苯基 | H | CH2CH3 |
1.218 | CH2CH3 | 3-氯苯基 | H | CH2CH3 |
1.219 | CH2CH3 | 3-三氟甲基苯基 | H | CH2CH3 |
1.220 | CH2CH3 | 3-硝基苯基 | H | CH2CH3 |
1.221 | CH2CH3 | 3-甲基苯基 | H | CH2CH3 |
1.222 | CH2CH3 | 3-甲磺酰基苯基 | H | CH2CH3 |
1.223 | CH2CH3 | 3-氰基苯基 | H | CH2CH3 |
1.224 | CH2CH3 | 4-氟苯基 | H | CH2CH3 |
1.225 | CH2CH3 | 4-氯苯基 | H | CH2CH3 |
1.226 | CH2CH3 | 4-溴苯基 | H | CH2CH3 |
1.227 | CH2CH3 | 4-二氟甲氧基苯基 | H | CH2CH3 |
1.228 | CH2CH3 | 2-氟-4-氯苯基 | H | CH2CH3 |
1.229 | CH2CH3 | 2-氯-4-氯苯基 | H | CH2CH3 |
1.230 | CH2CH3 | 2-甲基-4-氯苯基 | H | CH2CH3 |
1.231 | CH2CH3 | 4-三氟甲基苯基 | H | CH2CH3 |
1.232 | CH2CH3 | 4-硝基苯基 | H | CH2CH3 |
1.233 | CH2CH3 | 4-甲基苯基 | H | CH2CH3 |
1.234 | CH2CH3 | 4-甲磺酰基苯基 | H | CH2CH3 |
1.235 | CH2CH3 | 4-氰基苯基 | H | CH2CH3 |
1.236 | OCH3 | H | 苯基 | H |
1.237 | OCH3 | H | 2-氟苯基 | H |
1.238 | OCH3 | H | 2-氯苯基 | H |
1.239 | OCH3 | H | 2-三氟甲基苯基 | H |
1.240 | OCH3 | H | 2-硝基苯基 | H |
1.241 | OCH3 | H | 2-甲基苯基 | H |
1.242 | OCH3 | H | 2-甲磺酰基苯基 | H |
1.243 | OCH3 | H | 2-氰基苯基 | H |
1.244 | OCH3 | H | 3-氟苯基 | H |
1.245 | OCH3 | H | 3-氯苯基 | H |
1.246 | OCH3 | H | 3-三氟甲基苯基 | H |
1.247 | OCH3 | H | 3-硝基苯基 | H |
1.248 | OCH3 | H | 3-甲基苯基 | H |
1.249 | OCH3 | H | 3-甲磺酰基苯基 | H |
1.250 | OCH3 | H | 3-氰基苯基 | H |
1.251 | OCH3 | H | 4-氟苯基 | H |
1.252 | OCH3 | H | 4-氯苯基 | H |
1.253 | OCH3 | H | 4-溴苯基 | H |
1.254 | OCH3 | H | 4-二氟甲氧基苯基 | H |
1.255 | OCH3 | H | 2-氟-4-氯苯基 | H |
1.256 | OCH3 | H | 2-氯-4-氯苯基 | H |
1.257 | OCH3 | H | 2-甲基-4-氯苯基 | H |
1.258 | OCH3 | H | 4-三氟甲基苯基 | H |
1.259 | OCH3 | H | 4-硝基苯基 | H |
1.260 | OCH3 | H | 4-甲基苯基 | H |
1.261 | OCH3 | H | 4-甲磺酰基苯基 | H |
1.262 | OCH3 | H | 4-氰基苯基 | H |
表2涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表3涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表4涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表5涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表6涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表7涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表8涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表9涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表10涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表11涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表12涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表13涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表14涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表15涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表16涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表17涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表18涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表19涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表20涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表21涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表22涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表23涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表24涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表25涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表26涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表27涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表28涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表29涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表30涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表31涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表32涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表33涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表34涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表35涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表36涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表37涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表38涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表39涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表40涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表41涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表42涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表43涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表44涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表45涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表46涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表47涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表48涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表49涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表50涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表51涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表52涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表53涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表54涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表55涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表56涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表57涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表58涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表59涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表60涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表61涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表62涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表63涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表64涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表65涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表66涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表67涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表68涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表69涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表70涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表71涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表72涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表73涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表74涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表75涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表76涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表77涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表78涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表79涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表80涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表81涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表82涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表83涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表84涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表85涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表86涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表87涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表88涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表89涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表90涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表91涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表92涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表93涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表94涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表95涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表96涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表97涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表98涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表99涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
表100涵盖下述类型的262种化合物:
其中G,R5,R6,R7,R8和R9全都是氢,而R1,R2,R3和R4如表1所述。
表101涵盖下述类型的262种化合物
其中G,R5,R6,R8和R9是氢,R7是甲基而R1,R2,R3和R4如表1所述。
表102涵盖下述类型的262种化合物
其中G和R5,R8和R9是氢,R6和R7是甲基而R1,R2,R3和R4如表1所述。
生物实施例
实施例A
将多种试验物种的种子播种于盆中的标准土壤中。于温室在受控条件下在栽培1天之后(出苗前)或在栽培10天之后(出苗后),将植物用喷雾水溶液喷雾,该喷雾水溶液衍生自原药活性成分在0.6ml丙酮和45ml含有10.6%Emulsogen EL(登记号61791-12-6)、42.2%N-甲基吡咯烷酮、42.2%二丙二醇一甲基醚(登记号34590-94-8)和0.2%X-77(登记号11097-66-8)的配制溶液中的配制剂。然后在温室中于最佳条件下生长供测试植物,直到14或15天后(苗后)和19或20天后(苗前),评价此测试(100=损伤全部植物;0=未损伤植物)。
测试植物:
大穗看麦娘(Alopecurus myosuroides)(ALOMY)、野燕麦(Avenafatua)(AVEFA)、多年黑麦草(Lolium perenne)(LOLPE)、法式狗毛草(Setaria faberi)(SETFA)、马唐(Digitaria sanguinalis)(DIGSA)、稗(Echinochloa crus-galli)(ECHCG)
苗前活性
苗后活性
实施例B
将多种试验物种的种子播种于盆中的标准土壤中。在玻璃房中,在受控条件下(24/16℃(白天/夜晚);14小时光照;65%湿度)栽培1天后(苗前)或栽培8天后(苗后),用喷雾水溶液来喷雾植物,该喷雾水溶液源自原药活性成分在含0.5%吐温20(聚氧乙烯失水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)的丙酮/水溶液(50∶50)中的配制剂。
然后将测试植物在玻璃房中于受控条件下生长(24/16℃,日间/夜间;14小时光照;65%湿度),每天浇水两次。13天之后,对于出苗前和出苗后评价测试(100=植物完全损伤;0=没有植物损伤)。
测试植物:
多年黑麦草(LOLPE),大穗看麦娘(ALOMY),稗(ECHCG),野燕麦(AVEFA)
苗前活性
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
T3 | 250 | 60 | 50 | 20 | 50 |
T4 | 250 | 100 | 100 | 100 | 90 |
T5 | 250 | 100 | 100 | 100 | 80 |
T7 | 250 | 80 | 70 | 100 | 50 |
T8 | 250 | 100 | 100 | 100 | 100 |
T9 | 250 | 60 | 20 | 20 | 0 |
T10 | 250 | 90 | 70 | 70 | 40 |
T11 | 250 | 70 | 30 | 20 | 0 |
T12 | 250 | 100 | 100 | 100 | 100 |
T13 | 250 | 30 | 30 | 10 | 0 |
T14 | 250 | 100 | 100 | 100 | 100 |
T15 | 250 | 100 | 70 | 100 | 100 |
T16 | 250 | 100 | 100 | 100 | 80 |
T17 | 250 | 100 | 100 | 100 | 100 |
T18 | 250 | 100 | 100 | 100 | 70 |
T21 | 250 | 100 | 100 | 90 | 70 |
T22 | 250 | 100 | 100 | 100 | 90 |
T23 | 250 | 100 | 100 | 100 | 100 |
T24 | 250 | 100 | 100 | 100 | 90 |
T26 | 250 | 100 | 70 | 100 | 60 |
T27 | 250 | 100 | 90 | 80 | 60 |
T29 | 250 | 100 | 70 | 90 | 50 |
T30 | 250 | 90 | 60 | 80 | 30 |
T31 | 250 | 90 | 80 | 80 | 90 |
T32 | 250 | 100 | 70 | 100 | 90 |
T33 | 250 | 90 | 60 | 90 | 50 |
T34 | 250 | 90 | 70 | 100 | 70 |
T35 | 250 | 70 | 30 | 40 | 10 |
T36 | 250 | 90 | 90 | 100 | 90 |
T37 | 250 | 100 | 100 | 100 | 90 |
T38 | 250 | 70 | 90 | 100 | 40 |
T39 | 250 | 100 | 100 | 100 | 100 |
T40 | 250 | 100 | 100 | 100 | 80 |
T41 | 250 | 90 | 70 | 100 | 90 |
T42 | 250 | 0 | 0 | 20 | 0 |
T43 | 250 | 100 | 80 | 100 | 100 |
T44 | 250 | 100 | 90 | 60 | 20 |
T46 | 250 | 10 | 50 | 10 | 10 |
T47 | 250 | 60 | 20 | 40 | 50 |
T48 | 250 | 90 | 90 | 100 | 90 |
T50 | 250 | 100 | 100 | 100 | 100 |
T51 | 250 | 100 | 80 | 80 | 90 |
T52 | 250 | 100 | 100 | 80 | 80 |
T53 | 250 | 40 | 30 | 0 | 0 |
T54 | 250 | 100 | 80 | 100 | 50 |
T55 | 250 | 100 | 80 | 90 | 60 |
T58 | 250 | 100 | 90 | 100 | 90 |
T59 | 250 | 100 | 90 | 100 | 90 |
T60 | 250 | 10 | 10 | 0 | 0 |
T61 | 250 | 90 | 70 | 90 | 80 |
T62 | 250 | 100 | 80 | 100 | 70 |
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
T63 | 250 | 100 | 70 | 100 | 90 |
T64 | 250 | 100 | 50 | 100 | 90 |
T65 | 250 | 80 | 70 | 100 | 80 |
T66 | 250 | 80 | 90 | 100 | 80 |
T67 | 250 | 100 | 90 | 100 | 90 |
T68 | 250 | 90 | 30 | 50 | 40 |
T69 | 250 | 10 | 0 | 20 | 10 |
T70 | 250 | 70 | 20 | 60 | 70 |
T71 | 250 | 30 | 20 | 10 | 20 |
T72 | 250 | 60 | 30 | 80 | 20 |
T73 | 250 | 80 | 40 | 80 | 80 |
T74 | 250 | 30 | 30 | 50 | 20 |
T75 | 250 | 80 | 30 | 70 | 70 |
T76 | 250 | 60 | 30 | 60 | 20 |
T77 | 250 | 0 | 0 | 0 | 0 |
T78 | 250 | 30 | 20 | 30 | 0 |
T79 | 250 | 90 | 60 | 60 | 20 |
T80 | 250 | 100 | 70 | 70 | 70 |
T81 | 250 | 80 | 80 | 60 | 80 |
T82 | 250 | 90 | 50 | 60 | 50 |
T83 | 250 | 90 | 60 | 90 | 70 |
T84 | 250 | 90 | 50 | 60 | 50 |
T85 | 250 | 60 | 60 | 30 | 20 |
T86 | 250 | 100 | 60 | 50 | 30 |
T87 | 250 | 100 | 90 | 60 | 90 |
T88 | 250 | 100 | 90 | 80 | 90 |
T89 | 250 | 70 | 50 | 60 | 10 |
T90 | 250 | 60 | 40 | 50 | 60 |
T91 | 250 | 70 | 20 | 60 | 40 |
T92 | 250 | 30 | 30 | 40 | 10 |
T93 | 250 | 90 | 60 | 90 | 60 |
T94 | 250 | 90 | 90 | 80 | 90 |
T95 | 250 | 100 | 90 | 60 | 90 |
T96 | 250 | 60 | 20 | 20 | 10 |
T97 | 250 | 70 | 30 | 60 | 30 |
T98 | 250 | 90 | 70 | 90 | 80 |
T99 | 250 | 60 | 20 | 60 | 30 |
T100 | 250 | 90 | 60 | 70 | 60 |
T101 | 250 | 50 | 20 | 50 | 30 |
T102 | 250 | 70 | 50 | 50 | 30 |
T103 | 250 | 30 | 30 | 10 | 20 |
T104 | 250 | 70 | 60 | 90 | 60 |
T105 | 250 | 60 | 20 | 40 | 30 |
T106 | 250 | 20 | 20 | 20 | 30 |
T107 | 250 | 70 | 80 | 70 | 60 |
T108 | 250 | 50 | 10 | 60 | 40 |
T109 | 250 | 0 | 0 | 0 | 0 |
T110 | 250 | 50 | 30 | 70 | 30 |
T111 | 250 | 90 | 40 | 80 | 40 |
T112 | 250 | 50 | 40 | 30 | 20 |
T113 | 250 | 70 | 60 | 90 | 70 |
T114 | 250 | 40 | 50 | 60 | 20 |
T118 | 250 | 40 | 40 | 30 | 20 |
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
T119 | 250 | 80 | 40 | 100 | 30 |
T120 | 250 | 20 | 30 | 30 | 10 |
T121 | 250 | 80 | 30 | 90 | 60 |
T122 | 250 | 50 | 20 | 70 | 20 |
T123 | 250 | 60 | 60 | 60 | 60 |
T124 | 250 | 20 | 20 | 30 | 10 |
T126 | 250 | 60 | 30 | 50 | 40 |
T128 | 250 | 50 | 70 | 60 | 40 |
T130 | 250 | 100 | 70 | 30 | 10 |
T131 | 250 | 90 | 70 | 100 | 70 |
T132 | 250 | 70 | 20 | 90 | 70 |
T135 | 250 | 40 | 0 | 60 | 30 |
T138 | 250 | 90 | 80 | 90 | 70 |
T139 | 250 | 80 | 70 | 90 | 60 |
T140 | 250 | 70 | 60 | 90 | 50 |
T141 | 250 | 80 | 80 | 80 | 80 |
T142 | 250 | 70 | 90 | 90 | 80 |
T143 | 250 | 100 | 80 | 100 | 50 |
T144 | 250 | 70 | 80 | 90 | 70 |
T145 | 250 | 50 | 60 | 20 | 30 |
T146 | 250 | 90 | 70 | 70 | 50 |
T147 | 250 | 30 | 50 | 40 | 10 |
T148 | 250 | 50 | 70 | 30 | 40 |
T149 | 250 | 20 | 30 | 30 | 10 |
T151 | 250 | 30 | 20 | 40 | 10 |
T156 | 250 | 100 | 80 | 100 | 70 |
T157 | 250 | 10 | 10 | 40 | 0 |
T158 | 250 | 90 | 80 | 100 | 70 |
T159 | 250 | 70 | 50 | 100 | 30 |
T160 | 250 | 90 | 30 | 70 | 40 |
T161 | 250 | 90 | 30 | 100 | 60 |
T162 | 250 | 70 | 40 | 50 | 50 |
T163 | 250 | 80 | 50 | 60 | 60 |
P5 | 250 | 100 | 100 | 100 | 80 |
P7 | 250 | 100 | 100 | 100 | 90 |
P9 | 250 | 40 | 30 | 20 | 0 |
P11 | 250 | 100 | 100 | 100 | 100 |
P13 | 250 | 100 | 100 | 100 | 90 |
P14 | 250 | 100 | 100 | 100 | 80 |
P15 | 250 | 100 | 100 | 100 | 90 |
P16 | 250 | 100 | 100 | 100 | 90 |
P17 | 250 | 100 | 100 | 90 | 90 |
P18 | 250 | 100 | 100 | 90 | 80 |
P20 | 250 | 100 | 100 | 80 | 90 |
P23 | 250 | 100 | 100 | 100 | 80 |
P24 | 250 | 100 | 100 | 90 | 90 |
P25 | 250 | 90 | 100 | 90 | 80 |
P26 | 250 | 100 | 100 | 90 | 80 |
P27 | 250 | 100 | 100 | 80 | 80 |
P28 | 250 | 100 | 70 | 20 | 30 |
P29 | 250 | 90 | 50 | 0 | 20 |
P30 | 250 | 100 | 100 | 80 | 90 |
P31 | 250 | 100 | 100 | 100 | 90 |
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
P34 | 250 | 100 | 90 | 100 | 90 |
P37 | 250 | 100 | 100 | 70 | 70 |
P42 | 250 | 40 | 30 | 30 | 0 |
P43 | 250 | 100 | 100 | 100 | 100 |
P44 | 250 | 100 | 100 | 100 | 90 |
P45 | 250 | 100 | 100 | 100 | 100 |
P46 | 250 | 90 | 70 | 100 | 60 |
P47 | 250 | 60 | 30 | 60 | 50 |
P48 | 250 | 80 | 70 | 40 | 60 |
P49 | 250 | 100 | 80 | 100 | 60 |
P50 | 250 | 100 | 100 | 100 | 100 |
P51 | 250 | 100 | 100 | 100 | 100 |
P53 | 250 | 100 | 60 | 90 | 70 |
P54 | 250 | 100 | 80 | 100 | 70 |
P55 | 250 | 100 | 100 | 100 | 90 |
P56 | 250 | 100 | 100 | 100 | 90 |
P57 | 250 | 60 | 50 | 30 | 70 |
P58 | 250 | 80 | 70 | 80 | 70 |
P59 | 250 | 80 | 50 | 70 | 30 |
P60 | 250 | 80 | 30 | 50 | 0 |
P61 | 250 | 90 | 50 | 80 | 30 |
P63 | 250 | 70 | 50 | 70 | 40 |
P64 | 250 | 80 | 70 | 80 | 70 |
P65 | 250 | 90 | 60 | 80 | 60 |
P67 | 250 | 100 | 80 | 90 | 90 |
P68 | 250 | 100 | 90 | 100 | 90 |
P71 | 250 | 100 | 90 | 100 | 100 |
苗后活性
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
T3 | 250 | 70 | 40 | 70 | 70 |
T4 | 250 | 100 | 100 | 100 | 100 |
T5 | 250 | 100 | 100 | 100 | 90 |
T6 | 250 | 10 | 20 | 10 | 0 |
T7 | 250 | 80 | 100 | 90 | 90 |
T8 | 250 | 100 | 100 | 100 | 100 |
T9 | 250 | 80 | 60 | 80 | 30 |
T10 | 250 | 70 | 70 | 80 | 80 |
T11 | 250 | 50 | 60 | 70 | 30 |
T12 | 250 | 100 | 100 | 100 | 100 |
T13 | 250 | 30 | 10 | 40 | 0 |
T14 | 250 | 100 | 100 | 100 | 100 |
T15 | 250 | 100 | 100 | 100 | 100 |
T16 | 250 | 100 | 100 | 100 | 100 |
T17 | 250 | 100 | 90 | 100 | 100 |
T18 | 250 | 100 | 80 | 90 | 70 |
T21 | 250 | 90 | 90 | 80 | 90 |
T22 | 250 | 100 | 90 | 100 | 100 |
T23 | 250 | 100 | 90 | 100 | 100 |
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
T24 | 250 | 100 | 90 | 100 | 100 |
T26 | 250 | 80 | 60 | 60 | 70 |
T27 | 250 | 80 | 70 | 80 | 70 |
T29 | 250 | 90 | 70 | 80 | 60 |
T30 | 250 | 80 | 80 | 80 | 70 |
T31 | 250 | 70 | 90 | 80 | 90 |
T32 | 250 | 90 | 90 | 90 | 90 |
T33 | 250 | 60 | 60 | 60 | 70 |
T34 | 250 | 90 | 90 | 100 | 100 |
T35 | 250 | 70 | 70 | 70 | 60 |
T36 | 250 | 80 | 80 | 90 | 90 |
T37 | 250 | 100 | 90 | 100 | 100 |
T38 | 250 | 100 | 100 | 100 | 100 |
T39 | 250 | 100 | 90 | 100 | 100 |
T40 | 250 | 100 | 80 | 100 | 90 |
T41 | 250 | 100 | 100 | 100 | 100 |
T42 | 250 | 20 | 0 | 30 | 0 |
T43 | 250 | 100 | 90 | 80 | 90 |
T44 | 250 | 70 | 60 | 80 | 40 |
T46 | 250 | 40 | 60 | 60 | 50 |
T47 | 250 | 30 | 30 | 60 | 50 |
T48 | 250 | 70 | 90 | 100 | 90 |
T50 | 250 | 100 | 100 | 100 | 100 |
T51 | 250 | 60 | 70 | 70 | 80 |
T52 | 250 | 90 | 90 | 100 | 80 |
T54 | 250 | 70 | 80 | 80 | 80 |
T55 | 250 | 60 | 70 | 70 | 50 |
T58 | 250 | 90 | 100 | 100 | 90 |
T59 | 250 | 100 | 90 | 90 | 100 |
T60 | 250 | 20 | 30 | 10 | 10 |
T61 | 250 | 90 | 90 | 100 | 100 |
T62 | 250 | 90 | 90 | 100 | 100 |
T63 | 250 | 90 | 90 | 90 | 100 |
T64 | 250 | 90 | 90 | 100 | 100 |
T65 | 250 | 90 | 90 | 100 | 100 |
T66 | 250 | 60 | 90 | 100 | 90 |
T67 | 250 | 100 | 90 | 100 | 100 |
T68 | 250 | 90 | 60 | 90 | 90 |
T69 | 250 | 30 | 30 | 20 | 30 |
T70 | 250 | 80 | 70 | 80 | 100 |
T71 | 250 | 40 | 30 | 70 | 80 |
T72 | 250 | 80 | 50 | 90 | 80 |
T73 | 250 | 80 | 90 | 90 | 100 |
T74 | 250 | 40 | 70 | 100 | 90 |
T75 | 250 | 100 | 90 | 90 | 100 |
T76 | 250 | 40 | 90 | 90 | 100 |
T77 | 250 | 40 | 30 | 20 | 40 |
T78 | 250 | 50 | 40 | 70 | 40 |
T79 | 250 | 60 | 60 | 70 | 80 |
T80 | 250 | 90 | 90 | 80 | 100 |
T81 | 250 | 90 | 90 | 80 | 100 |
T82 | 250 | 90 | 90 | 80 | 100 |
T83 | 250 | 90 | 80 | 70 | 100 |
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
T84 | 250 | 100 | 90 | 90 | 100 |
T85 | 250 | 90 | 90 | 80 | 90 |
T86 | 250 | 70 | 40 | 80 | 80 |
T87 | 250 | 90 | 70 | 70 | 90 |
T88 | 250 | 90 | 90 | 90 | 100 |
T89 | 250 | 40 | 30 | 40 | 20 |
T90 | 250 | 80 | 70 | 80 | 100 |
T91 | 250 | 50 | 40 | 50 | 90 |
T92 | 250 | 20 | 30 | 40 | 60 |
T93 | 250 | 70 | 60 | 60 | 70 |
T94 | 250 | 90 | 100 | 90 | 100 |
T95 | 250 | 100 | 90 | 70 | 100 |
T96 | 250 | 60 | 60 | 40 | 40 |
T97 | 250 | 60 | 70 | 80 | 70 |
T98 | 250 | 100 | 100 | 90 | 100 |
T99 | 250 | 50 | 70 | 90 | 90 |
T100 | 250 | 80 | 90 | 60 | 90 |
T101 | 250 | 40 | 40 | 20 | 40 |
T102 | 250 | 80 | 90 | 40 | 90 |
T103 | 250 | 50 | 50 | 30 | 60 |
T104 | 250 | 80 | 70 | 70 | 90 |
T105 | 250 | 50 | 30 | 30 | 40 |
T106 | 250 | 30 | 40 | 30 | 10 |
T107 | 250 | 90 | 70 | 60 | 90 |
T108 | 250 | 70 | 70 | 40 | 70 |
T110 | 250 | 50 | 30 | 40 | 80 |
T111 | 250 | 80 | 80 | 70 | 90 |
T112 | 250 | 30 | 40 | 30 | 30 |
T113 | 250 | 100 | 90 | 70 | 100 |
T114 | 250 | 50 | 40 | 30 | 40 |
T116 | 250 | 90 | 60 | 50 | 90 |
T118 | 250 | 30 | 60 | 40 | 80 |
T119 | 250 | 90 | 90 | 90 | 80 |
T120 | 250 | 30 | 30 | 10 | 20 |
T121 | 250 | 90 | 80 | 80 | 100 |
T122 | 250 | 80 | 60 | 70 | 30 |
T123 | 250 | 70 | 80 | 60 | 90 |
T124 | 250 | 20 | 30 | 20 | 30 |
T126 | 250 | 70 | 50 | 60 | 70 |
T127 | 250 | 20 | 20 | 20 | 10 |
T128 | 250 | 50 | 40 | 50 | 90 |
T130 | 250 | 90 | 60 | 60 | 70 |
T131 | 250 | 100 | 90 | 90 | 90 |
T132 | 250 | 70 | 70 | 100 | 80 |
T133 | 250 | 0 | 20 | 90 | 30 |
T135 | 250 | 70 | 80 | 90 | 80 |
T136 | 250 | 30 | 50 | 60 | 70 |
T138 | 250 | 90 | 90 | 70 | 90 |
T139 | 250 | 90 | 90 | 100 | 90 |
T140 | 250 | 90 | 90 | 90 | 60 |
T141 | 250 | 70 | 80 | 60 | 90 |
T142 | 250 | 70 | 90 | 60 | 90 |
T143 | 250 | 60 | 60 | 60 | 80 |
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
T144 | 250 | 80 | 80 | 80 | 90 |
T145 | 250 | 40 | 60 | 30 | 50 |
T146 | 250 | 80 | 80 | 70 | 90 |
T147 | 250 | 40 | 60 | 50 | 70 |
T148 | 250 | 70 | 80 | 60 | 100 |
T149 | 250 | 40 | 30 | 20 | 40 |
T151 | 250 | 20 | 30 | 40 | 10 |
T152 | 250 | 30 | 20 | 10 | 10 |
T153 | 250 | 20 | 10 | 10 | 20 |
T156 | 250 | 100 | 90 | 70 | 90 |
T157 | 250 | 30 | 30 | 60 | 50 |
T158 | 250 | 100 | 100 | 100 | 100 |
T159 | 250 | 100 | 90 | 100 | 90 |
T160 | 250 | 100 | 40 | 70 | 60 |
T161 | 250 | 100 | 70 | 90 | 90 |
T162 | 250 | 90 | 60 | 70 | 80 |
T163 | 250 | 100 | 90 | 90 | 100 |
P4 | 250 | 30 | 60 | 20 | 40 |
P5 | 250 | 100 | 100 | 100 | 90 |
P7 | 250 | 100 | 100 | 90 | 80 |
P9 | 250 | 40 | 30 | 50 | 10 |
P11 | 250 | 100 | 90 | 100 | 90 |
P13 | 250 | 100 | 90 | 100 | 90 |
P14 | 250 | 100 | 90 | 90 | 90 |
P15 | 250 | 100 | 100 | 100 | 90 |
P16 | 250 | 100 | 100 | 100 | 100 |
P17 | 250 | 100 | 100 | 100 | 90 |
P18 | 250 | 100 | 90 | 90 | 90 |
P20 | 250 | 100 | 100 | 100 | 90 |
P23 | 250 | 100 | 90 | 90 | 90 |
P24 | 250 | 100 | 90 | 90 | 90 |
P25 | 250 | 100 | 90 | 100 | 90 |
P26 | 250 | 100 | 100 | 100 | 90 |
P27 | 250 | 100 | 80 | 90 | 80 |
P28 | 250 | 100 | 70 | 60 | 70 |
P29 | 250 | 100 | 80 | 30 | 70 |
P30 | 250 | 100 | 100 | 90 | 100 |
P31 | 250 | 100 | 90 | 100 | 90 |
P34 | 250 | 100 | 80 | 60 | 90 |
P37 | 250 | 90 | 90 | 90 | 90 |
P42 | 250 | 40 | 60 | 70 | 70 |
P43 | 250 | 100 | 100 | 100 | 90 |
P44 | 250 | 100 | 100 | 100 | 100 |
P45 | 250 | 100 | 100 | 90 | 100 |
P46 | 250 | 80 | 90 | 70 | 90 |
P47 | 250 | 60 | 70 | 50 | 60 |
P48 | 250 | 90 | 90 | 90 | 100 |
P49 | 250 | 100 | 80 | 100 | 90 |
P50 | 250 | 100 | 100 | 100 | 100 |
P51 | 250 | 100 | 100 | 100 | 100 |
P53 | 250 | 20 | 60 | 70 | 40 |
P54 | 250 | 40 | 70 | 80 | 50 |
P55 | 250 | 100 | 90 | 100 | 100 |
化合物编号 | 用量g/公顷 | LOLPE | ALOMY | ECHCG | AVEFA |
P56 | 250 | 100 | 90 | 90 | 100 |
P57 | 250 | 60 | 80 | 70 | 80 |
P58 | 250 | 90 | 90 | 70 | 90 |
P59 | 250 | 80 | 90 | 70 | 80 |
P60 | 250 | 70 | 80 | 40 | 80 |
P61 | 250 | 90 | 90 | 90 | 90 |
P62 | 250 | 80 | 70 | 70 | 70 |
P63 | 250 | 80 | 90 | 70 | 90 |
P64 | 250 | 90 | 100 | 90 | 100 |
P65 | 250 | 90 | 90 | 90 | 90 |
P67 | 250 | 100 | 100 | 100 | 100 |
P68 | 250 | 100 | 90 | 100 | 90 |
P69 | 250 | 40 | 0 | 80 | 20 |
P71 | 250 | 100 | 100 | 100 | 90 |
实施例C
将冬小麦品种′Hereward′的种子播种于盆中的标准土壤中。在受控条件下于温室(24/16℃,白天/夜晚;14小时光照;65%湿度)中栽培8天之后,用喷雾水溶液喷雾植物,该水溶液衍生自原药活性成分在含有0.5%吐温20(聚氧乙烯去水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)的丙酮/水(50∶50)溶液中的配制剂。
在开始温室测试之前,用禾谷类除草安全剂解草酯的用量为0.5克每千克无水种子的可湿性粉剂配制剂对冬小麦品种′Hereward′的种子进行种子处理。在施用试验化合物8天之前,在每1.5英寸塑料盆中将一粒种子播种入砂壤土,深度为1cm,在受控条件下于温室(24/16℃,白天/夜晚;14小时光照;65%湿度)中进行浇灌和栽培。出苗后用含水喷雾溶液喷雾植物,该含水喷雾溶液衍生自原药活性成分在含有0.5%吐温20(聚氧乙烯去水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)的丙酮/水(50∶50)溶液中的配制剂。
然后将测试植物在玻璃房中于受控条件下生长(24/16℃,日间/夜间;14小时光照;65%湿度),每天浇水两次。13天之后,对于出苗前和出苗后评价测试(100=植物完全损伤;0=没有植物损伤)。
Claims (24)
1.式I化合物
其中:
R1是氢,甲基,乙基,正丙基,异丙基,卤代甲基,卤代乙基,卤素,乙烯基,乙炔基,甲氧基,乙氧基,卤代甲氧基,卤代乙氧基,环丙基或卤代环丙基,
R2和R3独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C2-C6卤代炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基,氰基,硝基,苯基,被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基;或者杂芳基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的杂芳基;
R4是氢,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基或氰基;
R5,R6,R7,R8和R9独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6卤代烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基,氰基,硝基,苯基,被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基;或者杂芳基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的杂芳基;或者苄基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苄基;或C3-C6环烷基C1-C3烷基,其中环或链亚甲基任选用氧或硫原子替换;或者
R6和R7或者R8和R9与它们连接至的碳原子一起形成任选经取代的任选含有氧、硫或氮原子的3-至8-元环;其中当R6与R7或者R8与R9形成的环是经取代的杂环基时环上存在可选取代基,在此情况下该一个或多个取代基独立地选自卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,硝基和氰基;
或者
R5和R6一起形成键;
Q是C3-C8饱和的或一不饱和的含有至少一个选自O、N和S的杂原子的杂环基,其是未经取代的或被下述基团取代:式=O、=N-R10残基或C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基C1-C2烷基,C3-C6环烷基,苯基,或者被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基;其中R10是C1-C6烷基,C1-C6卤代烷基,C3-C7环烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷基羰基,C1-C6卤代烷基羰基,C1-C6烷氧羰基,C1-C6烷基氨基羰基,C2-C8二烷基氨基羰基,C1-C6卤代烷基亚磺酰基或C1-C6卤代烷基磺酰基;
m是1、2或3;
其中当m是2或3时R6或R7可以具有不同的含义;并且
G是氢或农业上可接受的金属,锍,铵或潜伏基团;
其中,当G是潜伏基团时则G选自下述基团:C1-C8烷基,C2-C8卤代烷基,苯基C1-C8烷基(其中该苯基任选由C1-C3烷基,C1-C3卤代烷基,C1-C3烷氧基,C1-C3卤代烷氧基,C1-C3烷硫基,C1-C3烷基亚磺酰基,C1-C3烷基磺酰基,卤素,氰基或硝基取代),杂芳基C1-C8烷基(其中该杂芳基任选由C1-C3烷基,C1-C3卤代烷基,C1-C3烷氧基,C1-C3卤代烷氧基,C1-C3烷硫基,C1-C3烷基亚磺酰基,C1-C3烷基磺酰基,卤素,氰基或硝基取代),C3-C8烯基,C3-C8卤代烯基,C3-C8炔基,C(Xa)-Ra,C(Xb)-Xc-Rb,C(Xd)-N(Rc)-Rd,-SO2-Re,-P(Xe)(Rf)-Rg和CH2-Xf-Rh;其中:
Xa,Xb,Xc,Xd,Xe和Xf各自独立地是氧或硫;
Ra是H,C1-C18烷基,C2-C18烯基,C2-C18炔基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔基C1-C5氧基烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基;苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基;或者杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基;
Rb是C1-C18烷基,C3-C18烯基,C3-C18炔基,C2-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C2-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C3-C5卤代烯基,C3-C8环烷基;苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基;或者杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基;和
Rc和Rd各自彼此独立是氢,C1-C10烷基,C3-C10烯基,C3-C10炔基,C2-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C2-C5烷基氨基烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基;苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基;杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基;杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基氨基;二杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二杂芳基氨基;苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基氨基;二苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二苯基氨基;或者C3-C7环烷基氨基,二-C3-C7环烷基氨基或C3-C7环烷氧基;或者Rc和Rd可以一起联接形成3-7元环,任选含有一个选自O或S的杂原子;和
Re是C1-C10烷基,C2-C10烯基,C2-C10炔基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基;苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基;杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基;杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基氨基;二杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二杂芳基氨基;苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基氨基;二苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二苯基氨基;或者C3-C7环烷基氨基,二C3-C7环烷基氨基,C3-C7环烷氧基,C1-C10烷氧基,C1-C10卤代烷氧基,C1-C5烷基氨基或C2-C8二烷基氨基;
Rf和Rg各自彼此独立是C1-C10烷基,C2-C10烯基,C2-C10炔基,C1-C10烷氧基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C1-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C2-C5烷基氨基烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C2-C5卤代烯基,C3-C8环烷基;苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基;杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基;杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基氨基;二杂芳基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二杂芳基氨基;苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的苯基氨基;二苯基氨基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的二苯基氨基;或者C3-C7环烷基氨基,二C3-C7环烷基氨基,C3-C7环烷氧基,C1-C10卤代烷氧基,C1-C5烷基氨基或C2-C8二烷基氨基;或者苄氧基或苯氧基,其中该苄基和苯基可以又被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代;并且
Rh是C1-C10烷基,C3-C10烯基,C3-C10炔基,C1-C10卤代烷基,C1-C10氰基烷基,C1-C10硝基烷基,C2-C10氨基烷基,C1-C5烷基氨基C1-C5烷基,C2-C8二烷基氨基C1-C5烷基,C3-C7环烷基C1-C5烷基,C1-C5烷氧基C1-C5烷基,C3-C5烯氧基C1-C5烷基,C3-C5炔氧基C1-C5烷基,C1-C5烷硫基C1-C5烷基,C1-C5烷基亚磺酰基C1-C5烷基,C1-C5烷基磺酰基C1-C5烷基,C2-C8亚烷基氨基氧基C1-C5烷基,C1-C5烷基羰基C1-C5烷基,C1-C5烷氧羰基C1-C5烷基,氨基羰基C1-C5烷基,C1-C5烷基氨基羰基C1-C5烷基,C2-C8二烷基氨基羰基C1-C5烷基,C1-C5烷基羰基氨基C1-C5烷基,N-C1-C5烷基羰基-N-C1-C5烷基氨基C1-C5烷基,C3-C6三烷基甲硅烷基C1-C5烷基,苯基C1-C5烷基(其中该苯基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳基C1-C5烷基(其中该杂芳基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),苯氧基C1-C5烷基(其中该苯基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),杂芳氧基C1-C5烷基(其中该杂芳基任选被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、卤素、氰基或硝基取代),C3-C5卤代烯基,C3-C8环烷基;苯基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素或硝基取代的苯基;或杂芳基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、氰基或硝基取代的杂芳基;
并且其中:
术语“杂芳基"是指含有至少一个杂原子并且由单环或双稠环构成的芳族环系。
2.根据权利要求1的化合物,其中:
卤代烷基是CF3,CF2Cl,CF2H,CCl2H,FCH2,ClCH2,BrCH2,CH3CHF,CF3CH2或CHF2CH2;
术语“杂芳基"是指含有至少一个杂原子并且由单环或双稠环构成的芳族环系;其中单环含有多至三个选自氮、氧和硫的杂原子,而双环系含有多至四个选自氮、氧和硫的杂原子;并且
术语“杂环基”是指含有多至8个原子的非芳族单环或双环环系,包括至少一个选自O、S和N的杂原子。
3.根据权利要求1的化合物,其中R1是甲基,乙基或甲氧基。
4.根据权利要求1的化合物,其中R2和R3独立地是氢,卤素,C1-C6烷基,C1-C6烷氧基,C2-C6烯基,C2-C6炔基,C2-C6卤代炔基,苯基或被C1-C4烷基,C1-C3卤代烷基,氰基,硝基,卤素或C1-C3烷基磺酰基取代的苯基。
5.根据权利要求4的化合物,其中R2和R3独立地是氢,氯,溴,甲基,甲氧基,乙基,乙氧基,乙烯基,乙炔基,苯基或被甲基、三氟甲基、氰基、硝基、氟、氯或甲磺酰基取代的苯基。
6.根据权利要求1的化合物,其中R2和R3独立地是噻吩基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噻吩基;呋喃基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的呋喃基;吡唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的吡唑基;噻唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噻唑基;噁唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噁唑基;异噻唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的异噻唑基;异噁唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的异噁唑基;三唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的三唑基;噁二唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噁二唑基;噻二唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的噻二唑基;四唑基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的四唑基;吡啶基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的吡啶基;嘧啶基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的嘧啶基;哒嗪基;被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的哒嗪基;吡嗪基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的吡嗪基;或者三嗪基或被C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的三嗪基。
7.根据权利要求1的化合物,其中R3是氢。
8.根据权利要求1的化合物,其中R4是氢,甲基,乙基,正丙基,异丙基,卤代甲基,卤代乙基,卤素,乙烯基,乙炔基,甲氧基,乙氧基,卤代甲氧基或卤代乙氧基。
9.根据权利要求8的化合物,其中R4是氢,甲基,乙基,氯,溴,乙烯基,乙炔基,甲氧基或乙氧基。
10.根据权利要求1的化合物,其中R5是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基或C1-C6卤代烷氧基。
11.根据权利要求1的化合物,其中R6和R7独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基或C1-C6卤代烷氧基。
12.根据权利要求1的化合物,其中R8和R9独立地是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基或C1-C6卤代烷氧基。
13.根据权利要求10的化合物,其中:
R5是氢或甲基;
R6和R7独立地是氢或甲基;和
R8和R9独立地是氢或甲基。
14.根据权利要求1至13中任一项的化合物,其中Q选自下式那些:
其中
R是氢,卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯基,C2-C6卤代烯基,C2-C6炔基,C2-C6卤代炔基,C3-C6烯氧基,C3-C6卤代烯氧基,C3-C6炔氧基,C3-C6环烷基,C1-C6烷硫基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷氧基磺酰基,C1-C6卤代烷氧基磺酰基,氰基,硝基,苯基;被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的苯基;或杂芳基或被C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、氰基、硝基、卤素、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代的杂芳基;
R’是氢,C1-C6烷基,C1-C6卤代烷基,C3-C7环烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷基羰基,C1-C6卤代烷基羰基,C1-C6烷氧羰基,C1-C6烷基氨基羰基,C2-C8二烷基氨基羰基,C6-C10芳基磺酰基,C6-C10芳基羰基,C6-C10芳基氨基羰基,C7-C16芳基烷基氨基羰基,C1-C9杂芳基磺酰基,C1-C9杂芳基羰基,C1-C9杂芳基氨基羰基或C2-C15杂芳基烷基氨基羰基;
R”是氢,C1-C6烷基,C1-C6卤代烷基,C3-C7环烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,C1-C6烷基羰基,C1-C6卤代烷基羰基,C1-C6烷氧羰基,C1-C6烷基氨基羰基,C2-C8二烷基氨基羰基,C1-C6卤代烷基亚磺酰基或C1-C6卤代烷基磺酰基;
n是0、1、2、3或4;和
A表示连接至-(CR6R7)m-部分的位置。
15.根据权利要求14的化合物,其中Q选自基团Q1,Q2,Q3,Q4,Q5,Q6,Q7,Q25,Q26,Q27,Q28,Q29,Q86,Q87,Q88,Q89或Q90。
16.根据权利要求15的化合物,其中Q选自基团Q1至Q7。
17.根据权利要求14的化合物,其中R和R’独立地是氢,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基或C1-C4卤代烷氧基;而R”是氢,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基或C1-C6卤代烷基羰基。
18.根据权利要求14的化合物,其中n是0、1或2。
19.根据权利要求1至13中任一项的化合物,其中m是1。
20.根据权利要求1至13中任一项的化合物,其中,当G是潜伏基团时则G是基团-C(Xa)-Ra或-C(Xb)-Xc-Rb,其中Xa、Ra、Xb、Xc和Rb的含义如权利要求1中所定义。
21.根据权利要求1至13中任一项的化合物,其中G是氢、碱金属或碱土金属。
22.除草组合物,其除了包含配制助剂之外还包含除草有效量的如权利要求1至21中任一项所定义的式I化合物。
23.在有用植物作物中防治禾本科草和杂草的方法,其包括将除草有效量的如权利要求1至21中任一项所定义的式I化合物或者包含所述化合物的组合物施用至植物或至其处所。
24.根据权利要求23的方法,其中使用所述组合物,并且其中所述有用植物作物是谷物,稻,玉米,油菜,糖用甜菜,甘蔗,大豆,棉花,向日葵,花生或种植园作物。
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Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
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GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
GB0822834D0 (en) * | 2008-12-15 | 2009-01-21 | Syngenta Ltd | Novel herbicides |
GB0912385D0 (en) | 2009-07-16 | 2009-08-26 | Syngenta Ltd | Novel herbicides |
CA2768596C (en) | 2009-07-31 | 2018-06-05 | Syngenta Limited | Herbicidally active heteroaryl-substituted cyclic diones or derivatives thereof |
WO2011073060A2 (en) * | 2009-12-18 | 2011-06-23 | Syngenta Participations Ag | Method of combating and controlling pests |
DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
CA2816415A1 (en) | 2010-11-02 | 2012-05-10 | Bayer Intellectual Property Gmbh | Phenyl-substituted bicyclooctane-1,3-dione-derivatives |
WO2012092827A1 (en) * | 2011-01-05 | 2012-07-12 | Syngenta Participations Ag | Chemical compounds |
ES2599807T3 (es) * | 2011-11-30 | 2017-02-03 | Syngenta Limited | Compuestos de 2-(fenilo sustituido)-ciclopentano-1,3-dionas, y derivados de los mismos |
CN103896827B (zh) * | 2012-12-24 | 2016-09-07 | 中化蓝天集团有限公司 | 三氟甲基取代的二氢吡啶酮类衍生物、其制备方法及应用 |
EA028524B1 (ru) * | 2013-04-19 | 2017-11-30 | Зингента Лимитед | Гербицидно активные соединения 2-(замещенный фенил)циклопентан-1,3-диона и их производные |
US10696686B2 (en) * | 2013-05-30 | 2020-06-30 | Syngenta Limited | Herbicidally active (alkynyl-phenyl)-substituted cyclic dione compounds and derivatives thereof |
GB201310047D0 (en) | 2013-06-05 | 2013-07-17 | Syngenta Ltd | Compounds |
GB201418567D0 (en) * | 2014-10-20 | 2014-12-03 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
GB201418764D0 (en) * | 2014-10-22 | 2014-12-03 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
PL3235799T3 (pl) | 2014-12-18 | 2022-05-02 | Nissan Chemical Corporation | Związek oksymowy i herbicyd |
WO2017217553A1 (ja) * | 2016-06-17 | 2017-12-21 | 日産化学工業株式会社 | オキシム化合物及び除草剤 |
GB201621626D0 (en) * | 2016-12-19 | 2017-02-01 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
WO2018131690A1 (ja) * | 2017-01-13 | 2018-07-19 | 日産化学工業株式会社 | ケトン若しくはオキシム化合物及び除草剤 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4551547A (en) * | 1980-11-10 | 1985-11-05 | Union Carbide Corporation | Biocidal 2-aryl-1, 3-cyclopentanedione enol ester compounds |
Family Cites Families (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4256659A (en) | 1977-03-28 | 1981-03-17 | Union Carbide Corporation | Method of preparing 2-aryl-1,3-cyclohexanedione compounds |
US4659372A (en) | 1977-03-28 | 1987-04-21 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds |
US4209532A (en) | 1977-03-28 | 1980-06-24 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclohexane dione compounds and alkali metal and ammonium salts thereof |
PT67818A (en) | 1977-03-28 | 1978-04-01 | Union Carbide Corp | Process for the synthesis of biocidal 2-aryl-1,3-cycloalkanedionas and their enol esters |
US4175135A (en) | 1978-07-18 | 1979-11-20 | Union Carbide Corporation | Method of controlling acarina ectoparasites on warmblooded animals by orally administering to the animal an ectoparasitically effective amount of a 2-aryl-1,3-cyclohexanedione compound, and alkali metal salts, ammonium salts and enol esters thereof |
US4283348A (en) | 1978-09-22 | 1981-08-11 | Union Carbide Corporation | Method of preparing 2-aryl-3-cyclopentanedione compounds |
US4526723A (en) | 1978-09-27 | 1985-07-02 | Union Carbide Corporation | Biocidal enol esters of non-ortho substituted 2-aryl-1-3-cycloalkanedione compounds |
US4338122A (en) | 1979-09-26 | 1982-07-06 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclopentanedione compounds and alkali metal and ammonium salts thereof |
US4409153A (en) | 1980-03-28 | 1983-10-11 | Union Carbide Corporation | O-(2-Aryl-3-oxo-1-cyclohexenyl) phosphates |
US4489012A (en) | 1982-02-23 | 1984-12-18 | Union Carbide Corporation | Enol-phosphorous esters of 2-aryl-1,3-cycloalkanediones compounds |
DE3239368A1 (de) * | 1982-10-23 | 1984-04-26 | Karl Engelhard Fabrik pharmazeutischer Präparate, 6000 Frankfurt | Verbindungen mit einem hydroxy-, oxo- und arylgruppen enthaltenden cyclopentenring, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische praeparate |
SE461700B (sv) * | 1988-08-15 | 1990-03-19 | Ovidiu Tanasescu | Anordning foer vaatrengoering av golv |
AU2925195A (en) | 1994-07-07 | 1996-02-09 | Bayer Aktiengesellschaft | 2-aryl cyclopentane-1,3-dione derivatives |
WO1996003366A1 (de) | 1994-07-21 | 1996-02-08 | Bayer Aktiengesellschaft | 2-(2,4,6-trimethylphenyl)-cyclopentan-1,3-dion-derivate |
GB9418762D0 (en) * | 1994-09-16 | 1994-11-02 | Bayer Ag | Use of substituted cyclopentane-DI-and-triones |
WO1996025395A1 (de) * | 1995-02-13 | 1996-08-22 | Bayer Aktiengesellschaft | 2-phenylsubstituierte heterocyclische 1,3-ketoenole als herbizide und pestizide |
US6316486B1 (en) | 1995-05-09 | 2001-11-13 | Bayer Aktiengesellschaft | Alkyl dihalogenated phenyl-substituted ketoenols useful as pesticides and herbicides |
DE19538218A1 (de) | 1995-10-13 | 1997-04-17 | Bayer Ag | Cyclopentan-1,3-dion-Derivate |
US6515184B1 (en) | 1995-10-13 | 2003-02-04 | Bayer Aktiengesellschaft | Cyclopentane-1,3-dione derivatives, herbicidal and pesticidal compositions containing them, methods of using them to combat pests and weeds and process for the preparation thereof |
DE19708607A1 (de) | 1997-03-03 | 1998-09-10 | Bayer Ag | 2-Arylcyclopentan-1,3-dione |
DE19808261A1 (de) * | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
CN1185234C (zh) * | 1998-03-13 | 2005-01-19 | 辛根塔参与股份公司 | 具有除草活性的3-羟基-4-芳基-5-氧代吡唑啉衍生物 |
DE19813354A1 (de) | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE69925610T2 (de) | 1998-09-15 | 2006-04-27 | Syngenta Participations Ag | Als herbicide verwendbare pyridin-ketone |
DE19854147A1 (de) | 1998-11-24 | 2000-05-25 | Basf Ag | Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht |
WO2000047585A1 (en) | 1999-02-11 | 2000-08-17 | Novartis Ag | 3-hydroxy-4-aryl-5-pyrazoline derivatives as herbicides |
CA2372836C (en) * | 1999-05-05 | 2009-01-20 | Aventis Pharma Limited | Substituted pyrrolidines as cell adhesion inhibitors |
WO2000068196A1 (fr) | 1999-05-11 | 2000-11-16 | Sankyo Company,Limited | Dérivés de dihydropyrrole à substitution n |
DE19935963A1 (de) | 1999-07-30 | 2001-02-01 | Bayer Ag | Biphenylsubstituierte cyclische Ketoenole |
WO2001017973A2 (de) | 1999-09-07 | 2001-03-15 | Syngenta Participations Ag | Neue herbizide |
ES2233451T3 (es) | 1999-09-07 | 2005-06-16 | Syngenta Participations Ag | Nuevos herbicidas. |
DE10016544A1 (de) * | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
DE10029077A1 (de) * | 2000-06-13 | 2001-12-20 | Bayer Ag | Thiazolylsubstituierte Heterocyclen |
DE10139465A1 (de) | 2001-08-10 | 2003-02-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern |
DE10249055A1 (de) | 2002-10-22 | 2004-05-06 | Bayer Cropscience Ag | 2-Phenyl-2-substituierte-1,3-diketone |
GT200300290A (es) | 2002-12-30 | 2004-10-13 | Herbicidas novedosos | |
DE10311300A1 (de) | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
DE10354629A1 (de) | 2003-11-22 | 2005-06-30 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
DE102004014620A1 (de) * | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
DE102004035133A1 (de) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern |
DE102004041529A1 (de) | 2004-08-27 | 2006-03-02 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Ketoenolen |
DE102004044827A1 (de) * | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
GB0427901D0 (en) | 2004-12-21 | 2005-01-19 | Univ Cranfield | Virtual imprinting |
DE102005059471A1 (de) | 2005-12-13 | 2007-07-12 | Bayer Cropscience Ag | Herbizide Zusammensetzungen mit verbesserter Wirkung |
DE102006000971A1 (de) | 2006-01-07 | 2007-07-12 | Bayer Cropscience Ag | 2,4,6-Trialkylphenylsubstituierte Cyclopentan-1,3-dione |
DE102006007882A1 (de) * | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
DE102006018828A1 (de) | 2006-04-22 | 2007-10-25 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
DE102006025874A1 (de) | 2006-06-02 | 2007-12-06 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
AR064300A1 (es) | 2006-12-14 | 2009-03-25 | Syngenta Participations Ag | Pirandionas,tiopirandionas y ciclohexanotrionas como herbicidas |
GB0704653D0 (en) | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
GB0704652D0 (en) | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
GB0710223D0 (en) | 2007-05-29 | 2007-07-11 | Syngenta Ltd | Novel Herbicides |
GB0819205D0 (en) * | 2008-10-20 | 2008-11-26 | Syngenta Ltd | Novel herbicides |
GB0822834D0 (en) * | 2008-12-15 | 2009-01-21 | Syngenta Ltd | Novel herbicides |
GB0912385D0 (en) * | 2009-07-16 | 2009-08-26 | Syngenta Ltd | Novel herbicides |
CA2768596C (en) * | 2009-07-31 | 2018-06-05 | Syngenta Limited | Herbicidally active heteroaryl-substituted cyclic diones or derivatives thereof |
WO2011073060A2 (en) * | 2009-12-18 | 2011-06-23 | Syngenta Participations Ag | Method of combating and controlling pests |
WO2012092827A1 (en) * | 2011-01-05 | 2012-07-12 | Syngenta Participations Ag | Chemical compounds |
-
2008
- 2008-07-03 GB GB0812310A patent/GB0812310D0/en not_active Ceased
-
2009
- 2009-07-01 PL PL09772473T patent/PL2313370T3/pl unknown
- 2009-07-01 EP EP09772473.6A patent/EP2313370B1/en active Active
- 2009-07-01 AU AU2009265680A patent/AU2009265680B2/en active Active
- 2009-07-01 NZ NZ590055A patent/NZ590055A/en not_active IP Right Cessation
- 2009-07-01 UA UAA201101185A patent/UA103625C2/ru unknown
- 2009-07-01 BR BRPI0914107-3A patent/BRPI0914107B1/pt active IP Right Grant
- 2009-07-01 KR KR20117002737A patent/KR20110031221A/ko not_active Application Discontinuation
- 2009-07-01 HU HUE09772473A patent/HUE028084T2/en unknown
- 2009-07-01 EA EA201170132A patent/EA021735B1/ru not_active IP Right Cessation
- 2009-07-01 MX MX2010014311A patent/MX2010014311A/es not_active Application Discontinuation
- 2009-07-01 DK DK09772473.6T patent/DK2313370T3/en active
- 2009-07-01 CN CN2009801294512A patent/CN102112439B/zh active Active
- 2009-07-01 CA CA2729724A patent/CA2729724C/en active Active
- 2009-07-01 ES ES09772473.6T patent/ES2553418T3/es active Active
- 2009-07-01 US US13/002,343 patent/US9096560B2/en active Active
- 2009-07-01 JP JP2011515449A patent/JP5524959B2/ja not_active Expired - Fee Related
- 2009-07-01 AR ARP090102459 patent/AR072459A1/es active IP Right Grant
- 2009-07-01 WO PCT/EP2009/058250 patent/WO2010000773A1/en active Application Filing
- 2009-07-02 CL CL2009001513A patent/CL2009001513A1/es unknown
- 2009-07-02 TW TW98122383A patent/TW201014819A/zh unknown
-
2010
- 2010-12-22 ZA ZA2010/09220A patent/ZA201009220B/en unknown
- 2010-12-23 IL IL210202A patent/IL210202A0/en unknown
-
2011
- 2011-01-18 CO CO11004798A patent/CO6341609A2/es not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4551547A (en) * | 1980-11-10 | 1985-11-05 | Union Carbide Corporation | Biocidal 2-aryl-1, 3-cyclopentanedione enol ester compounds |
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BRPI0914107B1 (pt) | 2022-01-11 |
WO2010000773A1 (en) | 2010-01-07 |
PL2313370T3 (pl) | 2016-01-29 |
JP5524959B2 (ja) | 2014-06-18 |
CN102112439A (zh) | 2011-06-29 |
NZ590055A (en) | 2012-06-29 |
BRPI0914107A2 (pt) | 2021-04-27 |
AU2009265680B2 (en) | 2014-05-22 |
AR072459A1 (es) | 2010-09-01 |
TW201014819A (en) | 2010-04-16 |
UA103625C2 (en) | 2013-11-11 |
EA201170132A1 (ru) | 2011-08-30 |
EP2313370B1 (en) | 2015-08-19 |
ZA201009220B (en) | 2011-09-28 |
GB0812310D0 (en) | 2008-08-13 |
AU2009265680A1 (en) | 2010-01-07 |
HUE028084T2 (en) | 2016-11-28 |
MX2010014311A (es) | 2011-02-15 |
DK2313370T3 (en) | 2015-11-30 |
CL2009001513A1 (es) | 2009-10-23 |
CA2729724C (en) | 2016-04-19 |
EA021735B1 (ru) | 2015-08-31 |
US20110263428A1 (en) | 2011-10-27 |
IL210202A0 (en) | 2011-03-31 |
CA2729724A1 (en) | 2010-01-07 |
KR20110031221A (ko) | 2011-03-24 |
CO6341609A2 (es) | 2011-11-21 |
US9096560B2 (en) | 2015-08-04 |
EP2313370A1 (en) | 2011-04-27 |
JP2011526597A (ja) | 2011-10-13 |
ES2553418T3 (es) | 2015-12-09 |
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