CN106458926B - 哒嗪酮除草剂 - Google Patents
哒嗪酮除草剂 Download PDFInfo
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- CN106458926B CN106458926B CN201580034886.4A CN201580034886A CN106458926B CN 106458926 B CN106458926 B CN 106458926B CN 201580034886 A CN201580034886 A CN 201580034886A CN 106458926 B CN106458926 B CN 106458926B
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- radical
- alkyl
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- haloalkyl
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- 239000004009 herbicide Substances 0.000 title claims description 48
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 447
- 239000000203 mixture Substances 0.000 claims abstract description 146
- 238000000034 method Methods 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- -1 C1–C7Alkoxy Chemical group 0.000 claims description 206
- 229910052736 halogen Inorganic materials 0.000 claims description 92
- 150000002367 halogens Chemical class 0.000 claims description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 54
- 239000003112 inhibitor Substances 0.000 claims description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 51
- 230000002363 herbicidal effect Effects 0.000 claims description 51
- 239000007787 solid Substances 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000004480 active ingredient Substances 0.000 claims description 34
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 33
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 33
- 239000003085 diluting agent Substances 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 25
- 230000015572 biosynthetic process Effects 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 20
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 18
- 239000011734 sodium Substances 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 230000012010 growth Effects 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 12
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
- 239000005604 Prosulfuron Substances 0.000 claims description 10
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 125000006826 (C2-C7) alkylcarbonyloxy group Chemical group 0.000 claims description 9
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 8
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 8
- 229930192334 Auxin Natural products 0.000 claims description 8
- 108010018763 Biotin carboxylase Proteins 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 239000002363 auxin Substances 0.000 claims description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 7
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 7
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 7
- 239000005472 Bensulfuron methyl Substances 0.000 claims description 7
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 7
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims description 7
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims description 7
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 7
- 108010001545 phytoene dehydrogenase Proteins 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 claims description 7
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005583 Metribuzin Substances 0.000 claims description 6
- 239000005586 Nicosulfuron Substances 0.000 claims description 6
- 239000005616 Rimsulfuron Substances 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 6
- GBHVIWKSEHWFDD-UHFFFAOYSA-N n-[2-(4,6-dimethoxy-1,3,5-triazine-2-carbonyl)-6-fluorophenyl]-1,1-difluoro-n-methylmethanesulfonamide Chemical compound COC1=NC(OC)=NC(C(=O)C=2C(=C(F)C=CC=2)N(C)S(=O)(=O)C(F)F)=N1 GBHVIWKSEHWFDD-UHFFFAOYSA-N 0.000 claims description 6
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 6
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 claims description 5
- 239000005496 Chlorsulfuron Substances 0.000 claims description 5
- 239000005514 Flazasulfuron Substances 0.000 claims description 5
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 claims description 5
- 239000005561 Glufosinate Substances 0.000 claims description 5
- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 5
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 5
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 claims description 4
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 claims description 4
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 claims description 4
- 239000005469 Azimsulfuron Substances 0.000 claims description 4
- VYSWYQJLFWCXEX-UHFFFAOYSA-N CC=1OC2=C(C1C=1C(N(N=C(C1O)C)C)=O)C=C(C=C2)C Chemical compound CC=1OC2=C(C1C=1C(N(N=C(C1O)C)C)=O)C=C(C=C2)C VYSWYQJLFWCXEX-UHFFFAOYSA-N 0.000 claims description 4
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims description 4
- 239000005644 Dazomet Substances 0.000 claims description 4
- 239000005529 Florasulam Substances 0.000 claims description 4
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims description 4
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- 239000005643 Pelargonic acid Substances 0.000 claims description 4
- 239000005592 Penoxsulam Substances 0.000 claims description 4
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 claims description 4
- 108010081996 Photosystem I Protein Complex Proteins 0.000 claims description 4
- 239000005619 Sulfosulfuron Substances 0.000 claims description 4
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 4
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims description 4
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 claims description 4
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 4
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 4
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 4
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- PYCINWWWERDNKE-UHFFFAOYSA-N 1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound N12N=C(CCC)C=CC2=NC(Cl)=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 PYCINWWWERDNKE-UHFFFAOYSA-N 0.000 claims description 3
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003666 Amidosulfuron Substances 0.000 claims description 3
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims description 3
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 claims description 3
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005566 Imazamox Substances 0.000 claims description 3
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 claims description 3
- QSTABXLLHBDGJH-UHFFFAOYSA-N OC1=C(C(N(N=C1C)C)=O)C1=C(OC2=C1C=C(C=C2C)C)C Chemical compound OC1=C(C(N(N=C1C)C)=O)C1=C(OC2=C1C=C(C=C2C)C)C QSTABXLLHBDGJH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005589 Oxasulfuron Substances 0.000 claims description 3
- 239000005607 Pyroxsulam Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 3
- YIANBKOBVRMNPR-UHFFFAOYSA-N cloransulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(O)=O YIANBKOBVRMNPR-UHFFFAOYSA-N 0.000 claims description 3
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical group CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000394 mitotic effect Effects 0.000 claims description 3
- GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 claims description 3
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 claims description 3
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 claims description 3
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 claims description 3
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- HVZIXFLYTGETNE-UHFFFAOYSA-N 5-hydroxy-2,6-dimethyl-4-(2,4,6-trimethyl-1-benzothiophen-3-yl)pyridazin-3-one Chemical compound OC1=C(C(N(N=C1C)C)=O)C=1C2=C(SC1C)C=C(C=C2C)C HVZIXFLYTGETNE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
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Classifications
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Abstract
Description
技术领域
本发明涉及某些哒嗪酮、它们的N-氧化物、盐和组合物,以及它们用于防治不期望的植被的方法。
背景技术
防治不期望的植被对于实现高作物效益是极其重要的。实现选择性防治杂草的生长是非常令人期望的,特别是在可用的作物中,如稻、大豆、糖用甜菜、玉米、马铃薯、小麦、大麦、西红柿和种植性作物等。在此类可用作物中未加抑制的杂草生长可引起产量的显著减少,由此导致消费者成本上升。在非耕作区防治不期望的植被也是重要的。为此目的,许多产品可商购获得,但是持续需要更有效、更经济、毒性更小、对环境更安全或具有不同作用位点的新型化合物。
发明内容
本发明涉及式1的化合物(包括所有立体异构体)、其N-氧化物及其盐、包含它们的农业组合物、以及它们作为除草剂的用途:
其中
W为O或S;
R1为H、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、 C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基、苄基或苯基;或者5-元或6-元饱和或部分饱和的杂环环,其包含选自碳以及至多1个O和1个S的环成员;
R2为H、卤素、-CN、-CHO、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C2–C8二烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C1–C7烷氧基、C1–C5烷硫基、C2–C3烷氧基羰基;或任选地被卤素、C1–C4烷基或C1–C4卤代烷基取代的苯基;
X为O、S或NR5;或者
X为-C(R6)=C(R7)-,其中与R6键合的碳原子还键合至与R4键合的碳原子,并且与R7键合的碳原子还键合至式1的苯环部分;
每个R3独立地为卤素、-CN、硝基、C1–C5烷基、C2–C5烯基、C2–C5炔基、C3–C5环烷基、C4–C5环烷基烷基、C1–C5卤代烷基、C3–C5卤代烯基、C3–C5卤代炔基、C2–C5烷氧基烷基、C1–C5烷氧基、C1–C5卤代烷氧基、C1–C5烷硫基、C1–C5卤代烷硫基或C2–C5烷氧基羰基;
R4、R6和R7独立地为H、卤素、硝基、-CN、C1–C5烷基、C2–C5烯基、 C2–C5炔基、C3–C5环烷基、C4–C5环烷基烷基、C1–C5卤代烷基、 C3–C5卤代烯基、C3–C5卤代炔基、C2–C5烷氧基烷基、C1–C5烷氧基、C1–C5卤代烷氧基、C1–C5烷硫基、C1–C4烷基亚磺酰基、C1–C4烷基磺酰基、C1–C5卤代烷硫基或C2–C5烷氧基羰基;
R5为H、C1–C3烷基或C1–C3卤代烷基;
G为G1或W1G1;
G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、 -CONR10R11、-S(O)2NR10R11或P(=O)R12;或C1–C4烷基、C2–C4烯基、C2–C4炔基、C1–C4卤代烷基、C2–C4卤代烯基、C2–C4卤代炔基、C1–C4烷氧基烷基、C3–C6环烷基或C4–C7环烷基烷基;或者5- 元或6-元杂环环;
W1为C1–C4烷二基或C2–C4烯二基;
R8和R10独立地为C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、 C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C4–C7环烷基烷基;或苯基、苄基或5-元至6-元杂环环,每个苯基、苄基或杂环环任选地被卤素、C1–C4烷基或C1–C4卤代烷基取代;
R9为C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C2–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C4–C7环烷基烷基;或苯基、苄基或5-元至6-元杂环环,每个苯基、苄基或杂环环任选地被卤素、C1–C4烷基或C1–C4卤代烷基取代;
R11为H、C1-C7烷基、C2–C7烯基、C2–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C1–C7卤代烷基或C2–C7烷氧基烷基;
R12为C1-C7烷基或C1-C7烷氧基;并且
n为0、1、2、3或4;
前提条件是当R4为H时,则X为-C(R6)=C(R7)-。
更具体地,本发明涉及式1的化合物(包括所有立体异构体)、其N- 氧化物或其盐。本发明还涉及除草剂组合物,所述除草剂组合物包含本发明的化合物(即除草有效量的)和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的组分。本发明还涉及用于防治不期望的植被生长的方法,所述方法包括使所述植被或其环境与除草有效量的本发明化合物(例如为本文所述组合物形式)接触。
如下所述,本发明也包括除草剂混合物,该除草剂混合物包含(a)选自式1的化合物、N-氧化物及其盐,和(b)至少一种附加活性成分,所述附加活性成分选自(b1)至(b16);以及(b1)至(b16)的化合物的盐。
具体实施方式
如本文所用,术语“包括”、“包含”、“内含”、“涵盖”、“具有”、“含有”、“包容”、“容纳”、“特征在于”或其任何其它变型旨在涵盖非排它性的包括,以任何明确指明的限定为条件。例如,包含一系列元素的组合物、混合物、工艺或方法不一定仅限于这些元素,而是可包括未明确列出的其他元素,或此类组合物、混合物、工艺或方法的其他固有元素。
连接短语“由…组成”不包括任何未指定的元素、步骤或成分。如果是在权利要求中,则此类词限制权利要求,以不包含除了通常与之伴随的杂质以外不是所述那些的物质。当短语“由…组成”出现在权利要求的主体的子句中,而非紧接前序时,其仅限制在该子句中提到的要素;其他元素总体上不会从权利要求中被排除。
连接短语“基本上由…组成”用于限定组合物或方法,所述组合物或方法除了字面公开的那些以外,还包括物质、步骤、部件、组分或元素,前提条件是,这些附加的物质、步骤、部件、组分或元素没有在很大程度上影响受权利要求书保护的本发明的基本特征和新型特征。术语“基本上由…组成”居于“包含”和“由…组成”中间。
当申请人使用开放式术语(诸如“包含”)来限定发明或其部分时,应当容易地理解到(除非另有指明)该说明应被解释为也使用了术语“基本上由…组成”或“由…组成”描述这一发明。
此外,除非明确指明相反,“或”是指包含性的“或”而非排他性的“或”。例如,条件A或B满足下列任一项:A为真实的(或存在的)且B为虚假的(或不存在的),A为虚假的(或不存在的)且B为真实的(或存在的),以及A和B均为真实的(或存在的)。
此外,涉及元素或组分示例(即出现)的数目在本发明元素或组分前的不定冠词“一个”或“一种”旨在为非限制性的。因此,应将“一个”或“一种”理解为包括一个或至少一个,并且元素或组分的词语单数形式也包括复数指代,除非有数字明显表示单数。
如本文所提及的,单独或以词语的组合使用的术语“幼苗”是指由种子的胚芽发育的植物幼苗。
如本文所指,术语“阔叶”可单独使用或以词语诸如“阔叶杂草”形式使用,是指双子叶或双子叶植物,双子叶植物是用于描述一类被子植物的术语,其以具有两个子叶的胚芽为特征。
如本文所用,术语“烷基化”是指其中亲核物质从含碳基团中置换离去基团诸如卤素或磺酸根的反应。除非另外指明,术语“烷基化”不限于烷基含碳基团。
在上述表述中,单独使用或在复合词诸如“烷硫基”或“卤代烷基”中使用的术语“烷基”包括直-链或支链的烷基,诸如甲基、乙基、正-丙基、异-丙基、或不同的丁基、戊基或己基异构体。“烯基”包括直-链或支链的烯烃,诸如乙烯基、1-丙烯基、2-丙烯基、以及不同的丁烯基、戊烯基和己烯基异构体。“烯基”还包括聚烯,诸如1,2-丙二烯基和2,4-己二烯基。“炔基”包括直-链或支链的炔烃,诸如乙炔基、1-丙炔基、2-丙炔基、以及不同的丁炔基、戊炔基和己炔基异构体。“炔基”还可包括由多个三键构成的部分,诸如2,5-己二炔基。
“烷氧基”包括例如甲氧基、乙氧基、正-丙氧基、异丙氧基、以及不同的丁氧基、戊氧基和己氧基异构体。“烷氧基烷基”表示烷基上的烷氧基取代。“烷氧基烷基”的示例包括CH3OCH2、CH3OCH2CH2、CH3CH2OCH2、 CH3CH2CH2CH2OCH2和CH3CH2OCH2CH2。“烷氧基烷氧基”表示烷氧基上的烷氧基取代。“烷硫基”包括支链或直-链的烷硫基部分,诸如甲硫基、乙硫基、以及不同的丙硫基、丁硫基、戊硫基和己硫基异构体。“烷硫基烷基”表示在烷基上的烷硫基取代。“烷硫基烷基”的示例包括CH3SCH2、 CH3SCH2CH2、CH3CH2SCH2、CH3CH2CH2CH2SCH2和CH3CH2SCH2CH2。“氰基烷基”表示被一个氰基基团取代的烷基基团。“氰基烷基”的示例包括NCCH2和NCCH2CH2(或者称之为CH2CH2CN)。
“环烷基”包括例如环丙基、环丁基、环戊基和环己基。术语“环烷基烷基”表示在烷基部分上的环烷基取代。“环烷基烷基”的示例包括环丙基甲基、环戊基乙基、以及其它键合到直-链或支链的烷基基团的环烷基部分。
单独的或在复合词诸如“卤代烷基”中的或者当用于描述诸如“被卤素取代的烷基”中时的术语“卤素”包括氟、氯、溴或碘。此外,当用于复合词诸如“卤代烷基”中时,或当用于描述诸如“被卤素取代的烷基”中时,所述烷基可以是被卤原子(其可以是相同的或不同的)部分地或完全地取代的。“卤代烷基”或“被卤素取代的烷基”的示例包括F3C、ClCH2、CF3CH2和CF3CCl2。术语“卤代烷氧基”、“卤代烷硫基”、“卤代烯基”、“卤代炔基”等等与术语“卤代烷基”类似地定义。“卤代烷氧基”的示例包括 CF3O-、CCl3CH2O-、HCF2CH2CH2O-和CF3CH2O-。“卤代烷硫基”的示例包括CCl3S-、CF3S-、CCl3CH2S-和ClCH2CH2CH2S-。“卤代烯基”的示例包括(Cl)2C=CHCH2-和CF3CH2CH=CHCH2-。“卤代炔基”的示例包括 HC≡CCHCl-、CF3C≡C-、CCl3C≡C-和FCH2C≡CCH2-。
“烷氧基羰基”表示键合到C(=O)部分上的直-链或支链的烷氧基部分。“烷氧基羰基”的示例包括CH3OC(=O)-、CH3CH2OC(=O)-、 CH3CH2CH2OC(=O)-、(CH3)2CHOC(=O)-和不同的丁氧基-或戊氧基羰基异构体。
取代基基团中的碳原子的总数由“Ci–Cj”前缀表示,其中i和j为1至 7的数。例如,C1-C4烷磺酰基命名为甲磺酰基至丁磺酰基;C2烷氧基烷基命名为CH3OCH2-;C3烷氧基烷基命名为例如CH3CH(OCH3)-、CH3OCH2CH2- 或CH3CH2OCH2-;并且C4烷氧基烷基命名为包含总计四个碳原子的被烷氧基基团取代的烷基基团的各种异构体,示例包括CH3CH2CH2OCH2-和CH3CH2OCH2CH2-。
当化合物被取代基取代,所述取代基具有指出所述取代基数可超过1个的下标时,所述取代基(当它们超过1时)独立地选自所定义的取代基如 (R3)n,其中n为1、2、3或4。当基团包含可为氢的取代基例如R2或R4时,当该取代基被认为是氢时,认识到这等同于所述基团是未取代的。当可变基团示出任选地连接到一个位置时,例如(R3)n,其中n可为0,即使未在可变基团定义中进行叙述,氢也可在所述位置处。当基团上的一个或多个位置被称为“没有取代的”或“未取代的”时,连接氢原子以占据任何自由价。
据信式1的化合物(其中G为H,即羟基官能)为结合至植物的酶或受体上的活性位点而对植物产生除草效应的化合物。其它式1的化合物(其中取代基G为可在植物或环境内转化为羟基部分的基团)提供类似的除草效应并且在本发明的范围之内。因此,G可为本领域已知的任何衍生物,其不消除式1的化合物的除草活性,并且在植物或土壤中被或者可被水解、氧化、还原或者以其它方式代谢,以提供呈离解或未离解形式(这取决于pH)的羧酸官能团。术语“环系”表示两个或更多个稠环。术语“二环环系”表示由两个稠环组成的环系。
本发明的化合物可作为一种或多种立体异构体存在。多种立体异构体包括对映体、非对映体、阻转异构体和几何异构体。立体异构体为组成相同但它们原子空间排列不同的异构体,并且包括对映体、非对映体、顺-反异构体(还称为几何异构体)和阻转异构体。阻转异构体由围绕单键旋转受限产生,其中旋转障碍足够高致使异构体分离。本领域的技术人员将会知道,当一种立体异构体相对于其它立体异构体富集时,或当其与其它立体异构体分离时,其可能更有活性和/或可能表现出有益的效果。另外,本领域的技术人员知道如何分离、富集和/或选择性地制备所述立体异构体。本发明的化合物可作为立体异构体的混合物、单独的立体异构体或作为光学活性的形式存在。
式1的化合物通常以多于一种的形式存在,因此式1包括它们代表的所有化合物晶体和非晶体形式。非结晶形式包括为固体的实施方案诸如蜡和树胶,以及为液体的实施方案诸如溶液和熔融物。晶体形式包括代表基本上单一晶型体的实施方案,和代表多晶型体(即不同晶型)的混合物的实施方案。术语“多晶型”是指可以不同晶型结晶的化合物的具体晶型,这些晶型在晶格中具有不同的分子排列和/或分子构象。由于晶格中存在或不存在可为微弱或强力结合的共结晶水或其它分子,因此虽然多晶型体可具有相同的化学组成,但是它们也可具有不同的组成。多晶型体可具有不同的化学、物理和生物特性,如结晶形状、密度、硬度、颜色、化学稳定性、熔点、吸湿性、可悬浮性、溶解速率和生物利用度。本领域的技术人员将会知道,相对于相同的式1的化合物的另一种多晶型体或多晶型体混合物,式1的化合物的多晶型体可显示出有益效应(例如制备可用制剂的适宜性,改善的生物性能)。式1的化合物的具体多晶型体的制备和分离可通过本领域技术人员已知的方法实现,例如采用所选溶剂和温度进行结晶。关于多态性广泛的论述参见 R.Hilfiker编辑的Polymorphism in the Pharmaceutical Industry,Wiley-VCH, Weinheim,2006。
本领域的技术人员将会理解,不是所有的含氮杂环都可以形成N-氧化物,因为氮需要有可氧化为氧化物的可用孤对电子;本领域的技术人员将识别出可形成N-氧化物的那些含氮杂环。本领域的技术人员还将会知道,叔胺可形成N-氧化物。用于制备杂环和叔胺的N-氧化物的合成方法是本领域的技术人员熟知的,包括用过氧酸(诸如过乙酸和间-氯过氧苯甲酸 (MCPBA))、过氧化氢、烷基氢过氧化物(诸如叔-丁基氢过氧化物)、过硼酸钠和双环氧乙烷(诸如二甲基双环氧乙烷)氧化杂环化合物和叔胺。用于制备N-氧化物的这些方法已广泛描述和综述于文献中,参见例如:T.L. Gilchrist于Comprehensive OrganicSynthesis,第7卷,第748–750页,S.V.Ley 编辑,Pergamon Press;M.Tisler和B.Stanovnik于Comprehensive Heterocyclic Chemistry,第3卷,第18–20页,A.J.Boulton和A.McKillop编辑,Pergamon Press;M.R.Grimmett和B.R.T.Keene于Advances inHeterocyclic Chemistry,第43卷,第149–161页,A.R.Katritzky编辑,Academic Press;M.Tisler 和B.Stanovnik于Advances in Heterocyclic Chemistry,第9卷,第285–291页,A.R.Katritzky和A.J.Boulton编辑,Academic Press;以及G.W.H. Cheeseman和E.S.G.Werstiuk于Advances in Heterocyclic Chemistry,第22 卷,第390–392页,A.R.Katritzky和A.J.Boulton编辑,Academic Press。
本领域的技术人员认识到,由于在环境和生理条件下化合物的盐与它们相应的非盐形式处于平衡,因此盐与非盐形式共享生物用途。因此,可使用多种式1的化合物的盐来防治不期望的植被(即是农业上适合的)。式1的化合物的盐包括与无机酸或有机酸形成的酸-加成盐,所述酸如氢溴酸、盐酸、硝酸、磷酸、硫酸、乙酸、丁酸、富马酸、乳酸、马来酸、丙二酸、草酸、丙酸、水杨酸、酒石酸、4-甲苯磺酸或戊酸。当式1的化合物包含酸性部分诸如烯醇官能(例如,当G为H时)时,盐还包括与有机碱或无机碱诸如吡啶、三乙基胺或氨、或酰胺、或者钠、钾、锂、钙、镁或钡的氢化物、氢氧化物或碳酸盐形成的那些。因此,本发明包括选自式1、其N-氧化物和其适用于农业的盐的化合物。
如发明内容中所述的本发明的实施方案包括(其中如以下实施方案中所用的式1包括其N-氧化物和其盐):
实施方案1.式1的化合物,其中W为O。
实施方案2.根据式1或实施方案1所述的化合物,其中X为O、S 或-C(R6)=C(R7)-。
实施方案3.根据实施方案2所述的化合物,其中X为O或S。
实施方案4.根据实施方案3所述的化合物,其中X为O。
实施方案5.根据实施方案3所述的化合物,其中X为S。
实施方案6.根据实施方案2所述的化合物,其中X为-C(R6)=C(R7)-。
实施方案7.根据式1或实施方案1所述的化合物,其中X为NR5。
实施方案7a.根据实施方案2所述的化合物,其中X为O、S、-CH=CH-、 -C(CH3)=CH-、-CH=CF-、-CH=CCl-或-CH=C(CH3)-。
实施方案7b:根据实施方案2所述的化合物,其中X为-CH=CH-、 -C(CH3)=CH-、-CH=CF-、-CH=CCl-或-CH=C(CH3)-。
实施方案7c:根据实施方案2所述的化合物,其中X为-CH=CH-、 -CH=CF-、-CH=CCl-或-CH=C(CH3)-。
实施方案7d:根据式1或实施方案1至7a中任一项所述的化合物,其中R1为H、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、 C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、 C3–C7卤代烯基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基、苄基或苯基。
实施方案7e:根据式1或实施方案1至7a中任一项所述的化合物,其中R1为H、C1–C7烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基或苄基。
实施方案8.根据式1或实施方案1至7中任一项所述的化合物,其中 R1为C1–C4烷基、C3–C4烯基、C3–C4炔基、C3–C4环烷基、C2–C3氰基烷基、 C1–C3卤代烷基或C2–C4烷氧基烷基。
实施方案9.根据实施方案8所述的化合物,其中R1为C1–C3烷基、烯丙基、炔丙基、CH2CH2CN、C1–C2卤代烷基或2-甲氧基乙基。
实施方案10.根据实施方案9所述的化合物,其中R1为甲基、乙基、正丙基或2-甲氧基乙基。
实施方案11.根据实施方案10所述的化合物,其中R1为甲基或乙基。
实施方案12.根据实施方案11所述的化合物,其中R1为甲基。
实施方案12a.根据式1所述的化合物,其中R1不为H。
实施方案12b:根据式1所述的化合物,其中R1不为苯基。
实施方案12c:根据式1所述的化合物,其中R2为H、卤素、-CN、-CHO、 C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C1–C4烷基羰基、 C2–C7烷基羰基氧基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C2–C8二烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C1–C7烷氧基或C1–C5烷硫基。
实施方案12d:根据式1所述的化合物,其中R2为H、卤素、-CN、-CHO、 C1–C7烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、C4–C7烷基环烷基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C2–C7烷氧基烷基或C1–C7烷氧基。
实施方案13.根据式1或实施方案1至12中任一项所述的化合物,其中 R2为H、卤素、-CN、C1–C4烷基、C3–C5环烷基、C1–C3卤代烷基、C2–C4烷氧基烷基或C1–C3烷氧基。
实施方案14.根据实施方案13所述的化合物,其中R2为H、卤素、C1–C3烷基、环丙基、C1–C2卤代烷基、甲氧基或乙氧基。
实施方案15.根据实施方案14所述的化合物,其中R2为H、甲基、乙基、正-丙基、CF3或甲氧基。
实施方案16.根据实施方案15所述的化合物,其中R2为甲基或乙基。
实施方案17.根据实施方案16所述的化合物,其中R2为甲基。
实施方案17a.根据式1所述的化合物,其中R2不为苯基。
实施方案18.根据式1或实施方案1至17中任一项所述的化合物,其中每个R3独立地为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基。
实施方案19.根据实施方案18所述的化合物,其中每个R3独立地为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基。
实施方案20.根据实施方案19所述的化合物,其中每个R3独立地为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基。
实施方案21.根据实施方案20所述的化合物,其中每个R3独立地为卤素、-CN、甲基、乙基、甲氧基或乙氧基。
实施方案22.根据实施方案21所述的化合物,其中每个R3独立地为F、 Cl、Br、甲基、乙基或甲氧基。
实施方案23.根据式1或实施方案1至22中任一项所述的化合物,其中 R4为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基。
实施方案24.根据实施方案23所述的化合物,其中R4为卤素、-CN、 C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基。
实施方案25.根据实施方案24所述的化合物,其中R4为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基。
实施方案26.根据实施方案25所述的化合物,其中R4为甲基或乙基。
实施方案27.根据实施方案26所述的化合物,其中R4为甲基。
实施方案28.根据式1或实施方案1至27中任一项所述的化合物,其中 R5为C1-C2烷基。
实施方案29.根据实施方案28所述的化合物,其中R5为甲基。
实施方案30.根据式1或实施方案1至29中任一项所述的化合物,其中 R6和R7独立地为H、卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、 C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基。
实施方案31.根据式1或实施方案1至30中任一项所述的化合物,其中 R6和R7独立地为H、卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、 C1–C2卤代烷基或C1–C2烷氧基。
实施方案32.根据式1或实施方案1至31中任一项所述的化合物,其中 R6和R7独立地为H、卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、 CF3、甲氧基或乙氧基。
实施方案34a.根据式1或实施方案1至32中任一项所述的化合物,其中R6和R7独立地为H、卤素或C1–C2烷基。
实施方案34b.根据式1或实施方案1至32中任一项所述的化合物,其中R6和R7独立地为H或卤素。
实施方案34c.根据式1或实施方案1至32中任一项所述的化合物,其中R6为H并且R7为卤素。
实施方案34d.根据式1或实施方案1至32中任一项所述的化合物,其中R6为卤素并且R7为H。
实施方案33.根据式1或实施方案1至32中任一项所述的化合物,其中 R6和R7独立地为H或C1–C2烷基。
实施方案34.根据式1或实施方案1至33中任一项所述的化合物,其中 R6为H或甲基(即CH3)。
实施方案35.根据式1或实施方案1至34中任一项所述的化合物,其中 R7为H或甲基(即CH3)。
实施方案36.根据实施方案34或35所述的化合物,其中R6为H并且 R7为H,或者R6为H并且R7为CH3,或者R6为CH3并且R7为H。
实施方案37.根据实施方案36所述的化合物,其中R6为H并且R7为H°
实施方案37a.根据式1或实施方案1至37中任一项所述的化合物,其中G为G1。
实施方案37b.根据式1或实施方案1至37a中任一项所述的化合物,其中G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、 -CONR10R11、-S(O)2NR10R11或P(=O)R12;或C3–C6环烷基或C4–C7环烷基烷基。
实施方案37c.根据式1或实施方案1至37a中任一项所述的化合物,其中G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、 -CONR10R11、-S(O)2NR10R11或P(=O)R12;或C4–C7环烷基烷基。
实施方案38.根据式1或实施方案1至37中任一项所述的化合物,其中 G1为H、-C(=O)R8、-CO2R9、-S(O)2R8、-CONR10R11、-S(O)2NR10R11或P(=O)R12。
实施方案39.根据实施方案38所述的化合物,其中G1为H、-C(=O)R8、 -CO2R9、-S(O)2R8或P(=O)R12。
实施方案39a.根据实施方案39所述的化合物,其中G1为H。
实施方案39b.根据实施方案39所述的化合物,其中G1为-C(=O)R8。
实施方案39c.根据实施方案39所述的化合物,其中G1为-CO2R9。
实施方案39d.根据实施方案39所述的化合物,其中G1为-S(O)2R8。
实施方案39e.根据实施方案39所述的化合物,其中G1为P(=O)R12。
实施方案40.根据式1或实施方案1至39e中任一项所述的化合物,其中R8和R10独立地为H、C1-C7烷基、C3-C7环烷基、C1-C3卤代烷基或C2-C7烷氧基烷基。
实施方案41.根据实施方案40所述的化合物,其中R8和R10独立地为H、 C1-C7烷基、C3-C7环烷基或C2-C7烷氧基烷基。
实施方案42.根据实施方案41所述的化合物,其中R8和R10独立地为 C1-C7烷基或C2-C7烷氧基烷基。
实施方案42a.根据实施方案1至40中任一项所述的化合物,其中R8为 C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基。
实施方案42b.根据实施方案41所述的化合物,其中R8独立地为C1–C3烷基或C2–C4烷氧基烷基。
实施方案42c.根据式1或实施方案1至37中任一项所述的化合物,其中G为WG1。
实施方案42d.根据式1或实施方案1至42a中任一项所述的化合物,其中W1为C1–C2烷二基或C2–C3烯二基。
实施方案42e.根据实施方案42b所述的化合物,其中W1为–CH2–或–CH=CH-。
实施方案42f.根据实施方案42c所述的化合物,其中W1为–CH2-。
实施方案43.根据式1或实施方案1至42中任一项所述的化合物,其中 R9为H、C1–C7烷基、C3–C7环烷基、C2–C3卤代烷基或C2–C7烷氧基烷基。
实施方案44.根据实施方案43所述的化合物,其中R9为H、C1–C7烷基、 C3–C7环烷基或C2–C7烷氧基烷基。
实施方案45.根据实施方案44所述的化合物,其中R9为C1–C7烷基或 C2–C7烷氧基烷基。
实施方案46.根据式1或实施方案1至45中任一项所述的化合物,其中 R11为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基。
实施方案47.根据实施方案46所述的化合物,其中R11为H、C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基。
实施方案48.根据实施方案1至47中任一项所述的化合物,其中R12为 C1–C3烷基或C1–C3烷氧基。
实施方案49.根据实施方案48所述的化合物,其中R12为CH3或OCH3。
实施方案48.根据式1或实施方案1至47中任一项所述的化合物,其中 n为0、1、2或3。
实施方案49.根据实施方案48所述的化合物,其中n为0、1或2。
实施方案50.根据实施方案48所述的化合物,其中n为1、2或3。
实施方案51.根据实施方案49或50所述的化合物,其中n为1或2。
本发明的实施方案,包括上文实施方案1-51以及本文所述的任何其它实施方案,可以任何方式组合,并且实施方案中的变量描述不仅涉及式1的化合物,而且还涉及可用于制备式1的化合物的起始化合物和中间体化合物。此外,本发明的实施方案,包括上文实施方案1-51和本文所述的任何其它实施方案,以及它们的任何组合,均涉及本发明的组合物和方法。
实施方案1-51的组合由以下示出:
实施方案A:式1的化合物,其中
W为O;
X为O、S、-CH=CH-、-C(CH3)=CH-、-CH=CF-、-CH=CCl-或 -CH=C(CH3)-;
R1为H、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、 C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、 C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基、苄基或苯基;
R2为H、卤素、-CN、-CHO、C1–C7烷基、C3–C8烷基羰基烷基、 C3–C8烷氧基羰基烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、 C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C2–C8二烷基氨基、 C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C1–C7烷氧基或C1–C5烷硫基;
每个R3独立地为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、 C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
R4为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、 C1–C2烷硫基或C1–C2卤代烷硫基;
G为G1;
G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、 -CONR10R11、-S(O)2NR10R11或P(=O)R12;或C3–C6环烷基或 C4–C7环烷基烷基;
R8和R10独立地为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R9为H、C1–C7烷基、C3–C7环烷基、C2–C3卤代烷基或C2–C7烷氧基烷基;
R11为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R12为C1-C3烷基或C1-C3烷氧基;
并且
n为0、1、2或3。
实施方案B.根据实施方案A所述的化合物,其中
X为-CH=CH-、-C(CH3)=CH-、-CH=CF-、-CH=CCl-或–CH=C(CH3)-;
R1为H、C1–C7烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、 C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基或苄基;
R2为H、卤素、-CN、-CHO、C1–C7烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、C4–C7烷基环烷基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、 C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、 C1–C7卤代烷基、C2–C7烷氧基烷基或C1–C7烷氧基;
每个R3独立地为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
R4为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
G1为H、-C(=O)R8、-CO2R9、-S(O)2R8、-CONR10R11、-S(O)2NR10R11或P(=O)R12;
R8、R9和R10独立地为H、C1-C7烷基、C3-C7环烷基或C2-C7烷氧基烷基;
R11为H、C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基;并且
R12为CH3或OCH3。
实施方案C:根据实施方案B所述的化合物,其中
X为-CH=CH-、-CH=CF-、-CH=CCl-或–CH=C(CH3)-,
R1为甲基、乙基、正丙基或2-甲氧基乙基;
R2为H、甲基、乙基、正丙基、CF3或甲氧基;
每个R3独立地为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
R4为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
G1为H、-C(=O)R8、-CO2R9、-S(O)2R8或P(=O)R12;
R8和R9独立地为C1–C7烷基或C2–C7烷氧基烷基;并且
n为1或2。
具体的实施方案包括式1的化合物,所述化合物选自:
4-(2,5-二甲基苯并[b]噻吩-3-基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物1),
5-羟基-2,6-二甲基-4-(2,5,7-三甲基苯并[b]噻吩-3-基)-3(2H)-哒嗪酮(化合物2),
5-羟基-2,6-二甲基-4-(2,4,6-三甲基苯并[b]噻吩-3-基)-3(2H)-哒嗪酮(化合物3),
5-羟基-2,6-二甲基-4-(2-甲基-3-苯并呋喃基)-3(2H)-哒嗪酮(化合物4),
5-羟基-4-(5-甲氧基-3-苯并呋喃基)-2,6-二甲基-3(2H)-哒嗪酮(化合物 5),
4-(5-氯-2-甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物6),
4-(2,5-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物 7),
4-(2,4-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物 8),
4-(2,7-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物 9),
4-(2-乙基-5-甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物10),
5-羟基-2,6-二甲基-4-(1-萘基)-3(2H)-哒嗪酮(化合物11),
5-羟基-2,6-二甲基-4-(2,5,7-三甲基-3-苯并呋喃基)-3(2H)-哒嗪酮(化合物12),
4-(5-乙基-2-甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物13),
5-(乙酰氧基)-4-(2,5-二甲基-3-苯并呋喃基)-2,6-二甲基-3(2H)-哒嗪酮(化合物14),
5-(乙酰氧基)-4-(2,7-二甲基-3-苯并呋喃基)-2,6-二甲基-3(2H)-哒嗪酮(化合物15),
5-(乙酰氧基)-2,6-二甲基-4-(2,5,7-三甲基-3-苯并呋喃基)-3(2H)-哒嗪酮(化合物16),
2,2-二甲基丙酸5-(2,5-二甲基-3-苯并呋喃基)-1,6-二氢-1,3-二甲基-6-氧代基-4-哒嗪酯(化合物17),
2,2-二甲基丙酸1,6-二氢-1,3-二甲基-6-氧代基-5-(2,5,7-三甲基-3-苯并呋喃基)-4-哒嗪酯(化合物18),以及
4-(2-乙基-4,6-二甲基苯并[b]噻吩-3-基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物19)。
具体的实施方案也包括式1的化合物,所述化合物选自化合物编号1、 3、11、23、25、27、28、29、32、42、47、57、59和60。化合物编号参见表A中的化合物索引。
本发明还涉及用于防治不期望的植被的方法,所述方法包括向植被所在地施用除草有效量的本发明化合物(例如为本文所述组合物形式)。值得注意的与使用方法相关的实施方案是涉及上述实施方案的化合物的那些。本发明的化合物可用于多种作物中的杂草防治,所述作物诸如小麦、大麦、玉米、大豆、向日葵、棉、油菜和稻,以及特色作物诸如甘蔗、柑橘、水果和坚果作物。本发明的化合物特别可用于选择性防治禾本科谷类作物中的杂草,所述作物诸如玉米、稻和小麦。
如发明内容中所述的本发明的实施方案包括(其中如以下实施方案中所用的式1包括其N-氧化物和其盐):
实施方案P1.式1的化合物,其中W为O。
实施方案P2.根据式1或实施方案P1所述的化合物,其中X为O、S 或-C(R6)=C(R7)-。
实施方案P3.根据实施方案P2所述的化合物,其中X为O或S。
实施方案P4.根据实施方案P3所述的化合物,其中X为O。
实施方案P5.根据实施方案P3所述的化合物,其中X为S。
实施方案P6.根据实施方案P2所述的化合物,其中X为-C(R6)=C(R7)-。
实施方案P7.根据式1或实施方案P1所述的化合物,其中X为NR5。
实施方案P8.根据式1或实施方案P1至P7中任一项所述的化合物,其中R1为C1–C4烷基、C3–C4烯基、C3–C4炔基、C3–C4环烷基、C2–C3氰基烷基、C1–C3卤代烷基或C2–C4烷氧基烷基。
实施方案P9.根据实施方案P8所述的化合物,其中R1为C1–C3烷基、烯丙基、炔丙基、CH2CH2CN、C1–C2卤代烷基或2-甲氧基乙基。
实施方案P10.根据实施方案P9所述的化合物,其中R1为甲基、乙基、正丙基或2-甲氧基乙基。
实施方案P11.根据实施方案P10所述的化合物,其中R1为甲基或乙基。
实施方案P12.根据实施方案P11所述的化合物,其中R1为甲基。
实施方案P13.根据式1或实施方案P1至P12中任一项所述的化合物,其中R2为H、卤素、-CN、C1–C4烷基、C3–C5环烷基、C1–C3卤代烷基、C2–C4烷氧基烷基或C1–C3烷氧基。
实施方案P14.根据实施方案P13所述的化合物,其中R2为H、卤素、 C1–C3烷基、环丙基、C1–C2卤代烷基、甲氧基或乙氧基。
实施方案P15.根据实施方案P14所述的化合物,其中R2为H、甲基、乙基、正-丙基、CF3或甲氧基。
实施方案P16.根据实施方案P15所述的化合物,其中R2为甲基或乙基。
实施方案P17.根据实施方案P16所述的化合物,其中R2为甲基。
实施方案P18.根据式1或实施方案P1至P17中任一项所述的化合物,其中每个R3独立地为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基。
实施方案P19.根据实施方案P18所述的化合物,其中每个R3独立地为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或 C1–C2烷氧基。
实施方案P20.根据实施方案P19所述的化合物,其中每个R3独立地为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基。
实施方案P21.根据实施方案P20所述的化合物,其中每个R3独立地为卤素、-CN、甲基、乙基、甲氧基或乙氧基。
实施方案P22.根据实施方案P21所述的化合物,其中每个R3独立地为 F、Cl、Br、甲基、乙基或甲氧基。
实施方案P23.根据式1或实施方案P1至P22中任一项所述的化合物,其中R4为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、 C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基。
实施方案P24.根据实施方案P23所述的化合物,其中R4为卤素、-CN、 C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基。
实施方案P25.根据实施方案P24所述的化合物,其中R4为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基。
实施方案P26.根据实施方案P25所述的化合物,其中R4为甲基或乙基。
实施方案P27.根据实施方案P26所述的化合物,其中R4为甲基。
实施方案P28.根据式1或实施方案P1至P27中任一项所述的化合物,其中R5为C1-C2烷基。
实施方案P29.根据实施方案P28所述的化合物,其中R5为甲基。
实施方案P30.根据式1或实施方案P1至P29中任一项所述的化合物,其中R6和R7独立地为H、卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基。
实施方案P31.根据式1或实施方案P1至P30中任一项所述的化合物,其中R6和R7独立地为H、卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基。
实施方案P32.根据式1或实施方案P1至P31中任一项所述的化合物,其中R6和R7独立地为H、卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基。
实施方案P33.根据式1或实施方案P1至P32中任一项所述的化合物,其中R6和R7独立地为H或C1–C2烷基。
实施方案P34.根据式1或实施方案P1至P33中任一项所述的化合物,其中R6为H或甲基(即CH3)。
实施方案P35.根据式1或实施方案P1至P34中任一项的化合物,其中 R7为H或甲基(即CH3)。
实施方案P36.根据实施方案P34或35所述的化合物,其中R6为H并且R7为H,或者R6为H并且R7为CH3,或者R6为CH3并且R7为H。
实施方案P37.根据实施方案P36所述的化合物,其中R6为H并且R7为H。
实施方案P38.根据式1或实施方案P1至P37中任一项所述的化合物,其中G为H、-C(=O)R8、-CO2R9、-S(O)2R8、-CONR10R11或-S(O)2NR10R11。
实施方案P39.根据实施方案P38所述的化合物,其中G为H、-C(=O)R8、 -CO2R9或-S(O)2R8。
实施方案P40.根据式1或实施方案P1至P39中任一项所述的化合物,其中R8和R10独立地为H、C1-C7烷基、C3-C7环烷基、C1-C3卤代烷基或C2-C7烷氧基烷基。
实施方案P41.根据实施方案P40所述的化合物,其中R8和R10独立地为H、C1-C7烷基、C3-C7环烷基或C2-C7烷氧基烷基。
实施方案P42.根据实施方案P41所述的化合物,其中R8和R10独立地为C1-C7烷基或C2-C7烷氧基烷基。
实施方案P43.根据式1或实施方案1至42中任一项所述的化合物,其中R9为H、C1–C7烷基、C3–C7环烷基、C2–C3卤代烷基或C2–C7烷氧基烷基。
实施方案P44.根据实施方案P43所述的化合物,其中R9为H、C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基。
实施方案P45.根据实施方案P44所述的化合物,其中R9为C1–C7烷基或C2–C7烷氧基烷基。
实施方案P46.根据式1或实施方案P1至P45中任一项所述的化合物,其中R11为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基。
实施方案P47.根据实施方案P46所述的化合物,其中R11为H、C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基。
实施方案P48.根据式1或实施方案P1至P47中任一项所述的化合物,其中n为0、1、2或3。
实施方案P49.根据实施方案P48所述的化合物,其中n为0、1或2。
实施方案P50.根据实施方案P48所述的化合物,其中n为1、2或3。
实施方案P51.根据实施方案P49或P50所述的化合物,其中n为1或2。
本发明的实施方案,包括上文实施方案P1–P51以及本文所述的任何其它实施方案,可以任何方式组合,并且实施方案中的变量描述不仅涉及式1 的化合物,而且还涉及可用于制备式1的化合物的起始化合物和中间体化合物。此外,本发明的实施方案,包括上文实施方案P1–P51以及本文所述的任何其它实施方案,以及它们的任何组合,均涉及本发明的组合物和方法。
实施方案P1–P51的组合可由以下示出:
实施方案PA式1的化合物,其中
W为O;
X为O、S、-CH=CH-、-C(CH3)=CH-或–CH=C(CH3)-;
R1为C1-C4烷基、C3–C4烯基、C3–C4炔基、C3–C4环烷基、C2–C3氰基烷基、C1–C3卤代烷基或C2–C4烷氧基烷基;
R2为H、卤素、-CN、C1–C4烷基、C3–C5环烷基、C1–C3卤代烷基、 C2–C4烷氧基烷基或C1–C3烷氧基;
每个R3独立地为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、 C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
R4为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、 C1–C2烷硫基或C1–C2卤代烷硫基;
G为H、-C(=O)R8、-CO2R9、-S(O)2R8、-CONR10R11或-S(O)2NR10R11;
R8和R10独立地为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R9为H、C1–C7烷基、C3–C7环烷基、C2–C3卤代烷基或C2–C7烷氧基烷基;
R11为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;并且
n为0、1、2或3。
实施方案PB根据实施方案PA所述的化合物,其中
R1为C1–C3烷基、烯丙基、炔丙基、CH2CH2CN、C1–C2卤代烷基或2-甲氧基乙基;
R2为H、卤素、C1–C3烷基、环丙基、C1–C2卤代烷基、甲氧基或乙氧基;
每个R3独立地为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
R4为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
R8、R9和R10独立地为H、C1-C7烷基、C3-C7环烷基或C2-C7烷氧基烷基;并且
R11为H、C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基。
实施方案PC根据实施方案PB所述的化合物,其中
R1为甲基、乙基、正丙基或2-甲氧基乙基;
R2为H、甲基、乙基、正丙基、CF3或甲氧基;
每个R3独立地为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
R4为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
G为H、-C(=O)R8、-CO2R9或-S(O)2R8;
R8和R9独立地为C1–C7烷基或C2–C7烷氧基烷基;并且
n为1或2。
还值得注意的实施方案是包含上述实施方案的化合物的本发明除草剂组合物。
本发明也包括除草剂混合物,该除草剂混合物包括(a)选自式1的化合物、其N-氧化物及其盐,和(b)至少一种附加活性成分,所述附加活性成分选自(b1)光系统II抑制剂、(b2)乙酰羟酸合酶(AHAS)抑制剂、(b3)乙酰-CoA 羧化酶(ACCase)抑制剂、(b4)生长素模拟物和(b5)5-烯醇-丙酮酰莽草酸-3-磷酸酯(EPSP)合酶抑制剂、(b6)光系统I电子转向剂(diverters)、(b7)原卟啉原氧化酶(PPO)抑制剂、(b8)谷氨酰胺合酶(GS)抑制剂、(b9)极长链脂肪酸 (VLCFA)延伸酶抑制剂、(b10)植物生长素输送抑制剂、(b11)八氢番茄红素脱氢酶(PDS)抑制剂、(b12)4-羟基苯基-丙酮酸双加氧酶(HPPD)抑制剂、 (b13)homogentisatesolenesyltransererase(HST)抑制剂、(b14)纤维素生物合成抑制剂、(b15)其它除草剂包括有丝分裂干扰物、有机砷化物、磺草灵、溴丁酰草胺、环庚草醚、苄草隆、棉隆、野燕枯、汰草龙、乙氧苯草胺、抑草丁、调节膦、氨基甲酰基膦酸乙酯铵盐、威百亩、甲基杀草隆、油酸、噁嗪草酮、壬酸和稗草畏,和(b16)除草剂安全剂;以及(b1)至(b16)的化合物的盐。
“光系统II抑制剂”(b1)是在QB-结合位置(niche)结合D-1蛋白质并由此阻挡叶绿体类囊体膜中的电子从QA向QB传输的化学化合物。通过光系统 II被阻断的电子通过一系列反应转移,以形成毒性化合物,所述毒性化合物破坏细胞膜并造成叶绿体溶胀、膜渗漏,并最终造成细胞破裂。QB-结合位置具有三个不同的结合位点:结合位点A结合三嗪诸如阿特拉津、三嗪酮诸如环嗪酮,和尿嘧啶诸如除草定,结合位点B结合苯基脲诸如敌草隆,并且结合位点C结合苯并噻二唑诸如灭草松、腈诸如溴苯腈以及苯基-哒嗪诸如达草特。光系统II抑制剂的示例包括莠灭净、氨唑草酮、阿特拉津、灭草松、除草定、溴酚肟、溴苯腈、氯溴隆、杀草敏、绿麦隆、枯草隆、苄草隆、氰草津、杀草隆、甜菜安、敌草净、噁唑隆、排草净、敌草隆,磺噻隆、非草隆、伏草隆、环嗪酮、碘苯腈、异丙隆、异噁隆、环草定、利谷隆、苯嗪草酮、甲基苯噻隆、溴谷隆、甲氧隆、嗪草酮、绿谷隆、草不隆、甲氯酰草胺、苯敌草、扑灭通、扑草净、敌稗、扑灭津、氯苯哒醇(pyridafol)、达草特、环草隆、西玛津、西草净、特丁噻草隆、特草定、甲氧去草净、特丁津、特丁净和草达津。值得注意的是与阿特拉津、溴苯腈或灭草松混合的本发明化合物。还值得注意的是本发明化合物与阿特拉津、溴苯腈或嗪草酮混合。
“AHAS抑制剂”(b2)是抑制乙酰羟酸合酶(AHAS)(还称为乙酰乳酸合酶(ALS))的化学化合物,从而通过抑制蛋白质合成和细胞生长所需的支链脂族氨基酸诸如缬氨酸、亮氨酸和异亮氨酸的制备来杀死植物。 AHAS抑制剂的示例包括酰嘧磺隆、四唑嘧磺隆、苄嘧磺隆-甲酯、双草醚钠、氯酯磺草胺、氯嘧磺隆-乙酯、氯磺隆、醚磺隆、环丙嘧磺隆、双氯磺草安、胺苯磺隆-甲酯、乙氧嘧磺隆、啶嘧磺隆、双氟磺草胺、氟酮磺隆钠、唑嘧磺草胺、氟啶嘧磺隆、氟啶嘧磺隆钠(flupyrsulfuron-sodium)、甲酰胺磺隆、氯吡嘧磺隆、咪草酸、甲氧咪草烟、甲咪唑烟酸、灭草烟、灭草喹、咪草烟、唑吡嘧磺隆、碘磺隆-甲酯(包括钠盐)、iofensulfuron(2-碘-N-[[(4- 甲氧基-6-甲基-1,3,5-三嗪-2-基)氨基]羰基]苯磺酰胺)、甲基二磺隆-甲酯、嗪吡嘧磺隆(3-氯-4-(5,6-二氢-5-甲基-1,4,2-二嗪-3-基)-N-[[(4,6-二甲氧基-2-嘧啶基)氨基]羰基]-1-甲基-1H-吡唑-5-磺酰胺)、磺草唑胺、甲磺隆、烟嘧磺隆、环氧嘧磺隆、五氟磺草胺、氟嘧磺隆、丙苯磺隆钠、丙嗪嘧磺隆(2-氯-N-[[(4,6- 二甲氧基-2-嘧啶基)氨基]羰基]-6-丙基咪唑[1,2-b]哒嗪-3-磺酰胺)、氟磺隆、吡嘧磺隆、嘧啶肟草醚、环酯草醚、嘧草醚、嘧草硫醚钠、砜嘧磺隆、甲嘧磺隆、磺酰磺隆、噻酮磺隆、噻磺隆、氟酮磺草胺(N-[2-[(4,6-二甲氧基-1,3,5- 三嗪-2-基)羰基]-6-氟苯基]-1,1-二氟-N-甲基甲磺酰胺)、醚苯磺隆、苯磺隆-甲酯、三氟啶磺隆(包括钠盐)、氟胺磺隆和三氟甲磺隆。值得注意的是,与砜嘧磺隆、噻磺隆、苯磺隆、烟嘧磺隆、甲磺隆、氟啶嘧磺隆、氯酯磺草胺、甲氧磺草胺或双氟磺草胺混合的本发明的化合物。还值得注意的是与烟嘧磺隆、氟啶磺隆或氯嘧磺隆混合的本发明的化合物。
“ACCase抑制剂”(b3)为抑制乙酰-CoA羧化酶的化学化合物,所述酶负责催化植物中脂质和脂肪酸合成的早期步骤。脂质是细胞膜的主要组分,没有脂质,则不能制造新细胞。乙酰CoA羧化酶的抑制和后续脂质制造的缺乏,导致细胞膜完整性丧失,尤其是在活跃生长区诸如分生组织中。最终苗和根茎生长停止,并且苗分生组织和根茎芽开始枯死。ACCase抑制剂的示例包括禾草灭、丁苯草酮、烯草酮、炔草酯、噻草酮、氰氟草酯、禾草灵、噁唑禾草灵、吡氟禾草灵、氟吡禾灵、唑啉草酯、环苯草酮、喔草酯、喹禾灵、烯禾啶、得杀草和肟草酮,包括拆分形式诸如精-噁唑禾草灵、精-吡氟禾草灵、精-氟吡禾灵和精-喹禾灵以及酯形式诸如炔-草酯、氰氟-草酯丁酯、禾草灵-甲基和精噁唑-禾草灵-乙酯。值得注意的是与唑啉草酯或喹禾灵混合的本发明化合物。
生长素是植物激素,其调节许多植物组织的生长。“生长素模拟物”(b4) 是模拟植物生长激素生长素的化学化合物,因此导致不受控制和无序的生长,从而导致易感物种的植株死亡。生长素模拟物的示例包括环丙嘧啶酸(6- 氨基-5-氯-2-环丙基-4-嘧啶羧酸)及其甲酯和乙酯和其钠盐和钾盐、氨草啶、-草除灵乙酯、草灭平、氯酰草膦、clomeprop、二氯吡啶酸、麦草畏、 2,4-D、2,4-DB、滴丙酸、氯氟吡氧乙酸、氟氯吡啶酯(4-氨基-3-氯-6-(4-氯 -2-氟-3-甲氧基苯基)-2-吡啶羧酸)、氟氯吡啶甲酯(4-氨基-3-氯-6-(4-氯-2-氟 -3-甲氧基苯基)-2-吡啶羧酸甲酯)、MCPA、MCPB、2甲4氯丙酸、毒莠定、二氯喹啉酸、氯甲喹啉酸、2,3,6-TBA、绿草定、和4-氨基-3-氯-6-(4-氯-2- 氟-3-甲氧基苯基)-5-氟-2-吡啶羧酸甲酯。特别值得注意的是,与麦草畏、氟草烟异辛酯、2,4-D、氟氯吡啶甲酯或MCPA混合的本发明化合物。还值得注意的是与麦草畏混合的本发明化合物。
“EPSP合酶抑制剂”(b5)为抑制酶,5-烯醇-丙酮酰莽草酸-3-磷酸酯合酶的化学化合物,所述酶涉及芳族氨基酸诸如酪氨酸、色氨酸和苯丙氨酸的合成。EPSP抑制剂除草剂易于通过植物叶吸收并在韧皮部中易位至生长点。草甘膦是属于该组的相对非选择性苗后除草剂。草甘膦包括酯和盐,诸如铵盐、异丙基铵盐、钾盐、钠盐(包括倍半钠盐)和三甲基锍盐(或者被称为草硫膦)。
“光系统I电子转向剂”(b6)为从光系统I中接收电子,并在数次循环之后产生羟基自由基的化学化合物。这些自由基极具反应性并易于破坏不饱和脂质,包括膜脂肪酸和叶绿素。这破坏细胞膜完整性,使得细胞和细胞器“渗漏”,从而导致叶片快速萎蔫和干枯,并最终导致植物死亡。该第二类型光合作用抑制剂的示例包括杀草快和百草枯。
“PPO抑制剂”(b7)为抑制酶原卟啉原氧化酶的化学化合物,其迅速地导致在植物中形成破坏细胞膜的高反应性化合物,从而导致细胞液渗出。 PPO抑制剂的示例包括三氟羧草醚钠、唑啶草酮、双苯嘧草酮、甲羧除草醚、氟丙嘧草酯、唑酮草酯、三唑酮草酯、甲氧除草醚、吲哚酮草-酯、异丙吡草酯、氟哒嗪-草酯、氟胺草酯、丙炔氟草胺、乙羧氟草醚、哒草氟、氟磺胺草醚、氟硝磺酰胺(halosafen)、乳氟禾草灵、丙炔噁草酮、噁草酮、乙氧氟草醚、环戊噁草酮、氟唑草胺、双唑草腈、吡草-醚、嘧啶肟草醚、甲磺草胺、噻二唑草胺、tiafenacil(N-[2-[[2-氯-5-[3,6-二氢-3-甲基-2,6-二氧-4-(三氟甲基)-1(2H)-嘧啶基]-4-氟苯基]硫]-1-氧代丙基]-β-丙氨酸甲酯)和3-[7-氟 -3,4-二氢-3-氧代-4-(2-丙炔-1-基)-2H-1,4-苯并噁嗪-6-基]二氢-1,5-二甲基l-6- 硫代-1,3,5-三嗪-2,4(1H,3H)-二酮。值得注意的是与嘧啶肟草醚、丙炔氟草胺或三唑酮草酯混合的本发明化合物。
“GS抑制剂”(b8)是抑制谷氨酰胺合酶的活性的化学化合物,植物使用所述酶以将氨转化为谷氨酰胺。因此,氨累积并且谷氨酰胺含量降低。由于氨毒性和其它代谢过程所需的氨基酸缺乏的联合效应,植物损害可能出现。GS抑制剂包括草胺磷及其酯和盐,诸如草胺磷-及其它草胺膦衍生物,精-草胺膦((2S)-2-氨基-4-(羟甲基氧膦基)丁酸)和双丙氨膦。
“VLCFA延伸酶抑制剂”(b9)为具有各种化学结构的除草剂,其抑制延伸酶。延伸酶是位于叶绿体中或附近的酶之一,其涉及VLCFA的生物合成。在植物中,极长链脂肪酸为疏水性聚合物的主要成分,其防止叶表面处的干燥并提供花粉粒的稳定性。此类除草剂包括乙草胺、甲草胺、莎稗磷、丁草胺、苯酮唑、二甲草胺、噻吩草胺、双苯酰草胺、fenoxasulfone(3-[[(2,5- 二氯-4-乙氧基苯基)甲基]磺酰基]-4,5-二氢-5,5-二甲基异噁唑)、四唑酰草胺、氟噻草胺、茚草酮、苯噻草胺、吡唑草胺、异丙甲草胺、萘丙胺、萘丙酰草胺、萘丙酰草胺-M((2R)-N,N-二乙基-2-(1-萘氧基)丙酰胺)、烯草胺、哌草磷、丙草胺、毒草胺、异丙草胺、罗克杀草砜、以及甲氧噻草胺,包括拆分形式诸如精-异丙甲草胺和氯乙酰胺以及氧乙酰胺。值得注意的是与罗克杀草砜、异丙甲草胺、乙草胺、噻吩草胺、甲草胺或氟噻草胺混合的本发明化合物。还值得注意的是与氟噻草胺混合的本发明化合物。
“生长素传输抑制剂”(b10)是抑制植物中生长素传输的化学物质,诸如通过与生长素-载体蛋白质结合。生长素传输抑制剂的示例包括氟吡草腙、萘草胺(还称为N-(1-萘基)邻氨甲酰基苯甲酸和2-[(1-萘基氨基)羰基] 苯甲酸)。
“PDS抑制剂”(b11)为在八氢番茄红素脱氢酶步骤抑制类胡萝卜素生物合成途径的化学化合物。PDS抑制剂的示例包括氟丁酰草胺、吡氟草胺、氟啶酮、氟咯草酮、呋草酮、氟草敏和氟吡酰草胺。
“HPPD抑制剂”(b12))是抑制4-羟基苯基丙酮酸双氧化酶合成的生物合成的化学物质。HPPD抑制剂的示例包括苯并双环酮、吡草酮、氟吡草酮(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]双环 [3.2.1]辛-3-烯-2-酮)、fenquinotrione(2-[[8-氯-3,4-二氢-4-(4-甲氧基苯基)-3-氧代-2-喹喔啉基]羰基]-1,3-环己二酮)、异噁氯草酮、异噁唑草酮、甲基磺草酮、磺酰草吡脱、吡唑特、苄草唑、磺草酮、特呋三酮、环磺酮、苯吡唑草酮、 5-氯-3-[(2-羟基-6-氧代-1-环己烯-1-基)羰基]-1-(4-甲氧基苯基)-2(1H)-喹喔啉酮、4-(2,6-二乙基-4-甲基苯基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮、4-(4-氟苯基)-6-[(2-羟基-6-氧代-1-环己烯-1-基)羰基]-2-甲基-1,2,4-三嗪-3,5(2H,4H)-二酮、5-[(2-羟基-6-氧代-1-环己烯-1-基)羰基]-2-(3-甲氧基苯基)-3-(3-甲氧基丙基)-4(3H)-嘧啶酮、2-甲基-N-(4-甲基-1,2,5-噁二唑-3-基)-3-(甲基亚磺酰基)-4-(三氟甲基)苯甲酰胺和2-甲基-3-(甲磺酰)-N-(1-甲基-1H-四唑-5- 基)-4-(三氟甲基)苯甲酰胺。值得注意的是本发明化合物与甲基磺草酮、异噁唑草酮、环磺酮、氟吡草酮、苯吡唑草酮(topramazone)或磺酰草吡脱的混合物。还值得注意的是与甲基磺草酮或磺酰草吡脱混合的本发明化合物。
HST(homogentisate solenesyltransererase)抑制剂(b13)破坏植物将尿黑酸转化成2-甲基-6-茄尼基-1,4-苯醌的能力,从而破坏类胡萝卜素生物合成。HST抑制剂的示例包括氟啶草、氯草定、3-(2-氯-3,6-二氟苯基)-4-羟基 -1-甲基-1,5-萘啶-2(1H)-酮、7-(3,5-二氯-4-吡啶基)-5-(2,2-二氟乙基)-8-羟基吡咯并[2,3-b]吡嗪-6(5H)-酮、和4-(2,6-二乙基-4-甲基苯基)-5-羟基-2,6-二甲基 -3(2H)-哒嗪酮。
HST抑制剂还包括式A和式B的化合物。
其中Rd1为H、Cl或CF3;Rd2为H、Cl或Br;Rd3为H或Cl;Rd4为H、Cl 或CF3;Rd5为CH3、CH2CH3或CH2CHF2;并且Rd6为OH或-OC(=O)-i-Pr;并且Re1为H、F、Cl、CH3或CH2CH3;Re2为H或CF3;Re3为H、CH3或 CH2CH3;Re4为H、F或Br;Re5为Cl、CH3、CF3、OCF3或CH2CH3;Re6为H、CH3、CH2CHF2或C≡CH;Re7为OH、-OC(=O)Et、-OC(=O)-i-Pr 或-OC(=O)-t-Bu;并且Ae8为N或CH。
纤维素生物合成抑制剂(bl4)抑制某些植物中纤维素的生物合成。它们在对幼嫩或快速生长植物出苗前施用或早期出苗后施用时是最有效的。纤维素生物合成抑制剂的示例包括赛草青、敌草腈、氟胺草唑、三嗪茚草胺 (N2-[(1R,2S)-2,3-二氢-2,6-二甲基-1H-茚-1-基]-6-(1-氟乙基)-1,3,5-三嗪-2,4-二胺)、异噁草胺和三嗪氟草胺。
其它除草剂(b15)包括通过多种不同作用模式而起作用的除草剂,诸如有丝分裂干扰剂(例如高效麦草氟-甲酯和高效麦草氟-异丙酯)、有机含砷化合物(例如DSMA和MSMA)、7,8-二氢蝶酸合成抑制剂、叶绿体类异戊二烯合成抑制剂和细胞壁生物合成抑制剂。其它除草剂包括具有未知作用模式的或不属于(bl)至(bl4)列出的具体类别中的或通过上文列出的作用模式的组合而起作用的那些除草剂。其它除草剂的示例包括苯草醚、磺草灵、杀草强、溴丁酰草胺、环庚草醚、异噁草酮、苄草隆、cyclopyrimorate(6-氯 -3-(2-环丙基-6-甲基苯氧基)-4-哒嗪基4-吗啉甲酸酯)、杀草隆、野燕枯、乙氧苯草胺、伏草隆、抑草丁、调节膦、氨基甲酰基膦酸乙酯铵盐、棉隆、莎扑隆、三唑酰草胺(1-(2,4-二氯苯基)-N-(2,4-二氟苯基)-1,5-二氢-N-(1-甲基乙基)-5-氧代-4H-1,2,4-三唑-4-酰胺)、威百亩、甲基杀草隆、油酸、噁嗪草酮、壬酸、稗草畏和5-[[(2,6-二氟苯基)甲氧基]甲基]-4,5-二氢-5-甲基-3-(3-甲基-2- 噻吩基)异唑。
“除草剂安全剂”(b16)为加入除草制剂中以消除或减少除草剂对某些作物的植物性毒素效应的物质。这些化合物保护作物免受除草剂伤害,但通常不阻止除草剂防治不期望的植被。除草剂安全剂的示例包括但不限于解草酮、解毒-酯、苄草隆、解草胺腈、环丙磺酰胺、杀草隆、二氯丙烯胺、 dicyclonon、哌草丹、解草唑、解草啶、解草安、氟草肟、解草噁唑、双苯噁唑酸-乙酯、吡唑解草酯-、甲基氨基甲酸4-氯苯基酯(mephenate)、去草酮、邻苯二甲酸酐、解草腈、N-(氨甲酰基)-2-甲基苯磺酰胺和N-(氨基羰基)-2- 氟苯磺酰胺、1-溴-4-[(氯甲基)磺酰基]苯、2-(二氯甲基)-2-甲基-1,3-二氧戊环 (MG 191)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(MON 4660)。
可由合成有机化学领域已知的一般方法,制备式1的化合物。本领域中已知有多种合成方法能够制备芳族的和非芳族的杂环环和环系;大量的综述参见八卷集的Comprehensive Heterocyclic Chemistry,A.R.Katritzky和C.W. Rees主编,PergamonPress,Oxford,1984和十二卷集的Comprehensive Heterocyclic Chemistry II,A.R.Katritzky,C.W.Rees和E.F.V.Scriven主编, Pergamon Press,Oxford,1996。
可使用如方案1-22中所述的以下方法和变型中的一种或多种来制备式 1的化合物。除非另外指明,式1–35的化合物中基团R1、R2、R3、R4、W、 X和G的定义如上文发明内容中所定义。除非另外指明,式1a、1b和1c为式1的化合物的子集,并且对于式1a–1c,所有的取代基如上文对式1所限定。除非另外指明,式6a、6b和6c为式6的化合物的子集,并且对于式6a–6c,所有的取代基如对式6所限定。
如方案1中所示,可通过在适当的溶剂中,在碱的存在下,使式1b的取代的5-羟基-3(2H)-哒嗪酮(即式1,其中W为O并且G为H)与式2的适宜亲电试剂(即Z1-G,其中Z1为离去基团,或者称之为离核体,诸如卤素)反应来制备式1a的哒嗪酮(式1的化合物的子集,其中W为O,并且 G如上所定义,但其不为氢)。代表式2(其中Z1为Cl)的试剂类别的一些示例包括:酰氯(G为-(C=O)R8)、氯甲酸酯(G为-CO2R9)、氨基甲酰氯 (G为-CONR10R11)、磺酰氯(G为-S(O)2R8)和氯磺酰胺(G为-S(O)2NR10R11)。用于该反应的适宜碱的示例包括但不限于碳酸钾、氢氧化钠、氢氧化钾、氢化钠或叔丁醇钾,并且根据所用具体碱,适当的溶剂可以是质子的或非质子的并且使用无水的或者作为含水混合物使用。用于该反应的优选溶剂包括乙腈、甲醇、乙醇、四氢呋喃、乙醚、1,2-二甲氧基乙烷、二氧杂环己烷、二氯甲烷或N,N-二甲基甲酰胺。反应可在一定的温度范围内进行,该温度通常在0℃至溶剂回流温度的范围内。
方案1
可通过使式3的酰肼酯(其中R30为烷基,通常为甲基或乙基)在碱和溶剂存在下环化,按照方案2所概述来制备式1b的取代的5-羟基-3(2H)-哒嗪酮。用于该反应的适宜碱包括但不限于碳酸钾、氢氧化钠、氢氧化钾、氢化钠、叔丁醇钾或1,8-二氮杂二环[5.4.0]十一碳-7-烯。根据所用具体碱,适当的溶剂可以是质子的或非质子的并且使用无水的或者作为含水混合物使用。用于该环化反应的溶剂包括乙腈、甲醇、乙醇、四氢呋喃、乙醚、二氧杂环己烷、1,2-二甲氧基乙烷、二氯甲烷或N,N-二甲基甲酰胺。用于该环化反应的温度通常在0℃至溶剂回流温度的范围内。用于使式 CH3(CO2C2H5)C=NNCH3C(=O)CH2Ar(其中Ar为取代的苯基而非式3所示的双环环系)的酰肼酯中间体环化成相应的4-芳基-5-羟基-哒嗪酮的文献方法公开于美国专利8541414和8470738中。这些专利中报道的相同条件适于将式3的腙酯环化成式1b的哒嗪酮。方案2的方法由合成实施例1的步骤F、合成实施例2的步骤H和合成实施例3的步骤H举例说明。
方案2
可通过在碱和溶剂存在下使式4的腙酯(其中R30为烷基,通常为甲基或乙基)与式5的酰氯偶联,按照方案3所概述来制备式3的取代的酰肼酯。用于该反应的优选的碱通常为叔胺诸如三乙胺或Hunig碱,但也可使用其它碱,包括N,N-二甲氨基吡啶、碳酸钾、氢氧化钠、氢氧化钾、氢化钠或叔丁醇钾。根据所用具体碱,适当的溶剂可以是质子的或非质子的,其中反应在无水条件下或者在Schotten-Baumann条件下作为含水混合物发生。用于该种在氮上进行酰化的溶剂包括乙腈、四氢呋喃、乙醚、二氧杂环己烷、甲苯、 1,2-二甲氧基乙烷、二氯甲烷或N,N-二甲基甲酰胺。用于该反应的温度可在 0℃至溶剂回流温度的范围内。用于制备式CH3(CO2C2H5)C=NNCH3C(=O)Ar (其中Ar为取代的苯基)的相关酰肼酯中间体的方法在专利文献已有所公布,参见美国专利8541414和8470738,以及美国专利申请公布2010/0267561。这些专利公布中所公开的过程可直接适用于制备中间体,该中间体可用于制备如方案3中所示的本发明化合物。方案3的方法由合成实施例1的步骤E、合成实施例2的步骤G和合成实施例3的步骤G举例说明。
方案3
通常在0℃至80℃的温度范围内,通过使式R1NHNH2的适当取代的肼与式R2(C=O)CO2R30的酮或醛酯(其中R30通常为甲基或乙基)在适宜的溶剂(诸如乙醇、甲醇、乙腈或二氧杂环己烷或二氯甲烷)中反应而容易地获得式4的腙酯。美国专利申请公布2007/0112038和2005/0256123公开了由甲肼和酮酸酯CH3(C=O)CO2C2H5形成腙的过程。式4的腙酯的制备通过合成实施例1的步骤D举例说明。
如方案4所示,式5的二环乙酰氯可通过酯水解并形成酰氯而由式6(其中R31通常为甲基或乙基)的相应的二环乙酸酯来制备。用于该转化的标准方法在文献中是已知的。例如,酯水解可通过将式6的酯的醇溶液和碱金属氢氧化物的水溶液加热,之后用无机酸进行酸化来实现。然后,形成的式7 的羧酸可通过在惰性溶剂诸如二氯甲烷中用草酰氯和催化量的N,N-二甲基甲酰胺进行处理而转变成式5的相应酰氯。J.Heterocyclic Chem.1983,20(6), 1697–1703;J.Med.Chem.2007,50(1),40–64;以及PCT专利公布WO 2005/012291、WO98/49141和WO 98/49158公开了苯并呋喃-乙酸酯和苯并噻吩-乙酸酯水解为相应的乙酸。Monatshefte für Chemie 1968,99(2)715–720 和专利公布WO 2004046122、WO 2009/038974以及JP09077767公开了苯并呋喃-乙酸和苯并噻吩-乙酸转化为相应的酰氯。方案4的水解步骤由合成实施例1的步骤C、合成实施例2的步骤F和合成实施例3的步骤F举例说明。方案4的酰氯形成步骤由合成实施例1的步骤E、合成实施例2的步骤G和合成实施例3的步骤G举例说明。
方案4
如方案5所示,式6a的苯并呋喃乙酸酯(即式6,其中X为O)可由式8的苯并呋喃-3-酮与式9的(三苯基正膦亚基)乙酸酯(其中R31通常为甲基或乙基)在惰性溶剂诸如四氢呋喃或甲苯中经由Wittig反应制备,或者在适宜溶剂(即通常为无水四氢呋喃或二氧杂环己烷)中在碱诸如氢化钠或叔丁醇钾存在下使用式10的膦酸酯乙酸酯(其中R31通常为甲基或乙基)通过 Wadsworth-Emmons反应制备。该反应包括使最初形成的环外双键(形成二氢苯并呋喃取代的不饱和酯)迁移到苯并呋喃环系内部,由此生成式6a的苯并呋喃乙酸酯。用于Wittig转化的实验条件提供于PCT专利公布WO 2008/074752中。温度范围通常为0℃至溶剂回流温度。在一些情况下,需要更久的加热来驱动与酯共轭的环外双键完全迁移到苯并呋喃环系内的内环位置。方案5的方法通过合成实施例2的步骤E和合成实施例3的步骤E举例说明。
方案5
如方案6所示,式8的取代的苯并呋喃-3-酮(其中R4为氢或烷基)可如下制备:首先在0℃至溶剂回流温度的温度范围内,在适当溶剂(例如乙腈、甲醇、乙醇、四氢呋喃、乙醚、1,2-二甲氧基乙烷、二氧杂环己烷或N,N- 二甲基甲酰胺)中,在碱诸如碳酸钾或氢化钠存在下,用式12的α-溴酯(其中R32通常为甲基或乙基)对式11的水杨酸酯进行烷基化。然后,在惰性溶剂诸如四氢呋喃、二氧杂环己烷、1,2-二甲氧基乙烷或N,N-二甲基甲酰胺中,用金属卤化物或醇化物(例如氢化钠或叔丁醇钾)处理式13的二酯,以形成相应的式8的苯并呋喃-3-酮。另选的用于使式13的二酯转变为式8的苯并呋喃-3-酮的更多分步方法报道于PCT专利公布WO 2008/074752中,而方案5中的方法使得式13的二酯能够环化,之后进行酯水解和脱羧,从而在一个便利步骤中提供式8的苯并呋喃-3-酮。方案6的方法的第一步骤通过合成实施例2的步骤A举例说明。
方案6
如方案7所示,通常在酸性条件下,并且优选地采用纯净的或者通常在惰性高沸点溶剂例如氯苯、二甲苯或甲苯中的多磷酸(PPA),通过使式14 的适当取代的苯硫基酮酯环化而容易地获得式6b的取代的苯并噻吩(即式 6,其中X为S,其中R4为氢或烷基)。氯苯通常为所选溶剂并且对于在氯苯中用PPA进行该环化的文献示例,参见J.HeterocyclicChem.1988,25, 1271-1272。还参见美国专利5376677,其公布的实验细节用于利用该PPA-介导的环化来制备苯并噻吩乙酸酯。方案7的方法通过合成实施例1的步骤 B示出。
方案7
如方案8所示,通过也在J.Heterocyclic Chem.1988,25,1271–1272和美国专利5376677中教导的方法,式14的取代的4-苯硫基-1,3-酮酯可通过在溶剂中在碱存在下用式16的4-溴-1,3-酮酯(即R4CHBr(C=O)CH2CO2R,其中R通常为甲基或乙基)对式15的苯硫酚进行烷基化而容易地制得。在极性非质子溶剂诸如乙腈或N,N-二甲基甲酰胺中用碱金属或碱土金属碳酸盐诸如碳酸钾进行烷化反应通常是优选的。方案8的方法通过合成实施例1的步骤A举例说明。
方案8
如方案9中所示,式6c的萘乙酸酯(即式6,其中X为-C(R6)=C(R7)-) 可由式17的适当取代的萘胺制备。根据该方法,在1,1-二氯乙烯(18)存在下,使式17的胺重氮化(优选地在乙腈中氯化铜的存在下,采用亚硝酸叔丁酯),以给出相应的式19的三氯乙基萘。然后,在适宜溶剂诸如式21的醇存在下,用适当的碱金属或碱土金属的醇盐诸如式20的醇钠加热式19的三氯乙基萘,之后例如用浓硫酸进行酸化,以提供式6c的萘乙酸酯。该方法教导于Pest.Manag.Sci.2011,67,1499–1521和美国专利5376677中。
方案9
用于制备式式6c的萘乙酸酯的另选方法示于方案10中。如Pest.Manag.Sci.2011,67,1499–1521中的方法所教导,可在惰性溶剂诸如二氯甲烷、二氯甲烷或四氯化碳中,在自由基条件(例如过氧化苯甲酰作为催化剂)下用 N-溴琥珀酰亚胺(NBS)溴化式22的甲基萘,以给出式23的萘甲基溴。通过使式23的化合物与碱金属或碱土金属氰化物(例如氰化钾)反应而使溴化物被氰化物取代来提供可水解的式24的萘乙腈,并且通常通过在回流下在酸性醇(例如甲醇或乙醇中的HCl)中加热而酯化为式6c的乙酸酯。
方案10
可如方案11中所示实现哒嗪酮环5-位处离去基团的水解。当LG基团为低级烷氧基、低级烷基硫化物(亚砜或砜)、卤化物或N-键合的唑时,其可通过在0℃至120℃的温度下,在溶剂诸如四氢呋喃、二甲氧基乙烷或二氧杂环己烷中用碱性试剂诸如氢氧化四丁基铵进行水解来移除。可用于该水解的其它氢氧化物试剂包括氢氧化钾、氢氧化锂和氢氧化钠(参见例如 WO 2009/086041)。当LG基团为低级烷氧基时,LG基团的水解也可利用脱烷基化试剂诸如三溴化硼或吗啉来实现(参见例如WO 2009/086041、WO 2013/160126和WO2013/050421)。
方案11
将卤素引入哒嗪酮的6-位可通过进行锌酸盐处理(zincation),之后进行卤化来实现。用于哒嗪酮的锌酸盐处理的条件、试剂和示例参见Verhelst, T.,博士论文,University of Antwerp,2012。通常,在-20℃至30℃下,在四氢呋喃中用Zn(TMP)-LiCl或Zn(TMP)2-MgCl2-LiCl溶液(可商购获得的)处理式26的哒嗪酮,以形成锌试剂。随后添加溴或碘提供式27的化合物(其中R2分别为Br或I)。该方法示于方案12中。对于多种适当的锌酸盐试剂的制备,参见Wunderlich,S.博士论文,University of Munich,2010和其中引用的参考文献,以及WO 2008/138946和WO 2010/092096。哒嗪酮环6-位上的锌酸盐处理可在哒嗪酮环4-位上的芳族/杂芳族取代基、烷氧基取代基或卤素存在下,或者在哒嗪酮环5-位上的卤素或烷氧基取代基存在下实现。
方案12
式28的化合物的R2取代基(其中R2为卤素或磺酸根)可进一步转化成其它官能团。如方案13所示,化合物(其中R2为烷基、环烷基或取代的烷基)可通过过渡金属催化式28的化合物反应来制备。对于这些类型反应的综述,参见:E.Negishi的Handbook ofOrganopalladium Chemistry for Organic Synthesis,John Wiley and Sons,Inc.,NewYork,2002,N.Miyaura 的Cross-Coupling Reactions:A Practical Guide,Springer,NewYork,2002, H.C.Brown等人的Organic Synthesis via Boranes,Aldrich Chemical Co.,Milwaukee,第3卷,2002,Suzuki等人的Chemical Reviews 1995,95,2457-2483 和Molander等人的Accounts of Chemical Research 2007,40,275-286。还可参见Gribble和Li编辑的Palladium in Heterocyclic Chemistry,第1卷, Pergamon Press,Amsterdam,2000以及Gribble和Li编辑的Palladium in Heterocyclic Chemistry,第2卷,PergamonPress,Amsterdam,2007。对于 Buchwald-Hartwig chemistry的综述,参见Yudin和Hartwig,Catalyzed Carbon-Heteroatom Bond Formation,2010,Wiley,New York。
方案13
用于将其它官能团引入式29的R-位的相关合成方法在本领域中是已知的。铜催化的反应可用于引入CF3基团。用于该反应的试剂的近来全面综述参见Wu,Neumann andBeller in Chemistry:An Asian Journal,2012,ASAP和其中引用的参考文献。对于将含硫取代基引入该位置,参见公开于WO 2013/160126的方法。对于引入氰基基团,参见WO 2014/031971。对于引入硝基基团,参见J.Am.Chem.Soc.,2009,12898。对于引入氟取代基,参见J.Am.Chem.Soc.,2014,3792。
如方案14所示,式28的化合物可通过使有机金属试剂与在4-位上具有反应性基团的式29的哒嗪酮反应来制备。根据离去基团,过渡金属催化剂是可取的。当离去基团为低级烷氧基、N-键合的唑(诸如吡唑或三唑)或磺酸根时,不需要催化剂,并且直接与镁试剂的反应可在4-位发生。反应可在不与有机镁试剂反应的各种溶剂中进行。通常反应条件包括:作为溶剂的四氢呋喃、-20℃至65℃的反应温度,和过量的有机镁试剂。当4-位上的反应性基团为卤素时,过渡金属催化剂和配体是有用的。可使用各种不同的偶联配偶体,包括硼(Suzuki Reaction)、锡(Stille Reaction)和锌(Negishi reaction);这些反应可通过钯和镍催化剂与各种不同的配体催化。用于这些反应的条件在本领域中是已知的;参见例如Palladium-Catalyzed Coupling Reactions: Practical Aspects and FutureDevelopment,Arpad Molnar,Wiley编辑,2013 和其中引用的文献。用于非催化过程的有机镁试剂可如下制备:通过将镁直接插入碳-卤素键(任选地在卤化锂存在下),通过与异-丙基卤化镁(任选地在卤化锂存在下)的Grignard交换反应,或者通过与镁盐诸如溴化镁醚化物反应来转化有机锂试剂。在这些反应中,可在哒嗪酮的R2上或5-位上存在对有机镁试剂呈惰性的各种基团。
方案14
式29的化合物在本领域中是已知的或者可通过Maes和Lemiere在ComprehensiveHeterocyclic Chemistry III,第8卷,Katritsky,Ramsden,Scriven 和Taylor编辑和其中引用的参考文献中所述的方法来制备。还可参见 Verhelst,博士论文(University ofAntwerp)和其中引用的参考文献。哒嗪酮上的官能团的转化还描述于Stevenson等人的J.Heterocyclic Chem.2005,42, 427;美国专利6,077,953;WO 2009/086041和其中引用的参考文献;美国专利2,782,195;WO 2013/160126;和WO 2013/050421中。
式1b的化合物还可通过使式31的磺酸酯在碱水溶液中水解来制备。适宜的碱包括氢氧化钠、氢氧化钾或氢氧化四丁基铵。典型的反应温度在0℃至80℃范围内,并且典型的反应时间为1-12小时。该方法示于方案15中。
方案15
式31的化合物可通过用碱处理式32的化合物进行环化来制备。可用于该方法的典型的碱包括碳酸钾、碳酸钠或碳酸铯。典型的溶剂包括乙腈、四氢呋喃或N,N-二甲基甲酰胺。该方法示于方案16中。
方案16
式32的化合物可通过方案17中所示的方法制备。在该方法中,式33 的化合物在碱存在下与式34的化合物偶联。可用于该方法的碱包括三乙胺、碳酸钠或碳酸钾、吡啶或二异丙基乙胺。
方案17
式33的化合物可通过本领域已知的方法制备。
式34的化合物可通过若干方法制备。在方案18所示的一种方法中,首先在三氯化铝的存在下用ClC(O)CO2Me处理式35的化合物。随后水解为羧酸,之后用草酰氯进行处理,提供式34的酰氯。
方案18
式35的化合物可商购获得或可通过本领域已知的方法制备。
如方案20中所示,式1c的化合物可通过使式30的化合物重排制备。该重排可在介于110℃和300℃之间的温度下进行。适宜的溶剂包括但不限于芳香烃诸如二甲苯、二乙苯和均三甲苯,以及卤代芳族化合物诸如二氯苯。可成功地使用其它高沸点溶剂诸如Dowtherm A和二甘醇二甲醚。特别在将离子液体添加至介质时,具有较低沸点的多种其它溶剂可与微波加热结合使用。
方案20
如方案21所示,可通过用式32的烷代卤将式31的哒嗪酮烷基化来制备式30的化合物。反应可在各种溶剂中进行,诸如丙酮、2-丁酮、乙腈、二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜和二甲基甲酰胺。酸受体的存在是优选的,诸如但不限于碳酸铯、碳酸钾、碳酸钠、氢氧化钾或氢氧化钠。离去基团Y可为卤素或磺酸根。
方案21
如方案22所示,还可通过式33的哒嗪酮与式33的醇的亲核置换反应来制备式30的化合物。适宜的溶剂包括二氧杂环己烷、二甲氧基乙烷、四氢呋喃、二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜和二甲基甲酰胺。适宜的酸受体包括但不限于氢化钠、氢化钾、叔丁醇钾、六甲基二硅基氨基钠、六甲基二硅基氨基钾和六甲基二硅基氨基锂。
方案22
如方案23所示,通常在0℃至室温的温度范围内,可用硫化试剂将式 1a的哒嗪酮(式1的化合物的子集,其中W为O)硫化以给出相应的式1c (即式1,其中W为S)的硫酮,该硫化试剂通常为吡啶中的五硫化二磷或适当溶剂(例如甲苯、四氢呋喃或二氧杂环己烷)中的Lawesson试剂(2,4- 二-(4-甲氧基苯基)-1,3-二硫杂-2,4-二磷杂环丁烷2,4-二硫化物)。
方案23
本领域的技术人员认识到,各种官能团可被转变成其它以提供不同的式 1的化合物。对于以简单并且直观的方式示出官能团互变的可贵资源,参见 Larock,R.C.,Comprehensive Organic Transformations:A Guide to Functional GroupPreparations,第2版,Wiley-VCH,New York,1999。
已经认识到,上述用于制备式1的化合物的某些试剂和反应条件可能与中间体中存在的某些官能团不相容。在这些情况下,将保护/去保护序列或官能团互变体掺入合成中将有助于获得所期望的产物。保护基团的使用和选择对于化学合成领域的技术人员将是显而易见的(参见例如Greene,T.W.; Wuts,P.G.M.Protective Groups in OrganicSynthesis第2版;Wiley:New York, 1991)。本领域的技术人员将认识到,在一些情况下,在按照任何单独方案中所示引入指定试剂后,可能需要实施未详细描述的附加常规合成步骤以完成式1的化合物的合成。本领域的技术人员还将认识到,需要以与制备式1 的化合物时呈现的具体序列不相同的次序来实施上文方案中示出的步骤的组合。
本领域的技术人员还将认识到,本文所述的式1的化合物和中间体可经历各种亲电反应、亲核反应、自由基反应、有机金属反应、氧化反应和还原反应,以添加取代基或修饰现有的取代基。
可用于制备本发明化合物的中间体的示例示于表I-1a至I-3d中。表I-1a 至I-3d中的R3基团的位置基于以下所示位次编号。
下列缩写用于随后的表中:Me代表甲基,Et代表乙基,Pr代表丙基,并且Ph代表苯基。
表I-1a
X为S,并且R为CO2Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
- | H | - | Me | - | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,并且R为CO2Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,并且R为CO2H。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,并且R为C(O)Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,并且R为CO2Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,并且R为CO2Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,并且R为CO2H。
X为-CH=CH-,并且R为C(O)Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CF-,并且R为CO2Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CF-,并且R为CO2Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CF-,并且R为CO2H。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CF-,并且R为C(O)Cl。
表I-1b
X为S,R1为Me,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为Et。
X为S,R1为Et,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为I。
X为-CH=CH-,R1为Et,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CCl-,R1为Et,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CCl-,R1为Et,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CCl-,R1为Et,并且R2为Br。
X为-CH=CCl-,R1为Et,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CCl-,R1为Et,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CCl-,R1为Et,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
表I-2a
X为S,并且R为CO2Na。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,并且R为CO2K。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,并且R为CO2H。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,并且R为C(O)Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,并且R为CO2Na。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,并且R为CO2K。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,并且R为CO2H。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,并且R为C(O)Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
表I-2b
X为S,R1为Me,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Me,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为I。
X为S,R1为Et,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R1为Et,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Br。
X为-CH=CH-,R1为Me,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Me,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R1为Et,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
表I-2c
表I-2c与表I-2b相同,不同的是R1为-SO2Ph。
表I-2d
表I-2d与表I-2b相同,不同的是R1为-SO2(4-甲基苯基)。
表I-2e
表I-2e与表I-2b相同,不同的是R1为-SO2(4-氯苯基)。
表I-3a
X为S,R为Me,R1为Me,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Me,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Me,并且R2为Br。
X为S,R为Me,R1为Me,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Me,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Me,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Et,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Et,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Et,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Et,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Et,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为S,R为Me,R1为Et,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Me,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Me,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Me,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Me,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Me,并且R2为Cl。
X为-CH=CH-,R为Me,R1为Me,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Et,并且R2为Me。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Et,并且R2为Et。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Et,并且R2为Br。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Et,并且R2为I。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Et,并且R2为Cl。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
X为-CH=CH-,R为Me,R1为Et,并且R2为OMe。
(R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> | (R<sup>3</sup>)<sub>n</sub> | R<sup>4</sup> |
– | H | – | Me | – | Et |
5-Me | H | 5-Me | Me | 5-Me | Et |
4,6-二-Me | H | 4,6-二-Me | Me | 4,6-二-Me | Et |
5,7-二-Me | H | 5,7-二-Me | Me | 5,7-二-Me | Et |
表I-3b
表I-3b与表I-3a相同,不同的是R为苯基。
表I-3c
表I-3c与表I-3a相同,不同的是R为4-甲基苯基。
表I-3d
表I-3d与表I-3a相同,不同的是R为4-氯苯基。
无需进一步详尽说明,据信本领域的技术人员使用前述说明可将本发明利用至其最大限度。以下非限制性实施例是本发明的例示。以下实施例中的步骤示出了整个合成转化中各步骤的过程,并且用于各步骤的起始物质并不必须由其过程描述于其它实施例或步骤中的具体制备步骤来制备。百分比均按重量计,除了色谱溶剂混合物或除非另外指明之外。除非另外指明,色谱溶剂混合物的份数和百分比均按体积计。除非另外指明,在CDCl3溶液中以距四甲基硅烷的低场ppm数为单位记录1H NMR波谱;“s”表示单峰,“d”表示双重峰,“t”表示三重峰,“q”表示四重峰,“m”表示多重峰,并且“br s”表示宽单峰。
合成实施例1
4-(2,5-二甲基苯并[b]噻吩-3-基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物
1)的制备
步骤A:4-[(4-甲基苯基)硫代]-3-氧代戊酸乙酯的制备
在氮气下(即在氮气气氛下)于室温下向碳酸钾(1.11g,8.03mmol) 的N,N-二甲基甲酰胺(DMF)(27mL)的混合物中添加4-甲基苯硫酚(0.626g, 5.04mmol)。使混合物冷却至0℃,然后在10分钟内通过注射器滴加4-溴-3- 氧代戊酸乙酯(1.25g,5.04mmol)。使混合物温热至室温,同时搅拌16h。然后将混合物倾注到盐酸水溶液(0.2M,80mL)中并用乙醚萃取(3×50mL)。使合并的萃取物干燥(MgSO4)并浓缩。通过快速色谱法(0至10%梯度的乙酸乙酯的己烷溶液)纯化粗制残余物,以获得为黄色油状物的标题产物 (0.82g)。
1H NMRδ7.27–7.31(m,2H),7.12(m,2H),4.18(m,2H),3.82(q,1H), 3.64–3.77(m,2H),2.33(s,3H),1.38(d,3H),1.24–1.30(m,3H)。
步骤B:2,5-二甲基苯并[b]噻吩-3-乙酸乙酯的制备
将多磷酸(1mL)添加至氯苯(无水,20mL)中,并且在氮气下将混合物加热至回流。在约30分钟内,经由注射器向混合物中滴加4-[(4-甲基苯基)硫代]-3-氧代戊酸乙酯(即步骤A的产物)(0.82g,3.08mmol)。使混合物保持回流16h。然后使混合物冷却至室温,并且将上层氯苯滗出至独立的烧瓶中并浓缩。通过快速色谱法(0至10%梯度的乙酸乙酯的己烷溶液) 纯化粗制残余物,以获得为白色固体的标题产物(0.33g)。
1H NMRδ7.61(d,1H),7.46(s,1H),7.10–7.12(m,1H),4.10–4.17(m,2H),3.74 (s,2H),2.53(s,3H),2.46(s,3H),1.22–1.25(m,3H)。
步骤C:2,5-二甲基苯并[b]噻吩-3-乙酸的制备
将2,5-二甲基苯并[b]噻吩-3-乙酸乙酯(即步骤B的产物)(0.33g, 1.33mmol)溶解于甲醇(50mL)中,并且添加氢氧化钠水溶液(2M,5mL, 10mmol)。将混合物加热回流3h。然后使混合物冷却,并且通过旋转蒸发除去溶剂。向残余物中添加水(50mL),并且通过小心添加浓盐酸将pH调节至~1。然后用二氯甲烷(3×50mL)萃取混合物,并且使合并的有机萃取物干燥(MgSO4)、过滤并通过旋转蒸发浓缩,以获得为白色固体的标题产物(0.26g)。
1H NMRδ7.62(d,1H),7.43(s,1H),7.11(m,1H),3.78(s,2H),2.53(s,3H), 2.46(s,3H)。
步骤D:2-(2-甲基肼亚基)丙酸甲酯的制备
向冷却至0℃的2-氧代丙酸甲酯(17.0mL,169mmol)和硫酸镁(20.46g, 170mmol)的三氯甲烷(250mL)悬浮液中添加甲基肼(9.0mL,166mmol) 的三氯甲烷(50mL)溶液。然后使反应混合物温热至室温。在室温下搅拌 24h之后,将反应混合物过滤。减压浓缩滤液,以给出为黄色固体的标题产物(21.16g),该产物直接用于下一步而无需进一步纯化。随后,通过快速色谱法纯化该样品的一部分,以提供灰白色固体。
1H NMRδ5.63(br s,1H),3.82(s,3H),3.22–3.24(m,3H),1.93(s,3H)。
步骤E:2-[2-[2-(2,5-二甲基苯并[b]噻吩-3-基)乙酰基]-2-甲基肼亚基]丙酸甲
酯的制备
向2,5-二甲基苯并[b]噻吩-3-乙酸(即步骤C的产物)(0.26g,1.2mmol) 的二氯甲烷(40mL)溶液中添加草酰氯(0.25mL,3.0mmol),之后添加催化量的DMF(3滴)。使混合物在氮气下搅拌2h,然后通过旋转蒸发浓缩。将包含酰氯的残余物溶解于乙腈(25mL)中并在氮气下于15min内滴加至冷却至0℃的2-(2-甲基肼亚基)丙酸甲酯(即步骤D的产物)(0.20g,1.5mmol) 和碳酸钾(0.28g,2.0mmol)在乙腈(20mL)中的混合物中。然后使反应混合物温热至室温并搅拌64h。通过旋转蒸发去除溶剂,并且将水(50mL)添加至残余物。水相用乙酸乙酯(3×50mL)萃取,并且将合并的有机萃取物用盐水(即饱和的氯化钠水溶液)(50mL)洗涤,干燥(MgSO4)、过滤并通过旋转蒸发浓缩。通过快速色谱法(10%至50%梯度的乙酸乙酯的己烷溶液)纯化残余物,以获得白色固体(0.23g)。
1H NMRδ7.55–7.61(m,1H),7.45–7.46(m,1H),7.04–7.09(m,1H),4.08–4.17 (m,2H),3.88(s,3H),3.34(s,3H),2.51(s,3H),2.42(s,3H),2.20(s,3H)。
步骤F:4-(2,5-二甲基苯并[b]噻吩-3-基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮的
制备
在30分钟时间内,在氮气下,经由注射器泵将2-[2-[2-(2,5-二甲基苯并 [b]噻吩-3-基)乙酰基]-2-甲基肼亚基]丙酸甲酯(即步骤E的产物)(0.23g, 0.69mmol)的DMF(无水,3mL)溶液添加于冷却至0℃的叔丁醇钾(3.0mL, 3mmol)的四氢呋喃溶液中。然后使反应混合物温热至室温,同时搅拌1h。将反应混合物倾注到盐酸水溶液(0.5M,100mL)中,并用乙酸乙酯萃取(3 ×50mL)。合并的有机萃取物用盐水(50mL)洗涤、干燥(MgSO4)、过滤并通过旋转蒸发浓缩,以获得粗制残余物(0.40g),该粗制残余物通过快速色谱法(0至40%梯度的乙酸乙酯的己烷溶液)纯化,以获得为白色固体的标题产物(118mg),即本发明的化合物。
1H NMRδ7.60(d,1H),7.09(m,1H),7.02(s,1H),6.91(br s,1H),3.52(s,3H),2.39(s,3H),2.21(s,3H),2.17(s,3H)。
合成实施例2
4-(2,5-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮(化合物7)的
制备
步骤A:2-(2-甲氧基-1-甲基-2-氧代乙氧基)-5-甲基苯甲酸甲酯的制备
使2-羟基-5-甲基苯甲酸甲酯(11.89g,71.5mmol)、2-溴丙酸甲酯(13.03g,78.0mmol)和碳酸钾(29.71g,215mmol)在丙酮(300mL)中的混合物加热回流18h。然后过滤反应混合物,并且通过旋转蒸发浓缩滤液,以获得为白色固体的标题产物(18.9g)。
1H NMRδ7.61(s,1H),7.15–7.24(m,1H),6.70–6.84(m,1H),4.73(m,1H), 3.89(s,3H),3.74(s,3H),2.30(s,3H),1.63–1.65(d,3H)。
步骤B:2-(1-羧基乙氧基)-5-甲基苯甲酸的制备
将2-(2-甲氧基-1-甲基-2-氧代乙氧基)-5-甲基苯甲酸甲酯(即步骤A的产物)(18.9g,71.5mmol)在四氢呋喃(100mL)、甲醇(100mL)和NaOH 水溶液(6M,100mL)的混合物中的溶液加热回流16h。然后将反应混合物冷却并通过旋转蒸发浓缩。将残余物溶解于水(150mL)中并用浓盐酸水溶液酸化至pH<2。用乙酸乙酯(2×125mL)萃取水相。用盐水洗涤合并的有机萃取物,干燥(MgSO4),过滤并通过旋转蒸发浓缩,以给出为黄色固体的标题产物(16.31g),该产物用于步骤C而无需进一步纯化。
1H NMRδ7.91(d,1H),7.36(m,1H),6.90(d,1H),4.99(m,1H),2.34(s,3H), 1.75–1.80(m,3H)。
步骤C:2,5-二甲基-3-苯并呋喃基乙酸酯的制备
将2-(1-羧基乙氧基)-5-甲基苯甲酸(即步骤B的产物)(16.3g,71mmol)、乙酸酐(145mL)和乙酸钠(11.93g,145mmol)的混合物加热回流3h。在冷却之后,将混合物添加至水(300mL)中并用二氯甲烷(2×150mL)萃取。干燥(MgSO4)并过滤有机萃取物,并且通过旋转蒸发浓缩滤液,以获得为淡棕色油状物的标题产物(14.43g),该产物用于步骤D而无需进一步纯化。
1H NMRδ7.22–7.25(m,1H),7.07–7.11(m,1H),7.01–7.04(m,1H),2.41(s, 3H),2.37(s,3H),2.34(s,3H)。
步骤D:2,5-二甲基-3(2H)-苯并呋喃酮的制备
将2,5-二甲基-3-苯并呋喃基乙酸酯(即步骤C的产物)(14.40g, 70.5mmol)、甲醇(150mL)和盐酸水溶液(1.0M,40mL,40mmol)的混合物在氮气下加热回流。然后通过旋转蒸发浓缩反应混合物。将残余物用水稀释并用乙醚(2×100mL)萃取。合并的有机萃取物用水和盐水洗涤、干燥(MgSO4)、过滤并浓缩。通过快速色谱法(0至15%梯度的乙酸乙酯的己烷溶液)纯化残余物,以获得为白色固体的标题产物(7.47g)。
1H NMRδ7.41–7.46(m,2H),6.99–7.02(m,1H),4.60–4.64(q,1H),2.35(s,3H),1.50–1.54(d,3H)。
步骤E:2,5-二甲基-3-苯并呋喃乙酸甲酯的制备
将2,5-二甲基-3(2H)-苯并呋喃酮(即步骤D的产物)(7.45g,45.9mmol)、 2-(三苯基正膦亚基)乙酸甲酯(20.43g,61.1mmol)和甲苯(300mL)的混合物加热回流66h。然后通过旋转蒸发浓缩反应混合物,并且将乙醚(200mL) 添加至粗制残余物。将该混合物过滤以除去固体,并且通过旋转蒸发浓缩滤液,以留下油性混合物(18g)。向该残余物中添加甲醇(40mL)和氯化氢甲醇溶液(0.5M,60mL,30mmol),并且将混合物加热回流16h。然后将反应混合物冷却并通过旋转蒸发浓缩。通过快速色谱法(0至10%梯度的乙酸乙酯的己烷溶液)纯化残余物,以提供为黄色油状物的标题产物(6.75g)。1H NMRδ7.19–7.27(m,2H),6.98–7.05(m,1H),3.693(s,3H),3.584(s,2H), 2.40–2.45(m,6H)。
步骤F:2,5-二甲基-3-苯并呋喃乙酸的制备
将氢氧化钠水溶液(5M,33mL,165mmol)添加至2,5-二甲基-3-苯并呋喃乙酸甲酯(即步骤E的产物)(6.75g,30.9mmol)的甲醇(120mL) 溶液中。将混合物加热至回流持续16h并然后冷却。通过旋转蒸发除去溶剂。向残余物中添加乙醚(100mL),并且用氢氧化钠水溶液(1N,2×100mL) 萃取所得的混合物。弃去醚层,并且将合并的萃取物水溶液用浓盐酸水溶液酸化至pH 1。用二氯甲烷(2×125mL)萃取所得的酸性含水混合物。合并的有机萃取物用盐水(100mL)洗涤,干燥(MgSO4),过滤并通过旋转蒸发浓缩,以获得为黄色固体的标题产物(4.93g),该产物用于步骤G而无需进一步纯化。
1H NMRδ7.22–7.28(m,2H),6.99–7.05(m,1H),3.61(s,2H),2.42(s,3H),2.41 (s,3H)。
步骤G:2-[2-[2-(2,5-二甲基-3-苯并呋喃基)乙酰基]-2-甲基肼亚基]丙酸甲酯
的制备
向2,5-二甲基-3-苯并呋喃乙酸(即步骤F的产物)(4.14g,20.2mmol) 的二氯甲烷(120mL)溶液中添加草酰氯(2.56mL,30.0mmol),之后添加催化量的DMF(5滴)。在氮气下使所得的混合物搅拌2h,然后通过旋转蒸发浓缩,以留下包含酰氯的残余物。将残余物溶解于乙腈(50mL)中,并且在25min内,在氮气下从加料漏斗滴加至冷却至0℃的2-(2-甲基肼亚基) 丙酸甲酯(2.81g,21.6mmol)和碳酸钾(3.18g,23.0mmol)的乙腈(30mL) 混合物中。然后使反应混合物温热至室温并搅拌64h。通过旋转蒸发去除溶剂,并且将水(150mL)添加至残余物。所得的混合物用乙酸乙酯(3×80mL) 萃取,并且将合并的有机萃取物用盐水(50mL)洗涤,干燥(MgSO4)、过滤并通过旋转蒸发浓缩。通过快速色谱法(10%至100%梯度的乙酸乙酯的己烷溶液)纯化残余物,以获得为白色固体的标题产物(3.08g)。
1H NMRδ7.32(m,1H),7.22–7.24(m,1H),6.98–6.99(m,1H),3.96(s,2H), 3.90(s,3H),3.35(s,3H),2.40(m,6H),2.20(s,3H)。
步骤H:4-(2,5-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮的制
备
在30分钟内,在氮气下,将2-[2-[2-(2,5-二甲基-3-苯并呋喃基)乙酰基]-2- 甲基肼亚基]丙酸甲酯(即步骤G的产物)(2.97g,9.39mmol)的无水DMF (25mL)溶液从加料漏斗添加于冷却至0℃的叔丁醇钾(25.0mL,25.0mmol) 的四氢呋喃溶液中。然后使反应混合物温热至室温并搅拌1h。将反应混合物倾注到盐酸水溶液(0.5M,150mL)中并用乙酸乙酯萃取(3×90mL)。合并的有机萃取物用盐水(100mL)洗涤、干燥(MgSO4)、过滤并通过旋转蒸发浓缩。通过快速色谱法(10%至75%梯度的乙酸乙酯的己烷溶液)纯化残余物,以获得为白色固体的标题产物(790mg),即本发明的化合物。
1H NMR(DMSO-d6)δ10.29(s,1H),7.39(m,1H),7.04(m,1H),6.95–7.01(m, 1H),3.60(s,3H),2.32(s,3H),2.25(m,6H)。
合成实施例3
5-羟基-2,6-二甲基-4-(2,5,7-三甲基-3-苯并呋喃基)-3(2H)-哒嗪酮(化合物
12)的制备
步骤A:丙酸2,4-二甲基苯酯的制备
在氮气下,将丙酰氯(2.44g,26.4mmol)滴加于冷却至0℃的2,4-二甲基苯酚(3.26g,24mmol)和三乙胺(3.51mL,25mmol)的二氯甲烷(35mL) 混合物中。将混合物搅拌16h,然后添加盐酸水溶液(0.2M,50mL)。分离有机相,并且用二氯甲烷(50mL)萃取水相。用盐水洗涤合并的有机相,干燥(MgSO4),过滤并浓缩,以获得为黄色油状物的标题产物(3.91g),该产物直接用于下一步骤而无需进一步纯化。
1H NMRδ7.03(s,1H),6.99(d,1H),6.87(d,1H),2.56–2.62(m,2H),2.30(s, 3H),2.14(s,3H),1.26–1.31(m,3H)。
步骤B:1-(2-羟基-3,5-二甲基苯基)-1-丙酮的制备
将氯化铝(3.10g,23.2mmol)添加至丙酸2,4-二甲基苯酯(即步骤A 的产物)(3.91g,21.9mmol)中,并且将形成的混合物加热至130℃持续 2h。然后使混合物冷却至室温,并且添加盐酸水溶液(1.0M,100mL),之后添加乙醚(100mL)。分离有机相,并且用乙醚(50mL)萃取水相。将合并的有机萃取物干燥(MgSO4)、过滤并浓缩,以获得为黄色结晶状固体的标题产物(3.71g),其直接用于下一步骤而无需进一步纯化。
1H NMRδ12.49(s,1H),7.40(s,1H),7.16(s,1H),3.03(m,2H),2.29(s,3H), 2.23(s,3H),1.22–1.25(m,3H)。
步骤C:2-溴-1-(2-羟基-3,5-甲基苯基)-1-丙酮的制备
从加料漏斗向溴化铜(II)(9.30g,41.6mmol)的乙酸乙酯(30mL)混合物中滴加溶于三氯甲烷(24mL)的1-(2-羟基-3,5-二甲基苯基)-1-丙酮(即步骤B的产物)(3.71g,20.8mmol)溶液。将所得的混合物加热至回流持续 16h,然后冷却至室温并使其过滤通过填充有硅藻土助滤剂的过滤漏斗。浓缩滤液,残余物用乙醚(100mL)稀释并用饱和乙二胺四乙酸二钠盐水溶液(100mL)洗涤。将有机相干燥(MgSO4)、过滤并通过旋转蒸发浓缩,以获得为棕色油状物的标题产物(5.33g),该产物直接用于下一步骤而无需进一步纯化。
1H NMRδ12.09(s,1H),7.39–7.44(m,1H),7.18–7.23(m,1H),5.31–5.40(m, 1H),2.29(s,3H),2.24(s,3H),1.90(d,3H)。
步骤D:2,5,7-三甲基-3(2H)-苯并呋喃酮的制备
将N,N-二甲基甲酰胺(25mL)和碳酸钾(4.15g,30mmol)添加至2- 溴-1-(2-羟基-3,5-甲基苯基)-1-丙酮(即步骤C的产物)(5.33g,20.7mmol) 中,并且将所得的混合物在室温下搅拌18h。然后添加水(150mL),并且用乙醚(3×80mL)萃取混合物。合并的有机萃取物用水洗涤,之后用盐水洗涤、干燥(MgSO4)、过滤并浓缩。通过快速色谱法(用0至10%梯度的乙酸乙酯的己烷溶液洗脱)纯化残余物,以获得为黄色油状物的标题产物 (2.13g)。
1H NMRδ7.26–7.28(m,1H),7.24–7.26(m,1H),4.59–4.64(m,1H),2.32(s, 3H),2.29(s,3H),1.52(d,3H)。
步骤E:2,5,7-三甲基-3-苯并呋喃乙酸甲酯的制备
将2,5,7-三甲基-3(2H)-苯并呋喃酮(即步骤D的产物)(2.07g, 11.7mmol)、2-(三苯基正膦亚基)乙酸甲酯(5.89g,17.6mmol)和甲苯(120mL) 的混合物加热回流66h。然后通过旋转蒸发浓缩反应混合物,并向残余物中添加乙醚(150mL)。过滤所得的混合物以除去固体,并通过旋转蒸发浓缩滤液,以留下油性混合物(6g)。向该残余物中添加甲醇(100mL)和氯化氢的甲醇溶液(0.5M,30mL,15mmol)。将所得的混合物加热至回流持续 16h并然后冷却。通过旋转蒸发浓缩混合物,以留下残余物,该残余物经快速色谱法(0至5%梯度的乙酸乙酯的己烷溶液)纯化,以获得为黄色油状物的标题产物(0.59g),该产物在下一步使用而无需进一步纯化。
1H NMRδ7.06(s,1H),6.83(s,1H),3.68(s,3H),3.57(s,2H),2.44(s,3H),2.42(s,3H),2.39(s,3H)。
步骤F:2,5,7-三甲基-3-苯并呋喃乙酸的制备
向2,5,7-三甲基-3-苯并呋喃乙酸甲酯(即步骤E的产物)(0.55g, 2.37mmol)的甲醇(50mL)溶液中添加氢氧化钠水溶液(5M,2mL,10mmol)。将所得的混合物加热至回流持续16h并然后冷却。通过旋转蒸发除去溶剂。向残余物中添加乙醚(100mL),并且用氢氧化钠水溶液(1N,2×100mL) 萃取所得的混合物。弃去醚层,并且将合并的碱性萃取物用浓盐酸水溶液酸化至pH 1。然后用二氯甲烷(2×125mL)萃取酸性含水混合物。将合并的有机萃取物干燥(MgSO4)、过滤并通过旋转蒸发浓缩,以获得为黄色固体的标题产物(0.52g),该产物用于下一步骤而无需进一步纯化。
1H NMRδ7.05(s,1H),6.84(s,1H),3.60(s,2H),2.43(s,3H),2.41(s,3H),2.38(s,3H)。
步骤G:2,5,7-三甲基-3-苯并呋喃乙酸2-(2-甲氧基-1-甲基-2-氧代亚乙基)-1-
甲基酰肼的制备
向2,5,7-三甲基-3-苯并呋喃乙酸(即步骤F的产物)(0.52g,2.38mmol) 的二氯甲烷(80mL)溶液中添加草酰氯(0.5mL,6.0mmol),之后添加催化量的DMF(3滴)。在氮气下使所得的混合物搅拌2h,然后通过旋转蒸发浓缩。将包含2,5,7-三甲基-3-苯并呋喃乙酰氯的残余物溶解于乙腈(50mL) 中,并且在25min内在氮气下从加料漏斗滴加于冷却至0℃的2-(2-甲基肼亚基)丙酸甲酯(0.35g,2.7mmol)和碳酸钾(0.69g,5.0mmol)的乙腈(30mL) 混合物中。然后,使反应混合物温热至室温并搅拌18h。通过旋转蒸发去除溶剂,并且向残余物中添加水(90mL)。所得的混合物用乙酸乙酯(3×50mL) 萃取,并且将合并的有机萃取物用盐水(50mL)洗涤,干燥(MgSO4)、过滤并通过旋转蒸发浓缩。通过快速色谱法(5%至50%梯度的乙酸乙酯的己烷溶液)纯化残余物,以获得为黄色固体的标题产物(0.32g)。
1H NMRδ7.14(s,1H),6.80(s,1H),3.95(s,2H),3.90(s,3H),3.35(s,3H),2.42(s,3H),2.41(s,3H),2.36(s,3H),2.19(s,3H)。
步骤H:5-羟基-2,6-二甲基-4-(2,5,7-三甲基-3-苯并呋喃基)-3(2H)-哒嗪酮的
制备
在1h内,在氮气下,通过注射器泵将2,5,7-三甲基-3-苯并呋喃乙酸2-(2- 甲氧基-1-甲基-2-氧代亚乙基)-1-甲基酰肼(即步骤G的产物)(0.31g, 1.0mmol)的N,N-二甲基甲酰胺(无水,5mL)溶液添加于冷却至0℃的叔丁醇钾(1M,5.0mL,5.0mmol)的四氢呋喃溶液中。使反应混合物温热至室温并搅拌1h。然后将混合物倾注到盐酸水溶液(0.5M,60mL)中并用乙酸乙酯萃取(3×50mL)。合并的有机萃取物用盐水(60mL)洗涤、干燥 (MgSO4)、过滤并通过旋转蒸发浓缩。通过快速色谱法(5%至100%梯度的乙酸乙酯的己烷溶液)纯化所得的残余物,以获得为白色固体的标题产物 (72.3mg),即本发明的化合物。
1H NMRδ6.88(s,1H),6.84(s,1H),5.86(br s,1H),3.74(s,3H),2.48(s,3H),2.38(s,3H),2.36(s,3H),2.34(s,3H)。
合成实施例4
4-(2,3-二甲基-1-萘基)-5-羟基-6-甲氧基-2-甲基-3(2H)-哒嗪酮(化合物46)的
制备
步骤A:5-氯-4,6-二甲氧基-2-甲基-3(2H)-哒嗪酮的制备
将4,5-二氯-6-甲氧基-2-甲基-3(2H)-哒嗪酮(2.00g,9.57mmol)和甲醇钠(2.00mL,在MeOH中25重量%溶液)合并于1,4-二氧杂环己烷(20mL) 中并在室温下搅拌过夜。将溶液浓缩至50%体积并在水(100mL)和乙酸乙酯(100mL)之间进行分配。用乙酸乙酯(3×100mL)萃取含水层。合并有机层,用盐水洗涤,经MgSO4干燥并浓缩。所得的残余物吸收至硅胶(1g) 上,并且通过MPLC采用0-100%乙酸乙酯/己烷梯度,使其通过预填充的40g 硅胶柱进行纯化。真空浓缩包含纯期望产物的级分,以获得1.78g为白色固体的标题化合物。
步骤B:5-氯-4-(2,3-二甲基-1-萘基)-6-甲氧基-2-甲基-3(2H)-哒嗪酮的制备
在氮气吹扫的配有温度计的100mL 2-颈RB烧瓶中,将1-溴-2,3-二甲基萘(1.41g,6.01mmol)溶解于无水四氢呋喃(15mL)中并经干冰/丙酮浴冷却至–78℃。在15分钟内滴加N-丁基锂(2.4mL,在己烷中的2.5M溶液),并且将反应混合物在-78℃下搅拌5分钟。然后移除冷却浴并使溶液温热至–50℃。然后一次性加入溴化镁醚化物(1.55g,6.01mmol),并且搅拌反应混合物并温热至–20℃。接着一次性加入步骤A的产物(0.700g,4.00mmol),并且搅拌反应混合物并温热至室温。在1h之后,将所得的绿色溶液倾注到饱和NH4Cl(100mL)溶液中,并且萃取到乙酸乙酯(4×50mL)中。合并有机层,经MgSO4干燥并真空浓缩。将所得的残余物溶解于二氯甲烷,吸收至硅胶(1g)上,并且通过MPLC采用0-100%乙酸乙酯/己烷梯度使其通过 40g硅胶柱进行纯化。合并包含纯期望产物的级分并真空浓缩,以获得0.290g 的标题化合物。
步骤C:4-(2,3-二甲基-1-萘基)-5-羟基-6-甲氧基-2-甲基-3(2H)-哒嗪酮的制备
将步骤B的产物(0.200g,0.608mmol)溶解于1,4-二氧杂环己烷(10mL) 中,并且用氢氧化四丁基铵(0.800mL,在水中的40重量%溶液)处理。将所得的溶液加热至回流并搅拌2h。然后使反应混合物冷却至室温并将其倾注到1N HCl(50mL)中并萃取到乙酸乙酯(4×20mL)中。合并有机层,经 MgSO4干燥并减压浓缩。使粗制固体溶解于二氯甲烷中并吸收至硅胶(1g) 上。纯化通过MPLC采用40%至100%乙酸乙酯/己烷梯度,通过40g硅胶柱而进行。合并包含期望产物的级分并真空浓缩,以获得0.130g的为白色固体的标题化合物,即,本发明的化合物。
合成实施例5
6-氯-4-(5-氯-2-甲基苯并[b]噻吩-2-基)-5-羟基-2-甲基哒嗪-3(2H)-酮(化合
物91)的制备
步骤A:6-氯-5-[(5-氯苯并[b]噻吩-3-基)甲氧基]-2-甲基哒嗪-3(2H)-酮的制备
在氮气下,将N,N-二甲基甲酰胺(20mL)和氢化钠(0.335g,8.37mmol) 的浆液用冰冷却15min。在氮气覆层下,分批添加5-氯-[b]噻吩-2-甲醇(1.33g, 6.7mmol)并在冰上搅拌15min。然后在氮气覆层下添加5,6-二氯-2-甲基 -3(2H)-哒嗪酮(1.00g,5.58mol)。移除冰浴,使反应混合物在室温下搅拌过夜。然后将所得反应混合物倾注到饱和氯化铵溶液和冰中(200mL)并萃取到乙醚(3×40mL)中。合并所得的有机层,经MgSO4干燥并吸收到硅胶(4g) 上。采用0至100%乙酸乙酯的己烷溶液的梯度洗脱,使用40g硅胶柱进行色谱分析,提供为黄色固体的标题化合物。(1.00g,53%收率)。
1H NMR(500MHz)δ7.78–7.71(m,2H),7.37–7.32(m,2H),5.35(s,2H),3.74 (s,3H)。
步骤B:6-氯-4-(5-氯-2-甲基苯并[b]噻吩-3-基)-5-羟基-2-甲基哒嗪-3(2H)-酮
的制备
在40mL闪烁小瓶中,将6-氯-5-[(5-氯苯并[b]噻吩-2-基)甲氧基]-2-甲基 哒嗪-3(2H)-酮(即以上步骤A获得的产物,0.250g,0.700mmol)溶解于5mL 二甲苯中并在175℃下搅拌过夜。然后将反应混合物冷却至室温并添加40mL的己烷。将所得沉淀过滤,用己烷洗涤并干燥,以给出为橙色固体的期望产物(0.100g)。
1H NMR(500MHz)δ7.71–7.69(m,1H),7.30–7.27(m,1H),7.26–7.24(m,1H), 3.80(s,3H),2.43(s,3H)。
通过本文所述的过程以及本领域已知的方法,可制备表1至表619的以下化合物。下列缩写用于随后的表中:t是指叔,s是指仲,n是指正,i是指异,Me是指甲基,Et是指乙基,Pr是指丙基,Bu是指丁基,Bu是指丁基,OMe是指甲氧基,CN是指氰基,S(O)2Me是指甲磺酰,并且“–”是指未被R3取代。
表1
W为O,X为S,R1为Me,R2为Me,并且G为H。
表2按照相同的方式构建,不同的是用下表2所列的行标题(即“W为 O,X为S,R1为Me,R2为Me,并且G为C(O)Me。”)替换行标题“W 为O,X为S,R1为Me,R2为Me,并且G为H。”。因此,表2中的第一项为式1的化合物,其中W为O,X为S,R1为Me,R2为Me,(R3)n为“–”(即n为0;未被R3取代),R4为H,并且G为C(O)Me。表3至表 627类似地构建。
制剂/应用
本发明的化合物一般可用作组合物即制剂中的除草剂活性成分,所述组合物具有至少一种用作载体的附加组分,所述附加组分选自表面活性剂、固体稀释剂和液体稀释剂。选择制剂或组合物成分,以符合活性成分的物理性质、施用方式和环境因素诸如土壤类型、水分和温度。
可用的制剂包括液体组合物和固体组合物。液体组合物包括溶液(包括乳油)、悬浮液、乳液(包括微乳液、水包油乳液、可流动浓缩物和/或悬乳液)等,它们可以任选地被稠化成凝胶。水性液体组合物的一般类型为可溶性浓缩物、悬浮液浓缩物、胶囊悬浮液、浓缩乳液、微乳液、水包油乳液、可流动浓缩物和悬乳液。非水性液体组合物的一般类型为乳油、可微乳化的浓缩物、可分散浓缩物和油分散体。
固体组合物的一般类型为粉剂、粉末、颗粒剂、球剂、粒料、锭剂、片剂、填充膜(包括种子包衣)等,它们可为水分散性的(“可润湿的”)或水溶性的。由成膜溶液或可流动悬浮液形成的膜和包衣尤其可用于种子处理。活性成分可被(微)胶囊包封,并且进一步形成悬浮液或固体制剂;另选地,可将整个活性成分制剂进行胶囊包封(或“包覆”)。胶囊包封可以控制或延迟活性成分的释放。可乳化的颗粒剂结合了乳油制剂和干颗粒制剂两者的优点。高-强度组合物主要用作进一步制剂的中间体。
可喷雾的制剂通常在喷雾之前分散在适宜的介质中。此类液体和固体制剂被配制成在喷雾介质,通常为水,但偶尔另一种合适介质类似于芳族烃或石蜡烃或植物油中易于稀释的。喷雾体积可以在每公顷约一升至几千升的范围内,但更典型地在每公顷约十升至几百升的范围内。可喷雾的制剂可在罐中与水或另一种适宜的介质混合,用于通过空气或地面施用来处理叶,或者用于施用到植物的生长介质中。液体和干燥制剂可以直接定量加入滴灌系统中,或在种植期间定量加入垄沟中。
所述制剂通常将包含有效量的活性成分、稀释剂和表面活性剂,其在以下大致范围内,总计为按重量计100%。
固体稀释剂包括例如,粘土诸如膨润土、蒙脱土、绿坡缕石和高岭土、石膏、纤维素、二氧化钛、氧化锌、淀粉、糊精、糖(例如乳糖、蔗糖)、二氧化硅、滑石、云母、硅藻土、脲、碳酸钙、碳酸钠和碳酸氢钠、以及硫酸钠。典型的固体稀释剂在Watkins等人,Handbook ofInsecticide Dust Diluent and Carriers,第2版,Dorland Books,Caldwell,New Jersey中有所描述。
液体稀释剂包括例如水、N,N-二甲基烷酰胺(例如N,N-二甲基甲酰胺)、柠檬烯、二甲基亚砜、N-烷基吡咯烷酮(例如N-甲基吡咯烷酮)、烷基磷酸盐(例如,三乙基磷酸盐)、乙二醇、三甘醇、丙二醇、双丙二醇、聚丙二醇、碳酸亚丙酯、碳酸亚丁酯、石蜡(例如白矿物油、正链烷烃、异链烷烃)、烷基苯、烷基萘、甘油、三乙酸甘油酯、山梨醇、芳族烃、脱芳构化脂族化合物、烷基苯、烷基萘、酮(诸如环己酮、2-庚酮、异佛尔酮和4-羟基-4- 甲基-2-戊酮)、乙酸酯(诸如乙酸异戊酯、乙酸己酯、乙酸庚酯、乙酸辛酯、乙酸壬酯、乙酸十三烷基酯和乙酸异冰片酯)、其它酯(诸如烷基化乳酸酯、二元酯、苯甲酸烷基酯和苯甲酸芳基酯和γ-丁内酯)、以及可以是直链、支链、饱和或不饱和的醇(诸如甲醇、乙醇、正-丙醇、异丙醇、正丁醇、异丁醇、正己醇、2-乙基己醇、正-辛醇、癸醇、异癸醇、异十八醇、鲸蜡醇、月桂醇、十三烷醇、油醇、环己醇、四氢糠醇、双丙酮醇、甲酚和苄醇)。液体稀释剂还包括饱和的和不饱和的脂肪酸(通常为C6–C22)的甘油酯,诸如植物种子和果实的油(例如橄榄油、蓖麻油、亚麻籽油、芝麻油、玉米(玉蜀黍)油、花生油、葵花籽油、葡萄籽油、红花油、棉籽油、大豆油、油菜籽油、椰子油和棕榈仁油)、动物源脂肪(例如牛脂、猪脂、猪油、鳕鱼肝油、鱼油)、以及它们的混合物。液体稀释剂还包括烷基化(例如甲基化、乙基化、丁基化)脂肪酸,其中脂肪酸可以通过源自植物和动物的甘油酯的水解获得,并且可通过蒸馏进行纯化。典型的液体稀释剂在Marsden,Solvents Guide,第2版,Interscience,New York,1950中有所描述。
本发明的固体组合物和液体组合物通常包含一种或多种表面活性剂。当添加到液体中时,表面活性剂(还被称为“表面活性试剂”)通常改变、最通常降低液体的表面张力。根据表面活性剂分子中的亲水基团和亲脂基团的性质,表面活性剂可用作润湿剂、分散剂、乳化剂或消泡剂。
表面活性剂可被归类为非离子表面活性剂、阴离子表面活性剂或阳离子表面活性剂。可用于本发明组合物的非离子表面活性剂包括但不限于:醇烷氧基化物,诸如基于天然醇和合成醇(其可以是支链或直链的)并且由醇和环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物制备的醇烷氧基化物;胺乙氧基化物、链烷醇酰胺和乙氧基化链烷醇酰胺;烷氧基化甘油三酯,诸如乙氧基化的大豆油、蓖麻油和油菜籽油;烷基苯酚烷氧基化物,诸如辛基苯酚乙氧基化物、壬基苯酚乙氧基化物、二壬基苯酚乙氧基化物和十二烷基苯酚乙氧基化物(由苯酚和环氧乙烷、环氧丙烷、环氧丁烷或它们混合物制备);由环氧乙烷或环氧丙烷制备的嵌段聚合物和其中末端嵌段由环氧丙烷制备的反式嵌段聚合物;乙氧基化脂肪酸;乙氧基化脂肪酯和油;乙氧基化甲酯;乙氧基化三苯乙烯基苯酚(包括由环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物制备的那些);脂肪酸酯、甘油酯、基于羊毛脂的衍生物、多乙氧基化酯(诸如多乙氧基化脱水山梨糖醇脂肪酸酯、多乙氧基化山梨醇脂肪酸酯和多乙氧基化甘油脂肪酸酯);其它脱水山梨糖醇衍生物,诸如脱水山梨糖醇酯;聚合物表面活性剂,诸如无规共聚物、嵌段共聚物、醇酸peg(聚乙二醇)树脂、接枝或梳型聚合物以及星型聚合物;聚乙二醇(peg);聚乙二醇脂肪酸酯;基于有机硅的表面活性剂;和糖衍生物,诸如蔗糖酯、烷基多苷和烷基多糖。
可用的阴离子表面活性剂包括但不限于:烷基芳基磺酸和它们的盐;羧化的醇或烷基苯酚乙氧基化物;二苯基磺酸酯衍生物;木质素和木质素衍生物,诸如木质素磺酸盐;马来酸或琥珀酸或它们的酸酐;烯烃磺酸酯;磷酸酯,诸如醇烷氧基化物的磷酸酯,烷基酚烷氧基化物的磷酸酯和苯乙烯基苯酚乙氧基化物的磷酸酯;基于蛋白质的表面活性剂;肌氨酸衍生物;苯乙烯基苯酚醚硫酸盐;油和脂肪酸的硫酸盐和磺酸盐;乙氧基化烷基酚的硫酸盐和磺酸盐;醇的硫酸盐;乙氧基化醇的硫酸盐;胺和酰胺的磺酸盐,诸如 N,N-烷基牛磺酸盐;苯、异丙基苯、甲苯、二甲苯以及十二烷基苯和十三烷基苯的磺酸盐;缩聚萘的磺酸盐;萘和烷基萘的磺酸盐;石油馏分的磺酸盐;磺基琥珀酰胺酸盐;以及磺基琥珀酸盐和它们的衍生物,诸如二烷基磺基琥珀酸盐。
可用的阳离子表面活性剂包括但不限于:酰胺和乙氧基化酰胺;胺,诸如N-烷基丙二胺、三亚丙基三胺和二亚丙基四胺,以及乙氧基化胺、乙氧基化二胺和丙氧基化胺(由胺和环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物制备);胺盐,诸如胺乙酸盐和二胺盐;季铵盐,诸如季盐、乙氧基化季盐和二季盐;以及胺氧化物,诸如烷基二甲基胺氧化物和双-(2-羟基乙基)- 烷基胺氧化物。
还可用于本发明组合物的是非离子表面活性剂和阴离子表面活性剂的混合物、或非离子表面活性剂和阳离子表面活性剂的混合物。非离子表面活性剂、阴离子表面活性剂和阳离子表面活性剂及其推荐用途在多个已公布的参考文献中有所公开,包括McCutcheon’s Division,The Manufacturing Confectioner Publishing Co.出版的McCutcheon’s Emulsifiers and Detergents,北美和国际年鉴版;Sisely和Wood,Encyclopedia of Surface Active Agents, Chemical Publ.Co.,Inc.,New York,1964;以及A.S.Davidson和B. Milwidsky,Synthetic Detergents,第七版,John Wiley andSons,New York, 1987。
本发明的组合物还可包含本领域技术人员已知为辅助制剂的制剂助剂和添加剂(其中一些也可被认为是起到固体稀释剂、液体稀释剂或表面活性剂作用)。此类制剂助剂和添加剂可控制:pH(缓冲剂)、加工过程中的起泡(消泡剂,诸如聚有机硅氧烷)、活性成分的沉降(悬浮剂)、粘度(触变增稠剂)、容器内的微生物生长(抗微生物剂)、产品冷冻(防冻剂)、颜色(染料/颜料分散体)、洗脱(成膜剂或粘着剂)、蒸发(防蒸发剂)、以及其它制剂属性。成膜剂包括例如聚乙酸乙烯酯、聚乙酸乙烯酯共聚物、聚乙烯吡咯烷酮-乙酸乙烯酯共聚物、聚乙烯醇、聚乙烯醇共聚物和蜡。制剂助剂和添加剂的示例包括McCutcheon分部TheManufacturing Confectioner Publishing Co.出版的McCutcheon’s Volume 2:Functional Materials,北美和国际年鉴版;以及PCT公开WO 03/024222中列出的那些。
通常通过将活性成分溶于溶剂中或者通过在液体或干燥稀释剂中研磨活性成分将式1的化合物和任何其它活性成分掺入本发明组合物中。可通过简单地混合所述成分来制备包括乳油的溶液。如果旨在用作乳油的液体组合物的溶剂是与水不混溶的,通常加入乳化剂使含有活性成分的溶剂在用水稀释时发生乳化。可使用介质研磨机来湿磨粒径为至多2,000μm的活性成分浆液,以获得具有低于3μm的平均直径的颗粒。含水浆液可以制备为成品悬浮液浓缩物(参见例如U.S.3,060,084)或通过喷雾干燥而进一步加工形成水分散性的颗粒剂。干燥制剂通常需要干燥研磨步骤,其产生2μm至10μm范围内的平均粒径。粉剂和粉末可以通过共混,并且通常通过研磨(例如用锤磨机或流能磨)来制备。可通过将活性物质喷雾在预成形颗粒载体上或者通过附聚技术来制备颗粒剂和球剂。参见Browning的“Agglomeration” (Chemical Engineering,1967年12月4日,第147–48页)、Perry的Chemical Engineer’s Handbook,第4版(McGraw-Hill,New York,1963,第8–57页及其后页)和WO 91/13546。球剂可根据U.S.4,172,714中所述的来制备。水-分散性和水-溶性颗粒剂可根据U.S.4,144,050、U.S.3,920,442和DE 3,246,493中的教导来制备。片剂可根据U.S.5,180,587、U.S.5,232,701和U.S. 5,208,030中的教导来制备。膜可根据GB 2,095,558和U.S.3,299,566中的教导来制备。
关于制剂领域的进一步信息,参见T.S.Woods的Pesticide Chemistry andBioscience,The Food-Environment Challenge中的“The Formulator’s Toolbox -Product Forms for Modern Agriculture”,T.Brooks和T.R.Roberts编辑, Proceedingsof the 9th International Congress on Pesticide Chemistry,The Royal Society ofChemistry,Cambridge,1999,第120-133页。还可参见U.S. 3,235,361,第6栏,第16行至第7栏,第19行和实施例10-41;U.S 3,309,192,第5栏,第43行至第7栏,第62行和实施例8、12、15、39、41、52、53、 58、132、138-140、162-164、166、167和169-182;U.S.2,891,855,第3栏,第66行至第5栏,第17行和实施例1-4;Klingman的Weed Control as a Science,JohnWiley and Sons,Inc.,New York,1961,第81-96页;Hance 等人的Weed ControlHandbook,第8版,Blackwell Scientific Publications, Oxford,1989;以及Developments in formulation technology,PJB Publications, Richmond,UK,2000。
在下列实施例中,全部百分比都是按重量计的,并且所有的制剂以常规的方式制备。化合物编号参照索引表A中的化合物。无需深入研究,据信本领域的技术人员根据以上所述内容可将本发明利用至最大限度。以下非限制性实施例是本发明的例示。除非另外说明,否则百分比按重量计。
实施例A
高浓度浓缩物
化合物1 98.5%
二氧化硅气凝胶 0.5%
合成无定形精细二氧化硅 1.0%
实施例B
可润湿性粉末
实施例C
颗粒剂
化合物1 10.0%
绿坡缕石颗粒剂(低挥发性物质,0.71/0.30mm;U.S.S. 90.0%
No.25–50筛目)
实施例D
挤出粒料
实施例E
乳油
化合物1 10.0%
聚氧乙烯山梨醇六油酸酯 20.0%
C6–C10脂肪酸甲酯 70.0%
实施例F
微乳液
实施例G
悬浮液浓缩物
实施例H
水乳液
实施例I
油分散体
本公开还包括以上实施例A至I,不同的是“化合物1”用“化合物2”、“化合物3”、“化合物4”、“化合物5”、“化合物6”、“化合物7”、“化合物8”、“化合物9”、“化合物10”、“化合物11”、“化合物12”、“化合物13”、“化合物14”、“化合物15”、“化合物16”、“化合物 17”、“化合物18”、“化合物19”、“化合物20”、“化合物21”、“化合物22”、“化合物23”、“化合物24”、“化合物25”、“化合物26”、“化合物27”、“化合物28”、“化合物29”、“化合物30”、“化合物 31”、“化合物32”、“化合物33”、“化合物34”、“化合物35”、“化合物36”、“化合物37”、“化合物38”、“化合物39”、“化合物40”、“化合物41”、“化合物42”、“化合物43”、“化合物44”、“化合物 45”、“化合物46”、“化合物47”、“化合物48”、“化合物49”、“化合物50”、“化合物51”、“化合物52”、“化合物53”、“化合物54”、“化合物55”、“化合物56”、“化合物57”、“化合物58”、“化合物59”、“化合物60”、“化合物61”、“化合物62”、“化合物63”、“化合物64”、“化合物65”、“化合物66”、“化合物67”、“化合物68”、“化合物69”、“化合物70”、“化合物71”、“化合物72”、“化合物73”、“化合物74”、“化合物75”、“化合物76”、“化合物77”、“化合物78”、“化合物79”、“化合物80”、“化合物81”、“化合物82”、“化合物83”、“化合物84”、“化合物85”、“化合物86”、“化合物87”、“化合物88”、“化合物89”、“化合物90”、“化合物91”、“化合物92”、“化合物93”、“化合物94”、“化合物95”、“化合物96”、“化合物97”、“化合物98”、“化合物99”、“化合物100”、“化合物101”、“化合物102”、“化合物103”、“化合物104”、“化合物105”、“化合物106”、“化合物107”、“化合物108”、“化合物109”、“化合物110”、“化合物111”、“化合物112”、“化合物113”、“化合物 114”、“化合物115”、“化合物116”、“化合物117”、“化合物118”、“化合物119”、“化合物120”、“化合物121”、“化合物122”、“化合物123”、“化合物124”、“化合物125”、“化合物126”、“化合物 127”、“化合物128”、“化合物129”、“化合物130”、“化合物131”、“化合物132”、“化合物133”、“化合物134”、“化合物135”、“化合物136”、“化合物137”、“化合物138”、“化合物139”、“化合物 140”、“化合物141”、“化合物142”、“化合物143”、“化合物144”、“化合物145”、“化合物146”、“化合物147”、“化合物148”、“化合物149”、“化合物150”、“化合物151”、“化合物152”、“化合物 153”、“化合物154”、“化合物155”、“化合物156”、“化合物157”、“化合物158”、“化合物159”、“化合物160”、“化合物161”、“化合物162”、“化合物163”、“化合物164”、“化合物165”、“化合物 166”、“化合物167”、“化合物168”、“化合物169”、“化合物170”、“化合物171”、“化合物172”、“化合物173”、“化合物174”、“化合物175”、“化合物176”、“化合物177”、“化合物178”、“化合物 179”、“化合物180”、“化合物181”、“化合物182”、“化合物183”、“化合物184”、“化合物185”、“化合物186”、“化合物187”或“化合物188”替代。
测试结果示出,本发明化合物是高活性出苗前和/或出苗后除草剂和/或植物生长调节剂。本发明化合物通常示出对于出苗后杂草防治(即在杂草从土壤中出苗之后施用)和出苗前杂草防治(即在杂草从土壤中出苗之前施用) 的最高活性。在期望完全防治所有植被的区域,诸如在燃料储槽、工业仓储区域、停车场、露天汽车电影院、机场、河岸、灌溉与其它水道、看板与高速公路及铁路结构体周围,它们中许多对于广谱出苗前和/或出苗后杂草防治具有效用。许多本发明化合物经由下列方式而可用于选择性防治作物/杂草混生中的禾草与阔叶杂草:在作物与杂草中进行选择性代谢,或对于作物与杂草中的生理抑制位点具有选择性活性,或在作物与杂草混生的环境之上或之中进行选择性施放。本领域的技术人员将认识到,在化合物或化合物组中,这些选择性因子的优选组合可易于通过实施常规生物和/或生化测定而确定。本发明化合物可示出对重要农作物的耐受性,所述农作物包括但不限于苜蓿、大麦、棉花、小麦、油菜、糖用甜菜、玉米(玉蜀黍)、高粱、大豆、稻、燕麦、花生、蔬菜、番茄、马铃薯、多年生种植作物包括咖啡、可可、油棕、橡胶、甘蔗、柑橘、葡萄、果树、坚果树、香蕉、车前草、菠萝、啤酒花、茶和森林诸如按树和针叶树(例如火炬松)、以及草皮物类(例如草地早熟禾、圣奥古斯丁草(St.Augustine grass)、Kentucky牛毛草和狗牙根草)。本发明化合物可用于经基因转化或选殖的作物,以掺入除草剂抗性,表达对无脊椎害虫具有毒性的蛋白质(诸如苏云金芽孢杆菌毒素)和/或表达其它可用性状。本领域技术人员将会知道,不是所有化合物对所有杂草均具有相同的效果。另选地,本主题化合物可用于改变植物生长。
由于本发明的化合物具有出苗前和出苗后除草活性,因此为通过杀灭或伤害非期望植物或减缓其生长来防治所述植物,通常由多种方法来施用所述化合物,所述方法涉及使除草有效量的本发明化合物、或包含所述化合物和至少一种表面活性剂、固体稀释剂或液体稀释剂的组合物接触所述非期望植物的叶子或其它部位,或接触所述非期望植物的环境,诸如所述非期望植物生长于其中的土壤或水,或所述非期望植物的种子或其它繁殖体周围的土壤或水。
本发明化合物的除草有效量由多种因素决定。这些因素包括:所选择的制剂、施用方法、所存在植被的量和类型、生长条件等。一般来讲,本发明化合物的除草有效量为约0.001kg/ha至20kg/ha,优选范围为约0.004kg/ha 至1kg/ha。本领域的技术人员可易于确定期望杂草防治程度所需的除草有效量。
在一个常见的实施方案中,将本发明的化合物通常以配制的组合物施用于包括期望植被(例如作物)和不期望植被(即杂草)的所在地,该期望植被和不期望植均可为与生长介质(例如土壤)接触的种子、幼苗和/或较大植株。在此所在地,可将包含本发明化合物的组合物直接施用于植物或其部分,特别是不期望的植被,和/或施用于与植物接触的生长介质。
在经本发明的化合物处理的所在地中,期望植被的植株品种和栽培品系可通过常规的繁殖和育种方法或通过基因工程方法获得。经基因修饰的植株 (转基因植物)为其中异源性基因(转基因)已被稳定整合进植株的基因组的那些。由它在植物基因组中的特定位置所限定的转基因被称为转化事件或转基因事件。
此所在地中经基因修饰的可根据本发明处理的植物栽培品系包括抵抗一种或多种生物胁迫的那些(害虫,诸如线虫动物、昆虫、螨虫、真菌等) 或非生物胁迫(干旱、低温、土壤盐化等),或其包含其它期望的特征。植株可经基因修饰以表现出性状,例如除草剂耐受性、昆虫耐受性、修饰的油特征或耐旱性。包括单个基因转化事件或转化事件的组合的可用的经基因修饰的植物列出于示例C中。示例C所列的基因修饰的附加信息可获自维护的公开数据库,例如U.S.Department of Agriculture。
就性状而言,在示例C中采用下列缩写T1至T37。“tol.”是指“耐受性”。连字符“-“表示条目不可用。
示例C
*阿根廷油菜(甘蓝型油菜(Brassica napus)),**波兰白菜(芜菁(B.rapa)),# 茄子
虽然最典型地,本发明的化合物用于防治不期望的植被,但是使期望的植被在经处理的所在地中与本发明的化合物接触可导致与期望植被的遗传性状的超加性的或协同增强效应,包括通过基因修饰引入的性状。例如,对植食性害虫或植物病害的耐受性、对生物胁迫/非生物胁迫的耐受性或贮存稳定性可比期望的植被的遗传性状中所期望的更大。
本发明的化合物还可与一种或多种其它生物学活性化合物或试剂混合形成多-组分杀虫剂,从而赋予甚至更广谱的农业保护作用,所述生物学活性化合物或试剂包括除草剂、除草剂安全剂、杀真菌剂、杀昆虫剂、杀线虫剂、杀菌剂、杀螨剂、生长调节剂诸如昆虫蜕皮抑制剂和生根刺激剂、化学不育剂、化学信息素、拒斥剂、诱虫剂、信息素、取食刺激剂、植物营养素、其它生物学活性化合物或昆虫病原细菌、病毒或真菌。本发明化合物与其它除草剂的混合物可扩大抵抗其它杂草物种的活性范围,并且抑制任何抗性生物类型的增殖。因此本发明还涉及包含式1的化合物(除草有效量)和至少一种附加生物学活性化合物或试剂(生物学有效量)的组合物,并且所述组合物还可包含表面活性剂、固体稀释剂或液体稀释剂中的至少一种。其它生物学活性化合物或试剂可配制到包含表面活性剂、固体稀释剂或液体稀释剂中的至少一种的组合物中。对于本发明的混合物,可将一种或多种其它生物学活性化合物或试剂与式1的化合物配制在一起以形成预混物,或者一种或多种其它生物学活性化合物或试剂可与式1的化合物分开配制,并且在施用前将制剂合并在一起(例如在喷雾罐中),或另选地,进行依次施用。
以下除草剂中的一种或多种与本发明化合物的混合物可特别用于杂草防治:乙草胺、三氟羧草醚及其钠盐、苯草醚、丙烯醛(2-丙烯醛)、甲草胺、禾草灭、莠灭净、氨唑草酮、酰嘧磺隆、环丙嘧啶酸及其酯(例如甲基、乙基)和盐(例如钠、钾)、氨草啶、杀草强、氨基磺酸铵、莎稗磷、磺草灵、阿特拉津、四唑嘧磺隆、氟丁酰草胺、草除灵、草除灵-乙酯、bencarbazone、氟草胺、呋草黄、苄嘧磺隆-甲酯、地散磷、灭草松、苯并双环酮、吡草酮、氟吡草酮、甲羧除草醚、双丙氨膦、双草醚及其钠盐、除草定、溴丁酰草胺、溴酚肟、溴苯腈、溴苯腈辛酸酯、丁草胺、氟丙嘧草酯、抑草磷、丁乐灵、丁苯草酮、丁草特、苯酮唑、卡草胺、三唑酮草酯、儿茶素、甲氧除草醚、草灭平、氯溴隆、氯甲丹、杀草敏、氯嘧磺隆-乙酯、绿麦隆、氯苯胺灵、氯磺隆、氯酞酸-二甲酯、赛草青、吲哚酮草酯、环庚草醚、醚磺隆、氯酰草膦、环苯草酮、烯草酮、炔草酯、异噁草酮、lomeprop、二氯吡啶酸、二氯吡啶酸-乙醇胺盐、氯酯磺草胺、苄草隆、氰草津、环草特、cyclopyrimorate、环丙嘧磺隆、噻草酮、氰氟草酯丁酯、2,4-D,及其丁氧基酯、丁酯、异辛酯和异丙酯及其二甲基铵盐、二乙醇胺盐和三乙醇胺盐、杀草隆、茅草枯、茅草枯钠、棉隆、2,4-DB及其二甲基铵盐、钾盐和钠盐、甜菜安、敌草净、麦草畏及其二乙二醇铵盐、二甲基铵盐、钾盐和钠盐、敌草腈、滴丙酸、禾草灵-甲基、双氯磺草安、野燕枯甲硫酸酯、吡氟草胺、氟吡草腙、噁唑隆、哌草丹、二甲草胺、排草净、噻吩草胺、噻吩草胺-P、噻节因、二甲胂酸及其钠盐、氨氟灵、特乐酚、双苯酰草胺、敌草快、氟硫草定、敌草隆、DNOC、草多索、EPTC、戊草丹、乙丁烯氟灵、胺苯磺隆-甲酯、乙嗪草酮、乙呋草黄、氯氟草醚、乙氧嘧磺隆、乙氧苯草胺、噁唑禾草灵-乙酯、精唑禾草灵-乙酯、fenoxasulfone、fenquinotrione、四唑酰草胺、非草隆、去草隆、麦草氟-甲酯、高效-麦草氟-异丙酯、高效-麦草伏-甲酯、啶嘧磺隆、双氟磺草胺、吡氟禾草灵-丁酯、精-吡氟禾草灵-丁酯、异丙吡草酯、氟酮磺隆、氟吡磺隆、氟消草、氟噻草胺、氟哒嗪、氟哒嗪草酯、唑嘧磺草胺、氟胺草酯、丙炔氟草胺、伏草隆、乙羧氟草醚、氟胺草唑、氟啶嘧磺隆及其钠盐、抑草丁、芴醇丁酯、氟啶酮、氟咯草酮、氯氟吡氧乙酸、呋草酮、哒草氟、氟磺胺草醚、甲酰胺磺隆、氨基甲酰基膦酸乙酯铵盐(fosamine-ammonium)、草胺磷、草铵膦、精草胺磷、草甘膦及其盐诸如铵盐、异丙基铵盐、钾盐、钠盐(包括倍半钠)和三甲基锍(或者称为草硫膦)、氟氯吡啶酯(halauxifen)、氟氯吡啶甲酯(halauxifen-methyl)、氯吡嘧磺隆、氟吡乙禾灵、氟吡甲禾灵、环嗪酮、咪草酸、甲氧咪草烟、甲咪唑烟酸、灭草烟(imazapyr)、灭草喹、灭草喹-铵、咪草烟、咪草烟-铵、唑吡嘧磺隆、茚草酮、三嗪茚草胺、 iofensulfuron、甲基碘磺隆、碘苯腈、碘苯腈辛酸酯、碘苯腈钠、三唑酰草胺(ipfencarbazone)、异丙隆、异噁隆、异噁草胺、异噁唑草酮、异噁氯草酮、乳氟禾草灵、环草定、利谷隆、抑芽丹、MCPA及其盐(例如MCPA- 二甲基铵盐、MCPA-钾盐和MCPA-钠盐、酯(例如MCPA-2-乙基己基酯、 MCPA-丁氧酯)和硫酯(例如MCPA-乙硫酯)、MCPB及其盐(例如MCPB- 钠盐)和酯(例如MCPB-乙酯)、2-甲-4-氯丙酸、精-2-甲-4-氯丙酸、苯噻草胺、氟磺酰草胺、甲磺胺磺隆、甲基磺草酮、威百亩、噁唑酰草胺、苯嗪草酮、吡唑草胺、嗪吡嘧磺隆、甲基苯噻隆、甲胂酸及其钙盐、单铵盐、单钠盐和二钠盐、甲基杀草隆、吡喃隆、溴谷隆、异丙甲草胺、精异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲磺隆、禾草特、绿谷隆、萘丙胺、萘丙酰草胺、萘丙酰草胺-M、萘草胺、草不隆、烟嘧磺隆、哒草伏、坪草丹、嘧苯胺磺隆、氨磺乐灵、丙炔噁草酮、噁草酮、环氧嘧磺隆、噁嗪草酮、乙氧氟草醚、百草枯二氯盐、克草猛、壬酸、二甲戊乐灵、五氟磺草胺、甲氯酰草胺、环戊噁草酮、氟草磺胺、烯草胺、pethoxyamid、苯敌草、毒莠定、毒莠定-钾盐、氟吡酰草胺、唑啉草酯、哌草磷、丙草胺、氟嘧磺隆、氨基丙乐灵、环苯草酮、扑灭通、扑草净、毒草胺、敌稗、喔草酯、扑灭津、苯胺灵、异丙草胺、丙苯磺隆、丙嗪嘧磺隆、戊炔草胺、苄草丹、氟磺隆、双唑草腈、吡草醚、磺酰草吡脱、双唑草腈(pyrazogyl)、吡唑特、苄草唑、吡嘧-磺隆、嘧啶肟草醚、稗草畏、达草特、环酯草醚、嘧草醚、嘧啶硫蕃(Pyrimisulfan)、嘧草硫醚、嘧草硫醚钠、罗克杀草砜、甲氧磺草胺、二氯喹啉酸、氯甲喹啉酸、灭藻醌、喹禾灵-乙酯、精-喹禾灵-乙酯、喹禾-糠-酯、砜嘧磺隆、嘧啶肟草醚、稀禾定、环草隆、西玛津、西草净、磺草酮、甲磺草胺、甲嘧磺隆、磺酰磺隆、2,3,6-TBA、TCA、TCA-钠盐、牧草胺、特丁噻草隆、特呋三酮、环磺酮、得杀草、特草定、特丁通、特丁津、特丁净、甲氧噻草胺、噻草啶、噻酮磺隆、噻磺隆、禾草丹、tiafenacil、仲草丹、苯吡唑草酮、肟草酮、野麦畏、氟酮磺草胺、醚苯磺隆、三嗪氟草胺、苯磺隆-甲酯、绿草定、三氯比、绿草定三乙铵盐、灭草环、草达津、三氟啶磺隆、氟乐灵、氟胺磺隆、三氟甲磺隆、灭草敌、3-(2-氯-3,6-二氟苯基)-4-羟基-1-甲基-1,5-萘啶-2(1H)- 酮、5-氯-3-[(2-羟基-6-氧代-1-环己烯-1-基)羰基]-1-(4-甲氧基苯基)-2(1H)-喹喔啉酮、2-氯-N-(1-甲基-1H-四唑-5-基)-6-(三氟甲基)-3-吡啶甲酰胺、7-(3,5- 二氯-4-吡啶基)-5-(2,2-二氟乙基)-8-羟基吡啶并[2,3-b]吡嗪-6(5H)-酮)、4-(2,6- 二乙基-4-甲基苯基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮)、5-[[(2,6-二氟苯基)甲氧基]甲基]-4,5-二氢-5-甲基-3-(3-甲基-2-噻吩基)异唑(前述methioxolin)、 3-[7-氟-3,4-二氢-3-氧代-4-(2-丙炔-1-基)-2H-1,4-苯并噁嗪-6-基]二氢-1,5-二甲基-6-硫代-1,3,5-三嗪-2,4(1H,3H)-二酮、4-(4-氟苯基)-6-[(2-羟基-6-氧代-1-环己烯-1-基)羰基]-2-甲基-1,2,4-三嗪-3,5(2H,4H)-二酮、4-氨基-3-氯-6-(4-氯-2- 氟-3-甲氧基苯基)-5-氟-2-吡啶甲酸甲酯、2-甲基-3-(甲磺酰)-N-(1-甲基-1H-四唑-5-基)-4-(三氟甲基)苯甲酰胺以及2-甲基-N-(4-甲基-1,2,5-噁二唑-3- 基)-3-(甲基亚磺酰基)-4-(三氟甲基)苯甲酰胺。其它除草剂还包括生物除草剂,诸如损毁链格孢(Alternaria destruens Simmons)、刺盘孢炭疽菌 (Colletotrichum gloeosporiodes(Penz.)Penz.&Sacc.)、稗内脐蠕孢菌 (Drechsiera monoceras)(MTB-951)、疣孢漆斑菌(Myrothecium verrucaria) (Albertini&Schweinitz)Ditmar:Fries、棕榈疫霉(Phytophthora palmivora) (Butl.)Butl.和菥蓂柄锈菌(Puccinia thlaspeos Schub)。
本发明化合物还可与植物生长调节剂以及植物生长调节生物体诸如蜡状芽孢杆菌(Bacillus cereus)菌株BP01结合地使用,所述植物生长调节剂诸如艾维激素、N-(苯基甲基)-1H-嘌呤-6-胺、丙酰芸苔素内酯、赤霉酸、赤霉素A4和A7、超敏蛋白、甲哌啶、调环酸钙、茉莉酮、硝酚钠和抗倒酯。
农用保护剂(即除草剂、除草剂安全剂、杀昆虫剂、杀真菌剂、杀线虫剂、杀螨剂、和生物制剂)的一般参考文献包括The Pesticide Manual,第13 版,C.D.S.Tomlin编辑,British Crop Protection Council,Farnham,Surrey, U.K.,2003,和The BioPesticideManual,第2版,L.G.Copping编辑,British Crop Protection Council,Farnham,Surrey,U.K.,2001。
对于其中使用一种或多种这些不同混合对的实施方案而言,混合对通常以类似于单独使用混合物对时的常规量的量使用。更具体地,在混合物中,活性成分通常以介于产品标签上指明单独使用活性成分的施用率的二分之一至满施用率之间的施用率来施用。这些量列出于参考文献诸如The Pesticide Manual and The BioPesticide Manual中。这些不同混合对(总量) 与式1的化合物的重量比通常介于约1:3000和约3000:1之间。值得注意的是介于约1:300和约300:1之间的重量比(例如介于约1:30和约30:1之间的比率)。本领域的技术人员可易于通过简单的实验来确定获得所期望的生物活性范围所需要的活性成分的生物学有效量。显然,包含这些附加组分可使杂草防治范围超越式1的化合物本身所防治的范围。
在某些情况下,本发明化合物与其它生物活性(尤其是除草)化合物或试剂(即活性成分)的组合对于杂草可获得大于累加(即协同)的效应,和 /或对于作物或其它期望植物可获得小于累加(即安全化)的效应。降低释放在环境中的活性成分的量,同时确保有效的害虫防治,一直是人们所期望的。使用较大量活性成分以提供更有效的杂草防治而不会造成过度作物伤害的能力也是期望的。当除草活性成分以获得农艺上令人满意的杂草防治程度的施用率对杂草产生协同作用时,此类组合可有利地用于降低作物生产成本,并且减少环境负荷。当除草活性成分的安全化发生于作物上时,此类组合可有利地用于通过减少杂草竞争而提高作物保护。
值得注意的是本发明化合物与至少一种其它除草活性成分的组合。特别值得注意的是其中其它除草活性成分具有与本发明化合物不同的作用位点的此类组合。在某些情况下,与至少一种具有类似防治范围但是不同作用位点的其它除草活性成分的组合将尤其有利于抗性管理。因此,本发明组合物还可包含具有相似防治范围但不同作用位点的(除草有效量的)至少一种附加的除草活性成分。
本发明的化合物也可与诸如以下的除草剂安全剂结合使用以提高对某些作物的安全性:二丙烯草胺、解草酮、解草酯、苄草隆、解草胺腈、环丙磺酰胺、杀草隆、二氯丙烯胺、dicyclonon、dietholate、哌草丹、解草唑、解草啶、解草安、氟草肟、解草噁唑、双苯恶唑酸-乙酯、吡唑解草酯、甲基氨基甲酸4-氯苯基酯、苯草酮萘二甲酸酐(1,8-萘二甲酸酐)、解草腈、N-(氨基羰基)-2-甲基苯磺酰胺、N-(氨基羰基)-2-氟苯磺酰胺、1-溴-4-[(氯甲基)磺酰基]苯(BCS)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(MON 4660)、2-(二氯甲基)-2-甲基-1,3-二噁戊烷(MG 191)、1,6-二氢-1-(2-甲氧基苯基)-6-氧代-2- 苯基-5-嘧啶羧酸乙酯、2-羟基-N,N-二甲基-6-(三氟甲基)吡啶-3-甲酰胺以及 3-氧代-1-环己烯-l-基1-(3,4-二甲基苯基)-l,6-二氢-6-氧代-2-苯基-5-嘧啶羧酸酯。解毒有效量的除草剂安全剂可与本发明化合物同时施用,或作为种子处理物施用。因此,本发明的一个方面涉及除草剂混合物,所述除草剂混合物包含本发明化合物和解毒有效量的除草剂安全剂。种子处理物对于选择性杂草防治尤为有用,因为它将解毒作用物理地限制在作物植物上。因此,尤其有用的本发明实施方案为用于选择性防治作物中不期望的植被生长的方法,所述方法包括使所述作物的所在地接触除草有效量的本发明化合物,其中所述作物自其长成的种子用解毒有效量的安全剂处理。安全剂的解毒有效量易于由本领域技术人员通过简单的实验确定。
值得注意的是包含以下物质的组合物:(除草有效量的)本发明化合物、 (有效量的)至少一种选自其它除草剂和除草剂安全剂的附加活性成分、以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的组分。
表A1列出了组分(a)与组分(b)的具体组合,例证了本发明的混合物、组合物和方法。组分(a)栏中化合物No.(化合物编号)(即化合物1) 标示于索引表A中。表A1的第二栏列出具体组分(b)化合物(例如第一行中的“2,4-D”)。表A1的第三栏、第四栏和第五栏列出了在将组分(a) 化合物典型施用于田间生长作物时,相对于组分(b)的重量比率范围(即(a):(b))。因此,例如,表A1第一行具体公开,组分(a)(即索引表A中化合物1)与2,4-D的组合通常以介于1:384–6:1之间的重量比率施用。表A1的其余行以类似方式构建。
表A1
表A2如同上表A1构造,不同的是“组分(a)”栏标题下面的条目被下文所示的相应组分(a)的栏条目替代。“组分(a)”栏中的化合物编号标示于索引表A中。因此,例如,表A2中“组分(a)”栏标题下面的条目全列举为“化合物2”(即索引表A中所标示的化合物2),并且表A2 中栏标题下方的第一行具体公开了化合物2与2,4-D的混合物。表A3至表 A60构造类似。
下列测试证明了本发明的化合物针对具体杂草的防治功效。然而,由所述化合物提供的杂草防治作用不限于这些物种。化合物的描述参见索引表A。以下缩写用于索引表中,如下所示:t为叔,Me为甲基,morph为吗啉基,Bn为苄基并且Bu为丁基。缩写“Cmpd.No.”代表“化合物编号”。缩写“Ex.”代表“实施例”,并且跟随有数字,表示其中制备所述化合物的实施例。使用大气压力化学离子化(AP+)观测的经由H+(分子量为1)加在所述分子上形成的最高同位素丰度的母离子的分子量(M+1)以±0.5Da 内的估计精度报告质谱。
索引表A
*1H NMR数据参见索引表B。
**1H NMR数据参见合成实施例。
#M-1峰。
索引表B
a 1H NMR数据以距四甲基硅烷的低场ppm数为单位。偶合由(s)-单峰、(d)-双峰、(t)-三重峰、(m)-多重峰、(br s)-宽单峰来标明。
本发明的生物学实施例
测试A
将选自稗草(Echinochloa crus-galli)、地肤(Kochia scoparia)、豚草 (大猪草,Ambrosia elatior)、意大利黑麦草(Italian ryegrass,Lolium multiflorum)、大马唐草(large crabgrass,Digitaria sanguinalis)、狗尾草 (giant foxtail,Setariafaberii)、牵牛花(Ipomoea spp.)、野苋菜(Amaranthus retroflexus)、绒毛叶(Abutilontheophrasti)、小麦(Triticum aestivum)和玉米(Zea mays)的植物物种的种子种植到壤土和砂土的共混物中并且采用定向土壤喷雾使用配制成包含表面活性剂的非植物毒性溶剂混合物的测试化学品进行出苗前处理。
同时,将选自这些作物与杂草物种以及黑草(Alopecurus myosuroides) 和猪殃殃(catchweed bedstraw,Galium aparine)的植物种植于包含相同的壤土和砂土的共混物的盆中,并且用以相同方式配制的测试化合物来进行出苗后施用处理。使用高度范围在2cm至10cm并且在一叶至二叶阶段的植物来进行出苗后处理。使经处理的植物与未经处理的对照物在温室中保持约10 天,之后将所有经处理的植物与未经处理的对照物比较,并且目视评估损伤。总结于表A中的植株响应评分基于0至100标度,其中0为无效果,而100 为完全防治。破折号(–)响应表示无测试结果。
测试B
在淹水稻田测试中使选自稻(Oryza sativa)、小花轮伞草(small-flowerumbrella sedge,Cyperus difformis)、沼生异蕊花(Heteranthera limosa)、和稗草(Echinochloa crus-galli)的植物物种生长至2叶阶段以供测试。在处理时,将测试盆注水至距土壤表面上方3cm,通过向田水直接施用测试化合物来处理,然后在测试期间保持该水深。将经处理的植株和对照物在温室中保持13天至15天,之后将所有物种与对照物进行对比,并且视觉评估。总结于表B中的植株响应评分基于0至100标度,其中0为无效果,而100为完全防治。破折号(–)响应表示无测试结果。
测试C
将选自以下的植物物种的种子种植到壤土和砂土的共混物中并且采用配制成包含表面活性剂的非植物毒性溶剂混合物的测试化学品进行出苗前处理:黑草(Alopecurusmyosuroides)、意大利黑麦草(Italian ryegrass,Lolium multiflorum)、小麦(冬小麦,Triticum aestivum)、猪殃殃(catchweed bedstraw, Galium aparine)、玉米(Zea mays)、大马唐草(large crabgrass,Digitaria sanguinalis)、狗尾草(giant foxtail,Setariafaberii)、约翰逊草(Sorghum halepense)、藜(Chenopodium album)、牵牛花(Ipomoeacoccinea)、油莎草(yellow nutsedge,Cyperus esculentus)、反枝苋(Amaranthusretroflexus)、豚草(大猪草,Ambrosia elatior)、大豆(Glycine max)、稗草(Echinochloacrus-galli)、油籽油菜(Brassica napus)、苋菜藤子(普通水麻,Amaranthus rudis)和绒毛叶(Abutilon theophrasti)。
与此同时,将选自这些作物和杂草物种的植物以及繁缕(长毛箐姑草, Stellariamedia)、地肤(Kochia scoparia)和野生燕麦(wild oat,Avena fatua) 种植到包含含有泥炭藓泥煤苔类、蛭石、湿润剂和起始营养物的Redi-栽培介质(Scotts Company,14111Scottslawn Road,Marysville,Ohio 43041)的盆中,并且通过出苗后施用以相同方式配制的测试化学品进行处理。使用 2cm至18cm高度范围内(一叶至四叶阶段)的植株进行出苗后处理。将经处理的植株和对照物在温室中保持13天至15天,之后将所有物种与对照物进行对比,并且视觉评估。总结于表C中的植株响应评分基于0至100标度,其中0为无效果,而100为完全防治。破折号(–)响应表示无测试结果。
测试D
将选自以下的植物物种的种子种植到粉砂壤土中并且采用配制成包含表面活性剂的非植物毒性溶剂混合物的测试化学品进行出苗前处理:蓝草 (一年生早熟禾,Poaannua)、黑草(Alopecurus myosuroides)、加拿大蓟 (Cirsium arvense)、金黄草(小子虉草(Phalaris minor))、繁缕(长毛箐姑草,Stellaria media)、多裂叶老鹳草(cutleafgeranium,Geranium dissectum)、猪殃殃(catchweed bedstraw,Galium aparine)、旱雀麦(downy bromegrass, Bromus tectorum)、田野罂粟(Papaver rhoeas)、原野紫罗兰(Violaarvensis)、绿狗尾草(green foxtail,Setaria viridis)、宝盖草(henbit deadnettle,Lamium amplexicaule)、意大利黑麦草(Italian ryegrass,Lolium multiflorum)、地肤(Kochia scoparia)、藜(Chenopodium album)、油菜籽(Brassica napus)、野苋菜(Amaranthus retroflexus)、春黄菊(白夏菊,Matricaria inodora)、俄罗斯蓟(Salsolakali)、婆婆纳(大婆婆纳,Veronica persica)、春大麦 (spring barley,Hordeumvulgare)、春小麦(spring wheat,Triticum aestivum)、野生荞麦(wild buckwheat,Polygonum convolvulus)、野生芥菜(wild mustard, Sinapis arvensis)、野生燕麦(wildoat,Avena fatua)、野生萝卜(wild radish, Raphanus raphanistrum)、盘固拉草(Aperaspica-venti)、冬大麦(winter barley, Hordeum vulgare)和冬小麦(winter wheat,Triticum aestivum)。
与此同时,将这些物种种植到包含含有泥炭藓泥煤苔藓类、蛭石、湿润剂和起始营养物的Redi-栽培介质(Scotts Company,14111Scottslawn Road,Marysville,Ohio43041)的盆中,并且通过出苗后施用以相同方式配制的测试化学品进行处理。植株高度在2cm至18cm(1-叶至4-叶阶段)范围内。将经处理的植株和对照物在受控生长环境中保持14天至21天,之后将所有物种与对照物进行对比,并且视觉评估。总结于表D中的植株响应评分基于0至100标度,其中0为无效果,而100为完全防治。破折号(–)响应表示无测试结果。
测试E
将选自以下的植物物种的种子种植到粉砂壤土中并且采用配制成包含表面活性剂的非植物毒性溶剂混合物的测试化学品进行出苗前处理:玉米 (Zea mays)、大豆(Glycine max)、绒毛叶(Abutilon theophrasti)、藜 (Chenopodium album)、猩猩草(Euphorbia heterophylla)、长芒苋(palmer pigweed,Amaranthus palmeri)、苋菜藤子(普通水麻,Amaranthus rudis)、伏生臂形草(Brachiaria decumbens)、大马唐草(largecrabgrass,Digitaria sanguinalis)、巴西马唐草(Brazilian crabgrass,Digitariahorizontalis)、洋野黍(fall panicum,Panicum dichotomiflorum)、狗尾草(giantfoxtail,Setaria faberii)、绿狗尾草(green foxtail,Setaria viridis)、牛筋草(Eleusine indica)、约翰逊草(Sorghum halepense)、豚草(大猪草,Ambrosia elatior)、稗草 (Echinochloa crus-galli)、蒺藜草(棘蒺藜草,Cenchrus echinatus)、金午时花(Sida rhombifolia)、意大利黑麦草(Lolium multiflorum)、鸭跖草(弗吉尼亚鸭跖草,Commelina virginica)、田旋花(Convolvulus arvensis)、牵牛花(Ipomoea coccinea)、龙葵(东方龙葵,Solanum ptycanthum)、地肤 (Kochia scoparia)、油莎草(yellownutsedge,Cyperus esculentus)、小蓬草(Conyza canadensis)和咸丰草(hairybeggarticks,Bidens pilosa)。
与此同时,将得自这些作物和杂草物种的植物以及苋菜藤子_RES1(抗 ALS&Triazine普通水麻,Amaranthus rudis)和苋菜藤子_RES2(抗ALS& HPPD普通水麻,Amaranthus rudis)种植到包含含有泥炭藓泥煤苔藓类、蛭石、湿润剂和起始营养物的Redi-栽培介质(Scotts Company,14111 Scottslawn Road,Marysville,Ohio43041)的盆中,并且通过出苗后施用以相同方式配制的测试化学品进行处理。用于出苗后处理的植株高度在2cm至 18cm(1-叶至4-叶阶段)范围内。将经处理的植株和对照物在温室中保持 14天至21天,之后将所有物种与对照物进行对比,并且视觉评估。总结于表E中的植株响应评分基于0至100标度,其中0为无效果,而100为完全防治。破折号(–)响应表示无测试结果。
测试F
该测试评估化合物1或化合物2与各种商业除草剂的混合物对多种植物物种的效应。将所选的多种植物物种的种子种植到砂壤土中,并采用配制成非植物毒性溶剂混合物的测试化学品进行出苗后或出苗前处理。使植物生长在使用补充照明的温室中以保持约16h的光周期;日间和夜间的温度分别为约24℃-30℃和19℃-21℃。通过灌水系统施用平衡肥料。将经处理的植物和对照物在温室中保持20天,此后将所有物种与对照物进行比较,并目测评估。植物响应等级概述于表F1至F4中,并且基于0至100标度,其中0为没有效果,而100为完全防治。破折号(–)响应表示无测试结果。施用率 (即“Rate”)以活性成分克数每公顷(g a.i./ha)表示。在下表中,KCHSC 为地肤(Kochia scoparia),LOLMU为意大利黑麦草(Lolium multiflorum), AMBEL为大猪草(Ambrosia elatior),ECHCG为稗草(Echinochloacrus-galli),SETVI为狗尾草(Setaria faberii),AMARE为红根苋(Amaranthusretroflexus),ALOMY为黑草(Alopecurus myosuroides)并且GALAP为猪殃殃(Galiumaparine)。“观测的”为观测效果。“Exp.”为由Colby公式计算出的预期效果。
采用Colby公式来确定根据混合物预计的除草效应。Colby公式(Colby, S.R.“Calculating Synergistic and Antagonistic Responses of HerbicideCombinations”,Weeds,15(1),第20–22页(1967))计算除草剂混合物的预计加和效应,对于两种活性成分具有下列形式:
Pa+b=Pa+Pb–(PaPb/100)
其中Pa+b为根据单独组分加和贡献预计的混合物效应百分比:
Pa为在与所述混合物中施用率相同的施用率下,观察到的第一活性成分的效应百分比,并且
Pb为在与所述混合物中施用率相同的施用率下,观察到的第二活性成分的效应百分比。
Colby公式所预期的结果和加性效应列出于表F1至F4。
表F1:当出苗后施用时,由化合物1自身以及与甲基磺草酮的组合获得的观测的和 预期的结果。
如从表F1中所列的结果可以看出,杂草物种的大部分观测结果大于/ 等于所预期的,由此示出在苗后除草施用中化合物1和甲基磺草酮对所有以上杂草物种有较高的协同增强效应。
表F2:当出苗前施用时,由化合物1自身以及与甲基磺草酮的组合获得的观测的和 预期的结果。
如从表F2中所列的结果可以看出,杂草物种的大部分观测结果大于/ 等于所预期的,由此示出在出苗前除草施用中化合物1和甲基磺草酮对所有以上杂草物种有较高的协同增强效应。
表F3:当苗后施用时,由化合物2自身以及与阿特拉津的组合获得的观测的和预期 的结果。
如从表F3中所列的结果可以看出,杂草物种的大部分观测结果大于/ 等于所预期的,由此示出在苗后除草施用中化合物2和阿特拉津对所有以上杂草物种有较高的协同增强效应。
表F4:当出苗前施用时,由化合物2自身以及与阿特拉津的组合获得的观测的和预 期的结果。
如从表F4中所列的结果可以看出,杂草物种的大部分观测结果大于/ 等于所预期的,由此示出在出苗前除草施用中化合物2和阿特拉津对所有以上杂草物种有协同/累加效应。
Claims (24)
1.一种选自式1的化合物及其盐,
其中,
W为O或S;
R1为H、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基、苄基或苯基;或者5-元或6-元饱和或部分饱和的杂环,其包含选自碳和至多1个O和1个S的环成员;
R2为H、卤素、-CN、-CHO、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C2–C8二烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C1–C7烷氧基、C1–C5烷硫基、C2–C3烷氧基羰基;或任选地被卤素、C1–C4烷基或C1–C4卤代烷基取代的苯基;
X为O或S;或者
X为-C(R6)=C(R7)-,其中与R6键合的碳原子还键合至与R4键合的碳原子,并且与R7键合的碳原子还键合至式1的苯环部分;
每个R3独立地为卤素、-CN、硝基、C1–C5烷基、C2–C5烯基、C2–C5炔基、C3–C5环烷基、C4–C5环烷基烷基、C1–C5卤代烷基、C3–C5卤代烯基、C3–C5卤代炔基、C2–C5烷氧基烷基、C1–C5烷氧基、C1–C5卤代烷氧基、C1–C5烷硫基、C1–C5卤代烷硫基或C2–C5烷氧基羰基;
R4、R6和R7独立地为H、卤素、硝基、-CN、C1–C5烷基、C2–C5烯基、C2–C5炔基、C3–C5环烷基、C4–C5环烷基烷基、C1–C5卤代烷基、C3–C5卤代烯基、C3–C5卤代炔基、C2–C5烷氧基烷基、C1–C5烷氧基、C1–C5卤代烷氧基、C1–C5烷硫基、C1–C4烷基亚磺酰基、C1–C4烷基磺酰基、C1–C5卤代烷硫基或C2–C5烷氧基羰基;
G为G1或W1G1;
G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、-CONR10R11、-S(O)2NR10R11或P(=O)R12;或C1–C4烷基、C2–C4烯基、C2–C4炔基、C1–C4卤代烷基、C2–C4卤代烯基、C2–C4卤代炔基、C1–C4烷氧基烷基、C3–C6环烷基或C4–C7环烷基烷基;或者5-元或6-元杂环;
W1为C1–C4烷二基或C2–C4烯二基;
R8和R10独立地为C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C4–C7环烷基烷基;或苯基、苄基或5-元至6-元杂环,每个苯基、苄基或杂环任选地被卤素、C1–C4烷基或C1–C4卤代烷基取代;
R9为C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C2–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C4–C7环烷基烷基;或苯基、苄基或5-元至6-元杂环,每个苯基、苄基或杂环任选地被卤素、C1–C4烷基或C1–C4卤代烷基取代;
R11为H、C1-C7烷基、C2–C7烯基、C2–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C1–C7卤代烷基或C2–C7烷氧基烷基;
R12为C1-C7烷基或C1-C7烷氧基;并且
n为0、1、2、3或4;
前提条件是当R4为H时,则X为-C(R6)=C(R7)-。
2.根据权利要求1所述的化合物,其中
W为O;
X为O、S、-CH=CH-、-C(CH3)=CH-、-CH=CF-、-CH=CCl-或-CH=C(CH3)-;
R1为H、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基、苄基或苯基;
R2为H、卤素、-CN、-CHO、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C2–C8二烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C1–C7烷氧基或C1–C5烷硫基;
每个R3独立地为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
R4为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
G为G1;
G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、-CONR10R11、-S(O)2NR10R11或P(=O)R12;或C3–C6环烷基或C4–C7环烷基烷基;
R8和R10独立地为C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R9为C1–C7烷基、C3–C7环烷基、C2–C3卤代烷基或C2–C7烷氧基烷基;
R11为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R12为C1-C3烷基或C1-C3烷氧基;并且
n为0、1、2或3。
3.根据权利要求2所述的化合物,其中
X为-CH=CH-、-C(CH3)=CH-、-CH=CF-、-CH=CCl-或-CH=C(CH3)-;
R1为H、C1–C7烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基或苄基;
R2为H、卤素、-CN、-CHO、C1–C7烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、C4–C7烷基环烷基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C2–C7烷氧基烷基或C1–C7烷氧基;
每个R3独立地为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
R4为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
G1为H、-C(=O)R8、-CO2R9、-S(O)2R8、-CONR10R11、-S(O)2NR10R11或P(=O)R12;
R8、R9和R10独立地为C1-C7烷基、C3-C7环烷基或C2-C7烷氧基烷基;
R11为H、C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基;并且
R12为CH3或OCH3。
4.根据权利要求3所述的化合物,其中
X为-CH=CH-、-CH=CF-、-CH=CCl-或-CH=C(CH3)-,
R1为甲基、乙基、正丙基或2-甲氧基乙基;
R2为H、甲基、乙基、正丙基、CF3或甲氧基;
每个R3独立地为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
R4为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
G1为H、-C(=O)R8、-CO2R9、-S(O)2R8或P(=O)R12;
R8和R9独立地为C1–C7烷基或C2–C7烷氧基烷基;并且
n为1或2。
5.根据权利要求1所述的化合物,其中
W为O或S;
R1为C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基或苯基;
R2为H、卤素、-CN、C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C2–C3氰基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C1–C7烷氧基、C1–C5烷硫基、C2–C3烷氧基羰基或苯基;
X为O或S;或者
X为-C(R6)=C(R7)-,其中与R6键合的碳原子还键合至与R4键合的碳原子,并且与R7键合的碳原子还键合至式1的苯环部分;
每个R3独立地为卤素、-CN、C1–C5烷基、C2–C5烯基、C2–C5炔基、C3–C5环烷基、C4–C5环烷基烷基、C1–C5卤代烷基、C3–C5卤代烯基、C3–C5卤代炔基、C2–C5烷氧基烷基、C1–C5烷氧基、C1–C5卤代烷氧基、C1–C5烷硫基、C1–C5卤代烷硫基或C2–C5烷氧基羰基;
R4、R6和R7独立地为H、卤素、-CN、C1–C5烷基、C2–C5烯基、C2–C5炔基、C3–C5环烷基、C4–C5环烷基烷基、C1–C5卤代烷基、C3–C5卤代烯基、C3–C5卤代炔基、C2–C5烷氧基烷基、C1–C5烷氧基、C1–C5卤代烷氧基、C1–C5烷硫基、C1–C5卤代烷硫基或C2–C5烷氧基羰基;
G为G1;
G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、-CONR10R11或-S(O)2NR10R11;
R8和R10独立地为C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C4–C7环烷基烷基、苯基或苄基;
R9为C1–C7烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C2–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C4–C7环烷基烷基、苯基或苄基;
R11为H、C1-C7烷基、C2–C7烯基、C2–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C1–C7卤代烷基或C2–C7烷氧基烷基;并且
n为0、1、2、3或4;
前提条件是当R4为H时,则X为-C(R6)=C(R7)-。
6.根据权利要求5所述的化合物,其中
W为O;
X为O、S、-CH=CH-、-C(CH3)=CH-或-CH=C(CH3)-;
R1为C1-C4烷基、C3–C4烯基、C3–C4炔基、C3–C4环烷基、C2–C3氰基烷基、C1–C3卤代烷基或C2–C4烷氧基烷基;
R2为H、卤素、-CN、C1–C4烷基、C3–C5环烷基、C1–C3卤代烷基、C2–C4烷氧基烷基或C1–C3烷氧基;
每个R3独立地为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
R4为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
G1为H、-C(=O)R8、-CO2R9、-S(O)2R8、-CONR10R11或-S(O)2NR10R11;
R8和R10独立地为C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R9为C1–C7烷基、C3–C7环烷基、C2–C3卤代烷基或C2–C7烷氧基烷基;
R11为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;并且
n为0、1、2或3。
7.根据权利要求6所述的化合物,其中
R1为C1–C3烷基、烯丙基、炔丙基、CH2CH2CN、C1–C2卤代烷基或2-甲氧基乙基;
R2为H、卤素、C1–C3烷基、环丙基、C1–C2卤代烷基、甲氧基或乙氧基;
每个R3独立地为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
R4为卤素、-CN、C1–C2烷基、-CH=CH2、-C≡CH、环丙基、C1–C2卤代烷基或C1–C2烷氧基;
R8、R9和R10独立地为C1-C7烷基、C3-C7环烷基或C2-C7烷氧基烷基;并且
R11为H、C1–C7烷基、C3–C7环烷基或C2–C7烷氧基烷基。
8.根据权利要求7所述的化合物,其中
R1为甲基、乙基、正丙基或2-甲氧基乙基;
R2为H、甲基、乙基、正丙基、CF3或甲氧基;
每个R3独立地为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
R4为卤素、-CN、甲基、乙基、-CH=CH2、-C≡CH、环丙基、CF3、甲氧基或乙氧基;
G1为H、-C(=O)R8、-CO2R9或-S(O)2R8;
R8和R9独立地为C1–C7烷基或C2–C7烷氧基烷基;并且
n为1或2。
9.根据权利要求1所述的化合物,所述化合物选自:
4-(2,5-二甲基苯并[b]噻吩-3-基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮,
5-羟基-2,6-二甲基-4-(2,5,7-三甲基苯并[b]噻吩-3-基)-3(2H)-哒嗪酮,
5-羟基-2,6-二甲基-4-(2,4,6-三甲基苯并[b]噻吩-3-基)-3(2H)-哒嗪酮,
5-羟基-2,6-二甲基-4-(2-甲基-3-苯并呋喃基)-3(2H)-哒嗪酮,
5-羟基-4-(5-甲氧基-3-苯并呋喃基)-2,6-二甲基-3(2H)-哒嗪酮,
4-(5-氯-2-甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮,
4-(2,5-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮,
4-(2,4-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮,
4-(2,7-二甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮,
4-(2-乙基-5-甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮,
5-羟基-2,6-二甲基-4-(1-萘基)-3(2H)-哒嗪酮,
5-羟基-2,6-二甲基-4-(2,5,7-三甲基-3-苯并呋喃基)-3(2H)-哒嗪酮,
4-(5-乙基-2-甲基-3-苯并呋喃基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮,
5-(乙酰氧基)-4-(2,5-二甲基-3-苯并呋喃基)-2,6-二甲基-3(2H)-哒嗪酮,
5-(乙酰氧基)-4-(2,7-二甲基-3-苯并呋喃基)-2,6-二甲基-3(2H)-哒嗪酮,
5-(乙酰氧基)-2,6-二甲基-4-(2,5,7-三甲基-3-苯并呋喃基)-3(2H)-哒嗪酮,
2,2-二甲基丙酸5-(2,5-二甲基-3-苯并呋喃基)-1,6-二氢-1,3-二甲基-6-氧代基-4-哒嗪酯,
2,2-二甲基丙酸1,6-二氢-1,3-二甲基-6-氧代基-5-(2,5,7-三甲基-3-苯并呋喃基)-4-哒嗪酯,以及
4-(2-乙基-4,6-二甲基苯并[b]噻吩-3-基)-5-羟基-2,6-二甲基-3(2H)-哒嗪酮。
10.一种除草剂组合物,所述除草剂组合物包含根据权利要求1所述的化合物和至少一种组分,所述组分选自表面活性剂、固体稀释剂和液体稀释剂。
11.一种除草剂组合物,所述除草剂组合物包含根据权利要求1所述的化合物、至少一种选自其它除草剂和除草剂安全剂的附加活性成分、和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的组分。
12.一种除草剂混合物,所述除草剂混合物包含(a)根据权利要求1所述的化合物,和(b)至少一种附加活性成分,所述附加活性成分选自(b1)光系统II抑制剂、(b2)乙酰羟酸合酶(AHAS)抑制剂、(b3)乙酰-CoA羧化酶(ACCase)抑制剂、(b4)生长素模拟物和(b5)5-烯醇-丙酮酸莽草酸-3-磷酸酯(EPSP)合酶抑制剂、(b6)光系统I电子转向剂、(b7)原卟啉原氧化酶(PPO)抑制剂、(b8)谷氨酰胺合成酶(GS)抑制剂、(b9)极长链脂肪酸(VLCFA)延伸酶抑制剂、(b10)生长素运输抑制剂、(b11)八氢番茄红素脱氢酶(PDS)抑制剂、(b12)4-羟基苯基-丙酮酸双加氧酶(HPPD)抑制剂、(b13)homogentisate solenesyltransererase(HST)抑制剂、(b14)纤维素生物合成抑制剂、(b15)其它除草剂,其选自有丝分裂干扰物、有机砷化物、黄草灵、溴丁酰草胺、环庚草醚、苄草隆、棉隆、燕麦枯、汰草龙、乙氧苯草胺、抑草丁、杀木膦、调节膦、威百亩、甲基杀草隆、油酸、嗪草酮、壬酸和稗草畏,和(b16)除草剂安全剂;以及(b1)至(b16)的化合物的盐。
13.一种用于防治不期望的植被生长的方法,所述方法包括使所述植被或其环境与除草有效量的根据权利要求1所述的化合物接触。
14.一种除草剂混合物,所述除草剂混合物包含根据权利要求1所述的化合物和至少一种选自下列的附加活性成分:酰嘧磺隆、四唑嘧磺隆、苄嘧磺隆-甲酯、双草醚钠、氯酯磺草胺、氯嘧磺隆-乙酯、氯磺隆、醚磺隆、环丙嘧磺隆、双氯磺草安、胺苯磺隆-甲酯、乙氧嘧磺隆、啶嘧磺隆、双氟磺草胺、氟酮磺隆钠、唑嘧磺草胺、氟啶嘧磺隆-、氟啶磺隆钠、甲酰氨基嘧磺隆、氯吡嘧磺隆、咪草酸、甲氧咪草烟、甲咪唑烟酸、灭草烟、灭草喹、咪草烟、咪唑磺隆、碘磺隆-甲酯、碘磺隆-甲酯钠、iofensulfuron(2-碘-N-[[(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)氨基]羰基]苯磺酰胺)、甲基二磺隆-甲酯、嗪吡嘧磺隆(3-氯-4-(5,6-二氢-5-甲基-1,4,2-二嗪-3-基)-N-[[(4,6-二甲氧基-2-嘧啶基)氨基]羰基]-1-甲基-1H-吡唑-5-磺酰胺)、磺草唑胺、甲磺隆-甲酯、烟嘧磺隆、环氧嘧磺隆、五氟磺草胺、氟嘧磺隆-甲酯、丙苯磺隆钠、丙嗪嘧磺隆(2-氯-N-[[(4,6-二甲氧基-2-嘧啶基)氨基]羰基]-6-丙基咪唑[1,2-b]哒嗪-3-磺酰胺)、氟磺隆、吡嘧磺隆、嘧啶肟草醚、环酯草醚、嘧草醚、嘧草硫醚钠、砜嘧磺隆、甲嘧磺隆、磺酰磺隆、噻酮磺隆、噻磺隆、氟酮磺草胺(N-[2-[(4,6-二甲氧基-1,3,5-三嗪-2-基)羰基]-6-氟苯基]-1,1-二氟-N-甲基甲磺酰胺)、醚苯磺隆、苯磺隆-甲酯、三氟啶磺隆、三氟啶磺隆钠、氟胺磺隆和三氟甲磺隆。
15.一种除草剂混合物,所述除草剂混合物包含与砜嘧磺隆、噻磺隆、苯磺隆、烟嘧磺隆、甲磺隆、氟啶嘧磺隆、氯酯磺草胺、甲氧磺草胺或双氟磺草胺相混合的根据权利要求1所述的化合物。
16.一种除草剂混合物,所述除草剂混合物包含与砜嘧磺隆相混合的根据权利要求1所述的化合物。
17.一种除草剂混合物,所述除草剂混合物包含与氯嘧磺隆相混合的根据权利要求1所述的化合物。
18.一种除草剂混合物,所述除草剂混合物包含与噻磺隆相混合的根据权利要求1所述的化合物。
19.一种除草剂混合物,所述除草剂混合物包含与苯磺隆相混合的根据权利要求1所述的化合物。
20.一种除草剂混合物,所述除草剂混合物包含与胺苯磺隆-甲酯相混合的根据权利要求1所述的化合物。
21.一种除草剂混合物,所述除草剂混合物包含与烟嘧磺隆相混合的根据权利要求1所述的化合物。
22.一种除草剂混合物,所述除草剂混合物包含与甲嘧磺隆相混合的根据权利要求1所述的化合物。
23.一种除草剂混合物,所述除草剂混合物包含与氯磺隆相混合的根据权利要求1所述的化合物。
24.一种选自式1的化合物及其盐,
其中,
W为O;
X为O、S、-CH=CH-、-C(CH3)=CH-、-CH=CF-、-CH=CCl-或-CH=C(CH3)-;
R1为H、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C3–C7烷硫基烷基、C1–C7烷氧基、苄基或苯基;
R2为H、卤素、-CN、-CHO、C1–C7烷基、C3–C8烷基羰基烷基、C3–C8烷氧基羰基烷基、C1–C4烷基羰基、C2–C7烷基羰基氧基、C4–C7烷基环烷基、C3–C7烯基、C3–C7炔基、C1–C4烷基亚磺酰基、C1–C4烷磺酰基、C1–C4烷基氨基、C2–C8二烷基氨基、C3–C7环烷基、C4–C7环烷基烷基、C2–C3氰基烷基、C1–C4硝基烷基、C2–C7卤代烷氧基烷基、C1–C7卤代烷基、C3–C7卤代烯基、C2–C7烷氧基烷基、C1–C7烷氧基或C1–C5烷硫基;
每个R3独立地为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
R4为卤素、-CN、C1–C3烷基、C2–C4烯基、C2–C4炔基、C3–C4环烷基、C1–C3卤代烷基、C1–C3烷氧基、C1–C2卤代烷氧基、C1–C2烷硫基或C1–C2卤代烷硫基;
G为G1;
G1为H、-C(=O)R8、-C(=S)R8、-CO2R9、-C(=O)SR9、-S(O)2R8、-CONR10R11、-S(O)2NR10R11或P(=O)R12;或C3–C6环烷基或C4–C7环烷基烷基;
R8和R10独立地为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R9为H、C1–C7烷基、C3–C7环烷基、C2–C3卤代烷基或C2–C7烷氧基烷基;
R11为H、C1–C7烷基、C3–C7环烷基、C1–C3卤代烷基或C2–C7烷氧基烷基;
R12为C1-C3烷基或C1-C3烷氧基;并且
n为0、1、2或3。
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