CN110357859B - 一种含不饱和基的喹唑啉二酮类化合物及其应用和一种农药除草剂 - Google Patents
一种含不饱和基的喹唑啉二酮类化合物及其应用和一种农药除草剂 Download PDFInfo
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- CN110357859B CN110357859B CN201910272370.3A CN201910272370A CN110357859B CN 110357859 B CN110357859 B CN 110357859B CN 201910272370 A CN201910272370 A CN 201910272370A CN 110357859 B CN110357859 B CN 110357859B
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- -1 Quinazoline diketone compound Chemical class 0.000 title claims abstract description 36
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 31
- 239000004009 herbicide Substances 0.000 title claims abstract description 28
- 239000000575 pesticide Substances 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 133
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 131
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 126
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 119
- 241000196324 Embryophyta Species 0.000 claims description 39
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000000361 pesticidal effect Effects 0.000 claims description 8
- 229940126214 compound 3 Drugs 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 150000008515 quinazolinediones Chemical class 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 241001290610 Abildgaardia Species 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940125898 compound 5 Drugs 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical group BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical group C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical group C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical group C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims description 2
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical group NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical group CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical group CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims description 2
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical group C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims description 2
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims description 2
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 claims description 2
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical group C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims description 2
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical group ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims description 2
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical group O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims description 2
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims description 2
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical group ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 claims description 2
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical group C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims description 2
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical group FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims description 2
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical group CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims description 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical group NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims description 2
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- A—HUMAN NECESSITIES
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
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- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
本发明涉及农药除草剂领域，公开了一种含不饱和基的喹唑啉二酮类化合物及其应用和一种农药除草剂，本发明的含不饱和基的喹唑啉二酮类化合物具有式(I)所示的结构。本发明提供的含不饱和基的喹唑啉二酮类化合物具有良好的防效和优异的安全性。
Description
技术领域
本发明涉及农药除草剂领域，具体涉及一种含不饱和基的喹唑啉二酮类化合物以及该含不饱和基的喹唑啉二酮类化合物的应用和一种含有该含不饱和基的喹唑啉二酮类化合物的农药除草剂。
背景技术
对羟基苯基丙酮酸双加氧酶(4-HPPD)在上个世纪90年代被确认为除草剂作用靶标。
4-HPPD广泛存在于需氧生物体内，其主要参与生物体内酪氨酸的代谢。在植物体内，酪氨酸的代谢产物对羟基苯基丙酮酸在4-HPPD的作用下生成尿黑酸，尿黑酸进一步转化成质体醌和生育酚。质体醌和生育酚是植物光合作用的重要前体。因此，通过抑制植物体内质体醌和生育酚的合成，阻碍植物的正常光合作用，致使植物发生白化症状而死亡。以HPPD为靶标的除草剂具有高效，低毒，对环境友好和对后茬作物安全性好等特点。因此，4-HPPD除草剂是一类非常具有研究价值和发展前景的除草剂。
2015年，CN104557739A首次筛选出含有喹唑啉二酮片段的HPPD类抑制剂分子，其代表性物质的结构如下，该物质主要用于防治高粱田等中的杂草：
随后，WO2017/140612A1在此基础上进一步公开了一系列HPPD类抑制剂分子，然而，在该现有技术中并未提供具体化合物的生物活性测试结果。并且，通过实验证实该现有技术中具体记载的化合物对水稻、小麦等作物并没有表现出足够的安全性，因此它们不能直接用于水稻田进行杂草的防治。
然而，水稻、玉米和小麦均是非常重要的粮食作物，水稻田、玉米田和小麦田杂草的防治，对提高水稻、玉米和小麦产量及解决世界粮食危机问题具有非常重要的作用。
特别地，现阶段，水稻田的恶性杂草稗草，抗性稗草，千金子等严重影响水稻的正常生长，尤其是抗性稗草发展的非常迅速，未来对抗性稗草的防治难度越来越大。
因此，提供对水稻田、玉米田和小麦田等中的杂草具有良好的防效以及高的安全性的新型HPPD类抑制剂具有重要意义。
发明内容
本发明的目的之一是利用结构的多样修饰以及创造性地引入具有特异选择性的活性片段以期改善分子成药性并克服现有技术存在的上述缺陷，提供一种能够用于水稻作物的HPPD除草剂。
本发明的目的之二是提供对水稻田、玉米田和小麦田等农作物种植地中的杂草具有良好的防效以及对农作物具有高的安全性的新型HPPD类抑制剂。
为了实现上述目的，本发明的第一方面提供一种含不饱和基的喹唑啉二酮类化合物，该化合物具有式(I)所示的结构：
其中，在式(I)中，
R1为烯丙基或炔丙基；
R2选自C1-6的烷基；
X选自C1-12的烷基、由1-6个选自卤素的原子取代的C6-10的芳基、由1-6个选自卤素的原子取代的C1-12的烷基、由C1-3的烷氧基取代的C1-12的烷基、C2-12的烯基、C2-12的炔基、含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基、由含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基取代的C1-12的烷基；
Y选自H、C1-6的烷基。
根据一种优选的具体实施方式，式(I)所示的化合物选自以下化合物中的至少一种：
化合物1：R1为烯丙基；R2为甲基；X为3-Cl-苯基；Y为甲基；
化合物2：R1为炔丙基；R2为甲基；X为3-Cl-苯基；Y为甲基。
化合物1所示的结构如下：
化合物1：
化合物2所示的结构如下：
化合物2：
根据另一种优选的具体实施方式，在式(I)中，
R1为烯丙基或炔丙基；
R2选自C1-3的烷基；
X选自C1-8的烷基、由1-3个选自F、Cl和Br的卤素取代的C6-10的芳基、由1-3个选自F、Cl和Br的卤素取代的C1-8的烷基、由C1-3的烷氧基取代的C1-8的烷基、C2-8的烯基、C2-8的炔基、含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基、由含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基取代的C1-8的烷基；
Y选自H、C1-3的烷基。
在该另一种优选的具体实施方式中，更优选在式(I)中，
R1为烯丙基或炔丙基；
R2选自甲基、乙基、正丙基、异丙基和环丙基；
X选自C1-6的烷基、由1-3个选自F、Cl和Br的卤素取代的苯基、由1-3个选自F、Cl和Br的卤素取代的C1-6的烷基、由C1-3的烷氧基取代的C1-6的烷基、C2-6的烯基、C2-6的炔基、含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基、由含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基取代的C1-6的烷基；
Y选自H、甲基、乙基、正丙基、异丙基和环丙基。
在该另一种优选的具体实施方式中，特别优选式(I)所示的化合物选自以下所列举的具体化合物中的至少一种。
化合物3：R1为烯丙基，R2为-CH3，X为-CH3，Y为-CH3；
化合物4：R1为烯丙基，R2为-CH3，X为-CH3，Y为
化合物5：R1为烯丙基，R2为-CH3，X为乙基，Y为-CH3；
化合物6：R1为烯丙基，R2为-CH3，X为乙基，Y为
化合物7：R1为烯丙基，R2为-CH3，X为正丙基，Y为-CH3；
化合物8：R1为烯丙基，R2为-CH3，X为正丙基，Y为
化合物9：R1为烯丙基，R2为-CH3，X为异丙基，Y为-CH3；
化合物10：R1为烯丙基，R2为-CH3，X为异丙基，Y为
化合物11：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物12：R1为烯丙基，R2为-CH3，X为
Y为
化合物13：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物14：R1为烯丙基，R2为-CH3，X为
Y为
化合物15：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物16：R1为烯丙基，R2为-CH3，X为
Y为
化合物17：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物18：R1为烯丙基，R2为-CH3，X为
Y为
化合物19：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物20：R1为烯丙基，R2为-CH3，X为
Y为
化合物21：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物22：R1为烯丙基，R2为-CH3，X为
Y为
化合物23：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物24：R1为烯丙基，R2为-CH3，X为
Y为
化合物25：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物26：R1为烯丙基，R2为-CH3，X为
Y为
化合物27：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物28：R1为烯丙基，R2为-CH3，X为
Y为
化合物29：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物30：R1为烯丙基，R2为-CH3，X为
Y为
化合物31：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物32：R1为烯丙基，R2为-CH3，X为
Y为
化合物33：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物34：R1为烯丙基，R2为-CH3，X为
Y为
化合物35：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物36：R1为烯丙基，R2为-CH3，X为
Y为
化合物37：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物38：R1为烯丙基，R2为-CH3，X为
Y为
化合物39：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物40：R1为烯丙基，R2为-CH3，X为
Y为
化合物41：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物42：R1为烯丙基，R2为-CH3，X为
Y为
化合物43：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物44：R1为烯丙基，R2为-CH3，X为
Y为
化合物45：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物46：R1为烯丙基，R2为-CH3，X为
Y为
化合物47：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物48：R1为烯丙基，R2为-CH3，X为
Y为
化合物49：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物50：R1为烯丙基，R2为-CH3，X为
Y为
化合物51：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物52：R1为烯丙基，R2为-CH3，X为
Y为
化合物53：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物54：R1为烯丙基，R2为-CH3，X为
Y为
化合物55：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物56：R1为烯丙基，R2为-CH3，X为
Y为
化合物57：R1为烯丙基，R2为-CH3，X为
Y为CH3；
化合物58：R1为烯丙基，R2为-CH3，X为
Y为
化合物59：R1为炔丙基，R2为-CH3，X为-CH3，Y为-CH3；
化合物60：R1为炔丙基，R2为-CH3，X为-CH3，Y为
化合物61：R1为炔丙基，R2为-CH3，X为乙基，Y为-CH3；
化合物62：R1为炔丙基，R2为-CH3，X为乙基，Y为
化合物63：R1为炔丙基，R2为-CH3，X为正丙基，Y为-CH3；
化合物64：R1为炔丙基，R2为-CH3，X为正丙基，Y为
化合物65：R1为炔丙基，R2为-CH3，X为异丙基，Y为-CH3；
化合物66：R1为炔丙基，R2为-CH3，X为异丙基，Y为
化合物67：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物68：R1为炔丙基，R2为-CH3，X为
Y为
化合物69：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物70：R1为炔丙基，R2为-CH3，X为
Y为
化合物71：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物72：R1为炔丙基，R2为-CH3，X为
Y为
化合物73：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物74：R1为炔丙基，R2为-CH3，X为
Y为
化合物75：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物76：R1为炔丙基，R2为-CH3，X为
Y为
化合物77：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物78：R1为炔丙基，R2为-CH3，X为
Y为
化合物79：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物80：R1为炔丙基，R2为-CH3，X为
Y为
化合物81：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物82：R1为炔丙基，R2为-CH3，X为
Y为
化合物83：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物84：R1为炔丙基，R2为-CH3，X为
Y为
化合物85：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物86：R1为炔丙基，R2为-CH3，X为
Y为
化合物87：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物88：R1为炔丙基，R2为-CH3，X为
Y为
化合物89：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物90：R1为炔丙基，R2为-CH3，X为
Y为
化合物91：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物92：R1为炔丙基，R2为-CH3，X为
Y为
化合物93：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物94：R1为炔丙基，R2为-CH3，X为
Y为
化合物95：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物96：R1为炔丙基，R2为-CH3，X为
Y为
化合物97：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物98：R1为炔丙基，R2为-CH3，X为
Y为
化合物99：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物100：R1为炔丙基，R2为-CH3，X为
Y为
化合物101：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物102：R1为炔丙基，R2为-CH3，X为
Y为
化合物103：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物104：R1为炔丙基，R2为-CH3，X为
Y为
化合物105：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物106：R1为炔丙基，R2为-CH3，X为
Y为
化合物107：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物108：R1为炔丙基，R2为-CH3，X为
Y为
化合物109：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物110：R1为炔丙基，R2为-CH3，X为
Y为
化合物111：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物112：R1为炔丙基，R2为-CH3，X为
Y为
化合物113：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物114：R1为炔丙基，R2为-CH3，X为
Y为
化合物115：R1为炔丙基，R2为-CH3，X为3-Cl-苯基；Y为-H；
化合物116：R1为炔丙基，R2为-CH3，X为3-Cl-苯基；Y为
化合物117：R1为炔丙基，R2为-CH2CH3，X为3-Cl-苯基；Y为-CH3；
化合物118：R1为炔丙基，R2为正丙基，X为3-Cl-苯基；Y为-CH3；
化合物119：R1为烯丙基，R2为正丙基，X为3-Cl-苯基；Y为-CH3。
本发明的发明人发现，本发明提供的含不饱和基的喹唑啉二酮类化合物相对于现有技术提供的结构接近的化合物，以及相对于本文的后文中提供的参照样本均明显具有更好的除草活性，特别地，本发明提供的化合物还明显具有更高的作物安全性。具体地，本发明的含不饱和基的喹唑啉二酮类化合物对田间杂草的防效特别优异，同时高剂量下，本发明提供的化合物对玉米、小麦和水稻均未产生任何药害。
进一步地，本发明的发明人还发现，本发明的化合物即便在增加使用剂量时，对作物仍然具有广谱的安全性。
本发明对合成式(I)所示的含不饱和基的喹唑啉二酮类化合物的方法没有特别的限定，本领域技术人员根据本发明提供的化合物结构结合化学领域内的合成方法能够获得合适的制备式(I)所示的含不饱和基的喹唑啉二酮类化合物的方法，本发明在此不再一一赘述。
例如，本发明的式(I)所示的含不饱和基的喹唑啉二酮类化合物可以根据如下合成路线合成：
在上述合成路线中，在酯化反应中，式(III)所示的化合物的合成方法例如可以为：将式(II)所示的化合物溶于溶剂中，加二氯亚砜，低温下搅拌反应。待反应完毕，脱干溶剂，剩余固体用溶剂溶解备用。低温下，将吡唑酮溶于溶剂中，并加入三乙胺，搅拌后，将用溶剂溶解的酰氯溶液滴加到反应体系中，TLC监测反应。待反应完毕，向反应体系中加入饱和NaHCO3溶液，萃取合并有机层，干燥浓缩进行柱层析得到式(III)所示的化合物。
在上述合成路线中，在重排反应中，式(IV)所示化合物的合成方法例如可以为：将式(III)所示的化合物、乙腈加入到烧瓶中，搅拌，加入Et3N和丙酮氰醇。TLC监测反应，待反应完成后，向反应体系中加入HCl溶液，继续搅拌，析出固体抽滤。
在上述合成路线中，在重排反应中，式(I)所示的化合物的合成方法可以在缚酸剂的条件下进行。
本发明的第二方面提供第一方面所述的含不饱和基的喹唑啉二酮类化合物在防治杂草中的应用。
优选地，所述杂草包括狗尾草、稗草、千金子、马唐、节节麦、苋菜、灰菜、苘麻、雀麦、野燕麦、看麦娘、日本看麦娘、黑麦草、饭包草、决明草、牵牛花、苍耳、莎草、大巢菜、反枝苋、假酸浆、鳢肠、马齿苋、刺苋、鬼针草、双穗雀稗、稻李氏禾、水竹叶、野慈姑、泽泻、雨久花、鸭跖草、鸭舌草、萤蔺、异型莎草等中的至少一种。
本发明的第三方面提供第一方面所述的含不饱和基的喹唑啉二酮类化合物在防治选自阔叶杂草、禾本科杂草和莎草科杂草中的至少一种杂草中的应用。
优选地，在本发明中，所述阔叶杂草包括苋菜、灰菜、苘麻、饭包草、决明草、牵牛、苍耳、反枝苋、假酸浆、鳢肠、马齿苋、刺苋、水竹叶、野慈姑、泽泻、雨久花、鸭跖草、鸭舌草和莎草中的至少一种。所述莎草包括萤蔺、异型莎草等。
优选地，在本发明中，所述禾本科杂草包括狗尾草、稗草、千金子、马唐、节节麦、雀麦、野燕麦、看麦娘、日本看麦娘、黑麦草、莎草、大巢菜、鬼针草、双穗雀稗、稻李氏禾中的至少一种。
本发明的第四方面提供第一方面所述的含不饱和基的喹唑啉二酮类化合物作为农药除草剂的应用。
本发明的第五方面提供一种农药除草剂，该农药除草剂由活性成分和辅料组成，所述活性成分包括前述第一方面中所述的含不饱和基的喹唑啉二酮类化合物中的至少一种。
优选地，在所述农药除草剂中，所述活性成分的含量为1～99.9999重量％。
根据一种优选的具体实施方式，所述活性成分中进一步包括安全剂。所述安全剂可以为本领域内常规使用的各种类型的安全剂。
例如，所述安全剂可以为吡唑解草酯、解毒喹、双苯噁唑酸、环丙磺酰胺、萘二甲酸酐、氯草烯安、R-28725、苯叉酰胺、解草酮、解草胺腈、解草唑、解草啶、BAS-145138、呋喃解草唑、喹啉衍生物、2,4-D、新型解毒剂T和赤霉素中的至少一种。
优选情况下，所述农药除草剂的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、毒饵、母液和母粉中的至少一种。
所述悬浮剂例如可以包括干悬浮剂、可分散油悬浮剂和水乳剂。
本发明的所述农药除草剂中的辅料包括但不限于表面活性剂、保护胶体、粘合剂、增稠剂、触变剂、渗透剂、螯合剂、染料、着色剂和聚合物等，例如还可以为充当载体的其它常规助剂。
本文中的载体表示一种或多种有机物、无机物、天然产物或合成的物质。它们有助于活性成分的施用，该载体一般是惰性的且必须是农业上可以接受的，特别是可以被处理植物所接受的。载体可以是固体的，如：陶土、天然或合成的硅酸盐、二氧化硅、树脂、蜡、固体肥料等；或者是液体的，如：水，醇类、酮类、石油馏分、芳烃或蜡烃、氯代烃、液化气等。
本发明所述表面活性剂的成分包括乳化剂，分散剂或润湿剂，它们可以是离子型的或非离子型的。可提及的实例是：聚丙烯酸盐、木质素磺酸盐、苯酚磺酸或萘磺酸盐、环氧乙烷与脂肪族醇或与脂肪族酸或与脂肪族胺与取代的苯酚(特别是烷基苯酚或芳基苯酚)的聚合物、磺酸琥珀酸盐、牛磺酸衍生物及醇的磷酸酯或多羟基乙基化的苯酚磷酸酯、烷基磺酸酯盐、烷基芳基磺酸盐、烷基硫酸盐、月桂基醚硫酸盐、脂肪醇硫酸盐、以及硫酸化十六-十七-十八烷醇以及硫酸化脂肪醇乙二醇醚，此外还有萘或萘磺酸与苯酚和甲醛的缩合物、聚氧乙烯辛基苯甲醚、乙氧基化异辛基醚、辛基酚或壬基酚、烷基苯基聚乙二醇醚、三丁基苯基聚乙二醇醚、三硬酯基苯基聚乙二醇醚、烷基芳基聚醚醇、醇和脂肪醇/氧化乙烯缩合物、乙氧基化蓖麻油、聚氧乙烯烷基醚、乙氧基化聚氧丙烯、月桂醇聚乙二醇醚缩醛、山梨醇酯、木素亚硫酸盐废液、以及蛋白质、变性蛋白、多糖、疏水改性淀粉、聚乙烯醇、聚羧酸盐、聚氧烷基化物、聚乙烯胺、聚乙烯吡咯烷酮以及共聚物。
本发明对制备所述农药除草剂的方法没有特别的限制，本领域技术人员可以采用农药领域内常规的制备方法进行制备以形成相应的试剂。
本发明所述的农药除草剂包括但不限于通过例如喷雾的方法用于农作物。
本发明提供的含不饱和基的喹唑啉二酮类化合物及含有该含不饱和基的喹唑啉二酮类化合物的农药除草剂具有HPPD类除草剂的全部优点，并且具有环境友好，后茬作物安全、用量低、时效性好、杀草谱广、安全性高等优点。
特别地，本发明提供的含不饱和基的喹唑啉二酮类化合物对玉米、小麦和水稻表现出了优良的作物安全性。
本发明提供的含不饱和基的喹唑啉二酮类化合物对阔叶杂草、禾本科杂草和莎草科杂草均具有很高的除草活性，尤其是对水稻田内杂草的防效显著，例如对水稻田中的禾本科杂草(稗草、千金子、双穗雀稗、狗尾草、马唐、稻李氏禾等)；阔叶杂草(水竹叶、野慈姑、泽泻、雨久花、鸭跖草、鸭舌草等)；莎草(萤蔺、异型莎草等)。
本发明提供的含不饱和基的喹唑啉二酮类化合物的除草活性优于商品化药剂硝磺草酮。
具体实施方式
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值，这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说，各个范围的端点值之间、各个范围的端点值和单独的点值之间，以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围，这些数值范围应被视为在本文中具体公开。
本发明选用以下物质作为参照样本：
化合物D1：
化合物D2：
化合物D3：
化合物D4：
化合物D5：
化合物D6：
化合物D7：
化合物D8：
化合物D9：
化合物D10：
化合物D11：
化合物D12：
化合物D13：
化合物D14：
根据一种优选的具体实施方式，以下提供本发明的化合物的制备方法，以下制备例中涉及的原料均为分析纯：
制备例1：采用如下合成路线合成原料化合物8a
化合物2a的制备：将2-甲基-6-氨基苯甲酸(即为化合物1a)(100mmol)溶于乙酸(1200ml)中，搅拌下滴加1mol/L的ICl乙酸溶液，滴加完毕继续搅拌反应2h。反应过程中会析出大量固体，TLC跟踪反应进程，反应完毕后。减压抽滤除去滤液，所得固体用乙酸500mL洗涤两次，干燥后即得灰白色固体，收率93％。
化合物3a的制备：氮气保护下，将化合物2a(20mmol)，吡啶30ml加入到100mL两颈瓶中。搅拌至固体完全溶解后，缓慢向反应体系中加入间氯苯基异氰酸酯(25mmol)。将反应液加热到100℃反应24小时。反应完毕后，反应液冷却至室温后缓慢加入冰水中并搅拌30分钟，所得固体抽滤、水洗、乙醚洗，干燥后即得化合物3a，产率为92％。
化合物4a的制备：将化合物3a(12mmol)，DMF(36mL)和KCO3(14mmol)加入到反应瓶中。搅拌反应30min后，缓慢滴加硫酸二甲酯(24mmol)，滴加完毕后室温搅拌反应过夜。TLC跟踪反应进程，反应完毕后，反应液缓慢倒入200mL冰水中。并剧烈搅拌30min，所得固体抽滤、水洗、乙醚洗涤，干燥后即得化合物4a，产率87％。
化合物5a的制备：将4a(12mmol)，CuCN(24mmol)加入到反应瓶中，氮气保护下加入60mL干燥的DMF，将体系加热到回流并反应约12h。TLC跟踪反应进程，反应完毕后减压蒸馏除去DMF，冷却后向反应瓶中加入60mL丙酮并剧烈搅拌30min，过滤除去反应瓶中不溶性的固体。滤液浓缩后得到白色固体；
化合物6a的制备：将所得的白色固体5a溶于乙酸(29mL)、水(124mL)，三氟甲磺酸(7.3mL)中，搅拌下缓慢滴加98mL浓硫酸。滴加完毕后，升温到回流并反应12h，TLC跟踪反应进程。反应完毕后将体系冷却到室温，并倒入到200mL冰水中剧烈搅拌30min。所得固体抽滤、水洗干燥后即得化合物6a，粗产率88％。
化合物7a的制备：将化合物5a(116.3mmol)，重蒸的DCM(581.5ml)加入到1000mL反应瓶中，冰水浴下缓慢滴加草酰氯(174.5mmol)；滴加完毕后，继续搅拌15min。缓慢滴加10滴DMF到反应体系中，滴加入完毕后，冰水浴下继续搅拌反应2h至固体完全溶解。反应完毕后减压脱除溶剂。将所制备的酰氯溶于200mL干燥的DCM中备用。
冰水浴下将1,3-二甲基-5-吡唑酮(174.5mmol)，DCM(350mL)加入到反应瓶中。缓慢滴加三乙胺(348.9mmol)滴加完毕后继续在该温度下继续搅拌15分钟。迅速将上述酰氯的二氯甲烷溶液滴加到该反应体系中，滴加时间控制在5min左右。滴加完毕后，继续反应15min。TLC跟踪反应进程至原料消失。反应完毕后，反应体系中析出固体，抽滤所得固体溶于二氯甲烷中并置于0℃下静置12小时。抽滤除去滤渣，剩余液体减压蒸馏得到白色固体，产率为92％。
化合物8a的制备：将化合物6a(45.7mmol)，干燥的乙腈685.5mL加入到反应瓶中。依次向反应液中加入三乙胺(91.4mmol)，丙酮氰醇(1.5ml)。搅拌下将上述反应体系加热到80℃，反应约30h。TLC跟踪反应进程至原料消失。反应完毕后，减压蒸馏除去溶剂，所得固体溶于二氯甲烷中，并用1M HCl溶液洗涤二氯甲烷有机相。分液收集有机相，有机相干燥脱溶后固体用甲醇重结晶。产率为94％。
制备例2：化合物1和化合物2的制备
将化合物8a(1.2mmol)溶于乙腈，依次加入K2CO3(1.44mmol)，3-溴丙炔(或3-溴丙炔烯)(2.4mmol)。升温至60℃，反应过夜。待反应完成后，冷却恢复至室温后，抽滤除去固体，收集滤液并进行柱层析，分离提纯得到最终产物。
制备例3：化合物3的制备
将10mmol的化合物3a加入到50mL单颈瓶中，加入18mL干燥的THF，室温下缓慢滴加15mmol的SOCl2，滴加完毕后75℃回流反应约1.5h，TLC跟踪反应进程，反应结束后脱干溶剂。加入20mL干燥的CHCl3，15mmol的2,5-二甲基-2,4-二氢-3H-吡唑-3-酮，15mmol的Et3N，反应约0.5h，TLC跟踪至酰氯消失。反应完毕后用20mL水洗一次，CH2Cl2萃取，每次用10mL的1摩尔/升的HCl洗2次，每次用10mL的饱和NaHCO3洗2次，无水Na2SO4干燥，过柱得化合物3b。
将5mmol化合物3b加入到50mL两颈瓶中，加入28mL无水乙腈，N2保护下加入10mmol的Et3N，0.018g(10％当量)的丙酮氰醇。室温下反应8h，TLC跟踪至反应原料消失。反应完毕后脱干乙腈，加入约30mL的CHCl3。每次用10mL的1摩尔/升的盐酸洗三次，饱和氯化钠每次10mL洗3次，有机层用无水硫酸钠干燥。减压脱去溶剂得浅黄色固体化合物3c。
将1mmol的化合物3c加入到50mL单颈瓶中，加入10mL干燥的DMF，加入1.1mmol碳酸钾，室温搅拌半小时，再加入1.1mmol溴丙烯，升温至40℃，TLC跟踪至原料消失，将体系倒入水浴中，CH2Cl2萃取，合并有机相，减压蒸馏，拌样柱层析分离提纯得到化合物3。
制备例4：化合物4的制备
将10mmol的化合物3a加入到50mL单颈瓶中，加入18mL干燥的THF，室温下缓慢滴加15mmol的SOCl2，滴加完毕后75℃回流反应约1.5h，TLC跟踪反应进程，反应结束后脱干溶剂。加入20mL干燥的CHCl3，15mmol的5-环丙基-2-甲基-2,4-二氢-3H-吡唑-3-酮，15mmol的Et3N，反应约0.5h，TLC跟踪至酰氯消失。反应完毕后用20mL水洗一次，CH2Cl2萃取，每次用10mL的1摩尔/升的HCl洗2次，每次用10mL的饱和NaHCO3洗2次，无水Na2SO4干燥，过柱，得化合物4b。
将5mmol化合物4b加入到50mL两颈瓶中，加入28mL无水乙腈，N2保护下加入10mmol的Et3N，0.05mmol(10％当量)的丙酮氰醇。室温下反应8h，TLC跟踪至反应原料消失。反应完毕后脱干乙腈，加入约30mL的CHCl3。每次用10mL的1摩尔/升的盐酸洗三次，饱和氯化钠每次10mL洗3次，有机层用无水硫酸钠干燥。减压脱去溶剂得浅黄色油状物，所得油状物用10mL甲醇重结晶可以得到化合物4c。
将1mmol的化合物4c加入到50mL单颈瓶中，加入10mL干燥的DMF，加入1.1mmol碳酸钾，室温搅拌半小时，再加入1.1mmol溴丙烯，升温至40℃，TLC跟踪至原料消失，将体系倒入水浴中，CH2Cl2萃取，合并有机相，减压蒸馏，拌样柱层析分离提纯得到化合物4。
本发明的参照样本中的化合物的制备方法参照前述制备例1-4。
上述参照样本以及本发明的化合物的表征数据分别列于表1中：
表1：化合物结构表征数据
采用前述参照样本以及本发明的化合物进行温室生物活性试验。
测试例1：温室普筛实验
用分析天平称取一定量的原药，用含1重量％吐温-80乳化剂的DMF溶解配成1重量％的母液，然后用蒸馏水稀释至不同浓度的储液备用。
供试杂草：参见表2。采用苗后茎叶喷雾：取内径7cm纸杯，装复合土(菜园土：育苗基质，1：2，v/v)至3/4处，直接播种测试靶标种子，覆土0.2cm，待长至4-5叶期备用。参照样本以及本发明的化合物均按照10g.a.i/mu；硝磺草酮按照10g.a.i/mu剂量在自动喷雾塔施药后，待叶面药液晾干后移入温室培养(温度保持为25-28℃，湿度保持为70％)，30天后调查结果，结果列于表2中。
调查方法：试验处理30天后目测靶标受害症状及生长抑制情况，并称地上部分鲜重，计算鲜重抑制率(％)，用鲜重抑制率表示防效(％)。
鲜重抑制率(％)＝(对照鲜重-处理鲜重)/对照鲜重×100
除草活性评价(耐药、轻微抑制、轻微白化、轻微畸形、严重畸形、完全白化、完全死亡等症状)：
G级-同对照，耐药，防效为小于10％；
F级-生长稍有影响，轻微抑制，活性差，防效为10％至小于20％；
E级-生长有影响，轻微白化，活性差，防效为20％至小于50％；
D级-生长有影响，轻微畸形，活性中等，防效为50％至小于70％；
C级-较敏感，严重畸形，活性较好，防效为70％至小于90％；
B级-极敏感，完全白化，活性好，进筛，防效为90％至小于100％；
A级-完全死亡，活性好，防效为100％。
表2：温室普筛除草活性实验结果
上述除草活性测试结果表明，本发明的化合物对杂草具有优异的防效。而且，在同等使用剂量下，本发明的化合物对狗尾草的防治效果优于商品化药剂硝磺草酮。
另外，从上述结果可以看出，当在分子中引入炔丙基或烯丙基时，获得的新化合物能够显著的增强对稗草的防治效果。这说明，针对本发明提供的式(I)所示结构的喹唑啉二酮类化合物，本发明的发明人特别发现的炔丙基片段和烯丙基片段对提高HPPD类抑制剂的除草活性具有明显的促进作用。
综合分析，炔丙基片段和烯丙基片段对提高本发明的HPPD类抑制剂的除草活性具有重要的作用。
测试例2：温室初筛实验
用分析天平称取一定量的原药，用含1重量％吐温-80乳化剂的DMF溶解配成1重量％的母液，然后用蒸馏水稀释至不同浓度的储液备用。
采用盆栽法：供试靶标参见表3和表4；取内径6cm花盆，装复合土(菜园土：育苗基质，1：2，v/v)至3/4处，直接播种杂草靶标(芽率≥85％)，覆土0.2cm，待测试靶标长至3叶期左右备用。各化合物按照表3和表4所示剂量在自动喷雾塔施药后，待杂草叶面药液晾干后移入温室培养，30天后调查结果，结果列于表3和表4中。
调查方法与测试例1中相同。
表3代表化合物除草活性初筛实验结果
表4代表化合物作物安全性初筛实验结果
分析初筛实验结果，随着使用剂量的降低，本发明的化合物对测试杂草的防效也有所降低。但是从测试的结果来看，当使用剂量降低至2g.a.i/mu时，本发明的化合物依然对杂草的防效仍能保持较高水平。
作物安全性试验表明，本发明的化合物在测试剂量下对玉米、小麦、籼稻、粳稻具有良好的作物安全性。
因此，在本发明中，炔丙基和烯丙基一方面提高了抑制剂分子的除草活性，另一方面改善了抑制剂分子的作物安全性。
因此，本发明的化合物的后续开发有望应用于多种田间杂草的防治，具有非常好的经济价值和社会效益。
结合目前的实验数据，充分说明本发明的化合物具有非常好的应用价值，可以作为HPPD类除草剂的候选药物分子。
同时鉴于本发明的化合物的超高的作物安全性和除草活性，有望开发成为多功能性除草剂，即同一除草剂用于防治不同作物的田间杂草，例如：玉米、小麦、粳稻、籼稻、油菜等。
以上详细描述了本发明的优选实施方式，但是，本发明并不限于此。在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，包括各个技术特征以任何其它的合适方式进行组合，这些简单变型和组合同样应当视为本发明所公开的内容，均属于本发明的保护范围。
Claims (11)
1.一种含不饱和基的喹唑啉二酮类化合物，该化合物具有式(I)所示的结构：
其中，在式(I)中，
R1为烯丙基或炔丙基；
R2选自C1-6的烷基；
X选自C1-12的烷基、由1-6个选自卤素的原子取代的C6-10的芳基、由1-6个选自卤素的原子取代的C1-12的烷基、由C1-3的烷氧基取代的C1-12的烷基、C2-12的烯基、C2-12的炔基、含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基、由含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基取代的C1-12的烷基；
Y选自H、C1-6的烷基。
2.根据权利要求1所述的化合物，其中，式(I)所示的化合物选自以下化合物中的至少一种：
化合物1：R1为烯丙基；R2为甲基；X为3-Cl-苯基；Y为甲基；
化合物2：R1为炔丙基；R2为甲基；X为3-Cl-苯基；Y为甲基。
3.根据权利要求1所述的化合物，其中，在式(I)中，
R1为烯丙基或炔丙基；
R2选自C1-3的烷基；
X选自C1-8的烷基、由1-3个选自F、Cl和Br的卤素取代的C6-10的芳基、由1-3个选自F、Cl和Br的卤素取代的C1-8的烷基、由C1-3的烷氧基取代的C1-8的烷基、C2-8的烯基、C2-8的炔基、含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基、由含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基取代的C1-8的烷基；
Y选自H、C1-3的烷基。
4.一种含不饱和基的喹唑啉二酮类化合物，该化合物具有式(I)所示的结构：
其中，在式(I)中，
R1为烯丙基或炔丙基；
R2选自甲基、乙基、正丙基和异丙基；
X选自C1-6的烷基、由1-3个选自F、Cl和Br的卤素取代的苯基、由1-3个选自F、Cl和Br的卤素取代的C1-6的烷基、由C1-3的烷氧基取代的C1-6的烷基、C2-6的烯基、C2-6的炔基、含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基、由含有选自O、N、S中的至少一种杂原子的C2-6的杂环烷基取代的C1-6的烷基；
Y选自H、甲基、乙基、正丙基、异丙基和环丙基。
5.一种含不饱和基的喹唑啉二酮类化合物，该化合物具有式(I)所示的结构：
其中，式(I)所示的化合物选自以下化合物中的至少一种：
化合物3：R1为烯丙基，R2为-CH3，X为-CH3，Y为-CH3；
化合物4：R1为烯丙基，R2为-CH3，X为-CH3，Y为
化合物5：R1为烯丙基，R2为-CH3，X为乙基，Y为-CH3；
化合物6：R1为烯丙基，R2为-CH3，X为乙基，Y为
化合物7：R1为烯丙基，R2为-CH3，X为正丙基，Y为-CH3；
化合物8：R1为烯丙基，R2为-CH3，X为正丙基，Y为
化合物9：R1为烯丙基，R2为-CH3，X为异丙基，Y为-CH3；
化合物10：R1为烯丙基，R2为-CH3，X为异丙基，Y为
化合物11：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物12：R1为烯丙基，R2为-CH3，X为
Y为
化合物13：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物14：R1为烯丙基，R2为-CH3，X为
Y为
化合物15：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物16：R1为烯丙基，R2为-CH3，X为
Y为
化合物17：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物18：R1为烯丙基，R2为-CH3，X为
Y为
化合物19：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物20：R1为烯丙基，R2为-CH3，X为
Y为
化合物21：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物22：R1为烯丙基，R2为-CH3，X为
Y为
化合物23：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物24：R1为烯丙基，R2为-CH3，X为
Y为
化合物25：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物26：R1为烯丙基，R2为-CH3，X为
Y为
化合物27：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物28：R1为烯丙基，R2为-CH3，X为
Y为
化合物29：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物30：R1为烯丙基，R2为-CH3，X为
Y为
化合物31：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物32：R1为烯丙基，R2为-CH3，X为
Y为
化合物33：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物34：R1为烯丙基，R2为-CH3，X为
Y为
化合物35：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物36：R1为烯丙基，R2为-CH3，X为
Y为
化合物37：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物38：R1为烯丙基，R2为-CH3，X为
Y为
化合物39：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物40：R1为烯丙基，R2为-CH3，X为
Y为
化合物41：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物42：R1为烯丙基，R2为-CH3，X为
Y为
化合物43：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物44：R1为烯丙基，R2为-CH3，X为
Y为
化合物45：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物46：R1为烯丙基，R2为-CH3，X为
Y为
化合物47：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物48：R1为烯丙基，R2为-CH3，X为
Y为
化合物49：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物50：R1为烯丙基，R2为-CH3，X为
Y为
化合物51：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物52：R1为烯丙基，R2为-CH3，X为
Y为
化合物53：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物54：R1为烯丙基，R2为-CH3，X为
Y为
化合物55：R1为烯丙基，R2为-CH3，X为
Y为-CH3；
化合物56：R1为烯丙基，R2为-CH3，X为
Y为
化合物57：R1为烯丙基，R2为-CH3，X为
Y为CH3；
化合物58：R1为烯丙基，R2为-CH3，X为
Y为
化合物59：R1为炔丙基，R2为-CH3，X为-CH3，Y为-CH3；
化合物60：R1为炔丙基，R2为-CH3，X为-CH3，Y为
化合物61：R1为炔丙基，R2为-CH3，X为乙基，Y为-CH3；
化合物62：R1为炔丙基，R2为-CH3，X为乙基，Y为
化合物63：R1为炔丙基，R2为-CH3，X为正丙基，Y为-CH3；
化合物64：R1为炔丙基，R2为-CH3，X为正丙基，Y为
化合物65：R1为炔丙基，R2为-CH3，X为异丙基，Y为-CH3；
化合物66：R1为炔丙基，R2为-CH3，X为异丙基，Y为
化合物67：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物68：R1为炔丙基，R2为-CH3，X为
Y为
化合物69：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物70：R1为炔丙基，R2为-CH3，X为
Y为
化合物71：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物72：R1为炔丙基，R2为-CH3，X为
Y为
化合物73：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物74：R1为炔丙基，R2为-CH3，X为
Y为
化合物75：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物76：R1为炔丙基，R2为-CH3，X为
Y为
化合物77：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物78：R1为炔丙基，R2为-CH3，X为
Y为
化合物79：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物80：R1为炔丙基，R2为-CH3，X为
Y为
化合物81：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物82：R1为炔丙基，R2为-CH3，X为
Y为
化合物83：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物84：R1为炔丙基，R2为-CH3，X为
Y为
化合物85：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物86：R1为炔丙基，R2为-CH3，X为
Y为
化合物87：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物88：R1为炔丙基，R2为-CH3，X为
Y为
化合物89：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物90：R1为炔丙基，R2为-CH3，X为
Y为
化合物91：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物92：R1为炔丙基，R2为-CH3，X为
Y为
化合物93：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物94：R1为炔丙基，R2为-CH3，X为
Y为
化合物95：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物96：R1为炔丙基，R2为-CH3，X为
Y为
化合物97：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物98：R1为炔丙基，R2为-CH3，X为
Y为
化合物99：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物100：R1为炔丙基，R2为-CH3，X为
Y为
化合物101：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物102：R1为炔丙基，R2为-CH3，X为
Y为
化合物103：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物104：R1为炔丙基，R2为-CH3，X为
Y为
化合物105：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物106：R1为炔丙基，R2为-CH3，X为
Y为
化合物107：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物108：R1为炔丙基，R2为-CH3，X为
Y为
化合物109：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物110：R1为炔丙基，R2为-CH3，X为
Y为
化合物111：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物112：R1为炔丙基，R2为-CH3，X为
Y为
化合物113：R1为炔丙基，R2为-CH3，X为
Y为-CH3；
化合物114：R1为炔丙基，R2为-CH3，X为
Y为
化合物115：R1为炔丙基，R2为-CH3，X为3-Cl-苯基；Y为-H；
化合物116：R1为炔丙基，R2为-CH3，X为3-Cl-苯基；Y为
化合物117：R1为炔丙基，R2为-CH2CH3，X为3-Cl-苯基；Y为-CH3；
化合物118：R1为炔丙基，R2为正丙基，X为3-Cl-苯基；Y为-CH3；
化合物119：R1为烯丙基，R2为正丙基，X为3-Cl-苯基；Y为-CH3。
6.权利要求1-5中任意一项所述的含不饱和基的喹唑啉二酮类化合物在防治杂草中的应用。
7.权利要求1-5中任意一项所述的含不饱和基的喹唑啉二酮类化合物在防治选自阔叶杂草、禾本科杂草和莎草科杂草中的至少一种杂草中的应用。
8.权利要求1-5中任意一项所述的含不饱和基的喹唑啉二酮类化合物作为农药除草剂的应用。
9.一种农药除草剂，该农药除草剂由活性成分和辅料组成，所述活性成分包括权利要求1-5中任意一项所述的含不饱和基的喹唑啉二酮类化合物中的至少一种。
10.根据权利要求8所述的农药除草剂，其中，所述活性成分的含量为1～99.9999重量％。
11.根据权利要求9或10所述的农药除草剂，其中，所述农药除草剂的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、毒饵、母液和母粉中的至少一种。
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| CN114989142A (zh) * | 2022-05-09 | 2022-09-02 | 沈阳万菱生物技术有限公司 | 一种吡唑类化合物的制备方法 |
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| CN117624136A (zh) * | 2022-09-01 | 2024-03-01 | 山东先达农化股份有限公司 | 一种含有吡唑-喹唑啉二酮结构的化合物和一种除草剂及应用 |
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