TWI713530B - 作為除草劑之嘧啶氧基苯衍生物 - Google Patents
作為除草劑之嘧啶氧基苯衍生物 Download PDFInfo
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- TWI713530B TWI713530B TW105116619A TW105116619A TWI713530B TW I713530 B TWI713530 B TW I713530B TW 105116619 A TW105116619 A TW 105116619A TW 105116619 A TW105116619 A TW 105116619A TW I713530 B TWI713530 B TW I713530B
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- Prior art keywords
- compound
- alkyl
- haloalkyl
- group
- alkoxy
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 49
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 394
- 239000000203 mixture Substances 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 172
- -1 C 1 -C 6 nitroalkyl Chemical group 0.000 claims description 139
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 150000002367 halogens Chemical class 0.000 claims description 64
- 239000003112 inhibitor Substances 0.000 claims description 61
- 230000002363 herbicidal effect Effects 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
- 239000004480 active ingredient Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000003085 diluting agent Substances 0.000 claims description 27
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 25
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 24
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 238000003786 synthesis reaction Methods 0.000 claims description 19
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 17
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 14
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 230000012010 growth Effects 0.000 claims description 13
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 12
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 12
- 229930192334 Auxin Natural products 0.000 claims description 12
- 239000002363 auxin Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 11
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 11
- 239000005562 Glyphosate Substances 0.000 claims description 10
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 9
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 9
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 9
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 9
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims description 8
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 8
- 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 8
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 8
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 8
- 229940097068 glyphosate Drugs 0.000 claims description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- 239000005504 Dicamba Substances 0.000 claims description 7
- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 7
- 239000005616 Rimsulfuron Substances 0.000 claims description 7
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 7
- 108010001545 phytoene dehydrogenase Proteins 0.000 claims description 7
- 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 7
- 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 6
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005489 Bromoxynil Substances 0.000 claims description 6
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 6
- 239000005529 Florasulam Substances 0.000 claims description 6
- 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 6
- 239000005578 Mesotrione Substances 0.000 claims description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 6
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- GBUQDHNLEZWHOS-UHFFFAOYSA-N 3,3,3-trifluoropropyl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OCCC(F)(F)F)C(=CC=C1)OC1=NC=C(C=N1)Cl GBUQDHNLEZWHOS-UHFFFAOYSA-N 0.000 claims description 5
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 5
- 239000005531 Flufenacet Substances 0.000 claims description 5
- FCOHEOSCARXMMS-UHFFFAOYSA-N Oxaziclomefone Chemical compound C1OC(C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C1=CC(Cl)=CC(Cl)=C1 FCOHEOSCARXMMS-UHFFFAOYSA-N 0.000 claims description 5
- 108090000854 Oxidoreductases Proteins 0.000 claims description 5
- 102000004316 Oxidoreductases Human genes 0.000 claims description 5
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 5
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims description 5
- 230000008166 cellulose biosynthesis Effects 0.000 claims description 5
- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 claims description 5
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 5
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 5
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 5
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 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 4
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 claims description 4
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 4
- 239000005644 Dazomet Substances 0.000 claims description 4
- 239000005509 Dimethenamid-P Substances 0.000 claims description 4
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 claims description 4
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 4
- 239000005563 Halauxifen-methyl Substances 0.000 claims description 4
- 239000005571 Isoxaflutole Substances 0.000 claims description 4
- 239000005574 MCPA Substances 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 claims description 4
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 4
- 239000005586 Nicosulfuron Substances 0.000 claims description 4
- 239000005643 Pelargonic acid Substances 0.000 claims description 4
- 108010081996 Photosystem I Protein Complex Proteins 0.000 claims description 4
- 239000005607 Pyroxsulam Substances 0.000 claims description 4
- 239000005620 Tembotrione Substances 0.000 claims description 4
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 4
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 4
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 4
- NPZYKQZYWNQMDV-UHFFFAOYSA-N but-3-enyl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OCCC=C)C(=CC=C1)OC1=NC=C(C=N1)Cl NPZYKQZYWNQMDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 4
- JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 claims description 4
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical group NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 claims description 4
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims description 4
- 229940088649 isoxaflutole Drugs 0.000 claims description 4
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical group COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 claims description 4
- 229940095102 methyl benzoate Drugs 0.000 claims description 4
- 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 4
- 230000003278 mimic effect Effects 0.000 claims description 4
- 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 4
- 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 4
- DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 claims description 4
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims description 4
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-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
- RFZZKBWDDKMWNM-GTBMBKLPSA-N (5s,7r,8s,9r)-8,9-dihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@]11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-GTBMBKLPSA-N 0.000 claims description 3
- OMTXNHCOMNRAJT-UHFFFAOYSA-N 3,3,3-trifluoropropyl 2-chloro-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound ClC1=C(C(=O)OCCC(F)(F)F)C(=CC=C1)OC1=NC=C(C=N1)Cl OMTXNHCOMNRAJT-UHFFFAOYSA-N 0.000 claims description 3
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 3
- 229940106987 Elongase inhibitor Drugs 0.000 claims description 3
- RFZZKBWDDKMWNM-UHFFFAOYSA-N Hydantocidin Natural products OC1C(O)C(CO)OC11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 3
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 3
- 230000000394 mitotic effect Effects 0.000 claims description 3
- KBESKGARASQJER-UHFFFAOYSA-N prop-2-enyl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OCC=C)C(=CC=C1)OC1=NC=C(C=N1)Cl KBESKGARASQJER-UHFFFAOYSA-N 0.000 claims description 3
- 229950003776 protoporphyrin Drugs 0.000 claims description 3
- QBSOCTPGWBPYNI-UHFFFAOYSA-N 1-[2-(5-bromopyrimidin-2-yl)oxyphenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OC1=NC=C(Br)C=N1 QBSOCTPGWBPYNI-UHFFFAOYSA-N 0.000 claims description 2
- OUXHRFRSSZRSMY-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-yl 2-bromo-6-(5-chloropyrimidin-2-yl)oxybenzoate Chemical compound BrC1=C(C(=O)OC(CC(F)(F)F)C)C(=CC=C1)OC1=NC=C(C=N1)Cl OUXHRFRSSZRSMY-UHFFFAOYSA-N 0.000 claims description 2
- 239000005476 Bentazone Substances 0.000 claims description 2
- 239000005561 Glufosinate Substances 0.000 claims description 2
- 108010051696 Growth Hormone Proteins 0.000 claims description 2
- 102100038803 Somatotropin Human genes 0.000 claims description 2
- 108090000992 Transferases Proteins 0.000 claims description 2
- 102000004357 Transferases Human genes 0.000 claims description 2
- 239000005626 Tribenuron Substances 0.000 claims description 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 2
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 2
- 239000000122 growth hormone Substances 0.000 claims description 2
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 claims description 2
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 230000004222 uncontrolled growth Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fertilizers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562171294P | 2015-06-05 | 2015-06-05 | |
| US62/171,294 | 2015-06-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201706253A TW201706253A (zh) | 2017-02-16 |
| TWI713530B true TWI713530B (zh) | 2020-12-21 |
Family
ID=56118068
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW112134013A TW202400564A (zh) | 2015-06-05 | 2016-05-27 | 作為除草劑之嘧啶氧基苯衍生物 |
| TW109140137A TWI828952B (zh) | 2015-06-05 | 2016-05-27 | 作為除草劑之嘧啶氧基苯衍生物 |
| TW105116619A TWI713530B (zh) | 2015-06-05 | 2016-05-27 | 作為除草劑之嘧啶氧基苯衍生物 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW112134013A TW202400564A (zh) | 2015-06-05 | 2016-05-27 | 作為除草劑之嘧啶氧基苯衍生物 |
| TW109140137A TWI828952B (zh) | 2015-06-05 | 2016-05-27 | 作為除草劑之嘧啶氧基苯衍生物 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US11053204B2 (OSRAM) |
| EP (2) | EP3303305B9 (OSRAM) |
| JP (3) | JP6949731B2 (OSRAM) |
| KR (2) | KR102651771B1 (OSRAM) |
| CN (2) | CN115785000A (OSRAM) |
| AR (2) | AR104915A1 (OSRAM) |
| AU (2) | AU2016270751B2 (OSRAM) |
| BR (1) | BR112017019995A2 (OSRAM) |
| CA (1) | CA2978480C (OSRAM) |
| CL (1) | CL2017002883A1 (OSRAM) |
| CO (1) | CO2017012518A2 (OSRAM) |
| DK (1) | DK3303305T3 (OSRAM) |
| EA (2) | EA202092716A1 (OSRAM) |
| ES (1) | ES2909328T3 (OSRAM) |
| IL (2) | IL292855B2 (OSRAM) |
| MX (2) | MX390067B (OSRAM) |
| MY (2) | MY199934A (OSRAM) |
| PE (2) | PE20180040A1 (OSRAM) |
| PL (1) | PL3303305T3 (OSRAM) |
| SG (2) | SG11201707220WA (OSRAM) |
| SI (1) | SI3303305T1 (OSRAM) |
| TW (3) | TW202400564A (OSRAM) |
| UA (1) | UA124297C2 (OSRAM) |
| UY (2) | UY36712A (OSRAM) |
| WO (1) | WO2016196606A1 (OSRAM) |
| ZA (2) | ZA201706197B (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA124329C2 (uk) | 2014-01-16 | 2021-09-01 | ЕфЕмСі КОРПОРЕЙШН | Піримідинілоксибензольні похідні як гербіциди |
| WO2018204164A1 (en) | 2017-05-02 | 2018-11-08 | Fmc Corporation | Pyrimidinyloxy benzo-fused compounds as herbicides |
| CN106946794B (zh) * | 2017-05-11 | 2019-07-05 | 赣南师范大学 | 一种2-嘧啶氧基苯甲酸衍生物及其制备方法和一种水面杂草除草剂 |
| EP3810589A1 (de) * | 2018-06-25 | 2021-04-28 | Bayer Aktiengesellschaft | Substituierte 2-heteroaryloxypyridine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| EP3670505A1 (de) * | 2018-12-18 | 2020-06-24 | Bayer AG | Substituierte pyridinyloxybenzole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| US11109588B2 (en) | 2019-02-19 | 2021-09-07 | Gowan Company, L.L.C. | Stable liquid formulations and methods of using the same |
| CN114401956A (zh) * | 2019-07-22 | 2022-04-26 | 拜耳公司 | 取代的n-苯基尿嘧啶、其盐以及作为除草剂的用途 |
| TW202130623A (zh) * | 2019-12-02 | 2021-08-16 | 美商富曼西公司 | 用於合成2-硫烷嘧啶的製程 |
| GB202005175D0 (en) * | 2020-04-08 | 2020-05-20 | Syngenta Crop Protection Ag | Improvements in or relating to organic compounds |
| CN113683550A (zh) * | 2020-05-18 | 2021-11-23 | 兰州大学 | 一种n-(氰基(2-氰基取代苯基)甲基)取代的三级胺的合成方法 |
| GB202016569D0 (en) | 2020-10-19 | 2020-12-02 | Syngenta Crop Protection Ag | Herbicidal compositions |
| US20240174618A1 (en) | 2021-02-04 | 2024-05-30 | Bayer Aktiengesellschaft | Substituted (2-heteroaryloxyphenyl)sulfonates, salts thereof and their use as herbicidal agents |
| CN113185467B (zh) * | 2021-04-20 | 2022-03-08 | 江苏乾元生物科技有限公司 | 一种苯嘧磺草胺的制备方法 |
| CN114380771B (zh) * | 2022-01-27 | 2023-07-21 | 浙江财和生物科技有限公司 | 氟噻草胺的制备方法 |
| CN118974024A (zh) | 2022-03-28 | 2024-11-15 | 拜耳公司 | 取代的2-c-吖嗪及其盐以及作为除草活性物质的用途 |
| JP2025512828A (ja) | 2022-03-28 | 2025-04-22 | バイエル・アクチエンゲゼルシヤフト | 置換２－アミノアジンおよびその塩、ならびにその除草性活性物質としての使用 |
| WO2025212359A1 (en) | 2024-03-30 | 2025-10-09 | Fmc Corporation | Bixlozone mixture, composition and herbicidal method |
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-
2016
- 2016-05-27 TW TW112134013A patent/TW202400564A/zh unknown
- 2016-05-27 TW TW109140137A patent/TWI828952B/zh active
- 2016-05-27 TW TW105116619A patent/TWI713530B/zh active
- 2016-06-01 PE PE2017002489A patent/PE20180040A1/es unknown
- 2016-06-01 KR KR1020177034950A patent/KR102651771B1/ko active Active
- 2016-06-01 MY MYPI2021005608A patent/MY199934A/en unknown
- 2016-06-01 PL PL16728543T patent/PL3303305T3/pl unknown
- 2016-06-01 MX MX2017013799A patent/MX390067B/es unknown
- 2016-06-01 IL IL292855A patent/IL292855B2/en unknown
- 2016-06-01 AU AU2016270751A patent/AU2016270751B2/en active Active
- 2016-06-01 DK DK16728543.6T patent/DK3303305T3/da active
- 2016-06-01 KR KR1020247009672A patent/KR20240045346A/ko active Pending
- 2016-06-01 PE PE2021000770A patent/PE20211472A1/es unknown
- 2016-06-01 BR BR112017019995A patent/BR112017019995A2/pt not_active Application Discontinuation
- 2016-06-01 CN CN202211453644.7A patent/CN115785000A/zh active Pending
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- 2016-06-01 EP EP16728543.6A patent/EP3303305B9/en active Active
- 2016-06-01 EA EA202092716A patent/EA202092716A1/ru unknown
- 2016-06-01 IL IL255172A patent/IL255172B/en unknown
- 2016-06-01 SI SI201631488T patent/SI3303305T1/sl unknown
- 2016-06-01 WO PCT/US2016/035229 patent/WO2016196606A1/en not_active Ceased
- 2016-06-01 CA CA2978480A patent/CA2978480C/en active Active
- 2016-06-01 SG SG11201707220WA patent/SG11201707220WA/en unknown
- 2016-06-01 JP JP2017562975A patent/JP6949731B2/ja active Active
- 2016-06-01 EA EA201792433A patent/EA037101B1/ru not_active IP Right Cessation
- 2016-06-01 UA UAA201800495A patent/UA124297C2/uk unknown
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2017
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2021
- 2021-02-03 AU AU2021200694A patent/AU2021200694B2/en not_active Ceased
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2023
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001187A1 (en) * | 1977-09-13 | 1979-03-21 | Ici Australia Limited | 2-phenoxy-pyrimidines and their use as pesticides |
| JPS54117486A (en) * | 1978-03-03 | 1979-09-12 | Sankyo Co Ltd | 2-phenoxypyrimidine derivative |
| JPS61236766A (ja) * | 1985-04-15 | 1986-10-22 | Sumitomo Chem Co Ltd | ｏ−置換フエノキシ複素環化合物、その製造法およびそれを有効成分とする除草剤 |
| EP0226104A2 (en) * | 1985-12-11 | 1987-06-24 | Ishihara Sangyo Kaisha, Ltd. | N-Benzoyl urea compounds, antitumorous compositions containing them, and process for their preparation |
Non-Patent Citations (1)
| Title |
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| Okada H, et al. "Synthesis and antitumor activities of novel benzoylphenylurea derivatives" Chem. Pharm. Bull 1991;39(9):2308-2315 * |
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