WO2021017817A1 - 一种包含r型吡啶氧基羧酸衍生物的除草组合物及其应用 - Google Patents
一种包含r型吡啶氧基羧酸衍生物的除草组合物及其应用 Download PDFInfo
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- WO2021017817A1 WO2021017817A1 PCT/CN2020/101901 CN2020101901W WO2021017817A1 WO 2021017817 A1 WO2021017817 A1 WO 2021017817A1 CN 2020101901 W CN2020101901 W CN 2020101901W WO 2021017817 A1 WO2021017817 A1 WO 2021017817A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- salt
- alkyl
- polyoxyethylene ether
- evaluation
- methyl
- Prior art date
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- -1 pyridyloxy carboxylic acid derivative Chemical class 0.000 title claims abstract description 201
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 48
- 241000196324 Embryophyta Species 0.000 claims abstract description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000003112 inhibitor Substances 0.000 claims abstract description 34
- 239000004480 active ingredient Substances 0.000 claims abstract description 25
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- AJPADPZSRRUGHI-RFZPGFLSSA-N 1-deoxy-D-xylulose 5-phosphate Chemical compound CC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O AJPADPZSRRUGHI-RFZPGFLSSA-N 0.000 claims abstract description 3
- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 claims abstract description 3
- 239000003688 hormone derivative Substances 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 239000012053 oil suspension Substances 0.000 claims description 134
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 66
- 239000005562 Glyphosate Substances 0.000 claims description 65
- 229940097068 glyphosate Drugs 0.000 claims description 65
- 239000003795 chemical substances by application Substances 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 31
- 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 26
- 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 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000005558 Fluroxypyr Substances 0.000 claims description 23
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 23
- YHKBGVDUSSWOAB-UHFFFAOYSA-N 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(CC(Cl)C(O)=O)=C(Cl)C=C1F YHKBGVDUSSWOAB-UHFFFAOYSA-N 0.000 claims description 21
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims description 21
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims description 17
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 17
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims description 16
- 239000005499 Clomazone Substances 0.000 claims description 15
- 239000005590 Oxyfluorfen Substances 0.000 claims description 15
- 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 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 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 14
- 239000005578 Mesotrione Substances 0.000 claims description 14
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 239000005489 Bromoxynil Substances 0.000 claims description 13
- 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 13
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 13
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 13
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 13
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 claims description 13
- 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 13
- 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 13
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000005497 Clethodim Substances 0.000 claims description 12
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims description 12
- 239000005507 Diflufenican Substances 0.000 claims description 12
- 239000005535 Flurochloridone Substances 0.000 claims description 12
- 239000005586 Nicosulfuron Substances 0.000 claims description 12
- 239000005592 Penoxsulam Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 12
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 claims description 12
- 239000005502 Cyhalofop-butyl Substances 0.000 claims description 11
- 239000005510 Diuron Substances 0.000 claims description 11
- 239000005597 Pinoxaden Substances 0.000 claims description 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 239000005614 Quizalofop-P-ethyl Substances 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000005618 Sulcotrione Substances 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 8
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 239000005504 Dicamba Substances 0.000 claims description 7
- 239000005630 Diquat Substances 0.000 claims description 7
- 239000007900 aqueous suspension Substances 0.000 claims description 7
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 239000004548 suspo-emulsion Substances 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims description 6
- 230000009261 transgenic effect Effects 0.000 claims description 6
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 5
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000005627 Triclopyr Substances 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 238000005516 engineering process Methods 0.000 claims description 5
- 239000004530 micro-emulsion Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 4
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical class NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical class CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 4
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000004714 phosphonium salts Chemical class 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 159000000000 sodium salts Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 3
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 3
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 claims description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims description 3
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 3
- 238000010362 genome editing Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 3
- 150000002780 morpholines Chemical class 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical class NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical class NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 2
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical class CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims description 2
- SWKPGMVENNYLFK-UHFFFAOYSA-N 2-(dipropylamino)ethanol Chemical class CCCN(CCC)CCO SWKPGMVENNYLFK-UHFFFAOYSA-N 0.000 claims description 2
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical class CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 claims description 2
- BCLSJHWBDUYDTR-UHFFFAOYSA-N 2-(propylamino)ethanol Chemical class CCCNCCO BCLSJHWBDUYDTR-UHFFFAOYSA-N 0.000 claims description 2
- OZICRFXCUVKDRG-UHFFFAOYSA-N 2-[2-hydroxyethyl(propyl)amino]ethanol Chemical class CCCN(CCO)CCO OZICRFXCUVKDRG-UHFFFAOYSA-N 0.000 claims description 2
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical class CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims description 2
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical class CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
- BFBKUYFMLNOLOQ-UHFFFAOYSA-N 2-butoxyethanamine Chemical class CCCCOCCN BFBKUYFMLNOLOQ-UHFFFAOYSA-N 0.000 claims description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical class CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical class CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 2
- PJHRMQPEENZCPK-UHFFFAOYSA-N 2-methylsulfanylpropan-1-amine Chemical class CSC(C)CN PJHRMQPEENZCPK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 239000004381 Choline salt Substances 0.000 claims description 2
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 2
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- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
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- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
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Classifications
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- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- 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
Definitions
- the invention belongs to the field of pesticides, and specifically relates to a herbicidal composition containing R-type pyridyloxy carboxylic acid derivatives and applications thereof.
- Chemical weed control is the most economical and effective method for the control of weeds in farmland.
- long-term continuous high-dose use of chemical herbicides of a single species or single mode of action is likely to cause problems such as weed resistance and resistance evolution.
- Reasonable compounding or mixing of herbicide compounds has the advantages of expanding the weed spectrum, improving the control effect, delaying the occurrence and development of weed resistance and resistance, and is one of the most effective methods to solve the above problems. Therefore, there is still a need to develop herbicidal composition varieties with high safety, broad herbicidal spectrum, synergistic effects and solving the problem of resistant weeds in production.
- the present invention provides a herbicidal composition containing an R-type pyridyloxy carboxylic acid derivative and its application.
- the composition can effectively control various weed problems such as grasses or broadleaf species, and has the characteristics of expanding the weed-killing spectrum, reducing the application amount, being able to produce synergistic effects and solving resistant weeds.
- the active ingredient A is selected from one or more of the R-type pyridyloxy carboxylic acid and its salt and ester derivatives as shown in formula I:
- R 1 and R 2 each independently represent halogen, C1-C6 alkyl, halogenated C1-C6 alkyl, and C3-C6 cycloalkyl;
- R 3 represents hydrogen, halogen, C1-C6 alkyl, halogenated C1-C6 alkyl
- Q represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, cyano, amino, nitro, formyl, C1- C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxycarbonyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, cyano C1-C6 alkyl, C1-C6 alkane Amino C1-C6 alkyl group, and at least one unsubstituted or selected from C1-C6 alkyl group, cyano group, halogenated C1-C6 alkyl group, C1-C6 alkylamino group, halogen, and C1-C6 alkoxy group Phenyl, benzyl, naphthyl, furyl, thi
- Y represents amino, C1-C6 alkylamino, C1-C6 alkylcarbonylamino, and unsubstituted or selected from C1-C6 alkyl, halogen, cyano, C1-C6 alkylamino, C1-C6 alkoxy And a phenylcarbonylamino, benzylamino or furylmethyleneamino group substituted by at least one of the halogenated C1-C6 alkyl groups;
- the salt is metal salt, ammonium salt NH 4 + , primary amine salt R”NH 2 , secondary amine salt (R”) 2 NH, tertiary amine salt (R”) 3 N, quaternary amine salt (R”) 4 N + , polyamine salt, morpholine salt, N-methylmorpholine salt, piperidine salt, pyridine salt, aminopropyl morpholine salt, Jeffamine D-230 salt, 2,4,6-tris(dimethyl Aminomethyl) phenol and sodium hydroxide salt, C1-C16 alkyl sulfonium salt (preferably C1-C6 alkyl sulfonium salt), C1-C16 alkyl sulfonium oxide salt (preferably C1-C6 alkyl sulfonium oxide salt), C1-C16 alkyl phosphonium salt (preferably C1-C6 alkyl phosphonium salt) or C1-C16 alkanol phosphonium salt (preferably C1-C6
- R" each independently represents a C1-C16 alkyl group, and is selected from one or more groups selected from halogen, hydroxy, C1-C6 alkoxy, C1-C6 alkylthio, and hydroxy C1-C6 alkoxy.
- Substituted C1-C16 alkyl preferably C1-C6 alkyl
- C2-C12 alkenyl preferably C2-C6 alkenyl
- C2-C12 alkynyl preferably C2-C6 alkynyl
- C3-C12 cycloalkane Group unsubstituted or substituted by C1-C6 alkyl phenyl or benzyl
- C1-C6 alkyl phenyl or benzyl preferably C1-C6 alkyl group, and is selected from one or more groups selected from halogen, hydroxy, C1-C6 alkoxy, C1-C6 alkylthio, and hydroxy C1-C6 alkoxy.
- X represents O or S
- M represents C1-C18 alkyl, halo C1-C8 alkyl, unsubstituted or substituted C3-C6 cycloalkyl with C1-C6 alkyl, C2-C6 alkenyl, halo C2-C6 alkenyl, C2- C6 alkynyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, cyano C1-C6 alkyl, nitro C1-C6 alkyl, C1-C6 alkoxy C1- C6 alkyl, -(C1-C6 alkyl)-Z, And unsubstituted or substituted with at least one group selected from C1-C6 alkyl, halogenated C1-C6 alkyl, cyano, C1-C6 alkylamino, halogen, and C1-C6 alkoxy , Tetrahydrofuryl, pyri
- Z stands for And unsubstituted or substituted with at least one group selected from C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylamino, halogenated C1-C6 alkyl, cyano and halogen Phenyl, tetrahydrofuranyl, pyridyl, pyrazolyl, thienyl, furanyl or naphthyl;
- R 4 , R 5 , and R 6 each independently represent hydrogen, C1-C6 alkyl, C1-C6 alkoxycarbonyl, and unsubstituted or selected from C1-C6 alkyl, C1-C6 alkoxy, C1- Phenyl substituted by at least one of C6 alkylamino, halogenated C1-C6 alkyl, cyano and halogen;
- R 7 represents C1-C6 alkyl, C2-C6 alkenyl,
- the active ingredient B is selected from one or more of the following compounds and their acids/salts/esters:
- ALS inhibitors Penoxsulam (CAS No.: 219714-96-2), Bispyrifen (CAS No. 125401-92-5), Pyrimsulfuron (CAS No. 93697-74-6) ), Nicosulfuron (CAS Number: 111991-09-4), Diflufenazone (CAS Number: 145701-23-1), Susulfuron-methyl (CAS Number: 122931-48-0), Imazethapyr Tobacco (CAS Number: 81335-77-5), Imazethapyr (CAS Number: 104098-48-8), Imazethapyr (CAS Number: 114311-32-9), Metsulfuron (CAS No.: 74222-97-2), Chlorfentrazone (CAS No.: 147150-35-4);
- ACCase inhibitors cyhalofop-butyl (CAS number: 122008-85-9), clodinafop-propargyl (CAS number: 105512-06-9), pinoxaden (CAS number: 243973-20-8) , Clethodim (CAS number: 99129-21-2), enoxydim (CAS number: 74051-80-2), quizalofop (CAS number: 100646-51-3), diflufena-ethyl (CAS number: 79241-46-6), high-efficiency fluroxypyr (CAS number: 72619-32-0);
- PSII inhibitors atrazine (CAS number: 1912-24-9), isoproteron (CAS number: 34123-59-6), chlorotoluron (CAS number: 15545-48-9), enemy Caolong (CAS Number: 330-54-1), Benzoxone (CAS Number: 25057-89-0), Bromoxynil (CAS Number: 1689-84-5), Dibaran (CAS Number: 709-98) -8);
- HPPD inhibitors ciclofenone (CAS number: 1855929-45-1), fentrazone (CAS number: 1622908-18-2), flufenone (CAS number: 1992017-55) -6), mesotrione (CAS number: 1911613-97-2), fursotrione (CAS number: 473278-76-1), mesotrione (CAS number: 104206-82-8), Cyclosulfone (CAS number: 335104-84-2), oxaflutole (CAS number: 210631-68-8), isoxaflutole (CAS number: 141112-29-0), bicyclazone ( CAS number: 156963-66-5);
- PDS inhibitors diflufenican (CAS number: 83164-33-4), flurochloridone (CAS number: 61213-25-0);
- DOXP inhibitor clomazone (CAS number: 81777-89-1);
- PPO inhibitors carfentrazone (CAS number: 128621-72-7), fomesafen (CAS number: 72178-02-0), acifluorfen (CAS number: 77501-60-1) ), oxyfluorfen (CAS number: 42874-03-3), lactofen (CAS number: 77501-63-4), acifluorfen (CAS number: 50594-66-6), Flumetsulam (CAS Number: 103361-09-7), Sulfentrazone (CAS Number: 122836-35-5), Safentrazone (CAS Number: 372137-35-4), Oxachlor (CAS Number: 19666-30-9), Oxachlor (CAS Number: 39807-15-3).
- Synthetic hormone inhibitors triclopyr (triclopyr, CAS number: 55335-06-3), 2-methyl-4-chloro (MCPA, CAS number: 94-74-6), dicamba (dicamba, CAS No. 1918-00-9), Aminopyralid (picloram, CAS No.: 1918-02-1), Aminopyralid (Aminopyralid, CAS No.
- EPSPS inhibitor Glyphosate (Glyphosate, CAS number: 1071-83-6);
- GS inhibitor Glufosinate ammonium (CAS number: 77182-82-2);
- PSI inhibitors Diquat (Diquat Dibromide monohydrate, CAS number: 6385-62-2), Paraquat (Paraquat dichloride, CAS number: 1910-42-5).
- R 1 and R 2 each independently represent fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, isopropyl, trifluoromethyl, and cyclopropyl;
- R 3 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl
- Q represents methyl, ethyl, propyl, isopropyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, cyano, amino, nitro, formyl, methoxy, methylthio, Methoxycarbonyl, monochloromethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, hydroxymethyl, Benzyl, naphthyl Furanyl Pyridyl Pyrimidinyl And unsubstituted or substituted thiazolyl Thienyl unsubstituted or substituted by fluorine Unsubstituted or substituted by methyl or fluorine Unsubstituted or substituted by at least one of methyl, trifluoromethyl, chloro and methoxy;
- the salt is alkali metal (such as sodium, lithium, potassium, cesium and rubidium) salt, alkaline earth metal (such as calcium, magnesium, barium and strontium) salt, and antimony, bismuth, cadmium, cerium, chromium, cobalt, scandium, titanium , Manganese, copper, iron, silver, gold, zinc, aluminum and other metal salts, amine salts such as ammonium salt, tetramethylammonium salt, tetraethylammonium salt, tetrapropylammonium salt, tetrabutylammonium salt, N -Cetyltrimethylamine salt, N-benzyltrimethylammonium salt, benzyltriethylammonium salt, choline salt, monomethylamine salt, dimethylamine salt, trimethylamine salt, monoethylamine Salt, diethylamine salt, triethylamine salt, n-propylamine salt, dipropylamine salt,
- X in said I-1 represents O or S
- M represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, ten Monoalkyl, dodecyl, octadecyl, trifluoromethyl, pentafluoroethyl, 3-chlorobutyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2, 2-Difluoroethyl, 2,2,2-trifluoroethyl, 4,4,4-trifluorobutyl, 2,2,3,3,3-pentafluoropropyl, cyclopropyl, cyclobutyl Group, cyclopentyl, cyclohexyl, allyl, 2-propynyl, meth
- R' represents hydrogen, methyl, ethyl, difluoromethyl.
- the active ingredient A is selected from one or more of the following compounds:
- the preparation method of the active ingredient A includes the following steps:
- W represents hydrogen or alkali metal, preferably K, Na;
- Hal represents halogen, preferably Br, Cl;
- the reaction is carried out in the presence of a catalyst and a solvent, preferably, the catalyst is TBAB, and the solvent is DCM, One or more combinations of DCE, ACN, THF, DMF.
- the solvent is selected from one or more combinations of methanol, ethanol, and isopropanol.
- the reaction is carried out in the presence of a dehydrating agent and a solvent.
- the dehydrating agent is DCC
- the solvent is selected from dichloromethane, dichloroethane, acetonitrile, and N,N-dimethylformamide. , N,N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, toluene, xylene, one or more combinations.
- the halide is preferably chlorinated or brominated; the reaction is carried out in the presence of a base and a solvent, and the base is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and cesium carbonate One or more than two; the solvent is selected from one of THF, 1,4-dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF, acetone, dichloromethane and chloroform One or more combinations; a catalyst can also be added during the reaction process, preferably DMAP.
- a base is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and cesium carbonate
- the solvent is selected from one of THF, 1,4-dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF,
- the salt is a pesticide acceptable salt, and preferably is formed by the reaction of the R-type pyridyloxy carboxylic acid compound of the present invention with a chemically acceptable basic compound.
- the above-mentioned pharmaceutically acceptable salts are easy to separate and can be purified by conventional separation methods, such as solvent extraction, dilution, recrystallization, column chromatography, and preparative thin layer chromatography.
- the weight ratio of A and B is 1:100-100:1 or 1:50-50:1; preferably 1:30-30:1 or 1:20-20:1; more preferably 1:10- 10:1 or 1:8 to 8:1; more preferably 1:5 to 5:1 or 1:1 to 2:1 or 1:1 to 1:2.
- the mass percentage of A and B in the herbicidal composition accounts for 1-95%, preferably 10-80% of the total.
- the herbicidal composition also includes conventional adjuvants, and the conventional adjuvants include carriers and/or surfactants.
- carrier refers to an organic or inorganic, natural or synthetic substance. They facilitate the application of the active ingredient.
- the carrier is generally inert and must be agriculturally acceptable, especially acceptable to the treated plants.
- the carrier can be solid, such as clay, natural or synthetic silicate, silica, resin, wax, solid fertilizer, etc.; or liquid, such as water, alcohols, ketones, petroleum fractions, aromatic or wax hydrocarbons, chlorine Hydrocarbon, liquefied gas, etc.
- the surface active agent may include an emulsifier, dispersant or wetting agent, and it may be ionic or non-ionic. Examples that may be mentioned are the salts of polyacrylic acid, lignosulfonate, phenolsulfonic acid or naphthalenesulfonic acid, ethylene oxide with aliphatic alcohols or with aliphatic acids or with aliphatic amines and substituted phenols (in particular Alkylphenol or arylphenol) polymers, sulfosuccinates, taurine derivatives (especially taurine alkane esters) and alcohol phosphate esters or polyhydroxyethylated phenol phosphate esters, Alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, lauryl ether sulfates, fatty alcohol sulfates, and sulfated cetyl, heptadecyl and stearyl alcohols and sulf
- composition may also contain various other components, such as protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers, chelating agents, dyes, colorants and polymers.
- composition of the present invention can be mixed with the following active substances, such as "Encyclopedia of World Pesticide New Variety Technologies", China Agricultural Science and Technology Press, 2010.9 and known substances in the literature cited here.
- the herbicide active substances mentioned below (Remarks: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, and the code when appropriate): acetochlor, butachlor, Alachlor, Propolachlor, Metolachlor, Refined Metolachlor, Pretilachlor, Tetrachlor, Metrachlor, Napropionate, R-Levonapropion, Propanochlor , Mefenacet, difenacet, diflufenican, chlorfenazone, flufenacet, bromobutyramide, dimethenamid, dimethenamid, ethoxylate Anichlor, flufenacet, metolachlor, metazachlor, clomazone
- the herbicidal composition further includes at least one safener selected from:
- Dichlorophenylpyrazoline-3-carboxylic acid (S1) compounds the preferred compound is, for example, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl 2-pyrazoline-3-carboxylic acid ethyl ester (S1-1, mefenpyr-diethyl, PM, pages 594-595), and are described in, for example, WO91/07874 and PM (the 594-595 pages) related compounds.
- Dichlorophenylpyrazole carboxylic acid derivatives preferred compounds are, for example, 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-Dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-Dichlorophenyl)-5-(1 ,1-Dimethyl-ethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4), 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl Esters (S1-5), and related compounds described in EP-A-333131 and EP-A-269806.
- Triazole carboxylic acid (S1) compounds the preferred compound is, for example, fenchlorazole, namely 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1 , 2,4-Triazole-3-carboxylic acid ethyl ester (S1-6) and related compounds (see EP-A-174562 and EP-A-346620).
- 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid compound preferably
- the compound is, for example, 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S1-7) or 5-phenyl-2-isoxazoline-3-carboxylic acid Ethyl acid (S1-8) and related compounds described in WO91/08202, or 5,5-diphenyl-2-isoxazoline described in patent application (WO-A-95/07897) Ethyl 3-carboxylate (S1-9, isoxadifen-ethyl) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid n-propyl ester (S1-10) Or 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline
- S2 8-quinolinoxyacetic acid (S2) compounds, preferably 1-methylhex-1-yl (5-chloro-8-quinolinoxy) acetate (S2-1, cloquintocet- mexyl), such as PM (pages 195-196), (1,3-dimethylbut-1-yl)(5-chloro-8-quinolinoxy)acetate (S2-2), 4- Allyloxybutyl (5-chloro-8-quinolinoxy) acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy) Yl) acetate (S2-4), (5-chloro-8-quinolinoxy) ethyl acetate (S2-5), (5-chloro-8-quinolinoxy) methyl acetate (S2- 6), (5-chloro-8-quinolinoxy) allyl acetate (S2-7), 2-(2-propylene iminooxy)-1-ethyl (5-chloro-8-
- 5-Chloro-8-quinolinyloxy)malonic acid compounds are, for example, (5-chloro-8-quinolinyloxy)diethyl malonate, (5-chloro-8 -Quinolinoxy) diallyl malonate, (5-chloro-8-quinolinoxy)-malonate methyl ethyl ester and related compounds described in EP-A-0582198.
- Phenoxyacetic acid, phenoxypropionic acid or aromatic carboxylic acid active compounds such as 2,4-dichlorophenoxyacetic acid (and ester) (2,4-D), 4-chloro-2- Methylphenoxypropionate (2-methyl-4-chloropropionic acid (mecoprop)), MCPA or 3,6-dichloro-2-methoxybenzoic acid (and ester) (dicamba) .
- the safener is preferably dibenzoxazole acid (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), pyrazolone (CAS: 135590-91-9), detox quinine (CAS : 99607-70-2), one or more of gibberellic acid (CAS: 7-06-5), furilazole (CAS: 121776-33-8), and metcamifen (CAS: 129531-12-0).
- salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group.
- 2 methyl 4 chloro derivatives include but are not limited to: 2 methyl 4 chloride sodium salt, potassium salt, dimethyl ammonium salt, isopropylamine salt, etc., and 2 methyl 4 chloro methyl, ethyl, isooctyl ester, ethyl sulfide Esters, etc.
- 2,4-D derivatives include but are not limited to: 2,4-D salts such as sodium salt, potassium salt, dimethylammonium salt, triethanolammonium salt, isopropylamine salt, choline, etc., and 2,4 -D ester such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.
- the salt of the compound is preferably in the form of the respective alkali metal salt, alkaline earth metal salt or ammonium salt, preferably in the form of the respective alkali metal salt, more preferably in the form of the respective sodium salt or potassium salt, Most preferred is the form of the respective sodium salt.
- composition of the present invention can be diluted or used directly by the user before use.
- the formulation can be prepared by the usual processing methods, that is, after mixing the active substance with a liquid solvent or a solid carrier, then adding one or more of surfactants such as dispersing agents, stabilizers, wetting agents, adhesives, defoamers, etc. kind.
- the specific formulations of the herbicidal composition are dispersible oil suspension, water suspension, suspoemulsion, wettable powder, emulsifiable concentrate, water dispersible granule (dry suspension), water emulsion, microemulsion.
- the composition of the present invention can be mixed with solid and liquid additives conventionally used in prior art formulations.
- the amount of effective ingredients used is also different, such as temperature, humidity, and the nature of the herbicide used. It can have a large variation range, for example, between 0.001 and 1.0 kg/ha, or more active substances, but preferably between 0.005 and 750 g/ha, especially between 0.005 and 500 g/ha.
- composition of the present invention can be applied to the leaves of plants to be treated by spraying, that is, applied to weeds, especially on the surfaces that are infested or easily affected by weeds.
- the present invention also provides an application of the herbicidal composition for controlling weeds; and a method for controlling the growth of unwanted plants, which includes applying the herbicidal composition to plants, plant parts, and plants.
- the herbicidal composition is used to selectively control weeds in useful crops, and more preferably, the useful crops are transgenic crops or crops processed by genome editing technology.
- the compounds of the invention can be used to treat all plants and plant parts.
- Plant varieties and cultivated lines can be obtained by conventional propagation and breeding methods or by genetic engineering methods.
- Genetically modified plants are those in which a heterologous gene (transgene) has been stably integrated into the plant's genome.
- the transgene defined by its specific position in the plant genome is called a transformation event or a transgenic event.
- the genetically modified plant cultivars that can be treated according to the present invention include those resistant to one or more biotic stresses (pests, such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, low temperature, soil salinization) Etc.), or it contains other desired features. Plants may be genetically modified to exhibit traits, such as herbicide tolerance, insect tolerance, modified oil characteristics, or drought tolerance. Available genetically modified plants containing a single genetic transformation event or a combination of transformation events are listed in Table 1. Additional information about the genetic modifications listed in Table 1 can be obtained from publicly available databases maintained, for example, through the United States Department of Agriculture.
- T1 to T37 are used for the traits in Table 1. "-" means the entry is not available.
- the herbicidal composition of the present invention When the herbicidal composition of the present invention is applied, an unexpected synergistic effect is obtained, and the herbicidal activity is more significant than the expected sum of the activities of a single herbicide and the activity of a single herbicide.
- the synergistic effect is manifested by reduced application rate, wider weed control spectrum, faster and more lasting weeding effect. These characteristics are required in the practice of weed control. In terms of the characteristics described, these new compositions are significantly superior to existing herbicides, achieve reduced usage, and are more environmentally friendly.
- composition of the present invention is environmentally friendly and is easily degraded in the environment.
- the herbicidal composition of the present invention has low cost and convenient use, and its popularization and application have huge economic and social benefits.
- dispersible oil suspension agent processing equipment mixing kettle, colloid mill, sand mill, shearing machine, etc.
- the above-mentioned dispersible oil suspension agent processing process put all the materials into the mixing kettle, stir and mix, pass through the colloid mill, then enter the three-stage sand mill of the sand mill, and finally shear evenly in the shearing machine. After the test is qualified, transfer To the tank filling.
- the above-mentioned water suspension agent processing equipment mixing kettle, colloid mill, sand mill, shearing machine, etc.
- the above-mentioned water suspension agent processing process put all the materials into the mixing kettle, stir and mix, pass through the colloid mill, then enter the three-stage sand mill of the sand mill, and finally cut uniformly in the shearing machine, and transfer to the storage after passing the test. Can filling.
- suspoemulsion processing equipment mixing kettle, colloid mill, sand mill, shearing machine, etc.
- the above suspoemulsion processing process put part of the materials and additives into the mixing kettle, stir and mix, pass through the colloid mill, then enter the three-stage sand mill of the sand mill, and transfer to the intermediate tank as the water phase after the sand mill is completed; Put part of the original medicine and cosolvent into the batching kettle, stir and dissolve until it is completely transparent, and stir evenly into the oil phase; finally open the shear in the shearing kettle, slowly drip the oil phase into the water phase, after all the materials are dripped , Continue to cut for 1 hour, after passing the test, transfer to the storage tank for filling.
- the above-mentioned water emulsion processing equipment vacuum pump, batching kettle, storage tank, shearing kettle.
- the above aqueous emulsion processing process put the original medicine and solvent into the batching kettle, stir to dissolve until completely transparent, then add the emulsifier, stir evenly into the oil phase, then pump the glycol, defoamer and deionized water into the shear In the kettle, finally, under the shearing state, the oil phase is slowly drawn into the shearing kettle. After all the materials are drawn in, continue to shear for 1 hour. After passing the test, transfer to the storage tank for filling.
- microemulsion processing equipment vacuum pump, batching kettle, storage tank.
- microemulsion processing process put the original drug and solvent into the batching kettle, stir to dissolve until completely transparent, then add the emulsifier, stir evenly, finally add deionized water, stir until the solution is completely transparent, and transfer to the storage tank after the test is qualified Filling.
- the above-mentioned EC processing equipment vacuum pump, batching kettle, storage tank.
- the above-mentioned emulsifiable concentrate processing process put the original medicine and solvent into the batching kettle, stir and dissolve until completely transparent, then add the emulsifier, stir evenly until the solution is completely transparent, and transfer to the storage tank for filling after passing the test.
- liquid processing equipment vacuum pump, batching kettle, storage tank.
- Table 151-206 Crabgrass, Amaranthus variegata, Shepherd's purse, Gooseweed were collected from Huangdao, Shandong Province, wild rape was collected from Si County, Anhui, Japan Mai Niang was collected from Tianchang, Anhui, and Granny was from Siyang, Jiangsu .
- the above-mentioned weeds are cultivated by pot culture. They are placed in an enamel dish in a 180 ⁇ 140mm plastic nutrient bowl. The top soil (4/5) collected from the farmland is air-dried and sieved. The soil moisture is initially controlled at 20%. Weed seeds with full and uniform grains are soaked in warm water at 25°C for 6 hours, and germinated in a biochemical incubator (dark) at 28°C. Weed seeds that have just been exposed to white are evenly placed on the soil surface, and then covered with 0.5 soil according to the size of the seed. -1cm.
- 3WP-2000 walking spray tower Nanjing Agricultural Machinery Research Institute, Ministry of Agriculture. GA10 1/10000 electronic balance (Germany); ZDR2000 intelligent data recorder (Hangzhou Zeda Instrument Co., Ltd.); SPX type intelligent biochemical incubator (Ningbo Jiangnan Instrument Factory).
- the required active ingredient A comes from the patent CN201911321469.4.
- the preparation examples of representative compounds are as follows. The synthesis methods of other compounds are similar, so the details are not repeated.
- the required active ingredients B, cicloflurzone, carfentrazone, flufentrazone, and trifentrazone are produced by the company, and the others are purchased by the reagent company.
- the original medicines all use acetone as the solvent, diluted with 0.1% emulsifier Tween-80 aqueous solution, and are now diluted.
- the action characteristics and toxicity of the two drugs should be measured, and the main purpose of the formulation should also be considered.
- the single and mixed dosages of A and B active ingredients are shown in the table respectively. Use water without chemicals and with the same solvent and emulsifier as a blank control.
- Table 1-48, 51-98, 101-148, 151-206 Each treatment was repeated 4 times, 3 pots per treatment each time, 20 weed seeds were sown in each pot, 60 plants in total per treatment.
- Table 207-216 Each treatment was repeated 4 times, 10 pots per treatment each time, 10 weed seeds per pot were sown, and 3 seedlings per pot were sown.
- Table 1-48, 51-98, 101-148 Test shared medicine once. At the 3 ⁇ 4 leaf stage of the weeds, thin the seedlings, keep 15 weeds in each pot, keep 45 weeds per treatment, and then continue to cultivate until 5-6 leaves of gramineous weeds and 6-7 leaves of broadleaf weeds for treatment .
- Table 151-206 Test shared medicine once. At the 3 ⁇ 4 leaf stage of the weeds, thin the seedlings, keep 15 weeds per pot, keep 45 plants per treatment, and then continue to cultivate until 4 ⁇ 5 leaves of gramineous weeds and 5 ⁇ 6 leaves of broadleaf weeds .
- Table 207-216 Test shared medicine once. At the 6-8 leaf stage of the weeds, thin the seedlings, maintain 3 weeds in each pot, reserve 30 plants for each treatment, and then continue to cultivate until the height of the small scabies is 10 cm for treatment.
- the whole seedling of the surviving weed was cut along the soil surface with a blade, and the fresh weight of the weed was weighed with an analytical balance. For weeds that have died, the fresh weight is zero.
- E-E0 value greater than 10% is synergistic, less than -10% is antagonistic, and between -10% and 10% is additive. And according to the actual control effect, herbicide characteristics, formula balance and other factors to determine the best ratio.
- X is the fresh weight inhibition rate when the amount of active ingredient A is P
- Y is the fresh weight inhibition rate when the amount of active ingredient B is Q.
- the test soil is quantitatively filled to 3/4 of the pot, and then watered from the bottom of the pot to make the soil completely wet to a saturated state. Spread the pretreated weed seeds evenly and quantitatively on the surface, cover 0.5-2cm of soil according to the seed size, and reserve 24 hours after sowing.
- GA10 one-tenth electronic balance (Germany); ZDR2000 intelligent data recorder (Hangzhou Zeda Instrument Co., Ltd.); SPX type intelligent biochemical incubator (Ningbo Jiangnan Instrument Factory), pipettes, etc.
- Table 17 The actual control effect and joint effect evaluation of A2 mixed quizalofop-p-ethyl on barnyardgrass
- Table 110 The actual control effect and joint effect evaluation of A4 mixed with metsulfuron on paddy field barnyardgrass
- Table 128 The actual control effect and combined effect evaluation of A3 blended fentrazone on wild rape
- Table 130 The actual control effect and joint effect evaluation of A4 mixed triazuron on paddy field barnyardgrass
- Table 135 The actual control effect and combined effect evaluation of A4 mixed isoxaflutole on paddy field barnyardgrass
- A+B dose A:B A corresponding dose of single-use prevention B corresponds to a single dose A+B prevention effect E0(%) E-E0 (%)
- the herbicidal composition prepared in Examples 1-150 was used to conduct field weed effect tests.
- Stem and leaf treatment When the weeds are in the 3-5 leaf stage, use a manual sprayer with a water volume of 30 kg/667m 2 and use stem and leaf spray treatment.
- test agents and dosages are shown in Table 217.
- the plot area is 50 square meters and each treatment is repeated 4 times. See Table 217 for the investigation of control effect 45 days after application.
- Test crops including glyphosate, 2,4-D resistance traits: Corn SmartStax TM Pro x Enlist TM (Event Name MON87427 x MON89034 x TC1507 x MON87411 x 59122 x DAS40278), soybean Conkesta Enlist E3 TM (Event Name DAS81419 x DAS44406).
- Stem and leaf treatment leaf age weeds 3-5 leaf stage, corn 3-5 leaf 1-heart stage, soybean second to third three-leaf stage.
- Weed fresh weight control effect (%) (blank control weed fresh weight-chemical treatment weed fresh weight) / blank control weed fresh weight ⁇ 100
- the present invention unexpectedly discovered that the composition is used for the prevention and control of Amaranthus edulis, Amaranthus variabilis, Amaranthus amaranthus, Solanum vulgaris, Channa intestines, Pork scorpion, Field convolvulus, Small scabies, Shepherd's purse, Abutilon, Persian mother-in-law, Arabian mother-in-law, cow chickweed, chickweed, wild rape, clove polygonum, Moshangcai, cocory, sorrel, cockles, cocklebur, artemisia sowing, quinoa, duck Broadleaf weeds such as dayflower, morning glory and other broad-leaved weeds, Mai Niang, Japanese Mai Niang, Chrysanthemum sinensis, Barnyardgrass, Barnyardgrass, Paddy barnyardgrass, Echinochloa crusgalli, Bristlegrass, Green Setaria, Golden Setaria, Horse Gramineous weeds such
- This synergistic effect is low.
- the performance is more significant under the dosage, can reduce the dosage, reduce the pollution to the environment, and the reasonable compounding reduces the agricultural cost, is highly effective against ALS, ACCase inhibitor resistant weeds, and has a good application prospect.
- it has been tested in wheat fields, corn fields, rice fields, peanuts, sugarcane, sorghum, millet, potatoes, rape, soybeans, cotton, vegetables, bluegrass, tall fescue, Zoysia grass and other fields, showing good selectivity and Excellent synergistic effect, can be developed into a herbicide mixture with broad market value.
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Abstract
Description
A+B剂量 | A:B | A对应剂量单用防 | B对应剂量单用 | A+B防效 | E0(%) | E-E0(%) |
(g a.i./ha) | 效(%) | 防效(%) | (%),E | |||
150+75 | 2:1 | 31.9 | 12.3 | 52.3 | 40.3 | 12.0 |
150+150 | 1:1 | 31.9 | 24.6 | 64.2 | 48.7 | 15.5 |
75+300 | 1:4 | 19.2 | 43.5 | 69.2 | 54.3 | 14.9 |
75+600 | 1:8 | 19.2 | 76.4 | 92.3 | 80.9 | 11.4 |
实施例序号 | 用量(g a.i./ha) | 鲜重防效(%) |
1 | 150 | 97.8 |
2 | 180 | 95.6 |
3 | 210 | 93.8 |
4 | 150 | 98.3 |
5 | 180 | 95.2 |
6 | 210 | 94.6 |
7 | 150 | 97.5 |
8 | 180 | 96.7 |
9 | 210 | 94.9 |
10 | 180 | 96.6 |
11 | 210 | 96.7 |
12 | 240 | 94.1 |
13 | 124.5 | 97.1 |
14 | 154.5 | 96.3 |
15 | 184.5 | 94.9 |
16 | 150 | 96.3 |
17 | 180 | 97.8 |
18 | 210 | 95.2 |
19 | 210 | 95.4 |
20 | 240 | 97.8 |
21 | 270 | 94.4 |
22 | 270 | 95.9 |
23 | 300 | 97.4 |
24 | 330 | 95.2 |
25 | 180 | 95.1 |
26 | 210 | 98.9 |
27 | 240 | 95.5 |
28 | 270 | 94.2 |
29 | 300 | 98.9 |
30 | 330 | 94.7 |
31 | 150 | 94.7 |
32 | 180 | 98.5 |
33 | 210 | 95.5 |
34 | 270 | 93.9 |
35 | 300 | 98.3 |
36 | 330 | 95.8 |
37 | 165 | 97.5 |
38 | 195 | 95.1 |
39 | 225 | 93.6 |
40 | 195 | 97.6 |
41 | 225 | 94.9 |
42 | 255 | 94.1 |
43 | 210 | 97.3 |
44 | 240 | 95.8 |
45 | 270 | 94.6 |
46 | 345 | 96.1 |
47 | 375 | 96.5 |
48 | 405 | 93.4 |
49 | 180 | 96.8 |
50 | 210 | 95.8 |
51 | 240 | 94.7 |
52 | 180 | 95.6 |
53 | 210 | 97.5 |
54 | 240 | 94.7 |
55 | 180 | 95.1 |
56 | 210 | 97.3 |
57 | 240 | 94.2 |
58 | 870 | 95.2 |
59 | 900 | 97.1 |
60 | 930 | 94.7 |
61 | 870 | 94.9 |
62 | 900 | 97.8 |
63 | 930 | 95.2 |
64 | 870 | 93.7 |
65 | 900 | 98.7 |
66 | 930 | 93.5 |
67 | 1020 | 94.4 |
68 | 1050 | 97.7 |
69 | 1080 | 95.3 |
70 | 720 | 93.2 |
71 | 750 | 97.5 |
72 | 780 | 95.3 |
73 | 300 | 92.7 |
74 | 330 | 96.5 |
75 | 360 | 95.3 |
76 | 1620 | 94.5 |
77 | 1650 | 94.9 |
78 | 1680 | 97.2 |
79 | 255 | 94.1 |
80 | 285 | 94.8 |
81 | 315 | 96.3 |
82 | 150 | 93.5 |
83 | 180 | 94.5 |
84 | 210 | 96.8 |
85 | 255 | 94.2 |
86 | 285 | 94.7 |
87 | 315 | 96.2 |
88 | 300 | 94.9 |
89 | 330 | 93.2 |
90 | 360 | 98.5 |
91 | 210 | 92.3 |
92 | 240 | 94.1 |
93 | 270 | 96.9 |
94 | 270 | 95.1 |
95 | 300 | 92.5 |
96 | 330 | 96.7 |
97 | 210 | 94.8 |
98 | 240 | 92.2 |
99 | 270 | 96.3 |
100 | 165 | 94.2 |
101 | 195 | 93.8 |
102 | 225 | 94.4 |
103 | 210 | 97.9 |
104 | 240 | 95.7 |
105 | 270 | 94.5 |
106 | 420 | 97.1 |
107 | 450 | 93.3 |
108 | 480 | 93.8 |
109 | 270 | 97.2 |
110 | 300 | 93.7 |
111 | 330 | 94.2 |
112 | 870 | 96.5 |
113 | 900 | 93.8 |
114 | 930 | 92.9 |
115 | 570 | 99.8 |
116 | 600 | 92.6 |
117 | 630 | 92.9 |
118 | 150 | 96.6 |
119 | 180 | 94.3 |
120 | 210 | 92.3 |
121 | 495 | 97.9 |
122 | 525 | 94.6 |
123 | 555 | 96.8 |
124 | 135 | 95.4 |
125 | 165 | 95.8 |
126 | 195 | 97.4 |
127 | 300 | 92.1 |
128 | 330 | 93.5 |
129 | 360 | 96.4 |
130 | 240 | 93.5 |
131 | 270 | 95.4 |
132 | 300 | 96.3 |
133 | 570 | 93.1 |
134 | 600 | 93.2 |
135 | 630 | 99.3 |
136 | 210 | 92.1 |
137 | 240 | 92.7 |
138 | 270 | 95.5 |
139 | 480 | 95.1 |
140 | 510 | 93.6 |
141 | 540 | 98.2 |
142 | 480 | 93.4 |
143 | 510 | 97.9 |
144 | 540 | 94.6 |
145 | 720 | 91.5 |
146 | 750 | 96.7 |
147 | 780 | 94.9 |
148 | 210 | 93.7 |
149 | 240 | 95.8 |
150 | 270 | 96.3 |
药剂 | 用药量(g a.i./ha) | 杂草鲜重防效(%) | 作物安全性-玉米 | 作物安全性-大豆 |
151 | 1125 | 93.1 | 安全 | 安全 |
152 | 900 | 96.4 | 安全 | 安全 |
153 | 877.5 | 97.2 | 安全 | 安全 |
154 | 945 | 95.2 | 安全 | 安全 |
155 | 1125 | 94.9 | 安全 | 安全 |
156 | 900 | 92.3 | 安全 | 安全 |
157 | 1125 | 91.7 | 安全 | 安全 |
158 | 900 | 93.9 | 安全 | 安全 |
159 | 1125 | 94.6 | 安全 | 安全 |
160 | 900 | 92.0 | 安全 | 安全 |
161 | 900 | 95.5 | 安全 | 安全 |
162 | 900 | 94.2 | 安全 | 安全 |
163 | 900 | 91.6 | 安全 | 安全 |
164 | 900 | 93.2 | 安全 | 安全 |
165 | 900 | 96.0 | 安全 | 安全 |
Claims (10)
- 一种包含R型吡啶氧基羧酸衍生物的除草组合物,其特征在于,包括除草有效量的活性成分A和活性成分B,其中,活性成分A选自如式Ⅰ所示的R型吡啶氧基羧酸及其盐、酯衍生物中的一种或多种:其中,R 1、R 2分别独立地代表卤素、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基;R 3代表氢、卤素、C1-C6烷基、卤代C1-C6烷基;Q代表C1-C6烷基,卤代C1-C6烷基,C3-C6环烷基,C2-C6烯基,C2-C6炔基,卤素,氰基,氨基,硝基,甲酰基,C1-C6烷氧基,C1-C6烷硫基,C1-C6烷氧羰基,羟基C1-C6烷基,C1-C6烷氧基C1-C6烷基,氰基C1-C6烷基,C1-C6烷氨基C1-C6烷基,以及未取代或被选自C1-C6烷基、氰基、卤代C1-C6烷基、C1-C6烷基氨基、卤素和C1-C6烷氧基中的至少一个基团所取代的苯基、苄基、萘基、呋喃基、噻吩基、噻唑基、吡唑基、吡啶基或嘧啶基;Y代表氨基,C1-C6烷基氨基,C1-C6烷基羰基氨基,以及未取代或被选自C1-C6烷基、卤素、氰基、C1-C6烷基氨基、C1-C6烷氧基和卤代C1-C6烷基中的至少一个基团所取代的苯基羰基氨基、苄基氨基或呋喃基亚甲基氨基;所述盐为金属盐、铵盐NH 4 +、伯胺盐R”NH 2、仲胺盐(R”) 2NH、叔胺盐(R”) 3N、季胺盐(R”) 4N +、多元胺盐、吗啉盐、N-甲基吗啉盐、哌啶盐、吡啶盐、氨基丙基吗啉盐、Jeff胺D-230盐、2,4,6-三(二甲基氨基甲基)苯酚和氢氧化钠的盐、C1-C16烷基锍盐、C1-C16烷基氧化锍盐、C1-C16烷基鏻盐或C1-C16烷醇鏻盐;其中,R”分别独立地代表未取代或被选自卤素、羟基、C1-C6烷氧基、C1-C6烷硫基、羟基C1-C6烷氧基中的一个或多个基团所取代的C1-C16烷基,C2-C12烯基,C2-C12炔基,C3-C12环烷基,未取代或被C1-C6烷基取代的苯基或苄基;M代表C1-C18烷基,卤代C1-C8烷基,未取代或被C1-C6烷基取代的C3-C6环烷基,C2-C6烯基,卤代C2-C6烯基,C2-C6炔基,C1-C6烷氧基,C1-C6烷氧羰基,C1-C6烷基磺酰基,氰基C1-C6烷基,硝基C1-C6烷基,C1-C6烷氧基C1-C6烷基,-(C1-C6烷基)-Z, 以及未取代或被选自C1-C6烷基、卤代C1-C6烷基、氰基、C1-C6烷基氨基、卤素和C1-C6烷氧基中的至少一个基团所取代的苯基、 四氢呋喃基、吡啶基、萘基、呋喃基、噻吩基、吡咯基、吡唑基或咪唑基;R 4、R 5、R 6分别独立地代表氢,C1-C6烷基,C1-C6烷氧基羰基,以及未取代或被选自C1-C6烷基、C1-C6烷氧基、C1-C6烷基氨基、卤代C1-C6烷基、氰基和卤素中的至少一个基团所取代的苯基;活性成分B选自以下化合物或其酸/盐/酯中的一种或多种:(1)ALS抑制剂:五氟磺草胺、双草醚、吡嘧磺隆、烟嘧磺隆、双氟磺草胺、砜嘧磺隆、咪草烟、甲基咪草烟、甲氧咪草烟、甲嘧磺隆、氯酯磺草胺;(2)ACCase抑制剂:氰氟草酯、炔草酯、唑啉草酯、烯草酮、烯禾啶、精喹禾灵、精吡氟禾草灵、高效氟吡甲禾灵;(3)PSII抑制剂:莠去津、异丙隆、绿麦隆、敌草隆、灭草松、溴苯腈、敌稗;(4)HPPD抑制剂:环吡氟草酮、双唑草酮、苯唑氟草酮、三唑磺草酮、呋喃磺草酮、硝磺草酮、环磺酮、苯唑草酮、异噁唑草酮、双环磺草酮;(5)PDS抑制剂:吡氟酰草胺、氟咯草酮;(6)DOXP抑制剂:异噁草松;(7)PPO抑制剂:唑草酮、氟磺胺草醚、乙羧氟草醚、乙氧氟草醚、乳氟禾草灵、三氟羧草醚、丙炔氟草胺、甲磺草胺、苯嘧磺草胺、噁草酮、丙炔噁草酮;(8)合成激素类抑制剂:三氯吡氧乙酸、2甲4氯、麦草畏、氨氯吡啶酸、氯氨吡啶酸、氯氟吡氧乙酸、氯氟吡啶酯、氟氯吡啶酯、二氯喹啉酸、二氯吡啶酸;(9)EPSPS抑制剂:草甘膦;(10)GS抑制剂:草铵膦;(11)PSI抑制剂:敌草快、百草枯。
- 根据权利要求1所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物,其特征在于,R 1、R 2分别独立地代表氟、氯、溴、碘、甲基、乙基、丙基、异丙基、三氟甲基、环丙基;R 3代表氢、氟、氯、溴、碘、甲基、三氟甲基;Q代表甲基,乙基,丙基,异丙基,环丙基,乙烯基,乙炔基,氟,氯,溴,氰基,氨基,硝基,甲酰基,甲氧基,甲硫基,甲氧羰基,一氯甲基,一氟甲基,二氟甲基,三氟甲基,2-氯乙基,2,2,2-三氟乙基,羟基甲基, 苄基,萘基,呋喃基,吡啶基,嘧啶基,以及未取代或被氯取代的噻唑基,未取代或被氟取代的噻吩基,未取代或被甲基或氟取代的 未取代或被甲基、三氟甲基、氯和甲氧基中的至少一个基团所取代的苯基;所述盐为钠盐、锂盐、钾盐、铯盐、铷盐、钙盐、镁盐、钡盐、锶盐、锑盐、铋盐、镉盐、铈盐、铬盐、钴盐、钪盐、钛盐、锰盐、铜盐、铁盐、银盐、金盐、锌盐、铝盐、铵盐、四甲基铵盐、四乙基铵盐、四丙基铵盐、四丁基铵盐、N-十六烷基三甲基胺盐、N-苄基三甲基铵盐、苄基三乙基铵盐、胆碱盐、一甲胺盐、二甲胺盐、三甲胺盐、一乙胺盐、二乙胺盐、三乙胺盐、正丙胺盐、二丙胺盐、三丙胺盐、一异丙胺盐、二异丙胺盐、三异丙胺盐、正丁胺盐、二丁胺盐、三丁胺盐、异丁胺盐、叔丁胺盐、戊胺盐、己胺盐、庚胺盐、辛胺盐、十二烷基胺盐、十四烷基胺盐、二烯丙基胺盐、环己胺盐、环十二烷基胺盐、苯胺盐、邻甲苯胺盐、间甲苯胺盐、对甲苯胺盐、二苯胺盐、苄胺盐、单乙醇胺盐、N-甲基单乙醇胺盐、N,N-二甲基乙醇胺盐、N-乙基单乙醇胺盐、N,N-二乙基乙醇胺盐、N-丙基单乙醇胺盐、N,N-二正丙基乙醇胺盐、N-丁基单乙醇胺盐、二乙醇胺盐、N-甲基二乙醇胺盐、N-乙基二乙醇胺盐、N-丙基二乙醇胺盐、N-丁基二乙醇胺盐、N,N-二丁基乙醇胺盐、三乙醇胺盐、三丙醇胺盐、三异丙醇胺盐、三(2-羟基丙基)胺盐、二甘醇胺盐、六亚甲基四胺盐、乙二胺盐、二亚乙基三胺盐、二甲基氨基丙胺盐、1,2-丙二胺盐、三乙烯二胺盐、三乙烯四胺盐、联苯胺盐、N,N-双[氨基丙基]甲胺盐、2-甲基硫基丙胺盐、2-丁氧基乙胺盐、AEPD盐、三(羟甲基)氨基甲烷盐、吗啉盐、N-甲基吗啉盐、哌啶盐、吡啶盐、氨基丙基吗啉盐、Jeff胺D-230盐、2,4,6-三(二甲基氨基甲基)苯酚和氢氧化钠的盐、三甲基锍盐、三乙基锍盐;所述Ⅰ-1中X代表O或S;M代表甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,戊基,己基,庚基,辛基,壬基,癸基,十一烷基,十二烷基,十八烷基,三氟甲基,五氟乙基,3-氯丁基,2-氟乙基,2-氯乙基,2-溴乙基,2,2-二氟乙基,2,2,2-三氟乙基,4,4,4-三氟丁基,2,2,3,3,3-五氟丙基,环丙基,环丁基,环戊基,环己基,烯丙基,2-丙炔基,甲氧基,乙氧羰基,甲基磺酰基, 四氢呋喃基,四氢呋喃基亚甲基,吡啶基,吡啶基亚甲基,萘基,萘基亚甲基,呋喃基,呋喃基亚甲基,噻吩基,噻吩基亚甲基, 以及未取代或甲基取代的 未取代或被甲基、二甲基氨基、氯、甲氧基、三氟甲基或异丙基取代的苯基,未取代或被三氟甲基、溴、氯、氟、甲氧基、氰基或甲基取代的苄基;R’代表氢、甲基、乙基、二氟甲基。
- 根据权利要求1-3任意一项所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物,其特征在于,A、B的重量比为1:100~100:1或1:50~50:1;优选为1:30~30:1或1:20~20:1;更优选为1:10~10:1或1:8~8:1;进一步优选为1:5~5:1或1:1~2:1或1:1~1:2。
- 根据权利要求1-4任意一项所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物,其特征在于,所述除草组合物中A和B的质量百分含量占总量的1-95%,优选10-80%。
- 根据权利要求1-4任意一项所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物,其特征在于,所述除草组合物中还包括常规助剂,优选地,所述常规助剂包括载体和/或表面活性剂。
- 根据权利要求1-4任意一项所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物,其特征在于,所述除草组合物进一步包括至少一种安全剂,优选地,所述安全剂选自双苯噁唑酸、cyprosulfamide、吡唑解草酯、解毒喹、赤霉酸、furilazole、metcamifen中的一种或多 种。
- 根据权利要求1-7任意一项所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物,其特征在于,所述除草组合物的具体制剂为可分散油悬浮剂、水悬浮剂、悬乳剂、可湿性粉剂、乳油、水分散粒剂、水乳剂或微乳剂。
- 如权利要求1-7任意一项所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物在防治杂草上的应用,优选地,将所述的除草组合物用于选择性防除有用作物中的杂草,更优选地,所述有用作物为转基因作物或者基因组编辑技术处理过的作物。
- 一种防治不想要的植物生长的方法,其包括将权利要求1-7任意一项所述的一种包含R型吡啶氧基羧酸衍生物的除草组合物施用于植物、植物部位、植物种子或植物生长的区域,优选地,将所述的除草组合物用于选择性防除有用作物中的杂草,更优选地,所述有用作物为转基因作物或者基因组编辑技术处理过的作物。
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EP4005384A4 (en) | 2023-07-19 |
CA3147473A1 (en) | 2021-02-04 |
PE20220703A1 (es) | 2022-05-04 |
AU2020322972A1 (en) | 2022-02-24 |
EP4005384A1 (en) | 2022-06-01 |
ZA202200908B (en) | 2022-04-28 |
MX2022000846A (es) | 2022-02-10 |
JP7494285B2 (ja) | 2024-06-03 |
CO2022000361A2 (es) | 2022-04-29 |
BR112022001311A2 (pt) | 2022-03-22 |
CL2022000133A1 (es) | 2022-08-19 |
JP2022549554A (ja) | 2022-11-28 |
AU2020322972B2 (en) | 2024-08-01 |
US20220264878A1 (en) | 2022-08-25 |
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