CN113661995A - 包含r型吡啶氧基羧酸衍生物和合成激素类抑制剂的除草组合物及其应用 - Google Patents
包含r型吡啶氧基羧酸衍生物和合成激素类抑制剂的除草组合物及其应用 Download PDFInfo
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- CN113661995A CN113661995A CN202010406451.0A CN202010406451A CN113661995A CN 113661995 A CN113661995 A CN 113661995A CN 202010406451 A CN202010406451 A CN 202010406451A CN 113661995 A CN113661995 A CN 113661995A
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- salt
- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 32
- 239000003112 inhibitor Substances 0.000 title claims abstract description 19
- 239000002253 acid Substances 0.000 title claims abstract description 18
- 239000003688 hormone derivative Substances 0.000 title claims abstract description 18
- -1 pyridyloxy carboxylic acid derivative Chemical class 0.000 claims abstract description 93
- 241000196324 Embryophyta Species 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 36
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 239000004480 active ingredient Substances 0.000 claims abstract description 17
- 238000009333 weeding Methods 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005558 Fluroxypyr Substances 0.000 claims abstract description 8
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005504 Dicamba Substances 0.000 claims abstract description 5
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims abstract description 5
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims abstract description 5
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005500 Clopyralid Substances 0.000 claims abstract description 4
- 239000005627 Triclopyr Substances 0.000 claims abstract description 4
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005468 Aminopyralid Substances 0.000 claims abstract description 3
- 239000005595 Picloram Substances 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 230000009261 transgenic effect Effects 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
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical class CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 4
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical class CNCCO OPKOKAMJFNKNAS-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
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002780 morpholines Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000004714 phosphonium salts Chemical class 0.000 claims description 4
- 150000003053 piperidines Chemical class 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
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 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
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical class CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims description 3
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical class CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical class OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 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
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 238000009472 formulation Methods 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
- 229920000768 polyamine Polymers 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 159000000000 sodium salts Chemical group 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl 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
- XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 claims description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 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
- 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
- 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
- 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
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005980 Gibberellic acid Substances 0.000 claims description 2
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical class CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-O N-dimethylethanolamine Chemical class C[NH+](C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-O 0.000 claims description 2
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical class CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical class CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 claims description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical class C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 235000019417 choline salt Nutrition 0.000 claims description 2
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims description 2
- HBGGBCVEFUPUNY-UHFFFAOYSA-N cyclododecanamine Chemical class NC1CCCCCCCCCCC1 HBGGBCVEFUPUNY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical class CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 150000005332 diethylamines Chemical class 0.000 claims description 2
- 150000004656 dimethylamines Chemical class 0.000 claims description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical class CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical class CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 claims description 2
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical class OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 239000004530 micro-emulsion Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical class C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical class CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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Classifications
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
技术领域
本发明属于农药领域,具体涉及一种包含R型吡啶氧基羧酸衍生物和合成激素类抑制剂的除草组合物及其应用。
背景技术
化学除草是农田杂草防除中最为经济、有效的手段,但长期连续高剂量地使用单一品种或单一作用方式的化学除草剂,容易造成杂草耐药和抗性演化等问题。除草剂化合物的合理复配或混配具有扩大杂草谱、提高防除效果、延缓杂草耐药性和抗药性的发生与发展等优点,是解决上述问题的最为有效的方法之一。因此生产上仍需开发安全性高、杀草谱广、能够产生增效作用并解决抗性杂草问题的除草组合物品种。
发明内容
为解决现有技术中存在的上述问题,本发明提供一种包含R型吡啶氧基羧酸衍生物和合成激素类抑制剂的除草组合物及其应用。该组合物能有效防除禾本科或阔叶类等各种杂草问题,具有扩大杀草谱、减少施用量、能够产生增效作用并解决抗性杂草等特点。
一种包含R型吡啶氧基羧酸衍生物和合成激素类抑制剂的除草组合物,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,R1、R2分别独立地代表卤素、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基;
R3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NH4 +、伯胺盐R”NH2、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(优选C1-C6烷基锍盐)、C1-C16烷基氧化锍盐(优选C1-C6烷基氧化锍盐)、C1-C16烷基鏻盐(优选C1-C6烷基鏻盐)或C1-C16烷醇鏻盐(优选C1-C6烷醇鏻盐);
其中,R”分别独立地代表C1-C16烷基,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(优选C1-C6烷基),C2-C12烯基(优选C2-C6烯基),C2-C12炔基(优选C2-C6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;
R4、R5、R6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选自以下合成激素类抑制剂除草化合物或其酸/盐中的一种或多种:
三氯吡氧乙酸(triclopyr,CAS号:55335-06-3)、2甲4氯(MCPA,CAS号:94-74-6)、麦草畏(dicamba,CAS号:1918-00-9)、氨氯吡啶酸(picloram,CAS号:1918-02-1)、氯氨吡啶酸(aminopyralid,CAS号:150114-71-9)、氯氟吡氧乙酸(fluroxypyr,CAS号:69377-81-7)、氯氟吡啶酯(florpyrauxifen benzyl,CAS号:1390661-72-9)、氟氯吡啶酯(halauxifen-methyl,CAS号:943831-98-9)、二氯喹啉酸(quinclorac,CAS号:84087-01-4)、二氯吡啶酸(clopyralid,CAS号:1702-17-6)。
优选地,R1、R2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;
R3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;
所述盐为碱金属(如钠、锂、钾、铯和铷)盐,碱土金属(如钙、镁、钡和锶)盐,以及锑、铋、镉、铈、铬、钴、钪、钛、锰、铜、铁、银、金、锌、铝等金属的盐,胺盐例如铵盐、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、多元胺盐(如六亚甲基四胺盐、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,锍盐如烷基锍盐(如三甲基锍盐、三乙基锍盐)、烷基氧化锍盐,鏻盐如烷基鏻盐或烷醇鏻盐;
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。
更优选地,活性成分A选自以下化合物中的一种或多种:
所述活性成分A的制备方法包括以下步骤:
将通式Ⅲ所示的化合物与通式Ⅱ所示的化合物进行反应制得通式I-1-1所示的化合物;其反应方程式如下:
其中,W代表氢或碱金属,优选K、Na;Hal代表卤素,优选Br、Cl;所述反应在催化剂和溶剂的存在下进行,优选地,所述催化剂为TBAB,所述溶剂为DCM、DCE、ACN、THF、DMF中的一种或多种组合。
将通式I-1-1所示的化合物在氢氧化锂水溶液和溶剂的存在下进行反应,制得通式I所示的化合物;其反应方程式如下:
优选地,所述溶剂选自甲醇、乙醇、异丙醇中的一种或多种组合。
将通式I所示的化合物与M-SH进行反应制得通式I-1-2所示的化合物;其反应方程式如下:
其中,所述反应在脱水剂和溶剂的存在下进行,优选地,所述脱水剂为DCC,所述溶剂选自二氯甲烷、二氯乙烷、乙腈、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲亚砜、四氢呋喃、甲苯、二甲苯中的一种或多种组合。
其中,卤代物优选氯代物或溴代物;所述反应在碱和溶剂的存在下进行,所述碱选自氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠和碳酸铯中的一种或两种以上;溶剂选自THF、1,4-二氧六环、甲苯、1,2-二氯乙烷、乙酸乙酯、乙腈、DMF、丙酮、二氯甲烷和氯仿中的一种或多种组合;所述反应过程中也可加入催化剂,优选DMAP。
所述盐为农药学上可接受的盐,较佳的为本发明所述R型吡啶氧基羧酸化合物与化学上可接受的碱性化合物反应生成。上述药学上可接受的盐容易分离,可采用常规分离方法提纯,如溶剂萃取、稀释、重结晶、柱色谱和制备薄层色谱等。
其中,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1:1~1:2。
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%。
所述除草组合物中还包含常规助剂,所述常规助剂包括载体、表面活性剂。
本文中的术语“载体”表示一种有机或无机、天然或合成的物质。它们有助于活性成分的施用,该载体一般是惰性的且必须是农业上可接受的,特别是被处理的植物所接受。载体可以是固体的,如陶土、天然或合成的硅酸盐、二氧化硅、树脂、蜡、固体肥料等;或者液体的,如水、醇类、酮类、石油馏分、芳烃或蜡烃、氯代烃、液化气等。
表面活性剂可包括乳化剂、分散剂或润湿剂,它可以是离子型或非离子型的。可提及的实例是聚丙烯酸的盐、木质素磺酸盐、苯酚磺酸或萘磺酸的盐、环氧乙烷与脂肪族醇或与脂族酸或与脂肪族胺与取代苯酚(特别是烷基苯酚或芳基苯酚)的聚合物、磺基琥珀酸盐、牛磺酸衍生物(特别是牛磺酸烷脂)及醇的磷酸酯或多羟乙基化的苯酚的磷酸酯、烷基磺酸盐、烷基芳基磺酸盐、烷基硫酸盐、月桂基醚硫酸盐、脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇以及硫酸化脂肪醇乙二醇醚,此外还有萘或萘磺酸与苯酚和甲醛的缩合物、聚氧乙烯辛基苯基醚、乙氧基化异辛基酚、辛基酚或壬基酚、烷基苯基聚乙二醇醚、三丁基苯基聚乙二醇醚、三硬脂基苯基聚乙二醇醚、烷基芳基聚醚醇、醇和脂肪醇/氧化乙烯缩合物、乙氧基化蓖麻油、聚氧乙烯烷基醚、乙氧基化聚氧丙烯、月桂醇聚乙二醇醚缩醛、山梨醇酯、木素亚硫酸盐废液,以及蛋白质、变性蛋白、多糖(例如甲基纤维素)、疏水改性淀粉、聚乙烯醇、聚羧酸盐、聚烷氧基化物、聚乙烯胺、聚乙烯吡咯烷酮及其共聚物。至少需要一种表面活性剂存在,以有利于活性成分在水中的分散并有利于使它们能正确地施用于植物。
上述组合物也可含有各种其他的组分,如保护胶体、粘合剂、增稠剂、触变剂、渗透剂、稳定剂、螯合剂、染料、着色剂和聚合物。
所述除草组合物进一步包括至少一种安全剂,具体可选自CN101194623A中提及的任何安全剂。优选地,所述安全剂选自双苯噁唑酸(CAS:163520-33-0)、cyprosulfamide(CAS:221667-31-8)、吡唑解草酯(CAS:135590-91-9)、解毒喹(CAS:99607-70-2)、赤霉酸(CAS:7-06-5)、furilazole(CAS:121776-33-8)、metcamifen(CAS:129531-12-0)中的一种或多种。
另外,本发明的组合物可以与以下活性物质混合,例如《世界农药新品种技术大全》,中国农业科学技术出版社,2010.9和这里引用的文献中的已知物质。
在本说明书的上下文中,如果使用活性化合物的通用名称的缩写形式,则在每种情况下包括所有的常规衍生物,例如酯和盐,以及异构体,特别是光学异构体,特别是一种或多种市售形式。如果通用名称表示酯或盐,则在每种情况下还包括所有其他的常规衍生物,例如其他的酯和盐、游离酸和中性化合物,以及异构体,特别是光学异构体,特别是一种或多种市售形式。给出的化合物的化学名称表示至少一种被通用名称涵盖的化合物,通常是优选的化合物。在磺酰胺如磺酰脲的情况下,盐还包括通过阳离子与磺酰胺基团中的氢原子交换而形成的盐。例如,2甲4氯衍生物包含但不限于:2甲4氯钠盐、钾盐、二甲铵盐、异丙胺盐等,以及2甲4氯甲酯、乙酯、异辛酯、乙硫酯等;2,4-D衍生物包含但不限于:2,4-D盐如钠盐、钾盐、二甲铵盐、三乙醇铵盐、异丙胺盐、胆碱等,以及2,4-D酯如甲酯、乙酯、丁酯、异辛酯等。
在本发明的上下文中,化合物的盐优选为各自的碱金属盐、碱土金属盐或铵盐的形式,优选为各自的碱金属盐的形式,更优选为各自的钠盐或钾盐的形式,最优选为各自的钠盐的形式。
本发明的组合物可以由使用者在使用前经稀释或直接使用。其配制可由通常的加工方法制备,即将活性物质与液体溶剂或固体载体混合后,再加入表面活性剂如分散剂、稳定剂、湿润剂、粘合剂、消泡剂等中的一种或几种。
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(干悬浮剂)、水乳剂、微乳剂。
简而言之,本发明的组合物可以和现有技术的配方中常规使用的固体和液体添加剂混合。随着外部条件的变化,有效成分的使用量也不同,外部条件为,例如温度、湿度、使用的除草剂的性质等等。它可以有大的变化幅度,例如在0.001到1.0kg/ha之间,或更多的活性物质,但优选在0.005到750g/ha之间,特别是在0.005到500g/ha之间。
另外,本发明的组合物可通过喷雾的方法被施用于待处理植物叶片上,即施用于杂草,特别是杂草侵扰或易侵扰影响的表面上。
进一步,本发明还提供一种所述除草组合物在防治杂草上的应用;以及提供一种防治不想要的植物生长的方法,其包括将所述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。
本发明化合物可用于处理所有植株和植株部分。植株品种和栽培品系可通过常规的繁殖和育种方法或通过基因工程方法获得。经基因修饰的植株(转基因植物)为其中异源性基因(转基因)已被稳定整合进植株的基因组的那些。由它在植物基因组中的特定位置所限定的转基因被称为转化事件或转基因事件。
经基因修饰的可根据本发明处理的植株栽培品系包括抵抗一种或多种生物胁迫的那些(害虫,诸如线虫动物、昆虫、螨虫、真菌等)或非生物胁迫(干旱、低温、土壤盐化等),或其包含其它期望的特征。植株可经基因修饰以表现出性状,例如除草剂耐受性、昆虫耐受性、修饰的油特征或耐旱性。包含单个基因转化事件或转化事件的组合的可用的经基因修饰的植株可参见CN106659159A。其中所列的基因修饰的另外的信息可得自例如通过美国农业部保持的公共可得的数据库。
当施用本发明的除草组合物时,获得了预料不到的增效效果,并且除草活性比使用单个除草剂的活性预期总和,以及单个除草剂的活性更为显著。增效效果表现为施用量减少、更宽的杂草控制谱、除草作用更快、更持久,这些特性是杂草控制实践过程中所需要的。就所描述的特性来说,这些新组合物明显地优越于现有的除草剂,达到减量使用,对环境更友好。
本发明的增效除草组合物还具有下述优点:
(1)本发明的组合物为环境友好型,在环境中均易于降解。
(2)本发明的除草组合物成本低、使用方便,其推广应用有巨大的经济效益和社会效益。
具体实施方式
下列实施例并非限制本发明,而只是用来说明本发明是如何实现的。对于某些杂草,这些实施例显示出特别显著的有效性。举例如下:
药效试验(苗后茎叶喷雾处理):
1)试验条件
1.1)、供试靶标
杂草采用盆栽法培养,用180х140mm塑料营养钵,摆放于搪瓷盘中,内装从农田采回经风干过筛的表层土壤(4/5处),土壤湿度初期均控制在20%,挑选籽粒饱满均一的杂草种子,用25℃温水浸泡6小时,在28℃生化培养箱(黑暗)中催芽,将刚刚露白的杂草种子均匀摆放在土壤表面,根据种子粒径大小然后覆土0.5-1cm。
1.2)、培养条件
在可控日光温室内进行,温度20~30℃,自然光照,相对湿度57%~72%。土壤类型为壤土,有机质含量为1.63%,pH=7.1,碱解氮84.3mg/kg,速效磷38.5mg/kg,速效钾82.1mg/kg。
1.3)、仪器设备
3WP-2000型行走式喷雾塔,农业部南京农业机械研究所。GA10型万分之一电子天平(德国);ZDR2000智能数据记录仪(杭州泽大仪器有限公司);SPX型智能生化培养箱(宁波江南仪器厂)。
2)试验设计
2.1)、试剂
所需活性成分A来自专利CN201911321469.4,代表性化合物的制备实施例如下,其他化合物的合成方法类似,故不再赘述。所需活性成分B由试剂公司购买。原药均采用丙酮作溶剂,用含量0.1%乳化剂吐温-80水溶液稀释,现用现稀释。
(1)化合物A1的合成
将化合物a(0.5g,2.13mmol),化合物b(313mg,2.55mmol),催化量的TBAB(10mg),DMF(10mL)置于圆底烧瓶中,室温15℃下搅拌24小时。液质检测少量原料剩余,即可处理。将反应液倒入到50mL水中,用甲基叔丁基醚萃取2次(50mL x 2),有机相干燥,浓缩,经柱层析分离纯化,得到化合物A67(300mg,收率50%)。化合物A67为白色固体。
将化合物A67(0.3g,1.06mmol)、甲醇(20mL)置于100mL单口瓶中,氢氧化锂(44.5mg,1.06mmol)溶解在2mL水中,室温下缓慢滴加到单口瓶中,室温搅拌12小时。液质检测原料反应完,用0.5M稀盐酸调pH至5-6,浓缩,用水和乙酸乙酯萃取。有机相干燥、浓缩得到化合物A1(200mg,收率70%),化合物A1为白色固体。
(2)化合物A2的合成
将化合物A1(200mg,0.74mmol),化合物c(75mg,0.74mmol),DCC(152mg,0.74mmol),无水DCM(20mL)置于100mL圆底烧瓶中,室温反应12小时。液质检测原料反应完,将反应液浓缩,经柱层析分离得到化合物A2(200mg,收率77%),化合物A2为白色固体。
2.2)、试验处理
2.2.1)、剂量设置
在确定A与活性成分B配比或含量时,应从两种药剂的作用特点及其毒力等衡量,还要考虑该配方的主要使用目的。本研究在前期预试的基础上,设A、B活性成分单用及混合用量分别见表格。以不含药剂、含相同溶剂及乳化剂的水作为空白对照。
2.2.2)、试验重复
每处理重复4次,每次每处理10盆,每盆播种杂草种子10粒,后定苗每盆3株。
2.3)、处理方式
2.3.1)、处理时间和次数
试验共用药1次。待杂草6~8叶期,间苗,保持每盆内杂草3株,每处理保留30株,然后继续培养至小飞蓬株高10厘米进行处理。
2.3.2)、使用器械和用药方法
将培养好的试材均匀摆放在面积0.5m2的平台上,用3WP-2000型行走式喷雾塔茎叶喷雾,喷液量按450公斤/公顷计。喷雾压力0.3MPa。待全部药液喷完后,关闭气阀,30秒后,打开喷雾塔门,取出营养钵。然后打开气阀,喷清水50mL,清洗喷液管。
3)试验方法
采用盆栽法。杂草培养见1.1),参照《农药室内生物测定试验准则除草剂》进行。用药方法见2.3.2),采用茎叶处理法。处理后移入温室常规培养。
4)数据调查与统计分析
4.1)、调查方法
采用绝对数调查法,用刀片沿土壤表面切断存活杂草整株幼苗,用分析天平称量杂草鲜重。对于已经死亡的杂草,按鲜重为零计。
4.2)、调查时间和次数
处理后24天调查,共调查1次。
4.3)、数据统计分析
用Gowing法计算各处理混合组合的理论鲜重抑制率(E0=X+Y-X*Y/100),然后与实测抑制率(E)相比较,评价二者混用对杂草的联合作用类型,当E-E0值大于10%为增效作用、小于-10%为拮抗作用、在-10%~10%之间为加成作用。并根据实际防效和除草剂特点、配方的平衡性等因素确定最佳配比。式中X为活性成分A用量为P时的鲜重抑制率;Y为活性成分B用量为Q时的鲜重抑制率。
统计结果见下表1-10。
表1 A2混配三氯吡氧乙酸对小飞蓬的实际防效与联合作用评价
表2 A2混配2甲4氯对小飞蓬的实际防效与联合作用评价
表3 A2混配麦草畏对小飞蓬的实际防效与联合作用评价
表4 A2混配氨氯吡啶酸对小飞蓬的实际防效与联合作用评价
表5 A2混配氯氨吡啶酸对小飞蓬的实际防效与联合作用评价
表6 A2混配氯氟吡氧乙酸对小飞蓬的实际防效与联合作用评价
表7 A2混配氯氟吡啶酯对小飞蓬的实际防效与联合作用评价
表8 A2混配氟氯吡啶酯对小飞蓬的实际防效与联合作用评价
表9 A2混配二氯喹啉酸对小飞蓬的实际防效与联合作用评价
表10 A2混配二氯吡啶酸对小飞蓬的实际防效与联合作用评价
经过大量试验和探索,本发明意外地发现,所述组合物用于防除阔叶类杂草、禾本科杂草等具有令人惊讶的、意想不到的增效作用,这种增效作用在低剂量下表现更为显著,可降低用药量,降低对环境的污染,且合理复配降低了农用成本,对ALS、ACCase抑制剂抗性杂草高效,具有很好的应用前景。同时经过测试在小麦田、玉米田、水稻田、花生、甘蔗、高粱、谷子、马铃薯、油菜、大豆、棉花、蔬菜、早熟禾、高羊茅、结缕草等大田中显示良好的选择性和优异的增效作用,可以开发成具有广泛市场价值的除草剂混剂。
Claims (10)
1.一种包含R型吡啶氧基羧酸衍生物和合成激素类抑制剂的除草组合物,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,R1、R2分别独立地代表卤素、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基;
R3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NH4 +、伯胺盐R”NH2、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;
R4、R5、R6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选自以下合成激素类抑制剂除草化合物或其酸/盐中的一种或多种:
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。
2.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和合成激素类抑制剂的除草组合物,其特征在于,
R1、R2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;
R3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。
4.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和合成激素类抑制剂的除草组合物,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1:1~1:2。
5.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和合成激素类抑制剂的除草组合物,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%。
6.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和合成激素类抑制剂的除草组合物,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或表面活性剂。
7.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和合成激素类抑制剂的除草组合物,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。
8.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和合成激素类抑制剂的除草组合物,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。
9.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和合成激素类抑制剂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。
10.一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和合成激素类抑制剂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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