CN115667231A - 取代的间苯二甲酸二酰胺及其用于除草剂的用途 - Google Patents
取代的间苯二甲酸二酰胺及其用于除草剂的用途 Download PDFInfo
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- CN115667231A CN115667231A CN202180038843.9A CN202180038843A CN115667231A CN 115667231 A CN115667231 A CN 115667231A CN 202180038843 A CN202180038843 A CN 202180038843A CN 115667231 A CN115667231 A CN 115667231A
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- ORHJUFUQMQEFPQ-UHFFFAOYSA-M potassium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [K+].CC1=CC(Cl)=CC=C1OCC([O-])=O ORHJUFUQMQEFPQ-UHFFFAOYSA-M 0.000 description 1
- LIOPHZNMBKHGAV-UHFFFAOYSA-M potassium;2-(phosphonomethylamino)acetate Chemical compound [K+].OC(=O)CNCP(O)([O-])=O LIOPHZNMBKHGAV-UHFFFAOYSA-M 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- ASBOANRLBWZXTM-UHFFFAOYSA-N propan-2-yl 3-(5-chloroquinolin-8-yl)peroxy-3-oxopropanoate Chemical compound C1=CN=C2C(OOC(=O)CC(=O)OC(C)C)=CC=C(Cl)C2=C1 ASBOANRLBWZXTM-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
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- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000003620 semiochemical Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 230000007330 shade avoidance Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- VPAOSFFTKWUGAD-TVKJYDDYSA-N skimmin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(C=CC(=O)O2)C2=C1 VPAOSFFTKWUGAD-TVKJYDDYSA-N 0.000 description 1
- SBFTZUUHPXPXLH-UHFFFAOYSA-N skimmin Natural products OCC1OC(C(O)C(O)C1O)c2ccc3C=CC(=O)Oc3c2 SBFTZUUHPXPXLH-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 1
- JUNDBKFAZXZKRA-MAFYXNADSA-M sodium;2-[(e)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylate Chemical compound [Na+].N=1C=CC=C(C([O-])=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 JUNDBKFAZXZKRA-MAFYXNADSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- VPAOSFFTKWUGAD-UHFFFAOYSA-N umbelliferone beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C=CC(=O)O2)C2=C1 VPAOSFFTKWUGAD-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P21/00—Plant growth regulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
本发明涉及作为除草剂的具有通式(I)的间苯二甲酸二酰胺。在该式(I)中,X和Y代表例如氢、烷基和卤素等基团。Z1和Z2代表例如烷基、环烷基和苯基等基团。Q代表杂环例如四唑基。
Description
本发明涉及除草剂的技术领域,尤其是用于选择性防治有用植物中的阔叶杂草和禾本科杂草的除草剂的技术领域。
WO 2012/028579 A1、WO 2012/126932 A1、WO2013/017559 A1和WO 2017/144402A1记载了尤其是具有除草活性的间苯二甲酰胺,它们的根本区别在于两种酰胺官能团上的取代基性质。
WO 2012/028579 A1记载了以下具有除草活性的间苯二甲酰胺:
2-氯-N3,N3-二甲基-4-(甲基磺酰基)-N1-(1-甲基-1H-1,2,4-三唑-5-基)间苯二甲酰胺、2-氯-N3-甲氧基-N3-甲基-4-(甲基磺酰基)-N1-(1-甲基-1H-1,2,4-三唑-5-基)间苯二甲酰胺、2-氯-N1-(1-乙基-1H-1,2,4-三唑-5-基)-N3,N3-二甲基-4-(甲基磺酰基)间苯二甲酰胺、2-氯-N1-(1-乙基-1H-1,2,4-三唑-5-基)-N3-甲氧基-N3-甲基-4-(甲基磺酰基)间苯二甲酰胺、2-氯-N3,N3-二甲基-4-(甲基磺酰基)-N1-(1-苯基-1H-1,2,4-三唑-5-基)间苯二甲酰胺、2-氯-N3-甲氧基-N3-甲基-4-(甲基磺酰基)-N1-(1-苯基-1H-1,2,4-三唑-5-基)间苯二甲酰胺、2-氯-N3,N3-二甲基-4-(甲基磺酰基)-N1-(1-甲基-1H-四唑-5-基)间苯二甲酰胺、2-氯-N3-甲氧基-N3-甲基-4-(甲基磺酰基)-N1-(1-甲基-1H-四唑-5-基)间苯二甲酰胺、2-氯-N1-(1-乙基-1H-四唑-5-基)-N3,N3-二甲基-4-(甲基磺酰基)间苯二甲酰胺、2-氯-N1-(1-乙基-1H-四唑-5-基)-N3-甲氧基-N3-甲基-4-(甲基磺酰基)间苯二甲酰胺、2-氯-N3,N3-二甲基-4-(甲基磺酰基)-N1-(1-苯基-1H-四唑l-5-基)间苯二甲酰胺、2-氯-N3-甲氧基-N3-甲基-4-(甲基磺酰基)-N1-(1-苯基-1H-四唑-5-基)间苯二甲酰胺。
WO2013/017559A1公开了以下具有除草活性的间苯二甲酰胺:
2-氯-N1-[1-(2-甲氧基乙基)-1H-四唑-5-基]-N3,N3-二甲基-4-(甲基磺酰基)间苯二甲酰胺、2-氯-N3-甲氧基-N1-[1-(2-甲氧基乙基)-1H-四唑-5-基]-N3-甲基-4-(甲基磺酰基)间苯二甲酰胺。
特别地,其中公开的间苯二甲酰胺总是具有叔酰胺基团。然而,由这些文献中已知的间苯二甲酰胺并不总是具有足够的除草功效和/或与作物植物的相容性。
已经发现,与现有技术中已知的间苯二甲酰胺相比,在苯环的2位和4位具有叔酰胺基团的间苯二甲酰胺具有较好的性能。因此,本发明提供式(I)的间苯二甲酰胺或其盐
其中符号和角标定义如下:
Q为Q1或Q2,
W为氮,
X为卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、R1O、R2(O)nS、R1O-(C1-C6)-烷基或R2S(O)n-(C1-C6)-烷基,
Y为卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、R1O或R2(O)nS,条件为当X为氯时,Y不为甲基磺酰基,
Z1,Z2彼此独立地为各自被s个选自卤素、氰基、R1C(O)、R1OC(O)、R1O和R2(O)nS的基团取代的以下基团:(C1-C6)-烷基、(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、(C1-C6)-烷基-O-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-烯基-(C1-C6)-烷基、(C2-C6)-炔基、(C2-C6)-炔基-(C1-C6)-烷基、(C1-C6)-烷氧基、R2S(O)n-(C1-C6)-烷基、R1C(O)、
R1OC(O)、R1C(O)-(C1-C6)-烷基、R1OC(O)-(C1-C6)-烷基、R1NH-(C1-C6)-烷基、R1 2N-(C1-C6)-烷基、R1NHC(O)-(C1-C6)-烷基或R1 2NC(O)-(C1-C6)-烷基,
或
各自被s个选自卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、R1C(O)和R1OC(O)的基团取代的以下基团:苯基、苯甲基、杂环或杂环-(C1-C6)-烷基,
或
Z1和Z2与它们所连接的氮原子一起形成四-、五-、六-或七
-元杂环,所述杂环包含n个选自O、S和N的其他杂原子作为环原子,并被m个选自以下的基团取代:羰基、卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基和卤代-(C1-C6)-烷氧基,
R1为(C1-C6)-烷基、卤代-(C1-C6)-烷基或(C3-C6)-环烷基,
R2为(C1-C6)-烷基,
Rx为(C1-C6)-烷基、(C1-C6)-烷基-O-(C1-C6)-烷基或苯基,
m为0、1、2或3,
n为0、1或2,
s为0、1、2、3或4。
在式(I)和以下所有式中,具有多于两个碳原子的烷基基团可为直链或支链的。烷基基团为例如甲基、乙基、正丙基或异丙基、正丁基、异丁基、叔丁基或2-丁基、戊基、己基,例如正己基、异己基和1,3-二甲基丁基。类似地,烯基为例如烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基丁-3-烯-2-基和1-甲基丁-2-烯-1-基。炔基为例如炔丙基、丁-2-炔-1-基、丁-3-炔-1-基和1-甲基丁-3-炔-1-基。多重键可位于各个不饱和基团中的任何位置。环烷基为具有三至六个碳原子的碳环饱和环体系,例如环丙基、环丁基、环戊基或环己基。卤素取代的烷基意指直链或支链烷基基团,其中这些基团中的一些或所有氢原子可被卤素原子替代,例如C1-C2-卤代烷基,例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基和1,1,1-三氟丙-2-基。
卤素代表氟、氯、溴或碘。
杂环基团(杂环基)为4-、5-或6-元环状基团,其除碳原子外包含至少一种选自N、O、S的杂原子,并且为饱和的、不饱和的、部分饱和的或杂芳族的,并且可为未被取代或被取代的,在这种情况下,键合点位于环原子上。杂环基团的实例为1-或2-或3-吡咯烷基、3,4-二氢-2H-吡咯-2-或3-基、2,3-二氢-1H-吡咯-1-或2-或3-或4-或5-基;2,5-二氢-1H-吡咯-1-或2-或3-基、1-或2-或3-或4-哌啶基;2,3,4,5-四氢吡啶-2-或3-或4-或5-基或6-基;1,2,3,6-四氢吡啶-1-或2-或3-或4-或5-或6-基;1,2,3,4-四氢吡啶-1-或2-或3-或4-或5-或6-基;1,4-二氢吡啶-1-或2-或3-或4-基;2,3-二氢吡啶-2-或3-或4-或5-或6-基;2,5-二氢吡啶-2-或3-或4-或5-或6-基,1-或2-或3-或4-氮杂环庚基(azepanyl)、2-或3-氧杂环戊基(oxolanyl)(=2-或3-四氢呋喃基);2,3-二氢呋喃-2-或3-或4-或5-基;2,5-二氢呋喃-2-或3-基,2-或3-或4-氧杂环己基(oxanyl)(=2-或3-或-4-四氢吡喃基);3,4-二氢-2H-吡喃-2-或3-或4-或5-或6-基;3,6-二氢-2H-吡喃-2-或3-或4-或5-或6-基;2H-吡喃-2-或3-或4-或5-或6-基;4H-吡喃-2-或3-或4-基,2-或3-或4-氧杂环庚基(oxepanyl);2-或3-四氢噻吩基;2,3-二氢噻吩-2-或3-或4-或5-基;2,5-二氢噻吩-2-或3-基;四氢-2H-噻喃-2-或3-或4-基;3,4-二氢-2H-噻喃-2-或3-或4-或5-或6-基;3,6-二氢-2H-噻喃-2-或3-或4-或5-或6-基;2H-噻喃-2-或3-或4-或5-或6-基;4H-噻喃-2-或3-或4-基;1-或2-或3-或4-吡唑烷基;4,5-二氢-3H-吡唑-3-或4-或5-基;4,5-二氢-1H-吡唑-1-或3-或4-或5-基;2,3-二氢-1H-吡唑-1-或2-或3-或4-或5-基;1-或2-或3-或4-咪唑烷基;2,3-二氢-1H-咪唑-1-或2-或3-或4-基;2,5-二氢-1H-咪唑-1-或2-或4-或5-基;4,5-二氢-1H-咪唑-1-或2-或4-或5-基;六氢哒嗪-1-或2-或3-或4-基;1,2,3,4-四氢哒嗪-1-或2-或3-或4-或5-或6-基;1,2,3,6-四氢哒嗪-1-或2-或3-或4-或5-或6-基;1,4,5,6-四氢哒嗪-1-或3-或4-或5-或6-基;3,4,5,6-四氢哒嗪-3-或4-或5-基;4,5-二氢哒嗪-3-或4-基;3,4-二氢哒嗪-3-或4-或5-或6-基;3,6-二氢哒嗪-3-或4-基;1,6-二氢吡嗪-1-或3-或4-或5-或6-基;六氢嘧啶-1-或2-或3-或4-基;1,4,5,6-四氢嘧啶-1-或2-或4-或5-或6-基;1,2,5,6-四氢嘧啶-1-或2-或4-或5-或6-基;1,2,3,4-四氢嘧啶-1-或2-或3-或4-或5-或6-基;1,6-二氢嘧啶-1-或2-或4-或5-或6-基;1,2-二氢嘧啶-1-或2-或4-或5-或6-基;2,5-二氢嘧啶-2-或4-或5-基;4,5-二氢嘧啶-4-或5-或6-基;1,4-二氢嘧啶-1-或2-或4-或5-或6-基;1-或2-或3-哌嗪基;1,2,3,6-四氢吡嗪-1-或2-或3-或5-或6-基;1,2,3,4-四氢吡嗪-1-或2-或3-或4-或5-或6-基;1,2-二氢吡嗪-1-或2-或3-或5-或6-基;1,4-二氢吡嗪-1-或2-或3-基;2,3-二氢吡嗪-2-或3-或5-或6-基;2,5-二氢吡嗪-2-或3-基;1,3-二氧杂环戊烷-2-或4-或5-基;1,3-二氧杂环戊烯-2-或4-基(1,3-dioxol-2-or 4-yl);1,3-二氧杂环己-2-或4-或5-基(1,3-dioxan-2-or4-or 5-yl);4H-1,3-二氧杂环己烯-2-或4-或5-或6-基(4H-1,3-dioxin-2-or 4-or 5-or6-yl);1,4-二氧杂环己-2-或3-或5-或6-基;2,3-二氢-1,4-二氧杂环己烯-2-或3-或5-或6-基;1,4-二氧杂环己烯-2-或3-基;1,2-二硫戊环-3-或4-基(1,3-dithiolan-3-or 4-yl);3H-1,2-二硫杂环戊烯-3-或4-或5-基(3H-1,2-dithiol-3-or 4-or 5-yl);1,3-二硫戊环-2-或4-基;1,3-二硫杂环戊烯-2-或4-基;1,2-二硫杂环己-3-或4-基(1,2-dithian-3-or 4-yl);3,4-二氢-1,2-二硫杂环己烯-3-或4-或5-或6-基(3,4-dihydro-1,2-dithiin-3-or 4-or 5-or 6-yl);3,6-二氢-1,2-二硫杂环己烯-3-或4-基;1,2-二硫杂环己烯-3-或4-基;1,3-二硫杂环己-2-或4-或5-基;4H-1,3-二硫杂环己烯-2-或4-或5-或6-基;异噁唑啉-2-或3-或4-或5-基;2,3-二氢异噁唑-2-或3-或4-或5-基;2,5-二氢异噁唑-2-或3-或4-或5-基;4,5-二氢异噁唑-3-或4-或5-基;1,3-噁唑啉-2-或3-或4-或5-基;2,3-二氢-1,3-噁唑-2-或3-或4-或5-基;2,5-二氢-1,3-噁唑-2-或4-或5-基;4,5-二氢-1,3-噁唑-2-或4-或5-基;1,2-噁嗪烷-2-或3-或4-或5-或6-基(1,2-oxazinan-2-or 3-or 4-or5-or 6-yl);3,4-二氢-2H-1,2-噁嗪-2-或3-或4-或5-或6-基;3,6-二氢-2H-1,2-噁嗪-2-或3-或4-或5-或6-基;5,6-二氢-2H-1,2-噁嗪-2-或3-或4-或5-或6-基;5,6-二氢-4H-1,2-噁嗪-3-或4-或5-或6-基;2H-1,2-噁嗪-2-或3-或4-或5-或6-基;6H-1,2-噁嗪-3-或4-或5-或6-基;4H-1,2-噁嗪-3-或4-或5-或6-基;1,3-噁嗪烷-2-或3-或4-或5-或6-基;3,4-二氢-2H-1,3-噁嗪-2-或3-或4-或5-或6-基;3,6-二氢-2H-1,3-噁嗪-2-或3-或4-或5-或6-基;5,6-二氢-2H-1,3-噁嗪-2-或4-或5-或6-基;5,6-二氢-4H-1,3-噁嗪-2-或4-或5-或6-基;2H-1,3-噁嗪-2-或4-或5-或6-基;6H-1,3-噁嗪-2-或4-或5-或6-基;4H-1,3-噁嗪-2-或4-或5-或6-基;吗啉-2-或3-或4-基;3,4-二氢-2H-1,4-噁嗪-2-或3-或4-或5-或6-基;3,6-二氢-2H-1,4-噁嗪-2-或3-或5-或6-基;2H-1,4-噁嗪-2-或3-或5-或6-基;4H-1,4-噁嗪-2-或3-基;异噻唑啉-2-或3-或4-或5-基;2,3-二氢异噻唑-2-或3-或4-或5-基;2,5-二氢异噻唑-2-或3-或4-或5-基;4,5-二氢异噻唑-3-或4-或5-基;1,3-噻唑啉-2-或3-或4-或5-基;2,3-二氢-1,3-噻唑-2-或3-或4-或5-基;2,5-二氢-1,3-噻唑-2-或4-或5-基;4,5-二氢-1,3-噻唑-2-或4-或5-基;1,3-噻嗪烷-2-或3-或4-或5-或6-基(1,3-thiazinan-2-or 3-or 4-or5-or 6-yl);3,4-二氢-2H-1,3-噻嗪-2-或3-或4-或5-或6-基;3,6-二氢-2H-1,3-噻嗪-2-或3-或4-或5-或6-基;5,6-二氢-2H-1,3-噻嗪-2-或4-或5-或6-基;5,6-二氢-4H-1,3-噻嗪-2-或4-或5-或6-基;2H-1,3-噻嗪-2-或4-或5-或6-基;6H-1,3-噻嗪-2-或4-或5-或6-基;4H-1,3-噻嗪-2-或4-或5-或6-基;4,2-二噁唑烷-2-或3-或5-基;1,4,2-二噁唑-3-或5-基;1,4,2-二噁嗪烷-2-或-3-或5-或6-基;5,6-二氢-1,4,2-二噁嗪-3-或5-或6-基;1,4,2-二噁嗪-3-或5-或6-基。
根据取代基的性质和它们的连接方式,通式(I)的化合物可作为立体异构体存在。例如,如果存在一个或多个不对称取代的碳原子,则可有对映异构体和非对映异构体。当n为1(亚砜)时,也会出现立体异构体。立体异构体可通过常规分离方法(例如通过色谱分离方法)从制备过程中获得的混合物中获得。同样可通过使用立体选择反应并使用光学活性起始材料和/或助剂选择性地制备立体异构体。本发明还涉及通式(I)涵盖但未明确定义的所有立体异构体及其混合物。
式(I)的化合物可形成盐。合适的碱为,例如,有机胺例如三烷基胺、吗啉、哌啶或吡啶;以及铵、碱金属或碱土金属的氢氧化物、碳酸盐和碳酸氢盐,特别是氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠和碳酸氢钾。这些盐为其中的酸性氢被农业上合适的阳离子所替代的化合物,例如金属盐,特别是碱金属盐或碱土金属盐,特别是钠盐和钾盐,或铵盐,与有机胺的盐或季铵盐,例如,具有式[NRR′R″R″′]+的阳离子的盐,其中R至R″′各自独立地为有机基团,特别是烷基、芳基、芳烷基或烷基芳基。还有用的为烷基锍盐和烷基氧化锍盐,例如(C1-C4)-三烷基锍盐和(C1-C4)-三烷基氧化锍盐。
式(I)的化合物可通过合适的无机酸或有机酸(例如无机酸,例如HCl、HBr、H2SO4、H3PO4或HNO3;或有机酸,例如羧酸如甲酸、乙酸、丙酸、乙二酸、乳酸或水杨酸或磺酸,例如对甲苯磺酸)与碱性基团(例如氨基、烷基氨基、二烷基氨基、哌啶基、吗啉基或吡啶基)的加合物形成反应从而形成盐。于是这些盐含有酸的共轭碱作为阴离子。
优选通式(I)的化合物,其中符号和角标具有以下含义:
Q为Q1,
Rx为Me、Et、Pr、i-Pr、c-Pr、(CH2)2OMe或Ph,
W为氮,
X为卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、c-Pr、OMe、OEt、SMe、SEt、CH2OMe或CH2SMe,
Y为卤素、卤代-(C1-C6)-烷基、OMe、SMe、S(O)Me、SO2Me、SEt、S(O)Et或SO2Et,
条件为当X为氯时,Y不为甲基磺酰基,
Z1,Z2独立地为(C1-C6)-烷基、(C3-C6)-环烷基、CH2c-Pr、卤代-(C1-C6)-烷基、(CH2)2OMe、(CH2)2SMe、烯丙基、炔丙基、C(O)CH3、C(O)-c-Pr、CO2Me、CO2Et、Ph、(2-Me)Ph、(4-F)Ph、CH2C(O)NMe2、CH2C(O)Me或CH2C(O)cPr。
或Z1和Z2同为(CH2)3或(CH2)4,
或W、Z1和Z2同为吡唑-1-基或L-脯氨酸-1-基乙基酯。
特别优选为通式(I)的化合物,其中符号和角标具有以下含义:
Q为Q1,
Rx为Me、Et或Pr,
W为氮,
X为F、Cl、Br、I、Me、Et、c-Pr、OMe、SMe、SEt或CH2OMe,
Y为F、Cl、Br、I、SMe、S(O)Me、SO2Me、CHF2、CF3或C2F5,
条件为当X为氯时,Y不为甲基磺酰基,
Z1,Z2独立地为Me、Et、c-Pr、CH2-c-Pr,CH2CHF2、CH2CF3、C(O)CH3、C(O)c-Pr、CO2Me、CO2Et、Ph或(2-Me)Ph,
或Z1和Z2同为(CH2)4,
或W、Z1和Z2同为吡唑-1-基或L-脯氨酸-1-基乙基酯,
R1为Me、Et或c-Pr,
R2为Me。
本发明的化合物可例如通过WO 2012/028579 A1的方案1中详细说明的方法制备。相应的苯甲酰氯或其母体苯甲酸原则上为已知的,并且可例如通过记载于WO1998/029383、EP418013、EP282944、JP2000319251或JP02045448中的方法进行制备。下文进一步描述的实施例进一步阐明了本发明的化合物的制备方法。
各反应混合物的后处理通常通过已知的方法实现,例如通过结晶、水萃取处理、通过色谱法或通过这些方法的组合。
根据取代基的性质和它们的连接方式,通式(I)的化合物可作为立体异构体存在。例如,如果存在一个或多个不对称取代的碳原子,则可有对映异构体和非对映异构体。当n为1(亚砜)时,也会出现立体异构体。立体异构体可通过常规分离方法,例如通过色谱分离方法,从制备过程中获得的混合物中获得。同样可通过使用立体选择性反应并使用光学活性起始材料和/或助剂选择性地制备立体异构体。本发明还涉及通式(I)涵盖但未明确定义的所有立体异构体及其混合物。
可通过上述反应合成的式(I)的化合物和/或其盐的集合也可以并行的方式制备,在这种情况下,可以手动、部分自动化或完全自动化的方式进行。例如,可自动进行反应、后处理或产品和/或中间体的纯化。总之,这被理解为意指例如由D.Tiebes在CombinatorialChemistry-Synthesis,Analysis,Screening(编辑:Günther Jung)中所描述的方法。
本发明的式(I)的化合物(和/或其盐),下文统称为“本发明的化合物”,对经济上重要的广谱单子叶和双子叶一年生有害植物具有优秀的除草功效。
因此,本发明还提供了一种防治不想要的植物或调节植物生长的方法(优选地在植物作物中),其中将本发明的一种或多种化合物施用于植物(例如,有害植物,例如单子叶或双子叶杂草或不想要的作物植物),种子(例如谷物、种子或营养繁殖体,例如块茎或带芽的嫩枝部分)或植物生长于其上的区域(例如栽培区域)。本发明的化合物可在例如播种前(如果合适,也可通过掺入土壤中)、出苗前或出苗后应用。可通过本发明的化合物防治的单子叶和双子叶杂草植物区系的一些代表的具体实例如下,尽管列举并不打算对特定物种施加限制。
单子叶有害植物属:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、蔗草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
双子叶杂草属:苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、蔓锦葵属(Anoda)、春黄菊属(Anthemis)、蔷薇属(Aphanes)、蒿属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针草属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、猪殃殃属(Galium)、木槿属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、粟米草属(Mullugo)、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦莴菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、三叶草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
当将本发明的化合物在出苗前施用于土壤表面时,要么完全阻止杂草幼苗出苗,要么杂草生长直至其已达子叶期,但随后停止生长。
如果在出苗后将活性成分施用至植物的绿色部位,则生长在处理后停止,且所述有害植物停留在施用时的生长阶段,或其在一定时间后完全死亡,从而以此方式在非常早的时期并以持久的方式消除对作物植物有害的杂草的竞争。
本发明的化合物可在有用的植物作物中具有选择性,也可作为非选择性除草剂施用。
凭借除草和植物生长调节性质,所述活性成分还可用于防治已知的或尚未开发的转基因植物作物中的有害植物。通常,转基因植物的特征在于特别有利的性质,例如对农用化学品产业中使用的某些活性成分(特别是某些除草剂)的抗性,对植物病害或植物病害的病原体(例如某些昆虫或微生物如真菌、细菌或病毒)的抗性。其他具体特征涉及例如有关采收物的产量、品质、储存性、组成和具体成分。例如,存在已知的淀粉含量增加或淀粉品质改变的转基因植物,或采收物中具有不同脂肪酸组成的那些转基因植物。其他特定性质在于对非生物胁迫因素(例如热、冷、干旱、盐和紫外辐射)的耐受性或抗性。
优选将本发明的式(I)的化合物或其盐使用于经济上重要的有益植物和观赏植物的转基因作物中。式(I)的化合物可用作有用有益植物作物中的除草剂,所述作物对除草剂的植物毒性作用具有抗性,或通过基因改造已使其对除草剂的植物毒性作用具有抗性。
生产与现有植物相比具有改进的性质的新的植物的常规方法在于,例如,传统的栽培方法和突变体的产生。或者,可借助重组方法产生具有改变性质的新的植物(参见,例如EP 0221044、EP 0131624)。所描述的为,例如,为了改进植物中合成的淀粉而对作物植物进行遗传修饰的几种情况(例如WO 92/011376 A、WO 92/014827 A、WO 91/019806 A),对草铵膦(glufosinate)类(参见,例如,EP 0242236 A、EP 0242246 A)、草甘磷(glyphosate)类(WO 92/000377 A)、磺酰脲类(EP 0257993A、US 5,013,659)的特定除草剂或对通过“基因叠加(gene stacking)”对这些除草剂的组合或混合物具有抗性的转基因作物植物,例如商品名或名称为OptimumTM GATTM(草甘膦ALS耐受性)的转基因作物植物,例如玉米或大豆。
-能产生苏云金芽孢杆菌(Bacillus thuringiensis)毒素(Bt毒素)的转基因作物植物,例如棉花,其使得植物能抵抗特定的害虫(EP 0142924 A,EP 0193259 A),
-具有改进的脂肪酸组成的转基因作物植物(WO 91/013972 A),
-具有新的成分或次级代谢物——例如新的植物抗毒素,其使抗病能力增强——的基因修饰的作物植物(EP 0309862 A,EP 0464461 A),
-光呼吸作用降低的基因修饰植物,其具有更高的产量和更高的胁迫耐受性(EP0305398 A),
-产生制药上或诊断上重要的蛋白质的转基因作物植物(“分子制药(molecularpharming)”),
-以产量更高或品质更好为特征的转基因作物植物,
-以例如上述新性质的结合(“基因叠加”)为特征的转基因作物植物。
原则上,用于制备具有改进的性质的新转基因植物的大量分子生物学技术为已知的;参见,例如I.Potrykus和G.Spangenberg(eds),Gene Transfer to Plants,SpringerLab Manual(1995),Springer Verlag Berlin,Heidelberg或Christou,"Trends in PlantScience"1(1996)423-431)。
为了进行这种遗传操作,可将能够产生突变或通过重组DNA序列产生序列改变的核酸分子引入质粒。借助于标准方法,可以例如进行碱基交换、去除部分序列或加入天然的或合成的序列。为了将DNA片段彼此连接,可以向片段加入接头(adapter)或连接体(linker);参见例如,Sambrook et al.,1989,Molecular Cloning,A Laboratory Manual,2nd ed.,Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY;或Winnacker"Gene und Klone”[Genes and Clones],VCH Weinheim,2nd edition,1996。
例如,基因产物活性降低的植物细胞的产生可以通过下列方法实现:通过表达至少一种相应的反义RNA、用于实现共抑制作用的正义RNA,或者通过表达至少一种特异性切割上述基因产物的转录物的合适地构建的核酶。为此,首先可使用包含基因产物的全部编码序列(包括可能存在的任何侧翼序列)的DNA分子,以及仅包含一部分编码序列的DNA分子,在这种情况下,这些部分必须足够长以在细胞中产生反义作用。也可使用与基因产物的编码序列具有高度同源性但不完全与其相同的DNA序列。
当在植物中表达核酸分子时,所合成的蛋白质可被定位在植物细胞的任何所需的区室中。然而,为了实现在特定的区室中的定位,可以例如将编码区与在特定区室中确保定位的DNA序列相连接。这种序列是本领域技术人员已知的(参见例如Braun等人,EMBO J.11(1992),3219-3227;Wolter等人,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald等人,Plant J.1(1991),95-106)。核酸分子也可在植物细胞的细胞器中表达。
转基因植物细胞可通过已知的技术再生以长成完整的植物。原则上,所述转基因植物可为任何所需植物品种的植物,即不仅可为单子叶植物,也可为双子叶植物。性质改变的转基因植物可通过同源(=天然)基因或基因序列的过表达、阻遏或抑制而获得,或通过异源(=外来)基因或基因序列的表达而获得。
本发明的化合物(I)可优选用于转基因作物中,所述转基因作物对以下物质具有抗性:生长调节剂,例如2,4-D、麦草畏(dicamba);或抑制重要的植物酶(例如乙酰乳酸合成酶(ALS)、EPSP合成酶、谷氨酰胺合成酶(GS)或羟基苯丙酮酸双加氧酶(HPPD))的除草剂;或选自磺酰脲、草甘膦、草铵膦或苯甲酰基异噁唑以及类似的活性成分的除草剂;或这些活性成分的任何所需的结合物。
本发明的化合物可特别优选地用于对草甘膦和草铵膦、草甘膦和磺酰脲或咪唑啉酮的结合物具有抗性的转基因作物植物。最优选地,本发明的化合物可用于例如商品名或名称为OptimumTM GATTM(草甘膦ALS耐受性的)的转基因作物植物,例如玉米或大豆。
当将本发明的活性成分用于转基因作物时,不仅会对其他作物中观察到的有害植物产生影响,而且经常对施用于特定的转基因作物产生特异性影响,例如,改变的或特别地拓宽的可被防治的杂草的谱,改变的可用于施用的施用率,优选地与转基因作物对其有抗性的除草剂的良好的相容性,并对转基因作物植物的生长和产量产生影响。
因此,本发明还涉及本发明的式(I)的化合物作为除草剂用于防治转基因作物植物中的有害植物的用途。
本发明的化合物可以可湿性粉剂、乳油、可喷洒溶液剂、撒粉产品或颗粒剂的形式用在常规制剂中。因此,本发明还提供含有本发明的化合物的除草和植物生长调节组合物。
本发明的化合物可以各种方式根据其所需的生物学和/或物理化学参数进行配制。可能的制剂包括,例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、乳油(EC)、乳剂(EW)例如水包油乳剂和油包水乳剂、可喷洒溶液剂、悬浮浓缩剂(SC)、基于油或水的分散剂、油混溶性溶液剂、胶囊悬浮剂(CS)、撒粉产品(DP)、拌种剂、用于撒播和土壤施用的颗粒剂、微粒形式的颗粒剂(GR)、喷洒颗粒剂、吸收颗粒剂和吸附颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。这些单独的制剂类型原则上均为已知的,并记载于例如:Winnacker-Küchler,"Chemische Technologie”[Chemical Technology],第7章,C.Hanser Verlag,慕尼黑,第4版,1986,Wade van Valkenburg,"PesticideFormulations",Marcel Dekker,N.Y.,1973,K.Martens,"Spray Drying"Handbook,第3版,1979,G.Goodwin Ltd.,伦敦。
必要的制剂助剂,例如惰性材料、表面活性剂、溶剂和其他添加剂同样为已知的,并描述于例如:Watkins,"Handbook of Insecticide Dust Diluents and Carriers",第2版,Darland Books,Caldwell N.J.;H.v.Olphen,"Introduction to Clay Colloid Chemistry",第2版,J.Wiley&Sons,N.Y.;C.Marsden,"Solvents Guide",第2版,Interscience,N.Y.1963;McCutcheon's"Detergents and Emulsifiers Annual",MC Publ.Corp.,Ridgewood N.J.;Sisley and Wood,"Encyclopedia of Surface Active Agents",Chem.Publ.Co.Inc.,N.Y.1964; [Interface-activeEthylene Oxide Adducts],Wiss.Verlagsgesell.,Stuttgart 1976;Winnacker-Küchler,"Chemische Technologie",第7章,C.Hanser Verlag Munich,第4版,1986。
基于这些制剂,还可制备与其他活性成分(例如杀虫剂、杀螨剂、除草剂、杀菌剂以及与安全剂、肥料和/或生长调节剂)的结合物,例如呈成品制剂或桶混物形式。
可用于本发明化合物的以混合制剂或桶混物形式的结合配伍物质为,例如,基于抑制例如以下物质的已知活性成分:乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮酰莽草酸-3-磷酸合成酶、谷氨酰胺合成酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光系统I、光系统II或原卟啉原氧化酶,如从例如Weed Research 26(1986)441-445或“The Pesticide Manual”,第16版,The British Crop ProtectionCouncil and the Royal Soc.of Chemistry,2006中和其中引用的文献中已知。可与本发明化合物结合的已知除草剂或植物生长调节剂为例如以下活性物质,其中所述活性成分根据国际标准化组织(ISO)通过其“通用名称”或化学名称或代码编号来表示。其总是包括所有使用形式,例如酸、盐、酯和所有异构形式例如立体异构体和旋光异构体,即使其未被明确地提及。
这种除草混合配伍物质的实例为:
乙草胺(acetochlor)、三氟羧草醚(acifluorfen)、三氟羧草醚(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、枯杀达(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、环丙嘧啶酸钾(aminocyclopyrachlor-potassium)、环丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯氨吡啶酸(aminopyralid)、杀草强(amitrole)、氨基磺酸铵(ammonium sulfamate)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、草除灵(benazolin-ethyl)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron)、苄嘧磺隆(bensulfuron-methyl)、地散磷(bensulide)、灭草松(bentazone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟吡草酮(bicyclopyron)、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠盐(bilanafos-sodium)、双草醚(bispyribac)、双草醚钠盐(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、丁酰溴苯腈(bromoxynil-butyrate)、溴苯腈钾(bromoxynil-potassium)、庚酰溴苯腈(bromoxynil-heptanoate)和辛酰溴苯腈(bromoxynil-octanoate)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁苯草酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑酮草酯(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、草灭畏(chloramben)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、双氯酚酸钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯酞酰亚胺(chlorophthalim)、绿麦隆(chlorotoluron)、氯酞酸二甲酯(chlorthal-dimethyl)、氯磺隆(chlorsulfuron)、3-[5-氯-4-(三氟甲基)哌啶-2-基]-4-羟基-1-甲基咪唑啉-2-酮、吲哚酮草酯(cinidon)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、氯酰草膦(clacyfos)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、异噁草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环草敌(cycloate)、cyclopyranil、cyclopyrimorate、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、环草津(cyprazine)、2,4-D、2,4-D-丁氧基乙酯(2,4-D-butotyl)、2,4-D-丁酯(2,4-D-butyl)、2,4-D-二甲基铵(2,4-D-dimethylammonium)、2,4-D-二乙醇胺(2,4-D-diolamine)、2,4-D-乙酯(2,4-D-ethyl)、2-乙基己酯(2-ethylhexyl)、2,4-D-异丁酯、2,4-D-异辛酯、2,4-D-异丙基铵、2,4-D-钾、2,4-D-三异丙醇铵和2,4-D-三乙醇胺、2,4-DB、2,4-DB-丁酯、2,4-DB-二甲基铵、2,4-DB-异辛酯、2,4-DB-钾和2,4-DB-钠、杀草隆(daimuron(dymron))、茅草枯(dalapon)、棉隆(dazomet)、正癸醇、甜菜安(desmedipham)、detosyl-pyrazolate(DTP)、麦草畏、敌草腈(dichlobenil)、2-(2,4-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2-(2,5-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、禾草灵(diclofop)、禾草灵(diclofop-methyl)、diclofop-P-methyl、双氯磺草胺(diclosulam)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、氟吡草腙(diflufenzopyr-sodium)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、dimetrasulfuron、氨氟灵(dinitramine)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、敌草快(diquat)、敌草快(diquat-dibromid)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、茵多酸(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-9600、F-5231(即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙磺酰胺)、F-7967(即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、精噁唑禾草灵(fenoxaprop-P-ethyl)、fenoxasulfone、fenquinotrione、四唑酰草胺(fentrazamide)、麦草伏(flamprop)、高效麦草氟异丙酯(flamprop-M-isopropyl)、高效麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen)、氯氟吡啶酯(florpyrauxifen-benzyl)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、氟酮磺隆(flucarbazone)、氟酮磺隆钠(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氟草隆(fluometuron)、抑草丁(flurenol)、芴丁酯(flurenol-butyl)、flurenol-dimethylammonium和芴醇甲酯(flurenol-methyl)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、四氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron)、氟啶嘧磺隆(flupyrsulfuron-methyl-sodium)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、氯氟吡氧乙酸(fluroxypyr-meptyl)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺胺草醚钠(fomesafen-sodium)、甲酰氨磺隆(foramsulfuron)、杀木膦(fosamine)、草铵膦、草铵膦铵、精草铵膦钠(glufosinate-P-sodium)、精草铵膦铵、精草铵膦钠、草甘膦、草甘膦铵、草甘膦异丙基铵、草甘膦二铵、草甘膦二甲基铵、草甘膦钾、草甘膦钠和草硫膦(glyphosate-trimesium)、H-9201(即O-(2,4-二甲基-6-硝基苯基)O-乙基异丙基硫代磷酰胺酯(O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate))、氟氯吡啶酯(halauxifen)、氟氯吡啶酯(halauxifen-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氟吡禾灵乙氧基乙酯、精氟吡禾灵乙氧基乙酯、氟吡甲禾灵(haloxyfop-methyl)、高效氟吡甲禾灵(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02(即(2,4-二氯苯氧基)乙基1-(二甲氧基磷酰基)乙酯)、4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑啉-2-酮、4-羟基-1-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑啉2-酮、咪草酯(imazamethabenz)、咪草酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟铵、甲咪唑烟酸(imazapic)、甲咪唑烟酸铵、咪唑烟酸(imazapyr)、咪唑烟酸异丙铵、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸亚铵(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、碘甲磺隆(iodosulfuron)、碘甲磺隆(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、辛酰碘苯腈(ioxynil-octanoate)、碘苯腈钾和碘苯腈钠、三唑酰草胺(ipfencarbazone)、异丙隆(isoproturon)、异噁隆(isouron)、异噁酰草胺(isoxaben)、异噁唑草酮(isoxaflutole)、特胺灵(karbutilate)、KUH-043(即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-噁唑)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA-丁氧基乙酯、MCPA-二甲基铵、MCPA-2-乙基己酯、MCPA-异丙基铵、MCPA-钾和MCPA-钠、MCPB、MCPB-甲酯、MCPB-乙酯和MCPB-钠、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠和2-甲-4-氯丙酸丁氧基乙酯、精2-甲-4-氯丙酸(mecoprop-P)、精2-甲-4-氯丙酸丁氧基乙酯、精2-甲-4-氯丙酸二甲基铵、精2-甲-4-氯丙酸-2-乙基己酯和精2-甲-4-氯丙酸钾、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、甲基二磺隆(mesosulfuron)、甲基二磺隆(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、嗪吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、异硫氰酸甲酯(methyl isothiocyanate)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、精异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-ester)、MT-5950(即N-[3-氯-4-(1-甲基乙基)-苯基]-2-甲基戊酰胺)、NGGC-011、敌草胺(napropamide)、NC-310(即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、壬酸(pelargonic acid)、氟草敏(norflurazon)、油酸(脂肪酸)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefon)、氧三酮(oxotrione)(lancotrione)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat)、百草枯(paraquatdichloride)、克草猛(pebulate)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚(pentachlorophenol)、环戊噁草酮(pentoxazone)、烯草胺(pethoxamid)、矿油(petroleum oils)、甜菜宁(phenmedipham)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆(primisulfuron-methyl)、氨氟乐灵(prodiamine)、环苯草酮(profoxydim)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、噁草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠(propoxycarbazone-sodium)、丙嗪嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚(pyraflufen-ethyl)、磺酰草吡唑(pyrasulfotole)、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、pyribambenz、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、达草止(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚(pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、嘧草硫醚钠(pyrithiobac-sodium)、砜吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、磺草酮(sulcotrion)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249(即5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基酯)、SYP-300(即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫代咪唑烷-4,5-二酮)、2,3,6-TBA、TCA(三氟乙酸)、TCA-钠、丁噻隆(tebuthiuron)、呋喃磺草酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁通(terbumeton)、特丁津(terbuthylazin)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、噻唑烟酸(thiazopyr)、噻酮磺隆(thiencarbazone)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、禾草丹(thiobencarb)、tiafenacil、tolpyralate、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、triafamone、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、苯磺隆(tribenuron-methyl)、三氯吡氧乙酸(triclopyr)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠(trifloxysulfuron-sodium)、trifludimoxazin、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、硫酸脲、灭草敌(vernolate)、ZJ-0862(即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苄基}苯胺),以及以下化合物:
作为可能的混合配伍物的植物生长调节剂的实例为:
苯并噻二唑(acibenzolar)、苯并噻二唑(acibenzolar-S-methyl)、氨基酮戊酸(5-aminolevulinic acid)、环丙嘧啶醇(ancymidol)、6-苄基氨基嘌呤、芸苔素内酯(brassinolide)、邻苯二酚(catechol)、矮壮素(chlormequat chloride)、调果酸(cloprop)、环丙酸酰胺(cyclanilide)、3-(环丙-1-烯基)丙酸、丁酰肼(daminozide)、棉隆(dazomet)、正癸醇、敌草克(dikegulac)、敌草克钠(dikegulac-sodium)、茵多酸(endothal)、茵多酸二钾(endothal-dipotassium)、茵多酸二钠(endothal-disodium),和单(N,N-二甲基烷基铵)、乙烯利(ethephon)、氟节胺(flumetralin)、抑草丁(flurenol)、芴丁酯(fiurenol-butyl)、呋嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤霉酸(gibberellic acid)、抗倒胺(inabenfide)、吲哚-3-乙酸(IAA)、4-吲哚-3-基丁酸、稻瘟灵(isoprothiolane)、烯丙苯噻唑(probenazole)、茉莉酸(jasmonic acid)、茉莉酸甲酯、马来酰肼、助壮素(mepiquat chloride)、1-甲基环丙烯、2-(1-萘基)乙酰胺、1-萘乙酸、2-萘氧基乙酸、硝基酚盐混合物(nitrophenolate mixture)、4-氧代-4[(2-苯乙基)氨基]丁酸、多效唑(paclobutrazole)、N-苯基邻苯二甲酸、调环酸(prohexadione)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmone)、水杨酸、独角金内酯(strigolactone)、四氧硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac)、抗倒酯(trinexapac-ethyl)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)。
可与本发明的式(I)的化合物结合使用以及任选地与其他活性成分(例如上述的杀虫剂、杀螨剂、除草剂、杀菌剂)结合使用的安全剂,优选地选自:
S1)式(S1)的化合物,
其中符号和角标具有以下含义:
nA为0至5、优选0至3的自然数;
RA 1为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
WA为未被取代或被取代的二价杂环基团,所述二价杂环基团选自具有1至3个选自N和O的环杂原子的部分不饱和或芳香五元杂环,其中至少一个氮原子和至多一个氧原子存在于环中,优选地所述基团选自(WA 1)至(WA 4),
mA为0或1;
RA 2为ORA 3、SRA 3或NRA 3RA 4,或具有至少一个氮原子和至多3个杂原子(优选地选自O和S)的饱和或不饱和3-至7-元杂环,其通过氮原子与(S1)中的羰基基团连接,并且为未被取代的或被选自(C1-C4)-烷基、(C1-C4)-烷氧基或任选取代的苯基所取代,优选地式ORA 3、NHRA 4或N(CH3)2,特别是式ORA 3的基团;
RA 3为氢或未被取代的或被取代的脂族烃基团,优选地具有总共1至18个碳原子;
RA 4为氢、(C1-C6)-烷基、(C1-C6)-烷氧基或被取代的或未被取代的苯基;
RA 5为H、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C8)-烷基、氰基或COORA 9,其中RA 9为氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C6)-羟烷基、(C3-C12)-环烷基或三-(C1-C4)-烷基硅烷基;
RA 6、RA 7、RA 8为相同的或不同的,且为氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C3-C12)-环烷基或被取代的或未被取代的苯基;
优选地:
a)二氯苯基吡唑啉-3-羧酸型的化合物(S1a),优选化合物例如1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-羧酸、1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-羧酸乙酯(S1-1)(“吡唑解草酯(mefenpyr-diethyl)”),以及如在WO-A-91/07874中记载的相关化合物;
b)二氯苯基吡唑羧酸的衍生物(S1b),优选化合物例如1-(2,4-二氯苯基)-5-甲基吡唑-3-羧酸乙酯(S1-2)、1-(2,4-二氯苯基)-5-异丙基吡唑-3-羧酸乙酯(S1-3)、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)吡唑-3-羧酸乙酯(S1-4),以及如在EP-A-333131和EP-A-269806中记载的相关化合物;
c)1,5-二苯基吡唑-3-羧酸的衍生物(S1c),优选化合物例如1-(2,4-二氯苯基)-5-苯基吡唑-3-羧酸乙酯(S1-5)、1-(2-氯苯基)-5-苯基吡唑-3-羧酸甲酯(S1-6),以及如在例如EP-A-268554中记载的相关化合物;
d)三唑羧酸型的化合物(S1d),优选化合物例如解草唑(fenchlorazole)(-乙酯),即1-(2,4-二氯苯基)-5-三氯甲基-(1H)-1,2,4-三唑-3-羧酸乙酯(S1-7),以及如在EP-A-174562和EP-A-346620中记载的相关化合物;
e)5-苄基-2-异噁唑啉-3-羧酸或5-苯基-2-异噁唑啉-3-羧酸或5,5-二苯基-2-异噁唑啉-3-羧酸型的化合物(S1e),优选化合物例如5-(2,4-二氯苄基)-2-异噁唑啉-3-羧酸乙酯(S1-8)或5-苯基-2-异噁唑啉-3-羧酸乙酯(S1-9),以及如在WO-A-91/08202中记载的相关化合物,或5,5-二苯基-2-异噁唑啉-3-羧酸(S1-10)或5,5-二苯基-2-异噁唑啉-3-羧酸乙酯(S1-11)(“双苯噁唑酸(isoxadifen-ethyl)”)或5,5-二苯基-2-异噁唑啉-3-羧酸正丙酯(S1-12)或5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-羧酸乙酯(S1-13),如专利申请WO-A-95/07897中所记载的。
S2)式(S2)的喹啉衍生物
其中符号和角标具有以下含义:
RB 1为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
nB为0至5、优选地0至3的自然数;
RB 2为ORB 3、SRB 3或NRB 3RB 4或具有至少一个氮原子和至多3个杂原子(优选地选自O和S)的饱和或不饱和3-至7-元杂环,其通过氮原子与(S2)中的羰基基团连接,并且其为未被取代的或被选自(C1-C4)-烷基、(C1-C4)-烷氧基或任选取代的苯基的基团所取代,优选地式ORB 3、NHRB 4或N(CH3)2,特别是式ORB 3的基团;
RB 3为氢或未被取代的或被取代的脂族烃基团,优选地具有总共1至18个碳原子;
RB 4为氢、(C1-C6)-烷基、(C1-C6)-烷氧基或被取代的或未被取代的苯基;
TB为未被取代的或被一个或两个(C1-C4)-烷基基团或被[(C1-C3)-烷氧基]羰基所取代的(C1或C2)-烷二基链;
优选地:
a)8-喹啉氧基乙酸型的化合物(S2a),优选地
(5-氯-8-喹啉氧基)乙酸1-甲基己酯(“解毒喹(cloquintocet-mexyl)”)(S2-1)、
(5-氯-8-喹啉氧基)乙酸1,3-二甲基丁-1-基酯(S2-2)、
(5-氯-8-喹啉氧基)乙酸4-烯丙氧基丁酯(S2-3)、
(5-氯-8-喹啉氧基)乙酸1-烯丙氧基丙-2-基酯(S2-4)、
(5-氯-8-喹啉氧基)乙酸乙酯(S2-5)、
(5-氯-8-喹啉氧基)乙酸甲酯(S2-6)、
(5-氯-8-喹啉氧基)乙酸烯丙酯(S2-7)、
(5-氯-8-喹啉氧基)乙酸2-(2-亚丙基亚氨氧基)-1-乙酯(S2-8)、(5-氯-8-喹啉氧基)乙酸2-氧代丙-1-基酯(S2-9),以及如EP-A-86750、EP-A-94349和EP-A-191736或EP-A-0492 366中记载的相关化合物,以及(5-氯-8-喹啉氧基)乙酸(S2-10)、其水合物和盐,例如其锂盐、钠盐、钾盐、钙盐、镁盐、铝盐、铁盐、铵盐、季铵盐、锍盐或鏻盐,如WO-A-2002/34048中所记载;
b)(5-氯-8-喹啉氧基)丙二酸型的化合物(S2b),优选化合物例如(5-氯-8-喹啉氧基)丙二酸二乙酯、(5-氯-8-喹啉氧基)丙二酸二烯丙酯、(5-氯-8-喹啉氧基)丙二酸甲基乙酯,以及如EP-A-0 582 198中记载的相关化合物。
S3)式(S3)的化合物
其中符号和角标的定义如下:
RC 1为(C1-C4)-烷基、(C1-C4)-卤代烷基、(C2-C4)-烯基、(C2-C4)-卤代烯基、(C3-C7)-环烷基,优选地二氯甲基;
RC 2、RC 3为相同的或不同的,并且为氢、(C1-C4)烷基、(C2-C4)烯基、(C2-C4)炔基、(C1-C4)卤代烷基、(C2-C4)卤代烯基、(C1-C4)烷基氨基甲酰基-(C1-C4)烷基、(C2-C4)烯基氨基甲酰基-(C1-C4)烷基、(C1-C4)烷氧基-(C1-C4)烷基、二氧杂环戊基-(C1-C4)烷基、噻唑基、呋喃基、呋喃基烷基、噻吩基、哌啶基、被取代的或未被取代的苯基、或RC 2和RC 3一起形成被取代的或未被取代的杂环,优选地噁唑烷、噻唑烷、哌啶、吗啉、六氢嘧啶或苯并噁嗪环;
优选地:
二氯乙酰胺型的活性成分,其通常被用作苗前安全剂(作用于土壤的安全剂),例如
“烯丙酰草胺(dichlormid)”(N,N-二烯丙基-2,2-二氯乙酰胺)(S3-1)、
来自Stauffer的“R-29148”(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)(S3-2)、
来自Stauffer的“R-28725”(3-二氯乙酰基-2,2-二甲基-1,3-噁唑烷)(S3-3)、
“解草嗪(benoxacor)”(4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪)(S3-4)、
来自PPG Industries的“PPG-1292”(N-烯丙基-N-[(1,3-二氧杂环戊-2-基)甲基]二氯乙酰胺)(S3-5)、
来自Sagro-Chem的“DKA-24”(N-烯丙基-N-[(烯丙基氨基羰基)甲基]二氯乙酰胺)(S3-6)、
来自Nitrokemia或Monsanto的“AD-67”或“MON 4660”(3-二氯乙酰基-1-氧杂-3-氮杂螺[4.5]癸烷)(S3-7)、
来自TRI-Chemical RT的“TI-35”(1-二氯乙酰基氮杂环庚烷)(S3-8)、
来自BASF的“diclonon”(dicyclonon)或“BAS145138”或“LAB145138”(S3-9)((RS)-1-二氯乙酰基-3,3,8a-三甲基全氢吡咯并[1,2-a]嘧啶-6-酮)、
“解草噁唑(furilazole)”或“MON 13900”((RS)-3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷)(S3-10),及其(R)异构体(S3-11)。
S4)式(S4)的N-酰基磺酰胺及其盐,
其中符号和角标定义如下:
AD为SO2-NRD 3-CO或CO-NRD 3-SO2
XD为CH或N;
RD 1为CO-NRD 5RD 6或NHCO-RD 7;
RD 2为卤素、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、硝基、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
RD 3为氢、(C1-C4)-烷基、(C2-C4)-烯基或(C2-C4)-炔基;
RD 4为卤素、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷基、苯基、(C1-C4)-烷氧基、氰基、(C1-C4)-烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
RD 5为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C5-C6)-环烯基、苯基或包含选自氮、氧和硫的vD杂原子的3-至6-元杂环基,其中最后七个基团被选自以下的vD取代基所取代:卤素、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C2)-烷基亚磺酰基、(C1-C2)-烷基磺酰基、(C3-C6)-环烷基、(C1-C4)-烷氧羰基、(C1-C4)-烷基羰基和苯基以及在环状基团的情况下,还包括(C1-C4)-烷基和(C1-C4)-卤代烷基;
RD 6为氢、(C1-C6)-烷基、(C2-C6)-烯基或(C2-C6)-炔基,其中最后三个基团被选自卤素、羟基、(C1-C4)-烷基、(C1-C4)-烷氧基和(C1-C4)-烷硫基的vD基团所取代,或
RD 5和RD 6与携带它们的氮原子一起形成吡咯烷基或哌啶基基团;
RD 7为氢、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、(C1-C6)-烷基、(C3-C6)-环烷基,其中最后两个基团被选自以下的vD取代基所取代:卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基,在环状基团的情况下,还包括(C1-C4)-烷基和(C1-C4)-卤代烷基;
nD为0、1或2;
mD为1或2;
vD为0、1、2或3;
其中,优选例如下面式(S4a)的N-酰基磺酰胺型的化合物,其例如从WO-A-97/45016中已知
其中
RD 7为(C1-C6)-烷基、(C3-C6)-环烷基,其中最后2个基团被选自以下的vD取代基所取代:卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基,在环状基团的情况下,还包括(C1-C4)-烷基和(C1-C4)-卤代烷基;
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD为1或2;
vD为0、1、2或3;
以及例如下面的式(S4b)的酰基氨磺酰基苯甲酰胺的化合物,其例如从WO-A-99/16744中已知,
例如那些化合物,其中
RD 5=环丙基和(RD 4)=2-OMe(“环丙磺酰胺(cyprosulfamide)”,S4-1),
RD 5=环丙基和(RD 4)=5-Cl-2-OMe(S4-2),
RD 5=乙基和(RD 4)=2-OMe(S4-3),
RD 5=异丙基和(RD 4)=5-Cl-2-OMe(S4-4)和
RD 5=异丙基和(RD 4)=2-OMe(S4-5)
以及
式(S4c)的N-酰基氨磺酰基苯基脲型的化合物,其例如从EP-A-365484中已知,
其中
RD 8和RD 9独立地为氢、(C1-C8)-烷基、(C3-C8)-环烷基、(C3-C6)-烯基、(C3-C6)-炔基,
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3,
mD为1或2;
例如
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲(“metcamifen”,S4-6),
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲,
1-[4-(N-4,5-二甲基苯甲酰氨磺酰基)苯基]-3-甲基脲,
以及
式(S4d)的N-苯基磺酰基对苯二甲酰胺,例如从CN 101838227中已知,
例如那些化合物,其中
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD为1或2;
RD 5为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C5-C6)-环烯基。
S5)来自羟基芳族化合物类和芳族脂族羧酸衍生物类的活性成分(S5),例如
3,4,5-三乙酰氧基苯甲酸乙酯、3,5-二甲氧基-4-羟基苯甲酸、3,5-二羟基苯甲酸、4-羟基水杨酸、4-氟水杨酸、2-羟基肉桂酸、2,4-二氯肉桂酸,如WO-A-2004/084631、WO-A-2005/015994、WO-A-2005/016001中所记载。
S6)来自1,2-二氢喹喔啉-2-酮类的活性成分(S6),例如
1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮、1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-硫酮、1-(2-氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮盐酸盐、1-(2-甲基磺酰基氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮,如WO-A-2005/112630中所记载。
S7)式(S7)的化合物,如WO-A-1998/38856中所记载,
其中符号和角标定义如下:
RE 1、RE 2独立地为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷基、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、硝基;
AE为COORE 3或COSRE 4
RE 3、RE 4独立地为氢、(C1-C4)-烷基、(C2-C6)-烯基、(C2-C4)-炔基、氰基烷基、(C1-C4)-卤代烷基、苯基、硝基苯基、苄基、卤代苄基、吡啶基烷基和烷基铵,
nE 1为0或1
nE 2、nE 3独立地为0、1或2,
优选地:
二苯基甲氧基乙酸,
二苯基甲氧基乙酸乙酯,
二苯基甲氧基乙酸甲酯(CAS登记号41858-19-9)(S7-1)。
S8)式(S8)的化合物,如WO-A-98/27049中所记载,
其中
XF为CH或N,
nF如果XF=N,则为0至4的整数和
如果XF=CH,则为0至5的整数,
RF 1为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、硝基、(C1-C4)-烷硫基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基,任选地被取代的苯基,任选地被取代的苯氧基,
RF 2为氢或(C1-C4)-烷基,
RF 3为氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述各含碳基团为未被取代的或被一个或多个取代、优选最高达三个相同或不同的选自卤素和烷氧基的基团取代;或其盐,
优选地化合物,其中
XF为CH,
nF为0至2的整数,
RF 1为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基,
RF 2为氢或(C1-C4)-烷基,
RF 3为氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述各含碳基团为未被取代的或被一个或多个、优选地最高达三个相同或不同的选自卤素和烷氧基的基团取代,
或其盐。
S9)来自3-(5-四唑基羰基)-2-喹诺酮类的活性成分(S9),例如
1,2-二氢-4-羟基-1-乙基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号219479-18-2)、1,2-二氢-4-羟基-1-甲基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号95855-00-8),如WO-A-1999/000020中所记载。
S10)式(S10a)或(S10b)的化合物
如WO-A-2007/023719和WO-A-2007/023764中所记载
其中
RG 1为卤素、(C1-C4)-烷基、甲氧基、硝基、氰基、CF3、OCF3,YG、
ZG彼此独立地代表O或S,
nG为0至4的整数,
RG 2为(C1-C16)-烷基、(C2-C6)-烯基、(C3-C6)-环烷基、芳基、苄基、卤代苄基,
RG 3为氢或(C1-C6)-烷基。
S11)氧基亚氨基化合物型的活性成分(S11),其已知为拌种剂,例如
“解草腈(oxabetrinil)”((Z)-1,3-二氧杂环戊-2-基甲氧基亚氨基(苯基)乙腈)(S11-1),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂,
“氟草肟(fluxofenim)”(1-(4-氯苯基)-2,2,2-三氟-1-乙酮O-(1,3-二氧杂环戊-2-基甲基)肟)(S11-2),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂,和
“解草胺腈(cyometrinil)”或“CGA-43089”((Z)-氰基甲氧基亚氨基(苯基)乙腈)(S11-3),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂。
S12)来自异硫代苯并二氢吡喃类(isothiochromanones)的活性成分(S12),例如[(3-氧代-1H-2-苯并噻喃-4(3H)-亚基)甲氧基]乙酸甲酯(CAS登记号205121-04-6)(S12-1)以及来自WO-A-1998/13361的相关化合物。
S13)来自组(S13)的一种或多种化合物:
“萘二甲酸酐”(1,8-萘二甲酸酐)(S13-1),其已知作为拌种安全剂在玉米中用于抵抗硫代氨基甲酸酯除草剂的损害,
“解草啶(fenclorim)”(4,6-二氯-2-苯基嘧啶)(S13-2),其已知作为在播种的稻中用于丙草胺的安全剂,
“解草胺(flurazole)”(2-氯-4-三氟甲基-1,3-噻唑-5-甲酸苄酯)(S13-3),其已知作为拌种安全剂在黍/高粱中用于抵抗甲草胺和异丙甲草胺的损害,
来自American cyanamid的“CL 304415”(CAS登记号31541-57-8)(4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸)(S13-4),其已知作为安全剂在玉米中用于抵抗咪唑啉酮的损害,
来自Nitrokemia的“MG 191”(CAS登记号96420-72-3)(2-二氯甲基-2-甲基-1,3-二氧戊环)(S13-5),其已知在玉米中用作安全剂,
来自Nitrokemia的“MG 838”(CAS登记号133993-74-5)(1-氧杂-4-氮杂螺[4.5]癸烷-4-二硫代甲酸2-丙烯酯)(S13-6),
“乙拌磷(disulfoton)”(O,O-二乙基S-2-乙硫基乙基二硫代磷酸酯)(S13-7),
“增效磷(dietholate)”(O,O-二乙基O-苯基硫代磷酸酯)(S13-8),
“mephenate”(甲基氨基甲酸4-氯苯基酯)(S13-9)。
S14)除对有害植物具有除草作用外,还对作物植物如稻具有安全剂作用的活性成分,例如
“哌草丹(dimepiperate)”或“MY-93”(1-苯基乙基哌啶-1-硫代甲酸S-1-甲酯),其已知作为安全剂在稻中用于抵抗除草剂禾草敌的损害,
“杀草隆(daimuron)”或“SK 23”(1-(1-甲基-1-苯基乙基)-3-对甲苯基脲),其已知作为安全剂在稻中用于抵抗除草剂唑吡嘧磺隆的损害,
“苄草隆(cumyluron)”=“JC-940”(3-(2-氯苯基甲基)-1-(1-甲基-1-苯乙基)脲,参见JP-A-60087270),其已知作为安全剂在稻中用于抵抗一些除草剂的损害,
“苯草酮(methoxyphenone)”或“NK 049”(3,3'-二甲基-4-甲氧基二苯甲酮),其已知作为安全剂在稻中用于抵抗一些除草剂的损害,
来自Kumiai的“CSB”(1-溴-4-(氯甲基磺酰基)苯)(CAS登记号54091-06-4),其已知作为安全剂在稻中用于抵抗一些除草剂的损害。
S15)式(S15)的化合物或其互变异构体
如WO-A-2007/131861和WO-A-2008/131860中所记载
其中,
RH 1为(C1-C6)-卤代烷基基团,和
RH 2为氢或卤素,和
RH 3、RH 4独立地为氢、(C1-C16)-烷基、(C2-C16)-烯基或(C2-C16)-炔基,
其中最后3个基团各自为未被取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)-卤代烷氧基]羰基、未被取代的或被取代的(C3-C6)-环烷基、未被取代的或被取代的苯基、和未被取代的或被取代的杂环基,
或(C3-C6)-环烷基、(C4-C6)-环烯基、在环的一侧稠合至4元至6元饱和或不饱和碳环的(C3-C6)-环烷基,在环的一侧稠合至4元至6元饱和或不饱和碳环的(C4-C6)-环烯基,
其中最后4个基团各自为未被取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)-卤代烷氧基]羰基、未被取代的或被取代的(C3-C6)环烷基、未被取代的或被取代的苯基、和未被取代的或被取代的杂环基,
或
RH 3为(C1-C4)-烷氧基、(C2-C4)-烯氧基、(C2-C6)-炔氧基或(C2-C4)-卤代烷氧基,和
RH 4为氢或(C1-C4)-烷基,或
RH 3和RH 4与直接连接的氮原子一起代表四元至八元杂环,所述杂环除氮原子外,还可包含其他环杂原子,优选最高达两个选自N、O和S的其他环杂原子,并且所述杂环为未被取代的或被一个或多个选自以下的基团取代:卤素、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基和(C1-C4)-烷硫基。
S16)主要用作除草剂但对作物植物具有安全剂作用的活性化合物,例如
(2,4-二氯苯氧基)乙酸(2,4-D)、
(4-氯苯氧基)乙酸、
(R,S)-2-(4-氯-邻甲苯氧基)丙酸(mecoprop)、
4-(2,4-二氯苯氧基)丁酸(2,4-DB)、
(4-氯-邻甲苯氧基)乙酸(MCPA)、
4-(4-氯-邻甲苯氧基)丁酸、
4-(4-氯苯氧基)丁酸、
3,6-二氯-2-甲氧基苯甲酸(麦草畏)、
3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor-ethyl)。
特别优选的安全剂为吡唑解草酯(mefenpyr-diethyl)、环丙磺酰胺(cyprosulfamide)、双苯噁唑酸(isoxadifen-ethyl)、解毒喹(cloquintocet-mexyl)、解草嗪(benoxacor)、烯丙酰草胺(dichlormid)和metcamifen。
可湿性粉剂为可在水中均匀分散的制剂,其除活性成分之外以及除稀释剂或惰性物质之外,还包含离子和/或非离子类型的表面活性剂(润湿剂、分散剂),例如聚乙氧基化烷基酚类、聚乙氧基化脂肪醇类、聚乙氧基化脂肪胺类、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木质素磺酸钠、2,2'-二萘基甲烷-6,6'-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为制备所述可湿性粉剂,在例如常规设备如锤式研磨机、鼓风式研磨机和喷气式研磨机中细磨活性除草成分,并同时或随后与制剂助剂混合。
乳油通过将活性成分溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或相对高沸点的芳族化合物或烃类)或有机溶剂的混合物中,并添加一种或多种离子和/或非离子表面活性剂(乳化剂)制备。可使用的乳化剂的实例为:烷基芳基磺酸钙,例如十二烷基苯磺酸钙,或非离子乳化剂如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷缩合产物、烷基聚醚、脱水山梨糖醇酯如脱水山梨糖醇脂肪酸酯或聚氧乙烯脱水山梨糖醇酯如聚氧乙烯脱水山梨糖醇脂肪酸酯。
撒粉产品通过将活性成分与细分散的固体一起研磨获得,所述细分散的固体例如滑石、天然粘土(如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮浓缩剂可为水基或油基的。其可借助市售珠磨机并任选添加例如已在上文针对其他制剂类型所列的表面活性剂通过例如湿式研磨法制备。
乳剂,例如水包油乳剂(EW),可使用水性有机溶剂和任选地已在上文例如针对其他制剂型所列的表面活性剂,借助例如搅拌器、胶体磨机和/或静态混合器制备。
颗粒剂可通过将活性成分喷洒至能够吸附的颗粒状惰性材料上制备或借助胶黏剂(例如聚乙烯醇、聚丙烯酸钠或矿物油)将活性成分浓缩物施用于载体物质(例如砂、高岭石或颗粒状惰性材料)的表面上制备。还可将合适的活性化合物以常规用于制备肥料颗粒的方式——如果需要与肥料相混合——成粒。
水分散性颗粒剂通常通过常规方法如喷雾干燥法、流化床造粒法、盘式造粒法、用高速混合器混合且在无固体惰性材料的情况下挤出而制备。
对于盘式颗粒、流化床颗粒、挤出颗粒和喷雾颗粒的制备,参见例如在“SprayDrying Handbook”第三版,1979,G.Goodwin Ltd.,London;J.E.Browning,“Agglomeration”,Chemical and Engineering 1967,第147页及后文;“Perry's ChemicalEngineer's Handbook”,第五版,McGraw Hill,New York 1973,第8-57页中的方法。
有关作物保护组合物制剂的其他详细信息,参见例如G.C.Klingman,“WeedControl as a Science”,John Wiley and Sons,Inc.,New York,1961,第81-96页和J.D.Freyer,S.A.Evans,“Weed Control Handbook”,第五版,Blackwell ScientificPublications,Oxford,1968,第101-103页。
农用化学制剂通常包含0.1重量%至99重量%,尤其是0.1重量%至95重量%的本发明化合物。在可湿性粉剂中,活性成分浓度为例如约10重量%至90重量%,补足至100重量%的余量由常规制剂成分组成。在乳油中,活性成分的浓度可为约1重量%至90重量%且优选地5重量%至80重量%。粉剂形式的制剂包含1重量%至30重量%的活性成分、优选地通常5重量%至20重量%的活性成分;可喷雾溶液剂包含约0.05重量%至80重量%、优选地2重量%至50重量%的活性成分。在水分散性颗粒剂的情况下,活性成分含量部分地取决于活性成分是液体形式还是固体形式,以及所使用的造粒助剂、填充剂等。在水分散性颗粒剂中,活性成分的含量例如为1至95重量%、优选10至80重量%。
此外,所提及的活性成分制剂任选地包含各种常规的粘着剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、防冻剂和溶剂、填充剂、载体和染料、消泡剂、蒸发抑制剂和影响pH和粘度的试剂。
基于这些制剂,还可以制备与其他农药活性物质(例如杀虫剂、杀螨剂、除草剂、杀菌剂)的结合物,以及与安全剂、肥料和/或生长调节剂的结合物,比如以成品制剂或桶混物的形式。
为进行施用,如果合适,以常规方式稀释市售形式的制剂,例如在可湿性粉剂、乳油、分散剂和水分散性颗粒剂的情况下用水稀释。粉剂型制剂、用于土壤施用的颗粒剂或撒播用颗粒剂和可喷雾溶液剂通常在施用前不用其他惰性物质进一步稀释。
式(I)的化合物及其盐的所需施用率根据外部条件(例如尤其是温度、湿度和使用的除草剂类型)变化。它可在宽范围内变化,例如活性物质的量为0.001到10.0kg/ha或更多,但它优选地为0.005到5kg/ha,更优选地为0.01到1.5kg/ha,更优选地为0.05到1kg/ha。这既适用于出苗前施用,也适用于苗后施用。
载体为一种天然的或合成的、有机或无机物质,将活性成分与其混合或组合以获得更好的施用性,特别是施用于植物或植物部位或种子。可为固体或液体的载体通常是惰性的,并且应合适在农业中使用。有用的固体或液体载体包括:例如铵盐和天然岩石粉,例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土,以及合成岩石粉,如细碎的二氧化硅、氧化铝和天然或合成硅酸盐、树脂、蜡、固体肥料、水、醇类,尤其是丁醇、有机溶剂、矿物油、植物油及其衍生物。同样也可使用这种载体的混合物。颗粒剂的有用的固体载体包括:例如,粉碎的和分馏的天然岩石,如方解石、大理石、浮石、海泡石、白云石,以及无机和有机谷类的合成颗粒,以及有机材料如锯屑、椰子壳、玉米棒轴和烟秆的颗粒。
合适的液化气体填充剂或载体是在标准温度和大气压力下为气态的液体,例如气溶胶喷射剂,例如卤代烃,或丁烷、丙烷、氮气和二氧化碳。
在制剂中,可以使用增粘剂,例如羧甲基纤维素、粉末、颗粒或胶乳形式的天然和合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,或天然磷脂,例如脑磷脂和卵磷脂,以及合成磷脂。其他添加剂可为矿物油和植物油。
当使用的填充剂为水时,也可以使用例如有机溶剂作为助溶剂。有用的液体溶剂基本上为:芳族化合物例如二甲苯、甲苯或烷基萘,氯化芳族化合物或氯化脂族烃例如氯苯、氯乙烯、二氯甲烷,脂族烃例如环己烷或石蜡,例如矿物油馏分、矿物油和植物油,醇类例如丁醇或乙二醇以及其醚类和酯类,酮类,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
本发明的组合物可另外地包含其他组分,例如表面活性剂。有用的表面活性剂为具有离子或非离子性质的乳化剂和/或泡沫形成剂、分散剂或润湿剂,或这些表面活性剂的混合物。其实例为聚丙烯酸盐、木质素磺酸盐、酚磺酸盐或萘磺酸盐、环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺的缩聚物、取代酚(优选地烷基酚或芳基酚)、磺基琥珀酸酯的盐、牛磺酸衍生物(优选地烷基牛磺酸酯)、聚乙氧基化醇或聚乙氧基化酚的磷酸酯、多元醇的脂肪酸酯以及含有硫酸根、磺酸根和磷酸根的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐、蛋白质水解物、木质素亚硫酸盐废液和甲基纤维素。如果其中一种活性成分和/或其中一种惰性载体不溶于水,并且在水中进行施用时,则必须存在表面活性剂。表面活性剂的比例为本发明组合物的5至40重量%。可以使用染料例如无机颜料例如氧化铁、氧化钛和普鲁士蓝,以及有机染料例如茜素染料、偶氮染料和金属酞菁染料,以及微量营养物例如铁、锰、硼、铜、钴、钼和锌的盐。
如果合适,还可存在其他另外的组分,例如保护胶体、粘结剂、胶粘剂、增稠剂、触变性物质、渗透剂、稳定剂、螯合剂、络合剂。一般来说,活性成分可与通常用于制剂目的的任何固体或液体添加剂结合。一般而言,本发明的组合物和制剂含有的活性成分为0.05重量%至99重量%、0.01重量%至98重量%、优选地0.1重量%至95重量%、更优选地0.5重量%到90重量%、最优选地10重量%至70重量%。可使用本发明的活性成分或组合物本身,或根据其各自的物理和/或化学性质,使用其制剂或由其制备的使用形式,例如气雾剂、胶囊悬浮剂、冷雾浓缩剂、温雾浓缩剂、胶囊颗粒剂、细颗粒剂、用于种子处理的可流动浓缩剂、即用型溶液剂、可除尘粉末剂、乳油、水包油乳剂、油包水乳剂、大颗粒剂、微颗粒剂、油分散性粉末剂、油混溶性流动浓缩剂、油混溶性液体剂、泡沫、糊剂、农药包衣种子、悬浮浓缩剂、悬乳浓缩剂、可溶性浓缩剂、悬浮剂、可喷雾粉末剂、可溶性粉末剂、粉剂和颗粒剂、水溶性颗粒剂或片剂、用于种子处理的水溶性粉末剂、可湿性粉末剂、浸渍有活性成分的天然产物和合成物质,以及聚合物质和种子包衣材料中的微胶囊剂,以及ULV冷雾和温雾制剂。
所提及的制剂可以本身已知的方式制备,例如通过将活性成分与至少一种常用的填充剂、溶剂或稀释剂、乳化剂、分散剂和/或粘结剂或固定剂、润湿剂、防水剂、任选地干燥剂和UV稳定剂以及任选地染料和颜料、消泡剂、防腐剂、二次增稠剂、增粘剂、赤霉素和其他加工助剂混合而制备。
本发明的组合物不仅包括已准备好使用并可用合适的设备施用至植物或种子上的制剂,还包括必须在使用前用水稀释的市售浓缩剂。
本发明的活性成分可以其本身或其(市售标准)制剂存在,或以由这些制剂作为与其他(已知)活性成分(例如杀虫剂、引诱剂、消毒剂、杀菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂、除草剂、肥料、安全剂或化学信息素)的混合物所制备的使用形式存在。
本发明用活性成分或组合物对植物和植物部位的处理通过常规处理方法直接实现或通过作用于其周围环境、栖息地或储存空间来实现,例如通过浸渍、喷雾、雾化(atomizing)、灌溉、蒸发、撒粉、雾化(fogging)、撒播、发泡、涂抹(painting)、撒布(spreading-on)、浇水(浇灌(drenching))、滴灌,并且在繁殖材料的情况下,特别是在种子的情况下,还可通过干种子处理、湿种子处理、浆料处理、结壳,用一层或多层包衣包覆等。也可通过超低容量法施用活性成分或将活性成分制剂或活性成分本身注入土壤中。
本发明的优点之一是本发明的活性成分和组合物的特定内吸性质意味着用这些活性成分和组合物处理种子不仅保护种子本身,而且保护出苗后得到的植物免受植物病原真菌的损害。这样,可省去播种时或播种后不久对作物的直接处理。
同样认为有利的是,本发明的活性成分或组合物也可特别用于转基因种子,在这种情况下,从该种子生长的植物能够表达对抗害虫的蛋白质。仅通过蛋白质(例如杀虫蛋白质)的表达,用本发明的活性成分或组合物处理此类种子可导致对某些害虫的防治。出人意料的是,在这种情况下可观察到进一步的协同效应,这另外增加了防止害虫侵袭的有效性。
本发明的组合物适用于保护在农业、温室、森林或园艺和葡萄栽培中使用的任何植物品种的种子。特别地,该种子为谷物类(例如小麦、大麦、黑麦、黑小麦、高粱/黍和燕麦)、玉米、棉花、大豆、水稻、土豆、向日葵、菜豆、咖啡、甜菜(例如糖用甜菜和饲用甜菜)、花生、油菜、罂粟、橄榄、椰子、可可、甘蔗、烟草、蔬菜(例如西红柿、黄瓜、洋葱和生菜)、草皮和观赏植物(另见下文)的种子。谷物类(如小麦、大麦、黑麦、黑小麦和燕麦)、玉米和水稻种子的处理特别重要。
如下文所述,用本发明的活性成分或组合物处理转基因种子具有特别的意义。这涉及含有至少一种能够表达具有杀虫性质的多肽或蛋白质的异源基因的植物种子。转基因种子中的异源基因可源自例如以下属种的微生物:芽孢杆菌、根瘤菌属(Rhizobium)、假单胞菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棒状杆菌属(Clavibacter)、球囊霉属(Glomus)或粘帚霉属(Gliocladium)。该异源基因优选地来源于芽孢杆菌属种,在这种情况下,该基因产物对欧洲玉米螟和/或西方玉米根虫有效。异源基因更优选地来源于苏云金芽孢杆菌。
在本发明的上下文中,将本发明的组合物单独或以合适的制剂施用于种子。优选地,将种子在其足够稳定以在处理过程中不发生损害的状态下处理。一般而言,种子可在收获和播种之间的任何时间进行处理。习惯上使用从植物中分离出来并且不含穗轴、壳、茎、表皮、毛或果肉的种子。例如,可使用已被采收、清洗并干燥至水分含量小于15重量%的种子。或者,也可使用例如干燥后用水处理然后再次干燥的种子。
通常,当处理种子时,必须确保选择施用于种子的本发明组合物和/或其他添加剂的量,使得种子的发芽不受损害并且不伤害由此长成的植物。特别是在某些施用率下可表现出植物毒性作用的活性成分的情况下,这必须被确保。
本发明的组合物可直接施用,即不包含任何其他组分并未经稀释。通常,优选将组合物以合适的制剂形式施用于种子。用于种子处理的合适的制剂和方法是本领域技术人员已知的并记载于例如以下文献中:US 4,272,417 A、US 4,245,432 A、US 4,808,430、US 5,876,739、US 2003/0176428 A1、WO 2002/080675 A1、WO 2002/028186 A2。
可将根据本发明使用的活性成分转化为常规拌种制剂,例如溶液剂、乳剂、悬浮剂、粉末剂、泡沫剂、膏剂或其他用于种子的包衣组合物,以及ULV制剂。
这些制剂以已知方式制备,通过将活性成分与常规添加剂(例如常规填充剂和溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、粘合剂、赤霉素以及水)混合。
可存在于根据本发明使用的拌种制剂中的染料为通常用于此种目的的所有染料。可使用微溶于水的颜料或易溶于水的染料。实例包括已知名称为Rhodamine B、C.I.Pigment Red 112和C.I.Solvent Red 1的染料。
可存在于根据本发明使用的拌种制剂中的有用润湿剂为促进润湿并通常用于农用化学活性成分的制剂的所有物质。可优选使用烷基萘磺酸盐,例如二异丙基萘磺酸盐或二异丁基萘磺酸盐。
可存在于根据本发明使用的拌种制剂中的合适的分散剂和/或乳化剂为通常用于农用化学活性成分的制剂的所有非离子、阴离子和阳离子分散剂。可优选使用非离子分散剂或阴离子分散剂或者非离子分散剂或阴离子分散剂的混合物。合适的非离子分散剂尤其包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚,以及其磷酸化或硫酸化衍生物。合适的阴离子分散剂尤其是木质素磺酸盐、聚丙烯酸盐和芳基磺酸盐-甲醛缩合物。
可存在于根据本发明使用的拌种制剂中的消泡剂为通常用于农用化学活性成分的制剂的所有泡沫抑制物质。可优选使用有机硅消泡剂和硬脂酸镁。
可存在于根据本发明使用的拌种制剂中的防腐剂为可用于农用化学组合物中此类目的的所有物质。实例包括二氯苯和苯甲醇半缩甲醛。
可存在于根据本发明使用的拌种制剂中的二次增稠剂为可用于农用化学组合物中此类目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土和细碎二氧化硅。
可存在于根据本发明使用的拌种制剂中的有用的粘合剂为可用于拌种产品中的所有常规粘合剂。优选的实例包括聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素(tylose)。
根据本发明使用的拌种制剂可直接地或在预先用水稀释后用于处理各种不同种子,包括转基因植物的种子。在这种情况下,与表达形成的物质的相互作用也可产生另外的协同效应。
为了用可根据本发明使用的拌种制剂或用通过添加水由其制备的制剂处理种子,有用的设备为通常可用于拌种的所有混合装置。具体而言,拌种方法为将种子放入混合器中,加入特定所需量的拌种制剂本身或预先用水稀释后的拌种制剂,并将它们混合直至制剂均匀分布在种子上。如果合适,在这之后进行干燥操作。
具有良好的植物相容性、有益的恒温毒性和良好的环境相容性的本发明的活性成分合适用于保护植物和植物器官,以提高采收产量,并改善采收作物的品质。它们可优选地用作作物保护剂。它们对通常敏感和抗性的物种具有活性,并对所有或特定的发育阶段具有活性。
可根据本发明处理的植物包括以下主要作物植物:玉米、大豆、棉花、芸苔属(Brassica)油籽,例如甘蓝型油菜(Brassica napus)(例如Canola)、蔓菁(Brassicarapa)、芥菜型油菜(B.juncea)(如(田)芥菜)和埃塞俄比亚芥(Brassica carinata)、水稻、小麦、糖用甜菜、甘蔗、燕麦、黑麦、大麦、黍和高粱、黑小麦、亚麻、葡萄和各种植物类群的各种水果和蔬菜,例如蔷薇科(Rosaceae sp.)(例如,梨果如苹果和梨,以及核果如杏、樱桃、扁桃和桃,以及浆果如草莓)、Ribesioidae sp.、胡桃科(Juglandaceae sp.)、桦木科(Betulaceae sp.)、漆树科(Anacardiaceae sp.)、壳斗科(Fagaceae sp.)、桑科(Moraceaesp.)、木犀科(Oleaceae sp.)、猕猴桃科(Actinidaceae sp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如香蕉树和香蕉林(banana plantation))、茜草科(Rubiaceae sp.)(例如咖啡)、山茶科(Theaceae sp.)、梧桐科(Sterculiceae sp.)、芸香科(Rutaceae sp.)(例如柠檬、橙和葡萄柚)、茄科(Solanaceae sp.)(例如番茄、土豆、辣椒、茄子)、百合科(Liliaceae sp.)、菊科(Compositae sp.)(如莴苣、洋蓟和菊苣——包括根菊苣、欧洲菊苣或普通菊苣)、伞形科(Umbelliferae sp.)(例如胡萝卜、荷兰芹、芹菜和块根芹)、葫芦科(Cucurbitaceae sp.)(例如黄瓜——包括小黄瓜、南瓜、西瓜、葫芦和甜瓜)、葱科(Alliaceae sp.)(例如韭菜和洋葱)、十字花科(Cruciferae sp.)(例如白球甘蓝、红球甘蓝、茎椰菜、花椰菜、抱子甘蓝、小白菜、球茎甘蓝、萝卜、辣根、水芹和大白菜)、豆科(Leguminosae sp.)(例如花生、豌豆和黄豆——例如菜豆和蚕豆)、藜科(Chenopodiaceaesp.)(例如瑞士甜菜、饲用甜菜、菠菜、甜菜根)、锦葵科(Malvaceae)(例如秋葵)、天门冬科(Asparagaceae)(例如芦笋);花园和森林中的有用植物和观赏植物;以及在各种情况下,这些植物的基因修饰型。
如上文所提及,可根据本发明处理所有植物及其部位。在优选的实施方式中,将野生植物物种和植物栽培种、或通过传统生物育种技术(例如杂交或原生质体融合)获得的那些植物及其部位进行处理。在另一优选实施方式中,将通过基因工程方法(如果合适的话,与传统方法结合)获得的转基因植物和植物栽培种(基因修饰生物体)及其部位进行处理。术语“部位”或“植物的部位”或“植物部位”已在上文中进行解释。根据本发明,特别优选对各市售常规植物栽培种的植物或那些正在使用的植物进行处理。植物栽培品种被理解为意指通过常规育种、诱变或重组DNA技术培育的具有新性质(“特性”)的植物。它们可为栽培种、品种、生物型和基因型。
本发明的处理方法可用于处理基因修饰的生物体(GMO),例如植物或种子。基因修饰植物(或转基因植物)是指异源基因已稳定整合到基因组中的植物。术语“异源基因”本质上意指在植物外提供或组装的基因,并且将该基因引入核基因组、叶绿体基因组或线粒体基因组后,由于其表达感兴趣的蛋白质或多肽或存在于植物中的另一种基因、或存在于植物中的被下调或关闭(例如通过反义技术、共抑制技术或RNAi技术[RNA干扰])的其他基因,而赋予转化植物新的或改善的农学或其他特性。位于基因组中的异源基因也被称为转基因。由在植物基因组中的特定存在定义的转基因称为转化或转基因事件。
根据植物种类或植物栽培种、它们的位置和生长条件(土壤、气候、植被期、食性),本发明的处理也可导致超加性(“协同”)效果。例如,超出实际预期效果的以下效果为可能的:可根据本发明使用的活性成分和组合物的施用率降低和/或活性谱拓宽和/或功效增强、植物生长更好、对高温或低温的耐受性增强、对干旱或对水或土壤盐分的耐受性增强、开花性能增强、采收更容易、加速成熟、采收产量更高、果实更大、株高更高、叶色更绿、更早开花、采收产品的质量和/或营养价值更高、果实中的糖浓度更高、储存稳定性更好和/或采收产品的可加工性。
在某些施用率下,本发明的活性成分结合物还可对植物具有强化作用。因此,它们适用于调动植物的防御系统以抵抗不想要的植物病原真菌和/或微生物和/或病毒的攻击。这可能是本发明的组合物活性增强例如抗真菌的原因之一。植物强化(抗性诱导)物质在本文中应理解为意指那些能够以如下方式刺激植物防御系统的物质或物质组合物:当随后接种不想要的植物病原真菌时,处理的植物对这些不想要的植物病原真菌表现出相当程度的抗性。因此,本发明的物质可用于保护植物在处理后的特定时间段内免受所提及的病原体的侵袭。在用活性成分处理植物后,实现保护的期间通常延长1至10天,优选地1至7天。
优选根据本发明处理的植物和植物栽培种包括具有能赋予这些植物特别有利、有用特性的遗传物质的所有植物(无论是通过育种和/或生物技术手段获得的)。
同样优选根据本发明处理的植物和植物栽培种对一种或多种生物胁迫因素具有抗性,意指这些植物对动物和微生物害虫(例如线虫、昆虫、螨虫、植物病原真菌、细菌、病毒和/或类病毒)具有更好的防御能力。
抗线虫植物的实例记载于例如以下美国专利申请中:11/765,491、11/765,494、10/926,819、10/782,020、12/032,479、10/783,417、10/782,096、11/657,964、12/192,904、11/396,808、12/166,253、12/166,239、12/166,124、12/166,209、11/762,886、12/364,335、11/763,947、12/252,453、12/209,354、12/491,396和12/497,221。
也可根据本发明处理的植物和植物栽培种为对一种或多种非生物胁迫因素具有抗性的那些植物。非生物胁迫条件可包括例如干旱、低温暴露、热暴露、渗透胁迫、水淹、土壤盐分增加、矿物质暴露增加、臭氧暴露、强光暴露、有限的氮营养素利用率、有限的磷营养素可用或避荫。
也可根据本发明处理的植物和植物品种为那些特征在于提高的产量特征的植物。所述植物中提高的产量可为以下因素的结果:例如,改善的植物生理机能、生长和发育,如水利用效率、持水效率、改善的氮利用率、增强的碳同化作用、改善的光合作用、提高的发芽率和加速的成熟。产量也可受到改进的植物结构的影响(在胁迫和非胁迫条件下),所述植物结构包括但不限于:提早开花、对杂交种子生产的开花控制、秧苗活力、植株大小、节间数和节间距、根系生长、种子大小、果实大小、荚果大小、荚果数或穗数、每个荚果或穗的种子数量、种子质量、增强的种子饱满度、减少的种子散布、减少的荚开裂以及抗倒伏。其他的产量特性包括种子组成,如碳水化合物含量、蛋白质含量、油含量和组成、营养价值、抗营养化合物减少、改善的可加工性和更好的贮存稳定性。
可根据本发明处理的植物为已经表现出杂种优势或杂种效应特征的杂种植物,所述特征通常导致更高的产量、活力、更好的健康和对生物和非生物胁迫因素的抗性。此类植物通常通过将近交雄性不育亲本系(雌性杂交亲本)与另一近交雄性可育亲本系(雄性杂交亲本)杂交而产生。杂交种子通常从雄性不育植物中采收并出售给种植者。雄性不育植物有时(例如在玉米中)可通过去雄(即机械去除雄性生殖器官或雄花)产生,但更典型的是,雄性不育是植物基因组中的遗传决定因素的结果。在这种情况下,特别是当种子是从杂种植物中采收的所需产品时,确保杂种植物中的雄性能育性得到完全恢复通常是有益的,所述杂种植物中含有导致雄性不育的遗传决定因素。这可通过确保雄性杂交育种亲本具有适当的能育性恢复基因来实现,所述基因能够在含有导致雄性不育的遗传决定因素的杂种植物中恢复雄性能育性。雄性不育的遗传决定因素可位于细胞质中。例如,记载了芸苔属种的细胞质雄性不育(CMS)的实例。然而,雄性不育的遗传决定因素也可位于核基因组中。雄性不育植物也可通过植物生物技术方法例如基因工程获得。获得雄性不育植物的特别有用的方法记载于WO 89/10396中,其中例如核糖核酸酶例如芽孢杆菌RNA酶(barnase)在雄蕊的绒毡层细胞中选择性地表达。然后,可通过在绒毡层细胞中表达核糖核酸酶抑制剂例如芽胞杆菌RNA酶抑制剂(Barstar)来恢复能育性。
可根据本发明处理的植物或植物栽培种(通过植物生物技术方法如基因工程获得的)为除草剂耐受性植物,即耐受一种或多种给定的除草剂的植物。这种植物可通过遗传转化或通过选择含有赋予此类除草剂耐受性的突变的植物而获得。
耐受除草剂的植物为例如耐受草甘膦的植物,即耐受除草剂草甘膦或其盐的植物。通过各种方法可使植物耐受草甘膦。因此,例如,耐受草甘膦的植物可通过用编码5-烯醇丙酮酸莽草酸-3-磷酸合酶(5-enolpyruvylshikimate-3-phosphate synthase)(EPSPS)的基因转化植物而获得。此种EPSPS基因的实例为细菌鼠伤寒沙门氏菌(Salmonellatyphimurium)的AroA基因(突变体CT7)(Comai等人,1983,Science,221,370-371)、细菌农杆菌属(Agrobacterium sp.)的CP4基因(Barry等人,1992,Curr.Topics PlantPhysiol.7,139-145)、编码矮牵牛属EPSPS(petunia EPSPS)(Shah等人,1986,Science233,478-481)、番茄EPSPS(Gasser等人,1988,J.Biol.Chem.263,4280-4289)或牛筋草EPSPS(Eleusine EPSPS)(WO 01/66704)的基因。它也可为突变的EPSPS。耐受草甘膦的植物还可通过表达编码草甘膦氧化还原酶的基因获得。耐受草甘膦的植物还可通过表达编码草甘膦乙酰转移酶的基因获得。耐受草甘膦的植物还可通过选择含有上述基因的天然存在的突变的植物获得。已记载了表达赋予草甘膦耐受性的EPSPS基因的植物。已记载了表达赋予草甘膦耐受性的其他基因例如脱羧酶基因的植物。
其他抗除草剂的植物是例如能耐受抑制谷氨酰胺合酶的除草剂(例如双丙氨磷、膦丝菌素(phosphinothricin)或草铵膦(glufosinate))的植物。这种植物可通过表达解除除草剂毒性的酶或抗抑制的谷氨酰胺合成酶的突变体获得。此种有效解毒酶的一个实例为编码膦丝菌素乙酰转移酶的酶(例如来自链霉菌属(Streptomyces)的bar或pat蛋白)。已记载了表达外源膦丝菌素乙酰转移酶的植物。
其他耐除草剂的植物也是已经致使耐受抑制羟基苯基丙酮酸双加氧酶(HPPD)的除草剂的植物。羟基苯基丙酮酸双加氧酶为催化其中对羟基苯基丙酮酸(HPP)转化为尿黑酸的反应的酶。耐受HPPD抑制剂的植物可用编码天然存在的抗HPPD酶的基因或编码突变或嵌合的HPPD酶的基因进行转化,如记载于WO 96/38567、WO 99/24585、WO 99/24586、WO2009/144079、WO 2002/046387或US 6,768,044中。通过用编码某些能形成尿黑酸的特定酶的基因转化植物,也可获得对HPPD抑制剂的耐受性,尽管HPPD抑制剂抑制天然的HPPD酶。此种植物记载于WO 99/34008和WO 02/36787中。除了编码耐受HPPD酶的基因之外,也可通过用编码预苯酸脱氢酶的基因转化植物而改善植物对HPPD抑制剂的耐受性,如记载于WO2004/024928。此外,可通过将编码代谢或降解HPPD抑制剂的酶(例如CYP450酶)的基因插入植物的基因组中,使其更耐受HPPD抑制剂(参见WO 2007/103567和WO 2008/150473)。
其他抗除草剂的植物是对乙酰乳酸合酶(ALS)抑制剂具有耐受性的植物。已知的ALS抑制剂包括例如磺酰脲、咪唑啉酮、三唑嘧啶、嘧啶基氧基(硫代)苯甲酸酯和/或磺酰基氨基羰基三唑啉酮除草剂。已知ALS酶(也称为乙酰羟酸合成酶,AHAS)中的不同突变赋予对不同除草剂和除草剂群组的耐受性,如记载于例如Tranel和Wright(Weed Science 2002,50,700-712)中。已记载了耐受磺酰脲的植物和耐受咪唑啉酮的植物的产生。还记载了其他耐受磺酰脲和咪唑啉酮的植物。
其他耐受咪唑啉酮和/或磺酰脲的植物可通过诱导突变、通过在除草剂的存在下在细胞培养物中选择或通过诱变育种获得(参见例如,对于大豆US 5,084,082、对于水稻WO97/41218、对于糖用甜菜US 5,773,702和WO 99/057965、对于莴苣US 5,198,599或对于向日葵WO 01/065922)。
还可根据本发明处理的植物或植物品种(通过植物生物技术方法例如基因工程获得)是抗虫的转基因植物,即对某些目标昆虫的侵害具有抗性的植物。这类植物可通过遗传转化或通过筛选含有赋予这种昆虫抗性的突变的植物而获得。
在本文中,术语“抗虫转基因植物”包括含有至少一个包含编码序列的转基因的任何植物,所述编码序列编码:
1)苏云金芽孢杆菌的杀虫晶体蛋白或其杀虫部分,例如由Crickmore等人(Microbiology and Molecular Biology Reviews 1998,62,807-813)编译、由Crickmore等人(2005)更新在苏云金芽孢杆菌毒素术语表中(在线网址:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/)的杀虫晶体蛋白,或其杀虫部分,例如Cry蛋白类Cry1Ab、Cry1Ac、Cry1B、Cry1C、Cry1D、Cry1F、Cry2Ab、Cry3Aa或Cry3Bb的蛋白质或其杀虫部分(例如EP-A 1999141和WO 2007/107302),或那些通过合成基因编码的蛋白质,如记载于美国专利申请12/249,016中;或者
2)苏云金芽孢杆菌的晶体蛋白或其部分,所述蛋白质或其部分在除苏云金芽孢杆菌之外的第二种晶体蛋白或其部分的存在下具有杀虫性,所述第二种晶体蛋白或其部分例如由Cy34和Cy35晶体蛋白组成的二元毒素(Nat.Biotechnol.2001,19,668-72;AppliedEnvironm.Microbiol.2006,71,1765-1774)或由Cry1A或Cry1F蛋白和Cry2Aa或Cry2Ab或Cry2Ae蛋白组成的二元毒素(美国专利申请12/214,022和EP08010791.5);或者
3)包含苏云金芽孢杆菌的两种不同杀虫晶体蛋白的部分的杂合杀虫蛋白,例如上述1)的蛋白质的杂合体或上述2)的蛋白质的杂合体,例如由玉米品系(event)MON98034产生的Cry1A.105蛋白(WO 2007/027777);或者
4)上述1)至3)中任一项的蛋白质,其中一些、特别地1至10个氨基酸被另一氨基酸取代,以获得对目标昆虫物种更高的杀虫活性,和/或扩展所影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中引入编码DNA中的改变,例如在玉米品系MON863或MON88017中的Cry3Bb1蛋白,或玉米品系MIR604中的Cry3A蛋白;或者
5)苏云金芽孢杆菌或蜡状芽孢杆菌(Bacillus cereus)的杀虫分泌蛋白,或其杀虫部分,例如列于
http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html的营养期杀虫蛋白(VIP),例如VIP3Aa蛋白类的蛋白质;或者
6)苏云金芽孢杆菌或蜡状芽孢杆菌的分泌蛋白,其在苏云金芽孢杆菌或蜡状芽孢杆菌的第二种分泌蛋白的存在下具有杀虫性,例如由VIP1A和VIP2A蛋白组成的二元毒素(WO 94/21795);或者
7)包含苏云金芽孢杆菌或蜡状芽孢杆菌的不同分泌蛋白的部分的杂合杀虫蛋白质,例如上述1)中蛋白质的杂合体或上述2)中蛋白质的杂合体;或者
8)上述5)至7)中任一项的蛋白质,其中一些,特别是1至10个氨基酸被另一氨基酸取代,以获得对目标昆虫物种更高的杀虫活性,和/或扩展所影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中引入编码DNA中的改变(同时仍编码杀虫蛋白),例如棉花品系COT 102中的VIP3Aa蛋白;或者
9)苏云金芽孢杆菌或蜡状芽孢杆菌的分泌蛋白,其在苏云金芽孢杆菌的结晶蛋白的存在下具有杀虫性,例如由蛋白VIP3和Cry1A或Cry1F组成的二元毒素(美国专利申请61/126083和61/195019),或由VIP3蛋白和Cry2Aa或Cry2Ab或Cry2Ae蛋白组成的二元毒素(美国专利申请12/214,022和EP 08010791.5);或者
10)根据上述要点9)的蛋白质,其中一些,特别是1至10个氨基酸已另一氨基酸取代,以获得对目标昆虫物种更高的杀虫活性,和/或扩展所影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中引入编码DNA中的改变(同时仍编码杀虫蛋白)。
当然,本文中所用的抗虫的转基因植物还包括含有编码上述1至10类中任一类蛋白质的基因的组合的任何植物。在一个实施方案中,抗虫的植物含有多于一种的编码上述1至10类的任一类蛋白质的转基因,通过使用对同一目标昆虫物种具有杀虫性但具有不同作用模式(例如结合到昆虫中不同的受体结合位点)的不同蛋白质,以扩展所影响的目标昆虫物种的范围或延迟对植物的昆虫抗性发展。
在本文中,“抗虫转基因植物”另外地包括任何含有至少一种转基因的植物,所述转基因含有用于产生双链RNA的序列,所述双链RNA在昆虫害虫食用食物后阻止该害虫的生长。
还可根据本发明处理的植物或植物栽培种(通过植物生物技术方法如基因工程获得的)对非生物胁迫因素具有耐受性。这种植物可通过遗传转化或通过选择含有赋予这种胁迫抗性的突变的植物而获得。特别有用的耐受胁迫的植物包括:
a)含有能够降低植物细胞或植物中的多腺苷二磷酸-核糖聚合酶(PARP)基因的表达和/或活性的转基因的植物;
b)含有能降低植物或植物细胞中PARG编码基因的表达和/或活性的增强胁迫耐受性的转基因的植物;
c)含有增强胁迫耐受性的转基因的植物,所述转基因编码烟酰胺腺嘌呤二核苷酸补救生物合成途径的植物功能酶,包括烟酰胺酶、烟酸磷酸核糖基转移酶、烟酸单核苷酸腺嘌呤转移酶、烟酰胺腺嘌呤二核苷酸合成酶或烟酰胺磷酸核糖基转移酶。
还可根据本发明处理的植物或植物栽培种(通过植物生物技术方法如基因工程获得)显示出采收产品的数量、品质和/或储藏稳定性的改变和/或采收产品特定成分的性能的改变,例如:
1)合成改性淀粉的转基因植物,该改性淀粉的物理化学性质、特别是直链淀粉含量或直链淀粉/支链淀粉比例、支化度、平均链长、侧链分布、粘度行为、胶凝强度、淀粉颗粒粒径和/或淀粉颗粒形态,同野生型植物细胞或植物中的合成淀粉相比发生了改变,使得该改性淀粉能更好地合适特定用途。
2)合成非淀粉碳水化合物聚合物的转基因植物,或合成与未进行基因修饰的野生型植物相比具有改变的性能的非淀粉碳水化合物聚合物的转基因植物。实例有:产生多聚果糖、尤其是菊糖和果聚糖类型的植物,产生α-1,4-葡聚糖的植物,产生α-1,6-分支的α-1、4-葡聚糖的植物,和产生交替物(alternan)的植物。
3)产生透明质酸的转基因植物。
4)转基因植物或杂种植物,例如具有特定特性的洋葱,例如“高可溶性固含量”、“低刺激性”(LP)和/或“长期储存”(LS)。
也可根据本发明处理的植物或植物栽培种(通过植物生物技术方法例如基因工程获得)是具有改变的纤维性质的植物,如棉株。这些植物可通过遗传转化、或通过筛选含有赋予这种改变的纤维性质的突变的植物而获得,包括以下植物:
a)植物如棉株,其含有纤维素合成酶基因的变型;
b)植物如棉株,其含有rsw2或rsw3同源核酸的变型,例如具有增加的蔗糖磷酸合酶表达的棉株;
c)植物如棉株,其具有增加的蔗糖合酶表达;
d)植物如棉株,其中纤维细胞基部处的胞间连丝门控的时间安排例如通过纤维选择性的β-1,3-葡聚糖酶的下调而被改变;
e)植物如棉株,其具有例如通过表达包括nodC的N-乙酰基葡糖胺转移酶基因和几丁质合成酶基因而改变了反应性的纤维。
还可根据本发明处理的植物或植物栽培种(通过植物生物技术方法例如基因工程获得)为具有改变的油组成特征的植物,如油籽油菜或有关的芸苔属植物。这类植物可通过遗传转化或通过筛选含有赋予这种改变的油特性的突变的植物而获得,所述植物包括:
a)产生具有高油酸含量的油的植物,如油籽油菜植物;
b)产生具有低亚麻酸含量的油的植物,如油籽油菜植物;
c)产生具有低饱和脂肪酸含量的油的植物,如油籽油菜植物。
也可根据本发明处理的植物或植物栽培种(其可通过植物生物技术方法如基因工程获得)是马铃薯之类的植物,其例如对马铃薯病毒Y(来自Tecnoplant,Argentina的SY230和SY233品系)具有病毒抗性,或其对病害例如马铃薯晚疫病具有抗性(例如RB基因),或其表现出降低的低温诱导甜味(其携带基因Nt-Inh,II-INV)或其表现出矮化表型(A-20氧化酶基因)。
也可根据本发明处理的植物或植物栽培种(通过植物生物技术方法例如基因工程获得)是具有改变的种子破碎特性的植物,例如油籽油菜或相关的芸苔属植物。这类植物可通过遗传转化或通过选择含有赋予此类改变的特征的突变的植物而获得,并且包括具有延迟或减少的种子破碎的植物例如油籽油菜。
可根据本发明处理的特别有用的转基因植物是具有转化品系或转化品系组合的植物,这些转化品系或转化品系的组合是美国的美国农业部(USDA)的动植物健康检验局(APHIS)授予或未决的非管制状态申请的主题。与此相关的信息可随时从APHIS(4700River Road Riverdale,MD 20737,USA)获得,例如通过网站http://www.aphis.usda.gov/brs/not_reg.html。在本申请的提交日期,具有以下信息的申请已在APHIS获得批准或待决:
-申请:申请的识别号。转化品系的技术说明可在APHIS网站上通过申请号获得的具体申请文件中找到。这些说明在本文中通过引用公开。
-申请的延期:指请求扩大较早的申请的范围或期限。
-机构:提交申请的人的姓名。
-规制物品:所涉及的植物物种。
-转基因表型:转化品系赋予植物的性状。
-转化品系或谱系:请求非管制状态的品系(有时也称为谱系)的名称。
-APHIS文件:APHIS已发布的有关申请的各种文件,或可应要求从APHIS获得的各种文件。
可根据本发明处理的特别有用的转基因植物是包含一种或多种编码一种或多种毒素的基因的植物,例如以下列商品名出售的转基因植物:YIELD(例如玉米、棉花、大豆)、(例如玉米)、(例如玉米)、(例如玉米)、(例如玉米)、(棉花)、(棉花)、Nucotn(棉花)、(例如玉米)、和(马铃薯)。可提及的耐除草剂植物的实例包括以下列商品名获得的玉米品种、棉花品种和大豆品种:Roundup(耐草甘膦,例如玉米、棉花、大豆)、Liberty(耐膦丝菌素,例如油籽油菜)、(耐咪唑啉酮)和(耐磺酰脲),例如玉米。可提及的抗除草剂的植物(以常规方式培育的除草剂耐受性的植物)包括以商品名(例如玉米)售卖的品种。
可根据本发明处理的特别有用的转基因植物是含有转化品系或转化品系的组合的植物,并且其列在例如多个国家或地区管理机构的数据库中(参见例如http://gmoinfo.jrc.it/gmp_browse.aspx和http://cera-gmc.org/index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode=&action=gm_crop_database&mode=Submit)。
本发明的活性成分或组合物还可用于材料的保护,以保护工业材料免受不想要的微生物例如真菌和昆虫的侵害和破坏。
此外,本发明的化合物可单独或与其他活性成分结合用作防污组合物。
在本文中,工业材料被理解为意指已制备用于工业中的非生物材料。例如,由本发明的活性成分保护其免受微生物改变或破坏的工业材料可以是粘合剂、施胶剂(size)、纸、壁纸和纸板、纺织品、地毯、皮革、木材、油漆和塑料制品、冷却润滑剂和可被微生物感染或破坏的其他材料。需要保护的材料范围还包括生产厂房和建筑物的部件,例如冷却水回路、冷却和加热系统以及通风系统和空调系统,它们可能会因微生物的繁殖而受到损害。本发明范围内的工业材料优选地包括粘合剂、施胶剂、纸和纸板、皮革、木材、油漆、冷却润滑剂和传热流体,更优选木材。本发明的活性成分或组合物可防止不利影响,例如腐烂、腐解、变色、脱色或霉菌的形成。此外,本发明的化合物可用于保护与盐水或微咸水接触的物体(尤其是船体、筛网、渔网、建筑物、系泊设备和信号系统)免受污染。
本发明用于控制不想要的真菌的方法也可用于保护储藏物品。本文中“储藏物品”被理解为意指植物或动物来源的天然物质或其天然来源的加工产品,需要对其进行长期保护。植物来源的储藏物品,例如植物或植物部位,如茎、叶、块茎、种子、果实、谷物,可在新鲜采收或加工后通过(预)干燥、润湿、粉碎、研磨、压榨或烘烤进行保护。储藏物品还包括未经加工的木材(例如建筑木材、电线杆和篱笆墙)和成品形式的木材(例如家具)。动物来源的储藏物品是,例如,生皮、皮革、毛皮和毛发。本发明的活性成分可防止不利影响,例如腐烂、腐解、变色、脱色或形成霉菌。
可根据本发明处理的真菌病害的病原体的非限制性实例包括:由白粉病病原体引起的病害,例如布氏白粉菌属种(Blumeria species),例如禾本科布氏白粉菌(Blumeriagraminis);叉丝单囊壳属种(Podosphaera species),例如白叉丝单囊壳(Podosphaeraleucotricha);单囊壳属种(Sphaerotheca species),例如单囊壳白粉菌(Sphaerothecafuliginea);钩丝壳属种(Uncinula species),例如葡萄钩丝壳(Uncinula necator);由锈病病原体引起的病害,例如胶锈菌属种(Gymnosporangium species),例如褐色胶锈菌(Gymnosporangium sabinae);驼孢锈菌属种(Hemileia species),例如咖啡驼孢锈菌(Hemileia vastatrix);层锈菌属种(Phakopsora species),例如豆薯层锈菌(Phakopsorapachyrhizi)或山水蛭层锈菌(Phakopsora meibomiae);柄锈菌属种(Puccinia species),例如隐匿柄锈菌(Puccinia recondita)或小麦叶锈菌(Puccinia triticina);单孢锈菌属种(Uromyces species),例如疣顶单孢锈菌(Uromyces appendiculatus);由来自卵菌的病原体引起的病害,例如盘梗霉属种(Bremia species),例如莴苣盘梗霉(Bremialactucae);霜霉属种(Peronospora species),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);疫霉属种(Phytophthora species),例如致病疫霉(Phytophthorainfestans);单轴霉属种(Plasmopara species),例如葡萄单轴霉(Plasmoparaviticola);假霜霉属种(Pseudoperonospora species),例如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonospora cubensis);腐霉属种(Pythium species),例如终极腐霉(Pythium ultimum);由以下病原体引起的叶斑枯病(leaf blotch disease)和叶萎蔫病(leaf wilt disease):例如链格孢属种
(Alternaria species),例如茄链格孢(Alternaria solani);尾孢属种(Cercospora species),例如甜菜生尾孢(Cercospora beticola);枝孢属种(Cladiosporium species),例如黄瓜枝孢(Cladiosporium cucumerinum);旋孢腔菌属种(Cochliobolus species),例如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:内脐蠕孢属(Drechslera),同物异名:长蠕孢属(Helminthosporium);炭疽菌属种(Colletotrichum species),例如菜豆炭疽菌(Colletotrichum lindemuthanium);锈斑病菌属种(Cycloconium species),例如油橄榄孔雀斑病菌(Cycloconium oleaginum);间座壳菌属种(Diaporthe species),例如柑桔间座壳(Diaporthe citri);痂囊腔菌属种(Elsinoe species),例如柑桔痂囊腔菌(Elsinoe fawcettii);盘长孢属种(Gloeosporiumspecies),例如悦色盘长孢(Gloeosporium laeticolor);小丛壳属种(Glomerellaspecies),例如围小丛壳(Glomerella cingulate);球座菌属种(Guignardia species),例如葡萄球座菌(Guignardia bidwelli);小球腔菌属种(Leptosphaeria species),例如斑污小球腔菌(Leptosphaeria maculans);巨座壳属种(Magnaporthe species),例如Magnaporthe grisea;微座孢属种(Microdochium species),例如雪霉微座孢(Microdochium nivale);球腔菌属种(Mycosphaerella species),例如禾生球腔菌(Mycosphaerella graminicola)和斐济球腔菌(M.fijiensis);暗球腔菌属种(Phaeosphaeria species),例如小麦颖枯病菌(Phaeosphaeria nodorum);核腔菌属种(Pyrenophora species),例如圆核腔菌(Pyrenophora teres);柱隔孢属种(Ramulariaspecies),例如辛加柱隔孢(Ramularia collo-cygni);、喙孢属种(Rhynchosporiumspecies),例如黑麦喙孢(Rhynchosporium secalis);壳针孢属种(Septoria species),例如芹菜壳针孢(Septoria apii)核瑚菌属种(Typhula species),例如肉孢核瑚菌(Typhulaincarnate);黑星菌属种(Venturia species),例如苹果黑星菌(Venturia inaequalis);由以下病原体引起的根和茎病害:例如,伏革菌属种(Corticium species),例如禾伏革菌(Corticium graminearum);镰刀菌属种(Fusarium species),例如尖孢镰刀菌(Fusariumoxysporum);顶囊壳属种(Gaeumannomyces species),例如禾顶囊壳(Gaeumannomycesgraminis);丝核菌属种(Rhizoctonia species),例如立枯丝核菌(Rhizoctonia solani);Tapesia属种(例如Tapesia acuformis);根串珠霉属种(Thielaviopsis species),例如根串珠霉(Thielaviopsis basicola);由以下病原体引起的穗和圆锥花序病害(包括玉米作物):例如链格孢属种,例如链格孢属种;曲霉属种(Aspergillus species),例如黄曲霉(Aspergillus flavus);枝孢属种(Cladosporium species),例如芽枝状枝孢霉;麦角菌属种(Claviceps species),例如紫色麦角菌(Claviceps purpurea);镰刀菌属种,例如黄色镰刀菌(Fusarium culmorum);赤霉属种(Gibberella species),例如玉蜀黍赤霉(Gibberella zeae);明梭孢属种(Monographella species),例如雪腐明梭孢(Monographella nivalis);壳针孢属种,例如颖枯壳针孢(Septoria nodorum);由黑粉菌(smut fungi)引起的病害,例如轴黑粉菌属种(Sphacelotheca species),例如黍轴黑粉菌(Sphacelotheca reiliana);腥黑粉菌属种(Tilletia species),例如小麦网腥黑粉菌(Tilletia caries)、小麦矮腥黑粉菌(T.controversa);条黑粉菌属种(Urocystisspecies),例如隐条黑粉菌(Urocystis occulta);黑粉菌属种(Ustilago species),例如裸黑粉菌(Ustilago nuda)、小麦散黑粉菌(U.nuda tritici)由以下病原体引起的果腐病:例如,曲霉属种(Aspergillus species),例如黄曲霉(Aspergillus flavus);葡萄孢属种(Botrytis species),例如灰葡萄孢(Botrytis cinerea);青霉属种(Penicilliumspecies),例如扩展青霉(Penicillium expansum)和产紫青霉(P.purpurogenum);核盘菌属种(Sclerotinia species),例如核盘菌(Sclerotinia sclerotiorum);轮枝菌属种(Verticilium species),例如黑白轮枝菌(Verticilium alboatrum);由以下病原体引起的种传和土传的腐烂和萎蔫病害,以及幼苗病害:例如镰刀菌属种(Fusarium species),例如黄色镰刀菌(Fusarium culmorum);疫霉属种(Phytophthora species)(例如恶疫霉(Phytophthora cactorum));腐霉属种(例如终极腐霉);丝核菌属种,例如立枯丝核菌;小核菌属种(Sclerotium species),例如齐整小核菌(Sclerotium rolfsii);由以下病原体引起的癌性病害、菌瘿和扫帚病:例如丛赤壳属种(Nectria species),例如仁果干癌丛赤壳菌(Nectria galligena);
由以下病原体引起的萎蔫病害:例如链核盘菌属种(Monilinia species),例如核果链核盘菌(Monilinia laxa);
由以下病原体引起的叶、花和果实的畸形:例如外囊菌属种(Taphrina species),例如畸形外囊菌(Taphrina deformans);由以下病原体引起的木本植物的退行性病害:例如依科属种(Esca species),例如厚孢小褐球壳(Phaeomoniella chlamydospora)和褐枝顶孢霉(Phaeoacremonium aleophilum)和地中海嗜蓝孢孔菌(Fomitiporiamediterranea);
由以下病原体引起的花和种子的病害:例如葡萄孢属种(例如灰葡萄孢);由以下病原体引起的植物块茎病害:例如,丝核菌属种(例如立枯丝核菌)、长蠕孢属种(Helminthosporium species),例如茄长蠕孢(Helminthosporium solani);由以下细菌性病原体引起的病害:例如黄单胞菌属种(Xanthomonas species),例如稻黄单胞菌白叶枯变种(Xanthomonas campestris pv.Oryzae);假单胞菌属种(Pseudomonas species),例如丁香假单胞菌黄瓜致病变种(Pseudomonas syringae pv.lachrymans);欧文氏菌属种(Erwinia species),例如解淀粉欧文氏菌(Erwinia amylovora)。
可优先防治以下大豆病害:
由以下病原体引起的叶、茎、荚和种子的真菌病害,例如:轮纹叶斑病(Alternarialeaf spot)(极细链格孢菌(Alternaria spec.atrans tenuissima))、炭疽病(Anthracnose)(Colletotrichum loeosporoides dematium var.truncatum)、褐斑病(大豆壳针孢(Septoria glycines))、桃叶穿孔病和叶枯病(cercospora leaf spot andblight)(菊池尾孢(Cercospora kikuchii))、笄霉(choanephora)叶枯病(漏斗笄霉(Choanephora infundibulifera trispora(同名)))、dactuliophora叶斑病(Dactuliophora glycines)、大豆霜霉病(downy mildew)(东北霜霉(Peronosporamanshurica))、内脐蠕孢(rechslera)枯萎病(Drechslera glycini)、蛙眼病(大豆尾孢(Cercospora sojina))、菜豆(leptosphaerulina)叶斑病(三叶草小光壳(Leptosphaerulina trifolii))、叶点霉(phyllostica)叶斑病(大豆生叶点霉(Phyllosticta sojaecola))、荚和茎枯萎病(大豆拟茎点霉(Phomopsis sojae))、白粉病(Microsphaera diffusa)、棘壳孢(pyrenochaeta)叶斑病(Pyrenochaeta glycines)、丝核菌地上部分、叶枯病和立枯病(立枯丝核菌)、锈病(豆薯层锈菌(Phakopsora pachyrhizi)、山蚂蝗层锈菌(Phakopsora meibomiae))、黑星病(大豆痂圆孢(Sphaceloma glycines))、匍柄霉(stemphylium)叶枯病(匍柄霉(Stemphylium botryosum))、靶斑病(target spot)(山扁豆生棒孢(Corynespora cassiicola))。
由以下病原体所致的位于根部和茎基部的真菌病害,例如黑色根腐病(blackroot rot)(野百合丽赤壳(Calonectria crotalariae))、炭腐病(菜豆生壳球孢(Macrophomina phaseolina))、镰孢枯萎病或萎蔫、根腐病以及荚和根颈腐烂(尖镰孢(Fusarium oxysporum)、直喙镰孢(Fusarium orthoceras)、半裸镰孢(Fusariumsemitectum)、木贼镰孢(Fusarium equiseti))、mycoleptodiscus根腐病(风眼莲孢霉(Mycoleptodiscus terrestris))、新赤壳属(neocosmospora)(侵菅新赤壳(Neocosmopspora vasinfecta))、荚和茎疫病(菜豆间座壳(Diaporthe phaseolorum))、茎溃疡(大豆北方茎溃疡病菌(Diaporthe phaseolorum var.caulivora))、疫霉腐病(大雄疫霉(Phytophthora megasperma))、褐茎腐病(大豆茎褐腐病菌(Phialophora regata))、腐霉病(瓜果腐霉(Pythium aphanidermatum)、畸雌腐霉(Pythium irregulare)、德巴利腐霉(Pythium debaryanum)、群结腐霉(Pythium myriotylum)、终极腐霉)、丝核菌根腐病、茎腐和立枯病(立枯丝核菌)、核盘菌茎腐病(核盘菌(Sclerotinia sclerotiorum))、核盘菌白绢病(Sclerotinia rolfsii)、根串珠霉根腐病(根串珠霉(Thielaviopsis basicola))。
能够降解或改变工业材料的微生物包括例如细菌、真菌、酵母、藻类和粘液生物(slime organism)。本发明的活性成分优选作用于真菌,尤其是霉菌、使木材变色和使木材破坏的真菌(担子菌纲(Basidiomycetes)),以及作用于粘液生物和藻类。实例包括以下属的微生物:链格孢属,链格孢属,例如细链格孢(Alternaria tenuis);毛壳菌属(Chaetomium),例如球毛壳菌(Chaetomium globosum);粉孢革菌属(Coniophora),例如Coniophora puetana;香菇属(Lentinus),例如虎皮香菇(Lentinus tigrinus);青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum);多孔菌属(Polyporus),例如杂色多孔菌(Polyporus versicolor);短梗霉属(Aureobasidium),例如出芽短梗霉菌(Aureobasidium pullulans);核茎点属(Sclerophoma),例如Sclerophoma pityophila;木霉属(Trichoderma),例如绿色木霉(Trichoderma viride);埃希氏菌属(Escherichia),例如大肠杆菌(Escherichia coli);假单胞菌属(Pseudomonas),例如铜绿假单胞菌(Pseudomonas aeruginosa);葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcus aureus)。
此外,本发明的活性成分还具有非常好的抗真菌活性。它们具有非常广泛的抗真菌活性谱,特别是针对皮肤癣菌(antimycotic)和酵母菌、霉菌和双相性真菌(diphasicfungi)(例如针对念珠菌属种(Candida species),例如白色念珠菌(Candida albicans)、光滑念珠菌(Candida glabrata))和絮状表皮癣菌(Epidermophyton floccosum)、曲霉属物种(例如黑曲霉(Aspergillus niger)和烟曲霉属(Aspergillus fumigatus))、毛癣菌属种(Trichophyton species)(例如须毛癣菌(Trichophyton mentagrophytes))、小孢子菌属种(Microsporon species)(例如犬小芽孢菌(Microsporon canis))和audouinii。这些真菌的列举绝不构成对可被防治的真菌谱的限制,而仅仅具有说明性特征。
因此,本发明的活性成分可用于医疗和非医疗应用。
如果合适,本发明的化合物在某些浓度或施用率下也可用作除草剂、安全剂、生长调节剂或改善植物特性的试剂,或用作杀微生物剂,例如杀真菌剂、抗真菌剂、杀菌剂、杀病毒剂(包括抗类病毒剂)或用作抗MLO(类支原体生物)和RLO(类立克次氏体生物)的药剂。视情况而定,它们也可用作合成其他活性成分的中间体或前体。
以下实施例说明本发明。
A.化学实施例
合成N3-乙基-N3-2-二甲基-N1-(1-甲基-1H-四唑-5-基)-4-(三氟甲基)间苯二甲酰胺
步骤1:制备3-(甲氧基羰基)-2-甲基-6-(三氟甲基)苯甲酸
在-70℃下在60分钟内,向初始加入的15g(43.5mmol)的3-碘-2-甲基-4-(三氟甲基)苯甲酸甲酯于400ml干燥的THF中,加入43.6ml(56.6mmol)的1.3M i-PrMgCl/LiCl的THF溶液。将反应溶液温热至-30℃并在该温度下再搅拌60分钟。随后,将其冷却回至-70℃,并引入气态CO2。此后——随着持续引入CO2和监测反应——将混合物温热至室温。转化结束后,将反应溶液在超声浴中脱气,然后浓缩至干燥。将残余物溶于水中,用2N HCl调节至pH3-4,并用二氯甲烷萃取。将有机相干燥并浓缩。残余物通过柱色谱法纯化(HPLC,正相,梯度:乙酸乙酯/正庚烷:5%→70%乙酸乙酯)。获得9g的3-(甲氧基羰基)-2-甲基-6-(三氟甲基)苯甲酸。
1H-NMR(400MHz,DMSO-d6):δ=14.08(br s,1H);7.94(d,1H);7.77(d,1H);3.89(s,3H);2.46(s,3H)。
步骤2:制备3-[乙基(甲基)氨基甲酰基]-2-甲基-4-(三氟甲基)苯甲酸甲酯
向初始加入的400mg(1.52mmol)的3-(甲氧基羰基)-2-甲基-6-(三氟甲基)苯甲酸于20ml的二氯甲烷中,加入数滴二甲基甲酰胺。随后,在室温下,加入0.2ml(2.28mmol)草酰氯,并将反应混合物在室温下搅拌2小时。将混合物浓缩后,将其与甲苯共蒸发两次。将残余物溶于5ml二氯甲烷中,并在0℃下滴加至0.2ml(2.28mmol)的N-甲基乙胺和0.5ml(3.05mmol)的Hünig碱于10ml二氯甲烷的溶液中。将反应混合物在室温下搅拌12小时,然后浓缩至干燥。将残余物通过柱色谱法纯化(HPLC,正相,梯度:乙酸乙酯/正庚烷:10%→70%乙酸乙酯)。获得424mg的3-[乙基(甲基)氨基甲酰基]-2-甲基-4-(三氟甲基)苯甲酸甲酯。
1H-NMR(400MHz,DMSO-d6):δ=7.93(d,1H);7.77(d,1H);3.89(s,3H);3.59(m,1H,异构体1),3.43(m,1H,异构体1);3.06(m,1H,异构体2);2.99(s,3H,异构体1);2.98(m,1H,异构体2);2.66(s,3H,异构体2);2.36(s,3H);1.13(t,3H,异构体1);0.99(t,3H,异构体2)。
步骤3:制备3-[乙基(甲基)氨基甲酰基]-2-甲基-4-(三氟甲基)苯甲酸
在室温下,向初始加入的于10ml甲醇中的424mg(1.39mmol)的3-[乙基(甲基)氨基甲酰基]-2-甲基-4-(三氟甲基)苯甲酸甲酯中,滴加于3ml水中的89mg(2.09mmol)的氢氧化钠溶液。将反应混合物在室温下搅拌4小时。随后,将反应混合物浓缩至干燥,并将残余物溶于20ml水中。用2N HCl将混合物调节至pH 3-4,过滤掉形成的沉淀并干燥。获得352mg的3-[乙基(甲基)氨基甲酰基]-2-甲基-4-(三氟甲基)苯甲酸。
1H-NMR(400MHz,DMSO-d6):δ=13.58(br s,1H);7.90(m,1H);7.73(d,1H);3.60(m,1H),异构体1);3.42(m,1H,异构体1);3.05(m,1H),异构体2);3.00(s,3H,异构体1);2.98(m,1H,异构体2);2.66(s,3H,异构体2);1.13(t,3H,异构体1);0.99(t,3H,异构体2)。
步骤4:制备N3-乙基-N3-2-二甲基-N1-(1-甲基-1H-四唑-5-基)-4-(三氟甲基)间苯二甲酰胺
在室温下,向初始加入的200mg(0.69mmol)的3-[乙基(甲基)氨基甲酰基]-2-甲基-4-(三氟甲基)苯甲酸于3ml吡啶中以及104.9mg(1.03mmol)的1-甲基-1H-四唑-5-胺中,加入0.09ml(1.03mmol)草酰氯。将反应混合物在室温下搅拌12小时。然后加入10ml水,用二氯甲烷萃取混合物。将有机相干燥并浓缩至干燥。通过柱色谱法纯化残余物(HPLC,C18,梯度:乙腈/水(++0.05%三氟乙酸),20/80→100/0在30分钟内)。获得44mg(连同混合的级份)的N3-乙基-N3-2-二甲基-N1-(1-甲基-1H-四唑-5-基)-4-(三氟甲基)间苯二甲酰胺(实施例编号1-20)。
下表中列出的实施例以类似于上述方法制备,或者可类似于上述方法获得。这些化合物是非常特别优选的。
本文中使用的缩写意指:
Me=甲基,Bu=丁基,Et=乙基,Pr=丙基,c=环,Ph=苯基
表1:本发明的通式(I)的化合物,其中Q为Q1,Rx为甲基,且其他取代基具有下文给出的定义。
表2:本发明的通式(I)的化合物,其中Q为Q1,Rx为乙基,且其他取代基具有如下定义。
表3:本发明的通式(I)的化合物,其中Q为Q1,Rx为丙基,且其他取代基具有以下给出的定义。
上述表格中所述的众多本发明的式(I)的化合物的NMR数据公开如下,以进一步表征:
实施例编号1-19:1H-NMR(400MHz,DMSO-d6):δ=11.80(br s);7.85(d,1H);7.81(d,1H);4.01(s,3H);3.04(s,3H);2.74(s,3H);2.29(s,3H);
实施例编号1-20:1H-NMR(400MHz,DMSO-d6):δ=11.82(br s,1H);7.85(d,1H);7.82(d,1H);4.01(s,3H);3.60(m,1H);3.45(m,1H);3.05(m,2H);3.00(s,3H);2.71(s,3H);2.30(s,3H);1.14(t,3H);1.02(t,3H);
实施例编号1-21:1H-NMR(400MHz,DMSO-d6):δ=11.79(br s,1H);7.84(d,1H);7.80(d,1H);4.01(s,3H);2.98(s,3H);2.88(m,1H);2.31(s,3H);0.81(m,2H);0.47(m,,2H);
实施例编号1-24:1H-NMR(400MHz,DMSO-d6):δ=11.81(br s,1H);7.89(d,1H);7.85(d,1H);6.30(tt,1H);4.02(s,3H);3.98(m,2H);2.84(s,3H);2.33(s,3H);
实施例编号1-31:1H-NMR(400MHz,DMSO-d6):δ=11.80(br s,1H);7.85(d,1H);7.81(d,1H);4.01(s,3H);3.56(m,1H);3.45(m,1H);3.06(m,2H);2.32(s,3H);1.16(t,3H);1.01(t,3H);
实施例编号1-32:1H-NMR(400MHz,DMSO-d6):δ=11.79(br s,1H);7.84(d,1H);7.80(d,1H);4.01(s,3H);3.55(m,1H);3.45(m,1H);2.51(m,1H);2.32(s,3H);1.16(t,3H);0.48(m,4H);
实施例编号1-40:1H-NMR(400MHz,DMSO-d6):δ=11.78(br s,1H);7.84(d,1H);7.79(d,1H);4.01(s,3H);2.67(m,1H);2.36(m,1H);2.29(s,3H);0.86(m,2H);0.81(m,2H);0.60(m,2H);0.46(m,2H);
实施例编号1-50:1H-NMR(400MHz,DMSO-d6):δ=11.72(br s,1H);7.80(d,1H);7.66(d,1H);6.89(t,1H);4.00(s,3H);3.05(s,3H);2.74(s,3H);2.28(s,3H);
实施例编号1-51:1H-NMR(400MHz,DMSO-d6):δ=11.72(br s,1H);7.79(d,1H);7.67(d,1H);6.89(t,1H);4.00(s,3H);3.54(m,2H);3.02(s,3H);2.29(s,3H);1.16(t,3H);
实施例编号1-59:1H-NMR(400MHz,DMSO-d6):δ=11.73(br s,1H);7.80(d,1H);7.68(d,1H);6.86(t,1H);4.01(s,3H);3.59(m,1H);3.47(m,1H);3.07(m,2H);2.31(s,3H);1.19(t,3H);0.99(t,3H);
实施例编号1-123:1H-NMR(400MHz,DMSO-d6):δ=12.01(br s,1H);8.00(s,2H);4.02(s,3H);3.04(s,3H);2.78(s,3H);
实施例编号1-124:1H-NMR(400MHz,DMSO-d6):δ=12.01(br s,1H);8.00(s,2H);4.02(s,3H);3.58(m,1H);3.48(m,1H);3.10(m,2H);3.01(s,3H);2.76(s,3H);1.14(t,3H);1.07(t,3H);
实施例编号1-125:1H-NMR(400MHz,DMSO-d6):δ=12.03(br s,1H);8.00(d,2H);4.01(s,3H);3.00(s,3H);2.60(m,1H);0.82(m,1H);0.72(m,1H);0.50(m,2H);
实施例编号1-126:1H-NMR(400MHz,DMSO-d6):δ=12.02(br s,1H);8.00(s,2H);4.02(br s,3H);3.43(m,2H);3.36(m,2H);3.11(s,3H);2.94(2,2H);2.83(s,3H);1.09(m,1H);0.86(m,1H);0.51(m,4H);0.32(m,2H);0.13(m,2H);
实施例编号1-128:1H-NMR(400MHz,DMSO-d6):δ=12.038(br s,1H);8.04(br s,2H);6.27(tt,1H);4.02(s,3H);4.00(m,2H);2.89(s,3H);
实施例编号1-135:1H-NMR(400MHz,DMSO-d6):δ=12.03(br s,1H);8.00(br s,2H);4.02(t,3H);3.55(m,1H);3.46(m,1H);3.10(m,2H);1.16(t,3H);1.05(t,3H);
实施例编号1-136:1H-NMR(400MHz,DMSO-d6):δ=12.06(br s,1H);8.00(br s,2H);4.02(s,3H);3.64(br s,1H);3.53(m,2H);1.17(t,3H);0.71(m,1H);0.51(m,3H);
实施例编号1-144:1H-NMR(400MHz,DMSO-d6):δ=12.03(br s,1H);7.99(br s,2H);4.01(s,3H);2.68(m,1H);0.83(m,5H);0.52(m,3H);
实施例编号1-152:1H-NMR(400MHz,DMSO-d6):δ=12.01(br s,1H);8.00(s,2H);4.02(s,3H);3.51(m,2H);3.12(m,1H);3.02(m,1H);1.88(m,4H);
实施例编号1-153:1H-NMR(400MHz,DMSO-d6):δ=12.11(br s,1H);8.75(br s,1H);8.20(d,1H);8.14(d,1H);7.97(s,1H);6.81(br s,1H);4.01(s,3H);
实施例编号1-154:1H-NMR(400MHz,DMSO-d6):δ=11.98(br s,1H);7.93(d,1H);7.82(d,1H);6.98(t,1H);4.01(s,3H);3.05(s,3H);2.78(s,3H);
实施例编号1-155:1H-NMR(400MHz,DMSO-d6):δ=11.97(br s,1H);7.93(br d,1H);7.82(d,1H);6.98(t,1H);4.02(s,3H);3.54(m,1H);3.02(m,1H);2.76(s,3H);1.16(t,3H);
实施例编号1-156:1H-NMR(400MHz,DMSO-d6):δ=11.99(br s,1H);7.93(d,1H);7.81(d,1H);6.96(t,1H);4.02(s,3H);3.02(s,3H);2.65(m,1H);0.79(m,1H);0.52(m,1H);0.44(m,2H);
实施例编号1-159:1H-NMR(400MHz,DMSO-d6):δ=11.99(br s,1H);7.99(d,1H);7.87(d,1H);7.01(t,1H);6.31(tt,1H);4.02(s,3H);3.98(m,2H);2.88(s,3H);
实施例编号1-166:1H-NMR(400MHz,DMSO-d6):δ=11.97(br s,1H);7.94(d,1H);7.82(d,1H);4.02(s,3H);3.59(m,1H);3.48(m,1H);3.10(m,2H);1.18(t,3H);1.04(t,3H);
实施例编号1-167:1H-NMR(400MHz,DMSO-d6):δ=11.99(br s,1H);7.92(d,1H);7.82(d,1H);6.94(t,1H);4.01(s,3H);3.73(m,1H);3.32(m,1H);2.68(m,1H);1.20(t,3H);0.69(m,1H);0.57(m,1H);0.42(m,2H);
实施例编号1-175:1H-NMR(400MHz,DMSO-d6):δ=11.98(br s,1H);7.92(br s,1H);7.82(d,1H);6.99(t,1H);4.01(s,3H);2.72(m,1H);2.50(m,1H);0.84(m,5H);0.59(m,1H);0.49(m,1H);0.40(m,1H);
实施例编号1-191:1H-NMR(400MHz,DMSO-d6):δ=11.91(br s,1H);7.87(d,1H);7.72(d,1H);4.00(s,3H);3.05(s,3H);2.82(s,3H);
实施例编号1-192:1H-NMR(400MHz,DMSO-d6):δ=11.91(br s,1H);7.87(d,1H);7.71(d,1H);4.00(s,3H);3.54(m 2H);3.02(s,3H);1.17(t,3H);
实施例编号1-200:1H-NMR(400MHz,DMSO-d6):δ=11.91(br s,1H);7.86(d,1H);7.71(d,1H);4.35(q,2H);3.99(s,3H);3.51(m,2H);3.13(m,2H);1.19(t,3H);1.09(t,3H);
实施例编号1-395:1H-NMR(400MHz,DMSO-d6):δ=11.82(br s,1H);7.95(d,1H);7.89(d,1H);4.01(s,3H);3.25(s,3H);3.01(s,3H);2.72(s,3H);2.31(s,3H);
实施例编号1-398:1H-NMR(400MHz,DMSO-d6):δ=11.83(s,1H);7.89(d,1H);7.81(d,1H);7.37-7.22(m,4H);4.02(s,3H);3.19(s,3H);
实施例编号1-399:1H-NMR(400MHz,DMSO-d6):δ=11.96(s,1H);7.86(d,1H);7.82(d,1H);7.38-7.25(m,3H);4.00(s,3H);3.09(s,3H);2.34(s,3H);
实施例编号1-400:1H-NMR(400MHz,DMSO-d6):δ=12.04(br s,1H);8.03(m,2H);4.48(m,1H);4.15(q,2H);4.02(t,3H);3.21(m,1H);2.31(m,1H);1.95(m,4H);1.21(t,3H);
实施例编号1-401:1H-NMR(400MHz,DMSO-d6):δ=11.80(br s,1H);7.87(d,1H);7.83(d,1H);4.56(m,1H);4.16(q,2H);4.02(s,3H);3.21(m,1H);3.08(m,1H);2.48(s,3H);2.31(m,1H);1.90(m,2H);1.23(t,3H);
实施例编号1-402:1H-NMR(400MHz,DMSO-d6):δ=11.98(br s,1H);8.01(d,1H);7.72(d,1H);7.00(t,1H);4.60(m,1H);4.21(m,2H);4.02(s,3H);3.28(m,1H);3.29(m,1H);2.38(m,1H);1.98(m,1H);1.91(m,2H);1.25(t,3H);
实施例编号2-19:1H-NMR(400MHz,DMSO-d6):δ=11.69(br s,1H);7.84(d,1H);7.81(d,1H);4.36(q,2H);3.04(s,3H);2.74(s,3H);2.29(s,3H);1.48(t,3H);
实施例编号2-21:1H-NMR(400MHz,DMSO-d6):δ=11.68(br s,1H);7.82(d,1H);7.80(d,1H);4.36(q,2H);2.98(s,3H);2.88(m,1H);2.30(s,3H);1.48(t,3H);0.82(m,1H);0.73(m,1H);0.52(m,1H);0.46(m,1H);
实施例编号2-31:1H-NMR(400MHz,DMSO-d6):δ=11.70(br s,1H);7.84(d,1H);7.81(d,1H);4.36(q,2H);3.57(m,1H);3.46(m,1H);3.07(m,2H);2.31(s,3H);1.48(t,3H);1.16(t,3H);1.01(t,3H);
实施例编号2-32:1H-NMR(400MHz,DMSO-d6):δ=11.68(br s,1H);7.83(d,1H);7.80(d,1H);4.36(q,2H);3.55(m,1H);3.45(m,1H);2.51(m,1H);2.32(s,3H);1.48(t,3H);1.16(t,3H);0.51(m,4H);
实施例编号2-50:1H-NMR(400MHz,DMSO-d6):δ=11.62(br s,1);7.89(d,1H);7.66(d,1H);6.89(t,1H);4.35(q,2H);3.05(s,3H);2.74(s,3H);2.28(s,3H);1.48(t,3H);
实施例编号2-51:1H-NMR(400MHz,DMSO-d6):δ=11.62(br s,1H);7.79(d,1H);7.67(d,1H);6.89(t,1H);4.35(q,2H);3.53(m,2H);3.03(s,3H);2.29(s,3H);1.48(t,3H);1.17(t,3H);
实施例编号2-59:1H-NMR(400MHz,DMSO-d6):δ=11.63(br s,1H);7.79(d,1H);7.68(d,1H);6.86(t,1H);4.35(q,2H);3.60(m,1H);3.46(m,1H);3.07(m,2H);2.30(s,3H);1.48(t,3H);1.19(t,3H);0.99(s,3H);
实施例编号2-123:1H-NMR(400MHz,DMSO-d6):δ=11.92(br s,1H);8.00(s,2H);4.38(q,2H);3.04(s,3H);2.79(s,3H);1.48(t,3H);
实施例编号2-124:1H-NMR(400MHz,DMSO-d6):δ=11.92(br s,1H);7.99(s,2H);4.38(q,2H);3.58(m,1H);3.47(m,1H);3.10(m,2H);3.00(s,3H);2.76(s,3H);1.48(t,3H);1.14(t,3H);1.07(t,3H);
实施例编号2-125:1H-NMR(400MHz,DMSO-d6):δ=11.94(br s,1H);7.99(d,2H);4.37(q,2H);3.00(s,3H);2.59(m,1H);1.47(t,3H);0.81(m,1H);0.70(m,1H);0.49(m,2H);
实施例编号2-126:1H-NMR(400MHz,DMSO-d6):δ=11.92(br s,1H);8.00(s,2H);4.38(q,2H);3.44(m,1H);3.35(m,1H);3.11(s,3H);2.94(m,2H);2.83(s,3H);1.48(t,3H);1.08(m,1H);0.86(m,1H);0.50(m,4H);0.32(m,2H);0.13(m,2H);
实施例编号2-128:1H-NMR(400MHz,DMSO-d6):δ=11.95(br s,1H);8.04(br s,2H);6.27(tt,1H);4.38(q,2H);3.98(m,2H);2.89(s,3H);1.48(t,3H);
实施例编号2-135:1H-NMR(400MHz,DMSO-d6):δ=11.93(br s,1H);7.99(br s,2H);4.37(q,2H);3.55(m,1H);3.47(m,1H);3.09(m,2H);1.47(t,3H);1.16(t,3H);1.05(t,3H);
实施例编号2-136:1H-NMR(400MHz,DMSO-d6):δ=11.94(br s,1H);7.99(br s,2H);4.37(q,2H);3.05(m,1H);3.48(m,1H);3.00(m,1H);1.49(t,3H);1.18(t,3H);0.70(m,2H);0.51(m,2H);
实施例编号2-144:1H-NMR(400MHz,DMSO-d6):δ=11.93(br s,1H);7.99(br s,2H);4.37(q,2H);2.68(m,2H);1.47(t,3H);0.85(m,5H);0.52(m,3H);
实施例编号2-152:1H-NMR(400MHz,DMSO-d6):δ=11.92(br s,1H);8.00(s,2H);4.38(q,2H);3.51(m,2H);3.12(m,1H);3.04(m,1H);1.88(m,4H);1.48(t,3H);
实施例编号2-153:1H-NMR(400MHz,DMSO-d6):δ=12.00(br s,1H);8.75(br s,1H);8.19(d,1H);8.14(d,1H);7.97(s,1H);6.81(br s,1H);4.36(q,2H);1.47(t,3H);
实施例编号2-154:1H-NMR(400MHz,DMSO-d6):δ=11.89(br s,1H);7.93(d,1H);7.82(d,1H);6.98(t,1H);4.37(q,2H);3.05(s,3H);2.78(s,3H);1.48(t,3H);
实施例编号2-155:1H-NMR(400MHz,DMSO-d6):δ=11.87(br s,1H);7.91(br s,1H);7.82(d,1H);6.98(t,1H);4.37(q,2H);3.53(m,1H);3.02(m,1H);2.76(s,3H);1.47(t,3H);1.16(t,3H);
实施例编号2-156:1H-NMR(400MHz,DMSO-d6):δ=11.87(br s,1H);7.92(d,1H);7.80(d,1H);6.96(t,1H);4.37(q,2H);3.02(s,3H);2.67(m,1H);1.48(t,3H);0.80(m,1H);0.52(m,1H);0.43(m,2H);
实施例编号2-159:1H-NMR(400MHz,DMSO-d6):δ=11.89(br s,1H);7.97(d,1H);7.85(d,1H);7.01(t,1H);6.31(tt,1H);4.38(q,2H);3.98(m,2H);2.88(s,3H);1.48(t,3H);
实施例编号2-166:1H-NMR(400MHz,DMSO-d6):δ=11.88(br s,1H);7.93(d,1H);7.82(d,1H);6.95(t,1H);4.37(q,2H);3.58(m,1H);3.48(m,1H);3.10(m,2H);1.48(t,3H);1.18(t,3H);1.04(t,3H);
实施例编号2-167:1H-NMR(400MHz,DMSO-d6):δ=11.87(br s,1H);7.92(br s,1H);7.82(d,1H);6.94(t,1H);4.37(q,2H);3.74(m,1H);3.33(m,1H);2.67(m,1H);1.48(t,3H);1.20(t,3H);0.69(m,1H);0.57(m,1H);0.41(m,2H);
实施例编号2-175:1H-NMR(400MHz,DMSO-d6):δ=11.86(br s,1H);7.90(br s,1H);7.82(d,1H);6.99(t,1H);4.37(q,2H);2.72(m,1H);2.50(m,1H);1.47(t,3H);0.85(m,5H);0.59(m,1H);0.50(m,1H);0.40(m,1H);
实施例编号2-191:1H-NMR(400MHz,DMSO-d6):δ=11.81(br s,1H);7.87(d,1H);7.71(d,1H);4.35(q,2H);3.05(s,3H);2.82(s,3H);1.47(t,3H);
实施例编号2-192:1H-NMR(400MHz,DMSO-d6):δ=11.81(br s,1H);7.87(d,1H);7.70(d,1H);4.36(q,2H);3.54(m,2H);3.02(s,3H);1.47(t,3H);1.17(t,3H);
实施例编号2-200:1H-NMR(400MHz,DMSO-d6):δ=11.82(br s,1H);7.86(d,1H);7.70(d,1H);4.35(q,2H);3.52(m,2H);3.13(m,2H);1.46(t,3H);1.19(t,3H);1.09(t,3H);
实施例编号2-340:1H-NMR(400MHz,DMSO-d6):δ=11.89(br s,1H);8.00(d,1H);7.92(d,1H);7.00(t,1H);4.60(m,1H);4.38(q,2H);4.20(m,2H);3.28(m,1H);3.19(m,1H);2.37(m,1H);1.99(m,1H);1.92(m,2H);1.49(t,3H);1.25(t,3H);
实施例编号2-398:1H-NMR(400MHz,DMSO-d6):δ=11.94(br s,1H);8.02(br s,1H);4.47(m,1H);4.38(m,2H);4.15(m,2H);3.21(m,1H);3.31(m,1H);1.96(m,4H);1.49(t,3H);1.22(t,3H);
实施例编号3-123:1H-NMR(400MHz,DMSO-d6):δ=11.90(br s,1H);7.99(s,2H);4.32(t,2H);3.04(s,3H);2.79(s,3H);1.89(m,2H);0.88(t,3H);
实施例编号3-124:1H-NMR(400MHz,DMSO-d6):δ=11.90(br s,1H);7.99(s,2H);4.32(t,2H);3.59(m,1H);3.46(m,1H);3.10(m 2H);3.00(s,3H);2.76(s,3H);1.89(m,2H);1.14(t,3H);1.06(t,3H);0.88(t,3H);
实施例编号3-126:1H-NMR(400MHz,DMSO-d6):δ=11.91(br s,1H);7.99(s,2H);4.33(t,2H);3.45(m,1H);3.35(m,1H);3.11(s,3H);2.94(m,2H);2.83(s,3H);1.89(m,2H);1.08(m,1H);0.88(t,3H);0.85(m,1H);0.51(m,4H);0.32(m,2H);0.13(m,2H);
实施例编号3-152:1H-NMR(400MHz,DMSO-d6):δ=11.91(br s,1H);7.99(s,2H);4.32(t,2H);3.50(m,2H);3.12(m,1H);3.04(m,1H);1.89(m,6H);0.88(t,3H);
实施例编号3-153:1H-NMR(400MHz,DMSO-d6):δ=11.98(br s,1H);8.75(s,1H);8.18(d,1H);8.14(d,1H);7.97(s,1H);6.81(s,1H);4.31(t,2H);1.88(m,2H);0.88(t,3H).
B.制剂实施例
a)通过如下方法获得撒粉产品:将10重量份式(I)的化合物和/或其盐与90重量份作为惰性物质的滑石混合,并将混合物在锤磨机中粉碎。
b)通过如下方法获得易于水分散的可湿性粉剂:将25重量份式(I)的化合物和/或其盐、64重量份作为惰性物质的含高岭土的石英、10重量份的木素磺酸钾和1重量份的作为润湿剂和分散剂的油酰基甲基牛磺酸钠混合,将混合物在销盘式研磨机(pinned-diskmill)中研磨。
c)通过如下方法获得易于水分散的分散浓缩剂:将20重量份式(I)的化合物和/或其盐与6重量份的烷基酚聚乙二醇醚(X 207)、3重量份的异十三醇聚乙二醇乙醚(8EO)和71重量份的石蜡矿物油(沸程为例如约255℃至高于277℃)混合,并将混合物在摩擦球磨机中研磨至低于5微米的细度。
d)通过如下方法获得乳油:将15重量份式(I)的化合物和/或其盐、75重量份作为溶剂的环己酮和10重量份作为乳化剂的乙氧基化壬基苯酚混合。
e)通过如下方法得到水分散性颗粒剂:
将如下物质混合
75重量份式(I)的化合物和/或其盐、
10重量份的木素磺酸钙、
5重量份的十二烷基硫酸钠、
3重量份的聚乙烯醇和
7重量份的高岭土,
将混合物在销盘式研磨机中研磨,并在流化床中通过喷雾施用作为制粒液体的水而粒化该粉末。
f)通过如下方法得到水分散性颗粒剂:
将以下物质在胶体磨机中均匀化并预粉碎
25重量份式(I)的化合物和/或其盐、
5重量份的2,2'-二萘基甲烷-6,6'-二磺酸钠、
2重量份的油酰基甲基牛磺酸钠、
1重量份的聚乙烯醇、
17重量份的碳酸钙和
50重量份的水,
随后在球磨机中研磨该混合物,并将所得悬浮液在喷雾塔中通过单相喷嘴雾化并干燥。
C.生物学实施例
用于有害植物的缩写意指:
ABUTH 苘麻(Abutilon theophrasti) ALOMY 大穗看麦娘(Alopecurus myosuroides)
AVEFA 野燕麦(Avena fatua) AMARE 反枝苋(Amaranthus retroflexus)
CYPES 水莎草(Cyperus esculentus) DIGSA 马唐(Digitaria sanguinalis)
ECHCG 稗草(Echinochloa crus-galli) HORMU 鼠大麦(Hordeum murinum)
LOLMU 多花黑麦草(Lolium multiflorum) LOLRI 硬直黑麦草(Lolium rigidum)
MATIN 淡甘菊(Matricaria inodora) PHBPU 圆叶牵牛(Pharbitis purpurea)
POLCO 卷茎蓼(Polygonum convolvulus) SETVI 狗尾草(Setaria viridis)
STEME 繁缕(Stellaria media) VERPE 阿拉伯婆婆纳(Veronica persica)
VIOTR 三色堇(Viola tricolor)
1.对有害植物的出苗前除草作用
将单子叶或双子叶杂草植物和作物植物的种子置于木纤维盆中的沙质壤土中,并用土壤覆盖。然后将本发明的化合物(以可湿性粉剂(WP)的形式或作为乳油(EC)配制)以水性悬浮液或乳液的形式施用于所覆盖土壤的表面,水施用率等同于600至800L/ha,同时加入0.2%的润湿剂。在处理后,将盆置于温室中,并将温室条件保持在对测试植物而言良好的生长条件下。在3周的测试期后,通过与未处理的对照组相比较,目测评估对测试植物的伤害(除草活性百分比(%):100%活性=植物已死亡,0%活性=与对照植物相同)。本发明的许多化合物对许多重要的有害植物表现出非常好的作用。下表以示例性的方式示出了本发明的化合物的苗后除草作用,除草活性以百分比表示。
表1a:在20g/ha下以%计的对ABUTH的苗前作用
表1b:在80g/ha下以%计的对ABUTH的苗前作用
表1c:在320g/ha下以%计的对ABUTH的苗前作用
表2a:在20g/ha下以%计的对ALOMY的苗前作用
表2b:在80g/ha下以%计的对ALOMY的苗前作用
表2c:在320g/ha下以%计的对ALOMY的苗前作用
表3a:在20g/ha下以%计的对AMARE的苗前作用
表3b:在80g/ha下以%计的对AMARE的苗前作用
表3c:在320g/ha下以%计的对AMARE的苗前作用
表4a:在20g/ha下以%计的对AVEFA的苗前作用
表4b:在80g/ha下以%计的对AVEFA的苗前作用
表4c:在320g/ha下以%计的对AVEFA的苗前作用
表5a:在20g/ha下以%计的对CYPES的苗前作用
表5b:在80g/ha下以%计的对CYPES的苗前作用
表5c:在320g/ha下以%计的对CYPES的苗前作用
表6a:在20g/ha下以%计的对ECHCG的苗前作用
表6b:在80g/ha下以%计的对ECHCG的苗前作用
表6c:在320g/ha下以%计的对ECHCG的苗前作用
表7a:在20g/ha下以%计的对MATIN的苗前作用
表7b:在80g/ha下以%计的对MATIN的苗前作用
表7c:在320g/ha下以%计的对MATIN的苗前作用
表8a:在80g/ha下以%计的对PHBPU的苗前作用
表8b:在320g/ha下以%计的对PHBPU的苗前作用
表9a:在20g/ha下以%计的对POLCO的苗前作用
表9b:在80g/ha下以%计的对POLCO的苗前作用
表9c:在320g/ha下以%计的对POLCO的苗前作用
表10a:在20g/ha下以%计的对SETVI的苗前作用
表10b:在80g/ha下以%计的对SETVI的苗前作用
表10c:在320g/ha下以%计的对SETVI的苗前作用
表11a:在20g/ha下以%计的对STEME的苗前作用
表11b:在80g/ha下以%计的对STEME的苗前作用
表11c:在320g/ha下以%计的对STEME的苗前作用
表12a:在20g/ha下以%计的对VERPE的苗前作用
表12b:在80g/ha下以%计的对VERPE的苗前作用
表12c:在320g/ha下以%计的对VERPE的苗前作用
表13a:在20g/ha下以%计的对VIOTR的苗前作用
表13b:在80g/ha下以%计的对VIOTR的苗前作用
表13c:在320g/ha下以%计的对VIOTR的苗前作用
表14a:在80g/ha下以%计的对LOLRI的苗前作用
表14b:在320g/ha下以%计的对LOLRI的苗前作用
表15a:在80g/ha下以%计的对HORMU的苗前作用
表15b:在320g/ha下以%计的对HORMU的苗前作用
表16a:在20g/ha下以%计的对DIGSA的苗前作用
表16b:在80g/ha下以%计的对DIGSA的苗前作用
2.对有害植物的苗后除草作用
将单子叶和双子叶杂草植物和作物植物的种子置于木纤维盆中的沙质壤土中,并用土壤覆盖,并于温室中在良好的生长条件下培育。在播种后2至3周,在单叶期处理试验植物。然后,将本发明的化合物(以可湿性粉剂(WP)形式或作为乳油(EC)配制)以水性悬浮液或乳液的形式喷洒至植物的绿色部位上,水施用率等同于600至800L/ha,同时添加0.2%的润湿剂。在将试验植物置于最佳生长条件的温室中约3周后,通过与未处理的对照组比较,目测评估制剂的作用(除草作用百分比(%):100%活性=植物死亡,0%活性=与对照植物相同)。本发明的许多化合物对许多重要的有害植物表现出良好的作用。下表以示例性的方式示例性说明了本发明化合物的苗后除草作用,除草活性以百分比表示。
表17a:在5g/ha下以%计的对ABUTH的苗后作用
表17b:在20g/ha下以%计的对ABUTH的苗后作用
表17c:在80g/ha下以%计的对ABUTH的苗后作用
表18a:在5g/ha下以%计的对ALOMY的苗后作用
表18b:在20g/ha下以%计的对ALOMY的苗后作用
表18c:在80g/ha下以%计的对ALOMY的苗后作用
表19a:在5g/ha下以%计的对AMARE的苗后作用
表19b:在20g/ha下以%计的对AMARE的苗后作用
表19c:在80g/ha下以%计的对AMARE的苗后作用
表20a:在5g/ha下以%计的对AVEFA的苗后作用
表20b:在20g/ha下以%计的对AVEFA的苗后作用
表20c:在80g/ha下以%计的对AVEFA的苗后作用
表21a:在5g/ha下以%计的对CYPES的苗后作用
表21b:在20g/ha下以%计的对CYPES的苗后作用
表21c:在80g/ha下以%计的对CYPES的苗后作用
表22a:在5g/ha下以%计的对ECHCG的苗后作用
表22b:在20g/ha下以%计的对ECHCG的苗后作用
表22c:在80g/ha下以%计的对ECHCG的苗后作用
表23a:在5g/ha下以%计的对MATIN的苗后作用
表23b:在20g/ha下以%计的对MATIN的苗后作用
表23c:在80g/ha下以%计的对MATIN的苗后作用
表24a:在5g/ha下以%计的对PHBPU的苗后作用
表24b:在20g/ha下以%计的对PHBPU的苗后作用
表24c:在80g/ha下以%计的对PHBPU的苗后作用
表25a:在5g/ha下以%计的对POLCO的苗后作用
表25b:在20g/ha下以%计的对POLCO的苗后作用
表25c:在80g/ha下以%计的对POLCO的苗后作用
表26a:在5g/ha下以%计的对SETVI的苗后作用
表26b:在20g/ha下以%计的对SETVI的苗后作用
表26c:在80g/ha下以%计的对SETVI的苗后作用
表27a:在5g/ha下以%计的对STEME的苗后作用
表27b:在20g/ha下以%计的对STEME的苗后作用
表27c:在80g/ha下以%计的对STEME的苗后作用
表28a:在5g/ha下以%计的对VERPE的苗后作用
表28b:在20g/ha下以%计的对VERPE的苗后作用
表28c:在80g/ha下以%计的对VERPE的苗后作用
表29a:在5g/ha下以%计的对VIOTR的苗后作用
表29b:在20g/ha下以%计的对VIOTR的苗后作用
表29c:在80g/ha下以%计的对VIOTR的苗后作用
表30a:在5g/ha下以%计的对LOLRI的苗后作用
表30b:在80g/ha下以%计的对LOLRI的苗后作用
表31a:在5g/ha下以%计的对HORMU的苗后作用
表31b:在20g/ha下以%计的对HORMU的苗后作用
表31c:在80g/ha下以%计的对HORMU的苗后作用
表32a:在5g/ha下以%计的对DIGSA的苗后作用
表32b:在20g/ha下以%计的对DIGSA的苗后作用
对比实验
在随后的实验中,在上述苗前和苗后方式的特定的条件下,将许多本发明的化合物和由D1(WO 2012/028579 A1)已知的结构最接近的化合物的除草作用进行比较。表中给出的实施例编号涉及的是各文献中公开的化合物。
表5:苗前除草作用
表6:苗后除草作用
Claims (12)
1.式(I)的间苯二甲酰胺或其盐
其中所述符号和角标定义如下:
Q为Q1或Q2
W为氮,
X为卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、R1O、R2(O)nS、R1O-(C1-C6)-烷基或R2S(O)n-(C1-C6)-烷基,
Y为卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、R1O或R2(O)nS,
条件为当X为氯时,Y不为甲基磺酰基,
Z1,Z2彼此独立地为各自被s个选自卤素、氰基、R1C(O)、R1OC(O)、R1O和R2(O)nS的基团取代的以下基团:(C1-C6)-烷基、(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、(C1-C6)-烷基-O-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-烯基-(C1-C6)-烷基、(C2-C6)-炔基、(C2-C6)-炔基-(C1-C6)-烷基、(C1-C6)-烷氧基、R2S(O)n-(C1-C6)-烷基、R1C(O)、R1OC(O)、R1C(O)-(C1-C6)-烷基、R1OC(O)-(C1-C6)-烷基、R1NH-(C1-C6)-烷基、R1 2N-(C1-C6)-烷基、R1NHC(O)-(C1-C6)-烷基或R1 2NC(O)-(C1-C6)-烷基,
或
各自被s个选自卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、R1C(O)和R1OC(O)的基团取代的以下基团:苯基、苯甲基、杂环或杂环-(C1-C6)-烷基,
或
Z1和Z2与它们所连接的氮原子一起形成四-、五-、六-或七-元杂环,所述杂环包含n个选自O、S和N的其他杂原子作为环原子,并被m个选自羰基、卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基和卤代-(C1-C6)-烷氧基的基团取代,
R1为(C1-C6)-烷基、卤代-(C1-C6)-烷基或(C3-C6)-环烷基,
R2为(C1-C6)-烷基,
Rx为(C1-C6)-烷基、(C1-C6)-烷基-O-(C1-C6)-烷基或苯基,
m为0、1、2或3,
n为0、1或2,
s为0、1、2、3或4。
2.根据权利要求1所述的间苯二甲酰胺,其中
Q为Q1或Q2
Rx为Me、Et、Pr、i-Pr、c-Pr、(CH2)2OMe或Ph,
W为氮,
X为卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、cPr、OMe、OEt、SMe、SEt、CH2OMe或CH2SMe,
Y为卤素、卤代-(C1-C6)-烷基、OMe、SMe、S(O)Me、SO2Me、SEt、S(O)Et或SO2Et,
条件为当X为氯时,Y不为甲基磺酰基,
Z1,Z2独立地为(C1-C6)-烷基、(C3-C6)-环烷基、CH2cPr、卤代-(C1-C6)-烷基、(CH2)2OMe、(CH2)2SMe、烯丙基、炔丙基、C(O)CH3、C(O)-c-Pr、CO2Me、CO2Et、Ph、(2-Me)Ph、(4-F)Ph、CH2C(O)NMe2、CH2C(O)Me或CH2C(O)cPr,
或Z1和Z2同为(CH2)3或(CH2)4,
或W、Z1和Z2同为吡唑-1-基或L-脯氨酸-1-基乙酯。
3.根据权利要求1或2所述的间苯二甲酰胺,其中
Q为Q1或Q2,
Rx为Me、Et或Pr,
W为氮,
X为F、Cl、Br、I、Me、Et、c-Pr、OMe、SMe、SEt、CH2OMe,
Y为F、Cl、Br、I、SMe、S(O)Me、SO2Me、CHF2、CF3或C2F5,
条件为当X为氯时,Y不为甲基磺酰基,
Z1,Z2独立地为Me、Et、c-Pr、CH2-c-Pr、CH2CHF2、CH2CF3、C(O)CH3、C(O)-c-Pr、CO2Me、CO2Et、Ph或(2-Me)Ph,
或Z1和Z2同为(CH2)4,
或W、Z1和Z2同为吡唑-1-基或L-脯氨酸-1-基乙酯,
R1为Me、Et或c-Pr,
R2为Me。
4.除草组合物或植物生长调节组合物,其特征在于,所述组合物包含根据权利要求1至3中任一项所述的一种或多种通式(I)的间苯二甲酰胺或其盐。
5.根据权利要求4所述的除草组合物,还包含制剂助剂。
6.根据权利要求4或5所述的除草组合物,包含至少一种选自杀昆虫剂、杀螨剂、除草剂、杀真菌剂、安全剂和/或生长调节剂的其他活性成分。
7.根据权利要求4或5所述的除草组合物,包含安全剂。
8.根据权利要求7所述的除草组合物,其中所述安全剂选自吡唑解草酯、环丙磺酰胺、双苯噁唑酸、解毒喹、解草嗪和烯丙酰草胺。
9.防治不想要的植物的方法,其特征在于,将有效量的至少一种根据权利要求1至3中任一项所述的式(I)的间苯二甲酰胺或根据权利要求4至8中任一项所述的除草组合物施用至植物或不想要的植被的位置。
10.根据权利要求1至3中任一项所述的式(I)的化合物或根据权利要求4至8中任一项所述的除草组合物用于防治不想要的植物的用途。
11.根据权利要求10所述的用途,其特征在于,将式(I)的间苯二甲酰胺用于防治有用植物作物中不想要的植物。
12.根据权利要求11所述的用途,其特征在于,所述有用植物为转基因有用植物。
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AR121785A1 (es) | 2022-07-06 |
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AU2021253460A1 (en) | 2022-11-03 |
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