CN103391925B - 5‑卤代吡唑甲酰胺 - Google Patents
5‑卤代吡唑甲酰胺 Download PDFInfo
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- CN103391925B CN103391925B CN201180065040.9A CN201180065040A CN103391925B CN 103391925 B CN103391925 B CN 103391925B CN 201180065040 A CN201180065040 A CN 201180065040A CN 103391925 B CN103391925 B CN 103391925B
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- XNQULTQRGBXLIA-UHFFFAOYSA-O phosphonic anhydride Chemical compound O[P+](O)=O XNQULTQRGBXLIA-UHFFFAOYSA-O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 230000037039 plant physiology Effects 0.000 description 1
- 230000004260 plant-type cell wall biogenesis Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- JPFWJDMDPLEUBD-ITJAGOAWSA-N polyoxorim Chemical compound O[C@@H]1[C@H](O)[C@@H]([C@H](NC(=O)[C@H]([C@H](O)[C@@H](O)COC(N)=O)N)C(O)=O)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 JPFWJDMDPLEUBD-ITJAGOAWSA-N 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- VBKNTGMWIPUCRF-UHFFFAOYSA-M potassium;fluoride;hydrofluoride Chemical compound F.[F-].[K+] VBKNTGMWIPUCRF-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 229960003761 propamidine Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- BAUQXSYUDSNRHL-UHFFFAOYSA-N pyrimorph Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=1C=NC(Cl)=CC=1)=CC(=O)N1CCOCC1 BAUQXSYUDSNRHL-UHFFFAOYSA-N 0.000 description 1
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036301 sexual development Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004564 water dispersible powder for slurry treatment Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000004549 water soluble granule Substances 0.000 description 1
- 239000004554 water soluble tablet Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及新颖的5‑卤代吡唑(硫代)甲酰胺、它们的制备方法、它们作为杀真菌剂活性剂(特别是以杀真菌剂组合物的形式)的用途,以及用这些化合物或组合物来防治植物病原性真菌(特别是植物的植物病原性真菌)的方法。
Description
本发明涉及新颖的5-卤代吡唑(硫代)甲酰胺、它们的制备方法、它们作为杀真菌剂活性剂(特别是以杀真菌剂组合物的形式)的用途,以及用这些化合物或组合物来防治植物病原性真菌(特别是植物的植物病原性真菌)的方法。
已知的是,众多甲酰胺具有杀真菌性能(参见,例如,WO–A 1998/03495、WO-A1998/03486和EP-A 0 589 313)。因而,1-甲基-3-三氟甲基-5-氟-吡唑甲酰胺和1,3-二甲基氟代吡唑甲酰胺是已知的(WO-A 2006/061215、WO-A 2005/042494、WO-A 2005/042493、WO-A 2008/095890、WO-A 2004/035589、WO-A 2003/074491)。这些化合物的活性良好;但是,在某些情况下,例如在低施用率下,所述活性有时不能令人满意。
本发明现在提供了新颖的式(I)的1-甲基-3-二卤代甲基-5-卤代吡唑(硫代)甲酰胺
其中
T代表氧或硫原子;
R代表氢、C1-C6-烷基磺酰基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-卤代烷基磺酰基、卤代-C1-C4-烷氧基-C1-C4-烷基或甲酰基;
Hal1和Hal2彼此独立地代表氯或氟;
L代表苯基,所述苯基可以被至多4个相同或不同的基团R1取代;
Q代表苯基,所述苯基可以被至多5个相同或不同的基团Rb取代;或者
Q代表卤素;硝基;氰基;异腈;羟基;氨基;硫烷基;五氟-λ6-硫烷基;甲酰基;甲酰基氧基;甲酰基氨基;任选地被取代的(肟基)-C1-C8-烷基;任选地被取代的(C1-C8-烷氧基亚氨基)-C1-C8-烷基;任选地被取代的(C2-C8-烯基氧基亚氨基)-C1-C8-烷基;任选地被取代的(C2-C8-炔基氧基亚氨基)-C1-C8-烷基;任选地被取代的(苄氧基亚氨基)-C1-C8-烷基;羧基;氨甲酰基;N-羟基氨甲酰基;氨基甲酸酯;任选地被取代的C1-C16-烷基;任选地被取代的C2-C8-烯基;任选地被取代的C2-C8-炔基;任选地被取代的C1-C16-烷氧基;任选地被取代的C1-C8-烷基硫烷基;任选地被取代的C1-C8-烷基亚磺酰基;任选地被取代的C1-C8-烷基磺酰基;任选地被取代的C1-C8-烷基氨基;任选地被取代的二-C1-C8-烷基氨基;任选地被取代的C2-C8-烯基氧基;任选地被取代的C3-C8-炔基氧基;任选地被取代的C3-C8-环烷基;任选地被取代的(C3-C8-环烷基)-C1-C8-烷基;任选地被取代的(C3-C8-环烷基)-(C3-C8-环烷基;任选地被取代的(C3-C8-环烷基)-C2-C8-烯基;任选地被取代的(C3-C8-环烷基)-C2-C8-炔基;任选地被取代的三(C1-C8)烷基甲硅烷基;任选地被取代的三(C1-C8)烷基甲硅烷基-C1-C8-烷基;任选地被取代的C1-C8-烷基羰基;任选地被取代的C1-C8-烷基羰基氧基;任选地被取代的C1-C8-烷基羰基氨基;任选地被取代的C1-C8-烷氧基羰基;任选地被取代的C1-C8-烷氧基羰基氧基;任选地被取代的C1-C8-烷基氨甲酰基;任选地被取代的二-C1-C8-烷基氨甲酰基;任选地被取代的C1-C8-烷基氨基羰基氧基;任选地被取代的二-C1-C8-烷基氨基羰基氧基;任选地被取代的N-(C1-C8-烷基)羟基氨甲酰基;任选地被取代的C1-C8-烷氧基氨甲酰基;任选地被取代的N-(C1-C8-烷基)-C1-C8-烷氧基氨甲酰基;C1-C8-芳基烷基,其任选地被至多6个相同或不同的基团Rb取代;C2-C8-芳基烯基,其任选地被至多6个相同或不同的基团Rb取代;C2-C8-芳基炔基,其任选地被至多6个相同或不同的基团Rb取代;芳氧基,其任选地被至多6个相同或不同的基团Rb取代;芳基硫烷基,其任选地被至多6个相同或不同的基团Rb取代;芳基氨基,其任选地被至多6个相同或不同的基团Rb取代;C1-C8-芳基烷氧基,其任选地被至多6个相同或不同的基团Rb取代;C1-C8-芳基烷基硫烷基,其任选地被至多6个相同或不同的基团Rb取代;C1-C8-芳基烷基氨基,其任选地被至多6个相同或不同的基团Rb取代;或二环[2.2.1]庚基;
R1、Rb彼此独立地代表卤素;硝基、氰基、C1-C12-烷基;C1-C6-卤代烷基,其具有1-9个相同或不同的卤素原子;C1-C6-烷氧基;C1-C6-卤代烷氧基,其具有1-9个相同或不同的卤素原子;C1-C6-烷基硫烷基;C1-C6-卤代烷基硫烷基,其具有1-9个相同或不同的卤素原子;C1-C6-烷基磺酰基;C1-C6-卤代烷基磺酰基,其具有1-9个相同或不同的卤素原子;C2-C12-烯基;C2-C12-炔基;C3-C7-环烷基;苯基;三(C1-C8)烷基甲硅烷基;三(C1-C8)烷基甲硅烷基-C1-C8-烷基;
其中,除非另外指出,根据本发明被取代的基团或取代基可以被一个或多个Rb取代;或者
Q和R1与它们连接的碳原子一起形成任选地被取代的5元、6元或7元碳环或饱和杂环;或者
Q和L一起形成式(W1)的基团,
其中
用*标记的键连接至酰胺;
X代表单键或双键;
Y代表氧、硫、N(R27)或(CR28R29)(CR30R31)m(CR32R33)n;
m代表0或1;
n代表0或1;
R21和R22彼此独立地代表氢、卤素、C1-C4-烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基;
R23、R24、R25和R26彼此独立地代表氢、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷基硫烷基、C1-C4-卤代烷基硫烷基、羟基甲基、C1-4-烷氧基甲基、C(O)CH3或C(O)OCH3;
R27代表氢、C1-C4-烷基、苄基(其中苯基任选地被独立地选自下述的基团取代至多3次:卤素、C1-C4-烷基、C1-C4-卤代烷基和C1-C4-烷氧基)、甲酰基、C(O)C1-C4-烷基(任选地被卤素或C1-C4-烷氧基取代)、C(=O)O-C1-C6-烷基(任选地被卤素、C1-C4-烷氧基或氰基取代)或C1-C4-烷氧基-(C1-C4)-亚烷基;
R28、R29、R30、R31、R32和R33彼此独立地代表氢、卤素、羟基、C1-C4-烷氧基、C1-C6-烷基[任选地被卤素、羟基、C1-C4-烷氧基、=O、芳基、O-C(O)-C1-C4-烷基或3-7元碳环(所述碳环自身任选地被至多3个甲基取代)取代]或C2-C6-烯基[任选地被卤素、羟基、C1-C4-烷氧基、=O、芳基、O-C(O)-C1-C4-烷基或3-7元碳环(所述碳环自身任选地被至多3个甲基取代)取代]或3-7元饱和环(所述环任选地被至多3个甲基取代,且任选地含有选自氮和氧的杂原子);或者
R28和R29与它们连接的碳原子一起形成基团C=O或3-5元碳环(所述碳环任选地被至多3个甲基取代,且任选地含有至多2个独立地选自氮和氧的杂原子);或者
R28和R29一起形成C1-C6-亚烷基(其任选地被至多4个基团取代,所述基团可以相同或不同,且可以选自:氟、氯、溴、甲基)或C3-C6-亚环烷基基团(其任选地被至多3个甲基取代)。
式(I)提供了根据本发明的1-甲基-3-二卤代甲基-5-卤代吡唑(硫代)甲酰胺的一般定义。在下面给出了在上文和下文中显示的式的优选基团定义。这些定义适用于式(I)的终产物,并同样适用于所有中间体。
T优选地代表氧原子,
R优选地代表氢,C1-C4-烷基磺酰基,C1-C3-烷氧基-C1-C3-烷基,在每种情况下具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基磺酰基、卤代-C1-C3-烷氧基-C1-C3-烷基;或甲酰基。
R特别优选地代表氢,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,正-、异-、仲-或叔-丁基磺酰基,甲氧基甲基,甲氧基乙基,乙氧基甲基,乙氧基乙基,三氟甲基磺酰基,三氟甲氧基甲基,或甲酰基。
R非常特别优选地代表氢、甲氧基甲基或甲酰基。
Hal1优选地代表氯。
Hal1优选地代表氟。
Hal2优选地代表氯。
Hal2优选地代表氟。
L优选地代表
其中用*标记的键与酰胺连接,而用#标记的键与Q连接;
R1如本文所定义,或者
R1和Q与它们连接的碳原子一起形成任选地被取代的5元或6元碳环或杂环。
L特别优选地代表L-1;
L此外特别优选地代表L-2;
R1优选地代表氢、氟、氯、甲基或三氟甲基。
R1特别优选地代表氢。
R1此外特别优选地代表氟,其中氟特别优选地位于酰基苯胺基团的4位、5位或6位,非常特别优选地位于4位或6位,尤其是4位[参见上面式(I)]。
R1此外特别优选地代表氯,其中氯特别优选地位于酰基苯胺基团的5位[参见上面式(I)]。氯此外特别优选地位于酰基苯胺基团的4位。
R1此外特别优选地代表甲基,其中甲基特别优选地位于酰基苯胺基团的3位[参见上面式(I)]。
R1此外特别优选地代表三氟甲基,其中三氟甲基特别优选地位于酰基苯胺基团的4位或5位[参见上面式(I)]。
Q和R1与它们所连接的碳原子一起优选地代表任选地被相同或不同的取代基单至四取代的5元或6元碳环或饱和杂环。
Q和R1与它们所连接的碳原子一起特别优选地代表任选地被甲基单、二或三取代的5元或6元碳环。
Q和R1与它们所连接的碳原子一起特别优选地代表5元或6元饱和杂环,所述杂环含有一个氧原子且任选地被甲基单、二或三取代。
L特别优选地代表L-1,其中Q和R1与它们所连接的碳原子一起非常特别优选地代表任选地被甲基单、二或三取代的5元或6元碳环。
L特别优选地代表L-1,其中Q和R1与它们所连接的碳原子一起非常特别优选地代表5元或6元饱和杂环,所述杂环含有一个氧原子且任选地被甲基单、二或三取代。
Q优选地代表Q1、Q2、Q3、Q4、Q5或Q6
Q1代表
其中用#标记的键与L连接;
R2代表氢、C1-C4-烷基或C1-C4-卤代烷基。
R2特别优选地代表氢,氟,氯,甲基,乙基,正-或异-丙基,或者代表它们中的每一个被选自氟、氯和溴的相同或不同的取代基单或多取代的甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基。
R2非常特别优选地代表氢、氟、氯、甲基、乙基、三氟甲基、二氟甲基、氟甲基、三氯甲基、二氯甲基、氯甲基、氯氟甲基、氟二氯甲基、二氟氯甲基、五氟乙基、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-2,2-二氟乙基、2-氯-2,2-二氟乙基、2-二氯-2-氟乙基、2,2,2-三氯乙基、1-氯丁基、七氟正丙基或七氟异丙基。
R2非常特别优选地代表氢、甲基或乙基。
R2特别优选地代表氢或甲基。
Z代表–CR3R4R5或–SiR3R4R5。
Z特别优选地代表–CR3R4R5。
Z此外特别优选地代表–SiR3R4R5。
s代表0、1、2或3。
s特别优选地代表0。
s特别优选地代表1。
s此外特别优选地代表2。
s非常特别优选地代表1。
t代表0或1。
t特别优选地代表0。
t特别优选地代表1。
条件是当Z是–CR3R4R5,且s代表1,且t代表0时,R2不是氢、甲基或乙基。
R3、R4、R5彼此独立地代表氢、C1-C8-烷基或C1-C6-卤代烷基,或者
R3和R4与它们连接的碳原子一起形成3-6元碳环饱和或不饱和环。
R3特别优选地代表氟,氯,溴,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,或者代表它们中的每一个被选自氟、氯和溴的相同或不同的取代基单或多取代的甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基。
R3特别优选地代表氟,氯,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,三氟甲基,二氟甲基,氟甲基,三氯甲基,二氯甲基,氯甲基,氯氟甲基,氟二氯甲基,二氟氯甲基,五氟乙基,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-2,2-二氟乙基,2-氯-2,2-二氟乙基,2-二氯-2-氟乙基,2,2,2-三氯乙基,1-氯丁基,七氟正丙基或七氟异丙基。
R3尤其非常优选地代表氯、甲基、乙基、异丙基或三氟甲基。
R4特别优选地代表氟,氯,溴,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,或者代表它们中的每一个被选自氟、氯和溴的相同或不同的取代基单或多取代的甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基。
R4特别优选地代表氟,氯,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,三氟甲基,二氟甲基,氟甲基,三氯甲基,二氯甲基,氯甲基,氯氟甲基,氟二氯甲基,二氟氯甲基,五氟乙基,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-2,2-二氟乙基,2-氯-2,2-二氟乙基,2-二氯-2-氟乙基,2,2,2-三氯乙基,1-氯丁基,七氟正丙基或七氟异丙基。
R4尤其非常优选地代表氯、甲基、乙基、异丙基或三氟甲基。
R5特别优选地代表氢,氟,氯,溴,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,或者代表它们中的每一个被选自氟、氯和溴的相同或不同的取代基单或多取代的甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基。
R5特别优选地代表氢,氟,氯,甲基,乙基,正-或异-丙基,异-、仲-或叔-丁基,三氟甲基,二氟甲基,氟甲基,三氯甲基,二氯甲基,氯甲基,氯氟甲基,氟二氯甲基,二氟氯甲基,五氟乙基,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-2,2-二氟乙基,2-氯-2,2-二氟乙基,2-二氯-2-氟乙基,2,2,2-三氯乙基,1-氯丁基,七氟正丙基或七氟异丙基。
R5尤其非常优选地代表氢、氯、甲基、乙基、异丙基或三氟甲基。
R3和R4此外与它们连接的碳原子一起特别优选地形成任选地被下述取代基取代的3-6元碳环或杂环饱和或不饱和环:卤素、甲基、乙基、甲氧基、三氟甲基或三氟甲氧基,
R3和R4此外与它们连接的碳原子一起特别优选地形成任选地被下述基团取代的3元、5元或6元碳环饱和环:甲基、乙基或三氟甲基,
R3和R4此外与它们连接的碳原子一起尤其非常优选地形成任选地被下述基团取代的6元碳环不饱和环:卤素、甲基、乙基、甲氧基、三氟甲基或三氟甲氧基。
Q2代表,其中用#标记的键与L连接。
R13代表氢、卤素、C1-C8-烷基或C1-C8-卤代烷基。
R13特别优选地代表氟,氯,溴,碘,C1-C6-烷基,在每种情况下具有1-13个氟、氯和/或溴原子的C1-C6-卤代烷基。
R13非常特别优选地代表氟,氯,溴,甲基,乙基,正-、异-丙基,正-、异-、仲-、叔-丁基,或者代表在每种情况下具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基。
R13尤其非常优选地代表氟、氯、甲基、乙基或三氟甲基。
R14、R15和R16彼此独立地代表氢、甲基或乙基;
R14、R15和R16彼此独立地特别优选地代表甲基或氢;
R14、R15非常特别优选地代表甲基或氢;而R16代表氢。
Q3代表
其中用#标记的键与L连接;
R17代表氢或卤素。
R18代表氢或卤素。
R17和R18彼此独立地特别优选地代表氢、氟、氯或溴;
R17和R18彼此独立地非常特别优选地代表氢或氟;
R17和R18尤其非常特别优选地代表氢;
R19代表任选地被取代的C2-C12-烷基、任选地被取代的C2-C12-烯基、任选地被取代的C2-C12-炔基、任选地被取代的C3-C12-环烷基、任选地被取代的苯基或杂环基。
R19特别优选地代表C2-C6-烷基、任选地被取代的C3-C8-环烷基、任选地被取代的苯基、吡啶基、噻吩基或呋喃基;
R19非常特别优选地代表乙基,正丙基,异丙基,正丁基,仲丁基,叔丁基,正戊基,新戊基,异戊基,正己基,异己基,正庚基,环丙基,环丁基,环戊基,环己基,环庚基,环辛基,a-甲基环丙基,2-、3-或4-卤代-取代的苯基,2-噻吩基,3-噻吩基或2-呋喃基;
R19尤其非常特别优选地代表乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、环丙基、环丁基、环戊基、环己基、a-甲基环丙基、4-氟苯基、4-溴苯基、4-氯苯基、2-噻吩基、3-噻吩基或2-呋喃基。
Q4代表
其中用#标记的键与L连接,
R34、R35和R36彼此独立地代表卤素、氰基、硝基、C1-C6-烷基、C2-C6-烯基、C1-C4-烷氧基、C1-C4-烷基硫烷基、C1-C4-烷基磺酰基、C3-C6-环烷基,或者代表在每种情况下具有1-5个卤素原子的C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷基硫烷基或C1-C4-卤代烷基磺酰基。
R34、R35和R36彼此独立地特别优选地代表氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,甲氧基,乙氧基,甲基硫烷基,乙基硫烷基,正-或异-丙基硫烷基,环丙基,三氟甲基,三氯甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲基硫烷基,二氟氯甲基硫烷基或三氟甲基硫烷基。
R34、R35和R36彼此独立地非常特别优选地代表氟、氯、溴、甲基、三氟甲基、二氟甲氧基或三氟甲氧基。
R34、R35和R36彼此独立地尤其非常优选地代表氟、氯、溴。
u代表0或1。
u特别优选地代表0。
u特别优选地代表1。
Q5代表
其中用#标记的键与L连接。
Q6代表
其中R37代表氢或氟且其中用#标记的键与L连接。
X优选地代表单键。
Y优选地代表氧、硫、N(R27)、CH2、CH2CH2、CH2CH2CH2、C(CH3)2、CH(CH3)、CH(C2H5)、C(CH3)(C2H5)、CH(OCH3)或C(OCH3)2;
Y特别优选地代表N(R27)、氧、硫、CH2、CH2CH2、CH2CH2CH2、C(CH3)2、CH(CH3)或CH(C2H5);
Y非常特别优选地代表N(R27)、氧、硫、CH2或CH2CH2;
Y特别优选地代表氧、CH2或N(R27)。
Y优选地代表氧、N(R27)或(CR28R29)(CR30R31)m(CR32R33)n。
Y特别优选地代表氧或(CR28R29)(CR30R31)m(CR32R33)n。
Y非常特别优选地代表(CR28R29)(CR30R31)m(CR32R33)n。
Y非常特别优选地代表(CR28R29)。
n优选地代表0。
m优选地代表0。
R21优选地代表氢、卤素或C1-C4-烷基。
R21特别优选地代表氢或卤素。
R21非常特别优选地代表氢。
R22优选地代表氢或甲基。
R22特别优选地代表氢。
R23优选地代表氢、C1-C4-烷基、卤素、C1-C4-卤代烷基、C1-C4-烷氧基、C(O)CH3或C(O)OCH3。
R23特别优选地代表氢、C1-C2-烷基、卤素、CF3、甲氧基、C(O)CH3或C(O)OCH3。
R23非常特别优选地代表氢、甲基、氯、CF3或甲氧基。
R23非常特别优选地代表氢或甲基。
R24优选地代表氢、C1-C4-烷基、卤素、C1-C4-卤代烷基、C1-C4-烷氧基、C(O)CH3或C(O)OCH3。
R24特别优选地代表氢、C1-C2-烷基、氯、CF3、甲氧基、C(O)CH3或C(O)OCH3。
R24非常特别优选地代表氢或甲基。
R25优选地代表氢、C1-C4-烷基、C1-C4-烷氧基或C(O)CH3。
R25特别优选地代表氢或甲基、甲氧基或C(O)CH3。
非常特别优选地,R25代表氢或甲基。
R26优选地代表氢、C1-C4-烷基、C1-C4-烷氧基或C(O)CH3。
R26特别优选地代表氢或甲基、甲氧基或C(O)CH3。
R26非常特别优选地代表氢或甲基。
R27优选地代表氢、C1-C4-烷基、苄基(其中苯基任选地被独立地选自下述的基团取代至多3次:卤素、C1-C4-烷基、C1-C4-卤代烷基和C1-C4-烷氧基)、甲酰基、C(O)C1-C4-烷基或C1-C4-烷氧基-(C1-C4)-亚烷基;
R27优选地代表氢、C1-C4-烷基、苄基、甲酰基、C(O)CH3或C(O) OC(CH3)3;
R27特别优选地代表氢或C1-C2-烷基。
R27优选地代表C1-C4-烷基、甲酰基、C(O)CH3或C(O)OC1-C6-烷基(任选地被卤素、CN或C1-C4-烷氧基取代)。
R27特别优选地代表C(O)OC1-C4-烷基。
R28、R29、R30、R31、R32和R33彼此独立地优选地代表氢、C1-C4-烷基或C1-C4-烷氧基。
R28、R29、R30、R31、R32和R33彼此独立地优选地为氢、C1-C2-烷基或甲氧基。
R28和R29彼此独立地优选地为氢、卤素、C1-C5-烷基、C1-C3-烷氧基、CH2OH、CH(O)、C3-C6-环烷基、CH2O-C(=O)CH3、CH2-C3-C6-环烷基或苄基;或者
R28和R29与它们连接的碳原子一起形成基团C=O或3-5元碳环;或者
R28和R29一起形成C1-C5-亚烷基、二氯亚乙烯基或C3-C6-亚环烷基基团。
R28和R29彼此独立地特别优选地代表氢、甲基、乙基、n-C3H7、i-C3H7、n-C4H9、仲(sec)-C4H9、i-C4H9、CH(C2H5)2、CH2-环丙基或环戊基;或者
R28和R29与它们连接的碳原子一起形成3-5元碳环。
R30优选地代表氢或甲基。
R31优选地代表氢或甲基。
R32优选地代表氢或甲基。
R33优选地代表氢或甲基。
优选的是,这样的式(I)的化合物,其中所有基团在每种情况下具有上面提及的优选含义。
特别优选的是,这样的式(I)的化合物,其中所有基团在每种情况下具有上面提及的特别优选的含义。
非常特别优选的是,这样的式(I)的化合物,其中所有基团在每种情况下具有上面提及的非常特别优选的含义。
尤其非常特别优选的是,这样的式(I)的化合物,其中所有基团在每种情况下具有上面提及的尤其非常特别优选的含义。
具有下式的新颖的(硫代)甲酰胺的下述群组是优选的,且在每种情况下应当理解为上述式(I)的化合物的子集
其中T、R、L、Q1具有上面给出的含义,且Hal代表氟或氯;
其中T、R、L、Q2具有上面给出的含义,且Hal代表氟或氯;
其中T、R、L、Q3具有上面给出的含义,且Hal代表氟或氯;
其中T、R、L、Q4具有上面给出的含义,且Hal代表氟或氯;
其中T、R、L、Q5具有上面给出的含义,且Hal代表氟或氯;
其中T、R、L、Q6具有上面给出的含义,且Hal代表氟或氯;
其中T、R、R21、R22、R23、R24、R25、R26具有上面给出的含义,且Hal代表氟或氯。
具有下式的新颖的(硫代)甲酰胺的下述群组是优选的,且在每种情况下应当理解为上述式(I)的化合物的子集
其中T、R、L和Q具有上面给出的含义,且Hal代表氟;
其中T、R、L和Q具有上面给出的含义,且Hal代表氯。
非常特别优选的是,这样的式(I)的化合物,其中
T代表氧;
R代表氢;
Hal1代表氟;
L代表L-1或L-2;
Q代表Q1、Q2、Q3、Q4、Q5或Q6;
R1代表氢或氟;
Q1代表
其中用#标记的键与L连接,
R2代表氢、甲基或乙基,
Z代表–CR3R4R5或–SiR3R4R5;
s代表0、1、2或3;
t代表0,
R3、R4、R5彼此独立地代表氢或甲基;
Q2代表,其中用#标记的键与L连接;
R13、15、16彼此独立地代表氢或甲基;
R14代表氢、甲基或乙基,
Q3代表,
其中用#标记的键与L连接;
R17、18代表氢;
R19代表环丙基;
Q4代表,
u代表0,
R34、R35和R36彼此独立地代表F、Cl、Br或三氟甲基,
其中用#标记的键与L连接;
Q5代表
Q6代表
或者Q和L一起形成式(W1-A)的基团,
其中用*标记的键连接至酰胺,
或者Q和L一起形成式(W1-B)的基团,
其中用*标记的键连接至酰胺,
饱和的或不饱和的烃基,例如烷基或烯基,在每种情况下可以是直链的或支链的,只要这是可能的,包括与杂原子相组合,例如,在烷氧基中。
芳基、芳基烷基、芳基烯基和芳基炔基以及含有这些术语的部分中含有的芳基部分可以是可被至多5个基团Rb(其可以相同或不同)取代的苯基,可被至多6个基团Rb(其可以相同或不同)取代的萘基。
任选地被取代的基团可以是单或多取代的,其中在多取代的情况下,所述取代基可以是相同的或不同的。因而,二烷基氨基的定义也包括被烷基非对称地取代的氨基,例如,甲基乙基氨基。
卤素-取代的基团,例如,卤代烷基,是单或多卤代的。在多卤代的情况下,所述卤素原子可以是相同的或不同的。卤素表示氟、氯、溴和碘,尤其是氟、氯和溴。
如果合适,根据本发明的化合物可以作为各种可能的异构形式的混合物而存在,所述异构形式特别是立体异构体,例如E和Z,苏式和赤式,和旋光异构体,以及,如果合适,互变异构体。要求保护的是E和Z异构体、苏式和赤式、以及旋光异构体、这些异构体的任意混合物、以及可能的互变体构形式。
在Q的根据本发明的变体中,存在至多2个立体中心(*)。要求保护的是所有非对映异构体和对映异构体,尤其是下述基团的非对映异构体和对映异构体
上述的一般的或优选的基团定义或举例说明可以根据需要在各自的范围和优选的范围之间进行组合。它们均适用于终产物,并且相应地适用于前体和中间体。具体地,在群组(I-a)至(I-i)中提及的化合物均可以与一般含义、优选含义、特别优选含义等相组合,其中,在这里也在每种情况下,在优选的范围之间的所有组合是可能的。
最后,已经发现,新颖的式(I)的1-甲基-3-二卤代甲基-5-卤代吡唑(硫代)甲酰胺具有非常好的杀微生物性能,且可以用于在作物保护和材料保护二者中防治不希望的微生物。
此外,已经发现,可如下得到式(I)的1-甲基-3-二卤代甲基-5-卤代吡唑甲酰胺(其中T代表氧原子):
如果合适的话在有催化剂存在下,如果合适的话在有缩合剂存在下,如果合适的话在有酸结合剂存在下,且如果合适的话在有稀释剂存在下,使式(II)的羧酸衍生物
其中
X1代表卤素或羟基,
Hal1和Hal2彼此独立地代表氯或氟;
与式(III)的胺衍生物反应
其中R、L和Q具有上面给出的含义。
这种合成式(I)的这类酰胺的方法已经在下述文献中进行了充分描述:
WO-A 2006/061215、WO-A 2005/042494、WO-A 2005/042493、WO-A 2008/095890、WO-A 2004/035589、WO-A 2003/074491。
使用的式(II)的酸和酰卤是新颖的,并如下所述进行合成:
其中
X1代表卤素或羟基。
优选的是,这样的式(II)的化合物,其中X1代表羟基、氯或氟。
本发明的另一个方面包括用于合成式(II)的酰氯的根据本发明的方法P1,如下面的反应路线所示:
。
式(IIa)的化合物5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醛从WO-A 2004/014138 (实施例35)已知。
在有氧化剂存在下,并且如果需要的话,在有溶剂存在下,进行根据本发明的方法P1中的步骤1。
在有酰卤形成剂存在下,并且如果需要的话,在有溶剂存在下,进行根据本发明的方法P1中的步骤2和5。
在有氟化剂存在下,并且如果需要的话,在有溶剂存在下,进行根据本发明的方法P1中的步骤3。
在有酸或碱存在下,并且如果需要的话,在有溶剂存在下,进行根据本发明的方法P1中的步骤4。
适合用于实现根据本发明的方法P1的步骤1的氧化剂是这类反应常用的所有无机和有机氧化剂。
优选的是,苄基三乙基高锰酸铵、溴、氯、间氯过苯甲酸、铬酸、氧化铬(VI)、过氧化氢、过氧化氢/三氟化硼、过氧化氢/脲加合物、2-羟基过氧六氟-2-丙醇、碘、过苯甲酸、硝酸过氧化乙酰、高锰酸钾、钌酸钾、吡啶鎓重铬酸盐、氧化钌(VIII)、氧化银(I)、氧化银(II)、亚硝酸银、亚氯酸钠、次氯酸钠、2,2,6,6-四甲基哌啶-1-氧基自由基(2,2,6,6-tetramethylpiperidine-1-oxyl)。
适合用于根据本发明的方法P1的步骤2和步骤5的酰卤形成剂是这类反应常用的所有有机和无机酰卤形成剂。
优选的是,光气、三氯化磷、五氯化磷、三氯氧磷;亚硫酰氯;或四氯化碳/三苯基膦。
适合用于根据本发明的方法P1的步骤3的氟化剂是这类反应常用的那些氟化剂。
优选的是,氟化铯;氟化钾;氟化钾/二氟化钙以及四丁基氟化铵。
适合用于根据本发明的方法P1的步骤1至5的溶剂是所有常规惰性有机溶剂。
优选的是,使用任选地卤化的脂族、脂环族或芳族烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢化萘;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;各种醚,例如乙醚、环戊基甲基醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、2-甲基四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或茴香醚;腈,例如乙腈、丙腈、正-或异-丁腈或苄腈;酰胺,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酸三酰胺;酯,例如乙酸甲酯或乙酸乙酯,亚砜,例如二甲亚砜,或砜,例如环丁砜。
当进行根据本发明的方法P1的步骤1至5时,反应温度可以在相对较宽范围内变化。通常,在0℃至160℃的温度,优选地在0℃至120℃的温度,进行所述步骤。
作为在根据本发明的方法P1中控制温度的措施,还可以使用微波技术。
除非另外指出,根据本发明的方法P1的所有步骤通常在大气压下进行。但是,还可以在升压或减压下(通常在0.1-10巴之间)操作。
为了实现根据本发明的方法P1的步骤1,式(IIa)的醛衍生物通常使用过量的氧化剂。但是,还可以使用其它比例的组分。
为了实现根据本发明的方法P1的步骤2和5,式(IIb)或(IIe)的羧酸衍生物通常使用过量的酰卤形成剂。但是,还可以使用其它比例的组分。
为了实现根据本发明的方法P1的步骤3,式(IIc)的酰卤衍生物通常使用过量的氟化剂。但是,还可以使用其它比例的组分。
为了实现根据本发明的方法P1的步骤4,式(IId)的酰氟衍生物通常使用过量的酸或碱。但是,还可以使用其它比例的组分。
本发明的另一个方面包括用于合成式(I)的1-甲基-3-二卤代甲基-5-卤代吡唑硫代甲酰胺的根据本发明的方法P2,其中T代表硫原子,如下面的反应路线所示:
其中Hal1、Hal2、R、L和Q如本文所定义,
任选地在有催化量或化学计算量或过量的碱(例如无机和有机碱)存在下。优选的是,使用碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠;杂环芳族碱,例如吡啶、甲基吡啶、二甲基吡啶、三甲基吡啶;以及叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基氨基吡啶或N-甲基-哌啶。
根据本发明的方法P2在硫化剂(thionating agent)存在下进行。
式(I)的原料酰胺衍生物可以如先前所述制备。
适合用于实现根据本发明的方法P2的硫化剂可以是硫(S)、氢硫酸(H2S)、硫化钠(Na2S)、硫氢化钠(NaHS)、三硫化二硼(B2S3)、硫化双(二乙基铝) ((AlEt2)2S)、硫化铵((NH4)2S)、五硫化二磷(P2S5)、劳森试剂(2,4-双(4-甲氧基苯基)-1,2,3,4-二硫杂二磷杂环丁烷2,4-二硫化物)或聚合物负载的硫化剂,例如在Journal of the ChemicalSociety, Perkin 1 (2001), 358中所述。
根据上述方法可以合成根据本发明的化合物。基于他的专门知识,本领域技术人员能够以合适的方式修改根据本发明的化合物的制备方法。
某些式(III)的胺是已知的:
式(III)的胺 | 作为下述实施例编号的起始原料 | 可以根据下述文献制备 |
2-(3-甲基丁基)苯胺 | 10 | EP-A 824099 |
2-(4-甲基戊-2-基)苯胺 | 11、12 | WO-A 2009/029383 |
2-(3,3-二甲基丁基)苯胺 | 13、14 | WO-A 2008/006576 |
2-(5-甲基己-3-基)苯胺 | 20 | WO-A 2002/038542 |
2-(4,4-二甲基戊-2-基)苯胺 | 21、22 | WO-A 2005/042494 |
2-[2-(三甲基甲硅烷基)乙基]苯胺 | 24、25 | WO-A 2005/049624 |
2-(1,1,2,3,3,3-六氟-丙氧基)苯胺 | 31、32 | WO-A 2007/017450 |
2-[1,1'-二(环丙基)-2-基]苯胺 | 46、47、48、49、50 | WO-A 2006/087223 |
2-(二环[2.2.1]庚-2-基)苯胺 | 51 | EP 96-116044 |
1,1,3-三甲基茚满-4-胺 | 64、65 | JP 62096472;EP-A 654464 |
9-异丙基-1,2,3,4-四氢-1,4-亚甲基萘-5-胺 | 66、67、68 | WO-A 2007/068417 |
9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-胺 | 71、72 | WO-A 2010/049228 |
4'-氯-5-氟联苯-2-胺 | 83、84 | WO-A 2008/014905 |
4'-氯-3',5-二氟联苯-2-胺 | 98 | DE-A 102005009458 |
4'-氯-3'-氟联苯-2-胺 | 99、100、101 | WO-A 2003/066609 |
3',4',5'-三氟联苯-2-胺 | 104、105、106 | WO-A 2006/087343 |
3',4'-二氯-5-氟联苯-2-胺 | 116、117 | DE-A 102004041531 |
4'-溴联苯-2-胺 | 139、140、141 | WO-A 2005040110 |
3'-氟-4'-(三氟甲基)联苯-2-胺 | 148、149 | WO-A 2003/066609 |
4'-溴-3'-氯联苯-2-胺 | 152、153 | WO-A 2003/066609 |
3-异丙氧基苯胺 | 169、170、171 | DE-A 2434430 |
本发明的化合物可根据上述一般制备方法制备。然而要理解,技术人员基于他的一般常识和可获得的出版物,能够根据所需合成的各种化合物的特性对所述方法进行调整。
在另一个方面,本发明也涉及一种杀真菌剂组合物,其包含有效且非植物毒性量的式(I)的活性化合物。
“有效且非植物毒性量”的表述是指这样的本发明组合物的量:其足以防治或破坏存在于或易于出现在作物上的真菌,并且该量不会使所述作物产生任何可察觉的植物毒性征状。该量根据以下因素可在宽范围内变化:待防治的真菌、作物的类型、气候条件和包含在本发明的杀真菌剂组合物中的化合物。该量可通过系统性田间试验来确定,这在本领域技术人员的能力范围内。
因而,根据本发明,提供了一种杀真菌剂组合物,其包含作为活性成分的有效量的本文定义的式(I)的化合物以及农业上可接受的支持物、载体或填充剂。
根据本发明,术语“支持物”表示天然或合成的有机或无机化合物,它与式(I)的活性化合物组合或联合使用,使活性化合物更容易施用,特别是施用到植物各部分。因此,此支持物通常是惰性的,并且应该是农业上可接受的。支持物可为固体或液体。合适的支持物的例子包括粘土、天然或合成的硅酸盐、硅土、树脂、蜡、固体肥料、水、醇(特别是丁醇)、有机溶剂、矿物油和植物油以及它们的衍生物。也可以使用这些支持物的混合物。
根据本发明的组合物也可以包含其它的组分。具体地,所述组合物还可包含表面活性剂。表面活性剂可为离子型或非离子型乳化剂、分散剂或润湿剂或这些表面活性剂的混合物。可以提及例如,聚丙烯酸盐、木质素磺酸盐、苯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、取代的酚(特别是烷基酚或芳基酚)、磺基丁二酸酯的盐、牛磺酸衍生物(特别是牛磺酸烷基酯)、聚氧乙基化(polyoxyethylated)醇或酚的磷酸酯、多元醇的脂肪酸酯,以及含有硫酸、磺酸和磷酸官能团的上述化合物的衍生物。当活性化合物和/或惰性支持物不溶于水时,和当用于施用的媒介试剂是水时,至少一种表面活性剂的存在通常是必要的。优选地,以组合物的重量计,表面活性剂的含量可以为5重量%至40重量%。
任选地,还可包括附加的组分,例如,保护性胶体、粘着剂、增稠剂、触变剂(thixotropic agents)、渗透剂、稳定剂、掩蔽剂。更一般地,活性化合物可根据常用的制剂技术与任何固体或液体添加剂相混合。
一般而言,本发明的组合物可含有0.05重量%至99重量%的活性化合物,优选为10重量%至70重量%的活性化合物。
本发明的组合物可以以各种形式使用,诸如气溶胶分配器、微胶囊悬浮剂、冷雾剂、粉剂、可乳化的浓缩物、水包油乳剂、油包水乳剂、微胶囊粒剂、细粒剂、种子处理悬浮剂、气体(在压力下)、气体发生产品、颗粒剂、热雾剂、大粒剂、微粒剂、油分散性粉剂、油悬浮剂、油溶性液体、糊剂、棒剂、种子处理粉剂、杀虫剂包衣的种子、可溶性浓缩物、可溶性粉剂、种子处理液剂、悬浮剂(可流动的浓缩物)、超低容量(ULV)液体、超低容量(ULV)混悬剂、水分散性粒剂或片剂、泥浆处理用的水分散性粉剂(water dispersible powder forslurry treatment)、水溶性粒剂或片剂、种子处理用水溶性粉剂和可湿性粉剂。这些组合物不仅包括通过合适的设备(如喷雾或撒粉设备)施用到待处理的植物或种子上的现成组合物,还包括在施用到作物之前必须稀释的浓缩商品组合物。
根据本发明的化合物还可与一种或多种以下物质混合:杀虫剂、杀真菌剂、杀细菌剂、引诱剂、杀螨剂或信息素活性物质或其它有生物活性的化合物。这样得到的混合物通常具有广谱的活性。与其它杀真菌剂化合物的混合物尤其有利。
合适的杀真菌剂混合用组分的例子可选自下述列表:
(1) 麦角固醇生物合成的抑制剂,例如(1.1)十二吗啉(aldimorph)(1704-28-5),(1.2) 阿扎康唑(60207-31-0), (1.3) 联苯三唑醇(55179-31-2), (1.4) 糠菌唑(116255-48-2), (1.5) 环丙唑醇(113096-99-4), (1.6) 苄氯三唑醇(75736-33-3),(1.7) 噁醚唑(119446-68-3), (1.8) 烯唑醇(83657-24-3), (1.9) R-烯唑醇(83657-18-5), (1.10) 吗菌灵(1593-77-7), (1.11) 吗菌灵醋酸盐(31717-87-0), (1.12) 氟环唑(106325-08-0), (1.13) 乙环唑(60207-93-4), (1.14) 氯苯嘧啶醇(60168-88-9),(1.15) 腈苯唑(114369-43-6), (1.16) 环酰菌胺(126833-17-8), (1.17) 苯锈啶(67306-00-7), (1.18) 丁苯吗啉(67306-03-0), (1.19) 氟喹唑(136426-54-5), (1.20)呋嘧醇(56425-91-3), (1.21) 氟硅唑(85509-19-9), (1.22) 粉唑醇(76674-21-0),(1.23) 呋菌唑(112839-33-5), (1.24) 呋醚唑(112839-32-4), (1.25) 己唑醇(79983-71-4), (1.26) 抑霉唑(60534-80-7), (1.27) 硫酸抑霉唑(58594-72-2), (1.28) 酰胺唑(86598-92-7), (1.29) 种菌唑(125225-28-7), (1.30) 叶菌唑(125116-23-6),(1.31) 腈菌唑(88671-89-0), (1.32) 萘替芬(65472-88-0), (1.33) 氟苯嘧啶醇(63284-71-9), (1.34) 恶咪唑(174212-12-5), (1.35) 多效唑(76738-62-0), (1.36)稻瘟酯(101903-30-4), (1.37) 配那唑(66246-88-6), (1.38) 病花灵(3478-94-2),(1.39) 咪鲜胺(67747-09-5), (1.40) 丙环唑(60207-90-1), (1.41) 丙硫菌唑(178928-70-6), (1.42) 稗草畏(88678-67-5), (1.43) 啶斑肟(88283-41-4), (1.44) 氯苯喹唑(103970-75-8), (1.45) 硅氟唑(149508-90-7), (1.46) 螺环菌胺(118134-30-8),(1.47) 戊唑醇(107534-96-3), (1.48) 特比萘芬(91161-71-6), (1.49) 氟醚唑(112281-77-3), (1.50) 三唑酮(43121-43-3), (1.51) 三唑醇(89482-17-7), (1.52)十三吗啉(81412-43-3), (1.53) 氟菌唑(68694-11-1), (1.54) 嗪氨灵(26644-46-2),(1.55) 灭菌唑(131983-72-7), (1.56) 烯效唑(83657-22-1), (1.57) 单克素(83657-17-4), (1.58) 烯霜苄唑(77174-66-4), (1.59) 伏立康唑(137234-62-9), (1.60) 1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇(129586-32-9), (1.61) 1-(2,2-二甲基-2,3-二氢-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯(110323-95-0), (1.62) N'-{5-(二氟甲基)-2-甲基-4-[3-(三甲基甲硅烷基)丙氧基]苯基}-N-乙基-N-甲基亚氨基甲酰胺, (1.63) N-乙基-N-甲基-N'-{2-甲基-5-(三氟甲基)-4-[3-(三甲基甲硅烷基)丙氧基]苯基}亚氨基甲酰胺和(1.64) 1H-咪唑-1-硫代甲酸[O-[1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基]]酯(111226-71-2)。
(2) 呼吸链复合物I或II的抑制剂,例如(2.1) 联苯吡菌胺(581809-46-3),(2.2) 啶酰菌胺(188425-85-6), (2.3) 萎锈灵(5234-68-4), (2.4) 氟嘧菌胺(130339-07-0), (2.5) 甲呋酰胺(24691-80-3), (2.6) 氟吡菌酰胺(658066-35-4), (2.7) 氟酰胺(66332-96-5), (2.8) 氟唑菌酰胺(907204-31-3), (2.9) 呋吡菌胺(123572-88-3),(2.10) 茂谷乐(60568-05-0), (2.11) 吡唑萘菌胺(顺式-差向异构的外消旋体1RS,4SR,9RS和反式-差向异构的外消旋体1RS,4SR,9SR的混合物) (881685-58-1), (2.12) 吡唑萘菌胺(反式-差向异构的外消旋体1RS,4SR,9SR), (2.13) 吡唑萘菌胺(反式-差向异构的对映异构体1R,4S,9S), (2.14) 吡唑萘菌胺(反式-差向异构的对映异构体1S,4R,9R),(2.15) 吡唑萘菌胺(顺式-差向异构的外消旋体1RS,4SR,9RS), (2.16) 吡唑萘菌胺(顺式-差向异构的对映异构体1R,4S,9R), (2.17) 吡唑萘菌胺(顺式-差向异构的对映异构体1S,4R,9S), (2.18) 灭锈胺(55814-41-0), (2.19) 氧化萎锈灵(5259-88-1), (2.20) 戊苯吡菌胺(494793-67-8), (2.21) 吡噻菌胺(183675-82-3), (2.22) 环苯吡菌胺(874967-67-6), (2.23) 噻呋酰胺(130000-40-7), (2.24) 1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-(三氟甲基)-1H-吡唑-4-甲酰胺, (2.25) 3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺, (2.26) 3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺, (2.27) N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺(1092400-95-7) (WO2008148570), (2.28) 5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺(1210070-84-0) (WO2010025451), (2.29) N-[9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺, (2.30) N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺和(2.31) N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺。
(3) 呼吸链复合物III的抑制剂,例如(3.1) 辛唑嘧菌胺(865318-97-4), (3.2)吲唑磺菌胺(348635-87-0), (3.3) 腈嘧菌酯(131860-33-8), (3.4) 氰霜唑(120116-88-3), (3.5) 甲香菌酯(850881-30-0), (3.6) 丁香菌酯(850881-70-8), (3.7) 醚菌胺(141600-52-4), (3.8) 烯肟菌酯(238410-11-2) (WO 2004/058723), (3.9) 噁唑菌酮(131807-57-3) (WO 2004/058723), (3.10) 咪唑菌酮(161326-34-7) (WO 2004/058723), (3.11) 菌螨酯(fenoxystrobin) (918162-02-4), (3.12) 氟嘧菌酯(361377-29-9) (WO 2004/058723), (3.13) 醚菌酯(143390-89-0) (WO 2004/058723), (3.14)苯氧菌胺(133408-50-1) (WO 2004/058723), (3.15) 肟醚菌胺(189892-69-1) (WO2004/058723), (3.16) 啶氧菌酯(117428-22-5) (WO 2004/058723), (3.17) 唑菌胺酯(175013-18-0) (WO 2004/058723), (3.18) 唑胺菌酯(915410-70-7) (WO 2004/058723), (3.19) 唑菌酯(862588-11-2) (WO 2004/058723), (3.20) 吡菌苯威(799247-52-2) (WO 2004/058723), (3.21) 三环吡菌威(triclopyricarb) (902760-40-1),(3.22) 肟菌酯(141517-21-7) (WO 2004/058723), (3.23) (2E)-2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺(WO 2004/058723), (3.24) (2E)-2-(甲氧基亚氨基)-N-甲基-2-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)乙酰胺(WO 2004/058723), (3.25) (2E)-2-(甲氧基亚氨基)-N-甲基-2-{2-[(E)-({1-[3-(三氟甲基)苯基]乙氧基}亚氨基)甲基]苯基}乙酰胺(158169-73-4), (3.26) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺(326896-28-0),(3.27) (2E)-2-{2-[({[(2E,3E)-4-(2,6-二氯苯基)亚丁-3-烯-2-基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺, (3.28) 2-氯-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)吡啶-3-甲酰胺(119899-14-8), (3.29) 5-甲氧基-2-甲基-4-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)-2,4-二氢-3H-1,2,4-三唑-3-酮,(3.30) (2E)-2-{2-[({环丙基[(4-甲氧基苯基)亚氨基]甲基}硫烷基)甲基]苯基}-3-甲氧基丙-2-烯酸甲酯(149601-03-6), (3.31) N-(3-乙基-3,5,5-三甲基环己基)-3-(甲酰基氨基)-2-羟基苯甲酰胺(226551-21-9), (3.32) 2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺(173662-97-0)和(3.33) (2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺(394657-24-0)。
(4) 有丝分裂和细胞分裂的抑制剂,例如(4.1)苯菌灵(17804-35-2), (4.2) 多菌灵(10605-21-7), (4.3) 咪唑菌(3574-96-7), (4.4) 乙霉威(87130-20-9), (4.5) 韩乐宁(162650-77-3), (4.6) 氟吡菌胺(239110-15-7), (4.7) 麦穗宁(3878-19-1),(4.8) 戊菌隆(66063-05-6), (4.9) 噻菌灵(148-79-8), (4.10) 甲基硫菌灵(23564-05-8), (4.11) 硫菌灵(23564-06-9), (4.12) 苯酰菌胺(156052-68-5), (4.13) 5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶(214706-53-3)和(4.14) 3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪(1002756-87-7)。
(5) 能够具有多位点作用的化合物,例如(5.1)波尔多液(8011-63-0), (5.2) 敌菌丹(2425-06-1), (5.3) 克菌丹(133-06-2) (WO 02/12172), (5.4) 百菌清(1897-45-6), (5.5) 氢氧化铜(20427-59-2), (5.6) 环烷酸铜(1338-02-9), (5.7) 氧化铜(1317-39-1), (5.8) 氧氯化铜(1332-40-7), (5.9) 硫酸铜(2+) (7758-98-7), (5.10) 苯氟磺胺(1085-98-9), (5.11) 二噻农(3347-22-6), (5.12) 多果定(2439-10-3), (5.13) 多果定游离碱, (5.14) 福美铁(14484-64-1), (5.15) 氟灭菌丹(719-96-0), (5.16) 灭菌丹(133-07-3), (5.17) 双胍辛盐(108173-90-6), (5.18) 双胍辛乙酸盐, (5.19) 双胍辛胺(13516-27-3), (5.20) 双八胍盐(169202-06-6), (5.21) 双胍辛胺乙酸盐(57520-17-9), (5.22) 代森锰铜(53988-93-5), (5.23) 代森锰锌(8018-01-7), (5.24) 代森锰(12427-38-2), (5.25) 代森联(9006-42-2), (5.26) 代森联锌(metiram zinc) (9006-42-2), (5.27) 喹啉铜(10380-28-6), (5.28) 丙烷脒(104-32-5), (5.29) 丙森锌(12071-83-9), (5.30) 硫磺和包括多硫化钙的硫磺制剂(7704-34-9), (5.31) 福美双(137-26-8), (5.32) 甲苯氟磺胺(731-27-1), (5.33) 代森锌(12122-67-7)和(5.34) 福美锌(137-30-4)。
(6) 能够诱导宿主防御的化合物,例如(6.1) 苯并噻二唑(135158-54-2), (6.2)异噻菌胺(224049-04-1), (6.3) 烯丙苯噻唑(27605-76-1)和(6.4) 噻酰菌胺(223580-51-6)。
(7) 氨基酸和/或蛋白质生物合成的抑制剂,例如(7.1) 胺扑灭(23951-85-1),(7.2) 灭瘟素(2079-00-7), (7.3) 嘧菌环胺(121552-61-2), (7.4) 春雷霉素(6980-18-3), (7.5) 春雷霉素盐酸盐水合物(19408-46-9), (7.6) 嘧菌胺(110235-47-7), (7.7)嘧霉胺(53112-28-0)和(7.8) 3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉(861647-32-7) (WO2005070917)。
(8) ATP产生的抑制剂,例如(8.1)三苯基乙酸锡(900-95-8), (8.2) 三苯基氯化锡(639-58-7), (8.3) 毒菌锡(76-87-9)和(8.4)硅噻菌胺(175217-20-6)。
(9) 细胞壁合成的抑制剂,例如(9.1) 苯噻菌胺(177406-68-7), (9.2) 烯酰吗啉(110488-70-5), (9.3) 氟吗啉(211867-47-9), (9.4) 异丙菌胺(140923-17-7),(9.5) 双炔酰菌胺(374726-62-2), (9.6) 多抗霉素(11113-80-7), (9.7) 多氧霉素(22976-86-9), (9.8) 有效霉素A (37248-47-8)和(9.9) 霜霉灭(283159-94-4; 283159-90-0)。
(10) 脂质和膜合成的抑制剂,例如(10.1) 联苯(92-52-4), (10.2) 地茂散(2675-77-6), (10.3) 氯硝胺(99-30-9), (10.4) 敌瘟磷(17109-49-8), (10.5) 土菌灵(2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) 异稻瘟净(26087-47-8),(10.8) 稻瘟灵(50512-35-1), (10.9) 霜霉威(25606-41-1), (10.10) 霜霉威盐酸盐(25606-41-1), (10.11) 硫菌威(19622-08-3), (10.12) 定菌磷(13457-18-6), (10.13)五氯硝基苯(82-68-8), (10.14) 四氯硝基苯(117-18-0)和(10.15)甲基立枯磷(57018-04-9)。
(11) 黑色素生物合成的抑制剂,例如(11.1) 加普胺(104030-54-8), (11.2) 双氯氰菌胺(139920-32-4), (11.3) 氰菌胺(115852-48-7), (11.4) 四氯苯酞(27355-22-2), (11.5) 咯喹酮(57369-32-1), (11.6) 三环唑(41814-78-2)和(11.7) {3-甲基-1-[(4-甲基苯甲酰基)氨基]丁-2-基}氨基甲酸-2,2,2-三氟乙酯(851524-22-6)(WO2005042474)。
(12) 核酸合成的抑制剂,例如(12.1) 苯霜灵(71626-11-4), (12.2) 精苯霜灵(benalaxyl-M, kiralaxyl) (98243-83-5), (12.3) 乙嘧酚磺酸酯(41483-43-6),(12.4) clozylacon (67932-85-8), (12.5) 二甲嘧酚(5221-53-4), (12.6) 乙嘧酚(23947-60-6), (12.7) 呋霜灵(57646-30-7), (12.8) 噁霉灵(10004-44-1), (12.9) 甲霜灵(57837-19-1), (12.10) 精甲霜灵(metalaxyl-M, mefenoxam) (70630-17-0),(12.11) 呋酰胺(58810-48-3), (12.12) 噁霜灵(77732-09-3)和(12.13)喹菌酮(14698-29-4)。
(13) 信号转导的抑制剂,例如(13.1) 乙菌利(84332-86-5), (13.2) 拌种咯(74738-17-3), (13.3) 咯菌腈(131341-86-1), (13.4) 异菌脲(36734-19-7), (13.5)腐霉利(32809-16-8), (13.6) 苯氧喹啉(124495-18-7)和(13.7) 乙烯菌核利(50471-44-8)。
(14) 能够起解联剂作用的化合物,例如(14.1) 乐杀螨(485-31-4), (14.2) 消螨普(131-72-6), (14.3) 嘧菌腙(89269-64-7), (14.4) 氟啶胺(79622-59-6)和(14.5)消螨多(131-72-6)。
(15) 其它化合物,例如(15.1) 苯噻清(21564-17-0), (15.2) 哒菌酮(163269-30-5), (15.3) 卡巴西霉素(70694-08-5), (15.4) 香芹酮(99-49-0), (15.5) 灭螨猛(2439-01-2), (15.6) 甲氧苯啶菌(pyriofenone) (chlazafenone) (688046-61-9),(15.7) 硫杂灵(11096-18-7), (15.8) 环氟菌胺(180409-60-3), (15.9) 霜脲氰(57966-95-7), (15.10) 环丙磺酰胺(221667-31-8), (15.11) 棉隆(533-74-4), (15.12) 咪菌威(62732-91-6), (15.13) 双氯酚(97-23-4), (15.14) 哒菌酮(62865-36-5), (15.15)野燕枯(49866-87-7), (15.16) 野燕枯甲基硫酸盐(43222-48-6), (15.17) 二苯胺(122-39-4), (15.18) ecomate, (15.19) 胺苯吡菌酮(473798-59-3), (15.20) 氟酰菌胺(154025-04-4), (15.21) 氟氯菌核利(41205-21-4), (15.22) 磺菌胺(106917-52-6),(15.23) 氟噻亚菌胺(304900-25-2), (15.24) 三乙膦酸铝(39148-24-8), (15.25) 三乙膦酸钙, (15.26) 三乙膦酸钠(39148-16-8), (15.27) 六氯苯(118-74-1), (15.28) 人间霉素(81604-73-1), (15.29) 磺菌威(66952-49-6), (15.30) 异硫氰酸甲酯(556-61-6), (15.31) 苯菌酮(220899-03-6), (15.32) 米多霉素(67527-71-3), (15.33) 多马霉素(7681-93-8), (15.34) 福美镍(15521-65-0), (15.35) 酞菌酯(10552-74-6),(15.36) 辛噻酮(26530-20-1), (15.37) oxamocarb (917242-12-7), (15.38)oxyfenthiin (34407-87-9), (15.39) 五氯苯酚和盐(87-86-5), (15.40) 苯醚菊酯,(15.41) 亚磷酸及其盐(13598-36-2), (15.42) 霜霉威乙膦酸盐, (15.43) 丙醇菌素-钠(88498-02-6), (15.44) 丙氧喹啉(189278-12-4), (15.45) 丁吡吗啉(868390-90-3),(15.45e) (2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮(1231776-28-5), (15.45z) (2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮(1231776-29-6), (15.46) 吡咯菌素(1018-71-9) (EP-A 1 559 320),(15.47) 异丁乙氧喹啉(376645-78-2), (15.48) 叶枯酞(76280-91-6), (15.49) 甲磺菌胺 (304911-98-6), (15.50) 咪唑嗪(72459-58-6), (15.51) 水杨菌胺(70193-21-4),(15.52) 氰菌胺(84527-51-5), (15.53) 2-甲基丙酸-(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰基氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-dioxonan-7-酯(517875-34-2) (WO2003035617), (15.54) 1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮(1003319-79-6) (WO2008013622), (15.55) 1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮(1003319-80-9) (WO2008013622), (15.56) 1-(4-{4-[5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮(1003318-67-9) (WO2008013622), (15.57) 1H-咪唑-1-甲酸-1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-酯(111227-17-9), (15.58) 2,3,5,6-四氯-4-(甲基磺酰基)吡啶(13108-52-6), (15.59) 2,3-二丁基-6-氯噻吩并[2,3-d]嘧啶-4(3H)-酮(221451-58-7), (15.60) 2,6-二甲基-1H,5H-[1,4]二噻吩并(dithiino)[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮, (15.61) 2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5R)-5-苯基-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮(1003316-53-7) (WO 2008013622), (15.62) 2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5S)-5-苯基-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮(1003316-54-8) (WO 2008013622), (15.63) 2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-{4-[4-(5-苯基-4,5-二氢-1,2-噁唑-3-基)-1,3-噻唑-2-基]哌啶-1-基}乙酮(1003316-51-5) (WO2008013622), (15.64) 2-丁氧基-6-碘-3-丙基-4H-色烯-4-酮, (15.65) 2-氯-5-[2-氯-1-(2,6-二氟-4-甲氧基苯基)-4-甲基-1H-咪唑-5-基]吡啶, (15.66) 2-苯基苯酚和盐(90-43-7), (15.67) 3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉(861647-85-0) (WO2005070917), (15.68) 3,4,5-三氯吡啶-2,6-二甲腈(17824-85-0),(15.69) 3-[5-(4-氯苯基)-2,3-二甲基-1,2-噁唑烷-3-基]吡啶, (15.70) 3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪, (15.71) 4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪, (15.72) 5-氨基-1,3,4-噻二唑-2-硫醇, (15.73) 5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-磺酰肼(134-31-6), (15.74) 5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺(1174376-11-4) (WO2009094442), (15.75) 5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺(1174376-25-0) (WO2009094442), (15.76) 5-甲基-6-辛基[1,2,4]三唑并[1,5-a]嘧啶-7-胺, (15.77) (2Z)-3-氨基-2-氰基-3-苯基丙-2-烯酸乙酯, (15.78) N'-(4-{[3-(4-氯苄基)-1,2,4-噻二唑-5-基]氧基}-2,5-二甲苯基)-N-乙基-N-甲基亚氨基甲酰胺,(15.79) N-(4-氯苄基)-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺, (15.80) N-[(4-氯苯基)(氰基)甲基]-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺, (15.81)N-[(5-溴-3-氯吡啶-2-基)甲基]-2,4-二氯吡啶-3-甲酰胺, (15.82) N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯吡啶-3-甲酰胺, (15.83) N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2-氟-4-碘吡啶-3-甲酰胺, (15.84) N-{(E)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺(221201-92-9), (15.85) N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺(221201-92-9), (15.86)N'-{4-[(3-叔丁基-4-氰基-1,2-噻唑-5-基)氧基]-2-氯-5-甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺, (15.87) N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-(1,2,3,4-四氢萘-1-基)-1,3-噻唑-4-甲酰胺(922514-49-6)(WO2007014290), (15.88) N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1R)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺(922514-07-6)(WO2007014290), (15.89) N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1S)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺(922514-48-5)(WO2007014290),(15.90){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸戊酯, (15.91) 吩嗪-1-甲酸, (15.92) 喹啉-8-醇(134-31-6),(15.93) 喹啉-8-醇硫酸盐(2:1) (134-31-6)和(15.94) {6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯。
(16) 其它化合物,例如(16.1) 1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺, (16.2) N-(4'-氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺, (16.3) N-(2',4'-二氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺, (16.4) 3-(二氟甲基)-1-甲基-N-[4'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺,(16.5) N-(2',5'-二氟联苯-2-基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-甲酰胺, (16.6)3-(二氟甲基)-1-甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺(从WO2004/058723已知), (16.7) 5-氟-1,3-二甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.8) 2-氯-N-[4'-(丙-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺(从WO 2004/058723已知), (16.9) 3-(二氟甲基)-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.10)N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.11) 3-(二氟甲基)-N-(4'-乙炔基联苯-2-基)-1-甲基-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.12) N-(4'-乙炔基联苯-2-基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.13) 2-氯-N-(4'-乙炔基联苯-2-基)吡啶-3-甲酰胺(从WO 2004/058723已知), (16.14) 2-氯-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺(从WO 2004/058723已知), (16.15) 4-(二氟甲基)-2-甲基-N-[4'-(三氟甲基)联苯-2-基]-1,3-噻唑-5-甲酰胺(从WO 2004/058723已知),(16.16) 5-氟-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.17) 2-氯-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺(从WO 2004/058723已知), (16.18) 3-(二氟甲基)-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.19) 5-氟-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺(从WO 2004/058723已知), (16.20) 2-氯-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺(从WO 2004/058723已知), (16.21) (5-溴-2-甲氧基-4-甲基吡啶-3-基)(2,3,4-三甲氧基-6-甲基苯基)甲酮(从EP-A 1 559 320已知), (16.22) N-[2-(4-{[3-(4-氯苯基)丙-2-炔-1-基]氧基}-3-甲氧基苯基)乙基]-N2-(甲磺酰基)缬氨酰胺(220706-93-4), (16.23) 4-氧代-4-[(2-苯乙基)氨基]丁酸和(16.24) {6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸-丁-3-炔-1-酯。
种类(1)-(16)的所有命名的混合用组分可任选地(如果它们的官能团能够)与合适的碱或酸形成盐。
包含式(I)的化合物与杀细菌剂化合物的混合物的本发明组合物也是特别有利的。合适的杀细菌剂混合用组分的例子可选自下述列表:溴硝丙二醇、双氯酚、2-氯-6-三氯甲基吡啶、福美镍、春雷霉素、辛噻酮、呋喃羧酸、土霉素、烯丙苯噻唑、链霉素、叶枯酞、硫酸铜和其它铜制剂。
本发明的式(I)的化合物和杀真菌剂组合物可用来治疗性或预防性地防治植物或作物的植物病原性真菌。
因而,根据本发明的另一个方面,提供了一种治疗性或预防性地防治植物或作物的植物病原性真菌的方法,该方法的特征在于,将本发明的式(I)的化合物或杀真菌剂组合物施用于种子、植物或植物果实、或者正在生长或需要生长植物的土壤。
本发明的处理方法还可用于处理繁殖材料,例如块茎和根茎,还有种子、幼苗或移栽(pricking out)幼苗以及植物或移栽植物。这种处理方法也可以用于处理根部。本发明的处理方法还可以用于处理植物的地上部分,例如有关植物的干、茎或梗、叶、花和果实。
根据本发明,所有植物和植物部分都可进行处理。植物是指所有植物和植物群体,例如需要和不需要的野生植物、品种以及植物变种(可受或不受植物品种权或植物育种者权保护的)。品种和植物变种可以为通过常规繁殖和育种方法或者通过生物工程和基因工程方法获得的植物,所述常规繁殖和育种方法可被一种或多种生物技术方法辅助或补充,例如通过使用双单倍体、原生质体融合、随机和定向突变、分子或遗传标记。植物部分是指植物的所有地上和地下部分和器官,例如苗、叶、花和根,由此例如可以列出叶、针叶、茎、枝、花、子实体、果实和种子以及根、球茎和根茎。作物和无性繁殖及有性繁殖材料,例如插条、球茎、根茎、纤匐枝和种子也属于植物部分。
在可用本发明的方法保护的植物中,可以提及主要大田作物,如玉米、大豆、棉花、芸苔属油菜如甘蓝型油菜(如卡诺拉油菜)、芜菁、芥菜(如芥末)和埃塞俄比亚芥,水稻、小麦、糖用甜菜、甘蔗、燕麦、黑麦、大麦、黍、黑小麦、亚麻、各种植物分类群的藤和各种水果和蔬菜,如蔷薇科物种(例如仁果类,如苹果和梨,以及核果类,如杏、樱桃、杏仁和桃,浆果类,如草莓)、茶蔗子科物种(Ribesioidae sp.)、胡桃科物种(Juglandaceae sp.)、桦木科物种(Betulaceae sp.)、漆树科物种(Anacardiaceae sp.)、山毛榉科物种(Fagaceae sp.)、桑科物种(Moraceae sp.)、木犀科物种(Oleaceae sp.)、猕猴桃科物种(Actinidaceae sp.)、樟科物种(Lauraceae sp.)、芭蕉科物种(Musaceae sp. )(例如香蕉树和plantings)、茜草科物种(Rubiaceae sp.)(例如咖啡)、山茶科物种(Theaceae sp.)、梧桐科物种(Sterculiceae sp.)、芸香科物种(Rutaceae sp.)(例如柠檬、橙子和葡萄柚);茄科物种(Solanaceae sp.)(例如,西红柿、马铃薯、胡椒、茄子)、百合科物种(Liliaceae sp.)、菊科物种(Compositiae sp.)(例如莴苣、朝鲜蓟和菊苣-包括根菊苣(root chicory)、苦苣或普通菊苣(common chicory))、伞形科物种(Umbelliferae sp.)(例如胡萝卜、香菜、芹菜和根芹菜)、葫芦科物种(Cucurbitaceae sp.)(例如黄瓜-包括小黄瓜、南瓜、西瓜、葫芦和甜瓜)、葱科物种(Alliaceae sp.)(例如洋葱和韭葱)、十字花科物种(Cruciferae sp.)(例如白球甘蓝、红球甘蓝、花茎甘蓝、花椰菜、抱子甘蓝、青菜、球茎甘蓝、小红萝卜、辣根、水芹、大白菜)、豆科物种(Leguminosae sp.)(例如花生、豌豆和豆类-诸如蔓菜豆和蚕豆)、藜科物种(Chenopodiaceae sp.)(例如饲用甜菜、叶用甜菜、菠菜、甜菜根)、锦葵科(Malvaceae)(例如秋葵)、天门冬科(Asparagaceae)(例如芦笋);园艺作物和森林作物;观赏植物;以及这些作物的遗传修饰的同系物。
根据本发明的处理方法可用于处理遗传修饰的生物体(GMOs),例如植物或种子。遗传修饰的植物(或转基因植物)是异源基因已经稳定整合到基因组中的植物。表述“异源基因”本质上表示这样一种基因,该基因在植物外部提供或组装,并且当该基因被引入核基因组、叶绿体基因组或线粒体基因组中时,其通过表达感兴趣的蛋白质或多肽、或者通过减量调节植物中存在的其它基因(诸基因)或使这些基因(诸基因)沉默(使用例如反义技术、共抑制技术或RNA干扰-RNAi技术),提供具有新的或改进的农学性质或其它性质的转化植物。位于基因组中的异源基因也称为转基因。通过其在植物基因组中的特定位置定义的转基因称为转化或转基因事件。
根据植物物种或植物品种、它们的场所和生长条件(土壤、气候、生长期、饮食),根据本发明的处理也可能产生附加效应。因此,例如,减少可根据本发明使用的活性化合物和组合物的施用率和/或拓宽其活性范围和/或增加其活性,有可能获得以下效果:更好的植物生长,对高温或低温的耐受性增加,对干旱或水或土壤盐含量的耐受性增加,开花性能提高,更容易收获,加快的成熟,更高的收获率,更大的果实,更高的植物高度,叶子的颜色更绿,开花更早,收获的产品的品质和/或营养价值更高,果实中糖浓度更高,收获的产品的储存稳定性和/或加工性更佳,这些益处超过了实际预期的效果。
在某些施用率下,根据本发明的活性化合物组合还可能在植物中产生加强效应。因此,它们也适合用于动员植物的防御系统来抵抗不利的微生物的进攻。如果合适,这种作用可能是根据本发明的组合例如在抵抗真菌方面活性增强的原因之一。在本申请上下文中,植物加强(抗性诱导)物质应理解为是指能以某种方式刺激植物的防御系统从而在随后被不利的微生物接种时经过处理的植物对这些微生物表现出明显的抵抗性的物质或物质的组合。在此情况中,不利的微生物应理解为是指植物病原性真菌、细菌和病毒。因此,根据本发明的物质可用于保护植物,使其在经过处理后的一段时间内能抵抗上述病原体的攻击。保护起作用的时间通常为在用活性化合物处理植物后1-10天,优选1-7天。
优选根据本发明处理的植物和植物品种包括所有具有遗传物质的植物,这些遗传物质赋予这些植物特别有利且有用的性质(无论是通过培育和/或生物技术手段获得的)。
也优选根据本发明处理的植物和植物品种能抵抗一种或多种生物胁迫,即所述植物对动物和微生物害虫表现出更佳的防御性,例如抵抗线虫、昆虫、螨、植物病原性真菌、细菌、病毒和/或类病毒。
抗线虫植物的例子描述于例如美国专利申请号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或12/497,221。
也可以根据本发明处理的植物和植物品种是对一种或多种非生物胁迫具有抵抗性的植物。非生物胁迫情况可包括例如干旱、冷温暴露、热暴露、渗透性应激、水灾、增加的土壤盐渍度、增加的矿物暴露、臭氧暴露、高光暴露、氮营养成分的有限利用率、磷营养成分的有限利用率、蔽阴。
也可以根据本发明处理的植物和植物品种是具有增强的产率特征的植物。所述植物的产率提高的原因可能是例如改进的植物生理学、生长和发育,例如水利用效率、水保持效率、改进的氮利用、增强的碳同化作用、改进的光合作用、提高的发芽效率和加快的成熟。产率还可能受到植物结构改进(在胁迫和非胁迫条件下)的影响,包括、但不限于早期开花、对杂交种子生产的开花控制、幼苗活力、植物尺寸、节间数目和距离、根生长、种子尺寸、果实尺寸、豆荚尺寸、豆荚或穗数目、每豆荚或穗的种子数目、种子质量、加强的种子灌浆(filling)、减小的种子散布、减小的豆荚开裂和抗倒伏性。其它产率特征包括种子组成,例如碳水化合物含量、蛋白质含量、油含量和组成、营养价值、抗营养化合物的减少、改进的加工性和更佳的储存稳定性。
具有上述特征的植物的例子非穷尽性地列在表A中。
可根据本发明处理的植物是已经表现出杂种优势或杂交活力特征并由此通常产生更佳的产率、活力、健康状况和对生物和非生物胁迫的抗性的杂交植物。这类植物通常通过将一个近亲交配的雄性不育的亲代系(母本)与另一个近亲交配的雄性能育的亲代系(父本)杂交而制得。杂种种子通常从雄性不育植物采集,出售给种植者。雄性不育植物有时(例如,在玉米中)可以通过去雄来生产,即机械除去雄性生殖器官(或雄花),但是更通常的是,雄性不育是植物基因组中遗传定子的结果。在那种情况中,特别是在种子是要从杂交植物中采集的所需产品时,其通常可用于确保杂交植物的雄性能育性得到完全恢复。这可以通过确保父本具有合适的育性恢复基因来实现,该育性恢复基因能恢复含有造成雄性不育的遗传定子的杂交植物的雄性能育性。造成雄性不育的遗传定子可位于细胞质中。细胞质雄性不育(CMS)的例子例如描述于芸苔属物种中(W0 92/05251、WO 95/09910、WO 98/27806、WO 05/002324、WO 06/021972和US 6,229,072)。但是,造成雄性不育的遗传定子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(例如遗传工程)得到。获得雄性不育植物的特别有用的手段描述于WO 89/10396中,其中,例如,核糖核酸酶如芽孢杆菌RNA酶选择性地表达在雄蕊的毯毡层细胞中。然后,可通过在毯毡层细胞中表达核糖核酸酶抑制剂如芽孢杆菌RNA酶抑制剂来恢复能育性(例如WO 91/002069)。
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如遗传工程得到)是耐受除草剂的植物,即能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赋予这种除草剂耐受性的突变的植物来获得。
例如,除草剂抗性的植物是耐草甘膦的植物,即对除草剂草甘膦或其盐具有耐受性的植物。可通过不同的手段使植物对草甘膦具有耐受性。例如,耐草甘膦的植物可通过用编码酶5-烯醇丙酮酰基莽草酸盐-3-磷酸合酶(EPSPS)的基因转化植物而获得。这类EPSPS基因的例子是细菌鼠伤寒沙门杆菌(Salmonella typhimurium)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 Plant Physiol. 7, 139-145)、编码矮牵牛EPSPS(Petunia EPSPS)的基因(Shah等人, 1986, Science 233, 478-481)、番茄EPSPS(TomatoEPSPS)(Gasser等人, 1988, J. Biol. Chem. 263, 4280-4289)、或牛筋草EPSPS(Eleusine EPSPS) (WO 01/66704)。这类基因还可以是突变的EPSPS,如在例如EP0837944、WO 00/66746、WO 00/66747或WO02/26995中所述。耐草甘膦的植物还可以通过表达编码草甘膦氧化还原酶的基因来得到,如美国专利号5,776,760和5,463,175中所描述。耐草甘膦的植物还可以通过表达编码草甘膦乙酰转移酶的基因来得到,例如如WO 02/36782、WO 03/092360、WO 05/012515和WO 07/024782中所描述的。耐草甘膦的植物还可以通过选择含上述基因的天然存在的突变的植物来得到,如例如WO 01/024615或WO 03/013226中所描述的。表达赋予草甘膦耐受性的EPSPS基因的植物描述于例如美国专利申请号11/517,991、10/739,610、12/139,408、12/352,532、11/312,866、11/315,678、12/421,292、11/400,598、11/651,752、11/681,285、11/605,824、12/468,205、11/760,570、11/762,526、11/769,327、11/769,255、11/943801或12/362,774中。包含赋予草甘膦耐受性的其它基因如脱羧酶基因的植物描述于例如美国专利申请11/588,811、11/185,342、12/364,724、11/185,560或12/423,926中。
其它除草剂抗性的植物是例如能耐受抑制谷氨酰胺合酶的除草剂(例如双丙氨膦、草胺膦(phosphinothricin)或草铵膦(glufosinate))的植物。这类植物可通过表达解毒除草剂的酶或对抑制作用具有抗性的突变谷氨酰胺合酶而得到,例如,描述于美国专利申请号11/760,602中。一种有效的解毒酶是编码草胺膦乙酰基转移酶的酶(例如来自链霉菌属物种的bar或pat蛋白)。例如,在美国专利号5,561,236、5,648,477、5,646,024、5,273,894、5,637,489、5,276,268、5,739,082、5,908,810和7,112,665中描述了表达外源草胺膦乙酰转移酶的植物。
其它能耐受除草剂的植物还有能耐受抑制羟苯丙酮酸二加氧酶(HPPD)的除草剂的植物。羟苯丙酮酸二加氧酶是催化对羟苯丙酮酸(HPP)转化为尿黑酸盐的反应的酶。对HPPD抑制剂具有耐受性的植物可用编码天然产生的抗性HPPD酶的基因或编码突变或嵌合HPPD酶的基因进行转化,如WO 96/38567、WO 99/24585、WO 99/24586、WO 2009/144079、WO2002/046387或US 6,768,044中所描述的。对HPPD抑制剂的耐受性还可以通过用编码某些能形成尿黑酸盐的酶的基因来转化植物而获得,虽然天然HPPD酶受到HPPD抑制剂的抑制。WO 99/34008和WO 02/36787中描述了这些植物和基因。植物对HPPD抑制剂的耐受性还可以通过用编码具有预苯酸脱氢酶(PDH)活性的酶的基因以及编码HPPD耐受酶的基因来转化植物而得到提高,如WO 2004/024928中所描述的。此外,可通过以下方式使植物更能耐受HPPD-抑制剂除草剂:向它们的基因组中加入编码能代谢或降解HPPD抑制剂的酶的基因,所述酶例如是CYP450酶,如WO 2007/103567和WO 2008/150473中所示。
其它耐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、三唑并嘧啶类、吡啶氧基(pryimidinyoxy)(硫代)苯甲酸盐或酯、和/或磺酰基氨基羰基三唑啉酮除草剂。已经知道,ALS酶(也称为乙酰羟酸合酶,AHAS)中的不同突变能提供对不同除草剂和除草剂群组的耐受性,如例如Tranel和Wright (2002, Weed Science 50:700-712)以及美国专利号5,605,011、5,378,824、5,141,870和5,013,659中所述。在美国专利号5,605,011、5,013,659、5,141,870、5,767,361、5,731,180、5,304,732、4,761,373、5,331,107、5,928,937和5,378,824以及国际公开WO96/33270中描述了磺酰脲耐受植物和咪唑啉酮耐受植物的生产。还在例如WO 2004/040012、WO2004/106529、WO 2005/020673、WO 2005/093093、WO 2006/007373、WO 2006/015376、WO2006/024351和WO 2006/060634中描述了其它咪唑啉酮耐受植物。例如,在WO 07/024782和美国专利申请号61/288958中还描述了其它耐受磺酰脲和咪唑啉酮的植物。
其它耐咪唑啉酮和/或磺酰脲的植物可通过诱变、在存在除草剂的情况下选择细胞培养物、或突变育种来获得,如例如美国专利5,084,082(对于大豆)、WO 97/41218(对于水稻)、美国专利5,773,702和WO 99/057965(对于糖用甜菜)、美国专利5,198,599(对于莴苣)、或WO 01/065922(对于向日葵)中所述。
同样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如遗传工程得到)是具有昆虫抗性的转基因植物,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选择含有赋予这种抗虫性的突变的植物来获得。
文中使用的“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)来自苏云金芽孢杆菌(Bacillus thuringiensis)的杀虫晶体蛋白或其杀虫部分,例如Crickmore等人(1998, Microbiology and Molecular Biology Reviews, 62:807-813)列出的杀虫晶体蛋白(Crickmore等(2005)对苏云金芽孢杆菌毒素命名进行了更新,在线参见http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/)或其杀虫部分,例如Cry蛋白类的蛋白Cry1Ab、Cry1Ac、Cry1B、Cry1C、Cry1D、Cry1F、Cry2Ab、Cry3Aa或Cry3Bb或其杀虫部分(例如EP 1999141和WO 2007/107302),或者被合成基因编码的这类蛋白,例如参见美国专利申请号12/249,016;或
2)来自苏云金芽孢杆菌的晶体蛋白或其部分,该晶体蛋白或其部分在来自苏云金芽孢杆菌的第二其它晶体蛋白或其部分存在下具有杀虫性,例如由Cry34和Cry35晶体蛋白构成的二元毒素(Moellenbeck等人. 2001, Nat. Biotechnol. 19: 668-72; Schnepf等人. 2006, Applied Environm. Microbiol. 71, 1765-1774),或由Cry1A或Cry1F蛋白和Cry2Aa或Cry2Ab或Cry2Ae蛋白构成的二元毒素(美国专利申请号12/214,022和EP08010791.5);或
3)杂合杀虫蛋白(hybrid insecticidal protein),其包含来自苏云金芽孢杆菌的不同杀虫晶体蛋白的部分,例如上面1)中所述蛋白的杂合体或上面2)中所述蛋白的杂合体,例如通过玉米事件MO N89034生产的Cry1A.105蛋白(WO 2007/027777);或
4)上述1)至3)中任一项的蛋白,其中一些(特别是1-10个)氨基酸已经被其它氨基酸替换,以得到对目标昆虫物种更高的杀虫活性,和/或扩大受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在编码DNA中引入变化,例如玉米事件MON863或MON88017中的Cry3Bb1蛋白或玉米事件MIR604中的Cry3A蛋白;或
5)来自苏云金芽孢杆菌或蜡状芽孢杆菌(Bacillus cereus)的杀虫分泌性蛋白,或其杀虫部分,例如在 http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html中所列的营养期杀虫蛋白(VIP),例如来自VIP3Aa蛋白类的蛋白;或
6)来自苏云金芽孢杆菌或蜡状芽孢杆菌的分泌性蛋白,该蛋白在来自苏云金芽孢杆菌或蜡状芽孢杆菌的第二分泌性蛋白存在下具有杀虫性,例如由VIP1A和VIP2A蛋白构成的二元毒素(WO 94/21795);或
7)杂合杀虫蛋白,其包含来自苏云金芽孢杆菌或蜡状芽孢杆菌的不同的分泌性蛋白的部分,例如上面1)中所述蛋白的杂合体或上面2)中所述蛋白的杂合体;或
8)上述5)-7)中任一项的蛋白,其中一些(特别是1-10个)氨基酸已经被其它氨基酸替换,以得到对目标昆虫物种更高的杀虫活性,和/或扩大受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在编码DNA中引入变化(同时仍然编码杀虫蛋白),例如棉花事件COT102中的VIP3Aa蛋白;或
9)来自苏云金芽孢杆菌或蜡状芽孢杆菌的分泌性蛋白,其在来自苏云金芽孢杆菌的结晶蛋白存在下具有杀虫性,例如由VIP3和Cry1A或Cry1F构成的二元毒素(美国专利申请号61/126083和61/195019),或由VIP3蛋白和Cry2Aa或Cry2Ab或Cry2Ae蛋白构成的二元毒素(美国专利申请号12/214,022和EP 08010791.5);
10)上述9)中的蛋白,其中一些(特别是1-10个)氨基酸已经被其它氨基酸替换,以得到对目标昆虫物种更高的杀虫活性,和/或扩大受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在编码DNA中引入变化(同时仍然编码杀虫蛋白)。
当然,文中所用的抗虫转基因植物还包括包含编码上述1-10类中任一类的蛋白质的基因的组合的任何植物。在一个实施方案中,抗虫植物含有不止一个编码上述1-10类中任一类的蛋白质的转基因,以扩大在使用指向不同目标昆虫物种的不同蛋白质时受影响的目标昆虫物种的范围,或者通过使用对相同目标昆虫物种具有杀虫性但具有不同作用模式(例如结合到昆虫不同受体结合位点)的不同蛋白质来延迟对植物的抗虫性发展。
文中所述的“抗虫转基因植物”还包括含有至少一种转基因的任何植物,该转基因包含表达后产生双链RNA的序列,其在被植物虫害摄入后抑制该植物虫害的生长,例如描述于WO 2007/080126、WO 2006/129204、WO 2007/074405、WO 2007/080127和WO 2007/035650。
也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如遗传工程得到)对非生物胁迫具有耐受性。这类植物可通过遗传转化或通过选择含有能赋予这种抗胁迫性的突变的植物来获得。特别有用的抗胁迫植物包括:
1)含有能减少植物细胞或植物中聚(ADP-核糖)聚合酶(PARP)基因表达和/或活性的转基因的植物,如WO 00/04173、WO/2006/045633、EP 04077984.5或EP 06009836.5中所述。
2)含有能减少植物或植物细胞中PARG编码基因表达和/或活性的耐胁迫性增强转基因的植物,如例如WO 2004/090140中所述。
3)含有一种耐胁迫性增强转基因的植物,该转基因编码烟酰胺腺嘌呤二核苷酸补救合成路径的植物功能酶,该酶包括烟酰胺酶、烟酰酸磷酸核糖基转移酶、烟酸单核苷酸磷酸腺苷转移酶、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,如例如在EP04077624.7、WO 2006/133827、PCT/EP07/002433、EP 1999263或WO 2007/107326中所述。
也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如遗传工程得到)表现出收获产品数量、品质和/或储存稳定性的改变,和/或收获产品特定成分的性质改变,例如:
1)合成变性淀粉的转基因植物,该变性淀粉与野生型植物细胞或植物中的合成淀粉相比,其物理化学性质,尤其是直链淀粉含量或直链淀粉/支链淀粉比值、支化度、平均链长、侧链分布、粘度行为、凝胶强度、淀粉粒度和/或淀粉颗粒形态改变,因而更适宜用于一些特殊应用。所述合成变性淀粉的转基因植物例如在以下文献中公开:EP 0571427、WO 95/04826、EP 0719338、WO 96/15248、WO 96/19581、WO 96/27674、WO 97/11188、WO 97/26362、WO 97/32985、WO 97/42328、WO 97/44472、WO 97/45545、WO 98/27212、WO 98/40503、WO99/58688、WO 99/58690、WO 99/58654、WO 00/08184、WO 00/08185、WO 00/08175、WO 00/28052、WO 00/77229、WO 01/12782、WO 01/12826、WO 02/101059、WO 03/071860、WO 2004/056999、WO 2005/030942、WO 2005/030941、WO 2005/095632、WO 2005/095617、WO 2005/095619、WO 2005/095618、WO 2005/123927、WO 2006/018319、WO 2006/103107、WO 2006/108702、WO 2007/009823、WO 00/22140、WO 2006/063862、WO 2006/072603、WO 02/034923、EP 06090134.5、EP 06090228.5、EP 06090227.7、EP 07090007.1、EP 07090009.7、WO 01/14569、WO 02/79410、WO 03/33540、WO 2004/078983、WO 01/19975、WO 95/26407、WO 96/34968、WO 98/20145、WO 99/12950、WO 99/66050、WO 99/53072、US 6,734,341、WO 00/11192、WO 98/22604、WO 98/32326、WO 01/98509、WO 01/98509、WO 2005/002359、US 5,824,790、US 6,013,861、WO 94/04693、WO 94/09144、WO 94/11520、WO 95/35026、WO 97/20936,
2)合成非淀粉碳水化合物聚合物的转基因植物,或合成与未经过遗传修饰的野生型植物相比具有改变的性质的非淀粉碳水化合物聚合物的转基因植物。例子是:产生多聚果糖、特别是菊糖和果聚糖类型的植物,如EP 0663956、WO 96/01904、WO 96/21023、WO 98/39460和WO 99/24593所述;产生α-1,4-葡聚糖的植物,如WO 95/31553、US 2002031826、US6,284,479、US 5,712,107、WO 97/47806、WO 97/47807、WO 97/47808和WO 00/14249所述;产生α-1,6支化的α-1,4-葡聚糖的植物,如WO 00/73422所述;产生alternan的植物,如例如WO 00/47727、WO 00/73422、EP 06077301.7、US 5,908,975和EP 0728213所述;
3)产生透明质烷(hyaluronan)的转基因植物,如例如WO 2006/032538、WO 2007/039314、WO 2007/039315、WO 2007/039316、JP 2006304779和WO 2005/012529所述;
4)转基因植物或杂种植物,例如具有“高可溶性固体含量”、“低刺激性”(LP)和/或“长储存性”(LS)等特征的洋葱,参见美国专利申请号12/020,360和61/054,026。
也可根据本发明处理的植物或植物品种(可通过植物生物技术方法如遗传工程得到)是具有改变的纤维特征的植物,如棉树。这类植物可通过遗传转化或通过选择含有赋予这种改变的纤维特征的突变的植物来获得,这类植物包括:
a)含有改变形式的纤维素合酶基因的植物,例如棉树,如WO 98/00549中所述;
b)含有改变形式的rsw2或rsw3同源核酸的植物,例如棉树,如WO 2004/053219中所述;
c)具有增强的蔗糖磷酸合酶表达的植物,例如棉树,如WO 01/017333中所述;
d)具有增强的蔗糖合酶表达的植物,例如棉树,如WO 02/45485中所述;
e)植物,例如棉树,其中在纤维状细胞基底处的胞间连丝开启的周期(timing ofthe plasmodesmatal gating)改变,例如通过减量调节纤维选择性的β-1,3-葡聚糖酶来实现,如WO 2005/017157或EP08075514.3或美国专利申请号61/128,938中所述;
f)具有改变的反应性(例如通过包括nodC的N-乙酰基葡糖胺转移酶基因和几丁质合成酶基因的表达来实现)的纤维的植物,例如棉树,如WO 2006/136351中所述。
也可以根据本发明处理的植物或植物品种(可通过植物生物技术方法如遗传工程得到)是具有改变的油分布(oil profile)特征的植物,例如油菜(oilseed rape)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这种改变的油分布特征的突变的植物来获得,这类植物包括:
a)产生具有高油酸含量的油的植物,例如油菜植物,如US 5,969,169、US 5,840,946或US 6,323,392或US 6,063,947中所述;
b)产生具有低亚麻酸含量的油的植物,例如油菜植物,如US 6,270,828、US 6,169,190或US 5,965,755中所述;
c)产生具有低水平饱和脂肪酸的油的植物,例如油菜植物,如例如美国专利号5,434,283或美国专利申请号12/668303中所述。
也可以根据本发明处理的植物或植物品种(可通过植物生物技术方法如遗传工程得到)是具有改变的种子落粒特征的植物,例如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这种改变的种子落粒特征的突变的植物来获得,并包括诸如具有延迟的或降低的种子落粒的油菜植物等植物,如美国专利申请号61/135,230 WO09/068313和WO10/006732中所述。
可根据本发明处理的特别有用的转基因植物是含转化事件或转化事件组合的植物,它们是向美国农业部(USDA)动植物卫生检验局(APHIS)提交的要求在美国非管制状态的请求的主题,无论这些请求被准予或仍然处在待审中。在任何时候,该信息很容易从APHIS(4700 River Road Riverdale, MD 20737, USA)获得,例如在其互联网站上(URLhttp://www.aphis.usda.gov/brs/not_reg.html)。在本申请的提交日当天,被APHIS审理中或被APHIS准予的要求非管制状态的请求是表B所列的那些,包括以下信息:
-请求(Petition):请求的识别号。转化事件的技术描述可在各请求文件中找到,而这些请求文件可根据该请求号从APHIS得到,例如从APHIS网站上获得。这些描述通过参考结合于本文。
-请求延伸(Extension of Petition):涉及要求进行延伸的在先的请求。
-机构(Institution):提交请求的实体的名称。
-管制项目(Regulated article):关注的植物物种。
-转基因表型(Transgenic phenotype):通过转化事件赋予植物的特性。
-转化事件或系(Transformation event or line):要求非管制状态的一个或多个事件(有时称为一个或多个系)的名称。
-APHIS文档:与请求相关的APHIS出版的各种文件,它们可以是向APHIS要求的。
其它特别有用的含单个转化事件或转化事件组合的植物例如在各个国家或地方性管理机构的数据库中列出(参见,例如http://gmoinfo.jrc.it/gmp_browse.aspx和http://www.agbios.com/dbase.php)。
更特别地,转基因植物包括在农艺学上中性或有益的位置含有转基因的植物,如表C中所列的任何专利文献中所述。
在可通过本发明方法防治的植物或作物疾病中,可提及的有:
白粉病(powdery mildew),例如:
布氏白粉菌属病(Blumeria diseases),例如由禾本科布氏白粉菌(Blumeria graminis)引起;
叉丝单囊壳属病(Podosphaera diseases),例如由白叉丝单囊壳(Podosphaera leucotricha)引起;
单丝壳属病(Sphaerotheca diseases),例如由苍耳单丝壳(Sphaerotheca fuliginea)引起;
钩丝壳属病(Uncinula diseases),例如由葡萄钩丝壳(Uncinula necator)引起;
锈病,例如:
胶锈菌属病(Gymnosporangium diseases),例如由赛宾胶锈菌(Gymnosporangium sabinae)引起;
驼孢锈属病(Hemileia diseases),例如由咖啡驼孢锈菌(Hemileia vastatrix)引起;
层锈菌属病(Phakopsora diseases),例如由豆薯层锈菌(Phakopsora pachyrhizi)或山马蝗层锈菌(Phakopsora meibomiae)引起;
柄锈菌属病(Puccinia diseases),例如由隐匿柄锈菌(Puccinia recondite)、禾柄锈菌(Puccinia graminis)或条形柄锈菌(Puccinia striiformis)引起;
单孢锈菌属病(Uromyces diseases),例如由疣顶单胞锈菌(Uromyces appendiculatus)引起;
卵菌纲病(Oomycete diseases),例如:
白锈病(Albugo diseases),例如由白锈菌(Albugo candida)引起;
盘梗霉属病(Bremia diseases),例如由莴苣盘梗霉(Bremia lactucae)引起;
霜霉属病(Peronospora diseases),例如由豌豆霜霉(Peronospora pisi)或芸苔根肿菌(P.brassicae)引起;
疫霉属病(Phytophthora diseases),例如由致病疫霉(Phytophthora infestans)引起;
单轴霉属病(Plasmopara diseases),例如由葡萄生单轴霉(Plasmopara viticola)引起;
假霜霉属病(Pseudoperonospora diseases),例如由葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonospora cubensis)引起;
腐霉属病(Pythium diseases),例如由终极腐霉(Pythium ultimum)引起;
叶斑病(Leafspot disease)、污叶病(leaf blotch disease)和叶枯病(leaf blight disease),例如:
链格孢属病(Alternaria diseases),例如由索兰尼链格孢(Alternaria solani)引起;
尾孢属病(Cercospora diseases),例如由甜菜生尾孢(Cercospora beticola)引起;
金孢子菌属病(Cladiosporum diseases),例如由瓜枝孢(Cladiosporium cucumerinum)引起;
旋孢腔菌属病(Cochliobolus diseases),例如由禾旋孢腔菌(Cochliobolus sativus(分生孢子形式:德氏霉属(Drechslera),同义词: 长蠕孢菌属(Helminthosporium))或宫部旋孢腔菌(Cochliobolus miyabeanus)引起;
刺盘孢属病(Colletotrichum diseases),例如由豆刺盘孢(Colletotrichum lindemuthanium)引起;
油橄榄孔雀斑病(Cycloconium diseases),例如由油橄榄孔雀斑菌(Cycloconium oleaginum)引起;
间座壳属病(Diaporthe diseases),例如由柑橘间座壳菌(Diaporthe citri)引起;
痂囊腔菌属病(Elsinoe diseases),例如由柑橘痂囊腔菌(Elsinoe fawcettii)引起;
盘长孢属病(Gloeosporium diseases),例如由悦色盘长孢(Gloeosporium laeticolor)引起;
小丛壳属病(Glomerella diseases),例如由围小丛壳菌(Glomerella cingulata)引起;
球座菌属病(Guignardia diseases),例如由葡萄球座菌(Guignardia bidwelli)引起;
小球腔菌属病(Leptosphaeria diseases),例如由斑点小球腔菌(Leptosphaeria maculans);颖枯小球腔菌(Leptosphaeria nodorum)引起;
稻瘟病(Magnaporthe diseases),例如由稻瘟病菌(Magnaporthe grisea)引起;
球腔菌属病(Mycosphaerella diseases),例如由禾生球腔菌(Mycosphaerella graminicola);落花生球腔菌(Mycosphaerella arachidicola);斐济球腔菌(Mycosphaerella fijiensisi)引起;
暗球腔菌属病(Phaeosphaeria diseases),例如由颖枯暗球腔菌(Phaeosphaeria nodorum)引起;
核腔菌属病(Pyrenophora diseases),例如由圆核腔菌(Pyrenophora teres)或偃麦草核腔菌(Pyrenophora tritici repentis)引起;
柱隔孢属病(Ramularia diseases),例如由辛加柱隔孢(Ramularia collo- cygni)或白斑柱隔孢(Ramularia areola)引起;
喙孢属病(Rhynchosporium diseases),例如由黑麦喙孢(Rhynchosporium secalis)引起;
壳针孢属病(Septoria diseases),例如由芹菜小壳针孢(Septoria apii)或番茄壳针孢(Septoria lycopercisi)引起;
核瑚菌属病(Typhula diseases),例如由肉孢核瑚菌(Typhulaincarnata)引起;
黑星菌属病(Venturia diseases),例如由苹果黑星菌(Venturia inaequalis)引起;
根、叶鞘和茎疾病,例如:
伏革菌属病(Corticium diseases),例如由禾伏革菌(Corticium graminearum)引起;
镰孢菌属病(Fusarium diseases),例如由尖孢镰刀菌(Fusarium oxysporum)引起;
顶囊壳属病(Gaeumannomyces diseases),例如由禾顶囊壳(Gaeumannomyces graminis)引起;
丝核菌属病(Rhizoctonia diseases),例如由立枯丝核菌(Rhizoctonia solani)引起;
帚枝霉属病(Sarocladium diseases),例如由稻帚枝霉(Sarocladium oryzae)引起;
小核菌病(Sclerotium diseases),例如由稻小核菌(Sclerotium oryzae)引起;
塔普斯(Tapesia)病,例如由塔普斯梭状芽孢杆菌(Tapesia acuformis)引起;
根串珠霉属病(Thielaviopsis diseases),例如由根串珠霉(Thielaviopsis basicola)引起;
耳穗和圆锥花序疾病,例如:
链格孢属病(Alternaria diseases),例如由链格孢属物种(Alternaria spp.)引起;
曲霉菌属病(Aspergillus diseases),例如由黄曲霉(Aspergillus flavus)引起;
枝孢属病(Cladosporium diseases),例如由枝孢属物种(Cladosporium spp.)引起;
麦角菌属病(Claviceps diseases),例如由黑麦麦角菌(Claviceps purpurea)引起;
镰孢属病(Fusarium diseases),例如由大刀镰孢菌(Fusarium culmorum)引起;
赤霉属病(Gibberella diseases),例如由玉蜀黍赤霉(Gibberella zeae)引起;
水稻云形病(Monographella diseases),例如由水稻云形菌(Monographella nivalis)引起;
黑穗病和腥黑穗病,例如:
轴黑粉菌属病(Sphacelotheca diseases),例如由丝轴黑粉菌(Sphacelotheca reiliana)引起;
腥黑粉菌属病(Tilletia diseases),例如由小麦网腥黑粉菌(Tilletia caries)引起;
条黑粉菌属病(Urocystis diseases),例如由隐条黑粉菌(Urocystis occulta)引起;
黑粉菌属病(Ustilago diseases),例如由裸黑粉菌(Ustilago nuda)引起;
果实腐烂和霉菌病,例如:
曲霉菌属病(Aspergillus diseases),例如由黄曲霉(Aspergillus flavus)引起;
葡萄孢属病(Botrytis diseases),例如由灰葡萄孢(Botrytis cinerea)引起;
青霉属病(Penicillium diseases),例如由扩展青霉(Penicillium expansum)引起;
根霉菌属病(Rhizopus diseases),例如由匍茎根霉菌(Rhizopus stolonifer)引起;
核盘菌属病(Sclerotinia diseases),例如由核盘菌(Sclerotinia sclerotiorum)引起;
轮枝孢属病(Verticillium diseases),例如由黑白轮枝孢(Verticillium alboatrum)引起;
种子和土壤传播的腐烂、发霉、枯萎、腐烂和猝倒病:
链格孢属病(Alternaria diseases),例如由甘蓝链格孢菌(Alternaria brassicicola)引起;
丝囊霉病(Aphanomyces diseases),例如由豌豆丝囊霉(Aphanomyces euteiches)引起;
壳二孢病(Ascochyta diseases),例如由兵豆壳二孢(Ascochyta lentis)引起;
曲霉菌属病(Aspergillus diseases),例如由黄曲霉(Aspergillus flavus)引起;
枝孢属病(Cladosporium diseases),例如由多主枝孢(Cladosporium herbarum)引起;
旋孢腔菌属病(Cochliobolus diseases),例如由禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:德氏霉属(Drechslera)、双极霉属(Bipolaris),同义词:长蠕孢菌属(Helminthosporium))引起;
刺盘孢属病(Colletotrichum diseases),例如由番茄刺盘孢(Colletotrichum coccodes)引起;
镰孢属病(Fusarium diseases),例如由大刀镰孢菌(Fusarium culmorum)引起;
赤霉属病(Gibberella diseases),例如由玉蜀黍赤霉(Gibberella zeae)引起;
壳球孢属病(Macrophomina diseases),例如由菜豆壳球孢(Macrophomina phaseolina)引起;
雪霉病(Monographella diseases),例如由小麦雪霉(Monographella nivalis)引起;
青霉属病(Penicillium diseases),例如由扩展青霉(Penicillium expansum)引起;
茎点霉属病(Phoma diseases),例如由甘蓝茎点霉(Phoma lingam)引起;
拟茎点霉属病(Phomopsis diseases),例如由大豆拟茎点霉(Phomopsis sojae)引起;
疫霉属病(Phytophthora diseases),例如由恶疫霉(Phytophthora cactorum)引起;
核腔菌属病(Pyrenophora diseases),例如由麦类核腔菌(Pyrenophora graminea)引起;
梨孢属病(Pyricularia diseases),例如由稻梨孢菌(Pyricularia oryzae)引起;
腐霉属病(Pythium diseases),例如由终极腐霉(Pythium ultimum)引起;
丝核菌属病(Rhizoctonia diseases),例如由立枯丝核菌(Rhizoctonia solani)引起;
根霉病(Rhizopus diseases),例如由米根霉(Rhizopus oryzae)引起;
小核菌病(Sclerotium diseases),例如由齐整小核菌(Sclerotium rolfsii)引起;
壳针孢属病(Septoria diseases),例如由颖枯壳针孢(Septoria nodorum)引起;
核瑚菌病(Typhula diseases),例如由肉孢核瑚菌(Typhula incarnata)引起;
轮枝孢属病(Verticillium diseases),例如由大丽花轮枝孢(Verticillium dahliae)引起;
溃疡病(Canker)、松碎(broom)和梢枯病,例如:
丛赤壳属病(Nectria diseases),例如由仁果干癌丛赤壳菌(Nectria galligena)引起;
枯萎病,例如:
链核盘菌属病(Monilinia diseases),例如由核果链核盘菌(Monilinia laxa)引起;
叶疱病或缩叶病,例如:
外担子菌属病(Exobasidium diseases),例如由坏损外担子菌(Exobasidium vexans)引起;
外囊菌属病(Taphrina diseases),例如由畸形外囊菌(Taphrina deformans)引起;
木质植物的衰退病,例如:
依科病(Esca diseases),例如由根霉格孢菌(Phaemoniella clamydospora)引起;
葡萄顶枯病(Eutypa dyeback),例如由葡萄弯孢壳(Eutypa lata)引起;
灵芝属病(Ganoderma diseases),例如由狭长孢灵芝(Ganoderma boninense)引起;
硬孔菌属病(Rigidoporus diseases),例如由木硬孔菌(Rigidoporus linosus)引起;
花和种子的疾病,例如:
葡萄孢属病(Botrytis diseases),例如由灰葡萄孢(Botrytis cinerea)引起;
根茎类疾病,例如:
丝核菌属病(Rhizoctonia diseases),例如由立枯丝核菌(Rhizoctonia solani)引起;
长蠕孢属病(Helminthosporium diseases),例如由茄病长蠕孢(Helminthosporium solani)引起;
根肿病,例如:
根肿菌属病(Plasmodiophora diseases),例如由芸苔根肿菌(Plamodiophora brassicae)引起;
由细菌生物引起的疾病,所述细菌生物例如:
黄单胞菌属物种,例如野油菜黄单胞菌水稻致病变种(Xanthomonas campestris pv.oryzae);
假单胞菌属物种,例如丁香假单胞菌黄瓜致病变种(Pseudomonas syringae pv.lachrymans);
欧文氏菌属物种,例如解淀粉欧文氏菌(Erwinia amylovora)。
本发明的组合物还可以用来抵抗易于在木材上或木材内部生长的真菌疾病。术语“木材”指所有种类的木材,以及对该木材进行加工(用于建筑物)的所有类型的加工材料,例如实体木材、高密度木材、层积材和胶合板。根据本发明处理木材的方法主要包括:使木材与本发明的一种或多种化合物或本发明的组合物接触;这包括例如直接施用、喷涂、浸渍、注入或任何其它合适的方式。
在根据本发明的处理方法中,对于应用于叶处理而言,活性化合物通常施用剂量一般且有利地为10-800克/公顷,优选50-300克/公顷。在种子处理的情况下,活性物质的施用剂量一般且有利地为2-200克/100千克种子,优选为3-150克/100千克种子。
应该清楚地理解,本文中指明的剂量是作为本发明方法的示例性例子给出。本领域技术人员知道如何调节(尤其是根据待处理的植物或作物的性质)施用剂量。
本发明的化合物或混合物也可以用于制备对治疗性或预防性处理人或动物真菌疾病有用的组合物,所述疾病例如霉菌病、皮肤病、发藓菌病和念珠菌病或由曲霉菌属物种(Aspergillus spp.)如烟曲霉(Aspergillus fumigatus)引起的疾病。
下面的实施例例示了根据本发明的式(I)的活性化合物1-甲基-3-二卤代甲基-5-卤代吡唑(硫代)甲酰胺和中间体的制备和用途。
从式(II)的化合物和式(III)的化合物合成根据本发明的式(I)的酰胺的操作:
5-氯-3-(二氟甲基)-1-甲基-N-[2-(4-甲基戊-2-基)苯基]-1H-吡唑-4-甲酰胺(实施例14)
将0.458 g (2.00 mmol) 5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯加入0.322 g (1.81 mmol) 2-(4-甲基戊-2-基)苯胺和0.377 g (2.72 mmol) 碳酸钾在30 mL乙腈中的混合物中,并将所述混合物在20℃搅拌过夜。在反应已经结束后,用水/乙酸乙酯萃取所述混合物。用硫酸钠干燥有机相,并在减压下浓缩。通过柱色谱法(流动相: 环己烷/乙酸乙酯梯度)纯化粗产物。得到0.580 g (理论值的78%) 5-氯-3-(二氟甲基)-1-甲基-N-[2-(4-甲基戊-2-基)苯基]-1H-吡唑-4-甲酰胺,其具有94%的含量(根据LC-MS)和4.01的logP (酸性)。
1H NMR (400 MHz, DMSO-d) δppm:0.7-0.80 (m, 1 H); 1.10-1.20 (m, 1 H);1.30-1.50 (m, 1 H); 3.10-3.20 (m, 1H); 3.90-4.00 (s, 1H); 7.10-7.40 (m, 1H)。
根据方法P1合成本发明的式(II)的羧酸衍生物的操作:
5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酸(实施例IIb)
在500 mL圆底烧瓶中,将6.0 g (31 mmol) 5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醛溶解在30 mL甲苯中。将2.4 g (62 mmol) 氢氧化钠在6 mL水中的溶液加入该反应混合物中,随后加入103 mL 30%浓度的过氧化氢水溶液。在加入过程中,保持温度低于37℃。然后将所述反应混合物在50℃搅拌7 h。冷却后,用100 mL水萃取有机相。用稀盐酸将水相酸化至pH 2。滤出形成的白色沉淀物,用20 mL水洗涤2次,并干燥。这样得到3.2 g 5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酸,为白色固体。
1H NMR (400 MHz, DMSO-d 6) δppm: 3.78 (s, 3H); 7.12 (t, 1H, J HF = 53.60Hz);13.19 (s, 1H);
IR (KBr): 1688 cm-1 (C=O);2200-3200 cm-1宽;
5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯(实施例IIc)
将3.2 g 5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酸和44.3 mL亚硫酰氯在回流下加热5 h。冷却后,将所述反应混合物在减压下浓缩,得到3.5 g 5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯,为黄色油。
1H NMR (400 MHz, CHCl3-d 6) δppm: 3.97 (s, 3H); 7.00 (t, J = 52.01 Hz,1 H);
IR (TQ): 1759和1725 cm-1 (C=O);
3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羰基氟(实施例IId)
在100℃,将5.0 g (22 mmol) 5-氯-3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯在15 mL甲苯中的溶液加入干燥的4.0 g (70 mmol) 氟化钾在21 mL四氢噻吩-1,1-二氧化物中的溶液中。然后将所述反应混合物在190-200℃搅拌22 h。在减压下除去溶剂,得到8 g3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羰基氟在四氢噻吩-1,1-二氧化物中的溶液(25%摩尔)。
1H NMR (250 MHz, CHCl3-d 6) δppm: 3.87 (s, 3H); 6.79 (t, J= 53.75 Hz, 1H);
19F NMR (250 MHz, CHCl3-d 6) δppm: 45.37 (s, COF);-117.5 (d, J= 28.2Hz);-131.6 (m);
5-氟-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酸(实施例IIe)
将67.5 g 3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羰基氟在四氢噻吩-1,1-二氧化物中的溶液(10%摩尔)逐滴加入到400 mL的1N NaOH水溶液中。在加入过程中,保持温度低于20℃。在室温搅拌2 h以后,用浓盐酸小心地将混合物酸化至pH 2。滤出形成的白色沉淀物,用水洗涤,并干燥。这样得到6 g 5-氟-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酸,为白色固体。
1H NMR (400 MHz, DMSO-d 6) δppm: 3.90 (s, 3H); 7.22 (t, 1H, J HF =53.55Hz);13.33 (s, 1H);
5-氟-3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯(实施例IIf)
将9.1 g 5-氟-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酸和75.5 mL亚硫酰氯在回流下加热1.5 h。冷却后,将所述反应混合物在减压下浓缩,得到10 g 5-氟-3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯,为黄色油。
GC-MS (M+.) = 212;片段: (M+.-Cl) = 177和(M+.-F) = 193;
如上所示的下述式(III)的胺是新颖的,并如下所述进行合成:
5-氟-4'-(三氟甲基)联苯-2-胺(实施例118的胺)的制备
在氩下,将9.0 g (37.9 mmol) 4-氟-2-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊-2-基)苯胺、10.25 g (45.5 mmol) 4-溴三氟甲苯、1.39 g (1.89 mmol) 1,1'-双(二苯基-膦基)二茂铁二氯化钯(II)和20.11 g (189 mmol)碳酸钠在200 mL DMSO和70 mL水中的混合物在90℃搅拌过夜。在反应已经结束后,将混合物冷却至室温,加入水,并用乙酸乙酯萃取混合物。用水再洗涤有机相1次,经硫酸钠干燥,并在减压下浓缩。通过柱色谱法(流动相: 环己烷/乙酸乙酯梯度)纯化粗产物。得到5.28 g (理论值的53%) 5-氟-4’-(三氟甲基)联苯-2-胺,其具有97%的含量(根据LC-MS)和3.52的logP (酸性)。
1H NMR (400MHz, CD3CN-d) δppm: 4.00-4.10 (s, 1 H); 6.78-6.80 (m, 1 H);6.90-7.00 (m, 1 H), 7.60-7.70 (m, 1 H), 7.80-7.90 (m, 1 H)。
根据方法P2从式(I)的酰胺合成本发明的式(I)的硫代酰胺的一般操作:
在13 mLChemspeed0.27 mmol的五硫化二磷(P2S5)。加入3 mL的酰胺(I) (0.54mmol)在二噁烷中的0.18摩尔溶液,并将所述混合物回流加热2小时。然后将温度冷却至80℃,并加入2.5 mL水。将所述混合物在80℃加热另外1小时。然后加入2 mL水,并用4 mL二氯甲烷萃取反应混合物2次。将有机相放在碱性氧化铝柱(2 g)上,用8 mL二氯甲烷洗脱2次。除去溶剂,并通过LCMS和NMR分析粗制的硫代酰胺衍生物。通过制备型LCMS进一步纯化不够纯的化合物。
根据式(I)的化合物的下述实施例列在下面的表1中:
其中R代表氢,且L具有下表1中的下述含义:
其中用*标记的键与酰胺连接;
或者
Q和R1与它们连接的碳原子一起形成任选地被取代的5元、6元或7元碳环或饱和杂环;
或者
L和Q一起形成式W1的基团
其中用*标记的键与酰胺连接;
在表1中,除非另外指出,M+H (ApcI+) 是指通过正大气压化学电离在质谱法中观察到的分子离子峰+1 a.m.u. (原子质量单位)。
在表1中,使用下述方法根据EEC Directive 79/831 Annex V.A8通过HPLC (高效液相色谱法) 在反相柱(C 18)上确定logP值:
温度:40℃;流动相:0.1%的甲酸水溶液和乙腈;从10%乙腈至90%乙腈的线性梯度。
使用具有已知logP值的非支链烷-2-酮(包含3-16个碳原子)进行校准(采用两个相邻烷酮之间的线性内插法,通过保留时间确定logP值)。使用200 nm至400 nm的紫外光谱和色谱信号的峰值,确定λ-max-值。
选择的实施例的NMR数据
NMR峰值罗列方法
选择的实施例的1H-NMR数据以1H-NMR峰值罗列的形式给出。对于每个信号峰,列出了δ值(单位为ppm)和在括号中的信号强度:
在NMR波谱的印刷实施例中,尖锐信号的强度与信号的高度(单位为厘米)有关,并表明信号强度的实际关系。宽峰信号的几个峰或信号的中间以及它们相对于谱中最强信号的相对强度都可以示出。
1H-NMR峰值罗列类似于经典1H-NMR印刷谱,因此通常包括所有峰,所述峰以典型的NMR解释列出。另外,它们可以显示例如溶剂的经典1H-NMR印刷信号、目标化合物的立体异构体(它们也是本发明的目标)、和/或杂质峰。为了在溶剂和/或水的δ范围内显示化合物信号,在我们的1H-NMR峰值罗列中显示了常规的溶剂峰(例如,在DMSO-d6中的DMSO峰和水峰),且通常平均而言显示高强度。
平均而言,目标化合物的立体异构体的峰和/或杂质峰通常具有比目标化合物(例如,纯度>90%)峰更低的强度。这些立体异构体和/或杂质对于特定的制备方法可能是典型的。因此,它们的峰可以有助于通过“副产物指纹”认识我们的制备方法的再现。专业人员(其用已知方法(MestreC,ACD-模拟,以及采用以经验为主地估计的预测值)计算目标化合物的峰)可以根据需要任选地采用额外的强度过滤器来分离目标化合物的诸峰。这种分离将类似于在经典1H-NMR解释中的相关峰拣选。
用途实施例
实施例A
链格孢属试验(番茄)/预防性的
溶剂:49 重量份的N,N-二甲基甲酰胺
乳化剂:1 重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物的制剂。该处理1天之后,给所述植株接种索兰尼链格孢的孢子水悬液。将所述植株在大约22℃且相对大气湿度为100%的培养室中保留1天。然后将所述植株放入大约20℃且相对大气湿度为96%的培养室中。
接种7天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表A的下列化合物在500 ppm的活性化合物浓度表现出70%或更高的效力:
。
实施例B
单丝壳属试验(黄瓜)/预防性的
溶剂:49 重量份的N,N-二甲基甲酰胺
乳化剂:1 重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物的制剂。该处理1天之后,给所述植株接种苍耳单丝壳的孢子水悬液。然后将所述植株放入大约23℃且相对大气湿度为大约70%的温室中。
接种7天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表B的下列化合物在500 ppm的活性化合物浓度表现出75%或更高的效力:
。
实施例C
黑星菌属试验(苹果)/预防性的
溶剂:24.5 重量份的丙酮
24.5 重量份的N,N-二甲基甲酰胺
乳化剂:1 重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物的制剂。喷涂层变干后,给所述植株接种苹果疮痂病致病菌(苹果黑星菌)的分生孢子水悬液,然后在大约20℃且相对大气湿度为100%的培养室中保留1天。
然后将所述植株放入大约21℃且相对大气湿度为大约90%的温室中。
接种10天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表C的下列化合物在100 ppm的活性化合物浓度表现出75%或更高的效力:
。
实施例D
单胞锈菌属试验(豆类)/预防性的
溶剂:24.5 重量份的丙酮
24.5 重量份的N,N-二甲基甲酰胺
乳化剂:1 重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物的制剂。喷涂层变干后,给所述植株接种豆锈致病菌(疣顶单胞锈菌)的孢子水悬液,然后在大约20℃且相对大气湿度为100%的培养室中保留1天。
然后将所述植株放入大约21℃且相对大气湿度为大约90%的温室中。
接种10天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表D的下列化合物在100 ppm的活性化合物浓度表现出70%或更高的效力:
。
在相同条件下,用化合物104和105在100 ppm的剂量观察到完全保护,而用在专利申请WO-2006/087343中公开的实施例9.12的化合物观察到100%的植株损伤,如表D2所示。
在国际专利WO-2006/087343中公开的实施例9.12与3-(二氟甲基)-1-甲基-N-(3',4',5'-三氟联苯-2-基)-1H-吡唑-4-甲酰胺[通用名: 氟唑菌酰胺]对应。
这些结果表明,根据本发明的化合物具有比在WO-2006/087343中公开的结构最接近的化合物更好的生物活性。
实施例E
葡萄孢属试验(豆类)/预防性的
溶剂:24.5 重量份的丙酮
24.5 重量份的N,N-二甲基甲酰胺
乳化剂:1 重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,给幼小植株喷涂活性化合物的制剂。喷涂层变干后,将2小块被灰葡萄孢生长物覆盖的琼脂放在每片叶上。将接种过的植株放入在20℃且相对大气湿度为100%的暗室。
接种2天之后,评价叶子上的病害的大小。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表E的下列化合物在100 ppm的活性化合物浓度表现出75%或更高的效力:
。
实施例F
雪腐镰孢(Fusarium nivale)(大孢变种)-试验(小麦)/预防性的
溶剂:49 重量份的N,N-二甲基乙酰胺
乳化剂:1 重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物或活性化合物组合与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物或活性化合物组合的制剂。
喷涂层变干后,使用喷砂法将植株轻微地损伤,然后给它们喷涂雪腐镰孢(大孢变种)的分生孢子混悬液。
将所述植株放入温室中处于大约10℃温度且相对大气湿度为大约100%的半透明培养室下。
接种5天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表F的下列化合物在500 ppm的活性化合物浓度表现出70%或更高的效力:
。
在相同条件下,用化合物66和67在250 ppm和500 ppm的活性成分剂量观察到良好(至少70%)保护至完全保护,而用在专利申请WO-2004/035589中公开的实施例15.202的化合物观察到一般水平(小于50%)保护至良好(至少70%)保护,如表F2所示。
在国际专利WO-2004/035589中公开的实施例15.202与3-(二氟甲基)-N-(9-异丙基-1,2,3,4-四氢-1,4-亚甲基萘-5-基)-1-甲基-1H-吡唑-4-甲酰胺[通用名: 吡唑萘菌胺]对应。
这些结果表明,根据本发明的化合物具有比在WO-2004/035589中公开的结构最接近的化合物更好的生物活性。
在相同条件下,用化合物71和72在250 ppm和500 ppm的活性成分剂量观察到优秀(至少94%)保护至完全保护,而用在专利申请WO-2008/131901中公开的实施例A1.1的化合物观察到良好(至少70%)保护,如表F3所示。
在国际专利WO-2008/131901中公开的实施例A1.1与N-[9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺[通用名:hambra]对应。
这些结果表明,根据本发明的化合物具有比在WO-2008/131901中公开的结构最接近的化合物更好的生物活性。
在相同条件下,用化合物12在250 ppm和500 ppm的活性成分剂量观察到良好(至少70%)保护至高(至少85%)保护,而用在专利申请WO-2003/010149中公开的实施例I-21的化合物观察到差(小于40%)保护,如表F4所示。
在国际专利WO-2003/010149中公开的实施例I-21与5-氟-1,3-二甲基-N-[2-(4-甲基戊-2-基)苯基]-1H-吡唑-4-甲酰胺[通用名: 戊苯吡菌胺]对应。
这些结果表明,根据本发明的化合物具有比在WO-2003/010149中公开的结构最接近的化合物更好的生物活性。
在相同条件下,用化合物47和48在500 ppm的活性成分剂量观察到高(至少85%)保护,而用在专利申请WO-2003/074491中公开的实施例2.34的化合物观察到一般水平(小于60%)保护,如表F5所示。
在国际专利WO-2003/074491中公开的实施例2.34与N-{2-[1,1'-二(环丙基)-2-基]苯基}-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺[通用名: 环苯吡菌胺]对应。
这些结果表明,根据本发明的化合物具有比在WO-2003/074491中公开的结构最接近的化合物更好的生物活性。
实施例G
小麦叶锈菌-试验(小麦)/预防性的
溶剂:49重量份的N,N-二甲基乙酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物或活性化合物组合与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物或活性化合物组合的制剂。
喷涂层变干后,给所述植株喷涂小麦叶锈菌的孢子混悬液。将所述植株在大约20℃且相对大气湿度为大约100%的培养室中保持48小时。
将所述植株放入大约20℃温度且相对大气湿度为大约80%的温室中。
接种8天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表G的下述化合物在500 ppm的活性化合物浓度表现出70%或更高的效力:
。
实施例H
圆核腔菌-试验(大麦)/预防性的
溶剂:49重量份的N,N-二甲基乙酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物或活性化合物组合与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物或活性化合物组合的制剂。
喷涂层变干后,给所述植株喷涂圆核腔菌的孢子混悬液。将所述植株在大约20℃且相对大气湿度为大约100%的培养室中保持48小时。
将所述植株放入大约20℃温度且相对大气湿度为大约80%的温室中。
接种8天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表H的下述化合物在500 ppm的活性化合物浓度表现出70%或更高的效力:
。
实施例I
小麦壳针孢(Septoria tritici)-试验(小麦)/预防性的
溶剂:49重量份的N,N-二甲基乙酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物或活性化合物组合与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验预防活性,以规定的施用率给幼小植株喷涂活性化合物或活性化合物组合的制剂。
喷涂层变干后,给所述植株喷涂小麦壳针孢的孢子混悬液。将所述植株在大约20℃且相对大气湿度为大约100%的培养室中保持48小时,此后在相对大气湿度为大约100%的半透明培养室中在大约15℃保持60小时。
将所述植株放入大约15℃温度且相对大气湿度为大约80%的温室中。
接种21天之后,评价试验。0%是指与未经处理的对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表I的下述化合物在500 ppm的活性化合物浓度表现出70%或更高的效力:
。
实施例J
梨孢属试验(水稻)/保护性的
溶剂:28.5重量份的丙酮
乳化剂:1.5重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂混合,并用水和规定量的乳化剂将浓缩物稀释至所需的浓度。
为了检验保护活性,以规定的施用率给幼小的水稻植株喷涂活性化合物制剂。处理1天后,给所述植株接种稻梨孢菌的孢子水悬液。然后将所述植株放入相对大气湿度为100%和25℃温度的温室中。
接种5天之后,进行评价。0%是指与对照组相当的效力,而100%的效力是指没有观察到感染。
在该试验中,根据本发明的得自表J的下述化合物在250 ppm的活性化合物浓度表现出80%或更高的效力:
。
在相同条件下,用化合物116在100 ppm和250 ppm的活性成分剂量观察到高(至少90%)保护至优秀(至少95%)保护,而用在专利申请WO-2003/070705中公开的实施例11的化合物观察到差(小于20%)保护至良好(至少70%)保护,如表J2所示。
在国际专利WO-2003/070705中公开的实施例11与N-(3',4'-二氯-5-氟联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺[通用名: 联苯吡菌胺]对应。
这些结果表明,根据本发明的化合物具有比在WO-2003/070705中公开的结构最接近的化合物更好的生物活性。
实施例K
丝核菌属试验(水稻)/保护性的
溶剂:28.5重量份的丙酮
乳化剂:1.5重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂混合,并用水和规定量的乳化剂将浓缩物稀释至所需的浓度。
为了检验保护活性,以规定的施用率给幼小的水稻植株喷涂活性化合物制剂。处理1天后,给所述植株接种立枯丝核菌的菌丝。然后将所述植株放入相对大气湿度为100%和25℃温度的温室中。
接种4天之后,进行评价。0%是指与对照组相当的效力,而100%的效力是指没有观察到感染。
在该试验中,根据本发明的得自表K的下述化合物在250 ppm的活性化合物浓度表现出95%或更高的效力:
。
实施例L
旋孢腔菌属试验(水稻)/保护性的
溶剂:28.5重量份的丙酮
乳化剂:1.5重量份的聚氧乙烯烷基苯基醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验保护活性,以规定的施用率给幼小植株喷涂活性化合物的制剂。喷涂1天后,给所述植株接种水稻褐斑病致病菌(宫部旋孢腔菌)的孢子水悬液。然后将所述植株放入大约25℃且相对大气湿度为大约100%的培养箱中保持1天。
接种4天之后,评价试验。0%是指与对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表L的下述化合物在250 ppm的活性化合物浓度表现出80%或更高的效力:
。
实施例M
层锈菌属试验(大豆)/保护性的
溶剂:28.5重量份的丙酮
乳化剂:1.5重量份的聚氧乙烯烷基苯基醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与规定量的溶剂和乳化剂混合,并用水将浓缩物稀释至所需的浓度。
为了检验保护活性,以规定的施用率给幼小植株喷涂活性化合物的制剂。喷涂1天后,给所述植株接种大豆锈病致病菌(豆薯层锈菌)的孢子水悬液。然后将所述植株放入大约20℃且相对大气湿度为大约80%的温室中。
接种11天之后,评价试验。0%是指与对照组相当的效力,而100%的效力是指没有观察到病害。
在该试验中,根据本发明的得自表M的下述化合物在250 ppm的活性化合物浓度表现出80%或更高的效力:
。
Claims (4)
1.式(I)的1-甲基-3-二卤代甲基-5-卤代吡唑甲酰胺
其中
T代表氧或硫原子;
R代表氢;
Hal1和Hal2彼此独立地代表氯或氟;
Q和L一起形成式(W1-A)的基团,
其中用*标记的键连接至酰胺,
2.根据权利要求1所述的化合物,其中T代表氧原子。
3.一种杀真菌剂组合物,其包含作为活性成分的有效量的根据权利要求1-2中的任一项所述的式(I)的化合物以及农业上可接受的支持物、载体或填充剂。
4.一种用于防治作物的植物病原性真菌的方法,其特征在于,将农艺学上有效的且基本上非植物毒性的量的根据权利要求1-2所述的化合物或根据权利要求3所述的杀真菌剂组合物施用于生长或能够生长植物的土壤、植物的叶子和/或植物的果实、或者植物的种子。
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CN109956904B (zh) * | 2017-12-22 | 2022-03-01 | 华中师范大学 | 吡唑酰胺类化合物及其应用和杀菌剂 |
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US20130296269A1 (en) | 2013-11-07 |
JP2013543859A (ja) | 2013-12-09 |
CN103391925A (zh) | 2013-11-13 |
EP2640707B1 (en) | 2017-03-15 |
JP5833663B2 (ja) | 2015-12-16 |
CN107266368A (zh) | 2017-10-20 |
MX2013005407A (es) | 2013-07-03 |
US9375004B2 (en) | 2016-06-28 |
EP2640707A1 (en) | 2013-09-25 |
WO2012065947A1 (en) | 2012-05-24 |
AR083876A1 (es) | 2013-03-27 |
BR112013012082A2 (pt) | 2016-07-19 |
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