CN1968934A - N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺及其作为杀真菌剂的用途 - Google Patents
N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺及其作为杀真菌剂的用途 Download PDFInfo
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- CN1968934A CN1968934A CNA2005800199122A CN200580019912A CN1968934A CN 1968934 A CN1968934 A CN 1968934A CN A2005800199122 A CNA2005800199122 A CN A2005800199122A CN 200580019912 A CN200580019912 A CN 200580019912A CN 1968934 A CN1968934 A CN 1968934A
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- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012266 salt solution Substances 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
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及式(I)的N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺,其中各取代基如下所定义:R1和R2相互独立地为卤素、C1-C6烷基、C1-C6卤代烷基、氰基、硝基、甲氧基、三氟甲氧基或二氟甲氧基。
Description
本发明涉及式I的N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺:
其中各取代基如下所定义:
R1和R2相互独立地为卤素、C1-C6烷基、C1-C6卤代烷基、氰基、硝基、甲氧基、三氟甲氧基或二氟甲氧基。
此外,本发明还涉及一种使用化合物I防治有害真菌的方法以及化合物I在制备杀真菌组合物中的用途。
N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺由EP-A 0589301已知,该文献还公开了一种制备它们的方法以及选***真菌剂、杀菌剂、杀螨剂、杀线虫剂和杀虫剂的可能混合配对列表。
WO 01/42223同样公开了在苯基环上单取代的N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺。
然而,所述的1-甲基-3-二氟甲基吡唑-4-甲酰苯胺尤其在低施用率下并不完全令人满意。
本发明的目的是提供尤其在低施用率下具有改进的杀真菌作用的新型1-甲基-3-二氟甲基吡唑-4-甲酰苯胺。
因此,我们发现了开头所定义的式I化合物。
优选式I的N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺:
其中各取代基如下所定义:
R1和R2相互独立地为氟、氯、氰基、甲基、甲氧基或三氟甲基。
此外还优选其中R1和R2相互独立地为氟、氯、氰基或甲氧基的式I化合物。
特别优选其中R1和R2相互独立地为氟或氯的式I化合物。
非常特别优选其中R1和R2位于苯基环的3和4位的式I化合物。
在本发明的化合物I中,优选列于下表中的式Ia-If化合物。
表A
序号 | R2 |
1 | 氟 |
2 | 氯 |
3 | 溴 |
4 | 碘 |
5 | 甲基 |
6 | 甲氧基 |
7 | 三氟甲基 |
8 | 三氟甲氧基 |
9 | 氰基 |
10 | 硝基 |
11 | 二氟甲氧基 |
表1:
化合物1.1-1.11
其中R1为氟且R2在每种情况下具有表A的含义之一的式Ia化合物。
表2:
化合物2.1-2.11
其中R1为氯且R2在每种情况下具有表A的含义之一的式Ia化合物。
表3:
化合物3.1-3.11
其中R1为溴且R2在每种情况下具有表A的含义之一的式Ia化合物。
表4:
化合物4.1-4.11
其中R1为碘且R2在每种情况下具有表A的含义之一的式Ia化合物。
表5:
化合物5.1-5.11
其中R1为甲基且R2在每种情况下具有表A的含义之一的式Ia化合物。
表6:
化合物6.1-6.11
其中R1为甲氧基且R2在每种情况下具有表A的含义之一的式Ia化合物。
表7:
化合物7.1-7.11
其中R1为三氟甲基且R2在每种情况下具有表A的含义之一的式Ia化合物。
表8:
化合物8.1-8.11
其中R1为三氟甲氧基且R2在每种情况下具有表A的含义之一的式Ia化合物。
表9:
化合物9.1-9.11
其中R1为氰基且R2在每种情况下具有表A的含义之一的式Ia化合物。
表10:
化合物10.1-10.11
其中R1为硝基且R2在每种情况下具有表A的含义之一的式Ia化合物。
表11:
化合物11.1-11.11
其中R1为二氟甲氧基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表12
化合物12.1-12.11
其中R1为氟且R2在每种情况下具有表A的含义之一的式Ib化合物。
表13:
化合物13.1-13.11
其中R1为氯且R2在每种情况下具有表A的含义之一的式Ib化合物。
表14:
化合物14.1-14.11
其中R1为溴且R2在每种情况下具有表A的含义之一的式Ib化合物。
表15:
化合物15.1-15.11
其中R1为碘且R2在每种情况下具有表A的含义之一的式Ib化合物。
表16:
化合物16.1-16.11
其中R1为甲基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表17:
化合物17.1-17.11
其中R1为甲氧基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表18:
化合物18.1-18.11
其中R1为三氟甲基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表19:
化合物19.1-19.11
其中R1为三氟甲氧基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表20:
化合物20.1-20.11
其中R1为氰基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表21:
化合物21.1-21.11
其中R1为硝基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表22:
化合物22.1-22.11
其中R1为二氟甲氧基且R2在每种情况下具有表A的含义之一的式Ib化合物。
表23:
化合物23.1-23.11
其中R1为氟且R2在每种情况下具有表A的含义之一的式Ic化合物。
表24:
化合物24.1-24.11
其中R1为氯且R2在每种情况下具有表A的含义之一的式Ic化合物。
表25:
化合物25.1-25.11
其中R1为溴且R2在每种情况下具有表A的含义之一的式Ic化合物。
表26:
化合物26.1-26.11
其中R1为碘且R2在每种情况下具有表A的含义之一的式Ic化合物。
表27:
化合物27.1-27.11
其中R1为甲基且R2在每种情况下具有表A的含义之一的式Ic化合物。
表28:
化合物28.1-28.11
其中R1为甲氧基且R2在每种情况下具有表A的含义之一的式Ic化合物。
表29:
化合物29.1-29.11
其中R1为三氟甲基且R2在每种情况下具有表A的含义之一的式Ic化合物。
表30:
化合物30.1-30.11
其中R1为三氟甲氧基且R2在每种情况下具有表A的含义之一的式Ic化合物。
表31:
化合物31.1-31.11
其中R1为氰基且R2在每种情况下具有表A的含义之一的式Ic化合物。
表32:
化合物32.1-32.11
其中R1为硝基且R2在每种情况下具有表A的含义之一的式Ic化合物。
表33:
化合物33.1-33.11
其中R1为二氟甲氧基且R2在每种情况下具有表A的含义之一的式Ic化合物。
表34:
化合物34.1-34.11
其中R1为氟且R2在每种情况下具有表A的含义之一的式Id化合物。
表35:
化合物35.1-35.11
其中R1为氯且R2在每种情况下具有表A的含义之一的式Id化合物。
表36:
化合物36.1-36.11
其中R1为溴且R2在每种情况下具有表A的含义之一的式Id化合物。
表37:
合物37.1-37.11
化其中R1为碘且R2在每种情况下具有表A的含义之一的式Id化合物。
表38:
化合物38.1-38.11
其中R1为甲基且R2在每种情况下具有表A的含义之一的式Id化合物。
表39:
化合物39.1-39.11
其中R1为甲氧基且R2在每种情况下具有表A的含义之一的式Id化合物。
表40:
化合物40.1-40.10
其中R1为三氟甲基且R2在每种情况下具有表A的含义之一的式Id化合物。
表41:
化合物41.1-41.11
其中R1为三氟甲氧基且R2在每种情况下具有表A的含义之一的式Id化合物。
表42:
化合物42.1-42.11
其中R1为氰基且R2在每种情况下具有表A的含义之一的式Id化合物。
表43:
化合物43.1-43.11
其中R1为硝基且R2在每种情况下具有表A的含义之一的式Id化合物。
表44:
化合物44.1-44.11
其中R1为二氟甲氧基且R2在每种情况下具有表A的含义之一的式Id化合物。
表45:
化合物45.1-45.11
其中R1为氟且R2在每种情况下具有表A的含义之一的式Ie化合物。
表46:
化合物46.1-46.11
其中R1为氯且R2在每种情况下具有表A的含义之一的式Ie化合物。
表47:
化合物47.1-47.11
其中R1为溴且R2在每种情况下具有表A的含义之一的式Ie化合物。
表48:
化合物48.1-48.11
其中R1为碘且R2在每种情况下具有表A的含义之一的式Ie化合物。
表49:
化合物49.1-49.11
其中R1为甲基且R2在每种情况下具有表A的含义之一的式Ie化合物。
表50:
化合物50.1-50.11
其中R1为甲氧基且R2在每种情况下具有表A的含义之一的式Ie化合物。
表51:
化合物51.1-51.11
其中R1为三氟甲基且R2在每种情况下具有表A的含义之一的式Ie化合物。
表52:
化合物52.1-52.11
其中R1为三氟甲氧基且R2在每种情况下具有表A的含义之一的式Ie化合物。
表53:
化合物53.1-53.11
其中R1为氰基且R2在每种情况下具有表A的含义之一的式Ie化合物。
表54:
化合物54.1-54.11
其中R1为硝基且R2在每种情况下具有表A的含义之一的式Ie化合物。
表55:
化合物55.1-55.11
其中R1为二氟甲氧基且R2在每种情况下具有表A的含义之一的式Ie化合物。
表56:
化合物56.1-56.11
其中R1为氟且R2在每种情况下具有表A的含义之一的式If化合物。
表57:
化合物57.1-57.11
其中R1为氯且R2在每种情况下具有表A的含义之一的式If化合物。
表58:
化合物58.1-58.11
其中R1为溴且R2在每种情况下具有表A的含义之一的式If化合物。
表59:
化合物59.1-59.11
其中R1为碘且R2在每种情况下具有表A的含义之一的式If化合物。
表60:
化合物60.1-60.11
其中R1为甲基且R2在每种情况下具有表A的含义之一的式If化合物。
表61:
化合物61.1-61.11
其中R1为甲氧基且R2在每种情况下具有表A的含义之一的式If化合物。
表62:
化合物62.1-62.11
其中R1为三氟甲基且R2在每种情况下具有表A的含义之一的式If化合物。
表63:
化合物63.1-63.11
其中R1为三氟甲氧基且R2在每种情况下具有表A的含义之一的式If化合物。
表64:
化合物64.1-64.11
其中R1为氰基且R2在每种情况下具有表A的含义之一的式If化合物。
表65:
化合物65.1-65.11
其中R1为硝基且R2在每种情况下具有表A的含义之一的式If化合物。
表66:
化合物66.1-66.11
其中R1为二氟甲氧基且R2在每种情况下具有表A的含义之一的式If化合物。
在本发明上下文中,卤素表示氟、氯、溴和碘,尤其是氟和氯。
术语“烷基”包括直链和支化烷基。它们优选为直链或支化C1-C6烷基。烷基的实例是尤其诸如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基的烷基。
卤代烷基为被一个或多个卤原子,尤其是氟和氯部分或完全卤代的上述烷基。优选存在1-3个卤原子,特别优选二氟甲基和三氟甲基。
制备式F化合物的方法由FP-A 0 589 301已知。
例如,使式II的1-甲基-3-二氟甲基吡唑甲酰卤与式III的苯胺反应,得到式I化合物:
式II中的基团Hal表示卤原子,如氯、溴和碘,尤其是氯或溴。
该反应通常在-20℃至100℃,优选0-50℃的温度下进行。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如***、二异丙醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲亚砜和二甲基甲酰胺,特别优选甲苯和四氢呋喃。
还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨化物,如氨基锂、氨基钠和氨基钾,碱金属和碱土金属碳酸盐,如碳酸锂和碳酸钙,还有碱金属碳酸氢盐,如碳酸氢钠,以及有机金属化合物,尤其是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,还有碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,此外还有有机碱,例如叔胺,如三甲基铵、三乙基胺、三异丙基胺和N-甲基哌啶,吡啶,取代吡啶,如可力丁、卢剔啶和4-二甲氨基吡啶,以及双环胺。
特别优选使用三乙基胺和吡啶。
碱通常基于化合物II以等摩尔量使用。然而,它们还可以过量5-30mol%,优选5-10mol%下使用或合适的话,在叔胺的情况下作为溶剂使用。
原料通常以等摩尔量相互反应。就产率而言,可能有利的是基于III以过量1-20mol%,优选1-10mol%使用II。
在作为杀真菌剂的施用形式中,本发明化合物I还可与其它活性化合物一起存在,例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或肥料一起存在。将作为杀真菌剂施用的化合物I或包含它们的组合物与其它杀真菌剂混合时,在许多情况下得到拓宽的杀真菌活性谱。
下列本发明化合物可以与其结合使用的杀真菌剂用来说明可能的组合但不限制它们:
·硫,二硫代氨基甲酸盐及其衍生物,如二甲基二硫代氨基甲酸铁(III)、二甲基二硫代氨基甲酸锌、亚乙基二-二硫代氨基甲酸锌、亚乙基二-二硫代氨基甲酸锰、乙二胺二-二硫代氨基甲酸锰锌、四甲基秋兰姆二硫化物、(N,N’-亚乙基二-二硫代氨基甲酸)锌的氨配合物、(N,N’-亚丙基二-二硫代氨基甲酸)锌的氨配合物、(N,N’-亚丙基二-二硫代氨基甲酸)锌或N,N’-聚丙烯二(硫代氨基甲酰基)二硫化物;
·硝基衍生物,如巴豆酸二硝基(1-甲基庚基)苯基酯、3,3-二甲基丙烯酸2-仲丁基-4,6-二硝基苯基酯、碳酸2-仲丁基-4,6-二硝基苯基·异丙基酯或5-硝基间苯二甲酸二异丙基酯;
·杂环物质,如2-十七烷基-2-咪唑啉乙酸盐、2,4-二氯-6-(邻氯苯胺基)-s-三嗪、邻苯二甲酰亚氨基硫代膦酸O,O-二乙基酯、5-氨基-1-[二(二甲氨基)氧膦基]-3-苯基-1,2,4-***、2,3-二氰基-1,4-二硫代蒽醌、2-硫代-1,3-二硫杂环戊二烯并[4,5-b]喹喔啉、1-(丁基氨基甲酰基)-2-苯并咪唑氨基甲酸甲酯、2-(甲氧基羰基氨基)苯并咪唑、2-(2-呋喃基)苯并咪唑、2-(4-噻唑基)苯并咪唑、N-(1,1,2,2-四氯乙硫基)四氢邻苯二甲酰亚胺、N-(三氯甲硫基)四氢邻苯二甲酰亚胺或N-(三氯甲硫基)邻苯二甲酰亚胺,
·N-二氯一氟甲硫基-N’,N’-二甲基-N-苯基硫酸二酰胺、5-乙氧基-3-三氯甲基-1,2,3-噻二唑、2-氰硫基甲硫基苯并噻唑、1,4-二氯-2,5-二甲氧基苯、4-(2-氯苯基亚肼基)-3-甲基-5-异唑酮、2-硫代吡啶 1-氧化物、8-羟基喹啉或其铜盐、2,3-二氢-5-甲酰苯胺基-6-甲基-1,4-氧硫杂环己二烯、2,3-二氢-5-甲酰苯胺基-6-甲基-1,4-氧硫杂环己二烯4,4-二氧化物、2-甲基-5,6-二氢-4H-吡喃-3-甲酰苯胺、2-甲基呋喃-3-甲酰苯胺、2,5-二甲基呋喃-3-甲酰苯胺、2,4,5-三甲基呋喃-3-甲酰苯胺、N-环己基-2,5-二甲基呋喃-3-甲酰胺、N-环己基-N-甲氧基-2,5-二甲基呋喃-3-甲酰胺、2-甲基N-苯甲酰苯胺、2-碘N-苯甲酰苯胺、N-甲酰基-N-吗啉2,2,2-三氯乙基缩醛、哌嗪-1,4-二基二-1-(2,2,2-三氯乙基)甲酰胺、1-(3,4-二氯苯胺基)-1-甲酰氨基-2,2,2-三氯乙烷、2,6-二甲基-N-十三烷基吗啉或其盐、2,6-二甲基-N-环十二烷基吗啉或其盐、N-[3-(对-(叔丁基)苯基)-2-甲基丙基]-顺式-2,6-二甲基吗啉、N-[3-(对-(叔丁基)苯基)-2-甲基丙基]哌啶、1-[2-(2,4-二氯苯基)-4-乙基-1,3-二氧戊环-2-基乙基]-1H-1,2,4-***、1-[2-(2,4-二氯苯基)-4-(正丙基)-1,3-二氧戊环-2-基乙基]-1H-1,2,4-***、N-(正丙基)-N-(2,4,6-三氯苯氧基乙基)-N’-咪唑基脲、1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-***-1-基)-2-丁酮、1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-***-1-基)-2-丁醇、(2RS,3RS)-1-[3-(2-氯苯基)-2-(4-氟苯基)环氧乙烷-2-基甲基]-1H-1,2,4-***、α-(2-氯苯基)-α-(4-氯苯基)-5-嘧啶甲醇、5-丁基-2-二甲氨基-4-羟基-6-甲基嘧啶、二(对氯苯基)-3-比啶甲醇、1,2-二(3-乙氧羰基-2-硫脲基)苯或1,2-二(3-甲氧基羰基-2-硫脲基)苯,
·嗜球果伞素类,如E-甲氧亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯、E-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基}-3-甲氧基丙烯酸甲酯、甲基E-甲氧亚氨基-[α-(2-苯氧基苯基)]乙酰胺、甲基E-甲氧亚氨基-[α-(2,5-二甲基苯氧基)-邻甲苯基]乙酰胺,
·苯胺基嘧啶类,如N-(4,6-二甲基嘧啶-2-基)苯胺、N-[4-甲基-6-(1-丙炔基)嘧啶-2-基]苯胺或N-[4-甲基-6-环丙基嘧啶-2-基]苯胺,
·苯基吡咯类,如4-(2,2-二氟-1,3-苯并间二氧杂环戊烯-4-基)吡咯-3-甲腈,
·肉桂酰胺类,如3-(4-氯苯基)-3-(3,4-二甲氧基苯基)丙烯酰吗啉,以及
·各种杀真菌剂,如十二烷基胍乙酸盐、3-[3-(3,5-二甲基-2-氧基环己基)-2-羟基乙基]戊二酰亚胺、六氯苯、N-(2,6-二甲基苯基)-N-(2-呋喃甲酰基)-DL-丙氨酸甲酯、N-(2,6-二甲基苯基)-N-(2’-甲氧基乙酰基)-DL-丙氨酸甲酯、N-(2,6-二甲基苯基)-N-氯乙酰基-D,L-2-氨基丁内酯、N-(2,6-二甲基苯基)-N-(苯基乙酰基)-DL-丙氨酸甲酯、5-甲基-5-乙烯基-3-(3,5-二氯苯基)-2,4-二氧代-1,3-唑烷、3-(3,5-二氯苯基)-5-甲基-5-甲氧基甲基-1,3-唑烷-2,4-二酮、3-(3,5-二氯苯基)-1-异丙基氨基甲酰基乙内酰脲、N-(3,5-二氯苯基)-1,2-二甲基环丙烷-1,2-二甲酰亚胺、2-氰基-N-(乙基氨基羰基)-2-[甲氧亚氨基]乙酰胺、1-[2-(2,4-二氯苯基)戊基]-1H-1,2,4-***、2,4-二氟-α-(1H-1,2,4-***基-1-甲基)二苯甲醇、N-(3-氯-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯-2-氨基吡啶、1-((二(4-氟苯基)甲基甲硅烷基)甲基)-1H-1,2,4-***。
式I化合物的特征在于对宽范围的植物病原性真菌具有高度活性,所述真菌尤其选自子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)、藻菌纲(Phycomycetes)和半知菌纲(Deuteromycetes)真菌。它们中的一些内吸起作用并因此可以用作叶面和土壤作用杀真菌剂。它们还可以用于拌种。
它们对在各种栽培植物如棉花、蔬菜品种(如黄瓜、豆类、西红柿、土豆和葫芦科植物)、大麦、禾草、燕麦、香蕉、咖啡、玉米、水果品种、稻、黑麦、大豆、葡萄藤、小麦、观赏植物、甘蔗以及大量种子中防治大量真菌尤其重要。
它们尤其适于防治下列植物病原性真菌:禾谷类上的禾白粉菌(Blumeria graminis)(白粉病),葫芦科植物上的二孢白粉菌(Erysiphecichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),苹果上的苹果白粉病菌(Podosphaera leucotricha),葡萄藤上的葡萄钩丝壳(Uncinulanecator),禾谷类上的柄锈菌(Puccinia)属,棉花、稻和草坪上的丝核菌(Rhizoctonia)属,禾谷类和甘蔗上的黑粉菌(Ustilago)属,苹果上的苹果黑星菌(Venturia inaequalis)(黑星病),禾谷类上的长蠕孢(Helminthosporium)属,小麦上的颖枯壳针孢(Septoria nodorum),草莓、蔬菜、观赏植物和葡萄藤上的灰葡萄孢(Botrytis cinerea)(灰霉病),花生上的花生褐斑病菌(Cercospora arachidicola),小麦和大麦上的眼斑病菌(Pseudocercosporellaherpotrichoides),稻上的稻瘟病菌(Pyricularia oryzae),土豆和西红柿上的致病疫霉(Phytophthora infestans),葡萄藤上的葡萄生单轴霉(Plasmopara viticola),啤酒花和黄瓜上的假霜霉(Pseudoperonospora)属,蔬菜和水果上的链格孢(Alternaria)属,香蕉上的球腔菌(Mycosphaerella)属以及链孢霉(Fusarium)属和轮枝孢(Verticillium)属,大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(P.meibomiae)。
取决于所需效果,本发明式I化合物的施用率尤其在农业栽培区域为0.01-8kg/ha,优选0.1-5kg/ha,尤其是0.1-3.0kg/ha。
对于化合物I而言,施用率尤其为0.01-1kg/ha,优选0.05-0.5kg/ha,尤其是0.05-0.3kg/ha。
在拌种中,混合物的施用率通常为0.001-250g/kg种子,优选0.01-100g/kg,尤其是0.01-50g/kg。
在植物病原性有害真菌的防治中,化合物I的施用在植物播种之前或之后或在植物出苗之前或之后对种子、植物或土壤喷雾或撒粉而进行。
可以将本发明的杀真菌化合物l制备成例如可直接喷雾溶液、粉末和悬浮液形式或高度浓缩的含水、油状或其他悬浮液、分散体、乳液、油分散体、糊、可撒粉产品撒播组合物或颗粒形式且可以通过喷雾、雾化、撒粉、撒播或浇灌而施用。使用形式取决于特定的意欲目的;在每种情况下都应确保本发明混合物尽可能精细和均匀地分布。
配制剂以本身已知的方式制备,例如通过加入溶剂和/或载体,若需要的话使用乳化剂和分散剂。适于该目的的溶剂/助剂主要为:
-水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
-载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂为芳族磺酸如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,以及烷基芳基磺酸盐,烷基硫酸盐,脂肪酸,烷基磺酸盐和月桂基醚硫酸盐,脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇或脂肪醇乙二醇醚的盐,磺化萘与甲醛的缩合物和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基酚、辛基酚或壬基酚,烷基苯基聚乙二醇醚或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯,月桂醇聚乙二醇醚乙酸酯,山梨醇酯,木素亚硫酸盐废液或甲基纤维素。
粉末、撒播组合物和可撒粉产品可以通过将化合物I与固体载体混合或一起研磨来制备。
颗粒(如涂敷颗粒、浸渍颗粒和均质颗粒)通常通过使活性化合物与固体载体粘附而制备。
填料和固体载体实例为矿土如硅胶、二氧化硅、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.1-95重量%,优选0.5-90重量%的化合物I。
活性化合物以90-100%,优选95-100%的纯度(根据NMR谱或HPLC)使用。
下列为配制剂的实例:
1.用水稀释的产品
A)水溶性浓缩物(SL)
将10重量份活性化合物溶于水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于环己酮中并加入分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。
C)乳油(EC)
将15重量份活性化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。用水稀释得到乳液。
D)乳液(EW,EO)
将40重量份活性化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。借助乳化机(Ultraturax)将该混合物引入水中并制成均相乳液。用水稀释得到乳液。
E)悬浮液(SC,OD)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入分散剂、湿润剂和水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。
F)水分散性颗粒和水溶性颗粒(WG,SG)
将50重量份活性化合物细碎研磨并加入分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。
G)水分散性粉末和水溶性粉末(WP,SP)
将75重量份活性化合物在转子-定子磨机中研磨并加入分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。
2.不稀释而施用的产品
H)可撒粉粉末(DP)
将5重量份活性化合物细碎研磨并与95%的细碎高岭土充分混合。这得到可撒粉产品。
I)颗粒(GR,FG,GG,MG)
将0.5重量份活性化合物细碎研磨并结合95.5%载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的颗粒。
J)ULV溶液(UL)
将10重量份活性化合物溶于有机溶剂如二甲苯中。这得到不经稀释而施用的产品。
活性化合物可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播组合物或颗粒形式),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;它们应在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而,还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
活性化合物在即用制剂中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至在没有添加剂的情况下施用活性化合物。
可以将各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂加入活性化合物中,甚至需要的话恰在紧临使用前加入(桶混合)。这些试剂与本发明组合物可以1∶10-10∶1的重量比混合。
化合物I或对应的配制剂通过用杀真菌有效量的化合物I处理有害真菌、其栖息地或需要防止它们的植物、种子、土壤、区域、材料或空间而施用。
施用可以在被有害真菌侵染之前或之后进行。
制备实施例
实施例1
1.)合成4,4-二氟-3-氧代丁酸乙酯1
将13.9g氢化钠加入300ml无水四氢呋喃中。在35-40℃下加入62g二氟乙酸乙酯在44g乙酸乙酯中的溶液。在40℃下搅拌7小时后将反应混合物搅入1升冰水中,使用浓度为10%的硫酸将pH调节为3并将该混合物萃取两次,在每种情况下使用300ml甲基叔丁基醚。合并的有机相用盐水洗涤两次,用硫酸钠干燥并减压浓缩。蒸馏残余物。得到59.1g无色油状产物,沸点(100mb)为90-94℃。
2.)合成2-乙氧基亚甲基-4,4-二氟-3-氧代丁酸乙酯2
将30g 4,4-二氟-3-氧代丁酸乙酯1、44g原甲酸三乙酯和55g乙酸酐的混合物在回流下搅拌4小时,然后蒸馏。得到35g无色油状产物,沸点为85-87℃。
3.)合成3-二氟甲基-1-甲基吡唑-4-甲酸乙酯3
在-40℃下将33.5g 2-乙氧基亚甲基-4,4-二氟-3-氧代丁酸乙酯2溶于250ml无水乙醇中。加入7g甲基肼并将该混合物在-40℃下搅拌1小时并在室温下搅拌15小时。减压浓缩反应混合物。将残余物从戊烷中再结晶。得到29.6g产物,熔点为50-51℃。
4.)合成3-二氟甲基-1-甲基吡唑-4-甲酸4
将19.3g 3-二氟甲基-1-甲基吡唑-4-甲酸乙酯和5.7g氢氧化钠溶于80ml乙醇和40ml水的混合物中。将该混合物在60℃下搅拌2小时。然后减压浓缩该混合物并将残余物在500ml冰水中处理,使用浓度为10%的盐酸将pH调为3。将该混合物用300ml THF和甲基叔丁基醚的混合物(2∶3)萃取两次。合并的有机相用稀氯化钠溶液洗涤3次,在硫酸钠上干燥并减压浓缩。得到14.5g浅黄色粉末状产物,熔点为192-193℃。
5.)合成邻-(3,4-二氯苯基)苯胺5
将0.14g四-三苯基膦钯(0)加入20.47g 2-溴苯胺、24.98g 3,4-二氯苯基硼酸和25.23g碳酸钠在150ml水和450ml乙二醇二甲基醚的混合物中的溶液中。将该混合物在回流下搅拌48小时。在减压下浓缩该混合物。将残余物在甲基叔丁基醚中处理,用碳酸氢钠溶液洗涤一次并用水洗涤四次,在硫酸钠上干燥并减压浓缩。使用甲苯和环己烷的混合物(1∶2)进行层析提纯得到15.5g浅黄色粉末状产物。
6.)合成3-二氟甲基-1-甲基-N-(邻-(3,4-二氯苯基)苯基)吡唑-4-甲酰胺6
将0-35g 3-二氟甲基-1-甲基吡唑-4-甲酸4、0.47g邻-(3,4-二氯苯基)苯胺5、0.3g三乙基胺和0.55g二-(2-氧代-3-唑烷基)磷酰氯溶于20ml甲苯中。将该混合物在室温下搅拌15小时,然后加入20ml甲基叔丁基醚并将该混合物用浓度为5%的氢氧化钠水溶液洗涤两次,用浓度为5%的盐酸洗涤两次并用盐水洗涤一次。将有机相在硫酸钠上干燥并在减压下浓缩。使用甲苯和甲基叔丁基醚的混合物(5∶1)进行层析提纯得到0.47g无色粉末状产物,熔点为129-130℃。
表67
化合物 | R1 | R2 | 熔点 |
67.1 | 3-Cl | 5-Cl | 131-132℃ |
67.2 | 3-Cl | 4-F | 129-130℃ |
67.3 | 3-F | 4-F | 122-123℃ |
67.4 | 3-Cl | 4-Cl | 129-130℃ |
67.5 | 2-Cl | 4-Cl | 123-124℃ |
67.6 | 2-F | 5-F | 139-141℃ |
67.7 | 2-F | 4-Cl | 124-126℃ |
67.8 | 2-CH3 | 4-Cl | 155-156℃ |
67.9 | 3-CH3 | 4-Cl | 145-146℃ |
67.10 | 2-CH3 | 4-F | 123-124℃ |
67.11 | 3-CH3 | 4-F | 130-132℃ |
67.12 | 3-F | 4-Cl | 166-167℃ |
67.13 | 2-F | 4-F | 90-92℃ |
67.14 | 2-CH3 | 4-OCH3 | 84-86℃ |
应用实施例
活性化合物的制备
使用溶剂/乳化剂体积比为99∶1的丙酮和/或DMSO与乳化剂UniperolEL(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)的混合物将活性化合物单独或联合配制成含有25mg活性化合物的储备溶液并配成10ml。然后用水将该混合物配成100ml。使用所述溶剂/乳化剂/水混合物将该储备溶液稀释至下述活性化合物浓度。或者将活性化合物以市售成品制剂使用并用水稀释至所述活性化合物浓度。
应用实施例1-对小麦隐匿柄锈菌(Puccinia recondita)引起的小麦褐锈病的治疗活性
将栽培品种为“Kanzler”的盆栽小麦秧苗的叶子用叶锈病菌(小麦隐匿柄锈菌)的孢子悬浮液接种。然后在20-22℃下将盆放置在高大气湿度(90-95%)的室中24小时。在此期间孢子萌发并且芽管穿透到叶组织中。第二天将侵染的植物用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。所述悬浮液或乳液如上所述制备。在喷雾涂层干燥之后,将试验植物在20-22℃和相对大气湿度为65-70%的温室中培养7天。然后测定锈病真菌在叶子上的发展程度。
化合物号 | 在PUCCRT K1和250ppm下的侵染(%) |
未处理 | 90 |
67.1 | 0 |
67.2 | 0 |
67.3 | 0 |
67.4 | 0 |
67.5 | 0 |
67.6 | 0 |
67.7 | 0 |
67.8 | 0 |
67.9 | 3 |
67.10 | 0 |
67.11 | 0 |
67.12 | 0 |
67.13 | 0 |
67.14 | 0 |
应用实施例2a)-对由灰葡萄孢(Botrytis cinerea)引起的柿子椒叶子上的灰霉病的活性,保护性施用
将栽培品种为“Neusiedler Ideal Elite”的柿子椒秧苗在充分发育出2-3片叶后用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将已处理植物用在浓度为2%的生物麦芽水溶液中含有1.7×106个孢子/ml的灰葡萄孢的孢子悬浮液接种。然后将试验植物置于22-24℃和高大气湿度的黑暗气候调节室中。5天后可以百分数肉眼测定叶子上的真菌侵染程度。
应用实施例2b)-对由网斑病菌(Pyrenophora teres)引起的大麦网斑病的活性,1天保护性施用
将盆栽大麦秧苗的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。喷雾涂层干燥24小时后,将试验植物用网斑病菌(Pyrenophora[同义词Drechslera]teres)-网斑病病原体的含水孢子悬浮液接种。然后将试验植物放入温度为20-24℃且相对大气湿度为95-100%的温室中。6天后以整个叶面积的侵染%肉眼测定病害的发展程度。
2a | 2b | |
化合物号 | 在BOTRCI P1和250ppm下的侵染(%) | 在PYRNTE P1和250ppm下的侵染(%) |
未处理 | 90 | 90 |
67.1 | 1 | |
67.2 | 0 | |
67.3 | 1 | |
67.4 | 0 | |
67.6 | 10 | |
67.7 | 5 | |
67.8 | 0 | |
67.9 | 0 | |
67.10 | 0 | |
67.11 | 0 | |
67.12 | 7 | |
67.13 | 5 |
对比试验1
对小麦隐匿柄锈菌(Puccinia recondita)引起的小麦褐锈病的治疗活性
将EP-A 0 589 301的化合物35与表67的本发明化合物67.1-67.14进行比较。将栽培品种为“Kanzler”的盆栽小麦秧苗的叶子用褐锈病菌(小麦隐匿柄锈菌)的孢子悬浮液接种。然后在20-22℃下将盆放置在高大气湿度(90-95%)的室中24小时。在此期间孢子萌发并且芽管穿透到叶组织中。第二天将侵染的植物用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。所述悬浮液或乳液如上所述制备。在喷雾涂层干燥之后,将试验植物在20-22℃和相对大气湿度为65-70%的温室中培养7天。然后测定锈病真菌在叶子上的发展程度。
化合物号 | 在PUCCRT K1和250ppm下的侵染(%) |
67.2 | 0 |
67.3 | 0 |
67.4 | 0 |
67.5 | 0 |
67.6 | 0 |
67.7 | 0 |
67.8 | 0 |
67.9 | 3 |
67.10 | 0 |
67.11 | 0 |
67.12 | 0 |
67.13 | 0 |
67.14 | 0 |
对比试验2
对由颖枯球腔菌(Leptosphaeria nodorum)引起的小麦叶枯病的活性
将EP-A 0 589301的化合物35与表67的本发明化合物67.1-67.14进行比较。将栽培品种为“Kanzler”的小麦植株的盆用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将盆用颖枯球腔菌(同义词颖枯壳多孢(Stagonospora nodorum),颖枯壳针孢(Septoria nodorum))的含水孢子悬浮液接种。然后将植物置于20℃和最大大气湿度的室中。8天后未处理但侵染的对照植物上的叶枯病发展到可以肉眼测定侵染百分数的程度。
化合物号 | 在LEPTNO P1和250ppm下的侵染(%) |
67.7 | 0 |
67.10 | 15 |
67.12 | 3 |
67.13 | 3 |
67.14 | 5 |
Claims (7)
1.式I的N-(邻苯基)-1-甲基-3-二氟甲基吡唑-4-甲酰苯胺:
其中各取代基如下所定义:
R1和R2相互独立地为卤素、C1-C6烷基、C1-C6卤代烷基、氰基、硝基、甲氧基、三氟甲氧基或二氟甲氧基。
2.根据权利要求1的式I的N-酰苯胺,其中R1和R2相互独立地为氟、氯、氰基、甲基、甲氧基或三氟甲基。
3.根据权利要求1或2的式I的N-酰苯胺,其中R1和R2相互独立地为氟、氯、氰基或甲氧基。
4.根据权利要求1的式I的N-酰苯胺,其中R1和R2相互独立地为氟或氯。
5.根据权利要求1-4中任一项的式I的N-酰苯胺,包括其中取代基R1和R2位于苯基环的3和4位的式I化合物。
6.一种防治有害真菌的方法,其中用根据权利要求1-5中任一项的式I的N-酰苯胺处理有害真菌、其栖息地或需要防止它们的植物、种子、土壤、区域、材料或空间。
7.一种杀真菌组合物,包含根据权利要求1的式I的N-酰苯胺和固体或液体载体。
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DE4231517A1 (de) * | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
WO2002008197A1 (de) * | 2000-07-24 | 2002-01-31 | Bayer Cropscience Ag | Biphenylcarboxamide |
DE10215292A1 (de) * | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Disubstitutierte Pyrazolylcarbocanilide |
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- 2005-06-16 CN CNA2005800199122A patent/CN1968934A/zh active Pending
- 2005-06-16 JP JP2007515882A patent/JP2008502636A/ja not_active Withdrawn
- 2005-06-16 BR BRPI0512118-3A patent/BRPI0512118A/pt not_active IP Right Cessation
- 2005-06-16 EP EP05750478A patent/EP1761498A1/de not_active Withdrawn
- 2005-06-17 TW TW094120117A patent/TW200615264A/zh unknown
- 2005-06-17 AR ARP050102525A patent/AR049524A1/es unknown
- 2005-06-17 UY UY28967A patent/UY28967A1/es unknown
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Also Published As
Publication number | Publication date |
---|---|
WO2005123690A1 (de) | 2005-12-29 |
AR049524A1 (es) | 2006-08-09 |
JP2008502636A (ja) | 2008-01-31 |
BRPI0512118A (pt) | 2008-02-06 |
TW200615264A (en) | 2006-05-16 |
UY28967A1 (es) | 2006-01-31 |
US20080108686A1 (en) | 2008-05-08 |
EP1761498A1 (de) | 2007-03-14 |
IL179448A0 (en) | 2007-05-15 |
PE20060096A1 (es) | 2006-03-16 |
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