CN102256490A - 用作植物生长调节剂的异噁唑衍生物 - Google Patents
用作植物生长调节剂的异噁唑衍生物 Download PDFInfo
- Publication number
- CN102256490A CN102256490A CN2009801504563A CN200980150456A CN102256490A CN 102256490 A CN102256490 A CN 102256490A CN 2009801504563 A CN2009801504563 A CN 2009801504563A CN 200980150456 A CN200980150456 A CN 200980150456A CN 102256490 A CN102256490 A CN 102256490A
- Authority
- CN
- China
- Prior art keywords
- compound
- alkyl
- formula
- chlorphenyl
- alkoxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000005648 plant growth regulator Substances 0.000 title claims description 13
- 150000002545 isoxazoles Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 356
- 239000000203 mixture Substances 0.000 claims abstract description 73
- 230000001105 regulatory effect Effects 0.000 claims abstract description 13
- 230000008635 plant growth Effects 0.000 claims abstract description 12
- -1 2-chlorphenyl Chemical group 0.000 claims description 129
- 125000003545 alkoxy group Chemical group 0.000 claims description 84
- 241000196324 Embryophyta Species 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 52
- 125000001188 haloalkyl group Chemical group 0.000 claims description 47
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 39
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 125000004414 alkyl thio group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 235000013339 cereals Nutrition 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 244000038559 crop plants Species 0.000 claims description 12
- 230000000855 fungicidal effect Effects 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 244000025254 Cannabis sativa Species 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000000417 fungicide Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 235000021028 berry Nutrition 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 claims description 4
- 241000335053 Beta vulgaris Species 0.000 claims description 4
- 240000008067 Cucumis sativus Species 0.000 claims description 4
- 240000007594 Oryza sativa Species 0.000 claims description 4
- 235000007164 Oryza sativa Nutrition 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 235000009566 rice Nutrition 0.000 claims description 4
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 3
- 241000345998 Calamus manan Species 0.000 claims description 3
- 235000014749 Mentha crispa Nutrition 0.000 claims description 3
- 244000246386 Mentha pulegium Species 0.000 claims description 3
- 235000016257 Mentha pulegium Nutrition 0.000 claims description 3
- 235000004357 Mentha x piperita Nutrition 0.000 claims description 3
- 240000004980 Rheum officinale Species 0.000 claims description 3
- 235000008081 Rheum officinale Nutrition 0.000 claims description 3
- 240000000111 Saccharum officinarum Species 0.000 claims description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 3
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 claims description 3
- 244000291414 Vaccinium oxycoccus Species 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 235000001050 hortel pimenta Nutrition 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 235000012950 rattan cane Nutrition 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 229940073608 benzyl chloride Drugs 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 244000024873 Mentha crispa Species 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 239000002585 base Substances 0.000 description 41
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 239000000243 solution Substances 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- 241000894006 Bacteria Species 0.000 description 18
- 239000002274 desiccant Substances 0.000 description 17
- 239000004009 herbicide Substances 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 235000002639 sodium chloride Nutrition 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 235000015097 nutrients Nutrition 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 241000209140 Triticum Species 0.000 description 11
- QKZHYYBXLJMLNM-UHFFFAOYSA-N methanimidoyl chloride Chemical compound ClC=N QKZHYYBXLJMLNM-UHFFFAOYSA-N 0.000 description 11
- 241000233866 Fungi Species 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000009036 growth inhibition Effects 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 102000003998 progesterone receptors Human genes 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 241000234642 Festuca Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 235000002595 Solanum tuberosum Nutrition 0.000 description 7
- 244000061456 Solanum tuberosum Species 0.000 description 7
- 239000000642 acaricide Substances 0.000 description 7
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 150000003851 azoles Chemical class 0.000 description 7
- 239000003899 bactericide agent Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- 230000002538 fungal effect Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000001069 nematicidal effect Effects 0.000 description 7
- 239000005645 nematicide Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 240000007241 Agrostis stolonifera Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 241000482268 Zea mays subsp. mays Species 0.000 description 6
- 150000001345 alkine derivatives Chemical class 0.000 description 6
- 235000013372 meat Nutrition 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 235000014347 soups Nutrition 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- 241000123650 Botrytis cinerea Species 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 4
- 235000017060 Arachis glabrata Nutrition 0.000 description 4
- 244000105624 Arachis hypogaea Species 0.000 description 4
- 235000010777 Arachis hypogaea Nutrition 0.000 description 4
- 235000018262 Arachis monticola Nutrition 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000004166 bioassay Methods 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 235000020232 peanut Nutrition 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000743339 Agrostis Species 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000005766 Dodine Substances 0.000 description 3
- UDSJPFPDKCMYBD-UHFFFAOYSA-N Metsulfovax Chemical compound S1C(C)=NC(C)=C1C(=O)NC1=CC=CC=C1 UDSJPFPDKCMYBD-UHFFFAOYSA-N 0.000 description 3
- 241001459558 Monographella nivalis Species 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241001597008 Nomeidae Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 244000292693 Poa annua Species 0.000 description 3
- 241000813090 Rhizoctonia solani Species 0.000 description 3
- 241001533598 Septoria Species 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 238000010958 [3+2] cycloaddition reaction Methods 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000012872 agrochemical composition Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000002223 anti-pathogen Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 239000004546 suspension concentrate Substances 0.000 description 3
- 239000003053 toxin Substances 0.000 description 3
- 231100000765 toxin Toxicity 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical group CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 2
- FFISWZPYNKWIRR-UHFFFAOYSA-N 5-oxidophenazin-5-ium Chemical compound C1=CC=C2[N+]([O-])=C(C=CC=C3)C3=NC2=C1 FFISWZPYNKWIRR-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000339490 Brachyachne Species 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 241001063191 Elops affinis Species 0.000 description 2
- 241000025852 Eremochloa ophiuroides Species 0.000 description 2
- 235000002756 Erythrina berteroana Nutrition 0.000 description 2
- 241000234643 Festuca arundinacea Species 0.000 description 2
- 241000508723 Festuca rubra Species 0.000 description 2
- 239000005784 Fluoxastrobin Substances 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 244000100545 Lolium multiflorum Species 0.000 description 2
- 240000004296 Lolium perenne Species 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 244000078639 Mentha spicata Species 0.000 description 2
- 239000005805 Mepanipyrim Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000005810 Metrafenone Substances 0.000 description 2
- 241001281801 Mycosphaerella arachidis Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 241000136254 Poa compressa Species 0.000 description 2
- 241000209049 Poa pratensis Species 0.000 description 2
- 241001123569 Puccinia recondita Species 0.000 description 2
- 108020004511 Recombinant DNA Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000044578 Stenotaphrum secundatum Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 240000001102 Zoysia matrella Species 0.000 description 2
- 241001360088 Zymoseptoria tritici Species 0.000 description 2
- WHDHEVMINMZADQ-UHFFFAOYSA-N [F].N1C=CC=C1 Chemical compound [F].N1C=CC=C1 WHDHEVMINMZADQ-UHFFFAOYSA-N 0.000 description 2
- CGIHPACLZJDCBQ-UHFFFAOYSA-N acibenzolar Chemical compound SC(=O)C1=CC=CC2=C1SN=N2 CGIHPACLZJDCBQ-UHFFFAOYSA-N 0.000 description 2
- 125000005157 alkyl carboxy group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical group CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- AQLPDLOXKZRZEV-UHFFFAOYSA-N dipyridin-3-ylmethanone Chemical compound C=1C=CN=CC=1C(=O)C1=CC=CN=C1 AQLPDLOXKZRZEV-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000012407 engineering method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000002038 ethyl acetate fraction Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- VDLGAVXLJYLFDH-UHFFFAOYSA-N fenhexamid Chemical compound C=1C=C(O)C(Cl)=C(Cl)C=1NC(=O)C1(C)CCCCC1 VDLGAVXLJYLFDH-UHFFFAOYSA-N 0.000 description 2
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 description 2
- GNVDAZSPJWCIQZ-UHFFFAOYSA-N flusulfamide Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 GNVDAZSPJWCIQZ-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical group CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical group CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 2
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 238000005375 photometry Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011265 semifinished product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical group CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000010455 vermiculite Substances 0.000 description 2
- 229910052902 vermiculite Inorganic materials 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BKBSMMUEEAWFRX-NBVRZTHBSA-N (E)-flumorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(F)=CC=1)=C\C(=O)N1CCOCC1 BKBSMMUEEAWFRX-NBVRZTHBSA-N 0.000 description 1
- ULDHMXUKGWMISQ-VIFPVBQESA-N (S)-(+)-Carvone Natural products CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- GVRWIAHBVAYKIZ-FNORWQNLSA-N (e)-dec-3-ene Chemical compound CCCCCC\C=C\CC GVRWIAHBVAYKIZ-FNORWQNLSA-N 0.000 description 1
- VTWKXBJHBHYJBI-VURMDHGXSA-N (nz)-n-benzylidenehydroxylamine Chemical class O\N=C/C1=CC=CC=C1 VTWKXBJHBHYJBI-VURMDHGXSA-N 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical group CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 1
- JXBLYSQTCABEMR-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-ylidene(methoxycarbonyl)azanium;chloride Chemical compound [Cl-].C1=CC=C2NC(=[NH+]C(=O)OC)NC2=C1 JXBLYSQTCABEMR-UHFFFAOYSA-N 0.000 description 1
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- OZOMQRBLCMDCEG-VIZOYTHASA-N 1-[(e)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(O1)=CC=C1\C=N\N1C(=O)NC(=O)C1 OZOMQRBLCMDCEG-VIZOYTHASA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- DGLHLIWXYSGYBI-UHFFFAOYSA-N 1-chloro-2-ethynylbenzene Chemical group ClC1=CC=CC=C1C#C DGLHLIWXYSGYBI-UHFFFAOYSA-N 0.000 description 1
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
- HCYLFVVAMIQOOJ-UHFFFAOYSA-N 1-phenylazulene Chemical compound C1=CC2=CC=CC=CC2=C1C1=CC=CC=C1 HCYLFVVAMIQOOJ-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LWEAHXKXKDCSIE-UHFFFAOYSA-M 2,3-di(propan-2-yl)naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S([O-])(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 LWEAHXKXKDCSIE-UHFFFAOYSA-M 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical group CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- DNBMPXLFKQCOBV-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OCCOCCOCC)=NC2=C1 DNBMPXLFKQCOBV-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical group CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical group CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- NUXCNUDGXUKOBN-UHFFFAOYSA-N 4-bromo-2-cyano-n,n-dimethyl-6-(trifluoromethyl)benzimidazole-1-sulfonamide Chemical compound C1=C(C(F)(F)F)C=C2N(S(=O)(=O)N(C)C)C(C#N)=NC2=C1Br NUXCNUDGXUKOBN-UHFFFAOYSA-N 0.000 description 1
- ZOMKCDYJHAQMCU-UHFFFAOYSA-N 4-butyl-1,2,4-triazole Chemical compound CCCCN1C=NN=C1 ZOMKCDYJHAQMCU-UHFFFAOYSA-N 0.000 description 1
- NNPRCLUGHFXSOU-UHFFFAOYSA-N 4-chloro-n-[cyano(ethoxy)methyl]benzamide Chemical compound CCOC(C#N)NC(=O)C1=CC=C(Cl)C=C1 NNPRCLUGHFXSOU-UHFFFAOYSA-N 0.000 description 1
- SBUKOHLFHYSZNG-UHFFFAOYSA-N 4-dodecyl-2,6-dimethylmorpholine Chemical compound CCCCCCCCCCCCN1CC(C)OC(C)C1 SBUKOHLFHYSZNG-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical group O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical group ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- LPULCTXGGDJCTO-UHFFFAOYSA-N 6-methylheptan-1-amine Chemical compound CC(C)CCCCCN LPULCTXGGDJCTO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LJQFHDUFUVMPSP-UHFFFAOYSA-N 8-methylnonan-1-amine Chemical compound CC(C)CCCCCCCN LJQFHDUFUVMPSP-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000003934 Abelmoschus esculentus Nutrition 0.000 description 1
- 240000004507 Abelmoschus esculentus Species 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001626535 Agrostis canina Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 102100034452 Alternative prion protein Human genes 0.000 description 1
- 239000005727 Amisulbrom Substances 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 239000005736 Benthiavalicarb Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000005738 Bixafen Substances 0.000 description 1
- 239000005739 Bordeaux mixture Substances 0.000 description 1
- 239000005740 Boscalid Substances 0.000 description 1
- 244000178993 Brassica juncea Species 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000005855 Brassica juncea var. subintegrifolia Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000005741 Bromuconazole Substances 0.000 description 1
- 239000005742 Bupirimate Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VLQLNHCGRAUVBE-UHFFFAOYSA-N C[As](O)(O)=O.N.[Fe+2] Chemical compound C[As](O)(O)=O.N.[Fe+2] VLQLNHCGRAUVBE-UHFFFAOYSA-N 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000009847 Cucumis melo var cantalupensis Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- JDZSMXLTQNHBRF-UHFFFAOYSA-N Dichlozoline Chemical compound O=C1C(C)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 JDZSMXLTQNHBRF-UHFFFAOYSA-N 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 239000005764 Dithianon Substances 0.000 description 1
- 239000005765 Dodemorph Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005774 Fenamidone Substances 0.000 description 1
- 239000005776 Fenhexamid Substances 0.000 description 1
- 239000005777 Fenpropidin Substances 0.000 description 1
- 241000192306 Festuca longifolia Species 0.000 description 1
- 241000410074 Festuca ovina Species 0.000 description 1
- 241000234645 Festuca pratensis Species 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005785 Fluquinconazole Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 229930184093 Furanether Natural products 0.000 description 1
- ILACEZQKVDMRMW-UHFFFAOYSA-N Furanether A Natural products C1C2=COC=C2C2C3CC(C)(C)CC3C1(C)O2 ILACEZQKVDMRMW-UHFFFAOYSA-N 0.000 description 1
- 241000223194 Fusarium culmorum Species 0.000 description 1
- UXDDRFCJKNROTO-UHFFFAOYSA-N Glycerol 1,2-diacetate Chemical group CC(=O)OCC(CO)OC(C)=O UXDDRFCJKNROTO-UHFFFAOYSA-N 0.000 description 1
- 239000004347 Glyceryl monoacetate Chemical group 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005566 Imazamox Substances 0.000 description 1
- FKWDSATZSMJRLC-UHFFFAOYSA-N Iminoctadine acetate Chemical compound CC([O-])=O.CC([O-])=O.CC([O-])=O.NC([NH3+])=NCCCCCCCC[NH2+]CCCCCCCCN=C(N)[NH3+] FKWDSATZSMJRLC-UHFFFAOYSA-N 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005797 Iprovalicarb Substances 0.000 description 1
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Chemical group C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical group CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005800 Kresoxim-methyl Substances 0.000 description 1
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
- 244000043158 Lens esculenta Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 239000005804 Mandipropamid Substances 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- 239000005808 Metalaxyl-M Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- FTCOKXNKPOUEFH-UHFFFAOYSA-N Myclozolin Chemical compound O=C1C(COC)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FTCOKXNKPOUEFH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- CYUIZYSKRBPGNU-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C12.[O].C1=CC=CC=C1 Chemical compound N1=CC=CC2=CC=CC=C12.[O].C1=CC=CC=C1 CYUIZYSKRBPGNU-UHFFFAOYSA-N 0.000 description 1
- ULWYIVYFPIPRRK-UHFFFAOYSA-N N1C=CC=CC=C1.[S] Chemical compound N1C=CC=CC=C1.[S] ULWYIVYFPIPRRK-UHFFFAOYSA-N 0.000 description 1
- JHXVRRJXCDAINK-UHFFFAOYSA-N NC(=O)N.N#CC#N Chemical compound NC(=O)N.N#CC#N JHXVRRJXCDAINK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VJAWBEFMCIINFU-UHFFFAOYSA-N Nitrothal-isopropyl Chemical group CC(C)OC(=O)C1=CC(C(=O)OC(C)C)=CC([N+]([O-])=O)=C1 VJAWBEFMCIINFU-UHFFFAOYSA-N 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- GPSSJHKOZAOGIF-UHFFFAOYSA-N O1C=CC=C1.N1C=CC=C1.[Cl] Chemical compound O1C=CC=C1.N1C=CC=C1.[Cl] GPSSJHKOZAOGIF-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005589 Oxasulfuron Substances 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- 239000005816 Penthiopyrad Substances 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- HEMINMLPKZELPP-UHFFFAOYSA-N Phosdiphen Chemical compound C=1C=C(Cl)C=C(Cl)C=1OP(=O)(OCC)OC1=CC=C(Cl)C=C1Cl HEMINMLPKZELPP-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 241000233629 Phytophthora parasitica Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000006597 Poa trivialis Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- JPFWJDMDPLEUBD-UHFFFAOYSA-N Polyoxin D Natural products OC1C(O)C(C(NC(=O)C(C(O)C(O)COC(N)=O)N)C(O)=O)OC1N1C(=O)NC(=O)C(C(O)=O)=C1 JPFWJDMDPLEUBD-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005821 Propamocarb Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005604 Prosulfuron Substances 0.000 description 1
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 239000005869 Pyraclostrobin Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000005831 Quinoxyfen Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- OSOSMTZOKLTVFS-UHFFFAOYSA-N S(=O)(=O)(O)C(C(=O)O)CC(=O)O.C(C)C(C[Na])CCCC Chemical compound S(=O)(=O)(O)C(C(=O)O)CC(=O)O.C(C)C(C[Na])CCCC OSOSMTZOKLTVFS-UHFFFAOYSA-N 0.000 description 1
- 241001518640 Sclerotinia homoeocarpa Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 244000046109 Sorghum vulgare var. nervosum Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005840 Tetraconazole Substances 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- 239000005847 Triazoxide Substances 0.000 description 1
- 239000005859 Triticonazole Substances 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 239000005860 Valifenalate Substances 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000005870 Ziram Substances 0.000 description 1
- 239000005863 Zoxamide Substances 0.000 description 1
- 101100339555 Zymoseptoria tritici HPPD gene Proteins 0.000 description 1
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical group 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- JSOJVSBOEOWZJX-UHFFFAOYSA-N [O].N1=CC=CC2=CC=CC=C21 Chemical compound [O].N1=CC=CC2=CC=CC=C21 JSOJVSBOEOWZJX-UHFFFAOYSA-N 0.000 description 1
- COGNCXJCCDGTDV-UHFFFAOYSA-N [O].N1C=CC=CC=C1 Chemical compound [O].N1C=CC=CC=C1 COGNCXJCCDGTDV-UHFFFAOYSA-N 0.000 description 1
- XALIRDFUFAEGQW-UHFFFAOYSA-N [SiH3]C=1C=CON=1 Chemical class [SiH3]C=1C=CON=1 XALIRDFUFAEGQW-UHFFFAOYSA-N 0.000 description 1
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- GMAUQNJOSOMMHI-JXAWBTAJSA-N alanycarb Chemical compound CSC(\C)=N/OC(=O)N(C)SN(CCC(=O)OCC)CC1=CC=CC=C1 GMAUQNJOSOMMHI-JXAWBTAJSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- BREATYVWRHIPIY-UHFFFAOYSA-N amisulbrom Chemical compound CN(C)S(=O)(=O)N1C=NC(S(=O)(=O)N2C3=CC(F)=CC=C3C(Br)=C2C)=N1 BREATYVWRHIPIY-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HUTDUHSNJYTCAR-UHFFFAOYSA-N ancymidol Chemical compound C1=CC(OC)=CC=C1C(O)(C=1C=NC=NC=1)C1CC1 HUTDUHSNJYTCAR-UHFFFAOYSA-N 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- WZEMSIKSCALWJZ-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO.CCO WZEMSIKSCALWJZ-UHFFFAOYSA-N 0.000 description 1
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- VVSLYIKSEBPRSN-PELKAZGASA-N benthiavalicarb Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@@H](NC(O)=O)C(C)C)=NC2=C1 VVSLYIKSEBPRSN-PELKAZGASA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- LDLMOOXUCMHBMZ-UHFFFAOYSA-N bixafen Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=C(F)C=C1C1=CC=C(Cl)C(Cl)=C1 LDLMOOXUCMHBMZ-UHFFFAOYSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-UHFFFAOYSA-N blasticidin-S Natural products O1C(C(O)=O)C(NC(=O)CC(N)CCN(C)C(N)=N)C=CC1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 1
- 229940118790 boscalid Drugs 0.000 description 1
- 244000275904 brauner Senf Species 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JOXAXMBQVHFGQT-UHFFFAOYSA-J copper;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Cu+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S JOXAXMBQVHFGQT-UHFFFAOYSA-J 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000011950 custard Nutrition 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- CJHXCRMKMMBYJQ-UHFFFAOYSA-N dimethirimol Chemical compound CCCCC1=C(C)NC(N(C)C)=NC1=O CJHXCRMKMMBYJQ-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Chemical group CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- PGQAXGHQYGXVDC-UHFFFAOYSA-N dodecyl(dimethyl)azanium;chloride Chemical compound Cl.CCCCCCCCCCCCN(C)C PGQAXGHQYGXVDC-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical group CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- VMNULHCTRPXWFJ-UJSVPXBISA-N enoxastrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)\C=C\C1=CC=C(Cl)C=C1 VMNULHCTRPXWFJ-UJSVPXBISA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- IGUYEXXAGBDLLX-UHFFFAOYSA-N ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-1,3-oxazolidine-5-carboxylate Chemical compound O=C1C(C(=O)OCC)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 IGUYEXXAGBDLLX-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 208000000283 familial pityriasis rubra pilaris Diseases 0.000 description 1
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 1
- JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
- GOWLARCWZRESHU-AQTBWJFISA-N ferimzone Chemical compound C=1C=CC=C(C)C=1C(/C)=N\NC1=NC(C)=CC(C)=N1 GOWLARCWZRESHU-AQTBWJFISA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- IPENDKRRWFURRE-UHFFFAOYSA-N fluoroimide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(Cl)=C(Cl)C1=O IPENDKRRWFURRE-UHFFFAOYSA-N 0.000 description 1
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- LTVDTKRMOQDRCH-UHFFFAOYSA-N furan;1h-pyrrole Chemical compound C=1C=CNC=1.C=1C=COC=1 LTVDTKRMOQDRCH-UHFFFAOYSA-N 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 235000019442 glyceryl monoacetate Nutrition 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 230000003450 growing effect Effects 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- WPOOICLZIIBUBM-UHFFFAOYSA-H iron;iron(3+);methyl-dioxido-oxo-$l^{5}-arsane Chemical compound [Fe].[Fe+3].[Fe+3].C[As]([O-])([O-])=O.C[As]([O-])([O-])=O.C[As]([O-])([O-])=O WPOOICLZIIBUBM-UHFFFAOYSA-H 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Chemical group CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- IXJOSTZEBSTPAG-UHFFFAOYSA-N methasulfocarb Chemical compound CNC(=O)SC1=CC=C(OS(C)(=O)=O)C=C1 IXJOSTZEBSTPAG-UHFFFAOYSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 1
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002885 octadecanoids Chemical class 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- JHIPUJPTQJYEQK-ZLHHXESBSA-N orysastrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CO\N=C(/C)\C(=N\OC)\C(\C)=N\OC JHIPUJPTQJYEQK-ZLHHXESBSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- WBTYBAGIHOISOQ-UHFFFAOYSA-N pent-4-en-1-yl 2-[(2-furylmethyl)(imidazol-1-ylcarbonyl)amino]butanoate Chemical compound C1=CN=CN1C(=O)N(C(CC)C(=O)OCCCC=C)CC1=CC=CO1 WBTYBAGIHOISOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- JPFWJDMDPLEUBD-ITJAGOAWSA-N polyoxorim Polymers 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
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- NWUWYYSKZYIQAE-LBAUFKAWSA-N propan-2-yl n-[3-methyl-1-[[(1s)-1-(4-methylphenyl)ethyl]amino]-1-oxobutan-2-yl]carbamate Chemical compound CC(C)OC(=O)NC(C(C)C)C(=O)N[C@@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-LBAUFKAWSA-N 0.000 description 1
- CPAUHNHNGALXSY-UHFFFAOYSA-N propan-2-yl n-butylcarbamate Chemical class CCCCNC(=O)OC(C)C CPAUHNHNGALXSY-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- CRFYLQMIDWBKRT-LPYMAVHISA-N pyribencarb Chemical compound C1=C(Cl)C(CNC(=O)OC)=CC(C(\C)=N\OCC=2N=C(C)C=CC=2)=C1 CRFYLQMIDWBKRT-LPYMAVHISA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 229960002132 pyrrolnitrin Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 230000021918 systemic acquired resistance Effects 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide 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
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及具有植物生长调节特性的式(I)异噁唑化合物,涉及包含它们的农业组合物,并且涉及所述化合物用于调节植物生长的用途。
Description
本发明涉及具有植物生长调节特性的异噁唑化合物,涉及包含它们的农业组合物,并涉及所述化合物用于调节植物生长的用途。
植物生长调节剂(PGRs)通常是用于加速或阻滞植物或其产品的生长或成熟速度或者改变其发育的任何物质或物质的混合物。PGRs影响植物的生长和分化,该过程一般且此后称为″植物保健″。因此,需要具有PGR活性的更多物质。
国际专利申请WO2006/031631提及具有杀真菌特性的一系列异噁唑衍生物。
已令人惊讶地发现本发明的异噁唑化合物展示植物生长调节特性,并因此适于在农业中用于改善和控制植物保健。
相应地,在第一方面,本发明提供式(I)化合物或其盐作为植物生长调节剂的用途
其中:
R1是任选用羟基,苯基或卤代苯基取代的烷基;烷氧基烷基;卤代烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,苯氧基,烷氧基炔基,氰基,或硝基取代的芳基;或者任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;
R2是烷基;烷氧基烷基;卤代烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基;或者任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;
R3是H;烷基;烷氧基;烷氧基烷基;卤代烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳氧基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳硫基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,烷氧基炔基,氰基,硝基取代的芳基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;或者烷基甲硅烷基;并且
R4是H或酰基。
植物生长调节剂能够,例如降低植物高度,刺激种子发芽,诱导开花,加深叶子着色,改变植物生长速率和调整结果的时机和效率。此外,PGRs可以展示显著的生长-调节特性,其能够引起栽培植物或收获作物的产量增加。
PGRs还可以具有取决于浓度的生长抑制作用。单子叶植物和双子叶植物的生长均可以得到抑制。抑制许多栽培植物的植物性生长使得可以在作物区域散播更多的植物,从而每单位面积可以获得更高产量。某些情况下抑制单子叶植物的植物性生长是希望和有利的,所述单子叶植物是例如栽培植物比如禾谷类。上述生长抑制具有经济价值。
将PGRs用于抑制禾谷类的高度生长也是重要的,原因是缩短茎杆会减少或完全消除在收获之前倒伏的风险。此外,PGRs能够引起禾谷类作物的茎杆强化,这同样抵抗倒伏。
另外,本发明也提供改善植物的包含本发明的异噁唑衍生物的组合物,该过程一般且此后称为″植物保健″。
例如,可以提及的有利特性是改善的作物特征,包括:出苗,作物产量,蛋白质含量,增加的活力,更快的/延缓的成熟,增加的种子出苗速度,改善的营养素利用效率,改善的氮利用效率,改善的用水效率,改善的油含量和/或品质,改善的可消化性,更快的/更均匀的熟化,改善的风味,改善的淀粉含量,更发达的根系(改善的根系生长),改善的逆境忍耐(例如对干旱、炎热、盐分、光照、UV、水分、寒冷),减少的乙烯(减少的产生和/或接受的抑制),分蘖增加,植物高度增加,更大的叶片,更少的死亡基生叶,更强壮的分蘖,更绿叶色,色素含量,光合活性,更少的输入需求(比如肥料或水),更少的种子需求,更多产的分蘖,更早的开花,谷物早熟,更少的植物倾倒(倒伏),增加的茎枝生长,增强的植株活力,增加的植株密度以及早期和更佳的发芽。
所获得的有利特性,特别是得自经处理种子的那些,包括例如改善的发芽和田间成苗,更佳的活力和更均匀的田间成苗。
特别地得自叶面和/或沟内施用的有利特性包括,例如,经改善的植物生长和植物发育、更佳的生长、更多分蘖、更绿的叶片、更大的叶片、更多的生物质、更佳的根部、经改善的植物压力耐受、更多的谷物产量、更多的收获生物质、经改善的收获品质(脂肪酸、代谢产物、油等的含量)、更易营销的产品(例如经改善的大小)、经改善的工序(例如更长的贮藏期限、对化合物的更佳提取)、经改善的种子品质(在随后的季节播种用于种子生产);或者本领域技术人员熟悉的任何其他优势。
因此,本发明的目的是提供适于应对上述挑战的组合物和方法。
本发明提供植物保护活性成分,其是根据本发明的式(I)异噁唑化合物,尤其是说明书中描述为优选的单独的异噁唑化合物,以及具有增加效力的混合物;还提供通过将所述化合物和混合物施用至植物或其处所改善植物健康的方法。
式(I)化合物的作用独立于任意杀真菌作用。根据本发明的式(I)异噁唑化合物,尤其是上文描述为优选化合物的单个异噁唑化合物展示植物保健特性。
本发明也涉及组合物,其包含如本文描述的活性化合物与适宜载体(例如农业载体)的组合,或基本上由其组成。
本发明的前述和其它目的和方面更详细地阐释如下。
″烷基″如本文所用是指饱和的烃残基,其可以是直链或支化的链或环(环烷基)并含有1至24个碳原子。在所述术语单独使用的情况下和在其用作复合术语比如卤代烷基和相似术语的一部分的情况下,该定义都适用。优选的直链和支化烷基可以含有1至8个碳原子,更优选1至4个碳,甚至更优选1至4个碳原子。代表性的烷基包括,例如甲基,乙基,异丙基,正丙基,正丁基,叔丁基,叔戊基,和2,5-二甲基己基。优选的环烷基可以含有3至12个碳原子,更优选4至10个碳,甚至更优选5至8个碳原子和最优选5或6个碳原子。优选的环烷基包括,例如环丁基,环丙基,环戊基和环己基。
″烯基″如本文所用是指直链或支化链的烃,其含有2至24个碳,更优选2至8个碳,还更优选2至6个碳原子,甚至更优选2至4个碳原子,且含有至少一个碳-碳双键。代表性的烯基包括,例如乙烯基,2-丙烯基,2-甲基-2-丙烯基,3-丁烯基,4-戊烯基,5-己烯基,2-庚烯基,2-甲基-1-庚烯基和3-癸烯基。
″炔基″如本文所用是指直链或支化链的烃基,其含有2至24个碳,更优选2至8个碳,还更优选2至6个碳原子,甚至更优选2至4个碳原子,且含有至少一个碳-碳三键。代表性的炔基包括,例如乙炔基,1-丙炔基,2-丙炔基,3-丁炔基,2-戊炔基和1-丁炔基。
代表性的烷氧基包括,例如甲氧基,乙氧基和叔丁氧基。
代表性的烷硫基包括,例如甲硫基,乙硫基,叔丁硫基和己硫基。
“杂环基”,如本文所用是指饱和的或部分不饱和的环状烃,其含有3至10个环原子,所述环原子中多至4个可以是杂原子比如氮、氧和硫。杂环基的实例是环氧乙烷基,氮杂环丁烷基,四氢呋喃基,硫杂环戊基,吡咯烷基,吡咯啉基,咪唑烷基,咪唑啉基,环丁砜基,二氧杂环戊基,二氢吡喃基,四氢吡喃基,哌啶基,吡唑啉基,吡唑烷基,二噁烷基,吗啉基,二噻烷基,硫吗啉基,哌嗪基,氮杂基,氧氮杂基,硫氮杂基,噻唑啉基和二氮杂环庚烷基。
″芳基″是指芳族取代基,其可以是单环或者稠合的、共价连接的或连接至共用基团比如亚乙基或亚甲基部分的多环。芳族环可以各自含有杂原子,因此如本文所用芳基涵盖杂芳基。芳基部分可以任选用独立选自卤素,硝基,烷基羧基,烷氧基和苯氧基的1至4个取代基取代。芳基的代表性实例包括苯基薁基,茚满基,茚基,萘基,四氢萘基,联苯基,二苯基甲基,2,2-二苯基-1-乙基,噻吩基,吡啶基和喹喔啉基。最优选,芳基是苯基。
″杂芳基″意指环状芳族烃,其含有3至10个环原子,所述环原子包括1至4个独立选自氮、氧和硫的杂原子。优选的杂芳基是五和六元环且含有一至三个独立选自氮、氧和硫的杂原子。杂芳基部分可以任选用1至4个独立选自卤素,硝基,烷基羧基,烷氧基和苯氧基的取代基取代。杂芳基的实例包括呋喃基,噻吩基,吡咯基,噁唑基,噻唑基,咪唑基,吡唑基,异噁唑基,异噻唑基,噁二唑基,三唑基,噻二唑基,吡啶基,嘧啶基,吡嗪基,吡喃基,哒嗪基,四唑基,三嗪基。
此外,术语杂芳基包括稠合的杂芳基,例如苯并咪唑基,苯并噁唑基,咪唑并吡啶基,苯并噁嗪基,苯并噻嗪基,噁唑并吡啶基,苯并呋喃基,喹啉基,喹唑啉基,喹喔啉基,苯并噻唑基,酞酰亚氨基,苯并呋喃基,苯并二氮杂基,吲哚基,异吲哚基,异苯并呋喃基,色烯基,呫吨基,吲嗪基,吲唑基,嘌呤基,喹嗪基,异喹啉基,酞嗪基,萘啶基和苯并[b]噻吩基。
酰基包括任意易水解的酰基,并包含例如,C(O)R5,C(O)OR5,C(O)NHR5和C(O)NR5R6,其中R5和R6各自独立选自烷基,烯基,炔基,杂环基,芳基和杂芳基。酰基可以任选用一个或多个例如1、2、3或4个卤素或OR5基团取代。优选的酰基是乙酰基,苯甲酰基和苯乙酰基。
″卤代″或″卤素″意指氟,氯,溴和碘并优选是氟或氯。
″卤代烷基″包括一卤代烷基,多卤代烷基和全卤代烷基,例如,氯甲基,2-溴乙基,2-氟乙基,2,2,2-三氟乙基,氯二氟甲基,三氯甲基,三氟甲基,五氟乙基和2-氯-3-氟戊基。
″有机碱″如本文所用包括,例如三乙胺,三异丁胺,三异辛基胺,三异癸基胺,二乙醇胺,三乙醇胺,吡啶,吗啉,及其混合物。优选类别的有机碱是有机胺。
″无机碱″如本文所用包括,例如碳酸钠,碳酸氢钠,碳酸钾,及其混合物。
″惰性溶剂″如本文所用包括任意适宜的惰性溶剂,其包括例如四氢呋喃,N-甲基吡咯烷酮,二甲基甲酰胺,甲苯,二甲醚,甲基叔丁基醚和二噁烷,二氯甲烷,氯仿,1,2-二氯乙烷,及其混合物。
″质子溶剂″如本文所用可以是任意适宜的质子溶剂,其包括例如甲醇,乙醇,异丙醇,正丁醇,乙二醇,甲基溶纤剂(Cellosolve),乙基溶纤剂(Cellosolve),环己醇,甘油,二乙二醇,三乙醇胺,聚乙二醇,仲丁醇,正丙醇和叔丁醇。
“任选经取代的”意指被一个或多个取代基,尤其是1、2、3或4个取代基取代。在基团可以选自许多备择基团的情况下,所选基团可以是相同或不同的。
″农业上可接受的盐″意指农业或园艺用途的成盐领域中已知和接受的阳离子的盐。优选,所述盐是可溶于水的。
式(I)化合物可以以不同的几何或旋光异构形式或以不同的互变异构体形式存在。可以存在一个或多个手性中心,在此情况中式(I)化合物可以作为纯对映体,对映体的混合物,纯非对映异构体或非对映异构体的混合物存在。分子中可以存在双键,比如C=C或C=N键,在此情况下式(I)化合物可以作为单独的异构体或异构体的混合物存在。可以存在互变异构中心。本发明涵盖全部这样的异构体和互变异构体及其所有比例的混合物以及同位素形式比如氘化的化合物。
式(I)化合物的适宜盐包括酸加成盐,例如与无机酸比如盐酸,氢溴酸,硫酸,硝酸或磷酸形成的那些,或者与有机羧酸比如草酸,酒石酸,乳酸,丁酸,甲苯酸,己酸或邻苯二甲酸,或者与磺酸比如甲磺酸,苯磺酸或甲苯磺酸形成的那些。有机羧酸的其他实例包括卤代酸,比如三氟乙酸。
N-氧化物是叔胺的氧化形式或者含氮杂芳族化合物的氧化形式。它们描述于许多书籍中,例如Angelo Albini和Silvio Pietra的“Heterocyclic N-oxides”,CRC Press,Boca Raton,Florida,1991。
在又一方面,本发明提供调节有用植物作物的植物生长的方法,其包括向所述植物,向所述植物的一个或多个部分,或向其处所或植物繁殖材料,施用如本文所定义的式(I)化合物。
本发明的优选实施方式如下文所定义同样适用于如本文所定义的发明的各个方面及其优选方面。
在一种优选实施方式中,R1是任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,苯氧基,烷氧基炔基,氰基,硝基取代的芳基;或者任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基或硝基取代的杂芳基。
优选,R1是任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,苯氧基,烷氧基炔基,氰基,或硝基取代的芳基;或者任选用卤素取代的杂芳基。
更优选,R1是任选用卤素,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C6-卤代烷氧基,苯氧基,甲氧基炔丙基,氰基,或硝基取代的苯基;或者呋喃基,噻吩基,吡啶基,或苯并噻吩基,各自任选用卤素取代。
最优选,R1是2-氯苯基,4-氯苯基,2,4-二氯苯基,2-氟苯基,2,4-二氟苯基,3,5-二氟苯基,4-三氟-甲基苯基,4-三氟甲氧基苯基或2-噻吩基。
在又一优选的实施方式中,R1是任选用羟基,苯基或卤代苯基取代的烷基;或者任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基或硝基取代的芳基烷基。
优选,R1是任选用羟基,苯基或卤代苯基取代的C1-C6-烷基;或者任选用卤素或烷基取代的芳基烷基。
更优选,R1是C1-C6-烷基;或任选用卤素或C1-C6-烷基取代的苯基-C1-C6-烷基。
最优选,R1是正戊基,叔丁基,苄基或4-氯苄基。
在优选的实施方式中,R2是任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基或硝基取代的杂芳基。
优选,R2是吡啶基,嘧啶基或异喹啉基,各自任选用卤素,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C6-卤代烷氧基,氰基,或硝基取代。
更优选,R2是2-、3-或4-吡啶基或5-嘧啶基,各自任选用卤素,C1-C6-卤代烷基,C1-C6-烷氧基或C1-C6-烷硫基取代。
最优选,R2是2-吡啶基,3-吡啶基,或5-嘧啶基,各自任选用甲基,氯,氟,甲氧基,硫代甲氧基或三氟甲基取代。
在一种优选的实施方式中,R3是烷基;烷氧基;烷氧基烷基;卤代烷基;任选用卤素取代的芳基烷基;任选用卤素取代的芳氧基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,烷氧基炔基,氰基或硝基取代的芳基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;或者烷基甲硅烷基;
优选,R3是烷基;烷氧基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,烷氧基炔基,氰基或硝基取代的芳基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基或硝基取代的杂芳基;或者烷基甲硅烷基。
更优选,R3是C1-C6-烷基;C1-C6-烷氧基;任选用卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,甲氧基炔丙基,氰基或硝基取代的苯基;呋喃基,噻吩基或吡啶基,各自任选用卤素,C1-C6-烷基或C1-C6-烷氧基取代;或者C1-C6-烷基甲硅烷基。
更优选,R3是苯基,3-氯苯基,4-氯苯基,4-氟苯基,3,5-二氟苯基,4-甲基苯基,2-噻吩基,5-氯-2-噻吩基,5-甲基-2-噻吩基,3-噻吩基,叔丁基或三甲基甲硅烷基。
在一种优选的实施方式中,R4是H,乙酰基,苯甲酰基和苯乙酰基。
最优选地,R4是H。
在本发明的一个优选方面中:
R1是任选用羟基,苯基或卤代苯基取代的烷基;任选用卤素或烷基取代的芳基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,苯氧基,烷氧基炔基,氰基,或硝基取代的芳基;或者任选用卤素取代的杂芳基;
R2是任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;
R3是烷基;烷氧基;烷氧基烷基;卤代烷基;任选用卤素取代的芳基烷基;任选用卤素取代的芳氧基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,烷氧基炔基,氰基,硝基取代的芳基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;或者烷基甲硅烷基;并且
R4是H或乙酰基。
在本发明更优选的方面中:
R1是C1-C6-烷基;或任选用卤素或C1-C6-烷基取代的苯基-C1-C6-烷基;任选用卤素,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C6-卤代烷氧基,苯氧基,甲氧基炔丙基,氰基,或硝基取代的苯基;或者呋喃基、噻吩基、吡啶基或苯并噻吩基,各自任选用卤素取代;
R2是吡啶基或嘧啶基,各自任选用卤素,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C6-卤代烷氧基,氰基,或硝基取代;
R3是C1-C6-烷基;C1-C6-烷氧基;任选用卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,甲氧基炔丙基,氰基或硝基取代的苯基;呋喃基,噻吩基或吡啶基,各自任选用卤素,C1-C6-烷基或C1-C6-烷氧基取代;或者C1-C6-烷基甲硅烷基;并且
R4是H。
根据本发明方法使用的优选式(I)化合物选自:
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物144);
3-(4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基卜异噁唑(化合物145);
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(化合物146);
3-(2,4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物147);
3-(2-氟-4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物148);
3-(4-氯苯基)-5-(2-甲氧基吡啶)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物149);
3-(4-氯苯基)-5-(4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物150);
3-(4-氯苯基)-5-(2,4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物151);
3-(2,4-氟-4-氯苯基)-5-(2-氯-4-氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(化合物152);和
(R)-3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(化合物153);
及其盐。
在又一方面,本发明提供调节有用植物作物的植物生长的方法,其包括向所述植物,向所述植物的一个或多个部分,或者向其处所或植物繁殖材料,施用如本文所定义的式(I)化合物,其中所述方法包括单独或与一种或多种常规植物保护配制辅剂结合地一次或多次施用一种或多种如本文所定义的化合物。
在又一方面中,本发明提供调节有用植物作物的植物生长的方法,其包括向所述植物,向所述植物的一个或多个部分,或向其处所或植物繁殖材料,施用如本文所定义的式(I)化合物,其中依次进行两次或更多次施用,并且其中所述两次或更多次施用具有浓度相同或不同的、或组合相同或不同的、或者两者都相同或不同的如本文所定义的化合物。
在本发明的优选实施方式中,有用植物作物选自禾谷类,稻,甜菜,豆科植物,油料植物,黄瓜植物,纤维植物,蔬菜,种植园作物,观赏植物,藤本植物,灌木类浆果(bushberries),蔓藤类浆果(caneberries),酸果蔓,胡椒薄荷,大黄,留兰香,甘蔗和草皮草。
在本发明的优选实施方式中,植物生长调节效果是抑制或阻滞植物生长。
在另一方面中,本发明提供农业组合物,其包含一种或多种如本文所定义的式(I)化合物和一种或多种常规植物保护辅剂。
另外,已发现式(I)化合物的对映体之一比另一对映体显著更具活性。
在又一方面中,本发明涉及式(I)化合物的(R)-对映体,指定为(R)-(I),其中R1,R2,R3和R4如本文所定义;及其盐。
优选的式(R)-(I)化合物包括本文表1化合物1至153和表2化合物154至195的(R)-对映体。
本发明提供作为单个对映体的式(R)-(I)化合物,其具有的对映体过量(e.e.)为至少40%,例如至少50%、60%、70%或80%,优选至少90%,更优选至少95%,还更优选至少98%并且最优选至少99%。
在又一方面中,本发明涉及式(I)化合物的(S)-对映体,指定为(S)-(I),其中R1,R2,R3和R4如本文所定义;及其盐。
本发明提供作为单个对映体的式(S)-(I)化合物,其具有的对映体过量(e.e.)为至少40%,例如至少50%、60%、70%或80%,优选至少90%,更优选至少95%,还更优选至少98%并且最优选至少99%。
优选的式(S)-(I)化合物包括本文表1化合物1至153和表2化合物154至195的(S)-对映体。
在又一方面中,本发明还涉及农业组合物,其包含如本文所定义的式(R)-(I)化合物,或其农业化学上可接受的盐,以及农业化学上可接受的稀释剂或载体。
在又一方面中,本发明还涉及农业组合物,其包含如本文所定义的式(S)-(I)化合物,或其农业化学上可接受的盐,以及农业化学上可接受的稀释剂或载体。
在又一方面,本发明涉及新的式(I)化合物,选自:
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物144);
3-(4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物145);
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(化合物146);
3-(2,4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物147);
3-(2-氟-4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物148);
3-(4-氯苯基)-5-(2-甲氧基吡啶)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物149);
3-(4-氯苯基)-5-(4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物150);
3-(4-氯苯基)-5-(2,4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑(化合物151);
3-(2,4-氟-4-氯苯基)-5-(2-氯-4-氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(化合物152);和
(R)-3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(化合物153);
及其盐。
“植物繁殖材料”意指植物的生殖部分,其包括全部种类的种子(果实、块茎、鳞茎、谷物等),根,根茎,插条,伐条等。植物繁殖材料还可以包括植物和幼苗,其有待在萌芽之后或者自土壤出苗之后进行移植。
“处所”意指待处理植物生长于其上的大田,或播种栽培植物的种子之处,或其中种子将被置于土壤中的场所。
待保护的有用植物作物一般包含,例如,下述植物种类:禾谷类(小麦,大麦,黑麦,燕麦,玉米(包括饲料用玉米,爆裂种玉米和甜玉米),稻,高粱和有关作物);甜菜(糖用甜菜和饲用甜菜);豆科植物(菜豆,小扁豆,豌豆,大豆);油料植物(油菜,芥菜,向日葵);黄瓜植物(西葫芦,黄瓜,甜瓜);纤维植物(棉花,亚麻,大麻,黄麻);蔬菜(菠菜,莴苣,芦笋,卷心菜,胡萝卜,茄子,洋葱,胡椒,番茄,马铃薯,辣椒,秋葵);种植园作物(香蕉,果树,橡胶树,树木苗圃),观赏植物(花卉,灌木,阅叶树和常青树,比如针叶树);以及其它植物比如藤本植物,灌木类浆果(bushberries)(比如越桔),蔓藤类浆果(caneberries),酸果蔓,胡椒薄荷,大黄,留兰香,甘蔗和草皮草包括,例如,冷季草皮草(例如,早熟禾属(Poa L.),比如草地早熟禾(Poa pratensis L.),普通早熟禾(Poatrivialis L.),加拿大早熟禾(Poa compressa L.)和早熟禾(Poa annua L.);剪股颖属(Agrostis L.),比如匍匐翦股颖(Agrostis palustris Huds.),细弱翦股颖(Agrostis tenius Sibth.),普通翦股颖(Agrostis canina L.)和小糠草(Agrostis alba L.);羊茅属(Festuca L.),比如苇状羊茅(Festucaarundinacea Schreb.),牛尾草(Festuca elatior L.)和细叶羊茅,比如紫羊茅(Festuca rubra L.),丛生型紫羊茅(Festuca rubra var.CommutataGaud.),羊茅(Festuca ovina L.)和长叶羊茅(Festuca longifolia);和黑麦草属(Lolium L.),比如多年黑麦草(Lolium perenne L.)和多花黑麦草(Lolium multiflorum Lam.))和暖季草皮草(例如,狗牙根属(Cynodon L.C.Rich),包括杂交和普通狗牙根;结缕草属(Zoysia Willd.),偏序钝叶草(Stenotaphrum secundatum(Walt.)Kuntze);和假俭草(Eremochloaophiuroides(Munro.)Hack.))。
术语“有用植物”还包括由于常规育种方法或基因工程方法使其耐受除草剂如溴苯腈或多类除草剂(比如HPPD抑制剂,ALS抑制剂;例如氟嘧磺隆,氟磺隆和三氟啶磺隆,EPSPS(5-烯醇-丙酮酰-莽草酸-3-磷酸-合成酶)抑制剂,GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)的有用植物。已通过常规育种方法(诱变)使其耐受咪唑啉酮类(例如甲氧咪草烟)的作物的实例是夏季油菜(Canola)。通过基因工程方法使之耐受除草剂或除草剂类的作物实例包括抗草甘膦和抗草铵膦的玉米品种,该品种可根据商品名Herculex和购得。
术语″有用植物″也包括这样的有用植物,其已通过使用重组DNA技术转化使其能够合成一种或多种选择性作用的毒素,所述毒素比如已知自产毒素细菌,特别是芽孢杆菌属(Bacillus)的那些。
术语″有用植物″也包括这样的有用植物,其已通过使用重组DNA技术转化使其能够合成具有选择性作用的抗病原物质,比如所谓的″发病机理-相关性蛋白″(PRPs,参见例如欧洲专利申请EP 0,392,225)。所述抗病原物质和能合成所述抗病原物质的转基因植物的实例已知于例如欧洲专利申请EP 0,392,225和EP 0,353,191以及国际专利申请WO 95/33818。所述转基因植物的制造方法是本领域技术人员通常已知的,并且描述于例如上述出版物中。
本发明的农业化学组合物通常包括0.1到99%重量,优选0.1到95%重量的式(I)化合物,99.9到1%重量,优选99.8到5%重量的固体或液体助剂,以及0到25%重量,优选0.1到25%重量的表面活性剂。
适宜地,本发明的农业化学组合物在病害发展之前施用。配制剂的用量和使用频率是本领域中常用的那些并将取决于这样的因素,比如植物的生长阶段和位置、时机和施用方法。有利的施用率通常是5g到2kg的活性成分(a.i.)每公顷(ha),优选10g到1kg活性成分/公顷,最优选20g到600g活性成分/公顷。当用作种子处理试剂时,适宜的施用率是10mg到1g活性成分每kg种子。
在实践中,如上文所指,包含式(I)化合物的农业化学组合物作为配制剂来施用,所述配制剂含有工业上已知或使用的各种助剂和载体。因此,它们可以配制为颗粒剂,可湿性粉剂或可溶性粉剂,乳油,可包衣糊剂,尘剂,可流动剂,溶液剂,悬浮剂或乳液剂或者控释形式比如微胶囊。这些配制剂更详细地描述如下并且可以含有0.5%重量至95%重量或更多的活性成分。最佳量将取决于配制剂,施用设备和待处理植物的性质。
浓悬浮剂是含水配制剂,其中悬浮有活性化合物的细分固体颗粒。所述配制剂包括抗沉剂(anti-settling agents)和分散剂,并可以还包括用来增强活性的润湿剂,以及消泡剂和晶体生长抑制剂。使用时,将这些浓悬浮剂稀释于水中,并通常作为喷雾剂施用至待处理的区域。活性成分的量可以是浓悬浮剂的0.5%至95%。
可湿性粉剂是在水中或其它液体载体中易于分散的细分颗粒形式。所述颗粒包含保留在固体基质中的活性成分。典型的固体基质包括漂白土、高岭土、硅土和其它易于润湿的有机或无机固体。可湿性粉剂通常含有5%至95%的活性成分和少量润湿剂、分散剂或乳化剂。
乳油是在水中或其它液体中可分散的匀质液体组合物并可以完全由活性化合物与液体或固体乳化剂组成,或者还可以含有液体载体比如二甲苯、重芳族的石脑油、异佛尔酮和其它非挥发性有机溶剂。在使用中,将上述乳油分散在水或其它液体中并通常作为喷雾施用至待处理区域。活性成分的量可以是乳油的0.5%至95%。
颗粒配制剂包括挤出物和相对粗的颗粒,并通常不加稀释地施用至需要处理的区域。颗粒配制剂的典型载体包括细砂,漂白土,凹凸棒石粘土,斑脱粘土,蒙脱石粘土,蛭石,珍珠岩,碳酸钙,砖,浮石,叶蜡石,高岭土,白云石,灰泥,木屑,玉米芯粉,磨碎的花生壳,糖类,氯化钠,硫酸钠,硅酸钠,硼酸钠,氧化镁,云母,氧化铁,氧化锌,氧化钛,氧化锑,冰晶石,石膏,硅藻土,硫酸钙以及吸收活性化合物或能用其包覆的其它有机或无机材料。颗粒配制剂通常含有5%至25%的活性成分,其可以包含表面活性剂如重芳族石脑油、煤油和其它石油级分,或植物油;和/或粘合剂如糊精、胶水或合成树脂。
粉尘剂是活性成分与细分固体的自由流动性混合物,所述细分固体是比如滑石、粘土、面粉和其它充当分散剂和载体的有机和无机固体。
微囊一般是包封在惰性多孔壳中的活性成分小滴或颗粒,所述惰性多孔壳使得所包封物质以受控速率释放至环境中。经包囊小滴的直径典型地为1至50微米。被包封的液体典型地构成胶囊重量的50至95%,并且除活性化合物以外还可以包含溶剂。包囊粒剂通常是具有密封颗粒孔口的多孔膜的多孔颗粒,活性成分以液体形式保留在颗粒孔中。颗粒的直径通常是1毫米到1厘米,优选1到2毫米。颗粒剂通过挤出、团聚或喷射造粒形成或是天然形成。这种材料的实例为蛭石、烧结粘土、高岭土、凹凸棒石粘土、锯屑和颗粒状碳。壳或膜材料包括天然或合成橡胶、纤维质材料、苯乙烯-丁二烯共聚物、聚丙烯腈、聚丙烯酸类、聚酯、聚酰胺、聚脲、聚氨酯和淀粉黄原酸酯。
用于农业化学应用的其它有用配制剂包括活性成分在其可以希望浓度完全溶解的溶剂中的简单溶液,所述溶剂是比如丙酮,烷基化萘,二甲苯和其它有机溶剂。还可以使用加压喷雾器,其中由于低沸点分散剂溶剂载体的汽化导致活性成分以细分形式分散。
用于将本发明组合物配制为上述配制剂类型的适宜农业助剂和载体是本领域技术人员所熟知的。
可以采用的液体载体包括,例如水,甲苯,二甲苯,石脑油,植物油,丙酮,甲乙酮,环己酮,乙酸酐,乙腈,苯乙酮,乙酸戊酯,2-丁酮,氯苯,环己烷,环己醇,乙酸烷基酯,二丙酮醇,1,2-二氯丙烷,二乙醇胺,对-二乙基苯,二乙二醇,二乙二醇松香酸酯,二乙二醇丁醚,二乙二醇乙醚,二乙二醇甲醚,N,N-二甲基甲酰胺,二甲亚砜,1,4-二噁烷,二丙二醇,二丙二醇甲醚,二丙二醇二苯甲酸酯,diproxitol,烷基吡咯烷酮,乙酸乙酯,2-乙基己醇,碳酸亚乙酯,1,1,1-三氯乙烷,2-庚酮,α蒎烯,d-柠檬烯,乙二醇,乙二醇丁醚,乙二醇甲醚,γ-丁内酯,甘油,甘油二乙酸酯,甘油单乙酸酯,甘油三乙酸酯,十六烷,己二醇,乙酸异戊酯,乙酸异冰片酯,异辛烷,异佛尔酮,异丙基苯,肉豆蔻酸异丙酯,乳酸,月桂胺,异亚丙基丙酮,甲氧基-丙醇,甲基异戊基酮,甲基异丁基酮,月桂酸甲酯,辛酸甲酯,油酸甲酯,二氯甲烷,间二甲苯,正己烷,正辛胺,十八烷酸,乙酸辛胺,油酸,油胺,邻二甲苯,苯酚,聚乙二醇(PEG400),丙酸,丙二醇,丙二醇单甲醚,对二甲苯,甲苯,磷酸三乙酯,三甘醇,二甲苯磺酸,石蜡,矿物油,三氯乙烯,全氯乙烯,乙酸乙酯,乙酸戊酯,乙酸丁酯,甲醇,乙醇,异丙醇,以及较高分子量的醇如戊醇、四氢糠醇、己醇、辛醇等,乙二醇,丙二醇,甘油和N-甲基-2-吡咯烷酮。水通常是用于稀释浓缩物的所选载体。
适宜的固体载体包括,例如滑石,二氧化钛,叶蜡石粘土,二氧化硅,凹凸棒石粘土,硅藻土(kieselguhr),白垩,硅藻土(diatomaxeousearth),石灰,碳酸钙,膨润土,漂白土,棉籽壳,小麦面粉,大豆面粉,浮石,木屑,胡桃壳粉和木质素。
在所述的液体和固体组合物中,特别是设计为在施用前用载体稀释的那些,有利地采用宽范围的表面活性剂。在使用时,这些试剂通常占配制剂重量的0.1%至15%。它们的特性可以是阴离子、阳离子、非离子或聚合物,并且可以用作乳化剂、润湿剂、助悬剂或者用于其他目的。典型的表面活性剂包括烷基硫酸酯盐,如月桂基硫酸酯二乙醇铵盐;烷基芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚-环氧烷烃加成产物,如壬酚-C.sub.18乙氧基化物;醇-环氧烷烃加成产物,如十三烷基醇-C.sub.16乙氧基化物;皂,如硬脂酸钠;烷基萘磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯盐,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季胺,如月桂基三甲基氯化铵;脂肪酸聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷与环氧丙烷嵌段共聚物;以及单烷基和二烷基磷酸酯盐。
通常用于农业组合物的其它助剂包括结晶抑制剂,粘度调节剂,助悬剂,喷雾滴调节剂,色素,抗氧化剂,起泡剂,消泡剂,遮光剂,增容剂,止泡剂,螯合剂,中和剂和缓冲剂,腐蚀抑制剂,染料,增香剂,展布剂,助渗剂,微量营养素,软化剂,润滑剂和粘着剂。
此外,其它杀生物活性成分或组合物可以与式(I)化合物相组合,并且用于本发明方法中,而且与式(I)化合物同时或按顺序施用。在同时施用的情况下,这些其它活性成分可以与式(I)化合物一起配制或者在例如喷雾槽中混合。这些其它杀生物活性成分可以是杀真菌剂,除草剂,杀昆虫剂,杀细菌剂,杀螨剂,杀线虫剂和/或植物生长调节剂。
因此,在一方面本发明提供组合物,其包含选自表1化合物143至153和表2化合物154至195的式(I)化合物,和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
额外地,本发明提供组合物在本发明方法中的用途,所述组合物包含选自表1化合物143至153和表2化合物154至195的式(I)化合物,和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
在又一方面中,本发明提供组合物,其包含式(I)化合物,所述化合物是式(R)-(I)的(R)-对映体,和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
额外地,本发明提供组合物在本发明方法中的用途,所述组合物包含式(I)化合物,所述化合物是式(R)-(I)的(R)-对映体,和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
在又一方面中,本发明提供组合物,其包含式(I)化合物,所述化合物是式(S)-(I)的(S)-对映体,和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
额外地,本发明提供组合物在本发明方法中的用途,所述组合物包含式(I)化合物,所述化合物是式(S)-(I)的(S)-对映体,和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
另外,本发明化合物还可以与一种或多种系统获得性抗性诱导剂(“SAR”诱导剂)一起施用。SAR诱导剂是已知的并描述于例如美国专利号US 6,919,298,其包括例如水杨酸类和商业SAR诱导剂活化酯。
尤其是,本发明涵盖的组合物包括,例如包含下述的组合物:式(I)化合物和活化酸(acibenzolar)(CGA245704),式(I)化合物和环丙嘧啶醇,式(I)化合物和棉铃威,式(I)化合物和aldimorph,式(I)化合物和吲唑磺菌胺(amisulbrom),式(I)化合物和敌菌灵,式(I)化合物和氧环唑,式(I)化合物和嘧菌酯,式(I)化合物和苯霜灵,式(I)化合物和苯噻菌胺(benthiavalicarb),式(I)化合物和苯菌灵,式(I)化合物和biloxazol,式(I)化合物和联苯三唑醇,式(I)化合物和联苯唑酰胺(bixafen),式(I)化合物和灭瘟素,式(I)化合物和啶酰菌胺,式(I)化合物和糠菌唑,式(I)化合物和乙嘧酚磺酸酯,式(I)化合物和敌菌丹,式(I)化合物和克菌丹,式(I)化合物和多菌灵,式(I)化合物和多菌灵盐酸盐,式(I)化合物和萎锈灵,式(I)化合物和环丙酰菌胺,式(I)化合物和香芹酮,式(I)化合物和CGA41396,式(I)化合物和CGA41397,式(I)化合物和灭螨猛,式(I)化合物和氯苯甲醚,式(I)化合物和百菌清,式(I)化合物和乙菌利(chlorozolinate),式(I)化合物和clozylacon,式(I)化合物和含铜化合物比如王铜、羟基喹啉酸铜、硫酸铜、妥尔铜和波尔多液,式(I)化合物和环氟苄酰胺,式(I)化合物和霜脲氰,式(I)化合物和环丙唑醇,式(I)化合物和嘧菌环胺,式(I)化合物和咪菌威,式(I)化合物和二-2-吡啶基二硫醚1,1’-二氧化物,式(I)化合物和苯氟磺胺,式(I)化合物和哒菌酮,式(I)化合物和菌核利,式(I)化合物和二氯萘醌,式(I)化合物和氯硝胺,式(I)化合物和双氯氰菌胺,式(I)化合物和乙霉威,式(I)化合物和苯醚甲环唑,式(I)化合物和野燕枯,式(I)化合物和氟嘧菌胺,式(I)化合物和O,O-二-异丙基-S-苄基硫代磷酸酯,式(I)化合物和dimefluazole,式(I)化合物和dimetconazole,式(I)化合物和烯酰吗啉,式(I)化合物和二甲嘧酚,式(I)化合物和二甲苯氧菌胺,式(I)化合物和烯唑醇,式(I)化合物和二硝基巴豆酸酯,式(I)化合物和二氰蒽醌,式(I)化合物和十二烷基二甲基氯化铵,式(I)化合物和十二环吗啉,式(I)化合物和多果定(dodine),式(I)化合物和多果定(doguadine),式(I)化合物和敌瘟磷,式(I)化合物和烯肟菌酯(enestrobin),式(I)化合物和氟环唑,式(I)化合物和噻唑菌胺,式(I)化合物和乙嘧酚,式(I)化合物和土菌灵,式(I)化合物和噁唑菌酮,式(I)化合物和咪唑菌酮(RPA407213),式(I)化合物和氯苯嘧啶醇,式(I)化合物和腈苯唑,式(I)化合物和甲呋酰胺,式(I)化合物和环酰菌胺(KBR2738),式(I)化合物和稻瘟酰胺,式(I)化合物和拌种咯,式(I)化合物和苯锈啶,式(I)化合物和丁苯吗啉,式(I)化合物和三苯基乙酸锡,式(I)化合物和三苯基氢氧化锡,式(I)化合物和福美铁,式(I)化合物和嘧菌腙,式(I)化合物和氟啶胺,式(I)化合物和氟吡菌胺,式(I)化合物和咯菌腈,式(I)化合物和氟嘧菌酯,式(I)化合物和氟酰菌胺,式(I)化合物和SYP-LI90(氟吗啉),式(I)化合物和氟吡菌酰胺,式(I)化合物和氟氯菌核利,式(I)化合物和氟喹唑,式(I)化合物和氟硅唑,式(I)化合物和磺菌胺,式(I)化合物和氟酰胺,式(I)化合物和粉唑醇,式(I)化合物和灭菌丹,式(I)化合物和三乙膦酸铝,式(I)化合物和麦穗宁,式(I)化合物和呋霜灵,式(I)化合物和呋吡菌胺,式(I)化合物和双胍辛,式(I)化合物和己唑醇,式(I)化合物和羟基异噁唑,式(I)化合物和噁霉灵(hymexazole),式(I)化合物和IKF-916(氰霜唑),式(I)化合物和抑霉唑,式(I)化合物和亚胺唑,式(I)化合物和双胍辛胺,式(I)化合物和双胍辛胺乙酸盐,式(I)化合物和种菌唑,式(I)化合物和异稻瘟净,式(I)化合物和异菌脲,式(I)化合物和缬霉威(SZX0722),式(I)化合物和丁基氨基甲酸异丙基酯(isopropanylbutyl carbamate),式(I)化合物和稻瘟灵,式(I)化合物和春雷霉素,式(I)化合物和醚菌酯,式(I)化合物和LY186054,式(I)化合物和LY211795,式(I)化合物和LY248908,式(I)化合物和代森锰,式(I)化合物和代森锰铜,式(I)化合物和代森锰锌,式(I)化合物和双炔酰菌胺,式(I)化合物和精甲霜灵,式(I)化合物和嘧菌胺,式(I)化合物和灭锈胺,式(I)化合物和甲霜灵,式(I)化合物和叶菌唑,式(I)化合物和磺菌威,式(I)化合物和代森联,式(I)化合物和代森联-锌,式(I)化合物和苯氧菌胺,式(I)化合物和苯菌酮(metrafenone),式(I)化合物和腈菌唑,式(I)化合物和甲菌利,式(I)化合物和甲胂酸铁铵(neoasozin),式(I)化合物和二甲基二硫代氨基甲酸镍,式(I)化合物和酞菌酯,式(I)化合物和氟苯嘧啶醇,式(I)化合物和呋酰胺,式(I)化合物和有机汞化合物,式(I)化合物和肟醚菌胺,式(I)化合物和噁霜灵,式(I)化合物和环氧嘧磺隆,式(I)化合物和喹啉铜,式(I)化合物和喹菌酮,式(I)化合物和噁咪唑(oxpoconazole),式(I)化合物和氧化萎锈灵,式(I)化合物和稻瘟酯,式(I)化合物和戊菌唑,式(I)化合物和戊菌隆,式(I)化合物和吡噻菌胺(penthiopyrad),式(I)化合物和叶枯净(phenazin oxide),式(I)化合物和氯瘟磷,式(I)化合物和含磷的酸类(phosphorus acids),式(I)化合物和四氯苯酞,式(I)化合物和啶氧菌酯(ZA1963),式(I)化合物和多抗霉素D,式(I)化合物和代森联(polyram),式(I)化合物和烯丙苯噻唑,式(I)化合物和咪鲜胺,式(I)化合物和腐霉利,式(I)化合物和霜霉威,式(I)化合物和丙环唑,式(I)化合物和丙森锌,式(I)化合物和丙酸,式(I)化合物和丙氧喹啉,式(I)化合物和丙硫菌唑,式(I)化合物和吡唑醚菌酯,式(I)化合物和吡菌磷,式(I)化合物和吡菌苯威(pyribencarb),式(I)化合物和啶斑肟,式(I)化合物和嘧霉胺,式(I)化合物和咯喹酮,式(I)化合物和氯吡呋醚,式(I)化合物和硝吡咯菌素,式(I)化合物和季铵化合物,式(I)化合物和喹甲硫酯(quinomethionate),式(I)化合物和苯氧喹啉(quinoxyfen),式(I)化合物和五氯硝基苯,式(I)化合物和硅噻菌胺,式(I)化合物和硅氟唑,式(I)化合物和sipconazole(F-155),式(I)化合物和五氯酚钠,式(I)化合物和螺环菌胺,式(I)化合物和链霉素,式(I)化合物和硫,式(I)化合物和戊唑醇,式(I)化合物和叶枯酞,式(I)化合物和四氯硝基苯,式(I)化合物和四氟醚唑,式(I)化合物和噻菌灵,式(I)化合物和噻呋酰胺,式(I)化合物和2-(氰硫基甲硫基)苯并噻唑,式(I)化合物和甲基硫菌灵,式(I)化合物和福美双,式(I)化合物和噻唑菌酰胺,式(I)化合物和timibenconazole,式(I)化合物和甲基立枯磷,式(I)化合物和甲苯氟磺胺,式(I)化合物和三唑酮,式(I)化合物和三唑醇,式(I)化合物和叶锈特,式(I)化合物和咪唑嗪,式(I)化合物和三环唑,式(I)化合物和十三吗啉,式(I)化合物和肟菌酯(CGA279202),式(I)化合物和嗪氨灵,式(I)化合物和氟菌唑,式(I)化合物和灭菌唑,式(I)化合物和有效霉素A,式(I)化合物和vapam,式(I)化合物和缬氨菌酯(valiphenal)式(I)化合物和乙烯菌核利,式(I)化合物和代森锌,式(I)化合物和福美锌,式(I)化合物和苯酰菌胺,式(I)化合物和3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶,式(I)化合物和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]嘧啶和式(I)化合物和N-(4-氯-2-硝基苯基)-N-乙基-4-甲基-苯磺酰胺。
式(I)化合物可以用下述方法制备。
式(I)化合物,其中R4=H可以这样制备:将亚氨代甲基氯(II)与炔类醇(III)进行[3+2]-环加成:
所述反应可以在惰性溶剂比如DCE(1,2-二氯乙烷)中的有机碱比如三乙胺存在下,或者在质子溶剂比如异丙醇中的无机碱比如碳酸氢钠存在下进行。反应的时间和温度不是关键,但可以是20至60℃的温度,持续1至24小时。
亚氨代甲基氯(II)可以用氯化试剂比如N-氯代琥珀酰亚胺或次氯酸钠(漂白)制备自相应肟,或者可以得自商业来源。
炔类醇(III)可以通过将有机金属炔(IV)(M=Li,MgX;X=Cl,Br)加至醛R2CHO(V)来获得,如下所示:
在某些情况中,在使用炔类醇(III)的相应酮(VI)的情况下,所述[3+2]-环加成进行得更快,收率更高:
用于制备式(I)化合物的式(VII)化合物描述如下,其中将异噁唑(VII)还原(例如用硼氢化钠),提供(I)。
在某些情况下,在[3+2]-环加成中区域异构体(VIII)与(I)一起产生。在生物学评价中,该区域异构体(VIII)一般比(I)活性更低。
炔类酮(VI)能够通过氧化制备自(III):例如以任意适宜的时间和温度(例如20℃,1至2小时)使用惰性溶剂比如DMSO(二甲亚砜)中的IBX(邻-亚碘酰苯甲酸)进行氧化。于0℃,在醇类溶剂(例如乙醇)中用硼氢化钠将异噁唑(VII)还原0.3至2小时,产生异噁唑(I)(R4=H)。
异噁唑,其中R4≠H,可以用标准酰化或氨基甲酰基化条件制备自(I)(R4=H)。例如,(I)的乙酸酯衍生物(R4=COCH3)这样合成自醇(I)(R=H):在室温下于醚溶剂中与乙酸酐和吡啶反应过夜。酰化可以在惰性溶剂(例如乙醚,二氯甲烷)中的有机碱存在下用酸酐(例如乙酸酐、丙酸酐)或酰氯(例如苯甲酰氯)来进行。氨基甲酰基化这样进行:用强碱比如氢化钠处理醇(I),随后用惰性溶剂比如DMF(二甲基甲酰胺)中的氨基甲酰氯(例如N,N-二甲基氨基甲酰氯)进行处理。
用于制备或分离单独对映体的常规技术包括自适宜的光学纯前体进行手性合成或者用例如手性高效液相色谱(HPLC)拆分外消旋体(或盐或衍生物的外消旋体)。另选地,外消旋体(或外消旋前体)可以与适宜的光学活性化合物例如羧酸反应,或者,在式(I)化合物含有酸性或碱性部分的情况下,与碱或酸比如1-苯基乙胺或酒石酸反应。所得非对映异构混合物可以通过色谱法和/或分步结晶得以分离,而所述非对映异构体之一或两者可以通过技术人员所熟知的手段转化为相应纯对映体。本领域技术人员已知的常规技术公开于例如E.L.Eliel和S.H.Wilen(Wiley,New York,1994)的Stereochemistry of Organic Compounds。
通过下述实施例来说明本发明。
实施例1:3-(2,6-二氯苯基)-4-[(3-吡啶基)-羟基甲基]-5-三甲基甲硅烷基-异噁唑(表1,化合物1)和
3-(2,6-二氯苯基)-5-[(3-吡啶基)-羟基甲基]-4-三甲基甲硅烷基异噁唑(表1,化合物2)
于55℃,将55mg(0.24mmol)的2,6-二氯-N-羟基苯亚氨代甲基氯,50mg(0.24mmol)的1-(3-吡啶基)-3-三甲基甲硅烷基-2-丙炔-1-醇,和20mg(0.24mmol)的碳酸氢钠在2mL异丙醇中的混合物加热24小时。反应混合物用乙醚稀释。醚层用饱和氯化钠溶液洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙醚。粗制产品通过制备型薄层色谱法(prep TLC)纯化,两种产品得以分离。
极性较低的产品(10mg,0.025mmol)确认为3-(2,6-二氯苯基)-4-[(3-吡啶基)羟基-甲基]-5-三甲基甲硅烷基异噁唑。1H NMR(CDCl3):δ0.45(br s,9),5.82(s,1),和7.40ppm(d,1)。MS m/z:393.0(M+H)。
极性较高的产品是3-(2,6-二氯苯基)-5-[(3-吡啶基)羟基甲基]-4-三甲基甲硅烷基异噁唑。1H NMR(CDCl3):δ0.20(m,9),6.12(s,1),7.80(d,1),和7.87ppm(d,1)。MS m/z:393.0(M+H)。
实施例2:5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(表1,化合物4)
于55℃,在配有加热沙浴的台式旋转摇床上加热53mg(0.24mmol)的2,4-二氯-N-羟基苯亚氨代甲基氯,50mg(0.21mmol)的1-(3-吡啶基)-3-(3-氯苯基)-2-丙炔-1-醇,和26mg(0.31mmol)的碳酸氢钠在2.5mL异丙醇中的混合物。在20小时之后,加入额外的20mg的2,4-二氯-N-羟基苯亚氨代甲基氯和10mg碳酸氢钠,搅拌反应混合物,再加热16小时。然后,用乙醚稀释混合物,溶液用饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙醚。粗制产品通过制备型TLC纯化,提供15mg(0.035mmol)的5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟基甲基]异噁唑。
1H NMR(CDCl3):δ5.92(br s,1),7.04(d ofd,1),7.12(d,1),7.72(m,1),8.86(br s,1),和8.29ppm(br s,2)。MS m/z:430.9(M+H)。
实施例3:5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)-乙酰氧基甲基]异噁唑
向43mg(0.10mmol)的5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟基甲基]异噁唑的2mL吡啶溶液加入19μL(0.20mmol)的乙酸酐。在室温下搅拌反应过夜,然后在真空下除去吡啶。将残余物分散于乙酸乙酯中,用饱和氯化钠洗涤,乙酸乙酯级分在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙酸乙酯。粗制产品通过制备型薄层色谱法(prep TLC)纯化,提供35mg(0.074mmol)的5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)乙酰氧基甲基]-异噁唑。
实施例4:3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羰基]异噁唑
向200mg(1.06mmol)的4,4-二甲基-1-吡啶基-2-戊炔-1-醇的2.5mL二甲亚砜(DMSO)溶液加入443mg(1.58mmol)的邻-亚碘酰苯甲酸(IBX)。在室温下搅拌反应混合物过夜,然后过滤除去固体。滤液用乙醚稀释,用饱和氯化钠溶液洗涤。分离有机级分,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙醚。直接使用酮式产品,4,4-二甲基-1-(3-吡啶基)-2-戊炔-1-酮(182mg),不加任意纯化。
于55℃,在台式旋转摇床上将72mg(0.32mmol)的2,4-二氯-N-羟基苯亚氨代甲基氯,60mg(0.32mmol)的4,4-二甲基-1-(3-吡啶基)-2-戊炔-1-酮,和32mg(0.38mmol,1.2当量)的碳酸氢钠在2.5mL异丙醇中的混合物加热16小时。第二次加入25mg亚氨代甲基氯和10mg碳酸氢钠,随后于55℃再加热20小时。冷却反应混合物,用乙醚稀释,然后用饱和碳酸氢钠洗涤。乙醚级分在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙醚。粗制产品通过制备型TLC纯化,提供92mg的油状产品,3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羰基]-异噁唑。1H NMR(CDCl3):δ1.47(s,9),7.90(m,1),7.60(br s,1)和8.72ppm(br s,1)。MS m/z:375.0(M+H)。
实施例5:3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羟基甲基]-异噁唑(表1,化合物7)
于0℃,向92mg(0.24mmol)的3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羰基]异噁唑的5mL乙醇溶液加入20mg(0.53mmol)的硼氢化钠。在2小时之后,将反应混合物倾至水中,产品用乙酸乙酯萃取数次。经合并的乙酸乙酯级分用饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙酸乙酯。粗制产品通过制备型TLC纯化,产生68mg(0.18mmol)3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羟基-甲基]异噁唑。1H NMR(CDCl3):δ1.52(s,9),6.14(br s,1),6.86(d,1),7.38(m,1),8.27(br s,1)和8.33ppm(m,1)。MS m/z:377.0(M+H)。
实施例6:5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(表1,化合物14)
在氮气氛下,向冷却至-78℃的655mg(4.8mmol)的2-氯苯基乙炔的10mL四氢呋喃(THF)溶液加入3.0mL(4.8mmol)的1.6M正丁基锂己烷溶液。在-78℃搅拌溶液2小时,然后加入514mg(4.8mmol)的3-吡啶甲醛的2.5mL四氢呋喃(THF)溶液。在3.5小时之后,将反应混合物倾至水中。有机产品用乙醚萃取数次。经合并的乙醚萃取物用饱和碳酸氢钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙醚,提供油状的3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-醇。
于55℃,在振摇下将52mg(0.23mmol)的2,4-二氯-N-羟基苯亚氨代甲基氯,50mg(0.21mmol)的3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-醇,和30mg(0.36mmol)的碳酸氢钠在3mL异丙醇中的混合物加热过夜。冷却反应混合物,用乙醚稀释,然后用饱和碳酸氢钠洗涤。乙醚级分在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙醚。粗制产品通过制备型TLC纯化,提供15mg(0.035mmol)的5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟基甲基]异噁唑。1H NMR(CDCl3):δ5.80(br s,1)。MS m/z:431.0(M+H)。
实施例7:5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑(表1,化合物14)
于55℃,在振摇下将56mg(0.25mmol)的2,4-二氯-N-羟基苯亚氨代甲基氯,60mg(0.25mmol)的3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-酮,和30mg(0.36mmol)的碳酸氢钠在2.5mL异丙醇中的混合物加热过夜。然后加入额外的30mg亚氨代甲基氯和15mg碳酸氢钠,将混合物再加热20小时。冷却反应混合物,用乙醚稀释,然后用饱和碳酸氢钠洗涤。乙醚级分在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙醚。粗制产品通过制备型TLC纯化,提供90mg(0.21mmol)的5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羰基]异噁唑。
1H NMR(CDCl3):δ7.16(m,1),7.60(m,2),7.92(m,1),8.53(brd,1),和8.74ppm(br s,1)。MS m/z:428.9(M+H)。
于0℃,向80mg(0.19mmol)的5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羰基]异噁唑的3mL乙醇溶液加入40mg(1.06mmol)的硼氢化钠。搅拌混合物2小时,然后用乙酸乙酯稀释。乙酸乙酯溶液用饱和氯化钠溶液洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙酸乙酯。粗制产品通过制备型TLC纯化,提供65mg(0.15mmol)的5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑。
1H NMR(CDCl3):δ5.80(br s,1),6.97(m,1),8.23(br s,1),和8.28ppm(br s,1)。
MS m/z:431.0(M+H)。
实施例8:5-(2-氯苯基)-3-(2,4-二氯苄基)-4-[(3-吡啶基)羟基甲基]-异噁唑(表1,化合物15)
于55℃,在密封小瓶中将59mg(0.25mmol)的2,4-二氯苄基亚氨代甲基氯(根据G.Kumaran和G.H.Kulkarni,J.Org.Chem.1997,62,1516制备),50mg(0.21mmol)的3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-酮,和43μL(0.31mmol)的三乙胺的mL二氯甲烷溶液加热过夜。冷却反应混合物,用乙醚稀释,用饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去溶剂。粗制产品通过制备型TLC纯化,提供50mg(0.11mmol)5-(2-氯苯基)-3-(2,4-二氯苄基)-4-[(3-吡啶基)羰基]异噁唑。
1H NMR(CDCl3):δ4.23(s,2),7.48(d,1),7.88(d of d,1),8.66(br d,1),8.70ppm(br s,1)。MS m/z:442.9(M+H)。
在室温下,向50mg(0.11mmol)的5-(2-氯苯基)-3-(2,4-二氯苄基)-4-[(3-吡啶基)羰基]异噁唑的15mL THF溶液加入21mg(0.56mmol)的硼氢化钠。在2小时之后,溶液用乙酸乙酯稀释,用饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去溶剂。粗制产品通过制备型TLC纯化,提供39mg(0.088mmol)的5-(2-氯苯基)-3-(2,4-二氯苄基)-4-[(3-吡啶基)羟基甲基]异噁唑。1H NMR(CDCl3):δ3.91(d,1),4.00(d,1),6.97(br s,1),7.64(d,1),8.42ppm(br m,2)。MS m/z:445.0(M+H)。
实施例9:5-(3-氯苯基)-3-(2-氟-5-三氟甲基苯基)-4-[(3-吡啶基)-羟基-甲基]异噁唑(表1,化合物29)
向643mg(3.10mmol)的2-氟-5-三氟甲基苯甲醛肟的5mL二甲基甲酰胺(DMF)溶液加入456mg(3.41mmol)的N-氯代琥珀酰亚胺(参见K.-C.Liu,B.R.Shelton,和R.K.Howe,J.Org.Chem.1980,45,3916)。在室温下搅拌反应混合物过夜,然后用乙酸乙酯稀释。乙酸乙酯溶液用饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去溶剂,提供675mg(2.79mmol)的纯的白色晶状2-氟-5-三氟甲基-N-羟基苯-亚氨代甲基氯。
于55℃,在振摇下将60mg(0.25mmol)的2-氟-5-三氟甲基-N-羟基苯亚氨代甲基氯,50mg(0.21mmol)的3-(3-氯苯基)1-(3-吡啶基)-2-丙炔-1-酮(类似上述程序地制备自3-氯苯基炔化锂和3-吡啶甲醛,随后进行IBX氧化),和26mg(0.36mmol)的碳酸氢钠在2.5mL异丙醇中的混合物加热过夜。加入额外的30mg亚氨代甲基氯和15mg碳酸氢钠,将反应再加热24小时。冷却混合物,用乙醚稀释。乙醚级分用饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去溶剂。残余物通过制备型TLC纯化,提供56mg(0.13mmol)的5-(3-氯苯基)-3-(2-氟-5-三氟甲基苯基)-4-[(3-吡啶基)羰基]异噁唑。1H NMR(CDCl3):δ7.10(t,1),7.41(m,1),7.52(m,1),8.65(br s,1),和8.86ppm(br s,1)。MS m/z:447.0(M+H)。
向56mg(0.13mmol)的5-(3-氯苯基)-3-(2-氟-5-三氟甲基-苯基)-4-[(3-吡啶基)羰基]异噁唑的2mL乙醇溶液加入24mg(0.63mmol)的硼氢化钠。在室温下经过2小时之后,反应混合物用乙酸乙酯稀释。溶液用饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去溶剂。残余物通过制备型TLC纯化,提供44mg(0.098mmol)的5-(3-氯苯基)-3-(2-氟-5-三氟甲基苯基)-4-[(3-吡啶基)羟基甲基]异噁唑。
1H NMR(CDCl3):δ6.01(s,1),7.01(m,1),7.83(m,1),8.27(m,1),和8.35ppm(br s,1)。MS m/z:449.0(M+H)。
实施例10:[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇(表1,化合物146)
(i)制备3-(2,4-二氟苯基)-1-吡啶-3-基-丙炔酮(3)
将1-乙炔基-2,4-二氟苯(24g,0.17mol)溶于THF(350ml),在-78℃冷却反应混合物。在70分钟内滴加2.5M的n-BuLi己烷溶液(76.5ml,0.19mol),保持温度在-70℃以下。在加入完成之后,在该温度将混合物再搅拌10分钟。在20分钟内,将Weinreb酰胺2(根据WO 05/097760,Letters in Organic Chemistry,4,20,2007制备)(28.9g,0.17mol)的THF(100ml)溶液滴加至上述溶液,保持温度在-70℃以下。然后,将混合物温热至-50℃,获得溶液,将其在该温度再搅拌1小时。反应混合物用饱和氯化铵溶液(100ml)淬灭,让其温热至室温。然后,将反应倾至乙酸乙酯/水混合物中。随后,水相用乙酸乙酯洗涤两次。经合并的有机层用盐水洗涤,在硫酸钠上干燥,过滤,浓缩。自乙醚重结晶粗制品,获得28g的希望产品。浓缩母液,残余物通过柱色谱法在氧化铝上纯化,用环己烷/乙酸乙酯3∶1混合物洗脱。共获得,29.8g(70%)的褐色化合物。
1H NMR(CDCl3):δ7.02(m,1),7.58(m,1),7.71(m,1),8.56(m,1)8.90(m,1)和9.48ppm(m,1)。MS m/z:244.0(M+H)。
(ii)制备[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲酮(5)
于85℃,将46.7g(0.22mol)的2-氟-4-氯-N-羟基苯亚氨代甲基氯(通过类似于实施例9制备2-氟-5-三氟甲基-N-羟基苯-亚氨代甲基氯的方法来制备),42g(0.17mol)的3-(2,4-二氟苯基)-1-吡啶-3-基-丙炔酮(3),和21.76g(0.26mol)的碳酸氢钠在500mL异丙醇中的混合物加热21小时。反应混合物用乙酸乙酯稀释,依次用饱和氯化铵、水和饱和氯化钠溶液洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙酸乙酯。自乙醚重结晶粗制品,获得所希望的产品,是淡黄色固体(50.28g,70.2%)。1H NMR(CDCl3):δ6.75(m,1),7.05(m,2),7.27(m,2),7.67(t,1),7.80(m,1),8.03(m,1),8.66(m,1)和8.82ppm(d,1)。MS m/z:415(M+H)。
(iii)制备[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇(6)
于0℃,向5(26.5g,63.9mmol)的THF/甲醇(400ml/40ml)混合物溶液加入2.42g(63.7mmol)的硼氢化钠。搅拌混合物1.5小时,然后用乙酸乙酯稀释。乙酸乙酯溶液用饱和氯化钠溶液洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙酸乙酯。反应混合物通过柱色谱法用庚烷/乙酸乙酯1∶1混合物纯化。获得所希望的化合物,是白色晶体(17.5g,66%)。mp=138-140℃。
1H NMR(CDCl3):δ4.19(bs,1),5.89(s,1),6.99(m,5),7.28(t,1),7.43(d,1),7.59(q,1),和8.19(d,1)和8.23ppm(d,1)。MS m/z:417(M+H)。
实施例11:(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇(表1,化合物153:(R)-146))
用外消旋混合物6作原料,通过制备型色谱法分离各对映体。
制备方法:
流动相:正庚烷/乙醇70/30(v/v)
流速:270ml/分
检测:UV 280nm
温度:25℃
分析方法:
流动相:正庚烷/乙醇/二乙胺70/30/0.1(v/v/v)
流速:1ml/分
检测:UV 230nm
温度:25℃
第一洗脱对映体具有的保留时间为7.6分钟([α]=+58.07,C=0.025M,THF),而第二对映体具有的保留时间为9.9分钟([α]=-57.59,C=0.025M,THF)。第一洗脱对映体是(R)-对映体。第二洗脱对映体是(S)-对映体。发现(R)-对映体具有主要的PGR活性。
表1的式(I)化合物可以通过类似方法制备。
表1
表2
实施例B1:对禾谷类的植物生长效果的生物学评价
在播种三周之后,在拔节开始时喷雾冬小麦和夏小麦植株。在叶片上方用喷管式喷雾器以各自225g a.i.(活性成分)/ha将经配制的试验化合物144、145和146喷雾于植物上。喷雾之后,将植物转移至温室,在喷雾28天之后相对未处理对照对植物生长减少进行视觉评价。结果概括于表2中。
表2:用225g活性成分/公顷的3种不同试验化合物喷雾夏小麦和冬小麦之后的百分比植物生长减少
实施例B2:对葡萄的植物生长调节效果的生物学评价
在喷雾室中,将5周龄葡萄幼苗栽培种(cv.)Gutedel用配制的试验化合物处理。于22℃和80%相对湿度(r.h.),在温室中温育8天的时间段,随后评价植物生长调节效果。
化合物144,145,147,148,149,150,151,152和153于200ppm显示植株高度降低
实施例B3:对小麦的植物生长调节效果的生物学评价
在喷雾室中,将2周龄小麦植物栽培种(cv.)Riband用配制的试验化合物处理。于22℃和80%相对湿度(r.h.),在温室中温育8天的时间段,随后评价植物生长调节效果。
化合物144于200ppm显示植株高度降低。
杀真菌化合物
已令人惊讶地发现衍生自化合物146的式(II)异噁唑化合物展示出乎意料的杀真菌活性,因此其适于用于农业中作为作物保护剂以抗击或预防真菌侵袭或者防治其它病虫害,比如对作物有害的杂草、昆虫或螨类。
相应地,在额外的方面中,本发明提供式(II)化合物
其中R4是H或酰基,优选H;
或其农业化学上可接受的盐。
在一种优选实施方式中,本发明提供化合物式(S)-(II)
其中R4是H或酰基;
或其农业化学上可接受的盐。
最优选,本发明提供化合物(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇(化合物(S)-(146))。
优选,作为单个对映体提供式(S)-(II)化合物,优选(S)-(146),其具有的对映体过量(e.e.)为至少40%,例如至少50%、60%、70%或80%,优选至少90%,更优选至少95%,还更优选至少98%和最优选至少99%。
相应地,提供组合物,其包含式(S)-(II)化合物,优选(S)-(146),和农业上可接受的稀释剂或载体。式(S)-(II)化合物,优选(S)-(146),及其组合物适于防治和预防植物病原性微生物,特别是真菌有机体,包括国际专利申请WO 2006/031631中公开的那些。
特别地,本发明提供防治或预防病原微生物侵染栽培植物的方法,其包括将式(S)-(II)化合物,优选(S)-(146),以有效防治所述微生物的量施用至所述植物、其部分或其处所。优选,上述有机体是真菌有机体,更优选,所述真菌有机体选自小麦壳针孢(Septoria tritici),颖枯壳多孢(Stagonospora nodorum),致病疫霉(Phytophthora infestans),灰葡萄孢(Botrytis cinerea),同果核盘菌(Sclerotinia homoeocarpa)和隐匿柄锈菌(Puccinia recondita)。
本发明也涵盖如本文和国际专利申请WO 2006/031631中描述的组合物、组合和植物。
生物学实施例:下述实施例中展示化合物(S)-(146)的上述杀真菌特性。
灰葡萄孢(Botrytis cinerea)(灰霉病):将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法测定生长抑制。化合物(S)-(146)于200ppm提供至少80%的灰葡萄孢防治。
落花生球腔菌(Mycosphaerella arachidis)(同义词:落花生尾孢(Cercospora arachidicola)),落花生(花生)褐斑病:将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法于620nm测定生长抑制。化合物(S)-(146)于200ppm提供至少80%的落花生球腔菌防治。
小麦壳针孢(Septoria tritici)(叶枯病):将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法测定生长抑制。化合物(S)-(146)于200ppm提供至少80%的小麦壳针孢防治。
雪腐明梭孢(Monographella nivalis)(同义词:雪腐微托菌(Microdochium nivale),雪腐镰孢(Fusarium nivale)),禾谷类的雪腐病、根腐病:将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法于620nm测定生长抑制。化合物(S)-(146)于200ppm提供至少80%的雪腐明梭孢防治。
大刀镰孢(Fusarium culmorum)(根腐病):将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,48小时之后通过光度法测定生长抑制。化合物(S)-(146)于200ppm提供至少80%的大刀镰孢防治。
立枯丝核菌(Rhizoctonia solani)(根腐病,猝倒病):将制备自新鲜液体培养物的上述真菌的菌丝体碎片直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌菌丝体的营养肉汤。在24℃温育试验板,48小时之后通过光度法测定生长抑制。化合物(S)-(146)于200ppm提供至少80%的立枯丝核菌防治。
Claims (25)
1.式(I)化合物或其盐作为植物生长调节剂的用途
其中
R1是任选用羟基,苯基或卤代苯基取代的烷基;烷氧基烷基;卤代烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,苯氧基,烷氧基炔基,氰基,或硝基取代的芳基;或者任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;
R2是烷基;烷氧基烷基;卤代烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基;或者任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;
R3是H;烷基;烷氧基;烷氧基烷基;卤代烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳氧基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的芳硫基烷基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,烷氧基炔基,氰基,硝基取代的芳基;任选用卤素,烷基,烯基,炔基,卤代烷基,烷氧基,烷硫基,卤代烷氧基,氰基,或硝基取代的杂芳基;或烷基甲硅烷基;
并且
R4是H或酰基。
2.根据权利要求1的用途,其中R1是任选用卤素,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C6-卤代烷氧基,苯氧基,甲氧基炔丙基,氰基,或硝基取代的苯基;或者呋喃基,噻吩基,吡啶基,或苯并噻吩基,各自任选用卤素取代。
3.根据权利要求2的用途,其中R1是2-氯苯基,4-氯苯基,2,4-二氯苯基,2-氟苯基,2,4-二氟苯基,3,5-二氟苯基,4-三氟-甲基苯基,4-三氟甲氧基苯基或2-噻吩基。
4.根据权利要求1的用途,其中R1是C1-C6-烷基;或者任选用卤素或C1-C6-烷基取代的苯基-C1-C6-烷基。
5.根据权利要求4的用途,其中R1是正戊基,叔丁基,苄基,或4-氯苄基。
6.根据权利要求1至5中任一项的用途,其中R2是吡啶基,嘧啶基或异喹啉基,各自任选用卤素,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C6-卤代烷氧基,氰基,或硝基取代。
7.根据权利要求6的用途,其中R2是2-吡啶基,3-吡啶基,或5-嘧啶基,各自任选用甲基,氯,氟,甲氧基,硫代甲氧基或三氟甲基取代。
8.根据权利要求1至7中任一项的用途,其中R3是C1-C6-烷基;C1-C6-烷氧基;任选用卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-烷硫基,甲氧基炔丙基,氰基或硝基取代的苯基;呋喃基,噻吩基或吡啶基,各自任选用卤素,C1-C6-烷基或C1-C6-烷氧基取代;或者C1-C6-烷基甲硅烷基。
9.根据权利要求8的用途,其中R3是苯基,3-氯苯基,4-氯苯基,4-氟苯基,3,5-二氟苯基,4-甲基苯基,2-噻吩基,5-氯-2-噻吩基,5-甲基-2-噻吩基,3-噻吩基,叔丁基,或三甲基甲硅烷基。
10.根据权利要求1至9中任一项的用途,其中R4是H。
11.根据权利要求1的用途,其中式(I)化合物选自:
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑;
3-(2,4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(2-氟-4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(2-甲氧基吡啶)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(2,4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(2,4-二氟苯基)-5-(2-氯-4-氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑;和
(R)-3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑;
及其盐。
12.化合物及其盐,所述化合物是如权利要求1至10中任一项中所定义的式(I)化合物的(R)-对映体。
13.化合物及其盐,所述化合物是如权利要求1至10中任一项中所定义的式(I)化合物的(S)-对映体。
14.式(I)化合物,选自:
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑;
3-(2,4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(2-氟-4-氯苯基)-5-(2-氯苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(2-甲氧基吡啶)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(4-氯苯基)-5-(2,4-氟苯基)-4-[(3-嘧啶基)羟基甲基]-异噁唑;
3-(2,4-二氟苯基)-5-(2-氯-4-氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑;和
(R)-3-(2-氟-4-氯苯基)-5-(2,4-二氟苯基)-4-[(3-吡啶基)羟基甲基]-异噁唑;
及其盐。
15.根据权利要求1的用途,其中式(I)化合物如权利要求12至14中任一项中所定义。
16.调节有用植物作物的植物生长的方法,其包括向所述植物、向所述植物的一个或多个部分或者向其处所或植物繁殖材料,施用如权利要求1至14中任一项中所定义的式(I)化合物。
17.根据权利要求16的方法,其包括一次或多次施用单独的或者与一种或多种常规植物保护配制辅剂结合的一种或多种式(I)化合物。
18.根据权利要求17的方法,其中两次或更多次施用依次进行,并且其中所述两次或更多次施用具有浓度相同或不同的、或组合相同或不同的、或者两者都相同或不同的式(I)化合物。
19.根据权利要求16至18中任一项的方法,其中所述有用栽培作物选自禾谷类,稻,甜菜,豆科植物,油料植物,黄瓜植物,纤维植物,蔬菜,种植园作物,观赏植物,藤本植物,灌木类浆果,蔓藤类浆果,酸果蔓,胡椒薄荷,大黄,留兰香,甘蔗和草皮草。
20.根据权利要求16至19中任一项的方法,其中所述植物生长调节效果是抑制或阻滞植物生长。
21.农业组合物,包含一种或多种如权利要求1至14中任一项中所定义的式(I)化合物,和一种或多种常规植物保护辅剂。
24.一种组合物,其包含根据权利要求22或权利要求23的化合物或其农业化学上可接受的盐,以及农业化学上可接受的稀释剂或载体。
25.根据权利要求22或权利要求23的化合物或者根据权利要求24的组合物作为杀真菌剂的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0823002.1A GB0823002D0 (en) | 2008-12-17 | 2008-12-17 | Isoxazoles derivatives with plant growth regulating properties |
GB0823002.1 | 2008-12-17 | ||
PCT/EP2009/066965 WO2010069881A2 (en) | 2008-12-17 | 2009-12-11 | Isoxazole derivatives for use as plant growth regulators |
Publications (1)
Publication Number | Publication Date |
---|---|
CN102256490A true CN102256490A (zh) | 2011-11-23 |
Family
ID=40343739
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009801507449A Pending CN102256491A (zh) | 2008-12-17 | 2009-12-11 | 用作杀真菌剂的异噁唑衍生物 |
CN2009801504563A Pending CN102256490A (zh) | 2008-12-17 | 2009-12-11 | 用作植物生长调节剂的异噁唑衍生物 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009801507449A Pending CN102256491A (zh) | 2008-12-17 | 2009-12-11 | 用作杀真菌剂的异噁唑衍生物 |
Country Status (23)
Country | Link |
---|---|
US (4) | US20110251066A1 (zh) |
EP (2) | EP2365751A1 (zh) |
JP (2) | JP2012512227A (zh) |
KR (2) | KR20110102463A (zh) |
CN (2) | CN102256491A (zh) |
AR (2) | AR074696A1 (zh) |
AU (2) | AU2009328243A1 (zh) |
BR (2) | BRPI0922262A2 (zh) |
CA (2) | CA2746963A1 (zh) |
CL (2) | CL2011001443A1 (zh) |
CO (2) | CO6382087A2 (zh) |
CR (2) | CR20110328A (zh) |
EA (2) | EA201100948A1 (zh) |
GB (1) | GB0823002D0 (zh) |
GE (1) | GEP20135948B (zh) |
IL (2) | IL213069A0 (zh) |
MA (2) | MA32906B1 (zh) |
MX (2) | MX2011006085A (zh) |
NI (2) | NI201100123A (zh) |
NZ (1) | NZ592997A (zh) |
TW (2) | TW201024288A (zh) |
WO (2) | WO2010069881A2 (zh) |
ZA (2) | ZA201103887B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105051196A (zh) * | 2013-03-14 | 2015-11-11 | 加利福尼亚大学董事会 | 正交配体激活的修饰的pyr/pyl受体 |
Families Citing this family (274)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0823002D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isoxazoles derivatives with plant growth regulating properties |
WO2012056003A1 (en) | 2010-10-28 | 2012-05-03 | Syngenta Participations Ag | Novel microbicides |
CA2815742A1 (en) | 2010-11-12 | 2012-05-18 | Syngenta Participations Ag | Novel microbiocides |
WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
WO2012143395A1 (en) * | 2011-04-20 | 2012-10-26 | Syngenta Participations Ag | 4,5-dihydro-isoxazole derivatives as fungicides |
WO2013007550A1 (en) | 2011-07-08 | 2013-01-17 | Syngenta Participations Ag | Fungicide mixtures |
WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
US9464056B2 (en) | 2012-06-22 | 2016-10-11 | E I Du Pont De Nemours And Company | Fungicidal 4-methylanilino pyrazoles |
US20150257383A1 (en) | 2012-10-12 | 2015-09-17 | Basf Se | Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
CN104955813A (zh) | 2012-11-27 | 2015-09-30 | 巴斯夫欧洲公司 | 取代的[1,2,4]三唑化合物 |
WO2014082881A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
WO2014082871A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
WO2014082879A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4]triazole compounds |
WO2014086856A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a biopesticide |
WO2014086854A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a plant growth regulator |
WO2014086850A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a fungicidal inhibitor of respiratory complex ii |
EP2746263A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Alpha-substituted triazoles and imidazoles |
EP2746256A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
EP2746277A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
CN105164111B (zh) | 2012-12-19 | 2018-11-20 | 巴斯夫欧洲公司 | 取代[1,2,4]三唑及其作为杀真菌剂的用途 |
WO2014095555A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2746278A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746255A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
WO2014095547A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2935237A1 (en) | 2012-12-19 | 2015-10-28 | Basf Se | Substituted [1,2,4]triazole compounds and their use as fungicides |
EP2746262A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds for combating phytopathogenic fungi |
EP2746266A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
WO2014095534A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2746279A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
EP2746264A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
WO2014095381A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
EA030875B1 (ru) | 2012-12-20 | 2018-10-31 | Басф Агро Б.В. | Композиции, содержащие триазольное соединение |
EP2746258A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746257A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746260A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746259A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
WO2014124850A1 (en) | 2013-02-14 | 2014-08-21 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
WO2014130409A2 (en) | 2013-02-21 | 2014-08-28 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazole mixtures |
EP2813499A1 (en) | 2013-06-12 | 2014-12-17 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2815647A1 (en) | 2013-06-18 | 2014-12-24 | Basf Se | Novel strobilurin-type compounds for combating phytopathogenic fungi |
EP2815649A1 (en) | 2013-06-18 | 2014-12-24 | Basf Se | Fungicidal mixtures II comprising strobilurin-type fungicides |
EP2826367A1 (en) | 2013-07-18 | 2015-01-21 | Basf Se | Fungicidal mixtures comprising boscalid and zoxamide |
WO2015011615A1 (en) | 2013-07-22 | 2015-01-29 | Basf Corporation | Mixtures comprising a trichoderma strain and a pesticide |
EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
EP2839745A1 (en) | 2013-08-21 | 2015-02-25 | Basf Se | Agrochemical formulations comprising a 2-ethyl-hexanol alkoxylate |
WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
CA2923101A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
WO2015055757A1 (en) | 2013-10-18 | 2015-04-23 | Basf Se | Use of pesticidal active carboxamide derivative in soil and seed application and treatment methods |
EP3080092B1 (en) | 2013-12-12 | 2019-02-06 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
US20160318897A1 (en) | 2013-12-18 | 2016-11-03 | Basf Se | Azole compounds carrying an imine-derived substituent |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
JP2017078022A (ja) * | 2014-02-28 | 2017-04-27 | クミアイ化学工業株式会社 | イソキサゾール誘導体及びそれを用いた農園芸用植物病害防除剤 |
PL3122732T3 (pl) | 2014-03-26 | 2018-08-31 | Basf Se | Podstawione związki [1,2,4]triazolowe i imidazolowe jako fungicydy |
EP2924027A1 (en) | 2014-03-28 | 2015-09-30 | Basf Se | Substituted [1,2,4]triazole and imidazole fungicidal compounds |
EP2949216A1 (en) | 2014-05-30 | 2015-12-02 | Basf Se | Fungicidal substituted alkynyl [1,2,4]triazole and imidazole compounds |
EP2949649A1 (en) | 2014-05-30 | 2015-12-02 | Basf Se | Fungicide substituted [1,2,4]triazole and imidazole compounds |
EP3151669B1 (en) | 2014-06-06 | 2020-10-28 | Basf Se | Use of substituted oxadiazoles for combating phytopathogenic fungi |
EP2952507A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
EP2952506A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
AR100743A1 (es) | 2014-06-06 | 2016-10-26 | Basf Se | Compuestos de [1,2,4]triazol sustituido |
EP2952512A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
EP3204390B1 (en) | 2014-10-06 | 2019-06-05 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
JP2017538860A (ja) | 2014-10-24 | 2017-12-28 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 固体粒子の表面荷電を改変するための、非両性の四級化可能な水溶性ポリマー |
BR112017009513A2 (pt) | 2014-11-06 | 2018-02-06 | Basf Se | utilização de um composto heterobicíclico, utilização dos compostos i, compostos, composição agrícola ou veterinária, método para o combate ou controle de pragas, método para a proteção de culturas e sementes |
EP3028573A1 (en) | 2014-12-05 | 2016-06-08 | Basf Se | Use of a triazole fungicide on transgenic plants |
AU2016214305B2 (en) | 2015-02-06 | 2020-10-08 | Basf Se | Pyrazole compounds as nitrification inhibitors |
CA3170386A1 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
WO2016128240A1 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound and two fungicides |
CA2980505A1 (en) | 2015-04-07 | 2016-10-13 | Basf Agrochemical Products B.V. | Use of an insecticidal carboxamide compound against pests on cultivated plants |
AU2016260805A1 (en) | 2015-05-12 | 2017-11-23 | Basf Se | Thioether compounds as nitrification inhibitors |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
EP3356341B1 (en) | 2015-10-02 | 2020-04-01 | Basf Se | Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents |
US20180279615A1 (en) | 2015-10-05 | 2018-10-04 | Basf Se | Pyridine derivatives for combating phytopathogenic fungi |
EP3371177A1 (en) | 2015-11-02 | 2018-09-12 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3165094A1 (en) | 2015-11-03 | 2017-05-10 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
BR112018008288A2 (pt) | 2015-11-04 | 2018-10-30 | Basf Se | uso de compostos de fórmula, compostos de fórmula, mistura, composição agroquímica e método para combater fungos |
EP3165093A1 (en) | 2015-11-05 | 2017-05-10 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3167716A1 (en) | 2015-11-10 | 2017-05-17 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3373732A1 (en) | 2015-11-13 | 2018-09-19 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
WO2017081312A1 (en) | 2015-11-13 | 2017-05-18 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
WO2017085100A1 (en) | 2015-11-19 | 2017-05-26 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
CA3003946A1 (en) | 2015-11-19 | 2017-05-26 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3383183B1 (en) | 2015-11-30 | 2020-05-27 | Basf Se | Compositions containing cis-jasmone and bacillus amyloliquefaciens |
CN108290840A (zh) | 2015-12-01 | 2018-07-17 | 巴斯夫欧洲公司 | 作为杀真菌剂的吡啶化合物 |
BR112018010140A8 (pt) | 2015-12-01 | 2019-02-26 | Basf Se | compostos de fórmula, composição, utilização de um composto de fórmula, método para o combate de fungos fitopatogênicos e semente |
EP3205208A1 (en) | 2016-02-09 | 2017-08-16 | Basf Se | Mixtures and compositions comprising paenibacillus strains or fusaricidins and chemical pesticides |
EP3426660A1 (en) | 2016-03-09 | 2019-01-16 | Basf Se | Spirocyclic derivatives |
US20190098899A1 (en) | 2016-03-10 | 2019-04-04 | Basf Se | Fungicidal mixtures iii comprising strobilurin-type fungicides |
US20190082696A1 (en) | 2016-03-11 | 2019-03-21 | Basf Se | Method for controlling pests of plants |
UA123912C2 (uk) | 2016-04-01 | 2021-06-23 | Басф Се | Біциклічні сполуки |
BR112018069897B1 (pt) | 2016-04-11 | 2023-01-17 | Basf Se | Composto de fórmula i, composição agroquímica, processo para a preparação de compostos de fórmula i, uso não terapêutico de compostos e método para o combate de fungos fitopatogênicos nocivos |
US20190276376A1 (en) | 2016-05-18 | 2019-09-12 | Basf Se | Capsules comprising benzylpropargylethers for use as nitrification inhibitors |
WO2018050421A1 (en) | 2016-09-13 | 2018-03-22 | Basf Se | Fungicidal mixtures i comprising quinoline fungicides |
WO2018054721A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018054711A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018054723A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018065182A1 (en) | 2016-10-04 | 2018-04-12 | Basf Se | Reduced quinoline compounds as antifuni agents |
WO2018073110A1 (en) | 2016-10-20 | 2018-04-26 | Basf Se | Quinoline compounds as fungicides |
EP3555050A1 (en) | 2016-12-16 | 2019-10-23 | Basf Se | Pesticidal compounds |
EP3555056A1 (en) | 2016-12-19 | 2019-10-23 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3339297A1 (en) | 2016-12-20 | 2018-06-27 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3338552A1 (en) | 2016-12-21 | 2018-06-27 | Basf Se | Use of a tetrazolinone fungicide on transgenic plants |
EP3571190A1 (en) | 2017-01-23 | 2019-11-27 | Basf Se | Fungicidal pyridine compounds |
EP3575286B1 (en) | 2017-01-26 | 2022-05-11 | Mitsui Chemicals Agro, Inc. | Pyridone compound and bactericide for agricultural and horticultural use, which uses said compound as active ingredient |
WO2018149754A1 (en) | 2017-02-16 | 2018-08-23 | Basf Se | Pyridine compounds |
BR112019015338B1 (pt) | 2017-02-21 | 2023-03-14 | Basf Se | Compostos de fórmula i, composição agroquímica, semente revestida, uso dos compostos e método para combater fungos nocivos fitopatogênicos |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
KR102596592B1 (ko) | 2017-03-28 | 2023-10-31 | 바스프 에스이 | 살충 화합물 |
AU2018241628B2 (en) | 2017-03-31 | 2022-03-17 | Basf Se | Pyrimidinium compounds and their mixtures for combating animal pests |
US20200187500A1 (en) | 2017-04-06 | 2020-06-18 | Basf Se | Pyridine compounds |
US20200045974A1 (en) | 2017-04-07 | 2020-02-13 | Basf Se | Substituted Oxadiazoles for Combating Phytopathogenic Fungi |
CA3059675A1 (en) | 2017-04-10 | 2018-10-18 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients |
US11000038B2 (en) | 2017-04-10 | 2021-05-11 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
MX2019012174A (es) | 2017-04-11 | 2019-11-25 | Mitsui Chemicals Agro Inc | Compuestos de piridona y fungicidas agricolas y horticolas que contienen los mismos como ingredientes activos. |
WO2018188962A1 (en) | 2017-04-11 | 2018-10-18 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
TW201838965A (zh) | 2017-04-20 | 2018-11-01 | 印度商Pi工業公司 | 新穎的苯胺化合物 |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
MX2019012813A (es) | 2017-04-26 | 2020-01-14 | Basf Se | Derivados de succinimida sustituida como plaguicidas. |
US20210084902A1 (en) | 2017-05-02 | 2021-03-25 | Basf Se | Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
WO2018202491A1 (en) | 2017-05-04 | 2018-11-08 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
CN110621669A (zh) | 2017-05-04 | 2019-12-27 | 巴斯夫欧洲公司 | 防除植物病原性真菌的取代5-卤代烷基-5-羟基异噁唑类 |
BR112019022206A2 (pt) | 2017-05-05 | 2020-05-12 | Basf Se | Misturas fungicidas, composição agroquímica, uso da mistura, métodos para controlar fungos nocivos fitopatogênicos e para a proteção de material de propagação de plantas e material de propagação vegetal |
CA3059282A1 (en) | 2017-05-10 | 2018-11-15 | Basf Se | Bicyclic pesticidal compounds |
WO2018210658A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
WO2018210659A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
WO2018210660A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
WO2018210661A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
EP3625215B1 (en) | 2017-05-18 | 2023-09-13 | PI Industries Ltd | Formimidamidine compounds useful against phytopathogenic microorganisms |
EP3630731B1 (en) | 2017-05-30 | 2023-08-09 | Basf Se | Pyridine and pyrazine compounds for combating phytopathogenic fungi |
WO2018219797A1 (en) | 2017-06-02 | 2018-12-06 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
EP3636636B1 (en) | 2017-06-08 | 2022-07-06 | Mitsui Chemicals Agro, Inc. | Pyridone compound and agricultural and horticultural fungicide |
CN110770235A (zh) | 2017-06-16 | 2020-02-07 | 巴斯夫欧洲公司 | 用于防除动物害虫的介离子咪唑鎓化合物和衍生物 |
EP3642203A1 (en) | 2017-06-19 | 2020-04-29 | Basf Se | Substituted pyrimidinium compounds and derivatives for combating animal pests |
US20200190043A1 (en) | 2017-06-19 | 2020-06-18 | Basf Se | 2-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryloxy](thio)acetamides for combating phytopathogenic fungi |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | SUBSTITUTED CYCLOPROPYL DERIVATIVES |
JP6944141B2 (ja) | 2017-06-28 | 2021-10-06 | 日産化学株式会社 | アルコキシアルキル基を有するイソシアヌル酸誘導体及びその製造方法 |
WO2019002158A1 (en) | 2017-06-30 | 2019-01-03 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI |
WO2019025250A1 (en) | 2017-08-04 | 2019-02-07 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR COMBATING PHYTOPATHOGENIC FUNGI |
WO2019038042A1 (en) | 2017-08-21 | 2019-02-28 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI |
EP3915379A1 (en) | 2017-08-29 | 2021-12-01 | Basf Se | Pesticidal mixtures |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
US11076596B2 (en) | 2017-09-18 | 2021-08-03 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019057660A1 (en) | 2017-09-25 | 2019-03-28 | Basf Se | INDOLE AND AZAINDOLE COMPOUNDS HAVING 6-CHANNEL SUBSTITUTED ARYL AND HETEROARYL CYCLES AS AGROCHEMICAL FUNGICIDES |
BR112020006037A2 (pt) | 2017-10-13 | 2020-10-06 | Basf Se | compostos, misturas pesticidas, composição agroquímica, métodos para controlar pragas de invertebrados, para proteger plantas e para proteção de material de propagação de plantas, semente e uso de compostos de fórmula (i) |
EP3713936B1 (en) | 2017-11-23 | 2021-10-20 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019115511A1 (en) | 2017-12-14 | 2019-06-20 | Basf Se | Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
CA3084405A1 (en) | 2017-12-15 | 2019-06-20 | Basf Se | Fungicidal mixture comprising substituted pyridines |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
EP3728204A1 (en) | 2017-12-20 | 2020-10-28 | PI Industries Ltd. | Fluoralkenyl compounds, process for preparation and use thereof |
UA127604C2 (uk) | 2017-12-21 | 2023-11-01 | Басф Се | Пестицидні сполуки |
BR112020012706A2 (pt) | 2018-01-09 | 2020-11-24 | Basf Se | uso de um composto de silietinil hetarila, composição para uso na redução de nitrificação, mistura agroquímica, métodos para reduzir a nitrificação e para tratamento de um fertilizante ou de uma composição |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
EP3746439A2 (en) | 2018-01-30 | 2020-12-09 | PI Industries Ltd. | Oxadiazoles for use in controlling phytopathogenic fungi |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
US20200354321A1 (en) | 2018-02-07 | 2020-11-12 | Basf Se | New pyridine carboxamides |
WO2019154665A1 (en) | 2018-02-07 | 2019-08-15 | Basf Se | New pyridine carboxamides |
EP3530118A1 (en) | 2018-02-26 | 2019-08-28 | Basf Se | Fungicidal mixtures |
EP3530116A1 (en) | 2018-02-27 | 2019-08-28 | Basf Se | Fungicidal mixtures comprising xemium |
WO2019166561A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of alkoxypyrazoles as nitrification inhibitors |
IL276745B2 (en) | 2018-02-28 | 2023-10-01 | Basf Se | Use of N-functional alkoxy pyrazole compounds as nitrification inhibitors |
EP3758491A1 (en) | 2018-02-28 | 2021-01-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
WO2019166252A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Fungicidal mixtures comprising fenpropidin |
WO2019166257A1 (en) | 2018-03-01 | 2019-09-06 | BASF Agro B.V. | Fungicidal compositions of mefentrifluconazole |
EP3533331A1 (en) | 2018-03-02 | 2019-09-04 | Basf Se | Fungicidal mixtures comprising pydiflumetofen |
EP3533333A1 (en) | 2018-03-02 | 2019-09-04 | Basf Se | Fungicidal mixtures comprising pydiflumetofen |
EP3536150A1 (en) | 2018-03-06 | 2019-09-11 | Basf Se | Fungicidal mixtures comprising fluxapyroxad |
WO2019171234A1 (en) | 2018-03-09 | 2019-09-12 | Pi Industries Ltd. | Heterocyclic compounds as fungicides |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
WO2019202459A1 (en) | 2018-04-16 | 2019-10-24 | Pi Industries Ltd. | Use of 4-substituted phenylamidine compounds for controlling disease rust diseases in plants |
WO2019219464A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019219529A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Mixtures comprising benzpyrimoxan and oxazosulfyl and uses and methods of applying them |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
ES2969872T3 (es) | 2018-07-23 | 2024-05-23 | Basf Se | Uso de un compuesto de tiazolidina sustituida como inhibidor de la nitrificación |
WO2020020777A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
CA3104048A1 (en) | 2018-07-25 | 2020-01-30 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
TW202009235A (zh) | 2018-08-17 | 2020-03-01 | 印度商皮埃企業有限公司 | 1,2-二硫醇酮化合物及其用途 |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
CA3112042A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
EP3860992A1 (en) | 2018-10-01 | 2021-08-11 | PI Industries Ltd. | Novel oxadiazoles |
WO2020070611A1 (en) | 2018-10-01 | 2020-04-09 | Pi Industries Ltd | Oxadiazoles as fungicides |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
WO2020095161A1 (en) | 2018-11-05 | 2020-05-14 | Pi Industries Ltd. | Nitrone compounds and use thereof |
EP3887357A1 (en) | 2018-11-28 | 2021-10-06 | Basf Se | Pesticidal compounds |
EP3670501A1 (en) | 2018-12-17 | 2020-06-24 | Basf Se | Substituted [1,2,4]triazole compounds as fungicides |
WO2020126591A1 (en) | 2018-12-18 | 2020-06-25 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
CN113784958B (zh) | 2019-04-08 | 2024-04-30 | Pi工业有限公司 | 用于控制或预防植物病原性真菌的噁二唑化合物 |
WO2020208509A1 (en) | 2019-04-08 | 2020-10-15 | Pi Industries Limited | Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi |
BR112021020231A2 (pt) | 2019-04-08 | 2021-12-07 | Pi Industries Ltd | Compostos de oxadiazol inovadores para controlar ou prevenir fungos fitopatogênicos |
EP3730489A1 (en) | 2019-04-25 | 2020-10-28 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
WO2020239517A1 (en) | 2019-05-29 | 2020-12-03 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2020244969A1 (en) | 2019-06-06 | 2020-12-10 | Basf Se | Pyridine derivatives and their use as fungicides |
WO2020244970A1 (en) | 2019-06-06 | 2020-12-10 | Basf Se | New carbocyclic pyridine carboxamides |
BR112021021028A2 (pt) | 2019-06-06 | 2021-12-14 | Basf Se | Uso dos compostos de fórmula i, compostos da fórmula i, composição e método para combater fungos fitopatogênicos |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
AR119774A1 (es) | 2019-08-19 | 2022-01-12 | Pi Industries Ltd | Compuestos de oxadiazol que contienen un anillo heteroaromático de 5 miembros para controlar o prevenir hongos fitopatogénicos |
WO2021063736A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | Bicyclic pyridine derivatives |
WO2021063735A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | New bicyclic pyridine derivatives |
AR120374A1 (es) | 2019-11-08 | 2022-02-09 | Pi Industries Ltd | Compuestos de oxadiazol que contienen anillos de heterociclilo fusionados para controlar o prevenir hongos fitopatogénicos |
CA3162521A1 (en) | 2019-12-23 | 2021-07-01 | Basf Se | Enzyme enhanced root uptake of agrochemical active compound |
US20230106291A1 (en) | 2020-02-28 | 2023-04-06 | BASF Agro B.V. | Methods and uses of a mixture comprising alpha-cypermethrin and dinotefuran for controlling invertebrate pests in t |
WO2021175669A1 (en) | 2020-03-04 | 2021-09-10 | Basf Se | Use of substituted 1,2,4-oxadiazoles for combating phytopathogenic fungi |
BR112022020612A2 (pt) | 2020-04-14 | 2022-11-29 | Basf Se | Mistura fungicida, composição agroquímica, uso não terapêutico da mistura e método para controlar fungos fitopatogênicos nocivos |
EP4143167B1 (en) | 2020-04-28 | 2024-05-15 | Basf Se | Pesticidal compounds |
EP3903582A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ii |
EP3903583A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iii |
EP3903584A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iv |
EP3903581A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors i |
AU2021263047A1 (en) * | 2020-04-29 | 2022-11-10 | Syngenta Crop Protection Ag | Crop enhancement |
EP3909950A1 (en) | 2020-05-13 | 2021-11-17 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP3945089A1 (en) | 2020-07-31 | 2022-02-02 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors v |
WO2021249800A1 (en) | 2020-06-10 | 2021-12-16 | Basf Se | Substituted [1,2,4]triazole compounds as fungicides |
EP3939961A1 (en) | 2020-07-16 | 2022-01-19 | Basf Se | Strobilurin type compounds and their use for combating phytopathogenic fungi |
WO2022017836A1 (en) | 2020-07-20 | 2022-01-27 | BASF Agro B.V. | Fungicidal compositions comprising (r)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- (1,2,4-triazol-1-yl)propan-2-ol |
EP3970494A1 (en) | 2020-09-21 | 2022-03-23 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors viii |
AR123264A1 (es) | 2020-08-18 | 2022-11-16 | Pi Industries Ltd | Nuevos compuestos heterocíclicos para combatir los hongos fitopatógenos |
UY39424A (es) | 2020-09-15 | 2022-03-31 | Pi Industries Ltd | Nuevos compuestos de picolinamida para combatir hongos fitopatógenos |
AR123501A1 (es) | 2020-09-15 | 2022-12-07 | Pi Industries Ltd | Nuevos compuestos de picolinamida para combatir hongos fitopatógenos |
AR123594A1 (es) | 2020-09-26 | 2022-12-21 | Pi Industries Ltd | Compuestos nematicidas y uso de los mismos |
CN116209355A (zh) | 2020-10-27 | 2023-06-02 | 巴斯夫农业公司 | 包含氯氟醚菌唑的组合物 |
WO2022090071A1 (en) | 2020-11-02 | 2022-05-05 | Basf Se | Use of mefenpyr-diethyl for controlling phytopathogenic fungi |
WO2022090069A1 (en) | 2020-11-02 | 2022-05-05 | Basf Se | Compositions comprising mefenpyr-diethyl |
WO2022106304A1 (en) | 2020-11-23 | 2022-05-27 | BASF Agro B.V. | Compositions comprising mefentrifluconazole |
EP4018830A1 (en) | 2020-12-23 | 2022-06-29 | Basf Se | Pesticidal mixtures |
AR124796A1 (es) | 2021-02-02 | 2023-05-03 | Basf Se | Acción sinérgica de dcd y alcoxipirazoles como inhibidores de la nitrificación |
EP4043444A1 (en) | 2021-02-11 | 2022-08-17 | Basf Se | Substituted isoxazoline derivatives |
TW202309047A (zh) | 2021-05-05 | 2023-03-01 | 印度商皮埃企業有限公司 | 用以防治植物病原真菌的新穎稠合雜環化合物 |
EP4337012A1 (en) | 2021-05-11 | 2024-03-20 | Basf Se | Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
CN117355520A (zh) | 2021-05-18 | 2024-01-05 | 巴斯夫欧洲公司 | 用作杀真菌剂的新型取代喹啉类 |
BR112023024017A2 (pt) | 2021-05-18 | 2024-02-06 | Basf Se | Compostos, composição, método para combater fungos fitopatogênicos e semente |
AU2022279357A1 (en) | 2021-05-18 | 2023-11-30 | Basf Se | New substituted pyridines as fungicides |
AR125955A1 (es) | 2021-05-21 | 2023-08-30 | Basf Se | Uso de un compuesto de alcoxi pirazol n-funcionalizado como inhibidor de nitrificación |
WO2022243521A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of ethynylpyridine compounds as nitrification inhibitors |
AR125925A1 (es) | 2021-05-26 | 2023-08-23 | Pi Industries Ltd | Composicion fungicida que contiene compuestos de oxadiazol |
EP4094579A1 (en) | 2021-05-28 | 2022-11-30 | Basf Se | Pesticidal mixtures comprising metyltetraprole |
WO2022268810A1 (en) | 2021-06-21 | 2022-12-29 | Basf Se | Metal-organic frameworks with pyrazole-based building blocks |
EP4119547A1 (en) | 2021-07-12 | 2023-01-18 | Basf Se | Triazole compounds for the control of invertebrate pests |
WO2023011958A1 (en) | 2021-08-02 | 2023-02-09 | Basf Se | (3-pirydyl)-quinazoline |
IL310497A (en) | 2021-08-02 | 2024-03-01 | Basf Se | (3-quinolyl)-quinazoline |
EP4140986A1 (en) | 2021-08-23 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4140995A1 (en) | 2021-08-27 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4151631A1 (en) | 2021-09-20 | 2023-03-22 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2023072671A1 (en) | 2021-10-28 | 2023-05-04 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ix |
WO2023072670A1 (en) | 2021-10-28 | 2023-05-04 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors x |
EP4194453A1 (en) | 2021-12-08 | 2023-06-14 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4198033A1 (en) | 2021-12-14 | 2023-06-21 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP4198023A1 (en) | 2021-12-16 | 2023-06-21 | Basf Se | Pesticidally active thiosemicarbazone compounds |
AR127972A1 (es) | 2021-12-17 | 2024-03-13 | Pi Industries Ltd | Novedosos compuestos de piridina carboxamida bicíclica sustituida fusionada para combatir hongos fitopatogénicos |
EP4238971A1 (en) | 2022-03-02 | 2023-09-06 | Basf Se | Substituted isoxazoline derivatives |
WO2023203066A1 (en) | 2022-04-21 | 2023-10-26 | Basf Se | Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers |
WO2023208447A1 (en) | 2022-04-25 | 2023-11-02 | Basf Se | An emulsifiable concentrate having a (substituted) benzaldehyde-based solvent system |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
EP4342885A1 (en) | 2022-09-20 | 2024-03-27 | Basf Se | N-(3-(aminomethyl)-phenyl)-5-(4-phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-amine derivatives and similar compounds as pesticides |
EP4361126A1 (en) | 2022-10-24 | 2024-05-01 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors xv |
WO2024104813A1 (en) | 2022-11-14 | 2024-05-23 | Basf Se | Fungicidal mixture comprising substituted pyridines |
WO2024104822A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Substituted tetrahydrobenzodiazepine as fungicides |
WO2024104818A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Substituted benzodiazepines as fungicides |
WO2024104823A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | New substituted tetrahydrobenzoxazepine |
WO2024104815A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Substituted benzodiazepines as fungicides |
WO2024104814A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Fungicidal mixture comprising substituted pyridines |
EP4389210A1 (en) | 2022-12-21 | 2024-06-26 | Basf Se | Heteroaryl compounds for the control of invertebrate pests |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1927847A (zh) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | 异噁唑类化合物作为杀菌剂的应用 |
CN101061125A (zh) * | 2004-09-10 | 2007-10-24 | 先正达有限公司 | 作为杀真菌剂的取代异唑 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
MXPA02001565A (es) * | 1999-08-13 | 2005-07-14 | Vertex Pharma | Inhibidores de cinasas c-jun n-terminal (jnk) y de otras cinasas proteicas. |
AR039329A1 (es) * | 2002-04-26 | 2005-02-16 | Lilly Co Eli | Derivados de triazol, antagonistas de receptor de taquicinina |
AU2005285130B2 (en) * | 2004-09-10 | 2011-09-15 | Syngenta Limited | Substituted isoxazoles as fungicides |
WO2006116355A1 (en) * | 2005-04-22 | 2006-11-02 | Kalypsys, Inc. | Ortho-terphenyl inhibitors of p38 kinase and methods of treating inflammatory disorders |
DE102005031412A1 (de) * | 2005-07-06 | 2007-01-11 | Bayer Cropscience Gmbh | 3-[1-Halo-1-aryl-methan-sulfonyl]-und 3-[1-Halo-1-heteroaryl-methan-sulfonyl]-isoxazolin-Derivate, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
US20100179059A1 (en) * | 2007-06-06 | 2010-07-15 | Basf Se | Fungicidal Mixtures |
GB0823002D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isoxazoles derivatives with plant growth regulating properties |
-
2008
- 2008-12-17 GB GBGB0823002.1A patent/GB0823002D0/en active Pending
-
2009
- 2009-12-11 NZ NZ592997A patent/NZ592997A/xx not_active IP Right Cessation
- 2009-12-11 MX MX2011006085A patent/MX2011006085A/es not_active Application Discontinuation
- 2009-12-11 GE GEAP200912303A patent/GEP20135948B/en unknown
- 2009-12-11 CN CN2009801507449A patent/CN102256491A/zh active Pending
- 2009-12-11 AU AU2009328243A patent/AU2009328243A1/en not_active Abandoned
- 2009-12-11 CN CN2009801504563A patent/CN102256490A/zh active Pending
- 2009-12-11 BR BRPI0922262-6A patent/BRPI0922262A2/pt not_active IP Right Cessation
- 2009-12-11 AU AU2009328244A patent/AU2009328244A1/en not_active Abandoned
- 2009-12-11 JP JP2011541361A patent/JP2012512227A/ja active Pending
- 2009-12-11 MX MX2011006250A patent/MX2011006250A/es not_active Application Discontinuation
- 2009-12-11 US US13/140,766 patent/US20110251066A1/en not_active Abandoned
- 2009-12-11 JP JP2011541360A patent/JP2012512226A/ja active Pending
- 2009-12-11 EA EA201100948A patent/EA201100948A1/ru unknown
- 2009-12-11 EA EA201100944A patent/EA201100944A1/ru unknown
- 2009-12-11 US US13/140,774 patent/US20110251069A1/en not_active Abandoned
- 2009-12-11 WO PCT/EP2009/066965 patent/WO2010069881A2/en active Application Filing
- 2009-12-11 CA CA2746963A patent/CA2746963A1/en not_active Abandoned
- 2009-12-11 EP EP09768392A patent/EP2365751A1/en not_active Withdrawn
- 2009-12-11 KR KR1020117016418A patent/KR20110102463A/ko not_active Application Discontinuation
- 2009-12-11 EP EP09774899A patent/EP2369933A2/en not_active Withdrawn
- 2009-12-11 US US13/133,708 patent/US8476446B2/en not_active Expired - Fee Related
- 2009-12-11 CA CA2746549A patent/CA2746549A1/en not_active Abandoned
- 2009-12-11 WO PCT/EP2009/066966 patent/WO2010069882A1/en active Application Filing
- 2009-12-11 BR BRPI0922644-3A patent/BRPI0922644A2/pt not_active IP Right Cessation
- 2009-12-11 KR KR1020117016610A patent/KR20110102470A/ko not_active Application Discontinuation
- 2009-12-16 AR ARP090104919A patent/AR074696A1/es not_active Application Discontinuation
- 2009-12-16 TW TW098143040A patent/TW201024288A/zh unknown
- 2009-12-16 AR ARP090104918A patent/AR074695A1/es not_active Application Discontinuation
- 2009-12-16 TW TW098143047A patent/TW201023746A/zh unknown
-
2011
- 2011-05-23 IL IL213069A patent/IL213069A0/en unknown
- 2011-05-23 IL IL213066A patent/IL213066A0/en unknown
- 2011-05-26 ZA ZA2011/03887A patent/ZA201103887B/en unknown
- 2011-05-26 ZA ZA2011/03893A patent/ZA201103893B/en unknown
- 2011-06-14 CR CR20110328A patent/CR20110328A/es unknown
- 2011-06-14 CL CL2011001443A patent/CL2011001443A1/es unknown
- 2011-06-14 CR CR20110327A patent/CR20110327A/es not_active Application Discontinuation
- 2011-06-15 MA MA33949A patent/MA32906B1/fr unknown
- 2011-06-15 MA MA33948A patent/MA32905B1/fr unknown
- 2011-06-15 NI NI201100123A patent/NI201100123A/es unknown
- 2011-06-15 NI NI201100122A patent/NI201100122A/es unknown
- 2011-06-15 CL CL2011001456A patent/CL2011001456A1/es unknown
- 2011-06-16 CO CO11075263A patent/CO6382087A2/es not_active Application Discontinuation
- 2011-06-16 CO CO11075268A patent/CO6390026A2/es not_active Application Discontinuation
-
2013
- 2013-07-02 US US13/934,030 patent/US20130296381A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101061125A (zh) * | 2004-09-10 | 2007-10-24 | 先正达有限公司 | 作为杀真菌剂的取代异唑 |
CN1927847A (zh) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | 异噁唑类化合物作为杀菌剂的应用 |
Non-Patent Citations (1)
Title |
---|
HUNG JIN KIM等: "A Facile Synthesis of Fluro[3,4-c]isoxazoles: Precursors to 3,4-Disubstituted Isoxazoles", 《J. ORG. CHEM.》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105051196A (zh) * | 2013-03-14 | 2015-11-11 | 加利福尼亚大学董事会 | 正交配体激活的修饰的pyr/pyl受体 |
CN105051196B (zh) * | 2013-03-14 | 2018-07-17 | 加利福尼亚大学董事会 | 正交配体激活的修饰的pyr/pyl受体 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102256490A (zh) | 用作植物生长调节剂的异噁唑衍生物 | |
CN110015977B (zh) | 一种丙二腈肟醚类化合物及其用途 | |
CA2579199C (en) | Substituted isoxazoles as fungicides | |
CN102448954A (zh) | 作为杀真菌剂的经取代喹唑啉 | |
CN105294668A (zh) | 杀虫化合物 | |
CN102939288A (zh) | 二氢吡咯衍生物的制备方法 | |
TW201920164A (zh) | 新型殺真菌雜環化合物 | |
CN103012393A (zh) | 用作杀真菌剂的异噻唑和吡唑衍生物 | |
CN101687843A (zh) | 作为杀真菌剂的经取代的芳族杂环化合物 | |
CN102256961A (zh) | 用作植物生长调节剂的吡咯衍生物 | |
CN102256962A (zh) | 用作植物生长调节剂的异噻唑和吡唑衍生物 | |
CN104582483A (zh) | 土壤有害生物控制的方法 | |
CN102256487A (zh) | 用作植物生长调节剂的噻吩、呋喃和吡咯衍生物 | |
CN105585521B (zh) | 一种双哌啶酮季铵盐(碱)类化合物及其用途 | |
CN104519739A (zh) | 大豆有害生物控制的方法 | |
JPS58201795A (ja) | 植物抽出物およびそれを有効成分として含有する農園芸用殺菌組成物 | |
JPH0466869B2 (zh) | ||
JPS59157071A (ja) | アゾ−ル誘導体、その製造法およびそれを有効成分とする農園芸用殺菌剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20111123 |