CN102946730A - N3-取代的-n1-磺酰基-5-氟嘧啶酮衍生物 - Google Patents
N3-取代的-n1-磺酰基-5-氟嘧啶酮衍生物 Download PDFInfo
- Publication number
- CN102946730A CN102946730A CN2011800316808A CN201180031680A CN102946730A CN 102946730 A CN102946730 A CN 102946730A CN 2011800316808 A CN2011800316808 A CN 2011800316808A CN 201180031680 A CN201180031680 A CN 201180031680A CN 102946730 A CN102946730 A CN 102946730A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- compound
- amino
- plant
- haloalkyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims description 31
- 241000196324 Embryophyta Species 0.000 claims description 30
- -1 4Be halogen Chemical class 0.000 claims description 16
- 241000894006 Bacteria Species 0.000 claims description 14
- 241000209140 Triticum Species 0.000 claims description 10
- 235000021307 Triticum Nutrition 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000002538 fungal effect Effects 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 4
- 244000105624 Arachis hypogaea Species 0.000 claims description 4
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 4
- 235000018262 Arachis monticola Nutrition 0.000 claims description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 claims description 4
- 241000335053 Beta vulgaris Species 0.000 claims description 4
- 241001533598 Septoria Species 0.000 claims description 4
- 230000000843 anti-fungal effect Effects 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 235000020232 peanut Nutrition 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 206010039509 Scab Diseases 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 244000053095 fungal pathogen Species 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 17
- 238000002360 preparation method Methods 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 230000000855 fungicidal effect Effects 0.000 description 21
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002917 insecticide Substances 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000000361 pesticidal effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 229920000847 nonoxynol Polymers 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 208000035126 Facies Diseases 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- FDYDGPMTLJGGMJ-UHFFFAOYSA-N 4-amino-1-(benzenesulfonyl)-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1S(=O)(=O)C1=CC=CC=C1 FDYDGPMTLJGGMJ-UHFFFAOYSA-N 0.000 description 2
- 241000235349 Ascomycota Species 0.000 description 2
- 241000221198 Basidiomycota Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229920005682 EO-PO block copolymer Polymers 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241000233654 Oomycetes Species 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241001360088 Zymoseptoria tritici Species 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000008135 aqueous vehicle Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000005516 engineering process Methods 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
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000009545 invasion Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FHTGJZOULSYEOB-UHFFFAOYSA-N 2,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1O FHTGJZOULSYEOB-UHFFFAOYSA-N 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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241001281801 Mycosphaerella arachidis Species 0.000 description 1
- 241001329956 Nothopassalora personata Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000087479 Pseudocercospora fijiensis Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 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
- 235000019485 Safflower oil Nutrition 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002009 alkene group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000012043 crude product Substances 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
- 230000006378 damage Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- QHDUJTCUPWHNPK-UHFFFAOYSA-N methyl 7-methoxy-2h-indazole-3-carboxylate Chemical compound COC1=CC=CC2=C(C(=O)OC)NN=C21 QHDUJTCUPWHNPK-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 230000035040 seed growth Effects 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
Abstract
Description
疾病对照百分数 | 评定 |
76-100 | A |
51-75 | B |
26-50 | C |
0-25 | D |
未测试 | E |
Claims (4)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US32785510P | 2010-04-26 | 2010-04-26 | |
US61/327,855 | 2010-04-26 | ||
PCT/US2011/033203 WO2011137002A1 (en) | 2010-04-26 | 2011-04-20 | N3-substituted-n1-sulfonyl-5-fluoropyrimidinone derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102946730A true CN102946730A (zh) | 2013-02-27 |
CN102946730B CN102946730B (zh) | 2015-02-04 |
Family
ID=44816310
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180031680.8A Active CN102946730B (zh) | 2010-04-26 | 2011-04-20 | N3-取代的-n1-磺酰基-5-氟嘧啶酮衍生物 |
Country Status (33)
Country | Link |
---|---|
US (1) | US8263603B2 (zh) |
EP (1) | EP2563129B1 (zh) |
JP (1) | JP5784705B2 (zh) |
KR (1) | KR101793766B1 (zh) |
CN (1) | CN102946730B (zh) |
AU (1) | AU2011245544B2 (zh) |
BR (1) | BR112012027439B1 (zh) |
CA (1) | CA2797226C (zh) |
CL (1) | CL2012002979A1 (zh) |
CO (1) | CO6592042A2 (zh) |
CR (1) | CR20120584A (zh) |
CY (1) | CY1117956T1 (zh) |
DK (1) | DK2563129T3 (zh) |
EC (1) | ECSP12012302A (zh) |
ES (1) | ES2588742T3 (zh) |
GT (1) | GT201200289A (zh) |
HK (1) | HK1182594A1 (zh) |
HN (1) | HN2012002272A (zh) |
HR (1) | HRP20161107T1 (zh) |
HU (1) | HUE029489T2 (zh) |
IL (1) | IL222646A (zh) |
LT (1) | LT2563129T (zh) |
ME (1) | ME02530B (zh) |
MX (1) | MX2012012530A (zh) |
NZ (1) | NZ603151A (zh) |
PL (1) | PL2563129T3 (zh) |
PT (1) | PT2563129T (zh) |
RS (1) | RS55239B1 (zh) |
RU (1) | RU2562840C2 (zh) |
SI (1) | SI2563129T1 (zh) |
SM (1) | SMT201600298B (zh) |
UA (1) | UA108101C2 (zh) |
WO (1) | WO2011137002A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106028816A (zh) * | 2013-12-31 | 2016-10-12 | 阿达玛马克西姆股份有限公司 | 用防治谷类中真菌的协同杀真菌混合物 |
CN106061972A (zh) * | 2013-12-31 | 2016-10-26 | 阿达玛马克西姆股份有限公司 | 5‑氟‑4‑亚氨基‑3‑(烷基/取代烷基)‑1‑(芳基磺酰基)‑3,4‑二氢嘧啶‑2(1h)‑酮及其制备方法 |
CN114901073A (zh) * | 2019-07-22 | 2022-08-12 | 阿达马蒂斯有限公司 | 杀真菌组合、混合物和组合物及其用途 |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101743791B1 (ko) * | 2009-08-07 | 2017-06-05 | 다우 아그로사이언시즈 엘엘씨 | N1-술포닐-5-플루오로피리미디논 유도체 |
HUE047711T2 (hu) * | 2012-12-28 | 2020-05-28 | Adama Makhteshim Ltd | N-(szubsztituált)-5-fluor-4-imino-3-metil-2-oxo-3,4-dihidropirimidin-1(2H)-karboxilát származékok |
UA117123C2 (uk) * | 2012-12-28 | 2018-06-25 | Адама Махтешім Лтд. | Похідні 1-(заміщений бензоїл)-5-фтор-4-іміно-3-метил-3,4-дигідропіримідин-2(1h)-ону |
UA117743C2 (uk) * | 2012-12-28 | 2018-09-25 | Адама Махтешім Лтд. | N-(заміщені)-5-фтор-4-іміно-3-метил-2-оксо-3,4-дигідропіримідин-1(2h)-карбоксамідні похідні |
US9642368B2 (en) * | 2012-12-31 | 2017-05-09 | Adama Makhteshim Ltd. | 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides |
MA41272A (fr) * | 2014-12-23 | 2017-10-31 | Adama Makhteshim Ltd | 5-fluoro-4-imino-3-(alkyle/alkyle substitué)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one en tant que traitement des semences |
JP6862939B2 (ja) * | 2016-03-11 | 2021-04-21 | 住友化学株式会社 | 植物病害防除組成物及び植物病害防除方法 |
JP7037507B2 (ja) * | 2017-01-26 | 2022-03-16 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
EP3611166B1 (en) | 2017-04-10 | 2022-09-21 | Mitsui Chemicals Agro, Inc. | Pyridone compound, and agricultural and horticultural fungicide having this as active component |
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 |
US11178870B2 (en) | 2017-04-11 | 2021-11-23 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
JP7157738B2 (ja) | 2017-06-08 | 2022-10-20 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
IL271950B1 (en) | 2017-07-17 | 2024-02-01 | Adama Makhteshim Ltd | Polymorphs of 5-fluoro-4-imino-3-methyl-1-tosyl-4,3-dihydropyrimidin-2-one |
TWI828725B (zh) | 2018-07-25 | 2024-01-11 | 日商三井化學植保股份有限公司 | 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑 |
CN113260255A (zh) | 2018-11-05 | 2021-08-13 | 阿达玛马克西姆有限公司 | 包含5-氟-4-亚氨基-3-甲基-1-甲苯磺酰基-3,4-二氢嘧啶-2-酮的混合物和组合物及其使用方法 |
IL296178A (en) * | 2020-03-09 | 2022-11-01 | Adama Makhteshim Ltd | Process for preparing 5-fluoro-4-imino-3-methyl-1-(toluene-4-sulfonyl)-4,3-dihydro-1h-pyrimidin-2-one |
IL297864A (en) | 2020-05-04 | 2023-01-01 | Adama Makhteshim Ltd | Mixtures and preparations containing 5-fluoro-4-imino-3-methyl-1-tosyl-4,3-dihydropyrimidin-2-one and methods of using them |
JP2023533554A (ja) | 2020-07-08 | 2023-08-03 | アダマ・マクテシム・リミテッド | 殺菌・殺カビ性混合物 |
EP4284173A1 (en) | 2021-01-27 | 2023-12-06 | Adama Makhteshim Ltd. | 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1 h)-one for controlling plant diseases |
CA3216622A1 (en) | 2021-05-04 | 2022-11-10 | Stefano Luca Giaffreda | Crystalline forms of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4- dihydropyrimidin-2-one, and mixtures, compositions and methods of use thereof |
WO2023042126A1 (en) * | 2021-09-15 | 2023-03-23 | Adama Makhteshim Ltd. | Process for preparing 5-fluoro-4-imino-3-methyl-1-(toluene-4-sulfonyl)-3,4-dihydro-1h-pyrimidin-2-one |
WO2023135535A1 (en) * | 2022-01-12 | 2023-07-20 | Adama Makhteshim Ltd. | Fungicidal mixtures comprising combination containing phthalimide fungicides |
WO2023166485A1 (en) | 2022-03-03 | 2023-09-07 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
WO2023228148A1 (en) | 2022-05-26 | 2023-11-30 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1328561A (zh) * | 1998-11-06 | 2001-12-26 | 辛根塔参与股份公司 | 用作杀真菌剂的嘧啶-4-烯胺 |
CN101312649A (zh) * | 2005-11-22 | 2008-11-26 | 石原产业株式会社 | 农业园艺用杀菌剂组合物以及植物病害的防除方法 |
WO2009094442A2 (en) * | 2008-01-22 | 2009-07-30 | Dow Agrosciences Llc | 5-fluoro pyrimidine derivatives |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HRP970239B1 (en) * | 1997-05-09 | 2004-04-30 | Inst Ru Er Bouekovic | Process for the preparation of sulfonyl-pyrimidine derivatives with antitumor activity |
CN104521977A (zh) * | 2008-08-01 | 2015-04-22 | 陶氏益农公司 | 5-氟胞嘧啶作为杀真菌剂的用途 |
UA112284C2 (uk) * | 2009-08-07 | 2016-08-25 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні 5-фторпіримідинону |
KR101743791B1 (ko) | 2009-08-07 | 2017-06-05 | 다우 아그로사이언시즈 엘엘씨 | N1-술포닐-5-플루오로피리미디논 유도체 |
-
2011
- 2011-04-20 LT LTEP11775446.5T patent/LT2563129T/lt unknown
- 2011-04-20 PT PT117754465T patent/PT2563129T/pt unknown
- 2011-04-20 ES ES11775446.5T patent/ES2588742T3/es active Active
- 2011-04-20 NZ NZ603151A patent/NZ603151A/xx unknown
- 2011-04-20 HU HUE11775446A patent/HUE029489T2/en unknown
- 2011-04-20 CN CN201180031680.8A patent/CN102946730B/zh active Active
- 2011-04-20 US US13/090,616 patent/US8263603B2/en active Active
- 2011-04-20 DK DK11775446.5T patent/DK2563129T3/en active
- 2011-04-20 BR BR112012027439-2A patent/BR112012027439B1/pt active IP Right Grant
- 2011-04-20 SI SI201130933A patent/SI2563129T1/sl unknown
- 2011-04-20 EP EP11775446.5A patent/EP2563129B1/en active Active
- 2011-04-20 RS RS20160719A patent/RS55239B1/sr unknown
- 2011-04-20 PL PL11775446T patent/PL2563129T3/pl unknown
- 2011-04-20 RU RU2012150293/13A patent/RU2562840C2/ru active
- 2011-04-20 MX MX2012012530A patent/MX2012012530A/es active IP Right Grant
- 2011-04-20 JP JP2013508042A patent/JP5784705B2/ja active Active
- 2011-04-20 AU AU2011245544A patent/AU2011245544B2/en active Active
- 2011-04-20 UA UAA201213412A patent/UA108101C2/ru unknown
- 2011-04-20 CA CA2797226A patent/CA2797226C/en active Active
- 2011-04-20 KR KR1020127030690A patent/KR101793766B1/ko active IP Right Grant
- 2011-04-20 ME MEP-2016-177A patent/ME02530B/me unknown
- 2011-04-20 WO PCT/US2011/033203 patent/WO2011137002A1/en active Application Filing
-
2012
- 2012-10-23 IL IL222646A patent/IL222646A/en active IP Right Grant
- 2012-10-24 CL CL2012002979A patent/CL2012002979A1/es unknown
- 2012-10-24 HN HN2012002272A patent/HN2012002272A/es unknown
- 2012-10-25 GT GT201200289A patent/GT201200289A/es unknown
- 2012-11-15 CR CR20120584A patent/CR20120584A/es unknown
- 2012-11-23 EC ECSP12012302 patent/ECSP12012302A/es unknown
- 2012-11-26 CO CO12213540A patent/CO6592042A2/es active IP Right Grant
-
2013
- 2013-08-27 HK HK13110019.1A patent/HK1182594A1/zh unknown
-
2016
- 2016-08-30 HR HRP20161107TT patent/HRP20161107T1/hr unknown
- 2016-08-31 CY CY20161100852T patent/CY1117956T1/el unknown
- 2016-09-01 SM SM201600298T patent/SMT201600298B/it unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1328561A (zh) * | 1998-11-06 | 2001-12-26 | 辛根塔参与股份公司 | 用作杀真菌剂的嘧啶-4-烯胺 |
CN101312649A (zh) * | 2005-11-22 | 2008-11-26 | 石原产业株式会社 | 农业园艺用杀菌剂组合物以及植物病害的防除方法 |
WO2009094442A2 (en) * | 2008-01-22 | 2009-07-30 | Dow Agrosciences Llc | 5-fluoro pyrimidine derivatives |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106028816A (zh) * | 2013-12-31 | 2016-10-12 | 阿达玛马克西姆股份有限公司 | 用防治谷类中真菌的协同杀真菌混合物 |
CN106061263A (zh) * | 2013-12-31 | 2016-10-26 | 阿达玛马克西姆股份有限公司 | 用防治谷类中真菌的协同杀真菌混合物 |
CN106061262A (zh) * | 2013-12-31 | 2016-10-26 | 阿达玛马克西姆股份有限公司 | 用防治谷类中真菌的协同杀真菌混合物 |
CN106061972A (zh) * | 2013-12-31 | 2016-10-26 | 阿达玛马克西姆股份有限公司 | 5‑氟‑4‑亚氨基‑3‑(烷基/取代烷基)‑1‑(芳基磺酰基)‑3,4‑二氢嘧啶‑2(1h)‑酮及其制备方法 |
CN106068268A (zh) * | 2013-12-31 | 2016-11-02 | 阿达玛马克西姆股份有限公司 | 5‑氟‑4‑亚氨基‑3‑(烷基/取代烷基)‑1‑(芳基磺酰基)‑3,4‑二氢嘧啶‑2(1h)‑酮及其制备方法 |
CN106061972B (zh) * | 2013-12-31 | 2020-01-17 | 阿达玛马克西姆股份有限公司 | 5-氟-4-亚氨基-3-(烷基/取代烷基)-1-(芳基磺酰基)-3,4-二氢嘧啶-2(1h)-酮及其制备方法 |
CN111217759A (zh) * | 2013-12-31 | 2020-06-02 | 阿达玛马克西姆股份有限公司 | 一种化合物及其制备方法 |
CN111362881A (zh) * | 2013-12-31 | 2020-07-03 | 阿达玛马克西姆股份有限公司 | 一种化合物及其制备方法 |
CN114794123A (zh) * | 2013-12-31 | 2022-07-29 | 阿达玛马克西姆股份有限公司 | 用防治谷类中真菌的协同杀真菌混合物 |
CN114931141A (zh) * | 2013-12-31 | 2022-08-23 | 阿达玛马克西姆股份有限公司 | 用防治谷类中真菌的协同杀真菌混合物 |
CN115380909A (zh) * | 2013-12-31 | 2022-11-25 | 阿达玛马克西姆股份有限公司 | 用防治谷类中真菌的协同杀真菌混合物 |
CN114901073A (zh) * | 2019-07-22 | 2022-08-12 | 阿达马蒂斯有限公司 | 杀真菌组合、混合物和组合物及其用途 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102946730A (zh) | N3-取代的-n1-磺酰基-5-氟嘧啶酮衍生物 | |
KR0185439B1 (ko) | 2-(2,6-디플루오로페닐)-4-(2-에톡시-4-t-부틸페닐)-2-옥사졸린 | |
RU2656101C2 (ru) | Производные 1-(замещенный бензоил)-5-фтор-4-имино-3-метил-3,4-дигидропиримидин-2(1h)-она | |
EP3150595B1 (en) | Derivatives of uk-2a | |
KR20150100865A (ko) | 곡류에서의 진균 방제를 위한 상승작용적 살진균 혼합물 | |
CN1044427C (zh) | 用带杂环的2-烷氧苯氧基硫酰脲类除草剂除灭杂草的方法 | |
KR20150100869A (ko) | N-(치환된)-5-플루오로-4-이미노-3-메틸-2-옥소-3,4-디히드로피리미딘-1(2h)-카르복스아미드 유도체 | |
CN102459256A (zh) | 一种偶氮环酰胺的固体形式 | |
RU2638556C2 (ru) | Производные n-(замещенного)-5-фтор-4-имино-3-метил-2-оксо-3,4-дигидропиримидин-1(2н)-карбоксилата | |
CN101337940A (zh) | 具杀虫活性的含氮杂环二氯烯丙醚类化合物 | |
CA2647381C (en) | Microemulsifiable formulations comprising azoxystrobin and propiconazole | |
CA3008648C (en) | Dendrimer and formulations thereof | |
CN104557710A (zh) | 含多取代基吡唑结构的吡唑肟类化合物的制备和应用 | |
CN1044428C (zh) | 除草剂 | |
CN110128352A (zh) | 哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用 | |
EA004574B1 (ru) | Оксимные о-эфирные соединения и фунгициды для применения в земледелии и садоводстве | |
CN103379826A (zh) | 5-氟胞嘧啶和其它杀真菌剂的协同性杀真菌相互作用 | |
JPH0558979A (ja) | 3,4−ジ(置換フエニル)酪酸誘導体および除草剤 | |
EP2938192B1 (en) | Fungicidal compositions for controlling leaf spots in sugar beets | |
CN102438993A (zh) | 用于控制真菌的化合物和方法 | |
TW202128018A (zh) | 除草劑組成物 | |
CN101389220B (zh) | 脱叶剂 | |
CN1461306A (zh) | 用作杀真菌剂的2-甲氧基亚氨基-2-(吡啶氧基甲基)苯基乙酰胺的噻唑衍生物 | |
JPS60146878A (ja) | スルホニルグアニジン誘導体,その製法及び除草剤 | |
CN104610248B (zh) | 一种多效价磺酰基三唑类化合物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1182594 Country of ref document: HK |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
REG | Reference to a national code |
Ref country code: HK Ref legal event code: GR Ref document number: 1182594 Country of ref document: HK |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20161228 Address after: Beersheba, Israel Patentee after: ADAMA MAKHTESHIM LTD. Address before: indiana Patentee before: Dow Agrosciences LLC |