CN1165229C - 基于吡啶酰胺和四氯间苯二腈的杀真菌混剂 - Google Patents
基于吡啶酰胺和四氯间苯二腈的杀真菌混剂 Download PDFInfo
- Publication number
- CN1165229C CN1165229C CNB988123339A CN98812333A CN1165229C CN 1165229 C CN1165229 C CN 1165229C CN B988123339 A CNB988123339 A CN B988123339A CN 98812333 A CN98812333 A CN 98812333A CN 1165229 C CN1165229 C CN 1165229C
- Authority
- CN
- China
- Prior art keywords
- alkyl
- methyl
- group
- compound
- halogen
- 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.)
- Expired - Lifetime
Links
- -1 pyridine amides Chemical class 0.000 title claims abstract description 104
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 9
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 title claims description 6
- 239000000417 fungicide Substances 0.000 title abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 4
- 239000005747 Chlorothalonil Substances 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 25
- 229940084434 fungoid Drugs 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 14
- 125000003118 aryl group Chemical group 0.000 abstract description 13
- 125000005843 halogen group Chemical group 0.000 abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 abstract description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 25
- 229910052801 chlorine Inorganic materials 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 14
- 230000000844 anti-bacterial effect Effects 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 11
- 230000001954 sterilising effect Effects 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 241000221785 Erysiphales Species 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 235000009754 Vitis X bourquina Nutrition 0.000 description 7
- 235000012333 Vitis X labruscana Nutrition 0.000 description 7
- 240000006365 Vitis vinifera Species 0.000 description 7
- 235000014787 Vitis vinifera Nutrition 0.000 description 7
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
- 241000123650 Botrytis cinerea Species 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 240000003768 Solanum lycopersicum Species 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 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 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- QSBQHEHNHCBCAA-UHFFFAOYSA-N 3,4-dihydrooxathiine Chemical compound C1CC=COS1 QSBQHEHNHCBCAA-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 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
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- 125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 240000005561 Musa balbisiana Species 0.000 description 2
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical class [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 description 2
- 244000000004 fungal plant pathogen Species 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229940087596 sodium phenolsulfonate Drugs 0.000 description 2
- BLXAGSNYHSQSRC-UHFFFAOYSA-M sodium;2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=CC=CC=C1S([O-])(=O)=O BLXAGSNYHSQSRC-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
- LMCBYQIBQXKCLN-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid;naphthalene Chemical class C1=CC=CC2=CC=CC=C21.C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 LMCBYQIBQXKCLN-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- JJJOZVFVARQUJV-UHFFFAOYSA-N 2-ethylhexylphosphonic acid Chemical compound CCCCC(CC)CP(O)(O)=O JJJOZVFVARQUJV-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006056 2-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-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
- 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
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- 125000006054 3-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 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 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000209763 Avena sativa Species 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 240000008384 Capsicum annuum var. annuum Species 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000005656 Fenazaquin Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
- 241000131448 Mycosphaerella Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-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
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 241001674391 Sphaerulina musiva Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZHPFOGOICBVVLO-UHFFFAOYSA-N [O].C1=CCCC1 Chemical compound [O].C1=CCCC1 ZHPFOGOICBVVLO-UHFFFAOYSA-N 0.000 description 1
- AYYSGGODZQILIT-UHFFFAOYSA-N [O].C1=CCCCC1 Chemical compound [O].C1=CCCCC1 AYYSGGODZQILIT-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006184 cosolvent 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
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 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
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-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
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 230000002371 mycocidal effect Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 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 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/74—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 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
一种杀真菌混剂，包括协同增效量的活性成分a)结构式Ib的酰胺化合物，R4是卤素和R11是被卤素取代的苯基，和b)四氯间苯二腈II。
Description
本发明涉及用于控制有害真菌的杀真菌混剂以及使用这些混剂控制有害真菌的方法。
WO 97/08952公开了结构式I酰胺化合物的混剂
A-CO-NR1R2 (I)
其中A是芳基，或芳族或非芳族的，具有1-3个选自O，N和S的杂原子的5-或6-元杂环；
其中芳基或杂环没有或有1，2或3个取代基，取代基各自独立地选自烷基、卤素、CHF2，CF3、烷氧基、卤代烷氧基、烷硫基、烷基亚磺酰基和烷基磺酰基；
R1是氢原子；
R2是没有或有1，2或3个取代基的苯基或环烷基，取代基选自烷基、链烯基、链炔基、烷氧基、链烯氧基、链炔氧基、环烷基、环链烯基、环烷氧基、环链烯氧基、苯基和卤素，其中脂族的和环脂族基团可以部分或全部卤代和/或环脂族基团可以有1-3个烷基取代基以及其中苯基上可以有1-5个卤原子和/或1-3个各自独立地选自烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基和卤代烷硫基的取代基，以及其中amidic苯基可与饱和的没有或有1或多个烷基取代基和/或有选自O和S的杂原子的5-元环缩合，以及已知作为杀螨剂的活性成分喹螨醚。
这些混剂对葡萄孢属真菌特别有效。
四氯间苯二腈(通用名：百菌清)，它的制备方法和对有害真菌的作用是已知的(参考“Pesticide Manual”，193页)。
亚胺菌类与百菌清的代表性混剂公开在EP-A 741 970中。
本发明的目的之一是提供另外一些控制有害真菌，特别是指出的含有百菌清作为活性成分的杀菌剂。
我们已经发现含有在开头定义的结构式I活性成分酰胺化合物和另一种杀真菌活性成分四氯间苯二腈II的混剂实现了发明目的。
本发明混剂有增效作用，因此特别适合控制有害真菌并且特别是蔬菜和葡萄上的白粉菌。
在本发明内容中，卤素是指氟、氯、溴和碘并特别是氟、氯和溴。
术语“烷基”包括直链和支链烷基基团。优选直链或支链C1-C12-烷基和特别是C1-C6-烷基。烷基基团的例子是烷基如，特别是甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1，1-二甲基乙基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1，2-二甲基丙基、1，1-二甲基丙基、2，2-二甲基丙基、1-乙基丙基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1，2-二甲基丁基、1，3-二甲基丁基、2，3-二甲基丁基、1，1-二甲基丁基、2，2-二甲基丁基、3，3-二甲基丁基、1，1，2-三甲基丙基、1，2，2-三甲基丙基、1-乙基丁基、2-乙基丁基、1-乙基-2-甲基丙基、正庚基、1-甲基己基、1-乙基戊基、2-乙基戊基、1-丙基丁基、辛基、癸基、十二烷基。
卤代烷基是指上面定义的烷基被一个或多个卤原子，特别是氟和氯部分或全部卤代。优选，1-3个卤素原子取代，并特别优选二氟甲烷或三氟甲基。
烷基和卤代烷基的上述定义相应地也适用于烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、烷基亚磺酰基和烷基磺酰基中的烷基和卤代烷基。
链烯基包括直链和支链链烯基。优选直链或支链C3-C12-链烯基并特别是C3-C6-链烯基。链烯基的例子包括2-丙烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1，1-二甲基-2-丙烯基、1，2-二甲基-2-丙烯基、1-乙基-2-丙烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1，1-二甲基-2-丁烯基、1，1-二甲基-3-丁烯基、1，1-二甲基-3-丁烯基、1，2-二甲基-2-丁烯基、1，2-二甲基-3-丁烯基、1，3-二甲基-2-丁烯基、1，3-二甲基-3-丁烯基、2，2-二甲基-3-丁烯基、2，3-二甲基-2-丁烯基、2，3-二甲基-3-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1，1，2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基，特别是2-丙烯基，2-丁烯基，3-甲基-2-丁烯基和3-甲基-2-戊烯基。
链烯基可以被一个或多个卤原子，特别是氟和氯部分或全部卤代。优选，1-3个卤素原子取代的链烯基。
链炔基包括直链和支链链炔基。优选直链或支链C3-C12-链炔基并特别是C3-C6链炔基。链炔基的例子包括2-丙炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-甲基-2-丁炔基、1，1-二甲基-2-丙炔基、1-乙基-2-丙炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、4-甲基-2-戊炔基、1，2-二甲基-2-丁炔基、1，1-二甲基-3-丁炔基、1，2-二甲基-3-丁炔基、2，2-二甲基-3-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基。
对链烯基和它的卤素取代基以及链炔基的上述定义也相应适用于链烯氧基和链炔氧基。
环烷基优选C3-C6-环烷基，如环丙基、环丁基，环戊基或环己基。如果环烷基被取代，优选1-3个C1-C4-烷基作为取代基。
环链烯基优选C4-C6-环链烯基，如环丁烯基，环戊烯基或环己烯基。如果环链烯基被取代，优选1-3个C1-C4-烷基作为取代基。
环烷氧基优选C5-C6-环烷氧基，如环戊氧基或环己氧基。如果环烷氧基被取代，优选1-3个C1-C4-烷基作为取代基。
环链烯氧基优选C5-C6-环链烯氧基，如环戊烯氧基或环己烯氧基。如果环链烯氧基被取代，优选1-3个C1-C4-烷基作为取代基。
芳基优选苯基。
如果A是苯基，它可以在任意位置带有一，二或三个上述取代基。这些取代基，各自独立地，优先选自烷基，二氟甲基，三氟甲基和卤素，特别是氯、溴和碘。特别优选2-位带有取代基的苯基。
如果A是5-元杂环，它特别是呋喃基、噻唑基、吡唑基、咪唑基、噁唑基、噻嗯基、***基或噻二唑基或它们相应的二氢或四氢衍生物。优选噻唑基或吡唑基。
如果A是6-元杂环，它特别是吡啶基或下面结构式的基团：
其中X和Y之一是O，S或NR9，其中NR9是氢或烷基，以及X和Y还可以是CH2、S、SO、SO2或NR9。虚线代表双键可有可无。
6-元芳族杂环特别优选吡啶基，特别是3-吡啶基或下面结构式的基团：
其中X是CH2、S、SO或SO2。
上面提到的杂环没有或有1，2或3个上述取代基，这些取代基，各自独立地，优先选自烷基，卤素，二氟甲基或三氟甲基。
A是特别优选下列结构式的基团：
其中R3，R4，R6，R7，R8和R9各自独立地是氢，烷基，特别是甲基，卤素，特别是氯，CHF2或CF3。
结构式I中的R1优选氢原子。
结构式I中的R2优选苯基。R2优选至少有一个取代基，并特别优选2-位。一个取代基(或多个取代基)优选自烷基、环烷基、环链烯基、卤素或苯基中的基团。
R2的取代基本身又可以被取代。脂族或环脂族取代基可以被部分或全部卤代，特别是氟化或氯化。它们优选有1，2或3个氟或氯原子。如果R2的取代基是苯基，此苯基可以优选被1-3个卤素原子取代，特别是氯原子，和/或优选烷基和烷氧基取代。特别优选，苯基在对位用卤素原子取代，即特别优选R2的取代基是对-卤素-取代的苯基。R2也可以与饱和的5-元环缩合，其中作为其一部分的5-元环可以有1-3个烷基取代基。
在这种情况下R2，例如是，二氢化茚基、苯并二氢噻吩基和氧杂二氢化茚基。优选二氢化茚基和2-氧杂二氢化茚基，其特别通过4-位与氮原子连接。
根据优选实施方案，本发明组合物包括结构式I的酰胺化合物，其中A定义如下：
苯基、吡啶基、二氢吡喃基、二氢氧硫杂环己二烯基、二氢氧硫杂环己二烯基氧化物、二氢氧硫杂环己二烯基二氧化物、呋喃基、噻唑基、吡唑基或噁唑基，其中这些基团可以有1，2或3个取代基，这些取代基，各自独立地，优先选自烷基，卤素，二氟甲基和三氟甲基。
根据另一个优选实施方案，A是：吡啶-3-基，其中2-位上没有取代基或被卤素、甲基、二氟甲基、三氟甲基、甲氧基、甲硫基、甲基亚磺酰基或甲基磺酰基取代；苯基，其中2-位上没有取代基或被甲基、三氟甲基、氯、溴或碘取代；
2-甲基-5，6-二氢吡喃-3-基；
2-甲基-5，6-二氢-1，4-氧硫杂环己二烯-3-基或它的4-氧化物或4，4-二氧化物；
2-甲基呋喃-3-基，其中4-位和/或5-位上没有取代基或被甲基取代；
噻唑-5-基，其中2-位和/或4-位上没有取代基或被甲基、氯、二氟甲基或三氟甲基取代；
噻唑-4-基，其中2-位和/或5-位上没有取代基或被甲基、氯、二氟甲基或三氟甲基取代；
1-甲基吡唑-4-基，其中3-位和/或5-位上没有取代基或被甲基、氯、二氟甲基或三氟甲基取代；或
噁唑-5-基，其中2-位和/或4-位上没有取代基或被甲基或氯取代。
根据另一个优选实施方案，本发明组合物包括结构式I的酰胺化合物，其中R2是没有或有1，2或3个上述取代基取代的苯基。
根据另一个优选实施方案，本发明组合物包括结构式I的酰胺化合物，其中R2是苯基，其在2-位上有下列取代基之一：
C3-C6-烷基、C5-C6-环链烯基、C5-C6-环烷氧基、环链烯氧基，其中这些基团可以被1，2或3个C1-C4-烷基取代，
苯基被1-5个卤素原子和/或1-3个选自，各自独立地，C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基和C1-C4-卤代烷硫基的取代基取代，
二氢化茚基或氧杂二氢化茚基，没有或被1，2或3个C1-C4-烷基取代。
根据另一个优选实施方案，本发明组合物包括结构式Ia的酰胺化合物，
其中
A是
X是亚甲基、硫、亚磺酰基或磺酰基(SO2)，
R3是甲基、二氟甲基、三氟甲基、氯、溴或碘，
R4是三氟甲基或氯，
R5是氢或甲基，
R6是甲基、二氟甲基、三氟甲基或氯，
R7是氢、甲基或氯，
R8是甲基、二氟甲基或三氟甲基，
R9是氢、甲基、二氟甲基、三氟甲基或氯，
R10是C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基或卤素。
根据特别的优选实施方案，本发明组合物包括结构式Ib的酰胺化合物，
其中
R4是卤素和
R11是被卤素取代的苯基。
EP-A-545 099和589 301中已经公开了上述的结构式I的酰胺化合物，在这里的描述仅作为参考。
结构式I的酰胺化合物的制备方法是已知的，例如，EP-A-545 099和589 301或以类似方法进行。
即使少量的结构式I的酰胺化合物也足以表现增效作用。酰胺化合物I和四氯间苯二腈的重量比优选20∶1-1∶20，特别是10∶1-1∶10。
由于它们的氮原子的碱性，化合物I可以与无机或有机酸或金属离子形成盐或加合物。
无机酸的例子包括氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸、硫酸、磷酸和硝酸。
适合的有机酸，例如，甲酸，碳酸和链烷酸，如乙酸、三氟乙酸、三氯乙酸和丙酸，还有乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(1-20个碳原子的直链或支链烷基磺酸)、芳基磺酸或芳基二磺酸(芳香基团，如苯基和萘基，带1或2个磺酸基团)、烷基膦酸(1-20个碳原子的直链或支链烷基膦酸)、芳基膦酸或芳基二膦酸(芳香基团，如苯基和萘基，带1或2个磷酸基团)，烷基或芳基可以进一步带有取代基，例如，对-甲苯磺酸、水杨酸、对-氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
适合的金属离子，特别是，第一至第八副族的金属离子，特别是铬、锰、铁、钴、镍、铜和锌，以及第二主族的元素，特别是钙和镁，和第三和第四主族元素，特别是铝、锡和铅。如适合，这些金属可以存在各种可接受的价态。
制备这些混剂时，优选使用纯活性成分I和II，并可以混合其它抗有害真菌或害虫如昆虫、蜘蛛或线虫的活性成分，或除草剂或植物生长调节活性成分或肥料。
化合物I和II的混剂，或化合物I和II同时，结合或分开使用，表现了对广谱的植物病原真菌的突出的杀菌作用，特别是来自子囊菌纲、担子菌纲，藻菌纲和半知菌纲的真菌。其中一些药剂是***作用，因此也可作为叶面和土壤使用的杀菌剂。
控制各种农作物上的大量真菌是非常重要的，例如棉花、各种蔬菜(如黄瓜、蚕豆、番茄、马铃薯和葫芦)、大麦、草皮、燕麦、香蕉、咖啡、玉米、各种果树、稻、黑麦、大豆、葡萄、小麦、观赏植物、甘蔗和各种种子。
特别适合控制以下植物病原真菌：禾谷类作物上的禾白粉菌(白粉菌)、葫芦上的二孢白粉菌和单丝壳白粉菌、苹果上的白叉丝单囊壳菌(苹果白粉菌)、葡萄上的葡萄钩丝壳菌、禾谷类作物上的柄锈菌属、棉花，水稻和草坪上的丝核菌属、禾谷类作物和甘蔗上的黑粉菌属、苹果黑星菌(斑点病)、禾谷类作物上的长蠕孢属、小麦的颍枯壳针孢菌(小麦颍枯病)、草莓，蔬菜，观赏植物和葡萄上的灰葡萄孢(灰霉病)、落花生尾孢(花生褐斑病)、小麦和大麦眼斑(基腐)病、稻梨孢菌、致病疫霉引起的马铃薯和番茄晚疫病、葡萄生单轴霉(葡萄霜霉病)、啤酒花和黄瓜上的假霜霉属、蔬菜和水果上的链格孢属、香蕉上的球腔菌属以及镰孢属和轮枝孢属真菌。
而且，本发明这些混剂特别优选用来控制葡萄和蔬菜，以及观赏植物上的白粉菌。
化合物I和II可以同时使用，即一起或分开或顺序使用，在分开使用时使用顺序对防治效果没有任何影响。
依据预定效果的特性，本发明混剂的使用比例，特别是对农作物，为0.01-8kg/ha，优选0.1-5kg/ha，特别是0.5-3.0kg/ha。
就化合物I来说，使用比例是0.01-2.5kg/ha，优选0.05-2.5kg/ha，特别是0.1-1.0kg/ha。
相应地，就化合物II来说，使用比例是0.01-10kg/ha，优选0.05-5kg/ha，特别是0.05-2.0kg/ha。
用于种子处理时，一般混剂的使用比例是0.001-250g/kg种子，优选0.01-100g/kg，特别是0.01-50g/kg。
为控制有害植物病原真菌，化合物I和II的分开或结合使用或化合物I和II的混剂的使用通过喷雾或喷粉种子、播前或播后、或出苗前或出苗后的植物或土壤来起作用。
本发明杀真菌的协同增效混剂或化合物I和II，可以制成例如现配现喷溶液，粉剂和悬浮剂的形式或高度浓缩的水性、油性或其它的悬浮剂、分散液、乳液、油分散液、糊剂、粉剂、撒施物或颗粒剂，并使用喷雾、雾化喷雾、喷粉、撒施或随水灌溉方法。使用剂型与应用目的有关；在任何情况下，都应该尽可能地使本发明混剂分布完全和均匀。
按照已知方法制备制剂，例如加入溶剂和/或载体填充活性成分，如需要使用乳化剂和分散剂，如使用水作为稀释剂也可以使用其它的有机溶剂作为助溶剂。适合此目的的助剂基本上包括：溶剂如芳烃(例如二甲苯)，氯代芳烃(例如氯苯)，石蜡(例如矿物油馏分)，醇(例如甲醇，丁醇)，酮(例如环己酮)，胺(例如乙醇胺，二甲基甲酰胺)和水；载体如经研磨的天然矿物(例如高岭土，粘土，滑石，白垩)和经研磨的合成矿物(例如细分散硅石，硅酸盐)；乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚，烷基磺酸盐和芳基磺酸盐)和分散剂如木素亚硫酸盐废液和甲基纤维素。
适合的表面活性剂是芳族磺酸，例如木素-、苯酚-、萘-和二丁基萘磺酸和脂肪酸，烷基-和烷基芳基磺酸、烷基、十二烷基醚和脂肪族醇硫酸的碱金属盐、碱土金属盐和铵盐以及硫酸化的十六-、硫酸化的十七-和十八碳醇或脂肪族醇乙二醇醚的盐、磺化萘和它的甲醛衍生物的缩合物、萘或萘磺酸与苯酚和甲醛的缩合物、聚氧乙烯辛基酚醚、乙氧基化异辛基-、辛基-或壬基苯酚、烷基苯酚-或三丁基苯基聚乙二醇醚、烷基芳基聚醚醇、异十三烷基醇、脂肪族醇/环氧乙烷缩合物、乙氧基化蓖麻油、聚氧乙烯烷基醚或聚氧丙烯，十二烷基醇聚乙二醇醚乙酸酯、山梨醇酯、木素亚硫酸盐废液或甲基纤维素。
制备药粉，撒施物和粉剂可以通过混合或联合研磨化合物I或II或化合物I和II与固体载体的混合物。
颗粒(例如包衣颗粒，浸渍颗粒或均一颗粒)的制备是通过将活性成分粘合在固体载体上。
填料或固体载体包括例如矿物质土，如硅胶、硅石、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、细粘土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁、研磨的合成材料和肥料，如硫酸铵、磷酸铵、硝酸铵、尿素和植物性的来源产品，如谷粉、树皮粉、木粉和坚果壳粉，纤维素粉或其它固体载体。一般，制剂中含有0.1-95％重量，优选0.5-90％重量的化合物I或II或化合物I和II的混剂。使用的活性成分纯度为90％-100％，优选95％-100％(根据NMR或HPLC谱)。
化合物I或II，混剂或相应制剂的应用方式为，用其杀菌有效量的混剂或分开使用的化合物I和II来处理有害真菌，它们的活动场所或防止它们到达的植物、种子、土壤、地区、材料或空间。
有害真菌侵染前后施用此混剂都有效果。
包括活性成分的这些制剂的实施例：
I.90重量份活性成分和10重量份N-甲基吡咯烷酮的溶液；这种溶液适于微滴施用；
II.20重量份活性成分，80重量份二甲苯，10重量份的8-10mol环氧乙烷与1mol油酸N-单乙醇酰胺加合物，5重量份十二烷基苯磺酸钙和5重量份的40mol环氧乙烷与1mol蓖麻油加合物的混合物；在水中均匀分散获得分散溶液；
III.20重量份活性成分，40重量份环己酮，30重量份异丁醇和20重量份的40mol环氧乙烷与1mol蓖麻油加合物的水分散液；
IV.20重量份活性成分，25重量份环己醇，65重量份的沸点210-280℃的矿物油馏分和10重量份的40mol环氧乙烷与1mol蓖麻油加合物的水分散液；
V.80重量份活性成分，3重量份二异丁基萘-1-磺酸钠，10重量份来自亚硫酸盐废液的木素磺酸钠和7重量份粉状硅胶在锤磨机中研磨的混合物；将混合物均匀地分散于水中获得喷雾混合物；
VI.3重量份活性成分和97重量份的均匀粉碎的高岭土形成紧密混合物；这种粉剂含有3％重量的活性成分；
VII.30重量份活性成分，92重量份粉状硅胶和8重量份已喷在这种硅胶表面上的石蜡油的紧密混合物；这种制剂对活性成分有好的粘结性；
VIII.40重量份活性成分，10重量份苯酚磺酸钠/脲/甲醛缩合物，2重量份硅胶和48重量份水的稳定水分散液；这种分散液可以进一步稀释；
IX.20重量份活性成分，2重量份十二烷基苯磺酸钙，8重量份脂肪醇聚乙二醇醚，20重量份苯酚磺酸钠/脲/甲醛缩合物和88重量份石蜡族矿物油的稳定油性分散液。
使用实施例
通过以下试验证实本发明混剂的增效作用：
活性成分，分开或一起，制成含有63％重量环己酮和27％重量乳化剂混合物的10％乳油，并用水稀释到所需浓度。
评估是以侵染叶片面积百分比为标准。将这些百分比转换成杀菌率。使用Abbot公式计算杀菌率(W)：
W＝(1-α)·100/β
α等于处理后的植物受真菌侵染％和
β等于未处理(对照)植物的真菌侵染％
杀菌率0表示相对于未处理对照植物的侵染水平；杀菌率100表示处理植物并未被侵染。
使用Colby公式计算活性成分混剂的预期杀菌效果[R.S.Colby，Weeds 15(1967)，20-22]，并与观察的杀菌效果相比较。
Colby公式：E＝X+Y-X·Y/100
E预期杀菌效果，当使用活性成分A和B的混剂，浓度为a和b时，
以未处理对照％表示
X杀菌效果，当使用活性成分A，浓度为a时，以未处理对照％表示
Y杀菌效果，当使用活性成分B，浓度为b时，以未处理对照％表示
应用实施例1-对辣椒上的灰葡萄孢的杀菌活性
由含有10％活性化合物，63％环己酮和27％乳化剂的储备溶液制成的活性成分水剂喷施绿色辣椒花盘至全部润湿。药膜干燥后2小时，用灰葡萄孢的孢子悬浮液接种果盘，其在2％强Biomalz溶液中含有1.7×106孢子/ml。随后将接种的果盘孵育在潮湿的培养箱中，18℃4天。然后肉眼观察发病果盘上灰葡萄孢的侵染。
施用的结构式I化合物是以下组分：
试验结果列于下面表1和2中。
表1：
| 实施例 | 活性成分(含量以ppm表示) | 在喷雾液中活性成分浓度ppm | 未处理对照杀菌率％ |
| IC | 未处理 | 0(100％侵染) | 0 |
| 2C | 化合物I.1 | 12.5 | 20 |
| 3C | 化合物I.2 | 50 | 85 |
| 4C | 化合物2 | 5012.5 | 00 |
表2：
| 实施例 | 本发明混剂(含量以ppm表示) | 观察的杀菌率 | 计算的杀菌率* |
| 5 | 12.5ppmI.1+12.5ppmII | 40 | 20 |
| 6 | 50ppmI.2+50ppmII | 97 | 85 |
*)使用Colby公式计算
试验结果显示在所有混合比例中观察的杀菌效果都高于使用Colby公式预先计算的杀菌效果。
应用实施例2-对番茄上的灰葡萄孢的杀菌活性
在盆栽的品种“GroBe Fleischtomate”的番茄叶片上，喷施由含有10％活性化合物，63％环己酮和27％乳化剂的储备溶液制成的水悬浮液至全部润湿。第二天，用灰葡萄孢疫霉属的游动孢子水悬浮液接种叶片。随后将植物放于水汽饱和的16-18℃的温室中。6天后，未处理的被侵染的对照植物上的番茄疫病发展到这样的程度，即侵染％可以通过肉眼观察确定。
试验结果列于下面表3和4中。
表3：
| 实施例 | 活性成分(含量以ppm表示) | 在喷雾液中活性成分浓度ppm | 相处理对照杀菌率％ |
| 7C | 对照(未处理) | (100％侵染) | 0 |
| 8C | 化合物I.1 | 0.8 | 0 |
| 9C | 化合物I.2 | 0.8 | 0 |
| 10C | 化合物II | 0.8 | 0 |
表4：
| 实施例 | 本发明混剂(含量以ppm表示) | 观察的杀菌率 | 计算的杀菌率* |
| 11 | 0.8ppmI.1+0.8ppmII | 50 | 0 |
| 12 | 0.8ppmI.2+0.8ppmII | 30 | 0 |
*)使用Colby公式计算
试验结果显示在所有混合比例中观察的杀菌效果都高于使用Colby公式预先计算的杀菌效果。
Claims (4)
1.一种杀真菌混剂，包括重量比范围为20∶1至1∶20的下述活性成分
a)结构式Ib的酰胺化合物，
其中
R4是卤素和
R11是被卤素取代的苯基；和
b)四氯间苯二腈II
2.根据权利要求1的杀真菌混剂，其中包括下列结构式的酰胺化合物：
3.根据权利要求1或2的杀真菌混剂，其由两部分组成，一部分是包括在固体或液体载体中的酰胺化合物Ib，另一部分是包括在固体或液体载体中的结构式II化合物。
4.一种控制有害真菌的方法，其包括用权利要求1-3中的任一项的杀真菌混剂来处理有害真菌，它们的活动场所或要保护不受其侵害的材料、植物、种子、土壤、地区或空间，其中活性化合物酰胺化合物Ib与结构式II化合物同时使用，一起或分开，或顺次使用。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19756385.6 | 1997-12-18 | ||
| DE19756385 | 1997-12-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1282214A CN1282214A (zh) | 2001-01-31 |
| CN1165229C true CN1165229C (zh) | 2004-09-08 |
Family
ID=7852431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB988123339A Expired - Lifetime CN1165229C (zh) | 1997-12-18 | 1998-12-15 | 基于吡啶酰胺和四氯间苯二腈的杀真菌混剂 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6410572B1 (zh) |
| EP (1) | EP1039807B1 (zh) |
| JP (1) | JP4287996B2 (zh) |
| KR (1) | KR100534510B1 (zh) |
| CN (1) | CN1165229C (zh) |
| AR (1) | AR018027A1 (zh) |
| AT (1) | ATE223153T1 (zh) |
| AU (1) | AU750991B2 (zh) |
| BR (1) | BR9813682B1 (zh) |
| CA (1) | CA2312994C (zh) |
| CO (1) | CO5040001A1 (zh) |
| CZ (1) | CZ293651B6 (zh) |
| DE (1) | DE59805454D1 (zh) |
| DK (1) | DK1039807T3 (zh) |
| EA (1) | EA003390B1 (zh) |
| ES (1) | ES2183439T3 (zh) |
| HU (1) | HUP0100064A3 (zh) |
| IL (2) | IL136471A0 (zh) |
| NZ (1) | NZ505623A (zh) |
| PL (1) | PL191033B1 (zh) |
| PT (1) | PT1039807E (zh) |
| SI (1) | SI1039807T1 (zh) |
| SK (1) | SK283641B6 (zh) |
| TW (1) | TW491686B (zh) |
| UA (1) | UA54576C2 (zh) |
| WO (1) | WO1999031983A1 (zh) |
| ZA (1) | ZA9811559B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100516425C (zh) * | 2005-10-12 | 2009-07-22 | 大连舒心科技建材有限公司 | 高强度凹型吊顶龙骨 |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE296806T1 (de) * | 1999-12-09 | 2005-06-15 | Syngenta Participations Ag | Pyrazolcarboxamide und pyrazolthioamide als fungizide |
| WO2002056688A1 (de) * | 2001-01-18 | 2002-07-25 | Basf Aktiengesellschaft | Fungizide mischungen aus benzophenonen und n-biphenylnikotinamiden |
| DE10250110A1 (de) * | 2002-10-28 | 2004-05-13 | Bayer Cropscience Ag | Thiazol-(bi)cycloalkyl-carboxanilide |
| DE10347090A1 (de) * | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| PE20070409A1 (es) * | 2005-06-29 | 2007-05-07 | Basf Ag | Mezclas fungicidas con base en bifenilamidas de acido pirazolcarboxilico disustituidas en 2,4 |
| JP2009500308A (ja) * | 2005-06-30 | 2009-01-08 | ビーエーエスエフ ソシエタス・ヨーロピア | ２，５−二置換ｎ−ビフェニルピラゾールカルボキサミドをベースとした殺菌剤混合物 |
| WO2007003564A1 (de) * | 2005-07-01 | 2007-01-11 | Basf Aktiengesellschaft | Fungizide mischungen auf der basis von 3,5-disubstituierten pyrazolcarbonsäurebiphenylamiden |
| US20090042725A1 (en) * | 2005-07-01 | 2009-02-12 | Basf Aktiengesellschaft | Fungicidal Mixtures Based on 3,5-Disubstituted N-Biphenyl-Pyrazolcarboxamides |
| JP2009500375A (ja) * | 2005-07-06 | 2009-01-08 | ビーエーエスエフ ソシエタス・ヨーロピア | １−メチルピラゾール−４−イルカルボキシアニリド類から製造される殺菌剤混合物 |
| EP1813151A1 (de) * | 2006-01-26 | 2007-08-01 | BASF Aktiengesellschaft | Fungizide Mischungen auf der Basis von 1-Methyl-pyrazol-4-yl-carbonsäureaniliden |
| JP2009502747A (ja) * | 2005-07-14 | 2009-01-29 | ビーエーエスエフ ソシエタス・ヨーロピア | １−メチル−ピラゾール−４−イルカルボキシアニリド類に基づく殺菌性混合物 |
| UA103008C2 (ru) * | 2007-09-26 | 2013-09-10 | Басф Се | Трехкомпонентные фунгицидные композиции, содержащие боскалид и хлороталонил |
| HUE029892T2 (en) | 2009-10-07 | 2017-04-28 | Dow Agrosciences Llc | Synergistic fungicidal preparations for fungi in cereals |
| CN102524256A (zh) * | 2011-12-23 | 2012-07-04 | 江阴苏利化学有限公司 | 一种含有氟酰胺和百菌清的杀菌组合物 |
| KR102148190B1 (ko) | 2012-12-28 | 2020-08-26 | 다우 아그로사이언시즈 엘엘씨 | 곡류에서의 진균 방제를 위한 상승작용적 살진균 혼합물 |
| CN103242308B (zh) * | 2013-05-24 | 2015-07-01 | 青岛农业大学 | 2-氟烟酰衍生物及其制备方法和其应用 |
| CN103348982B (zh) * | 2013-07-15 | 2016-06-15 | 江苏龙灯化学有限公司 | 一种杀真菌混合物 |
| CN106028814A (zh) | 2013-12-26 | 2016-10-12 | 美国陶氏益农公司 | 大环吡啶酰胺作为杀真菌剂的用途 |
| US9955691B2 (en) | 2014-07-08 | 2018-05-01 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
| JP6742319B2 (ja) | 2014-12-30 | 2020-08-19 | ダウ アグロサイエンシィズ エルエルシー | 殺真菌活性を有するピコリンアミド化合物 |
| AU2015374376B2 (en) | 2014-12-30 | 2018-02-15 | Dow Agrosciences Llc | Picolinamides with fungicidal activity |
| CA2972403A1 (en) | 2014-12-30 | 2016-07-07 | Dow Agrosciences Llc | Picolinamide compounds with fungicidal activity |
| ES2841906T3 (es) | 2014-12-30 | 2021-07-12 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
| BR112017013676A2 (pt) | 2014-12-30 | 2018-01-09 | Dow Agrosciences Llc | uso de compostos de picolinamida como fungicidas |
| US10231452B2 (en) | 2016-08-30 | 2019-03-19 | Dow Agrosciences Llc | Thiopicolinamide compounds with fungicidal activity |
| WO2018045012A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity |
| US10111432B2 (en) | 2016-08-30 | 2018-10-30 | Dow Agrosciences Llc | Picolinamide N-oxide compounds with fungicidal activity |
| US10173982B2 (en) | 2016-08-30 | 2019-01-08 | Dow Agrosciences Llc | Picolinamides as fungicides |
| BR102018000183B1 (pt) | 2017-01-05 | 2023-04-25 | Dow Agrosciences Llc | Picolinamidas, composição para controle de um patógeno fúngico, e método para controle e prevenção de um ataque por fungos em uma planta |
| TW201842851A (zh) | 2017-05-02 | 2018-12-16 | 美商陶氏農業科學公司 | 用於穀類中的真菌防治之協同性混合物 |
| CN110996665B (zh) | 2017-05-02 | 2021-10-26 | 陶氏益农公司 | 无环吡啶酰胺化合物作为针对草坪草上的真菌病害的杀真菌剂的用途 |
| TWI774761B (zh) | 2017-05-02 | 2022-08-21 | 美商科迪華農業科技有限責任公司 | 用於穀物中的真菌防治之協同性混合物 |
| BR102019004480B1 (pt) | 2018-03-08 | 2023-03-28 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
| US11639334B2 (en) | 2018-10-15 | 2023-05-02 | Corteva Agriscience Llc | Methods for synthesis of oxypicolinamides |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1581527A (en) * | 1976-08-18 | 1980-12-17 | Lilly Industries Ltd | Fungicidal formulations |
| IT1114941B (it) * | 1977-12-27 | 1986-02-03 | Sipcam Spa | Fumero - studio consulenza brevetti s.n.c.via s.agnese,12 milano |
| JPS5495728A (en) * | 1978-01-12 | 1979-07-28 | Yoshitomi Pharmaceut Ind Ltd | Marine anti-fouling agent |
| JPS56167605A (en) * | 1980-05-30 | 1981-12-23 | Nippon Nohyaku Co Ltd | Seed disinfectant |
| JPS57149204A (en) * | 1981-03-10 | 1982-09-14 | Kumiai Chem Ind Co Ltd | Preservative and mildew-proofing agent of wood |
| ES2011602T3 (es) * | 1986-08-12 | 1994-07-16 | Mitsubishi Chem Ind | Derivados de piridinacarboxamida y su uso como fungicidas. |
| IL103614A (en) * | 1991-11-22 | 1998-09-24 | Basf Ag | Carboxamides for controlling botrytis and certain novel such compounds |
| GB9401780D0 (en) | 1994-01-31 | 1994-03-23 | Nickerson Biocem Ltd | Modified plants |
| TW349094B (en) | 1995-09-05 | 1999-01-01 | Basf Ag | Compositions and methods for controlling harmful fungi |
| TW384208B (en) * | 1995-09-22 | 2000-03-11 | Basf Ag | Compositions and methods for controlling harmful fungi |
| DE19615977A1 (de) * | 1996-04-22 | 1997-10-23 | Basf Ag | Mittel und Verfahren zur Bekämpfung von Schadpilzen |
-
1998
- 1998-12-14 TW TW087120736A patent/TW491686B/zh not_active IP Right Cessation
- 1998-12-15 NZ NZ505623A patent/NZ505623A/xx unknown
- 1998-12-15 HU HU0100064A patent/HUP0100064A3/hu unknown
- 1998-12-15 AT AT98966338T patent/ATE223153T1/de active
- 1998-12-15 WO PCT/EP1998/008226 patent/WO1999031983A1/de active IP Right Grant
- 1998-12-15 ES ES98966338T patent/ES2183439T3/es not_active Expired - Lifetime
- 1998-12-15 US US09/581,795 patent/US6410572B1/en not_active Expired - Lifetime
- 1998-12-15 UA UA2000074345A patent/UA54576C2/uk unknown
- 1998-12-15 CZ CZ20002227A patent/CZ293651B6/cs not_active IP Right Cessation
- 1998-12-15 PL PL341310A patent/PL191033B1/pl unknown
- 1998-12-15 SK SK815-2000A patent/SK283641B6/sk not_active IP Right Cessation
- 1998-12-15 AU AU22732/99A patent/AU750991B2/en not_active Ceased
- 1998-12-15 KR KR10-2000-7006701A patent/KR100534510B1/ko not_active IP Right Cessation
- 1998-12-15 PT PT98966338T patent/PT1039807E/pt unknown
- 1998-12-15 IL IL13647198A patent/IL136471A0/xx active IP Right Grant
- 1998-12-15 CA CA002312994A patent/CA2312994C/en not_active Expired - Lifetime
- 1998-12-15 BR BRPI9813682-8A patent/BR9813682B1/pt not_active IP Right Cessation
- 1998-12-15 EA EA200000673A patent/EA003390B1/ru not_active IP Right Cessation
- 1998-12-15 SI SI9830153T patent/SI1039807T1/xx unknown
- 1998-12-15 DK DK98966338T patent/DK1039807T3/da active
- 1998-12-15 DE DE59805454T patent/DE59805454D1/de not_active Expired - Lifetime
- 1998-12-15 JP JP2000524996A patent/JP4287996B2/ja not_active Expired - Fee Related
- 1998-12-15 CN CNB988123339A patent/CN1165229C/zh not_active Expired - Lifetime
- 1998-12-15 EP EP98966338A patent/EP1039807B1/de not_active Expired - Lifetime
- 1998-12-17 ZA ZA9811559A patent/ZA9811559B/xx unknown
- 1998-12-18 CO CO98075480A patent/CO5040001A1/es unknown
- 1998-12-18 AR ARP980106491A patent/AR018027A1/es active IP Right Grant
-
2000
- 2000-05-31 IL IL136471A patent/IL136471A/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100516425C (zh) * | 2005-10-12 | 2009-07-22 | 大连舒心科技建材有限公司 | 高强度凹型吊顶龙骨 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1165229C (zh) | 基于吡啶酰胺和四氯间苯二腈的杀真菌混剂 | |
| CN1206916C (zh) | 基于酰胺化合物和吡咯的杀真菌混剂 | |
| CN1213656C (zh) | 基于酰胺化合物和吡啶衍生物的杀真菌混合物 | |
| CN100337543C (zh) | 基于酰胺化合物和吡啶衍生物的杀真菌混合物 | |
| CN1197373A (zh) | 控制有害真菌的组合物和方法 | |
| CN1129357C (zh) | 控制有害真菌的组合物及方法 | |
| CN1282213A (zh) | 基于酰胺化合物和吗啉或哌啶衍生物的杀真菌混合物 | |
| CN1200651A (zh) | 用抑制细胞色素复合物ⅲ呼吸作用的活性物质与喹螨醚结合消灭寄生真菌的方法 | |
| CN1220433C (zh) | 增效除草混合物 | |
| CN1099220A (zh) | 杀微生物剂 | |
| CN1165228C (zh) | 基于吡啶酰胺和氯苯嘧啶醇的杀真菌混合物 | |
| CN1165227C (zh) | 基于吡啶酰胺和吗啉或哌啶衍生物的杀真菌混合物 | |
| CN1436044A (zh) | 杀菌剂活性化合物组合物 | |
| CN1282212A (zh) | 基于酰胺化合物和苯并咪唑或释放它们的前体的杀真菌混合物 | |
| CN1336798A (zh) | 包含噻吩并[2,3－d]嘧啶－4－酮的杀真菌组合物 | |
| CN1294491A (zh) | 基于三(肟醚)衍生物和丝核菌杀真菌剂的杀真菌混合物 | |
| CN1069636C (zh) | 甲氨酰羧酰胺 | |
| CN1149924C (zh) | 基于三(肟醚)衍生物和其它嗜球果伞素的杀真菌混合物 | |
| CN1144523C (zh) | 基于三(肟醚)衍生物和抗性诱导剂的杀真菌混合物 | |
| CN1711020A (zh) | 基于***并嘧啶衍生物和酰胺化合物的杀真菌混合物 | |
| CN1191756C (zh) | 基于酰胺化合物和吡啶衍生物的杀真菌混合物 | |
| CN1122442C (zh) | 杀真菌混剂 | |
| CN1158922C (zh) | 基于吗啉或哌啶衍生物和肟醚衍生物的杀菌混剂 | |
| CN87103191A (zh) | 杀真菌的吡啶基环丙烷甲酰胺类化合物 | |
| CN1255040A (zh) | 防治有害真菌的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CX01 | Expiry of patent term |
Granted publication date: 20040908 |
|
| CX01 | Expiry of patent term |