ES2536305T3 - Pesticidas mesoiónicos de pirido[1,2-a]pirimidina - Google Patents
Pesticidas mesoiónicos de pirido[1,2-a]pirimidinaInfo
- Publication number
- ES2536305T3 ES2536305T3 ES11808109.0T ES11808109T ES2536305T3 ES 2536305 T3 ES2536305 T3 ES 2536305T3 ES 11808109 T ES11808109 T ES 11808109T ES 2536305 T3 ES2536305 T3 ES 2536305T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- compounds
- test
- days
- 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.)
- Active
Links
- 239000000575 pesticide Substances 0.000 title description 5
- VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical compound C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- DBHFICNYODFKBO-UHFFFAOYSA-N n-(pyrimidin-5-ylmethyl)pyridin-2-amine Chemical compound C=1N=CN=CC=1CNC1=CC=CC=N1 DBHFICNYODFKBO-UHFFFAOYSA-N 0.000 claims abstract description 5
- XLVVEEAVMUODOZ-UHFFFAOYSA-N n-pyridin-2-yl-1-pyrimidin-5-ylmethanimine Chemical compound C=1N=CN=CC=1C=NC1=CC=CC=N1 XLVVEEAVMUODOZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000012360 testing method Methods 0.000 description 87
- 240000007594 Oryza sativa Species 0.000 description 39
- 229940126214 compound 3 Drugs 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 35
- 239000000203 mixture Substances 0.000 description 32
- 241000607479 Yersinia pestis Species 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- -1 methoxy, ethoxy, n-propoxy, isopropoxy group Chemical group 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 238000011282 treatment Methods 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 239000002689 soil Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 235000002639 sodium chloride Nutrition 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 230000012010 growth Effects 0.000 description 14
- 239000012265 solid product Substances 0.000 description 13
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- 230000015572 biosynthetic process Effects 0.000 description 11
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- 230000000694 effects Effects 0.000 description 10
- 239000004576 sand Substances 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 8
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- 241001556089 Nilaparvata lugens Species 0.000 description 8
- 235000021329 brown rice Nutrition 0.000 description 8
- 238000013461 design Methods 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
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- 239000002917 insecticide Substances 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 230000009885 systemic effect Effects 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241001057636 Dracaena deremensis Species 0.000 description 6
- 239000005907 Indoxacarb Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 244000181917 Rubus leucodermis Species 0.000 description 5
- 235000011036 Rubus leucodermis Nutrition 0.000 description 5
- 235000003942 Rubus occidentalis Nutrition 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 230000003071 parasitic effect Effects 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 241000237858 Gastropoda Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 244000000013 helminth Species 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- LHZOTJOOBRODLL-UHFFFAOYSA-O 4-oxo-1-(pyrimidin-5-ylmethyl)-3-[3-(trifluoromethyl)phenyl]-5h-pyrido[1,2-a]pyrimidine-1,5-diium-2-olate Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC=NC=2)C(O)=C1C1=CC=CC(C(F)(F)F)=C1 LHZOTJOOBRODLL-UHFFFAOYSA-O 0.000 description 3
- 241001600408 Aphis gossypii Species 0.000 description 3
- 241000995027 Empoasca fabae Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 125000004995 haloalkylthio group Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000000590 parasiticidal effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241000238421 Arthropoda Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 241000242722 Cestoda Species 0.000 description 2
- 241001414720 Cicadellidae Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000086608 Empoasca vitis Species 0.000 description 2
- 241000927584 Frankliniella occidentalis Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000256682 Peregrinus maidis Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
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- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
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- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
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- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- FREJAOSUHFGDBW-UHFFFAOYSA-N pyrimidine-5-carbaldehyde Chemical compound O=CC1=CN=CN=C1 FREJAOSUHFGDBW-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QSLPNSWXUQHVLP-FIBGUPNXSA-N trideuterio($l^{1}-sulfanyl)methane Chemical compound [2H]C([2H])([2H])[S] QSLPNSWXUQHVLP-FIBGUPNXSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000004235 valence bond calculation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061427855P | 2010-12-29 | 2010-12-29 | |
| US201061427855P | 2010-12-29 | ||
| US201161550675P | 2011-10-24 | 2011-10-24 | |
| US201161550675P | 2011-10-24 | ||
| PCT/US2011/066798 WO2012092115A1 (en) | 2010-12-29 | 2011-12-22 | Mesoionic pyrido [1,2 -a] pyrimidine pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2536305T3 true ES2536305T3 (es) | 2015-05-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11808109.0T Active ES2536305T3 (es) | 2010-12-29 | 2011-12-22 | Pesticidas mesoiónicos de pirido[1,2-a]pirimidina |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8895738B2 (enExample) |
| EP (1) | EP2658856B1 (enExample) |
| JP (1) | JP5911510B2 (enExample) |
| KR (1) | KR101897840B1 (enExample) |
| CN (2) | CN105198874A (enExample) |
| AR (1) | AR084646A1 (enExample) |
| AU (1) | AU2011352379B2 (enExample) |
| BR (1) | BR112013009935B8 (enExample) |
| CA (1) | CA2817902A1 (enExample) |
| CO (1) | CO6761321A2 (enExample) |
| ES (1) | ES2536305T3 (enExample) |
| HU (1) | HUE025531T2 (enExample) |
| IL (1) | IL225859A (enExample) |
| MA (1) | MA34830B1 (enExample) |
| MX (1) | MX358389B (enExample) |
| PH (1) | PH12013501402A1 (enExample) |
| RU (1) | RU2585616C2 (enExample) |
| SG (1) | SG189206A1 (enExample) |
| TW (1) | TWI528899B (enExample) |
| UY (1) | UY33842A (enExample) |
| WO (1) | WO2012092115A1 (enExample) |
| ZA (1) | ZA201302430B (enExample) |
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| TWI401023B (zh) | 2008-02-06 | 2013-07-11 | Du Pont | 中離子農藥 |
| UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| KR20140018865A (ko) * | 2010-12-27 | 2014-02-13 | 스미또모 가가꾸 가부시끼가이샤 | 절지동물 해충 방제 조성물 및 절지동물 해충의 방제 방법 |
| WO2012104273A1 (de) | 2011-02-01 | 2012-08-09 | Bayer Cropscience Ag | Heteroarylpiperidin und -piperazinderivate als fungizide |
| TWI572587B (zh) | 2011-12-15 | 2017-03-01 | 杜邦股份有限公司 | 丙二酸二鹽及用以製備丙二醯基二鹵化物之方法 |
| JP2017141250A (ja) * | 2012-06-21 | 2017-08-17 | 住友化学株式会社 | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| JP6119362B2 (ja) * | 2012-06-21 | 2017-04-26 | 住友化学株式会社 | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| EP2684879A1 (en) | 2012-07-09 | 2014-01-15 | Basf Se | Substituted mesoionic compounds for combating animal pests |
| WO2014053404A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
| JP2015532274A (ja) | 2012-10-01 | 2015-11-09 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 栽培植物へのｎ−チオ−アントラニルアミド化合物の使用 |
| AU2013326645A1 (en) | 2012-10-01 | 2015-04-23 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
| CN104768379A (zh) | 2012-10-01 | 2015-07-08 | 巴斯夫欧洲公司 | 控制鱼尼汀-调节剂杀虫剂耐药性昆虫的方法 |
| WO2014053403A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling insecticide resistant insects |
| WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
| US9718762B2 (en) | 2012-10-31 | 2017-08-01 | Syngenta Participations Ag | Insecticidal compounds |
| WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
| US10117430B2 (en) | 2012-12-14 | 2018-11-06 | Basf Se | Malononitrile compounds for controlling animal pests |
| BR112015014753B8 (pt) | 2012-12-20 | 2020-03-03 | Basf Agro Bv | composições, uso de uma composição, método para o combate de fungos fitopatogênicos e uso dos componentes |
| BR112015015503A2 (pt) | 2012-12-27 | 2017-07-11 | Basf Se | composto substituído, composição veterinária, utilização de um composto, método para o controle de pragas de invertebrados e para o tratamento ou proteção de um animal e material de propagação do vegetal |
| ES2746932T3 (es) | 2013-01-09 | 2020-03-09 | Basf Agro Bv | Proceso para la preparación de oxiranos y triazoles sustituidos |
| US20160050930A1 (en) | 2013-03-28 | 2016-02-25 | Syngenta Limited | Methods of controlling neonicotinoid resistant pests |
| AR096022A1 (es) | 2013-04-11 | 2015-12-02 | Basf Se | Compuestos de pirimidinio sustituido, útiles para combatir plagas de animales |
| EP2986598B1 (en) | 2013-04-19 | 2017-03-29 | Basf Se | N-substituted acyl-imino-pyridine compounds and derivatives for combating animal pests |
| BR112015031439A2 (pt) | 2013-06-21 | 2017-07-25 | Basf Se | métodos para o combate ou controle das pragas, para o tratamento, prevenção e proteção de culturas de soja, para o controle e proteção do material de propagação dos vegetais de soja, para o combate ou controle das pragas e utilização de um composto de fórmula i |
| EP3016949B1 (en) | 2013-07-02 | 2020-05-13 | Syngenta Participations AG | Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents |
| US10512267B2 (en) | 2013-07-08 | 2019-12-24 | BASF Agro, B.V. | Compositions comprising a triazole compound and a biopesticide |
| PL3022185T3 (pl) | 2013-07-15 | 2018-02-28 | Basf Se | Związki szkodnikobójcze |
| EP3046919B1 (en) | 2013-09-19 | 2019-08-07 | Basf Se | N-acylimino heterocyclic compounds |
| WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
| BR112016008555A8 (pt) | 2013-10-18 | 2020-03-10 | Basf Agrochemical Products Bv | usos do composto carboxamida ativo pesticida e método de proteção de material de propagação vegetal |
| EP2873668A1 (en) | 2013-11-13 | 2015-05-20 | Syngenta Participations AG. | Pesticidally active bicyclic heterocycles with sulphur containing substituents |
| WO2015071389A1 (en) * | 2013-11-15 | 2015-05-21 | Nestec S.A. | Compositions for use in the prevention or treatment of urt infections in infants or young children at risk |
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| WO2015091649A1 (en) | 2013-12-18 | 2015-06-25 | Basf Se | N-substituted imino heterocyclic compounds |
| JP6469111B2 (ja) | 2013-12-20 | 2019-02-13 | シンジェンタ パーティシペーションズ アーゲー | 有害生物防除活性を有する硫黄含有置換基を伴う置換５，５−二環式複素環 |
| EP3086644A1 (en) | 2013-12-23 | 2016-11-02 | Syngenta Participations AG | Benzoxaborole fungicides |
| WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
| WO2015177063A1 (en) | 2014-05-19 | 2015-11-26 | Syngenta Participations Ag | Insecticidally active amide derivatives with sulfur-substituted phenyl or pyridine groups |
| AU2015281187B2 (en) | 2014-06-25 | 2018-10-04 | BASF Agro B.V. | Pesticidal compositions |
| CN104082333A (zh) * | 2014-07-03 | 2014-10-08 | 广西农喜作物科学有限公司 | 含噻虫胺的杀虫组合物 |
| KR102424208B1 (ko) | 2014-07-04 | 2022-07-21 | 스미또모 가가꾸 가부시끼가이샤 | 유해 생물 방제 조성물 및 그 용도 |
| WO2016091731A1 (en) | 2014-12-11 | 2016-06-16 | Syngenta Participations Ag | Pesticidally active tetracyclic derivatives with sulfur containing substituents |
| WO2016120182A1 (en) | 2015-01-30 | 2016-08-04 | Syngenta Participations Ag | Pesticidally active amide heterocyclic derivatives with sulphur containing substituents |
| US10273221B2 (en) | 2015-03-27 | 2019-04-30 | Syngenta Participations Ag | Microbiocidal heterobicyclic derivatives |
| AU2016247473A1 (en) | 2015-04-17 | 2017-11-09 | Basf Agrochemical Products B.V. | Method for controlling non-crop pests |
| JP2018513190A (ja) | 2015-04-24 | 2018-05-24 | シンジェンタ パーティシペーションズ アーゲー | 硫黄置換５員環複素環を有する有害生物防除に活性な多環式誘導体 |
| ES2762947T3 (es) | 2015-04-24 | 2020-05-26 | Syngenta Participations Ag | Derivados policíclicos con actividad plaguicida con anillos heterocíclicos de cinco miembros sustituidos con azufre |
| ES2762958T3 (es) | 2015-07-01 | 2020-05-26 | Syngenta Participations Ag | Derivados tetracíclicos activos como plaguicidas con sustituyentes que contienen azufre |
| AR106070A1 (es) | 2015-09-23 | 2017-12-06 | Syngenta Participations Ag | Benzamidas sustituidas con isoxazolina como insecticidas |
| EP3353173B1 (en) | 2015-09-25 | 2021-07-21 | Syngenta Participations AG | Pesticidally active polycyclic derivatives with 5-membered sulfur containing heterocyclic ring systems |
| WO2017050751A1 (en) | 2015-09-25 | 2017-03-30 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| US10556884B2 (en) | 2015-09-28 | 2020-02-11 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| SI3361870T1 (sl) | 2015-10-14 | 2020-07-31 | Syngenta Participations Ag | Fungicidni sestavki |
| WO2017067839A1 (en) | 2015-10-23 | 2017-04-27 | Syngenta Participations Ag | Microbiocidal phenylamidine derivatives |
| WO2017067837A1 (en) | 2015-10-23 | 2017-04-27 | Syngenta Participations Ag | Microbiocidal phenylamidine derivatives |
| BR112018008467A2 (pt) | 2015-10-28 | 2018-11-06 | Syngenta Participations Ag | derivados de oxadiazol microbiocidas |
| CN108349915A (zh) | 2015-11-04 | 2018-07-31 | 先正达参股股份有限公司 | 杀微生物的苯胺衍生物 |
| CN108290885A (zh) | 2015-11-23 | 2018-07-17 | 先正达参股股份有限公司 | 具有含硫和含环丙基的取代基的杀有害生物活性杂环衍生物 |
| AU2016363632A1 (en) * | 2015-12-03 | 2018-06-07 | Bayer Cropscience Aktiengesellschaft | Mesoionic halogenated 3-(acetyl)-1-((1,3-thiazol-5-yl)methyl)-1h-imidazo(1,2-a)pyridin-4-ium-2-olate derivatives and related compounds as insecticides |
| AU2016371496B2 (en) * | 2015-12-14 | 2021-01-14 | Fmc Corporation | Heterocycle-substituted bicyclic azole pesticides |
| BR112018012338A2 (pt) | 2015-12-17 | 2018-12-04 | Syngenta Participations Ag | derivados de oxadiazol microbiocidas |
| MX2018007527A (es) | 2015-12-22 | 2018-09-07 | Syngenta Participations Ag | Derivados de pirazol activos como pesticidas. |
| CN105532680B (zh) * | 2016-01-27 | 2018-06-01 | 江西省农业科学院植物保护研究所 | 一种含三氟苯嘧啶和环氧虫啶的高效复配农药组合物 |
| WO2017134066A1 (en) | 2016-02-05 | 2017-08-10 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| CA3012901A1 (en) | 2016-02-18 | 2017-08-24 | Syngenta Participations Ag | Pesticidally active pyrazole derivatives |
| JP2019514845A (ja) | 2016-03-15 | 2019-06-06 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物オキサジアゾール誘導体 |
| WO2017162868A1 (en) | 2016-03-24 | 2017-09-28 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| WO2017174449A1 (en) | 2016-04-07 | 2017-10-12 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| JP2019514860A (ja) | 2016-04-08 | 2019-06-06 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性オキサジアゾール誘導体 |
| EP3442969A1 (en) | 2016-04-12 | 2019-02-20 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
| WO2017178408A1 (en) | 2016-04-15 | 2017-10-19 | Syngenta Participations Ag | Microbiocidal silicon containing aryl derivatives |
| TW201738229A (zh) | 2016-04-26 | 2017-11-01 | 杜邦股份有限公司 | 製備ｎ－［（５－嘧啶基）甲基］－２－吡啶胺之方法 |
| WO2017207757A1 (en) | 2016-06-03 | 2017-12-07 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| AR108745A1 (es) | 2016-06-21 | 2018-09-19 | Syngenta Participations Ag | Derivados de oxadiazol microbiocidas |
| US10757941B2 (en) | 2016-07-22 | 2020-09-01 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| WO2018015449A1 (en) | 2016-07-22 | 2018-01-25 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| EP3487855A1 (en) | 2016-07-22 | 2019-05-29 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
| WO2018029242A1 (en) | 2016-08-11 | 2018-02-15 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| WO2018041729A2 (en) | 2016-09-01 | 2018-03-08 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| WO2018055133A1 (en) | 2016-09-23 | 2018-03-29 | Syngenta Participations Ag | Microbiocidal tetrazolone derivatives |
| CN109923112A (zh) | 2016-09-23 | 2019-06-21 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
| CN109890208B (zh) | 2016-09-28 | 2021-10-22 | 先正达参股股份有限公司 | 杀真菌组合物 |
| RU2019112871A (ru) | 2016-09-28 | 2020-10-29 | Ниппон Каяку Кабусики Кайся | Новое мезоионное инсектицидное соединение |
| EP3522715B1 (en) | 2016-10-06 | 2021-01-20 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
| JP7077314B2 (ja) | 2016-10-27 | 2022-05-30 | シンジェンタ パーティシペーションズ アーゲー | 硫黄およびヒドロキシルアミン置換基を有する有害生物防除的に活性な複素環式誘導体 |
| WO2018091389A1 (en) | 2016-11-17 | 2018-05-24 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| WO2018095795A1 (en) | 2016-11-23 | 2018-05-31 | Syngenta Participations Ag | Pesticidally active polycyclic derivatives with sulfur containing substituents |
| US10961248B2 (en) | 2016-12-01 | 2021-03-30 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| EP3554242A1 (en) | 2016-12-15 | 2019-10-23 | Syngenta Participations AG | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| BR112019012262A2 (pt) * | 2016-12-16 | 2019-12-03 | Bayer Ag | imidazopiridinas mesoiônicas para uso como inseticidas |
| EP3336086A1 (en) | 2016-12-19 | 2018-06-20 | Syngenta Participations Ag | Pesticidally active azetidine sulfone amide isoxazoline derivatives |
| EP3336087A1 (en) | 2016-12-19 | 2018-06-20 | Syngenta Participations Ag | Pesticidally active azetidine sulfone amide isoxazoline derivatives |
| TWI772367B (zh) | 2017-02-16 | 2022-08-01 | 瑞士商先正達合夥公司 | 殺真菌組成物 |
| TWI793104B (zh) | 2017-02-21 | 2023-02-21 | 瑞士商先正達合夥公司 | 具有含硫取代基的殺有害生物活性雜環衍生物 |
| UY37623A (es) | 2017-03-03 | 2018-09-28 | Syngenta Participations Ag | Derivados de oxadiazol tiofeno fungicidas |
| EP3592738A1 (en) | 2017-03-10 | 2020-01-15 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
| TW201840542A (zh) | 2017-03-22 | 2018-11-16 | 瑞士商先正達合夥公司 | 殺有害生物活性環丙基甲基醯胺衍生物 |
| US11213032B2 (en) | 2017-03-23 | 2022-01-04 | Syngenta Participations Ag | Insecticidal compounds |
| EP3601275A1 (en) | 2017-03-23 | 2020-02-05 | Syngenta Participations AG | Insecticidal compounds |
| CN113979962A (zh) | 2017-03-31 | 2022-01-28 | 先正达参股股份有限公司 | 杀真菌组合物 |
| BR112019020134B1 (pt) | 2017-03-31 | 2023-05-09 | Syngenta Participations Ag | Composições fungicidas |
| BR112019020693B1 (pt) | 2017-04-03 | 2023-11-28 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas, suas composições, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos utilizando tais compostos e seus usos |
| WO2018184988A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| EP3606919A1 (en) | 2017-04-05 | 2020-02-12 | Syngenta Participations AG | Pesticidally active pyrazole derivatives |
| BR112019020756B1 (pt) | 2017-04-05 | 2023-11-28 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbicidas, composição agroquímica compreendendo os mesmos, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso desses compostos |
| BR112019020735B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas e seu uso, composição agroquímica e método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos |
| WO2018185185A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Pesticidally active pyrazole derivatives |
| WO2018184987A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| US11472797B2 (en) | 2017-04-05 | 2022-10-18 | Syngenta Participations Ag | Pesticidally active pyrazole derivatives |
| WO2018184986A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| WO2018184985A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| WO2018185211A1 (en) | 2017-04-06 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| US20200037600A1 (en) * | 2017-04-12 | 2020-02-06 | Bayer Aktiengesellschaft | Mesoionic imidazopyridines as insecticides |
| WO2018197315A1 (en) | 2017-04-25 | 2018-11-01 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| JP7309615B2 (ja) | 2017-05-02 | 2023-07-18 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する有害生物防除に活性な複素環式誘導体 |
| CN110612301B (zh) | 2017-05-08 | 2023-05-23 | 先正达参股股份有限公司 | 具有含硫的苯基和吡啶基取代基的咪唑并嘧啶衍生物 |
| EP3621964B1 (en) * | 2017-05-09 | 2022-03-02 | FMC Corporation | Mesoionic insecticides |
| WO2018206419A1 (en) | 2017-05-12 | 2018-11-15 | Syngenta Participations Ag | Microbiocidal heterobicyclic derivatives |
| CN106973923A (zh) * | 2017-05-13 | 2017-07-25 | 北京科发伟业农药技术中心 | 一种含三氟苯嘧啶的杀虫组合物 |
| WO2018215304A1 (en) | 2017-05-22 | 2018-11-29 | Syngenta Participations Ag | Tetracyclic pyridazine sulphur containing compounds and their use as pesticides |
| WO2018219773A1 (en) | 2017-06-02 | 2018-12-06 | Syngenta Participations Ag | Fungicidal compositions |
| WO2018219825A1 (en) | 2017-06-02 | 2018-12-06 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| US11154058B2 (en) | 2017-06-14 | 2021-10-26 | Syngenta Participations Ag | Fungicidal compositions |
| CN107156151A (zh) * | 2017-06-16 | 2017-09-15 | 江苏天容集团股份有限公司 | 含有三氟苯嘧啶和杀虫双的杀虫组合物 |
| CN110770235A (zh) | 2017-06-16 | 2020-02-07 | 巴斯夫欧洲公司 | 用于防除动物害虫的介离子咪唑鎓化合物和衍生物 |
| UY37775A (es) | 2017-06-19 | 2019-01-31 | Syngenta Participations Ag | Derivados de pirazol activos como plaguicida |
| CN107156152A (zh) * | 2017-06-22 | 2017-09-15 | 江苏天容集团股份有限公司 | 含有三氟苯嘧啶和杀虫磺的杀虫组合物 |
| CN107232214A (zh) * | 2017-06-22 | 2017-10-10 | 江苏天容集团股份有限公司 | 含有三氟苯嘧啶和杀螟丹的杀虫组合物 |
| CA3067309A1 (en) | 2017-06-28 | 2019-01-03 | Syngenta Participations Ag | Fungicidal compositions |
| WO2019008072A1 (en) | 2017-07-05 | 2019-01-10 | Syngenta Participations Ag | HETEROCYCLIC DERIVATIVES HAVING PESTICIDE ACTIVITY HAVING SUBSTITUENTS CONTAINING SULFUR |
| EP3649128A1 (en) | 2017-07-07 | 2020-05-13 | Syngenta Participations AG | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| WO2019011926A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| WO2019011929A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| WO2019011928A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| BR112020000465B1 (pt) | 2017-07-11 | 2024-02-20 | Syngenta Participations Ag | Derivados oxadiazol microbiocidas |
| WO2019012001A1 (en) | 2017-07-12 | 2019-01-17 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| WO2019012011A1 (en) | 2017-07-12 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| BR112020000463A2 (pt) | 2017-07-13 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
| AR112673A1 (es) | 2017-08-11 | 2019-11-27 | Syngenta Participations Ag | Derivados de pirazol activos como plaguicidas |
| EP3665166A1 (en) | 2017-08-11 | 2020-06-17 | Syngenta Participations AG | Pesticidally active pyrazole derivatives |
| US20200288713A1 (en) | 2017-08-11 | 2020-09-17 | Syngenta Participations Ag | Pesticidally active pyrazole derivatives |
| AR112672A1 (es) | 2017-08-11 | 2019-11-27 | Syngenta Participations Ag | Derivados de tiofeno activos como plaguicidas |
| WO2019042932A1 (en) * | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
| CN111107745B (zh) | 2017-09-13 | 2021-12-07 | 先正达参股股份有限公司 | 杀真菌组合物 |
| ES2908668T3 (es) | 2017-09-13 | 2022-05-03 | Syngenta Participations Ag | Derivados de quinolina (tio)carboxamida microbiocidas |
| EP3681285B1 (en) | 2017-09-13 | 2021-11-17 | Syngenta Participations AG | Microbiocidal quinoline (thio)carboxamide derivatives |
| US11241011B2 (en) | 2017-09-13 | 2022-02-08 | Syngenta Participations Ag | Microbiocidal quinoline (thio)carboxamide derivatives |
| ES2896598T3 (es) | 2017-09-13 | 2022-02-24 | Syngenta Participations Ag | Derivados de quinolina (tio)carboxamida microbiocidas |
| US20200267978A1 (en) | 2017-09-13 | 2020-08-27 | Syngenta Participations Ag | Microbiocidal quinoline (thio)carboxamide derivatives |
| US11178869B2 (en) | 2017-09-13 | 2021-11-23 | Syngenta Participations Ag | Microbiocidal quinoline (thio)carboxamide derivatives |
| CN111093372B (zh) | 2017-09-13 | 2022-05-27 | 先正达参股股份有限公司 | 杀微生物的喹啉(硫代)羧酰胺衍生物 |
| JP7267262B2 (ja) | 2017-09-18 | 2023-05-01 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物活性な複素環式誘導体 |
| CN109553615B (zh) * | 2017-09-26 | 2020-09-22 | 沈阳中化农药化工研发有限公司 | 一种嘧啶盐类化合物及其用途 |
| UY37913A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan un grupo terminal cuaternario |
| UY37912A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan grupos terminales heteroarilo o heteroariloxi |
| WO2019068819A1 (en) | 2017-10-06 | 2019-04-11 | Syngenta Participations Ag | PYRROLE DERIVATIVES ACTIVE ON THE PESTICIDE PLAN |
| EP3692038A1 (en) | 2017-10-06 | 2020-08-12 | Syngenta Participations AG | Pesticidally active pyrrole derivatives |
| WO2019076778A1 (en) | 2017-10-16 | 2019-04-25 | Syngenta Participations Ag | HETEROCYCLIC DERIVATIVES HAVING PESTICIDAL ACTIVITY HAVING SUBSTITUENTS CONTAINING SULFUR AND SULFONIMIDAMIDES |
| WO2019086474A1 (en) | 2017-10-31 | 2019-05-09 | Syngenta Participations Ag | Pesticidally active mesoionics heterocyclic compounds |
| WO2019096709A1 (en) | 2017-11-15 | 2019-05-23 | Syngenta Participations Ag | Microbiocidal picolinamide derivatives |
| CN111356679A (zh) | 2017-11-20 | 2020-06-30 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
| KR102697953B1 (ko) | 2017-11-29 | 2024-08-21 | 신젠타 파티서페이션즈 아게 | 살미생물 티아졸 유도체 |
| WO2019034796A1 (en) | 2017-12-01 | 2019-02-21 | Syngenta Participations Ag | NEW PYRIMIDINE DERIVATIVES |
| WO2019115404A1 (en) | 2017-12-13 | 2019-06-20 | Syngenta Participations Ag | Pesticidally active mesoionic heterocyclic compounds |
| CN111566087A (zh) | 2017-12-19 | 2020-08-21 | 先正达参股股份有限公司 | 杀微生物的吡啶甲酰胺衍生物 |
| WO2019134840A1 (en) * | 2018-01-05 | 2019-07-11 | Basf Se | Control of pests of soybean plants with mesoionic compounds |
| BR112020014341A2 (pt) | 2018-01-15 | 2020-12-08 | Syngenta Participations Ag | Derivados heterocíclicos pesticidamente ativos com substituintes contendo enxofre |
| WO2019173173A1 (en) | 2018-03-05 | 2019-09-12 | E. I. Du Pont De Nemours And Company | Process and intermidiates for the preparation of certain mesoionic pesticides |
| CN110452238B (zh) * | 2018-04-18 | 2020-08-11 | 东莞市东阳光农药研发有限公司 | 嘧啶鎓化合物及其用途 |
| WO2019219689A1 (en) | 2018-05-18 | 2019-11-21 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfoximine containing substituents |
| CN108373468B (zh) * | 2018-05-18 | 2019-12-17 | 武汉工程大学 | 一种n-2-吡啶-5-嘧啶甲胺的制备方法 |
| WO2019229088A1 (en) | 2018-05-30 | 2019-12-05 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| WO2019229089A1 (en) | 2018-05-31 | 2019-12-05 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| AR115495A1 (es) | 2018-06-06 | 2021-01-27 | Syngenta Crop Protection Ag | Derivados heterocíclicos con sustituyentes que contienen azufre activos como plaguicidas |
| KR102808245B1 (ko) | 2018-06-06 | 2025-05-14 | 신젠타 크롭 프로텍션 아게 | 설폭시민 함유 치환체를 갖는 살충 활성 헤테로사이클릭 유도체 |
| US20210163459A1 (en) | 2018-06-19 | 2021-06-03 | Syngenta Crop Protection Ag | Pesticidally active azetidine sulfones amide isoxazoline derivatives |
| WO2019243253A1 (en) | 2018-06-19 | 2019-12-26 | Syngenta Crop Protection Ag | Pesticidally active isoxazoline derivatives containing an amide group and an azetidine sulfone group |
| WO2019243263A1 (en) | 2018-06-19 | 2019-12-26 | Syngenta Participations Ag | Insecticidal compounds |
| WO2019243256A1 (en) | 2018-06-19 | 2019-12-26 | Syngenta Crop Protection Ag | Pesticidally active isoxazoline derivatives containing an amide group and an azetidine sulfone group |
| AU2019293690A1 (en) | 2018-06-29 | 2020-12-17 | Syngenta Participations Ag | Pesticidally active azole-amide compounds |
| US20210269426A1 (en) | 2018-06-29 | 2021-09-02 | Syngenta Crop Protection Ag | Microbiocidal oxadiazole derivatives |
| EP3818058A1 (en) | 2018-07-02 | 2021-05-12 | Syngenta Crop Protection AG | 3-(2-thienyl)-5-(trifluoromethyl)-1,2,4-oxadiazole derivatives as agrochemical fungicides |
| WO2020011808A1 (en) | 2018-07-13 | 2020-01-16 | Syngenta Crop Protection Ag | Pesticidally-active bicyclic heteroaromatic compounds |
| CN112689631A (zh) | 2018-07-16 | 2021-04-20 | 先正达农作物保护股份公司 | 杀微生物的噁二唑衍生物 |
| WO2020025658A1 (en) | 2018-08-03 | 2020-02-06 | Syngenta Crop Protection Ag | Pesticidally-active bicyclic heteroaromatic compounds |
| US20210238176A1 (en) | 2018-08-07 | 2021-08-05 | Syngenta Crop Protection Ag | Pesticidally-active bicyclic heteroaromatic compounds |
| CN109006842A (zh) * | 2018-08-13 | 2018-12-18 | 广东顾地丰生物科技有限公司 | 一种含三氟苯嘧啶和哌虫啶的高效复配农药组合物 |
| WO2020035565A1 (en) | 2018-08-17 | 2020-02-20 | Syngenta Crop Protection Ag | Pesticidally-active mesoionic bicyclic heteroaromatic compounds |
| EP3853207B1 (en) | 2018-09-19 | 2022-10-19 | Syngenta Crop Protection AG | Microbiocidal quinoline carboxamide derivatives |
| EP3856715A1 (en) | 2018-09-26 | 2021-08-04 | Syngenta Participations Ag | Insecticidal compounds |
| WO2020070049A1 (en) | 2018-10-02 | 2020-04-09 | Syngenta Participations Ag | Pesticidally active benzene- and azine-amide compounds |
| WO2020070132A1 (en) | 2018-10-06 | 2020-04-09 | Syngenta Participations Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
| JP2022504304A (ja) | 2018-10-06 | 2022-01-13 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリンジヒドロ－（チアジン）オキサジン誘導体 |
| TW202035404A (zh) | 2018-10-24 | 2020-10-01 | 瑞士商先正達農作物保護公司 | 具有含亞碸亞胺的取代基之殺有害生物活性雜環衍生物 |
| AR117291A1 (es) | 2018-12-14 | 2021-07-28 | Syngenta Crop Protection Ag | Compuestos heterocíclicos de cianamida con actividad pesticida |
| WO2020120694A1 (en) | 2018-12-14 | 2020-06-18 | Syngenta Participations Ag | Pesticidally-active bicyclic heteroaromatic compounds |
| WO2020127345A1 (en) | 2018-12-21 | 2020-06-25 | Syngenta Participations Ag | Pesticidally active pyrazole derivatives |
| WO2020141135A1 (en) | 2018-12-31 | 2020-07-09 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| US20220061324A1 (en) | 2018-12-31 | 2022-03-03 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| WO2020164993A1 (en) | 2019-02-13 | 2020-08-20 | Syngenta Crop Protection Ag | Pesticidally active pyrazole derivatives |
| WO2020164994A1 (en) | 2019-02-13 | 2020-08-20 | Syngenta Crop Protection Ag | Pesticidally active pyrazole derivatives |
| EP3696175A1 (en) | 2019-02-18 | 2020-08-19 | Syngenta Crop Protection AG | Pesticidally active azole-amide compounds |
| TW202100015A (zh) | 2019-02-28 | 2021-01-01 | 瑞士商先正達農作物保護公司 | 具有含硫取代基之殺有害生物活性雜環衍生物 |
| CN111620867A (zh) * | 2019-02-28 | 2020-09-04 | 东莞市东阳光农药研发有限公司 | 介离子杀虫剂 |
| TW202045011A (zh) | 2019-02-28 | 2020-12-16 | 瑞士商先正達農作物保護公司 | 具有含硫取代基之殺有害生物活性雜環衍生物 |
| BR112021017698A2 (pt) | 2019-03-08 | 2021-11-16 | Syngenta Crop Protection Ag | Derivados heterocíclicos ativos em termos pesticidas com substituintes contendo enxofre |
| CN110151762A (zh) * | 2019-05-19 | 2019-08-23 | 青海大学 | 一种噻虫啉的新用途 |
| EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
| EP3975718A1 (en) | 2019-05-29 | 2022-04-06 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
| WO2021009311A1 (en) | 2019-07-17 | 2021-01-21 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| CN112442026B (zh) * | 2019-08-27 | 2023-08-08 | 东莞市东阳光农药研发有限公司 | 介离子衍生物及其制备方法和应用 |
| CN110495463B (zh) * | 2019-09-10 | 2021-08-24 | 泰安市农业科学研究院 | 含三氟苯嘧啶的增效杀虫剂组合物及其应用 |
| CN112851665B (zh) * | 2019-11-28 | 2023-08-08 | 东莞市东阳光农药研发有限公司 | 新型介离子化合物及其在农业中的应用 |
| CN111183999A (zh) * | 2020-03-06 | 2020-05-22 | 江苏丘陵地区镇江农业科学研究所 | 含有三氟苯嘧啶和嘧菌酯的组合物、种子处理剂及应用 |
| CN111296463A (zh) * | 2020-03-17 | 2020-06-19 | 浙江中山化工集团股份有限公司 | 一种含有三氟苯嘧啶和虫螨腈复合杀虫剂 |
| CN111592539B (zh) * | 2020-06-03 | 2022-11-15 | 江西农业大学 | 一种三氟苯嘧啶的制备方法 |
| CN113951268A (zh) * | 2020-07-21 | 2022-01-21 | 江苏功成生物科技有限公司 | 一种含三氟苯嘧啶的卫生杀虫组合物及其应用 |
| WO2022180096A1 (en) | 2021-02-26 | 2022-09-01 | Syngenta Crop Protection Ag | Pesticidal compositions |
| CN115211434A (zh) * | 2021-04-19 | 2022-10-21 | 江苏扬农化工股份有限公司 | 一种含有虱螨脲和三氟苯嘧啶的杀蝇组合物及其应用 |
| JP7695476B2 (ja) * | 2021-09-21 | 2025-06-18 | ラジーブ ラソッド | 新規な殺有害生物剤組成物 |
| JP2024541320A (ja) | 2021-11-10 | 2024-11-08 | コルテバ アグリサイエンス エルエルシー | 特定のメソイオン性殺虫剤の調製プロセス |
| CN113956081B (zh) * | 2021-11-10 | 2023-02-28 | 江苏科技大学 | 利用蝇蛆生物转化蚕沙废弃物的方法及其产物应用 |
| JP2025526908A (ja) | 2022-08-18 | 2025-08-15 | コルテバ アグリサイエンス エルエルシー | ある特定のメソイオン性殺有害生物剤の中間体の調製及び単離プロセス |
| CN118359606A (zh) * | 2023-01-19 | 2024-07-19 | 华东理工大学 | 三氟苯嘧啶多晶型及其制备方法 |
| CN118894851A (zh) * | 2023-04-28 | 2024-11-05 | 帕潘纳(北京)科技有限公司 | 嘧啶嗡盐类化合物及其应用 |
| CN117720535B (zh) | 2023-12-13 | 2025-05-13 | 贵州大学 | 一种含1,2,4-噁二唑结构的吡啶并[1, 2-a]嘧啶类介离子衍生物及其制备和用途 |
| CN120774912A (zh) * | 2024-04-09 | 2025-10-14 | 青岛清原化合物有限公司 | 一种介离子嘧啶鎓类化合物及其应用 |
| CN120774913A (zh) * | 2024-04-09 | 2025-10-14 | 青岛清原化合物有限公司 | 一种介离子嘧啶鎓类化合物及其应用 |
| CN118661740B (zh) * | 2024-06-20 | 2025-10-03 | 青岛恒宁生物科技有限公司 | 一种含三氟苯嘧啶的杀虫组合物及其应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| EP0777964B1 (en) | 1989-08-30 | 2001-11-14 | Kynoch Agrochemicals (Proprietary) Limited | Preparation of a dosage device |
| BR9106147A (pt) | 1990-03-12 | 1993-03-09 | Du Pont | Granulos de pesticidas dispersaveis em agua ou soluveis em agua feitos a partir de ligantes termo-ativados |
| ES2091878T3 (es) | 1990-10-11 | 1996-11-16 | Sumitomo Chemical Co | Composicion plaguicida. |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| TWI401023B (zh) * | 2008-02-06 | 2013-07-11 | Du Pont | 中離子農藥 |
| MX2012001651A (es) * | 2009-08-05 | 2012-03-16 | Du Pont | Pesticidas mesoionicos. |
| UA110924C2 (uk) * | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| US20120122680A1 (en) * | 2009-08-05 | 2012-05-17 | E.I. Du Pont De Nemours And Company | Mesoionic pesticides |
| UA107804C2 (en) * | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| WO2012106495A1 (en) | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| TWI572587B (zh) * | 2011-12-15 | 2017-03-01 | 杜邦股份有限公司 | 丙二酸二鹽及用以製備丙二醯基二鹵化物之方法 |
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2011
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- 2011-12-22 MA MA36116A patent/MA34830B1/fr unknown
- 2011-12-22 BR BR112013009935A patent/BR112013009935B8/pt active IP Right Grant
- 2011-12-22 CN CN201510524967.4A patent/CN105198874A/zh active Pending
- 2011-12-22 CN CN201180062994.4A patent/CN103459387B/zh active Active
- 2011-12-22 KR KR1020137019825A patent/KR101897840B1/ko active Active
- 2011-12-22 AU AU2011352379A patent/AU2011352379B2/en active Active
- 2011-12-22 RU RU2013135410/04A patent/RU2585616C2/ru active
- 2011-12-22 SG SG2013024237A patent/SG189206A1/en unknown
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