CA2916766C - Isothiazoline compounds for combating invertebrate pests - Google Patents
Isothiazoline compounds for combating invertebrate pests Download PDFInfo
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- CA2916766C CA2916766C CA2916766A CA2916766A CA2916766C CA 2916766 C CA2916766 C CA 2916766C CA 2916766 A CA2916766 A CA 2916766A CA 2916766 A CA2916766 A CA 2916766A CA 2916766 C CA2916766 C CA 2916766C
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- alkyl
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- cycloalkyl
- compounds
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- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 60
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 331
- 239000000203 mixture Substances 0.000 claims abstract description 85
- 239000000463 material Substances 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 36
- -1 C3-C8-halocycloalkyl Chemical group 0.000 claims description 629
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 167
- 125000005842 heteroatom Chemical group 0.000 claims description 116
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 150000002431 hydrogen Chemical class 0.000 claims description 60
- 229910052736 halogen Inorganic materials 0.000 claims description 54
- 150000002367 halogens Chemical class 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 42
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 31
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004043 oxo group Chemical group O=* 0.000 claims description 21
- 241001465754 Metazoa Species 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 239000002689 soil Substances 0.000 claims description 15
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 206010061217 Infestation Diseases 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 9
- 238000009395 breeding Methods 0.000 claims description 9
- 230000001488 breeding effect Effects 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 7
- 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 6
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 4
- 125000006416 CBr Chemical group BrC* 0.000 claims description 4
- 125000006414 CCl Chemical group ClC* 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 125000006519 CCH3 Chemical group 0.000 claims description 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 241000244206 Nematoda Species 0.000 abstract description 23
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- 150000003254 radicals Chemical class 0.000 description 113
- 241000196324 Embryophyta Species 0.000 description 101
- 239000000460 chlorine Substances 0.000 description 96
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 86
- 229910052717 sulfur Inorganic materials 0.000 description 73
- 125000000623 heterocyclic group Chemical group 0.000 description 66
- 229920006395 saturated elastomer Polymers 0.000 description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 44
- 239000003112 inhibitor Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 34
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 31
- 241000238631 Hexapoda Species 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- 239000003053 toxin Substances 0.000 description 23
- 231100000765 toxin Toxicity 0.000 description 22
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 21
- 229910052731 fluorine Inorganic materials 0.000 description 21
- 108090000623 proteins and genes Proteins 0.000 description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 19
- 239000013543 active substance Substances 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 102000004169 proteins and genes Human genes 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 229930195729 fatty acid Natural products 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 16
- 235000018102 proteins Nutrition 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 15
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 14
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 14
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- 230000000749 insecticidal effect Effects 0.000 description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 14
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 11
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 10
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- 125000003118 aryl group Chemical group 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 10
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
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- 241000239223 Arachnida Species 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
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- 238000007792 addition Methods 0.000 description 9
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- 125000005843 halogen group Chemical group 0.000 description 9
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- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 8
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- 239000004215 Carbon black (E152) Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 239000003744 tubulin modulator Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361838370P | 2013-06-24 | 2013-06-24 | |
| US61/838,370 | 2013-06-24 | ||
| US201361896137P | 2013-10-28 | 2013-10-28 | |
| US61/896,137 | 2013-10-28 | ||
| PCT/EP2014/063106 WO2014206911A1 (en) | 2013-06-24 | 2014-06-23 | Isothiazoline compounds for combating invertebrate pests |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2916766A1 CA2916766A1 (en) | 2014-12-31 |
| CA2916766C true CA2916766C (en) | 2021-05-04 |
Family
ID=50981521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2916766A Active CA2916766C (en) | 2013-06-24 | 2014-06-23 | Isothiazoline compounds for combating invertebrate pests |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP3013819B1 (enExample) |
| JP (1) | JP2016527208A (enExample) |
| CN (1) | CN105473582A (enExample) |
| BR (1) | BR112015032346A2 (enExample) |
| CA (1) | CA2916766C (enExample) |
| ES (1) | ES2688893T3 (enExample) |
| MX (1) | MX368592B (enExample) |
| WO (1) | WO2014206911A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9744542B2 (en) | 2013-07-29 | 2017-08-29 | Apeel Technology, Inc. | Agricultural skin grafting |
| KR20170102359A (ko) | 2015-01-16 | 2017-09-08 | 아비스타 파마 솔루션즈, 아이엔씨. | 항기생충 화합물 |
| WO2016187581A1 (en) | 2015-05-20 | 2016-11-24 | Apeel Technology, Inc. | Plant extract compositions and methods of preparation thereof |
| ES2935595T3 (es) | 2015-09-16 | 2023-03-08 | Apeel Tech Inc | Método de formación de un recubrimiento protector aplicando compuestos de glicéridos de ácidos grasos a una superficie |
| ES2797697T3 (es) | 2015-12-10 | 2020-12-03 | Apeel Tech Inc | Proceso para despolimerizar cutina |
| TWI731928B (zh) | 2016-01-26 | 2021-07-01 | 美商ａＰＥＥＬ科技公司 | 製備及保存經消毒產品之方法 |
| WO2018094269A1 (en) | 2016-11-17 | 2018-05-24 | Apeel Technology, Inc. | Compositions formed from plant extracts and methods of preparation thereof |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| JP2021503465A (ja) | 2017-11-16 | 2021-02-12 | アビスタ ファーマ ソリューションズ，インコーポレーテッド | 単一エナンチオマーの抗寄生生物化合物 |
| TWI812673B (zh) | 2018-02-12 | 2023-08-21 | 美商富曼西公司 | 用於防治無脊椎害蟲之萘異噁唑啉化合物 |
| US12245605B2 (en) | 2018-09-05 | 2025-03-11 | Apeel Technology, Inc. | Compounds and formulations for protective coatings |
| CN115443066A (zh) | 2020-03-04 | 2022-12-06 | 阿比尔技术公司 | 涂覆的农业产品和相应的方法 |
| CN116457332A (zh) | 2020-10-30 | 2023-07-18 | 阿比尔技术公司 | 组合物及其制备方法 |
| MX2024002926A (es) | 2021-09-08 | 2024-03-26 | Apeel Tech Inc | Compuestos y formulaciones para recubrimientos protectores. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558082B (zh) * | 2004-03-05 | 2015-09-30 | 日产化学工业株式会社 | 异噁唑啉取代苯甲酰胺化合物的制备中间体 |
| JP2013518084A (ja) * | 2010-02-01 | 2013-05-20 | ビーエーエスエフ ソシエタス・ヨーロピア | 有害動物を駆除するための置換されたケトン性イソオキサゾリン化合物および誘導体 |
| EP2755969B1 (en) * | 2011-09-13 | 2017-01-18 | Syngenta Participations AG | Isothiazoline derivatives as insecticidal compounds |
| CN104169278B (zh) * | 2011-12-23 | 2017-10-24 | 巴斯夫欧洲公司 | 防治无脊椎动物害虫的异噻唑啉化合物 |
-
2014
- 2014-06-23 MX MX2015018015A patent/MX368592B/es active IP Right Grant
- 2014-06-23 JP JP2016522423A patent/JP2016527208A/ja active Pending
- 2014-06-23 CN CN201480043338.3A patent/CN105473582A/zh active Pending
- 2014-06-23 EP EP14732176.4A patent/EP3013819B1/en not_active Not-in-force
- 2014-06-23 CA CA2916766A patent/CA2916766C/en active Active
- 2014-06-23 BR BR112015032346A patent/BR112015032346A2/pt not_active Application Discontinuation
- 2014-06-23 WO PCT/EP2014/063106 patent/WO2014206911A1/en not_active Ceased
- 2014-06-23 ES ES14732176.4T patent/ES2688893T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CA2916766A1 (en) | 2014-12-31 |
| MX368592B (es) | 2019-10-08 |
| MX2015018015A (es) | 2016-07-13 |
| CN105473582A (zh) | 2016-04-06 |
| EP3013819B1 (en) | 2018-08-15 |
| EP3013819A1 (en) | 2016-05-04 |
| JP2016527208A (ja) | 2016-09-08 |
| ES2688893T3 (es) | 2018-11-07 |
| BR112015032346A2 (pt) | 2017-07-25 |
| WO2014206911A1 (en) | 2014-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190530 |