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 (OSRAM) |
| JP (1) | JP2016527208A (OSRAM) |
| CN (1) | CN105473582A (OSRAM) |
| BR (1) | BR112015032346A2 (OSRAM) |
| CA (1) | CA2916766C (OSRAM) |
| ES (1) | ES2688893T3 (OSRAM) |
| MX (1) | MX368592B (OSRAM) |
| WO (1) | WO2014206911A1 (OSRAM) |
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 |
| BR112017015137A2 (pt) | 2015-01-16 | 2018-01-30 | Avista Pharma Solutions, Inc. | compostos antiparasíticos |
| JP7157531B2 (ja) | 2015-05-20 | 2022-10-20 | アピール テクノロジー，インコーポレイテッド | 植物抽出物組成物およびその調製方法 |
| WO2017048951A1 (en) | 2015-09-16 | 2017-03-23 | Apeel Technology, Inc. | Precursor compounds for molecular coatings |
| JP6549326B2 (ja) | 2015-12-10 | 2019-07-24 | アピール テクノロジー，インコーポレイテッド | 保護コーティングを形成するための植物抽出物組成物 |
| EP3407713A1 (en) | 2016-01-26 | 2018-12-05 | Apeel Technology, Inc. | Method for preparing and preserving sanitized products |
| EP3541192B1 (en) | 2016-11-17 | 2025-06-25 | Apeel Technology, Inc. | Methods of preparing fatty acid esters from crosslinked polyesters |
| 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 |
| JP2023548012A (ja) | 2020-10-30 | 2023-11-15 | アピール テクノロジー，インコーポレイテッド | 組成物及びその調製方法 |
| JP2024532457A (ja) | 2021-09-08 | 2024-09-05 | アピール テクノロジー，インコーポレイテッド | 保護コーティング用の化合物及び配合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4883296B2 (ja) * | 2004-03-05 | 2012-02-22 | 日産化学工業株式会社 | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
| CN102762543B (zh) * | 2010-02-01 | 2016-03-09 | 巴斯夫欧洲公司 | 用于防除动物害虫的取代的酮型异*唑啉化合物和衍生物 |
| BR122018069466B1 (pt) * | 2011-09-13 | 2019-04-02 | Syngenta Participations Ag | Derivados isotiazolina como compostos inseticidas |
| KR20140115329A (ko) * | 2011-12-23 | 2014-09-30 | 바스프 에스이 | 무척추동물 해충 퇴치를 위한 이소티아졸린 화합물 |
-
2014
- 2014-06-23 WO PCT/EP2014/063106 patent/WO2014206911A1/en not_active Ceased
- 2014-06-23 CN CN201480043338.3A patent/CN105473582A/zh active Pending
- 2014-06-23 ES ES14732176.4T patent/ES2688893T3/es active Active
- 2014-06-23 EP EP14732176.4A patent/EP3013819B1/en not_active Not-in-force
- 2014-06-23 BR BR112015032346A patent/BR112015032346A2/pt not_active Application Discontinuation
- 2014-06-23 CA CA2916766A patent/CA2916766C/en active Active
- 2014-06-23 JP JP2016522423A patent/JP2016527208A/ja active Pending
- 2014-06-23 MX MX2015018015A patent/MX368592B/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016527208A (ja) | 2016-09-08 |
| WO2014206911A1 (en) | 2014-12-31 |
| BR112015032346A2 (pt) | 2017-07-25 |
| CN105473582A (zh) | 2016-04-06 |
| MX368592B (es) | 2019-10-08 |
| EP3013819B1 (en) | 2018-08-15 |
| MX2015018015A (es) | 2016-07-13 |
| EP3013819A1 (en) | 2016-05-04 |
| CA2916766A1 (en) | 2014-12-31 |
| ES2688893T3 (es) | 2018-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190530 |