ES2817098T3 - Compuestos de isotiazolinas sustituidas con naftilo - Google Patents
Compuestos de isotiazolinas sustituidas con naftilo Download PDFInfo
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- ES2817098T3 ES2817098T3 ES14731658T ES14731658T ES2817098T3 ES 2817098 T3 ES2817098 T3 ES 2817098T3 ES 14731658 T ES14731658 T ES 14731658T ES 14731658 T ES14731658 T ES 14731658T ES 2817098 T3 ES2817098 T3 ES 2817098T3
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- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 288
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 288
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 250
- 125000005347 halocycloalkyl group Chemical group 0.000 claims abstract description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 72
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 68
- 150000002367 halogens Chemical group 0.000 claims abstract description 68
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 46
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 39
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 37
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 10
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims description 777
- -1 area Substances 0.000 claims description 643
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 241000607479 Yersinia pestis Species 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 241001465754 Metazoa Species 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 206010061217 Infestation Diseases 0.000 claims description 9
- 150000002466 imines Chemical class 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 7
- 235000013305 food Nutrition 0.000 claims description 5
- 238000009395 breeding Methods 0.000 claims description 4
- 230000001488 breeding effect Effects 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 229910052705 radium Inorganic materials 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 86
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 85
- 125000000232 haloalkynyl group Chemical group 0.000 abstract description 64
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract description 50
- 125000000262 haloalkenyl group Chemical group 0.000 abstract description 35
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 abstract description 27
- 150000003254 radicals Chemical class 0.000 description 108
- 125000005842 heteroatom Chemical group 0.000 description 92
- 125000000623 heterocyclic group Chemical group 0.000 description 78
- 241000196324 Embryophyta Species 0.000 description 73
- 125000001424 substituent group Chemical group 0.000 description 67
- 229910052717 sulfur Inorganic materials 0.000 description 67
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 49
- 229910052760 oxygen Inorganic materials 0.000 description 49
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000011575 calcium Substances 0.000 description 38
- 229920006395 saturated elastomer Polymers 0.000 description 35
- 239000002904 solvent Substances 0.000 description 32
- 125000004414 alkyl thio group Chemical group 0.000 description 31
- 125000000304 alkynyl group Chemical group 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 150000001412 amines Chemical class 0.000 description 28
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 26
- 125000004995 haloalkylthio group Chemical group 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 241000244206 Nematoda Species 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 24
- 108090000623 proteins and genes Proteins 0.000 description 24
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 239000003053 toxin Substances 0.000 description 23
- 231100000765 toxin Toxicity 0.000 description 23
- 108700012359 toxins Proteins 0.000 description 23
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 22
- 125000001931 aliphatic group Chemical group 0.000 description 22
- 239000002585 base Substances 0.000 description 21
- 239000003112 inhibitor Substances 0.000 description 21
- 102000004169 proteins and genes Human genes 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 239000013543 active substance Substances 0.000 description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 241000238631 Hexapoda Species 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 description 15
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 14
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
- 125000004438 haloalkoxy group Chemical group 0.000 description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 13
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- 241000894007 species Species 0.000 description 13
- 150000003573 thiols Chemical class 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 12
- 230000000749 insecticidal effect Effects 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 11
- 238000005576 amination reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 11
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 241000209149 Zea Species 0.000 description 10
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 10
- 235000005822 corn Nutrition 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 10
- 125000004434 sulfur atom Chemical group 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000255925 Diptera Species 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 7
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 7
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- 241000239223 Arachnida Species 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 241000238421 Arthropoda Species 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 241000219146 Gossypium Species 0.000 description 6
- 241000255777 Lepidoptera Species 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 108020004511 Recombinant DNA Proteins 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 235000011118 potassium hydroxide Nutrition 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 150000003871 sulfonates Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 5
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000005562 Glyphosate Substances 0.000 description 5
- 241000257303 Hymenoptera Species 0.000 description 5
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 5
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000012190 activator Substances 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 5
- 238000007112 amidation reaction Methods 0.000 description 5
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 5
- 235000019800 disodium phosphate Nutrition 0.000 description 5
- 229910000397 disodium phosphate Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940097068 glyphosate Drugs 0.000 description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-M glyphosate(1-) Chemical compound OP(O)(=O)CNCC([O-])=O XDDAORKBJWWYJS-UHFFFAOYSA-M 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 238000005580 one pot reaction Methods 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 4
- 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 239000005561 Glufosinate Substances 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 241000256602 Isoptera Species 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000238887 Ornithodoros Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000336929 Sogata Species 0.000 description 4
- 241001161749 Stenchaetothrips biformis Species 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 230000009435 amidation Effects 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
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- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
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- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
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- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
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- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
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- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
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- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
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- 235000011008 sodium phosphates Nutrition 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004300 thiazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])SC1([H])* 0.000 description 1
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- 229940116861 trichinella britovi Drugs 0.000 description 1
- 229940096911 trichinella spiralis Drugs 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- KRTNITDCKAVIFI-UHFFFAOYSA-N tridecyl benzenesulfonate Chemical class CCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 KRTNITDCKAVIFI-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
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-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
- 238000007039 two-step reaction Methods 0.000 description 1
- 150000003672 ureas Chemical class 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
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000000664 voltage gated sodium channel blocking agent Substances 0.000 description 1
- 235000020234 walnut Nutrition 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
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361838354P | 2013-06-24 | 2013-06-24 | |
| PCT/EP2014/063101 WO2014206907A1 (en) | 2013-06-24 | 2014-06-23 | Naphthyl- or isoquinolinyl-substituted isothiazoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2817098T3 true ES2817098T3 (es) | 2021-04-06 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14731658T Active ES2817098T3 (es) | 2013-06-24 | 2014-06-23 | Compuestos de isotiazolinas sustituidas con naftilo |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10327446B2 (enExample) |
| EP (1) | EP3013807B1 (enExample) |
| JP (1) | JP6407987B2 (enExample) |
| CN (1) | CN105473564A (enExample) |
| BR (1) | BR112015032344A2 (enExample) |
| CA (1) | CA2916824C (enExample) |
| ES (1) | ES2817098T3 (enExample) |
| MX (1) | MX374351B (enExample) |
| WO (1) | WO2014206907A1 (enExample) |
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| CR20160402A (es) | 2014-02-03 | 2017-02-07 | Basf Se | Compuesto de ciclopenteno y ciclopentadieno para controlar plagas de invertebrados |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | Substituted cyclopropyl derivatives |
| CN111333512A (zh) * | 2020-03-09 | 2020-06-26 | 江苏君若药业有限公司 | 阿福拉纳关键中间体4-乙酰基-1-萘甲酸酯的制备 |
| CN114380762A (zh) * | 2022-01-23 | 2022-04-22 | 贵州大学 | 异恶唑啉酰肼衍生物及其制备方法和用途 |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| CN118765716B (zh) * | 2024-09-09 | 2024-12-06 | 云南省农业科学院药用植物研究所 | 一种中华腐生牛肝菌菌种培养方法 |
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| JP2007106756A (ja) * | 2005-09-14 | 2007-04-26 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
| TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| AU2008235089B8 (en) * | 2007-04-10 | 2014-04-10 | Bayer Intellectual Property Gmbh | Insecticidal aryl isoxazoline derivatives |
| CN101815706A (zh) * | 2007-06-13 | 2010-08-25 | 杜邦公司 | 异*唑啉杀昆虫剂 |
| JP5316808B2 (ja) * | 2007-06-29 | 2013-10-16 | 日産化学工業株式会社 | 置換イソキサゾリン又はエノンオキシム化合物および有害生物防除剤 |
| JP5365806B2 (ja) * | 2007-09-10 | 2013-12-11 | 日産化学工業株式会社 | 置換イソキサゾリン化合物及び有害生物防除剤 |
| JP5676262B2 (ja) * | 2007-10-03 | 2015-02-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 有害無脊椎生物の防除用ナフタレンイソキサゾリン化合物 |
| JP2009286773A (ja) * | 2008-03-14 | 2009-12-10 | Bayer Cropscience Ag | 殺虫性縮環式アリール類 |
| EP2382196B1 (en) * | 2008-12-23 | 2015-08-12 | Basf Se | Imine compounds for combating invertebrate pests |
| 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 |
| EP2536698B1 (en) * | 2010-02-17 | 2015-06-10 | Syngenta Participations AG | Isoxazoline derivatives as insecticides |
| WO2013026933A1 (en) * | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
| BR122018069466B1 (pt) * | 2011-09-13 | 2019-04-02 | Syngenta Participations Ag | Derivados isotiazolina como compostos inseticidas |
| US20140343085A1 (en) * | 2011-11-29 | 2014-11-20 | Novartis Ag | Use of aryl derivatives for controlling ectoparasites |
| KR20140115329A (ko) | 2011-12-23 | 2014-09-30 | 바스프 에스이 | 무척추동물 해충 퇴치를 위한 이소티아졸린 화합물 |
-
2014
- 2014-06-23 WO PCT/EP2014/063101 patent/WO2014206907A1/en not_active Ceased
- 2014-06-23 EP EP14731658.2A patent/EP3013807B1/en active Active
- 2014-06-23 JP JP2016522420A patent/JP6407987B2/ja not_active Expired - Fee Related
- 2014-06-23 MX MX2015018019A patent/MX374351B/es active IP Right Grant
- 2014-06-23 CA CA2916824A patent/CA2916824C/en not_active Expired - Fee Related
- 2014-06-23 US US14/757,414 patent/US10327446B2/en active Active
- 2014-06-23 BR BR112015032344A patent/BR112015032344A2/pt not_active Application Discontinuation
- 2014-06-23 ES ES14731658T patent/ES2817098T3/es active Active
- 2014-06-23 CN CN201480043335.XA patent/CN105473564A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2916824A1 (en) | 2014-12-31 |
| MX374351B (es) | 2025-03-06 |
| CN105473564A (zh) | 2016-04-06 |
| US10327446B2 (en) | 2019-06-25 |
| JP2016530226A (ja) | 2016-09-29 |
| WO2014206907A1 (en) | 2014-12-31 |
| JP6407987B2 (ja) | 2018-10-17 |
| BR112015032344A2 (pt) | 2017-07-25 |
| US20160374342A1 (en) | 2016-12-29 |
| EP3013807A1 (en) | 2016-05-04 |
| MX2015018019A (es) | 2016-07-06 |
| EP3013807B1 (en) | 2020-04-08 |
| CA2916824C (en) | 2021-05-25 |
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