ES2817098T3 - Compuestos de isotiazolinas sustituidas con naftilo - Google Patents

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Publication number

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

Authority

ES

Spain

Prior art keywords

hydrogen

formula

compounds

alkyl

group

Prior art date

2013-06-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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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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