PT1417176E - Antranilidamidas substituídas para controlar pragas de invertebrados - Google Patents

Info

Publication number

PT1417176E

PT1417176E PT02761486T PT02761486T PT1417176E PT 1417176 E PT1417176 E PT 1417176E PT 02761486 T PT02761486 T PT 02761486T PT 02761486 T PT02761486 T PT 02761486T PT 1417176 E PT1417176 E PT 1417176E

Authority

PT

Portugal

Prior art keywords

alkyl

independently

compound

optionally substituted

formula

Prior art date

2001-08-16

Links

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• Global Dossier
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• 241000607479 Yersinia pestis Species 0.000 title claims abstract description 61
• PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 284
• 239000000203 mixture Substances 0.000 claims abstract description 96
• 238000000034 method Methods 0.000 claims abstract description 80
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
• -1 R11 Chemical group 0.000 claims description 151
• 239000000460 chlorine Substances 0.000 claims description 147
• 125000001424 substituent group Chemical group 0.000 claims description 89
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 46
• 150000002367 halogens Chemical class 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• 238000002360 preparation method Methods 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• 241000196324 Embryophyta Species 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
• 239000007787 solid Substances 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 17
• 239000003085 diluting agent Substances 0.000 claims description 16
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 230000004224 protection Effects 0.000 claims description 13
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 102220024746 rs199473444 Human genes 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 11
• 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 description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 10
• 102220060025 rs141586345 Human genes 0.000 claims description 10
• 239000004094 surface-active agent Substances 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 241001465754 Metazoa Species 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 239000007788 liquid Substances 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• 101150020251 NR13 gene Proteins 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 235000013305 food Nutrition 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 101100082497 Oryza sativa subsp. japonica PCF3 gene Proteins 0.000 claims description 3
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 2
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• ZRKIFBFLGUNORU-UHFFFAOYSA-N n-[4-benzamido-2-methyl-6-(propan-2-ylcarbamoyl)phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound C=1C(C)=C(NC(=O)C=2N(N=C(C=2)C(F)(F)F)C=2C(=CC=CN=2)Cl)C(C(=O)NC(C)C)=CC=1NC(=O)C1=CC=CC=C1 ZRKIFBFLGUNORU-UHFFFAOYSA-N 0.000 claims description 2
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 2
• 229910052721 tungsten Inorganic materials 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
• 230000008520 organization Effects 0.000 claims 3
• 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
• 241000985282 Symbion Species 0.000 claims 1
• BOLTYJBKIGEYIN-UHFFFAOYSA-N n-[4-acetyl-2-methyl-6-(propan-2-ylcarbamoyl)phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound CC(C)NC(=O)C1=CC(C(C)=O)=CC(C)=C1NC(=O)C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl BOLTYJBKIGEYIN-UHFFFAOYSA-N 0.000 claims 1
• 101150035983 str1 gene Proteins 0.000 claims 1
• 229910052740 iodine Inorganic materials 0.000 abstract description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 392
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
• 238000006243 chemical reaction Methods 0.000 description 59
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 55
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• 238000012360 testing method Methods 0.000 description 42
• 239000002904 solvent Substances 0.000 description 39
• 239000002253 acid Substances 0.000 description 35
• 241000238631 Hexapoda Species 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 238000003786 synthesis reaction Methods 0.000 description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
• 239000000243 solution Substances 0.000 description 24
• 230000009418 agronomic effect Effects 0.000 description 23
• 230000015572 biosynthetic process Effects 0.000 description 23
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• 229910002092 carbon dioxide Inorganic materials 0.000 description 20
• 239000003153 chemical reaction reagent Substances 0.000 description 19
• 238000003556 assay Methods 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 15
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 15
• 238000009472 formulation Methods 0.000 description 15
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 15
• 230000003647 oxidation Effects 0.000 description 15
• 238000007254 oxidation reaction Methods 0.000 description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• 239000007921 spray Substances 0.000 description 14
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 13
• 241000238876 Acari Species 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 12
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
• 125000004076 pyridyl group Chemical group 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 11
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
• 240000008042 Zea mays Species 0.000 description 11
• 125000003118 aryl group Chemical group 0.000 description 11
• 238000005859 coupling reaction Methods 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• 238000006722 reduction reaction Methods 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• 239000002689 soil Substances 0.000 description 11
• HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 10
• 241000254032 Acrididae Species 0.000 description 10
• 241000254173 Coleoptera Species 0.000 description 10
• 244000299507 Gossypium hirsutum Species 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 10
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 10
• 230000008878 coupling Effects 0.000 description 10
• 238000010168 coupling process Methods 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 10
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• 241001124076 Aphididae Species 0.000 description 9
• 229920000742 Cotton Polymers 0.000 description 9
• 241000258937 Hemiptera Species 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
• 239000013543 active substance Substances 0.000 description 9
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 9
• 230000006378 damage Effects 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 9
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 241000244206 Nematoda Species 0.000 description 8
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 238000011156 evaluation Methods 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 150000003512 tertiary amines Chemical class 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
• 241000255925 Diptera Species 0.000 description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• 241001674048 Phthiraptera Species 0.000 description 7
• 235000020971 citrus fruits Nutrition 0.000 description 7
• 238000002425 crystallisation Methods 0.000 description 7
• 230000008025 crystallization Effects 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 235000005911 diet Nutrition 0.000 description 7
• 230000037213 diet Effects 0.000 description 7
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 7
• 150000004820 halides Chemical class 0.000 description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
• 239000002917 insecticide Substances 0.000 description 7
• 238000002156 mixing Methods 0.000 description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
• 125000002098 pyridazinyl group Chemical group 0.000 description 7
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 7
• 238000006467 substitution reaction Methods 0.000 description 7
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 6
• 241000239290 Araneae Species 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
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• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
• 150000001298 alcohols Chemical class 0.000 description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 150000001805 chlorine compounds Chemical class 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 235000005822 corn Nutrition 0.000 description 6
• 238000006297 dehydration reaction Methods 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 235000013399 edible fruits Nutrition 0.000 description 6
• 238000000605 extraction Methods 0.000 description 6
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 6
• 125000005322 morpholin-1-yl group Chemical group 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 6
• 229910052698 phosphorus Inorganic materials 0.000 description 6
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• 235000009566 rice Nutrition 0.000 description 6
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• KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
• 239000005660 Abamectin Substances 0.000 description 5
• 241000193388 Bacillus thuringiensis Species 0.000 description 5
• 241000207199 Citrus Species 0.000 description 5
• 241000721621 Myzus persicae Species 0.000 description 5
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
• 235000002595 Solanum tuberosum Nutrition 0.000 description 5
• 244000061456 Solanum tuberosum Species 0.000 description 5
• 239000000370 acceptor Substances 0.000 description 5
• 230000010933 acylation Effects 0.000 description 5
• 238000005917 acylation reaction Methods 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 230000029936 alkylation Effects 0.000 description 5
• 238000005804 alkylation reaction Methods 0.000 description 5
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