NZ570099A - Pesticides containing a bicyclic bisamide structure - Google Patents

Info

Publication number

NZ570099A

NZ570099A NZ570099A NZ57009907A NZ570099A NZ 570099 A NZ570099 A NZ 570099A NZ 570099 A NZ570099 A NZ 570099A NZ 57009907 A NZ57009907 A NZ 57009907A NZ 570099 A NZ570099 A NZ 570099A

Authority

NZ

New Zealand

Prior art keywords

spp

chloro

iponz

july

received

Prior art date

2006-02-16

Links

• Espacenet
• Global Dossier
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• 239000000575 pesticide Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 418
• 125000001424 substituent group Chemical group 0.000 claims abstract description 32
• 238000000034 method Methods 0.000 claims abstract description 29
• 241000238631 Hexapoda Species 0.000 claims abstract description 15
• 241000238876 Acari Species 0.000 claims abstract description 8
• -1 cyano, hydroxy Chemical group 0.000 claims description 206
• 239000000203 mixture Substances 0.000 claims description 140
• 230000000694 effects Effects 0.000 claims description 65
• 239000004480 active ingredient Substances 0.000 claims description 55
• 229910052736 halogen Inorganic materials 0.000 claims description 52
• 150000002367 halogens Chemical class 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 30
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 239000011593 sulfur Substances 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
• 239000001301 oxygen Substances 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 241000607479 Yersinia pestis Species 0.000 claims description 15
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 230000000749 insecticidal effect Effects 0.000 claims description 12
• 239000000463 material Substances 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 229920006395 saturated elastomer Polymers 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 238000009472 formulation Methods 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
• 241000256244 Heliothis virescens Species 0.000 claims description 6
• 230000000361 pesticidal effect Effects 0.000 claims description 6
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
• 150000001204 N-oxides Chemical class 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 abstract description 143
• 230000008569 process Effects 0.000 abstract description 7
• 125000002619 bicyclic group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 264
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 168
• YJXNJQHBVKTWCC-UHFFFAOYSA-N (3-cyclopent-2-en-1-yl-2-methyl-4-oxocyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(C2C=CCC2)C(=O)C1 YJXNJQHBVKTWCC-UHFFFAOYSA-N 0.000 description 163
• 229910000272 alkali metal oxide Inorganic materials 0.000 description 111
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 98
• 239000007787 solid Substances 0.000 description 97
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
• 239000002253 acid Substances 0.000 description 66
• 238000006243 chemical reaction Methods 0.000 description 61
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
• 239000000047 product Substances 0.000 description 58
• 239000000126 substance Substances 0.000 description 50
• 238000000746 purification Methods 0.000 description 47
• 238000003818 flash chromatography Methods 0.000 description 45
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 39
• 239000002904 solvent Substances 0.000 description 39
• 239000000725 suspension Substances 0.000 description 39
• 239000003053 toxin Substances 0.000 description 39
• 231100000765 toxin Toxicity 0.000 description 39
• 108700012359 toxins Proteins 0.000 description 39
• 239000007858 starting material Substances 0.000 description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• 241000196324 Embryophyta Species 0.000 description 30
• 239000012267 brine Substances 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• 239000000243 solution Substances 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 27
• 238000005481 NMR spectroscopy Methods 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 238000011161 development Methods 0.000 description 24
• 230000018109 developmental process Effects 0.000 description 24
• 239000011734 sodium Substances 0.000 description 24
• 240000008042 Zea mays Species 0.000 description 23
• 229910052794 bromium Inorganic materials 0.000 description 23
• 239000003153 chemical reaction reagent Substances 0.000 description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• 239000003480 eluent Substances 0.000 description 21
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 20
• 150000002431 hydrogen Chemical class 0.000 description 20
• 238000002844 melting Methods 0.000 description 20
• 230000008018 melting Effects 0.000 description 20
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 19
• 230000008878 coupling Effects 0.000 description 19
• 238000010168 coupling process Methods 0.000 description 19
• 238000005859 coupling reaction Methods 0.000 description 19
• 229910052740 iodine Inorganic materials 0.000 description 19
• 235000009973 maize Nutrition 0.000 description 19
• 239000000741 silica gel Substances 0.000 description 19
• 229910002027 silica gel Inorganic materials 0.000 description 19
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 238000007792 addition Methods 0.000 description 18
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
• XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 17
• 238000012360 testing method Methods 0.000 description 17
• 238000004440 column chromatography Methods 0.000 description 16
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 16
• 239000010410 layer Substances 0.000 description 16
• 239000012085 test solution Substances 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000002585 base Substances 0.000 description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
• 238000001914 filtration Methods 0.000 description 14
• 239000012071 phase Substances 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 108090000623 proteins and genes Proteins 0.000 description 11
• 230000009261 transgenic effect Effects 0.000 description 11
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
• 239000007864 aqueous solution Substances 0.000 description 10
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
• 238000001035 drying Methods 0.000 description 10
• 239000004009 herbicide Substances 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 150000001340 alkali metals Chemical class 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 239000002267 larvicidal agent Substances 0.000 description 9
• 102000004169 proteins and genes Human genes 0.000 description 9
• 239000004094 surface-active agent Substances 0.000 description 9
• QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
• 229920000742 Cotton Polymers 0.000 description 8
• 241000219146 Gossypium Species 0.000 description 8
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 8
• 238000011534 incubation Methods 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 230000026267 regulation of growth Effects 0.000 description 8
• AOPYBRLTXWCZAV-UHFFFAOYSA-N (1-cyclopropylcyclopropyl)azanium;chloride Chemical compound [Cl-].C1CC1C1([NH3+])CC1 AOPYBRLTXWCZAV-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 239000005995 Aluminium silicate Substances 0.000 description 7
• 241001124076 Aphididae Species 0.000 description 7
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
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• 150000007513 acids Chemical class 0.000 description 7
• 235000012211 aluminium silicate Nutrition 0.000 description 7
• 238000000354 decomposition reaction Methods 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
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• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
• 239000002169 Metam Substances 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• 241001147398 Ostrinia nubilalis Species 0.000 description 6
• 241000500437 Plutella xylostella Species 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• 125000001309 chloro group Chemical group Cl* 0.000 description 6
• 235000014113 dietary fatty acids Nutrition 0.000 description 6
• GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 6
• 235000013399 edible fruits Nutrition 0.000 description 6
• 239000000194 fatty acid Substances 0.000 description 6
• 229930195729 fatty acid Natural products 0.000 description 6
• JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 6
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• 238000010626 work up procedure Methods 0.000 description 6
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• VAQCTXKRYXEHBE-UHFFFAOYSA-N 5-chloro-7-[2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carbonyl]-1h-pyrazolo[3,4-f][3,1]benzoxazin-9-one Chemical compound N1=C(C(F)(F)F)C=C(C(=O)C=2OC(=O)C3=C4NN=CC4=CC(Cl)=C3N=2)N1C1=NC=CC=C1Cl VAQCTXKRYXEHBE-UHFFFAOYSA-N 0.000 description 5
• IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 5
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• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 5
• 229950008167 abamectin Drugs 0.000 description 5
• GDZNYEZGJAFIKA-UHFFFAOYSA-N acetoprole Chemical compound NC1=C(S(C)=O)C(C(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GDZNYEZGJAFIKA-UHFFFAOYSA-N 0.000 description 5
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• 239000012298 atmosphere Substances 0.000 description 5
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• 230000001418 larval effect Effects 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• MMJIKDUYHKCIKA-UHFFFAOYSA-N methyl 6-amino-5-bromo-1h-indazole-7-carboxylate Chemical compound COC(=O)C1=C(N)C(Br)=CC2=C1NN=C2 MMJIKDUYHKCIKA-UHFFFAOYSA-N 0.000 description 5
• 229940102396 methyl bromide Drugs 0.000 description 5
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