DK175588B1 - Benzothiadiazoler og deres anvendelse i fremgangsmåder og midler mod plantesygdomme - Google Patents

Info

Publication number

DK175588B1

DK175588B1 DK198804676A DK467688A DK175588B1 DK 175588 B1 DK175588 B1 DK 175588B1 DK 198804676 A DK198804676 A DK 198804676A DK 467688 A DK467688 A DK 467688A DK 175588 B1 DK175588 B1 DK 175588B1

Authority

DK

Denmark

Prior art keywords

alkyl

halogen

benzo

thiadiazole

substituted

Prior art date

1987-08-21

Links

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• 238000000034 method Methods 0.000 title claims abstract description 48
• 201000010099 disease Diseases 0.000 title claims abstract description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 11
• FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 title claims description 7
• -1 SO3M Chemical group 0.000 claims abstract description 215
• 150000001875 compounds Chemical class 0.000 claims abstract description 183
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 162
• 150000002367 halogens Chemical group 0.000 claims abstract description 147
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 144
• 239000001257 hydrogen Substances 0.000 claims abstract description 144
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 93
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 74
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 48
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 44
• 230000003053 immunization Effects 0.000 claims abstract description 43
• 239000000203 mixture Substances 0.000 claims abstract description 43
• 239000002585 base Substances 0.000 claims abstract description 29
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 28
• 150000001340 alkali metals Chemical class 0.000 claims abstract description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
• 150000007514 bases Chemical class 0.000 claims abstract description 15
• 229910006069 SO3H Inorganic materials 0.000 claims abstract description 13
• 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 13
• 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims abstract description 13
• 150000003839 salts Chemical class 0.000 claims abstract description 13
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 13
• 150000007529 inorganic bases Chemical class 0.000 claims abstract description 10
• 238000002649 immunization Methods 0.000 claims abstract description 9
• 150000003512 tertiary amines Chemical class 0.000 claims abstract description 6
• 239000004480 active ingredient Substances 0.000 claims abstract description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 129
• 239000013543 active substance Substances 0.000 claims description 114
• 229910052717 sulfur Chemical group 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 58
• 229910052760 oxygen Inorganic materials 0.000 claims description 57
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 54
• 239000001301 oxygen Substances 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
• 238000002360 preparation method Methods 0.000 claims description 44
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 229910052757 nitrogen Inorganic materials 0.000 claims description 38
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
• 239000002253 acid Substances 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 239000012442 inert solvent Substances 0.000 claims description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
• 230000008569 process Effects 0.000 claims description 25
• 229920006395 saturated elastomer Polymers 0.000 claims description 25
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
• 125000004429 atom Chemical group 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 21
• 206010061217 Infestation Diseases 0.000 claims description 20
• 125000004434 sulfur atom Chemical group 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• COAIOOWBEPAOFY-UHFFFAOYSA-N 1,2,3-benzothiadiazole-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1SN=N2 COAIOOWBEPAOFY-UHFFFAOYSA-N 0.000 claims description 19
• 125000002837 carbocyclic group Chemical group 0.000 claims description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 229910052721 tungsten Inorganic materials 0.000 claims description 18
• 239000003054 catalyst Substances 0.000 claims description 17
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 125000001589 carboacyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 239000011593 sulfur Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 229910052698 phosphorus Inorganic materials 0.000 claims description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 11
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• CUIIHNPMMCYAMK-UHFFFAOYSA-N methyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1SN=N2 CUIIHNPMMCYAMK-UHFFFAOYSA-N 0.000 claims description 11
• 150000002772 monosaccharides Chemical group 0.000 claims description 11
• 239000011574 phosphorus Substances 0.000 claims description 11
• 244000005700 microbiome Species 0.000 claims description 10
• 239000002904 solvent Substances 0.000 claims description 10
• 239000003638 chemical reducing agent Substances 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
• 229910052783 alkali metal Inorganic materials 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 8
• 150000007530 organic bases Chemical class 0.000 claims description 8
• 230000003032 phytopathogenic effect Effects 0.000 claims description 8
• QFSYOEAIWXEDMZ-UHFFFAOYSA-N 1,2,3-benzothiadiazole-7-carbonitrile Chemical compound N#CC1=CC=CC2=C1SN=N2 QFSYOEAIWXEDMZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 6
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 6
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 6
• MSTOXOOJRZJTEH-UHFFFAOYSA-N 4,6-dibromo-1,2,3-benzothiadiazole-7-carbonitrile Chemical compound BrC1=CC(Br)=C2N=NSC2=C1C#N MSTOXOOJRZJTEH-UHFFFAOYSA-N 0.000 claims description 5
• NWWJLYWHZMUZGI-UHFFFAOYSA-N 4-chloro-1,2,3-benzothiadiazole-7-carbonitrile Chemical compound ClC1=CC=C(C#N)C2=C1N=NS2 NWWJLYWHZMUZGI-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
• 230000002378 acidificating effect Effects 0.000 claims description 5
• 239000002168 alkylating agent Substances 0.000 claims description 5
• 229940100198 alkylating agent Drugs 0.000 claims description 5
• 150000008064 anhydrides Chemical class 0.000 claims description 5
• 150000007524 organic acids Chemical class 0.000 claims description 5
• DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 5
• 239000008096 xylene Substances 0.000 claims description 5
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
• 150000002429 hydrazines Chemical class 0.000 claims description 4
• 150000007857 hydrazones Chemical class 0.000 claims description 4
• 125000000962 organic group Chemical group 0.000 claims description 4
• 239000000376 reactant Substances 0.000 claims description 4
• 229910052710 silicon Inorganic materials 0.000 claims description 4
• 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
• LXDHQFIXZWZUGL-UHFFFAOYSA-N 1,2,3-benzothiadiazole-7-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1SN=N2 LXDHQFIXZWZUGL-UHFFFAOYSA-N 0.000 claims description 3
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 3
• FFPKROHWFAFXFH-UHFFFAOYSA-N ethyl 5-fluoro-1,2,3-benzothiadiazole-7-carboxylate Chemical class CCOC(=O)C1=CC(F)=CC2=C1SN=N2 FFPKROHWFAFXFH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 150000002576 ketones Chemical class 0.000 claims description 3
• 229910052987 metal hydride Inorganic materials 0.000 claims description 3
• 150000004681 metal hydrides Chemical class 0.000 claims description 3
• 150000007522 mineralic acids Chemical class 0.000 claims description 3
• 239000010703 silicon Substances 0.000 claims description 3
• IDKLGMFOKNOKNK-UHFFFAOYSA-N (4-methoxyphenyl)methyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)C1=CC=CC2=C1SN=N2 IDKLGMFOKNOKNK-UHFFFAOYSA-N 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
• RQFMLINCSOTOKN-UHFFFAOYSA-N 3-hydroxypropyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound OCCCOC(=O)C1=CC=CC2=C1SN=N2 RQFMLINCSOTOKN-UHFFFAOYSA-N 0.000 claims description 2
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 2
• 239000004471 Glycine Substances 0.000 claims description 2
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
• WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 2
• GOXYFBXOCNAECF-UHFFFAOYSA-N cyclobutylidenehydrazine Chemical compound NN=C1CCC1 GOXYFBXOCNAECF-UHFFFAOYSA-N 0.000 claims description 2
• GDCXPYOIUNMIKT-UHFFFAOYSA-N ethyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1SN=N2 GDCXPYOIUNMIKT-UHFFFAOYSA-N 0.000 claims description 2
• OOZJDKPXLJDCPH-UHFFFAOYSA-N n'-cyclopentyl-1,2,3-benzothiadiazole-7-carbohydrazide Chemical compound C=1C=CC=2N=NSC=2C=1C(=O)NNC1CCCC1 OOZJDKPXLJDCPH-UHFFFAOYSA-N 0.000 claims description 2
• GVPORHLBKJQAKZ-UHFFFAOYSA-N n'-phenyl-1,2,3-benzothiadiazole-7-carbohydrazide Chemical compound C=1C=CC=2N=NSC=2C=1C(=O)NNC1=CC=CC=C1 GVPORHLBKJQAKZ-UHFFFAOYSA-N 0.000 claims description 2
• NWEOOTGSFXAKRE-UHFFFAOYSA-N n-(cyclohexylideneamino)-1,2,3-benzothiadiazole-7-carboxamide Chemical compound C=1C=CC=2N=NSC=2C=1C(=O)NN=C1CCCCC1 NWEOOTGSFXAKRE-UHFFFAOYSA-N 0.000 claims description 2
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 150000002923 oximes Chemical class 0.000 claims description 2
• CMSYAUUNBBRLCA-UHFFFAOYSA-N pentyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound CCCCCOC(=O)C1=CC=CC2=C1SN=N2 CMSYAUUNBBRLCA-UHFFFAOYSA-N 0.000 claims description 2
• GQNOPGDRQSASFF-UHFFFAOYSA-N propan-2-yl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CC2=C1SN=N2 GQNOPGDRQSASFF-UHFFFAOYSA-N 0.000 claims description 2
• 229910000077 silane Inorganic materials 0.000 claims description 2
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
• RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 58
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
• DDVGFZQBIZMMRV-UHFFFAOYSA-N 6-chloro-1,2,3-benzothiadiazole-7-carbonitrile Chemical compound ClC1=CC=C2N=NSC2=C1C#N DDVGFZQBIZMMRV-UHFFFAOYSA-N 0.000 claims 3
• QMZFXYJIPXOVOV-UHFFFAOYSA-N 6-chloro-1,2,3-benzothiadiazole-7-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C=CC2=C1SN=N2 QMZFXYJIPXOVOV-UHFFFAOYSA-N 0.000 claims 3
• 150000001341 alkaline earth metal compounds Chemical class 0.000 claims 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
• 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
• NZBWCDZDVBWHOD-UHFFFAOYSA-N cycloheptylhydrazine Chemical compound NNC1CCCCCC1 NZBWCDZDVBWHOD-UHFFFAOYSA-N 0.000 claims 1
• PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 claims 1
• YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
• 108090000623 proteins and genes Proteins 0.000 claims 1
• 230000001526 topogenic effect Effects 0.000 claims 1
• 125000002091 cationic group Chemical group 0.000 abstract description 4
• 150000003335 secondary amines Chemical class 0.000 abstract description 2
• 244000045561 useful plants Species 0.000 abstract 1
• 241000196324 Embryophyta Species 0.000 description 120
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
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• 239000002689 soil Substances 0.000 description 35
• 239000000243 solution Substances 0.000 description 35
• 239000000725 suspension Substances 0.000 description 33
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 239000007921 spray Substances 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 230000001580 bacterial effect Effects 0.000 description 23
• 239000000126 substance Substances 0.000 description 23
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• 238000003756 stirring Methods 0.000 description 19
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
• 230000002538 fungal effect Effects 0.000 description 18
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• 238000002474 experimental method Methods 0.000 description 16
• 238000011534 incubation Methods 0.000 description 16
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 241000894006 Bacteria Species 0.000 description 15
• 230000005764 inhibitory process Effects 0.000 description 15
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• 235000015097 nutrients Nutrition 0.000 description 14
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
• 238000009472 formulation Methods 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
• 235000019441 ethanol Nutrition 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
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• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
• 240000008067 Cucumis sativus Species 0.000 description 9
• 241001330975 Magnaporthe oryzae Species 0.000 description 9
• 240000007594 Oryza sativa Species 0.000 description 9
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