DK175588B1 - Benzothiadiazoler og deres anvendelse i fremgangsmåder og midler mod plantesygdomme - Google Patents
Benzothiadiazoler og deres anvendelse i fremgangsmåder og midler mod plantesygdomme Download PDFInfo
- 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
Links
- 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
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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
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- 230000001580 bacterial effect Effects 0.000 description 23
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
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- 238000002474 experimental method Methods 0.000 description 16
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- 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
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- 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
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- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- XPPHXNSMZZHFLE-UHFFFAOYSA-N methyl 6-fluoro-1,2,3-benzothiadiazole-7-carboxylate Chemical compound COC(=O)C1=C(F)C=CC2=C1SN=N2 XPPHXNSMZZHFLE-UHFFFAOYSA-N 0.000 description 1
- SUJWQHRDFZPNFR-UHFFFAOYSA-N methyl 7-(1,2,4-triazol-1-yl)-1,2,3-benzothiadiazole-4-carboxylate Chemical compound C1=2SN=NC=2C(C(=O)OC)=CC=C1N1C=NC=N1 SUJWQHRDFZPNFR-UHFFFAOYSA-N 0.000 description 1
- CAAOYUDESBLEKC-UHFFFAOYSA-N methyl 7-trimethylsilyl-1,2,3-benzothiadiazole-4-carboxylate Chemical compound COC(=O)C1=CC=C([Si](C)(C)C)C2=C1N=NS2 CAAOYUDESBLEKC-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 239000002855 microbicide agent Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- UTJZGQOTYGZCKY-UHFFFAOYSA-N n'-cycloheptyl-1,2,3-benzothiadiazole-7-carbohydrazide Chemical compound C=1C=CC=2N=NSC=2C=1C(=O)NNC1CCCCCC1 UTJZGQOTYGZCKY-UHFFFAOYSA-N 0.000 description 1
- JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- YHPAGYGORMDWBP-UHFFFAOYSA-N n-(cyclopentylideneamino)-1,2,3-benzothiadiazole-7-carboxamide Chemical compound C=1C=CC=2N=NSC=2C=1C(=O)NN=C1CCCC1 YHPAGYGORMDWBP-UHFFFAOYSA-N 0.000 description 1
- WDESYCUJKHIIOJ-UHFFFAOYSA-N n-(dicyanomethyl)-1,2,3-benzothiadiazole-7-carboxamide Chemical compound N#CC(C#N)NC(=O)C1=CC=CC2=C1SN=N2 WDESYCUJKHIIOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UUJZTYDDXSALLA-UHFFFAOYSA-N naphthalen-1-ylmethyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1COC(=O)C1=CC=CC2=C1SN=N2 UUJZTYDDXSALLA-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- FDJSESZWPWMLEC-UHFFFAOYSA-N nonane Chemical compound CCCCCCCC[CH2+] FDJSESZWPWMLEC-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- MOYNWSIECWYBMT-UHFFFAOYSA-N o-methyl 2-methyl-3,5-dinitrobenzenecarbothioate Chemical compound COC(=S)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1C MOYNWSIECWYBMT-UHFFFAOYSA-N 0.000 description 1
- JKPGOFMXSSVBSO-UHFFFAOYSA-N o-methyl 3,5-diamino-2-benzylbenzenecarbothioate Chemical compound COC(=S)C1=CC(N)=CC(N)=C1CC1=CC=CC=C1 JKPGOFMXSSVBSO-UHFFFAOYSA-N 0.000 description 1
- JTMTUIJTZSBAGE-UHFFFAOYSA-N o-methyl 3,5-diamino-2-dodecylbenzenecarbothioate Chemical compound CCCCCCCCCCCCC1=C(N)C=C(N)C=C1C(=S)OC JTMTUIJTZSBAGE-UHFFFAOYSA-N 0.000 description 1
- NRNCXEALLQXPJQ-UHFFFAOYSA-N o-methyl 3,5-diamino-2-propan-2-ylbenzenecarbothioate Chemical compound COC(=S)C1=CC(N)=CC(N)=C1C(C)C NRNCXEALLQXPJQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002892 organic cations Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- LGGNBHZZNNEZCQ-UHFFFAOYSA-N propyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound CCCOC(=O)C1=CC=CC2=C1SN=N2 LGGNBHZZNNEZCQ-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- OBNWPPAWWUFOPM-UHFFFAOYSA-N pyridin-2-ylmethyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound C=1C=CC=2N=NSC=2C=1C(=O)OCC1=CC=CC=N1 OBNWPPAWWUFOPM-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 230000000405 serological effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- VOTRIHMEBPGDEL-UHFFFAOYSA-N tert-butyl 1,2,3-benzothiadiazole-7-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CC2=C1SN=N2 VOTRIHMEBPGDEL-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/82—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 three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/10—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to heterocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH322987 | 1987-08-21 | ||
CH322987 | 1987-08-21 |
Publications (3)
Publication Number | Publication Date |
---|---|
DK467688D0 DK467688D0 (da) | 1988-08-19 |
DK467688A DK467688A (da) | 1989-02-22 |
DK175588B1 true DK175588B1 (da) | 2004-12-13 |
Family
ID=4251434
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK198804676A DK175588B1 (da) | 1987-08-21 | 1988-08-19 | Benzothiadiazoler og deres anvendelse i fremgangsmåder og midler mod plantesygdomme |
Country Status (25)
Country | Link |
---|---|
US (3) | US4931581A (fr) |
EP (1) | EP0313512B1 (fr) |
JP (1) | JP2964144B2 (fr) |
KR (1) | KR970001484B1 (fr) |
CN (3) | CN1025614C (fr) |
AT (1) | ATE82668T1 (fr) |
AU (1) | AU620558B2 (fr) |
BG (4) | BG60283B2 (fr) |
BR (1) | BR8804264A (fr) |
CA (1) | CA1339571C (fr) |
CZ (1) | CZ285601B6 (fr) |
DD (1) | DD282609A5 (fr) |
DE (2) | DE3876211D1 (fr) |
DK (1) | DK175588B1 (fr) |
ES (1) | ES2052772T3 (fr) |
GR (1) | GR3006949T3 (fr) |
HU (1) | HU210904B (fr) |
IE (1) | IE62910B1 (fr) |
IL (1) | IL87503A (fr) |
MX (1) | MX9202664A (fr) |
NZ (1) | NZ225877A (fr) |
PT (1) | PT88307B (fr) |
SK (1) | SK570388A3 (fr) |
TR (1) | TR25187A (fr) |
ZA (1) | ZA886157B (fr) |
Families Citing this family (113)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5302607A (en) * | 1989-02-21 | 1994-04-12 | Ciba-Geigy Corporation | Compositions for protecting plants against disease |
ATE95815T1 (de) * | 1989-02-21 | 1993-10-15 | Ciba Geigy Ag | Mittel zum schutz von pflanzen gegen krankheiten. |
ATE102613T1 (de) * | 1989-02-21 | 1994-03-15 | Ciba Geigy Ag | Mittel zum schutz von pflanzen gegen krankheiten. |
ATE109139T1 (de) * | 1989-03-08 | 1994-08-15 | Ciba Geigy Ag | Mittel zum schutz von pflanzen gegen krankheiten. |
US5229384A (en) * | 1989-09-26 | 1993-07-20 | Ciba-Geigy Corporation | Compositions for protecting plants from diseases |
ATE102614T1 (de) * | 1989-09-26 | 1994-03-15 | Ciba Geigy Ag | Benzo-1,2,3-thiadiazol-derivate und ihre verwendung zum schutz von pflanzen gegen krankheiten. |
TW207999B (fr) * | 1991-03-06 | 1993-06-21 | Ciba Geigy Ag | |
US5260423A (en) * | 1991-03-06 | 1993-11-09 | Ciba-Geigy Corporation | Substituted benzo-1,2,3-thiadiazoles |
ES2101823T3 (es) * | 1991-06-05 | 1997-07-16 | Ciba Geigy Ag | Derivados benzo-1,2,3-tiadiazol. |
ATE317438T1 (de) * | 1992-07-01 | 2006-02-15 | Cornell Res Foundation Inc | Auslöser von überempfindlichkeitsreaktionen in pflanzen |
US5708139A (en) * | 1993-05-17 | 1998-01-13 | Cornell Research Foundation, Inc. | Pseudomonas syringae pv syringae hrpZ gene |
US5616590A (en) * | 1994-06-30 | 1997-04-01 | Ciba-Geigy Corporation | Plant microbicides |
AU695287B2 (en) * | 1994-10-17 | 1998-08-13 | Novartis Ag | Process for the preparation of substituted 3-aminobnzonitriles |
US5945437A (en) * | 1995-01-23 | 1999-08-31 | Novartis Finance Corporation | Crop protection products |
US6031153A (en) * | 1995-01-23 | 2000-02-29 | Novartis Ag | Method for protecting plants |
TW330146B (en) * | 1995-01-23 | 1998-04-21 | Novartis Ag | Crop protection composition and method of protecting plants |
DE69635307T2 (de) * | 1995-06-07 | 2006-07-13 | Cornell Research Foundation, Inc. | Induzierte widerstandsfähigkeit gegen überempfindlichkeitsreaktionen bei pflanzen |
US5850015A (en) * | 1995-06-07 | 1998-12-15 | Cornell Research Foundation, Inc. | Hypersensitive response elicitor from Erwinia chrysanthemi |
TW318777B (fr) * | 1995-06-29 | 1997-11-01 | Novartis Ag | |
TW353068B (en) * | 1995-12-11 | 1999-02-21 | Novartis Ag | Anti-fungus crop protection products |
EP0780394A1 (fr) * | 1995-12-20 | 1997-06-25 | Novartis AG | Microbicides |
US6498265B2 (en) | 1995-12-21 | 2002-12-24 | Syngenta Investment Corporation | 3-amino-2-mercaptobenzoic acid derivatives and processes for their preparation |
KR100471948B1 (ko) * | 1995-12-21 | 2005-07-07 | 신젠타 파티서페이션즈 아게 | 3-아미노-2-머캅토벤조산유도체및이들의제조방법 |
PT780372E (pt) | 1995-12-21 | 2002-04-29 | Syngenta Participations Ag | Derivados do acido 3-amino-2-mercaptobenzoico e processos para a sua preparacao |
US5847147A (en) | 1996-12-20 | 1998-12-08 | Novartis Corp. | 3-Amino-2-mercaptobenzoic acid derivatives and processes for their preparation |
US6002013A (en) * | 1995-12-21 | 1999-12-14 | Novartis Corporation | 3-amino-2-mercaptobenzoic acid derivatives and processes for their preparation |
DE19603576A1 (de) * | 1996-02-01 | 1997-08-07 | Bayer Ag | Acylierte 4-Amino und 4-Hydrazinopyrimidine |
JPH1017566A (ja) * | 1996-07-05 | 1998-01-20 | Nippon Bayeragrochem Kk | 1,2,3−ベンゾチアジアゾール誘導体及び植物病害防除剤 |
FR2751845B1 (fr) * | 1996-07-30 | 1998-09-11 | Rhone Poulenc Agrochimie | Nouvelle composition fongicide comprenant une 2-imidazoline- 5-one |
US6235974B1 (en) | 1996-12-05 | 2001-05-22 | Cornell Research Foundation, Inc. | Hypersensitive response induced resistance in plants by seed treatment with a hypersensitive response elicitor |
US6277814B1 (en) | 1997-01-27 | 2001-08-21 | Cornell Research Foundation, Inc. | Enhancement of growth in plants |
US6998515B1 (en) | 1997-01-27 | 2006-02-14 | Cornell Research Foundation, Inc. | Use of a nucleic acid encoding a hypersensitive response elicitor polypeptide to enhance growth in plants |
US5977060A (en) * | 1997-02-28 | 1999-11-02 | Cornell Research Foundation, Inc. | Insect control with a hypersensitive response elicitor |
JP4444382B2 (ja) * | 1997-03-26 | 2010-03-31 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 害虫駆除組成物 |
DE19716257A1 (de) | 1997-04-18 | 1998-10-22 | Bayer Ag | Fungizide Wirkstoffkombination |
US6297236B1 (en) | 1998-04-06 | 2001-10-02 | Bayer Aktiengesellschaft | Fungicide active substance combinations |
NZ501138A (en) | 1997-05-30 | 2002-11-26 | Cornell Res Foundation Inc | Hypersensitive response elicitor protein or polypeptide fragments from Erwinia |
HUP0004224A3 (en) | 1997-06-04 | 2002-11-28 | Basf Ag | Synergetic fungicidal mixture and its use |
US6201023B1 (en) | 1997-06-10 | 2001-03-13 | Agrogene Ltd. | Methods and compositions to protect crops against plant parasitic nematodes |
US6172184B1 (en) | 1997-08-06 | 2001-01-09 | Cornell Research Foundation, Inc. | Hypersensitive response elicitor from Pseudomonas syringae and its use |
US6228644B1 (en) * | 1997-08-06 | 2001-05-08 | Cornell Research Foundation, Inc. | Hypersensitive response elicitor from Erwinia amylovora, its use, and encoding gene |
US6262018B1 (en) | 1997-08-06 | 2001-07-17 | Cornell Research Foundation, Inc. | Hypersensitive response elicitor from Erwinia amylovora and its use |
GB9718036D0 (en) | 1997-08-27 | 1997-10-29 | Ciba Geigy Ag | Method for protecting plants |
US6333302B1 (en) | 1997-09-03 | 2001-12-25 | Cornell Research Foundation, Inc. | Use of hypersensitive response elicitor protein or polypeptide from Clavibacter michiganensis for disease resistance, growth enhancement and insect control |
CN1055086C (zh) * | 1998-04-13 | 2000-08-02 | 陕西省中国科学院西北植物研究所 | 5-胺基-1.2.3-噻二唑的制备方法 |
EP1434080A3 (fr) | 1998-04-22 | 2004-12-15 | Teijin Chemicals, Ltd. | Lentille opthalmique |
US6858707B1 (en) | 1998-10-05 | 2005-02-22 | Eden Bioscience Corporation | Hypersensitive response elicitor fragments which are active but do not elicit a hypersensitive response |
US6960705B2 (en) | 1998-10-05 | 2005-11-01 | Eden Bioscience Corporation | Nucleic acid encoding a hypersensitive response elicitor from Xanthomonas campestris |
US6624139B1 (en) | 1998-11-05 | 2003-09-23 | Eden Bioscience Corporation | Hypersensitive response elicitor-induced stress resistance |
US6281168B1 (en) | 1999-01-19 | 2001-08-28 | American Cyanamid Co. | Herbicidal compositions and method of safening herbicides using benzothiazole derivatives |
HUP0203563A3 (en) | 1999-12-13 | 2003-03-28 | Bayer Ag | Fungicidal combinations of active substances and use thereof |
US20020144310A1 (en) * | 2000-01-28 | 2002-10-03 | Lightfoot David A. | Isolated polynucleotides and polypeptides relating to loci underlying resistance to soybean cyst nematode and soybean sudden death syndrome and methods employing same |
DE10019758A1 (de) * | 2000-04-20 | 2001-10-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
DE10103832A1 (de) * | 2000-05-11 | 2001-11-15 | Bayer Ag | Fungizide Wirkstoffkombinationen |
DE10049804A1 (de) * | 2000-10-09 | 2002-04-18 | Bayer Ag | Wirkstoffkombinationen mit fungiziden und akariziden Eigenschaften |
DE10141618A1 (de) * | 2001-08-24 | 2003-03-06 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
AR037413A1 (es) | 2001-11-27 | 2004-11-10 | Valent Biosciences Corp | Composicion herbicida intensificada |
US7338969B2 (en) | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
US7335779B2 (en) * | 2002-03-08 | 2008-02-26 | Quonova, Llc | Modulation of pathogenicity |
BR0308325A8 (pt) * | 2002-03-11 | 2018-03-20 | Basf Se | método para imunizar plantas contra bacterioses, e, uso de um composto |
KR20040097264A (ko) | 2002-04-04 | 2004-11-17 | 밸런트 바이오사이언시즈 코포레이션 | 강화된 제초제 조성물 |
KR101063178B1 (ko) * | 2002-12-16 | 2011-09-08 | 밸런트 바이오사이언시즈 코포레이션 | Ps-ii 억제제 및 sar 유도인자를 포함하는 제초제조성물 |
EP2078753A3 (fr) | 2002-12-26 | 2010-12-15 | Syngenta Participations AG | Polypeptides de type prolifération de cellules et leurs utilisations |
US20070197492A1 (en) * | 2003-05-06 | 2007-08-23 | Aldo Ammendola | Modulation of Pathogenicity |
DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
EP2311965A1 (fr) | 2004-03-08 | 2011-04-20 | Syngenta Participations AG. | Protéines de graines de maïs riches en glutamine et promoteur |
DE102005015677A1 (de) | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
US8754009B2 (en) | 2005-06-09 | 2014-06-17 | Bayer Cropscience Ag | Active compound combinations |
ITMI20051558A1 (it) | 2005-08-09 | 2007-02-10 | Isagro Spa | Miscele e-o composizioni sinergiche cin elevata attivita'fungicida |
EP2272968A3 (fr) | 2005-09-08 | 2011-08-31 | Chromatin, Inc. | Plantes modifiées avec mini-chromosomes |
CN101058574B (zh) * | 2005-12-14 | 2010-05-26 | 南开大学 | 苯并[1,2,3]噻二唑衍生物及其合成方法和用途 |
US7342500B2 (en) * | 2006-03-24 | 2008-03-11 | Mark Iv Industries, Corp. | Compact microstrip transponder antenna |
DE102006023263A1 (de) * | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
GB2442069A (en) * | 2006-09-25 | 2008-03-26 | Syngenta Participations Ag | Combination for protecting plants comprising acibenzolar-S-methyl and a silver salt |
CA2584934A1 (fr) | 2007-04-17 | 2008-10-17 | University Of Guelph | Gene et proteine de detection de sucre regules par l'azote et modulation associee |
DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
EP2090168A1 (fr) | 2008-02-12 | 2009-08-19 | Bayer CropScience AG | Méthode destinée à l'amélioration de la croissance des plantes |
CA2704518C (fr) | 2007-12-03 | 2018-02-20 | Syngenta Participations Ag | Ingenierie de proteines a susceptibilite enzymatique |
DE102008006622A1 (de) | 2008-01-29 | 2009-07-30 | Rheinisch-Westfälische Technische Hochschule Aachen | Verwendung von Benzothiadiazolen |
DE102008041695A1 (de) * | 2008-08-29 | 2010-03-04 | Bayer Cropscience Ag | Methoden zur Verbesserung des Pflanzenwachstums |
CN101492429B (zh) * | 2008-12-10 | 2010-12-15 | 上海泰禾(集团)有限公司 | 一种苯并-[1,2,3]-噻二唑-7-甲酸三氟乙酯的提纯方法 |
CN102365018B (zh) | 2009-03-25 | 2014-10-29 | 拜尔农作物科学股份公司 | 具有协同作用的活性成分结合物 |
BR112012001080A2 (pt) * | 2009-07-16 | 2015-09-01 | Bayer Cropscience Ag | Combinações de substâncias ativas sinérgicas contendo feniltriazóis |
GB0920892D0 (en) * | 2009-11-27 | 2010-01-13 | Syngenta Participations Ag | Plant growth regulation |
CN101743978A (zh) * | 2009-12-23 | 2010-06-23 | 深圳诺普信农化股份有限公司 | 含有活化酯的杀菌组合物 |
CN101836640B (zh) * | 2010-03-04 | 2014-06-11 | 中国农业科学院蔬菜花卉研究所 | 一种诱抗剂在控制园艺作物土传病害上的应用 |
CN103118541A (zh) | 2010-07-20 | 2013-05-22 | 拜耳知识产权有限责任公司 | 邻氨基苯甲酰胺衍生物通过灌注、土混、浇灌处理、滴注施用、注射至土壤、茎杆或花、在水培体系中通过处理栽植穴或浸渍施用、漂浮或种子箱施用或通过处理种子来防治昆虫和蛛螨的用途,以及增加植物对非生物胁迫的胁迫耐受性的用途 |
SG187968A1 (en) * | 2010-09-04 | 2013-04-30 | Merck Patent Gmbh | Conjugated polymers |
WO2013014245A1 (fr) | 2011-07-26 | 2013-01-31 | Helmholtz Zentrum München Deutsches Forschungszentrum Für Gesundheit Und Umwelt (Gmbh) | Composition phytosanitaire contenant des acides alpha-hydroxylés |
CN102532059B (zh) * | 2011-12-29 | 2016-11-02 | 华东理工大学 | 苯并[1,2,3]噻二唑含氟衍生物作为植物抗病激活剂的应用 |
US10524474B1 (en) | 2012-04-12 | 2020-01-07 | Syngenta Participations Ag | Method of controlling phytopathogenic diseases on turfgrass |
US10568327B1 (en) | 2012-04-12 | 2020-02-25 | Syngenta Participations Ag | Method of controlling phytopathogenic diseases on turfgrass |
US10517298B1 (en) | 2012-04-13 | 2019-12-31 | Syngenta Participations Ag | Method of controlling phytopathogenic diseases on turfgrass |
US9770028B1 (en) | 2012-04-13 | 2017-09-26 | Syngenta Participations Ag | Method of improving turfgrass abiotic stress tolerance |
CN102731434A (zh) * | 2012-07-10 | 2012-10-17 | 南开大学 | 1,2,3-噻二唑的苯并羧酸酯类衍生物的制备及植物激活抗病活性 |
EP2687097A1 (fr) | 2012-07-16 | 2014-01-22 | Universite D'angers | Agents de potentialisation pour protéger des plantes contre des infections fongiques |
US11566260B2 (en) | 2012-07-16 | 2023-01-31 | Universite D'angers | Potentiating agents for protecting plants from fungal infections |
CN104814033B (zh) * | 2012-08-25 | 2017-08-25 | 郑芝红 | 一种含环己磺菌胺的农药组合物 |
CN103651467B (zh) * | 2012-08-31 | 2015-09-09 | 陕西美邦农药有限公司 | 一种含环己磺菌胺的杀菌组合物 |
CN104886077A (zh) * | 2012-09-21 | 2015-09-09 | 陕西美邦农药有限公司 | 一种含氟唑活化酯与甲氧基丙烯酸酯类的杀菌组合物 |
JP6313312B2 (ja) | 2012-10-02 | 2018-04-18 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 農薬としての複素環化合物 |
WO2014060381A1 (fr) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Composés hétérocycliques pour la lutte contre les nuisibles |
US20150284380A1 (en) | 2012-10-31 | 2015-10-08 | Bayer Cropscience Ag | Novel heterocyclic compounds as pest control agents |
WO2015004028A1 (fr) | 2013-07-08 | 2015-01-15 | Bayer Cropscience Ag | Dérivés de sulfures et sulfoxydes d'aryles hexacycliques à liaison c‑n utilisés comme pesticides |
CA2918452A1 (fr) | 2013-07-15 | 2015-01-22 | Donald Danforth Plant Science Center | Augmentation de la production d'huile et de la tolerance au stress dans des plantes |
KR101661706B1 (ko) | 2014-06-24 | 2016-10-04 | 한국생명공학연구원 | 미생물로부터 리소포스파티딜에탄올아민 18:1의 생산 방법 |
AU2015346281B2 (en) | 2014-11-12 | 2021-12-02 | Nmc, Inc. | Transgenic plants with engineered redox sensitive modulation of photosynthetic antenna complex pigments and methods for making the same |
EP2910126A1 (fr) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Combinaisons de composés actifs à propriétés insecticides |
PL232272B1 (pl) | 2015-07-28 | 2019-05-31 | Fundacja Univ Im Adama Mickiewicza W Poznaniu | Zastosowanie amidów 7-karboksybenzo[1,2,3]tiadiazolu jako regulatora wzrostu roślin |
WO2019214858A1 (fr) | 2018-05-08 | 2019-11-14 | Technische Universität München | Activation d'immunité déclenchée par des motifs dans des plantes par élicitation réduite spécifique de lipooligosaccharide (lore) et ses variants |
CN109096226B (zh) * | 2018-07-19 | 2020-12-25 | 浙江工业大学 | 以2,1,3-苯并噻二唑为导向基的芳基碳氢活化乙酰氧基化方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1176799A (en) * | 1966-10-21 | 1970-01-07 | Shell Int Research | Novel Biocides and their preparation |
FR1541415A (fr) * | 1966-10-21 | 1968-10-04 | Shell Int Research | Compositions biocides contenant des dérivés 1, 2, 3,-thiadiazoles, nouveaux 1, 2, 3-thiadiazoles, et leur préparation |
DE2728523C2 (de) * | 1977-06-23 | 1986-02-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-Methyl-1,2,3-thiadiazol-5-carbonsäure-(cyclohexylmethyl)-amid, Mittel mit herbizider und wachstumsregulatorischer Wirkung enthaltend diese Verbindung sowie Verfahren zu seiner Herstellung |
-
1988
- 1988-08-17 EP EP88810561A patent/EP0313512B1/fr not_active Expired - Lifetime
- 1988-08-17 DE DE8888810561T patent/DE3876211D1/de not_active Expired - Lifetime
- 1988-08-17 DE DE19775050C patent/DE19775050I2/de active Active
- 1988-08-17 AT AT88810561T patent/ATE82668T1/de not_active IP Right Cessation
- 1988-08-17 ES ES88810561T patent/ES2052772T3/es not_active Expired - Lifetime
- 1988-08-18 US US07/234,241 patent/US4931581A/en not_active Expired - Lifetime
- 1988-08-19 AU AU21156/88A patent/AU620558B2/en not_active Expired
- 1988-08-19 BG BG085287A patent/BG60283B2/bg unknown
- 1988-08-19 DD DD88319083A patent/DD282609A5/de not_active IP Right Cessation
- 1988-08-19 CZ CS885703A patent/CZ285601B6/cs not_active IP Right Cessation
- 1988-08-19 HU HU884408A patent/HU210904B/hu unknown
- 1988-08-19 PT PT88307A patent/PT88307B/pt not_active IP Right Cessation
- 1988-08-19 CA CA000575243A patent/CA1339571C/fr not_active Expired - Lifetime
- 1988-08-19 DK DK198804676A patent/DK175588B1/da not_active IP Right Cessation
- 1988-08-19 ZA ZA886157A patent/ZA886157B/xx unknown
- 1988-08-19 IE IE254288A patent/IE62910B1/en not_active IP Right Cessation
- 1988-08-19 TR TR88/0608A patent/TR25187A/xx unknown
- 1988-08-19 IL IL8750388A patent/IL87503A/en not_active IP Right Cessation
- 1988-08-19 SK SK5703-88A patent/SK570388A3/sk unknown
- 1988-08-19 NZ NZ225877A patent/NZ225877A/en unknown
- 1988-08-22 KR KR1019880010672A patent/KR970001484B1/ko not_active IP Right Cessation
- 1988-08-22 CN CN88106178A patent/CN1025614C/zh not_active Expired - Fee Related
- 1988-08-22 JP JP63207990A patent/JP2964144B2/ja not_active Expired - Lifetime
- 1988-08-22 BR BR8804264A patent/BR8804264A/pt not_active IP Right Cessation
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1989
- 1989-10-03 BG BG089893A patent/BG60296B2/bg unknown
- 1989-10-03 BG BG089894A patent/BG60297B2/bg unknown
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1991
- 1991-04-10 US US07/683,582 patent/US5190928A/en not_active Expired - Lifetime
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1992
- 1992-06-04 MX MX9202664A patent/MX9202664A/es unknown
- 1992-07-20 CN CN92108687A patent/CN1033354C/zh not_active Expired - Lifetime
- 1992-07-20 CN CN92108697A patent/CN1033299C/zh not_active Expired - Lifetime
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1993
- 1993-01-29 GR GR920402876T patent/GR3006949T3/el unknown
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1994
- 1994-01-18 BG BG098377A patent/BG61053B2/xx unknown
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1995
- 1995-03-14 US US08/405,488 patent/US5523311A/en not_active Expired - Lifetime
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