CA1059520A - S-triazolo (5,1-b) benzothiazoles - Google Patents
S-triazolo (5,1-b) benzothiazolesInfo
- Publication number
- CA1059520A CA1059520A CA242,835A CA242835A CA1059520A CA 1059520 A CA1059520 A CA 1059520A CA 242835 A CA242835 A CA 242835A CA 1059520 A CA1059520 A CA 1059520A
- Authority
- CA
- Canada
- Prior art keywords
- triazolo
- benzothiazole
- methyl
- compound
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KXTBPEZJLWXNEV-UHFFFAOYSA-N [1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical class S1C2=CC=CC=C2N2C1=NC=N2 KXTBPEZJLWXNEV-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 241000233866 Fungi Species 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 20
- -1 2-hydroxy-5-methyl-s-triazolo[5,1-b]benzothiazole 5-chloro-s-triazolo[5,1-b]benzothiazole 5-fluoro-2-methyl-s-triazolo[5,1-b]benzothiazole 5-methyl-s-triazolo[5,1-b]benzothiazole Chemical compound 0.000 claims description 16
- 230000002411 adverse Effects 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002085 enols Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- SXDQPPNODZHYJA-UHFFFAOYSA-N 2-imino-1,3-benzothiazol-3-amine Chemical class C1=CC=C2SC(=N)N(N)C2=C1 SXDQPPNODZHYJA-UHFFFAOYSA-N 0.000 abstract description 3
- 241000196324 Embryophyta Species 0.000 description 40
- 238000012360 testing method Methods 0.000 description 37
- 239000006185 dispersion Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002689 soil Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 241000209094 Oryza Species 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 235000007164 Oryza sativa Nutrition 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 235000009566 rice Nutrition 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 244000046052 Phaseolus vulgaris Species 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 235000021028 berry Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- 238000004452 microanalysis Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- AYEUDHSBNGFAOK-UHFFFAOYSA-N 2,5-dimethyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound S1C2=C(C)C=CC=C2N2C1=NC(C)=N2 AYEUDHSBNGFAOK-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- 241000221577 Uromyces appendiculatus Species 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- MFWMPLIPAZFWQI-UHFFFAOYSA-N 5-fluoro-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound FC1=CC=CC2=C1SC1=NC=NN21 MFWMPLIPAZFWQI-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- CHKQALUEEULCPZ-UHFFFAOYSA-N amino 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S(=O)(=O)ON)C(C)=C1 CHKQALUEEULCPZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical class CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
- ZYBFXFIGFRENIX-UHFFFAOYSA-N 5-methoxy-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound COC1=CC=CC2=C1SC1=NC=NN21 ZYBFXFIGFRENIX-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 101100108536 Rattus norvegicus Aldh3a1 gene Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- PDGKPDALSDRSHF-UHFFFAOYSA-N [1,3]thiazolo[3,2-b][1,2,4]triazole Chemical class N1=CN=C2SC=CN21 PDGKPDALSDRSHF-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- LFLDIKDHDLWZNL-UHFFFAOYSA-N n-(2-imino-4-methyl-1,3-benzothiazol-3-yl)acetamide Chemical compound C1=CC=C2SC(=N)N(NC(=O)C)C2=C1C LFLDIKDHDLWZNL-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PYSBNSKTLPBETN-UHFFFAOYSA-N 2,7-dimethyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound S1C2=CC=C(C)C=C2N2C1=NC(C)=N2 PYSBNSKTLPBETN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- QVXJJLKDAKPHFH-UHFFFAOYSA-N 2-imino-4-methoxy-1,3-benzothiazol-3-amine Chemical compound COC1=CC=CC2=C1N(N)C(=N)S2 QVXJJLKDAKPHFH-UHFFFAOYSA-N 0.000 description 1
- UEVHEHGTVUXSAC-UHFFFAOYSA-N 2-imino-4-methyl-1,3-benzothiazol-3-amine Chemical compound CC1=CC=CC2=C1N(N)C(=N)S2 UEVHEHGTVUXSAC-UHFFFAOYSA-N 0.000 description 1
- PSCPPDIXOMCFTR-UHFFFAOYSA-N 2-methyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound S1C2=CC=CC=C2N2C1=NC(C)=N2 PSCPPDIXOMCFTR-UHFFFAOYSA-N 0.000 description 1
- YELMWJNXDALKFE-UHFFFAOYSA-N 3h-imidazo[4,5-f]quinoxaline Chemical class N1=CC=NC2=C(NC=N3)C3=CC=C21 YELMWJNXDALKFE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CHKQKYSWAZYXFX-UHFFFAOYSA-N 4-chloro-2-imino-1,3-benzothiazol-3-amine Chemical compound C1=CC=C2SC(=N)N(N)C2=C1Cl CHKQKYSWAZYXFX-UHFFFAOYSA-N 0.000 description 1
- YEBCRAVYUWNFQT-UHFFFAOYSA-N 4-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=CC2=C1N=C(N)S2 YEBCRAVYUWNFQT-UHFFFAOYSA-N 0.000 description 1
- FEYNPIANFWGXQH-UHFFFAOYSA-N 5-chloro-2-methyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound S1C2=C(Cl)C=CC=C2N2C1=NC(C)=N2 FEYNPIANFWGXQH-UHFFFAOYSA-N 0.000 description 1
- IMTIKLBVRGLJKL-UHFFFAOYSA-N 5-chloro-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound ClC1=CC=CC2=C1SC1=NC=NN21 IMTIKLBVRGLJKL-UHFFFAOYSA-N 0.000 description 1
- KUQACLZFVMPDER-UHFFFAOYSA-N 5-ethyl-2-methyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound CCC1=CC=CC2=C1SC1=NC(C)=NN21 KUQACLZFVMPDER-UHFFFAOYSA-N 0.000 description 1
- OMVOESDTFYPQEP-UHFFFAOYSA-N 5-fluoro-2-methyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound S1C2=C(F)C=CC=C2N2C1=NC(C)=N2 OMVOESDTFYPQEP-UHFFFAOYSA-N 0.000 description 1
- YSMODUONRAFBET-UHFFFAOYSA-N 5-hydroxylysine Chemical group NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
- RFPZRBBRRPIWDL-UHFFFAOYSA-N 5-methoxy-2-methyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound COC1=CC=CC2=C1SC1=NC(C)=NN21 RFPZRBBRRPIWDL-UHFFFAOYSA-N 0.000 description 1
- QHHDLCGKFZOWRO-UHFFFAOYSA-N 5-methyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound CC1=CC=CC2=C1SC1=NC=NN21 QHHDLCGKFZOWRO-UHFFFAOYSA-N 0.000 description 1
- LGCNECZFDPBSJP-UHFFFAOYSA-N 6-ethyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound CCC1=CC=C2N3N=CN=C3SC2=C1 LGCNECZFDPBSJP-UHFFFAOYSA-N 0.000 description 1
- MPTJOBPMQBPBGM-UHFFFAOYSA-N 7-ethyl-1h-[1,2,4]triazolo[5,1-b][1,3]benzothiazol-2-one Chemical compound CCC1=CC=C2SC3=NC(O)=NN3C2=C1 MPTJOBPMQBPBGM-UHFFFAOYSA-N 0.000 description 1
- VCZPPHNXQICOTK-UHFFFAOYSA-N 7-methyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound CC1=CC=C2SC3=NC=NN3C2=C1 VCZPPHNXQICOTK-UHFFFAOYSA-N 0.000 description 1
- KATHSUHRDUEEDC-UHFFFAOYSA-N 8-fluoro-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound FC1=CC=CC2=C1N1N=CN=C1S2 KATHSUHRDUEEDC-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000190150 Bipolaris sorokiniana Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- 241000222235 Colletotrichum orbiculare Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000006165 Knowles reaction Methods 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- ZXQSTAALUNLITN-UHFFFAOYSA-N N-(3-amino-4-methoxy-1,3-benzothiazol-2-ylidene)acetamide Chemical compound C(C)(=O)N=C1SC2=C(N1N)C(=CC=C2)OC ZXQSTAALUNLITN-UHFFFAOYSA-N 0.000 description 1
- PLSHWHOMBADWEG-UHFFFAOYSA-N N-(3-amino-6-chloro-1,3-benzothiazol-2-ylidene)acetamide Chemical compound C(C)(=O)N=C1SC2=C(N1N)C=CC(=C2)Cl PLSHWHOMBADWEG-UHFFFAOYSA-N 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- FTZWGASIQCPNBR-UHFFFAOYSA-N NN1C(SC2=C1C(=CC=C2)OC)=NC(=O)OC.C(C)(=O)N=C2SC1=C(N2N)C=CC(=C1)CC.C(C)(=O)N=C1SC2=C(N1N)C(=CC=C2)F Chemical compound NN1C(SC2=C1C(=CC=C2)OC)=NC(=O)OC.C(C)(=O)N=C2SC1=C(N2N)C=CC(=C1)CC.C(C)(=O)N=C1SC2=C(N1N)C(=CC=C2)F FTZWGASIQCPNBR-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 206010034962 Photopsia Diseases 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- PIRYKGLQLCKQPG-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoline Chemical class C1=CC=C2N3C=NN=C3C=CC2=C1 PIRYKGLQLCKQPG-UHFFFAOYSA-N 0.000 description 1
- BBWDQWYZQIERSU-UHFFFAOYSA-N [1,3]thiazolo[2,3-c][1,2,4]triazole Chemical compound C1=NN=C2SC=CN21 BBWDQWYZQIERSU-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 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 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- POGRUOXQFUTZSA-UHFFFAOYSA-N methyl N-(3-amino-4-chloro-1,3-benzothiazol-2-ylidene)carbamate Chemical compound NN1C(SC2=C1C(=CC=C2)Cl)=NC(=O)OC POGRUOXQFUTZSA-UHFFFAOYSA-N 0.000 description 1
- GAGHSOWEYZMQJL-UHFFFAOYSA-N methyl n-(3-amino-4-methyl-1,3-benzothiazol-2-ylidene)carbamate Chemical compound C1=CC(C)=C2N(N)C(=NC(=O)OC)SC2=C1 GAGHSOWEYZMQJL-UHFFFAOYSA-N 0.000 description 1
- MSQSYVUICNFIBI-UHFFFAOYSA-N n'-(2-methylphenyl)acetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1C MSQSYVUICNFIBI-UHFFFAOYSA-N 0.000 description 1
- BANWEHUUBXLWNI-UHFFFAOYSA-N n-(3-amino-4-methyl-1,3-benzothiazol-2-ylidene)acetamide Chemical compound C1=CC(C)=C2N(N)C(=NC(=O)C)SC2=C1 BANWEHUUBXLWNI-UHFFFAOYSA-N 0.000 description 1
- RRPKGUUYTHFUPN-UHFFFAOYSA-N n-hydroxy-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(S(=O)(=O)NO)C(C)=C1 RRPKGUUYTHFUPN-UHFFFAOYSA-N 0.000 description 1
- XMJJPCJUQLGGND-UHFFFAOYSA-N n-hydroxy-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NO)C=C1 XMJJPCJUQLGGND-UHFFFAOYSA-N 0.000 description 1
- YKSVNSKYIUPAKW-UHFFFAOYSA-N n-hydroxymethanesulfonamide Chemical compound CS(=O)(=O)NO YKSVNSKYIUPAKW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000065 phosphene Inorganic materials 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IUMRBKDMFRMZFM-UHFFFAOYSA-N tetrazolo[5,1-b][1,3]benzothiazole Chemical compound C1=CC=C2N3N=NN=C3SC2=C1 IUMRBKDMFRMZFM-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 229910000634 wood's metal Inorganic materials 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54782975A | 1975-02-07 | 1975-02-07 | |
| US05/547,828 US3974286A (en) | 1975-02-07 | 1975-02-07 | S-Triazolo [5,1-b]benzothiazoles as fungicidal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1059520A true CA1059520A (en) | 1979-07-31 |
Family
ID=27068669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,835A Expired CA1059520A (en) | 1975-02-07 | 1975-12-31 | S-triazolo (5,1-b) benzothiazoles |
Country Status (22)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6017763B2 (ja) * | 1976-04-28 | 1985-05-07 | クミアイ化学工業株式会社 | イモチ病防除用殺菌組成物 |
| JPS639785A (ja) * | 1986-06-30 | 1988-01-16 | Daiwa Handotai Sochi Kk | 半導体プロセス用ガス供給制御バルブ装置 |
| JP2790299B2 (ja) * | 1989-02-01 | 1998-08-27 | 保土谷化学工業株式会社 | ペンゾチアゾール誘導体 |
-
1975
- 1975-12-30 GR GR49700A patent/GR58592B/el unknown
- 1975-12-31 IL IL48772A patent/IL48772A/xx unknown
- 1975-12-31 CA CA242,835A patent/CA1059520A/en not_active Expired
-
1976
- 1976-01-02 IN IN18/CAL/76A patent/IN142196B/en unknown
- 1976-01-02 IE IE5/76A patent/IE42229B1/en unknown
- 1976-01-09 PH PH17953A patent/PH14585A/en unknown
- 1976-01-15 MX MX763632U patent/MX3779E/es unknown
- 1976-01-20 AR AR261973A patent/AR217397A1/es active
- 1976-01-23 YU YU00188/76A patent/YU18876A/xx unknown
- 1976-01-29 FR FR7602435A patent/FR2300093A1/fr active Granted
- 1976-01-30 GB GB3704/76A patent/GB1531052A/en not_active Expired
- 1976-01-31 EG EG51/76A patent/EG12116A/xx active
- 1976-02-02 NL NL7601015A patent/NL7601015A/xx not_active Application Discontinuation
- 1976-02-05 CH CH143576A patent/CH609702A5/xx not_active IP Right Cessation
- 1976-02-05 IT IT19953/76A patent/IT1061008B/it active
- 1976-02-06 DE DE19762604726 patent/DE2604726A1/de not_active Withdrawn
- 1976-02-06 SU SU762320303A patent/SU722461A3/ru active
- 1976-02-06 AU AU10912/76A patent/AU500047B2/en not_active Expired
- 1976-02-06 BR BR7600773A patent/BR7600773A/pt unknown
- 1976-02-06 ES ES444974A patent/ES444974A1/es not_active Expired
- 1976-02-07 JP JP51012732A patent/JPS616076B2/ja not_active Expired
-
1978
- 1978-05-08 TR TR19140A patent/TR19140A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX3779E (es) | 1981-07-07 |
| SU722461A3 (ru) | 1980-03-15 |
| DE2604726A1 (de) | 1976-08-19 |
| IE42229B1 (en) | 1980-07-02 |
| IT1061008B (it) | 1982-10-20 |
| ES444974A1 (es) | 1977-08-16 |
| TR19140A (tr) | 1978-05-31 |
| NL7601015A (nl) | 1976-08-10 |
| IN142196B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-11 |
| IL48772A (en) | 1979-05-31 |
| PH14585A (en) | 1981-09-24 |
| FR2300093A1 (fr) | 1976-09-03 |
| IE42229L (en) | 1976-08-07 |
| AU1091276A (en) | 1977-08-11 |
| JPS51102000A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-08 |
| AU500047B2 (en) | 1979-05-10 |
| EG12116A (en) | 1978-06-30 |
| FR2300093B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-13 |
| AR217397A1 (es) | 1980-03-31 |
| YU18876A (en) | 1982-10-31 |
| CH609702A5 (en) | 1979-03-15 |
| BR7600773A (pt) | 1976-08-31 |
| JPS616076B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-02-24 |
| GR58592B (en) | 1977-11-10 |
| IL48772A0 (en) | 1976-02-29 |
| GB1531052A (en) | 1978-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100271913B1 (ko) | 특정한 트리아졸로피리미딘 유도체, 이의 제조방법, 상기 화합물을 함유한 조성물 및 살균제로서 이들의 사용 | |
| JP3002786B2 (ja) | 有害生物防除組成物 | |
| JP2003506466A (ja) | 殺真菌剤 | |
| RU2065861C1 (ru) | N-пиразолил-1,2,4-триазоло-[1,5-с]-пиримидин-2-сульфонамидные соединения, способ их получения, гербицидная композиция и способ борьбы с нежелательной растительностью | |
| US3764681A (en) | Certain tetrazolo-(1,5-a) quinoline compounds as fungus control agents | |
| AU606697B2 (en) | 6,7-dihydropyrazolo-(1,5-a) (1,3,5) triazine-2-sulphonamides, processes for their preparation and their use as herbicides and plant growth regulators | |
| KR870001694B1 (ko) | 티아(옥사) 디아졸 유도체의 제조방법 | |
| JPH07504403A (ja) | 置換されたフェニル複素環式除草剤 | |
| EP0405808B1 (en) | Phenoxyalkylamine derivatives and insecticides, acaricides and fungicides | |
| CA1059520A (en) | S-triazolo (5,1-b) benzothiazoles | |
| JPS6222763A (ja) | 新規なｎ−（２−フルオロフエニル）−アゾリジン及びその製造方法、並びに除草及び植物生長調節用組成物 | |
| CA1090332A (en) | Polycyclic nitrogen-containing compounds | |
| US4075218A (en) | S-Triazolo[5,1-b]benzothiazoles | |
| KR19990028282A (ko) | 살충성 트리스-옥시미노 헤테로고리 화합물 | |
| JPH069621A (ja) | 殺虫剤 | |
| US4859231A (en) | (6,7-)dihydro-(1,2,4) triazolo (1,5-A) (1,3,5) Triazine-2-sulphonamides, and their use as herbicides and plant growth regulators | |
| PL154972B1 (en) | Fungicide | |
| CA1068702A (en) | 4,5-dihydrotetrazolo (1,5-a) quinoxalines | |
| US4001227A (en) | Tetrazolo- and triazolobenzothiazines | |
| CA1292229C (en) | Pyridinyl-s-triazine derivatives, method for production thereof and a fungicide containing them as the active ingredient | |
| US3987196A (en) | Tetrazolo(1,5-a)quinoxalines for control of phytopathogens | |
| KR960009116B1 (ko) | 시아노아세트아미드 유도체, 그의 제조방법 및 그것을 유효 성분으로 함유하는 식물병 예방제 | |
| JPS5855481A (ja) | ヘテロ−置換されたピリド−４−オン誘導体類、それらの製造方法及び除草剤としてのそれらの使用 | |
| EP0340828B1 (en) | 5-Fluoromethyl-1,2,4-triazolo(1,5-a)-pyrimidine-2-sulfonamides, process for their preparation and compositions for their use as herbicides | |
| CA1081120A (en) | Fungicidal 3-phenyl-5-(substituted methyl) isoxazoles |