IE42229B1 - Benzothiazole derivatives and their use as fungicides - Google Patents
Benzothiazole derivatives and their use as fungicidesInfo
- Publication number
- IE42229B1 IE42229B1 IE5/76A IE576A IE42229B1 IE 42229 B1 IE42229 B1 IE 42229B1 IE 5/76 A IE5/76 A IE 5/76A IE 576 A IE576 A IE 576A IE 42229 B1 IE42229 B1 IE 42229B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- benzothiazole
- methyl
- triazolo
- compounds
- Prior art date
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 239000000417 fungicide Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 241000233866 Fungi Species 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 230000002411 adverse Effects 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 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 claims description 3
- 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 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 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 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- LZMMPXYRHZESNZ-UHFFFAOYSA-N 5-chloro-1h-[1,2,4]triazolo[5,1-b][1,3]benzothiazol-2-one Chemical compound S1C2=C(Cl)C=CC=C2N2C1=NC(O)=N2 LZMMPXYRHZESNZ-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- NUXANMZNMRDIRL-UHFFFAOYSA-N 5-ethyl-[1,2,4]triazolo[5,1-b][1,3]benzothiazole Chemical compound CCC1=CC=CC2=C1SC1=NC=NN21 NUXANMZNMRDIRL-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
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- 230000010933 acylation Effects 0.000 abstract description 2
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- 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
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation 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
- 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
- COTKWNDCGCBCGE-UHFFFAOYSA-N methyl n-(3-amino-1,3-benzothiazol-2-ylidene)carbamate Chemical compound C1=CC=C2N(N)C(=NC(=O)OC)SC2=C1 COTKWNDCGCBCGE-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
- 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
- 239000002736 nonionic surfactant Substances 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 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
- 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
- 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
- HHFCAUSIBNOUOP-UHFFFAOYSA-N tetrazolo[1,5-a]quinoline Chemical class C1=CC2=NN=NN2C2=CC=CC=C21 HHFCAUSIBNOUOP-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 (2)
| Publication Number | Publication Date |
|---|---|
| IE42229L IE42229L (en) | 1976-08-07 |
| IE42229B1 true IE42229B1 (en) | 1980-07-02 |
Family
ID=27068669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE5/76A IE42229B1 (en) | 1975-02-07 | 1976-01-02 | Benzothiazole derivatives and their use as fungicides |
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 |
| 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 |
| CA1059520A (en) | 1979-07-31 |
| GR58592B (en) | 1977-11-10 |
| IL48772A0 (en) | 1976-02-29 |
| GB1531052A (en) | 1978-11-01 |
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