CA1090350A - Herbicidally active 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-ide salts - Google Patents
Herbicidally active 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-ide saltsInfo
- Publication number
- CA1090350A CA1090350A CA278,903A CA278903A CA1090350A CA 1090350 A CA1090350 A CA 1090350A CA 278903 A CA278903 A CA 278903A CA 1090350 A CA1090350 A CA 1090350A
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- compound
- general formula
- compounds
- thiadiazolin
- 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
- IDAFAPNAZCWRKV-UHFFFAOYSA-N 1,1-dimethyl-3-(1,3,4-thiadiazol-2-yl)urea Chemical class CN(C)C(=O)NC1=NN=CS1 IDAFAPNAZCWRKV-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 4
- 239000011734 sodium Chemical group 0.000 claims abstract description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 48
- 241000196324 Embryophyta Species 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 229910003002 lithium salt Inorganic materials 0.000 claims description 6
- 159000000002 lithium salts Chemical class 0.000 claims description 6
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 23
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- RSZWTIKSIIRBLH-UHFFFAOYSA-N 3-(5-ethyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CCC1=NN=C(NC(=O)N(C)C)S1 RSZWTIKSIIRBLH-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HRANAGQIKSICPC-UHFFFAOYSA-N 1,1-dimethyl-3-[5-(2-methylpropyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CC(C)Cc1nnc(NC(=O)N(C)C)s1 HRANAGQIKSICPC-UHFFFAOYSA-N 0.000 description 1
- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical class C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- LTQKIFCNCIFEHG-UHFFFAOYSA-N 1,2-oxazole 1H-pyrimidin-2-one Chemical class C=1C=NOC=1.O=C1N=CC=CN1 LTQKIFCNCIFEHG-UHFFFAOYSA-N 0.000 description 1
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- CMQJDYXIZIONAP-UHFFFAOYSA-N 1,3,4-thiadiazol-2-ylurea Chemical class NC(=O)NC1=NN=CS1 CMQJDYXIZIONAP-UHFFFAOYSA-N 0.000 description 1
- ZLOTYHZOJPLLGG-UHFFFAOYSA-N 1-sulfanylidenethiadiazinane Chemical class S=S1CCCNN1 ZLOTYHZOJPLLGG-UHFFFAOYSA-N 0.000 description 1
- FHWUZEFEQVWCCX-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-ethyl-N,N-dimethyl-1,3,4-thiadiazole-3-carboxamide Chemical compound CN(C(=O)N1C(SC(=N1)CC)=NC(N(C)C)=O)C FHWUZEFEQVWCCX-UHFFFAOYSA-N 0.000 description 1
- MHFOSTSHKXQVAO-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-N,N-dimethyl-1,3,4-thiadiazole-3-carboxamide Chemical class CN(C(=O)N1C(SC=N1)=NC(N(C)C)=O)C MHFOSTSHKXQVAO-UHFFFAOYSA-N 0.000 description 1
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- UGPLXUASBAGPJF-UHFFFAOYSA-N 5-propan-2-yl-2,3-dihydro-1,3,4-thiadiazole Chemical compound CC(C)C1=NNCS1 UGPLXUASBAGPJF-UHFFFAOYSA-N 0.000 description 1
- RWYWFKMNBXSVGS-UHFFFAOYSA-N 5-propyl-2,3-dihydro-1,3,4-thiadiazole Chemical compound C(CC)C=1SCNN=1 RWYWFKMNBXSVGS-UHFFFAOYSA-N 0.000 description 1
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- QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 0.000 description 1
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- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2623657.7 | 1976-05-24 | ||
| DE19762623657 DE2623657A1 (de) | 1976-05-24 | 1976-05-24 | 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-id-salze, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1090350A true CA1090350A (en) | 1980-11-25 |
Family
ID=5979098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA278,903A Expired CA1090350A (en) | 1976-05-24 | 1977-05-20 | Herbicidally active 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-ide salts |
Country Status (36)
| Country | Link |
|---|---|
| JP (1) | JPS52144671A (en]) |
| AT (1) | AT355368B (en]) |
| AU (1) | AU512025B2 (en]) |
| BE (1) | BE854971A (en]) |
| BG (1) | BG27900A3 (en]) |
| BR (1) | BR7702545A (en]) |
| CA (1) | CA1090350A (en]) |
| CH (1) | CH630234A5 (en]) |
| CS (1) | CS195333B2 (en]) |
| DD (1) | DD129853A5 (en]) |
| DE (1) | DE2623657A1 (en]) |
| DK (1) | DK143228C (en]) |
| EG (1) | EG12841A (en]) |
| ES (1) | ES458100A1 (en]) |
| FI (1) | FI64362C (en]) |
| FR (1) | FR2352809A1 (en]) |
| GB (1) | GB1582571A (en]) |
| GR (1) | GR72091B (en]) |
| HU (1) | HU180092B (en]) |
| IE (1) | IE45196B1 (en]) |
| IL (1) | IL52034A (en]) |
| IN (1) | IN155913B (en]) |
| IT (1) | IT1080397B (en]) |
| LU (1) | LU77391A1 (en]) |
| MX (1) | MX4627E (en]) |
| NL (1) | NL7704219A (en]) |
| NZ (1) | NZ184056A (en]) |
| PH (1) | PH14097A (en]) |
| PL (1) | PL102738B1 (en]) |
| PT (1) | PT66587B (en]) |
| RO (1) | RO72225A (en]) |
| SE (1) | SE422792B (en]) |
| SU (1) | SU701538A3 (en]) |
| TR (1) | TR20262A (en]) |
| YU (1) | YU39588B (en]) |
| ZA (1) | ZA773127B (en]) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1195672A (en) * | 1968-02-01 | 1970-06-17 | Mobil Oil Corp | Novel Urea Derivatives and Herbicides containing the same |
| US3565901A (en) * | 1969-01-29 | 1971-02-23 | Air Prod & Chem | Certain salts of 1,3,4-thiadiazol-2-ylureas |
| CH556862A (en) * | 1970-01-15 | 1974-12-13 | Air Prod & Chem | 1-(1,3,4-Thiadiazol-2-yl)-urea derivs as herbicides - and fungicides, prepd. from 2-amino-1,3,4-thiadiazoles |
| CH554886A (fr) * | 1970-01-15 | 1974-10-15 | Air Prod & Chem | Procede de preparation de thiadiazoles. |
| CH570391A5 (en) * | 1970-01-15 | 1975-12-15 | Air Prod & Chem | 1,3,4-Thiadiazole herbicides and fungicides - prepd. by reaction of carbamoyl chlorides with alkali metal derivs. of 2-amino-1,3,4-thiadiazoles |
| JPS5235672B2 (en]) * | 1972-05-22 | 1977-09-10 | ||
| US3803164A (en) * | 1972-05-22 | 1974-04-09 | Lilly Co Eli | Simplified one vessel preparation of 1-(5-alkyl-1,3,4-thiadiazol-2-yl)-1,3-dialkyl-ureas with azeotropic drying |
| JPS4929189A (en]) * | 1972-07-07 | 1974-03-15 | ||
| FR2237894A1 (en) * | 1973-06-29 | 1975-02-14 | Velsicol Chemical Corp | Thidiazolyl ureidoacetaldehyde acetals - as herbicies |
| JPS5220533A (en) * | 1975-08-05 | 1977-02-16 | Nippon Soken Inc | Collision detection apparatus |
-
1976
- 1976-05-24 DE DE19762623657 patent/DE2623657A1/de not_active Withdrawn
-
1977
- 1977-03-29 DK DK137577A patent/DK143228C/da not_active IP Right Cessation
- 1977-03-30 YU YU839/77A patent/YU39588B/xx unknown
- 1977-04-08 SU SU772468119A patent/SU701538A3/ru active
- 1977-04-18 NL NL7704219A patent/NL7704219A/xx not_active Application Discontinuation
- 1977-04-22 ES ES458100A patent/ES458100A1/es not_active Expired
- 1977-04-22 BR BR7702545A patent/BR7702545A/pt unknown
- 1977-04-26 BG BG036126A patent/BG27900A3/xx unknown
- 1977-04-26 FI FI771323A patent/FI64362C/fi not_active IP Right Cessation
- 1977-04-27 IN IN609/CAL/77A patent/IN155913B/en unknown
- 1977-05-04 MX MX775713U patent/MX4627E/es unknown
- 1977-05-05 IL IL52034A patent/IL52034A/xx unknown
- 1977-05-09 GB GB19295/77A patent/GB1582571A/en not_active Expired
- 1977-05-10 NZ NZ184056A patent/NZ184056A/xx unknown
- 1977-05-13 IE IE989/77A patent/IE45196B1/en unknown
- 1977-05-17 TR TR20262A patent/TR20262A/xx unknown
- 1977-05-19 PH PH19788A patent/PH14097A/en unknown
- 1977-05-19 CS CS773305A patent/CS195333B2/cs unknown
- 1977-05-20 CH CH627377A patent/CH630234A5/de not_active IP Right Cessation
- 1977-05-20 DD DD7700199045A patent/DD129853A5/xx unknown
- 1977-05-20 CA CA278,903A patent/CA1090350A/en not_active Expired
- 1977-05-20 RO RO7790421A patent/RO72225A/ro unknown
- 1977-05-21 PL PL1977198291A patent/PL102738B1/pl unknown
- 1977-05-23 SE SE7705982A patent/SE422792B/xx unknown
- 1977-05-23 FR FR7715683A patent/FR2352809A1/fr active Granted
- 1977-05-23 PT PT66587A patent/PT66587B/pt unknown
- 1977-05-23 GR GR53537A patent/GR72091B/el unknown
- 1977-05-23 AU AU25418/77A patent/AU512025B2/en not_active Expired
- 1977-05-23 EG EG311/77A patent/EG12841A/xx active
- 1977-05-23 HU HU77SCHE607A patent/HU180092B/hu unknown
- 1977-05-23 IT IT23863/77A patent/IT1080397B/it active
- 1977-05-23 LU LU77391A patent/LU77391A1/xx unknown
- 1977-05-24 ZA ZA00773127A patent/ZA773127B/xx unknown
- 1977-05-24 BE BE177847A patent/BE854971A/xx not_active IP Right Cessation
- 1977-05-24 JP JP6038277A patent/JPS52144671A/ja active Pending
- 1977-05-24 AT AT370077A patent/AT355368B/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |