IE35564B1 - Herbicidally active thiadiazolylureas and their manufacture and use - Google Patents
Herbicidally active thiadiazolylureas and their manufacture and useInfo
- Publication number
- IE35564B1 IE35564B1 IE1065/71A IE106571A IE35564B1 IE 35564 B1 IE35564 B1 IE 35564B1 IE 1065/71 A IE1065/71 A IE 1065/71A IE 106571 A IE106571 A IE 106571A IE 35564 B1 IE35564 B1 IE 35564B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogen atom
- hal
- thiadiazole derivatives
- esters
- halides
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000004867 thiadiazoles Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- -1 carbamoyl halides Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- FVQNWQHWKMGOOW-UHFFFAOYSA-N N-(1H-pyrazol-5-ylsulfanyl)methanamine Chemical class CNSC1=NNC=C1 FVQNWQHWKMGOOW-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 150000001726 carbonic acid ester halides Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007530 organic bases Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1365556 Thiadiazole derivatives SCHERING AG 27 July 1971 [3 Sept 1970 24 Nov 1970] 35130/71 Heading C2C [Also in Division A5] Novel thiadiazole derivatives of the Formula (I) wherein R 1 is a C 1-3 alkyl group, n is 1 or 2 and when n is 1, R 2 is a hydrogen atom or a methyl group, and when n is 2, R 2 is a methyl group, are prepared by (1) oxidizing the corresponding compound in which n is zero, (2) reacting corresponding methylamino thiodiazole derivatives with (a) carbamoyl halides (Hal-CO-NR 2 -CH 3 ), (b) methyl isocyanate (R 2 then being a hydrogen atom), or (c) carbonic acid ester halides, thiolcarbonic acid ester halides or phosgene and then with amines R 2 NHCH 3 or (3) reacting thiodiazole ureas substituted in the nucleus by -SO 2 -B groups, B being a hydrogen atom, a metal equivalent or a group obtainable by addition of a hydrogen atom to a tertiary organic base, with alkylating agents of the formula R 1 -Hal, wherein Hal is a chlorine, bromine or iodine atom, or with esters of sulphuric acid or esters of aromatic sulphonic acids. Herbicidal compositions comprise the above thiadiazole derivatives together with suitable carriers. Reference has been directed by the Comptroller to Specification 1,195,672.
[GB1365556A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2044442A DE2044442C2 (en) | 1970-09-03 | 1970-09-03 | 1,1,3-Trimethyl-3 - (- 5-Ethylsulfonyl-1,3,4-Thiadiazol-2-yl) -urea with herbicidal action |
| DE19702059328 DE2059328C2 (en) | 1970-11-24 | 1970-11-24 | 1,1,3-Trimethyl-3- (5-ethylsulfinyl-1,3,4-thiadiazol-2-YL) urea |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35564L IE35564L (en) | 1972-03-03 |
| IE35564B1 true IE35564B1 (en) | 1976-03-18 |
Family
ID=25759699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1065/71A IE35564B1 (en) | 1970-09-03 | 1971-08-24 | Herbicidally active thiadiazolylureas and their manufacture and use |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5327339B1 (en) |
| AT (1) | AT310497B (en) |
| BE (1) | BE772168A (en) |
| BR (1) | BR7105556D0 (en) |
| CA (1) | CA942751A (en) |
| CH (1) | CH554636A (en) |
| CS (1) | CS167939B2 (en) |
| DK (1) | DK130182B (en) |
| EG (1) | EG10379A (en) |
| ES (1) | ES393478A1 (en) |
| FI (1) | FI55838C (en) |
| FR (1) | FR2107182A5 (en) |
| GB (1) | GB1365556A (en) |
| HU (1) | HU162898B (en) |
| IE (1) | IE35564B1 (en) |
| IL (1) | IL37529A (en) |
| KE (1) | KE2545A (en) |
| LU (1) | LU63804A1 (en) |
| NL (1) | NL174044C (en) |
| RO (3) | RO58556A (en) |
| SE (1) | SE375305B (en) |
| YU (1) | YU34419B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2246461C2 (en) * | 1972-09-21 | 1985-07-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3- (5-butylsulfonyl-1,3,4-thiadiazol-2-yl) urea and herbicidal agents containing this compound |
-
1971
- 1971-07-21 ES ES393478A patent/ES393478A1/en not_active Expired
- 1971-07-23 FI FI2099/71A patent/FI55838C/en active
- 1971-07-27 GB GB3513071A patent/GB1365556A/en not_active Expired
- 1971-07-27 CS CS5488A patent/CS167939B2/cs unknown
- 1971-07-27 YU YU1958/71A patent/YU34419B/en unknown
- 1971-08-04 DK DK381371AA patent/DK130182B/en unknown
- 1971-08-19 IL IL37529A patent/IL37529A/en unknown
- 1971-08-24 IE IE1065/71A patent/IE35564B1/en unknown
- 1971-08-25 BR BR5556/71A patent/BR7105556D0/en unknown
- 1971-08-30 EG EG387/71A patent/EG10379A/en active
- 1971-08-31 LU LU63804D patent/LU63804A1/xx unknown
- 1971-09-01 AT AT763471A patent/AT310497B/en not_active IP Right Cessation
- 1971-09-02 HU HUSC348A patent/HU162898B/hu unknown
- 1971-09-02 SE SE7111133A patent/SE375305B/xx unknown
- 1971-09-02 FR FR7131774A patent/FR2107182A5/fr not_active Expired
- 1971-09-03 BE BE772168A patent/BE772168A/en not_active IP Right Cessation
- 1971-09-03 RO RO68110A patent/RO58556A/ro unknown
- 1971-09-03 JP JP6801471A patent/JPS5327339B1/ja active Pending
- 1971-09-03 CH CH1296171A patent/CH554636A/en not_active IP Right Cessation
- 1971-09-03 RO RO77408A patent/RO71694B/en unknown
- 1971-09-03 CA CA122,104A patent/CA942751A/en not_active Expired
- 1971-09-03 NL NLAANVRAGE7112198,A patent/NL174044C/en not_active IP Right Cessation
- 1971-09-03 RO RO7177407A patent/RO71809A/en unknown
-
1975
- 1975-07-16 KE KE2545*UA patent/KE2545A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT310497B (en) | 1973-10-10 |
| CS167939B2 (en) | 1976-05-28 |
| BE772168A (en) | 1972-03-03 |
| RO71809A (en) | 1982-05-10 |
| FI55838C (en) | 1979-10-10 |
| BR7105556D0 (en) | 1973-02-15 |
| LU63804A1 (en) | 1972-01-06 |
| CH554636A (en) | 1974-10-15 |
| DK130182B (en) | 1975-01-13 |
| RO71694B (en) | 1984-03-31 |
| DK130182C (en) | 1975-08-11 |
| SE375305B (en) | 1975-04-14 |
| NL7112198A (en) | 1972-03-07 |
| YU195871A (en) | 1978-12-31 |
| GB1365556A (en) | 1974-09-04 |
| IL37529A0 (en) | 1971-11-29 |
| HU162898B (en) | 1973-04-28 |
| RO58556A (en) | 1975-10-15 |
| IL37529A (en) | 1977-04-29 |
| FI55838B (en) | 1979-06-29 |
| KE2545A (en) | 1975-08-01 |
| NL174044C (en) | 1984-04-16 |
| RO71694A (en) | 1984-03-15 |
| FR2107182A5 (en) | 1972-05-05 |
| YU34419B (en) | 1979-07-10 |
| IE35564L (en) | 1972-03-03 |
| JPS5327339B1 (en) | 1978-08-08 |
| ES393478A1 (en) | 1974-10-01 |
| EG10379A (en) | 1976-10-31 |
| CA942751A (en) | 1974-02-26 |
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