DE2044442C2 - 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung - Google Patents
1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider WirkungInfo
- Publication number
- DE2044442C2 DE2044442C2 DE2044442A DE2044442A DE2044442C2 DE 2044442 C2 DE2044442 C2 DE 2044442C2 DE 2044442 A DE2044442 A DE 2044442A DE 2044442 A DE2044442 A DE 2044442A DE 2044442 C2 DE2044442 C2 DE 2044442C2
- Authority
- DE
- Germany
- Prior art keywords
- urea
- herbicidal
- mentioned
- methyl
- thiadiazol
- 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
- 230000002363 herbicidal effect Effects 0.000 title claims description 12
- VRRNATHLUQTFGC-UHFFFAOYSA-N 1-(5-ethylsulfonyl-1,3,4-thiadiazol-2-yl)-1,3,3-trimethylurea Chemical compound CCS(=O)(=O)C1=NN=C(N(C)C(=O)N(C)C)S1 VRRNATHLUQTFGC-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 14
- 241000196324 Embryophyta Species 0.000 claims description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
- -1 Azol-2-yl Chemical group 0.000 claims description 11
- 239000000969 carrier Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 230000000052 comparative effect Effects 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000012050 conventional carrier Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 244000237956 Amaranthus retroflexus Species 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000207890 Ipomoea purpurea Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 240000004385 Centaurea cyanus Species 0.000 description 2
- 235000005940 Centaurea cyanus Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000005498 Setaria italica Species 0.000 description 2
- 235000007226 Setaria italica Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 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 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000000080 wetting agent 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)
- 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)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2044442A DE2044442C2 (de) | 1970-09-03 | 1970-09-03 | 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung |
| ZA714620A ZA714620B (en) | 1970-09-03 | 1971-07-13 | Herbicidally active thiadiazolylureas and their manufacture and use |
| ES393478A ES393478A1 (es) | 1970-09-03 | 1971-07-21 | Procedimiento para la preparacion de herbicidas. |
| FI2099/71A FI55838C (fi) | 1970-09-03 | 1971-07-23 | Saosom herbicider anvaendbara 1,1,3-trimetyl-1,3,4-tiadiazolylkarbamider |
| GB3513071A GB1365556A (en) | 1970-09-03 | 1971-07-27 | Herbicidally active thiadiazolylureas and their manufacture and u se |
| YU1958/71A YU34419B (en) | 1970-09-03 | 1971-07-27 | Process for preparing thiadiazolyl-carbamides |
| CS5488A CS167939B2 (enrdf_load_stackoverflow) | 1970-09-03 | 1971-07-27 | |
| DK381371AA DK130182B (da) | 1970-09-03 | 1971-08-04 | Herbicidt middel. |
| IL37529A IL37529A (en) | 1970-09-03 | 1971-08-19 | Herbicidally active 1,1,3-trimethyl-3-(5-substituted-1,3,4thiadiazol-2-yl)ureas their manufacture and preparations containing them |
| IE1065/71A IE35564B1 (en) | 1970-09-03 | 1971-08-24 | Herbicidally active thiadiazolylureas and their manufacture and use |
| BR5556/71A BR7105556D0 (pt) | 1970-09-03 | 1971-08-25 | Processo para a preparacao de tiadiazolilureias e composicoes herbicidas a base destas |
| PL1971150227A PL81808B1 (enrdf_load_stackoverflow) | 1970-09-03 | 1971-08-27 | |
| EG387/71A EG10379A (en) | 1970-09-03 | 1971-08-30 | Process for preparation of thiadizolyl urea and their use as herbicides |
| LU63804D LU63804A1 (enrdf_load_stackoverflow) | 1970-09-03 | 1971-08-31 | |
| AT763471A AT310497B (de) | 1970-09-03 | 1971-09-01 | Herbizide Mittel |
| AU33020/71A AU477072B2 (en) | 1970-09-03 | 1971-09-02 | Herbicidally active thiadiazolylureas and their manufacture and use |
| SE7111133A SE375305B (enrdf_load_stackoverflow) | 1970-09-03 | 1971-09-02 | |
| HUSC348A HU162898B (enrdf_load_stackoverflow) | 1970-09-03 | 1971-09-02 | |
| FR7131774A FR2107182A5 (enrdf_load_stackoverflow) | 1970-09-03 | 1971-09-02 | |
| CH1296171A CH554636A (de) | 1970-09-03 | 1971-09-03 | Herbicides mittel. |
| NLAANVRAGE7112198,A NL174044C (nl) | 1970-09-03 | 1971-09-03 | Werkwijze voor het bereiden van herbicide thiadiazolylalkylureumverbindingen, alsmede werkwijze voor het bereiden van deze verbindingen bevattende herbicide preparaten. |
| CA122,104A CA942751A (en) | 1970-09-03 | 1971-09-03 | Herbicidally active thiadiazolylureas |
| RO7177407A RO71809A (ro) | 1970-09-03 | 1971-09-03 | Procedeu pentru prepararea unor tiadiazoli-uree |
| RO68110A RO58556A (enrdf_load_stackoverflow) | 1970-09-03 | 1971-09-03 | |
| JP6801471A JPS5327339B1 (enrdf_load_stackoverflow) | 1970-09-03 | 1971-09-03 | |
| BE772168A BE772168A (fr) | 1970-09-03 | 1971-09-03 | Thiadiazolylurees a action herbicide, leur procede de preparation et leur utilisation |
| RO77408A RO71694B (ro) | 1970-09-03 | 1971-09-03 | Procedeu de preparare a unor derivati ai tiadiazolilureei |
| KE2545*UA KE2545A (en) | 1970-09-03 | 1975-07-16 | Herbicidally active thiadiazolylureas and their manufacture and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2044442A DE2044442C2 (de) | 1970-09-03 | 1970-09-03 | 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2044442A1 DE2044442A1 (en) | 1972-03-09 |
| DE2044442C2 true DE2044442C2 (de) | 1983-11-03 |
Family
ID=5781886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2044442A Expired DE2044442C2 (de) | 1970-09-03 | 1970-09-03 | 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU477072B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2044442C2 (enrdf_load_stackoverflow) |
| PL (1) | PL81808B1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA714620B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2246461C2 (de) * | 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)-harnstoff und herbizide Mittel enthaltend diese Verbindung |
| GB1561636A (en) * | 1975-11-07 | 1980-02-27 | Lilly Industries Ltd | Herbicidal combinations |
| DE2607481A1 (de) * | 1976-02-20 | 1977-08-25 | Schering Ag | 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-id-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| ZA775225B (en) * | 1977-08-29 | 1978-03-29 | Lilly Co Eli | Herbicidal combinations |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695847C3 (de) * | 1967-06-09 | 1978-09-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazole |
| GB1195672A (en) * | 1968-02-01 | 1970-06-17 | Mobil Oil Corp | Novel Urea Derivatives and Herbicides containing the same |
| CH502762A (de) * | 1968-07-17 | 1971-02-15 | Agripat Sa | Neue Thiadiazolyl-harnstoffe enthaltendes herbizides Mittel |
| CH521711A (de) * | 1968-12-23 | 1972-04-30 | Bayer Ag | Herbizides Mittel |
-
1970
- 1970-09-03 DE DE2044442A patent/DE2044442C2/de not_active Expired
-
1971
- 1971-07-13 ZA ZA714620A patent/ZA714620B/xx unknown
- 1971-08-27 PL PL1971150227A patent/PL81808B1/pl unknown
- 1971-09-02 AU AU33020/71A patent/AU477072B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA714620B (en) | 1972-04-26 |
| DE2044442A1 (en) | 1972-03-09 |
| AU3302071A (en) | 1973-03-08 |
| PL81808B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| AU477072B2 (en) | 1976-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8125 | Change of the main classification |
Ipc: C07D285/12 |
|
| 8126 | Change of the secondary classification |
Ipc: A01N 43/82 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |