IL30585A - Compounds 1,2,4- Thiodiazolyl urea, their preparation and use for weed control - Google Patents
Compounds 1,2,4- Thiodiazolyl urea, their preparation and use for weed controlInfo
- Publication number
- IL30585A IL30585A IL30585A IL3058568A IL30585A IL 30585 A IL30585 A IL 30585A IL 30585 A IL30585 A IL 30585A IL 3058568 A IL3058568 A IL 3058568A IL 30585 A IL30585 A IL 30585A
- Authority
- IL
- Israel
- Prior art keywords
- urea
- formula
- admixture
- carrier
- reaction
- Prior art date
Links
- 235000013877 carbamide Nutrition 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title description 9
- -1 1,2,4-thiadiazolyl ureas Chemical class 0.000 title description 4
- 239000004009 herbicide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 23
- 241000196324 Embryophyta Species 0.000 claims description 22
- 239000004202 carbamide Substances 0.000 claims description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000007639 Anthemis cotula Nutrition 0.000 description 1
- 235000010960 Atriplex hastata Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000008645 Chenopodium bonus henricus Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 244000214240 Galinsoga parviflora Species 0.000 description 1
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 241001456088 Hesperocnide Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001310793 Podium Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000003960 organic solvent 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
- 230000008635 plant growth Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 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
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0053530 DE1670924B2 (de) | 1967-09-19 | 1967-09-19 | 1,2,4-thiadiazolyl-harnstoffderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL30585A0 IL30585A0 (en) | 1968-10-24 |
| IL30585A true IL30585A (en) | 1972-01-27 |
Family
ID=7106387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL30585A IL30585A (en) | 1967-09-19 | 1968-08-20 | Compounds 1,2,4- Thiodiazolyl urea, their preparation and use for weed control |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3686198A (de) |
| AT (1) | AT293090B (de) |
| BE (1) | BE721091A (de) |
| CH (1) | CH513194A (de) |
| DE (1) | DE1670924B2 (de) |
| DK (1) | DK123529B (de) |
| ES (1) | ES358290A1 (de) |
| FR (1) | FR1581394A (de) |
| GB (1) | GB1181186A (de) |
| IL (1) | IL30585A (de) |
| MY (1) | MY7000155A (de) |
| NL (1) | NL155547B (de) |
| SE (1) | SE336799B (de) |
| YU (1) | YU33525B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917478A (en) * | 1970-03-19 | 1975-11-04 | Ciba Geigy Corp | Herbicidal compositions and methods utilizing thiadiazolis ureas |
| CH549338A (de) * | 1970-03-19 | 1974-05-31 | Agripat Sa | Herbizides mittel. |
| US4021225A (en) * | 1971-02-26 | 1977-05-03 | Gulf Research & Development Company | Combating unwanted vegetation with 1,3,4-thiadiazole-2-sulfonamides |
| US3830641A (en) * | 1971-07-13 | 1974-08-20 | Fmc Corp | 1,2,3-thiadiazol-5-ylcarbamate herbicide compositions |
| US4228290A (en) * | 1979-01-25 | 1980-10-14 | Olin Corporation | Amino ester derivatives of 3-trihalomethyl-1,2,4-thiadiazoles |
| US4207090A (en) * | 1979-01-25 | 1980-06-10 | Olin Corporation | Amino ester derivatives of 3-trihalomethyl-1,2,4-thiadiazoles and their use as herbicides |
| DE3019259A1 (de) * | 1979-05-23 | 1980-12-04 | Ciba Geigy Ag | Salze von herbiziden 1,2,4-thiadiazolyl-5-harnstoffderivaten und deren verwendung |
| US4224449A (en) * | 1979-08-08 | 1980-09-23 | Olin Corporation | Biuret derivatives of 3-trihalomethyl-1,2,4-thiadiazoles |
| DE3172309D1 (en) * | 1980-06-27 | 1985-10-24 | Beiersdorf Ag | Substituted 3,5-diamino-1,2,4-oxadiazoles and 3,5-diamino-1,2,4-thiadiazoles, their preparation and pharmaceutical compositions containing them |
| DE3030530A1 (de) | 1980-08-13 | 1982-03-18 | Beiersdorf Ag, 2000 Hamburg | Alkyl- und cycloalkylsubstituierte 2-(2-(-hydroxy-3-tert-butylamino-propoxy)-5-acylaminophenyl)-1,3,4-oxadiazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zubereitungen |
| US4353920A (en) * | 1980-08-25 | 1982-10-12 | Olin Corporation | Use of selected 3-trihalomethyl-5-ureido-1,2,4-oxadiazoles and -1,2,4-thiadiazoles as agricultural viricides |
-
1967
- 1967-09-19 DE DE1967F0053530 patent/DE1670924B2/de active Granted
-
1968
- 1968-08-20 CH CH1250868A patent/CH513194A/de not_active IP Right Cessation
- 1968-08-20 IL IL30585A patent/IL30585A/en unknown
- 1968-09-12 SE SE12315/68A patent/SE336799B/xx unknown
- 1968-09-16 YU YU2169/68A patent/YU33525B/xx unknown
- 1968-09-18 GB GB44361/68A patent/GB1181186A/en not_active Expired
- 1968-09-18 DK DK449768AA patent/DK123529B/da unknown
- 1968-09-19 AT AT913968A patent/AT293090B/de not_active IP Right Cessation
- 1968-09-19 FR FR1581394D patent/FR1581394A/fr not_active Expired
- 1968-09-19 BE BE721091D patent/BE721091A/xx unknown
- 1968-09-19 ES ES358290A patent/ES358290A1/es not_active Expired
- 1968-09-19 NL NL6813437.A patent/NL155547B/xx unknown
-
1969
- 1969-10-01 US US862908A patent/US3686198A/en not_active Expired - Lifetime
-
1970
- 1970-12-31 MY MY1970155A patent/MY7000155A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES358290A1 (es) | 1970-06-01 |
| DE1670924B2 (de) | 1976-11-18 |
| IL30585A0 (en) | 1968-10-24 |
| NL6813437A (de) | 1969-03-21 |
| MY7000155A (de) | 1970-12-31 |
| FR1581394A (de) | 1969-09-12 |
| YU33525B (en) | 1977-06-30 |
| AT293090B (de) | 1971-09-27 |
| CH513194A (de) | 1971-09-30 |
| DE1670924A1 (de) | 1971-04-01 |
| SE336799B (de) | 1971-07-19 |
| DK123529B (da) | 1972-07-03 |
| BE721091A (de) | 1969-03-19 |
| GB1181186A (en) | 1970-02-11 |
| US3686198A (en) | 1972-08-22 |
| NL155547B (nl) | 1978-01-16 |
| YU216968A (en) | 1976-12-31 |
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