DE2017842A1 - Neue Thiadiazolharnstoffe, herbicide Massen und Verfahren zur Regelung des Pflanzenwachstums - Google Patents
Neue Thiadiazolharnstoffe, herbicide Massen und Verfahren zur Regelung des PflanzenwachstumsInfo
- Publication number
- DE2017842A1 DE2017842A1 DE19702017842 DE2017842A DE2017842A1 DE 2017842 A1 DE2017842 A1 DE 2017842A1 DE 19702017842 DE19702017842 DE 19702017842 DE 2017842 A DE2017842 A DE 2017842A DE 2017842 A1 DE2017842 A1 DE 2017842A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- thiadiazole
- formula
- hydrogen atom
- thiadiazole ureas
- 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.)
- Ceased
Links
- -1 thiadiazole ureas Chemical class 0.000 title claims description 21
- 235000013877 carbamide Nutrition 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- 230000002363 herbicidal effect Effects 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 title claims description 5
- 230000008635 plant growth Effects 0.000 title claims description 5
- 230000001105 regulatory effect Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005109 alkynylthio group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000003106 haloaryl group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 230000002942 anti-growth Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 239000007787 solid Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 11
- 230000035784 germination Effects 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 235000011293 Brassica napus Nutrition 0.000 description 4
- 240000008100 Brassica rapa Species 0.000 description 4
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 244000152970 Digitaria sanguinalis Species 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000132536 Cirsium Species 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- GDGIVSREGUOIJZ-UHFFFAOYSA-N 5-amino-3h-1,3,4-thiadiazole-2-thione Chemical compound NC1=NN=C(S)S1 GDGIVSREGUOIJZ-UHFFFAOYSA-N 0.000 description 1
- QCMMKDSALYWVRF-UHFFFAOYSA-N 5-propan-2-ylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CC(C)SC1=NN=C(N)S1 QCMMKDSALYWVRF-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000115721 Pennisetum typhoides Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 239000000443 aerosol Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000020004 porter Nutrition 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- ISYCTVJTNGTOOM-UHFFFAOYSA-N thiadiazole;urea Chemical compound NC(N)=O.C1=CSN=N1 ISYCTVJTNGTOOM-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000133 toxic exposure Toxicity 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81807869A | 1969-04-21 | 1969-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2017842A1 true DE2017842A1 (de) | 1970-11-05 |
Family
ID=25224610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702017842 Ceased DE2017842A1 (de) | 1969-04-21 | 1970-04-14 | Neue Thiadiazolharnstoffe, herbicide Massen und Verfahren zur Regelung des Pflanzenwachstums |
Country Status (5)
| Country | Link |
|---|---|
| CA (1) | CA1002957A (enrdf_load_stackoverflow) |
| CH (1) | CH562558A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2017842A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2039331B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1290223A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2059328A1 (de) * | 1970-11-24 | 1972-06-08 | Schering Ag | Thiadiazolylharnstoffe mit herbizider Wirkung |
| JPS52102277A (en) * | 1976-02-20 | 1977-08-27 | Schering Ag | 22dimethylcarbamoyliminoo 1*3*44thiadiazolinee33ido derivatives * production thereof and herbicide containing same |
| JPS535166A (en) * | 1976-06-30 | 1978-01-18 | Gulf Oil Corp | Method of combating weeds in soybean field and substituted benzyl compound |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH502762A (de) * | 1968-07-17 | 1971-02-15 | Agripat Sa | Neue Thiadiazolyl-harnstoffe enthaltendes herbizides Mittel |
| US3990881A (en) * | 1975-08-25 | 1976-11-09 | Eli Lilly And Company | 5-(Hetero-ring sulfamoyl)-1,3,4-thiadiazol-2-ylureas |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670925B2 (de) * | 1967-09-19 | 1977-03-10 | Bayer Ag, 5090 Leverkusen | 1,3,4-thiadiazolylharnstoffe |
| GB1195672A (en) * | 1968-02-01 | 1970-06-17 | Mobil Oil Corp | Novel Urea Derivatives and Herbicides containing the same |
| GB1266172A (enrdf_load_stackoverflow) * | 1968-03-13 | 1972-03-08 |
-
1970
- 1970-02-26 GB GB1290223D patent/GB1290223A/en not_active Expired
- 1970-03-03 CA CA076,326A patent/CA1002957A/en not_active Expired
- 1970-04-14 DE DE19702017842 patent/DE2017842A1/de not_active Ceased
- 1970-04-20 FR FR7014293A patent/FR2039331B2/fr not_active Expired
- 1970-04-21 CH CH594570A patent/CH562558A5/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2059328A1 (de) * | 1970-11-24 | 1972-06-08 | Schering Ag | Thiadiazolylharnstoffe mit herbizider Wirkung |
| JPS52102277A (en) * | 1976-02-20 | 1977-08-27 | Schering Ag | 22dimethylcarbamoyliminoo 1*3*44thiadiazolinee33ido derivatives * production thereof and herbicide containing same |
| JPS535166A (en) * | 1976-06-30 | 1978-01-18 | Gulf Oil Corp | Method of combating weeds in soybean field and substituted benzyl compound |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2039331B2 (enrdf_load_stackoverflow) | 1974-08-09 |
| CA1002957A (en) | 1977-01-04 |
| GB1290223A (enrdf_load_stackoverflow) | 1972-09-20 |
| CH562558A5 (enrdf_load_stackoverflow) | 1975-06-13 |
| FR2039331A2 (enrdf_load_stackoverflow) | 1971-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: RHONE-POULENC INC., NEW YORK, N.Y:, US |
|
| 8128 | New person/name/address of the agent |
Representative=s name: KOHLER, M., DIPL.-CHEM. DR.RER.NAT. GERNHARDT, C., |
|
| 8162 | Independent application | ||
| 8128 | New person/name/address of the agent |
Representative=s name: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., 8000 MUENCHEN |
|
| 8131 | Rejection |