DE2430467C2 - Thiadiazolylimidazolidinone - Google Patents
ThiadiazolylimidazolidinoneInfo
- Publication number
- DE2430467C2 DE2430467C2 DE2430467A DE2430467A DE2430467C2 DE 2430467 C2 DE2430467 C2 DE 2430467C2 DE 2430467 A DE2430467 A DE 2430467A DE 2430467 A DE2430467 A DE 2430467A DE 2430467 C2 DE2430467 C2 DE 2430467C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- compounds
- tert
- ecm
- hydroxy
- 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
- 241000196324 Embryophyta Species 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 37
- 239000000203 mixture Substances 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 12
- -1 Azol-2-yl Chemical group 0.000 description 12
- 230000006735 deficit Effects 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 101001074628 Homo sapiens Phosphatidylinositol-glycan biosynthesis class W protein Proteins 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 102100036253 Phosphatidylinositol-glycan biosynthesis class W protein Human genes 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 235000011331 Brassica Nutrition 0.000 description 4
- 241000219198 Brassica Species 0.000 description 4
- 241000219312 Chenopodium Species 0.000 description 4
- 240000008853 Datura stramonium Species 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- 235000011999 Panicum crusgalli Nutrition 0.000 description 4
- 235000008515 Setaria glauca Nutrition 0.000 description 4
- 244000010062 Setaria pumila Species 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- 241000209200 Bromus Species 0.000 description 3
- 241001547427 Cissampelos pareira Species 0.000 description 3
- 244000152970 Digitaria sanguinalis Species 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- LTEUXHSAYOSFGQ-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)F)S1 LTEUXHSAYOSFGQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 241000217446 Calystegia sepium Species 0.000 description 2
- 241000508725 Elymus repens Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000158928 Scolochloa festucacea Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- TWAUUVMXSRYMPA-UHFFFAOYSA-N 2-tert-butyl-5-isocyanato-1,3,4-thiadiazole Chemical compound CC(C)(C)C1=NN=C(N=C=O)S1 TWAUUVMXSRYMPA-UHFFFAOYSA-N 0.000 description 1
- UKBBXRBDAMPGNW-UHFFFAOYSA-N 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1-methyl-1-(2-oxoethyl)urea Chemical compound O=CCN(C)C(=O)NC1=NN=C(C(C)(C)C)S1 UKBBXRBDAMPGNW-UHFFFAOYSA-N 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000722731 Carex Species 0.000 description 1
- 241001111317 Chondrodendron tomentosum Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37520373A | 1973-06-29 | 1973-06-29 | |
| US38341773A | 1973-07-27 | 1973-07-27 | |
| US38800573A | 1973-08-13 | 1973-08-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2430467A1 DE2430467A1 (de) | 1975-01-23 |
| DE2430467C2 true DE2430467C2 (de) | 1983-07-21 |
Family
ID=27409234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2430467A Expired DE2430467C2 (de) | 1973-06-29 | 1974-06-25 | Thiadiazolylimidazolidinone |
Country Status (22)
| Country | Link |
|---|---|
| AR (1) | AR216038A1 (enExample) |
| AT (1) | AT335449B (enExample) |
| AU (1) | AU473700B2 (enExample) |
| BE (1) | BE813958A (enExample) |
| BR (1) | BR7405280A (enExample) |
| CA (1) | CA1017747A (enExample) |
| CH (1) | CH589409A5 (enExample) |
| DE (1) | DE2430467C2 (enExample) |
| DK (1) | DK141202B (enExample) |
| EG (1) | EG11069A (enExample) |
| ES (1) | ES424486A1 (enExample) |
| FR (1) | FR2235127B1 (enExample) |
| GB (1) | GB1450289A (enExample) |
| IL (1) | IL44428A (enExample) |
| IT (1) | IT1049287B (enExample) |
| MY (1) | MY7900229A (enExample) |
| NL (1) | NL7405880A (enExample) |
| NO (1) | NO140382C (enExample) |
| PH (1) | PH10348A (enExample) |
| SE (1) | SE401922B (enExample) |
| SU (1) | SU554814A3 (enExample) |
| YU (1) | YU36520B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1150271A (en) * | 1979-08-10 | 1983-07-19 | Jerome M. Lavanish | 3-¬5-¬1-(alkyloxy or alkylthio)alkyl, alkynyl, alkenyl, or haloalkyl|-1,3,4- thiadiazol-2-yl|-4-hydroxy-1-methyl-2- imidazolidinones |
| AU581763B2 (en) * | 1985-06-14 | 1989-03-02 | Ppg Industries, Inc. | Herbicidal imidazolidinone derivatives |
| GB201419829D0 (en) * | 2014-11-07 | 2014-12-24 | Syngenta Participations Ag | Herbicidal compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2013406A1 (de) * | 1970-03-20 | 1971-10-07 | 1(13 4 Thiadiazol 2 yl) lmidazohdi non (2) Derivate, Verfahren zu ihrer Her stellung und ihre Verwendung als herbizide | |
| DE2013418A1 (de) * | 1970-03-20 | 1971-10-07 | I (1,3,4 Thiadiazol 2 yl) lmidazohdi non (2) Derivate, Verfahren zu ihrer Her stellung und ihre Verwendung als herbizide |
-
1974
- 1974-02-08 AR AR252264A patent/AR216038A1/es active
- 1974-03-15 IL IL44428A patent/IL44428A/en unknown
- 1974-03-19 CA CA195,374A patent/CA1017747A/en not_active Expired
- 1974-03-21 ES ES424486A patent/ES424486A1/es not_active Expired
- 1974-03-26 PH PH15660*A patent/PH10348A/en unknown
- 1974-03-29 YU YU00885/74A patent/YU36520B/xx unknown
- 1974-04-19 BE BE143416A patent/BE813958A/xx not_active IP Right Cessation
- 1974-04-30 NO NO741560A patent/NO140382C/no unknown
- 1974-05-02 NL NL7405880A patent/NL7405880A/xx not_active Application Discontinuation
- 1974-05-06 CH CH613574A patent/CH589409A5/xx not_active IP Right Cessation
- 1974-05-09 DK DK258074AA patent/DK141202B/da not_active IP Right Cessation
- 1974-05-13 SE SE7406371A patent/SE401922B/xx unknown
- 1974-05-29 IT IT51279/74A patent/IT1049287B/it active
- 1974-06-18 AU AU70162/74A patent/AU473700B2/en not_active Expired
- 1974-06-19 EG EG232/74A patent/EG11069A/xx active
- 1974-06-25 FR FR7422142A patent/FR2235127B1/fr not_active Expired
- 1974-06-25 DE DE2430467A patent/DE2430467C2/de not_active Expired
- 1974-06-27 BR BR5280/74A patent/BR7405280A/pt unknown
- 1974-06-28 AT AT538074A patent/AT335449B/de not_active IP Right Cessation
- 1974-06-28 SU SU2049687A patent/SU554814A3/ru active
- 1974-06-28 GB GB2871674A patent/GB1450289A/en not_active Expired
-
1979
- 1979-12-30 MY MY229/79A patent/MY7900229A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO140382B (no) | 1979-05-14 |
| BR7405280D0 (pt) | 1975-01-21 |
| MY7900229A (en) | 1979-12-31 |
| AU7016274A (en) | 1975-12-18 |
| SE401922B (sv) | 1978-06-05 |
| ATA538074A (de) | 1976-07-15 |
| SU554814A3 (ru) | 1977-04-15 |
| IT1049287B (it) | 1981-01-20 |
| NO140382C (no) | 1979-08-22 |
| CH589409A5 (enExample) | 1977-07-15 |
| NO741560L (enExample) | 1975-01-27 |
| FR2235127B1 (enExample) | 1980-02-08 |
| GB1450289A (en) | 1976-09-22 |
| IL44428A (en) | 1977-08-31 |
| CA1017747A (en) | 1977-09-20 |
| DE2430467A1 (de) | 1975-01-23 |
| FR2235127A1 (enExample) | 1975-01-24 |
| AR216038A1 (es) | 1979-11-30 |
| DK141202B (da) | 1980-02-04 |
| DK141202C (enExample) | 1980-07-21 |
| ES424486A1 (es) | 1976-06-01 |
| DK258074A (enExample) | 1975-02-17 |
| IL44428A0 (en) | 1974-06-30 |
| SE7406371L (enExample) | 1974-12-30 |
| NL7405880A (enExample) | 1974-12-31 |
| PH10348A (en) | 1976-12-20 |
| YU88574A (en) | 1982-02-25 |
| BE813958A (fr) | 1974-08-16 |
| BR7405280A (pt) | 1976-02-24 |
| AT335449B (de) | 1977-03-10 |
| YU36520B (en) | 1984-02-29 |
| EG11069A (en) | 1976-11-30 |
| AU473700B2 (en) | 1976-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |