IL44428A - 3-alkyl-1-(5-substituted-1,3,4-thiadiazol-2-yl)-5-hydroxy-2-imidazolidinones - Google Patents
3-alkyl-1-(5-substituted-1,3,4-thiadiazol-2-yl)-5-hydroxy-2-imidazolidinonesInfo
- Publication number
- IL44428A IL44428A IL44428A IL4442874A IL44428A IL 44428 A IL44428 A IL 44428A IL 44428 A IL44428 A IL 44428A IL 4442874 A IL4442874 A IL 4442874A IL 44428 A IL44428 A IL 44428A
- Authority
- IL
- Israel
- Prior art keywords
- thiadiazol
- methyl
- hydroxy
- imidazolidin
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 42
- 241000196324 Embryophyta Species 0.000 claims description 30
- -1 as2sfe-Xif$£3⁄4: Chemical group 0.000 claims description 24
- 230000002363 herbicidal effect Effects 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 231100000331 toxic Toxicity 0.000 claims description 4
- 230000002588 toxic effect Effects 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- QSTJOOUALACOSX-UHFFFAOYSA-N 1,5-dihydroimidazol-2-one Chemical compound O=C1NCC=N1 QSTJOOUALACOSX-UHFFFAOYSA-N 0.000 claims 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 52
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 28
- 238000010992 reflux Methods 0.000 description 28
- 239000011521 glass Substances 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 17
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 13
- 239000000539 dimer Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000012047 saturated solution Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 208000027418 Wounds and injury Diseases 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 208000014674 injury Diseases 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 239000000428 dust Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 3
- LJGUQVJJWFWIBA-UHFFFAOYSA-N 2-isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical class FC(F)(F)C1=NN=C(N=C=O)S1 LJGUQVJJWFWIBA-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- 101001074628 Homo sapiens Phosphatidylinositol-glycan biosynthesis class W protein Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 102100036253 Phosphatidylinositol-glycan biosynthesis class W protein Human genes 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 240000000321 Abutilon grandifolium Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 244000055702 Amaranthus viridis Species 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 241001148727 Bromus tectorum Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
- 235000005853 Cyperus esculentus Nutrition 0.000 description 2
- 240000001505 Cyperus odoratus Species 0.000 description 2
- 240000008853 Datura stramonium Species 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 240000003176 Digitaria ciliaris Species 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
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 240000001549 Ipomoea eriocarpa Species 0.000 description 2
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
- 235000003403 Limnocharis flava Nutrition 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
- 235000008515 Setaria glauca Nutrition 0.000 description 2
- 235000001155 Setaria leucopila Nutrition 0.000 description 2
- 244000010062 Setaria pumila Species 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 208000037974 severe injury Diseases 0.000 description 2
- 230000009528 severe injury Effects 0.000 description 2
- ILGDOMACGBCIPG-UHFFFAOYSA-N 2-(ethylamino)acetaldehyde Chemical compound CCNCC=O ILGDOMACGBCIPG-UHFFFAOYSA-N 0.000 description 1
- QXTRPGAMVIONMK-UHFFFAOYSA-N 2-amino-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(N)S1 QXTRPGAMVIONMK-UHFFFAOYSA-N 0.000 description 1
- MPGORFJBWBACSB-UHFFFAOYSA-N 2-isocyanato-5-methylsulfinyl-1,3,4-thiadiazole Chemical class CS(=O)C1=NN=C(N=C=O)S1 MPGORFJBWBACSB-UHFFFAOYSA-N 0.000 description 1
- QYOSQYFLNBXVKF-UHFFFAOYSA-N 2-isocyanato-5-methylsulfonyl-1,3,4-thiadiazole Chemical class CS(=O)(=O)C1=NN=C(N=C=O)S1 QYOSQYFLNBXVKF-UHFFFAOYSA-N 0.000 description 1
- DRHLSQJZTGPDMP-UHFFFAOYSA-N 5-methoxy-1,3,4-thiadiazol-2-amine Chemical compound COC1=NN=C(N)S1 DRHLSQJZTGPDMP-UHFFFAOYSA-N 0.000 description 1
- ZQWRZVFWBDLVBP-UHFFFAOYSA-N 5-propoxy-1,3,4-thiadiazol-2-amine Chemical compound CCCOC1=NN=C(N)S1 ZQWRZVFWBDLVBP-UHFFFAOYSA-N 0.000 description 1
- UWXTXBIBHSFVCG-UHFFFAOYSA-N 5-propylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CCCSC1=NN=C(N)S1 UWXTXBIBHSFVCG-UHFFFAOYSA-N 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 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
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (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 |
|---|---|
| IL44428A0 IL44428A0 (en) | 1974-06-30 |
| IL44428A true IL44428A (en) | 1977-08-31 |
Family
ID=27409234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44428A IL44428A (en) | 1973-06-29 | 1974-03-15 | 3-alkyl-1-(5-substituted-1,3,4-thiadiazol-2-yl)-5-hydroxy-2-imidazolidinones |
Country Status (22)
| Country | Link |
|---|---|
| AR (1) | AR216038A1 (it) |
| AT (1) | AT335449B (it) |
| AU (1) | AU473700B2 (it) |
| BE (1) | BE813958A (it) |
| BR (1) | BR7405280A (it) |
| CA (1) | CA1017747A (it) |
| CH (1) | CH589409A5 (it) |
| DE (1) | DE2430467C2 (it) |
| DK (1) | DK141202B (it) |
| EG (1) | EG11069A (it) |
| ES (1) | ES424486A1 (it) |
| FR (1) | FR2235127B1 (it) |
| GB (1) | GB1450289A (it) |
| IL (1) | IL44428A (it) |
| IT (1) | IT1049287B (it) |
| MY (1) | MY7900229A (it) |
| NL (1) | NL7405880A (it) |
| NO (1) | NO140382C (it) |
| PH (1) | PH10348A (it) |
| SE (1) | SE401922B (it) |
| SU (1) | SU554814A3 (it) |
| YU (1) | YU36520B (it) |
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 DE DE2430467A patent/DE2430467C2/de not_active Expired
- 1974-06-25 FR FR7422142A patent/FR2235127B1/fr not_active Expired
- 1974-06-27 BR BR5280/74A patent/BR7405280A/pt unknown
- 1974-06-28 GB GB2871674A patent/GB1450289A/en not_active Expired
- 1974-06-28 SU SU2049687A patent/SU554814A3/ru active
- 1974-06-28 AT AT538074A patent/AT335449B/de not_active IP Right Cessation
-
1979
- 1979-12-30 MY MY229/79A patent/MY7900229A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES424486A1 (es) | 1976-06-01 |
| SU554814A3 (ru) | 1977-04-15 |
| NL7405880A (it) | 1974-12-31 |
| PH10348A (en) | 1976-12-20 |
| IT1049287B (it) | 1981-01-20 |
| SE7406371L (it) | 1974-12-30 |
| BE813958A (fr) | 1974-08-16 |
| AU473700B2 (en) | 1976-07-01 |
| ATA538074A (de) | 1976-07-15 |
| MY7900229A (en) | 1979-12-31 |
| CA1017747A (en) | 1977-09-20 |
| YU36520B (en) | 1984-02-29 |
| BR7405280D0 (pt) | 1975-01-21 |
| AU7016274A (en) | 1975-12-18 |
| NO140382B (no) | 1979-05-14 |
| FR2235127A1 (it) | 1975-01-24 |
| DK141202B (da) | 1980-02-04 |
| CH589409A5 (it) | 1977-07-15 |
| NO741560L (it) | 1975-01-27 |
| EG11069A (en) | 1976-11-30 |
| DE2430467A1 (de) | 1975-01-23 |
| IL44428A0 (en) | 1974-06-30 |
| BR7405280A (pt) | 1976-02-24 |
| FR2235127B1 (it) | 1980-02-08 |
| AR216038A1 (es) | 1979-11-30 |
| GB1450289A (en) | 1976-09-22 |
| NO140382C (no) | 1979-08-22 |
| DE2430467C2 (de) | 1983-07-21 |
| AT335449B (de) | 1977-03-10 |
| DK258074A (it) | 1975-02-17 |
| DK141202C (it) | 1980-07-21 |
| SE401922B (sv) | 1978-06-05 |
| YU88574A (en) | 1982-02-25 |
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