CA1151179A - Combating unwanted vegetation with 1,3,4- thiadiazole-2-sulfonamides - Google Patents
Combating unwanted vegetation with 1,3,4- thiadiazole-2-sulfonamidesInfo
- Publication number
- CA1151179A CA1151179A CA000134958A CA134958A CA1151179A CA 1151179 A CA1151179 A CA 1151179A CA 000134958 A CA000134958 A CA 000134958A CA 134958 A CA134958 A CA 134958A CA 1151179 A CA1151179 A CA 1151179A
- Authority
- CA
- Canada
- Prior art keywords
- structural formula
- methyl
- yield
- sulfonamide
- thiadiazole
- 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
- AXNSXSNCIZLUMJ-UHFFFAOYSA-N 1,3,4-thiadiazole-2-sulfonamide Chemical class NS(=O)(=O)C1=NN=CS1 AXNSXSNCIZLUMJ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 230000001590 oxidative effect Effects 0.000 claims abstract description 11
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 11
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 231100000208 phytotoxic Toxicity 0.000 claims description 6
- 230000000885 phytotoxic effect Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- HJVKPKIEEZCWBB-UHFFFAOYSA-N (4-sulfamoylthiadiazol-5-yl)urea Chemical compound NC(=O)NC=1SN=NC=1S(N)(=O)=O HJVKPKIEEZCWBB-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000003335 secondary amines Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 34
- 238000005660 chlorination reaction Methods 0.000 abstract description 7
- 230000002363 herbicidal effect Effects 0.000 abstract description 7
- 239000004009 herbicide Substances 0.000 abstract description 7
- MLRBKPMYTYCDOQ-UHFFFAOYSA-N 1-[5-(dimethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1,3,3-trimethylurea Chemical compound CN(C)C(=O)N(C)C1=NN=C(S(=O)(=O)N(C)C)S1 MLRBKPMYTYCDOQ-UHFFFAOYSA-N 0.000 abstract 1
- 240000006122 Chenopodium album Species 0.000 description 19
- 235000009344 Chenopodium album Nutrition 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 17
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 12
- 235000004135 Amaranthus viridis Nutrition 0.000 description 12
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 12
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 12
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 12
- 240000003768 Solanum lycopersicum Species 0.000 description 12
- 235000011292 Brassica rapa Nutrition 0.000 description 11
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 11
- 235000010469 Glycine max Nutrition 0.000 description 11
- 240000007807 Sisymbrium officinale Species 0.000 description 11
- 241001148727 Bromus tectorum Species 0.000 description 10
- 235000005853 Cyperus esculentus Nutrition 0.000 description 10
- 244000075634 Cyperus rotundus Species 0.000 description 10
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 10
- 240000003176 Digitaria ciliaris Species 0.000 description 10
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 10
- 235000005476 Digitaria cruciata Nutrition 0.000 description 10
- 235000006830 Digitaria didactyla Nutrition 0.000 description 10
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 10
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 10
- 235000014716 Eleusine indica Nutrition 0.000 description 10
- 244000248416 Fagopyrum cymosum Species 0.000 description 10
- 244000068988 Glycine max Species 0.000 description 10
- 240000006394 Sorghum bicolor Species 0.000 description 10
- 235000006923 Sorghum x drummondii Nutrition 0.000 description 10
- 241001506766 Xanthium Species 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 9
- 240000004658 Medicago sativa Species 0.000 description 9
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 241000894007 species Species 0.000 description 9
- 235000017016 Setaria faberi Nutrition 0.000 description 8
- 241000820191 Setaria magna Species 0.000 description 8
- 235000002248 Setaria viridis Nutrition 0.000 description 8
- 240000003461 Setaria viridis Species 0.000 description 8
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 235000017060 Arachis glabrata Nutrition 0.000 description 7
- 235000010777 Arachis hypogaea Nutrition 0.000 description 7
- 244000105624 Arachis hypogaea Species 0.000 description 7
- 235000018262 Arachis monticola Nutrition 0.000 description 7
- 235000020232 peanut Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 244000058871 Echinochloa crus-galli Species 0.000 description 6
- 235000015505 Sorghum bicolor subsp. bicolor Nutrition 0.000 description 6
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 6
- 244000062793 Sorghum vulgare Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000283903 Ovis aries Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CIIBBRJFKALYAK-UHFFFAOYSA-N 1,3,4-thiadiazole-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=NN=CS1 CIIBBRJFKALYAK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JVLFMTZUPSBCNJ-UHFFFAOYSA-N 3,5-difluoropyridin-2-amine Chemical compound NC1=NC=C(F)C=C1F JVLFMTZUPSBCNJ-UHFFFAOYSA-N 0.000 description 2
- JMRAYTPNXKJWAX-UHFFFAOYSA-N 5-(methylamino)-3H-1,3,4-thiadiazole-2-thione Chemical compound CNC1=NN=C(S)S1 JMRAYTPNXKJWAX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- OWTDUWLWAOCZOO-UHFFFAOYSA-N 5-(ethylamino)-3h-1,3,4-thiadiazole-2-thione Chemical compound CCNC1=NNC(=S)S1 OWTDUWLWAOCZOO-UHFFFAOYSA-N 0.000 description 1
- 241001290610 Abildgaardia Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 241001167018 Aroa Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000004535 Avena sterilis Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- LVRCEUVOXCJYSV-UHFFFAOYSA-N CN(C)S(=O)=O Chemical compound CN(C)S(=O)=O LVRCEUVOXCJYSV-UHFFFAOYSA-N 0.000 description 1
- BSIOKXNNEUIOMT-UHFFFAOYSA-N CNC.C(=O)(Cl)Cl Chemical compound CNC.C(=O)(Cl)Cl BSIOKXNNEUIOMT-UHFFFAOYSA-N 0.000 description 1
- 101100123850 Caenorhabditis elegans her-1 gene Proteins 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241001630921 Chlorida Species 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001483078 Phyto Species 0.000 description 1
- 101100014660 Rattus norvegicus Gimap8 gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000030538 Thecla Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000004222 uncontrolled growth Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 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
- 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
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA208,502A CA999871A (en) | 1972-02-17 | 1974-09-05 | 2-(1,3,3-trimethylureldo)-1,3,4-thiadiazole-5-n,n-dimethylsulfonamide |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US119,417 | 1971-02-26 | ||
| US05/119,417 US4021225A (en) | 1971-02-26 | 1971-02-26 | Combating unwanted vegetation with 1,3,4-thiadiazole-2-sulfonamides |
| US00177178A US3824247A (en) | 1971-02-26 | 1971-09-01 | 2-(1,3,3-trimethylureido)-1,3,4-thiadiazole-5-n,n-dimethylsulfonamide |
| US177,178 | 1971-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1151179A true CA1151179A (en) | 1983-08-02 |
Family
ID=26817318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000134958A Expired CA1151179A (en) | 1971-02-26 | 1972-02-17 | Combating unwanted vegetation with 1,3,4- thiadiazole-2-sulfonamides |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3824247A (OSRAM) |
| BE (1) | BE779943A (OSRAM) |
| CA (1) | CA1151179A (OSRAM) |
| DE (1) | DE2209010A1 (OSRAM) |
| FR (2) | FR2126419B1 (OSRAM) |
| GB (1) | GB1390272A (OSRAM) |
| NL (1) | NL7202523A (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4049670A (en) * | 1968-12-23 | 1977-09-20 | Bayer Aktiengesellschaft | N-(2-Ethylsulfonyl-1,3,4-thiadiazol-5-yl)-N-methyl-N'-methylurea |
| US3932437A (en) * | 1971-09-01 | 1976-01-13 | Gulf Research & Development Company | Multistep synthesis for certain 1,3,4-thiadiazoles and intermediate |
| US4028090A (en) * | 1974-10-15 | 1977-06-07 | Eli Lilly And Company | Herbicidal use of 5-cyanoalkyl-1,3,4-thiadiazol-2-ylureas |
| US4165229A (en) * | 1976-05-06 | 1979-08-21 | Eli Lilly And Company | Herbicidal method |
| US4097263A (en) * | 1976-11-22 | 1978-06-27 | Gulf Oil Corporation | 5-Acylamino-1,3,4-thiadiazole-2-sulfonamides and use as herbicides |
| US4187098A (en) * | 1978-11-24 | 1980-02-05 | Gulf Oil Corporation | Selectively herbicidal N-(5-substituted-2-thiadiazolyl)-thiocarboxamides |
| US4562260A (en) * | 1984-07-03 | 1985-12-31 | Union Carbide Corporation | Preparation of 1,3,4-thiadiazole-5-sulfonamides |
-
1971
- 1971-09-01 US US00177178A patent/US3824247A/en not_active Expired - Lifetime
-
1972
- 1972-02-15 GB GB688372A patent/GB1390272A/en not_active Expired
- 1972-02-17 CA CA000134958A patent/CA1151179A/en not_active Expired
- 1972-02-25 FR FR727206478A patent/FR2126419B1/fr not_active Expired
- 1972-02-25 NL NL7202523A patent/NL7202523A/xx not_active Application Discontinuation
- 1972-02-25 DE DE19722209010 patent/DE2209010A1/de not_active Ceased
- 1972-02-28 BE BE779943A patent/BE779943A/xx not_active IP Right Cessation
- 1972-11-06 FR FR7239124A patent/FR2170376A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2126419B1 (OSRAM) | 1973-08-10 |
| BE779943A (fr) | 1972-06-16 |
| GB1390272A (en) | 1975-04-09 |
| FR2126419A1 (OSRAM) | 1972-10-06 |
| NL7202523A (OSRAM) | 1972-08-29 |
| DE2209010A1 (de) | 1972-08-31 |
| US3824247A (en) | 1974-07-16 |
| FR2170376A5 (OSRAM) | 1973-09-14 |
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