CA1024151A - Preparation process of new thiadiazole derivatives - Google Patents
Preparation process of new thiadiazole derivativesInfo
- Publication number
- CA1024151A CA1024151A CA211,904A CA211904A CA1024151A CA 1024151 A CA1024151 A CA 1024151A CA 211904 A CA211904 A CA 211904A CA 1024151 A CA1024151 A CA 1024151A
- Authority
- CA
- Canada
- Prior art keywords
- thiadiazole
- radical
- atome
- diéthoxythiophosphoryloxy
- groupe
- 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
- 238000002360 preparation method Methods 0.000 title 1
- 150000004867 thiadiazoles Chemical class 0.000 title 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- -1 phosphoryloxy group Chemical group 0.000 claims abstract description 7
- 150000003254 radicals Chemical class 0.000 claims description 27
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 229940095054 ammoniac Drugs 0.000 claims description 2
- WMTVHVATSLCUKN-UHFFFAOYSA-N (5-benzylsulfanyl-1,2,4-thiadiazol-3-yl)oxy-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(SCC=2C=CC=CC=2)=N1 WMTVHVATSLCUKN-UHFFFAOYSA-N 0.000 claims 1
- ABLIGYUHUXFSQG-UHFFFAOYSA-N (5-ethylsulfanyl-1,2,4-thiadiazol-3-yl) dimethyl phosphate Chemical compound CCSC1=NC(OP(=O)(OC)OC)=NS1 ABLIGYUHUXFSQG-UHFFFAOYSA-N 0.000 claims 1
- BRWPHEOKPPHRCZ-UHFFFAOYSA-N 3-dimethoxyphosphinothioyloxy-n,n-dimethyl-1,2,4-thiadiazol-5-amine Chemical compound COP(=S)(OC)OC1=NSC(N(C)C)=N1 BRWPHEOKPPHRCZ-UHFFFAOYSA-N 0.000 claims 1
- AJUXGGXQZPTZJL-UHFFFAOYSA-N [5-[(2,4-dichlorophenyl)methylsulfanyl]-1,2,4-thiadiazol-3-yl]oxy-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(SCC=2C(=CC(Cl)=CC=2)Cl)=N1 AJUXGGXQZPTZJL-UHFFFAOYSA-N 0.000 claims 1
- BQWONGJGXUBPCW-UHFFFAOYSA-N [5-[(4-chlorophenyl)methoxy]-1,2,4-thiadiazol-3-yl]oxy-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(OCC=2C=CC(Cl)=CC=2)=N1 BQWONGJGXUBPCW-UHFFFAOYSA-N 0.000 claims 1
- RLAQZSOKSYRTOA-UHFFFAOYSA-N [5-[(4-chlorophenyl)methylsulfanyl]-1,2,4-thiadiazol-3-yl] dimethyl phosphate Chemical compound COP(=O)(OC)OC1=NSC(SCC=2C=CC(Cl)=CC=2)=N1 RLAQZSOKSYRTOA-UHFFFAOYSA-N 0.000 claims 1
- PNVZEKVQKPXPMN-UHFFFAOYSA-N [5-[(4-chlorophenyl)methylsulfanyl]-1,2,4-thiadiazol-3-yl]oxy-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(SCC=2C=CC(Cl)=CC=2)=N1 PNVZEKVQKPXPMN-UHFFFAOYSA-N 0.000 claims 1
- VQWGNJLIUNRHPF-UHFFFAOYSA-N [5-[(4-chlorophenyl)methylsulfanyl]-1,2,4-thiadiazol-3-yl]oxy-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=NSC(SCC=2C=CC(Cl)=CC=2)=N1 VQWGNJLIUNRHPF-UHFFFAOYSA-N 0.000 claims 1
- DXXKGLDOJFRFPY-UHFFFAOYSA-N diethoxy-[(5-ethoxy-1,2,4-thiadiazol-3-yl)oxy]-sulfanylidene-$l^{5}-phosphane Chemical compound CCOC1=NC(OP(=S)(OCC)OCC)=NS1 DXXKGLDOJFRFPY-UHFFFAOYSA-N 0.000 claims 1
- HGBLRZZIPGLOER-UHFFFAOYSA-N diethoxy-[(5-methylsulfanyl-1,2,4-thiadiazol-3-yl)oxy]-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(SC)=N1 HGBLRZZIPGLOER-UHFFFAOYSA-N 0.000 claims 1
- HMDVREWWXXLLRZ-UHFFFAOYSA-N diethoxy-[[5-[(4-methylphenyl)methylsulfanyl]-1,2,4-thiadiazol-3-yl]oxy]-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(SCC=2C=CC(C)=CC=2)=N1 HMDVREWWXXLLRZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- HTXXFOOSRRSQBL-UHFFFAOYSA-N 3-hydroxy-2h-thiadiazole Chemical compound ON1NSC=C1 HTXXFOOSRRSQBL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 239000005645 nematicide Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 11
- 238000013019 agitation Methods 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000500891 Insecta Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- FKTUXVQEOXYNMO-UHFFFAOYSA-N cyanocarbamodithioic acid Chemical compound SC(=S)NC#N FKTUXVQEOXYNMO-UHFFFAOYSA-N 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 241000255601 Drosophila melanogaster Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 241000212342 Sium Species 0.000 description 2
- 241000985245 Spodoptera litura Species 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- LOCFEBZCHQFGKQ-UHFFFAOYSA-N 5-methylsulfanyl-1,2,4-thiadiazole Chemical compound CSC1=NC=NS1 LOCFEBZCHQFGKQ-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- YDJKOALREUJGEA-UHFFFAOYSA-N C(C)SC1=NC=NS1 Chemical compound C(C)SC1=NC=NS1 YDJKOALREUJGEA-UHFFFAOYSA-N 0.000 description 1
- 101100402341 Caenorhabditis elegans mpk-1 gene Proteins 0.000 description 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 241000399934 Ditylenchus Species 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
- 241000244205 Panagrellus Species 0.000 description 1
- 241000244198 Panagrellus silusiae Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 101150058891 alc1 gene Proteins 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- TUZCOAQWCRRVIP-UHFFFAOYSA-N butoxymethanedithioic acid Chemical compound CCCCOC(S)=S TUZCOAQWCRRVIP-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- PDEWZQSQJDXSOG-UHFFFAOYSA-N n,n-dimethyl-1,2,4-thiadiazol-5-amine Chemical compound CN(C)C1=NC=NS1 PDEWZQSQJDXSOG-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/65392—Five-membered rings containing two nitrogen atoms
- C07F9/65397—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7338223A FR2249092B1 (xx) | 1973-10-26 | 1973-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1024151A true CA1024151A (en) | 1978-01-10 |
Family
ID=9126960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA211,904A Expired CA1024151A (en) | 1973-10-26 | 1974-10-22 | Preparation process of new thiadiazole derivatives |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5071677A (xx) |
| AR (1) | AR210251A1 (xx) |
| BE (1) | BE821420A (xx) |
| BR (1) | BR7408951A (xx) |
| CA (1) | CA1024151A (xx) |
| CH (1) | CH594691A5 (xx) |
| DD (2) | DD118225A5 (xx) |
| DE (1) | DE2450815A1 (xx) |
| DK (1) | DK559474A (xx) |
| FR (1) | FR2249092B1 (xx) |
| GB (1) | GB1434699A (xx) |
| HU (1) | HU171036B (xx) |
| IE (1) | IE41208B1 (xx) |
| IL (1) | IL45926A (xx) |
| LU (1) | LU71167A1 (xx) |
| NL (1) | NL7413912A (xx) |
| PH (1) | PH12199A (xx) |
| SU (1) | SU607531A3 (xx) |
| ZA (1) | ZA746781B (xx) |
-
1973
- 1973-10-26 FR FR7338223A patent/FR2249092B1/fr not_active Expired
-
1974
- 1974-10-22 CA CA211,904A patent/CA1024151A/en not_active Expired
- 1974-10-24 PH PH16447A patent/PH12199A/en unknown
- 1974-10-24 JP JP49122004A patent/JPS5071677A/ja active Pending
- 1974-10-24 LU LU71167A patent/LU71167A1/xx unknown
- 1974-10-24 DD DD181897A patent/DD118225A5/xx unknown
- 1974-10-24 NL NL7413912A patent/NL7413912A/xx not_active Application Discontinuation
- 1974-10-24 IL IL45926A patent/IL45926A/en unknown
- 1974-10-24 DD DD190828A patent/DD123475A5/xx unknown
- 1974-10-24 GB GB4685674A patent/GB1434699A/en not_active Expired
- 1974-10-24 BE BE149830A patent/BE821420A/xx unknown
- 1974-10-24 HU HU74RO00000807A patent/HU171036B/hu unknown
- 1974-10-25 BR BR8951/74A patent/BR7408951A/pt unknown
- 1974-10-25 IE IE2204/74A patent/IE41208B1/xx unknown
- 1974-10-25 DE DE19742450815 patent/DE2450815A1/de not_active Withdrawn
- 1974-10-25 AR AR256266A patent/AR210251A1/es active
- 1974-10-25 CH CH1434374A patent/CH594691A5/xx not_active IP Right Cessation
- 1974-10-25 ZA ZA00746781A patent/ZA746781B/xx unknown
- 1974-10-25 DK DK559474A patent/DK559474A/da unknown
-
1975
- 1975-08-07 SU SU752162198A patent/SU607531A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| HU171036B (hu) | 1977-10-28 |
| IL45926A (en) | 1977-08-31 |
| AR210251A1 (es) | 1977-07-15 |
| SU607531A3 (ru) | 1978-05-15 |
| BE821420A (fr) | 1975-04-24 |
| IE41208L (en) | 1975-04-26 |
| GB1434699A (en) | 1976-05-05 |
| ZA746781B (en) | 1975-11-26 |
| FR2249092B1 (xx) | 1977-01-07 |
| IL45926A0 (en) | 1974-12-31 |
| DE2450815A1 (de) | 1975-04-30 |
| IE41208B1 (en) | 1979-11-07 |
| LU71167A1 (xx) | 1975-06-24 |
| BR7408951A (pt) | 1976-05-04 |
| PH12199A (en) | 1978-11-28 |
| DD118225A5 (xx) | 1976-02-20 |
| NL7413912A (nl) | 1975-04-29 |
| JPS5071677A (xx) | 1975-06-13 |
| DK559474A (xx) | 1975-07-07 |
| DD123475A5 (xx) | 1976-12-20 |
| FR2249092A1 (xx) | 1975-05-23 |
| CH594691A5 (xx) | 1978-01-31 |
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