SU927115A3 - Способ получени производных 2-сульфинил-5-сульфонил-1,3,4-тиадиазола - Google Patents
Способ получени производных 2-сульфинил-5-сульфонил-1,3,4-тиадиазола Download PDFInfo
- Publication number
- SU927115A3 SU927115A3 SU802959549A SU2959549A SU927115A3 SU 927115 A3 SU927115 A3 SU 927115A3 SU 802959549 A SU802959549 A SU 802959549A SU 2959549 A SU2959549 A SU 2959549A SU 927115 A3 SU927115 A3 SU 927115A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- thiadiazole
- diadiazole
- ethylsulfonyl
- butylsulfonyl
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 230000008569 process Effects 0.000 title description 2
- BMRPEMSWZYKQQT-UHFFFAOYSA-N 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazole Chemical compound O=S=C1SC(=S(=O)=O)N=N1 BMRPEMSWZYKQQT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 239000013543 active substance Substances 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 21
- 238000002474 experimental method Methods 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 210000005069 ears Anatomy 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 124
- -1 cyclopropyl 2-propenyl Chemical group 0.000 description 38
- 239000002689 soil Substances 0.000 description 22
- 230000002538 fungal effect Effects 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 125000006100 1-methylbutyl sulfinyl group Chemical group 0.000 description 14
- 241000233866 Fungi Species 0.000 description 13
- 206010028851 Necrosis Diseases 0.000 description 13
- 230000017074 necrotic cell death Effects 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 230000009471 action Effects 0.000 description 11
- 235000013339 cereals Nutrition 0.000 description 10
- 125000006118 1-ethylbutyl sulfinyl group Chemical group 0.000 description 9
- 230000000855 fungicidal effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 235000000292 Gouania lupuloides Nutrition 0.000 description 8
- 244000299452 Gouania lupuloides Species 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000003902 lesion Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 240000004713 Pisum sativum Species 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000006148 1-ethylbutyl sulfonyl group Chemical group 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 206010017533 Fungal infection Diseases 0.000 description 4
- 208000031888 Mycoses Diseases 0.000 description 4
- 229940088623 biologically active substance Drugs 0.000 description 4
- 231100000676 disease causative agent Toxicity 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
- 241000223218 Fusarium Species 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- 241001281803 Plasmopara viticola Species 0.000 description 3
- 241000233639 Pythium Species 0.000 description 3
- 235000007238 Secale cereale Nutrition 0.000 description 3
- 244000082988 Secale cereale Species 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000006130 1-methylbutyl sulfonyl group Chemical group 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000548268 Citrus deliciosa Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000282858 Hyracoidea Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001459558 Monographella nivalis Species 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 241001311547 Patina Species 0.000 description 1
- 235000002245 Penicillium camembertii Nutrition 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 241000514371 Ustilago avenae Species 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 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
- 230000001133 acceleration Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000019674 grape juice Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 208000018655 severe necrosis Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- 239000004563 wettable powder 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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792933008 DE2933008A1 (de) | 1979-08-13 | 1979-08-13 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU927115A3 true SU927115A3 (ru) | 1982-05-07 |
Family
ID=6078481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802959549A SU927115A3 (ru) | 1979-08-13 | 1980-08-11 | Способ получени производных 2-сульфинил-5-сульфонил-1,3,4-тиадиазола |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4369185A (OSRAM) |
| JP (1) | JPS5629580A (OSRAM) |
| AR (1) | AR224906A1 (OSRAM) |
| AT (1) | AT366888B (OSRAM) |
| AU (1) | AU533363B2 (OSRAM) |
| BE (1) | BE884764A (OSRAM) |
| BR (1) | BR8005061A (OSRAM) |
| CA (1) | CA1146946A (OSRAM) |
| CH (1) | CH645366A5 (OSRAM) |
| CS (1) | CS212722B2 (OSRAM) |
| DD (1) | DD152468A5 (OSRAM) |
| DE (1) | DE2933008A1 (OSRAM) |
| DK (1) | DK327780A (OSRAM) |
| EG (1) | EG14322A (OSRAM) |
| ES (1) | ES494075A0 (OSRAM) |
| FI (1) | FI802537A7 (OSRAM) |
| FR (1) | FR2463133A1 (OSRAM) |
| GB (1) | GB2058058B (OSRAM) |
| GR (1) | GR69848B (OSRAM) |
| HU (1) | HU187307B (OSRAM) |
| IE (1) | IE50105B1 (OSRAM) |
| IL (1) | IL60823A (OSRAM) |
| IT (1) | IT1132389B (OSRAM) |
| LU (1) | LU82703A1 (OSRAM) |
| MA (1) | MA18933A1 (OSRAM) |
| MX (1) | MX6142E (OSRAM) |
| NL (1) | NL8004440A (OSRAM) |
| NO (1) | NO150437C (OSRAM) |
| NZ (1) | NZ194566A (OSRAM) |
| PH (1) | PH17442A (OSRAM) |
| PL (1) | PL124268B1 (OSRAM) |
| PT (1) | PT71673B (OSRAM) |
| RO (1) | RO80302A (OSRAM) |
| SE (1) | SE440502B (OSRAM) |
| SU (1) | SU927115A3 (OSRAM) |
| TR (1) | TR20990A (OSRAM) |
| YU (1) | YU190380A (OSRAM) |
| ZA (1) | ZA804950B (OSRAM) |
| ZW (1) | ZW18880A1 (OSRAM) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695847C3 (de) * | 1967-06-09 | 1978-09-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazole |
| NL6713712A (OSRAM) * | 1967-10-10 | 1969-04-14 | ||
| DE2533605A1 (de) * | 1975-07-26 | 1977-02-03 | Bayer Ag | Antiparasitenmittel |
-
1979
- 1979-08-13 DE DE19792933008 patent/DE2933008A1/de not_active Withdrawn
-
1980
- 1980-07-15 CH CH543580A patent/CH645366A5/de not_active IP Right Cessation
- 1980-07-25 SE SE8005391A patent/SE440502B/sv unknown
- 1980-07-28 YU YU01903/80A patent/YU190380A/xx unknown
- 1980-07-30 DK DK327780A patent/DK327780A/da unknown
- 1980-08-04 NL NL8004440A patent/NL8004440A/nl not_active Application Discontinuation
- 1980-08-05 NZ NZ194566A patent/NZ194566A/xx unknown
- 1980-08-07 RO RO80101925A patent/RO80302A/ro unknown
- 1980-08-07 MX MX808964U patent/MX6142E/es unknown
- 1980-08-08 PT PT71673A patent/PT71673B/pt unknown
- 1980-08-08 ES ES494075A patent/ES494075A0/es active Granted
- 1980-08-08 TR TR20990A patent/TR20990A/xx unknown
- 1980-08-09 MA MA19134A patent/MA18933A1/fr unknown
- 1980-08-09 EG EG481/80A patent/EG14322A/xx active
- 1980-08-11 PL PL1980226188A patent/PL124268B1/pl unknown
- 1980-08-11 DD DD80223242A patent/DD152468A5/de unknown
- 1980-08-11 IT IT24108/80A patent/IT1132389B/it active
- 1980-08-11 JP JP10934380A patent/JPS5629580A/ja active Pending
- 1980-08-11 GB GB8026125A patent/GB2058058B/en not_active Expired
- 1980-08-11 AR AR282117A patent/AR224906A1/es active
- 1980-08-11 GR GR62643A patent/GR69848B/el unknown
- 1980-08-11 LU LU82703A patent/LU82703A1/de unknown
- 1980-08-11 SU SU802959549A patent/SU927115A3/ru active
- 1980-08-12 IL IL60823A patent/IL60823A/xx unknown
- 1980-08-12 CA CA000358074A patent/CA1146946A/en not_active Expired
- 1980-08-12 US US06/178,703 patent/US4369185A/en not_active Expired - Lifetime
- 1980-08-12 AT AT0413480A patent/AT366888B/de not_active IP Right Cessation
- 1980-08-12 HU HU802006A patent/HU187307B/hu unknown
- 1980-08-12 AU AU61382/80A patent/AU533363B2/en not_active Ceased
- 1980-08-12 FI FI802537A patent/FI802537A7/fi not_active Application Discontinuation
- 1980-08-12 NO NO802405A patent/NO150437C/no unknown
- 1980-08-12 BR BR8005061A patent/BR8005061A/pt unknown
- 1980-08-13 BE BE0/201744A patent/BE884764A/fr not_active IP Right Cessation
- 1980-08-13 CS CS805585A patent/CS212722B2/cs unknown
- 1980-08-13 ZW ZW188/80A patent/ZW18880A1/xx unknown
- 1980-08-13 ZA ZA00804950A patent/ZA804950B/xx unknown
- 1980-08-13 IE IE1702/80A patent/IE50105B1/en unknown
- 1980-08-13 FR FR8017906A patent/FR2463133A1/fr active Granted
- 1980-08-13 PH PH24441A patent/PH17442A/en unknown
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