JP3294612B2 - ほとんど粉粒を含まないテトラヒドロ−３，５−ジメチル−１，３，５−チアジアジン−２−チオン顆粒の製造方法、この方法により得た同顆粒、これを用いた土壌殺菌方法、線虫類、植物胞子体、土壌真菌類の防除方法、同顆粒の使用法 - Google Patents
ほとんど粉粒を含まないテトラヒドロ−３，５−ジメチル−１，３，５−チアジアジン−２−チオン顆粒の製造方法、この方法により得た同顆粒、これを用いた土壌殺菌方法、線虫類、植物胞子体、土壌真菌類の防除方法、同顆粒の使用法Info
- Publication number
- JP3294612B2 JP3294612B2 JP51140193A JP51140193A JP3294612B2 JP 3294612 B2 JP3294612 B2 JP 3294612B2 JP 51140193 A JP51140193 A JP 51140193A JP 51140193 A JP51140193 A JP 51140193A JP 3294612 B2 JP3294612 B2 JP 3294612B2
- Authority
- JP
- Japan
- Prior art keywords
- granules
- dimethyl
- thione
- tetrahydro
- thiadiazine
- 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 - Fee Related
Links
- 239000008187 granular material Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 30
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000002245 particle Substances 0.000 title claims description 19
- 239000002689 soil Substances 0.000 title claims description 15
- 239000000843 powder Substances 0.000 title claims description 10
- 241000233866 Fungi Species 0.000 title claims description 6
- 241000244206 Nematoda Species 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000004659 sterilization and disinfection Methods 0.000 title claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 34
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 241001061127 Thione Species 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- DMDWPICFPZMEEW-UHFFFAOYSA-N 1,3,5-thiadiazine-2-thione Chemical compound S=C1N=CN=CS1 DMDWPICFPZMEEW-UHFFFAOYSA-N 0.000 claims 2
- YPXQSGWOGQPLQO-UHFFFAOYSA-N 5-nitro-1,3-dihydrobenzimidazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2N=C(S)NC2=C1 YPXQSGWOGQPLQO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- PFTZLFKMQOYCLG-UHFFFAOYSA-N 3,5-dimethyl-1,3,5-thiadiazinane Chemical compound CN1CSCN(C)C1 PFTZLFKMQOYCLG-UHFFFAOYSA-N 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims 1
- 230000000249 desinfective effect Effects 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- -1 1,2-ethylene, 1,3-propylene Chemical group 0.000 abstract description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 9
- 239000013543 active substance Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical group CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- 239000005644 Dazomet Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- ZHEVWUDSIBINSL-UHFFFAOYSA-N n'-methylethene-1,2-diamine Chemical group CNC=CN ZHEVWUDSIBINSL-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- 239000011686 zinc sulphate 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
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/34—1,3,5-Thiadiazines; Hydrogenated 1,3,5-thiadiazines
-
- 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
- A01N43/88—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 six-membered rings with three ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Processing Of Solid Wastes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4142571 | 1991-12-21 | ||
| DE4142571.5 | 1991-12-21 | ||
| PCT/EP1992/002907 WO1993013085A1 (de) | 1991-12-21 | 1992-12-15 | Verfahren zur herstellung eines weitgehend staubfreien tetrahydro-3,5-dimethyl-1,3,5-thiadiazin-2-thion granulats |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07502520A JPH07502520A (ja) | 1995-03-16 |
| JP3294612B2 true JP3294612B2 (ja) | 2002-06-24 |
Family
ID=6447885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51140193A Expired - Fee Related JP3294612B2 (ja) | 1991-12-21 | 1992-12-15 | ほとんど粉粒を含まないテトラヒドロ−３，５−ジメチル−１，３，５−チアジアジン−２−チオン顆粒の製造方法、この方法により得た同顆粒、これを用いた土壌殺菌方法、線虫類、植物胞子体、土壌真菌類の防除方法、同顆粒の使用法 |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5495017A (OSRAM) |
| EP (1) | EP0618912B1 (OSRAM) |
| JP (1) | JP3294612B2 (OSRAM) |
| KR (1) | KR100214400B1 (OSRAM) |
| CN (2) | CN1034076C (OSRAM) |
| AT (1) | ATE145401T1 (OSRAM) |
| AU (1) | AU663912B2 (OSRAM) |
| CA (1) | CA2122257C (OSRAM) |
| CZ (1) | CZ286137B6 (OSRAM) |
| DE (1) | DE59207557D1 (OSRAM) |
| DK (1) | DK0618912T3 (OSRAM) |
| ES (1) | ES2094521T3 (OSRAM) |
| GE (1) | GEP20043182B (OSRAM) |
| GR (1) | GR3021759T3 (OSRAM) |
| HU (1) | HU213906B (OSRAM) |
| IL (1) | IL104081A (OSRAM) |
| MD (1) | MD1672G2 (OSRAM) |
| MY (1) | MY108046A (OSRAM) |
| NZ (1) | NZ246337A (OSRAM) |
| PH (1) | PH31677A (OSRAM) |
| PL (1) | PL172752B1 (OSRAM) |
| RO (1) | RO113855B1 (OSRAM) |
| RU (1) | RU2119919C1 (OSRAM) |
| SK (1) | SK279914B6 (OSRAM) |
| TJ (1) | TJ280B (OSRAM) |
| TR (1) | TR27346A (OSRAM) |
| TW (1) | TW316265B (OSRAM) |
| UA (1) | UA37200C2 (OSRAM) |
| WO (1) | WO1993013085A1 (OSRAM) |
| ZA (1) | ZA929813B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU748665B2 (en) | 1997-07-23 | 2002-06-06 | Kanesho Soil Treatment Sprl/Bvba | Plant protection products in the form of a granulate with controlled release of the active agent |
| CZ304039B6 (cs) | 2000-08-17 | 2013-09-04 | Basf Aktiengesellschaft | Zpusob prípravy prostredku z tetrahydro-3,5-dimethyl-1,3,5-thiadiazin-2-thionu obsahujícího cástice |
| RU2368603C2 (ru) * | 2007-08-27 | 2009-09-27 | Институт нефтехимии и катализа РАН | СПОСОБ ПОЛУЧЕНИЯ 5-(n-ЭТИЛКАРБОКСИФЕНИЛ)-, 5-(n-β-ДИЭТИЛАМИНОЭТИЛКАРБОКСИФЕНИЛ)- И 5-(n-СУЛЬФАЦЕТАМИДФЕНИЛ)-1,3,5-ДИТИАЗИНАНОВ |
| RU2447067C1 (ru) * | 2010-08-11 | 2012-04-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Способ получения 1,3,5-тиадиазинан-4-(ти)онов |
| CN106831649B (zh) * | 2016-12-27 | 2019-09-27 | 浙江海正化工股份有限公司 | 一种棉隆制备工艺 |
| CN107353259A (zh) * | 2017-09-05 | 2017-11-17 | 南通派斯第农药化工股份有限公司 | 一种棉隆的生产工艺 |
| CN107540635B (zh) * | 2017-09-30 | 2018-05-22 | 台州市大鹏药业有限公司 | 一种抗板结的棉隆制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838389A (en) * | 1952-09-03 | 1958-06-10 | Union Carbide Corp | Method of combatting weeds |
| US2838839A (en) * | 1955-12-22 | 1958-06-17 | Gasdorf Gus | Mooring device |
| FR1229662A (fr) * | 1957-08-10 | 1960-09-08 | Bayer Ag | Procédé de préparation de dérivés de la tétrahydro-thiamidine-thione |
| FR1554038A (OSRAM) * | 1968-01-12 | 1969-01-17 | ||
| JPS61202885A (ja) * | 1985-03-07 | 1986-09-08 | Tomoegawa Paper Co Ltd | 感熱記録材料 |
| JP2009210073A (ja) * | 2008-03-05 | 2009-09-17 | Shiroki Corp | 係合部材 |
-
1992
- 1992-12-14 IL IL10408192A patent/IL104081A/en not_active IP Right Cessation
- 1992-12-15 ES ES93901680T patent/ES2094521T3/es not_active Expired - Lifetime
- 1992-12-15 EP EP93901680A patent/EP0618912B1/de not_active Expired - Lifetime
- 1992-12-15 HU HU9401352A patent/HU213906B/hu unknown
- 1992-12-15 JP JP51140193A patent/JP3294612B2/ja not_active Expired - Fee Related
- 1992-12-15 SK SK581-94A patent/SK279914B6/sk not_active IP Right Cessation
- 1992-12-15 AT AT93901680T patent/ATE145401T1/de active
- 1992-12-15 PL PL92304144A patent/PL172752B1/pl unknown
- 1992-12-15 US US08/244,742 patent/US5495017A/en not_active Expired - Lifetime
- 1992-12-15 GE GEAP19922428A patent/GEP20043182B/en unknown
- 1992-12-15 MD MD96-0267A patent/MD1672G2/ro not_active IP Right Cessation
- 1992-12-15 AU AU32564/93A patent/AU663912B2/en not_active Expired
- 1992-12-15 CA CA002122257A patent/CA2122257C/en not_active Expired - Lifetime
- 1992-12-15 TJ TJ96000366A patent/TJ280B/xx unknown
- 1992-12-15 NZ NZ246337A patent/NZ246337A/en unknown
- 1992-12-15 DE DE59207557T patent/DE59207557D1/de not_active Expired - Lifetime
- 1992-12-15 WO PCT/EP1992/002907 patent/WO1993013085A1/de not_active Ceased
- 1992-12-15 RO RO94-00804A patent/RO113855B1/ro unknown
- 1992-12-15 RU RU94046247A patent/RU2119919C1/ru not_active IP Right Cessation
- 1992-12-15 UA UA94075644A patent/UA37200C2/uk unknown
- 1992-12-15 DK DK93901680.4T patent/DK0618912T3/da active
- 1992-12-15 CZ CZ19941115A patent/CZ286137B6/cs not_active IP Right Cessation
- 1992-12-16 TW TW081110105A patent/TW316265B/zh not_active IP Right Cessation
- 1992-12-18 ZA ZA929813A patent/ZA929813B/xx unknown
- 1992-12-18 MY MYPI92002348A patent/MY108046A/en unknown
- 1992-12-21 CN CN92115325A patent/CN1034076C/zh not_active Expired - Lifetime
- 1992-12-21 PH PH45483A patent/PH31677A/en unknown
- 1992-12-21 TR TR01210/92A patent/TR27346A/xx unknown
-
1994
- 1994-06-20 KR KR1019940702156A patent/KR100214400B1/ko not_active Expired - Lifetime
-
1996
- 1996-05-13 CN CN96106277A patent/CN1061077C/zh not_active Expired - Lifetime
- 1996-11-21 GR GR960403136T patent/GR3021759T3/el unknown
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