JPS6317833B2 - - Google Patents
Info
- Publication number
- JPS6317833B2 JPS6317833B2 JP56215628A JP21562881A JPS6317833B2 JP S6317833 B2 JPS6317833 B2 JP S6317833B2 JP 56215628 A JP56215628 A JP 56215628A JP 21562881 A JP21562881 A JP 21562881A JP S6317833 B2 JPS6317833 B2 JP S6317833B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- present
- dimethyl
- general formula
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 4
- FNLMKLJJRWRDRY-UHFFFAOYSA-N 1-(2,3,3a,4-tetrahydro-1,3-benzothiazol-2-yl)imidazolidin-2-one Chemical class O=C1NCCN1C1SC2=CC=CCC2N1 FNLMKLJJRWRDRY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 35
- 239000013078 crystal Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- -1 tetrahydrobenzothiazolylimidazolidine derivative Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 2
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- 240000001341 Reynoutria japonica Species 0.000 description 2
- 235000018167 Reynoutria japonica 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
- 244000197975 Solidago virgaurea Species 0.000 description 2
- 235000000914 Solidago virgaurea Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- STGAKXYPJXIYKL-UHFFFAOYSA-N (5,5-dimethyl-7-oxo-4-phenyl-4,6-dihydro-1,3-benzothiazol-2-yl) carbamate Chemical compound CC1(C)CC(=O)C=2SC(OC(N)=O)=NC=2C1C1=CC=CC=C1 STGAKXYPJXIYKL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001520921 Leersia virginica Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21562881A JPS58110582A (ja) | 1981-12-24 | 1981-12-24 | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を有効成分とする除草剤 |
| DE3246705A DE3246705C2 (de) | 1981-12-24 | 1982-12-17 | Tetrahydrobenzthiazolderivate und diese Verbindungen als wirksamen Bestandteil enthaltende herbizide Mittel |
| CA000418102A CA1193261A (en) | 1981-12-24 | 1982-12-20 | Derivatives of tetrahydrobenzothiazole and herbicidal compositions containing the same as an active ingredient |
| AU91667/82A AU553468B2 (en) | 1981-12-24 | 1982-12-20 | Benthiazole-imidazolidene one derivatives and herbicides |
| US06/451,796 US4481027A (en) | 1981-12-24 | 1982-12-21 | Derivatives of tetrahydrobenzothiazole and herbicidal compositions _containing the same as an active ingredient |
| BR8207472A BR8207472A (pt) | 1981-12-24 | 1982-12-23 | Derivado de tetraidrobenzotiazol, composto e composicao herbicida |
| ES518858A ES8502700A1 (es) | 1981-12-24 | 1982-12-23 | Procedimiento para la fabricacion de derivados de tetrahidrobenzotiazol. |
| GB08236627A GB2111996B (en) | 1981-12-24 | 1982-12-23 | Herbicidal derivatives of tetrahydrobenzothiazole |
| IT24960/82A IT1153883B (it) | 1981-12-24 | 1982-12-23 | Derivati di tetraidrobenzotiazolo e composizioni erbicide che li contengono come ingredienti attivi |
| FR8221679A FR2519000B1 (pl) | 1981-12-24 | 1982-12-23 | |
| ES535951A ES8506011A1 (es) | 1981-12-24 | 1984-09-14 | Procedimiento para la obtencion de un derivado de tetrahidrobenzotiazol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21562881A JPS58110582A (ja) | 1981-12-24 | 1981-12-24 | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を有効成分とする除草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58110582A JPS58110582A (ja) | 1983-07-01 |
| JPS6317833B2 true JPS6317833B2 (pl) | 1988-04-15 |
Family
ID=16675545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21562881A Granted JPS58110582A (ja) | 1981-12-24 | 1981-12-24 | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を有効成分とする除草剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58110582A (pl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58194883A (ja) * | 1982-05-10 | 1983-11-12 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を含有する除草剤 |
| JPS59186979A (ja) * | 1983-04-08 | 1984-10-23 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾ−ル誘導体及び該誘導体を含有する除草剤 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS535163A (en) * | 1976-05-20 | 1978-01-18 | Velsicol Chemical Corp | 11benzothiazolyllimidazolidianes |
| JPS55133381A (en) * | 1979-03-02 | 1980-10-17 | Velsicol Chemical Corp | Tetrahydrobenzothiazolylimidazolidinone |
-
1981
- 1981-12-24 JP JP21562881A patent/JPS58110582A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS535163A (en) * | 1976-05-20 | 1978-01-18 | Velsicol Chemical Corp | 11benzothiazolyllimidazolidianes |
| JPS55133381A (en) * | 1979-03-02 | 1980-10-17 | Velsicol Chemical Corp | Tetrahydrobenzothiazolylimidazolidinone |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58110582A (ja) | 1983-07-01 |
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