CS263578B1 - 6-x-3-aryloxy/methyl/acetyl-2-benzothiazolinones - Google Patents
6-x-3-aryloxy/methyl/acetyl-2-benzothiazolinones Download PDFInfo
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- CS263578B1 CS263578B1 CS877785A CS778587A CS263578B1 CS 263578 B1 CS263578 B1 CS 263578B1 CS 877785 A CS877785 A CS 877785A CS 778587 A CS778587 A CS 778587A CS 263578 B1 CS263578 B1 CS 263578B1
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Abstract
Riešenie vynálezu sa týká 6-X-3-aryloxy- (metyl)acetyl-2-benzotiazolinónov všeobecného vzorca I w k ··*». v ktorom X je H, Br; R je H, CH3, jeden alebo dva atómy chlóru. Spósob výroby 6-X-3-aryloxy- (metylacetyl-2-benzotiazolinónov všeobecného vzorca I je založený na acylácii 2-benzotiazolinónu alebo jeho bróm derivátu chloridmi kyselin ALFA-aryloxypropionových za přítomnosti bázy pri teplote 40 až 70 °C. Zlúčeniny sa vyznačujú herbicídnou účinnosťou.The solution of the invention relates to 6-X-3-aryloxy-(methyl)acetyl-2-benzothiazolinones of the general formula I w k ··*». in which X is H, Br; R is H, CH3, one or two chlorine atoms. The method of producing 6-X-3-aryloxy-(methylacetyl-2-benzothiazolinones of the general formula I is based on the acylation of 2-benzothiazolinone or its bromo derivative with ALFA-aryloxypropionic acid chlorides in the presence of a base at a temperature of 40 to 70 °C. The compounds are characterized by herbicidal activity.
Description
283578
Vynález sa týká 6-X-3-aryloxy(metyl)ace-tyl-2-benzotiazolinónov a sposobu leh pří-pravy. Tieto zlúfieniny mají herbicídne účin-ky.
Za zlúčenín benzotiazolu sú známe pesti-cidně přípravky ako napr. benzotiazuron ametabenztiazuron využívané v ροϊηοhospo-dářské] praxi. Aj 3-hálogénalkyl, 3-alkyl ale-bo 3-acetyl deriváty 2-benzotiazolinómu savyznačuji! širokým spektrom účinku a tonajma herbicídnym, moríoregulačným a fun- gicídnym účinkom (D*Amico, J. J.: Eur. Pat.Appl. 2 932; D‘Amico, J. J.: USA pat. 4 187 098,D‘Amico, J. J.: USA pat. 576 512, Nedá, I.:Jap. pat. 92 956 (1979); Jap. pat. 105 605(1980) Cs. pat. 172118 (1974); Lácová M.,Sidóová E., Konečný V.: Čs. aut. osv·. 246 247(1986). Přitom je známe, že východiskový 2--benzotiazolinón a jeho 6-bróm derivát jebiologicky neúčinný.
Teraz sa zistili 6-X-3-aryloxy( metyl jacetyl--2-benzotiazolinóny všeobecného vzorce I
zX
CO-CH-0
v ktorom X znamená vodík alebo bróm a Rje vodík, metyl alebo 1 až 2 atómy chlóru. Súčasne bol zistený spósob přípravy zlú-čenín všeobecného vzorca I acyláciou 2- -benzotiazolinónu chloridmi kyselin a-aryl-oxypropionových s výhodou pri teplote 40až 70 °C v přítomnosti bázy, čo možno zná-zorniť schémou: /?
CH. I -3 O-CH-COC1, v ktorej substituenty X a R majú už uvede-ný význam. U zlúčenín podlá všeobecného vzorca Iholi súčasne zistené herbicídne účinky, na-příklad 6-bróm-3- (2-metyl-4-chlórfenoxy-(metyl )acetyl-2-benzotiazolinón pri preemer-gentnej aplikácii v dávke 5 kg/ha 100 % in-hiboval rast v skleníkových podmienkoch amodelových rastlín Panicům miliaceum, Le-pidlům sativum a Sinapis alba, pri postemer-gentnej aplikácii v dávke 2,5 kg/ha 100 %inhiboval rast Lepidium sativum a Sinapisalba a na 80 % inhiboval rast Fagopyrumvulgare.
Nasledujúce příklady ilustrujú, ale neob-medzujú predmet vynálezu. Příklad 1
Spósob přípravy 6-X-3-aryloxy( metyl )ace- tyl-2-benzotiazolinónov
Do roztoku 2-benzotiazolinónu, resp. 6--bróm-2-benzotiazolinónu (50 mmólov) v di-metylformamide, resp. v acetóne, resp. v ichzmesi (20 cm3) sa přidá chlorid kyseliny a--aryloxypropiónovej (60 mmólov) a mieša saasi 10 minút. Potom sa prikvapká pyridin a-lebo trietylamín (60 mmólov) a mieša sa priteplote 40 až 70 °C asi 1 hodinu. Po ochlade-ní sa acetón móže oddestilovať, destilačnýzvyšok sa vyleje do vody, zneutralizuje(NaHCO3, Na2CO3 a pod.). Vylúčená zraze-nina sa odsaje a prekryštalizuje z etanolu,resp. zo zmesi etanol-dimetylformamid, ale-bo etanoldimetylsulfoxíd.
Podlá příkladu 1 bolí připravené nasle-dujúce zlúčeniny: a) 3- [ 4-chlórf eraoxy {metyl) acetyl] -2-ben- zotiazolinón, teplota topenia 108 až 111 °C.
283578
The invention relates to 6-X-3-aryloxy (methyl) acetyl-2-benzothiazolinones and to a process for the preparation thereof. These compounds have herbicidal effects.
Benzothiazole compounds are known to be pesticidal agents such as the benzothiazuron ametabenzothiazuron used in the commercial practice. The 3-haloalkylalkyl, 3-alkyl or 3-acetyl derivatives of 2-benzothiazolinoma are also indicated by the following. a broad spectrum of action and tonicity with herbicidal, mororegulatory and functional effects (D * Amico, JJ: Eur. Pat.Appl. 2 932; D'Amico, JJ: US Pat. No. 4,187,098, D'Amico, JJ: US Pat. No. 576,512, Nedá, I.:Jap., 92, 956 (1979), Jap., Pat., 105, 605 (1980), Cs: 172118 (1974), Lácová M., Sidóová E., Konečný V .: Cs. It is known that the starting 2-benzothiazolinone and its 6-bromo derivative are biologically ineffective.
6-X-3-aryloxy (methyl jacetyl-2-benzothiazolinones of formula I) have now been found
zX
CO-CH-O
wherein X is hydrogen or bromo and R is hydrogen, methyl or 1 to 2 chloro atoms. At the same time, a process for the preparation of compounds of formula I by acylation of 2-benzothiazolinone with .alpha.-aryl-oxypropionic acid chlorides, preferably at 40 DEG to 70 DEG C. in the presence of a base, has been found.
CH. I-O-CH-COCl in which X and R are as defined above. Herbicidal effects, for example 6-bromo-3- (2-methyl-4-chlorophenoxy- (methyl) acetyl-2-benzothiazolinone, at 5 kg / ha and 100% for preemergence) were found for the compounds of formula (I). inhibited growth in the greenhouse conditions of the amodel plants to Panic miliaceum, sativum and Sinapis alba, inhibited the growth of Lepidium sativum and Sinapisalba at 100% in post-emergent application at 2.5 kg / ha and inhibited Fagopyrumvulgar growth by 80%.
The following examples illustrate but do not limit the invention. Example 1
A method for preparing 6-X-3-aryloxy (methyl) acetyl-2-benzothiazolinones
To a solution of 2-benzothiazolinone, respectively. 6-bromo-2-benzothiazolinone (50 mmol) in dimethylformamide, respectively. in acetone, respectively. in a mixture (20 cm 3) of α-aryloxypropionic acid chloride (60 mmol) is added and the mixture is stirred for 10 minutes. Pyridine or triethylamine (60 mmol) was then added dropwise and the mixture was stirred at 40-70 ° C for about 1 hour. After cooling, acetone can be distilled off, the distillation residue is poured into water, neutralized (NaHCO3, Na2CO3, etc.). The precipitate formed is filtered off with suction and recrystallized from ethanol, respectively. from a mixture of ethanol-dimethylformamide or ethanol-dimethylsulfoxide.
The following compounds were prepared according to Example 1: a) 3- [4-chlorophenoxy (methyl) acetyl] -2-benzothiazolinone, mp 108-111 ° C.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877785A CS263578B1 (en) | 1987-10-30 | 1987-10-30 | 6-x-3-aryloxy/methyl/acetyl-2-benzothiazolinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877785A CS263578B1 (en) | 1987-10-30 | 1987-10-30 | 6-x-3-aryloxy/methyl/acetyl-2-benzothiazolinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS778587A1 CS778587A1 (en) | 1988-09-16 |
| CS263578B1 true CS263578B1 (en) | 1989-04-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS877785A CS263578B1 (en) | 1987-10-30 | 1987-10-30 | 6-x-3-aryloxy/methyl/acetyl-2-benzothiazolinones |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS263578B1 (en) |
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1987
- 1987-10-30 CS CS877785A patent/CS263578B1/en unknown
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|---|---|
| CS778587A1 (en) | 1988-09-16 |
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