PL140272B1 - Herbicide and method of manufacture of novel derivatives of chloroacetamide - Google Patents

Herbicide and method of manufacture of novel derivatives of chloroacetamide Download PDF

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PL140272B1
PL140272B1 PL83240481A PL24048183A PL140272B1 PL 140272 B1 PL140272 B1 PL 140272B1 PL 83240481 A PL83240481 A PL 83240481A PL 24048183 A PL24048183 A PL 24048183A PL 140272 B1 PL140272 B1 PL 140272B1
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Sandoz Sa
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  • Thiazole And Isothizaole Compounds (AREA)
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Description

Przedmiotem wynalazku jest srodek chwastobójczy i sposób wytwarzania nowych pochod¬ nych chloroacetamidu stanowiacych substancje czynna. Nowe zwiazki przedstawione sa wzo¬ rem 1, w którym Ar oznacza grupe tiofenu lub izotiazolu zwiazana poprzez pierscieniowy atom wegla z atomem azotu grupy N/Y/COCJ^Cl, z która jest polaczona, przy czym grupa Ar moze byc niepodstawiona lub podstawiona jednym lub kilkoma podstawnikami, takimi jak atomy chlorowca, np. fluor, chlor i brom; rodniki C1-Zf-alkilowe, grupy Cg^-alkanoilowe, grupy C/«NOC1-Zf-alkilo/-C1^-alkilowe, C/O-C^-alkilo^-O, ,-alkilowe, 0,^-alkil-S, C1-Zf-alkil-S0, C^-alkoksy-karbonylowe i/lub grupy C^-alkoksylowe, Y oznacza grupe weglowodorowa, taka jak rodnik C^g-alkilowy, C^g-alkenylowy, C, 8-alkinylowy, przy czym taka grupa weglowodorowa jest niepodstawiona lub podstawiona chlorowcem, takim jak fluor, chlor lub brom, albo oznacza grupe Ctl/R^/-CQY^9 w której R-| oznacza atom wodoru lub rodnik C^-alkilowy, a Y1 oznacza grupe C^-alkoksylowa, CL^-alkinyloksylowa, C^-alkiloaminowa dwu-ZC^-alkiloZ-aminowa lub grupe NH-N«C/C1 ,-alkilowa/2, albo ozna¬ cza grupe R^-Az, w której R2 oznacza grupe CK2 lub CH2-CH2 niepodstawiona lub podstawio¬ na rodnikiem C^c-alkilowym, a Az oznacza aromatyczny pierscien heterocykliczny, taki Jak diazol lub triazol, zwiazany poprzez jeden ze swych atomów azotu z TU, 5-czlonowy pier¬ scien heterocykliczny zwiazany poprzez pierscieniowy atom wegla z R^ i posiadajacy 1-3 heteroatomy, takie jak tlen, siarka lub azot, albo grupa pirymidylowa, albo Y oznacza grupe A-O-R*, w której R, oznacza atom wodoru lub rodnik Cj o-alkilowy, niepodstawiony lub podstawiony chlorowcem, grupa cyjanowa lub alkoksylowa, C1 «-alkilenowa niepodsta¬ wiona albo podstawiona grupa C^-alkoksylowa, przy czym A moze byc polaczone z R, two¬ rzac nasycony, zawierajacy tlen pierscien heterocykliczny zawierajacy 1 lub 2 atomy tle¬ nu jako heteroatomy, przy czym atomy azotu i tlenu, które sa zwiazane z A, rozdzielone sa przez 1 lub 2 atomy wegla, albo Y oznacza grupe o wzorze 2, w którym R^ oznacza rod¬ nik C^-alkiIowy, a FL i Re' niezaleznie od siebie oznaczaja wodór lub rodnik metylowy.2 140 272 Jako ewentualne podstawniki Ar nie wystepujace w pozycji orto w stosunku do N-pod- stawionej grupy chloroacetyloaminowej wymienia sie korzystnie rodniki C^^-alkilowe, np. rodnik metylowy, atomy chlorowca, np. chloru, bromu, oraz grupy C^-alkoksykarbo- nylowe, np. COOCH*. N-podstawiona grupa chioroacetyloaminowa jest korzystnie zwiazana z pierscieniowym atomem wegla w pozycjip w stosunku do heteroatomów w pierscieniu, tak wiec w pozycji 3, gdy Ar stanowi tiofen i w pozycji 4, gdy Ar oznacza izotiazol. Korzy¬ stna podgrupa tej ostatniej grupy sa zwiazki, w których grupa Ar jest podstawiona w po¬ zycji orto, zwlaszcza w pozycji orto-orto w stosunku do N-podstawionej grupy acetyloami- nowej, szczególnie gdy podstawniki sa wybrane z grupy wyzej podanej. Atom azotu w pier¬ scieniu moze byc niepodstawiony lub podstawiony. Jezeli jest podstawiony, to korzystnie jest podstawiony rodnikiem C^^-alkilowym, zwlaszcza metylowym lub etylowym. Szczególnie korzystna podgrupa zwiazków o wzorze 1 sa zwiazki, w których Ar stanowi tiofen, zwlasz¬ cza zas oznacza grupe 3-tienylowa co najmniej 2,4-dwupodstawiona, a zwlaszcza zwiazki 3-tienylowe, w których podstawniki w pozycji 2 i 4 stanowia rodniki C^^-alkilowe i gru¬ py C^^-alkoksylowe.W przypadku, gdy Y, R*, R^ oznaczaja grupy weglowodorowe podstawione chlorowcem, ta¬ kim chlorowcem korzystnie jest chlor lub brom, tak podstawiona grupa weglowodorowa Jest korzystnie monopodstawiona. Jezeli Y oznacza grupe weglowodorowa podstawiona chlorowcem, to chlorowiec na ogól korzystnie nie wystepuje w pozycji 1, o ile przewidziane jest sto¬ sowanie tego zwiazku jako herbicydu (takie 1-chlorowcowane zwiazki sa na ogól nietrwale, stanowia one jednak cenne produkty posrednie do produkcji innych zwiazków o wzorze 1, np. takich, w których Y oznacza grupe alkoksyalkilowa lub pirazolilometylowa); korzyst¬ nym przykladem takiego znaczenia Y jest grupa 2-chloroetylowa.W przypadku, gdy Y, R,, R^ oznaczaja rodniki C|_Q-alkilowe, C«_8-alkenylowe lub C^g-alkinylowe, zawieraja one korzystnie do 5 atomów wegla. W przypadku, gdy R1 oznacza rodnik C1-5-alkilowy, jest to korzystnie rodnik metylowy lub etylowy, zwlaszcza metylo¬ wy. W przypadku, gdy R2 oznacza grupe CH2, moze ona byó podstawiona przez 1 lub 2, ko¬ rzystnie przez 1 rodnik C^ --alkilowy. W przypadku, gdy R^ oznacza grupe CH2CH2» m PL PL PL

Claims (10)

1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych chloroacetamidu o wzorze 1, w którym Ar ozna¬ cza grupe tiofenu lub izotiazolu zwiazana poprzez pierscieniowy atom wegla z atomem azotu grupy N/Y/COCHpCl, z która jest polaczona, przy czym grupa Ar moze byc niepodstawiona lub podstawiona przez jeden lub wiecej podstawników, takich jak atomy chlorowca, np. fluoru, chloru i bromu, grupy C^-alkilowe, Cp_^-alkanoilowe, C/«N0Cj_/+-alkilo/-C] ,-alkilowe, C/OC^-alkilo^-C^,-alkilowe, C^-alkil-S, C1-B^-alkil-S0, C^-alkoksykarbonylowe i/lub C^-alkoksylowe, Y oznacza grupe weglowodorowa, taka jak rodnik C^g-alkilowy, CL g-alkenylowy, CL g-alkinylowy, przy czym taka grupa weglowodorowa jest niepodstawiona albo podstawiona chlorowcem, takim jak fluor, chlor lub brom, albo oznacza grupe CH/R^/-C0Y^f w której R,, oznacza atom wodoru lub rodnik C| --alkilowy, a Y^ oznacza grupe C1 c-alkoksylowaf C, c-alkinyloksylowa, C^-alkiloaminowa, dwu/C^-alkiW-aminowa, NH-N-C/Oj ,-alkilowa/2 albo Y oznacza grupe R2-Az, w której R2 oznacza rodnik CH2 lub CH2-CH2 niepodstawiony lub podstawiony rodnikiem ^ e-alkilowym, a Az oznacza aromatyczny pierscien heterocykliczny, taki jak diazol lub triazol zwiazany z Rp poprzez jeden ze swych atomów azotu, 5-czlonowy pierscien heterocykliczny zwiazany z Rp poprzez pierscieniowy atom wegla i zawierajacy 1-3 heteroatomy, takie jak tlen, siarka lub azot, albo grupe pirymidylowa, albo Y oznacza grup^ A-O-Rz* w której R, oznacza atom wodoru albo rodnik Cj ^-alkilowy niepodstawiony lub podstawiony chlorowcem, grupa cyjanowa lub alkoksylowa, a A oznacza grupe C^ o-alkilenowa niepodstawiona albo podstawiona grupa ^ .-alkoksylowa, przy czym A moze byc zwiazane z R, tworzac nasycony, zawierajacy tlen pierscien heterocykliczny zawierajacy 1 lub 2 atomy tlenu jako heteroatomy, przy czym atomy azotu i tlenu, które sa polaczone z A sa rozdzielone 1 lub 2 atomami wegla, albo oznacza grupe o wzorze 2, w której R^ oznacza ro¬ dnik C* --alkilowy, a Re i RJ niezaleznie od siebie oznaczaja atom wodoru lub rodnik me¬ tylowy, znamienny tym, ze zwiazek o wzorze 3, w którym Ar ma znaczenie wy¬ zej podane, poddaje sie reakcji ze zwiazkiem o wzorze kf w którym Y ma znaczenie wyzej po¬ dane, a L oznacza grupe odszczepialna zdolna do odszczepienia w warunkach reakcji N-alki- lowania.
2. srodek chwastobójczy zawierajacy substancje czynna i dopuszczalny w srodkach chwa¬ stobójczych rozcienczalnik, znamienny tym, ze- jako substancje czynna zawie¬ ra nowe pochodne chloroacetamidu o wzorze 1, w którym Ar oznacza grupe tiofenu lub izo¬ tiazolu zwiazana poprzez pierscieniowy atom wegla z atomem azotu grupy N/Y/C0CH2C1, z któ¬ ra jest polaczona, przy czym grupa Ar moze byc niepodstawiona lub podstawiona przez jeden lub wiecej podstawników, takich jak atomy chlorowca, np. fluoru, chloru i bromu, grupy10 1^0 272 C^-alkilowe, C2_^-alkanoilowe, CZ-NOC^-alkilo/Cj^-alkilowe, C/OC^-alkilo/^-C^- -alkilowe, G^-alkil-S, C^^-alkil-SO, C^-alkoksykarbonylowe i/lub C^-alkoksylowe, Y oznacza grupe weglowodorowa, taka jak rodnik C^g-alkilowy, C* Q-alkenylowy, Cj_Q-alki- nylowy, przy czym taka grupa weglowodorowa jest niepodstawiona albo podstawiona chlorow¬ cem, takim jak fluor, chlor lub brom, albo oznacza grupe CH/R-j/-C0Y1f w której Hj oznacza atom wodoru lub rodnik C^ c-alkilowy, a Y1 oznacza grupe C^ --alkoksylowa, C» c-alkinylo- ksylowa, a^-alkiloaminowa, dwu-Zc^^-alkil ©/-aminowa, NH-NsC/C^,-alkilowa^, albo Y oznacza grupe F^-Az, w której F^ oznacza rodnik CH2 lub CH2-CH2 niePocistawioRy lub pod¬ stawiony rodnikiem C^ ^-alkilowym, a Az oznacza aromatyczny pierscien heterocykliczny, taki jak diazol lub triazol zwiazany z .^ poprzez jeden ze swych atomów azotu, 5-czlono- wy pierscien heterocykliczny zwiazany z R^ poprzez pierscieniowy atom wegla i zawieraja¬ cy 1-3 heteroatomy, takie jak tlen, siarka lub azot, albo grupe pirymidylowa albo Y ozna¬ cza grupe A-O-R*, w której R- oznacza atom wodoru albo rodnik Cj o-alkilowy niepodstawio- ny lub podstawiony chlorowcem, grupa cyjanowa lub alkoksylowa, a A oznacza grupe C^g-al- Jcil*nowa niepodstawiona albo podstawiona grupa Gj c-alkoksylowa, przy czym A moze byc zwiazane z R» tworzac nasycony, zawierajacy tlen pierscien heterocykliczny zawierajacy 1 lub 2 atomy tlenu jako heteroatomy, przy czym atomy azotu i tlenu, które sa polaczone z A, sa rozdzielone 1 lub 2 atomami wegla, albo oznacza grupe o wzorze 2, w której R^ oznacza rodnik ^ =-alkilowy, a FU i Rj niezaleznie od siebie oznaczaja atom wodoru lub rodnik metylowy,
3. Srodek wedlug zastrz. 2, znamienny tym, ze zawiera zwiazek o wzo¬ rze 1, w którym Ar jest co najmniej dwupodstawiony w pozycji o, o'do grupy chioroaceta¬ midowej podstawnikami okreslonymi w zastrz. 1, a ewentualny dodatkowy podstawnik tego pierscienia heteroaromatycznego wybrany jest z grupy obejmujacej rodnik C^^-alkilowy, chlorowiec i grupe C^^-alkoksykarbonylowa.
4. srodek wedlug zastrz. 2, znamienny tym, ze zawiera zwiazki o wzo¬ rze 1, w którym Rp oznacza CK2 lub CH/CH*/, Az oznacza grupe 1-pirazolilowa lub 3,5^-dwu- metylo-1-pirazolilcwa, A oznacza CH2, CH2-CH2 lub ich monometylowana pochodna, a R, oznacza rodnik C^-alkilowy.
5. srodek wedlug zastrz. U9 znamienny tym, ze zawiera zwiazek o wzorze 1, w którym Ar oznacza grupe 3-tienylowa, 2,k-dwup odstawiona podstawnikami takimi, jak grupa Cj^-alkilowa i C^-alkoksylc^a.
6. Srodek wedlug zastrz. 59 znamienny tym, ze zawiera zwiazek o //zorze 1, w który™ Ar i Y maja odpowiednio nastepujace znaczenia: a/ 2,^-dwumetylc-3-yl i pira- zolilo-1-metyl, b/ 2,k-dwun:etylo-ti?n-3-yl i 1-/pirazolilc-1/-etyl, 0/ 2,4-dwumetylo¬ wi en-3-yl i CHgOCgH^,. d/ 2,4-dvunetylc-tien-3-yl i C^OC^n, e/ 2-n:etylo-4-etylc-tier.- -3-y1 i CHgOCgKct £/ 2-metylc-^-metoksy-tien-3-yl i pirazolilo-i-metyl i g/ 2-metylo-^- -metoksy-tien-3-yl i CH2CH20C2K5 *
7. srodek wedlug zastrz. 5, znamienny tym, ze zawiera zwiazek o wzorze 1, w którym Ar oznacza grupe 2,4-dwumetylo-tien-3-ylowa, a Y oznacza grupe CH/CH»/CH20CH,.
8. srodek wedlug zastrz. 2, znamienny tym, ze zawiera 0,01-99 % wago¬ wych substancji czynnej, 0-20 % wagowych dopuszczalnego w srodkach chwastobójczych srod¬ ka powierzchniowo czynnego i 1-99,99 % wagowych dopuszczalnego w srodkach chwastobój¬ czych rozcienczalnika lub rozcienczalników.
9. » srodek wedlug zastrz. 8, znamienny tym, ze zawiera 10-80 % wagowych substancji czynnej.
10. Srodek wedlug zastrz. 8, znamienny tym, ze zawiera 0,01 - 25 % wa¬ gowych substancji czynnej.140 272 Ar N- WZÓR 1 C0CH2CI ¦Y CH — C = NORA R5 Ri WZdR2 Ar NH COCH2Cl WZ0R3 LY WZÓR 4 /N=l CH(CH3) N 1 WZÓR 5 CH, Ti N O—Me ¦S* WZÓR 6 N N CH, Ji "0 WZÓR 7 Et N— CH2 l^N •Me WZÓR 8 N N S' CH2 VcJ Me WZÓR 9140 272 N N J Ji CH- H WZÓR 10 N N ¦Me SMe Me WZÓR 11 CH 2 i / WZÓR 12 CH^ O j WZÓR 13 Pracownia Poligraficzna UF PRL. Naklad 100 egz. Cena 130 zl PL PL PL PL
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