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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  • Health & Medical Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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 The subject of the invention is a herbicide and a method for preparing new chloroacetamide derivatives constituting the active substance. The new compounds are represented by the formula 1, in which Ar is a thiophene or isothiazole group linked through a ring carbon atom to the nitrogen atom of the N/Y/COCJ^Cl group to which it is connected, and the Ar group may be unsubstituted or substituted with one or more several halogen substituents, e.g. fluorine, chlorine and bromine; C1-Zf-alkyl radicals, C6-alkanoyl groups, C1-NOC1-Zf-alkyl/-C1^-alkyl groups, C/O-C1-alkyl^-O, ,-alkyl, 0,^-alkyl-S , C1-Zf-alkyl-S0, C6-alkoxy-carbonyl and/or C1-6-alkoxy groups, Y is a hydrocarbon group such as a C1-6-alkyl, C1-8-alkenyl, C1-8-alkynyl radical, wherein such hydrocarbon group is unsubstituted or substituted by a halogen such as fluorine, chlorine or bromine, or is a Ctl/R^/-CQY^9 group wherein R-| means a hydrogen atom or a C1-3-alkyl radical, and Y1 means a C1-3-alkoxy, C1-alkynyloxy, C1-alkylamino di-ZC1-alkylZ-amino group or an NH-N1C/C1,-alkyl/2 group , or denotes the group R1-Az, in which R2 denotes the group CK2 or CH2-CH2 unsubstituted or substituted by a C1-c-alkyl radical, and Az denotes an aromatic heterocyclic ring such as diazole or triazole, bonded through one of its nitrogen atoms from TU, a 5-membered heterocyclic ring bonded through a ring carbon atom to R2 and having 1-3 heteroatoms such as oxygen, sulfur or nitrogen, or a pyrimidyl group, or Y is an A-O-R* group, in which R , denotes a hydrogen atom or a C10-alkyl radical, unsubstituted or substituted by halogen, a cyano or alkoxy group, a C1-alkylene group unsubstituted or a substituted C1-alkoxy group, wherein A may be combined with R to form a saturated, an oxygen-containing heterocyclic ring containing 1 or 2 oxygen atoms as heteroatoms, the nitrogen and oxygen atoms which are bonded to A being separated by 1 or 2 carbon atoms, or a C1-alkyl radical, and FL and Re' independently of each other represent hydrogen or a methyl radical. 2 140 272 Possible Ar substituents not occurring in the ortho position with respect to the N-substituted chloroacetylamino group are preferably C2 radicals. 1-alkyl groups, e.g. the methyl radical, halogen atoms, e.g. chlorine, bromine, and C1-alkoxycarbonyl groups, e.g. COOCH*. The N-substituted chioroacetylamino group is preferably bonded to the ring carbon atom in the p position relative to the heteroatoms in the ring, so in the 3-position when Ar is thiophene and in the 4-position when Ar is isothiazole. A preferred subgroup of this last group are compounds in which the Ar group is substituted in the ortho position, especially in the ortho-ortho position with respect to the N-substituted acetylamino group, especially when the substituents are selected from the group given above. The nitrogen atom in the ring may be unsubstituted or substituted. If substituted, it is preferably substituted with a C1-4-alkyl radical, especially a methyl or ethyl radical. A particularly preferred subgroup of compounds of formula I are compounds in which Ar is thiophene and in particular a 3-thienyl group at least 2,4-disubstituted, and especially 3-thienyl compounds in which the substituents in positions 2 and 4 are radicals. C1-4-alkyl and C1-4-alkoxy groups. When Y, R*, R6 represent hydrocarbon groups substituted with halogen, such halogen is preferably chlorine or bromine, the hydrocarbon group so substituted is preferably monosubstituted. If Y is a hydrocarbon group substituted with a halogen, the halogen is generally preferably absent in the 1-position if the compound is to be used as a herbicide (such 1-halogenated compounds are generally unstable, but they constitute valuable intermediates in the production of other compounds of formula 1, e.g. those in which Y is an alkoxyalkyl or pyrazolylmethyl group); A preferred example of this meaning Y is the 2-chloroethyl group. When Y, R, R6 represent C1-Q-alkyl, C1-8-alkenyl or C1-8-alkynyl radicals, they preferably contain up to 5 atoms coal. If R1 is a C1-5-alkyl radical, it is preferably a methyl or ethyl radical, especially a methyl radical. In the case where R2 is a CH2 group, it may be substituted by 1 or 2, preferably by 1 C1-alkyl radical. In the case where R^ is the group 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.1. Patent claims 1. A method for preparing new chloroacetamide derivatives of formula 1, in which Ar is a thiophene or isothiazole group linked through a ring carbon atom to the nitrogen atom of the N/Y/COCHpCl group to which it is connected, and the Ar group may be unsubstituted or substituted by one or more substituents such as halogen atoms, e.g. fluorine, chlorine and bromine, C1-3-alkyl, C1-1-alkanoyl, C1-N0C1-+-alkyl/-C1-alkyl groups, C1-OC4-alkyl^-C^,-alkyl, C^-alkyl-S, C1-B^-alkyl-S0, C^-alkoxycarbonyl and/or C^-alkoxy, Y is a hydrocarbon group, such as a radical C16-alkyl, C18-alkenyl, C18-alkynyl, wherein such hydrocarbon group is unsubstituted or substituted by a halogen such as fluorine, chlorine or bromine, or is a CH/R1-C0Y3 group wherein R, , means a hydrogen atom or a C| radical --alkyl, and Y^ is a C1-alkoxylaf C, c-alkynyloxy, C1-alkylamino, di/C^-alkyl-amino, NH-N-C/Oj,-alkyl/2 group or Y is an R2-Az group , wherein R2 is a CH2 or CH2-CH2 radical unsubstituted or substituted with a ?-alkyl radical, and Az is an aromatic heterocyclic ring such as a diazole or triazole bonded to Rp through one of its nitrogen atoms, a 5-membered heterocyclic ring bonded to Rp through a ring carbon atom and containing 1-3 heteroatoms such as oxygen, sulfur or nitrogen, or a pyrimidyl group, or Y is an A-O-Rz* group in which R is a hydrogen atom or a C1-3-alkyl radical unsubstituted or substituted with halogen, a cyano or alkoxy group, and A is an unsubstituted C10-alkylene group or a substituted the nitrogen and oxygen atoms which are connected to A are separated by 1 or 2 carbon atoms, or represents a group of formula 2 in which R^ represents a C*-alkyl radical, and Re and RJ independently of each other represent a hydrogen atom, or a methyl radical, characterized in that the compound of formula 3, in which Ar has the meaning given above, is reacted with the compound of formula kf in which Y has the meaning given above and L is a leaving group capable of being split off under N-alkylation reaction conditions. 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,2. a herbicide containing an active substance and a diluent acceptable in herbicides, characterized in that the active substance contains new chloroacetamide derivatives of formula 1, in which Ar is a thiophene or isothiazole group linked through a ring carbon atom to the nitrogen atom of the N/Y/C0CH2C1 group to which it is connected, the Ar group may be unsubstituted or substituted by one or more substituents such as halogen atoms, e.g. fluorine, chlorine and bromine, groups 10 1^0 272 C ^-alkyl, C2_^-alkanoyl, CZ-NOC^-alkyl/Cj^-alkyl, C/OC^-alkyl/^-C^-alkyl, G^-alkyl-S, C^^-alkyl-SO , C1-6-alkoxycarbonyl and/or C1-3-alkoxy, Y represents a hydrocarbon group such as a C1-6-alkyl, C1-Q-alkenyl, C1-Q-alkynyl radical, such hydrocarbon group being unsubstituted or substituted by halo. ce, such as fluorine, chlorine or bromine, or represents a CH/R-j/-C0Y1f group in which Hj represents a hydrogen atom or a C1-c-alkyl radical and Y1 represents a C1-alkoxy, C1-c-alkynyl-xyl group , α^-alkylamino, di-Zc^^-alkyl©/-amino, NH-NsC/C^,-alkyl^, or Y is the F^-Az group, in which F^ is the radical CH2 or CH2-CH2 non-opposite or substituted with a C1-4-alkyl radical, and Az is an aromatic heterocyclic ring such as a diazole or triazole bonded to R^ through one of its nitrogen atoms, a 5-membered heterocyclic ring bonded to R^ through a ring carbon atom and containing 1-3 heteroatoms such as oxygen, sulfur or nitrogen, or a pyrimidyl group, or Y is an A-O-R* group, in which R- is a hydrogen atom or a C10-alkyl radical unsubstituted or substituted by halogen, a cyano group or alkoxy, and A is a C18-al-Jcil*new unsubstituted or substituted Gjc-alkoxy group, wherein A can be bonded to R" to form a saturated, oxygen-containing heterocyclic ring containing 1 or 2 oxygen atoms as heteroatoms, wherein the nitrogen and oxygen atoms which are connected to A are separated by 1 or 2 carbon atoms, or denotes a group of the formula 2 in which R^ denotes a ^-alkyl radical, and FU and Rj independently of each other denote a hydrogen atom, or methyl radical, 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.3. The agent according to claim 2, characterized in that it contains a compound of formula 1, in which Ar is at least disubstituted in the position o, o' to the chloroacetamide group with substituents defined in claim 2. 1, and the optional additional substituent of said heteroaromatic ring is selected from the group consisting of C16-alkyl, halogen and C16-alkoxycarbonyl. 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.4. agent according to claim 2, characterized in that it contains compounds of formula 1 in which Rp is CK2 or CH/CH*, Az is a 1-pyrazolyl or 3,5-dimethyl-1-pyrazolyl group, A is CH2, CH2-CH2 or a monomethylated derivative thereof, and R, is a C4-alkyl radical. 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.5. agent according to claim U9 characterized in that it contains a compound of formula 1, in which Ar is a 3-thienyl, 2-k-dup group substituted with substituents such as C1-3-alkyl and C1-3-alkoxyl. 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 *6. Agent according to claim. 59, characterized in that it contains a compound with the formula 1, in which Ar and Y have the following meanings, respectively: a/ 2,1-dimethyl-3-yl and pyrazolyl-1-methyl, b/ 2,k- din:ethyl-ti-n-3-yl and 1-(pyrazolyl-1)-ethyl, 0/2,4-dimethyl en-3-yl and CHgOCgH^,. d/ 2,4-dimethylc-thien-3-yl and C^OC^n, e/ 2-n:ethyl-4-ethyl-tier.-3-y1 and CHgOCgKct £/ 2-methylc-^-methoxy -thien-3-yl and pyrazolyl-i-methyl and g/ 2-methyl-^- -methoxy-thien-3-yl and 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,.7. agent according to claim 5, characterized in that it contains a compound of formula 1, in which Ar is a 2,4-dimethyl-thien-3-yl group and Y is a CH/CH»/CH20CH group. 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.8. agent according to claim 2, characterized in that it contains 0.01-99% by weight of the active substance, 0-20% by weight of a herbicide-acceptable surfactant and 1-99.99% by weight of a herbicide-acceptable diluent or diluents . 9. » srodek wedlug zastrz. 8, znamienny tym, ze zawiera 10-80 % wagowych substancji czynnej.9. » agent according to claim 8, characterized in that it contains 10-80% by weight of the active substance. 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 PL10. The agent according to claim 8, characterized in that it contains 0.01 - 25% by weight of the active substance. 140 272 Ar CH3) N 1 MODEL 5 CH, Ti N O—Me ¦S* MODEL 6 N N CH, Ji "0 MODEL 7 Et N— CH2 l^N •Me MODEL 8 N N S' CH2 VcJ Me MODEL 9140 272 N N J Ji CH- H MODEL 10 N N ¦Me SMe Me PATTERN 11 CH 2 i / PATTERN 12 CH^ O j PATTERN 13 Printing Studio UF PRL. Edition 100 copies. Price PLN 130 PL PL PL PL
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DE3303388A1 (en) 1983-08-11
HU193036B (en) 1987-08-28
JPH0645617B2 (en) 1994-06-15
NL190919B (en) 1994-06-01
NL350007I2 (en) 2003-01-06
FR2523967A1 (en) 1983-09-30
CZ86783A3 (en) 1993-01-13
IE830247L (en) 1983-08-09
NL190919C (en) 1994-11-01
AU1119483A (en) 1983-08-18
KR840003634A (en) 1984-09-15
DK53583A (en) 1983-08-10
ES519588A0 (en) 1985-03-01
AU566009B2 (en) 1987-10-08
SK86783A3 (en) 1995-01-12
JPS58148868A (en) 1983-09-05
IT8319474A0 (en) 1983-02-08
FR2530631A1 (en) 1984-01-27
CA1248538A (en) 1989-01-10
MY8700168A (en) 1987-12-31
EG16720A (en) 1990-06-30
IL67852A (en) 1986-07-31
CZ278361B6 (en) 1993-12-15
IL67852A0 (en) 1983-06-15
NL350007I1 (en) 2002-12-02
IT1163085B (en) 1987-04-08
DK53583D0 (en) 1983-02-08
SK277784B6 (en) 1995-01-12

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