PL131693B1 - Herbicide - Google Patents
Herbicide Download PDFInfo
- Publication number
- PL131693B1 PL131693B1 PL1981229717A PL22971781A PL131693B1 PL 131693 B1 PL131693 B1 PL 131693B1 PL 1981229717 A PL1981229717 A PL 1981229717A PL 22971781 A PL22971781 A PL 22971781A PL 131693 B1 PL131693 B1 PL 131693B1
- Authority
- PL
- Poland
- Prior art keywords
- propen
- radical
- group
- hydroxy
- meaning given
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title description 3
- 239000004009 herbicide Substances 0.000 title description 3
- -1 alkyl radical Chemical class 0.000 description 40
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100125371 Caenorhabditis elegans cil-1 gene Proteins 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Opis patentowy opublikowano: 1087 04 30 131693 Int. Cl.3 AOIN 43/50 A01N 43/80 Twórca wynalazku — Uprawniony z patentu: PPG Industries, Inc., Pittsburgh (Stany Zjednoczone Ameryki) Srodek chwastobójczy Przemiotem wynalazku jest srodek chwastobój¬ czy zawierajacy nosnik,, substancje pomocnicza o- raz suibistancje czynna.Cecha srodka wedlug wynalazku jest to, ze ja¬ ko czynna substancje zawiera jeden lub wieksza liczbe zwiajzlkófw o ogólnym wzorze 1, w którym A oznacza gruipe o wzorze 2a lub 2b, w których ta wzorach Tl oznacza rodnik alkilowy o 1—6 ato¬ mach wegla, rodnik alkenyiloiwy zawierajacy do 5 aitomów wegla, rodnik alkinylowy zawierajacy do 5 atomów wegla., rodnik cykloalkiiowy, taki' jak rodnik cyklopropylcwy, cykloibutylowy, cyklopsmty- 1owy lub cyklohelkisylowy, albo rodnik chfloirowpo- alkilowy zawierajacy do 6 atomów wegla, lub tez R oznacza. grupe o wzorze —R4—O—R5 lub o wzo¬ rze —R4^S^R5, w których to wzorach R4 ozna¬ cza rodnik alkilenowy zawierajacy do 6 atomów wegla i R5 oznacza rodnik akilowy. o 1—'6 atomach wegla, albo tez R oznacza grupe o wzorze 3 lub o wzorze 4r w których to wzorach Z oznacza grupe nitrowa, atom chloru, bromu lub fluoru, albo rod¬ nik alkilowy o 1—® atomach wegla, n oznacza, liczbe izero, 1, 2 lub 3, a R4 ma wyzej podane zna¬ czenie, R2 oznacza, grupe hydroksylowa, atom chloru lub atom bromu, R3 oznacza atom wodoru, rodnik alkilowy o 1—4 atomach wegla rodnik alli- lowy lu/b grnilpe hydroksylowa, a R1 oznacza rod¬ nik alkilowy o 1^3 atomach wegla lub rodnik al- Mlowy.Ponizej podano przyklady zwiazków o wizorze 1 10 15 ujelte w dwie grupy i w podgrupy.Grupa 1. Zwiazki o wzorze 1, w którym A ozna¬ cza grupe o wzorze 2Jb. 1. R1 oznacza rodnik allililowy, a. Rs oznacza rodnik allilowy, a.l. R oznacza, grupe o waorze 3 lub 4, R2 ma wyzej podane znaczenie; Przykladami takich zwiazków isa: 3-{3-i[l -(/'4-chlorofen^o/-'lHmetyloetylo]-i5)-izoksa1zo- lilo) -1,5-dwu -/"2-piropen-jl -ylo/^4-hydroksyimidazo- lidynon-2, 3-;[i3-/)l-fenylioetyiloi/-5-,iz€ikEazolilo}-l,5-dwu-i/S:-pro pen-l'-ylo^-4j-hydr'Oksyimidaizolidynón-2^ 3h[3-./)1-cfenoksypropyloiZ-S-izok^aizolilo] -.1,5-dwu-,/i2^- jpropen-l-ylo/-4-chkroimidatzolidynon-2i i 3- {3'-i[H-yi2i,4-idwuchHorafendksy/-)l-.metylloetylo]-6-fi- zdksaizoliila}-ii yS-dwu-^-ipropen^l -ylo/^-hydroksy- imidazoilidynon-2, a.2. R oznacza grupe —R4^S—R5 i R2 ma wyzej podane znaczenie, np. 3-[3-/1 -imetylo-1 Hmetyiloti'oetylo/^5-iizok,sazolilo]Hi,6- -diwun/12'-ipropenHl-ylo/-4i-hydroksyimidazolidynon-& 25 3- {3-ifl nmetylo-lH/lHmetyloeityaotio/-etylo]-i5-izoksal- zolillo} ^1,5^dwu-^-propen-l-yloA^KJhQoroamiidazolo- dynon^L. a.3i. iR oznacza gruipe —4R4—O—R5, a R2 ma wyzej podane znaczenie, np. 30 3h[3^/11-metoksy-4l'-;metylóetylo/-5-4zokjsazOlilo]-il,5- 131 6933 -dwun/aiproipen-!l-ylo/^f4-hydrofcsyimida,zolidynon-2 i % 3-[i3-/l -etoksy-fl. -meitylO'buitylo/-5-izoksaizloiliilo] -11,5- ndwiWEi-p:open^l-ylo/-4-hydrokisyimidazalidyn0n-2. a.4. R oznacza rodnik chloroiwcoailkilowy o 1*—6 atomach wegla i R2 ma wyzej podane zna¬ czenie, nip. 3-i[i3H/,lHchl'0(ro-'lHmetylDeity(lo/-J5Hizolksazoillilo]-!l,5i- ^dwxi-/2-proipen-il-ylo/-4^hydroksyiMidaizoiidynion-2 34,3h/UHchlorometytlo-l nmelty^loetylo/-5i-:izolkteaz61ilo]- Hl^SJHdfwu-i/^-propen-il -ylo/-4-hydrokisyimiidaizio)lidy- non-2 i 3-[&-/I1-cMctfomeftylo-]i'-efl;yloetyW ni,5Mdwu-/E-propen^l-ylo/-4-ch)lorO(imiidaizioilidynon- 2. a.5. R oznacza grupe —CF3 i R2 ma wyzej podat¬ ne znaczenie, nip. 3n/3-itrójfluorome1;yllcK15-iizok!saizolilo1M,^-idwii-/2- ^prqpan-il-yilo/^-hydroksyin^da'zodJidynoin-2' i 3n/3^trójflluoromeityio^S-iizoks aizol'ilo/-il ,'5Hdrwiu-y!2- -|propen-1-ylo/-4-ibiromoimidaaollidynonH2 a.6. R oznacza rodnik cykloallkilowy i R2 ma wy¬ zej podane znaczenie, np. " 3-jA3^ykloheks^lo-5-izolksazcli^ pen-/l -ylo/-4-ihydirofcsyimMazolidynon-2, 3-/3^cykflopropylo-l5-izoksalzolillo/^l,5Hdiwu-1/l2^prO'- peh-l-yllo/-4Hhydrokisyimlidaadlidynofn-2 i 3n/3-cyklopent;ylo-i5-izoksazoiiilo/-il ,5-d|wui-/2Hpro- pen-il -ylot a.7. R oznacza rodnilk alkilowy o 1—6 atomach wegla i R2 • ma wyzej podane znaczenie,, np. 3-13-yi-imetyloeltytlo/^-izoksazoiliilo] -11,5-.dwiu-,/12^pro- pen-i-yiloA4j-hydroksyimidaizolidynon-2 i 3-[3-/l^etyloHi-metyiloetyioZ-ShiizoIksazolilo]Jl,5Mdwu- -/2-piropen-il -yilo/-4-hydroksyimiicfazodlidynon-2.. a.8. R oznacza rodnik 111-irzejd.iburtylowy i R2 ma wyzej podane znaczenie, nip. 3-[3-/l,Jl^diwumetyloetyloi/^HizoksazOlilo]-ii ,15-dwu-/ /2-ipropen-il -yLo/-4-hydroksyiimidalzoliidynon-2 i 3-{3slJl^a^umeityfloetty11o/-M /2-pr oipen- a.9. R oznacza irodnik aUkanylowy lub alkinylowy zawierajacy do 5 aftomów wegla i R2 ma wy¬ zej podane znaczenie, np. 3-[3-/1 „1-dwuimetylo^npropyn-l-yloZ-S-izokisaizolli- lo]-l,5'-diwu-/2-propein-1-ylo/-4-hydroksyimidazoli- dynon-2- i 3-[:3-/l ,1-dwume.tylo-2-pr Open-tl-ylo/H^izoksazoli- lo]-lJ5-dwui-[/i2r-propen-ir^ dynon-2. b. R3 odznacza rodnik alkilowy o 1—4,atomach wegla x . \ b.jl. R 0'znacza grupe o-wzorze 3 lub 4 i R2 ma wyzej podane znaczenie, np. 3- {3-lpl -^,4-idwumetylofenyloM-mety!loety11o]-5- -izoJkisaizoliilo}-4-hydrok;sy-'5-eitylO'-(l-./12Hpropen-!l'-yilO'/ /-imidazollidynon-2 i 3-{3- [1n/2-chlorofenylo/-lnmetyfloet Yk]-5Hizoksazo- lilo} -4-hydrokisy-S-metylo-l-^-ipropen-1-yiloMmi- dazolidyinon-2. b.2. R oznacza, grupe —R4^S—R5 i R2 ma wyzej podane znaczenie, np. 3~{3hflimetylo-1 Hmetylot«ioeitylo/-!5-(Lzoksazol/ilo]-4- -hydroksy-5-me(tylo-l -/l2npropen-a-yloMmidazdli- dynon-2 i 131 693 34!3J/1 Hmei;ylotiioetylc)/-i5-!iiZoksazolilo]-4-hydroksy- . -5Hpriopyio-il^-ipropen-i-ylo/^imlidazolidynon-2.. b.3. R oznacza grupe -^R4^0-R5 i R2 ma wyzej podane znaczenie, np. 5 3- [3-,yil'-me1;okisy-il -metyloeityl!0/-5-iizoksazolilo]-4- -hydroksy-(5HmeitylOnl-/2-ipropen-il-yio/-imi'dazoli- dynon-2 i S-P^lHmeftoksyetyW-SHizoksaz^^^ tylo-\l -^2Hpropen-l -ylo^imidazolidynon-2., w b.4. R oznacza rodnik cMorowcoallkilaiwy i R2 ma wyzej podane znaczenie, np. 3-{3-/l-chloro-dHmetyloetylo/--5i-lizok'sazolilo]-i4-hy- xdrok:sy-'5i^me!tylcHl'-/2i-propen-il-ylo/-iimiidazoilidy- nonn2 i - W 343-/1-chlorometylo-1-mettyloetylo^5r4zoksazoli- loj-^hyckoksy-ei-metyio-il V2-|propen-l-ylo^^inpfida- zolMynon-2, b.5. !R oznacza grupe -HCF3 i R2 ma wyzej poda¬ ne znaczenie, n\p«- 20 y3^trójtfiuorometyllo-5-izoksiazoLi^ -me1;ylo-l-yi2HprcirenHl-yilCl/-:imidafzolidynon-2 d Sn/^trójfluoromeitylo-Si-Tzcteazalilo/^-chloro-S-bu- tyflo-1-/2-propen-fl -yloZ-limida&olidynon-2. b.6. jR oznacza rodnik cyMoaUkilowy i R2 ma wy- 25 zej podane znaczenie, np.S-ZG-cyklopropylo-S-izoksazic^liloM-hydrokisy-iS-ime- . ty'lo-l^12^pr'qlpen-ll-ylo/-inl)idazolidynon-2 i 3-/3^cykloheksylO'-5-d^oksaizolilo^4-hydroiKsy-6-'bu- tylo-1-^npropen-1-yla'-imjidazoli'dynon-2. 30 b.7. R oznacza rodnik alMlowy o. .1.-^6 atomach wegla i R2 ma wyzej podane znaczeniie, np. 3-[3V1-metylo^t^loM-izoksazolilo^-hydroksy-5- nmetyio-l-/2Mpropen-il-yloi'-im^dazolidynon-2 i 3-{-Al-etylo-il^metyloetylo/na-feoksazolilo]-4-(hydro- 35 ksy-SHrnetyllo-l-/2i-propen-ll-yla'-imlidazolidynon-2. b.8. R oznacza rodnik Ill-rzedjbultylowy i R2 ma wyzej podane znaczenie, np* . 3-[3-AVl-^woinietyloetylóy1j5-iizofcsazolilo]-4-hydro- ksy-5-meltylo-d-/l2-propen-1-yila-im^dazoiMdynon-2 i 40 3-[i3^.,l-dw^metyloe4;yloA5^izok^.zolilo]-4K:hloro- -5-meitylQ-l -/2-pro|pen-l-ylaMimidazoliidynon-2. b.9. IR oznacza rodnik alkenylowy lub alkinylowy zawierajacy do 5 aitomów wegla i R2 ma wy¬ zej podane znaczenie, np. 45 3-[3-/l,l^dwumetylo-2^propyn-l-ylo^^izoksazoli- 1o ]-4-hydrdkJsy-5-meftylo-1 n/^i^paropen-l -ylot/imida- zolidynon-2 i -•'-.'• . ¦ ' ' / 3-i[3-/ljldwume^tylo-a-jpropein-il-yllo/-'5-izoksazolii- lo] -4- hydiroksy-5nmetylo-1 -1(2-'pr0|pen-l-ylo/-imi- w dazolid3nnon-2. c^ R8 oznacza atom wodoru^. cil^ R oznacza grupe o wzorze 3 lub 4 i R2 ma wyzej podane znaczenie, np. . 3-{3^/l-fenoklsy-l-metyloetyilo/-5-(i(zoksa,zolilo]-4- 55 -hydroksy-l»/2-propen-l-ylovA-imidazolidynon-2 i 3"-[i3-/il-fenylo-1-metyl'Oetytlo/-5-izoksazoliio]-4-hy- droksy-1 -/2-propen-l-yla'-imidaizolidynon-2., cX R o'znacza gnupe —R4^S—^R5 i R2 ma wyzej podane znaczeniie, np.W 3-{3-/l -mertyloHl-nieltylo*ioeitylo/-i5-iizoksazolilo]-4- -hydroksy-r-y!2-ipropen-il-ylo/-imidazolidynon-2 i 3- [3VI-meitylotioetyilo/-i5-izolk'sazolilo]-4-hydrok,sy- : -l-/2l-prppen-l-y]io»/-ijmidazolidynon-B. c.3. R oznacza grupe ^r^o—R5(i R2 ma wyzej 65 . podane znaczenie, np.131693 tf 3-{3-4-metoksyJl-metyloetyio/MS-izoksazolilo]-4- -hydroksy-/lV2!ipropeai-l-ylo/-iimlidazo|lidyniOln^ i 3^[3-;11^metokisyetylo^5-izoksazo'l^ -l^/^ipropen^l-yiloZ-aJTuidaizolidyinon^. , c.4. R oznacza- rodnik chilorowcoailkilowy i R2 ma wyzej podane znaczenie, rup^ 3h[3-/1-chloro-il-nieitylofeltyilo^S-izoiksaiz^liao]^4-hy- droksy-1-/2^propen-l-yio/-iimid'azolidynon-2 i 3-[3-/1-chlorometylo-il HmeityloetyiO'/-5-i'zoksa;zoli- lo] ni V2-piropen-1-ylo/-timiidazolMynon-2. c.f5. R oznacza grupe —iGF3 i R2 ma wyzej podane znaczenie, np. - S-ZS^ójfluorom^tylo-SHiz^saiz^liloli-^-hydr^okisy-l- -/2Hpropen-^ylo/-imiid^zolidynon-2. c.6. R oznacza rodnik cykloalkiilowy i R2 ma wyzej podane znaczenie, np. 3^3-cykloheJk]sylo-5-i,zioksazolijlo/-4-hydjr€kBy-il-/2'- ipiropen^l-ylo^imidazoiMdyno'n-2 i 3-/3-cyklopentylo-5^izoksazo1iiilo/-4-chloiro-l-/2-p(rO'- pen-H-yioZ-imidazollidynon^. i c.7. R oznacza rodnik alkilowy o 1—16 atomach /wegla i R2 ma wyzej podane znaczenie, np. 3- [3-711 nmetyloetyW-S-iziotesalzodillO']-4^'hyidiroksy-1- -/l2-propen-l:-yioMmidazolMynon-2 i 3-[3-/l-etyIo-l-metyloeltylo/-5-izoksazoliJlo] -4-hydro^ • ksy-1-M-propen-il-yloMmidaizOllidynonHa. \ c.8. /R oznacza rodnik 111-irzed.butylowy i R2 ma' wyzej podane znaczenie, np, 3^[3-/1,1Hdlwiumeftyloeityilo/-5Hizoksazoailo] -4-hydro- ksy-il-^^ropen^l-yiloy^-aimadaizolildynon^ i 3- [3-/11,1-idwiumeityloeftyao-5-izoksa'zoliao]-4-cMaro- -ii V2h-propen-il-yloZ-imidazolidynon-B* c.,9; (R oznacza ,rodnik -ailkenylowy" luib alkinylo- \ wy ^aiwlieirajacy do 5 atomów wegla i R2 ma wyzej podane znaczenie, np. 3- [,3-)(l,11'Hdwiimetylo-2-pr opyn-l-yW-5-izoksaizoli- lo]-4-hy.dorolkisy-l~y!2ipiro|pen-il^ylo/-iniidaizolliidynon- -2i ". . 3-i [i3-i/11., 1-idwume!tylo-l2ipa:open-il -yioZ-iS^izoksazoli- lo]^4-hydroksy-lTy!2-p(rqpen-il-yilo/,^imida!zolidynon-2. d. R3 oznacza grupe hydroksylowa. dvi. R oznacza grupe o wzorze 3 lirfo 4 i R2 ma wyzej podane znaczenie, np. 3-[3-/1-tfaaokisy-lnmetyloatyloiAS-Lzoksazolilo1] -A5- -dwuhydrdksy-1-Vt2-propen-il'-yloA^im|idazolli]dynon- -2 i 3-[3-yil-fenyToetylo^-iS-izoksazolido]-4,i5-dwuhydro- ksy-il-yi2ipropen-l-ylo/HimiJdazolidynon-2.: . _ d.2. R oznacza grupe —R4^S—R5 i R2 ma wy¬ zej podane znaczenie, nip; ' 3^3-^I-imetylo-il-nietylotioetylo/^-izoksazolilo]- -4,5-dwiuhydrok sy-l-7l2-piropen-1 -yio/^imiidaizolidy- non-2 i 3- [3-yilnmetylotioetyloi/-i5i-iizoksafeoi!illo}-4,5-dwiuhy^ drokisy-1 n/12-propem-l-yiloZ-imMazolidynon-2. d.3. R oznacza grupe -^R*—O—(R5 i R2 ma wy¬ zej podane znaczenie, np. 3- [3-/1 -metoksyHl-nieltyiloe(tylot'-l5i-izoksazoililo]-i4,5- ^dwuhydiroksy-il-T^-piropen-l-yloZ-Lm-idazolidynon- -2 i 3-,[3i-y)l-metoksyetyl'a,-5^daoksa|zoililo]-4^Hdwuhy- droksy-l-/!2r|propen-tt-yio/-imiidaizalidynon-2.. d.4. R oznacza rodnik chlorowcoalkilowy i R2 ma wyzej podane znaczenie, np. 3-[3-^l-chlloro-lHme(tyloetylo/-i5=!ijzoiksazaliilo]-4,5- -dwuhyidroksy-'l:-^prqpen-a-ylo/-imida,zoiiidynon- -2i . - 3H[3-^l-chloromeityloHl^mei;ylc^ylo/-5-izoksaizoli- llo]-4j5Hdwuhydroksy-l^/12-)propen-l-ylo/-imidazoli- 5 dynon-2. d)5. R, oznacza girupe ^CF3 i R2 ma wyzej poda¬ ne znaczenie, np. 3-iy13-trójfluorometylo^5'-izc)kisazolilo/-4,5-fdwuhy- - dn:oksyjl-y2-pTopen-l-yio/-LrnlidaizOliiJdynon-2 i 10 3-yi3^trójcfiliuorome(tylo-5.-«izoksazoililo/-4-lbromo-5- -hydroksy-1-v12-propen^1-yloZ-imidazOlidynon-^.. d.6, R oznacza rodnik cykloalkilowy i R2 ma wy¬ zej podane znaczenie, np. 3-/3-cykloheksylo-6-izc)ksazoli,lo/-4^5-diwuhydrioksy- 15 -l-^propen-l-yioZ-imiidazolidynon^ i 3-^3-cy(kJloprapylio-l5-izokisaEOlliiilo/-4,5^dwuihydrOk.sy- ' -II-/2npropen-il'-ylo/-limidazoliidynon-2. d.7. R oznacza rodnik alkilowy o 1^6 aitomach .wegla i R2 ma wyzej podane znaczenie, np. 20 3-[3-y11-meityloeltyW-5-i'ZokisazoldlO']^4,f5-idiwuhydro- ksy-fl-vf2-propen-fl-ylo/-im'iidazo(]!iidynon-2 i 3-'{i3-/l ,jl-dwuimetylopropylo/-5/-izoksa!zolLlo]-4,5- -dwuhydiroksy-1-/2-piropen-l -ylo/-imiidawloidynon-2., d.8. R oznacza rodnik IILrzejd.butylowy i R2 ma 25 ' wyzej podane znaczenie, np.- 3-f3^/l ,1 -dwumetyloetytfoZ-Snizokisazolilo] -4,5-idwu- hydroltosy-ilry!2-ip(ropen-l-ylO'/-djrnjidazolidynon-2 i 3--[3-/l;l-dwumert;y!loe,tyLlo/'-Si-ilzioksazolilo]-4-cWloro- -5-hyidroksy-ll-/Ehpropen-1 -yloZ-fimiidazOlidynon-ST 30 dJ9. R oznacza rodnik ailkenylowy lulb alkinylowy zawierajacy do 5 atomów wegla i R2 ma wy- .zej podane znaczenie, np.. 3-i[3-/l,l:-dwumeltylo-i2-propyn-l-ylo/-i5-jizdk]saizioli- lo]-4j5Klwuhydiroksy-fl-/2-propen-1-ylo/-i/midazo- 35 !Mdynon-2i i ¦ 3-[3-/1,1-dwu-metyio-il-piropen-1-ylo/-i5-i!zoksazoli- lo]r4,5^diwuhydroksyHl-/l2ipropenjl-ylo/-iimiidaizoli- dynon^2., 2. R1 oznacza rodnik alkilowy o 1—3 aitomach 40 wegla, a. R8 oznacza rodnik alllilowy. a.l. R oznacza grupe o wzorze' 3 lub 4 i R2 ma wyzej podane znaczenie, np. 3-i[3-/l-fenylo-jl -meitylloetyloi/-5-iizoksazolilo]-4-hy- 4* dir'Oksy-5^12Hpropen-l:-ylo/-l-meltyloimidazOlidynon- -2 i 3-/[3-7!l-fenoksyeltyW-l5-izoPKis)aizoliilo]-4-hydrokSy-,5- -/2-propen-ll -ylo/-l-metyloiimMaizOlidynon--2. a.2; R oznacza grupe —R4-^S^R &i R2 ma wyzej M podane znaczenie, n|p, ¦ 3-[3-y?lnmetylo-1-meltyloetylo!/-5-izok:sazolilO']-4-hy- droksy-lS-Za-propen-l -ylio/-lHmetyloimiida'zolidy- non-2i i . 3- [3-/1-metylotioetylo/-'5i-Tzoksaizolilo]'-4-hydroksy- 55 -'5^y12ipropen-il-ylo/-l^eityloimida'zolidynon-2.. a.3^ jR oznacza grupe —^R4^0—R5 i R2 ma: wyzej podane znaczenie,, np, 3-[3-/l-meltoksy-llHmetyloeltyloZ-ISHiizoksazOlilo]-4- -hyckoksy-5-/2-propen-tl-ylo/^l-metyloimiidaizolidy- 60 non-2 i - 3- ta-yll -metokisyetylo/-5^izok's:a!zolilo]l-4-hydirdkjsy- -5-/2iprapDn^l-ylo/-'l:-mieityloimiidazoiiidynon-2. x aA R oznacza- (rodnik chloroweoailkilowy o 1—6 aitomach wetgla i R2 ma wyzej podane znacze- '* nie, np.131693 M&-/1-oMoco-a nme/tyloe^ diiK]&isy-5-.yi2ipirc)!pen-l-yl(/Hl-propyloimidazolNdy- inon-3 i 3-[S-Zl-chikHroimetyilo-l-meftyloeftyilo./-5-izoksazoli- lo] -4-hydrokls^-lnmeltyloM5-/2-propen-l-yloZ-timida- zolidynón-& aJ5. flR-oznacza grupe -hCF3 i R2 ma wyzej po¬ dane znaczenie, np. 3-/34rójfliiorometylo-5-izoksaz
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/122,633 US4268679A (en) | 1980-02-19 | 1980-02-19 | 3-[5- or 3-Substituted-5- or 3-isoxazolyl]-1-allyl or alkyl-4-substituted-5-substituted or unsubstituted-2-imidazolidinones |
| US06/207,151 US4507145A (en) | 1980-02-19 | 1980-11-18 | Herbicidal 3-[substituted 3- or 5-isoxazolyl]-1-4-, or 5-substituted-2-imidazolidinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL229717A1 PL229717A1 (pl) | 1982-08-16 |
| PL131693B1 true PL131693B1 (en) | 1984-12-31 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981229717A PL131693B1 (en) | 1980-02-19 | 1981-02-17 | Herbicide |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4507145A (pl) |
| EP (1) | EP0034456B1 (pl) |
| KR (1) | KR850000575B1 (pl) |
| AR (1) | AR227176A1 (pl) |
| AT (1) | ATE8993T1 (pl) |
| AU (1) | AU521876B2 (pl) |
| BG (1) | BG35322A3 (pl) |
| BR (1) | BR8100804A (pl) |
| CA (1) | CA1215988A (pl) |
| DD (1) | DD156564A5 (pl) |
| DE (1) | DE3165474D1 (pl) |
| DK (1) | DK151804C (pl) |
| ES (1) | ES8207527A1 (pl) |
| FI (1) | FI70014C (pl) |
| GR (1) | GR82688B (pl) |
| HU (1) | HU191030B (pl) |
| IE (1) | IE50840B1 (pl) |
| IL (1) | IL62093A (pl) |
| NO (1) | NO157978C (pl) |
| OA (1) | OA06749A (pl) |
| PH (1) | PH16614A (pl) |
| PL (1) | PL131693B1 (pl) |
| PT (1) | PT72524B (pl) |
| RO (1) | RO81607A2 (pl) |
| YU (1) | YU43762B (pl) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4857099A (en) * | 1982-02-12 | 1989-08-15 | American Cyanamid Company | Terrestrial and aquatic herbicidal methods |
| JPS58194869A (ja) * | 1982-05-10 | 1983-11-12 | Sankyo Co Ltd | イソオキサゾリノン誘導体及び殺虫・殺ダニ剤 |
| CA1189512A (en) * | 1982-06-01 | 1985-06-25 | John Krenzer | Urea compositions of matter |
| US4471123A (en) * | 1983-04-29 | 1984-09-11 | Eli Lilly And Company | Synthesis of isoxazolyl imidazolidinones |
| EP0129928B1 (en) * | 1983-06-27 | 1987-09-02 | Shell Internationale Researchmaatschappij B.V. | Oxazolyl-substituted diazaheterocycles |
| JPS6092285A (ja) * | 1983-10-26 | 1985-05-23 | Shionogi & Co Ltd | イソオキサゾ−ル系環状尿素類 |
| US4604127A (en) * | 1984-07-17 | 1986-08-05 | Eli Lilly And Company | Herbicidal pyridazinylimidazolidinone compounds |
| US4600430A (en) * | 1985-02-22 | 1986-07-15 | Eli Lilly And Company | Pyridinylimidazolidinone compounds |
| JPS6296479A (ja) | 1985-10-23 | 1987-05-02 | Shionogi & Co Ltd | ポリフルオロアルキルイソオキサゾリルアミン類 |
| GB9225377D0 (en) * | 1992-12-04 | 1993-01-27 | Ici Plc | Herbicides |
| WO2016071361A2 (en) * | 2014-11-07 | 2016-05-12 | Syngenta Participations Ag | Herbicidal compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3544582A (en) * | 1965-04-06 | 1970-12-01 | Hoffmann La Roche | Process for preparing aminoisoxazoles |
| US3773780A (en) * | 1971-03-10 | 1973-11-20 | Bayer Ag | 1-(1,3,4-thiadiazol-2-yl)-imidazolidinone-(2)compounds |
| US3847935A (en) * | 1972-04-12 | 1974-11-12 | Upjohn Co | 5-substituted 1-(3h,1,4-benzodiazepin-2-yl)-2-imidazolidinones |
| US4038410A (en) * | 1974-03-14 | 1977-07-26 | Schering Aktiengesellschaft | Nitroimidazole derivatives and process for the preparation thereof |
| EP0002881A1 (en) * | 1977-11-02 | 1979-07-11 | FISONS plc | 5-Isoxazolylurea derivatives, their preparation, their use and compositions containing them |
| US4268679A (en) * | 1980-02-19 | 1981-05-19 | Ppg Industries, Inc. | 3-[5- or 3-Substituted-5- or 3-isoxazolyl]-1-allyl or alkyl-4-substituted-5-substituted or unsubstituted-2-imidazolidinones |
| NZ197589A (en) * | 1980-07-07 | 1984-11-09 | Lilly Co Eli | 3-(isoxazol-3 or 5-yl)-4 hydroxyimidazolidin-2-ones and corresponding imidazolin-2-ones |
-
1980
- 1980-11-18 US US06/207,151 patent/US4507145A/en not_active Expired - Lifetime
-
1981
- 1981-01-23 AU AU66580/81A patent/AU521876B2/en not_active Ceased
- 1981-02-09 IL IL62093A patent/IL62093A/xx unknown
- 1981-02-10 DE DE8181300531T patent/DE3165474D1/de not_active Expired
- 1981-02-10 EP EP81300531A patent/EP0034456B1/en not_active Expired
- 1981-02-10 AT AT81300531T patent/ATE8993T1/de active
- 1981-02-10 BR BR8100804A patent/BR8100804A/pt unknown
- 1981-02-12 ES ES499350A patent/ES8207527A1/es not_active Expired
- 1981-02-13 DK DK065381A patent/DK151804C/da not_active IP Right Cessation
- 1981-02-16 YU YU387/81A patent/YU43762B/xx unknown
- 1981-02-16 RO RO81103430A patent/RO81607A2/ro unknown
- 1981-02-16 FI FI810467A patent/FI70014C/fi not_active IP Right Cessation
- 1981-02-16 AR AR284301A patent/AR227176A1/es active
- 1981-02-16 BG BG050853A patent/BG35322A3/xx unknown
- 1981-02-16 GR GR64156A patent/GR82688B/el unknown
- 1981-02-17 PL PL1981229717A patent/PL131693B1/pl unknown
- 1981-02-17 DD DD81227680A patent/DD156564A5/de not_active IP Right Cessation
- 1981-02-17 KR KR1019810000494A patent/KR850000575B1/ko not_active Expired
- 1981-02-17 PT PT72524A patent/PT72524B/pt unknown
- 1981-02-17 HU HU81381A patent/HU191030B/hu not_active IP Right Cessation
- 1981-02-18 NO NO810553A patent/NO157978C/no unknown
- 1981-02-18 CA CA000371136A patent/CA1215988A/en not_active Expired
- 1981-02-18 IE IE331/81A patent/IE50840B1/en unknown
- 1981-02-19 OA OA57332A patent/OA06749A/xx unknown
- 1981-02-19 PH PH25232A patent/PH16614A/en unknown
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