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HRP20161113T1 - N-(1,3,4-oksadiazol-2-il)arilkarboksamidi i njihova uporaba kao herbicida - Google Patents

N-(1,3,4-oksadiazol-2-il)arilkarboksamidi i njihova uporaba kao herbicida Download PDF

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HRP20161113T1
HRP20161113T1 HRP20161113TT HRP20161113T HRP20161113T1 HR P20161113 T1 HRP20161113 T1 HR P20161113T1 HR P20161113T T HRP20161113T T HR P20161113TT HR P20161113 T HRP20161113 T HR P20161113T HR P20161113 T1 HRP20161113 T1 HR P20161113T1
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alkyl
halo
cycloalkyl
heterocyclyl
hydrogen
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Arnim Köhn
Hartmut Ahrens
Ralf Braun
Simon DÖRNER-RIEPING
Stefan Lehr
Ines Heinemann
Isolde HÄUSER-HAHN
Elmar Gatzweiler
Christopher Hugh Rosinger
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Bayer Intellectual Property Gmbh
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    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/82—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 three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • C07F9/65306—Five-membered rings containing two nitrogen atoms
    • C07F9/65312—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 2

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (12)

1. N-(1,3,4-oksadiazol-2-il)arilkarboksamidi s formulom (I) ili njihove soli [image] naznačeni time da su supstituenti definirani kako slijedi: A je N ili CY, R je vodik, (C1-C6)-alkil, R1O-(C1-C6)-alkil, CH2R6, (C3-C7)-cikloalkil, halo-(C1-C6)-alkil, (C2-C6)-alkenil, halo-(C2-C6)-alkenil, (C2-C6)-alkinil, halo-(C2-C6)-alkinil, OR1, NHR1, metoksikarbonil, etoksikarbonil, metoksikarbonilmetil, etoksikarbonilmetil, metilkarbonil, trifluormetilkarbonil, dimetilamino, acetilamino, metilsulfenil, metilsulfinil, metilsulfonil, ili heteroaril, heterociklil, benzil ili fenil svaki supstituiran s radikalima iz skupine koju čine halogen, nitro, cijano, (C1-C6)-alkil, halo-(C1-C6)-alkil, (C3-C6)-cikloalkil, S(O)n-(C1-C6)-alkil, (C1-C6)-alkoksi, halo-(C1-C6)-alkoksi, (C1-C6)-alkoksi-(C1-C4)-alkil, X je nitro, halogen, cijano, formil, tiocijanato, (C1-C6)-alkil, halo-(C1-C6)-alkil, (C2-C6)-alkenil, halo-(C2-C6)-alkenil, (C2-C6)-alkinil, halo-(C3-C6)-alkinil, (C3-C6)-cikloalkil, halo-(C3-C6)-cikloalkil, (C3-C6)-cikloalkil-(C1-C6)-alkil, halo-(C3-C6)-cikloalkil-(C1-C6)-alkil, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OR1, OCOR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkil-S(O)nR2, (C1-C6)-alkil-OR1, (C1-C6)-alkil-OCOR1, (C1-C6)-alkil-OSO2R2, (C1-C6)-alkil-CO2R1, (C1-C6)-alkil-SO2OR1, (C1-C6)-alkil-CON(R1)2, (C1-C6)-alkil-SO2N(R1)2, (C1-C6)-alkil-NR1COR1, (C1-C6)-alkil-NR1SO2R2, NR1R2, P(O)(OR5)2, CH2P(O)(OR5)2, (C1-C6)-alkilheteroaril, (C1-C6)-alkilheterociklil, gdje su dva potonja radikala svaki supstituirani s halogenom, (C1-C6)-alkilom, halo-(C1-C6)-alkilom, S(O)n-(C1-C6)-alkilom, (C1-C6)-alkoksi, halo-(C1-C6)7alkoksi radikalima, te gdje heterociklil nosi n okso skupina, Y je vodik, nitro, halogen, cijano, tiocijanato, (C1-C6)-alkil, halo-(C1-C6)-alkil, (C2-C6)-alkenil, halo-(C2-C6)-alkenil, (C2-C6)-alkinil, halo-(C2-C6)-alkinil, (C3-C6)-cikloalkil, (C3-C6)-cikloalkenil, halo-(C3-C6)-cikloalkil, (C3-C6)-cikloalkil-(C1-C6)-alkil, halo-(C3-C6)-cikloalkil-(C1-C6)-alkil, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, CO (NOR1) R1, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, (C1-C6)-alkil-S(O)nR2, (C1-C6)-alkil-OR1, (C1-C6)-alkil-OCOR1, (C1-C6)-alkil-OSO2R2, (C1-C6)-alkil-CO2R1, (C1-C6)-alkil-CN, (C1-C6)-alkil-SO2OR1, (C1-C6)-alkil-CON(R1)2, (C1-C6)-alkil-SO2N(R1)2, (C1-C6)-alkil-NR1COR1, (C1-C6)-alkil-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O) (OR5)2, (C1-C6)-alkilfenil, (C1-C6)-alkilheteroaril, (C1-C6)-alkilheterociklil, fenil, heteroaril ili heterociklil, gdje su 6 potonjih radikala svaki supstituiran s radikalima iz skupine koju čine halogen, nitro, cijano, (C1-C6)-alkil, halo-(C1-C6)-alkil, (C3-C6)-cikloalkil, S(O)n-(C1-C6)-alkil, (C1-C6)-alkoksi, halo-(C1-C6)-alkoksi, (C1-C6)-alkoksi-(C1-C4)-alkil i cijanometil, te gdje heterociklil nosi n okso skupina, Z je halogen, cijano, tiocijanato, (C1-C6)-alkil, (C1-C6)-alkoksi, halo-(C1-C6)-alkil, (C2-C6)-alkenil, halo-(C2-C6)-alkenil, (C2-C6)-alkinil, halo-(C2-C6)-alkinil, (C3-C6)-cikloalkil, halo-(C3-C6)-cikloalkil, (C3-C6)-cikloalkil-(C1-C6)-alkil, halo-(C3-C6)-cikloalkil-(C1-C6)-alkil, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkil-S(O)nR2, (C1-C6)-alkil-OR1, (C1-C6)-alkil-OCOR1, (C1-C6)-alkil-OSO2R2, (C1-C6)-alkil-CO2R1, (C1-C6)-alkil-SO2OR1, (C1-C6)-alkil-CON(R1)2, (C1-C6)-alkil-SO2N(R1)2, (C1-C6)-alkil-NR1COR1, (C1-C6)-alkil-NR1SO2R2, N(R1)2, P(O)(OR5)2, heteroaril, heterociklil ili fenil, gdje su tri potonja radikala svaki supstituiran s radikalima iz skupine koju čine halogen, nitro, cijano, (C1-C6)-alkil, halo-(C1-C6)-alkil, (C3-C6)-cikloalkil, S(O)n-(C1-C6)-alkil, (C1-C6)-alkoksi ili halo-(C1-C6)-alkoksi, te gdje heterociklil nosi n okso skupina, ili Z može također biti vodik ako Y je S(O)nR2 radikal, R1 je vodik, (C1-C6)-alkil, (C1-C6)-haloalkil, (C2-C6)-alkenil, (C2-C6)-haloalkenil, (C2-C6)-alkinil, (C2-C6)-haloalkinil, (C3-C6)-cikloalkil, (C3-C6)-cikloalkenil, (C3-C6)-halocikloalkil, (C1-C6)-alkil-O-(C1-C6)-alkil, (C3-C6)-cikloalkil-(C1-C6)-alkil, fenil, fenil-(C1-C6)-alkil, heteroaril, (C1-C6)-alkilheteroaril, heterociklil, (C1-C6)-alkilheterociklil, (C1-C6)-alkil-O-heteroaril, (C1-C6)-alkil-O-heterociklil, (C1-C6)-alkil-NR3-heteroaril, (C1-C6)-alkil-NR3-heterociklil, gdje je 21 potonjih radikala supstituirano s radikalima iz skupine koju čine cijano, halogen, nitro, tiocijanato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 i (C1-C4)-alkoksi-(C2-C6)-alkoksikarbonil, te gdje heterociklil nosi n okso skupina, R2 je (C1-C6)-alkil, (C1-C6)-haloalkil, (C2-C6)-alkenil, (C2-C6)-haloalkenil, (C2-C6)-alkinil, (C2-C6)- haloalkinil, (C3-C6)-cikloalkil, (C3-C6)-cikloalkenil, (C3-C6)-halocikloalkil, (C1-C6)-alkil-O-(C1-C6)-alkil, (C3-C6)-cikloalkil-(C1-C6)-alkil, fenil, fenil-(C1-C6)-alkil, heteroaril, (C1-C6)-alkilheteroaril, heterociklil, (C1-C6)-alkilheterociklil, (C1-C6)-alkil-O-heteroaril, (C1-C6)-alkil-O-heterociklil, (C1-C6)-alkil-NR3-heteroaril, (C1-C6)-alkil-NR3-heterociklil, gdje je 21 potonjih radikala supstituirano s radikalima iz skupine koju čine cijano, halogen, nitro, tiocijanato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 i (C1-C4)-alkoksi-(C2-C6)-alkoksikarbonil, te gdje heterociklil nosi n okso skupina, R3 je vodik, (C1-C6)-alkil, (C2-C6)-alkenil, (C2-C6-alkinil, (C3-C6-cikloalkil ili (C3-C6)-cikloalkil-(C1-C6)-alkil, R4 je (C1-C6)-alkil, (C2-C6)-alkenil ili (C2-C6)-alkinil, R5 je metil ili etil, R6 je acetoksi, acetamido, N-metilacetamido, benzoiloksi, benzamido, N-metilbenzamido, metoksikarbonil, etoksikarbonil, benzoil, metilkarbonil, piperidinilkarbonil, morfolinilkarbonil, trifluormetilkarbonil, aminokarbonil, metilaminokarbonil, dimetilaminokarbonil, (C1-C6)-alkoksi, (C3-C6)-cikloalkil, ili heteroaril, heterociklil ili fenil svaki supstituiran s radikalima iz skupine koju čine metil, etil, metoksi, trifluormetil i halogen, n je 0, 1 ili 2; s je 0, 1, 2 ili 3, pod uvjetom da a) X i Z nisu oba isti radikal iz skupine koju čine klor, fluor, metoksi i metil kada Y je vodik, b) X nije hidroksil kada Y je vodik i Z je metoksi, c) X nije klor ili brom kada Y je vodik i Z je fluor, d) X nije fluor kada Y je vodik i Z je brom, e) X ili Z nije vodik kada A je dušik, f) R nije trifluormetil kada X je acetoksi i Z je metil.
2. N-(1,3,4-oksadiazol-2-il)arilkarboksamidi prema zahtjevu 1, naznačeni time da A je N ili CY, R je vodik, (C1-C6)-alkil, (C3-C7)-cikloalkil, halo-(C1-C6)-alkil, (C3-C7)-cikloalkilmetil, metoksikarbonilmetil, etoksikarbonilmetil, acetilmetil, metoksimetil, metoksietil, benzil, pirazin-2-il, furan-2-il, tetrahidrofuran-2-il, morfolin, dimetilamino, ili fenil supstituiran s radikalima iz skupine koju čine metil, metoksi, trifluormetil i halogen; X je nitro, halogen, cijano, (C1-C6)-alkil, halo-(C1-C6)-alkil, (C3-C6)-cikloalkil, OR1, S(O)nR2, (C1-C6)-alkil-S(O)nR2, (C1-C6)-alkil-OR1, (C1-C6)-alkil-CON (R1)2, (C1-C6)-alkil-SO2N(R1)2, (C1-C6)-alkil-NR1COR1, (C1-C6)-alkil-NR1SO2R2, (C1-C6)-alkilheteroaril, (C1-C6)-alkilheterociklil, gdje su dva potonja radikala svaki supstituirani s halogenom, (C1-C6)-alkil, halo-(C1-C6)-alkil, S(O)n-(C1-C6)-alkil, (C1-C6)-alkoksi, halo-(C1-C6)-alkoksi radikalima, te gdje heterociklil nosi n okso skupina, Y je vodik, nitro, halogen, cijano, (C1-C6)-alkil, (C1-C6)-haloalkil, OR1, S(O)nR2, SO2N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (C1-C6)-alkil-S(O)nR2, (C1-C6)-alkil-OR1, (C1-C6)-alkil-CON(R1)2, (C1-C6)-alkil-SO2N(R1)2, (C1-C6)-alkil-NR1COR1, (C1-C6)-alkil-NR1SO2R2, (C1-C6) alkilfenil, (C1-C6)-alkilheteroaril, (C1-C6)-alkilheterociklil, fenil, heteroaril ili heterociklil, gdje su 6 potonjih radikala svaki supstituiran s radikalima iz skupine koju čine halogen, nitro, cijano, (C1-C6)-alkil, halo-(C1-C6)-alkil, (C3-C6)-cikloalkil, S(O)n-(C1-C6)-alkil, (C1-C6)-alkoksi, halo-(C1-C6)-alkoksi, (C1-C6)-alkoksi-(C1-C9)-alkil i cijanometil, te gdje heterociklil nosi n okso skupina, Z je halogen, cijano, nitro, metil, halo-(C1-C6)-alkil, (C3-C6)-cikloalkil, S(O)nR2, 1,2,4-triazol-1-il, pirazol-1-il, ili Z može također biti vodik ako Y je S(O)nR2 radikal, R1 je vodik, (C1-C6)-alkil, (C2-C6)-alkenil, (C2-C6)-alkinil, (C3-C6)-cikloalkil, (C3-C6)-cikloalkil-(C1-C6)-alkil, (C1-C6)-alkil-O-(C1-C6)-alkil, fenil, fenil-(C1-C6)-alkil, heteroaril, (C1-C6)-alkilheteroaril, heterociklil, (C1-C6)-alkilheterociklil, (C1-C6)-alkil-O-heteroaril, (C1-C6)-alkil-O-heterociklil, (C1-C6)-alkil-NR3-heteroaril ili (C1-C6)-alkil-NR3-heterociklil, gdje je 16 potonjih radikala supstituirano s radikalima iz skupine koju čine cijano, halogen, nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 i (C1-C4)-alkoksi-(C2-C6)-alkoksikarbonil, te gdje heterociklil nosi n okso skupina, R2 je (C1-C6)-alkil, (C3-C6)-cikloalkil ili (C3-C6)-cikloalkil-(C1-C6)-alkil, gdje ta tri gore navedena radikala mogu svaki biti supstituirani s radikalima iz skupine koju čine halogen i OR3, R3 je vodik ili (C1-C6)-alkil, R4 je (C1-C6)-alkil, n je 0, 1 ili 2; s je 0, 1, 2 ili 3, pod uvjetom da a) X i Z nisu oba isti radikal iz skupine koju čine klor, fluor, metoksi i metil kada Y je vodik, b) X nije hidroksil kada Y je vodik i Z je metoksi, c) X nije klor ili brom kada Y je vodik i Z je fluor, d) X nije fluor kada Y je vodik i Z je brom, e) X ili Z nije vodik kada A je dušik, f) R nije trifluormetil kada X je acetoksi i Z je metil.
3. Herbicidni pripravci, naznačeni time da sadrže herbicidno aktivni udio barem jednog spoja formule (I) prema zahtjevu 1 ili 2.
4. Herbicidni pripravci prema zahtjevu 3, naznačeni time da su u smjesi s pomoćnim sredstvima za formuliranje.
5. Herbicidni pripravci prema zahtjevu 3 ili 4, naznačeni time da sadrže barem jednu dodatnu pesticidno aktivnu tvar iz skupine koju čine insekticidi, akaricidi, herbicidi, fungicidi, zaštitna sredstva i regulatori rasta.
6. Herbicidni pripravci prema zahtjevu 5, naznačeni time da sadrže zaštitnu tvar.
7. Herbicidni pripravci prema zahtjevu 6, naznačeni time da sadrže ciprosulfamid, klokvintocet-meksil, mefenpir-dietil ili izoksadifen-etil.
8. Herbicidni pripravci prema bilo kojem od zahtjeva 5 do 7, naznačeni time da sadrže dodatni herbicid.
9. Postupak za suzbijanje neželjenih biljaka, naznačen time da se učinkovita količina barem jednog spoja formule (I) prema zahtjevu 1 ili 2 ili herbicidnog pripravka prema bilo kojem od zahtjeva 3 do 8 primjenjuje na biljke ili na mjesto neželjene vegetacije.
10. Uporaba spojeva s formulom (I) prema zahtjevu 1 ili 2 ili herbicidnih pripravaka prema bilo kojem od zahtjeva 3 do 8, naznačena time da je za suzbijanje neželjenih biljaka.
11. Uporaba prema zahtjevu 10, naznačena time da se spojevi s formulom (I) koriste za suzbijanje neželjenih biljaka u usjevima korisnih biljaka.
12. Uporaba prema zahtjevu 11, naznačena time da korisne biljke su transgene korisne biljke.
HRP20161113TT 2011-03-22 2016-08-31 N-(1,3,4-oksadiazol-2-il)arilkarboksamidi i njihova uporaba kao herbicida HRP20161113T1 (hr)

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