HRP20110592T1 - Spojevi 2-aril-5-heteroaril-cikloheksan-1,3-diona i njihova uporaba kao herbicida - Google Patents
Spojevi 2-aril-5-heteroaril-cikloheksan-1,3-diona i njihova uporaba kao herbicida Download PDFInfo
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- HRP20110592T1 HRP20110592T1 HR20110592T HRP20110592T HRP20110592T1 HR P20110592 T1 HRP20110592 T1 HR P20110592T1 HR 20110592 T HR20110592 T HR 20110592T HR P20110592 T HRP20110592 T HR P20110592T HR P20110592 T1 HRP20110592 T1 HR P20110592T1
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- Prior art keywords
- c5alkyl
- halogen
- nitro
- cyano
- substituted
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- 239000004009 herbicide Substances 0.000 title claims 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 66
- 150000002367 halogens Chemical class 0.000 claims abstract 66
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 55
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 54
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims abstract 43
- 150000001875 compounds Chemical class 0.000 claims abstract 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 35
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 30
- 239000001257 hydrogen Substances 0.000 claims abstract 30
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims abstract 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 24
- 150000002431 hydrogen Chemical class 0.000 claims abstract 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 21
- -1 ethylnyl Chemical group 0.000 claims abstract 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract 6
- 229920002554 vinyl polymer Polymers 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 125000004969 haloethyl group Chemical group 0.000 claims abstract 4
- 125000004970 halomethyl group Chemical group 0.000 claims abstract 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 2
- 125000006772 (C1-C6) haloalkylsulfonyloxy group Chemical group 0.000 claims abstract 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000005240 diheteroarylamino group Chemical group 0.000 claims 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 229910020008 S(O) Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 230000002363 herbicidal effect Effects 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 2
- 241000196324 Embryophyta Species 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 150000001543 aryl boronic acids Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 2
- 239000003223 protective agent Substances 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 241000209504 Poaceae Species 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000006410 propenylene group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D309/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/04—Seven-membered rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
- C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Spoj formule (I) naznačen time, daR1 je metil, etil, n-propil, izo-propil, ciklopropil, halometil, haloetil, halogen, vinil, etilnil, metoksi, etoksi, halometoksi ili haloetoksi; R2 i R3 su neovisno, vodik, halogen, C1-C6alkil, C1-C6haloalkil, C1-C6alkoksi, C1-C6haloalkoksi, C2-C6alkenil, C2-C6haloalkenil, C2-C6alkinil, C3-C6alkeniloksi, C3-C6haloalkeniloksi, C3-C6alkiniloksi, C3-C6cikloalkil, C1-C6alkiltio, C1-C6alkilsulfinil, C1-C6alkilsulfonil, C1-C6alkilsulfoniloksi, C1-C6haloalkilsulfoniloksi, cijano, nitro, fenil; fenil supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil; ili heteroaril ili heteroaril supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil; R4 je vodik, metil, etil, n-propil, izo-propil, halometil, haloetil, halogen, vinil, etilnil, metoksi, etoksi, halometoksi ili haloetoksi; X je O, S, S(O) ili S(O)2; R5 je vodik ili metil; R6 je vodik, metil ili etil, ili tvori dvostruku vezu, koja veže atom ugljika, na koji je R6 priključen, sa susjednim atomom ugljika od R7 ili R8; R7 i R8 su neovisno jedan od drugoga C1-C5alkilen, koji je nesupstituiran ili supstituiran sa metil ili etil, ili C2-C5alkenilen, koji je nesupstituiran ili supstituiran sa metil ili etil; a G je vodik, alkalijski metal, alkalijski zemni metal, sulfonij, amonij ili latentna skupina; pri čemu, kada je G latentna skupina tada G je : C1-C8alkil, C2-C8haloalkil, fenilC1-C8alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), heteroarilC1-C8alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), C3-C8 alkenil, C3-C8 haloalkenil, C3-C8 alkinil, C(Xa)-Ra, C(Xb)-Xc-Rb, C(Xd)-N(Rc-Rd, -SO2-Re, -P(Xe)(Rf)-Rg ili CH2-Xf-Rh; gdje Xa, Xb, Xc, Xd, Xe i Xf su neovisno jedan od drugoga kisik ili sumpor; i gdje Ra je H, C1-C18alkil, C2-C18alkenil, C2-C18alkinil, C1-C10haloalkil, C1-C10cijanoalkil, C1-C10nitroalkil, C1-C10 aminoalkil, C1-C5alkilaminoC1-C5alkil, C2-C8dialkilaminoC1-C5alkil, C3-C7cikloalkilC1-C5alkil, C1-C5alkoksiC1-C5alkil, C3-C5alkeniloksiC1-C5alkil, C3-C5alkinilC1-C5oksialkil, C1-C5alkiltioC1-C5alkil, C1-C5alkilsulfinilC1-C5alkil, C1-C5alkilsulfonilC1-C5alkil, C2-C8alkilidenaminoksiC1-C5alkil, C1-C5alkilkarbonilC1-C5alkil, C1-C5 alkoksikarbonilC1-C5alkil, aminokarbonilC1-C5alkil, C1-C5alkilaminokarbonilC1-C5alkil, C2-C8dialkilaminokarbonilC1-C5alkil, C1-C5alkilkarbonilaminoC1-C5alkil, N-C1-C5alkilkarbonil-N-C1-C5alkilaminoC1-C5alkil, C3-C6trialkilsililC1-C5alkil, fenilC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-
Claims (33)
1. Spoj formule (I)
[image]
naznačen time, da
R1 je metil, etil, n-propil, izo-propil, ciklopropil, halometil, haloetil, halogen, vinil, etilnil, metoksi, etoksi, halometoksi ili haloetoksi;
R2 i R3 su neovisno, vodik, halogen, C1-C6alkil, C1-C6haloalkil, C1-C6alkoksi, C1-C6haloalkoksi, C2-C6alkenil, C2-C6haloalkenil, C2-C6alkinil, C3-C6alkeniloksi, C3-C6haloalkeniloksi, C3-C6alkiniloksi, C3-C6cikloalkil, C1-C6alkiltio, C1-C6alkilsulfinil, C1-C6alkilsulfonil, C1-C6alkilsulfoniloksi, C1-C6haloalkilsulfoniloksi, cijano, nitro, fenil;
fenil supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil; ili heteroaril ili heteroaril supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil;
R4 je vodik, metil, etil, n-propil, izo-propil, halometil, haloetil, halogen, vinil, etilnil, metoksi, etoksi, halometoksi ili haloetoksi; X je O, S, S(O) ili S(O)2; R5 je vodik ili metil; R6 je vodik, metil ili etil, ili tvori dvostruku vezu, koja veže atom ugljika, na koji je R6priključen, sa susjednim atomom ugljika od R7 ili R8;
R7 i R8 su neovisno jedan od drugoga C1-C5alkilen, koji je nesupstituiran ili supstituiran sa metil ili etil, ili C2-C5alkenilen, koji je nesupstituiran ili supstituiran sa metil ili etil; a G je vodik, alkalijski metal, alkalijski zemni metal, sulfonij, amonij ili latentna skupina;
pri čemu, kada je G latentna skupina tada G je : C1-C8alkil, C2-C8haloalkil, fenilC1-C8alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), heteroarilC1-C8alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), C3-C8 alkenil, C3-C8 haloalkenil, C3-C8 alkinil, C(Xa)-Ra, C(Xb)-Xc-Rb, C(Xd)-N(Rc-Rd, -SO2-Re, -P(Xe)(Rf)-Rg ili CH2-Xf-Rh;
gdje Xa, Xb, Xc, Xd, Xe i Xf su neovisno jedan od drugoga kisik ili sumpor; i gdje Ra je H, C1-C18alkil, C2-C18alkenil, C2-C18alkinil, C1-C10haloalkil, C1-C10cijanoalkil, C1-C10nitroalkil, C1-C10 aminoalkil, C1-C5alkilaminoC1-C5alkil, C2-C8dialkilaminoC1-C5alkil, C3-C7cikloalkilC1-C5alkil, C1-C5alkoksiC1-C5alkil, C3-C5alkeniloksiC1-C5alkil, C3-C5alkinilC1-C5oksialkil, C1-C5alkiltioC1-C5alkil, C1-C5alkilsulfinilC1-C5alkil, C1-C5alkilsulfonilC1-C5alkil, C2-C8alkilidenaminoksiC1-C5alkil, C1-C5alkilkarbonilC1-C5alkil, C1-C5 alkoksikarbonilC1-C5alkil, aminokarbonilC1-C5alkil, C1-C5alkilaminokarbonilC1-C5alkil, C2-C8dialkilaminokarbonilC1-C5alkil, C1-C5alkilkarbonilaminoC1-C5alkil, N-C1-C5alkilkarbonil-N-C1-C5alkilaminoC1-C5alkil, C3-C6trialkilsililC1-C5alkil, fenilC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), heteroarilC1-C5alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili nitro), C2-C5haloalkenil, C3-C8cikloalkil; fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; ili heteroaril ili heteroaril supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; i
Rb je C1-C18alkil, C3-C18alkenil, C3-C18alkinil, C2-C10haloalkil, C1-C10cijanoalkil, C1-C10nitroalkil, C2-C10 aminoalkil, C1-C5alkilaminoC1-C5alkil, C2-C8dialkilaminoC1-C5alkil, C3-C7cikloalkilC1-C5alkil, C1-C5alkoksiC1-C5alkil, C3-C5alkeniloksiC1-C5alkil, C3-C5alkiniloksiC1-C5alkil, C1-C5alkiltioC1-C5alkil, C1-C5alkilsulfinilC1-C5alkil, C1-C5alkilsulfonilC1-C5alkil, C2-C8alkilidenaminoksiC1-C5alkil, C1-C5alkilkarbonilC1-C5alkil, C1-C5alkoksikarbonilC1-C5alkil, aminokarbonilC1-C5alkil, C1-C5alkilaminokarbonilC1-C5alkil, C2-C8dialkilaminokarbonilC1-C5alkil, C1-C5alkilkarbonilaminoC1-C5alkil, N-C1-C5alkilkarbonil-N-C1-C5alkilaminoC1-C5alkil, C3-C6trialkilsililC1-C5alkil, fenilC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), heteroarilC1-C5alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), C3-C5haloalkenil, C3-C8cikloalkil; fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro;
ili heteroaril ili heteroaril supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro;
a Rci Rd su svaki neovisno od drugoga vodik, C1-C10alkil, C3-C10alkenil, C3-C10alkinil, C2-C10haloalkil, C1-C10cijanoalkil, C1-C10nitroalkil, C1-C10aminoalkil, C1-C5alkilaminoC1-C5alkil, C2-C8dialkilaminoC1-C5alkil, C3-C7cikloalkilC1-C5alkil, C1-C5alkoksiC1-C5alkil, C3-C5alkeniloksiC1-C5alkil, C3-C5 alkiniloksiC1-C5alkil, C1-C5alkiltioC1-C5alkil, C1-C5alkilsulfinilC1-C5alkil, C1-C5alkilsulfonilC1-C5alkil, C2-C8alkilidenaminoksiC1-C5alkil, C1-C5alkilkarbonilC1-C5alkil, C1-C5alkoksikarbonilC1-C5alkil, aminokarbonilC1-C5alkil, C1-C5alkilaminokarbonilC1-C5alkil, C2-C8dialkilaminokarbonilC1-C5alkil, C1-C5alkilkarbonilaminoC1-C5alkil, N-C1-C5a kilkarbonil-N-C2-C5alkilaminoalkil, C3-C6trialkilsililC1-C5alkil, fenilC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), heteroarilC1-C5alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), C2-C5haloalkenil, C3-C8cikloalkil; fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; heteroaril ili heteroaril supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; heteroarilamino ili heteroarilamino supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; diheteroarilamino ili diheteroarilamino supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; fenilamino ili fenilamino supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; difenilamino ili difenilamino supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; ili C3-C7cikloalkilamino, di-C3-C7cikloalkilamino ili C3-C7cikloalkoksi;
ili Rci Rd mogu spojeni zajedno tvoriti 3-7-člani prsten, opcijski sadržavajući jedan heteroatom odabran od O ili S; a Reje C1-C10alkil, C2-C10alkenil, C2-C10alkinil, C1-C10haloalkil, C1-C10cijanoalkil, C1-C10nitroalkil, C1-C10aminoalkil, C1-C5alkilaminoC1-C5alkil, C2-C8dialkilaminoC1-C5alkil, C3-C7cikloalkilC1-C5alkil, C1-C5 alkoksiC1-C5alkil, C3-C5alkeniloksiC1-C5alkil, C3-C5alkiniloksiC1-C5alkil, C1-C5alkiltioC1-C5alkil, C1-C5alkilsulfinilC1-C5alkil, C1-C5alkilsulfonilC1-C5alkil, C2-C8alkilidenaminoksiC1-C5alkil, C1-C5alkilkarbonilC1-C5alkil, C1-C5alkoksikarbonilC1-C5alkil, aminokarbonilC1-C5alkil, C1-C5alkilaminokarbonilC1-C5alkil, C2-C8dialkilaminokarbonilC1-C5alkil, C1-C5alkilkarbonilaminoC1-C5alkil, N-C1-C5alkilkarbonil-N-C1-C5alkilaminoC1-C5alkil, C3-C6trialkilsililC1-C5alkil, fenilC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), heteroarilC1-C5alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano ili sa nitro), C2-C5haloalkenil, C3-C8cikloalkil; fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; heteroaril ili heteroaril supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; heteroarilamino ili heteroarilamino supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; diheteroarilamino ili diheteroarilamino supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; fenilamino ili fenilamino supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; difenilamino ili difenilamino supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; ili C3-C7cikloalkilamino, diC3-C7cikloalkilamino, C3-C7cikloalkoksi, C1-C10alkoksi, C1-C10haloalkoksi, C1-C5alkilamino ili C2-C8dialkilamino; Rfi R9su svaki neovisno od drugoga C1-C10alkil, C2-C10alkenil, C2-C10alkinil, C1-C10alkoksi, C1-C10haloalkil, C1-C10cijanoalkil, C1-C10nitroalkil, C1-C10aminoalkil, C1-C5alkilaminoC1-C5alkil, C2-C8dialkilaminoC1-C5alkil, C3-C7cikloalkilC1-C5alkil, C1-C5alkoksiC1-C5alkil, C3-C5alkeniloksiC1-C5alkil, C3-C5alkiniloksiC1-C5alkil, C1-C5alkiltioC1-C5alkil, C1-C5alkilsulfinilC1-C5alkil, C1-C5alkilsulfonilC1-C5alkil, C2-C8alkilidenaminoksiC1-C5alkil, C1-C5alkilkarbonilC1-C5alkil, C1-C5alkoksikarbonilC1-C5alkil, aminokarbonilC1-C5alkil, C1-C5alkilaminokarbonilC1-C5alkil, C2-C8dialkilaminokarbonilC1-C5alkil, C1-C5alkilkarbonilaminoC1-C5alkil, N-C1-C5alkilkarbonil-N-C2-C5alkilaminoalkil, C3-C6trialkilsililC1-C5alkil, fenilC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), heteroarilC1-C5alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C30alkilsulfinil, C1-C3alkilsulfonil, halogen, cijano, ili sa nitro), C2-C5haloalkenil, C3-C8cikloalkil; fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; heteroaril ili heteroaril supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro;
heteroarilamino ili heteroarilamino supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; diheteroarilamino ili diheteroarilamino supstituiran sa C1-C3 alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; fenilamino ili fenilamino supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro;
difenilamino ili difenilamino supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; ili C3-C7cikloalkilamino, diC3-C7cikloalkilamino, C3-C7cikloalkoksi, C1-C10haloalkoksi, C1-C5alkilamino ili C2-C8dialkilamino;
ili benziloksi ili fenoksi gdje benzil i fenil skupina mogu u povratu biti supstituirane sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro; a
Rh je C1-C10alkil, C3-C10alkenil, C3-C10alkinil, C1-C10haloalkil, C1-C10cijanoalkil, C1-C10nitroalkil, C2-C10aminoalkil, C1-C5alkilaminoC1-C5alkil, C2-C8dialkilamino-C1-C5alkil, C3-C7cikloalkilC1-C5alkil, C1-C5alkoksiC1-C5alkil, C3-C5alkeniloksiC1-C5alkil, C3-C5alkiniloksiC1-C5alkil, C1-C5alkiltioC1-C5alkil, C1-C5alkilsulfinilC1-C5alkil, C1-C5alkilsulfonilC1-C5alkil, C2-C8alkilidenaminoksiC1-C5alkil, C1-C5alkilkarbonilC1-C5alkil, C1-C5 alkoksikarbonilC1-C5alkil, aminokarbonilC1-C5alkil, C1-C5alkilaminokarbonilC1-C5alkil, C2-C8dialkilaminokarbonilC1-C5alkil, C1-C5alkilkarbonilaminoC1-C5alkil, N-C1-C5alkilkarbonil-N-C1-C5alkilaminoC1-C5alkil, C3-C6trialkilsililC1-C5alkil, fenilC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), heteroarilC1-C5alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), fenoksiC1-C5alkil (gdje je fenil opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), heteroariloksiC1-C5alkil (gdje je heteroaril opcijski supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, C1-C3alkiltio, C1-C3alkilsulfinil, C1-C3 alkilsulfonil, halogen, cijano ili sa nitro), C3-C5haloalkenil, C3-C8cikloalkil; fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen ili nitro; ili heteroaril ili heteroaril supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, halogen, cijano ili nitro.
2. Spoj prema zahtjevu 1, naznačen time, da
R1 je metil, etil, vinil, etilnil, metoksi ili halogen.
3. Spoj prema zahtjevu 2, naznačen time, da
R1 je metil ili etil.
4. Spoj prema zahtjevu 1, 2 ili 3, naznačen time, da
R2je vodik, halogen, metil, etil, fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil.
5. Spoj prema zahtjevu 4, naznačen time, da
R2je vodik ili metil.
6. Spoj prema zahtjevu 1, 2 ili 3, naznačen time, da
R3je vodik, halogen, metil, etil, fenil ili fenil supstituiran sa C1-C3alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil.
7. Spoj prema zahtjevu 6, naznačen time, da
R3je vodik ili fenil supstituiran sa halogen.
8. Spoj prema zahtjevu 1, 2 ili 3, naznačen time, da
R2i R3 su neovisno vodik, metil, etil, halogen; fenil opcijski supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil; ili heteroaril opcijski supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro, halogen, C1-C3alkiltio, C1-C3alkilsulfinil ili C1-C3alkilsulfonil.
9. Spoj prema zahtjevu 1, 2, 3 ili 8, naznačen time, da
R4 je vodik, metil, etil, vinil ili etilnil.
10. Spoj prema zahtjevu 9, naznačen time, da
R4 je vodik, metil ili etil.
11. Spoj prema zahtjevu 1, 2, 3, 8, 9 ili 10, naznačen time, da
R1, R2 i R4 su neovisno jedan od drugoga metil ili etil, a R3 je vodik.
12. Spoj prema zahtjevu 1, naznačen time, da
R1je metil ili etil, R2 je vodik, a R3 je fenil ili fenil supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro ili halogen; ili heteroaril ili heteroaril supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3 haloalkoksi, cijano, nitro ili halogen.
13. Spoj prema zahtjevu 1, naznačen time, da
R1 je metil ili etil,
R2 je fenil ili fenil supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi,
C1-C3haloalkoksi, cijano, nitro ili halogen; ili heteroaril ili heteroaril supstituiran sa C1-C4alkil, C1-C3haloalkil, C1-C3alkoksi, C1-C3haloalkoksi, cijano, nitro ili halogen,
R3 je vodik, i
R4 je vodik, metil ili etil.
14. Spoj prema bilo kojem zahtjevu 1 do 3 ili 8 do 13, naznačen time, da
R5 je vodik.
15. Spoj prema bilo kojem zahtjevu 1 do 3 ili 8 do 14, naznačen time, da
R6 je vodik.
16. Spoj prema bilo kojem zahtjevu 1 do 3 ili 8 do 15, naznačen time, da
R7i R8 su neovisno jedan od drugoga metilen, etilen, propilen ili propenilen.
17. Spoj prema zahtjevu 16, naznačen time, da
R7i R8 su etilen.
18. Spoj prema bilo kojem zahtjevu 1 do 3 ili 8 do 17, naznačen time, da
latentna skupina G je C(Xa)-Ra ili C (Xb)-Xc-Rb, a značenja od Xa, Ra, Xb, Xc i Rb su određena za njih u zahtjevu 1.
19. Spoj prema bilo kojem zahtjevu 1 do 3 ili 8 do 17, naznačen time, da
G je vodik, alkalijski metal ili alkalijski zemni metal.
20. Spoj prema zahtjevu 19, naznačen time, da
G je vodik.
21. Spoj prema bilo kojem zahtjevu 1 do 3 ili 8 do 20, naznačen time, da
X je O ili S.
22. Spoj prema bilo kojem zahtjevu 1 do 3 ili 8 do 20, naznačen time, da
X je S(O) ili S(O)2.
23. Postupak priprave spoja formule (I) prema zahtjevu 1, pri čemu G je vodik, naznačen time, da
obuhvaća reakciju spoja formule (Z)
[image]
gdje R6, R7, R8 i X imaju značenja koja su im naznačena u zahtjevu 1, a Ar je opcijski supstituirana fenilna skupina sa aril boronskom kiselinom formule (AA)
[image]
gdje R1, R2, R3 i R4 imaju značenja koja su im naznačena u zahtjevu 1, u prisutnosti paladij katalizatora i baze.
24. Postupak priprave spoja formule (I) prema zahtjevu 1, pri čemu G je vodik, naznačen time, da
obuhvaća ciklizaciju spoja formule (B)
[image]
gdje R1, R2, R3, R4, R5, R6, R7, R8 i X imaju značenja koja su ima naznačena u zahtjevu 1, a R je alkil, pod kiselim uvjetima ili u bazičnim okolnostima.
25. Postupak priprave spoja formule (I) prema zahtjevu 1, pri čemu G je alkil, acil, fosforil ili sulfonil skupina, naznačen time, da
obuhvaća tretiranje spoja formule (A)
[image]
gdje R1, R2, R3, R4, R5, R6, R7, R8 i X imaju značenja koja su im naznačena u zahtjevu 1, sa spojem formule G -Y, gdje G predstavlja alkil, acil, fosforil ili sulfonil skupinu koja se treba pripojiti, a Y je pogodna nukleofuga, u prisutnosti barem jednog ekvivalenta baze.
26. Postupak priprave spoja formule (I) prema zahtjevu 1, pri čemu G je vodik, naznačen time, da
obuhvaća ciklizaciju spoja formule (B)
[image]
gdje R1, R2, R3, R4, R5, R6, R7, R8 i X imaju značenja koja su im naznačena u zahtjevu 1, a R je vodik, u kiselim uvjetima.
27. Postupak priprave spoja formule (I) prema zahtjevu 1, pri čemu G je C1-C4 alkil, a R5, R6, R7 i R8imaju značenja koja su im naznačena u zahtjevu 1, naznačen time, da
obuhvaća tretiranje spoja formule (KK)
[image]
gdje G je C1-C4alkil, Hal je klor, brom ili jod, s aril boronskom kiselinom formule (AA)
[image]
gdje R1, R2, R3 i R4 imaju značenja koja su im naznačena u zahtjevu 1, u prisutnosti baze, otapala i paladij katalizatora.
28. Postupak priprave spoja formule (I) prema zahtjevu 1, pri čemu G je H, naznačen time, da obuhvaća hidrolizu spoja formule (I) pri čemu G je C1-C4 alkil u kiselim uvjetima.
29. Postupak suzbijanja trava i korova u prinosima usjeva korisnih biljaka, naznačen time, da obuhvaća primjenu herbicidno učinkovite količine spoja formule (I) koji je određen u bilo kojem zahtjevu 1 do 22, ili sastava koji sadrži takav spoj, na biljke ili na mjesto usjeva.
30. Herbicidni sastav, naznačen time, da dodatno uz sadržaj formulacijskih pomoćnih sredstava, obuhvaća herbicidno učinkovitu količinu spoja formule (I) koji je određen u bilo kojem zahtjevu 1 do 22.
31. Sastav, prema zahtjevu 30, naznačen time, da dodatno uz sadržaj spoja formule (I) obuhvaća neki drugi herbicid za sudjelovanje u mješavini.
32. Sastav, prema zahtjevu 30, naznačen time, da dodatno uz sadržaj spoja formule (I) obuhvaća i neškodljivo zaštitno sredstvo.
33. Sastav, prema zahtjevu 30, naznačen time, da dodatno uz sadržaj spoja formule (I) obuhvaća neki drugi herbicid za sudjelovanje u mješavini i zaštitno sredstvo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0704653.5A GB0704653D0 (en) | 2007-03-09 | 2007-03-09 | Novel herbicides |
| PCT/EP2008/001840 WO2008110307A1 (en) | 2007-03-09 | 2008-03-07 | 2-aryl-5-heterocyclyl-cyclohexane-1,3-dione compounds and their use as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110592T1 true HRP20110592T1 (hr) | 2011-09-30 |
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| HR20110592T HRP20110592T1 (hr) | 2007-03-09 | 2011-08-10 | Spojevi 2-aril-5-heteroaril-cikloheksan-1,3-diona i njihova uporaba kao herbicida |
Country Status (19)
| Country | Link |
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| US (1) | US8536351B2 (hr) |
| EP (1) | EP2134699B1 (hr) |
| JP (1) | JP5457200B2 (hr) |
| KR (1) | KR20090119991A (hr) |
| CN (1) | CN101730688B (hr) |
| AR (1) | AR065649A1 (hr) |
| AT (1) | ATE509016T1 (hr) |
| AU (1) | AU2008226073B2 (hr) |
| BR (1) | BRPI0808683B1 (hr) |
| CA (1) | CA2679343C (hr) |
| CO (1) | CO6210770A2 (hr) |
| DK (1) | DK2134699T3 (hr) |
| ES (1) | ES2366596T3 (hr) |
| GB (1) | GB0704653D0 (hr) |
| HR (1) | HRP20110592T1 (hr) |
| PL (1) | PL2134699T3 (hr) |
| PT (1) | PT2134699E (hr) |
| RU (1) | RU2009136668A (hr) |
| WO (1) | WO2008110307A1 (hr) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2102181B1 (en) * | 2006-12-14 | 2014-06-18 | Syngenta Participations AG | 4-phenyl-pyrane-3,5-diones, 4-phenyl-thiopyrane-3,5-diones and cyclohexanetriones as novel herbicides |
| GB0704652D0 (en) * | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| GB0710223D0 (en) * | 2007-05-29 | 2007-07-11 | Syngenta Ltd | Novel Herbicides |
| GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
| GB0714981D0 (en) | 2007-08-01 | 2007-09-12 | Syngenta Ltd | Novel herbicides |
| GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| EA020918B1 (ru) | 2007-12-13 | 2015-02-27 | Зингента Лимитед | 4-фенилпиран-3,5-дионы, 4-фенилтиопиран-3,5-дионы и 2-фенилциклогексан-1,3,5-трионы в качестве гербицидов |
| GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
| GB0819205D0 (en) * | 2008-10-20 | 2008-11-26 | Syngenta Ltd | Novel herbicides |
| GB0822834D0 (en) | 2008-12-15 | 2009-01-21 | Syngenta Ltd | Novel herbicides |
| GB0900641D0 (en) | 2009-01-15 | 2009-02-25 | Syngenta Ltd | Novel herbicides |
| WO2010081687A1 (en) * | 2009-01-19 | 2010-07-22 | Bayer Cropscience Ag | Use of 2-aryl-5-heterocyclyl-cyclohexane-l,3-dione compounds as insecticides, acaricides and / or fungicides |
| GB0901086D0 (en) | 2009-01-22 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901834D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901835D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| ES2632567T3 (es) | 2009-03-11 | 2017-09-14 | Bayer Intellectual Property Gmbh | Cetoenoles sustituidos con haloalquilmetilenoxi-fenilo |
| BR112012001160A2 (pt) * | 2009-07-17 | 2016-03-01 | Syngenta Ltd | compostos herbicidas, seu processo de preparação, composição herbicida, e método para controle de gramíneas e ervas daninhas em culturas de plantas úteis |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| BR112012030473A2 (pt) * | 2010-05-31 | 2015-09-29 | Syngenta Participations Ag | pesticidas baseados em derivados pirrolidina espiroheterocíclicos |
| UA113753C2 (xx) | 2012-01-26 | 2017-03-10 | Фенілзаміщені кетоеноли для боротьби з паразитами риб | |
| US9615577B2 (en) * | 2012-12-21 | 2017-04-11 | Syngenta Limited | Herbicidally active cyclic dione compounds, or derivatives therefor, substituted by a phenyl which has an alkynyl-containing substituent |
| BR112015029940B1 (pt) * | 2013-05-30 | 2021-08-17 | Syngenta Limited | Compostos de dionas cíclicas substituídas com alquinilfenil e seus derivados, composição herbicida compreendendo os referidos compostos e método de controle de ervas daninhas de gramíneas monocotiledôneas |
| GB201411418D0 (en) * | 2014-06-26 | 2014-08-13 | Syngenta Participations Ag | Compounds |
| CN110734386A (zh) * | 2019-10-28 | 2020-01-31 | 新乡市锦源化工有限公司 | 一种对氨基乙酰苯胺的制备方法 |
| CN113121341A (zh) * | 2019-12-31 | 2021-07-16 | 江苏中旗科技股份有限公司 | 一种合成2,6-二乙基-4-甲基苯乙酸酯的方法 |
| CN113754613B (zh) * | 2021-09-27 | 2023-06-30 | 北京工商大学 | 一种4-烯醇的苯硫基环醚化方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4659372A (en) * | 1977-03-28 | 1987-04-21 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds |
| US4256659A (en) * | 1977-03-28 | 1981-03-17 | Union Carbide Corporation | Method of preparing 2-aryl-1,3-cyclohexanedione compounds |
| US4409153A (en) * | 1980-03-28 | 1983-10-11 | Union Carbide Corporation | O-(2-Aryl-3-oxo-1-cyclohexenyl) phosphates |
| US4351666A (en) * | 1980-06-27 | 1982-09-28 | Union Carbide Corporation | Enol derivatives of 2-aryl-1,3-cyclohexanedione compound as sugar enhancer for plants |
| ZW12488A1 (en) * | 1987-09-25 | 1988-11-23 | Chevron Res | 2-/1-(5-halothienylmethoxyimino)ethyl/-3-hydroxy-5-(tetrahydro-2h-thiopyranyl)-cyclohex-2-en-1-one and derivatives thereof and their use as selective herbicides and to control lateral buds in tobacco plants |
| JPH02726A (ja) * | 1987-11-28 | 1990-01-05 | Nippon Soda Co Ltd | シクロヘキセノン誘導体、その製造方法及び除草剤 |
| ATE109458T1 (de) * | 1990-10-19 | 1994-08-15 | Basf Ag | Ungesättigte cyclohexenonoximether. |
| DE10016544A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
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2007
- 2007-03-09 GB GBGB0704653.5A patent/GB0704653D0/en not_active Ceased
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2008
- 2008-03-07 BR BRPI0808683A patent/BRPI0808683B1/pt not_active IP Right Cessation
- 2008-03-07 CN CN2008800137859A patent/CN101730688B/zh not_active Expired - Fee Related
- 2008-03-07 ES ES08716354T patent/ES2366596T3/es active Active
- 2008-03-07 CA CA2679343A patent/CA2679343C/en not_active Expired - Fee Related
- 2008-03-07 RU RU2009136668/04A patent/RU2009136668A/ru not_active Application Discontinuation
- 2008-03-07 AU AU2008226073A patent/AU2008226073B2/en not_active Ceased
- 2008-03-07 WO PCT/EP2008/001840 patent/WO2008110307A1/en active Application Filing
- 2008-03-07 JP JP2009552127A patent/JP5457200B2/ja not_active Expired - Fee Related
- 2008-03-07 DK DK08716354.9T patent/DK2134699T3/da active
- 2008-03-07 PL PL08716354T patent/PL2134699T3/pl unknown
- 2008-03-07 US US12/530,476 patent/US8536351B2/en not_active Expired - Fee Related
- 2008-03-07 PT PT08716354T patent/PT2134699E/pt unknown
- 2008-03-07 KR KR1020097021081A patent/KR20090119991A/ko not_active Application Discontinuation
- 2008-03-07 AR ARP080100955A patent/AR065649A1/es active IP Right Grant
- 2008-03-07 EP EP08716354A patent/EP2134699B1/en not_active Not-in-force
- 2008-03-07 AT AT08716354T patent/ATE509016T1/de active
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Also Published As
| Publication number | Publication date |
|---|---|
| ATE509016T1 (de) | 2011-05-15 |
| PL2134699T3 (pl) | 2011-10-31 |
| PT2134699E (pt) | 2011-08-25 |
| BRPI0808683A2 (pt) | 2014-08-12 |
| EP2134699A1 (en) | 2009-12-23 |
| CO6210770A2 (es) | 2010-10-20 |
| US8536351B2 (en) | 2013-09-17 |
| WO2008110307A1 (en) | 2008-09-18 |
| CA2679343C (en) | 2015-09-29 |
| EP2134699B1 (en) | 2011-05-11 |
| AR065649A1 (es) | 2009-06-24 |
| CN101730688B (zh) | 2012-06-20 |
| RU2009136668A (ru) | 2011-04-20 |
| GB0704653D0 (en) | 2007-04-18 |
| US20100113270A1 (en) | 2010-05-06 |
| ES2366596T3 (es) | 2011-10-21 |
| CN101730688A (zh) | 2010-06-09 |
| AU2008226073A1 (en) | 2008-09-18 |
| JP5457200B2 (ja) | 2014-04-02 |
| KR20090119991A (ko) | 2009-11-23 |
| DK2134699T3 (da) | 2011-08-29 |
| CA2679343A1 (en) | 2008-09-18 |
| JP2010520866A (ja) | 2010-06-17 |
| BRPI0808683B1 (pt) | 2016-07-19 |
| AU2008226073B2 (en) | 2014-01-23 |
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