EP3986877A1 - Hydroxyisoxazoline und derivate davon - Google Patents
Hydroxyisoxazoline und derivate davonInfo
- Publication number
- EP3986877A1 EP3986877A1 EP20733959.9A EP20733959A EP3986877A1 EP 3986877 A1 EP3986877 A1 EP 3986877A1 EP 20733959 A EP20733959 A EP 20733959A EP 3986877 A1 EP3986877 A1 EP 3986877A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- halo
- trifluoromethyl
- phenyl
- oxazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical class OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 134
- -1 Ci-Cs-alkyl Chemical group 0.000 claims description 269
- 150000001875 compounds Chemical class 0.000 claims description 221
- 238000000034 method Methods 0.000 claims description 77
- 125000005843 halogen group Chemical group 0.000 claims description 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000002015 acyclic group Chemical group 0.000 claims description 34
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 241000233866 Fungi Species 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 125000001544 thienyl group Chemical group 0.000 claims description 26
- 229910052801 chlorine Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 23
- 239000011737 fluorine Chemical group 0.000 claims description 22
- 230000003032 phytopathogenic effect Effects 0.000 claims description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 19
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 235000013399 edible fruits Nutrition 0.000 claims description 18
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000002541 furyl group Chemical group 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 17
- 125000000335 thiazolyl group Chemical group 0.000 claims description 17
- 125000001425 triazolyl group Chemical group 0.000 claims description 17
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 16
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 7
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- XRJFLLYLWDDKBG-UHFFFAOYSA-N C(C)N1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound C(C)N1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F XRJFLLYLWDDKBG-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- BYXRARLLIMWPKT-UHFFFAOYSA-N C(C)N1N=CC=C1C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound C(C)N1N=CC=C1C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F BYXRARLLIMWPKT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- UJTPUTHEMDDPEO-UHFFFAOYSA-N CC1=NOC(=C1C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F)C Chemical compound CC1=NOC(=C1C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F)C UJTPUTHEMDDPEO-UHFFFAOYSA-N 0.000 claims description 2
- GVSOAIIMVAPOKT-UHFFFAOYSA-N CC=1N(C(=CC=1)C)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound CC=1N(C(=CC=1)C)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F GVSOAIIMVAPOKT-UHFFFAOYSA-N 0.000 claims description 2
- GHNGJIJZUAQLAY-UHFFFAOYSA-N CN1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound CN1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F GHNGJIJZUAQLAY-UHFFFAOYSA-N 0.000 claims description 2
- SDKWDAKIEMFGEC-UHFFFAOYSA-N CN1N=CC=C1C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound CN1N=CC=C1C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F SDKWDAKIEMFGEC-UHFFFAOYSA-N 0.000 claims description 2
- SQZPPYRMRDKUKK-UHFFFAOYSA-N ClC=1N(C(=CN=1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F)C Chemical compound ClC=1N(C(=CN=1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F)C SQZPPYRMRDKUKK-UHFFFAOYSA-N 0.000 claims description 2
- JFTBRTXHTYTVKY-UHFFFAOYSA-N FC=1C=C(C=CC=1N1C=NC=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound FC=1C=C(C=CC=1N1C=NC=C1)C1=NOC(C1)(O)C(F)(F)F JFTBRTXHTYTVKY-UHFFFAOYSA-N 0.000 claims description 2
- VQWQPDMMPUVHJW-UHFFFAOYSA-N N1N=C(C=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound N1N=C(C=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F VQWQPDMMPUVHJW-UHFFFAOYSA-N 0.000 claims description 2
- IAXRWBGZPIQYMJ-UHFFFAOYSA-N N1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F IAXRWBGZPIQYMJ-UHFFFAOYSA-N 0.000 claims description 2
- FZBXHYOFOPCZPE-UHFFFAOYSA-N O1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F Chemical compound O1N=CC(=C1)C1=CC=C(C=C1)C1=NOC(C1)(O)C(F)(F)F FZBXHYOFOPCZPE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 abstract description 28
- 241000196324 Embryophyta Species 0.000 description 179
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 238000012360 testing method Methods 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- 201000010099 disease Diseases 0.000 description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- 230000008569 process Effects 0.000 description 28
- 239000004480 active ingredient Substances 0.000 description 26
- 244000005700 microbiome Species 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000003112 inhibitor Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 238000009472 formulation Methods 0.000 description 18
- 150000003254 radicals Chemical group 0.000 description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
- 241000894120 Trichoderma atroviride Species 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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- 229950007146 tigolaner Drugs 0.000 description 1
- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- C07D413/10—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 carbon chain containing aromatic rings
-
- 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
- C07D261/08—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19181796 | 2019-06-21 | ||
| PCT/EP2020/066932 WO2020254487A1 (en) | 2019-06-21 | 2020-06-18 | Hydroxyisoxazolines and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP3986877A1 true EP3986877A1 (de) | 2022-04-27 |
Family
ID=67001695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP20733959.9A Withdrawn EP3986877A1 (de) | 2019-06-21 | 2020-06-18 | Hydroxyisoxazoline und derivate davon |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP3986877A1 (de) |
| AR (1) | AR119200A1 (de) |
| BR (1) | BR112021025700A2 (de) |
| TW (1) | TW202115049A (de) |
| UY (1) | UY38762A (de) |
| WO (1) | WO2020254487A1 (de) |
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| DE3639877A1 (de) | 1986-11-21 | 1988-05-26 | Bayer Ag | Hetarylalkyl substituierte 5- und 6-ringheterocyclen |
| KR100616372B1 (ko) | 1997-05-09 | 2006-08-28 | 아그라퀘스트 인코퍼레이티드 | 식물병들과 옥수수 근벌레를 억제하기 위한 신규한Ｂａｃｉｌｌｕｓ 균주 |
| EP0998468A1 (de) | 1997-07-23 | 2000-05-10 | Basf Aktiengesellschaft | Substituierte 3-phenylisoxazoline |
| US6245551B1 (en) | 1999-03-30 | 2001-06-12 | Agraquest, Inc. | Strain of Bacillus pumilus for controlling plant diseases caused by fungi |
| JP4071036B2 (ja) | 2001-11-26 | 2008-04-02 | クミアイ化学工業株式会社 | バシルスｓｐ．Ｄ７４７菌株およびそれを用いた植物病害防除剤および害虫防除剤 |
| GB0213715D0 (en) | 2002-06-14 | 2002-07-24 | Syngenta Ltd | Chemical compounds |
| TWI312272B (en) | 2003-05-12 | 2009-07-21 | Sumitomo Chemical Co | Pyrimidine compound and pests controlling composition containing the same |
| GB0414438D0 (en) | 2004-06-28 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| EP1794167A4 (de) | 2004-09-10 | 2009-10-21 | Syngenta Ltd | Substituierte isoxazole als fungizide |
| RU2394819C2 (ru) | 2004-10-20 | 2010-07-20 | Кумиай Кемикал Индастри Ко., Лтд. | Инсектицид, акарицид и нематоцид, содержащие в качестве активного компонента производное 3-триазолилфенилсульфида |
| EA014057B1 (ru) | 2005-10-06 | 2010-08-30 | Ниппон Сода Ко., Лтд. | Поперечно связанные соединения циклических аминов и средства для борьбы с вредителями |
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| WO2009051956A2 (en) | 2007-10-16 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Pyrazole-substituted isoxazoline insecticides |
| JP5268461B2 (ja) | 2008-07-14 | 2013-08-21 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | Ｐｆ１３６４物質、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤 |
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| EP2184273A1 (de) | 2008-11-05 | 2010-05-12 | Bayer CropScience AG | Halogen-substituierte Verbindungen als Pestizide |
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| CN103524422B (zh) | 2013-10-11 | 2015-05-27 | 中国农业科学院植物保护研究所 | 苯并咪唑衍生物及其制备方法和用途 |
| EP3057430A4 (de) | 2013-10-17 | 2017-09-13 | Dow AgroSciences LLC | Verfahren zur herstellung von pestizidverbindungen |
| CN105636440A (zh) | 2013-10-17 | 2016-06-01 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| JP2017078022A (ja) | 2014-02-28 | 2017-04-27 | クミアイ化学工業株式会社 | イソキサゾール誘導体及びそれを用いた農園芸用植物病害防除剤 |
| TW201613866A (en) | 2014-07-07 | 2016-04-16 | Bayer Cropscience Ag | Process for preparing fluorinated iminopyridine compounds |
| EP3259992B1 (de) | 2015-02-17 | 2019-01-02 | Nippon Soda Co., Ltd. | Agrochemische zusammensetzungen |
| EP3838914A1 (de) | 2015-03-26 | 2021-06-23 | Bayer Cropscience LP | Paenibacillus-stamm, antimykotische verbindungen und verfahren zu deren verwendung |
| US20210084900A1 (en) | 2017-05-04 | 2021-03-25 | Basf Se | Substituted 5-(haloalkyl)-5-hydroxy-isoxazoles for Combating Phytopathogenic Fungi |
| BR112020003266A2 (pt) | 2017-08-17 | 2020-10-13 | Bayer Aktiengesellschaft | 3-fenil-5-trifluorometilisoxazolina-5-carboxamidas herbicidamente ativas de ésteres e ácidos ciclopentilcarboxílicos |
| AU2018390964A1 (en) | 2017-12-22 | 2020-07-02 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
-
2020
- 2020-06-18 BR BR112021025700A patent/BR112021025700A2/pt unknown
- 2020-06-18 WO PCT/EP2020/066932 patent/WO2020254487A1/en active Application Filing
- 2020-06-18 EP EP20733959.9A patent/EP3986877A1/de not_active Withdrawn
- 2020-06-19 AR ARP200101738A patent/AR119200A1/es unknown
- 2020-06-19 TW TW109120765A patent/TW202115049A/zh unknown
- 2020-06-22 UY UY0001038762A patent/UY38762A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112021025700A2 (pt) | 2022-02-08 |
| AR119200A1 (es) | 2021-12-01 |
| WO2020254487A1 (en) | 2020-12-24 |
| UY38762A (es) | 2021-01-29 |
| TW202115049A (zh) | 2021-04-16 |
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