US20110251069A1 - Isoxazole derivatives for use as plant growth regulators - Google Patents
Isoxazole derivatives for use as plant growth regulators Download PDFInfo
- Publication number
- US20110251069A1 US20110251069A1 US13/140,774 US200913140774A US2011251069A1 US 20110251069 A1 US20110251069 A1 US 20110251069A1 US 200913140774 A US200913140774 A US 200913140774A US 2011251069 A1 US2011251069 A1 US 2011251069A1
- Authority
- US
- United States
- Prior art keywords
- alkyl
- haloalkyl
- alkynyl
- alkenyl
- halogen
- 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.)
- Abandoned
Links
- 239000005648 plant growth regulator Substances 0.000 title description 17
- 150000002545 isoxazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 327
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 230000008635 plant growth Effects 0.000 claims abstract description 21
- 230000001105 regulatory effect Effects 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 208
- 125000001188 haloalkyl group Chemical group 0.000 claims description 200
- 229910052736 halogen Inorganic materials 0.000 claims description 187
- 125000003342 alkenyl group Chemical group 0.000 claims description 175
- 125000000304 alkynyl group Chemical group 0.000 claims description 174
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 174
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 172
- 125000003545 alkoxy group Chemical group 0.000 claims description 169
- 125000004414 alkyl thio group Chemical group 0.000 claims description 167
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 166
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 163
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 163
- 125000005843 halogen group Chemical group 0.000 claims description 136
- 241000196324 Embryophyta Species 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 34
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 28
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 25
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 235000013339 cereals Nutrition 0.000 claims description 9
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
- 125000005252 haloacyl group Chemical group 0.000 claims description 6
- 241000209504 Poaceae Species 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 235000016068 Berberis vulgaris Nutrition 0.000 claims description 4
- 241000335053 Beta vulgaris Species 0.000 claims description 4
- 240000008067 Cucumis sativus Species 0.000 claims description 4
- BLJUKUYABALEQD-UHFFFAOYSA-N [4-(2-chlorophenyl)-2-(2,4-difluorophenyl)thiophen-3-yl]-pyridin-3-ylmethanol Chemical compound C=1C=CN=CC=1C(O)C=1C(C=2C(=CC=CC=2)Cl)=CSC=1C1=CC=C(F)C=C1F BLJUKUYABALEQD-UHFFFAOYSA-N 0.000 claims description 4
- 235000014749 Mentha crispa Nutrition 0.000 claims description 3
- 244000246386 Mentha pulegium Species 0.000 claims description 3
- 235000016257 Mentha pulegium Nutrition 0.000 claims description 3
- 235000004357 Mentha x piperita Nutrition 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 244000299790 Rheum rhabarbarum Species 0.000 claims description 3
- 235000009411 Rheum rhabarbarum Nutrition 0.000 claims description 3
- 240000000111 Saccharum officinarum Species 0.000 claims description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 3
- 240000001717 Vaccinium macrocarpon Species 0.000 claims description 3
- 235000021019 cranberries Nutrition 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 235000001050 hortel pimenta Nutrition 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 244000038559 crop plants Species 0.000 claims 2
- 244000024873 Mentha crispa Species 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 116
- 229930192474 thiophene Natural products 0.000 abstract description 61
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 51
- 150000003233 pyrroles Chemical class 0.000 abstract description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 82
- -1 phenylacetyl Chemical group 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- 150000002367 halogens Chemical class 0.000 description 53
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 48
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 235000002639 sodium chloride Nutrition 0.000 description 27
- 0 *C1=C([1*])C(C([2*])O[4*])=C([3*])C1 Chemical compound *C1=C([1*])C(C([2*])O[4*])=C([3*])C1 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 15
- 239000012442 inert solvent Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 244000045561 useful plants Species 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000012280 lithium aluminium hydride Substances 0.000 description 10
- 125000002524 organometallic group Chemical group 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 125000004076 pyridyl group Chemical group 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- VSCRGDVBLMBOIZ-UHFFFAOYSA-N [4-(4-chlorophenyl)-2-(5-chlorothiophen-2-yl)thiophen-3-yl]-pyridin-3-ylmethanol Chemical compound C=1C=CN=CC=1C(O)C=1C(C=2C=CC(Cl)=CC=2)=CSC=1C1=CC=C(Cl)S1 VSCRGDVBLMBOIZ-UHFFFAOYSA-N 0.000 description 8
- 239000002274 desiccant Substances 0.000 description 8
- 230000000855 fungicidal effect Effects 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 229910010084 LiAlH4 Inorganic materials 0.000 description 7
- CYCBSHZUFMQBNA-UHFFFAOYSA-N [2,4-bis(3-chlorophenyl)thiophen-3-yl]-pyridin-3-ylmethanol Chemical compound C=1C=CN=CC=1C(O)C=1C(C=2C=C(Cl)C=CC=2)=CSC=1C1=CC=CC(Cl)=C1 CYCBSHZUFMQBNA-UHFFFAOYSA-N 0.000 description 7
- 230000000895 acaricidal effect Effects 0.000 description 7
- 239000000642 acaricide Substances 0.000 description 7
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 239000003899 bactericide agent Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000000417 fungicide Substances 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000005645 nematicide Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 241000482268 Zea mays subsp. mays Species 0.000 description 6
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- 239000012043 crude product Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000011593 sulfur Chemical group 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- LWCKBCGXMDMADT-UHFFFAOYSA-N [2-(3-chlorophenyl)-4,5-dimethylthiophen-3-yl]-pyridin-3-ylmethanol Chemical compound CC1=C(C)SC(C=2C=C(Cl)C=CC=2)=C1C(O)C1=CC=CN=C1 LWCKBCGXMDMADT-UHFFFAOYSA-N 0.000 description 5
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- 125000002541 furyl group Chemical group 0.000 description 5
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 4
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229960002622 triacetin Drugs 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-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
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-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
- 238000009834 vaporization Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011787 zinc oxide Substances 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
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- C07D413/02—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
- C07D413/06—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 only aliphatic carbon atoms
Definitions
- the present invention relates to thiophene, furan and pyrrole compounds having plant growth regulating properties, to agricultural compositions comprising them, and to the use of said compounds for regulating plant growth.
- Plant growth regulators are generally any substances or mixtures of substances intended to accelerate or retard the rate of growth or maturation, or otherwise alter the development of plants or their produce. PGRs affect growth and differentiation of plants, a process which is commonly and hereinafter referred to as “plant health”. There exists a need for further substances having PGR activity.
- the thiophene, furan and pyrrole compounds of the present invention exhibit plant growth regulating properties and are therefore suitable for use in agriculture for the improvement and control of plant health.
- the present invention provides for the use of a compound of the formula (I)
- Plant growth regulators can, for example, reduce plant height, stimulate seed germination, induce flowering, darken leaf coloring, change the rate of plant growth and modify the timing and efficiency of fruiting.
- PGRs may exhibit pronounced growth-regulating properties which can result in an increase in the yield of cultivated plants or harvested crops.
- PGRs may also have a growth inhibiting action which is dependent on concentration.
- the growth of both monocots and dicots may be inhibited.
- Inhibition of the vegetative growth of many cultivated plants permits more plants to be sown in a crop area, so that a higher yield may be obtained per unit of area.
- Inhibition of the vegetative growth of monocot plants, e.g. cultivated plants such as cereals, is sometimes desirable and advantageous. Such a growth inhibition is of economic interest.
- PGRs for inhibiting the growth in height of cereals is also important, as shortening the stalks diminishes or completely eliminates the danger of lodging before harvesting. Additionally, PGRs are able to bring about a strengthening of the stalks in crops of cereals and this too counteracts lodging.
- compositions comprising the thiophene, furan and pyrrole derivatives of the present invention that improve plants, a process which is commonly and hereinafter referred to as “plant health”.
- advantageous properties are improved crop characteristics including: emergence, crop yield, protein content, increased vigour, faster/delayed maturation, increased speed of seed emergence, improved nutrient utilization efficiency, improved nitrogen utilization efficiency, improved water use efficiency, improved oil content and /or quality, improved digestibility, faster/more even ripening, improved flavor, improved starch content, more developed root system (improved root growth), improved stress tolerance (e.g.
- tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf color, pigment content, photosynthetic activity, less input needed (such as fertilizers or water), less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, enhanced plant vigor, increased plant stand and early and better germination.
- Advantageous properties obtained, especially from treated seeds include, for example, improved germination and field establishment, better vigor and more homogeneous field establishment.
- Advantageous properties obtained, especially from foliar and/or in-furrow application include, for example, improved plant growth and plant development, better growth, more tillers, greener leafes, largers leaves, more biomass, better roots, improved stress tolerance of the plants, more grain yield, more biomass harvested, improved quality of the harvest (content of fatty acids, metabolites, oil etc), more marketable products (e.g. improved size), improved process (e.g. longer shelf-life, better extraction of compounds), improved quality of seeds (for being seeded in the following seasons for seed production); or any other advantages familiar to a person skilled in the art.
- the present invention provides plant-protecting active ingredients that are thiophene, furan and pyrrole compounds of formula (I) according to the invention, in particular the individual thiophene, furan and pyrrole compounds described in the description as being preferred, and mixtures with increased efficacy and to a method of improving the health of plants by applying said compounds and mixtures to the plants or the locus thereof.
- the action of the compounds of formula (I) is separate to any fungicidal action.
- the thiophene, furan and pyrrole compounds of formula (I) according to the invention in particular the individual thiophene, furan and pyrrole compounds described in the above description as being preferred compounds exhibit plant health properties.
- compositions comprising or consisting essentially of an active compound as described herein in combination with a suitable carrier (e.g., an agricultural carrier).
- a suitable carrier e.g., an agricultural carrier
- Alkyl refers to a saturated hydrocarbon radical which may be straight-chain or branched-chain or cyclic (cycloalkyl) and contains from 1 to 24 carbon atoms. This definition applies both when the term is used alone and when it is used as part of a compound term, such as haloalkyl and similar terms.
- Preferred straight chain and branched alkyl groups may contain 1 to 8 carbon atoms, more preferably 1 to 4 carbons, even more preferably, 1 to 4 carbon atoms.
- Representative alkyl groups include, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, t-amyl, and 2,5-dimethylhexyl.
- Preferred cycloalkyl groups may contain 3 to 12 carbon atoms, more preferably 4 to 10 carbons, even more preferably, 5 to 8 carbon atoms and most preferably 5 or 6 carbon atoms.
- Preferred cycloalkyl groups include, for example, cyclobutyl, cyclopropyl, cyclopentyl and cyclohexyl.
- alkenyl refers to a straight or branched chain hydrocarbon containing from 2 to 24 carbons, more preferably 2 to 8 carbons, yet more preferably, 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and containing at least one carbon-carbon double bond.
- Representative alkenyl groups include, for example, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, 2-heptenyl, 2-methyl-1-heptenyl and 3-decenyl.
- Alkynyl refers to a straight or branched chain hydrocarbon group containing from 2 to 24 carbons, more preferably 2 to 8 carbons, yet more preferably, 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and containing at least one carbon-carbon triple bond.
- Representative alkynyl groups include, for example, acetylenyl, 1-propynyl, 2-propynyl, 3-butynyl, 2-pentynyl and 1-butynyl.
- alkoxy groups include, for example, methoxy, ethoxy and t-butoxy.
- alkylthio groups include, for example, methylthio, ethylthio, t-butylthio and hexylthio.
- Aryl refers to an aromatic substituent which may be a single ring or multiple rings which are fused together, linked covalently or linked to a common group such as an ethylene or methylene moiety.
- the aromatic rings may each contain heteroatoms and hence aryl encompasses heteroaryl as used herein.
- Aryl moieties may be optionally substituted with 1 to 4 substituents independently selected from halogen, nitro, alkylcarboxyl, alkoxy and phenoxy.
- aryl include phenyl azulenyl, indanyl, indenyl, naphthyl, tetrahydronaphthyl, biphenyl, diphenylmethyl, 2,2-diphenyl-1-ethyl, thienyl, pyridyl and quinoxalyl. Most preferably, aryl is phenyl.
- Heteroaryl means a cyclic, aromatic hydrocarbon containing 3 to 10 ring-atoms including 1 to 4 heteroatoms independently selected from nitrogen, oxygen and sulfur. Preferred heteroaryl groups are five and six membered rings and contain from one to three heteroatoms independently selected from nitrogen, oxygen and sulphur. Heteroaryl moieties may be optionally substituted with 1 to 4 substituents independently selected from halogen, nitro, alkylcarboxyl, alkoxy and phenoxy.
- heteroaryl groups include furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyranyl, pyridazinyl, tetrazolyl, triazinyl.
- heteroaryl includes fused heteroaryl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl, phthalimido, benzofuranyl, benzodiazepinyl, indolyl, isoindolyl, isobenzofuranyl, chromenyl, xanthenyl, indolizinyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, phthalazinyl, naphthyridinyl and benzo[b]thienyl.
- benzimidazolyl benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazo
- Heterocyclyl refers to a saturated or partially unsaturated cyclic hydrocarbon containing from 3 to 10 ring-atoms up to 4 of which may be hetero-atoms such as nitrogen, oxygen and sulfur.
- heterocyclyl groups are oxiranyl, azetidinyl, tetrahydrofuranyl, thiolanyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl, sulfolanyl, dioxolanyl, dihydropyranyl, tetrahydropyranyl, piperidinyl, pyrazolinyl, pyrazolidinyl, dioxanyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl, azepinyl, oxazepinyl, thiazepinyl, thiazolinyl and diazapanyl.
- Acyl includes any readily hydrolysable acyl groups, and comprises, for example, C(O)R 6 , C(O)OR 6 , C(O)NHR 6 and C(O)NR 6 R 7 , wherein R 6 and R 7 are each independently selected from alkyl, alkenyl, akynyl, heterocyclyl, aryl and heteroaryl.
- Acyl groups may be optionally substituted with one or more, for example 1, 2, 3 or 4, halo or OR 6 groups.
- Preferred acyl groups are acetyl, benzoyl and phenylacetyl.
- Halo or “halogen” means fluoro, chloro, bromo and iodo and is preferably fluoro or chloro.
- Haloalkyl includes monohaloalkyl, polyhaloalkyl and perhaloalkyl, for example, chloromethyl, 2-bromoethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, chlorodifluoromethyl, trichloromethyl, trifluoromethyl, pentafluoroethyl and 2-chloro-3-fluoropentyl.
- Organic base as used herein includes, for example, triethylamine, triisobutylamine, triiooctylamine, triisodecylamine, diethanolamine, triethanolamine, pyridine, morpholine, and mixtures thereof.
- a preferred category of organic base is organic amines.
- Organic base includes, for example, sodium carbonate, sodium bicarbonate, potassium carbonate, and mixtures thereof.
- “Inert solvent” as used herein includes any suitable inert solvent including, for example, tetrahydrofuran, N-methylpyrrolidone, dimethylformamide, toluene, dimethyl ether, methyl t-butyl ether and dioxane, methylene chloride, chloroform, 1,2-dichloroethane, and mixtures thereof.
- Protic solvent as used herein may be any suitable protic solvent including, for example, methanol, ethanol, isopropanol, n-butanol, ethylene glycol, methyl Cellosolve, ethyl Cellosolve, cyclohexanol, glycerol, diethylene glycol, triethanolamine, polyethylene glycol, sec-butanol, n-propanol and tert-butanol.
- Optionally substituted means substituted by one or more substituents, in particular, one, two, three or four substituents. In the case where groups may be selected from a number of alternative groups, the selected groups may be the same or different.
- Agriculturally acceptable salt means a salt the cation of which is known and accepted in the art for the formation of salts for agricultural or horticultural use.
- the salts are water-soluble.
- the compounds of formula (I) may exist in different geometric or optical isomeric forms or in different tautomeric forms.
- One or more centres of chirality may be present, in which case compounds of the formula (I) may be present as pure enantiomers, mixtures of enantiomers, pure diastereomers or mixtures of diastereomers.
- Suitable salts of the compounds of formula (I) include acid addition salts such as those with an inorganic acid such as hydrochloric, hydrobromic, sulphuric, nitric or phosphoric acid, or an organic carboxylic acid such as oxalic, tartaric, lactic, butyric, toluic, hexanoic or phthalic acid, or a sulphonic acid such as methane, benzene or toluene sulphonic acid.
- organic carboxylic acids include haloacids such as trifluoroacetic acid.
- N-oxides are oxidised forms of tertiary amines or oxidised forms of nitrogen containing heteroaromatic compounds. They are described in many books for example in “Heterocyclic N-oxides” by Angelo Albini and Silvio Pietra, CRC Press, Boca Raton, Fla., 1991.
- the present invention provides a method of regulating plant growth of crops of useful plants, which comprises applying to said plants, to one or more parts of said plants, or to the locus thereof or plant propagation material, a compound of formula (I) as defined herein.
- the present invention relates to the use of a compound of the formula (I) as defined herein wherein said compound of formula I is selected from the group consisting of compounds of formula (Ia), compounds of formula (Ib), and compounds of formula (Ic):
- R is H or C 1 -C 8 -alkyl. More preferably, R is H or C 1 -C 4 -alkyl. Most preferably, R is H or methyl.
- R 1 is aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro; or heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro.
- R 1 is aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, phenoxy, cyano, or nitro; or heteroaryl optionally substituted with halogen.
- R 1 is phenyl optionally substituted with halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkoxy, cyano, or nitro; or furanyl, thienyl, pyridyl, or benzothienyl, each optionally substituted with halogen.
- R 1 is 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 4-trifluoro-methylphenyl, 4-trifluoromethoxyphenyl, 2-thienyl, 3-thienyl, 5-chloro-2-thienyl or 5-chloro-2-furyl.
- R 1 is alkyl; or arylalkyl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro.
- R 1 is C 1 -C 6 -alkyl; or arylalkyl optionally substituted with halogen or alkyl.
- R 1 is C 1 -C 6 -alkyl; or phenyl-C 1 -C 6 -alkyl optionally substituted with halogen or C 1 -C 6 -alkyl.
- R 1 is n-pentyl, t-butyl, benzyl or 4-chlorobenzyl.
- R 2 is heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano or nitro.
- R 2 is pyridyl, pyrimidinyl or isoquinolyl, each optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano or nitro.
- R 2 is pyridyl, pyrimidinyl or isoquinolyl, each optionally substituted with halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkoxy, cyano, or nitro.
- R 2 is 2-, 3- or 4-pyridyl or 5-pyrimidinyl, each optionally substituted with halogen, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio.
- R 2 is 2-pyridyl, 3-pyridyl, or 5-pyrimidinyl, each optionally substituted with methyl, chloro, fluoro, methoxy, thiomethoxy or trifluoromethyl.
- R 3 is alkyl; alkoxyalkyl; haloalkyl; arylalkyl optionally substituted with halogen; aryloxyalkyl optionally substituted with halogen; aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, alkoxyalkynyl, cyano or nitro; heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, cyano, or nitro; or alkylsilyl;
- R 3 is alkyl; aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro; heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, nitro; or alkylsilyl
- R 3 is C 1 -C 6 -alkyl; phenyl optionally substituted with halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, cyano or nitro; furanyl, thienyl or pyridyl, each optionally substituted with halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; or C 1 -C 6 -alkylsilyl.
- R 3 is phenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 4-methylphenyl, 2-thienyl, 5-chloro-2-thienyl, 5-methyl-2-thienyl, 3-thienyl, t-butyl or trimethylsilyl.
- R 4 is H, acetyl, benzoyl or phenylacetyl. Most preferably, R 4 is H.
- R 5 is H, alkyl or haloalkyl.
- R 5 is C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl.
- R 5 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl.
- R 5 is methyl.
- Preferred compounds of formula (I) for use according to the methods of the present invention are selected from:
- the present invention provides a method of regulating plant growth of crops of useful plants, which comprises applying to said plants, to one or more parts of said plants, or to the locus thereof or plant propagation material, a compound of formula (I) as defined herein
- the present invention provides a method of regulating plant growth of crops of useful plants, which comprises one or more applications of one of more compounds of formula (I) alone or in conjunction with one or more customary plant protection formulating auxiliaries.
- the present invention provides a method of regulating plant growth of crops of useful plants, which comprises applying to said plants, to one or more parts of said plants, or to the locus thereof or plant propagation material, a compound of formula (I) as defined herein, wherein two or more applications are carried out in sequence, and wherein the two or more applications have the same or different concentration or combinations of compounds as defined herein or both.
- the present invention provides a method of regulating plant growth of crops of useful plants, wherein the crops of useful plants are selected from cereals, rice, beets, leguminous plants, oil plants, cucumber plants, fibre plants, vegetables, plantation crops, ornamentals, vines, bushberries, caneberries, cranberries, peppermint, rhubarb, spearmint, sugar cane and turf grasses.
- crops of useful plants are selected from cereals, rice, beets, leguminous plants, oil plants, cucumber plants, fibre plants, vegetables, plantation crops, ornamentals, vines, bushberries, caneberries, cranberries, peppermint, rhubarb, spearmint, sugar cane and turf grasses.
- the plant growth regulating effect is an inhibition or a retardation of the plant growth.
- the present invention provides an agricultural composition comprising one or more compounds of formula (I) as defined herein and one or more customary plant protection auxiliaries.
- the present invention is directed to the (R)-enantiomers of the compounds of formula (I), designated (R)-(I), wherein X, R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
- Preferred compounds of formula (R)-(I) include the (R)-enantiomers of compounds 1 to 175 of Table 1 herein.
- the present invention provides the compound of formula (R)-(I) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- the present invention is directed to the (S)-enantiomers of the compounds of formula (I), designated (S)-(I), wherein X, R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
- the present invention provides the compound of formula (S)-(I) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- Preferred compounds of formula (S)-(I) include the (S)-enantiomers of compounds 1 to 175 of Table 1 herein.
- the present invention is directed to the (R)-enantiomers of the compounds of formula (la), designated (R)-(Ia), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
- Preferred compounds of formula (R)-(Ia) include the (R)-enantiomers of compounds 1 to 82 and 175 of Table 1 herein.
- the present invention provides the compound of formula (R)-(la) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- the present invention is directed to the (R)-enantiomers of the compounds of formula (Ib), designated (R)-(lb), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
- Preferred compounds of formula (R)-(Ib) include the (R)-enantiomers of compounds 83 to 128 of Table 1 herein.
- the present invention provides the compound of formula (R)-(Ib) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- the present invention is directed to the (R)-enantiomers of the compounds of formula (lc), designated (R)-(lc), wherein R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
- Preferred compounds of formula (R)-(lc) include the (R)-enantiomers of compounds 129 to 174 of Table 1 herein.
- the present invention provides the compound of formula (R)-(lc) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- the present invention is directed to the (S)-enantiomers of the compounds of formula (Ia), designated (S)-(Ia), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
- Preferred compounds of formula (S)-(Ia) include the (S)-enantiomers of compounds 1 to 82 and 175 of Table 1 herein.
- the present invention provides the compound of formula (S)-(Ia) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- the present invention is directed to the (S)-enantiomers of the compounds of formula (Ib), designated (S)-(Ib), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
- Preferred compounds of formula (S)-(Ib) include the (S)-enantiomers of compounds 83 to 128 of Table 1 herein.
- the present invention provides the compound of formula (S)-(Ib) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- the present invention is directed to the (S)-enantiomers of the compounds of formula (Ic), designated (S)-(Ic), wherein R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
- Preferred compounds of formula (S)-(Ic) include the (S)-enantiomers of compounds 129 to 174 of Table 1 herein.
- the present invention provides the compound of formula (S)-(Ic) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- Plant propagation material means the generative parts of a plant including seeds of all kinds (fruit, tubers, bulbs, grains etc), roots, rhizomes, cuttings, cut shoots and the like. Plant propagation material may also include plants and young plants which are to be transplanted after germination or after emergence from the soil.
- Locus means the fields on which the plants to be treated are growing, or where the seeds of cultivated plants are sown, or the place where the seed will be placed into the soil.
- the crops of useful plants to be protected typically comprise, for example, the following species of plants: cereals (wheat, barley, rye, oats, maize (including field corn, pop corn and sweet corn), rice, sorghum and related crops); beet (sugar beet and fodder beet); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, sunflowers); cucumber plants (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); vegetables (spinach, lettuce, asparagus, cabbages, carrots, eggplants, onions, pepper, tomatoes, potatoes, paprika, okra); plantation crops (bananas, fruit trees, rubber trees, tree nurseries), ornamentals (flowers, shrubs, broad-leaved trees and evergreens, such as conifers); as well as other plants such as vines, bushberries (such as blueberries), caneberries, cranberries, peppermint, rhubar
- ryegrasses Lolium L.
- ryegrasses such as perennial ryegrass ( Lolium perenne L.) and annual (Italian) ryegrass ( Lolium multiflorum Lam.)) and warm-season turf grasses ( for example, Bermudagrasses ( Cynodon L. C. Rich), including hybrid and common Bermudagrass; Zoysiagrasses ( Zoysia Willd. ), St. Augustinegrass ( Stenotaphrum secundatum (Walt.) Kuntze); and centipedegrass ( Eremochloa ophiuroides (Munro.) hack.)).
- Bermudagrasses Cynodon L. C. Rich
- Zoysiagrasses Zoysia Willd.
- St. Augustinegrass Stenotaphrum secundatum (Walt.) Kuntze
- centipedegrass Eremochloa ophiuroides (Munro.)
- useful plants also includes useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as HPPD inhibitors, ALS inhibitors; for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
- herbicides like bromoxynil or classes of herbicides
- EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors
- GS glutamine synthetase
- PPO protoporphyrinogen-oxidase
- imazamox by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
- crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
- useful plants also includes useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known from toxin-producing bacteria, especially those of the genus Bacillus.
- useful plants also includes useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as the so-called “pathogenesis-related proteins” (PRPs, see e.g. European patent application EP 0,392,225).
- PRPs pathogenesis-related proteins
- Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from European patent applications EP 0,392,225 and EP 0,353,191, and International patent application WO 95/33818.
- the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
- the agrochemical compositions of the present invention will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula (I), 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
- the agrochemical compositions of the present invention are applied prior to disease development.
- Rates and frequency of use of the formulations are those conventionally used in the art and will depend on factors such as the developmental stage of the plant and on the location, timing and application method.
- Advantageous rates of application are normally from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, most preferably from 20 g to 600 g a.i./ha.
- convenient rates of application are from 10 mg to 1 g of active substance per kg of seeds.
- the agrochemical compositions comprising a compound of formula (I) are applied as a formulation containing the various adjuvants and carriers known to or used in the industry. They may therefore be formulated as granules, wettable or soluble powders, emulsifiable concentrates, coatable pastes, dusts, flowables, solutions, suspensions or emulsions, or as controlled release forms such as microcapsules. These formulations are described in more detail below and may contain from 0.5% to 95% or more by weight of the active ingredient. The optimum amount will depend on formulation, application equipment and nature of the plant to be treated.
- Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
- Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers.
- the particles contain the active ingredient retained in a solid matrix.
- Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
- Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
- Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in treatment is required.
- Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound.
- Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils;
- Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
- Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates.
- Encapsulated droplets are typically 1 to 50 microns in diameter.
- the enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.
- Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
- Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring.
- Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
- compositions for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
- Pressurised sprayers wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.
- Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.
- Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate
- Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
- a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes.
- Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.
- alcohol-alkylene oxide addition products such as tridecyl alcohol-C.sub. 16 ethoxylate
- soaps such as sodium stearate
- alkylnaphthalenesulfonate salts such as sodium dibutylnaphthalenesulfonate
- dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate
- sorbitol esters such as sorbitol oleate
- quaternary amines such as lauryl trimethylammonium chloride
- polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
- salts of mono and dialkyl phosphate esters such as mono and dialkyl phosphate esters.
- adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
- biocidally active ingredients or compositions may be combined with the compound of formula (I) and used in the methods of the invention and applied simultaneously or sequentially with the compound of formula (I). When applied simultaneously, these further active ingredients may be formulated together with the compound of formula (I) or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.
- the present invention provides a composition comprising a compound of formula (I), which is compound 175 of Table 1, and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- the present invention provides for the use of a composition in the methods of the present invention, said composition comprising a compound of formula (I), which is compound 175 of Table 1, and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- a composition comprising a compound of formula (I), which is compound 175 of Table 1, and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- the present invention provides a composition comprising a compound of formula (I), which is the (R)-enantiomer of formula (R)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- a compound of formula (I) which is the (R)-enantiomer of formula (R)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- the present invention provides for the use of a composition in the methods of the present invention, said composition comprising a compound of formula (I), which is the (R)-enantiomer of formula (R)-(I), and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- the present invention provides a composition comprising a compound of formula (I), which is the (S)-enantiomer of formula (S)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- a compound of formula (I) which is the (S)-enantiomer of formula (S)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- the present invention provides for the use of a composition in the methods of the present invention, said composition comprising a compound of formula (I), which is the (S)-enantiomer of formula (S)-(I), and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
- the compounds of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer).
- SAR inducers are known and described in, for example, U.S. Pat. No. 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.
- compositions encompassed by the present invention include, for example, compositions comprising a compound of formula (I) and acibenzolar (CGA245704), a compound of formula (I) and ancymidol, a compound of formula (I) and alanycarb, a compound of formula (I) and aldimorph, a compound of formula (I) and amisulbrom, a compound of formula (I) and anilazine, a compound of formula (I) and azaconazole, a compound of formula (I) and azoxystrobin, a compound of formula (I) and benalaxyl, a compound of formula (I) and benthiavalicarb, a compound of formula (I) and benomyl, a compound of formula (I) and biloxazol, a compound of formula (I) and bitertanol, a compound of formula (I) and bixafen, a compound of formula (I) and blasticidin S, a compound of formula
- compositions of generic structure Ia wherein R and R 4 ⁇ H may be prepared by the [3+2]-cycloaddition of an acetylenethiolate anion II and an acetylenic ketone III to give thiophene ketone IV which upon reduction provides the corresponding thiophene alcohol Ia (see L. S. Rodinova, M. L. Petrov, and A. A. Petrov, Zhurnal Organicheskoi Khimii 1981, 17(10), 2071-2075 for a related thiophene synthesis):
- the [3+2]-cycloaddition reaction is carried out by preforming the acetylenethiolate in an inert solvent such as THF (tetrahydrofuran) at low temperature, preferably ⁇ 78 °, and then adding it to a solution of the acetylenic ketone III in an inert solvent or solvent mixture, such as THF and acetonitrile, at temperatures ranging from 0° C. to ⁇ 20° C.
- the acetylenethiolate II is prepared from the reaction of sulfur with a lithium salt (VI) of a terminal acetylene V (H. G. Raubenheimer, G. J. Kruger, C. F. Marais, R. Otte, and J. T. Z. Hattingh, Organometallics 1988, 7, 1853-1858) :
- Lithium acetylide VI is formed by the treatment of terminal acetylene V with a strong base such as n-butyllithium in an inert solvent such as THF at low temperature, preferably from ⁇ 40° C. to ⁇ 78° C. Addition of sulfur to acetylide VI at low temperature ( ⁇ 40° C. to ⁇ 78° C.) and reaction for 1.5-3 hr gives the acetylenethiolate II. Reduction of thiophene ketone IV is effected with a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C.
- a strong base such as n-butyllithium in an inert solvent such as THF
- the Heck reaction may be employed to arylate activated thiophenes that are intermediates in the synthesis of la when R 1 and R 3 are aryl (L. Lavenot, C. Gozzi, K. IIg, I Orlova, V. Penalva, and M. Lemaire, Journal of Organometallic Chem. 1998, 567, 49-55).
- thiophene-3-carboxaldehyde VII may be selectively arylated with aryl iodide R 3 I in the presence of a transition metal catalyst such as a palladium(II) catalyst to give a 2-arylated intermediate VIII.
- a transition metal catalyst such as a palladium(II) catalyst
- a second palladium-catalyzed arylation with another aryl iodode R 1 I then gives the 2,4-diarylthiophen-3-carboxaldehyde IX.
- an organometallic reagent R 2 M produces the compositions of generic structure Ia (R and R 4 ⁇ H).
- the Heck reaction is typically carried out in solvents such as acetonitrile or water, or in mixtures of the two, at temperatures in the range of 20-80° C. for 4-72 hrs.
- the typical palladium catalysts are palladium chloride, usually used in association with lithium chloride, or palladium acetate used with tetra-n-butylammonium bromide with or without a phosphine such as triphenylphosphine.
- the addition of the organometallic reagent R 2 M is typically conducted in an inert solvent such as ether or THF under N 2 atmosphere at 0-20° C. for 1-5 hrs.
- the organometallic reagent may be an organolithium reagent, or preferably an organomagnesium reagent.
- compositions of generic structure Ia wherein R 4 ⁇ H may also be prepared by the Michael addition of a substituted ⁇ -mercaptoketone X (R′ ⁇ H) to acetylenic ketone III to give the dihydrothienyl intermediate XI. Dehydration of XI to thiophene XII and subsequent reduction of XII provides the composition Ia (R 4 ⁇ H).
- the Michael addition is carried out by reaction of the ⁇ -mercaptoketone X (R′ ⁇ H) and the acetylenic ketone III in the presence of a base, preferably an organic base such as morpholine, and an inert solvent such as diethoxymethane at elevated temperatures such as reflux temperature for 1-8hrs.
- a base preferably an organic base such as morpholine
- an inert solvent such as diethoxymethane
- ⁇ -acetylthioketone X R′ ⁇ COCH 3
- the base such as morpholine cleaves the thioester to the requisite ⁇ -mercaptoketone X (R′ ⁇ H) in situ.
- Intermediate XI is efficiently dehydrated by treatment with p-toluenesulfonic acid or acetic anhydride in toluene at elevated temperatures (80-100° C.) for 12-48 hrs. to produce the thienyl ketone XII, reduction of which is accomplished as above with a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C.
- a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol
- ⁇ -acetylthioketones X (R′ ⁇ COCH 3 ) and ⁇ -mercaptoketones X (R′ ⁇ H) are readily available by treating the corresponding ⁇ -bromoketones XIII with thioacetic acid in a basic medium to give X (R′ ⁇ COCH 3 ), which upon treatment with aqueous base (e.g., aqueous NaOH) produces X (R′ ⁇ H).
- aqueous base e.g., aqueous NaOH
- compositions lb may be prepared from XIII (R ⁇ H) or its chloro analog by reaction with the ⁇ -ketoester XIV under base catalyzed conditions to give the dihydrofuran XV (see F. Feist, Chem, Ber. 1902, 35, 1537-44), dehydration of which produces the furan XVI.
- This dehydration is efficiently effected by treatment of XV with p-toluenesulfonic acid or acetic anhydride in toluene at elevated temperatures (80-100° C.) for 12-48 hrs.
- Oxidation of XVII to aldehyde my be effected with reagents including activated MnO 2 , o-iodosobenzoic acid (IBX) in DMSO, or CrO 3 /pyr in inert solvents such as dichloromethane.
- the addition of the organometallic reagent to aldehyde XVIII is typically conducted in an inert solvent such as ether or THF under N 2 atmosphere at 0-20° C. for 1-5 hrs.
- the organometallic reagent may be an organolithium reagent, or preferably an organomagnesium reagent.
- furyl ester XVI may be hydrolyzed to furoic acid XIX under aqueous basic conditions such as aqueous NaOH or LiOH.
- Conversion of the acid XIX to the Weinreb amide XX may be accomplished by coupling XIX and N,O-hydroxylamine hydrochloride using 1-hydroxybenzotriazole (HOBT) and diisopropylcarbodiimide (DIC) in the presence of diisopropylethylamine (DIEA) in an inert solvent such as dichloromethane (DCM).
- HOBT 1-hydroxybenzotriazole
- DIC diisopropylcarbodiimide
- DIEA diisopropylethylamine
- DCM dichloromethane
- ketone XXI reduction of which is accomplished as above with a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C. to produce compound Ib (R 4 ⁇ H).
- a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C. to produce compound Ib (R 4 ⁇ H).
- compositions Ic may be prepared using an approach similar to that employed for the thiophenes Ia, i.e., but adding ⁇ -aminoketones XXII to the alkynylketone III in the Michael addition.
- Reaction conditions similar to those used to prepare the aforementioned furans lb may be employed.
- Ester XXVII may also be hydrolyzed to its corresponding acid XXX and converted to its Weinreb amide XXXI as above. Addition of organometallic agent R 2 MgX′ gives the ketone XXXII, reduction of which produces compound Ic (R 4 ⁇ H).
- the red solution was warmed to room temperature and added to a solution of 400 mg (1.66 mmol) of 3-(3-chlorophenyI)-1-(3-pyridyl)-2-propyn-1-one in 4 mL of THF and 1 mL of acetonitrile.
- the reaction solution was stirred for 2 hr at room temperature, and was then poured into water.
- the aqueous layer was extracted several times with ether.
- the combined ether extracts were washed with saturated sodium chloride and dried over magnesium sulfate. The drying agent was filtered off, and the ether was removed by rotoevaporation.
- Compounds 1 to 175 all contain one asymmetrical carbon atom which is the carbon atom linked to one single hydroxy substituent (OH).
- Compound 175 showed plant height decrease at 200 ppm.
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GBGB0823002.1A GB0823002D0 (en) | 2008-12-17 | 2008-12-17 | Isoxazoles derivatives with plant growth regulating properties |
PCT/EP2009/066963 WO2010069880A2 (en) | 2008-12-17 | 2009-12-11 | Thiophene, furan and pyrrole derivatives for use as plant growth regulators |
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US13/133,708 Expired - Fee Related US8476446B2 (en) | 2008-12-17 | 2009-12-11 | Isoxazole derivatives for use as fungicides |
US13/140,766 Abandoned US20110251066A1 (en) | 2008-12-17 | 2009-12-11 | Isoxazole derivatives for use as plant growth regulators |
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US13/934,030 Abandoned US20130296381A1 (en) | 2008-12-17 | 2013-07-02 | Isoxazole derivatives for use as fungicides |
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Families Citing this family (275)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0823002D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isoxazoles derivatives with plant growth regulating properties |
CN103180307A (zh) | 2010-10-28 | 2013-06-26 | 先正达参股股份有限公司 | 新颖的杀微生物剂 |
WO2012062844A1 (en) | 2010-11-12 | 2012-05-18 | Syngenta Participations Ag | Novel microbiocides |
WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
WO2012143395A1 (en) * | 2011-04-20 | 2012-10-26 | Syngenta Participations Ag | 4,5-dihydro-isoxazole derivatives as fungicides |
WO2013007550A1 (en) | 2011-07-08 | 2013-01-17 | Syngenta Participations Ag | Fungicide mixtures |
WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
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US20150257383A1 (en) | 2012-10-12 | 2015-09-17 | Basf Se | Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
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WO2014082880A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4] triazole compounds |
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EP2746264A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
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EP2935224A1 (en) | 2012-12-19 | 2015-10-28 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
PL2934147T3 (pl) | 2012-12-20 | 2020-06-29 | BASF Agro B.V. | Kompozycje zawierające związki triazolowe |
EP2746260A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746259A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
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EP2746257A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
WO2014124850A1 (en) | 2013-02-14 | 2014-08-21 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
WO2014130409A2 (en) | 2013-02-21 | 2014-08-28 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazole mixtures |
EP2970996B1 (en) * | 2013-03-14 | 2019-08-21 | The Regents of The University of California | Modified pyr/pyl receptors activated by orthogonal ligands |
EP2813499A1 (en) | 2013-06-12 | 2014-12-17 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2815649A1 (en) | 2013-06-18 | 2014-12-24 | Basf Se | Fungicidal mixtures II comprising strobilurin-type fungicides |
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WO2015011615A1 (en) | 2013-07-22 | 2015-01-29 | Basf Corporation | Mixtures comprising a trichoderma strain and a pesticide |
EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
EP2839745A1 (en) | 2013-08-21 | 2015-02-25 | Basf Se | Agrochemical formulations comprising a 2-ethyl-hexanol alkoxylate |
WO2015036058A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
BR122021013202B1 (pt) | 2013-10-18 | 2022-03-08 | Basf Agrochemical Products B.V. | Uso do composto carboxamida ativo pesticida e método de proteção de material de propagação vegetal |
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CN105829296A (zh) | 2013-12-18 | 2016-08-03 | 巴斯夫欧洲公司 | 带有亚胺衍生的取代基的唑类化合物 |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
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 |
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EP2924027A1 (en) | 2014-03-28 | 2015-09-30 | Basf Se | Substituted [1,2,4]triazole and imidazole fungicidal compounds |
EP2949216A1 (en) | 2014-05-30 | 2015-12-02 | Basf Se | Fungicidal substituted alkynyl [1,2,4]triazole and imidazole compounds |
EP2949649A1 (en) | 2014-05-30 | 2015-12-02 | Basf Se | Fungicide substituted [1,2,4]triazole and imidazole compounds |
AR100743A1 (es) | 2014-06-06 | 2016-10-26 | Basf Se | Compuestos de [1,2,4]triazol sustituido |
EP2952507A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
CN106455572B (zh) | 2014-06-06 | 2020-01-14 | 巴斯夫欧洲公司 | 取代噁二唑在防除植物病原性真菌中的用途 |
EP2952512A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
EP2952506A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
BR112017005140A2 (pt) | 2014-10-06 | 2018-01-23 | Basf Se | compostos, mistura, composição, métodos para a proteção de culturas e para o combate ou controle de praga de invertebrados, método não terapêutico para o tratamento de animais infestados ou infectados por parasitas e semente |
EP3209818B1 (de) | 2014-10-24 | 2019-12-11 | Basf Se | Organische pestizid-teilchen |
US20180368404A1 (en) | 2014-11-06 | 2018-12-27 | Basf Se | 3-pyridyl heterobicyclic compound for controlling invertebrate pests |
EP3028573A1 (en) | 2014-12-05 | 2016-06-08 | Basf Se | Use of a triazole fungicide on transgenic plants |
US10556844B2 (en) | 2015-02-06 | 2020-02-11 | Basf Se | Pyrazole compounds as nitrification inhibitors |
WO2016128261A2 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
WO2016128240A1 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound and two fungicides |
BR112017021450B1 (pt) | 2015-04-07 | 2021-12-28 | Basf Agrochemical Products B.V. | Métodos de controle de pragas, método de melhoria da saúde vegetal e semente revestida |
EP3294690A1 (en) | 2015-05-12 | 2018-03-21 | Basf Se | Thioether compounds as nitrification inhibitors |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
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WO2017060148A1 (en) | 2015-10-05 | 2017-04-13 | Basf Se | Pyridine derivatives for combating phytopathogenic fungi |
US20190135798A1 (en) | 2015-11-02 | 2019-05-09 | Basf Se | Substituted Oxadiazoles for Combating Phytopathogenic Fungi |
EP3165094A1 (en) | 2015-11-03 | 2017-05-10 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
WO2017076740A1 (en) | 2015-11-04 | 2017-05-11 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3165093A1 (en) | 2015-11-05 | 2017-05-10 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3167716A1 (en) | 2015-11-10 | 2017-05-17 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
BR112018009566A2 (pt) | 2015-11-13 | 2018-11-06 | Basf Se | compostos, mistura, composição agroquímica, uso de compostos e método para combater fungos nocivos fitopatogênicos |
WO2017081312A1 (en) | 2015-11-13 | 2017-05-18 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
CN108347937A (zh) | 2015-11-19 | 2018-07-31 | 巴斯夫欧洲公司 | 用于防除植物病原性真菌的取代噁二唑 |
WO2017085100A1 (en) | 2015-11-19 | 2017-05-26 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
PL3383183T3 (pl) | 2015-11-30 | 2020-11-16 | Basf Se | Kompozycje zawierające cis-jasmon i bacillus amyloliquefaciens |
BR112018010140A8 (pt) | 2015-12-01 | 2019-02-26 | Basf Se | compostos de fórmula, composição, utilização de um composto de fórmula, método para o combate de fungos fitopatogênicos e semente |
EP3383849B1 (en) | 2015-12-01 | 2020-01-08 | Basf Se | Pyridine compounds as fungicides |
EP3205208A1 (en) | 2016-02-09 | 2017-08-16 | Basf Se | Mixtures and compositions comprising paenibacillus strains or fusaricidins and chemical pesticides |
WO2017153217A1 (en) | 2016-03-09 | 2017-09-14 | Basf Se | Spirocyclic derivatives |
WO2017153200A1 (en) | 2016-03-10 | 2017-09-14 | Basf Se | Fungicidal mixtures iii comprising strobilurin-type fungicides |
EP3426042A1 (en) | 2016-03-11 | 2019-01-16 | Basf Se | Method for controlling pests of plants |
MX2018012016A (es) | 2016-04-01 | 2019-01-24 | Basf Se | Compuestos biciclicos. |
US10986839B2 (en) | 2016-04-11 | 2021-04-27 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
MX2018014176A (es) | 2016-05-18 | 2019-02-28 | Basf Se | Capsulas que comprenden bencilpropargileteres para usar como inhibidores de la nitrificacion. |
US20190200612A1 (en) | 2016-09-13 | 2019-07-04 | Basf Se | Fungicidal mixtures i comprising quinoline fungicides |
WO2018054723A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018054721A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018054711A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018065182A1 (en) | 2016-10-04 | 2018-04-12 | Basf Se | Reduced quinoline compounds as antifuni agents |
WO2018073110A1 (en) | 2016-10-20 | 2018-04-26 | Basf Se | Quinoline compounds as fungicides |
MX2019007120A (es) | 2016-12-16 | 2019-09-16 | Basf Se | Compuestos plaguicidas. |
WO2018114393A1 (en) | 2016-12-19 | 2018-06-28 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3339297A1 (en) | 2016-12-20 | 2018-06-27 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3338552A1 (en) | 2016-12-21 | 2018-06-27 | Basf Se | Use of a tetrazolinone fungicide on transgenic plants |
BR112019014061A2 (pt) | 2017-01-23 | 2020-02-04 | Basf Se | compostos de fórmula i, intermediários b, intermediários c, intermediários ii e intermediários d, composição, uso, método para combater fungos fitopatogênicos, semente e processo para a síntese dos compostos de fórmula i |
CA3050864A1 (en) | 2017-01-26 | 2018-08-02 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
WO2018149754A1 (en) | 2017-02-16 | 2018-08-23 | Basf Se | Pyridine compounds |
BR112019015338B1 (pt) | 2017-02-21 | 2023-03-14 | Basf Se | Compostos de fórmula i, composição agroquímica, semente revestida, uso dos compostos e método para combater fungos nocivos fitopatogênicos |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
UA125313C2 (uk) | 2017-03-28 | 2022-02-16 | Басф Се | Пестициди |
CN116102580A (zh) | 2017-03-31 | 2023-05-12 | 巴斯夫欧洲公司 | 用于防除动物害虫的嘧啶鎓化合物及其混合物 |
EP3606914A1 (en) | 2017-04-06 | 2020-02-12 | Basf Se | Pyridine compounds |
US20200045974A1 (en) | 2017-04-07 | 2020-02-13 | Basf Se | Substituted Oxadiazoles for Combating Phytopathogenic Fungi |
US11147272B2 (en) | 2017-04-10 | 2021-10-19 | Mitsui Chemicals Argro, Inc. | Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients |
EP3611166B1 (en) | 2017-04-10 | 2022-09-21 | Mitsui Chemicals Agro, Inc. | Pyridone compound, and agricultural and horticultural fungicide having this as active component |
WO2018188962A1 (en) | 2017-04-11 | 2018-10-18 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
CN110234627B (zh) | 2017-04-11 | 2023-09-01 | 三井化学植保株式会社 | 吡啶酮化合物及以吡啶酮化合物作为有效成分的农园艺用杀菌剂 |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
EP3612514B1 (en) | 2017-04-20 | 2022-03-30 | PI Industries Ltd | Novel phenylamine compounds |
US20200190073A1 (en) | 2017-04-26 | 2020-06-18 | Basf Se | Substituted succinimide derivatives as pesticides |
WO2018202428A1 (en) | 2017-05-02 | 2018-11-08 | Basf Se | Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
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WO2018202491A1 (en) | 2017-05-04 | 2018-11-08 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
EP3618628A1 (en) | 2017-05-05 | 2020-03-11 | Basf Se | Fungicidal mixtures comprising triazole compounds |
US11591335B2 (en) | 2017-05-10 | 2023-02-28 | Basf Se | Bicyclic pesticidal compounds |
WO2018210658A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
WO2018210661A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
WO2018210660A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
WO2018210659A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
EP3625215B1 (en) | 2017-05-18 | 2023-09-13 | PI Industries Ltd | Formimidamidine compounds useful against phytopathogenic microorganisms |
BR112019025295A2 (pt) | 2017-05-30 | 2020-06-23 | Basf Se | Compostos, composição, uso de um composto da fórmula i, método para combater fungos fitopatogênicos e semente |
WO2018219797A1 (en) | 2017-06-02 | 2018-12-06 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
WO2018225829A1 (ja) | 2017-06-08 | 2018-12-13 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
BR112019025331A2 (pt) | 2017-06-16 | 2020-06-23 | Basf Se | Compostos da fórmula (i), composição, métodos de proteção de safras e de combate, método não terapêutico de tratamento, semente, uso dos compostos e uso de composto |
BR112019025191B1 (pt) | 2017-06-19 | 2023-11-28 | Basf Se | Compostos de pirimidínio substituídos, composição, método para proteger culturas, semente revestida, uso dos compostos e uso de um composto |
WO2018234139A1 (en) | 2017-06-19 | 2018-12-27 | Basf Se | 2 - [[5- (TRIFLUOROMETHYL) -1,2,4-OXADIAZOL-3-YL] ARYLOXY] (THIO) ACETAMIDES FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | SUBSTITUTED CYCLOPROPYL DERIVATIVES |
WO2019003767A1 (ja) | 2017-06-28 | 2019-01-03 | 日産化学株式会社 | アルコキシアルキル基を有するイソシアヌル酸誘導体及びその製造方法 |
WO2019002158A1 (en) | 2017-06-30 | 2019-01-03 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI |
WO2019025250A1 (en) | 2017-08-04 | 2019-02-07 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR COMBATING PHYTOPATHOGENIC FUNGI |
WO2019038042A1 (en) | 2017-08-21 | 2019-02-28 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI |
WO2019042800A1 (en) | 2017-08-29 | 2019-03-07 | Basf Se | PESTICIDE MIXTURES |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
EP3684761A1 (en) | 2017-09-18 | 2020-07-29 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019057660A1 (en) | 2017-09-25 | 2019-03-28 | Basf Se | INDOLE AND AZAINDOLE COMPOUNDS HAVING 6-CHANNEL SUBSTITUTED ARYL AND HETEROARYL CYCLES AS AGROCHEMICAL FUNGICIDES |
WO2019072906A1 (en) | 2017-10-13 | 2019-04-18 | Basf Se | IMIDAZOLIDINE PYRIMIDINIUM COMPOUNDS FOR CONTROL OF HARMFUL ANIMALS |
US11147275B2 (en) | 2017-11-23 | 2021-10-19 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019115511A1 (en) | 2017-12-14 | 2019-06-20 | Basf Se | Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
US11839214B2 (en) | 2017-12-15 | 2023-12-12 | Basf Se | Fungicidal mixture comprising substituted pyridines |
EP3728204A1 (en) | 2017-12-20 | 2020-10-28 | PI Industries Ltd. | Fluoralkenyl compounds, process for preparation and use thereof |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
US11512054B2 (en) | 2017-12-21 | 2022-11-29 | Basf Se | Pesticidal compounds |
BR112020012706A2 (pt) | 2018-01-09 | 2020-11-24 | Basf Se | uso de um composto de silietinil hetarila, composição para uso na redução de nitrificação, mistura agroquímica, métodos para reduzir a nitrificação e para tratamento de um fertilizante ou de uma composição |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
AU2019213693B2 (en) | 2018-01-30 | 2022-09-22 | Pi Industries Ltd. | Oxadiazoles for use in controlling phytopathogenic fungi |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
WO2019154665A1 (en) | 2018-02-07 | 2019-08-15 | Basf Se | New pyridine carboxamides |
US20200354321A1 (en) | 2018-02-07 | 2020-11-12 | Basf Se | New pyridine carboxamides |
EP3530118A1 (en) | 2018-02-26 | 2019-08-28 | Basf Se | Fungicidal mixtures |
EP3530116A1 (en) | 2018-02-27 | 2019-08-28 | Basf Se | Fungicidal mixtures comprising xemium |
BR112020015467A2 (pt) | 2018-02-28 | 2020-12-08 | Basf Se | Misturas fungicidas, composição fungicida, métodos para controlar fungos fitopatogênicos, para melhorar a saúde das plantas e para proteção de material de propagação de plantas contra fungos fitopatogênicos e material de propagação de planta |
MX2020009022A (es) | 2018-02-28 | 2020-10-12 | Basf Se | Uso de alcoxipirazoles como inhibidores de la nitrificacion. |
IL302719A (en) | 2018-02-28 | 2023-07-01 | Basf Se | Use of N-functional alkoxy pyrazole compounds as nitrification inhibitors |
WO2019166558A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
US11917995B2 (en) | 2018-03-01 | 2024-03-05 | BASF Agro B.V. | Fungicidal compositions of mefentrifluconazole |
EP3533333A1 (en) | 2018-03-02 | 2019-09-04 | Basf Se | Fungicidal mixtures comprising pydiflumetofen |
EP3533331A1 (en) | 2018-03-02 | 2019-09-04 | Basf Se | Fungicidal mixtures comprising pydiflumetofen |
EP3536150A1 (en) | 2018-03-06 | 2019-09-11 | Basf Se | Fungicidal mixtures comprising fluxapyroxad |
EP3762367A1 (en) | 2018-03-09 | 2021-01-13 | PI Industries Ltd. | Heterocyclic compounds as fungicides |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
BR112020020959A2 (pt) | 2018-04-16 | 2021-01-19 | Pi Industries Ltd. | Uso de compostos de fenilamidina 4-substituídospara controlar doenças de ferrugem em vegetais |
KR20210008036A (ko) | 2018-05-15 | 2021-01-20 | 바스프 에스이 | 벤즈피리목산 및 옥사조술필을 포함하는 혼합물 및 이의 용도 및 이의 적용 방법 |
WO2019219464A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
US20210340073A1 (en) | 2018-07-23 | 2021-11-04 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
HUE064943T2 (hu) | 2018-07-23 | 2024-04-28 | Basf Se | Szubsztituált tiazolidin vegyület alkalmazása nitrifikációs inhibitorként |
TWI828725B (zh) | 2018-07-25 | 2024-01-11 | 日商三井化學植保股份有限公司 | 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑 |
TW202009235A (zh) | 2018-08-17 | 2020-03-01 | 印度商皮埃企業有限公司 | 1,2-二硫醇酮化合物及其用途 |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
BR112021004526A2 (pt) | 2018-09-28 | 2021-06-08 | Basf Se | uso do composto, métodos de proteção de plantas, de controle ou combate a pragas invertebradas e de tratamento de sementes e semente |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
US20210387954A1 (en) | 2018-10-01 | 2021-12-16 | Pi Industries Limited | Oxadiazoles as fungicides |
AR116558A1 (es) | 2018-10-01 | 2021-05-19 | Pi Industries Ltd | Oxadiazoles |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
WO2020095161A1 (en) | 2018-11-05 | 2020-05-14 | Pi Industries Ltd. | Nitrone compounds and use thereof |
WO2020109039A1 (en) | 2018-11-28 | 2020-06-04 | Basf Se | Pesticidal compounds |
EP3670501A1 (en) | 2018-12-17 | 2020-06-24 | Basf Se | Substituted [1,2,4]triazole compounds as fungicides |
US20230031024A1 (en) | 2018-12-18 | 2023-02-02 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
BR112021020231A2 (pt) | 2019-04-08 | 2021-12-07 | Pi Industries Ltd | Compostos de oxadiazol inovadores para controlar ou prevenir fungos fitopatogênicos |
AR118614A1 (es) | 2019-04-08 | 2021-10-20 | Pi Industries Ltd | Compuestos de oxidazol para controlar o prevenir hongos fitopatogénicos |
MX2021012325A (es) | 2019-04-08 | 2022-05-18 | Pi Industries Ltd | Nuevos compuestos de oxadiazol para controlar o prevenir hongos fitopatogénicos. |
EP3730489A1 (en) | 2019-04-25 | 2020-10-28 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
EP3975718A1 (en) | 2019-05-29 | 2022-04-06 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2020244970A1 (en) | 2019-06-06 | 2020-12-10 | Basf Se | New carbocyclic pyridine carboxamides |
WO2020244969A1 (en) | 2019-06-06 | 2020-12-10 | Basf Se | Pyridine derivatives and their use as fungicides |
US20220235005A1 (en) | 2019-06-06 | 2022-07-28 | Basf Se | Fungicidal n-(pyrid-3-yl)carboxamides |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
AR119774A1 (es) | 2019-08-19 | 2022-01-12 | Pi Industries Ltd | Compuestos de oxadiazol que contienen un anillo heteroaromático de 5 miembros para controlar o prevenir hongos fitopatogénicos |
WO2021063735A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | New bicyclic pyridine derivatives |
WO2021063736A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | Bicyclic pyridine derivatives |
AR120374A1 (es) | 2019-11-08 | 2022-02-09 | Pi Industries Ltd | Compuestos de oxadiazol que contienen anillos de heterociclilo fusionados para controlar o prevenir hongos fitopatogénicos |
AU2020414327A1 (en) | 2019-12-23 | 2022-07-07 | Basf Se | Enzyme enhanced root uptake of agrochemical active compound |
US20230106291A1 (en) | 2020-02-28 | 2023-04-06 | BASF Agro B.V. | Methods and uses of a mixture comprising alpha-cypermethrin and dinotefuran for controlling invertebrate pests in t |
US20230142542A1 (en) | 2020-03-04 | 2023-05-11 | Basf Se | Use of substituted 1,2,4-oxadiazoles for combating phytopathogenic fungi |
WO2021209360A1 (en) | 2020-04-14 | 2021-10-21 | Basf Se | Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
EP3903584A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iv |
EP3903582A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ii |
EP3903581A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors i |
EP3903583A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iii |
BR112022021631A2 (pt) | 2020-04-28 | 2022-12-06 | Basf Se | Compostos, composição, métodos para combater ou controlar pragas invertebradas, para proteger plantas em crescimento e para tratar ou proteger um animal, semente e uso de um composto |
MX2022013278A (es) * | 2020-04-29 | 2022-11-14 | Syngenta Crop Protection Ag | Mejora de cultivos. |
EP3909950A1 (en) | 2020-05-13 | 2021-11-17 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP3945089A1 (en) | 2020-07-31 | 2022-02-02 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors v |
WO2021249800A1 (en) | 2020-06-10 | 2021-12-16 | Basf Se | Substituted [1,2,4]triazole compounds as fungicides |
EP3939961A1 (en) | 2020-07-16 | 2022-01-19 | Basf Se | Strobilurin type compounds and their use for combating phytopathogenic fungi |
WO2022017836A1 (en) | 2020-07-20 | 2022-01-27 | BASF Agro B.V. | Fungicidal compositions comprising (r)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- (1,2,4-triazol-1-yl)propan-2-ol |
EP3970494A1 (en) | 2020-09-21 | 2022-03-23 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors viii |
UY39385A (es) | 2020-08-18 | 2022-02-25 | Pi Industries Ltd | Nuevos compuestos heterocíclicos para combatir los hongos fitopatógenos |
AR123502A1 (es) | 2020-09-15 | 2022-12-07 | Pi Industries Ltd | Nuevos compuestos de picolinamida para combatir hongos fitopatógenos |
AR123501A1 (es) | 2020-09-15 | 2022-12-07 | Pi Industries Ltd | Nuevos compuestos de picolinamida para combatir hongos fitopatógenos |
TW202229241A (zh) | 2020-09-26 | 2022-08-01 | 印度商皮埃企業有限公司 | 殺線蟲化合物及其用途 |
EP4236691A1 (en) | 2020-10-27 | 2023-09-06 | BASF Agro B.V. | Compositions comprising mefentrifluconazole |
WO2022090071A1 (en) | 2020-11-02 | 2022-05-05 | Basf Se | Use of mefenpyr-diethyl for controlling phytopathogenic fungi |
WO2022090069A1 (en) | 2020-11-02 | 2022-05-05 | Basf Se | Compositions comprising mefenpyr-diethyl |
WO2022106304A1 (en) | 2020-11-23 | 2022-05-27 | BASF Agro B.V. | Compositions comprising mefentrifluconazole |
EP4018830A1 (en) | 2020-12-23 | 2022-06-29 | Basf Se | Pesticidal mixtures |
CN116829521A (zh) | 2021-02-02 | 2023-09-29 | 巴斯夫欧洲公司 | Dcd和烷氧基吡唑作为硝化抑制剂的协同增效作用 |
EP4043444A1 (en) | 2021-02-11 | 2022-08-17 | Basf Se | Substituted isoxazoline derivatives |
BR112023022854A2 (pt) | 2021-05-05 | 2024-01-23 | Pi Industries Ltd | Compostos heterocíclicos fusionados inovadores para combater fungos fitopatogênicos |
WO2022238157A1 (en) | 2021-05-11 | 2022-11-17 | Basf Se | Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
CN117355520A (zh) | 2021-05-18 | 2024-01-05 | 巴斯夫欧洲公司 | 用作杀真菌剂的新型取代喹啉类 |
CN117355518A (zh) | 2021-05-18 | 2024-01-05 | 巴斯夫欧洲公司 | 用作杀真菌剂的新型取代吡啶类 |
CA3218900A1 (en) | 2021-05-18 | 2022-11-24 | Wassilios Grammenos | New substituted pyridines as fungicides |
AR125955A1 (es) | 2021-05-21 | 2023-08-30 | Basf Se | Uso de un compuesto de alcoxi pirazol n-funcionalizado como inhibidor de nitrificación |
CA3219022A1 (en) | 2021-05-21 | 2022-11-24 | Barbara Nave | Use of ethynylpyridine compounds as nitrification inhibitors |
AR125925A1 (es) | 2021-05-26 | 2023-08-23 | Pi Industries Ltd | Composicion fungicida que contiene compuestos de oxadiazol |
EP4094579A1 (en) | 2021-05-28 | 2022-11-30 | Basf Se | Pesticidal mixtures comprising metyltetraprole |
AU2022296764A1 (en) | 2021-06-21 | 2024-01-04 | Basf Se | Metal-organic frameworks with pyrazole-based building blocks |
EP4119547A1 (en) | 2021-07-12 | 2023-01-18 | Basf Se | Triazole compounds for the control of invertebrate pests |
KR20240042626A (ko) | 2021-08-02 | 2024-04-02 | 바스프 에스이 | (3-퀴놀릴)-퀴나졸린 |
AU2022321882A1 (en) | 2021-08-02 | 2024-02-15 | Basf Se | (3-pirydyl)-quinazoline |
EP4140986A1 (en) | 2021-08-23 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4140995A1 (en) | 2021-08-27 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4151631A1 (en) | 2021-09-20 | 2023-03-22 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2023072670A1 (en) | 2021-10-28 | 2023-05-04 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors x |
WO2023072671A1 (en) | 2021-10-28 | 2023-05-04 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ix |
EP4194453A1 (en) | 2021-12-08 | 2023-06-14 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4198033A1 (en) | 2021-12-14 | 2023-06-21 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP4198023A1 (en) | 2021-12-16 | 2023-06-21 | Basf Se | Pesticidally active thiosemicarbazone compounds |
AR127972A1 (es) | 2021-12-17 | 2024-03-13 | Pi Industries Ltd | Novedosos compuestos de piridina carboxamida bicíclica sustituida fusionada para combatir hongos fitopatogénicos |
EP4238971A1 (en) | 2022-03-02 | 2023-09-06 | Basf Se | Substituted isoxazoline derivatives |
WO2023203066A1 (en) | 2022-04-21 | 2023-10-26 | Basf Se | Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers |
WO2023208447A1 (en) | 2022-04-25 | 2023-11-02 | Basf Se | An emulsifiable concentrate having a (substituted) benzaldehyde-based solvent system |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
EP4342885A1 (en) | 2022-09-20 | 2024-03-27 | Basf Se | N-(3-(aminomethyl)-phenyl)-5-(4-phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-amine derivatives and similar compounds as pesticides |
EP4361126A1 (en) | 2022-10-24 | 2024-05-01 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors xv |
WO2024104813A1 (en) | 2022-11-14 | 2024-05-23 | Basf Se | Fungicidal mixture comprising substituted pyridines |
WO2024104823A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | New substituted tetrahydrobenzoxazepine |
WO2024104818A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Substituted benzodiazepines as fungicides |
WO2024104814A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Fungicidal mixture comprising substituted pyridines |
WO2024104815A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Substituted benzodiazepines as fungicides |
WO2024104822A1 (en) | 2022-11-16 | 2024-05-23 | Basf Se | Substituted tetrahydrobenzodiazepine as fungicides |
EP4389210A1 (en) | 2022-12-21 | 2024-06-26 | Basf Se | Heteroaryl compounds for the control of invertebrate pests |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
DE60039616D1 (de) * | 1999-08-13 | 2008-09-04 | Vertex Pharma | INHIBITOREN DER c-JUN N-TERMINALEN KINASE (JNK) UND ANDERE PROTEIN-KINASEN |
CN1312136C (zh) * | 2002-04-26 | 2007-04-25 | 伊莱利利公司 | 用作速激肽受体拮抗剂的三唑衍生物 |
US7338967B2 (en) * | 2004-09-10 | 2008-03-04 | Syngenta Limited | Substituted isoxazoles as fungicides |
JP4988576B2 (ja) * | 2004-09-10 | 2012-08-01 | シンジェンタ リミテッド | 殺真菌剤としての置換されたイソオキサゾール |
EP1871770A1 (en) * | 2005-04-22 | 2008-01-02 | Kalypsys, Inc. | Ortho-terphenyl inhibitors of p38 kinase and methods of treating inflammatory disorders |
DE102005031412A1 (de) * | 2005-07-06 | 2007-01-11 | Bayer Cropscience Gmbh | 3-[1-Halo-1-aryl-methan-sulfonyl]-und 3-[1-Halo-1-heteroaryl-methan-sulfonyl]-isoxazolin-Derivate, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
CN100410244C (zh) * | 2005-09-08 | 2008-08-13 | 沈阳化工研究院 | 异噁唑类化合物作为杀菌剂的应用 |
WO2008148859A2 (en) * | 2007-06-06 | 2008-12-11 | Basf Se | Fungicidal mixtures |
GB0823002D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isoxazoles derivatives with plant growth regulating properties |
-
2008
- 2008-12-17 GB GBGB0823002.1A patent/GB0823002D0/en active Pending
-
2009
- 2009-12-11 WO PCT/EP2009/066965 patent/WO2010069881A2/en active Application Filing
- 2009-12-11 JP JP2011541361A patent/JP2012512227A/ja active Pending
- 2009-12-11 EP EP09774899A patent/EP2369933A2/en not_active Withdrawn
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