WO1998023156A1 - Methyl substituted fungicides and arthropodicides - Google Patents
Methyl substituted fungicides and arthropodicides Download PDFInfo
- Publication number
- WO1998023156A1 WO1998023156A1 PCT/US1997/021944 US9721944W WO9823156A1 WO 1998023156 A1 WO1998023156 A1 WO 1998023156A1 US 9721944 W US9721944 W US 9721944W WO 9823156 A1 WO9823156 A1 WO 9823156A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenyl
- pyridinyl
- ocf
- dime
- naphthalenyl
- Prior art date
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 281
- 239000000417 fungicide Substances 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 311
- 238000000034 method Methods 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 241000238421 Arthropoda Species 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 7
- 244000000004 fungal plant pathogen Species 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 395
- -1 6-chloro-4-pyrimidinyl Chemical group 0.000 claims description 341
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 125000001188 haloalkyl group Chemical group 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 22
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 18
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 229910052804 chromium Inorganic materials 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 238000007667 floating Methods 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- FXNJWMDYBXUAHE-UHFFFAOYSA-N 5-methoxy-2-methyl-4-[2-methyl-6-(3-methylphenoxy)phenyl]-1,2,4-triazol-3-one Chemical compound COC1=NN(C)C(=O)N1C1=C(C)C=CC=C1OC1=CC=CC(C)=C1 FXNJWMDYBXUAHE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- XKUZUXHCVSWZQQ-UHFFFAOYSA-N FC=1C=C(OC2=C(C(=CC=C2)C)N2C(N(N=C2OC)C)=O)C=CC1 Chemical compound FC=1C=C(OC2=C(C(=CC=C2)C)N2C(N(N=C2OC)C)=O)C=CC1 XKUZUXHCVSWZQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 119
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 238000012360 testing method Methods 0.000 description 70
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 28
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 27
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 27
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 27
- 229940126543 compound 14 Drugs 0.000 description 27
- 229940126142 compound 16 Drugs 0.000 description 27
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 26
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 241000607479 Yersinia pestis Species 0.000 description 17
- 229910052794 bromium Inorganic materials 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 125000001246 bromo group Chemical group Br* 0.000 description 16
- 229910052801 chlorine Inorganic materials 0.000 description 16
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
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- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 10
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 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
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 238000007280 thionation reaction Methods 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
- 125000005490 tosylate group Chemical group 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 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
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- XQXGWWXFFSHSFZ-UHFFFAOYSA-N tris[4-(trifluoromethoxy)phenyl]bismuthane Chemical compound C1=CC(OC(F)(F)F)=CC=C1[Bi](C=1C=CC(OC(F)(F)F)=CC=1)C1=CC=C(OC(F)(F)F)C=C1 XQXGWWXFFSHSFZ-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/12—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Definitions
- This invention relates to certain methyl substituted fungicides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides and arthropodicides.
- the control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumers.
- the control of arthropod pests is also extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
- the control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
- X is OR 1 , SCOJ ⁇ J R 1 or halogen;
- A is O, S, N, NR 5 or CR 7 ;
- G is C or N; provided that when G is C, A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, A is N or CR 7 and the floating double bond is attached to A;
- W is O; S; NH; N(C r C 6 alkyl); or NO(C r C 6 alkyl);
- Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring having the R 3 and R 4 substituents and the moiety on the right side of the linkage is bonded to Z;
- Z is independently selected from: i) C]-C JO alkyl, CI -CJ Q haloalkyl or phenyl each optionally substituted with R 9 and optionally substituted with one or more R 10 ; ii) a ring selected from 5 or 6-membered aromatic heterocyclic ring, each heterocyclic ring containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring contains no more than 3 nitrogens, no more than 1 oxygen, and
- R 7 is H, halogen or methyl
- R 8 is H, C r C 3 alkyl, C r C 3 alkoxy, C r C 3 alkylthio, C r C 3 haloalkyl, C 2 -C 3 alkenyl,
- R 9 is halogen; Ci-C alkyl; C j -Cg haloalkyl; C j -Cg alkoxy; C Cg haloalkoxy; C 2 -Cg alkenyl; C 2 -C 6 haloalkenyl; C 2 -Cg alkynyl; C j -Cg alkylthio;
- R 12 is halogen, Cj-Cg alkyl, Cj-Cg haloalkyl, C j -C 6 alkoxy, C j -Cg haloalkoxy, C 2 -Cg alkenyl, C 2 -Cg haloalkenyl, C 2 -Cg alkynyl, C j -Cg alkylthio, C r C 6 haloalkylthio, C r C 6 alkylsulfinyl, C r C 6 alkylsulfonyl or C 3 -C 6 cycloalkyl;
- R 13 is halogen, Cj-Cg alkyl, Cj-Cg haloalkyl, C j -Cg alkoxy, C j -Cg haloalkoxy or cyano; m is 0, 1 or 2; n is 0, 1 or 2; r is 1, 2, 3 or 4; and s is 0 or 1.
- This invention provides a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula I including all geometric and stereoisomers, N-oxide, and agriculturally suitable salts thereof, provided that when T is T 1 , then i) when Y is -O-, X is OMe, R 3 is CH 3 and R 4 is H, then Z is other than 6-chloro-4-pyrimidinyl and 6-chloro-2-pyrazinyl; ii) when Y is a direct bond, X is Cl, R 3 is CH 3 and R 4 is H, then Z is other than
- This invention also provides selected compounds of Formula I which are considered particularly effective fungicides and arthropodicides. Specifically, this invention provides compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, and agricultural compositions containing them and their use as fungicides and arthropodicides, provided that
- R 10 other than methyl and halogen; and ix) when Y is -CH 2 O-, R 3 is CH 3 , Z is phenyl substituted with R 10 in the 2-position and R 10 is methyl or halogen, then Z is substituted with at least one
- R 9 or R 10 other than methyl and halogen
- haloalkylthio straight-chain or branched alkyl, such as, methyl, ethyl, r ⁇ -propyl, z ' -propyl, or the different butyl, pentyl or hexyl isomers.
- alkyl used alone or in the compound word “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, «-propyl, z ' -propyl, or the different butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl isomers.
- Alkenyl includes straight-chain or branched alkenes such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers.
- Alkenyl also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl.
- Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
- Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
- Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
- Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
- Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
- alkylsulfinyl examples include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
- alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
- Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
- halogen either alone or in compound words such as “haloalkyl” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
- haloalkenyl “haloalkynyl”, “haloalkoxy”, “haloalkylthio”, and the like, are defined analogously to the term “haloalkyl”.
- haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
- haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
- haloalkylthio examples include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
- aromatic heterocyclic rings are defined as those rings which satisfy the H ⁇ ckel rule. Examples include: a 5- or 6- membered aromatic heterocyclic ring containing 1 to 4 heteroatoms such as furanyl, furazanyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, oxadiazolyl, imidazolyl, isoxazolyl, thiazolyl, thiadiazolyl isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl and triazinyl with said ring attached through any available carbon or nitrogen.
- the aromatic heterocyclic ring when the aromatic heterocyclic ring is furanyl, it can be 2-furanyl or 3-furanyl, for pyrrolyl, the aromatic heterocyclic ring is 1 -pyrrolyl, 2-pyrrolyl or 3-pyrrolyl, for pyridyl, the aromatic ring is 2-pyridyl, 3-pyridyl or 4-pyridyl and similarly for other aromatic heterocyclic rings.
- the Y substituent is preferably attached to the aromatic ring of the tetrahydronaphthalene (i.e., the ring which satisfies the H ⁇ ckel rule).
- Cj-C The total number of carbon atoms in a substituent group is indicated by the "Cj-C;" prefix where i and j are numbers from 1 to 10.
- C j -C 3 alkylthio designates methylthio through propylthio.
- alkylcarbonyl include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
- a group contains a substituent which can be hydrogen, for example R 2 or R 7 , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
- a group is optionally substituted with a substituent, for example with R 1 , then, when the group is not substituted with that substituent, it is recognized that this is equivalent to said group having a hydrogen substituent.
- Compounds of this invention can exist as one or more stereoisomers.
- the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
- one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). (See, e.g., U.S. Provisional Patent Application Serial No.
- the present invention comprises compounds selected from Formula I and agriculturally suitable salts thereof.
- the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
- the salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
- inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
- Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1.
- Z is phenyl, pyridinyl, thiazolyl or thiadiazolyl, each optionally substituted with R 9 and optionally substituted with one or more R 10 ;
- R 9 is halogen, C j -Cg alkyl, C j -Cg alkoxy, C j -Cg haloalkyl or C Cg haloalkoxy;
- R 10 is halogen, C r C 6 alkyl, C r C 6 alkoxy, C r C 6 haloalkyl or
- Z is phenyl, pyridinyl, thiazolyl or thiadiazolyl, each optionally substituted with R 9 and optionally substituted with one or more R 10 ;
- R 9 is halogen, C j -Cg alkyl, C j -Cg alkoxy, C j -Cg haloalkyl or C j -Cg haloalkoxy;
- R 10 is halogen, C r C 6 alkyl, C r C 6 alkoxy, C r C 6 haloalkyl or
- G is N
- Z is phenyl, pyridinyl, thiazolyl or thiadiazolyl, each optionally substituted with R 9 and optionally substituted with one or more R 10 ;
- R 8 is CH 3 ;
- R 9 is halogen, Cj-Cg alkyl, C j -Cg alkoxy, C j -Cg haloalkyl or
- R 10 is halogen, C r C 6 alkyl, C r C 6 alkoxy, C r C 6 haloalkyl or Cj-Cg haloalkoxy; provided that i) when X is OMe, R 3 is CH 3 and R 4 is H, then Z is other than 3-(trifluoromethyl)phenyl; and ii) when X is OMe, R 3 is H and R 4 is CH 3 , then Z is other than 3-(trifluoromethyl)phenyl. Preferred 4.
- T is T 1 ;
- A is N;
- G is N;
- Z is thienyl optionally substituted with R 9 and optionally substituted with one or more R 10 ;
- R 8 is CH 3 ;
- R 9 is halogen or C ⁇ -C 3 alkyl; and R 10 is halogen or C r C 3 alkyl.
- This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
- the preferred compositions of the present invention are those which comprise the above preferred compounds.
- This invention also relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of the compounds of the invention (e.g., as a composition described herein).
- the preferred methods of use are those involving the above preferred compounds.
- This invention also relates to arthropodicidal compositions comprising arthropodicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
- This invention also relates to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of the compounds of the invention (e.g., as a composition described herein).
- the preferred methods of use are those involving the above preferred compounds.
- T T 1
- G G is N
- A is N and the floating double bond is attached to A
- W is O
- X is OCH 3
- R 8 is H, C r C 3 alkyl, C r C 3 haloalkyl, C 2 -C 3 alkenyl, C -C 3 alkynyl, cyclopropyl or cyano
- Z is phenyl optionally substituted with R 9 and optionally substituted with R 10
- R 9 is H, halogen, -C alkyl, C r C 6 haloalkyl, C j -Cg alkoxy, C r C 6 haloalkoxy, C -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C
- R 9 is H, halogen, C j -C 6 alkyl, C j -Cg haloalkyl, Cj-Cg alkoxy, Cj-Cg haloalkoxy, C -C 6 alkenyl, C -Cg haloalkenyl, C 2 -C 6 alkynyl,
- Compounds 1-10 and 40 in Index Table A are Compounds 1-10 and 40 in Index Table A. Also of note are compounds of Formula I other than Compounds 1-10 and 40 in Index Table A (e.g., Compounds 11-39 and 41-71 in Index Table A and Compound 72 in Index Table B).
- the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-46.
- the definitions of T, A, G, W, X, Y, Z, R ⁇ -R 21 , m, n, r and s in the compounds of Formulae 1-62 below are as defined above in the Summary of the Invention.
- Compounds of Formulae Ia-Iy are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-Iy are as defined above for Formula I.
- a compound of Formula I wherein T is T 1 and R 2 is H may exist as tautomer la or lb, or both la and lb.
- Procedures 1) to 5 describe syntheses involving construction of the heterocycle after the formation of the aryl moiety.
- Procedure 5) describes syntheses of the aryl moiety with the T-moiety already in place.
- Suitable solvents are selected from the group consisting of polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
- polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide
- ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether
- ketones such as
- Use of trimethylsilyldiazomethane requires a protic cosolvent such as methanol.
- Suitable Lewis acids include trimethylsilyl triflate and tetrafluoroboric acid.
- the alkyl trichloroacetimidates can be prepared from the appropriate alcohol and trichloroacetonitrile as described in the literature (J. Danklmaier and H. H ⁇ nig, Synth. Commun., (1990), 10, 203).
- a trialkyloxonium tetrafluoroborate e.g., Meerwein's salt
- the use of trialkyloxonium salts as powerful alkylating agents is well known in the art (see U. Sch ⁇ llkopf, U. Groth, C. O.ng, Angew. Chem., Int. Ed. Engl, (1981), 10, 798).
- Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
- alkali metal alkoxides such as potassium tert-butoxide
- inorganic bases such as sodium hydride and potassium carbonate
- pyridine or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
- the nucleophiles of Formula 6 are N-substituted hydroxylamines (HO- ⁇ HR 2 ) and substituted hydrazines (H ⁇ (R 5 )- ⁇ HR 2 ). Examples of such nucleophiles are N-methylhydroxylamine and methylhydrazine.
- Compounds of Formula lb can be prepared by reaction of nitrile esters of Formula 7 with ambident nucleophiles of Formula 6. See M. Scobie and G. Tennant, J Chem. Soc, Chem. Comm., (1994), 2451. Alkylation of lb with alkyl halides in the presence of base provides compounds of Formula lc. Alternatively, treatment of lb with alkylamines or alkoxyamines provides compounds of Formula lc.
- W N(C j -C alkyl) or NO(C j -Cg alkyl)
- Esters of Formula 5a can be prepared from copper (I)-catalyzed reaction of malonate esters with substituted iodobenzenes of Formula 8 according to methods adapted from A. Osuka, T. Kobayashi and H. Suzuki, Synthesis , (1983), 67, and illustrated in Scheme 3.
- R C j -C 4 alkyl
- malonate esters of Formula 5a can be prepared by treating phenyl acetic acid esters of Formula 9a with a dialkyl carbonate or alkyl chloro formate in the presence of a suitable base such as, but not limited to, sodium metal and sodium hydride (Scheme 4).
- a suitable base such as, but not limited to, sodium metal and sodium hydride (Scheme 4).
- Nitrile esters of Formula 7 can be prepared similarly from compounds of Formula 10.
- R C j -C 4 alkyl
- Esters of Formula 9a (compounds of Formula 9 wherein E 1 is OR) can be prepared from acid-catalyzed alcoholysis of phenyl acetonitriles of Formula 10 or by esterification of phenyl acetic acids of Formula 11 as illustrated in Scheme 5 (see Org. Synth, Coll. Vol. I, (1941), 270).
- Phenyl acetic acid esters of Formula 9b (compounds of Formula 9a wherein Y is Y 1 ) can also be prepared by copper (I)-catalyzed condensation of phenyl halides of Formula 12 with compounds of Formula 13 as described in EP-A-307,103 and illustrated below in Scheme 6.
- Compounds of Formula 12 can be prepared by the Arndt-Eistert synthesis starting from benzoic acids of Formula 14 as illustrated in Scheme 7, (see F. Arndt, B. Eistert, Ber. 68, 200 (1935); T. Aoyama, T. Shioiri, Tetrahedron Letters 11, 4461 (1980)).
- a halogenating agent such as thionyl chloride
- an alkylating agent such as diazomethane
- Compounds of Formula 14 can be prepared from nitrobenzoic acids of Formula 15 by a modification of the Sandmayer Reaction as taught in S. Kanoh, H. Muramoto, N. Kobayashi, M. Motoi and H. Suda, Bull. Chem. Soc. Jpn. 60, 3659 (1987) and M. P. Doyle, J Org. Chem. 41, 2426 (1977) (Scheme 8).
- the compound can be prepared by nitration and reduction of commercially available 2,5-dimethylbenzoic acid as taught in A.N. Fugiwara, E. M. Acton, Can. J. Chem. 48, 1346 (1970).
- esters of Formula 9c can also be prepared by forming the Y 2 bridge using conventional nucleophilic substitution chemistry (Scheme 9). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 17 or 18 with a nucleophilic ester of Formula 16 affords compounds of Formula 9c.
- a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compound of Formula 16.
- R C j -C 4 alkyl
- Lg Br, Cl, I, OS0 2 CH 3 , OS0 2 (4-Me-Ph)
- Compounds of Formula 16 can be prepared from compounds of Formula 12 by methods taught in Chem. Pharm. Bull 33 (12), 5184 (1985) or J. Org. Chem. 53 (2) 439, (1988). For example treatment of compounds of Formula 12 with a metal hydroxide, such as sodium hydroxide, in a polar protic solvent in the presence of a metal species such as copper yields compound 16a (compounds of Formula 16 where R 14 is OH).
- Compounds of Formula 16b (compounds of Formula 16 where R 14 is CH 2 OH or CH 2 SH) can be prepared by metal-halogen exchange in compounds of Formula 12 followed by quenching with the appropriate electrophile.
- reducing agents sodium borohydride (NaBH 4 ), sodium cyanoborohydride (NaCNBH 4 ) and diisobutylaluminum hydride (DIBAL-H) (Scheme 10).
- Suitable inert solvents are methanol, ethanol, methylene chloride and THF, (see M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons: New York, (1986)).
- esters of Formula 9d can also be prepared by forming the Y 3 bridge from substituted hydroxylamines 16d and carbonyl compounds 19.
- the hydroxylamines 16d are in turn prepared from esters 16c.
- Compounds of Formula 16c where the Lg is Br, Cl, I, OSO 2 CH 3 or OSO 2 (4-Me-Ph) can be prepared from compounds of Formula 16b, (see March, J. Advanced Organic Chemistry, 3rd ed., John Wiley: New York, (1985). This method has been described in EP-A-600,835 and is illustrated in Scheme 11.
- Compounds of Formula 20a can be prepared from compounds of Formula Id (compounds of Formula 1 wherein X 1 is OH) by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives (Scheme 13).
- halogenating agents such as thionyl chloride or phosphorus oxybromide
- compounds of Formula Id can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, />-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 20b.
- the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).
- sulfonyl compounds of Formula 20c can be prepared by oxidation of the corresponding thio compound of Formula 21 using well-known methods for the oxidation of sulfur (see Schrenk, K. in The Chemistry ofSulphones and Sulphoxides; Patai, S. et al., Eds.; Wiley: New York, (1988)).
- Suitable oxidizing reagents include met ⁇ -chloro-peroxybenzoic acid, hydrogen peroxide and Oxone® (KHSO 5 ).
- halo-compounds of Formula 20d can be prepared from hydrazides of Formula 22 as illustrated in Scheme 15.
- the compound of Formula 22 is treated with excess of a thionyl halide such as thionyl chloride.
- the product formed first is the ring-closed compound of Formula 23 which can be isolated or converted in situ to the compound of Formula 20d; see P. Molina, A. Tarraga, A. Espinosa, Synthesis, (1989), 923 for a description of this process.
- the hydrazides of Formula 22 can be prepared as illustrated in Scheme 16. Condensation of the isocyanate of Formula 24 with the hydrazine of Formula H 2 NNR 2 R 15 in an inert solvent such as tetrahydrofuran affords the hydrazide.
- R C j -C 4 alkyl 25a
- Q 4 H, C j -Cg alkyl, C j -Cg alkoxy
- the carbonylating agents can be alkyl chloroformates or dialkyl carbonates. Some of these carbonylating reactions may require the addition of a base to effect reaction.
- Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or triethylenediamine.
- Suitable solvents include polar aprotic solvents such as acetonitrile, dimethylformamide, or dimethyl sulfoxide; ethers such as tetrahydrofuran, dimethoxyethane or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; or halocarbons such as dichloromethane or chloroform.
- the reaction temperature can vary between 0 °C and 150 °C and the reaction time can be from 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates.
- Q 1 and Q 2 are independently Cl, OCCl 3 , 0(C j -C 4 alkyl), 1 -imidazolyl, 1,2,4-triazolyl
- N-Amino-ureas of Formula 26 can be prepared as illustrated in Scheme 20.
- Treatment of an aniline of Formula 27 with phosgene, thiophosgene, NN'-carbonyldiimidazole, or NN'-thiocarbonyldiimidazole produces the isocyanate or isothiocyanate of Formula 28.
- a base can be added for reactions with phosgene or thiophosgene.
- Subsequent treatment of the iso(thio)cyanate with an R 2 -substituted hydrazine produces the N-amino-urea of Formula 26.
- Compounds of Formula 29 can be prepared by contacting benzyl halides, mesylates or tosylates of Formula 30 with various nucleophiles (Scheme 22).
- the appropriate alcohol or thiol is treated with a base, for example sodium hydride, to form the corresponding alkoxide or thioalkoxide which acts as the nucleophile.
- Lg Br, Cl, I, OS0 CH 3 , OS0 2 (4-Me-Ph)
- Formula 30a (compounds of Formula 30 where the Lg group has been replaced with OH) by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives (Scheme 23).
- Compounds of Formula 30a can also be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, />-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 30.
- the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).
- Formula 1 f compounds can be prepared by reaction of Formula 28 iso(thio)cyanates or Formula 28a carbodiimides with Formula 35 esters. As described above, base may be added to accelerate the reaction and subsequent cyclization to Formula If compounds.
- Carbodiimides 28a can be prepared as shown in Scheme 25, starting with compounds of Formula 28 and forming compounds of Formula 34 which are dehydrated to give compounds of Formula 28a.
- the (thio)ureas or amidines of Formula 32 can be prepared by either of the methods illustrated in Scheme 26.
- an iso(thio)cyanate of Formula 28 or carbodiimide of Formula 28a can be condensed with an amine of Formula R 2 -NH 2 to form the urea or amidine.
- the anilines and iso(thio)cyanates of Formulae 27 and 28, respectively, are commercially available or prepared by well-known methods.
- isothiocyanates can be prepared by methods described in J. Heterocycl. Chem. , (1990), 17, 407.
- Isocyanates can be prepared as described in March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp 944, 1166.
- Compounds of Formula Im (compounds of Formula I where T is T 1 , X is OR 1 , R 1 is CH 3 , R 2 is CH 3 , W is O, A is N, G is N, Y 5 is -O-, -OCH 2 - or -SCHR 1 ] -) can be prepared by forming the Y 5 bridge using conventional nucleophilic substitution chemistry (Scheme 30). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 17 or 18 with nucleophilic compounds of Formula 36 affords compounds of Formula Im.
- a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compounds of Formula 37.
- an additional substituent on Z which activates the leaving group (Lg) can be advantageous (e.g., when Lg-Z is 2-chloro-3 -nitro thiophene, the activating nitro group can be removed after coupling by reduction to the amine followed by diazotization and reduction to provide compounds of Formula Im).
- Benzyl halides of Formula 38 can be prepared by radical halogenation of the corresponding alkyl compound of Formula 39a, see WO 96/38425. Benzyl halides can also be prepared by the acidic cleavage of the corresponding methyl ether of Formula 39b under conditions which provide the halide, see Scheme 31. Methods for preparing the corresponding compounds of Formula 38 wherein the T 1 group has been replaced by T 2 are described in WO 94/05620. Methods for preparing the corresponding compounds of Formula 38 wherein the T 1 group has been replaced by T 3 are described in EP-A-254,426, EP-A-299,694 and AU-A-55899/90.
- compounds of Formula 38 can be prepared from the corresponding alcohol of Formula 40 by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives.
- compounds of Formula 40 can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, / toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 41.
- the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine) see Scheme 32.
- Compounds of Formula 40 can be prepared by reducing esters of Formula 44 or aldehydes of Formula 43 with an appropriate reducing agent, (M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons pp. 147-160, (1986)).
- an appropriate reducing agent M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons pp. 147-160, (1986)
- DIBAL-H diisobutylaluminum hydride
- Compounds of Formula 43 can be reduced with sodium borohydride in a protic solvent such as methanol or ethanol, Scheme 34.
- Esters of Formula 44 can be prepared from anthranilic acid esters of Formula 45 according to the procedures described in Scheme 35.
- Esters 45 can be prepared from readily accessible anthranilic acids by esterification techniques well known in the art.
- a formaldehyde equivalent i.e., dimethylformamide or methyl chloro formate
- compounds of Formula 48 can be prepared from compounds of Formula 46 by metallation using an alkyllithium followed by quenching with a trialkoxy borane, (Scheme 38), see Organic Synthesis via Boranes; Wiley: New York, (1975).
- R Cj-C 4 alkyl
- Compounds of Formula 54 are prepared by nitration of commercially available 2,5-dimethylphenol 53 as taught in M. Quertani, P. Girard and H. B. Kagan, Tetrahedron Letters, 13, 4315 (1982), Scheme 40.
- R 0 P(CgH 5 ) 3 + (Cl. Br or l)
- R 0 P(O(Cj-C4 alkyl)) 2
- the olefin of Formula Ip can also be prepared by reversing the reactivity of the reactants in the Wittig or Horner-Emmons condensation.
- 2-alkylphenyl derivatives of Formula 56 can be converted into the corresponding dibromo -compounds of Formula 57a as illustrated in Scheme 42 (see Synthesis, (1988), 330).
- the dibromo- compounds can be hydrolyzed to the carbonyl compounds of Formula 57b, which in turn can be condensed with a phosphorus-containing nucleophile of Formula 58 or 59 to afford the olefins of Formula Ip.
- NBS jV-bromosuccinimide 57b
- Carbamates of Formula lu can be prepared by reacting benzyl alcohols of Formula 61 with iso(thio)cyanates of Formula 62 (Scheme 44).
- a base such as triethylamine can be added to catalyze the reaction.
- Compounds of Formula Iw may be prepared by methods described in EP-A- 178,826, EP-A-341,845 and EP-A-464,381.
- a triarylbismuth compound or a substituted phenylboronic acid in the presence of cupric acetate and a tertiary amine such as pyridine or triethylamine as illustrated in Scheme 46.
- organobismuth reagents in the preparation of diary 1 ethers is well known in the art (see Tetrahedron Lett., (1986), 17, 3619, and Tetrahedron Lett., (1987), 18, 887).
- Boronic acids are well known in the literature (see Ada Chem. Scand. 1993, 47, 221 and references therein).
- Step A Preparation of N-(2-methoxy-6-methylphenyl)-2,2- dimethylhvdrazinecarboxamide
- phosgene 108 g, 1.09 moles
- 2-methoxy-6-methylaniline 125.0 g, 911 mmol
- Step B Preparation of 5-chloro-2.4-dihvdro-4-(2-methoxy-6-methylphenyl)-2- methyl-3H-l,2,4-triazol-3-one
- the title compound of Step A (100.0 g, 447.9 mmol) was suspended in ethyl acetate (1 L) and added dropwise, via mechanical pump, over 3.5 h to a stirring solution of phosgene (177 g, 1.79 moles) in ethyl acetate (1.5 L) which was heated at reflux. After the addition was complete, the mixture was heated at reflux for a further 3 h, cooled to room temperature and stirred overnight.
- Step D Preparation of 2.4-dihydro-4-(2-hvdroxy-6-methylphenyl)-5-methoxy-2- methyl-3H- 2.4-triazol-3-one
- tetrahydrofuran 1.5 L
- Step E Preparation of 2.4-dihydro-5-methoxy-2-methyl-4-[6-methyl-2-r3- ftrifluoromethyl phenoxy]phenyll-3H- 1.2.4-triazol-3-one
- 2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-5-methoxy-2-methyl-3H- l,2,4-triazol-3-one (0.50 g, 2.13 mmol)
- methylene chloride 15 mL
- Step B 2,4-dihydro-5-methoxy-2-methyl-4- 2-methyl-6-( ' 2-thienyloxy phenyll-3H-
- 6-OCHF 2 -2-pyridinyl 3-Et-phenyl 1-naphthalenyl 1 ,2,3 ,4-tetrahydro-2-naphthalenyl
- 6-(2,2,2-trifluoroethoxy)-4- 4-(2,2,2-trifluoroethoxy)-2- pyrimidinyl pyrimidinyl pyrimidinyl 3,5-diMe-phenyl 2-naphthalenyl 5,6,7,8-tetrahydro-2-naphthalenyl) 4-OCF 3 -phenyl 3-NBu-phenyl 4-/-Bu-phenyl 6-(2,2,2-trifluoroethoxy)-2- 3-SCF 3 -phenyl 4-SCF 3 -phenyl pyrazinyl 4-CF 3 -6-Me-2-pyridinyl 4 ,6-diMe-2-pyridiny 1 3,5-di(CF 3 )-phenyl 3-(CH 3 C ⁇ C)-phenyl Y -CH 2 0-
- Y -OCH 2 - Z 2-Me-phenyl 2,5-diMe-phenyl 3-CF 3 -phenyl 4-CF -phenyl 4-Me-phenyl 4-?-Bu-phenyl 3-Cl-phenyl 4-Cl-phenyl 2-Me-5-Cl-phenyl 3-?-Bu-phenyl 2-naphthalenyl 1 -naphthalenyl 3 -pyridinyl 4-pyridinyl 6-Me-2-pyridinyl 5,6,7,8-tetrahydro-2-naphthalenyl
- 6-(2,2,2-trifluoroethoxy)-4- 4-(2,2,2-trifluoroethoxy)-2- pyrimidinyl pyrimidinyl pyrimidinyl 3,5-diMe-phenyl 2-naphthalenyl 5,6,7, 8-tetrahydro-2-naphthalenyl) 4-OCF 3 -phenyl 3-Z-Bu-phenyl 4-/-Bu-phenyl 6-(2,2,2-trifluoroethoxy)-2- 3-SCF 3 -phenyl 4-SCF 3 -phenyl pyrazinyl 4-CF 3 -6-Me-2-pyridiny 1 4,6-diMe-2-pyridinyl 3,5-di(CF 3 )-phenyl 3-(CH 3 C ⁇ C)-phenyl Y -CH 2 0-
- 6-(2,2,2-trifluoroethoxy)-4- 4-(2,2,2-trifluoroethoxy)-2- pyrimidinyl pyrimidinyl pyrimidinyl 3,5-diMe-phenyl 2-naphthalenyl 5,6,7,8-tetrahydro-2-naphthalenyl 4-OCF 3 -phenyl 3-t-Bu-phenyl 4-t-Bu-phenyl 6-(2,2,2-trifluoroethoxy)-2- 3-SCF 3 -phenyl 4-SCF 3 -phenyl pyrazinyl 4-CF3-6-Me-2 -pyridinyl 4,6-diMe-2-pyridinyl 3,5-di(CF 3 )-phenyl Y -CH 2 0-
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Abstract
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BR9713415-5A BR9713415A (en) | 1996-11-26 | 1997-11-25 | Method for controlling arthropods, compost, fungicidal composition, arthropodicidal composition and method for controlling plant diseases |
JP52488998A JP2001506984A (en) | 1996-11-26 | 1997-11-25 | Methyl-substituted fungicides and arthropodicides |
AU54633/98A AU5463398A (en) | 1996-11-26 | 1997-11-25 | Methyl substituted fungicides and arthropodicides |
EP97948597A EP0944314A1 (en) | 1996-11-26 | 1997-11-25 | Methyl substituted fungicides and arthropodicides |
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US3361496P | 1996-12-19 | 1996-12-19 | |
US60/033,614 | 1996-12-19 | ||
US4884497P | 1997-06-06 | 1997-06-06 | |
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Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
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US6489487B1 (en) | 1998-08-03 | 2002-12-03 | Sumitomo Chemical Company, Limited | Triazolone derivatives, use thereof, and intermediates therefor |
US6824830B1 (en) * | 1999-10-20 | 2004-11-30 | Aventis Cropscience Gmbh | Wood treatment |
US7144888B2 (en) | 2002-08-08 | 2006-12-05 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
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Also Published As
Publication number | Publication date |
---|---|
EP0944314A1 (en) | 1999-09-29 |
AU5463398A (en) | 1998-06-22 |
CZ184599A3 (en) | 1999-09-15 |
JP2001506984A (en) | 2001-05-29 |
KR20000057254A (en) | 2000-09-15 |
BR9713415A (en) | 2000-04-18 |
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