WO1996017851A1 - Arthropodicidal and fungicidal organosilanes and organogermanes - Google Patents
Arthropodicidal and fungicidal organosilanes and organogermanes Download PDFInfo
- Publication number
- WO1996017851A1 WO1996017851A1 PCT/US1995/015236 US9515236W WO9617851A1 WO 1996017851 A1 WO1996017851 A1 WO 1996017851A1 US 9515236 W US9515236 W US 9515236W WO 9617851 A1 WO9617851 A1 WO 9617851A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- formula
- phenyl
- haloalkyl
- compound
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 6
- 150000001282 organosilanes Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 248
- 238000000034 method Methods 0.000 claims abstract description 70
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 241000238421 Arthropoda Species 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 244000000004 fungal plant pathogen Species 0.000 claims abstract description 5
- -1 phenylethynyl Chemical group 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 15
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 6
- 238000007667 floating Methods 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 235000001508 sulfur Nutrition 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- NHSHFPLRPPZPLA-UHFFFAOYSA-N methyl 2-[2-[[1-[3-[dimethyl(phenyl)silyl]phenyl]ethylideneamino]oxymethyl]phenyl]-2-methoxyiminoacetate Chemical compound C[Si](C=1C=C(C=CC1)C(C)=NOCC1=C(C=CC=C1)C(C(=O)OC)=NOC)(C1=CC=CC=C1)C NHSHFPLRPPZPLA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
- 239000000243 solution Substances 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 239000002585 base Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 241000607479 Yersinia pestis Species 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 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 14
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 0 CC1(*)/C=C(\*C(O*)=O)/C(/N*)=C\C(C)(*)/C=C1 Chemical compound CC1(*)/C=C(\*C(O*)=O)/C(/N*)=C\C(C)(*)/C=C1 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000012038 nucleophile Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 7
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 7
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 7
- 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 7
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 7
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 7
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 7
- 239000005757 Cyproconazole Substances 0.000 description 7
- 239000005758 Cyprodinil Substances 0.000 description 7
- 239000005777 Fenpropidin Substances 0.000 description 7
- 239000005778 Fenpropimorph Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000005839 Tebuconazole Substances 0.000 description 7
- 150000001728 carbonyl compounds Chemical class 0.000 description 7
- 229940125758 compound 15 Drugs 0.000 description 7
- 229940126142 compound 16 Drugs 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- 229940125810 compound 20 Drugs 0.000 description 7
- 229940125833 compound 23 Drugs 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 235000013601 eggs Nutrition 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 7
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000009418 agronomic effect Effects 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 239000012677 causal agent Substances 0.000 description 6
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- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
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- 241001454293 Tetranychus urticae Species 0.000 description 5
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- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
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- 150000002690 malonic acid derivatives Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
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- 241001425390 Aphis fabae Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 230000029936 alkylation Effects 0.000 description 4
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- 238000006073 displacement reaction Methods 0.000 description 4
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- DSYJPVVMWAWYGA-UHFFFAOYSA-N 1-(3-trimethylsilylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC([Si](C)(C)C)=C1 DSYJPVVMWAWYGA-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
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- 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
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07F7/30—Germanium compounds
-
- 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
-
- 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
- A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
-
- 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
-
- 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
Definitions
- This invention relates to certain (hetero)arylsilanes and (hetero)arylgermanes, their N-oxides, agriculturally-suitable salts and compositions, and methods of their use as fungicides and arthropodicides.
- EP-A-398,692 discloses amides of Formula i as fungicides for crop protection.
- Compounds of Formula i are:
- R 1 and R 2 are each hydrogen, lower alkyl, or lower cycloalkyl
- R 3 is lower alkyl, or lower cycloalkyl
- A is, inter alia, a phenyl group or a heterocyclic group optionally substituted with not more than three substituents chosen from, among others, lower alkyl- substituted silyl;
- CA 2,032,045 discloses compounds of Formula ii as fungicides for crop
- R 1 is aryl or heteroaryl
- R 4 and R 5 are, inter alia, aryl or heteroaryl
- each aryl and heteroaryl group can have one or more substituents selected from, among others, tri(C 1-4 alkyl)silyl.
- WO 93/08183 discloses compounds of Formula iii as fungicides for crop protection.
- Compounds of Formula iii are:
- X is N or CH
- R 1 is C 1 -C 4 alkyl
- R 2 and R 3 are, among others, independently C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl,
- each substituted aryl and heteroaryl group is substituted by one, two or three substituents selected from, among others, trimethylsilyl.
- EP-A-596,692 discloses processes to compounds of Formula iv useful as fungicides for crop protection.
- Compounds of Formula iv are:
- A is, inter alia, a phenyl group or a heterocyclic group optionally substituted with substituents chosen from, among others, lower alkylsilyl;
- R 1 and R 2 are independently H or lower alkyl.
- This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural
- compositions containing them and their use as fungicides and arthropodicides are included in compositions containing them and their use as fungicides and arthropodicides:
- A is O; S; N; NR 5 ; or CR 14 ;
- 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 14 and the floating double bond is attached to A;
- W is O; S; NH; N(C 1 -C 6 alkyl); or NO(C 1 -C 6 alkyl);
- X is OR 1 ; S(O m R 1 ; or halogen; R 1 and R 5 are each independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl;
- R 2 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; hydroxy; C 1 -C 2 alkoxy; or acetyloxy;
- R 3 and R 4 are each independently H; halogen; cyano; nitro; hydroxy; C 1 -C 6 alkyl;
- C 1 -C 6 haloalkyl C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 2 -C 6 alkenyloxy; C 2 -C 6 alkynyloxy; C 1 -C 6 alkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; formyl;
- Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring and the moiety on the right side of the linkage is bonded to Z;
- R 6 is independently H or C 1 -C 3 alkyl
- R 7 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; cyano; or morpholinyl;
- Z is phenyl substituted with R 8 , R 9 , and R 10 ; or Z is a 5 to 14-membered aromatic heterocyclic ring system selected from the group monocyclic ring, fused bicyclic ring and fused tricyclic ring, each aromatic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each aromatic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each aromatic ring system substituted with R 8 and optionally substituted with one of R 9 , R 10 , or both R 9 and R 10 ; or Y and Z are taken together to form
- R 3 , Y, and Z are taken together with the phenyl ring to form a naphthalene moiety substituted on either ring with R 8 and on either ring with R 4 ;
- J is -CH 2 -; -CH 2 CH 2 -; -OCH 2 -; -CH 2 O-; -SCH 2 -; -CH 2 S-; -N(R 16 )CH 2 -; or
- R 8 is SiR 19 R 20 R 21 or GeR 19 R 20 R 21 ;
- R 9 is H; 1-2 halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6
- C 3 -C 6 cycloalkyl; C 3 -C 6 alkenyloxy; CO 2 (C 1 -C 6 alkyl); NH(C 1 -C 6 alkyl); N(C 1 -C 6 alkyl) 2 ; -C(R 18 ) NOR 17 ; cyano; nitro; SF 5 ; SiR 22 R 23 R 24 ; or GeR 22 R 23 R 24 ; or R 9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, orpyrimidinyloxy each substituted with R 11 and R 12 ;
- R 10 is H; halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C 4 alkoxy; nitro; or cyano; or R 1 1 and R 12 are each independently H; halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl;
- R 13 is independently C 1 -C 4 alkyl
- R 14 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl;
- R 15 , R 16 , R 17 , and R 18 are each independently H; C 1 -C 3 alkyl; or phenyl
- R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 are each independentiy C 1 -C 6 alkyl; C 1 -C 6
- alkenyl C 1 -C 4 alkoxy; or phenyl
- n are each independently 0, 1 or 2;
- p, r, and s are each independently 0 or 1;
- q 1 or 2;
- R 8 is GeR 19 R 2 ⁇ R 21 .
- alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl 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 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.
- Alkynyloxy includes straight-chain or branched alkynyloxy moieties.
- 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. For example, 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.
- aromatic heterocyclic ring system includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic.
- halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
- 1-2 halogen indicates that one or two of the available positions for that substituent may be halogen.
- alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
- haloalkyl include F 3 C, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 .
- haloalkenyl "haloalkynyl”
- haloalkoxy and the like, are defined analogously to the term “haloalkyl”.
- haloalkynyl include HC ⁇ CCH Cl, CF 3 OC, CCl 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
- haloalkoxy include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
- haloalkylthio include CCl 3 S, CF 3 S, CCl 3 CH 2 S and ClCH 2 CH 2 CH 2 S.
- C i -C j The total number of carbon atoms in a substituent group is indicated by the "C i -C j " prefix where i and j are numbers from 1 to 6.
- C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl.
- alkylcarbonyl examples include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
- Stereoisomers 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).
- the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
- the present invention comprises compounds selected from Formula I, N-oxides 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.
- the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a phenol.
- R 1 , R 2 , and R 5 are each independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; or C 2 -C 4 alkoxycarbonyl.
- preferred alkyl groups include C 1 -C 3 alkyl; preferred haloalkyl groups include C 1 -C 3 haloalkyl; preferred alkenyl groups include allyl; preferred haloalkenyl groups include haloallyl; preferred alkynyl groups include propargyl; preferred haloalkynyl groups include halopropargyl; and preferred cycloalkyl groups include cyclopropyl.
- W is O or S; embodiments where R 3 and R 4 are each independently H, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, or phenyl substituted with R 9 and R 10 ; embodiments where R 9 is other than SF 5 ; and embodiments where R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 are each independently C 1 -C 6 alkyl, C 1 -C 4 alkoxy, or phenyl.
- Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1.
- W is O when E is E 1 ;
- R 1 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl
- R 2 is H; C 1 -C 3 alkyl; C 1 -C 3 haloalkyl; or cyclopropyl;
- R 3 and R 4 are each independently H; halogen; cyano; nitro; C 1 -C 6 alkyl;
- -C(R 7 ) N-O-; -CH 2 OC(O)NH-; or a direct bond;
- R 7 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 alkynyl;
- Z is phenyl substituted with R 8 , R 9 , and R 10 ; or Z is , , , ,
- R 3 , Y, and Z are taken together with the phenyl ring to form a naphthalene moiety substituted on either ring with R 8 and with a floating R 4 ;
- R 9 is H; 1-2 halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 1 -C 6 alkylthio; C 3 -C 6 cycloalkyl; CO 2 (C 1 -C 6 alkyl);
- R 9 is phenyl, phenoxy, pyridinyl, pyridinyloxy, pyrimidinyl, or pyrimidinyloxy each optionally substituted with R 11 and R 12 ;
- R 25 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; or phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano.
- Z is phenyl substituted with R 8 , R 9 , and R 10 ; or Z is Z-1 to Z-21, each substituted with R 8 and optionally substituted with one of R 9 , R 10 , or both R 9 , and R 10 ; or
- J is -CH 2 - or -CH 2 CH 2 -;
- R 1 is C 1 -C 3 alkyl
- R 2 is H or C 1 -C 2 alkyl
- R 7 is H; C 1 -C 3 alkyl; or C 1 -C 3 haloalkyl; and
- Z is phenyl substituted with R 8 , R 9 , and R 10 ; or Z is Z-16, Z-18, or Z-1, each substituted with R 8 and optionally substituted with one of R 9 .
- R 10 or both R 9 and R 10 .
- E is E 1 ;
- A is O or NR 5 ;
- G is C
- R 7 is H; C 1 -C 2 alkyl; or C 1 -C 2 haloalkyl.
- E is E 1 ;
- A is N or CR 14 ;
- G is N
- R 7 is H; C 1 -C 2 alkyl; or C 1 -C 2 haloalkyl.
- E is E 2 , E 3 , E 4 , E 5 , or E 6 .
- R 1 is methyl
- R 2 is methyl
- Z is phenyl substituted with R 8 , R 9 , and R 10 .
- This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula I and at least one of a surfactant, a solid diluent or a liquid diluent.
- fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula I 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 Formula I (e.g., as a composition described herein).
- a fungicidally effective amount of the compounds of Formula I 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
- 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 Formula I (e.g., as a composition described herein).
- the preferred methods of use are those involving the above preferred compounds.
- the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-30.
- the definitions of E, A, G, W, X, Y, Z, J, R 1 -R 24 , m, n, p, r, s and q in the compounds of Formulae 1-44d below are as defined above in the Summary of the Invention.
- a compound of Formula I wherein E is E 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 E-moiety amide ring 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,
- ketones such as acetone or 2-butanone
- hydrocarbons such as toluene or benzene
- halocarbons such as dichloromethane or chloroform.
- trimethylsilyldiazomethane (CH 3 ) 3 Si) on compounds of Formuli 1 (Method 1).
- a protic cosolvent such as methanol.
- trichloroacetimidates of Formula 3 and a Lewis acid catalyst.
- 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), 20, 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. Deng, Angew. Chem., Int. Ed. Engl., (1981), 20, 798).
- Appropriate bases include alkali metal alkoxides such as potassium tm-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine,
- DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
- DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
- triethylenediamine 1,8-diazabicyclo[5.4.0]undec-7-ene
- Formula 5 with an ambident nucleophile of Formula 6 (Scheme 2).
- 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.
- the preparation of the malonate esters of Formula 5 can be prepared by methods described hereinafter.
- Compounds of Formula laa can be prepared by reaction of nitrile esters of Formula 5b with ambident nucleophiles of Formula 6. See M. Scobie and G. Tennant, J. Chem. Soc, Chem.
- Alkylation of laa with alkyl halides in the presence of base provides compounds of Formula lab.
- treatment of laa with alkylamines or alkoxyamines provides compounds of Formula lab.
- Esters of Formula 5a can be prepared from copper (I)-catalyzed reaction of malonate esters of Formula 7 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.
- malonate esters of Formula 5a can be prepared by treating phenyl acetic acid esters of Formula 9 with a dialkyl carbonate or alkyl chloroformate 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 5b can be prepared similarly from compounds of Formula 10.
- Esters of Formula 9 can be prepared from acid-catalyzed alcoholysis of phenyl acetonitriles of Formula 10 or by estenfication 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 9a can also be prepared by
- esters of Formula 9 can also be prepared by forming the Y 2 bridge using conventional nucleophilic substitution chemistry (Scheme 7). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 15 or 16 with a nucleophilic ester of Formula 14 affords compounds of Formula 9b.
- a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compound of Formula 14.
- the leaving group Lg 1 in the amides of Formula 17 is any group known in the art to undergo a displacement reaction of this type. Examples of suitable leaving groups include chlorine, bromine, and sulfonyl and sulfonate groups. Examples of suitable inert solvents are dimethylformamide or dimethyl sulfoxide.
- Compounds of Formula 17a can be prepared from compounds of Formula lb (compounds of Formula 1 wherein X is OH) by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding
- compounds of Formula lb can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, p-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 17a.
- the reaction with the sulfonyl halides may be performed in the presence of a suitable base
- sulfonyl compounds of Formula 17b can be prepared by oxidation of the corresponding thio compound of Formula 18 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 mer ⁇ -chloro-peroxybenzoic acid, hydrogen peroxide and Oxone® (KHSO 5 ).
- the diacyl compound of Formula 19 is treated with excess of a thionyl halide such as thionyl chloride.
- the product formed first is the ring-closed compound of Formula 20 which can be isolated or converted in situ to the compound of Formula 17c; see P. Molina, A. Ta ⁇ aga, A.
- the hydrazides of Formula 19 can be prepared as illustrated in Scheme 13. Condensation of the isocyanate of Formula 21 with the hydrazine of Formula H 2 NNR 2 R 27 in an inert solvent such as tetrahydrofuran affords the hydrazide.
- Ketene dithioacetals of Formula 22a or 22b can be prepared by condensing phenyl acetic acid esters of Formula 9 or amides of Formula 9a, respectively, with carbon disulfide in the presence of a suitable base, followed by reaction with two equivalents of an R 1 -halide, such as iodomethane orpropargyl bromide (Scheme 15). Conversion of 22b to 22c can be accomplished by reaction with trialkyl tetrafluoroborates.
- the carbonylating agents of Formula 24 are carbonyl or thiocarbonyl transfer reagents such as phosgene, thiophosgene, diphosgene
- the compounds of Formula 24 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 te rt-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or
- alkali metal alkoxides such as potassium te rt-butoxide
- inorganic bases such as sodium hydride and potassium carbonate
- pyridine or tertiary amines such as triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or
- Suitable solvents include polar aprotic solvents such as acetonitrile, dimethylformamide, or dimethyl sulfoxide; ethers such as tetrahydrofuran,
- 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.
- N-Amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17. Treatment of an aniline of Formula 25 with phosgene, thiophosgene,
- N,N'-carbonyldiimidazole, or N,N'-thiocarbonyldiimidazole produces the isocyanate or isothiocyanate of Formula 26.
- 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 23.
- 2-halocarboxylic acid chlorides 2-halocarboxylic acid esters or 2-haloacyl imidazoles.
- the initial acylation on the aniline nitrogen is followed by an intramolecular displacement of the 2-halo group to effect cyclization.
- Base may be added to accelerate the acylation and/or the subsequent cyclization.
- Suitable bases include triethylamine and sodium hydride.
- Formula lb compounds can be prepared by reaction of
- Formula 26 iso(thio)cyanates or Formula 26a carbodiimides with Formula 28a esters.
- base may be added to accelerate the reaction and subsequent cyclization to Formula lb compounds.
- Carbodiimides 26a can be prepared as shown in Scheme 18, starting with compounds of Formula 26.
- the (thio)ureas or amidines of Formula 27 can be prepared by either of the methods illustrated in Scheme 19.
- an iso(thio)cyanate of Formula 26 or carbodiimide of Formula 26a 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 25 and 26, respectively, are commercially available or prepared by well-known methods.
- isothiocyanates can be prepared by methods described in J. Heterocycl. Chem., (1990), 27, 407.
- Isocyanates can be prepared as described in March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp 944, 1166.
- thionating reagents such as P 2 S 5 or Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide]
- 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.
- Benzyl halides of Formula 29 can be prepared by radical halogenation of the corresponding alkyl compound (i.e., H instead of halogen in Formula 29), or by acidic cleavage of the corresponding methyl ether (i.e., OMe instead of halogen in Formula 29).
- Formula 14a provides compounds of Formula Iff.
- the olefins of Formula Ig can be converted to the saturated compounds of Formula Hi by hydrogenation over a metal catalyst such palladium on carbon as is well-known in the art (Rylander, Catalytic Hydrogenation in Organic Synthesis;
- the olefin of Formula Ig can also be prepared by reversing the reactivity of the reactants in the Wittig or Horner-Emmons condensation.
- 2-alkylphenyl derivatives of Formula 31 can be converted into the corresponding dibromo-compounds of Formula 33 as illustrated in Scheme 23 (see Synthesis, (1988), 330).
- the dibromo-compounds can be hydrolyzed to the carbonyl compounds of Formula 34, which in tum can be condensed with a phosphorus-containing nucleophile of Formula 35 or 36 to afford the olefins of Formula Ig.
- Carbamates of Formula Ik can be prepared by reacting benzyl alcohols of Formula 38 with isocyanates of Formula 39 (Scheme 25). A base such as triethylamine can be added to catalyze the reaction.
- Scheme 26 may be prepared by methods described in WO 93/15046.
- Silicon- or germanium-containing compounds can be prepared using methods well-known in the art.
- Conventional references on the art of preparing silyl- and germyl-substituted compounds see The Organic Compounds of Germanium, Michel Lesabre, Pierre Mazerolles, and Jacques Satgé, Dietmar Seyferth, ed., John Wiley & Sons, NY; C. Eaborn and K. C. Pande, J. Chem. Soc. (1960) 3200-3203; M. Wieber and
- a second method is deprotonation of compounds of Formula 40b using a strong base such as a lithioamide or an organolithium reagent, followed by treatment with a silyl- or germyl-halide of Formula 42.
- a strong base such as a lithioamide or an organolithium reagent
- these methods may require protection and deprotection sequences for certain V moieties which may be incompatible with the reagents. See the preparation of Intermediate 1 in the Examples for an example of a protection-deprotection strategy.
- One skilled in the art would also recognize that, in some cases, additional synthetic steps after the introduction of R 8 would be necessary to prepare a particular V group as it is depicted in any individual scheme. See the preparation of Intermediate 2 in the Examples for an example of this strategy.
- Formula 41 which would be coupled to another moiety to provide a third molecule which could be elaborated further to provide compounds of Formula I.
- R 8 can be introduced as a substituent on a reagent of Formula 41 which can be elaborated further to provide the compounds of this invention or their precursors.
- a more specific illustration of the strategy for introduction of R 8 into compounds of Formula I is shown in Scheme 29 (see below). This Scheme illustrates an example of preparation of Z-OH in Scheme 21 followed by coupling to give compounds of the invention.
- R 8 can be introduced as the final step in which compounds of Formula I are prepared from compounds of Formula 42a or b (see Scheme 28).
- Compounds of Formula Io can be made using a protection/deprotection scheme to prepare the requisite phenols of Formula 44d. Protection of the halophenol, followed by electrophilic substitution by R 8 and then deprotection yields compounds of Formula 44d which are coupled to compounds of Formula 29 in refluxing methyl ethyl ketone (MEK, or a similar solvent) in the presence of a base (preferably potassium carbonate) to give compounds of Formula Io.
- MEK methyl ethyl ketone
- protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products.
- the use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991).
- One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I.
- Step B The title compound of Step B (31.5 g) was added to a solution of HCl in methanol (prepared by adding 20 mL of acetyl chloride slowly to 200 mL of methanol). The mixture was heated to 60°C for 1.5 h. The solvent was removed in vacuo. The residue was taken up in 100 mL of diethyl ether and stirred at room temperature for 30 min. The ether was decanted off and the solid was taken up in 100 mL of tetrahydrofuran and heated to ⁇ 50°C. The mixture was then cooled in an ice water bath and the solid collected by filtration to provide 11.5 g (47% yield) of the title compound of Step C as a white solid melting at 169- 170°C.
- Step D Methyl 2-[[[[[1-[3-
- Step E Dimethyl [2-[[[[[1-[3- (trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]propanedioate
- Step D The title compound of Step D (2.1 g) was dissolved in 10 mL of dimethyl carbonate. A slurry of 455 mg of sodium hydride (60% oil dispersion) in 10 mL of tetrahydrofuran was added and the mixture was heated to reflux 3 h. The mixture was cooled, quenched with 15 mL of 1N HCl solution and extracted with ethyl acetate (3x25 mL). The combined organic layers were dried (MgSO 4 ), filtered and concentrated in vacuo to yield 2.8 g of crude product, the title compound of Step E, as an amber oil.
- Step F 5-Methoxy-2-methyl-4-[2-[[[[[ 1-[3- (trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3(2H)-isoxazolone
- N-methylhydroxylamine hydrochloride (1.43 g) was dissolved in 25 mL of methanol.
- a solution of 1.92 g of potassium hydroxide dissolved in 25 mL of methanol was added while cooling the reaction mixture with an ice bath. After 15 minutes, the precipitated potassium chloride was removed by filtration. To the filtrate was added a solution of 2.8 g of the title compound of Step E in 10 mL of methanol. The resulting mixture was stirred at room temperature overnight.
- Step A 2.2-Dimethyl-N-(2-methylphenyl)hydrazinecarboxamide
- o-Tolyl isocyanate (10.0 g) was dissolved in 75 mL of toluene under nitrogen. The solution was cooled to 5°C and to this solution was slowly added a solution in toluene of 1,1 -dimethylhydrazine (5.7 mL). After the addition, the ice-bath was removed and the resulting slurry allowed to stir an additional 10 minutes. The solid was filtered off and rinsed successively with hexane, a small amount of 20% diethyl ether/hexane, and then hexanes again. This afforded 11.1 g (77%) of the title compound of Step A.
- Step B 5-Chloro 2,4-dihydro-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-one
- Step D 4-[2-(Bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol- 3-one
- N-bromosuccinimide (6.53 g) followed by a catalytic amount of benzoyl peroxide.
- the solution was heated at reflux for 2 h.
- Another 1.63 g of N-bromosuccinimide and a catalytic amount of benzoyl peroxide were added and the solution was heated at reflux for an hour.
- methylene chloride was added and the organic layer was washed successively with water, 0.1 ⁇ sodium thiosulfate solution, and then saturated aqueous NaCl.
- Step E 2,4-Dihydro-5-methoxy-2-methyl-4-[2-[[[[[1-[3- (trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3- one
- Step A Methyl 2-[[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]methyl]- ⁇ - (methoxyimino)benzeneacetate
- Triethylamine (2.8 mL) was added to a solution of 5 g of methyl 2-(bromomethyl)- ⁇ -(methoxyimino)benzeneacetate and 2.83 g of N-hydroxy-phthalimide in 12 mL of N-methylpy ⁇ olidone.
- the reaction mixture was stirred at room temperature for 72 h and then poured into 75 mL of ice water. The precipitate was removed by filtration and redissolved in methylene chloride. The organic phase was washed with 30 mL of water, dried (MgSO 4 ), filtered and concentrated in vacuo to yield 5.0 g (80% yield) of the title compound of Step A as a gray powder melting at 103-105°C. 1 ⁇ ⁇ MR (CDCl 3 ):
- Step B 2-[( Aminooxy)methyl]- ⁇ -(methoxyimino)-N-methyl-benzeneacetamide
- Step A The title compound of Step A (5.0 g) was dissolved in 33 mL of 40% aqueous methylamine solution and heated to reflux for 4 hours. The solution was cooled and extracted with methylene chloride (3 ⁇ 30 mL) and the organic phase was washed with 30 mL of water. The organic phase was dried (MgSO 4 ), filtered and concentrated in vacuo to yield 5 g of a dark amber oil. Trituration in methyl tert-butyl ether/hexane provided 1.1 g (34% yield) of the title compound of Step B as an off-white solid melting at 91-93°C.
- Step C ⁇ -(Methoxyimino)-N-methyl-2-[[[[1-[3- (trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]benzeneacetamide
- Step C 1-[4-(Trimethylgermyl)phenyl]ethanone oxime
- Step D Methyl ⁇ -(methoxymethylene)-2-[[[[1-[4-
- Step C The title compound of Step C (0.13 g, 0.52 mmol) was dissolved in DMF (3 mL), treated with sodium hydride (0.02 g, 0.8 mmol) [60% mineral oil dispersion], and then stirred at room temperature for 30 min.
- Methyl 2-(bromomethyl)- ⁇ - (methoxymethylene)benzeneacetate (0.15 g, 0.52 mmol) was dissolved in DMF (3 mL) and added to the above solution. The mixture was stirred overnight, then poured into water (55 mL) and extracted with diethyl ether (5 ⁇ 50 mL) and once with ethyl acetate (50 mL).
- Step A Methyl ⁇ -(methoxyimino)-2-[[[[1-[3- (trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]benzeneacetate
- Step A (4-Bromo-2-methylphenoxy)(1,1-dimethylethyl)dimethylsilane
- Step B ( 1,1-Dimethylethyl)dimethy][2-methyl-4-(trimethylgermyl)phenoxy]silane
- Step D Methyl ⁇ -(methoxyimino)-2-[[2-methyl-4- (trimethylgermyl)phenoxy]methyl]benzeneacetate
- Step C The title compound of Step C was dissolved in 30 mL of 2-butanone. 0.5 g of finely ground (mortar and pestle) potassium carbonate was added followed by 0.5 g of methyl 2-(bromomethyl)- ⁇ -(methoxyimino)benzeneacetate and the resulting mixture was heated to reflux overnight. Evaporation of the solvent in vacuo was followed by partitioning between water and ethyl acetate. The resulting aqueous phase was extracted with ethyl acetate and diethyl ether.
- finely ground (mortar and pestle) potassium carbonate was added followed by 0.5 g of methyl 2-(bromomethyl)- ⁇ -(methoxyimino)benzeneacetate and the resulting mixture was heated to reflux overnight. Evaporation of the solvent in vacuo was followed by partitioning between water and ethyl acetate. The resulting aqueous phase was extracted with ethyl acetate and diethyl ether.
- Step B 1-[3-(Trimethylsilyl)phenyl]ethanone (Intermediate 1)
- Step C 1-[3-(Trimethylsilyl)phenyl]ethanone oxime (Intermediate 2)
- TMS trimethylsilyl
- TBDMS t-BuMe 2 Si.
- composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
- the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
- Useful formulations include liquids such as solutions (including emulsifiable
- Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble.
- Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation;
- the entire formulation of active ingredient can be encapsulated (or
- Encapsulation can control or delay release of the active ingredient.
- Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare.
- High-strength compositions are primarily used as intermediates for further formulation.
- the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
- Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
- Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, NN-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and
- Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
- Liquid diluents include, for example, water,
- Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding a in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry 's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in
- the compounds of this invention are useful as plant disease control agents.
- the present invention therefore further comprises a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, or to the plant seed or seedling to be protected, an effective amount of a compound of the invention or a fungicidal composition containing said compound.
- the compounds and compositions of this invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These pathogens include Plasmopara viticola, Phytophthora infestans,
- Peronospora tabacina Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium oxysporum, Verticillium dahliae, Pythium
- the compounds of this invention also exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, stem or root feeding, seed-feeding, aquatic and
- arthropods includes insects, mites and nematodes which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the an will appreciate that not all compounds are equally effective against all growth stages of all pests.
- all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders Thysanoptera, Orthoptera and
- the compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes.
- the compounds are active against southern corn rootworm (Diabrotica undecimpunctata howard ⁇ ), aster leafhopper (Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall army worm (Spodopterafrugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypif), Russian wheat aphid (Diuraphis noxia), English grain aphid (Sitobion avenae), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatellafurcifer ⁇ ), green leafhopper (Nephotettix cincticeps), brown plant
- Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banksi and Oligonychus pratensis;
- Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus calif ornicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 and WO 92/00673 for more detailed pest descriptions.
- insecticides fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
- insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, fonophos, imidacloprid, isofenphos, malathion,
- insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, deltame
- metaldehyde methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, rotenone, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides such as azoxystrobin (ICIA5504), benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper
- mixtures of a compound of the invention with a fungicide selected from the group cyproconazole, cyprodinil (CGA 219417), epoxyconazole (BAS 480F), fenpropidin, fenpropimorph, flusilazole and tebuconazole.
- a fungicide selected from the group cyproconazole, cyprodinil (CGA 219417), epoxyconazole (BAS 480F), fenpropidin, fenpropimorph, flusilazole and tebuconazole.
- a fungicide selected from the group cyproconazole, cyprodinil (CGA 219417), epoxyconazole (BAS 480F), fenpropidin, fenpropimorph, flusilazole and tebuconazole.
- compound numbers refer to compounds in Index Tables A-E
- compound numbers refer to compounds in Index Tables A-E
- CGA 219417 compound 2 and epoxyconazole (BAS 480F); compound 2 and fenpropidin; compound 2 and fenpropimorph; compound 2 and flusilazole; compound 2 and tebuconazole; compound 15 and cyproconazole; compound 15 and cyprodinil (CGA 219417); compound 15 and epoxyconazole (BAS 480F); compound 15 and fenpropidin; compound 15 and fenpropimorph; compound 15 and flusilazole;
- compound 15 and tebuconazole compound 16 and cyproconazole; compound 16 and cyprodinil (CGA 219417); compound 16 and epoxyconazole (BAS 480F); compound 16 and fenpropidin; compound 16 and fenpropimorph; compound 16 and flusilazole;
- compound 20 and tebuconazole compound 23 and cyproconazole; compound 23 and cyprodinil (CGA 219417); compound 23 and epoxyconazole (BAS 480F); compound 23 and fenpropidin; compound 23 and fenpropimorph; compound 23 and flusilazole; and compound 23 and tebuconazole.
- Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing.
- the compounds can also be applied to the seed to protect the seed and seedling.
- rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions.
- Foliage can normally be protected when treated at a rate of from less than 1 g/ha to 5,000 g/ha of active ingredient.
- Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed.
- Arthropod pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
- the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of the invention, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
- a preferred method of application is by spraying.
- granular formulations of these compounds can be applied to the plant foliage or the soil.
- Other methods of application include direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others.
- the compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.
- the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
- a preferred method o application involves spraying a water dispersion or refined oil solution of the compound Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.
- the rate of application required for effective control will depend on such factors a the species of arthropod to be controlled, the pest's life cycle, life stage, its size, locationo time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg hectar may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient o as much as 150 mg/square meter may be required.
- control efficacy represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding.
- pathogen and arthropod pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-E for compound descriptions.
- Test compounds were first dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem ® 014 (polyhydric alcohol esters). The resulting test suspensions were then used in Tests A-F. Spraying these 200 ppm test suspensions to the point of run-off on the test plants is the equivalent of a rate of 500 g/ha.
- test suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore dust of Erysiphe graminis f sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at 20°C for 7 days, after which disease ratings were made.
- TESTB Erysiphe graminis f sp. tritici
- test suspension was sprayed to the point of run-off on wheat seedlings.
- seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made.
- Puccinia recondita the causal agent of wheat leaf rust
- test suspension was sprayed to the point of run-off on rice seedlings.
- seedlings were inoculated with a spore suspension of Pyricularia oryzae (the causal agent of rice blast) and incubated in a saturated atmosphere at 27°C for 24 h, and then moved to a growth chamber at 30°C for 5 days, after which disease ratings were made.
- Pyricularia oryzae the causal agent of rice blast
- test suspension was sprayed to the point of run-off on tomato seedlings.
- seedlings were inoculated with a spore suspension of Phytophthora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth, chamber at 20°C for 5 days, after which disease ratings were made.
- Phytophthora infestans the causal agent of potato and tomato late blight
- test suspension was sprayed to the point of run-off on grape seedlings.
- seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 h, moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 h, after which disease ratings were made.
- Plasmopara viticola the causal agent of grape downy mildew
- test suspension was sprayed to the point of run-off on cucumber seedlings.
- seedlings were inoculated with a spore suspension of Botrytis cinerea (the causal agent of gray mold on many crops) and incubated in a saturated atmosphere at 20°C for 48 h, and moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
- Botrytis cinerea the causal agent of gray mold on many crops
- Results for Tests A-F are given in Table A.
- a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control (relative to the controls).
- a dash (-) indicates no test results.
- ND indicates disease control not determined due to phytotoxicity.
- Test units each consisting of a H.I.S. (high impact styrene) tray with 16 cells were prepared. Wet filter paper and approximately 8 cm 2 of lima bean leaf was placed into twelve of the cells. A 0.5-cm layer of wheat germ diet was placed into the four remaining cells. Fifteen to twenty third-instar larvae of fall armyworm (Spodoptera frugiperda) were placed into a 230-mL (8-ounce) plastic cup. Solutions of each of the test compounds in 75:25 acetone-distilled water solvent were sprayed into the tray and cup.
- H.I.S. high impact styrene
- Spraying was accomplished by passing the tray and cup on a conveyer belt directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.14 kilograms of active ingredient per hectare (about 0.14 pounds per acre) at 207 kPa (30 p.s.i.).
- the insects were transferred from the 230-mL cup to the H.I.S. tray (one insect per cell).
- the trays were covered and held at 27°C and 50% relative humidity for 48 hours, after which time readings were taken on the twelve cells with lima bean leaves. The four remaining cells were read at 6-8 days for delayed toxicity.
- the following gave control efficacy levels of 80% or greater: 13, 21, and 22.
- Test units each consisting of a 230-mL (8-ounce) plastic cup containing a 6.5-cm 2 (1-square-inch) plug of a wheatgerm diet, were prepared. The test units were sprayed as described in TEST G with individual solutions of the test compounds. After the spray on the cups had dried, five second-instar larvae of the southern corn rootworm (Diabrotica undecimpunctata howardi) were placed into each cup. The cups were held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. The same units were read again. at 6-8 days for delayed toxicity. Of the compounds tested, the following gave control efficacy levels of 80% or greater: 11, 19, and 22.
- Pieces of kidney bean leaves each approximately 6.5 cm 2 (1 square inch) in area, that had been infested on the undersides with 25 to 30 adult mites (Tetranychus urticae), were sprayed with their undersides facing up on a hydraulic sprayer with a solution of the test compound in 75:25 acetone-distilled water solvent. Spraying was accomplished by passing the leaves, on a conveyor belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.14 kilograms of active ingredient per hectare (about 0.14 pounds per acre) at 207 kPa (30 p.s.i.).
- the leaf squares were then placed underside-up on a square of wet cotton in a petri dish and the perimeter of the leaf square was tamped down onto the cotton with forceps so that the mites could not escap onto the untreated leaf surface.
- the test units were held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 7, 10, 11, 13, 19, 21, 22, 24, and 25.
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95940809A EP0869963A1 (en) | 1994-12-08 | 1995-11-28 | Arthropodicidal and fungicidal organosilanes and organogermanes |
AU42438/96A AU4243896A (en) | 1994-12-08 | 1995-11-28 | Arthropodicidal and fungicidal organosilanes and organogermanes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US35200294A | 1994-12-08 | 1994-12-08 | |
US08/352,002 | 1994-12-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996017851A1 true WO1996017851A1 (en) | 1996-06-13 |
Family
ID=23383379
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1995/015236 WO1996017851A1 (en) | 1994-12-08 | 1995-11-28 | Arthropodicidal and fungicidal organosilanes and organogermanes |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0869963A1 (en) |
AU (1) | AU4243896A (en) |
IL (1) | IL115894A0 (en) |
WO (1) | WO1996017851A1 (en) |
ZA (1) | ZA959560B (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997000612A1 (en) * | 1995-06-20 | 1997-01-09 | E.I. Du Pont De Nemours And Company | Arthropodicidal and fungicidal cyclic amides |
WO1998005652A2 (en) * | 1996-08-01 | 1998-02-12 | E.I. Du Pont De Nemours And Company | Arthropodicidal and fungicidal cyclic amides |
WO1998020003A1 (en) * | 1996-11-01 | 1998-05-14 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
WO1998023156A1 (en) * | 1996-11-26 | 1998-06-04 | E.I. Du Pont De Nemours And Company | Methyl substituted fungicides and arthropodicides |
US6057352A (en) * | 1995-05-17 | 2000-05-02 | E. I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
US6096895A (en) * | 1995-05-17 | 2000-08-01 | E. I. Du Pont De Nemours And Company | Heterocyclic dihydrazole compounds and their use for controlling fungal plant diseases |
US6469209B1 (en) | 1999-07-05 | 2002-10-22 | Dongbu Hannong Chemical Co., Ltd. | Acrylate-type fungicide |
CN106431977A (en) * | 2015-08-12 | 2017-02-22 | 沈阳中化农药化工研发有限公司 | Unsaturated oxime ether compound and application thereof |
CN112661732A (en) * | 2020-12-23 | 2021-04-16 | 湖南加法检测有限公司 | Furanol derivative and preparation method and application thereof |
CN115836049A (en) * | 2020-07-08 | 2023-03-21 | 巴斯夫欧洲公司 | Use of strobilurin-type compounds to control phytopathogenic fungi containing the amino acid substitution F129L in the mitochondrial cytochrome b protein conferring tolerance to Qo inhibitor VI |
Citations (4)
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EP0398692A2 (en) * | 1989-05-17 | 1990-11-22 | SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. | Alkoxyiminoacetamide derivatives and their use as fungicides |
EP0433233A1 (en) * | 1989-12-14 | 1991-06-19 | Ciba-Geigy Ag | Heterocyclic compounds |
EP0596692A2 (en) * | 1992-11-02 | 1994-05-11 | Shionogi Seiyaku Kabushiki Kaisha | A process for producing (E)-alkoxyimino or hydroxyiminoacetamide compounds and intermediates therefor |
WO1994026700A1 (en) * | 1993-05-18 | 1994-11-24 | Ciba-Geigy Ag | O-benzyl oxime ether derivatives and their use as pesticides |
-
1995
- 1995-11-06 IL IL11589495A patent/IL115894A0/en unknown
- 1995-11-10 ZA ZA959560A patent/ZA959560B/en unknown
- 1995-11-28 EP EP95940809A patent/EP0869963A1/en not_active Ceased
- 1995-11-28 AU AU42438/96A patent/AU4243896A/en not_active Abandoned
- 1995-11-28 WO PCT/US1995/015236 patent/WO1996017851A1/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0398692A2 (en) * | 1989-05-17 | 1990-11-22 | SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. | Alkoxyiminoacetamide derivatives and their use as fungicides |
EP0433233A1 (en) * | 1989-12-14 | 1991-06-19 | Ciba-Geigy Ag | Heterocyclic compounds |
EP0596692A2 (en) * | 1992-11-02 | 1994-05-11 | Shionogi Seiyaku Kabushiki Kaisha | A process for producing (E)-alkoxyimino or hydroxyiminoacetamide compounds and intermediates therefor |
WO1994026700A1 (en) * | 1993-05-18 | 1994-11-24 | Ciba-Geigy Ag | O-benzyl oxime ether derivatives and their use as pesticides |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6057352A (en) * | 1995-05-17 | 2000-05-02 | E. I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
US6096895A (en) * | 1995-05-17 | 2000-08-01 | E. I. Du Pont De Nemours And Company | Heterocyclic dihydrazole compounds and their use for controlling fungal plant diseases |
WO1997000612A1 (en) * | 1995-06-20 | 1997-01-09 | E.I. Du Pont De Nemours And Company | Arthropodicidal and fungicidal cyclic amides |
WO1998005652A2 (en) * | 1996-08-01 | 1998-02-12 | E.I. Du Pont De Nemours And Company | Arthropodicidal and fungicidal cyclic amides |
WO1998005652A3 (en) * | 1996-08-01 | 1998-06-11 | E I De Pount De Nemours And Co | Arthropodicidal and fungicidal cyclic amides |
WO1998020003A1 (en) * | 1996-11-01 | 1998-05-14 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
WO1998023156A1 (en) * | 1996-11-26 | 1998-06-04 | E.I. Du Pont De Nemours And Company | Methyl substituted fungicides and arthropodicides |
US6469209B1 (en) | 1999-07-05 | 2002-10-22 | Dongbu Hannong Chemical Co., Ltd. | Acrylate-type fungicide |
CN106431977A (en) * | 2015-08-12 | 2017-02-22 | 沈阳中化农药化工研发有限公司 | Unsaturated oxime ether compound and application thereof |
CN115836049A (en) * | 2020-07-08 | 2023-03-21 | 巴斯夫欧洲公司 | Use of strobilurin-type compounds to control phytopathogenic fungi containing the amino acid substitution F129L in the mitochondrial cytochrome b protein conferring tolerance to Qo inhibitor VI |
CN112661732A (en) * | 2020-12-23 | 2021-04-16 | 湖南加法检测有限公司 | Furanol derivative and preparation method and application thereof |
CN112661732B (en) * | 2020-12-23 | 2023-08-04 | 湖南化研院检测技术有限公司 | Furanol derivative and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
AU4243896A (en) | 1996-06-26 |
EP0869963A1 (en) | 1998-10-14 |
IL115894A0 (en) | 1996-01-31 |
ZA959560B (en) | 1997-05-12 |
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