WO2011087837A2 - Fungicidal 2-(bicyclic aryloxy)carboxamides - Google Patents
Fungicidal 2-(bicyclic aryloxy)carboxamides Download PDFInfo
- Publication number
- WO2011087837A2 WO2011087837A2 PCT/US2010/061765 US2010061765W WO2011087837A2 WO 2011087837 A2 WO2011087837 A2 WO 2011087837A2 US 2010061765 W US2010061765 W US 2010061765W WO 2011087837 A2 WO2011087837 A2 WO 2011087837A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oxy
- compound
- alkyl
- naphthalenyl
- dimethylethyl
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 90
- 150000003857 carboxamides Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 297
- 239000000203 mixture Substances 0.000 claims abstract description 161
- 201000010099 disease Diseases 0.000 claims abstract description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000000417 fungicide Substances 0.000 claims description 245
- -1 Ci-C6 alkyl Chemical group 0.000 claims description 139
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 239000007787 solid Substances 0.000 claims description 58
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 26
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 20
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
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- 125000006519 CCH3 Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
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- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 10
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
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- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
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- 244000000004 fungal plant pathogen Species 0.000 claims description 7
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 7
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 6
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- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 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
- PTUNHAVZBPLAGF-UHFFFAOYSA-N 2-methoxy-n-(1-methoxy-2-methylpropan-2-yl)-2-(7-prop-1-ynylnaphthalen-2-yl)oxyacetamide Chemical compound C1=CC(C#CC)=CC2=CC(OC(OC)C(=O)NC(C)(C)COC)=CC=C21 PTUNHAVZBPLAGF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 4
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- VSXKFUXTBIZMRK-UHFFFAOYSA-N 2-(7-ethynylnaphthalen-2-yl)oxy-n-(2-methylpent-3-yn-2-yl)butanamide Chemical compound C1=CC(C#C)=CC2=CC(OC(CC)C(=O)NC(C)(C)C#CC)=CC=C21 VSXKFUXTBIZMRK-UHFFFAOYSA-N 0.000 claims description 3
- CSWZPNPUZXAVMT-UHFFFAOYSA-N 2-(7-methoxynaphthalen-2-yl)oxy-n-prop-2-enylpropanamide Chemical compound C1=CC(OC(C)C(=O)NCC=C)=CC2=CC(OC)=CC=C21 CSWZPNPUZXAVMT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 3
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 2
- CITSQYUPXSLORQ-UHFFFAOYSA-N 2-(7-bromonaphthalen-2-yl)oxy-n-[1-(dimethylaminomethylideneamino)-2-methylpropan-2-yl]butanamide Chemical compound C1=CC(Br)=CC2=CC(OC(CC)C(=O)NC(C)(C)CN=CN(C)C)=CC=C21 CITSQYUPXSLORQ-UHFFFAOYSA-N 0.000 claims description 2
- LLLYBRUKEGAQAC-UHFFFAOYSA-N 2-(7-ethoxynaphthalen-2-yl)oxy-n-(2-methylbut-3-yn-2-yl)butanamide Chemical compound C1=CC(OC(CC)C(=O)NC(C)(C)C#C)=CC2=CC(OCC)=CC=C21 LLLYBRUKEGAQAC-UHFFFAOYSA-N 0.000 claims description 2
- FOSYPSGVFYGWQG-UHFFFAOYSA-N n-(1-methoxy-2-methylpropan-2-yl)-2-(7-prop-1-ynylnaphthalen-2-yl)oxybutanamide Chemical compound C1=CC(C#CC)=CC2=CC(OC(CC)C(=O)NC(C)(C)COC)=CC=C21 FOSYPSGVFYGWQG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 244000053095 fungal pathogen Species 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 204
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 103
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- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
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- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/21—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with the sulfur atom of the thio group bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/30—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/42—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/62—Isoquinoline or hydrogenated isoquinoline ring systems
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- This invention relates to certain bicyclic aryloxy carboxamides, their N-oxides, salts and compositions, and methods of their use as fungicides.
- World Patent Publication WO 2008/110355 discloses certain bicyclic aryloxy carboxamides as fungicides.
- This invention is directed to compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as fungicides:
- Q is O or S
- Z 1 and Z 2 are each independently CR 9 or ⁇ ;
- R 1 is C 1 -C 2 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4
- haloalkenyl C 2 -C 4 haloalkynyl, C 3 -C 4 halocycloalkyl, C 4 -C 5 cycloalkylalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfinylalkyl, C 2 -C 4 alkylsulfonylalkyl, C 2 -C 4 cyanoalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6
- alkoxycarbonyl C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy
- R 2 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 - C 6 cyanoalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl or benzyloxy(C 2 -
- R 3 is Cj-Cg alkyl, C2-C8 alkenyl or C2-C8 alkynyl, each optionally substituted with substituents independently selected from halogen, hydroxy, cyano, nitro, amino,
- R 3 is NR 12 R 13 ;
- R 4 , R 5 , R 7 and R 8 are each independently selected from hydrogen, halogen, cyano, amino, nitro, -CHO, Cj-C ⁇ alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Cj-C ⁇ haloalkyl, C 2 -Cg haloalkenyl, C 2 -Cg haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C 3 -C 6 cycloalkenyl, C 2 -Cg alkoxyalkyl, C 2 -Cg alkylthioalkyl, C 2 -Cg alkylcarbonyl, C 2 -C6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2
- haloalkylsulfonyl C3-C9 trialkylsilyl, Cj-Cg alkylamino, C 2 -C 6 dialkylamino, C 2 -C 6 haloalkylamino, C 2 -C 6 halodialkylamino and C 2 -C 6 alkylcarbonylamino;
- R 6 is halogen, cyano, amino, nitro, -CHO, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6
- alkynyl C 1 -Cg haloalkyl, C 2 -Cg haloalkenyl, C 2 -Cg haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8
- cycloalkylalkyl C 3 -C 6 cycloalkenyl, C 2 -Cg alkoxyalkyl, C 2 -Cg alkylthioalkyl, C 2 -Cg alkylcarbonyl, C 2 -Cg haloalkylcarbonyl, C 2 -Cg alkoxycarbonyl, C 2 -Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C 2 -Cg cyanoalkyl, C 1 -Cg alkoxy, Cj-Cg haloalkoxy, C 2 -Cg alkoxyalkoxy, Cj-Cg alkylthio, Cj-Cg haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -Cg hal
- alkylsulfonyl C 1 -Cg haloalkylsulfonyl, C3-C9 trialkylsilyl, C 1 -Cg alkylamino, C2-C6 dialkylamino, C2-C6 haloalkylamino, C2-C6 halodialkylamino and C2- Cg alkylcarbonylamino;
- each R 10 is independently selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 - cycloalkyl and C 3 -C 6 halocycloalkyl;
- each R 11 is independently selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6
- each R 12 is independently selected from hydrogen, CHO, C 1 -C ⁇ alkyl, C 1 -C ⁇
- each R 13 is independently selected from CHO, C 1 -Cg alkyl, C 1 -Cg haloalkyl and C2-
- each R 14 is independently C 1 -Cg alkyl or C 1 -Cg haloalkyl
- each R 15 is independently selected from CHO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 2 - Cg alkoxyalkyl;
- each R 16 and R 19 is independently hydrogen or C1-C3 alkyl
- each R 17 is independently C 1 -C ⁇ alkyl or C 1 -C ⁇ alkoxy;
- each R 18 is independently C 1 -Cg alkyl
- each R 20 is independently selected from halogen, cyano, C 1 -Cg alkyl, C 1 -Cg
- haloalkyl C2-Cg alkylcarbonyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy and C 1 -Cg alkylthio;
- each R 20a is independently selected from cyano, C 1 -Cg alkyl, C 1 -Cg haloalkyl and
- each R 21 is a 5-membered unsaturated heterocyclic ring containing 2-4 carbon atoms and 1-3 nitrogen atoms as ring members, wherein the heterocyclic ring is optionally substituted with up to 2 substituents independently selected from R 20 on carbon atom ring members and R 20a on nitrogen atom ring members;
- the compound of Formula 1 is other than 2-[(7-methoxy-2-naphthalenyl)oxy]-N-(2- propen-l-yl)-propanamide.
- this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt thereof.
- This invention also relates to a fungicidal composition
- a fungicidal composition comprising (a) a compound of the invention (i.e. in a fungicidally effective amount); and (b) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
- This invention also relates to a fungicidal composition
- a fungicidal composition comprising (a) a compound of the invention; and (b) at least one other fungicide (e.g., at least one other fungicide having a different site of action).
- This invention further 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, a fungicidally effective amount of a compound of the invention (e.g., as a composition described herein).
- compositions, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
- plant includes members of Kingdom Plantae, particularly seed plants (Spermatopsida), at all life stages, including young plants (e.g., germinating seeds developing into seedlings) and mature, reproductive stages (e.g., plants producing flowers and seeds).
- Portions of plants include geotropic members typically growing beneath the surface of the growing medium (e.g., soil), such as roots, tubers, bulbs and corms, and also members growing above the growing medium, such as foliage (including stems and leaves), flowers, fruits and seeds.
- seedling used either alone or in a combination of words means a young plant developing from the embryo of a seed.
- alkyl used either alone or in compound words such as “alkylthio” or '3 ⁇ 4aloalkyl” includes straight-chain or branched alkyl such as methyl, ethyl, w-propyl, /-propyl, or the different butyl, pentyl or hexyl isomers.
- Alkenyl includes straight-chain or branched alkenes such as ethenyl, 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 also includes moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
- Alkoxy includes, for example, methoxy, ethoxy, w-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
- Alkoxyalkyl denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
- Alkoxyalkoxy denotes alkoxy substitution on alkoxy.
- 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. Examples of “alkylsulfinyl” include CH 3 S(0)-, CH 3 CH 2 S(0)-, CH 3 CH 2 CH 2 S(0)-, (CH 3 ) 2 CHS(0)- and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
- alkylsulfonyl examples include CH 3 S(0) 2 -, CH 3 CH 2 S(0) 2 -, CH 3 CH 2 CH 2 S(0) 2 -, (CH 3 ) 2 CHS(0) 2 -, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
- Alkylthioalkyl denotes alkylthio substitution on alkyl.
- alkylthioalkyl examples include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
- Cyanoalkyl denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH 2 , NCCH 2 CH 2 and CH 3 CH(CN)CH 2 .
- Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
- alkylcycloalkyl denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, z ' -propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl.
- cycloalkylalkyl denotes cycloalkyl substitution on an alkyl moiety.
- cycloalkylalkyl examples include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups.
- Cycloalkenyl includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl.
- halogen either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F 3 C-, C1CH 2 -, CF 3 CH 2 - and CF 3 CC1 2 -.
- halocycloalkyl haloalkoxy
- haloalkynyl haloalkynyl
- haloalkoxy include CF 3 0-, CC1 3 CH 2 0-, HCF 2 CH 2 CH 2 0- and CF 3 CH 2 0-.
- haloalkylthio include CC1 3 S-, CF 3 S-, CC1 3 CH 2 S- and C1CH 2 CH 2 CH 2 S-.
- haloalkylsulfinyl examples include CF 3 S(0)-, CC1 3 S(0)-, CF 3 CH 2 S(0)- and CF 3 CF 2 S(0)-.
- haloalkylsulfonyl examples include CF 3 S(0) 2 -, CC1 3 S(0) 2 -, CF 3 CH 2 S(0) 2 - and CF 3 CF 2 S(0) 2 -.
- haloalkynyl examples include HC ⁇ CCHC1-, CF 3 C ⁇ C-, CC1 3 C ⁇ C- and FCH 2 C ⁇ CCH 2 -.
- haloalkoxyalkoxy examples include CF 3 OCH 2 0-, C1CH 2 CH 2 0CH 2 CH 2 0-, Cl 3 CCH 2 OCH 2 0- as well as branched alkyl derivatives.
- alkylcarbonyl include CH 3 C(0), CH 3 CH 2 CH 2 C(0) and (CH 3 ) 2 CHC(0).
- halodialkylamino denotes a dialkylamino group substituted on at least one alkyl moiety with one or more halogenatoms which may be the same or different.
- halodialkylamino include CF 3 (CH 3 )N-, (CF 3 ) 2 N- and CH 2 C1(CH 3 )N-.
- Trialkylsilyl includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl.
- CJ-C 4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl
- C 2 alkoxyalkyl designates CH 3 OCH 2 -
- C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 )-, CH 3 OCH 2 CH 2 - or CH 3 CH 2 OCH 2 -
- C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 - and CH 3 CH 2 OCH 2 CH 2 -.
- a "ring” as a component of Formula 1 is carbocyclic or heterocyclic.
- the term “ring system” denotes two or more fused rings.
- the terms “bicyclic ring system” and “fused bicyclic ring system” denote a ring system consisting of two fused rings, in which either ring can be saturated, partially unsaturated, or fully unsaturated unless otherwise indicated.
- the term “fused heterobicyclic ring system” denotes a fused bicyclic ring system in which at least one ring atom is not carbon.
- carbocyclic ring denotes a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon.
- a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring.
- saturated carbocyclic refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.
- heterocyclic ring denotes a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Huckel's rule, then said ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
- Aromatic indicates that each of the ring atoms is essentially in the same plane and has a 7-orbital perpendicular to the ring plane, and that (4n + 2) ⁇ electrons, where n is a positive integer, are associated with the ring to comply with Huckel's rule.
- aromatic ring system denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic.
- an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.
- R 3 is a 3-, 4-, 5- or 6-membered saturated carbocyclic ring, a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl ring is attached to Formula 1 as defined in the Summary of the Invention and the ring may be optionally substituted with up to 5 substituents selected from a group of substituents as defined in the Summary of Invention.
- R 3 When R 3 is a 3-, 4-, 5- or 6-membered heterocyclic ring, the ring may be saturated or unsaturated and optionally substituted with up to 5 substituents selected from a group of substituents as defined in the Summary of Invention.
- R 3 When R 3 is a 3-, 4-, 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 though any available carbon or nitrogen ring atom, unless otherwise described.
- R 3 can independently be (among others) a 3-, 4-, 5- or
- 6-membered heterocyclic ring which may be saturated, partially unsaturated, or fully unsaturated and optionally substituted with up to 5 substituents selected from a group of substituents as defined in the Summary of Invention for R 3 .
- Examples of a 3-, 4-, 5- or 6-membered fully unsaturated heterocyclic ring include the rings U-l through U-66 illustrated in Exhibit 1 wherein R v is any substituent as defined in the Summary of the Invention for R 3 (i.e. R 20 on carbon ring members and R 20a on nitrogen ring members) and r is an integer from 0 to 5, limited by the number of available positions on each U-ring.
- R v is any substituent as defined in the Summary of the Invention for R 3 (i.e. R 20 on carbon ring members and R 20a on nitrogen ring members) and r is an integer from 0 to 5, limited by the number of available positions on each U-ring.
- R v is any substituent as defined in the Summary of the Invention for R 3 (i.e. R 20 on carbon ring members and R 20a on nitrogen ring members) and r is an integer from 0 to 5, limited by the number of available positions on each U-ring.
- R v groups are shown on rings U-l through U-66, it is noted that they do not need to be present since they are optional substituents. Note that when r is 0, this means the ring is unsubstituted. The nitrogen atoms that require substitution to fill their valence are substituted with H or R v . Note that when the attachment point between (R ⁇ and the U-ring is illustrated as floating, (Rv),. can be attached to any available carbon atom or nitrogen atom of the U-ring.
- Examples of a 3-, 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring include the rings G-l through G-45 as illustrated in Exhibit 2 wherein R v is any substituent as defined in the Summary of the Invention R 3 (i.e. R 20 on carbon ring members and R 20a on nitrogen ring members) and r is an integer from 0 to 5, limited by the number of available positions on each G-ring.
- R v is any substituent as defined in the Summary of the Invention R 3 (i.e. R 20 on carbon ring members and R 20a on nitrogen ring members) and r is an integer from 0 to 5, limited by the number of available positions on each G-ring.
- the optional substituents corresponding to (R ⁇ , can be attached to any available carbon or nitrogen by replacing a hydrogen atom. Note that when the attachment point on the G-ring is illustrated as floating, the G-ring can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the G-ring by replacement of a hydrogen atom.
- R 3 comprises a ring selected from G-33, G-34, G-35 and G-41 through G-45
- G 2 is O, S or N.
- G 2 is N, the nitrogen atom can complete its valence by substitution with either H or the substituents corresponding to R v as defined in the Summary of Invention for R 3 .
- R 21 is a 5-membered unsaturated heterocyclic ring.
- Examples of a 5-membered unsaturated heterocyclic ring containing 2-4 carbon atoms and 1-3 nitrogen atoms are in Exhibit 1 (U-l 1, U-12, U-13, U-20, U-21, U-22, U-23, U-30, U-31, U-32, U-33, U-36, U-37, U-38, U-39, U-40, U-49, U-50, U-51, U-52 and U-53) and Exhibit 2 (G-18, G-23 and G-24).
- the ring may be optionally substituted with up to 2 substituents independently selected from R 20 on carbon atoms and R 20a on nitrogen atom ring members.
- 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). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
- the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
- nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides.
- nitrogen-containing heterocycles which can form N-oxides.
- tertiary amines can form N-oxides.
- N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and w-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
- MCPBA peroxy acids
- alkyl hydroperoxides such as t-butyl hydroperoxide
- sodium perborate sodium perborate
- dioxiranes such as dimethyldioxirane
- salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms.
- the salts of the compounds of Formula 1 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.
- salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium.
- the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
- Compounds selected from Formula 1, stereoisomers, N-oxides, and salts thereof, typically exist in more than one form, and Formula 1 thus includes all crystalline and noncrystalline forms of the compounds that Formula 1 represents.
- Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
- Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
- polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice.
- Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
- a polymorph of a compound represented by Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by Formula 1.
- Preparation and isolation of a particular polymorph of a compound represented by Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
- Embodiments of the present invention as described in the Summary of the Invention include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):
- Embodiment 1 A compound of Formula 1 wherein Q is O.
- Embodiment 2 A compound of Formula 1 or Embodiment 1 wherein Z 2 is CR 9 .
- Embodiment 3 A compound of Formula 1 or Embodiment 1 or 2 wherein Z 1 is CR 9 .
- Embodiment 4 A compound of Formula 1 or any one of Embodiments 1 through 3 wherein R 1 is C1-C2 alkyl or C1-C 4 alkoxy.
- Embodiment 5 A compound of Embodiment 4 wherein R 1 is methyl, ethyl or methoxy.
- Embodiment 5a A compound of Embodiment 5 wherein R 1 is methyl or ethyl.
- Embodiment 5b A compound of Embodiment 5 wherein R 1 is methoxy.
- Embodiment 6 A compound of Formula 1 or any one of Embodiments 1 through 5 wherein R 2 is hydrogen.
- Embodiment 7a A compound of Formula 1 or any one of Embodiments 1 through 6 wherein R 3 is C 1 -Cg alkyl or C3 ⁇ Cg alkynyl, each optionally substituted with up to 3 substituents independently selected from cyano, hydroxy, fluoro, OR 15 and CHO.
- Embodiment 7b A compound of Formula 1 or any one of Embodiments 1 through 6 wherein R 3 is C 1 -Cg alkyl or C 3 -C 8 alkynyl, each optionally substituted with up to 3 substituents independently selected from hydroxy, fluoro, OR 15 and CHO.
- Embodiment 7b A compound of Formula 1 or any one of Embodiments 1 through 6 wherein R 3 is C 1 -Cg alkyl or C3 ⁇ Cg alkynyl, each optionally substituted with up to 3 substituents independently selected from hydroxy, fluoro, OR 15 and CHO.
- Embodiment 8a A compound of Embodiment 7a wherein R 3 is C 1 -Cg alkyl optionally substituted with cyano or OR 15 .
- Embodiment 8b A compound of Embodiment 7a wherein R 3 is C 3 -Cg alkynyl.
- Embodiment 8 A compound of Embodiment 7 wherein R 3 is C 1 -Cg alkyl optionally substituted with OR 15 or fluoro.
- Embodiment 9a A compound of Embodiment 8a wherein R 3 is C(CH3)2CN,
- Embodiment 9 A compound of Embodiment 8 wherein R 3 is C(CH 3 ) 2 CH 2 OCH 3 , C(CH 3 ) 2 CH 2 OCH 2 OCH 3 , C(CH 3 ) 3 or C(CH 3 ) 2 (CH 2 F).
- Embodiment 9b A compound of Embodiment 8 wherein R 3 is C(CH 3 ) 2 CH 2 OCH 3 ,
- Embodiment 9c A compound of Embodiment 9 wherein R 3 is C(CH 3 ) 2 CH 2 OCH 3 .
- Embodiment 9d A compound of Embodiment 9 wherein R 3 is C(CH 3 ) 3 .
- Embodiment 9e A compound of Embodiment 8b wherein R 3 is C(CH 3 ) 2 C ⁇ CH or
- Embodiment 10 A compound of Formula 1 or any one of Embodiments 1 through 9 wherein R 3 includes a tertiary carbon atom, and R 3 is bonded to the remainder of Formula 1 through the tertiary carbon atom
- Embodiment 11 A compound of Formula 1 or any one of Embodiments 1 through 10 wherein R 4 , R 5 , R 7 , R 8 and R 9 are each independently selected from hydrogen and C 1 -C 6 alkyl.
- Embodiment 12 A compound of Embodiment 11 wherein R 4 , R 5 , R 7 , R 8 and R 9 are each independently selected from hydrogen, methyl and ethyl.
- Embodiment 13a A compound of Formula 1 or any one of Embodiments 1 through 12 wherein R 6 is halogen, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy or C 2 -C 3 alkynyl.
- Embodiment 13 A compound of Formula 1 or any one of Embodiments 1 through 12 wherein R 6 is halogen, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy or C 2 alkynyl.
- Embodiment 14 A compound of Embodiment 13 wherein R 6 is halogen, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy.
- Embodiment 14a A compound of Embodiment 13a wherein R 6 is halogen, C 1 -C 2 alkoxy or C 2 -C 3 alkynyl.
- Embodiment 15 A compound of Embodiment 14 wherein R 6 is bromo, iodo, methoxy or difluoromethoxy.
- Embodiment 15a A compound of Embodiment 14a wherein R 6 is bromo, methoxy, ethoxy, C ⁇ CH or C ⁇ CCH 3 .
- Embodiment 16 A compound of Formula 1 or any one of Embodiments 1 through 15 wherein R 10 is hydrogen or C 1 -C ⁇ alkyl.
- Embodiment 17 A compound of Embodiment 16 wherein R 10 is hydrogen.
- Embodiment 18 A compound of Formula 1 or any one of Embodiments 1 through 17 wherein R 12 is hydrogen or C 1 -C 6 alkyl.
- Embodiment 19 A compound of Formula 1 or any one of Embodiments 1 through 18 wherein R 13 is CHO or Ci-C 6 alkyl.
- Embodiment 20 A compound of Formula 1 or any one of Embodiments 1 through 19 wherein R 15 is CHO, Ci-C 6 alkyl or C 2 -C 6 alkoxyalkyl.
- Embodiment 21 A compound of Embodiment 20 wherein R 15 is CHO, methyl or
- Embodiment 21a A compound of Embodiment 20 wherein R 15 is methyl or
- Embodiments of this invention can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1.
- embodiments of this invention including Embodiments 1-21 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
- Embodiment AA A compound of Formula 1 wherein
- Q is O or S
- Z 1 and Z 2 are each independently CR 9 or N;
- R 1 is Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C3-C 4 cycloalkyl, C3 ⁇ C 4
- halocycloalkyl C -C5 cycloalkylalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfinylalkyl, C 2 -C 4 alkylsulfonylalkyl, C 2 - C 4 cyanoalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
- R 2 is hydrogen, C 1 -C ⁇ alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C ⁇
- N(R 12 )C( O)NR 12 R 13 , OS0 2 R 14 , OS0 2 NR 12 R 13 , NR 12 SO 2 R 14 , NR 12 SO 2 NR 12 R 13 , OR 15 , NR 12 R 13 , S(0) n R 14 , S0 2 R 12 R 13 ,
- R 3 is NR 12 R 13 ;
- R 3 is a 3-, 4-, 5- or 6-membered saturated carbocyclic ring optionally
- R 4 , R 5 , R 7 and R 8 are each independently selected from hydrogen, halogen, cyano, amino, nitro, -CHO, C 1 -C ⁇ alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -Cg haloalkyl, C 2 -Cg haloalkenyl, C 2 -Cg haloalkynyl, C3- Cg cycloalkyl, C 3 -C 6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2
- dialkylaminocarbonyl C 2 -C 6 cyanoalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy, C 2 -C 6 alkoxyalkoxy, C 1 -Cg alkylthio, C 1 -Cg
- haloalkylthio C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C ⁇ haloalkylsulfonyl, C3-C9 trialkylsilyl, C 1 -C ⁇ alkylamino, C 2 -Cg dialkylamino, C 2 -C 6 haloalkylamino, C 2 -C 6 halodialkylamino and C 2 -C 6 alkylcarbonylamino;
- R 6 is halogen, cyano, amino, nitro, -CHO, C 1 -C ⁇ alkyl, C 2 -C 6 alkenyl, C 2 - Cg alkynyl, C 1 -Cg haloalkyl, C 2 -Cg haloalkenyl, C 2 -Cg haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4- C 8 cycloalkylalkyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -Cg alkylcarbonyl, C 2 -Cg haloalkylcarbonyl, C 2 -Cg alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3 ⁇ Cg
- dialkylaminocarbonyl C 2 -C 6 cyanoalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C2-C6 alkoxyalkoxy, C 1 -C ⁇ alkylthio, C 1 -C ⁇
- haloalkylthio C 1 -Q alkylsulfinyl, C 1 -C ⁇ haloalkylsulfinyl, C 1 -C ⁇ alkylsulfonyl, C 1 -Q haloalkylsulfonyl, C 1 -C ⁇ alkylamino, C2-C6 dialkylamino, C2-C6 haloalkylamino, C2-C6 halodialkylamino or C2- C 6 alkylcarbonylamino;
- each R 9 is independently selected from hydrogen, halogen, cyano, amino, nitro, -CHO, Ci ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C4-Cg alkylcycloalkyl, C4-Cg cycloalkylalkyl, C 3 -C 6 cycloalkenyl, C2-C6 alkoxyalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylcarbonyl, C2-C alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3- C 8 dialkylaminocarbonyl, C 2 -C 6 cyanoalkyl, C ⁇ -
- haloalkylthio C 1 -C 6 alkylsulfinyl, C!-C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -Cg haloalkylsulfonyl, C3-C9 trialkylsilyl, C 1 -Cg alkylamino, C2-C6 dialkylamino, C2-Cg haloalkylamino, C2-C6 halodialkylamino and C2-Cg alkylcarbonylamino;
- each R 10 is independently selected from hydrogen, C 1 -Cg alkyl, C 1 -Cg
- each R 11 is independently selected from C 1 -Cg alkyl, C 1 -Cg haloalkyl, C3- Cg cycloalkyl and C 3 -C 6 halocycloalkyl;
- each R 12 is independently selected from hydrogen, CHO, C 1 -Cg alkyl, C 1 -Cg haloalkyl and C2 ⁇ Cg alkylcarbonyl;
- each R 13 is independently selected from CHO, C 1 -Cg alkyl, C 1 -Cg haloalkyl and C 2 -Cg alkylcarbonyl;
- each R 14 is independently C 1 -Cg alkyl or C 1 -Cg haloalkyl
- each R 15 is independently selected from CHO, C 1 -Cg alkyl, C 1 -Cg haloalkyl and C2-C6 alkoxyalkyl;
- each R 16 and R 19 is independently hydrogen or C1-C3 alkyl
- each R 17 is independently C 1 -Cg alkyl or C 1 -Cg alkoxy;
- each R 18 is independently C 1 -Cg alkyl
- each R 20 is independently selected from halogen, cyano, C 1 -Cg alkyl, C 1 -Cg haloalkyl, C2-C6 alkylcarbonyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy and Ci-C 6 alkylthio;
- each R 20a is independently selected from cyano, C 1 -Cg alkyl, C 1 -C 6
- each R 21 is a 5-membered unsaturated heterocyclic ring containing 2-4 carbon atoms and 1-3 nitrogen atoms as ring members, wherein the heterocyclic ring is optionally substituted with up to 2 substituents independently selected from R 20 on carbon atom ring members and R 20a on nitrogen atom ring members;
- each n is independently 0, 1 or 2;
- the compound of Formula 1 is other than 2-[(7-methoxy-2-naphthalenyl)oxy]- N-(2-propen- 1 -yl)-propanamide.
- Embodiment A A compound of Formula 1 as described in the Summary of the
- Z 2 is CR 9 ;
- R 1 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy
- R 2 is hydrogen
- R 3 is C 1 -Cg alkyl or C2-C8 alkynyl, each optionally substituted with up to 3 substituents independently selected from hydroxy, OR 15 and CHO;
- R 4 , R 5 , R 7 , R 8 and R 9 are each independently selected from hydrogen and C 1 -C 6 alkyl;
- R 6 is halogen, C1-C2 alkoxy, C1-C2 haloalkoxy or C2 alkynyl.
- Embodiment Al A compound of Formula 1 as described in the Summary of the
- Z 2 is CR 9 ;
- R 1 is C1-C2 alk l or C1-C 4 alkoxy
- R 2 is hydrogen
- R 3 is C 1 -Cg alkyl or C2-C8 alkynyl, each optionally substituted with up to 3 substituents independently selected from cyano, hydroxy, OR 15 and CHO;
- R 4 , R 5 , R 7 , R 8 and R 9 are each independently selected from hydrogen and C 1 -C ⁇ alkyl;
- R 6 is halogen, C1-C2 alkoxy, C1-C2 haloalkoxy or C2-C3 alkynyl.
- Embodiment B A compound of Embodiment A wherein
- Z 1 is CR 9 ;
- R 1 is methyl, ethyl or methoxy
- R 3 is C 1 -Cg alkyl optionally substituted with OR 15 or fluoro;
- R 4 , R 5 , R 7 , R 8 and R 9 are each independently selected from hydrogen, methyl and ethyl;
- R 6 is halogen, C1-C2 alkoxy or C1-C2 haloalkoxy.
- Embodiment Bl A compound of Embodiment Al wherein
- Z 1 is CR 9 ;
- R 1 is methyl, ethyl or methoxy
- R 3 is C 1 -Cg alkyl optionally substituted with cyano or OR 15 ;
- R 4 , R 5 , R 7 , R 8 and R 9 are each independently selected from hydrogen, methyl and ethyl;
- R 6 is halogen, C1-C2 alkoxy or C2-C3 alkynyl.
- Embodiment B A compound of Embodiment Al wherein
- Z 1 is CR 9 ;
- R 1 is methyl, ethyl or methoxy
- R 3 is C 3 -C 8 alkynyl
- R 4 , R 5 , R 7 , R 8 and R 9 are each independently selected from hydrogen, methyl and ethyl;
- R 6 is halogen, C1-C2 alkoxy or C2-C3 alkynyl.
- Embodiment C A compound of Embodiment B wherein
- R 3 is C(CH3) 2 CH 2 OCH3, C(CH 3 )2CH20CH 2 OCH3, C(CH 3 ) 3 or C(CH 3 ) 2 (CH 2 F);
- R 6 is bromo, iodo, methoxy or difluoromethoxy.
- Embodiment CI A compound of Embodiment Bl wherein
- R 3 is C(CH 3 ) 2 CN, C(CH 3 ) 2 CH 2 OCH 3 , C(CH 3 ) 2 CH 2 OCH 2 OCH 3 or
- R 6 is bromo, methoxy, ethoxy, C ⁇ CH or C ⁇ CCH 3 ..
- Embodiment C2 A compound of Embodiment B2 wherein
- R 3 is C(CH 3 ) 2 C ⁇ CH or C(CH 3 ) 2 C ⁇ CCH 3 ;
- R 6 is bromo, methoxy, ethoxy, C ⁇ CH or C ⁇ CCH 3 ..
- Specific embodiments include compounds of Formula 1 selected from the group consisting of:
- This invention provides a fungicidal composition
- a fungicidal composition comprising a compound of Formula 1 (including all stereoisomers, N-oxides, and salts thereof), and at least one other fungicide.
- a compound of Formula 1 including all stereoisomers, N-oxides, and salts thereof
- at least one other fungicide are compositions comprising a compound corresponding to any of the compound embodiments described above.
- This invention provides a fungicidal composition
- a fungicidal composition comprising a compound of Formula 1 (including all stereoisomers, N-oxides, and salts thereof) (i.e. in a fungicidally effective amount), and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
- a compound of Formula 1 including all stereoisomers, N-oxides, and salts thereof
- additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
- This invention provides a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of Formula 1 (including all stereoisomers, N-oxides, and salts thereof).
- a compound of Formula 1 including all stereoisomers, N-oxides, and salts thereof.
- embodiment of such methods are methods comprising applying a fungicidally effective amount of a compound corresponding to any of the compound embodiments describe above.
- the compounds are applied as compositions of this invention.
- Compounds of Formula la can be prepared by the reaction of 1 molar equivalent of a compound of Formula 2 with 1-1.5 molar equivalents of an activating reagent such as 2-chloro-l-methylpyridinium iodide and 1-5 molar equivalents of a compound of Formula 3 in the presence of 1-10 molar equivalents of a base such as N,N-diisopropylethylamine as shown in Scheme 1.
- an activating reagent such as 2-chloro-l-methylpyridinium iodide
- a base such as N,N-diisopropylethylamine as shown in Scheme 1.
- the reaction can be carried out in an inert solvent such as diethyl ether, tetrahydrofuran, methylene chloride, toluene or xylene at temperatures, between -20 to 60 °C, and preferably from -10 °C to ambient temperatures for a period of time ranging from 1 hour to 4 days.
- the reaction mixture is then concentrated and the residue is column chromatographed (over silica gel with eluents such as solutions of ethyl acetate or dichloromethane in hexanes) to give the desired compound of Formula la.
- compounds of Formula la i.e. Formula 1 wherein Q is O
- compounds of Formula 5 can also be prepared by the reaction of compounds of Formula 4 with compounds of Formula 5 in the presence of a base such as CS2CO3, 2CO3 or KOC(CH 3 ) 3 as shown in Scheme 2.
- the reaction can be carried out by adding 0.7 to 3 molar equivalent of a compound of Formula 5 to a suspension or solution prepared by adding 1-20 molar equivalents of a base such as CS2CO3, K2CO3, or KOC(CH 3 ) 3 to a solution of 1 molar equivalent of a compound of Formula 4 in an solvent such as acetone, diethyl ether, tetrahydrofuran, methylene chloride, N,N-dimethylformamide, t-butanol or toluene under ⁇ 2 at temperatures between -20 to 30 °C.
- a base such as CS2CO3, K2CO3, or KOC(CH 3 ) 3
- an solvent such as acetone, diethyl ether, tetrahydrofuran, methylene chloride, N,N-dimethylformamide, t-butanol or toluene under ⁇ 2 at temperatures between -20 to 30 °C.
- reaction mixture can be stirred at temperatures between -20 to 110 °C, preferably from 10°C to 90 °C, for a period of time ranging from 1 hour to 4 days.
- the reaction mixture is then brought to room temperature and filtered.
- the filtrate is dried over a drying agent such as MgS0 4 or Na 2 S0 4 and then concentrated.
- the residue is column chromatographed (over silica gel with eluents such as solutions of ethyl acetate or dichloromethane in hexanes) to give the desired compounds of Formula la.
- LG is CI, Br, I, OS0 2 CH 3 , OS0 2 CF 3 or OS0 2 (4-CH 3 -Ph)
- Compounds of Formula lb can be prepared by treating compounds of Formula la with Lawesson's reagent or P 2 S 5 as shown in Scheme 3 using methods taught in: Heterocycles 1995, 40, 271-8; J. Med. Chem. 2008, 51, 8124-8134; J. Med. Chem.1990, 33, 2697-706; Synthesis 1989, 396-7; J. Chem. Soc, Perkin Trans. 1, 1988, 1663-8; Tetrahedron 1988 44, 3025-36; J. Org. Chem. 1988 53, 1323-6 or slight modification thereof.
- Compounds of Formula 2 can be prepared by the reaction of 1 molar equivalent of a compound of Formula 6 with 1-35 molar equivalents of a hydroxide base (e.g. NaOH, LiOH or KOH) as shown in Scheme 4.
- a hydroxide base e.g. NaOH, LiOH or KOH
- the reaction can be carried out in a solvent mixture containing water and an organic solvent such as tetrahydrofuran, or methanol at temperatures between 0 to 70 °C, and preferably from 0 to 35 °C for a period of time ranging from 1 hour to 4 days.
- the reaction mixture is then acidified by addition of an acid such as hydrochloric acid and extracted with an organic solvent such as ethyl acetate.
- the organic layer is dried over a drying agent such as sodium sulfate or magnesium sulfate and is then concentrated to give the desired compound of Formula 2.
- R is C ⁇ -Cs alkyl
- Compounds of Formula 6 can be prepared by the reaction of compounds of Formula 4 with compounds of Formula 7 in the presence of a base such as Cs 2 C0 3 , 2 C0 3 or KOC(CH 3 ) 3 as shown in Scheme 5.
- the reaction can be carried out by adding 0.7 to 3 molar equivalent of a compound of Formula 7 to a suspension or solution prepared by adding 1-20 molar equivalents of a base such as Cs2C0 3 , 2 C0 3 or KOC(CH 3 ) 3 to a solution of 1 molar equivalents of a compound of Formula 4 in an solvent such as acetone, diethyl ether, tetrahydrofuran, methylene chloride, N,N-dimethylformamide, t-butanol or toluene under N 2 at temperatures between -20 to 30 °C.
- reaction mixture can be stirred at temperatures between -20 to 110 °C, preferably from 10 to 90 °C, for a period of time ranging from 1 hour to 4 days.
- the reaction mixture is then brought to room temperature and filtered.
- the filtrate is dried over a drying agent such as MgS0 4 or Na 2 S04 and then concentrated.
- the residue is column chromatographed (over silica gel with eluents such as solutions of ethyl acetate or dichloromethane in hexanes) to give the desired compounds of Formula 6.
- LG is CI, Br, I, OS0 2 CH 3 , OS0 2 CF 3 or OS0 2 (4-CH 3 -Ph) and R JU is Ci-C 5 alk l
- Compounds of Formula 4a can be prepared according to the method of Scheme 6 by the refluxing of compounds of Formula 4b (i.e. Formula 4 wherein Z 1 is N, Z 2 is CH and R 4 is CO2H) in high-boiling aromatic or nonaromatic solvents such as toluene, benzene or nitrobenzene, N-methyl-2- pyrrolidone or N,N-dimethylformamide in a temperature range between 50 to 300 °C, and preferably from 180 to 250 °C.
- aromatic or nonaromatic solvents such as toluene, benzene or nitrobenzene, N-methyl-2- pyrrolidone or N,N-dimethylformamide
- the reaction is carried out by adding a compound of Formula 4b to a reaction vessel containing pre-heated solvent and stirring for a time period between 10 min and 6 h or until the evolution of carbon dioxide has ceased.
- the reaction product is isolated as a solid from filtering the hot reaction mixture and then further purified via crystallization from various mixtures of water and polar solvents such as alcohols or N, N-dimethylformamide to afford compounds of Formula 4a.
- Compounds of Formula 4b can be prepared by the reaction of compounds of Formula 8 with bromo-pyruvic acid or ethyl bromopyruvate in the presence of bases such as KOH, NaOH or LiOH in aqueous reaction mixtuures as shown in Scheme 7.
- the reaction is carried out by adding the compound of Formula 8 to a solution of 5 to 20 molar equivalents of the hydroxide base in water which is warmed by dissolution of the base.
- the reaction mixture is stirred until it reaches ambient conditions and is then treated with 1 to 20 molar equivalents of pyruvic acid in one portion with stirring at 25 °C for a period of 2 to 30 days.
- the compound of Formula 8 is precipitated from the reaction mixture by acidification to pH 1 to 5 with concentrated acids such as HC1 or HBr.
- the solids are collected and washed with various mixtures of ethanol and water and air dried to afford compounds of Formula 4b.
- Step A Preparation of methyl 2-[(7-bromo-2-naphthalenyl)oxy]butanoate
- Step C Preparation of 2-[(7-bromo-2-naphthalenyl)oxy]-N-(2-methoxy-l,l- dimethylethyl)butanamide
- Step B) (309 mg, 1 mmol) and 2-chloro-l-methylpyridinium iodide (281 mg, 1.1 mmol) in dichloromethane (6 mL) at 0 °C was added N,N-diisopropylethylamine (0.7 ml, 4 mmol). The reaction mixture was stirred at ambient temperature for 15 minutes. A solution of l-methoxy-2-methyl-2-propanamine (114 mg, 1.1 mmol) in dichloromethane (1 mL) was added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with 10 mL of dichloromethane. The reaction mixture was washed with water (2 x 15 mL).
- the reaction mixture was diluted with dichloromethane (30 mL). The reaction mixture was washed with water twice (2 x 45 mL). The organic phase was dried (MgSC ⁇ ) and concentrated under reduced pressure. The residue was purified by column chromatography (with solutions of ethyl acetate in hexanes in volume ratios from 10 to 53 % as eluents) to give the title compound (0.94 g), a compound of the present invention, as a solid (m.p. 115-116 °C).
- Step A Preparation of 2-bromo-N-(2-hydroxy- 1 , 1 -dimethylethyl)butanamide
- Step C Preparation of 2-[(7-cyano-2-naphthalenyl)oxy]-N-[2-(methoxymethoxy)-l,l- dimethylethyl]butanamide
- a solution of potassium hydroxide (39.60 g, 707.0 mmol) in water (200 mL) at 50 °C was treated with 5-bromoisatin (10.00 g, 44.2 mmol) in one portion. After 1.5 h the reaction temperature had decreased to 20 °C.
- the resulting mixture was treated with bromopyruvic acid (20.69 g, 123.9 mmol) and stirred at 20 °C for 6 days.
- the mixture was treated with concentrated aqueous hydrochloric acid to decrease the pH to 4.
- the resulting precipitate was collected on a coarse frit glass funnel and washed with ethanol then water.
- the resultant oil was purified by column chromatographed on silica gel (with ethyl acetate/hexanes as the eluent). The desired fractions were combined and concentrated to give the title compound as an orange solid (5.0 g).
- Step D Preparation of 2-[(6-bromo-3-quinolinyl)oxy]-N-(l,l-dimethylethyl)- butanamide
- Step A Preparation of 1 , 1 -dimethylethyl-N-(2-methoxy- 1 , 1 -dimethylethyl)carbamate
- N-Boc-2-amino-2-methyl-l-propanol 15 g, 79 mmoles
- tetra-N- butylammonium bisulfate 2.68 g, 7.9 mmol
- toluene 150 mL
- 50% aqueous sodium hydroxide (30 mL) and iodomethane (16.8 g, 118.3 mmol)
- the mixture was treated with additional iodomethane (16.8 g, 118 mmol) and stirred for 48 h at 25 °C.
- the reaction mixture was treated with a third portion of iodomethane (16.8 g, 118 mmol) and stirred for 24 h at 25 °C.
- the reaction mixture was then poured into water and extracted with diethyl ether. The organic phase was washed with brine, dried (MgSC ⁇ ) and concentrated under reduced pressure to give the title compound as a colorless oil (12.2 g).
- Step B Preparation of l-methoxy-2-methyl-2-propanamine hydrochloride
- Step B Preparation of methyl 2-[(6-iodo-3-quinolinyl)oxy]-2-methoxyacetate
- Step D Preparation of N-(l,l-dimethyl-2-propyn-l-yl)-2-[(6-iodo-3-quinolinyl)oxy]- 2-methoxyacetamide
- Step 4 the subject compound, a compound of the present invention was prepared from 2-[(6-iodo-3-quinolinyl)oxy]-2- methoxyacetic acid (i.e. the product of Step C) as a white solid.
- the reaction mixture was poured into water and extracted with ethyl acetate.
- the organic phase was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- the residue was dissolved in dichloromethane, treated with silica gel (5 g) and concentrated to a dry powder.
- the powder was chromatographed on a silica gel column employing a gradient elution from 20% ethyl acetate/hexanes to 100% ethyl acetate over 15.0 min. The desired fractions were combined and concentrated to give the title compound, a compound of the present invention, as an oil (71.0 mg).
- the reaction mixture was treated with methanol (5.0 mL) and stirred for 10 minutes. The mixture was then poured into water and extracted with ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane (50.0 mL), treated with silica gel (15 g) and concentrated to a dry powder. The powder was chromatographed on a silica gel column employing a gradient elution from 10% ethyl acetate/hexanes to 90% ethyl acetate/hexanes over 15.0 min. The desired fractions were combined and concentrated to give the title compound, a compound of the present invention, as an oil (0.35 g).
- Step A Preparation of 7-methoxy-2-naphthalenyl 1,1,1 -trifluoromethanesulfonate
- the ether solution was washed with saturated aqueous NaCl solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- the residue was dissolved in dichloromethane (50 mL), treated with silica gel (15 g) and concentrated to a dry powder.
- the powder was chromatographed on a silica gel column employing an isocratic elution of 5.0 % ethyl acetate/hexanes. The desired fractions were combined and concentrated to give the title compound (1.35 g) as a solid.
- Step D Preparation of methyl 2-[(7-ethyl-2-naphthalenyl)oxy]butanoate
- Step F Preparation of 2-[(7-ethyl-2-naphthalenyl)oxy]-N-(2-methoxy-l,l- dimethylethyl)butanamide
- Step A Preparation of 7-methoxy-2-naphthalenyl 1,1,2,2,3,3,4,4,4-nonafluoro-l- butanesulfonate
- the organic phase was dried over magnesium sulfate and filtered.
- the dried dichloromethane solution was treated with silica gel (50 g) and concentrated to a dry powder.
- the powder was chromatographed on a silica gel column employing an isocratic elution of 10.0 % ethyl acetate/hexanes. The desired fractions were combined and concentrated to give the title compound (28.0 g) as a solid.
- Step C Preparation of 7-[l-[[(2-methoxy-l,l-dimethylethyl)amino]carbonyl]- propoxy]-2-naphthalenyl 1, 1,2,2,3,3,4, 4,4-nonafluoro-l-butanesulfonate A mixture of 7-hydroxy-2-naphthalenyl 1, 1,2,2,3,3,4,4, 4-nonafluoro-l-butanesulfonate
- Step D Preparation of 2-[(7-ethenyl-2-naphthalenyl)oxy]-N-(2-methoxy-l,l- dimethylethyl)butanamide
- Step C the product of Step C) (1.0 g, 1.63 mmoles), bis-diphenylphosphinepalladium(II) dichloride (0.057 g, .082 mmoles), lithium chloride (0.55 g, 13.0 mmoles) and tributyl(vinyl)tin (0.65 g, 2.04 mmoles) in dimethylformamide (75 mL) was stirred at 100 °C for 18 h. The mixture was cooled to 25 °C, poured into saturated aqueous NaCl solution and extracted with ethyl acetate. The organic phase was washed with saturated aqueous NaCl solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- Step A Preparation of l,r-(2,7-naphthalenediyl) bis(l,l,l-trifluoromethanesulfonate)
- 2,7-dihydroxynaphthalene 5.4 g, 34 mmol
- pyridine 9.06 mL, 112 mmole
- the mixture was cooled to 0 °C under a nitrogen atomosphere with stirring using an ice/acetone bath.
- To this mixture at 0 °C was then added trifluoromethanesulfonic anhydride (13.24 mL, 78.6 mmole) portionwise. After the addition, the mixture was stirred at ambient temperature for 2.5 hours.
- Step B Preparation of 7-hydroxy-2-naphthalenyl 1,1,1-trifluoromethanesulfonate
- reaction mixture was then cooled to 0 °C and additional potassium t-butoxide (0.9 g, 8 mmol) was added with stirring and ice/acetone bath cooling.
- the reaction mixture was stirred at ambient temperature for 2 hours.
- Ethyl acetate (350 mL), saturated aqueous NaCl solution (350 mL) and IN hydrochloric acid aqueous solution (20 mL) were added to the reaction mixture and the organic phase was separated, dried over MgSC-4 and concentrated.
- the residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 5 to 53 % as eluents) to give the title compound (2 g) as an oil.
- Step C Preparation of methyl 2-[[7-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]- oxy]butanoate
- Step D Preparation of methyl 2-[[7-[2-(trimethylsilyl)ethynyl]-2-naphthalenyl]- oxy]butanoate
- reaction mixture was purged with nitrogen for 10 minutes treated sequentially with triethylamine (7.5 mL) and ethynyltrimethylsilane (787 mg, 8 mmole).
- triethylamine 7.5 mL
- ethynyltrimethylsilane 787 mg, 8 mmole
- the mixture was stirred at room temperature under nitrogen atomosphere overnight and was then concentrated under reduced pressure.
- the residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 5 to 40 % as eluents) to give the title compound (730 mg) as an oil.
- Step F Preparation of 2-[(7-ethynyl-2-naphthalenyl)oxy]-N-(2-methoxy-l,l- dimethylethyl)-butanamide
- the reaction mixture was stirred at room temperature for 4 hours and then diluted with 50 mL of dichloromethane.
- the reaction mixture was washed with water twice (60 mL each) and the organic phase was separated, dried over MgS0 4 and concentrated under reduced pressure.
- the residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 5 to 53 % as eluents) to give the title compound, a compound of the present invention, as an oil (564 mg).
- Step A Preparation of methyl 2-methoxy-2-[[7-[[(trifluoromethyl)sulfonyl]oxy]-2- naphthalenyl] oxy] acetate
- Step B Preparation of methyl 2-methoxy-2-[[7-[2-(trimethylsilyl)ethynyl]-2- naphthalenyl] oxy] acetate
- Methyl 2-methoxy-2- [ [7- [ [(trifluoromethyl)sulfonyl] oxy] -2 -naphthalenyl] oxy] acetate i.e. the product of Step A) (1.35 g, 3.42 mmol), tetrahydrofuran (35 mL), bis(triphenylphosphine)palladium(II) dichloride (0.33 g, 0.47 mmole) and copper (I) iodide (178 mg, 0.94 mmole) were combined at room temperature under a nitrogen atomosphere.
- the reation mixture was purged with nitrogen for another 10 minutes and then treated sequentially with triethylamine (15 mL) and ethynyltrimethylsilane (1.23 g, 12.50 mmole).
- Step C Preparation of 2-[(7-ethynyl-2-naphthalenyl)oxy]-2-methoxyacetic acid
- Step D Preparation of 2-[(7-ethynyl-2-naphthalenyl)oxy]-2-methoxy-N-(2-methoxy- l,l-dimethylethyl)acetamide
- Step A Preparation of methyl 2-[(7-bromo-2-naphthalenyl)-oxy]-2-methoxyacetate
- Step B Preparation of 2-[(7-bromo-2-naphthalenyl)-oxy]-2-methoxyacetic acid
- Step C Preparation of 2-[(7-bromo-2-naphthalenyl)oxy]-2-methoxy-N-(2-methoxy-
- the reaction mixture was stirred at room temperature for 4 and then diluted with 35 mL of dichloromethane.
- the reaction mixture was washed with water twice (50 mL each).
- the organic phase was dried over magnesium sulfate and was concentrated under reduced pressure.
- the residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 10 to 65 % as eluents) to give the title compound, a compound of the present invention, as a solid, (375 mg), mp 81-82 °C.
- reaction mixture stirred at 0 °C for 21 minutes and then at ambient temperature for 1 hour.
- the reaction mixture was then diluted with ethyl acetate (60 mL) and saturated aqueous ammonium chloride solution (40 mL).
- the organic phase was separated and the aqueous phase was extracted with ethyl acetate (50 mL).
- the organic phases were combined, washed with saturated aqueous NaCl solution (80 mL), dried over magnesium sulfate and concentrated under reduced pressure.
- Step A Preparation of 2-bromo-7-[[(l,l-dimethylethyl)dimethylsilyl]oxy]naphthalene
- dichloromethane 21 mL
- imidazole 1.5 g, 22 mmole
- t-butyldimethylsilylchloride 1.66 g, 11 mmole
- the reaction mixture was stirred at room temperature overnight.
- the reaction mixture was diluted with dichloromethane (70 mL) and the resulting mixture was washed with saturated aqueous NaHCC ⁇ solution twice (100 mL each).
- Step B Preparation of 2-[[(l,l-dimethylethyl)dimethylsilyl]oxy]-7-iodonaplitlialene
- Step D Preparation of methyl 2-[(7-iodo-2-naphthalenyl)oxy]-2-methoxyacetate
- Step F Preparation of 2-[(7-iodo-2-naphthalenylyl)oxy]-2-methoxy-N-(2-methoxy- l,l-dimethylethyl)acetamide
- the reaction mixture was diluted with 30 mL of dichloromethane and washed with water twice (35 mL each). The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 10 to 53 % as eluents) to give the title compound, a compound of the present invention, as an oil (135 mg).
- Step B Preparation of methyl 2-[(7-ethoxy-2-naphthalenyl)oxy]butanoate
- Step D Preparation of N-(l-cyano-l-methylethyl)-2-[(7-ethoxy-2-naphthalenyl)oxy]- butanamide
- the reaction mixture was diluted with 10 mL of dichloromethane, and then washed with H 2 0 (2 x 15 mL).
- the organic phase was dried (MgSC ⁇ ) and concentrated under reduced pressure.
- the resultant residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 10 to 90 % as eluents) to give the title compound, a compound of the present invention, as a solid (70 mg).
- R 8 is H; Z 1 is CH; Z 2 is CH
- a compound of Formula 1 of this invention (including N-oxides and salts thereof) will generally be used as a fungicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serve as a carrier.
- a composition i.e. formulation
- additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serve as a carrier.
- 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.
- Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like, which optionally can be thickened into gels.
- aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion.
- nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
- compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment.
- Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
- An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
- Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting. Liquid and solid formulations can be applied onto seeds of crops and other desirable vegetation as seed treatments before planting to protect developing roots and other subterranean plant parts and/or foliage through systemic uptake.
- 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 wei ht.
- Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
- Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
- Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy- 4-methyl-2-pentan
- Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C 6 -C 2 2) > such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof.
- plant seed and fruit oils e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel
- animal-sourced fats e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil
- Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation.
- alkylated fatty acids e.g., methylated, ethylated, butylated
- Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
- the solid and liquid compositions of the present invention often include one or more surfactants.
- surfactants also known as “surface-active agents”
- surface-active agents generally modify, most often reduce, the surface tension of the liquid.
- surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
- Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene
- Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of e
- Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
- amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amine
- Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon 's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
- compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
- formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes.
- Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone- vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
- formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
- the compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent.
- Solutions, including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water.
- Active ingredient slurries, with particle diameters of up to 2,000 ⁇ can be wet milled using media mills to obtain particles with average diameters below 3 ⁇ .
- Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 um range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques.
- Pellets can be prepared as described in U.S. 4,172,714.
- Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
- Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
- Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
- Compound 51 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%
- Compound 7 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium magnesium bentonite 59.0%
- Compound 20 20.00% polyvinylpyrrolidone-vinyl acetate copolymer 5.00% montan acid wax 5.00% calcium ligninsulfonate 1.00% polyoxyethylene/polyoxypropylene block copolymers 1.00% stearyl alcohol (POE 20) 2.00% polyorganosilane 0.20% colorant red dye 0.05% water 65.75%
- Water-soluble and water-dispersible formulations are typically diluted with water to form aqueous compositions before application.
- Aqueous compositions for direct applications to the plant or portion thereof typically at least about 1 ppm or more (e.g., from 1 ppm to 100 ppm) of the compound(s) of this invention.
- 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 to be protected, an effective amount of a compound of the invention or a fungicidal composition containing said compound.
- the compounds and/or 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, turf, vegetable, field, cereal, and fruit crops.
- pathogens include: Oomycetes, including Phytophthora diseases such as Phytophthora infestans, Phytophthora megasperma, Phytophthora parasitica, Phytophthora cinnamomi and Phytophthora capsici, Pythium diseases such as Pythium aphanidermatum, and diseases in the Peronosporaceae family such as Plasmopara viticola, Peronospora spp. (including Peronospora tabacina and Peronospora parasitica), Pseudoperonospora spp.
- Phytophthora diseases such as Phytophthora infestans, Phytophthora megasperma, Phytophthora parasitica, Phytophthora cinnamomi and Phytophthora capsici
- Pythium diseases such as Pythium aphanidermatum
- diseases in the Peronosporaceae family such as
- Botrytis diseases such as Botrytis cinerea, Monilinia fructicola, Sclerotinia diseases such as Sclerotinia sclerotiorum, Magnaporthe grisea, Phomopsis viticola, Helminthosporium diseases such as Helminthosporium tritici repentis, Pyrenophora teres, anthracnose diseases such as Glomerella or Colletotrichum spp.
- Puccinia spp. such as Puccinia recondita, Puccinia striiformis, Puccinia hordei, Puccinia graminis and Puccinia arachidis
- Rutstroemia floccosum also known as Sclerontina homoeocarpd
- compositions or combinations also have activity against bacteria such as Erwinia amylovora, Xanthomonas campestris, Pseudomonas syringae, and other related species.
- 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 seeds to protect the seeds and seedlings developing from the seeds.
- the compounds can also be applied through irrigation water to treat plants.
- this aspect of the present invention can also be described as a method for protecting a plant or plant seed from diseases caused by fungal pathogens comprising applying a fungicidally effective amount of a compound of Formula 1, an N-oxide, or salt thereof to the plant (or portion thereof) or plant seed (directly or through the environment (e.g., growing medium) of the plant or plant seed).
- Rates of application for these compounds can be influenced by factors such as the plant diseases to be controlled, the plant species to be protected, ambient moisture and temperature and should be determined under actual use conditions.
- a fungicidally effective amount can be influenced by factors such as the plant diseases to be controlled, the plant species to be protected, ambient moisture and temperature and should be determined under actual use conditions.
- One skilled in the art can easily determine through simple experimentation the fungicidally effective amount necessary for the desired level of plant disease control.
- Foliage can normally be protected when treated at a rate of from less than about 1 g/ha to about 5,000 g/ha of active ingredient.
- Seed and seedlings can normally be protected when seed is treated at a rate of from about 0.1 to about 10 g per kilogram of seed.
- Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including fungicides, insecticides, nematocides, bactericides, acaricides, herbicides, herbicide safeners, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
- fungicides insecticides, nematocides, bactericides, acaricides, herbicides, herbicide safeners
- growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus
- the present invention also pertains to a composition
- a composition comprising a compound of Formula 1 (in a fungicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent.
- the other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent.
- one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
- composition which in addition to the compound of Formula 1 includes at least one fungicidal compound selected from the group consisting of the classes (1) methyl benzimidazole carbamate (MBC) fungicides; (2) dicarboximide fungicides; (3) demethylation inhibitor (DMI) fungicides; (4) phenylamide fungicides; (5) amine/morpholine fungicides; (6) phospholipid biosynthesis inhibitor fungicides; (7) carboxamide fungicides; (8) hydroxy(2-amino-)pyrimidine fungicides; (9) anilinopyrimidine fungicides; (10) N-phenyl carbamate fungicides; (11) quinone outside inhibitor (Qol) fungicides; (12) phenylpyrrole fungicides; (13) quinoline fungicides; (14) lipid peroxidation inhibitor fungicides; (15) melanin biosynthesis inhibitors-reductase (MBI-R) fungicides;
- Methyl benzimidazole carbamate fungicides include benzimidazole and thiophanate fungicides.
- the benzimidazoles include benomyl, carbendazim, Albendazole and thiabendazole.
- the thiophanates include thiophanate and thiophanate-methyl.
- DMT Demethylation inhibitor
- FRAC Field Action Committee
- C14-demethylase which plays a role in sterol production.
- Sterols such as ergosterol, are needed for membrane structure and function, making them essential for the development of functional cell walls. Therefore, exposure to these fungicides results in abnormal growth and eventually death of sensitive fungi.
- DMI fungicides are divided between several chemical classes: azoles (including triazoles and imidazoles), pyrimidines, piperazines and pyridines.
- the triazoles include azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole (including diniconazole-M), epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, itraconazole, triadimefon, triadimenol, triticonazole and uniconazole.
- the imidazoles include clotrimazole, imazalil, oxpoconazole, prochloraz, pefurazoate and triflumizole.
- the pyrimidines include fenarimol and nuarimol.
- the piperazines include triforine.
- the pyridines include pyrifenox. Biochemical investigations have shown that all of the above mentioned fungicides are DMI fungicides as described by K. H. Kuck et al. in Modern Selective Fungicides - Properties, Applications and Mechanisms of Action, H. Lyr (Ed.), Gustav Fischer Verlag: New York, 1995, 205-258.
- Phenylamide fungicides are specific inhibitors of RNA polymerase in Oomycete fungi. Sensitive fungi exposed to these fungicides show a reduced capacity to incorporate uridine into rRNA. Growth and development in sensitive fungi is prevented by exposure to this class of fungicide.
- Phenylamide fungicides include acylalanine, oxazolidinone and butyrolactone fungicides.
- the acylalanines include benalaxyl, benalaxyl-M, fiiralaxyl, metalaxyl and metalaxyl- M/mefenoxam.
- the oxazolidinones include oxadixyl.
- the butyro lactones include ofurace.
- Amine/morpholine fungicides include morpholine, piperidine and spiroketal-amine fungicides.
- the morpholines include aldimorph, dodemorph, fenpropimorph, tridemorph and trimorphamide.
- the piperidines include fenpropidin and piperalin.
- the spiroketal-amines include spiroxamine.
- Phospholipid biosynthesis inhibitor fungicides include phophorothiolate and dithiolane fungicides.
- the phosphorothiolates include edifenphos, iprobenfos and pyrazophos.
- the dithiolanes include isoprothiolane.
- Carboxamide fungicides (Fungicide Resistance Action Committee (FRAC) code 7) inhibit Complex II (succinate dehydrogenase) fungal respiration by disrupting a key enzyme in the Krebs Cycle (TCA cycle) named succinate dehydrogenase. Inhibiting respiration prevents the fungus from making ATP, and thus inhibits growth and reproduction.
- Carboxamide fungicides include benzamides, furan carboxamides, oxathiin carboxamides, thiazole carboxamides, pyrazole carboxamides and pyridine carboxamides.
- the benzamides include benodanil, flutolanil and mepronil.
- the furan carboxamides include fenfuram.
- the oxathiin carboxamides include carboxin and oxycarboxin.
- the thiazole carboxamides include thifluzamide.
- the pyrazole carboxamides include furametpyr, penthiopyrad, bixafen, isopyrazam, N-[2-(15,2 ?)-[l,r-bicyclopropyl]-2-ylphenyl]-3- (difluoromethyl)-l -methyl- lH-pyrazole-4-carboxamide and penflufen (N-[2-(l,3-dimethyl- butyl)phenyl]-5-fluoro- 1 ,3-dimethyl- lH-pyrazole-4-carboxamide).
- the pyridine carboxamides include boscalid.
- FRAC Federal Communications Commission
- Anilinopyrimidine fungicides (Fungicide Resistance Action Committee (FRAC) code 9) are proposed to inhibit biosynthesis of the amino acid methionine and to disrupt the secretion of hydrolytic enzymes that lyse plant cells during infection. Examples include cyprodinil, mepanipyrim and pyrimethanil.
- N-Phenyl carbamate fungicides (Fungicide Resistance Action Committee (FRAC) code 10) inhibit mitosis by binding to ⁇ -tubulin and disrupting microtubule assembly. Inhibition of microtubule assembly can disrupt cell division, transport within the cell and cell structure. Examples include diethofencarb.
- Quinone outside inhibitor fungicides include methoxyacrylate, methoxycarbamate, oximino acetate, oximinoacetamide, oxazolidinedione, dihydrodioxazine, imidazolinone and benzylcarbamate fungicides.
- the methoxyacrylates include azoxystrobin, enestroburin (SYP-Z071), picoxystrobin and pyraoxystrobin (SYP-3343).
- the methoxycarbamates include pyraclostrobin and pyrametostrobin (SYP-4155).
- the oximinoacetates include kresoxim-methyl and trifloxystrobin.
- the oximinoacetamides include dimoxystrobin, metominostrobin, orysastrobin, a-[methoxyimino] -N-methyl-2- [ [ [ 1 -[3 -(trifluoromethyl)phenyl] ethoxy] imino] - methyl]benzeneacetamide and 2- [ [ [3 -(2, 6-dichlorophenyl)- 1 -methyl-2-propen- 1 -ylidene] - amino]oxy]methyl]-a-(methoxyimino)-N-methylbenzeneacetamide.
- the oxazolidinediones include famoxadone.
- the dihydrodioxazines include fluoxastrobin.
- the imidazolinones include fenamidone.
- the benzylcarbamates include pyribencarb.
- Quinoline fungicides (Fungicide Resistance Action Committee (FRAC) code 13) are proposed to inhibit signal transduction by affecting G-proteins in early cell signaling. They have been shown to interfere with germination and/or appressorium formation in fungi that cause powder mildew diseases. Quinoxyfen and tebufloquin are examples of this class of fungicide.
- Lipid peroxidation inhibitor fungicides are proposed to inhibit lipid peroxidation which affects membrane synthesis in fungi. Members of this class, such as etridiazole, may also affect other biological processes such as respiration and melanin biosynthesis.
- Lipid peroxidation fungicides include aromatic carbon and 1,2,4-thiadiazole fungicides.
- the aromatic carbon fungicides include biphenyl, chloroneb, dicloran, quintozene, tecnazene and tolclofos- methyl.
- the 1,2,4-thiadiazole fungicides include etridiazole.
- MMI-R Mellanin biosynthesis inhibitors-reductase
- Melanin biosynthesis inhibitors-reductase fungicides include isobenzofuranone, pyrroloquinolinone and triazolobenzothiazole fungicides.
- the isobenzofuranones include fthalide.
- the pyrroloquinolinones include pyroquilon.
- the triazolobenzothiazoles include tricyclazole.
- MBI-D Melanin biosynthesis inhibitors-dehydratase fungicides
- FRAC Field Action Committee
- scytalone dehydratase in melanin biosynthesis Melanin in required for host plant infection by some fungi.
- Melanin biosynthesis inhibitors-dehydratase fungicides include cyclopropanecarboxamide, carboxamide and propionamide fungicides.
- the cyclopropanecarboxamides include carpropamid.
- the carboxamides include diclocymet.
- the propionamides include fenoxanil.
- Squalene-epoxidase inhibitor fungicides include thiocarbamate and allylamine fungicides.
- the thiocarbamates include pyributicarb.
- the allylamines include naftifine and terbinafine.
- Polyoxin fungicides (Fungicide Resistance Action Committee (FRAC) code 19) inhibit chitin synthase. Examples include polyoxin.
- Quinone inside inhibitor (Qil) fungicides (Fungicide Resistance Action Committee (FRAC) code 21) inhibit Complex III mitochondrial respiration in fungi by affecting ubiquinol reductase. Reduction of ubiquinol is blocked at the "quinone inside" (Qi) site of the cytochrome bc ⁇ complex, which is located in the inner mitochondrial membrane of fungi. Inhibiting mitochondrial respiration prevents normal fungal growth and development.
- Quinone inside inhibitor fungicides include cyanoimidazole and sulfamoyltriazole fungicides.
- the cyanoimidazoles include cyazofamid.
- the sulfamoyltriazoles include amisulbrom
- Benzamide fungicides (Fungicide Resistance Action Committee (FRAC) code 22) inhibit mitosis by binding to ⁇ -tubulin and disrupting microtubule assembly. Inhibition of microtubule assembly can disrupt cell division, transport within the cell and cell structure. Examples include zoxamide.
- Glucopyranosyl antibiotic protein synthesis fungicides
- FRAC Field Resistance Action Committee
- “Carbamate fungicides” (Fungicide Resistance Action Committee (FRAC) code 28) are considered multi-site inhibitors of fungal growth. They are proposed to interfere with the synthesis of fatty acids in cell membranes, which then disrupts cell membrane permeability. Propamacarb, propamacarb-hydrochloride, iodocarb, and prothiocarb are examples of this fungicide class.
- Oxidative phosphorylation uncoupling fungicides inhibit fungal respiration by uncoupling oxidative phosphorylation. Inhibiting respiration prevents normal fungal growth and development.
- This class includes 2,6-dinitroanilines such as fluazinam, pyrimidonehydrazones such as ferimzone and dinitrophenyl crotonates such as dinocap, meptyldinocap and binapacryl.
- Carboxylic acid fungicides (Fungicide Resistance Action Committee (FRAC) code 31) inhibit growth of fungi by affecting deoxyribonucleic acid (DNA) topoisomerase type II (gyrase). Examples include oxolinic acid.
- Heteroaromatic fungicides include isoxazole and isothiazolone fungicides.
- the isoxazoles include hymexazole and the isothiazolones include octhilinone.
- Phosphonate fungicides include phosphorous acid and its various salts, including fosetyl-aluminum.
- Phthalamic acid fungicides include teclofthalam.
- CAA Carboxylic acid amide
- Carboxylic acid amide fungicides include cinnamic acid amide, valinamide carbamate and mandelic acid amide fungicides.
- the cinnamic acid amides include dimethomorph and flumorph.
- the valinamide carbamates include benthiavalicarb, benthiavalicarb-isopropyl, iprovalicarb, valifenalate and valiphenal.
- the mandelic acid amides include mandipropamid, N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-l-yl]oxy]-3- methoxyphenyl] ethyl] -3 -methyl-2- [(methylsulfonyl)amino]butanamide and N- [2- [4- [[3 -(4- chlorophenyl)-2-propyn- 1 -yl] oxy] -3 -methoxyphenyl] ethyl] -3 -methyl-2- [(ethylsulfonyl)amino]butanamide.
- Benzamide fungicides (Fungicide Resistance Action Committee (FRAC) code 43) inhibit growth of fungi by delocalization of spectrin-like proteins.
- Examples include acylpicolide fungicides such as fluopicolide and fluopyram.
- Host plant defense induction fungicides include benzo-thiadiazole, benzisothiazole and thiadiazole-carboxamide fungicides.
- the benzo-thiadiazoles include acibenzolar-S-methyl.
- the benzisothiazoles include probenazole.
- the thiadiazole-carboxamides include tiadinil and isotianil.
- Multi-site contact fungicides inhibit fungal growth through multiple sites of action and have contact/preventive activity.
- This class of fungicides includes: (45.1)
- Copper fungicides are inorganic compounds containing copper, typically in the copper(II) oxidation state; examples include copper oxychloride, copper sulfate and copper hydroxide, including compositions such as Bordeaux mixture (tribasic copper sulfate).
- Sulfur fungicides are inorganic chemicals containing rings or chains of sulfur atoms; examples include elemental sulfur.
- Dithiocarbamate fungicides contain a dithiocarbamate molecular moiety; examples include mancozeb, metiram, propineb, ferbam, maneb, thiram, zineb and ziram.
- Phthalimide fungicides contain a phthalimide molecular moiety; examples include folpet, captan and captafol.
- Chloronitrile fungicides contain an aromatic ring substituted with chloro and cyano; examples include chlorothalonil.
- Sulfamide fungicides include dichlofluanid and tolyfluanid.
- Guanidine fungicides include dodine, guazatine, iminoctadine albesilate and iminoctadine triacetate.
- Triazine fungicides include anilazine.
- Quinone fungicides include dithianon.
- Fungicides other than fungicides of classes (1) through (45) include certain fungicides whose mode of action may be unknown. These include: (46.1) “thiazole carboxamide fungicides” (Fungicide Resistance Action Committee (FRAC) code U5), (46.2) “phenyl-acetamide fungicides” (Fungicide Resistance Action Committee (FRAC) code U6), (46.3) “quinazolinone fungicides” (Fungicide Resistance Action Committee (FRAC) code U7), (46.4) "benzophenone fungicides” (Fungicide Resistance Action Committee (FRAC) code U8) and (46.5) "triazolopyrimidine fungicides”.
- the thiazole carboxamides include ethaboxam.
- the phenyl-acetamides include cyflufenamid and N-
- the quinazolinones include proquinazid and 2-butoxy-6- iodo-3-propyl-4H-l-benzopyran-4-one.
- the benzophenones include metrafenone.
- the (b46) class also includes bethoxazin, neo-asozin (ferric methanearsonate), pyrrolnitrin, quinomethionate, N- [2- [4- [[3 -(4-chlorophenyl)-2-propyn- 1 -yl] oxy] -3 -methoxyphenyl] ethyl] - 3-methyl-2-[(methylsulfonyl)amino]butanamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-l- yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide, 2-[[2- fluoro-5-(trifluoromethyl)phenyl]thio]-2-[3-(2-methoxyphenyl)-2-thiazolidinyl- idene]acet
- the triazolopyrimidines include ametoctradin.
- Other fungicides whose mode of action may be unknown include pentyl N-[4-[[[[(l-methyl-lH-tetrazol-5- yl)phenylmethylene] amino] oxy] methyl] -2-thiazolyl]carbamate, pentyl N- [6- [ [ [ [( 1 -methyl- lH-tetrazol-5-yl)phenylmethylene]amino]oxy]methyl]-2-pyridinyl]carbamate and Hambra®.
- a mixture comprising a compound of Formula 1 and at least one fungicidal compound selected from the group consisting of the aforedescribed classes (1) through (46).
- a composition comprising said mixture (in fungicidally effective amount) and further comprising at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
- a mixture comprising a compound of Formula 1 and at least one fungicidal compound selected from the group of specific compounds listed above in connection with classes (1) through (46).
- a composition comprising said mixture (in fungicidally effective amount) and further comprising at least one additional surfactant selected from the group consisting of surfactants, solid diluents and liquid diluents.
- insecticides such as abamectin, acephate, acetamiprid, acrinathrin, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyantraniliprole (3-bromo- l-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-lH- pyrazole-5-carboxamide), cyflumetofen, cyfluthrin,
- Bacillus thuringiensis subsp. kurstaki and the encapsulated delta-endotoxins of Bacillus thuringiensis (e.g., Cellcap, MPV, MPVII); entomopathogenic fungi, such as green muscardine fungus; and entomopathogenic virus including baculovirus, nucleopolyhedro virus (NPV) such as HzNPV, Af PV; and granulosis virus (GV) such as CpGV.
- NPV nucleopolyhedro virus
- GV granulosis virus
- Compounds of this invention and compositions thereof can be applied to plants genetically transformed to express proteins toxic to invertebrate pests (such as Bacillus thuringiensis delta-endotoxins).
- proteins toxic to invertebrate pests such as Bacillus thuringiensis delta-endotoxins.
- the effect of the exogenously applied fungicidal compounds of this invention may be synergistic with the expressed toxin proteins.
- the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30: 1).
- weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30: 1).
- One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of diseases controlled beyond the spectrum controlled by the compound of Formula 1 alone.
- combinations of a compound of this invention with other biologically active (particularly fungicidal) compounds or agents can result in a greater-than-additive (i.e. synergistic) effect. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable.
- synergism of fungicidal active ingredients occurs at application rates giving agronomically satisfactory levels of fungal control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load.
- a combination of a compound of Formula 1 with at least one other fungicidal active ingredient is such a combination where the other fungicidal active ingredient has different site of action from the compound of Formula 1.
- a combination with at least one other fungicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management.
- a composition of the present invention can further comprise a biologically effective amount of at least one additional fungicidal active ingredient having a similar spectrum of control but a different site of action.
- compositions which in addition to compound of Formula 1 include at least one compound selected from the group consisting of (1) alkylenebis(dithiocarbamate) fungicides; (2) cymoxanil; (3) phenylamide fungicides; (4) proquinazid (6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone); (5) chlorothalonil; (6) carboxamides acting at complex II of the fungal mitochondrial respiratory electron transfer site; (7) quinoxyfen; (8) metrafenone; (9) cyflufenamid; (10) cyprodinil; (11) copper compounds; (12) phthalimide fungicides; (13) fosetyl-aluminum; (14) benzimidazole fungicides; (15) cyazofamid; (16) fluazinam; (17) iprovalicarb; (18) propamocarb; (19) validomycin; (20) dichloroph
- Sterol biosynthesis inhibitors control fungi by inhibiting enzymes in the sterol biosynthesis pathway.
- Demethylase-inhibiting fungicides have a common site of action within the fungal sterol biosynthesis pathway, involving inhibition of demethylation at position 14 of lanosterol or 24-methylene dihydrolanosterol, which are precursors to sterols in fungi. Compounds acting at this site are often referred to as demethylase inhibitors, DMI fungicides, or DMIs.
- the demethylase enzyme is sometimes referred to by other names in the biochemical literature, including cytochrome P-450 (14DM). The demethylase enzyme is described in, for example, J. Biol. Chem.
- DMI fungicides are divided between several chemical classes: azoles (including triazoles and imidazoles), pyrimidines, piperazines and pyridines.
- the triazoles include azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole (including diniconazole-M), epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, quinconazole, simeconazole, tebuconazole, itraconazole, triadimefon, triadimenol, triticonazole and uniconazole
- the imidazoles include clotrimazole, econazole, imazalil, isoconazole, miconazole, oxpoconazole, prochloraz and triflumizole.
- the pyrimidines include fenarimol, nuarimol and triarimol.
- the piperazines include triforine.
- the pyridines include buthiobate and pyrifenox. Biochemical investigations have shown that all of the above mentioned fungicides are DMI fungicides as described by K. ⁇ . Kuck et al. in Modern Selective Fungicides - Properties, Applications and Mechanisms of Action, ⁇ . Lyr (Ed.), Gustav Fischer Verlag: New York, 1995, 205-258.
- bc ⁇ Complex Fungicides (group 28) have a fungicidal mode of action which inhibits the bc ⁇ complex in the mitochondrial respiration chain.
- the bc ⁇ complex is sometimes referred to by other names in the biochemical literature, including complex III of the electron transfer chain, and ubihydroquinone ytochrome c oxidoreductase. This complex is uniquely identified by Enzyme Commission number ECl.10.2.2.
- the bc ⁇ complex is described in, for example, J. Biol. Chem. 1989, 264, 14543-48; Methods Enzymol. 1986, 126, 253-71; and references cited therein.
- Strobilurin fungicides such as azoxystrobin, dimoxystrobin, enestroburin (SYP-Z071), fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin and trifloxystrobin are known to have this mode of action (H. Sauter et al., Angew. Chem. Int. Ed. 1999, 38, 1328-1349).
- Other fungicidal compounds that inhibit the bc ⁇ complex in the mitochondrial respiration chain include famoxadone and fenamidone.
- Alkylenebis(dithiocarbamate)s include compounds such as mancozeb, maneb, propineb and zineb.
- Phenylamides (group (3)) include compounds such as metalaxyl, benalaxyl, furalaxyl and oxadixyl.
- Carboxamides include compounds such as boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil, oxycarboxin, thifluzamide, penthiopyrad and N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH- pyrazole-4-carboxamide (PCT Patent Publication WO 2003/010149), and are known to inhibit mitochondrial function by disrupting complex II (succinate dehydrogenase) in the respiratory electron transport chain.
- complex II succinate dehydrogenase
- Copper compounds include compounds such as copper oxychloride, copper sulfate and copper hydroxide, including compositions such as Bordeaux mixture (tribasic copper sulfate).
- Phthalimides include compounds such as folpet and captan.
- Benzimidazole fungicides include benomyl and carbendazim.
- Dichlorophenyl dicarboximide fungicides include chlozolinate, dichlozoline, iprodione, isovaledione, myclozolin, procymidone and vinclozolin.
- ⁇ -DMI sterol biosynthesis inhibitors include morpholine and piperidine fungicides.
- the morpholines and piperidines are sterol biosynthesis inhibitors that have been shown to inhibit steps in the sterol biosynthesis pathway at a point later than the inhibitions achieved by the DMI sterol biosynthesis (group (27)).
- the morpholines include aldimorph, dodemorph, fenpropimorph, tridemorph and trimorphamide.
- the piperidines include fenpropidin.
- a NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet and (brs)-broad singlet.
- test suspensions for Tests A-C were first dissolved in acetone in an amount equal to 11 % of the final volume and then suspended at the desired concentration (in ppm) in acetone and purified water (50/50 mix by volume) containing 250 ppm of the surfactant Trem® 014 (polyhydric alcohol esters). The resulting test suspensions were then used in Tests A-C. Spraying a 40 ppm test suspension to the point of run-off on the test plants was the equivalent of a rate of 800 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 Blumeria graminis f. sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at 20 °C for 8 days, after which time disease ratings were visually made.
- test suspension was sprayed to the point of run-off on wheat seedlings.
- seedlings were inoculated with a spore suspension oiSeptoria tritici (the causal agent of wheat leaf blotch) and incubated in a saturated atmosphere at 20 °C for 48 h, and then moved to a growth chamber at 20 °C for 19 days, after which time disease ratings were visually made.
- test suspension was sprayed to the point of run-off on tomato seedlings.
- seedlings were inoculated with a spore suspension oiBotrytis cinerea (the causal agent of tomato botrytis) and incubated in saturated atmosphere at 20 °C for 48 h, and then moved to a growth chamber at 27 °C for 3 additional days, after which time disease ratings were visually made.
- oiBotrytis cinerea the causal agent of tomato botrytis
- Results for Tests A-C are given in Table A. In the Table, 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. All results are from applications of 40 ppm.
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Application Number | Priority Date | Filing Date | Title |
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JP2012546191A JP2013515084A (en) | 2009-12-22 | 2010-12-22 | Bactericidal and fungicidal 2- (bicyclic aryloxy) carboxamide |
US13/513,056 US20120283216A1 (en) | 2009-12-22 | 2010-12-22 | Fungicidal 2-(bicyclic aryloxy)carboxamides |
BR112012015297A BR112012015297A2 (en) | 2009-12-22 | 2010-12-22 | "Compound, fungicidal composition and method for controlling plant diseases caused by fungal plant pathogens" |
CN2010800591069A CN102844296A (en) | 2009-12-22 | 2010-12-22 | Fungicidal 2-(bicyclic aryloxy)carboxamides |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013063243A1 (en) * | 2011-10-25 | 2013-05-02 | New York University | Small molecule malarial aldolase-trap enhancers and glideosome inhibitors |
US9937176B2 (en) | 2014-09-02 | 2018-04-10 | Nippon Shinyaku Co., Ltd. | Pyrazolothiazole compound and medicine comprising same |
US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2017160124A (en) * | 2014-07-24 | 2017-09-14 | 日本曹達株式会社 | Aryloxy compound and pest control agent |
JP2018199622A (en) * | 2015-10-21 | 2018-12-20 | 日本曹達株式会社 | Amide compound and pest controlling agent |
ES2896598T3 (en) * | 2017-09-13 | 2022-02-24 | Syngenta Participations Ag | Microbiocidal quinoline (thio)carboxamide derivatives |
ES2894762T3 (en) * | 2017-09-13 | 2022-02-15 | Syngenta Participations Ag | Microbiocidal quinoline (thio)carboxamide derivatives |
US20200267978A1 (en) * | 2017-09-13 | 2020-08-27 | Syngenta Participations Ag | Microbiocidal quinoline (thio)carboxamide derivatives |
Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
GB2095558A (en) | 1981-03-30 | 1982-10-06 | Avon Packers Ltd | Formulation of agricultural chemicals |
DE3246493A1 (en) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING WATER-DISPERSIBLE GRANULES |
WO1991013546A1 (en) | 1990-03-12 | 1991-09-19 | E.I. Du Pont De Nemours And Company | Water-dispersible or water-soluble pesticide granules from heat-activated binders |
US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
US5208030A (en) | 1989-08-30 | 1993-05-04 | Imperial Chemical Industries Plc | Active ingredient dosage device |
US5232701A (en) | 1990-10-11 | 1993-08-03 | Sumitomo Chemical Company, Limited | Boron carbonate and solid acid pesticidal composition |
WO2003010149A1 (en) | 2001-07-25 | 2003-02-06 | Bayer Cropscience Ag | Pyrazolylcarboxanilides as fungicides |
WO2003024222A1 (en) | 2001-09-21 | 2003-03-27 | E. I. Du Pont De Nemours And Company | Anthranilamide arthropodicide treatment |
US20050143381A1 (en) | 2003-12-19 | 2005-06-30 | Guixue Yu | Azabicyclic heterocycles as cannabinoid receptor modulators |
WO2005082880A1 (en) | 2004-02-26 | 2005-09-09 | Wyeth | DIBENZO CHROMENE DERIVATIVES AND THEIR USE AS ERβ SELECTIVE LIGANDS |
WO2006058700A1 (en) | 2004-12-01 | 2006-06-08 | Syngenta Participations Ag | Acetamide compounds as fungicides |
WO2006113552A2 (en) | 2005-04-15 | 2006-10-26 | Smithkline Beecham Corporation | Cyanoarylamines |
WO2007022900A1 (en) | 2005-08-24 | 2007-03-01 | Bayer Cropscience Ag | Preparation of thioalkylamines with high yields |
EP1806339A1 (en) | 2005-12-21 | 2007-07-11 | Ucb, S.A. | Process for the preparation of 2-oxo-1-pyrrolidine derivatives |
WO2007136571A1 (en) | 2006-05-15 | 2007-11-29 | Merck & Co., Inc. | Pro-drugs of tertiary alcohols |
WO2008008539A2 (en) | 2006-07-14 | 2008-01-17 | Amgen Inc. | Fused heterocyclic derivatives useful as inhibitors of the hepatocyte growth factor receptor |
WO2008103277A2 (en) | 2007-02-16 | 2008-08-28 | Amgen Inc. | Nitrogen-containing heterocyclyl ketones and their use as c-met inhibitors |
WO2008110355A1 (en) | 2007-03-14 | 2008-09-18 | Syngenta Participations Ag | Quinoline derivatives as fungicides |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3702964A1 (en) * | 1987-01-30 | 1988-08-11 | Shell Agrar Gmbh & Co Kg | Aryloxy carboxylic acid derivatives, their preparation and their use |
-
2010
- 2010-12-13 TW TW099143569A patent/TW201124078A/en unknown
- 2010-12-21 AR ARP100104831A patent/AR079666A1/en unknown
- 2010-12-22 UY UY33147A patent/UY33147A/en not_active Application Discontinuation
- 2010-12-22 MX MX2012007223A patent/MX2012007223A/en not_active Application Discontinuation
- 2010-12-22 AU AU2010341457A patent/AU2010341457A1/en not_active Abandoned
- 2010-12-22 CN CN2010800591069A patent/CN102844296A/en active Pending
- 2010-12-22 KR KR1020127019176A patent/KR20120104390A/en not_active Application Discontinuation
- 2010-12-22 WO PCT/US2010/061765 patent/WO2011087837A2/en active Application Filing
- 2010-12-22 BR BR112012015297A patent/BR112012015297A2/en not_active IP Right Cessation
- 2010-12-22 JP JP2012546191A patent/JP2013515084A/en active Pending
- 2010-12-22 US US13/513,056 patent/US20120283216A1/en not_active Abandoned
- 2010-12-22 EP EP10798443A patent/EP2516385A2/en not_active Withdrawn
Patent Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
GB2095558A (en) | 1981-03-30 | 1982-10-06 | Avon Packers Ltd | Formulation of agricultural chemicals |
DE3246493A1 (en) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING WATER-DISPERSIBLE GRANULES |
US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
US5208030A (en) | 1989-08-30 | 1993-05-04 | Imperial Chemical Industries Plc | Active ingredient dosage device |
WO1991013546A1 (en) | 1990-03-12 | 1991-09-19 | E.I. Du Pont De Nemours And Company | Water-dispersible or water-soluble pesticide granules from heat-activated binders |
US5232701A (en) | 1990-10-11 | 1993-08-03 | Sumitomo Chemical Company, Limited | Boron carbonate and solid acid pesticidal composition |
WO2003010149A1 (en) | 2001-07-25 | 2003-02-06 | Bayer Cropscience Ag | Pyrazolylcarboxanilides as fungicides |
WO2003024222A1 (en) | 2001-09-21 | 2003-03-27 | E. I. Du Pont De Nemours And Company | Anthranilamide arthropodicide treatment |
US20050143381A1 (en) | 2003-12-19 | 2005-06-30 | Guixue Yu | Azabicyclic heterocycles as cannabinoid receptor modulators |
WO2005082880A1 (en) | 2004-02-26 | 2005-09-09 | Wyeth | DIBENZO CHROMENE DERIVATIVES AND THEIR USE AS ERβ SELECTIVE LIGANDS |
WO2006058700A1 (en) | 2004-12-01 | 2006-06-08 | Syngenta Participations Ag | Acetamide compounds as fungicides |
WO2006113552A2 (en) | 2005-04-15 | 2006-10-26 | Smithkline Beecham Corporation | Cyanoarylamines |
WO2007022900A1 (en) | 2005-08-24 | 2007-03-01 | Bayer Cropscience Ag | Preparation of thioalkylamines with high yields |
EP1806339A1 (en) | 2005-12-21 | 2007-07-11 | Ucb, S.A. | Process for the preparation of 2-oxo-1-pyrrolidine derivatives |
WO2007136571A1 (en) | 2006-05-15 | 2007-11-29 | Merck & Co., Inc. | Pro-drugs of tertiary alcohols |
WO2008008539A2 (en) | 2006-07-14 | 2008-01-17 | Amgen Inc. | Fused heterocyclic derivatives useful as inhibitors of the hepatocyte growth factor receptor |
WO2008103277A2 (en) | 2007-02-16 | 2008-08-28 | Amgen Inc. | Nitrogen-containing heterocyclyl ketones and their use as c-met inhibitors |
WO2008110355A1 (en) | 2007-03-14 | 2008-09-18 | Syngenta Participations Ag | Quinoline derivatives as fungicides |
Non-Patent Citations (67)
Title |
---|
"Comprehensive Heterocyclic Chemistry II", 1996, PERGAMON PRESS |
"Comprehensive Heterocyclic Chemistry", 1984, PERGAMON PRESS |
"Developments in formulation technology", 2000, PJB PUBLICATIONS |
"McCutcheon's Emulsifiers and Detergents", MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO. |
"McCutcheon's Volume 2: Functional Materials", MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO. |
"Perry's Chemical Engineer's Handbook", 1963, MCGRAW-HILL, pages: 8 - 57 |
"The BioPesticide Manual", 2001, BRITISH CROP PROTECTION COUNCIL, FARNHAM |
"The Pesticide Manual", 2003, BRITISH CROP PROTECTION COUNCIL |
A. S. DAVIDSON; B. MILWIDSKY: "Synthetic Detergents", 1987, JOHN WILEY AND SONS |
ANGEW. CHEM. INT. ED. ENG., vol. 46, 2007, pages 7259 - 7261 |
ANGEW. CHEM. INT. ED. ENG., vol. 47, 2008, pages 7511 - 7514 |
BIOORG. MED. CHEM., vol. 13, 2005, pages 5463 - 5474 |
BIOORG. MED. CHEM., vol. 15, 2007, pages 2827 - 2836 |
BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 December 1967 (1967-12-04), pages 147 - 48 |
CHEMISTRY LETTERS, 1994, pages 597 - 600 |
G. W. H. CHEESEMAN; E. S. G. WERSTIUK: "Advances in Heterocyclic Chemistry", vol. 22, ACADEMIC PRESS, pages: 390 - 392 |
GREENE, T. W.; WUTS, P. G. M.: "Protective Groups in Organic Synthesis", 1991, WILEY |
H. SAUTER ET AL., ANGEW. CHEM. INT. ED., vol. 38, 1999, pages 1328 - 1349 |
HANCE ET AL.: "Weed Control Handbook", 1989, BLACKWELL SCIENTIFIC PUBLICATIONS |
HETEROCYCLES, vol. 40, 1995, pages 271 - 8 |
J. AM. CHEM. SOC., vol. 124, 2002, pages 5380 - 5401 |
J. AM. CHEM. SOC., vol. 128, 2006, pages 4976 - 4985 |
J. AM. CHEM. SOC., vol. 130, 2008, pages 8923 - 8930 |
J. BIOL. CHEM., vol. 264, 1989, pages 14543 - 48 |
J. BIOL. CHEM., vol. 267, 1992, pages 13175 - 79 |
J. CHEM. RES., SYNOP., 1995, pages 166 - 7 |
J. CHEM. SOC., PERKIN TRANS., vol. 1, 1988, pages 1663 - 8 |
J. FLUOR. CHEM., vol. 128, 2007, pages 1271 - 1279 |
J. MED. CHEM., vol. 33, 1990, pages 2697 - 706 |
J. MED. CHEM., vol. 42, 1999, pages 3557 - 3571 |
J. MED. CHEM., vol. 46, 2003, pages 691 - 701 |
J. MED. CHEM., vol. 48, 2005, pages 3953 - 3979 |
J. MED. CHEM., vol. 50, 2007, pages 21 - 39 |
J. MED. CHEM., vol. 50, 2007, pages 6554 - 6569 |
J. MED. CHEM., vol. 51, 2008, pages 7380 - 7395 |
J. MED. CHEM., vol. 51, 2008, pages 8124 - 8134 |
J. ORG. CHEM., vol. 53, 1988, pages 1323 - 6 |
J. ORG. CHEM., vol. 71, 2006, pages 1471 - 1479 |
J. ORG. CHEM., vol. 71, 2006, pages 5921 - 5929 |
J. ORG. CHEM., vol. 73, 2008, pages 4721 - 4724 |
K. H. KUCK ET AL.: "Modern Selective Fungicides - Properties, Applications and Mechanisms of Action", 1995, GUSTAV FISCHER VERLAG, pages: 205 - 258 |
KLINGMAN: "Weed Control as a Science", 1961, JOHN WILEY AND SONS, INC., pages: 81 - 96 |
M. R. GRIMMETT; B. R. T. KEENE: "Advances in Heterocyclic Chemistry", vol. 43, PERGAMON PRESS, pages: 149 - 161 |
M. TISLER; B. STANOVNIK: "Advances in Heterocyclic Chemistry", vol. 9, ACADEMIC PRESS, pages: 285 - 291 |
M. TISLER; B. STANOVNIK: "Comprehensive Heterocyclic Chemistry", vol. 3, PERGAMON PRESS, pages: 18 - 20 |
MARSDEN: "Solvents Guide", 1950, INTERSCIENCE |
METHODS ENZYMOL., vol. 126, 1986, pages 253 - 71 |
ORGANIC LETTERS, vol. 8, 2006, pages 2843 - 2846 |
ORGANIC LETTERS, vol. 9, 2007, pages 5259 - 5262 |
SISELY; WOOD: "Encyclopedia of Surface Active Agents", 1964, CHEMICAL PUBL. CO., INC. |
SYNLETT, 1997, pages 1187 - 1189 |
SYNLETT, 2008, pages 2023 - 2027 |
SYNTHESIS, 1998, pages 729 - 734 |
SYNTHESIS, 2003, pages 2047 - 2052 |
SYNTHESIS, 2006, pages 4143 - 4150 |
SYNTHESIS, vol. 396, 1989, pages 7 |
T. L. GILCHRIST, COMPREHENSIVE ORGANIC SYNTHESIS, vol. 7, pages 748 - 750 |
T. S. WOODS: "Pesticide Chemistry and Bioscience, The Food-Environment Challenge", 1999, THE ROYAL SOCIETY OF CHEMISTRY, article "The Formulator's Toolbox - Product Forms for Modern Agriculture", pages: 120 - 133 |
TETRAHEDRON, ASYMMETRY, vol. 4, 1993, pages 1105 - 12 |
TETRAHEDRON, vol. 44, 1988, pages 3025 - 36 |
TETRAHEDRON, vol. 50, 1994, pages 5335 - 44 |
TETRAHEDRON, vol. 60, 2004, pages 4019 - 4029 |
TETRAHEDRON, vol. 64, 2008, pages 3197 - 3203 |
TETRAHEDRON, vol. 64, 2008, pages 5085 - 5090 |
TETRAHEDRON, vol. 64, 2008, pages 8155 - 8158 |
TETRAHEDRON, vol. 65, 2009, pages 638 - 643 |
WATKINS ET AL.: "Handbook of Insecticide Dust Diluents and Carriers", DORLAND BOOKS |
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US9873661B2 (en) | 2011-10-25 | 2018-01-23 | New York University | Small molecule malarial Aldolase-TRAP enhancers and glideosome inhibitors |
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US9999622B2 (en) | 2014-09-02 | 2018-06-19 | Nippon Shinyaku Co., Ltd. | Pyrazolothiazole compound and medicine comprising same |
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WO2011087837A3 (en) | 2012-01-12 |
AR079666A1 (en) | 2012-02-08 |
TW201124078A (en) | 2011-07-16 |
BR112012015297A2 (en) | 2017-06-27 |
US20120283216A1 (en) | 2012-11-08 |
EP2516385A2 (en) | 2012-10-31 |
JP2013515084A (en) | 2013-05-02 |
KR20120104390A (en) | 2012-09-20 |
CN102844296A (en) | 2012-12-26 |
AU2010341457A1 (en) | 2012-05-24 |
WO2011087837A9 (en) | 2011-09-09 |
MX2012007223A (en) | 2012-07-17 |
UY33147A (en) | 2011-07-29 |
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