WO1997000612A1 - Arthropodicidal and fungicidal cyclic amides - Google Patents

Arthropodicidal and fungicidal cyclic amides Download PDF

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Publication number
WO1997000612A1
WO1997000612A1 PCT/US1996/010326 US9610326W WO9700612A1 WO 1997000612 A1 WO1997000612 A1 WO 1997000612A1 US 9610326 W US9610326 W US 9610326W WO 9700612 A1 WO9700612 A1 WO 9700612A1
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Prior art keywords
alkyl
chr
haloalkyl
phenyl
alkoxy
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PCT/US1996/010326
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English (en)
French (fr)
Inventor
Richard James Brown
Dominic Ming-Tak Chan
Michael Henry Howard, Jr.
Dilon Jancey Daniel
David Alan Clark
Thomas Paul Selby
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E.I. Du Pont De Nemours And Company
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Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to PL96324291A priority Critical patent/PL324291A1/xx
Priority to AU61770/96A priority patent/AU6177096A/en
Priority to IL12267096A priority patent/IL122670A0/xx
Priority to EP96919422A priority patent/EP0836384A1/en
Priority to NZ310884A priority patent/NZ310884A/en
Priority to MX9710259A priority patent/MX9710259A/es
Priority to BR9609001A priority patent/BR9609001A/pt
Priority to JP9503876A priority patent/JPH11508257A/ja
Publication of WO1997000612A1 publication Critical patent/WO1997000612A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • This invention relates to certain cyclic amides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides and
  • the control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumers.
  • the control of arthropod pests is also extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
  • the control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • WO 95/14009 discloses cyclic amides of Formula i as fungicides:
  • A is O; S; ⁇ ; ⁇ R 5 ; or CR 14 ;
  • G is C or ⁇ ; provided that when G is C, A is O, S or ⁇ R 5 and the floating double bond is attached to G; and when G is ⁇ , A is ⁇ or CR 14 and the floating double bond is attached to A;
  • W is O or S
  • X is OR 1 ; S (O) m R 1 ; or halogen;
  • R 1 , R 2 , and R 5 are each independently, in part, H or C 1 -C 6 alkyl;
  • R 3 and R 4 are each independently, in part, H; halogen; cyano; nitro; C 1 -C 6 alkyl;
  • R 6 is independently H or C 1 -C 3 alkyl
  • R 7 is, in part, H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; or C 1 -C 6 alkoxy;
  • Z is, in part, an optionally substituted phenyl, 3 to 14-membered nonaromatic
  • heterocyclic ring system or 5 to 14-membered aromatic heterocyclic ring system
  • R 14 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl;
  • n 0, 1 or 2.
  • this publication does not disclose compounds where the optional substituents on Z are themselves substituted with C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 alkenyloxy, C 3 - C6 haloalkenyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 3 -C 6 alkenylthio, C 3 -C 6 haloalkenylthio, or SF 5 .
  • This invention involves compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof:
  • E is selected from:
  • A is O; S; N; NR 5 ; or CR 14 ;
  • G is C or N; provided that when G is C, then A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, then A is N or CR 14 and the floating double bond is attached to A;
  • W is O; S; NH; N(C 1 -C 6 alkyl); or NO(C 1 -C 6 alkyl);
  • X is H; OR 1 ; S(O) m R 1 ; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 3 -C 6 cycloalkyl; cyano; NH 2 ; NHR 1 ; N(C 1 -C 6 alkyl)R 1 ; NH(C 1 -C 6 alkoxy); or
  • R 1 is C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6
  • alkynyl C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; or C 2 -C 4 alkoxycarbonyl;
  • R 2 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; hydroxy; C 1 -C 2 alkoxy; or acetyloxy;
  • R 3 and R 4 are each independently halogen; cyano; nitro; hydroxy; C 1 -C 6 alkyl;
  • C 1 -C 6 haloalkyl C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 2 -C 6 alkenyloxy; C 2 -C 6 alkynyloxy; C 1 -C 6 alkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; formyl; C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl; NH 2 C(O);
  • R 5 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; or C 2 -C 4 alkoxycarbonyl;
  • -CR 6 CR 6 -; -C ⁇ C-; -CHR 15 O-; -OCHR 15 -; -CHR 15 S(O) n -; -S(O) n CHR 15 -;
  • Z 1 is H or -A 3 -Z
  • W 1 is O or S
  • a 1 is O; S; NR 15 ; or a direct bond;
  • a 2 is O; NR 15 ; or a direct bond;
  • each R 6 is independently H; 1-2 CH 3 ; C 2 -C 3 alkyl; C 1 -C 3 alkoxy; C 3 -C 6
  • alkoxycarbonylamino NH 2 C(O)NH; (C 1 -C 3 alkyl)NHC(O)NH; (C 1 -C 3 alkyl) 2 NC(O)NH; N(C 1 -C 3 alkyl) 2 ; piperidinyl; morpholinyl;
  • each R 7 is independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 1 -C 6 alkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; C 1 -C 6 haloalkylthio; C 1 -C 6 haloalkylsulfmyl; C 1 -C 6 haloalkylsulfonyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy;
  • a ring system selected from 3 to 14-membered monocyclic, fused bicyclic and fused tricyclic nonaromatic heterocyclic ring systems and 5 to
  • each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each nonaromatic or aromatic heterocyclic ring system substituted with R 9 and optionally substituted with one or more R 10 ;
  • each Q is independently selected from the group -CHR 13 -, -NR 13 -, -O-, and
  • R 8 is H; 1-2 halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6
  • C 3 -C 6 cycloalkyl C 3 -C 6 alkenyloxy; CO 2 (C 1 -C 6 alkyl); NH(C 1 -C 6 alkyl);
  • N(C 1 -C 6 alkyl) 2 cyano; nitro; SiR 19 R 20 R 21 ; or GeR 19 R 20 R 21 ;
  • R 9 is H; 1-2 halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6
  • C 3 -C 6 cycloalkyl C 3 -C 6 alkenyloxy; CO 2 (C 1 -C 6 alkyl); NH(C 1 -C 6 alkyl);
  • N(C 1 -C 6 alkyl) 2 ; -C(R 18 ) NOR 17 ; cyano; nitro; SF 5 ; SiR 22 R 23 R 24 ; or
  • R 9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R 11 , R 12 , or both R 1 1 and R 12 ;
  • each R 10 is independently halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C ⁇ -C 4 alkoxy; nitro; or cyano; or
  • R 9 and an R 10 when R 9 and an R 10 are attached to adjacent atoms on Z, R 9 and said adjacently attached R 10 can be taken together as -OCH 2 O- or -OCH 2 CH 2 O-; each CH 2 group of said taken together R 9 and R 10 optionally substituted with 1-2 halogen; or
  • R 7 and said adjacently attached R 10 can be taken together as -(CH 2 ) r -J- such that J is attached to Z;
  • J is -CH 2 -; -CH 2 CH 2 -; -OCH 2 -; -CH 2 O-; -SCH 2 -; -CH 2 S-; -N(R 16 )CH 2 -; or
  • R 11 and R 12 are each independently 1-2 halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl;
  • haloalkylsulfonyl C 3 -C 6 alkenylthio; C 3 -C 6 haloalkenylthio; C 2 -C 6 alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R 26 ) 2 ; SF 5 ;
  • each R 13 is independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; or phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano;
  • R 14 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl;
  • R 7 and the adjacently attached R 15 can be taken together as -CH 2 -(CH 2 ) s -; -O-(CH 2 ) s -; -S-(CH 2 ) s -; or
  • R 16 , R 17 , and R 18 are each independently H; C 1 -C 3 alkyl; C 3 -C 6 cycloalkyl; or phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano;
  • R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 are each independently C 1 -C 6 alkyl; C 2 -C 6
  • alkenyl C 1 -C 4 alkoxy; or phenyl
  • each R 25 is independently C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 2 -C 4 alkenyl; C 1 -C 4 alkoxy; or phenyl;
  • each R 26 is independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano; each R 27 is independently C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkyn
  • r is 0 or 1 ;
  • s 2 or 3.
  • This invention provides a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, provided that:
  • E 1,2-phenylene optionally substituted with one of R 3 , R 4 , or both R 3 and R 4 ;
  • X is OR 1 , S(O)mR 1 or halogen;
  • R 9 is SiR 22 R 23 R 24 or GeR 22 R 23 R 24 ; then Z is other than phenyl or a 5 to 14-membered aromatic heterocyclic ring system each substituted with R 9 and optionally substituted with one or more R 10 ;
  • This invention also provides selected compounds of Formula I which are considered particularly effective fungicides and arthropodicides.
  • this invention provides compounds of Formula IA including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, and agricultural compositions containing them and their use as fungicides and arthropodicides:
  • E is 1,2-phenylene optionally substituted with one of R 3 , R 4 , or both R 3 and R 4 ;
  • A is O or N;
  • G is C or N; provided that when G is C, then A is O and the floating double bond is attached to G; and when G is N, then A is N and the floating double bond is attached to A;
  • W is O
  • X is OR 1 ;
  • R 1 is C 1 -C 3 alkyl
  • R 2 is H or C 1 -C 2 alkyl
  • R 3 and R 4 are each independently halogen; cyano; nitro; C 1 -C 6 alkyl; C 1 -C 6
  • haloalkyl C 1 -C 6 alkoxy; or C 1 -C 6 haloalkoxy; C 1 -C 6 alkylsulfonyl; C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl; (C 1 -C 4 alkyl)NHC(O);
  • Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; 1,3,4-oxadiazolyl;
  • R 9 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy;
  • each R 10 is independently halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C 4 alkoxy; nitro; or cyano; or
  • R 9 and an R 10 when R 9 and an R 10 are attached to adjacent atoms on Z, R 9 and said adjacently attached R 10 can be taken together as -OCH 2 O- or -OCH 2 CH 2 O-; each CH 2 group of said taken together R 9 and R 10 optionally substituted with 1-2 halogen;
  • R 11 and R 12 are each independently 1-2 halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl;
  • haloalkylsulfonyl C 3 -C 6 alkenylthio; C 3 -C 6 haloalkenylthio; C 2 -C 6 alkylthioalkylthio; nitro; cyano; thiocyanato; hydroxy; N(R 26 ) 2 ; SF 5 ;
  • R 15 is H; C 1 -C 3 alkyl; or cyclopropyl
  • R 17 and R 18 are each independently H; C 1 -C 3 alkyl; C 3 -C 6 cycloalkyl; or phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano;
  • R 22 , R 23 , and R 24 are each independently C 1 -C 6 alkyl; C 2 -C 6 alkenyl; C 1 -C 4
  • This invention also provides certain compounds of Formula I which are useful as fungicides and arthropodicides.
  • this invention provides compounds of Formula IB including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, and agricultural compositions containing them and their use as fungicides and arthropodicides:
  • E is selected from:
  • G and Y are attached to the same ring, then G and Y are attached to adjacent ring members, each aromatic heterocyclic ring system optionally substituted with one of R 3 , R 4 , or both R 3 and R 4 ;
  • A is O; S; N; NR 5 ; or CR 14 ;
  • G is C or N; provided that when G is C, then A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, then A is N or CR 14 and the floating double bond is attached to A;
  • W is O; S; NH; N(C 1 -C 6 alkyl); or NO(C 1 -C 6 alkyl);
  • X is H; OR 1 ; S(O ) m R 1 ; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 3 -C 6 cycloalkyl; cyano; NH 2 ; NHR 1 ; N(C 1 -C 6 alkyl) R 1 ; NH(C 1 -C 6 alkoxy); or
  • R 1 is C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6
  • alkynyl C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; or C 2 -C 4 alkoxycarbonyl;
  • R 2 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; hydroxy; C 1 -C 2 alkoxy; or acetyloxy;
  • R 3 and R 4 are each independently halogen; cyano; nitro; hydroxy; C 1 -C 6 alkyl;
  • C 2 -C 6 haloalkyl C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 2 -C 6 alkenyloxy; C 2 -C 6 alkynyloxy; C 1 -C 6 alkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; formyl;
  • R 25 3 Si-C ⁇ C-; or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R 8 and optionally substituted with one or more R 10 ; or when E is 1,2-phenylene and R 3 and R 4 are attached to adjacent atoms, R 3 and R 4 can be taken together as C 3 -C 5 alkylene, C 3 -C 5 haloalkylene, C 3 -C 5 alkenylene or C 3 -C 5 haloalkenylene each optionally substituted with 1-2 C 1 -C 3 alkyl;
  • R 5 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; or C 2 -C 4 alkoxycarbonyl;
  • -CR 6 CR 6 -; -C ⁇ C-; -CHR 15 O-; -OCHR 15 -; -CHR 15 S(O) n -; -S(O) n CHR 15 -;
  • Z 1 is H or -A 3 -Z
  • W 1 is O or S
  • a 1 is O; S; NR 15 ; or a direct bond;
  • a 2 is O; NR 15 ; or a direct bond;
  • each R 6 is independently H; 1-2 CH 3 ; C 2 -C 3 alkyl; C 1 -C 3 alkoxy; C 3 -C 6
  • alkoxycarbonylamino NH 2 C(O)NH; (C 1 -C 3 alkyl)NHC(O)NH;
  • each R 7 is independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 1 -C 6 alkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; C 1 -C 6 haloalkylthio; C 1 -C 6 haloalkylsulfinyl; C 1 -C 6 haloalkylsulfonyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 ⁇ C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy
  • a ring system selected from 3 to 14-membered monocyclic, fused bicyclic and fused tricyclic nonaromatic heterocyclic ring systems and 5 to
  • each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each nonaromatic or aromatic heterocyclic ring system substituted with R 9 and optionally substituted with one or more R 10 ;
  • each Q is independently selected from the group -CHR 13 -, -NR 13 -, -O-, and
  • R 8 is H; 1-2 halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6
  • N(C 1 -C 6 alkyl) 2 cyano; nitro; SiR 19 R 20 R 21 ; or GeR 19 R 20 R 21 ;
  • R 9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each substituted with R 1 1 and optionally substituted with R 12 ;
  • each R 10 is independently halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C 4 alkoxy; nitro; or cyano; or when R 9 and an R 10 are attached to adjacent atoms on Z, R 9 and said adjacently attached R 10 can be taken together as -OCH 2 O- or -OCH 2 CH 2 O-; each CH 2 group of said taken together R 9 and R 10 optionally substituted with 1-2 halogen; or
  • R 7 and said adjacently attached R 10 can be taken together as -(CH 2 ) r -J- such that J is attached to Z;
  • J is -CH 2 -; -CH 2 CH 2 -; -OCH 2 -; -CH 2 O-; -SCH 2 -; -CH 2 S-; -N(R 16 )CH 2 -; or
  • R 11 is C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 2 -C 6 alkoxyalkyl; C 2 -C 6 alkyl thioalkyl; C 3 -C 6 alkoxy alkynyl; C 7 -C 10
  • R 12 is 1-2 halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6
  • haloalkenyl C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 2 -C 6 alkoxyalkyl; C 2 -C 6 alkylthioalkyl; C 3 -C 6 alkoxy alkynyl; C 7 -C 10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; C 1 -C 4 alkoxy; C 1 -C 4 haloalkoxy; C 3 -C 6 alkenyloxy;
  • each R 13 is independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; or phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano;
  • R 14 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl;
  • each R 15 is independently H; C 1 -C 3 alkyl; C 3 -C 6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C 1 -C 4 alkyl,
  • R 7 and the adjacently attached R 15 can be taken together as -CH 2 -(CH 2 ) s -; -O-(CH 2 ) s -; -S-(CH 2 ) s -; or
  • R 16 is H; C 1 -C 3 alkyl; C 3 -C 6 cycloalkyl; or phenyl optionally substituted with
  • R 19 , R 20 , and R 21 are each independently C 1 -C 6 alkyl; C 2 -C 6 alkenyl; C 1 -C 4
  • each R 25 is independently C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 2 -C 4 alkenyl; C 1 -C 4
  • each R 26 is independently H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; or phenyl or benzyl, each optionally substituted on the phenyl ring with halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or cyano; each R 27 is independently C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkyn
  • r is 0 or 1 ;
  • s 2 or 3.
  • This invention also provides compounds of Formula II including all geometric and stereoisomers which are useful as intermediates for the preparation of the fungicides and arthropodicides of Formula I where Y is oxygen:
  • E is 1,2-phenylene optionally substituted with one of R 3 , R 4 , or both R 3 and R 4 ;
  • A is O; S; N; NR 5 ; or CR 14 ;
  • G is C or N; provided that when G is C, then A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, then A is N or CR 14 and the floating double bond is attached to A;
  • W is O; S; NH; N(C 1 -C 6 alkyl); or NO(C 1 -C 6 alkyl);
  • X is OR 1 ; S(O) m R 1 ; or halogen;
  • R 1 is C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6
  • alkynyl C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; or C 2 -C 4 alkoxycarbonyl;
  • R 2 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; hydroxy; C 1 -C 2 alkoxy; or acetyloxy;
  • R 3 and R 4 are each independently halogen; cyano; nitro; hydroxy; C 1 -C 6 alkyl;
  • C 1 -C 6 haloalkyl C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 2 -C 6 alkenyloxy; C 2 -C 6 alkynyloxy; C.-C 6 alkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; formyl; C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl; NH 2 C(O);
  • R 3 and R 4 can be taken together as C 3 -C 5 alkylene, C 3 -C 5 haloalkylene, C 3 -C 5 alkenylene or C 3 -C 5 haloalkenylene each optionally substituted with 1-2 C 1 -C 3 alkyl; R 5 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkeny
  • R 8 is H; 1-2 halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6
  • each R 10 is independently halogen; C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C 4 alkoxy; nitro; or cyano;
  • R 14 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl;
  • R 19 , R 20 and R 21 are each independently C 1 -C 6 alkyl; C 2 -C 6 alkenyl; C 1 -C 4
  • each R 25 is independently C 1 -C 4 alkyl; C 1 -C 4 haloalkyl; C 2 -C 4 alkenyl; C 1 -C 4 alkoxy; or phenyl; and
  • n 0, 1 or 2.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers.
  • 1-2 CH 3 indicates that the substituent can be methyl or, when there is a hydrogen attached to the same atom, the substituent and said hydrogen can both be methyl.
  • Alkenyl includes straight-chain or branched alkenes such as vinyl, 1-propenyl,
  • Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
  • Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkylene denotes a straight-chain alkanediyl. Examples of “alkylene” include CH 2 CH 2 CH 2 ,
  • Alkoxy includes, for example, methoxy, ethoxy, n-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 ,
  • Alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • Alkynyloxy includes straight-chain or branched alkynyloxy moieties.
  • alkynyloxy examples include HC ⁇ CCH 2 O, CH 3 OCCH 2 O and CH 3 C ⁇ CCH 2 CH 2 O.
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylfhio, butylthio, pentylthio and hexylthio isomers.
  • Alkylthioalkyl denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” 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 .
  • Alkylthioalkylthio denotes alkylthio substitution on alkylthio. Analogously,
  • alkylthioalkoxy denotes alkylthio substitution on alkoxy.
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • Alkenylthio is defined analogously to the above examples.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Cycloalkenyl includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and
  • Trialkylsilylalkoxyalkoxy denotes trialkylsilylalkoxy substitution on alkoxy.
  • Examples of “trialkylsilylalkoxyalkoxy” includes, for example,
  • aromatic carbocyclic ring system includes fully aromatic carbocycles and carbocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the H ⁇ ckel rule is satisfied).
  • nonaromatic carbocyclic ring system denotes fully saturated carbocycles as well as partially or fully unsaturated carbocycles where the H ⁇ ckel rule is not satisfied by any of the rings in the ring system.
  • aromatic heterocyclic ring system includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the H ⁇ ckel rule is satisfied).
  • nonaromatic heterocyclic ring system denotes fully saturated heterocycles as well as partially or fully unsaturated heterocycles where the H ⁇ ckel rule is not satisfied by any of the rings in the ring system.
  • the heterocyclic ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • 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.
  • halogen either alone or in compound words such as “haloalkyl” includes fluorine, chlorine, bromine or iodine.
  • 1-2 halogen indicates that one or two of the available positions for that substituent may be halogen which are independently selected.
  • alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haloalkyl include F 3 C, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 .
  • haloalkenyl “haloalkynyl", “haloalkoxy", and the like, are defined analogously to the term “haloalkyl”.
  • CF 3 CH 2 CH CHCH 2 .
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CCl 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CCl 3 S, CF 3 S, CCl 3 CH 2 S and ClCH 2 CH 2 CH 2 S.
  • haloalkylsulfinyl examples include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O).
  • haloalkylsulfonyl examples include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • C i -C j The total number of carbon atoms in a substituent group is indicated by the "C i -C j " prefix where i and j are numbers from 1 to 10.
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl.
  • alkylcarbonyl examples include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • alkoxycarbonyl when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s).
  • the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the present invention comprises compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • the salts of the compounds of the invention include acid- addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a phenol.
  • E is selected from the group 1,2-phenylene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, 2,7-, 1,2-, and 2,3-naphthalenediyl; 1H-pyrrole-1,2-, 2,3- and 3,4-diyl; 2,3- and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl;
  • 4,5-isothiazolediyl 4,5-thiazolediyl; 4,5-thiazolediyl; 1H-1,2,3-triazole-1,5- and 4,5-diyl; 2H-1,2,3-triazole-4,5-diyl; 1H-1,2,4-triazole- 1,5-diyl; 4H-1,2,4-triazole-3,4-diyl; 1,2,3-oxadiazole-4,5-diyl;
  • W is O
  • R 1 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl
  • R 2 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; or C 3 -C 6 cycloalkyl;
  • R 3 and R 4 are each independently halogen; cyano; nitro; C 1 -C 6 alkyl;
  • C 1 -C 6 haloalkyl C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 1 -C 6 alkylthio; C 1 -C 6 alkylsulfonyl; C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl;
  • -CH CH-; -C ⁇ C-; -CH 2 O-; -OCH 2 -; -CH 2 S(O) n -; -S(O) n CH 2 -;
  • R 7 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 alkylthio;
  • R 7 and said adjacently attached R 10 can be taken together as -(CH 2 ) r -J- such that J is attached to Z;
  • Z is selected from the group C 1 -C 10 alkyl; C 3 -C 8 cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; 1H-pyrrolyl; furanyl; thienyl; 1H-pyrazolyl; 1H-imidazolyl; isoxazolyl; oxazolyl;
  • azulenyl and thiazolo[2,3-c]-1,2,4-triazolyl; each group substituted with R 9 and optionally substituted with one or more R 10 ; and R 15 is ⁇ ; C 1 -C 3 alkyl; or C 3 -C 6 cycloalkyl.
  • E is selected from the group 1,2-phenylene; 1,6-, 1,7-, 1,2-, and 2,3-naphfhalenediyl; 2,3- and 3,4-furandiyl; 2,3- and
  • Z is selected from the group phenyl; naphthalenyl; 2-thiazolyl;
  • 1,3,4-thiadiazolyl pyridinyl; and pyrimidinyl; each group substituted with R 9 and optionally substituted with one or more R 10 ;
  • R 7 is ⁇ ; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 alkylthio;
  • R 7 and said adjacently attached R 10 can be taken together as -(CH 2 ) r -J- such that J is attached to Z;
  • J is -CH 2 - or -CH 2 CH 2 -;
  • E is 1 ,2-phenylene optionally substituted with one of R 3 , R 4 , or both R 3 and R 4 ;
  • A is O or N
  • X is OR 1 ;
  • R 1 is C 1 -C 3 alkyl
  • R 2 is H or C 1 -C 2 alkyl
  • -CH CH-; -C ⁇ C-; -CH 2 O-; -OCH 2 -; -CH 2 S(O) n -; -S(O) n CH 2 -; or a direct bond;
  • Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl;
  • 1,3,4-oxadiazolyl 1,2,4-thiadiazolyl; and 1,3,4-thiadiazolyl; each group substituted with R 9 and optionally substituted with R 10 ; and R 15 is H; C 1 -C 3 alkyl; or cyclopropyl.
  • R 1 is methyl
  • R 2 is methyl
  • R 9 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 1 -C 6 alkylthio; C 1 -C 6 haloalkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; C 3 -C 6 cycloalkyl;
  • R 9 is phenyl, benzyl, phenoxy, pyridinyl, thienyl, furanyl, or pyrimidinyl each optionally substituted with one of R 11 , R 12 , or both R 11 and R 12 .
  • Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; and
  • Y is -O-
  • R 9 is phenyl optionally substituted with one of R 11 , R 12 , or both R 1 1 and R 12 .
  • Most preferred are methods of Preferred 5 where the compound is selected from the group:
  • Preferred compounds of Formula IA for reasons of better arthropodicidal or fungicidal activity and/or ease of synthesis are:
  • R 1 is methyl
  • R 2 is methyl
  • R 9 is H; halogen; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 1 -C 6 alkylthio; C 1 -C 6 haloalkylthio; C 1 -C 6 alkylsulfinyl; C 1 -C 6 alkylsulfonyl; C 3 -C 6 cycloalkyl;
  • SiR 22 R 23 R 24 ; or GeR 22 R 23 R 24 ; or R 9 is phenyl, benzyl, phenoxy, pyridinyl, thienyl, furanyl, or pyrimidinyl each optionally substituted with one of R 11 , R 12 , or both R 11 and R 12 .
  • Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl;
  • Y is -O-
  • R 9 is phenyl optionally substituted with one of R 11 , R 12 , or both R 11 and R 12 .
  • This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula IA and at least one of a surfactant, a solid diluent or a liquid diluent.
  • fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula IA and at least one of a surfactant, a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds of Formula IA.
  • This invention also relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of the compounds of Formula IA and the compositions described herein.
  • the preferred methods of use are those involving the above preferred compounds of Formula IA.
  • This invention also relates to arthropodicidal compositions comprising
  • This invention also relates to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of the compounds of Formula IA and the compositions described herein.
  • the preferred methods of use are those involving the above preferred compounds of
  • arthropodicidal activity and/or ease of synthesis are:
  • E is selected from the group 1,2-phenylene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-,
  • W is O
  • R 1 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl
  • R 2 is ⁇ ; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; or C 3 -C 6 cycloalkyl;
  • R 3 and R 4 are each independently halogen; cyano; nitro; C 1 -C 6 alkyl;
  • C 1 -C 6 haloalkyl C 1 -C 6 alkoxy; C 1 -C 6 haloalkoxy; C 1 -C 6 alkylthio; C 1 -C 6 alkylsulfonyl; C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl; (C 1 -C 4 alkyl)N ⁇ C(O); (C 1 -C 4 alkyl) 2 NC(O); benzoyl; or phenylsulfonyl;
  • -CH CH-; -C ⁇ C-; -CH 2 O-; -OCH 2 -; -CH 2 S(O) n -; -S(O) n CH 2 -;
  • R 7 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 alkylthio;
  • R 7 and said adjacently attached R 10 can be taken together as -(CH 2 ) r -J- such that J is attached to Z;
  • Z is selected from the group C 1 -C 10 alkyl; C 3 -C 8 cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; 1H-pyrrolyl; furanyl; thienyl; 1H-pyrazolyl; 1H-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; 1H-1,2,3-triazolyl; 2H-1,2,3-triazolyl;
  • pyridazinyl pyrimidinyl; pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl;
  • 1,2,4,5-tetrazinyl 1H-indolyl; benzofuranyl; benzo[b]thiophenyl; 1H- indazolyl;1H- benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl; isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl; 1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-1H-indenyl;
  • azulenyl and thiazolo[2,3-c]-1,2,4-triazolyl; each group substituted with R 9 and optionally substituted with one or more R 10 ; and R 15 is ⁇ ; C 1 -C 3 alkyl; or C 3 -C 6 cycloalkyl.
  • E is selected from the group 1,2-phenylene; 1,6-, 1,7-, 1,2-, and
  • Z is selected from the group phenyl; naphthalenyl; 2-thiazolyl;
  • 1,3,4-thiadiazolyl pyridinyl; and pyrimidinyl; each group substituted with R 9 and optionally substituted with one or more R 10 ;
  • R 7 is H; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxy; C 1 -C 6 alkylthio;
  • J is -CH 2 - or -CH 2 CH 2 -;
  • E is 1,2-phenylene optionally substituted with one of R 3 , R 4 , or both R 3 and R 4 ;
  • A is O or N
  • X is OR 1 ;
  • R 1 is C 1 -C 3 alkyl
  • R 2 is H or C 1 -C 2 alkyl
  • -CH CH-; -C ⁇ C-; -CH 2 O-; -OCH 2 -; -CH 2 S(O) n -; -S(O) n CH 2 -; or a direct bond;
  • Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl;
  • 1,3,4-oxadiazolyl 1,2,4-thiadiazolyl; and 1,3,4-thiadiazolyl; each group substituted with R 9 and optionally substituted with R 10 ; and R 15 is H; C 1 -C 3 alkyl; or cyclopropyl.
  • R 1 is methyl
  • R 2 is methyl
  • R 9 is phenyl, benzyl, phenoxy, pyridinyl, thienyl, furanyl, or pyrimidinyl each substituted with R 1 1 and optionally substituted with R 12 .
  • Preferred 5B Compounds of Preferred 4B wherein:
  • Z is selected from the group 2-thiazolyl; 1,2,4-oxadiazolyl; and
  • Y is -O-
  • R 9 is phenyl substituted with R 1 1 and optionally substituted with R 12 .
  • Most preferred are compounds of Preferred 5B selected from the group:
  • This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula IB and at least one of a surfactant, a solid diluent or a liquid diluent.
  • fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula IB and at least one of a surfactant, a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds of Formula IB .
  • This invention also relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of the compounds of Formula IB and the compositions described herein.
  • the preferred methods of use are those involving the above preferred compounds of Formula IB.
  • This invention also relates to arthropodicidal compositions comprising
  • This invention also relates to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of the compounds of Formula IB and the compositions described herein.
  • the preferred methods of use are those involving the above preferred compounds of
  • W is O
  • R 1 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl
  • R 2 is ⁇ ; C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; or C 3 -C 6 cycloalkyl; and R 3 and R 4 are each independently halogen; cyano; nitro; C--C 6 alkyl;
  • C 1 -C 6 alkylsulfonyl C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl; (C 1 -C 4 alkyl)NHC(O); (C 1 -C 4 alkyl) 2 NC(O); benzoyl; or phenylsulfonyl.
  • A is O or N
  • X is OR 1 or halogen
  • R 1 is C 1 -C 3 alkyl
  • R 2 is H or C 1 -C 2 alkyl
  • R 3 and R 4 are each independently halogen; C 1 -C 3 alkyl; C 1 -C 3 alkoxy; or C 1 -C 3 alkylthio.
  • A is N;
  • R 1 is methyl
  • R 2 is methyl
  • R 3 and R 4 are each independently halogen or methyl.
  • R 7 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio,
  • R 11 and R 12 are each independently halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulf
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-33.
  • One skilled in the art will recognize that compounds of Formula IA and IB are encompassed by Formula I and, therefore, can be prepared by these procedures.
  • the definitions of E, A, G, W, X, R 1 -R 27 , Y, Z 1 , W 1 , A 1 -A 3 , Z, Q, J, m, n, p, r and s in the compounds of Formulae 1-58 below are as defined above in the Summary of the Invention.
  • Formulae Ia-Im are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-Im are as defined above for Formula I.
  • a compound of Formula I wherein R 2 is H may exist as tautomer la or lb, or both la and lb.
  • the present invention comprises all tautomeric forms of compounds of Formula I.
  • Procedures 1) to 5 describe syntheses involving construction of the amide ring after the formation of the aryl moiety (E-Y-Z).
  • Procedure 5) describes syntheses of the aryl moiety (E-Y-Z) with the amide ring already in place.
  • the compounds of Formula I are prepared by treating compounds of Formula 1 with an appropriate alkyl transfer reagent in an inert solvent with or without additional acidic or basic reagents or other reagents (Scheme 1).
  • Suitable solvents are selected from the group consisting of polar aprotic solvents such as acetonitrile,
  • ketones such as acetone or 2-butanone
  • hydrocarbons such as toluene or benzene
  • halocarbons such as dichloromethane or chloroform.
  • trimethylsilyldiazomethane (CH 3 ) 3 Si) on dicarbonyl compounds of Formula 1 (Method 1).
  • a protic cosolvent such as methanol.
  • compounds of Formula I can also be prepared by contacting carbonyl compounds of Formula 1 with alkyl trichloroacetimidates of Formula 3 and a Lewis acid catalyst.
  • Suitable Lewis acids include trimethylsilyl triflate and tetrafluoroboric acid.
  • the alkyl trichloroacetimidates can be prepared from the appropriate alcohol and trichloroacetonitrile as described in the literature (J. Danklmaier and H. Hönig, Synth. Commun., (1990), 20, 203).
  • Compounds of Formula I can also be prepared from compounds of Formula 1 by treatment with a trialkyloxonium tetrafluoroborate (i.e., Meerwein's salt) of Formula 4 (Method 3).
  • a trialkyloxonium tetrafluoroborate i.e., Meerwein's salt
  • the use of trialkyloxonium salts as powerful alkylating agents is well known in the art (see U. Schöllkopf, U. Groth, C. Deng, Angew. Chem., Int. Ed. Engl., (1981), 20, 798).
  • alkylating agents which can convert carbonyl compounds of Formula 1 to compounds of Formula I are dialkyl sulfates such as dimethyl sulfate, haloalkyl sulfonates such as methyl trifluoromethanesulfonate, and alkyl halides such as iodomethane and propargyl bromide (Method 4). These alkylations can be conducted with or without additional base.
  • Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, or tertiary amines such as triethylamine, pyridine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
  • alkali metal alkoxides such as potassium tert-butoxide
  • inorganic bases such as sodium hydride and potassium carbonate
  • tertiary amines such as triethylamine, pyridine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
  • X OH
  • X OH
  • the nucleophiles of Formula 6 are N-substituted hydroxylamines (HO- ⁇ HR 2 ) and substituted hydrazines (H ⁇ (R 5 )- ⁇ HR 2 ). Examples of such nucleophiles are N-methylhydroxylamine and methylhydrazine.
  • the malonate esters of Formula 5 can be prepared by methods described hereinafter.
  • Esters of Formula 5a can be prepared from copper (I)-catalyzed reaction of malonate esters of Formula 7 with substituted aryl halides of Formula 8 according to methods adapted from A. Osuka, T. Kobayashi and H. Suzuki, Synthesis, (1983), 67 and M. S. Malamas, T. C. Hohman, and J. Millen, J. Med. Chem., 1994, 37, 2043-2058, and illustrated in Scheme 3. Procedures to prepare compounds of Formula 8 are described below (see Scheme 32).
  • Malonate esters of Formula 5a can also be prepared from diester carboxylic acids of Formula 5b after modification of the carboxylic acid functional group to the appropriate Y and Z group.
  • a copper (I)-catalyzed coupling of malonates of Formula 7 with orthobromocarboxylic acids of Formula 8a can be used to prepare compounds of Formula 5b as shown in Scheme 3.
  • Methods to prepare compounds of Formula 8a are common in the art (see P. Beak, V. Snieckus, Acc. Chem. Res., (1982), 15, 306 and Org. React., (1979), 26, 1 and references therein).
  • malonate esters of Formula 5a can be prepared by treating aryl acetic acid esters of Formula 9 with a dialkyl carbonate or alkyl chloroformate in the presence of a suitable base such as, but not limited to, sodium metal or sodium hydride (Scheme 4).
  • a suitable base such as, but not limited to, sodium metal or sodium hydride (Scheme 4).
  • a suitable base such as, but not limited to, sodium metal or sodium hydride
  • Esters of Formula 9 can be prepared from acid-catalyzed alcoholysis of aryl acetonitriles of Formula 10 or esterification of aryl acetic acids of Formula 11 as illustrated in Scheme 5 (see Org. Synth., Coll. Vol. I, (1941), 270).
  • esters of formula 9 can be prepared by palladium (O)-catalyzed cross coupling reaction of aryl iodides of Formula 8 with a Reformatsky reagent or an alkoxy(trialkylstannyl)acetylene followed by hydration (Scheme 5).
  • a Reformatsky reagent or an alkoxy(trialkylstannyl)acetylene followed by hydration (Scheme 5).
  • Aryl acetic acid esters of Formula 9a can also be prepared by copper (I)-catalyzed condensation of aryl halides of Formula 12 with compounds of Formula 13 as described in EP-A-307,103 and illustrated below in Scheme 6.
  • esters of Formula 9 can also be prepared by forming the Y 2 bridge using conventional nucleophilic substitution chemistry (Scheme 7). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 15 or 16 with a nucleophilic ester of Formula 14 affords compounds of Formula 9b.
  • a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compound of Formula 14.
  • esters of Formula 9 can also be prepared by forming the Y 3 bridge from substituted hydroxylamine 9d and carbonyl compounds 14a.
  • the hydroxylamine 9d is in turn prepared from esters 9c. This method has been described in EP-A-600,835 and illustrated in Scheme 8.
  • Compounds of Formula I can also be prepared by reaction of Formula 17 compounds with alkali metal alkoxides (R 1 O-M + ), alkali metal thioalkoxides (R 1 S-M + ), or an amine derivative in a suitable solvent (Scheme 9).
  • the leaving group Lg 1 in the amides of Formula 17 are any group known in the art to undergo a displacement reaction of this type. Examples of suitable leaving groups include chlorine, bromine, and sulfonyl and sulfonate groups. Examples of suitable inert solvents are dimethylformamide or dimethyl sulf oxide, dimethoxyethane methanol.
  • compounds of Formula lb can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methanesulfonyl chloride, p-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 17a.
  • the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).
  • sulfonyl compounds of Formula 17b can be prepared by oxidation of the corresponding thio compound of Formula 18 using well-known methods for the oxidation of sulfur (see Schrenk, K. In The Chemistry of Sulphones and Sulphoxides; Patai, S. et al., Eds.; Wiley: New York, 1988).
  • Suitable oxidizing reagents include meta-chloro-peroxybenzoic acid, hydrogen peroxide and Oxone ® (KHSO 5 ).
  • the diacyl compound of Formula 19 is treated with excess thionyl halide, for example excess thionyl chloride.
  • the product formed first is the ring-closed compound of Formula 20 which can be isolated or converted in situ to the compound of Formula 17c; see P. Molina, A.
  • the hydrazides of Formula 19 can be prepared as illustrated in Scheme 13.
  • Ketene dithioacetals of Formula 22a can be prepared by condensing arylacetic acid esters of Formula 9 with carbon disulfide in the presence of a suitable base, followed by reaction with two equivalents of an R 1 -halide, such as iodomethane or propargyl bromide (Scheme 15).
  • the carbonylating agents of Formula 24 are carbonyl or thiocarbonyl transfer reagents such as phosgene, thiophosgene, diphosgene
  • the compounds of Formula 24 can be alkyl chloroformates or dialkyl carbonates. Some of these carbonylating reactions may require the addition of a base to effect reaction.
  • Appropriate bases include alkali metal alkoxides such as potassium tm-butoxide, inorganic bases such as sodium hydride and potassium carbonate, tertiary amines such as triethylamine and triethylenediamine, pyridine, or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
  • Suitable solvents include polar aprotic solvents such as acetonitrile, dimethylformamide, or dimethyl sulfoxide; ethers such as tetrahydrofuran,
  • reaction temperature can vary between 0°C and 150°C and the reaction time can be from 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates.
  • N-Amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17.
  • N,N'-carbonyldiimidazole, or N,N'-thiocarbonyldiimidazole produces the isocyanate or isothiocyanate of Formula 26.
  • a base can be added for reactions with phosgene or thiophosgene.
  • Subsequent treatment of the iso(thio)cyanate with an R 2 -substituted hydrazine produces the N-amino-urea of Formula 23.
  • 2-halocarboxylic acid chlorides 2-halocarboxylic acid esters or 2-haloacyl imidazoles.
  • the initial acylation on the arylamino nitrogen is followed by an intramolecular displacement of the 2-halo group to effect cyclization.
  • Base may be added to accelerate the acylation and/or the subsequent cyclization.
  • Suitable bases include triethylamine and sodium hydride.
  • Formula le compounds can be prepared by reaction of Formula 26 isocyanates with Formula 28a esters. As described above, base may be added to accelerate the reaction and subsequent cyclization to Formula 1e compounds.
  • the ureas of Formula 27 can be prepared by either of the methods illustrated in Scheme 19.
  • an isocyanate or isothiocyanate of Formula 26 can be condensed with an amine of Formula R 2 -NH 2 to form the urea.
  • the arylamine and iso(thio)cyanates of Formulae 25 and 26, respectively, are commercially available or prepared by well-known methods.
  • isothiocyanates can be prepared by methods described in J. Heterocycl. Chem., (1990), 27, 407.
  • Isocyanates can be prepared as described in March, J. Advanced Organic
  • thionating reagents such as P 2 S 5 or Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4- diphosphetane-2,4-disulfide
  • the appropriate alcohol or thiol is treated with a base, for example sodium hydride, to form the corresponding alkoxide or thioalkoxide which acts as the nucleophile.
  • aryl halides of Formula 29 can be prepared by radical halogenation of the corresponding alkyl compound (i.e., H instead of halogen in Formula 29), or by acidic cleavage of the corresponding methylether (i.e., OMe instead of halogen in Formula 29).
  • Other aryl halides of Formula 29 can be prepared from the appropriate alcohols of Formula 30 by well known halogenation methods in the art (see Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; 3rd ed., Part B, Plenum: New York, (1990), p 122).
  • the olefins of Formula lg can be converted to the saturated compounds of Formula Ih by hydrogenation over a metal catalyst such as palladium on carbon as is well-known in the art (Rylander, Catalytic Hydrogenation in Organic Synthesis;
  • Formula li alkynes can be prepared by halogenation/dehalogenation of Formula lg olefins using procedures well-known in the art (March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), p 924). Additionally, Formula li alkynes can be prepared by well-known reaction of aryl halides with alkyne derivatives in the presence of catalysts such as nickel or palladium (see J. Organomet. Chem., (1975), 93 253-257).
  • the olefin of Formula lg can also be prepared by reversing the reactivity of the reactants in the Wittig or Horner-Emmons condensation.
  • 2-alkylaryl derivatives of Formula 33 can be converted into the corresponding dibromo-compound of Formula 34 as illustrated in Scheme 23 (see Synthesis, (1988), 330).
  • the dibromo- compound can be hydrolyzed to the carbonyl compound of Formula 35, which in turn can be condensed with a phosphorus-containing nucleophile of Formula 36 or 37 to afford the olefin of Formula lg.
  • compounds of Formula 35 can be prepared by oxidation of the corresponding alcohols of Formula 30.
  • Vinylhalides of Formula Ij can be prepared by reacting phosphorus reagents of Formulae 37a or 37b with carbonyl compounds of Formula 35 (Scheme 23).
  • the preparations of halides of Formula 37a from the appropriate diethylphosphonoacetate are described by McKenna and Khawli in J. Org. Chem., (1986), 51, 5467.
  • the thiono esters of Formula 37b can be prepared from esters of Formula 37a by converting the carbonyl oxygen of the ester to a thiocarbonyl (see Chem. Rev., (1984), 84, 17 and Tetrahedron Lett., (1984), 25, 2639).
  • Carbamates of Formula II can be prepared by reacting aryl alcohols of Formula 30 with isocyanates of Formula 39 (Scheme 25). A base such as triethylamine can be added to catalyze the reaction. As shown, carbamates of Formula II can be further alkylated to provide the carbamates of Formula Im.
  • the compounds of the present invention are prepared by combinations of reactions as illustrated in the Schemes 1-25 in which Z is a moiety as described in the summary.
  • Preparation of the compounds containing the radical Z as described in the summary, substituted with L can be accomplished by one skilled in the art by the appropriate combination of reagents and reaction sequences for a particular Z-L.
  • Such reaction sequences can be developed based on known reactions available in the chemical art. For a general reference, see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley:
  • Compounds of Formula 40 can be prepared from compounds of Formula 39a (Scheme 27) by Friedel-Crafts acylation with compounds of Formula 42. (See Olah, G. "Friedel-Crafts and Related Reactions," Interscience, New York (1963-1964) for a general review). Compounds of Formula 40 may also be prepared by reaction of acyl halides, anhydrides, esters, or amides of Formula 45 with organometallic reagents of Formula 44. (See March, J.
  • the organometallic compounds of Formula 44 may be prepared by reductive metallation or halogen-metal exchange of a halogen-containing compound of Formula 43 using, for example, magnesium or an organolithium reagent, or by deprotonation of compounds of Formula 39a using a strong base such as a lithioamide or an organolithium reagent, followed by transmetallation.
  • Compounds of Formula 43 may be prepared by reaction of compounds of Formula 39a (Scheme 28) with, for example, bromine or chlorine, with or without additional catalysts, under free-radical or aromatic electrophilic halogenation conditions, depending on the nature of Z.
  • Alternative sources of halogen such as N- halosuccinimides, tert-butyl hypohalites or SO 2 Cl 2 , may also be used. (See March, J.
  • Compounds of Formula 48 can be prepared from compounds of Formula 40b by treatment with peracids such as perbenzoic or peracetic acid, or with other peroxy compounds in the presence of an acid catalysts, followed by hydrolysis of the resultant ester.
  • peracids such as perbenzoic or peracetic acid
  • acid catalysts such as sodium bicarbonate
  • Formula 48 corresponds to
  • Formula 13 in Scheme 6 when Y 1 O and reagent HO-Z in Scheme 21.
  • Compounds of Formula 52 can be prepared from compounds of Formula 48 by conversion to the dialkylthiocarbamates of Formula 50 followed by rearrangement to Formula 51 and subsequent hydrolysis. See M. S. Newman and H. A. Karnes, J. Org. Chem. (1966), 31, 3980-4.
  • Compounds of Formula 53 can be converted to compounds of Formulae 43, 48 or 52 via the diazonium compounds 54, by treatment with nitrous acid followed by subsequent reaction (Scheme 30). See reviews by Hegarty , pt. 2, pp 511-91 and Schank, pt. 2, pp 645-657, in Patai, "The Chemistry of Diazonium and Diazo Groups," Wiley, New York (1978).
  • Treatment of Formula 54 compounds with cuprous halides or iodide ions yield compounds of Formula 43.
  • Treatment of Formula 54 compounds with cuprous oxide in the presence of excess cupric nitrate provides compounds of
  • Compounds of Formula 53 can be prepared from compounds of Formula 39a by nitration, followed by reduction (Scheme 31).
  • nitrating agents are available (see Schofield, " Aromatic Nitration," Cambridge University Press, Cambridge (1980)). Reduction of nitro compounds can be accomplished in a number of ways (see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp 1 103-4 and references therein).
  • Iodides of Formula 8 can be prepared from compounds of Formula 58 by the methods described above in Schemes 21-25 for various Y-Z combinations.
  • Compounds of Formula 58 can in turn be prepared from compounds of Formula 57 by functional group interconversions which are well known to one skilled in the art.
  • the compounds of Formula 57 can be prepared by treating compounds of Formula 56 with an organolithium reagent such as n-BuLi or LDA followed by trapping the intermediate with iodine (Beak, P., Snieckus, V. Ace. Chem. Res., (1982), 15, 306).
  • suitable bases for example, K 2 CO 3 , KO-t-Bu or NaH
  • suitable solvents for example, acetone, dimethylformamide, dimethyl sulfoxide or tetrahydrofuran
  • Compounds of Formula Lg-Z may be prepared according to literature procedures, for example, Comprehensive Heterocyclic Chemistry, Pergamon Press, vol. 6, 1984, pp 463-511 or J. Org. Chem. (1973), 38, 469 or J. Het. Chem. (1979), 961 for the preparation of 1,2,4-thiadiazoles, U.S. 5,166,165 or J. Chem. Soc., Perkin Trans. 1 (1983), 967 for the preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles, EP 446,010 or J. Med. Chem. (1992), 35, 3691 for the preparation of 1,2,4-oxadiazoles.
  • R 9 may be introduced via a palladium(0)-catalyzed cross coupling reaction with the appropriate nucleophile containing R 9 , such as arylboronic acids, aryl or alkyl zinc reagents, and substituted acetylenes.
  • protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products.
  • the use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991).
  • One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I.
  • One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I.
  • Step B Preparation of 5-chloro-2.4-dihydro-4-(2-methoxyphenyl)-2-methyI-3H- 1,2,4-triazol-3-one
  • Step B The title compound of Step B (7.7 g) was dissolved in 65 mL of dichloromethane under nitrogen, cooled to -78 °C, and 34 mL of a 1.0 M boron tribromide solution in dichloromethane was then added over 0.5 h with stirring. After the addition, the cooling bath (dry ice/acetone) was kept in place for an additional 0.5 h and then the reaction was allowed to warm to room temperature. Ice was added to the reaction mixture which was then diluted with diethyl ether and the product was extracted using IN aqueous sodium hydroxide solution. The aqueous layer was acidified with 6N aqueous hydrochloric acid solution and extracted with dichloromethane and then with ethyl acetate. The organic layers were combined, dried (MgSO 4 ), filtered and concentrated under reduced pressure. The resulting residue was triturated with diethyl ether to afford 5.54 g of the title .
  • Step D Preparation of 2,4-dihydro-4-(2-hyclroxyphenyl)-5-methoxy-2-methyl- 3H-1,2,4-triazol-3-one
  • Step E Preparation of 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol-
  • Step B To a solution of the title compound of Step B (10.36 g, 43.06 mmol) in water (100 mL) is added methylene chloride (200 mL), benzyltriethylammonium chloride (0.8 g) and perchloromethyl mercaptan (4.7 mL, 32.6 mmol) and the mixture is cooled in an ice bath. With efficient stirring, sodium hydroxide (6.89 g) in water (100 mL) is then added drop wise such that the internal temperature does not exceed 10 °C. After the addition is complete, the cooling bath is removed and the reaction mixture stirred for a further 1.5 h. The organic layer is then separated, dried over magnesium sulfate and concentrated.
  • methylene chloride 200 mL
  • benzyltriethylammonium chloride 0.8 g
  • perchloromethyl mercaptan 4.7 mL, 32.6 mmol
  • Step B Preparation of 2-(4-chlorophenyl)-5-(methylsulfonyl)-1,3,4-oxadiazole
  • Step C Preparation of 4-[2-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2- yl]oxy]phenyl] -2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one
  • potassium carbonate 406 mg
  • Step B The mixture was stirred overnight before being diluted with methylene chloride and washed with water.
  • Example 4 To a solution of the title compound of Example 4 (307 mg, 0.71 mmol) in DMF (4 mL) was added copper(I) iodide (14 mg), triethylamine (0.347 mL), 3,3-dimethyl-1- butyne (0.219 mL) and bis(triphenylphosphine)palladium(II) chloride (25 mg). The mixture was stirred for 40 h at ambient temperature before being diluted with ethyl acetate, washed with 1N ⁇ Cl and dried over magnesium sulfate.
  • Example 7 To a solution of the title compound of Example 6 (300 mg, 0.629 mmol) in methanol (3 mL) was added potassium carbonate (87 mg). The mixture was stirred at ambient temperature for 10 min before being diluted with water and extracted three times with methylene chloride. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization from ethanol afforded the title compound of Example 7 (153 mg), a compound of the invention, as a white solid melting at 177-178 °C.
  • Step B Preparation of [3-[5-[2- (1 ,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-
  • Example 9 Purification by column chromatography (silica gel, 30% and then 40% ethyl acetate in benzene) gave the title compound of Example 9 (4.8 g), a compound of the invention.
  • Step C Preparation of 4-[2-[[3-(2-furanyl)-1,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4- dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one
  • Step B Preparation of 4-[2-[[3-(2,5-dichloro-3-thienyl)- 1,2,4-thiadiazol-5- ylloxy]phenyl]-2,4-dihydro-5-methoxy-2-methyI-3H-1,2,4-triazol-3-one
  • potassium carbonate (1.21 g)
  • the mixture was stirred at ambient temperature for 30 h at which point extra potassium carbonate (0.6 g) was added.
  • Step D Preparation of 4-[2-[[3-(1,1-dimethylethyl)- 1,2.4-thiadiazol-5- yl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one
  • Step D a compound of invention, as an off white solid melting at 110-1 1 1 °C. -H NMR (CDCl 3 ) ⁇ 7.58 (d,1H), 7.50 (m,1H), 7.47 (m,1H), 7.44 (m,1H), 3.78 (s,3H), 3.40 (s,3H), 1.36 (s,9H).
  • Example 15 To a solution of the title compound of Example 15 (333 mg, 1.0 mmol) and tetrakis(triphenylphosphine)palladium (60 mg) in nitrogen-purged tetrahydrofuran (2.8 mL) was added a solution of bromo(4-cyanophenyl)zinc (2.8 mL, 0.5M in tetrahydrofuran, available from Rieke Metals, Inc.). The resulting dark solution was stirred for 22 h at room temperature and an additional 1.5 mL of the organozinc reagent was then added to complete the reaction.
  • the title compound was prepared according to Zubets, I. V.; Boikov, Yu. A.;
  • Step C Preparation of 4-[2-[[5-(4-chlorophenyl)-1,3,4-thiadiazol-2- yl]oxylphenyl[-2,4-dihydro-5-methoxy-2 methyl-3H-1,2,4-triazol-3-one
  • the title compound of Step B (0.46 g, 2 mmol)
  • the title compound of Step D in Example 1 (0.44 g, 2 mmol)
  • potassium carbonate 0.8 g, 5.8 mmol
  • Step B The title compound of Step B (3 g) was dissolved in 50 mL of acetonitrile and to this solution was added with stirring 2.5 g of copper(II) chloride followed by 2 mL of tert-butylnitrite (dropwise). Nitrogen evolution was evident and the reaction exothermically warmed to approximately 30 °C. The dark reaction mixture was stirred for 45 min and was then partitioned between 200 mL of ethyl acetate and 200 mL of distilled water. The organic layer was separated, washed with IN aqueous HCl, water, and then saturated aqueous NaCl. The organic layer was dried over MgSO 4 and then was concentrated under reduced pressure to give a dark oil/solid residue.
  • Step D Preparation of 4-[2-[[5-bromo-4-[3-(trifluoromethyl)phenyl]-2- thiazolyl]oxy]phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-
  • 1,1-Dimethylhydrazine (55.0 g, 911 mmol) was added dropwise over 30 min and then the mixture was allowed to warm to room temperature and stir overnight. The mixture was cooled, filtered, and the solid was washed with ethyl acetate and dried to provide 200.0 g of the title compound of Step A as a white solid melting at 151-153 °C.
  • Step B Preparation of 5-chloro-2,4-dihydro-4-(2-methoxy-6-methylphenyl)-2- methyl-3H-1,2,4-triazol-3-one
  • Step A The title compound of Step A (100.0 g, 447.9 mmol) was suspended in ethyl acetate (1 L) and added dropwise, via mechanical pump, over 3.5 h to a stirring solution of phosgene ( 177 g, 1.79 moles) in ethyl acetate (1.5 L) which was heated at reflux. After the addition was complete, the mixture was heated at reflux for a further 3 h, cooled to room temperature and stirred overnight. The solution was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and water and extracted four times with ethyl acetate.
  • Step C Preparation of 5-chloro-2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-2- methyl-3H-1,2,4-triazol-3-one
  • Step D Preparation of 2.4-dihydro-4-(2-hydroxy-6-methylphenyll)- 5-methoxy-2- methyl-3H-1,2,4-triazol-3-one
  • Step A Preparation of 2.4-dihydro-5-methoxy-2-methyl-4-[2-[[tris(1- methylethyl)silylloxylphenyl]-3H-1,2,4-triazol-3-one
  • Step B Preparation of 4-[2-ethyl-6-[[tris( 1-methylethyl)silyl]oxy]phenyl]-2,4- dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one
  • Step C Preparation of 4-[2-[[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-thiadiazol-
  • composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsif ⁇ able
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation;
  • the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water,
  • Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in
  • the compounds of this invention are useful as plant disease control agents.
  • the present invention therefore further comprises a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, or to the plant seed or seedling to be protected, an effective amount of a compound of the invention or a fungicidal composition containing said compound.
  • the compounds and compositions of this invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These pathogens include Plasmopara viticola, Phytophthora infestans,
  • Peronospora tabacina Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium oxysporum, Verticillium dahliae, Pythium
  • the compounds of this invention also exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, stem or root feeding, seed-feeding, aquatic and
  • arthropods includes insects, mites and nematodes which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests.
  • all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders Thysanoptera, Orthoptera and
  • the compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes.
  • the compounds are active against southern corn rootworm (Diabrotica undecimpunctata howardi), aster leafhopper (Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall armyworm (Spodopterafrugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), English grain aphid (Sitobion avenae), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatellafurcifera), green leafhopper (Nephotettix cincticeps), brown planthopper
  • the compounds are active on mites, demonstrating ovicidal, larvicidal and chemosterilant activity against such families as Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri,
  • Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 and WO 92/00673 for more detailed pest descriptions.
  • Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, fonophos, imidacloprid, isofenphos, malathion,
  • insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, deltame
  • metaldehyde methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, rotenone, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides such as azoxystrobin (ICIA5504), benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper
  • Preferred for better control of plant diseases caused by fungal plant pathogens e.g., lower use rate or broader spectrum of plant pathogens controlled
  • resistance management are mixtures of a compound of this invention with a fungicide selected from the group cyproconazole, cyprodinil (CGA 219417), epoxyconazole (BAS 480F), fenpropidin, fenpropimorph, flusilazole and tebuconazole.
  • Specifically preferred mixtures are selected from the group: compound 290 and cyproconazole; compound 290 and cyprodinil (CGA 219417); compound 290 and epoxyconazole (BAS 480F); compound 290 and fenpropidin; compound 290 and fenpropimorph; compound 290 and flusilazole;
  • compound 290 and tebuconazole compound 295 and cyproconazole; compound 295 and cyprodinil (CGA 219417); compound 295 and epoxyconazole (BAS 480F);
  • compound 343 and cyprodinil CGA 219417
  • compound 343 and epoxyconazole BAS 480F
  • compound 343 and fenpropidin compound 343 and fenpropimorph
  • compound 343 and fenpropimorph compound 343 and fenpropimorph
  • compound 358 and fenpropimorph compound 358 and flusilazole; compound 358 and tebuconazole; compound 507 and cyproconazole; compound 507 and cyprodinil
  • compound 507 and tebuconazole compound 515 and cyproconazole; compound 515 and cyprodinil (CGA 219417); compound 515 and epoxyconazole (BAS 480F);
  • compound 538 and cyprodinil CGA 219417
  • compound 538 and epoxyconazole BAS 480F
  • compound 538 and fenpropidin compound 538 and fenpropimorph
  • compound 538 and flusilazole compound 538 and tebuconazole
  • compound 699 and cyproconazole compound 699 and cyprodinil (CGA 219417)
  • compound 699 and epoxyconazole (BAS 480F); compound 699 and fenpropidin; compound 699 and fenpropimorph; compound 699 and flusilazole; and compound 699 and tebuconazole.
  • Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing.
  • the compounds can also be applied to the seed to protect the seed and seedling.
  • rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions.
  • Foliage can normally be protected when treated at a rate of from less than 1 g/ha to 5,000 g/ha of active ingredient.
  • Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed.
  • Arthropod pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of the invention, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • a preferred method of application is by spraying.
  • granular formulations of these compounds can be applied to the plant foliage or the soil.
  • the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.
  • the rate of application required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.
  • control efficacy represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding.
  • Me 2 N dimethylamino
  • MeS(O) methylsulf ⁇ nyl
  • cCompound contains 28% by weight of 2,4-dihydro-5-methoxy-2-methyl-4-[5-methyl-2- [[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4- triazol-3-one which is also a compound of this invention.

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PCT/US1996/010326 1995-06-20 1996-06-13 Arthropodicidal and fungicidal cyclic amides WO1997000612A1 (en)

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PL96324291A PL324291A1 (en) 1995-06-20 1996-06-13 Anthropodicidal and fungicidal cyclic amides
AU61770/96A AU6177096A (en) 1995-06-20 1996-06-13 Arthropodicidal and fungicidal cyclic amides
IL12267096A IL122670A0 (en) 1995-06-20 1996-06-13 Arthropodicidal and fungicidal cyclic amides
EP96919422A EP0836384A1 (en) 1995-06-20 1996-06-13 Arthropodicidal and fungicidal cyclic amides
NZ310884A NZ310884A (en) 1995-06-20 1996-06-13 Arthropodicidal and fungicidal cyclic amides
MX9710259A MX9710259A (es) 1995-06-20 1996-06-13 Amidas ciclicas fungicidas y artropodicidas.
BR9609001A BR9609001A (pt) 1995-06-20 1996-06-13 Método para controle de artrópodes composto composicão fungicida e método para controlar doencas de planta
JP9503876A JPH11508257A (ja) 1995-06-20 1996-06-13 殺節足動物性及び殺菌・殺カビ性環式アミド

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WO1998020003A1 (en) * 1996-11-01 1998-05-14 E.I. Du Pont De Nemours And Company Fungicidal cyclic amides
WO1998023156A1 (en) * 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Methyl substituted fungicides and arthropodicides
WO1998005652A3 (en) * 1996-08-01 1998-06-11 E I De Pount De Nemours And Co Arthropodicidal and fungicidal cyclic amides
WO1998033381A1 (en) * 1997-01-30 1998-08-06 E.I. Du Pont De Nemours And Company Fungicidal mixtures
WO1998033382A1 (en) * 1997-01-30 1998-08-06 E.I. Du Pont De Nemours And Company Fungicidal compositions
WO1999011129A1 (en) * 1997-09-04 1999-03-11 E.I. Du Pont De Nemours And Company Enantiomerically enriched compositions and their pesticidal use
WO1999018102A1 (en) * 1997-10-08 1999-04-15 E.I. Du Pont De Nemours And Company Fungicidal and arthropodicidal cyclic amides
WO1999020615A3 (de) * 1997-10-16 1999-06-24 Basf Ag Pestizide substituierte phenylcarbamate, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung
US6200997B1 (en) 1998-02-05 2001-03-13 Basf Aktiengesellschaft Heterocyclyl-substituted phenyl compounds, processes and intermediates for their preparation and their use for controlling harmful fungi and animal pests
WO2001019803A1 (de) * 1999-09-15 2001-03-22 Basf Aktiengesellschaft Ungesättigte oximether und ihre verwendung zur bekämpfung von schadpilzen und tierischen schädlingen
WO2001028331A1 (en) * 1999-10-20 2001-04-26 Aventis Cropscience Gmbh Wood treatment
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JP2002507599A (ja) * 1998-03-26 2002-03-12 バイエル・アクチエンゲゼルシヤフト アリールフェニル置換された環式ケトエノール類
EP1103548A4 (en) * 1998-08-03 2002-05-08 Sumitomo Chemical Co TRIAZOLONE DERIVATIVES, THEIR USE, AND INTERMEDIATE PRODUCTS OBTAINED FROM SUCH DERIVATIVES
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WO1998004525A1 (en) * 1996-07-27 1998-02-05 Agrevo Uk Limited Fungicidal n-aryl five-membered cyclic imides
WO1998005652A3 (en) * 1996-08-01 1998-06-11 E I De Pount De Nemours And Co Arthropodicidal and fungicidal cyclic amides
WO1998020003A1 (en) * 1996-11-01 1998-05-14 E.I. Du Pont De Nemours And Company Fungicidal cyclic amides
WO1998023156A1 (en) * 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Methyl substituted fungicides and arthropodicides
EP1310169A3 (en) * 1997-01-30 2003-08-27 E.I. Du Pont De Nemours And Company Fungicidal mixture
WO1998033381A1 (en) * 1997-01-30 1998-08-06 E.I. Du Pont De Nemours And Company Fungicidal mixtures
WO1998033382A1 (en) * 1997-01-30 1998-08-06 E.I. Du Pont De Nemours And Company Fungicidal compositions
JP2001511779A (ja) * 1997-01-30 2001-08-14 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー 殺菌・殺カビ性混合物
WO1999011129A1 (en) * 1997-09-04 1999-03-11 E.I. Du Pont De Nemours And Company Enantiomerically enriched compositions and their pesticidal use
WO1999018102A1 (en) * 1997-10-08 1999-04-15 E.I. Du Pont De Nemours And Company Fungicidal and arthropodicidal cyclic amides
WO1999020615A3 (de) * 1997-10-16 1999-06-24 Basf Ag Pestizide substituierte phenylcarbamate, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung
US6200997B1 (en) 1998-02-05 2001-03-13 Basf Aktiengesellschaft Heterocyclyl-substituted phenyl compounds, processes and intermediates for their preparation and their use for controlling harmful fungi and animal pests
JP2002507599A (ja) * 1998-03-26 2002-03-12 バイエル・アクチエンゲゼルシヤフト アリールフェニル置換された環式ケトエノール類
US6294567B1 (en) 1998-04-23 2001-09-25 Sumitomo Chemical Company, Limited Pyrazolinone derivatives
EP1103548A4 (en) * 1998-08-03 2002-05-08 Sumitomo Chemical Co TRIAZOLONE DERIVATIVES, THEIR USE, AND INTERMEDIATE PRODUCTS OBTAINED FROM SUCH DERIVATIVES
US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor
WO2001019803A1 (de) * 1999-09-15 2001-03-22 Basf Aktiengesellschaft Ungesättigte oximether und ihre verwendung zur bekämpfung von schadpilzen und tierischen schädlingen
WO2001028331A1 (en) * 1999-10-20 2001-04-26 Aventis Cropscience Gmbh Wood treatment
RU2240690C2 (ru) * 1999-10-20 2004-11-27 Авентис Кропсайенс Гмбх Обработка древесины
US6824830B1 (en) 1999-10-20 2004-11-30 Aventis Cropscience Gmbh Wood treatment
US7144888B2 (en) 2002-08-08 2006-12-05 Amgen Inc. Vanilloid receptor ligands and their use in treatments
US7332511B2 (en) 2002-08-08 2008-02-19 Amgen Inc. Vanilloid receptor ligands and their use in treatments
US7148221B2 (en) 2002-08-08 2006-12-12 Amgen Inc. Vanilloid receptor ligands and their use in treatments
US8227469B2 (en) 2004-02-11 2012-07-24 Amgen Inc. Vanilloid receptor ligands and their use in treatments
US7511044B2 (en) 2004-02-11 2009-03-31 Amgen Inc. Vanilloid receptor ligands and their use in treatments
US7534798B2 (en) 2004-02-11 2009-05-19 Amgen Inc. Vanilloid receptor ligands and their use in treatments
US7652049B2 (en) 2004-07-02 2010-01-26 Merck & Co., Inc. CETP inhibitors
US8735435B2 (en) 2004-07-02 2014-05-27 Merck Sharp & Dohme Corp. CETP inhibitors
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BR9609001A (pt) 1999-06-29
PL324291A1 (en) 1998-05-11
ZA965196B (en) 1997-12-19
CZ394097A3 (cs) 1998-09-16
HUP9901228A3 (en) 2001-11-28
NZ310884A (en) 1999-04-29
EP0836384A1 (en) 1998-04-22
KR19990028230A (ko) 1999-04-15
HUP9901228A2 (hu) 1999-07-28
IL122670A0 (en) 1998-08-16
MX9710259A (es) 1998-03-29
AU6177096A (en) 1997-01-22

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