EP1387612A1 - Amides bicycliques a fusion pyridinyle utilises comme fongicides - Google Patents

Amides bicycliques a fusion pyridinyle utilises comme fongicides

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Publication number
EP1387612A1
EP1387612A1 EP02744275A EP02744275A EP1387612A1 EP 1387612 A1 EP1387612 A1 EP 1387612A1 EP 02744275 A EP02744275 A EP 02744275A EP 02744275 A EP02744275 A EP 02744275A EP 1387612 A1 EP1387612 A1 EP 1387612A1
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EP
European Patent Office
Prior art keywords
ome
och
alkyl
compound
ocf
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EP02744275A
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German (de)
English (en)
Inventor
Ying Song
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EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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Publication of EP1387612A1 publication Critical patent/EP1387612A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Definitions

  • This invention relates to certain bicyclic amides having a pyridinyl ring fused through two adjacent carbon atoms to a second ring, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides.
  • WO 99/42447 discloses certain benzamides of formula i as fungicides
  • R 1 is H, alkyl, or acyl
  • R 2 is H or alkyl
  • GB 2219797 discloses certain fused pyridinyl compounds of Formula ii
  • X is NHCO or NHSO 2 ;
  • Ar is an optionally substituted phenyl;
  • R 4 is alkyl, alkoxy, aryl or aralkyl;
  • m is 1, 2 or 3 and n is 1, 2 or 3.
  • Phytophthora spp. and Plasmopara spp. are in constant demand by growers. Combinations of fungicides are often used to facilitate disease control and to retard resistance development. It is desirable to enhance the activity spectrum and the efficacy of disease control by using mixtures of active ingredients that provide a combination of curative, systemic and preventative control of plant pathogens. Also desirable are combinations that provide greater residual control to allow for extended spray intervals. It is also very desirable to combine fungicidal agents that inhibit different biochemical pathways in the fungal pathogens to retard development of resistance to any one particular plant disease control agent.
  • This invention involves compounds of Formula I (including all geometric and stereoisomers), N-oxides, agriculturally suitable salts and compositions thereof:
  • B is a substituted phenyl or pyridinyl ring;
  • L is O or S;
  • R 1 is H; or C C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C3-C6 cycloalkyl, each optionally substituted;
  • R is H; or C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -Cg alkoxycarbonyl, C 2 -Cg ajkylaminocarbonyl or C 3 -Cg dialkylaminocarbonyl; and n is 1 or 2.
  • this invention includes 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 a compound of Formula I (including all geometric and stereoisomers, N-oxides and agriculturally suitable salts thereof) or a composition comprising said compound.
  • This invention also includes fungicidal compositions comprising (1) a fungicidally effective amount of a compound of Formula I (including all geometric and stereoisomers, N-oxides and agriculturally suitable salts thereof); and (2) (i) at least one other insecticide, fungicide, nematocide, bactericide, acaricide, growth regulator, chemosterilant, semiochemical, repellent, attractant, pheromone, feeding stimulant or other biologically active compound; and/or (ii) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
  • fungicidal compositions comprising (1) a fungicidally effective amount of a compound of Formula I (including all geometric and stereoisomers, N-oxides and agriculturally suitable salts thereof); and (2) (i) at least one other insecticide, fungicide, nematocide, bactericide, acaricide, growth regulator, chemosterilant, semi
  • compositions comprising (a) at least one compound of Formula I; and (b) at least one compound selected from the group consisting of
  • A is a substituted fused pyridinyl ring and B is a substituted phenyl or pyridinyl ring.
  • substituted in connection with these A or B rings refers to groups that have at least one non-hydrogen substituent that does not extinguish the fungicidal activity.
  • Examples of Formula I incorporating said A and B rings in which A is substituted with one or two substituents selected from R 5 and B is substituted with from one to three substituents selected from R 6 include the rings illustrated in Exhibit 1 wherein m is an integer from 1 to 2 and p is an integer from 1 to 3.
  • attachment point between (R 5 ) m and A and (R 6 ) p and B is illustrated as floating, and (R 5 ) m and (R 6 ) p can be attached to any available carbon atom of the phenyl or pyridinyl rings.
  • R 5 when attached to A and R 6 when attached to B include each R 5 and each R 6 is independently C r C 6 alkyl, C 2 -Cg alkenyl, C 2 -C6 alkynyl, C 3 -C 6 cycloalkyl, C r C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl,
  • R 1 can be (among others) C ⁇ -Cg alkyl, C 2 -Cg alkenyl, C -Cg alkynyl or C 3 -Cg cycloalkyl, each optionally substituted.
  • R 1 groups that are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the fungicidal activity possessed by the unsubstituted analog.
  • R 1 groups are those that are optionally substituted by replacement of a hydrogen on a carbon atom of the R 1 group with one or more (up to the total number of hydrogens available for replacement in any specific R 1 group) substituents independently selected from the group consisting of halogen, CN, NO 2 , hydroxy, -C4 alkoxy, C 1 -C 4 alkylthio, C 1 -C4 alkylsulfinyl, -C4 alkylsulfonyl, C 2 -C 4 alkoxycarbonyl, C1-C4 alkylamino, C 2 -C 8 dialkylamino and C 3 -Cg cycloalkylamino.
  • substituents are Usted in the examples above, it is noted that they do not need to be present since they are optional substituents.
  • R 1 groups optionally substituted with from one to five substituents.
  • N-oxides of Formula I are illustrated as 1-5 through 1-10 in Exhibit 2, wherein R 1 , R 3 , R 5 , R 6 , W, m and p are as defined above.
  • each R 5 and each R 6 can be (among others) a phenyl ring, a 5- or 6-membered heteroaromatic ring, a benzyl ring or a phenoxy ring, each ring optionally substituted with from one to three groups independently selected from R 7 .
  • the term "optionally substituted" in connection with these groups refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog.
  • An example of a phenyl ring optionally substituted with one to three groups independently selected from R 7 is the ring illustrated as R x -56 in Exhibit 3, wherein x is either 5 or 6 and r is an integer from one to three.
  • Examples of 5- or 6-membered heteroaromatic rings optionally substituted with one to three groups independently selected from R 7 include the rings R -1 through R x -55 illustrated in Exhibit 3, wherein x is either 5 or 6 and r is an integer from one to three.
  • An example of a benzyl ring optionally substituted with one to three groups independently selected from R 7 is the ring illustrated as R x -57 in Exhibit 3, wherein x is either 5 or 6 and r is an integer from one to three.
  • An example of a phenoxy ring optionally substituted with one to three groups independently selected from R 7 is the ring illustrated as R x -58 in Exhibit 3, wherein x is either 5 or 6 and r is an integer from one
  • R 7 groups represented as (R 7 ) r
  • R x - 1 through R x -58 they do not need to be present since they are optional substituents.
  • the nitrogen atoms that require substitution to fill their valence are substituted with H or R 7 .
  • some R x groups can only be substituted with less than three R 7 groups (e.g. R x -15, R x -16, R x -17 through R -20 and R x -31 through R x -33 can only be substituted with one R 7 ).
  • R 7 r when the attachment point between (R 7 ) r and the R x group is illustrated as floating, (R 7 ) r can be attached to any available carbon atom of the R x group.
  • optionally substituted in connection with the linking chain J refers to J-groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog.
  • optionally substituted J-groups include the J-groups illustrated in Exhibit 4.
  • the J-groups in Exhibit 4 are illustrated such that the left end of the J-group is attached to the A-ring at the 3-position and the right end of the J-group is attached to the carbon atom bearing the N(R 3 )WB moiety.
  • the J-groups in Exhibit 4 can be optionally substituted by replacement of a hydrogen on a carbon atom or nitrogen atom of the J-group with one or more (up to the total number of hydrogens available for replacement in any specific J-group) substituents independently selected from the group consisting of C ⁇ -C 2 alkyl, halogen, CN, NO 2 and C ⁇ -C alkoxy. Although these substituents are listed, it is noted that they do not need to be present since they are optional substituents. Of note are J-groups optionally substituted with from one to four substituents selected from the group above.
  • alkyl used either alone or in compound words such as "alkylthio" or "haloalkyl” includes straight-chain or branched alkyl, such as methyl, ethyl, ⁇ -propyl, z ' -propyl, or the different butyl, pentyl or hexyl isomers.
  • Alkenyl includes straight chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl” also includes polyenes such as
  • Alkynyl includes straight chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl andhexynyl isomers. "Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy” includes, for example, methoxy, ethoxy, /z-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Alkylthio includes branched or straight chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylfhio isomers.
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
  • alkylsulfinyl examples include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • alkylamino "dialkylamino” and the like, are defined analogously to the above examples.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH and CF 3 CC1 2 .
  • ialoalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
  • haloalkylsulfinyl examples include CF 3 S(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 .
  • Aromaatic indicates that each of the ring atoms is essentially in the same plane and has a >-orbital perpendicular to the ring plane, and in which (4n + 2) ⁇ electrons, when n is 0 or a positive integer, are associated with the ring to comply with H ⁇ ckel's rule.
  • hetero in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains, no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
  • the t rms "heteroaromatic ring” includes fully aromatic heterocycles.
  • the heterocyclic ring can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • aryl refers to aromatic hydrocarbon moieties including phenyl, tolyl and naphthalenyl which may be optionally substituted.
  • aralkyl is an alkyl moiety substituted with an aryl moiety including phenylalkyls such as benzyl (which may be optionally substituted).
  • nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides.
  • nitrogen containing heterocycles which can form N-oxides.
  • tertiary amines can form N-oxides.
  • N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and -chloroperbenzoic acid (MCPB A), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane.
  • peroxy acids such as peracetic and -chloroperbenzoic acid (MCPB A)
  • hydrogen peroxide such as peracetic and -chloroperbenzoic acid (MCPB A)
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethydioxirane
  • C r C alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 -C 8 dialkylamino designates, for example, (CH 3 ) 2 ⁇ , (CH 3 CH 2 ) 2 N, CH 3 CH 2 (CH 3 )N, CH 3 CH 2 CH 2 (CH 3 )N or (CH 3 ) 2 CHN(CH 3 ) containing a total of from 2 to 8 carbon atoms.
  • substituents When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (R)j_ j , then the number of substituents may be selected from the integers between i and j inclusive.
  • Compounds involved in 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 may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • R 1 and J of Formula I are different, then said formula possesses a chiral center at the carbon to which they are commonly bonded.
  • This invention comprises racemic mixtures of equal parts of Formula F and Formula I".
  • this invention includes compounds and compositions that are enriched in an enantiomer of the Formula I' or Formula I" compared to the racemic mixture. Included are compounds and compositions involving the essentially pure enantiomers of Formula I' or Formula I". For example, this invention includes compounds of Formula I that are enriched in an enantiomer of the Formula F compared to the racemic mixture. Included are the essentially pure enantiomers of Formula F . This invention also includes compositions wherein component (a) is enriched in a component (a) enantiomer of Formula I" compared to the racemic rnixture.
  • This invention also includes compounds of Formula I that are enriched in an enantiomer of the Formula I" compared to the racemic mixture. Included are the essentially pure enantiomers of Formula I". This invention also includes compositions wherein component (a) is enriched in a component (a) enantiomer of Formula I" compared to the racemic mixture.
  • one enantiomer is present in greater amounts than the other and the extent of enrichment can be defined by an expression of enantiomer excess ("ee"), which is defined as 100(2x-l) where x is the mole fraction of the dominant enantiomer in the mixture, (e.g., an ee of 20% corresponds to a 60:40 ratio of enantiomers).
  • ee enantiomer excess
  • enantiomerically pure embodiments of the more active isomer are enantiomerically pure embodiments of the more active isomer.
  • the salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • 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, hthium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
  • organic bases e.g., pyridine, ammonia, or triethylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, hthium, calcium, magnesium or barium
  • This invention provides a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of a compound of Formula I including all geometric and stereoisomers, N-oxides and agriculturally suitable salts thereof (e.g. as a component of a composition described herein).
  • Preferred 1 Preferred are methods comprising compounds of Formula I wherein
  • B is substituted with from one to three substituents independently selected fromR6;
  • R 1 is H; or Cj-Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , hydroxy, C1-C4 alkoxy, C 1 -C4 alkylthio, C -C4 alkylsulfinyl, -C 4 alkylsulfonyl, C 2 -C 4 alkoxycarbonyl, C1-C4 alkylamino, C 2 -Cg dialkylamino and C 3 -Cg cycloalkylamino; each R 5 and each R 6 is independently C ⁇ -C 6 alkyl, C 2 -C6 alkenyl, C 2 -C6 alkynyl, C 3 -C 6 cycloalkyl, C
  • each R 5 and each R 6 is independently C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Cj-Cg haloalkyl, C 2 ⁇ C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CO 2 H, CONH 2 , NO 2 , hydroxy, C r C 4 alkoxy, C r C 4 haloalkoxy, C1-C4 alkylthio, C ⁇ -C ⁇ alkylsulfinyl, C ⁇ alkylsulfonyl, C1-C4 haloalkylthio, C !
  • each R 5 and each R 6 is independently phenyl, benzyl or phenoxy, each optionally substituted with C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C r C 4 haloalkyl, C 2 -C 4 haloalkenyl, C
  • J is selected from -CH 2 CH 2 - -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -OCH 2 - -OCH 2 CH 2 -, -OCH 2 CH 2 CH 2 -, -CH 2 NHCH 2 - -CH 2 N(C r C 2 alkyl)CH 2 -,-CONHCO- and -CON(C r C 2 alkyl)CO-; and each R 5 and each R 6 is independently Ci-Cg alkyl, C 2 -C 6 alkenyl, C 2 -Cg alkynyl, C 3 -Cg cycloalkyl, C Cg haloalkyl, C 2 -Cg haloalkenyl, C 2 -Cg haloalkynyl, C 3 -Cg halocycloalkyl, halogen, CN, NO 2 , C1-C 4 alkoxy, C1-C4 haloal
  • each R 5 is independently halogen, CN, NO 2 , C r C 2 alkyl, C r C 2 haloalkyl, C r C 2 alkoxy, C r C 2 haloalkoxy, C r C 2 alkylthio, C]-C alkylsulfinyl and C ⁇ -C 2 alkylsulfonyl, C ⁇ -C 2 haloalkylthio, C ⁇ -C 2 haloalkylsulfinyl C ⁇ C 2 haloalkylsulfonyl, C 2 -C4 alkoxycarbonyl or C 2 -C4 alkylaminocarbonyl.
  • R 5 is CH 3 , CI, Br, I, CN, NO 2 , CF 3 , CO 2 CH 3 , CONHCH 3 CH 3 , OCF 3 , OCHF 2 , OCH 2 CF 3 , OCF 2 CF 3 , OCF 2 CF 2 H, OCHFCF 3 , SCF 3 , SCHF 2 , SCH 2 CF 3 , SCF 2 CF 3 , SCF 2 CF 2 H, SCHFCF 3 , SOCF 3 , SOCHF 2 , SOCH 2 CF 3 , SOCF 2 CF 3 , SOCF 2 CF 2 H, SOCHFCF 3 , SO 2 CF 3 , SO 2 CHF 2 , SO 2 CH 2 CF 3 , SO 2 CF 2 CF 3 , SO 2 CF 2 CF 2 H or SO 2 CHFCF 3 .
  • each R 6 is independently C ⁇ -C 2 alkyl, C ⁇ _-C 2 haloalkyl, halogen, CN, C ⁇ C alkoxy, C 1 -C haloalkoxy, C ⁇ C 2 alkylthio, C ⁇ -C 2 alkylsulfinyl or C 1 -C 2 alkylsulfonyl and at least one R 6 is located in a position ortho to the link with W.
  • Methods of Preferred 6 wherein J is -CH 2 CH 2 - or -CH 2 CH 2 CH 2 -.
  • Preferred 8 Methods of Preferred 7 wherein each R 5 is independently CH 3 , CI, Br, I, CN, NO 2 , CF 3 , OCF 3 , OCHF 2 , SCF 3 , SCHF 2 , CO 2 CH 3 or CONHCH 3 .
  • R 5 is CH 3 , CI, Br, CN, NO 2 , CF 3 , CO 2 CH 3 or CONHCH 3 .
  • Preferred 14 Methods of any of Preferred 2 through Preferred 13 wherein R 1 is H and R 3 is H. Specifically preferred are the methods comprising a compound selected from the group consisting of 2-chloro-6-methoxy-N-(5,6,7,8-tetiahydro-3-methyl-8-quinolinyl)-4- pyridinecarboxamide,
  • This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of Formula I.
  • the preferred compositions of the present invention are those which comprise the compounds recited in Preferred 1 through Preferred 14 above.
  • Preferred compounds are those recited in Preferred 1 through Preferred 14 above, subject to the proviso above.
  • a specifically preferred compound is 2-chloro-6-methoxy-N-(5,6,7,8-tetrahydro-3- methyl- 8 -quinolinyl)-4-pyridinecarboxamide.
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-19.
  • Compounds of Formulae la, lb and Ic are subsets of the compounds of Formula I, and all substituents for Formulae la, lb and Ic are as defined above for Formula I.
  • the definitions of A, B, J, L, W, R 1 through R 6 andm in the compounds of Formulae 1-19 below are as defined above.
  • the compounds of Formula la are prepared by treating amine or amine salts of Formula 1 with an appropriate acid chloride in an inert solvent with two molar equivalents of a base (e.g. triethylamine (Et ⁇ ), polymer supported diisopropylethylamine or potassium carbonate) present.
  • a base e.g. triethylamine (Et ⁇ ), polymer supported diisopropylethylamine or potassium carbonate
  • Formula lb are prepared by treating amine or amine salts of Formula 1 with an appropriate sulfonyl chloride in an inert solvent with two molar equivalents of a base (e.g. triethylamine, polymer supported diisopropylethylamine or potassium carbonate) present.
  • a base e.g. triethylamine, polymer supported diisopropylethylamine or potassium carbonate
  • Suitable solvents are selected from the group consisting of ethers such as tettahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
  • compounds of Formula la can be synthesized by reacting the amine or amine salts of Formula 1 with an appropriate carboxylic acid in the presence of an organic dehydrating reagent such as 1,3-dicyclohexylcarbodiimide (DCC) or l-[3- (Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) as depicted in Scheme 2.
  • organic dehydrating reagent such as 1,3-dicyclohexylcarbodiimide (DCC) or l-[3- (Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) as depicted in Scheme 2.
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and halocarbons such as dichlorome
  • Intermediate amine la a compound of Formula 1 wherein A is a 2-pyridyl ring bearing the indicated substituents, J 1 is -(CH 2 ) q -, q is 1, 2, 3 or 4 and R 1 and R 3 are both hydrogen, can be prepared from the commercially available pyridines of Formula 2 (Scheme 3).
  • the CH 2 attached ortho to the pyridine nitrogen atom of Formula 2 can be substituted with NH 2 by a sequence of steps comprising hydrogen peroxide oxidation, acylation, hydrolysis, chlorination, azide displacement and reduction (e.g. catalytic hydrogenation using H 2 and palladium on carbon as catalyst) in procedures analogous to those found in WO00/56729 to provide the amine la.
  • J is (CH 2 ) q and q is 1, 2, 3 or 4
  • J 2 may also be optionally substituted with one or more (up to the total number of hydrogens available for replacement in any specific J- group) substituents independently selected from the group alkyl (e.g. CH(CH 3 )O, C(CH 3 ) 2 O, or CH(CH 2 CH 3 )O), halogen, C ⁇ , ⁇ O 2 and C r C 2 alkoxy.
  • substituents independently selected from the group alkyl (e.g. CH(CH 3 )O, C(CH 3 ) 2 O, or CH(CH 2 CH 3 )O), halogen, C ⁇ , ⁇ O 2 and C r C 2 alkoxy.
  • J may be optionally subsUtuted
  • compounds of Formula 1 c (wherein A and J are as previously defined and R 1 is hydrogen) can be prepared by treating compounds of Formula 7 with isoamyl nitrite and a base such as potassium t-butoxide (t-BuOK) followed by reduction of the resulting oximes of Formula 8 (Scheme 5).
  • the reduction can be accomplished, for example, with hthium aluminum hydride, zinc and acetic acid, or catalytic hydrogenation.
  • compounds of Formula lc (wherein A and J are defined and R 1 is hydrogen) can be prepared by reductive amination of compounds of Formula 9 as shown in Scheme 6.
  • Many methods for reductive amination have been reported. For some leading references, see Jerry March, Advanced Organic Chemistry: Reactions, Mechanism and Structure, Third Edition, John Wiley & Sons, New York, 1985, pp. 798-800.
  • Compounds of Formula 6a wherein J 2 is optionally substituted -CH 2 O- or -CH CH O- can be prepared by transesterification of N-(diphenylmethylene)glycine esters of Formula 9 with the corresponding alcohols of Formula 10 under basic conditions (Scheme 7).
  • Compounds of Formula 6b wherein J 2 is optionally substituted -CH 2 ⁇ H-, -CH 2 CH 2 NH-, -CH N(C ⁇ -C alkyl)- or -CH CH N(C ⁇ -C 2 alkyl)- can be prepared by amidation of N-(diphenylmethylene)glycine esters of Formula 9 with the corresponding amines of Formula 11.
  • Compounds of Formula 6 wherein J 2 is optionally substituted -CO ⁇ H- or -CO ⁇ (Cj-C 2 alkyl) can be prepared by amidation of N-(diphenylmethylene)glycine esters of Formula 9 with the corresponding amides of Formula 15.
  • J and J may be optionally substituted
  • R 8 is HorC ⁇ -C 2 alkyl
  • compounds of Formula 10a wherein J 3 is optionally substituted -CH 2 OH can be prepared by ortho-lithiation of a compound of Formula 12 followed by reaction with an aldehyde or aldehyde synthon (e.g. paraformaldehyde) or ketone.
  • compounds of Formula 10b wherein J 3 is optionally substituted -CH CH OH can be prepared by ortho-lithiation followed by reaction with an epoxide.
  • Ortho-litiations can be accomphshed by treatment of the substrate with a strong hthium base such as hthium diisopropylamide (LDA) and are typically carried out at reduced temperatures.
  • a strong hthium base such as hthium diisopropylamide (LDA)
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether and hydrocarbons such as hexane, heptane or ethylbenzene.
  • compounds of Formula 10c wherein J 3 is -CH OH also can be prepared by ortho-lithiation of a compound of Formula 12 and reactipn with carbon dioxide to provide a compound of Formula 13, followed by reduction using hthium aluminum hydride (LAH) in a suitable solvent such as toluene.
  • LAH hthium aluminum hydride
  • Some isonicotinic acids of Formula 13 may be available commercially.
  • Q 1 and Q 2 are independently H or C ! -C 2 alkyl 10b
  • compounds of Formula 10c wherein J 3 is -CH OH also can be prepared by ortho-lithiation of a compound of Formula 12 and reaction with carbon dioxide to provide a compound of Formula 13, followed by reduction using hthium aluminum hydride (LAH) in a suitable solvent such as toluene.
  • LAH hthium aluminum hydride
  • Some isonicotinic acids of Formula 13 may be available commercially.
  • Compounds of Formula 11a can be synthesized from nitriles of Formula 14 by reduction of the nitrile using hthium aluminum hydride (LAH) in a suitable solvent such as toluene to give the corresponding aminomethyl intermediates (Scheme 10).
  • Compounds of Formula 11a can also be synthesized from primary amides of Formula 15 wherein R 8 is H by reduction using hthium aluminum hydride (LAH) in a suitable solvent such as toluene.
  • Compounds of Formula 1 lb can be synthesized from secondary amides of Formula 15 wherein R 8 is C ⁇ C alkyl by reduction using hthium aluminum hydride (LAH) in a suitable solvent such as toluene.
  • Compounds of Formula 1 lb can also be synthesized by reductive -unination of formaldehyde or acetaldehyde with compounds of Formula 11a.
  • Reductive amination with formaldehyde can be accomplished in the presence of formic acid under Eschweiler-Clarke procedures (see Jerry March, Advanced Organic Chemistry: Reactions, Mechanism and Structure, Third Edition, John Wiley & Sons, New York, 1985, pp. 798-800 and references therein).
  • Compounds of Formula 15 may be prepared from compounds of Formula 13 by conversion to the corresponding acid chloride and subsequent reaction with ammonia or a primary amine (Scheme 11).
  • Methods of converting carboxylic acids to the corresponding acid chloride are well-known in the art and include, for example, treatment with thionyl chloride or oxalyl chloride.
  • the acid chloride is treated with the amine or amine salt in an inert solvent with two molar equivalents of a base (e.g. triethylamine, polymer supported dhsopropylethylamine or potassium carbonate) present.
  • a base e.g. triethylamine, polymer supported dhsopropylethylamine or potassium carbonate
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
  • compounds of Formula 15 can be synthesized by reacting the appropriate amine or amine salt with a carboxylic acid of Formula 13 in the presence of an organic dehydrating reagent such as 1,3-dicyclohexylcarbodiimide (DCC) or l-[3- (Dimethylammo)propyl]-3-e1hylcarbooUimide hydrochloride (EDC).
  • DCC 1,3-dicyclohexylcarbodiimide
  • EDC 1,3-dicyclohexylcarbodiimide
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
  • compounds of Formula 1 la can be synthesized by reacting compounds of Formula 16, wherein LG is a leaving group such as Br, CI, methanesulfonyl (-OSO Me) or para-toluenesulfonyl (-OSO -p-Tol), with ammonia in a protic solvent such as methanol (Scheme 12).
  • LG is a leaving group such as Br, CI, methanesulfonyl (-OSO Me) or para-toluenesulfonyl (-OSO -p-Tol)
  • a protic solvent such as methanol
  • Compounds of Formula 11a can also be prepared by reacting compounds of Formula 16 with a potassium salt of phthalimide followed by reaction with either aminoethanol or hydrazine in an alcohol solvent to provide the desired aminomethyl intermediates Formula 11a.
  • LG is CI, Br, -OS0 2 Me, -OSO2-P-T0I
  • compounds of Formula 16 wherein LG is -OSO 2 Me or -OSO -p-Tol (16a) can be prepared by reacting a compound of Formula 10c with the corresponding sulfonyl chloride in the presence of a base such as triethylamine, polymer supported diisopropylethylamine or potassium carbonate.
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
  • Compounds of Formula 16 wherein LG is Br or CI (16b) can be prepared by treatment of compounds of Formula 17 with halogenating agents such as bromine, chlorine, or N-halosuccinimides under free radical conditions. These transformations are typically carried out with activation by visible or ultraviolet light (hv) and peroxides and are well known in the art.
  • halogenating agents such as bromine, chlorine, or N-halosuccinimides under free radical conditions.
  • LG is -OS02Me or -OSO2-P-T0I
  • Compounds of Formula l ie can be prepared from compounds of Formula 16 by displacement with cyanide followed by reduction with, for example, hthium aluminum hydride (Scheme 14).
  • Compounds of Formula 8 can be prepared by intramolecular free-radical acylation of compounds of Formula 18 (Scheme 15). These acylations can be carried out in the presence of t-butyl hydroperoxide, sulfuric acid and ferrous sulfate (see Chem. Communications, 1969, 201 and Gazz. Chun. ltd. 1977, 107, 491 for leading references). Scheme 15
  • Compounds of Formula 18 wherein J is OCH 2 orNHCH 2 (18a or 18b respectively) can be prepared by alkylation of compounds of Formula 19 with bromoacetaldehyde diethyl acetal followed by acidic hydrolysis of the acetal protecting group (Scheme 16).
  • Compounds of Formula 18 wherein J is OCH 2 CH 2 orNHCH 2 CH 2 (18c or 18d respectively) can be prepared by Michael addition of acrolein by compounds of Formula 19.
  • 8a J J is OCH 2 8e J D is N(C ⁇ -C 2 alkyl)CH2 8b J 5 is NHCH 2 8f J 5 is N(C ⁇ -C 2 alkyl)CH 2 CH 2 8c J 5 is OCH 2 CH 2 8d J 5 is NHCH 2 CH 2 LG 1 is CI, Br, I, -OS0 2 Me, -OS0 2 -p-Tol
  • J 6 is CH 2 NH or CH 2 CH 2 NH
  • Methanesulfonyl chloride (25.6 g) was added slowly to a solution of the oil (24 g) and triethylamine in dichloromethane (150 mL) at 0 °C. The reaction mixture was slowly warmed up to room temperature and then heated to reflux overnight. The mixture was cooled to room temperature and partitioned between water and dichloromethane. The combined organic extract was dried (Na 2 SO4) and concentrated. The residue was purified by flash chromatography on silica gel (using a gradient of 10% to 60% ethyl acetate in hexanes as eluent) to give the title compound as a light yellowish oil (21.8 g).
  • T and V are both Cl andU is H
  • T Cl and V and U are both Me
  • T Cl and V and U are both Me
  • This invention also includes fungicidal compositions comprising (1)' a fungicidally effective amount of a compound of Formula I (including all geometric md stereoisomers, N-oxides and agriculturally suitable salts thereof); and (2) (i) at least one other insecticide, fungicide, nematocide, bactericide, acaricide, growth regulator, chemosterilant, semiochemical, repellent, attractant, pheromone, feeding stimulant or other biologically active compound; and/or (ii) at least one additional component selected from the group consisting of surfactants, solid diluents and Hquid diluents.
  • fungicidal compositions comprising (1)' a fungicidally effective amount of a compound of Formula I (including all geometric md stereoisomers, N-oxides and agriculturally suitable salts thereof); and (2) (i) at least one other insecticide, fungicide, nematocide, bactericide, acaricide, growth regulator,
  • compositions comprising (a) at least one compound of Formula I; and (b) at least one compound selected from the group consisting of
  • the weight ratios of component (b) to component (a) typically is from 100:1 to 1:100, preferably is from 30:1 to 1:30, and more preferably is from 10:1 to 1:10. Of note are compositions wherein the weight ratio of component (b) to component (a) is from 10:1 to 1:1.
  • Strobilurin fungicides such as azoxystrobin, kresoxim-methyl, metommostrobin/fenominostrobin (SSF-126), picoxystrobin, pyraclostrobin and trifloxystrobin are known to have a fungicidal mode of action which inhibits the bc ⁇ complex in the mitochondrial respiration chain (Angew. Chem. Int. Ed., 1999, 38, 1328-1349).
  • the bci complex is sometimes referred to by other names in the biophemical literature, including complex III of the electron transfer chain, and ub ydroquino exytochrome c oxidoreductase. It is uniquely identified by the Enzyme Commission number ECl .10.2.2.
  • the bc ⁇ complex is described in, for example, J. Biol. Chem. 1989, 264, 14543-38; Methods Enzymol. 1986, 126, 253-71 ; and references cited therein.
  • the Sterol Biosynthesis Inhibitor Fungicides component (b4) or (b5)
  • the class of sterol biosynthesis inhibitors includes DMI and non-DMI compounds, thai control fungi by inhibiting enzymes in the sterol biosynthesis pathway.
  • DMI fungicides have a common site of action within the fungal sterol biosynthesis pathway; that is, an inhibition of demethylation at position 14 of lanosterol or 24-methylene dihydrolanosterol, which are precursors to sterols in fungi.
  • Compounds acting at this site are often referred to as demethylase inhibitors, DMT fungicides, or DMTs.
  • the demethylase enzyme is sometimes referred to by other names in the biochemical literature, including cytochrome P-450
  • DMI fungicides fall into several classes: azoles (including triazoles and imidazoles), pyrimidines, piperazines and pyridines.
  • the triazoles includes bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, ipconazole, metconazole, penconazole, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole and uniconazole.
  • the imidazoles include clotrimazole, econazole, imazalil, isoconazole, miconazole and prochloraz.
  • the pyrimidines include fenarimol, nuarimol and triarimol.
  • the piperazines include triforine.
  • the pyridines include buthiobate and pyrifenox. Biochemical investigations have shown that all of the above mentioned fungicides are DMI fungicides as described by K. H. Kuck, et al. in Modem Selective Fungicides - Properties, Applications and Mechanisms of Action, Lyr, H., Ed.; Gustav Fischer Verlag: New York, 1995, 205-258.
  • the DMI fungicides have been grouped together to distinguish them from other sterol biosynthesis inhibitors, such as, the morpholine and piperidine fungicides.
  • the morpholines and piperidines are also sterol biosynthesis inhibitors but have been shown to inhibit later steps in the sterol biosynthesis pathway.
  • the morpholines include aldimorph, dodemorph, fenpropimorph, tridemorph and trimorphamide.
  • the piperidines include fenpropidin.
  • Biochemical investigations have shown that all of the above mentioned morpholine and piperidine fungicides are sterol biosynthesis inhibitor fungicides as described by K. H. Kuck, et al. in Modern Selective Fungicides - Properties, Applications and Mechanisms of Action, Lyr, H., Ed.; Gustav Fischer Verlag: New York, 1995, 185-204.
  • Pyrimidinone fungicides include compounds of Formula II
  • G is a fused phenyl, thiophene or pyridine ring;
  • R l is C r C 6 alkyl;
  • R 2 is C1-C 6 alkyl or C ⁇ Cg alkoxy; R 3 is halogen; and R 4 is hydrogen or halogen.
  • pyrimidinone fungicides selected from the group: 6-bromo-3-propyl-2-propyloxy-4(3H)-qumazolinone, 6,8-diiodo-3-propyl-2-propyloxy-4(3i ⁇ -qumazolinone, 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone,
  • Phenylamides such as metalaxyl, benalaxyl and oxadixyl
  • fungicides that can be included in compositions of this invention in combination with a Formula I compound or as an additional component in combination with component (a) and component (b) are acibenzolar, benalaxyl, benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), carpropamid, captafol, captan, carbendazim, chloroneb, 5 chlorothalonil, copper oxychloride, copper salts such as copper sulfate and copper hydroxide, cyazofamid, cymoxanil, cyprodinil, (S)-3,5-dichloro-N-(3-chloro-l -ethyl- 1- methyl- 2-oxopropyl)-4-methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, dimethomorph, diniconazole-M, dode o h, dod
  • Formula I with fungicides of a different biochemical mode of action (e.g. mitochondrial respiration inhibition, inhibition of protein synthesis by interference of the synthesis of ribosomal R ⁇ A or inhibition of beta-tubulin synthesis) that can be particularly advantageous for resistance management.
  • fungicides of a different biochemical mode of action e.g. mitochondrial respiration inhibition, inhibition of protein synthesis by interference of the synthesis of ribosomal R ⁇ A or inhibition of beta-tubulin synthesis
  • Examples include combinations of compounds of Formula I (e.g. Compound 1) with strobilurins such as
  • azoxystrobin kresoxim-methyl, pyraclostrobin and triflo ystrobin
  • carbendazim mitochondrial respiration inhibitors such as famoxadone and fenamidone
  • benomyl cymoxanil
  • dimethomorph folpet
  • fosetyl-aluminum metalaxyl
  • mancozeb maneb.
  • alkylenebis(dithiocarbamate)s such as mancozeb, maneb, propineb and zineb
  • ph alimids such as folpet
  • copper salts such as copper sulfate and copper hydroxide
  • strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin
  • mitochondrial respiration inhibitors such as
  • phenylamides such as metalaxyl
  • phosphonates such as fosetyl-AL dimethomorph
  • pyrimidinone fungicides such as 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and 6-chloro-2-propoxy-3- propylmieno[2,3- ⁇ pyrimidin-4(3H)-one
  • other fungicides such as cymoxanil.
  • fungicides for controlling potato diseases including alkylenebis(dithiocarbamate)s such as mancozeb, maneb, propineb and zineb; copper salts such as copper sulfate and copper hydroxide; strobilurins such as pyraclostrobin and trifloxystrobin; mitochondrial respiration inhibitors such as famoxadone and fenamidone; phenylamides such as metalaxyl; carbamates such as propamocarb; phenylpyridylamines such as fluazinam and other fungicides such as chlorothalonil, cyazofa id, cymoxanil, dimethomorph, zoxamid and ipro valicarb.
  • alkylenebis(dithiocarbamate)s such as mancozeb, maneb, propineb and zineb
  • copper salts such as copper sulfate and copper hydrox
  • component (b) comprises at least one compound from each of two different groups selected from (bl), (b2), (b3), (b4), (b5), (b6), (b7), (b8) and (b9).
  • the weight ratio of the compound(s) of the first of these two component (b) groups to the compound(s) of the second of these component (b) groups typically is from 100:1 to 1:100, more typically from 30:1 to 1:30 and most typically from 10:1 to 1:10.
  • component (b) comprises at least one compound selected from (bl), for example mancozeb
  • a second component (b) group for example, from (b2), (b3), (b6), (b7), (b8) or (b9).
  • the overall weight ratio of component (b) to component (a) is from 30:1 to 1:30 and the weight ratio of component (bl) to component (a) is from 10:1 to 1:1.
  • 6-chloro-2- propoxy-3-propyltMeno[2,3- ⁇ pyrimidin-4(3H)-one, folpet, captan and fosetyl-aluminum a compound selected from the group consisting of famoxadone, fenamidone, azoxystrobin, kresox n-methyl, pyraclostrobin, trifl
  • component (b) comprises at least one compound selected from (b2), for example famoxadone, and at least one compound selected from a second component (b) group, for example, from (bl), (b3), (b6), (b7), (b8) or (b9).
  • the overall weight ratio of component (b) to component (a) is from 30: 1 to 1:30 and the weight ratio of component (b2) to component (a) is from 10:1 to 1:1.
  • compositions comprising mixtures of component (a) (preferably a compound from Index Table A, B or C) with famoxadone and a compound selected from the group consisting of mancozeb, maneb, propineb, zineb, cymoxanil, metalaxyl, benalaxyl, oxadixyl, 6-iodo-3-propyl-2-propyloxy- 4(3H)-quinazolmone, 6-chloro-2-propoxy-3-propyltMeno[2,3- ⁇ pyrimid -4(3H)-one, folpet, captan and fosetyl-aluminum.
  • component (a) preferably a compound from Index Table A, B or C
  • famoxadone a compound selected from the group consisting of mancozeb, maneb, propineb, zineb, cymoxanil, metalaxyl, benalax
  • compositions wherein component (b) comprises the compound of (b3), in other words cymoxanil, and at least one compound selected from a second component (b) group, for example, from (bl), (b2), (b6), (b7), (b8) or (b9).
  • component (b) comprises the compound of (b3), in other words cymoxanil, and at least one compound selected from a second component (b) group, for example, from (bl), (b2), (b6), (b7), (b8) or (b9).
  • the overall weight ratio of component (b) to component (a) is from 30: 1 to 1 :30 and the weight ratio of component (b3) to component (a) is from 10:1 to 1:1.
  • compositions comprising mixtures of component (a) (preferably a compound from Index Table A, B or C) with cymoxanil and a compound selected from the group consisting of famoxadone, fenamidone, azoxystrobin, kresoxim-methyl, pyraclostrobin, trifloxystrobin, mancozeb, maneb, pi pineb, zineb, metalaxyl, benalaxyl, oxadixyl, 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone,
  • component (b) comprises at least one compound selected from (b6), for example metalaxyl, and at least one compound selected from a second component (b) group, for example, from (bl), (b2), (b3), (b7), (b8) or (b9).
  • the overall weight ratio of component (b) to component (a) is from 30: 1 to 1 :30 and the weight ratio of component (b6) to component (a) is from 10:1 to 1:3.
  • compositions comprising mixtures of component (a) (preferably a compound from Index Table A, B or C) with metalaxyl or oxadixyl and a compound selected from the group consisting of famoxadone, fenamidone, azoxystrobin, kresoxim-methyl, pyraclostrobin, trifloxystrobin, cymoxanil, mancozeb, maneb, propineb, zineb, 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone, 6- chloro-2-propoxy-3-propylmieno[2,3-( ⁇ pyrimidin-4(3H)-one, folpet, captan and fosetyl- aluminum.
  • component (a) preferably a compound from Index Table A, B or C
  • metalaxyl or oxadixyl preferably a compound from Index Table A, B or C
  • component (b) comprises at least one compound selected from (b7), for example 6-iodo-3-propyl-2-propyloxy-4(3H)- quinazolinone or 6-chloro-2-propoxy-3-propyltMeno[2,3- ⁇ i]pyrimidin-4(3H)-one
  • a second component (b) group for example, from (bl), (b2), (b3), (b6), (b8) or (b9).
  • compositions wherein the weight ratio of component (b6) to component (a) is from 1:4.5 to 1:9.
  • these compositions include compositions comprising mixtures of component (a) (preferably a compound from Index Table A, B or C) with 6-iodo-3-propyl-2-propyloxy-4(3H)- quinazolinone or 6-chloro-2-propoxy-3-propylt eno[2,3- ⁇ pyrimidin-4(3H)-one and a compound selected from the group consisting of famoxadone, fenamidone, azoxystrobin, kresoxim-methyl, pyraclostrobin, trifloxystrobin, cymoxanil, mancozeb, maneb, propineb, zineb, metalaxyl, benalaxyl, oxadixyl, folpet, captan and fosetyl-aluminum.
  • compositions wherein component (b) comprises the compound of (b9), in other words fosetyl-aginanum, and at least one compound selected from a second component (b) group, for example, from (bl), (b2), (b3), (b6) or (b7).
  • component (b) comprises the compound of (b9), in other words fosetyl-avarnum, and at least one compound selected from a second component (b) group, for example, from (bl), (b2), (b3), (b6) or (b7).
  • the overall weight ratio of component (b) to component (a) is from 30: 1 to 1 :30 and the weight ratio of component (b9) to component (a) is from 10: 1 to 1:1.
  • compositions comprising mixtures of component (a) (preferably a compound from Index Table A, B or C) with fosetyl-aluminum and a compound selected from the group consisting of famoxadone, fenamidone, azoxystrobin, kresoxim-methyl, pyraclostrobin, trifloxystrobin, manco-jeb, maneb, propineb, zineb, metalaxyl, benalaxyl, oxadixyl, 6-iodo-3-propyl-2-propyloxy-4(3H)-qumazolinone, 6- chloro-2-propoxy-3-propylthieno[2,3-rf]pyrimidin-4(3H)-one, folpet, captan and cymoxanil.
  • component (a) preferably a compound from Index Table A, B or C
  • strobilurins such as azoxystrobin, kresoxim-methyl, pyraclostrobin and trifloxystrobin
  • morpholines such as fenpropidine and fenpropimorph
  • triazoles such as bromuconazole, cyproconazole, difenoconazole, epoxyconazole, flusilazole, ipconazole, metconazole, propiconazole, tebuconazole and triticonazole
  • pyrimidinone fungicides benomyl; carbendazim; chlorothalonil; dimethomorph; folpet; mancozeb; maneb; quinoxyfen; validamycin and vinclozolin.
  • fungicides giving an even broader spectrum of agricultural protection including azoxystrobin, kresoxim-methyl, pyrclostrobin, trifloxystrobin, benomyl, carbendazim, chlorothalonil, dimethomorph, folpet, mancozeb, maneb, quinoxyfen, validamycin, vinclozolin, fenpropidine, fenpropimorph, bromuconazole, cyproconazole, difenoconazole, epoxyconazole, flusilazole, ipconazole, metconazole, propiconazole, tebuconazole and triticonazole.
  • fungicides of a different mode of action e.g. mitochondrial respiration inhibition, inhibition of protein synthesis by interference of the synthesis of ribosomal RNA or inhibition of beta-tubulin synthesis
  • examples include combinations of compounds of Formula I (e.g. Compound Al) with azoxystrobin, kresoxim-methyl, pyrclostrobin, trifloxystrobin, carbendazim, famoxadone, fenamidone, benomyl, cymoxanil, dimethomorph, folpet, fosetyl-aluminum, metalaxyl, mancozeb, maneb.
  • These combinations can be particularly advantageous for resistance management, especially where the fungicides of the combination control the same or similar diseases.
  • fungicides for controlling grape diseases including dithiocarbamates such as mancozeb, maneb, propineb and zineb, phthalimids such as folpet, copper salts such as copper sulfate and copper hydroxide, strobilurins such as azoxystrobin, pyrclostrobin and trifloxystrobin, , phenylamides such as metalaxyl, phosphonates such as fosetyl-aluminum, morpholines such as dimethomorph, and other fungicides such as cymoxanil, famoxadone and fenamidone.
  • dithiocarbamates such as mancozeb, maneb, propineb and zineb
  • phthalimids such as folpet
  • copper salts such as copper sulfate and copper hydroxide
  • strobilurins such as azoxystrobin, pyrclostrobin and trifloxystrobin
  • fungicides for controlling potato diseases including dithiocarbamates such as mancozeb, maneb, propineb and zineb, copper salts such as copper sulfate and copper hydroxide, strobilurins such as pyrclostrobin and trifloxystrobin, phenylamides such as metalaxyl, carbamates such as propamocarb, phenylpyriylamines such as fluazinam, morpholines such as dimethomorph, and other fungicides such as chlorothalonil, cyazofamid, cymoxanil, famoxadone, fenamidone, zoxamid and iprovalicarb.
  • dithiocarbamates such as mancozeb, maneb, propineb and zineb
  • copper salts such as copper sulfate and copper hydroxide
  • strobilurins such as pyrclostrobin and trifloxy
  • Preferred compositions comprise a compound of component (a) mixed with cymoxanil.
  • Preferred compositions comprise a compound of component (a) mixed with a compound selected from (bl). More preferred is a composition wherein the compound of (bl) is mancozeb.
  • Preferred compositions comprise a compound of component (a) mixed with a compound selected from (b2).
  • compositions wherein the compound of (b2) is famoxadone.
  • Preferred compositions comprise a compound of component (a) mixed with two compounds selected from two different groups selected from (bl), (b2), (b3), (b4), (b5), (b6), (b7), (b8) and (b9).
  • Preferred compositions are those wherein component (a) is selected from the compounds of Formula I indicated in Preferred 1 through 14 above.
  • Compounds of this invention can also be mixed with one or more insecticides, 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.
  • compositions of this invention can be formulated are: insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlo ⁇ yrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, fonophos, imidacloprid, isofenphos, malathion, metaldehyde, methamidophos, methidathion, methomy
  • Formulation Compounds of this invention will generally be used as a formulation or 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 apphcation and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and or suspoemulsions) and the like which optionally can be thickened into gels.
  • 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; alternatively 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 (e.g. from 0.01-99.99 weight percent) of active ingredient together with diluent and/or 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, Hgnin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
  • 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, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
  • 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.
  • Preferred suspension concentrates include those containing, in addition to the active ingredient, from 5 to 20% nonionic surfactant (for example, polyethoxylated fatty alcohols) optionally combined with 50-65% liquid diluents and up to 5% anionic surfactants.
  • Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning,
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
  • Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
  • Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • the compounds and compositions of Formula I are useful as plant disease control agents.
  • the present invention therefore 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 preferred methods of use are those involving the compounds or compositions preferred above.
  • the compounds and compositions of Formula I 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.
  • pathogens include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum, Septoria tritici, Cercosporidiumpersonatum, 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, Sphaerothecafulig
  • Plant disease control is ordinarily accomplished by applying an effective amount of a compound of Formula I 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 apphcation for these compounds can be influenced by many factors of the environment and should be determined under actual us e 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.
  • the following TESTS demonstrate the control efficacy of compounds suitable for use in accordance with this invention on specific pathogens.
  • the pathogen control protection afforded by the compounds is not limited, however, to these species.
  • These TESTS can also be used to demonstrate the control efficacy of compositions of this invention on specific pathogens.
  • Test suspensions comprising a single active ingredient are sprayed to demonstrate the control efficacy of the active ingredient individually.
  • the active ingredients can be combined in the appropriate amounts in a single test suspension,
  • stock solutions of individual active ingredients can be prepared and then combined in the appropriate ratioj and diluted to the final desired concentration to form a test suspension or
  • test suspensions comprising single active ingredients can be sprayed sequentially in the desired ratio.
  • Synergism has been described as "the cooperative action of two components [e.g. component (a) and component (b)] of a mixture, such that the total effect is greater or more prolonged than the sum of the effects of the two (or more) taken independently” (see Tames, P. M. L., Neth. J. Plant Pathology, 1964, 70, 73-80).
  • the presence of a synergistic effect between two active ingredients is established with the aid of the Colby equation (see Colby, S. R.
  • test compounds are first dissolved in acetone in an amount equal to 3% of the final volume and then suspended at the desired concentration (in ppm) in acetone and purified water (50/50 mix) containing 250 ppm of the surfactant Trem® 014 (polyhydric alcohol esters). The resulting test suspensions are then used in the following tests. Spraying a 200 ppm test suspension to the point of run-off on the test plants is the equivalent of a rate of 500 g/ha. TEST A
  • test suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore dust of Erysiphe graminis f. sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at 20 °C for 7 days, after which disease ratings were made.
  • test suspension was sprayed to the point of run-off on wheat seedlings.
  • seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20 °C for 24 hours, and then moved to a growth chamber at 20 °C for 6 days, after which disease ratings were made.
  • TEST C The test suspension was sprayed to the point of run-off on tomato seedlings.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un procédé de lutte contre les maladies de plantes engendrées par des pathogènes végétaux, qui consiste à appliquer à la plante touchée (tout ou partie), ou bien à la graine ou à la plantule, une quantité fongicide efficace d'un composé représenté par la formule I (englobant tous les isomères géométriques et les stéréoisomères correspondants), y compris les N-oxydes, sels appropriés à l'agriculture et compositions correspondants. Dans ladite formule, A et N-C=C forment ensemble un cycle pyridynyle fusionné substitué; B est un cycle phényle ou pyridinyle substitué; J est une chaîne de liaison éventuellement substituée comprenant entre 2 et 5 membres, dont au moins un membre carbone, éventuellement un ou deux membres carbone sous la forme C(=O), et éventuellement un membre pouvant être azote et oxygène; W est C=L ou SOn; L est O ou S; R1 est H; ou alkyle C¿1?-C6, alcényle C2-C6, alkynyle C2-C6 ou cycloalkyle C3-C6, chacun éventuellement substitué; R3 est H; ou alkyle C1-C6, alcényle C2-C6, alkynyle C2-C6 ou cycloalkyle C3-C6, alkylcarbonyle C2-C6, alcoxycarbonyle C2-C6, alkylaminocarbonyle ou dialkylaminocarbonyle C3-C8; et n vaut 1 ou 2. L'invention concerne également des compositions fongicides renfermant un composé représenté par la formule I, y compris les N-oxydes et sels appropriés à l'agriculture correspondants. L'invention concerne enfin des composés représentés par la formule I, y compris les N-oxydes et sels appropriés à l'agriculture correspondants, à condition que, lorsque B est un cycle phényle substitué, lorsque W est C=O ou SO2, lorsque R3 est H et lorsque J est une chaîne saturée comprenant entre 2 et 4 atomes de carbone, avec ou sans substitution (entre un et trois substituants peuvent être alkyle, alcoxy, aryle ou aralkyle), les composés sont des N-oxydes.
EP02744275A 2001-05-15 2002-05-14 Amides bicycliques a fusion pyridinyle utilises comme fongicides Withdrawn EP1387612A1 (fr)

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AR045875A1 (es) * 2003-10-27 2005-11-16 Merck & Co Inc Procedimiento para la preparacion del antagonista ccr-2
JP5034293B2 (ja) * 2005-07-14 2012-09-26 住友化学株式会社 カルボキサミド化合物及びこれを含有する植物病害防除剤
US8044043B2 (en) * 2008-04-11 2011-10-25 Bristol-Myers Squibb Company CGRP receptor antagonists
CA2761639C (fr) 2009-05-29 2016-06-07 Raqualia Pharma Inc. Derives de carboxamide substitues par aryle comme inhibiteurs des canaux calciques ou sodiques
ES2896400T3 (es) 2014-08-01 2022-02-24 Nuevolution As Compuestos activos frente a bromdominios
US11691971B2 (en) 2020-06-19 2023-07-04 Incyte Corporation Naphthyridinone compounds as JAK2 V617F inhibitors
WO2021257863A1 (fr) 2020-06-19 2021-12-23 Incyte Corporation Composés de pyrrolotriazine utilisés en tant qu'inhibiteurs de v617f de jak2
WO2022006456A1 (fr) 2020-07-02 2022-01-06 Incyte Corporation Composés de pyridone tricyclique en tant qu'inhibiteurs de v617f de jak2
WO2022006457A1 (fr) 2020-07-02 2022-01-06 Incyte Corporation Composés d'urée tricycliques en tant qu'inhibiteurs de v617f de jak2
WO2022046989A1 (fr) 2020-08-27 2022-03-03 Incyte Corporation Composés d'urée tricycliques en tant qu'inhibiteurs de v617f de jak2
WO2022140231A1 (fr) 2020-12-21 2022-06-30 Incyte Corporation Composés de déazaguanine utilisés en tant qu'inhibiteurs de v617f de jak2
AR125273A1 (es) 2021-02-25 2023-07-05 Incyte Corp Lactamas espirocíclicas como inhibidores de jak2 v617f
US12084430B2 (en) 2022-03-17 2024-09-10 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors

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WO1996037473A1 (fr) * 1995-05-23 1996-11-28 Hoechst Schering Agrevo Gmbh 2,3-cycloalcenopyridines substituees, leur procede de preparation, agents contenant ces composes et leur utilisation comme pesticides et fongicides
TW575562B (en) * 1998-02-19 2004-02-11 Agrevo Uk Ltd Fungicides

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CN1509140A (zh) 2004-06-30
IL158009A0 (en) 2004-03-28
PL367200A1 (en) 2005-02-21
JP2004529943A (ja) 2004-09-30
ZA200307375B (en) 2004-09-22
MXPA03010436A (es) 2004-03-09
AR033893A1 (es) 2004-01-07
WO2002091830A1 (fr) 2002-11-21
BR0209687A (pt) 2004-09-14

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