WO1995007278A1 - Aminopyrimidines fongicides, acaricides et arthropodicides - Google Patents

Aminopyrimidines fongicides, acaricides et arthropodicides Download PDF

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Publication number
WO1995007278A1
WO1995007278A1 PCT/US1994/008499 US9408499W WO9507278A1 WO 1995007278 A1 WO1995007278 A1 WO 1995007278A1 US 9408499 W US9408499 W US 9408499W WO 9507278 A1 WO9507278 A1 WO 9507278A1
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alkyl
haloalkyl
phenyl
halogen
alkoxy
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PCT/US1994/008499
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Joseph Eugene Drumm, Iii
Renee Marie Lett
Thomas Martin Stevenson
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E.I. Du Pont De Nemours And Company
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Priority to AU75518/94A priority Critical patent/AU7551894A/en
Publication of WO1995007278A1 publication Critical patent/WO1995007278A1/fr

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    • 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/30—Germanium compounds

Definitions

  • the present invention comprises aminopyrimidines useful as fungicides, miticides and arthropodicides.
  • the compounds of this invention are distinguished from those described in WO 92/08704, EP 323,757, EP 519,211 and
  • This invention comprises compounds of Formula I, including all enantiomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides, miticides and arthropodicides in both agronomic and nonagronomic environments.
  • the compounds are:
  • A is C 1 -C 3 straight or branched chain alkylene or C 3 -C 6 cycloalkylene
  • any one carbon atom of A can be optionally substituted with
  • R 1 is H, C 1 -C 3 alkyl or C 1 -C 3 alkoxy
  • R 2 is H, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or SCN;
  • R 3 is H, formyl, C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl;
  • R 4 is C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, CN, C(O)R 5 , CO 2 R 5 , C(O)N(R 5 )R 6 , N 3 , NO 2 , N(R 5 )R 6 , N(R 7 )C(O)R 5 , N(R 7 )C(O)N(R 5 )R 6 ,
  • R 5 and R 7 are 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 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 1 -C 4 nitroalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -C 6 cycloalkyl, C 4 -C 6 cycloalkenyl, C 3 -C 8 halocycloalkyl, phenyl optionally substituted with W 1 , or benzyl optionally substituted on the phenyl ring with W 1 ;
  • R 6 is H or C 1 -C 4 alkyl
  • R 5 and R 6 can be taken together when attached to the same atom as
  • Q is a 8-, 9- or 10-membered fused carbobicyclic or fused heterobicyclic ring system; or Q is a 5- or 6-membered heteromonocyclic ring; said Q containing 1 to 4 heteroatoms independently selected from the group
  • Exemplary values of Q include:
  • R 8 is H, halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkylthio, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl;
  • Z is H, CN, halogen, NO 2 C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyloxy, C 4 -C 6
  • cycloalkenyl C 4 -C 6 cycloalkenyloxy, C 3 -C 8 cycloalkylalkyl, C 1 -C 6 alkylthio, C 2 -C 6 alkylthioalkyl, 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(O)R 9 or X(R 10 )(R 11 )R 12 ; or Z is C 1 -C 6 alkyl substituted with CN, NO 2 , C(O)R 9 , C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl or X(R 10 )(R 11 )R 12 ; or Z is phenyl, phenoxy, benzyloxy or U, each optionally substituted with 1 or 2 substituents independently selected from W; provided that (i) when Q is thienyl or furyl and A is C 1 -C 3 alkylene or C 1 -C 3 alkylene substituted with C 1 -C 6 alkyl or C 3
  • W is halogen, dioxolanyl, dithiolanyl, CN, NO 2 , CO 2 R 14 , C(O)R 14 ,
  • U is a heteromonocyclic ring substituted by W and containing 1 to 4
  • heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur;
  • Exemplary values of U include:
  • R 9 is H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, phenyl or benzyl, each phenyl or benzyl optionally substituted on the phenyl ring with R 22 ;
  • R 10 and R 12 are independently C 1 -C 4 alkyl
  • R 11 is C 1 -C 4 alkyl, C 1 -C 4 alkoxyalkyl or phenyl optionally substituted with R22.
  • R 13 and R 14 are independently H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 4 -C 6 cycloalkenyl, C 3 -C 8 alkynyl, C 1 -C 4 haloalkyl, phenyl or benzyl, each phenyl or benzyl optionally substituted with R 16 ;
  • R 15 and R 17 are independently H, formyl, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 1 -C 6 alkylsulfonyl;
  • R 16 is halogen, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6
  • alkoxycarbonyl C 1 -C 6 alkylthio, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
  • R 18 and R 19 are independently H, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 3 -C 6
  • alkynyl C 1 -C 4 haloalkyl, phenyl or benzyl, each phenyl or benzyl optionally substituted with R 20 ;
  • R 20 is H, halogen, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6
  • R 22 is halogen, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylsulfonyl;
  • X is Si or Ge
  • n 0, 1 or 2;
  • n 1 or 2.
  • Preferred Compounds A are compounds of Formula I wherein:
  • A is C 1 -C 3 straight or branched chain alkylene or C 3 -C 4 cycloalkylene, wherein any one carbon atom of A can be optionally substituted with R 4 ;
  • R 1 is H, CH 3 or OCH 3 ;
  • R 2 is H, halogen, CN or OCH 3 ;
  • R 3 is H
  • R 4 is C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, CN, C(O)R 5 , CO 2 R 5 , OR 5 , or
  • R 5 is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
  • Z is H, CN, halogen, NO 2 C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkoxyalkoxy, C(O)R 9 or X(R 10 )(R 11 )R 12 ; or Z is phenyl, phenoxy, benzyloxy or U, each optionally substituted with 1 or 2 substituents independently selected from W;
  • W is halogen, dioxolanyl, dithiolanyl, CN, NO 2 , CO 2 R 14 , C(O)R 14 , OR 13 , SR 13 , S(O) 2 R 13 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 3 -C 8 cycloalkyl or X(R 10 )(R 11 )R 12 ;
  • R 10 and R 12 are independently C 1 -C 4 alkyl
  • R 11 is C 1 -C 4 alkyl or phenyl
  • R 13 and R 14 are independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, phenyl or benzyl, each phenyl or benzyl optionally substituted with R 16 ; and
  • R 16 is halogen, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy.
  • Preferred Compounds B are compounds of Preferred A wherein Q is one of to Q-53.
  • Preferred Compounds C are compounds of Preferred A wherein Q is one of Q-54 to Q-72.
  • Preferred Compounds D are compounds of Preferred A wherein Q is one of Q-73 to Q-97.
  • Stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers and geometric isomers.
  • One skilled in the art will appreciate that one stereoisomer may be more active than the others and how to separate said stereoisomers.
  • the present invention comprises mixtures, individual stereoisomers, and optically active mixtures of compounds of Formula I as well as agriculturally suitable salts thereof.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” denotes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers.
  • alkenyl denotes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.
  • Alkenyl also denotes polyenes such as 1,3-hexadiene and 2,4,6-heptatriene.
  • Alkynyl denotes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 3-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also denote moieties comprised of multiple triple bonds such as 2,7-octadiyne and
  • Alkoxy denotes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • alkoxyalkyl denotes alkoxy substitution on alkyl.
  • Alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • alkynyloxy denotes straight-chain or branched alkynyloxy moieties. Examples include HC ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and
  • Alkylthio denotes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfinyl denotes both enantiomers of an alkylsulfinyl group.
  • alkylsulfonyl include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 ,
  • Cycloalkyl denotes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • cycloalkyloxy denotes the same groups linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy.
  • Cycloalkenyl denotes groups such as cyclopentenyl and cyclohexenyl.
  • cycloalkenyloxy denotes the same groups linked through an oxygen atom such as cyclopentenyloxy and cyclohexenyloxy.
  • cycloalkylalkyl examples include cyclopropylmethyl, cyclohexylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups.
  • Alkylcarbonyl denotes carbonyl with an attached straight or branch-chained alkyl group.
  • Alkoxycarbonyl denotes carbonyl with an attached straight or branch-chained alkoxy group.
  • halogen either alone or in compound words such as “haloalkyl”, denotes 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, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 . Examples of
  • haloalkynyl 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, CF 2 HCH 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 CH 2 ClCH 2 CH 2 S.
  • haloalkylsulfonyl examples include CF 3 SO 2 , CCl 3 SO 2 , CF 3 CH 2 SO 2 and CF 3 CF 2 SO 2 .
  • haloalkoxyalkoxy examples include
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkoxy designates CH 3 OCH 2 O
  • C 3 alkoxyalkoxy designates, for example,
  • C 4 alkoxyalkoxy designates the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 O, and
  • alkoxyalkyl examples include CH 3 OCH 2 ,
  • Nitroalkyl designates a straight or branched-chain alkyl group substituted with NO 2 .
  • Cyanoalkyl designates a straight or branched-chain alkyl group substituted with CN.
  • the term "fused carbobicyclic ring system" is defined as comprising two fused rings wherein the two ring share two consecutive carbon atoms. The ring atoms are limited to carbon with the total number of ring atoms being 8, 9 or 10. One or two of the carbon atoms can optionally be substituted with O to form carbonyl. Each ring of the ring system can be independently fully unsaturated, partially unsaturated or fully saturated.
  • fused heterobicyclic ring system is defined as a bicyclic ring comprising two rings wherein the two rings share two consecutive atoms.
  • the total number of ring atoms is 8, 9 or 10 and 1-4 of the ring atoms are heteroatoms selected from the group 0-4 N, 0-2 O and 0-2 S.
  • One or two of the carbon atoms can optionally be substituted with O to form carbonyl.
  • Each ring of the ring system can be independently fully unsaturated, partially unsaturated or fully saturated.
  • Examples include quinolyl, isoquinolyl, quinoxalinyl, benzofuryl, isobenzofuranyl, benzimidazoyl, benzothienyl, benzodioxolyl, chromanyl, indolinyl, isoindolyl, thienofuranyl, benzoxazolyl, coumarinyl, chromanyl, indolizinyl, imidazothiazolyl, thienofuranyl andpurinyl, said ring systems attached through any available carbon or nitrogen.
  • heteromonocyclic ring is defined as a 5- or 6-membered ring which can be fully unsaturated, partially unsaturated or fully saturated and contains 1 to 4 heteroatoms selected from the group 0-4 N, 0-2 O and 0-2 S. One of the carbon atoms of the ring can optionally be substituted with O to from carbonyl. Examples of heteromonocyclic rings include pyrrolidinyl, imidazolinyl,
  • Z 1 represents a displaceable group such as a halogen, pyridinium or an alkyl-or arylsulfonyloxy group
  • R 1 , R 2 , R 3 , and Q are as previously defined for Formula I.
  • the reaction of pyrimidine II with amine in is best carried out in the presence of an acid acceptor or base.
  • the base can be triethylamine, pyridine, sodium hydride, or potassium carbonate.
  • the synthetic process can be carried out in the absence or presence of a solvent. Suitable solvents include ethanol, toluene, propanol, xylene, N, N-dimethylformamide, and N, N-dimethylacetamide.
  • Preferred temperatures for this process are about 20°C to 200°C with temperatures between 60°C and 150°C being particularly preferred.
  • Compounds of Formula I where R 1 is a CH 3 group can be best prepared by reacting an amine of Formula in with a pyrimidine of Formula II where R 1 is CH 3 .
  • Compounds of Formula I wherein R 3 other than H can be prepared as as shown in Scheme I from amine of Formula III wherein R 3 is H or by reacting compounds of Formula I wherein R 3 is H by reaction with an appropriate alkylating or acylating agent.
  • the phthalimides of Formula IV are prepared by phthalimide displacement on a compound of Formula V containing an appropriate leaving group (Scheme 3).
  • a leaving group such as halogen, pyridinium or sulfonate
  • the displacement reactions are carried out by heating compounds of Formula V with potassium phthalimide in a dipolar aprotic solvent like N-methylpyrrolidone ( ⁇ MP).
  • the compounds of Formula V can be prepared from the corresponding alcohol by halogenation or sulfonylation of the corresponding alcohol derivative.
  • the haloalkyl derivatives can be prepared by free-radical halogenation of the appropriate alkyl derivative.
  • Compounds of Formula V can also be made directly from acyclic precursors. For example, the methods of Brigg, et al.,
  • Oximes of Formula VI can be reduced using lithium aluminum hydride or Raney nickel alloy (Obata et. al. Pestic. Sci., (1992), 34, 133) or titanium trichloride/sodium cyanoborohydride (Leeds et al. Syn. Commun., (1988), 18, 777). Oximes of Formula VI can be prepared from the corresponding ketones of Formula VII (Scheme 6).
  • ketones of Formula VII are either commercially available or prepared by methods known to those skilled in the art. Some ketones may be prepared using a Friedel-Crafts acylation as schown in Scheme 7. See for, example, Bonjouklian, Syn. Commun. (1985) 15(8), 711.
  • the required amine of Formula III may be made directly from the ketone by reductive amination according to the procedure of Borch et. al., J. Am. Chem. Soc. (1971), 93, 2987.
  • esters of Formula I Reduction of esters of Formula I with a reducing agent, for example, lithium aluminum hydride, gives an alcohol of Formula I where A is equal to CHCH 2 OH.
  • a reducing agent for example, lithium aluminum hydride
  • the reaction is best performed in an ether solvent that dissolves the starting ester (tetrahydrofiiran) and at reduced temperatures (0°C).
  • Esters of Formula I where A is equal to CHCO 2 Me can be prepared according to Scheme 1 using amines of Formula in where A is equal to CHCO 2 Me.
  • Compounds where A is OR 5 , OC(O)R 5 , OCO 2 R 5 , OC(O)N(R 6 )R 7 or OS(O) 2 R 5 can be made from the corresponding alcohol as shown in Scheme 10.
  • LG is a leaving group such as halogen or sulfonate and R 5
  • R 4 is C(O)R 5 , C(O) 2 R 5 ,C(O)N(R 6 )R 7 or S(O) 2 R 5
  • the alcohols of Formula I can be prepared from other compounds of Formula I wherein A is substituted with R 4 , R 4 being C(O)R 5 or C(O) 2 R 5 .
  • These esters and ketones of Formula I can be prepared according to Scheme 1 using amines of Formula HI where A is substituted with C(O)R 5 or C(O) 2 R 5 .
  • certain alcohols can be prepared by reduction compounds of Formula I wherein that portion of the carbon chain direcdy linking the aminopyrimidine and Q moieties contains a carbon which is part of a carbonyl group.
  • the alcohol can also serve as the starting material for preparing compounds of Formula I wherein R 4 is CN, SR 5 , N 3 and SCN.
  • R 4 is CN, SR 5 , N 3 and SCN.
  • the compounds of Formula I wherein A is substituted with R 4 , R 4 being a substituted amino group wherein the nitrogen atom is attached to the A group, can be prepared from compounds of Formula I where R 4 is NH 2 as schown in
  • the amines of Formula I wherein R 4 is NH 2 can be prepared from the appropriate ketone through reductive amination such as the procedure of Borch, or from the alcohol via the Mitsunobu reaction. Alternatively, the amines can be prepared, as discussed, from the corresponding halides, via the phthlamide, or by reduction of the corresponding oxime.
  • a general method for various Q groups can be found in 1 ,3-Dipolar
  • Pyrimidines of Formula II can be prepared by a variety of literature methods. Some particularly efficient processes are described by Foster et al. in Org. Syn., (1955), 35, 80 and by JP 58 (83) 222, 070, EP 370,391 and EP 511.219.
  • Step A 2-((5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl)methyl)-1H- isoindole-1,3(2H)dione
  • Step B 5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazole-3-methanamine
  • Step A The product of Step A (2.71 g, 7.3 mmol) of was dissolved (heat) in 30 mL methanol. The solution was treated with 0.43 mL (8.8 mmol) of hydrazine hydrate and heated to reflux for 3 h during which time a precipitate formed. After cooling, 30 mL of diethyl ether was added, followed by 50 mL of 6% potassium carbonate. The aqueous layer was extracted 3 times with diethyl ether. The organic layers were combined, dried (MgSO 4 ) and concentrated to give 1.39 g (78% yield) of an orange solid. 1 H NMR (CDCl 3 ), ⁇ 8.2 (d,2H), 7.8 (d,2H), 4.074 (s,2H), 1.8 (brd,3H).
  • Step C 5-chloro-6-ethyl-N-[[5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-
  • Step B trimethvl[5-(2-methyl-1,3-dioxolan-2-yl)-2-thienyl]germane
  • Step D 1-[5-(trimethylgermyl)-2-thienyl]ethanone oxime
  • Step F 5-cMoro-6-ethyl-N-[1-[5-(trimethylgermyl)-2-thienyl]-ethyl]-4- pyrimidinamine
  • Step A N-(3-butenyl)-5-chloro-6-ethyl-4-pyrimidinamine
  • Step A The product of Step A (0.76 g) was treated with benzhydroximidoyl chloride (0.7 g) in ether (40 mL). Then triethylamine (1.2 mL) was added dropwise. The reaction was stirred at room temperature overnight. The mixture was diluted with water and the layers were separated. The ether layer was dried over magnesium sulfate and the solvent was removed at reduced pressure.
  • Dichloroformaldoxime was prepared by the method of Torssell et. al.
  • Example 4 The product of Example 4 (0.43 g) was mixed with 4-fluorophenol (3.3 g) and potassium carbonate (1.1 g) and heated to 120°C. for 3 h. The mixture was diluted with water and sodium hydroxide until pH 12. The mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate.
  • Step B 1-[6-(4-Fluorophenoxy)-2-pyridinyl]-1-ethanone
  • Step A The product of Step A (6.5 g, 24 mmol) was dissolved in 30 mL of tetrahydrofuran (THF), cooled to -78°C and treated with n-butyllithium (10.4 mL of 2.5 M, 26 mmol). After 30 min, N,N-dimethylacetamide (2.4 mL, 26 mmol) in 10 mL of the THF was added dropwise. The reaction mixture was stirred at -78°C for 10 min and then at room temperature for 3 h. After cooling the mixture to about 5°C, 40 mL of saturated aqueous NaHCO 3 solution and 100 mL of methylene chloride were added.
  • THF tetrahydrofuran
  • Step C 1-[6-(4-Fluorophenoxy)-2-pyridinyl]-1-ethanone oxime
  • Step B The product of Step B (5.5 g. 24 mmol) was dissolved in 25 mL of methanol and combined with a solution of hydroxylamine hydrochloride (2.9 g. 42 mmol) and sodium acetate (5.7 g, 42 mmol) in 20 mL of water. The mixture was heated at reflux for 3.5 h and then cooled to room temperature and treated with 100 mL of methylene chloride. The mixture was partitioned, the aqueous phase extracted with methylene chloride, and the combined organic phases were dried (MgSO 4 ). The slvent was concentrated under vacuum and the crude residue was
  • Step C The product of Step C (3.6 g, 15 mmol) was dissolved in 200 mL of methanol and treated with ammonium acetate (13 g, 160 mmol) and sodium cyanoborohydride (2.8 g, 45 mmol) at 22°C.
  • Step E 5-Chloro-6-ethyl-N-[1-[6-(4-fluorophenoxy)-2-pyridinyl]ethyl]-4- pyrimidinamine
  • Step D The product of Step D (3.5 g, 15 mmol), triethylamine (4.2 mL, 30 mmol), and 4,5-dichloro-6-ethyl-pyrimidine (2.6 g, 15 mmol) were dissolved in 11 mL of toluene and heated to 110°C for 20 h. The mixture was cooled to room
  • TMG Ge(CH 3 ) 3
  • cPr cyclopropyl
  • the compounds in Table 1 can be referred to by line number and column number.
  • the compounds named in line 1 can be referred to as 1-1, 1-2, 1-3, 1-4, 1-5 and 1-6 (as designated by line number-column number). All other specific compounds covered in Table 1 can be designated in an analogous fashion.
  • the present invention further comprises agricultural compositions containing one or more compounds of Formula I as previously defined.
  • Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Use formulations include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • 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 100 weight percent.
  • Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill.
  • Water-dispersible granules can be produced by agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259.
  • Suspensions are prepared by wet-milling; see, for example, U.S. 3,060,084.
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration
  • Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.
  • Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • the compounds of this invention are useful as plant disease control agents.
  • the present invention therefore further comprises a method for controlling fungi, mites, or foliar, aquatic, and soil inhabiting arthropod pests, or plant diseases caused thereby, 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 Formula I or a 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.
  • pathogens include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum,
  • 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 aphanidermatum, Phytophthora megasperma and other generea and species closely related to these pathogens.
  • the compounds of this invention are also exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term includes insect, 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.
  • arthropods term includes insect, mites and nematodes
  • 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, Phthiraptera, Siphonoptera, Blattaria, Thysanaura and Pscoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes.
  • the compounds are also 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, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banksi and Oligonychus pratensis; Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and
  • Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematicides, bactericides, acaricides, semiochemicals, repellants, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • combinations with other biologically active compounds having a similiar spectrum of control but a different mode of action will be particularly advantageous for resistance management.
  • insecticides such as monocrotophos, carbofuran, tetrachlorvinphos, malathion, parathion-methyl, methomyl, chlordimeform, diazinon, deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin, profenofos, sulprofos, triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fipronil, flufenprox, fonophos, isofenphos, methidathion, methamidophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon, methoxychlor
  • Arthropod pests are controlled and protection of agronomic crops, animal and human health is achieved by applying one or more of the compounds of tihds 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.
  • a preferred method of application is by spraying.
  • granular formulations of these compounds can be applied to the plant foliage or the soil.
  • Other methods of application include direct and residual sprays, aerial sprays, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, and many others.
  • the compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.
  • 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.
  • 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 (term includes diluents, and surfactants) and possibly in combination with a food depending on the contemplated end use.
  • suitable carriers term includes diluents, and surfactants
  • 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, and synergists and other solvents such as piperonyl butoxide often enhance compound efficacy.
  • the rate of application required for effective arthropod 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.
  • Rates of application for these compounds as plant disease control agents 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 10,000 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.
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem ® 014 (polyhydric alcohol esters). The resulting test suspension s were then used int he following tests. TEST A
  • test suspensions were 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 growth chamber at 20°C for 7 days, after which disease ratings were made. Of the compounds tested, the following gave 70% disease control or higher: 1, 3, 4, 5, 6, 7, 11, 15, 16, 17, 18, 19, 21, 22, 23, 24, 26, 27, 29, 34, 35, 36, 37, 38, 39, 40, 41, 43, 48, 49, 50, 51, 52, 54, 55, 57, 58, 61, 62, 63, 65, 67, 68, 69, 70, 74, 75.
  • test suspensions were sprayed to the point of run-off on wheat seedlings.
  • the seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made.
  • the following gave 70% disease control or higher: 3, 5, 7, 11, 15, 16, 17, 18, 19, 21, 22, 23, 24, 26, 27, 32, 33, 34, 35, 36, 37, 38, 41, 46, 48, 49, 50, 51, 52, 53, 54, 55, 57, 58, 59, 61, 62, 63, 65, 67, 68, 69, 70, 72, 74, 75.
  • test suspensions were sprayed to the point of run-off on tomato seedlings.
  • seedlings were inoculated with a spore suspension of Phytophthora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 h, and then incubated in a saturated atmosphere at 20°C for 5 days, after which disease ratings were made.
  • Phytophthora infestans the causal agent of potato and tomato late blight
  • test suspensions were sprayed to the point of run-off on grape seedlings.
  • the following day the seedlings are inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings are made.
  • the following gave 70% disease control or higher: 5, 15, 17, 18, 19, 20, 21, 22, 23, 24, 33, 35, 37, 43, 48, 49, 50, 51, 52. 53, 55, 57, 59, 61, 62, 63, 65, 67, 68, 70, 71, 72, 74.
  • Test units each consisting of a H.I.S. (high impact styrene) tray with 16 cells were prepared.
  • Wet filter paper is place in the 12 ounce (345 mL) with approximately approximately 8 cm 2 of lima bear leaf.
  • Fiftteen to twenty third-instar larvae of fall armyworm (Spodoptera frugiperda) were placed into an 8 ounce (230 mL) plastic cup. Solutions of each of the test compounds in
  • 75/25 acetone/distilled water solvent were sprayed into the tray and cup. Spraying was accomplished by passing the tray and cup, on a conveyer belt, direcdy beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg/ha) at 30 p.s.i. (207 kPa). The insects were transferred from the 8 ounce cup to the HIS tray (one insect per cell). The trays were then covered and held at 27°C and 50% relative humidity for 48 hours, after which time readings were taken on the 12 cells with lima bean leaves. The 4 remaining cells were read at 7 days for a delayed toxicity reading. Of the compounds tested, the following resulted in greater than or equal to 80% mortality and/or development activity: 19, 22, 63, 65.
  • Test umts each consisting of an 8 ounce (230 mL) plastic cup containing a one-inch square (2.54 cm 2 ) of a wheatgerm diet, were prepared. The test units were sprayed as describe in TEST E with individual solutions of the test compounds. After the spray on the cups had dried, five second-instar larvae of the southern com rootworm (Diabrotica undecimpunctata howardi) were placed into each cup. The cups were then held at 27°C and 50% relative humidity for 48 h, after which time mortality readings were taken. The same units were read again at 8 days. Of the compounds tested, the following gave mortality and or
  • Test units were prepared from a series of 12 ounce (350 mL) cups, each containing oat (Avena sativa) seedlings in a 1 inch (2.54 cm) layer of sterilized soil.
  • the test units were sprayed as described in TEST E with individual solutions of the test compounds. After the oats had dried from the spraying, between 10 and 15 adult aster leafhoppers (Mascrosteles fascifrons) were aspirated into each of the cups.
  • the cups were covered with vented lids and held at 27°C and
  • Test units consisting of 9 ounce (260 mL) cups containing five adult boll weevils (Anthonomus grandis grandis) were prepared. The test units were sprayed as described in TEST E with individual solutions of the test compounds. Each cup was covered with a vented lid and held at 27°C and 50% relative humidity for 48 h, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 5, 19, 22, 24, 43, 44, 48, 55, 58, 63, 65, 68, 72, 74.
  • kidney bean leaves that had been infested on the undersides with 25 to 30 adult mites (Tetranychus urticae) were sprayed with their undersides facing up on a hydraulic sprayer with a solution of the test compound in 75/25 acetone/distilled water solvent. Spraying was accomplished by passing the leaves, on a conveyor belt, direcdy beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg/ha) at 30 p.s.i. (207 kPa).
  • the leaf squares were then placed underside-up on square of wet cotton in a petri dish and the perimeter of the leaf square was tamped down onto the cotton with forceps so that the mites cannot escape onto the untreated leaf surface.
  • the test units were held at 27°C and 50% relative humidity for 48 h, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 3, 5, 11, 15, 16, 17, 18, 19, 22, 23, 24, 27, 32, 33, 34, 36, 37, 41, 42, 43, 44, 48, 49, 50, 53, 62, 63, 65, 68, 71, 72, 74.

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Abstract

L'invention concerne des composés dotés d'une activité fongicide, acaricide et arthropodicide de la formule (I) dans laquelle A représente alkylène C1-C3 à chaîne droite ou ramifiée ou cycloalkylène C3-C6, où l'un quelconque des atomes de carbone de A peut être éventuellement substitué; R1 représente H, alkyle C¿1?-C3 ou alcoxy C1-C3; R?2¿ représente H, halogène, CN, alkyle C¿1?-C6, alcoxy C1-C6 ou SCN; R?3¿ représente H, formyle, alkyle C¿1?-C6, alkylcarbonyle C2-C6 ou alcoxycarbonyle C2-C6 et Q représente un système cyclique carbobicyclique fusionné ou hétérobicyclique fusionné à 8, 9 ou 10 éléments; ou bien Q représente un cycle hétéromonocyclique à 5 ou 6 éléments. Q comporte un 1 à 4 hétéroatomes sélectionnés indépendemment dans le groupe azote 0-4, oxygène 0-2 et soufre 0-2 et substitués par Z et à nouveau substitués avec 1 ou 2 substituants sélectionnés indépendemment à partir de R?8¿.
PCT/US1994/008499 1993-09-09 1994-08-04 Aminopyrimidines fongicides, acaricides et arthropodicides WO1995007278A1 (fr)

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US5852023A (en) * 1995-03-29 1998-12-22 Hoechst Schering Agrevo Gmbh Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides
WO2001055143A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives de benzoxazole et leur utilisation comme pesticides
WO2003077656A1 (fr) * 2002-03-15 2003-09-25 Ciba Specialty Chemicals Holding Inc. 4-aminopyrimidines et leur utilisation pour le traitement antimicrobien de surfaces
JP2009524677A (ja) * 2006-01-25 2009-07-02 シンタ ファーマシューティカルズ コーポレーション 炎症および免疫関連使用用のチアゾールおよびチアジアゾール化合物
WO2010025851A1 (fr) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Thiényl-aminopyrimidines en tant que fongicides
WO2012096061A1 (fr) * 2011-01-14 2012-07-19 株式会社エス・ディー・エス バイオテック Dérivé de pyrimidine en tant qu'agent de lutte contre les organismes nuisibles à usage agricole et horticole
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US20150011569A1 (en) * 2011-12-15 2015-01-08 Philadelphia Health & Education Corporation D/B/A Drexel University College Of Medicine NOVEL P13K p110 INHIBITORS AND METHODS OF USE THEREOF
WO2015032280A1 (fr) * 2013-09-06 2015-03-12 中国中化股份有限公司 Composé arylpyridine (pyrimidine) et utilisation associée
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WO2019105275A1 (fr) 2017-11-29 2019-06-06 沈阳中化农药化工研发有限公司 Composé de pyrimidine substitué, procédé de préparation associé et utilisation correspondante
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