LV10084B - Fungicides - Google Patents

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Publication number
LV10084B
LV10084B LVP-92-487A LV920487A LV10084B LV 10084 B LV10084 B LV 10084B LV 920487 A LV920487 A LV 920487A LV 10084 B LV10084 B LV 10084B
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hydrogen
alkyl
general formula
oxygen
compounds
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LVP-92-487A
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LV10084A (lv
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Patrick Jelf Crowley
Alasdair Thomas Glen
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Ici Plc
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Priority claimed from GB898902323A external-priority patent/GB8902323D0/en
Priority claimed from GB898923366A external-priority patent/GB8923366D0/en
Application filed by Ici Plc filed Critical Ici Plc
Publication of LV10084A publication Critical patent/LV10084A/lv
Publication of LV10084B publication Critical patent/LV10084B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N43/44—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Claims (10)

  1. LV 10084 IZGUDROJUMA FORMULA Savienojumi ar vispārīgo formulu (l):
    'NR1R2 D' B (I), kur A un B neatkarīgi viens no otra ir H, fluors, hlors, broms, Cx-Cu alkil-, Cji-C^ alkoksi- vai halogēn(C1-C^)alkilgrupa, ar nosacījumu, ka abi vienlaikus nevar būt H; D un E neatkarīgi viens no otra ir H vai fluors; R1 ir H vai CA-C^ alkilgrupa vai C^-C^ alkoksigrupa; R2 ir Ci-C^ alkil-, C^-C^ alkoksi- vai neobligāti aizvietota fenilgrupa; vai arī R1 un R2 kopā ar slāpekļa atomu, pie kura tie pievienoti, veido morfolīna, piperidīna, pirolidīna vai azetidīna ciklu, kas var būt aizvietoti ar C±-Cķ alkilgrupu; R3 ir ūdeņradis; Ru ir trihlormetil-, C2-Cs alkilgrupa (kas var būt aizvietota ar halogēnu, Ci-C8 alkoksigrupu vai R'S(o)n grupu, kurā R* ir Ci-C* alkil-, C2-CB alkenil- vai C2-Cķ alkinilgrupa, bet n = 0, 1 vai 2), ciklopropilgrupa (kas var būt aizvietota ar halogēnu vai Ci-C,* alkilgrupu), C2-CB alkenil-, C2-Ca alkinil-, Ci-C8 alkoksi-, mono- vai difci-CtJalkilaminogrupa vai R’ON=c(cn) grupa, kur R' ‘ ir Ci-C* alkilgrupa, vai arī R3 un Ru kopā ar grupu C(o)N, pie kuras .tie pievienoti, veido azetidiņ-2-ona gredzenu, kas var būt aizvietots ar halogēnu vai Ci-C* alkilgrupu; X un Υ neatkarīgi viens no otra ir skabeklis vai sērs.
  2. 2. Savienojumi atbilstoši 1.p., kas atšķiras ar to, ka A un B neatkarīgi ciens no otra ir H, fluors, hlors, vai broms ar nosacījumu, ka abi vienlaicīgi nevar būt H; D un E ir ūdeņraži; R Air ūdeņradis, vai Ci-C^ alkilgrupa; R2 ir C^-C,* alkil-, Ci-C^, alkoksi- vai fenilgrupa; vai arī R1 un R2 kopā ar slāpekļa atomu, pie kura tie pievienoti, veido morfolīna, piperidīna, pirolidīna vai azetidīna ciklus; R3 ir ūdeņradis; R&quot;- ir C3-CB alkilgrupa (kas var būt aizvietota ar halogēnu, metoksi- metiltio- vai metilsulfonilgrupu), cik-lopropilgrupa ( kas var būt aizvietota ar metilgrupu), C3-Ce alke-nil-, C3-CB alkinil-, C±-C^ alkoksigrupa vai grupa CH30N=C(CN); X un Y abi ir skābekļi.
  3. 3. Savienojumi atbilstoši 1.p., kas atšķiras ar to, ka A ir hlors; B, D un E visi ir ūdeņraži; R1 ir ūdeņradis, metil- vai etil-grupa; R2 ir metil-, etil- vai fenilgrupa; vai arī R1 un R2 kopā ar slāpekļa atomu, pie kura tie pievienoti, veido morfolīna vai piperidīna ciklu; R3 ir ūdeņradis; R1* ir 03-0* alkil- vai ciklopropilgru-pa; X un Y abi ir skābekļi.
  4. 4. Savienojumi atbilstoši 1.p., kas atšķiras ar to, ka Δ ir hlors; B, D un E visi ir ūdeņraži; R1 un R2 neatkarīgi viens no otra ir metil- vai etilgrupa, vai arī kopā ar slāpekļa atomu, pie kura tie pievienoti, veido morfolīna vai piperidīna ciklu; R3 ir ūdeņradis; Rw ir izopropil-, terc-butil- vai ciklopropilgrupa; X un Y ir skābekļi.
  5. 5. Savienojumi ar formulu (1.1):
    N(CH3) kur A un B neatkarīgi viens no otra ir hlors, broms vai metilgrupa, vai arī ūdeņradis; Z ir fluors, hlors, broms, metil-, etil- vai - 3 - LV 10084 metoksigrupa.
  6. 6. Savienojumi .atbilstoši 5.p., kas atšķiras ar to, ka B ir ūdeņradis vai A un B abi ir hlora atomi vai metilgrupas.
  7. 7. Savienojumi atbilstoši 5.p., kas atšķiras ar to, ka A ir hlors vai broms, B ir ūdeņradis, vai arī A un B abi ir hlora atomi; Z ir metilgrupa.
  8. 8. Paņēmiens savienojumu atbilstoši 1.p. iegūšanai, kas atšķiras ar to, ka veic sekojošus procesus: a) ja X un Y abi ir skābekļi un R3 ir ūdeņradis, tad i) uz savienojumu ar vispārīgo formulu (vi) :
    iedarbojas ar hloranhidrīdu R**C0CI piemērotā organiskā šķīdinātājā bāzes klātbūtnē; ii) uz savienojumu ar vispārīgo formulu (IX):
    iedarbojas ar amīnu RAR2NH piemērotā organiskā šķīdinātājā bāzes vai R1R2NH pārākuma klātbūtnē; yai iii) uz savienojumu ar vispārīgo formulu (XXXIII):
    (XXXIII) iedarbojas ar amīdu R^-CO-NHa un bāzi; b) ja X un Y abi ir skābekļi, bet R3 un R1* kopā ar grupu c(o)N veido sekojošas formulas gredzenu: 4 - Ο ιι .c.
    i) tad savienojumu ar vispārīgo formulu (X) :
    'NR1R2 (X) apstrādā ar divfāzu sistēmu, kas sastāv no organiska šķīdinātāja un ūdens, fāžu pārneses katalizatora klātbūtnē; o) ja X un Y abi ir skābekļi, R3 ir ūdeņradis, bet R1* ir sekojoša grupa:
    i) tad savienojumu ar vispārīgo formulu (XVII):
    (XVII) apstrādā ar fluora pārneses reaģentu piemērotā šķīdinātāja; d) ja X un Y abi ir skābekļi, bet R3 ir ūdeņradis un R*4, ir sekojoša grupa: R\ fch2—— Ra/ i) tad savienojumu ar vispārīgo formulu (XIX): 0
    (XIX) apstrādā ar fluorēšanas aģentu piemērotā šķīdinātājā; vai ii) uz savienojumu ar vispārīgo formulu (Vl) :
    - 5 - LV 10084 iedarbojas ar sekojošas formulas (XXXV) hloranhidrīdu: 0 S &quot; fch2-zC—C—Cl R8 piemērotā šķīdinātājā bāzes klātbūtnē; e) ja X ir skābeklis vai sērs, Y ir sērs, bet R3 ir ūdeņradis: i) tad savienojumu ar vispārīgo formulu (II):
    S/ SNR1R2 * (II) apstrādā ar tionēšanas aģentu piemērotā šķīdinātājā, pie kam rodas savienojums ar vispārīgo formulu (i) , kur X ir skābeklis, Y ir sērs, bet R3 ir ūdeņradis, vai arī savienojumu ar formulu (i) maisījums, kur vienam X ir skābeklis un Y ir sērs, bet otram X un Y abi ir sēra atomi, abiem R3 ir ūdeņradis; f) ja X ir sērs, Y ir skābeklis, bet R3 ir ūdeņradis, tad: i) uz izocianātu ar vispārīgo formulu (XXIII): s=c=n— (Cy&gt; —c: ip2 NR^R (XXIII) iedarbojas ar metalorganisko reaģentu RuL i vai R^MgHal piemērotā šķīdinātājā temperatūras intervālā no -78° līdz +25°C; vai ii) hloranhidrīdu (XXVI):
    (XXVI) apstrādā ar amīnu R1R2NH bāzes klātbūtnē; vai arī g) ja X un Y abi ir skābekļi, R3 ir ūdeņradis, bet R** ir sekojoša grupa: R8 R* ' 0CH2-3C— Ra/ - 6 - i) tad uz savienojumu ar vispārīgo formulu (XIX): hoch2
    “NR1R2 D' 'B (XIX) iedarbojas ar halogenīdu R''Hal piemērotā šķīdinātājā bāzes klātbūtnē ; kur Δ, B, D, E, R1, R2 un R1* atbilst 1.p. norādītajām nozīmēm, izņemot speciāli minētos gadījumus, bet R5 un RB ir ūdeņradis, Cx-Cu al-kilgrupa vai halogēns, R8 un R8 ir ūdeņradis, c^c,,. alkil- vai Ci-C^ halogēnalkilgrupa, R'' ir Ci~Cķ alkilgrupa, X' ir hlors, broms vai jods, Hal nozīmē halogēnu, bet L ir atšķeļama grupa.
  9. 9. Fungicīdu kompozīcija, kas atšķiras ar to, ka satur efektīvu daudzumu fungicīda no savienojumiem atbilstoši 1.p., fungicīdiem piemērotu nesēju un atšķaidītāju.
  10. 10. Metode sēnīšu apkarošanai, kas atšķiras ar to, ka ietver augu, sēklu vai augu infekcijas vietas apstrādi ar savienojumu atbilstoši 1.p. vai kompozīciju atbilstoši 9.p.
LVP-92-487A 1989-02-02 1992-12-24 Fungicides LV10084B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898902323A GB8902323D0 (en) 1989-02-02 1989-02-02 Fungicides
GB898923366A GB8923366D0 (en) 1989-10-17 1989-10-17 Fungicides

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LV10084A LV10084A (lv) 1994-05-10
LV10084B true LV10084B (en) 1995-02-20

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US (2) US4999381A (lv)
EP (1) EP0381330B1 (lv)
JP (1) JP2688530B2 (lv)
KR (1) KR0145295B1 (lv)
CN (1) CN1024004C (lv)
AP (1) AP123A (lv)
AR (1) AR246734A1 (lv)
AU (1) AU617238B2 (lv)
BR (1) BR9000477A (lv)
CA (1) CA2008291A1 (lv)
DE (1) DE69005466T2 (lv)
EG (1) EG19119A (lv)
ES (1) ES2062320T3 (lv)
GB (1) GB9002370D0 (lv)
HU (1) HU206191B (lv)
IE (1) IE62559B1 (lv)
IL (1) IL93076A (lv)
LV (1) LV10084B (lv)
MY (1) MY106000A (lv)
NZ (1) NZ232127A (lv)
PL (2) PL163362B1 (lv)
PT (1) PT93030B (lv)
SK (1) SK23690A3 (lv)

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GB9016582D0 (en) * 1990-07-27 1990-09-12 Ici Plc Fungicides
GB9016581D0 (en) * 1990-07-27 1990-09-12 Ici Plc Fungicides
GB9016580D0 (en) * 1990-07-27 1990-09-12 Ici Plc Fungicides
EP0468681B1 (en) * 1990-07-27 1995-05-24 Zeneca Limited Alfa-fluorocarboxylic acid derivatives as intermediates for the preparation of fungicides
GB9016578D0 (en) * 1990-07-27 1990-09-12 Ici Plc Fungicides
US5639949A (en) * 1990-08-20 1997-06-17 Ciba-Geigy Corporation Genes for the synthesis of antipathogenic substances
US5662898A (en) * 1990-08-20 1997-09-02 Ciba-Geigy Corporation Genes for the synthesis of antipathogenic substances
CA2119155C (en) * 1991-10-18 1999-06-15 Dennis Paul Phillion Fungicides for the control of take-all disease of plants
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HU206191B (en) 1992-09-28
HUT52752A (en) 1990-08-28
US5280044A (en) 1994-01-18
IE900145L (en) 1990-08-02
AU617238B2 (en) 1991-11-21
DE69005466T2 (de) 1994-04-14
US4999381A (en) 1991-03-12
KR900012535A (ko) 1990-09-01
BR9000477A (pt) 1991-01-15
IE62559B1 (en) 1995-02-08
PL163362B1 (pl) 1994-03-31
PT93030A (pt) 1990-08-31
PL163155B1 (pl) 1994-02-28
SK278842B6 (sk) 1998-03-04
MY106000A (en) 1995-02-28
EP0381330B1 (en) 1993-12-29
CA2008291A1 (en) 1990-08-02
HU900221D0 (en) 1990-03-28
GB9002370D0 (en) 1990-04-04
KR0145295B1 (ko) 1998-07-15
EG19119A (en) 1994-11-30
AR246734A1 (es) 1994-09-30
PT93030B (pt) 1995-12-29
ES2062320T3 (es) 1994-12-16
SK23690A3 (en) 1998-03-04
JP2688530B2 (ja) 1997-12-10
CN1024004C (zh) 1994-03-16
LV10084A (lv) 1994-05-10
EP0381330A1 (en) 1990-08-08
IL93076A (en) 1994-02-27
AP123A (en) 1991-03-03
AP9000159A0 (en) 1990-01-31
NZ232127A (en) 1991-07-26
AU4887190A (en) 1990-08-09
CN1046523A (zh) 1990-10-31
DE69005466D1 (de) 1994-02-10
JPH02247158A (ja) 1990-10-02

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