NO313416B1 - Fungicide trifluormetylamino-triazolopyrimidiner, fremgangsmåte for fremstilling og anvendelse derav - Google Patents
Fungicide trifluormetylamino-triazolopyrimidiner, fremgangsmåte for fremstilling og anvendelse derav Download PDFInfo
- Publication number
- NO313416B1 NO313416B1 NO19994973A NO994973A NO313416B1 NO 313416 B1 NO313416 B1 NO 313416B1 NO 19994973 A NO19994973 A NO 19994973A NO 994973 A NO994973 A NO 994973A NO 313416 B1 NO313416 B1 NO 313416B1
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- triazolo
- pyrimidine
- trifluoroethyl
- trifluoro
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 36
- -1 trifluoromethylamino-triazolopyrimidines Chemical class 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 241000233866 Fungi Species 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000006308 propyl amino group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000006309 butyl amino group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000000417 fungicide Substances 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
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- 239000001257 hydrogen Substances 0.000 claims description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- 229960005322 streptomycin Drugs 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000021918 systemic acquired resistance Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000006478 transmetalation reaction Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
BAKGRUNN FOR OPPFINNELSEN
Foreliggende oppfinnelse vedrører bestemte triazolopyrimidinforbindelser, en fremgangsmåte for deres fremstilling, preparater inneholdende slike forbindelser, en metode for å bekjempe en sopp på et voksested omfattende behandling av voksestedet med slike forbindelser og anvendelse av dem som fungicider.
EP-A-0 071 792 krever forbindelser med den generelle formel
hvor R<1> representerer alkyl, halogen, alkoksy, cyano, cykloalkyl, aryl, aryloksy, aryltio, aralkyl, aryltio, arylalkyl, arylalkyloksy eller arylalkyltio, hver eventuelt substituert med halogen eller alkoksy; eller (R<1>)n representerer en benzen-, indan-eller tetrahydronaftalenring kondensert med fenylringen, idet aromatiske grupper i gruppene ovenfor eventuelt er substituert med alkyl, alkoksy, halogen eller cyano;
n er 1 eller 2; R2 og R<3> er hver hydrogen, alkyl eller aryl, A representerer et nitrogenatom eller en CR4 gruppe, og R<4> er som R<2>, men kan også være halogen, cyano eller alkoksykarbonyl, eller kan sammen med R3 danne en alkylenkjede inneholdende opptil to dobbeltbindinger. Forbindelsene er nevnt å være aktive mot forskjellige fytopatogene sopp, spesielt de fra phycomycetklassen. Imidlertid er bevis på fungicid aktivitet funnet for disse forbindelser mot Plasmopara viticola, et medlem av oomycetklassen av sopp.
EP 0 550 113-A2 krever forbindelser med den generelle formel 1
hvor R<1> representerer en eventuelt substituert alkyl-, alkenyl-, alkadienyl-, cykloalkyl-, bicykloalkyl- eller heterocyklylgruppe; R2 representerer et hydrogenatom eller en alkylgruppe; eller R<1> og R<2> sammen med det mellomliggende nitrogenatom representerer en eventuelt substituert heterocyklisk ring; R3 representerer en eventuelt substituert arylgruppe; og R<4> representerer et hydrogen- eller halogenatom eller en gruppe -NR<5>R<6> hvor R5 representerer et hydrogenatom eller en amino-, alkyl-, cykloalkyl- eller bicykloalkylgruppe, og R<6 >representerer et hydrogenatom eller en alkylgruppe. Således er forbindelser hvor R<1> er en trifluormetylalkylgruppe generelt omfattet av denne patentsøknad. Imidlertid er det ikke en eneste forbindelse beskrevet hvor R<1> er en trifluormetylalkylgruppe.
OPPSUMMERING AV OPPFINNELSEN
Foreliggende oppfinnelse tilveiebringer en forbindelse med formel I
hvor
R<1> representerer et hydrogenatom eller en metylgruppe, og
R<2> representerer et hydrogen atom eller en Ci-Ci0-alkylgruppe,
Hal representerer et halogenatom,
f.o.m. L1 t.o.m. L5 representerer hver uavhengig et hydrogen- eller halogenatom eller en metyl-, metoksky- eller nitrogruppe.
De nye forbindelser viser en utmerket selektiv fungicid aktivitet i forskjellige avlinger.
Det er en mål for foreliggende oppfinnelse å tilveiebringe nye, selektive fungicide forbindelser.
Det er også en mål for foreliggende oppfinnelse å tilveiebringe metoder for kontroll av uønsket sopp ved å kontakte nevnte planter med en fungicid effektiv mengde av de nye forbindelser.
Det er et annet mål for foreliggende oppfinnelse å tilveiebringe selektive fungicide preparater inneholdende de nye forbindelser som aktive bestanddeler.
Disse og andre mål og trekk ifølge foreliggende oppfinnelse vil bli klarere fra den detaljerte beskrivelse angitt nedenunder og fra medfølgende krav.
DETALJERT BESKRIVELSE AV DE FORETRUKNE UTFØRELSESFORMER
Det har overraskende blitt funnet at de nye forbindelsene med formel I
hvor R<1>, R<2>, Hal og L<1> gjennom L5 har betydningen gitt ovenfor for formel I viser en utmerket fungicid aktivitet mot et bredt område av sopp.
Generelt, hvis ikke annet er angitt, kan betegnelsen halogenatom som anvendt her angi et brom-, jod-, klor- eller fluoratom og er spesielt et brom-, Mor-eller fluoratom.
Hal representerer fluor, klor, brom eller jod, spesielt klor.
Eventuelt substituerte grupper kan være usubstituerte eller ha fra én opptil det maksimalt mulige antall substituenter. Typisk er 0 til 3 substituenter til stede.
Oppfinnelsen angår spesielt forbindelser med den generelle formel I hvor R2 kan være rettkjedet eller forgrenet, inneholder opptil 10 karbonatomer, fortrinnsvis opptil 9 karbonatomer, mer foretrukket opptil 6 karbonatomer
Omfattet innenfor omfanget av foreliggende oppfinnelse er (R)- og (S)-isomerer og atropisomerer av forbindelser med den generelle formel I, som har et chiralt senter, eller hvor substituentene L<1> eller L<1> og L2 er forskjellige fra L5 eller L5 og L<4> og racematene derav og salter, N-oksyder og syreaddisjonsforbindelser.
Spesielt interessant aktivitet er funnet ved (S)-isomere forbindelser med den generelle formel I, hvor gruppen -CH(CF3)R<1> er chiral.
Slike forbindelser med formel l hvor minst én av R<1> og R<2> representerer et hydrogenatom, er spesielt foretrukket.
Spesielt foretrukket er forbindelser med formel I, hvor fenylgruppen
Forbindelsene i henhold til den generelle formel I er oljer, gummier eller overveiende krystallinske faste materialer. De er overlegne gjennom sine verdifulle fungicide egenskaper, spesielt sine økede systemiske virkning og øket fungicid toksisitet mot ris-sykdommer og pulver-meldugg. For eksempel kan de anvendes i jordbruket eller beslektede områder for kontroll av fytopatogen sopp så som Altemaria solani, Botrytis cinerea, Cercospora beticola, Cladosporium herbarum, Corticium rolfsii, Erysiphe graminis, Helminthosporium tritici repentis, Leptosphaeria nodorum, Mikronectriella nivalis, Monilinia fructigena, Mycosphaerella ligulicola, Mycosphaerella pinodes, Pyricularia grisea f. sp. oryzae, Rhizoktonia solani, Venturia inaequalis, Uncinula necator og Sclerotinia sclerotiorum, spesielt for kontroll av Uncinula necator, Pyricularia grisea f. sp. oryzae og Rhizoktonia solani. Forbindelsene med den generelle formel I ifølge oppfinnelsen har en høy fungicid aktivitet innenfor et bredt konsentrasjonsområde og kan anvendes i jordbruket uten noen som helst vanskeligheter.
Videre viser forbindelsene ifølge oppfinnelsen øket gjenværende kontroll av sopp, spesielt av drue-pulver-meldugg sammenlignet med konvensjonelle fungicider.
Gode resultater med hensyn til kontroll av fytopatogen sopp blir oppnådd med en forbindelse som definert i formel I hvor:
minst én av L<1> og L5 representerer et halogenatom.
Spesielt gode resultater med hensyn til kontroll av fytopatogen sopp blir oppnådd ved anvendelse av, for eksempel de følgende forbindelser med formel I: 5-klor-6-(2-klor-6-fluorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-7-(2,2,2-trifluoretylamino)-6-(2,4,6-trifluorfenyl)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-(2,2,2-trifluoretylaminoH1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[2-(1,1,1 -trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluorfenyl)-7-[2-(1,1,1-trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4,6-trifluorfenyl)-7-[2-(1,1,1 -trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-metylfenyl)-7-[2-(1,1,1 -trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-fluorfenyl)-7-[2-(1,1,1-trifluor)propylaminoH1.2,4]triazolo[1,5-a]pyrimidi^ 5-klor-6-(2-klorfenyl)-7-[2-(1,1,1-trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klor-6-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klor-6-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klorfenyl)-7-[N-(2,2>2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-ajpyrimidin
5-klor-6-(2-klor-6-fiuorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)amino]^
[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-fluorfenyl)-7-[N-(2,2,2-trifluoret7l)-N-(2-metylpropyl)-amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)am [1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)-amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-fluofrenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2>4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-fluofrenyl)-7-[N-(2,2,2-trifluoretyl)-N-isopropylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(216-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-isopropylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-isopropylamino [1,2,4]triazolo[1,5-ajpyrimidin
5-klor-6-(2-klor-6-fluorfenyl)-7-[N-(2)2>2-trifluoretyl)-N-isopropylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(1-fenyletyl)amino]-[1,2,4]triazolo[1,5-ajpyrimidin
5-klor-6-(2-fluorfenyl)-7-[N,N-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-ajpyrimidin
5-klor-6-(2-metylfenyl)-7-[N,N-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klorfenyl)-7-[N,N-di-(2I2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klor-6-fluorfenyl)-7-[N,N-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-ajpyrimidin
5-klor-6-(2,6-difluorfenyl)-7-[N,N-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4I6-trifluorfenyl)-7-[N,N-di-(2I2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluofrenyl)-7-[N,-(2,2,2-trifluoretyl)-N-(1I2-dimetylpropyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(214,6-trifluorfenyl)-7-[Nr(2,2,2-trifluoretyl)-N-(trimeytlsilylme [1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-brom-5-klorfenyl)-7-[2-(1,1,1 -trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrim 5-klor-6-(4-klorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrim 5-klor-6-(4-bromfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrim 5-klor-6-(4-metoksyfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyri 5-klor-6-(4-nitrofenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrim 5-klor-6-(2-fluorfenyl)-7-(1-fenyl-2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klor-6-fluorfenyl)-7-[2-(1,1,1-trifluor)butylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klor-6-fIuorfenyl)-7-(1-fenyl-2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-fluorfenyl)-7-[2-(1,1,1-trifluor)butylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-(1-fenyl-2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4,6-trifIuorfenyl)-7-(1-fenyl-2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4,6-trifluorfenyl)-7-[2-(1,1,1 -trifluor)butylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-k!or-6-(2,6-difluorfenyl)-7-[2-(1,1,1-trifluor)butylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2-klorfenyl)-7-[2-(1,1,1-trifluor)butylamino]-[1,2,4]triazolo[1,5-a]py 5-klor-6-(2-klorfenyl)-7-(1-fenyl-2,2l2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,4-difluofrenyl)-7-(2,2,2-trifluoretylaminoH1I2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[2-(1,1,1 -trifluor)-3-metylbutylamino]-[1,2,4]triazolo[1,5-a]pyrimidin
5-klor-6-(2,6-difluor-4-metoksyfenyl)-7-[2-(1,1,1 -trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin.
Foreliggende oppfinnelse tilveiebringer videre en fremgangsmåte for fremstilling av en forbindelse med formel I som definert ovenfor, som omfatter
behandling av en forbindelse med den generelle formel II
hvor
f.o.m. L<1> t.o.m. L5 og Hal er som definert forut;
med et amin eller amid med den generelle formel III
hvor
R<1> og R2 er som definert ovenfor,
M representerer et hydrogenatom eller et fritt eller kompleksert metallatom, fortrinnsvis valgt fra gruppen bestående av Li, Na, K, Zn og Cu,
hvilket gir en forbindelse med formel I
Forbindelser med formel II er kjente, f.eks. fra EP 0 550 113, og blir vanligvis fremstilt ved omsetning av 3-amino-1,2,4-triazol med en 2-fenyl-substituert malonsyreester med formel IV,
hvor R representerer alkyl, under alkaliske betingelser, fortrinnsvis ved anvendelse av høytkokende tertiære aminer som for eksempel tri-n-butylamin.
De resulterende 5,7-dihydroksy-6-fenyltriazolopyrimidiner blir deretter behandlet med et halogeneringsmiddel, fortrinnsvis med et bromerings- eller kloreringsmiddel, så som fosforoksybromid eller fosforoksyklorid, alene eller i nærvær av et løsningsmiddel. Reaksjonen blir hensiktsmessig utført ved en temperatur i området fra 0 °C til 150 °C, idet den foretrukne reaksjonstemperatur er fra 80 °C til 125 °C.
Reaksjonen mellom 5,7-dihalogen-6-fenyltriazolopyrimidinene med formel II og aminet eller amidet med formel III blir hensiktsmessig utført i nærvær av et løsningsmiddel. Egnede løsningsmidler omfatter etere, så som dioksan, dietyleter og, spesielt, tetrahydrofuran, halogenerte hydrokarboner så som diklormetan og aromatiske hydrokarboner, for eksempel toluen. Reaksjonen blir hensiktsmessig utført ved en temperatur i området fra 0 °C til 70 °C, idet den foretrukne reaksjon temperatur er fra 10 °C til 35 °C. Det er også foretrukket at reaksjonen blir utført i nærvær av en base. Egnede baser omfatter tertiære aminer, så som trietylamin og uorganiske baser, så som kaliumkarbonat eller natriumkarbonat. Alternativt kan et overskudd av forbindelsen med formel III tjene som en base.
Forbindelsene ifølge oppfinnelsen kan også oppnås ved omsetning av et 7-amino-5-halogen-6-fenyltriazolopyrimidin med en trifluoralkansyre eller et reaktivt derivat derav, spesielt med trifluoreddiksyreanhydrid, i nærvær av en base og påfølgende reduksjon av det resulterende trifluoralkansyreamid.
Aminene med formel III hvor M representerer et hydrogenatom, er velkjente i litteraturen eller kommersielt tilgjengelige, eller kan fremstilles analogt med metoder som er kjente som sådanne. Amidene med formel III hvor M representerer et metallatom blir som regel oppnådd fra de tilsvarende aminer (M = hydrogen) ved omsetning med en alkyllitiumforbindelse, eventuelt fulgt av en transmetalliseringsreaksjon.
På grunn av utmerket aktivitet kan forbindelsene med formel I anvendes ved dyrking av alle planter hvor infeksjon med fytopatogen sopp ikke er ønsket, f.eks. cerealier, solanplanteavlinger, rotgrønnsaker, grønnsaker, epler, vin.
Forbindelsene med den generelle formel I er funnet å ha fungicid aktivitet.
Følgelig tilveiebringer oppfinnelsen videre et fungicid preparat som omfatter en aktiv bestanddel, hvilken er minst én forbindelse med formel I som definert ovenfor og én eller flere bærere. En metode for fremstilling av et slikt preparat er også tilveiebrakt, som omfatter å bringe en forbindelse med formel I som definert ovenfor i forbindelse med bæreren(e). Et slikt preparat kan inneholde én eneste aktiv bestanddel eller en blanding av flere aktive bestanddeler ifølge foreliggende oppfinnelse. Det er også klart at forskjellige isomerer eller blandinger av isomerer kan ha forskjellige aktivitetsnivåer eller aktivitetsspektre, og således kan preparater omfatte individuelle isomere eller blandinger av isomere.
Et preparat ifølge oppfinnelsen inneholder fortrinnsvis fra 0,5 vekt-% til 95 vekt-% aktiv bestanddel.
En bærer i et preparat ifølge oppfinnelsen er hvilket som helst materiale med hvilket den aktive bestanddel formuleres for å lette applikasjon på stedet som skal behandles, som for eksempel kan være en plante, frø, jord eller vann hvor en plante vokser, eller for å lette lagring, transport eller handling. En bærer kan være et fast stoff eller en væske omfattende materiale som normalt er en gass, men som har blitt komprimert til å danne en væske.
Preparatene kan fremstilles i f.eks. emulsjonskonsentrater, løsninger, olje-i-vann-emulsjoner, fuktbare pulvere, oppløselige pulvere, suspensjonskonsentrater, støv, granulater, vann-dispergerbare granulater, mikro-kapsler, geler, tabletter og andre formuleringsformer ved velkjente prosedyrer. Disse prosedyrer omfatter grundig blanding og/eller maling av de aktive bestanddelene med andre substanser, så som fyllmidler, løsningsmidler, faste bærere, overflate aktive forbindelser (overflateaktive midler) og eventuelt faststoff- og/eller flytende hjelpemidler og/eller tilsetningsmidler. Applikasjonsformen så som sprøyting, atomisering, dispergering eller helling kan velges i likhet med preparatene i henhold til de ønskede mål og de foreliggende gitte omstendigheter.
Løsningsmidler kan være aromatiske hydrokarboner, f.eks. Solvesso<®> 200, substituert naftalener, ftalsyreestere, så som dibutyl- eller dioktylftalat, alifatiske hydrokarboner, f.eks. cykloheksan eller paraffiner, alkoholer og glykoler så vel som deres etere og estere, f.eks. etanol, etylenglykolmono- og dimetyleter, ketoner så som cykloheksanon, sterkt polare løsningsmidler så som N-metyl-2-pyrrolidon eller y-butyrolakton, høyere alkylpyrrolidoner, f.eks. n-oktylpyrrolidon eller cykloheksylpyrrolidon, epoksyderte plante-oljeestere, f.eks. metylert kokos- eller soabønneoljeestere og vann. Blandinger av forskjellig væsker er ofte egnet.
Faste bærere, som kan anvendes for støv, fuktbare pulvere, vann-dispergerbare granulater eller granulater, kan være mineralske fyllmidler, så som kalsitt, talkum, kaolin, montmorillonit eller attapulgit. De fysiske egenskaper kan forbedres ved tilsetning av høydispergert silikagel eller polymerer. Bærere for granulater kan være porøse materialer, f.eks. pimpestein, kaolin, sepiolit, bentonitt; ikke-sorptive bærere kan være kalsitt eller sand. I tillegg kan flere pre-granulerte uorganiske eller organiske materialer anvendes, så som dolomitt eller knuste planterester.
Pesticide preparater blir ofte formulert og transportert i en konsentrert form som deretter blir fortynnet av brukeren før applikasjon. Tilstedeværelsen av små mengder bærer som er et overflateaktivt middel letter denne fortynningsprosessen. Således er fortrinnsvis minst én bærer i et preparat ifølge oppfinnelsen et overflateaktivt middel. For eksempel kan preparatet inneholde to eller flere bærere, hvorav minst én er et overflateaktivt middel.
Overflateaktive midler kan være ikke-ioniske, anioniske, kationiske eller zwitterioniske substanser med gode dispersings-, emulgerings- og fukte-egenskaper avhengig av egenskapene til forbindelsen i henhold til den generelle formel I som skal formuleres. Overflateaktive midler kan også bety blandinger av individuelle overflateaktive midler.
Preparatene ifølge foreliggende oppfinnelse kan for eksempel formuleres som fuktbare pulvere, vanndispergerbare granulater, støv, granulater, tabletter, løsninger, emulgerbare konsentrater, emulsjoner, suspensjonskonsentrater og aerosol-preparater. Fuktbare pulvere inneholder vanligvis 5 til 90 vekt-% aktiv bestanddel, og inneholder vanligvis i tillegg til faststoff-inertbærer, 3 til 10 vekt-% dispergerings- og fuktemidler og, om nødvendig, 0 til 10 vekt-% stabilisator(er) og/eller andre additiver så som penetranter eller klebemidler. Støv blir vanligvis formulert som et støvkonsentrat som har en lignende sammensetning som et fuktbart pulver, men uten et dispergeringsmiddel og kan fortynnes i felten med ytterligere fast bærer, hvilket gir et preparat vanligvis inneholdende 0,5 til 10 vekt-% aktiv bestanddel. Vanndispergerbare granulater og granulater blir vanligvis fremstilt så de har en størrelse mellom 0,15 mm og 2,0 mm og kan fremstilles ved en rekke teknikker. Generelt vil disse typer av granulater inneholde 0,5 til 90 vekt-% aktiv bestanddel og 0 til 20 vekt-% additiver så som stabilisatorer, overflateaktive midler, langsom-frigjøringsmodifiseringsmidler og bindemidler. De såkalt "tørre flytbare" består av relativt små granulater som har en relativt høy konsentrasjon av aktiv bestanddel. Emulgerbare konsentrater inneholder vanligvis i tillegg til et løsningsmiddel eller en blanding av løsningsmidler, 1 til 80% vekt/volum aktiv bestanddel, 2 til 20% vekt/volum emulgeringsmidler og 0 til 20% vekt/volum andre additiver så som stabiliseringsmidler, penetranter og korrosjonsinhibitorer. Suspensjonskonsentrater blir vanligvis malt slik at det oppnåes et stabilt, ikke-sedimenterende flytbart produkt, og inneholder vanligvis 5 til 75% vekt/volum aktiv bestanddel, 0,5 til 15% vekt/volum dispergeringsmidler, 0,1 til 10% vekt/volum suspenderingsmidler så som beskyttende kolloider og thixotrope midler, 0 til 10% vekt/volum andre additiver så som skumdempere, korrosjonsinhibitorer, stabiliseringsmidler, penetranter og klebemidler og vann eller en organisk væske, hvor den aktive bestanddel er hovedsakelig uoppløselig; visse organiske faste stoffer eller uorganiske salter kan være til stede oppløst i preparatet for å hjelpe til å forhindre sedimentering og krystallisering eller som anti-frysemidler for vann.
Vandige dispersjoner og emulsjoner, for eksempel preparater oppnådd ved fortynning av formulert produkt ifølge oppfinnelsen med vann, ligger også innenfor omfanget av foreliggende oppfinnelse.
Av spesiell interesse ved økning av varigheten til den beskyttende aktivitet av forbindelsene ifølge foreliggende oppfinnelse er anvendelse av en bærer som vil bevirke langsom frigjøring av de pesticide forbindelser til omgivelsene til en plante som skal beskyttes.
Den biologiske aktiviteten til den aktive bestanddel kan også økes ved å innta et hjelpmiddel i sprøytefortynningen. Et hjelpemiddel er definert her som en substans som kan øke den biologiske aktiviteten til en aktiv bestanddel, men ikke selv er betydelig biologisk aktiv. Tilsetningsmiddelet kan enten inngå i preparatet som et co-formuleringsmiddel eller bærer, eller kan tilsettes sprøytetanken sammen med preparatet inneholdende den aktive bestanddel.
Som råvare kan preparatene fortrinnsvis foreligge i en konsentrert form, mens sluttbrukeren generelt anvender fortynnete preparater. Preparatene kan fortynnes til en konsentrasjon ned til 0,001% aktiv bestanddel. Dosene ligger vanligvis i området fra 0,01 til 10kga.i./ha.
Eksempler på formuleringer ifølge oppfinnelsen er:
Emulsionskonsentrat ( EC)
Preparatene ifølge foreliggende oppfinnelse kan også omfatte andre forbindelser som har biologisk aktivitet, f.eks. forbindelser som har lignende eller kompletterende pesticid aktivitet eller forbindelser som har plantevekstregulerende, fungicid eller insekticid aktivitet. Disse blandinger av pesticider kan ha et bredere aktivitetspektrum enn forbindelsen med den generelle formel I alene. Videre kan de andre pesticider ha en synergistisk effekt på den pesticide aktivitet av forbindelsen med den generelle formel I.
Den andre fungicide forbindelse kan for eksempel være én som også er i stand til bekjempe sykdommer på cerealier (f.eks. hvete) slik som forårsakes av Erysipha, Puccinia, Septoria, Gibberella og Helminthosporium spp., frø- og jord-plantesykdommer på solan-avlinger og pulver-meldugg og skabb på epler osv. Disse blandinger av fungicider kan ha et bredere aktivitetsspektrum enn forbindelsen med den generelle formel I alene. Videre kan det andre fungicid ha en synergistisk effekt på de fungicide aktiviteter av forbindelsen med den generelle formel I.
Eksempler på de andre fungicide forbindelser er anilazin, azoksystrobin, benalaxyl, benomyl, bethoksazin, binapakryl, bitertanol, blasticidin S, Bordeaux blanding, bromuconazol, bupirimat, captafol, captan, karbendazim, karboxin, carpropamid, chlorbenztiazon, chlorothalonil, chlozolinat, kobber-holdige forbindelser så som kobber-oksyklorid og kobbersulfat, cykloheksimid, cymoksanil, cypofuram, cyproconazol, cyprodinil, dichlofluanid, dichlon, dichloran, diclobutrazol, diclocymet, diclomezin, diethofenkarb, difenoconazole, diflumetorim, dimethirimol, dimethomorf, diniconazol, dinocap, ditalimfos, ditianon, dodemorph, dodine, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoksadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenheksamid, fenpiclonil, fenpropidin, fenpropimorph, fentin, fentin acetat, fentin hydroksyd, ferimzone, fluazinam, fludioksonil, flumetover, flukinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatin, heksaconazole, imazalil, iminoktadine, ipconazole, iprodione, isoprotiolane, kasugamycin, kitazin P, kresoxim-metyl, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methfuroksam, myclobutanil, neoasozin, nikkel dimetylditiokarbamat, nitrothalisopropyl, nuarimol, ofurace, organo-kvikksølvforbindelser, oxadixyl, oxykarboxin, penconazole, pencycuron, fenazineoksyd, ftalid, polyoxin D, polyram, probenazole, prochloraz, procymidione, propamocarb, propikonazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, quinomethionate, quinoksyfen, quintozene, spiroxamine, SSF-126, SSF-129, streptomycin, svovel, tebuconazole, tecloftalame, tecnazene, tetraconazole, tiabendazole, thifluzamide, tiophanat-metyl, thiram, tolclofosmethyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin A, vinclozolin, XRD-563, zarilamid, zineb, ziram
I tillegg kan kombinasjonspreparatene ifølge oppfinnelsen inneholde minst én forbindelse med formel I og hvilken som helst av de følgende klasser biologiske kontrollmidler så som virus, bakterier, nematoder, sopp og andre mikroorganismer som er egnet til kontroll av insekter, gressarter eller plante-sykdommer eller til å indusere vertsresistens hos plantene. Eksempler på slike biologiske kontrollmidler er: Bacillus thuringiensis, Verticillium lecanii, Autographica califomica NPV, Beauvaria bassiana, Ampelomyces kisqualis, Bacilis subtilis, Pseudomonas klorraphis, Pseudomonas fluorescens, Steptomyces griseoviridis og Trichoderma harzianum.
Videre kan kombinasjonspreparatene ifølge oppfinnelsen inneholde minst én forbindelse med formel I og et kjemisk middel som induserer den systemiske tilegnede resistens hos planter, så som for eksempel nikotinsyre eller derivater derav eller BION.
Forbindelsene med den generelle formel I kan blandes med jord, torv eller andre rotmedier for beskyttelse av plantene mot frø-bårede, jord-bårede eller bladsoppsykdommer.
Oppfinnelsen tilveiebringer i tillegg anvendelse som fungicid av en forbindelse med den generelle formel I som definert ovenfor eller et preparat som definert ovenfor og en metode for bekjempelse av sopp på et voksested, som omfatter behandling av voksestedet, som for eksempel kan være planter utsatt for eller gjenstand for soppangrap, frø av slike planter eller mediet hvor slike planter vokser eller er skal vokse, med slik en forbindelse eller preparat.
Foreliggende oppfinnelse har bred anvendelse ved beskyttelse av avlinger og prydplanter mot soppangrep. Typiske avlinger som kan beskyttes omfatter vinranker, kornavlinger så som hvete og bygg, ris, sukkerroer, toppfrukter, peanutter, poteter, grønnsaker og tomater. Varigheten av beskyttelsen er normalt avhengig av den valgte enkelte forbindelse og også en rekke eksterne faktorer, så som klima, hvis påvirkning normalt blir påvirket ved anvendelse av en egnet formulering.
De følgende eksempler illustrerer videre foreliggende oppfinnelse. Det skal imidlertid forstås at oppfinnelsen ikke bare er begrenset til de spesielle eksempler gitt nedenfor.
Eksempel 1
5-Klor-6-(2-klor-6-fluorfenyl)-7-N-(2,2,2-trifluoretylamino)-1,2,4-triazolo[1,5a]pyrimidin
En blanding av 2,2,2-trifluoretylamin (4,2 mmoles) og diklormetan (10 ml) blir satt til en blanding av 5,7- diklor-6-(2-klor-6-fluorfenyl)-1,2,4-triazolo[1,5a]pyrimidin (1,4 mmol) og diklormetan (30 ml) under omrøring. Reaksjonsblandingen blir rørt 16 timer ved romtemperatur, deretter vasket to ganger med 1 N saltsyre og én gang med vann. Det organiske laget blir skilt fra, tørket med vannfritt natriumsulfat, og løsningsmidlet blir avdampet under redusert trykk. Behandling av den resulterende lyse brune olje med fe/f.-butyl metyleter (50 ml) gir beige krystaller som har et smeltepunkt på 194-197 °C.
Eksempler 2- 69
De følgende eksempler (Tabell I; struktur og smeltepunkt) blir syntetisert analogt med Eksempel 1.
Biologiske undersøkelser
A. Bestemmelse av minimum hemmende konsentrasjon av testforbindelser i seriell fortynning av test med forskjellige fytopatogene sopp
MIC (Minimum hemmende konsentrasjon) verdi som indikerer den laveste konsentrasjon av den aktive bestanddel i vekstmediet som forårsaker en total hemning av myecelvekst, blir bestemt ved serielle fortynningstester ved anvendelse av mikrotiterplater med 24 eller 48 brønner pr. plate. Fortynningen av testforbindelsene i næringsløsningen og fordelingen til brønnene blir utført med en TECAN RSP 5000 Robotic Sample Processor. De følgende testforbindelses-konsentrasjoner blir anvendt: 0,05, 0,10, 0,20, 0,39, 0,78, 1,56, 3,13, 6,25, 12,50, 25,00, 50,00 og 100,00 mg/ml. For fremstilling av næringsløsningen blir V8 vegetabilsk saft (333 ml) blandet med kalsiumkarbonat (4,95 g), sentrifugert, supernatanten (200 ml) fortynnet med vann (800 ml) og autoklavert ved 121 °C i 30 min.
De respective inokula ( Alternaria solani, ALTESO; Botrytis cinerea, BOTRCI; Leptosphaeria nodorum, LEPTNO; Fytoftora infestans, PHYTIN; Magnaporthe grisea f. sp. oryzae, PYRIOR; Pyrenophora teres, PYRNTE; Rhizoktonia solani, RHIZSO;) blir tilsatt i brønnene som sporesuspensjoner (50 ml; 5x10<5>/ml) eller agarskiver (6 mm) av en agarkultur av soppen.
Etter 6-12 dagers inkubering ved egnet temperaturer (18-25°C) blir MIC-verdier bestemt ved visuell inspeksjon av platene (Tabell II; n. t. = ikke testet).
<*> 5-Klor-6-(2-klorfenyl)-7-N-etylamino-1,2,4-triazolo[1,5a]pyrimidin har vært anvendt som standard; denne forbindelsen svarer til forbindelsen i eksempel 2, hvor 7-(2,2,2-trifluoretyl)aminogruppen har blitt erstattet med en vanlig 7-etylaminogruppe.
B. Bestemmelse av kontrollrester av drue-pulvermeldugg på vinrankeblader
Metode for evaluering av forbindelsene med formel I til å kontrollere pulvermeldugg på druer ( Uncinula necator)
Testplanter
Avskjæringer av Muller-Thurgau-kultur ble dyrket i veksthus ved temperaturer mellom 18 °C og 25 °C og 50 til 70 % relativ fuktighet. Når 6 til 8 blader hadde utviklet seg, ble plantene skåret tilbake til 3 - 4 like store blader. Planter ble dyrket i potter inneholdende FLORAGAD som et substrat.
Applikasjon
Tre til fire planter pr. behandling ble anvendt. Applikasjon av forbindelsene med formel I ble utført 3 dager før infeksjon i de profylaktiske tester. Testplantene ble sprøytet til avdrypping i et sprøytekabinett ved anvendelse av 20 ml sprøytevask. Forbindelsene med formel I ble oppløst i aceton i en konsentrasjon på 0,5 %. Stamløsningen ble fortynnet med vann, hvilket gir de endelige konsentrasjoner. Formulerte fungicider ble også fortynnet med vann før applikasjon.
Infeksjon
Plantene ble kunstig infisert med conidier av Uncinula necator ved å støve sporer fra friskt sporulerende drueblader fra Uncinula necator stamkulturen over testplantene. Sporene fikk sette seg på bladene i 1 time. Plantene forble i veksthuset uten ytterligere lys ved temperaturer mellom 16 °C og 30 °C i 24 timer.
Evaluering
Evaluering ble utført 21 dager etter infeksjon ved å bestemme prosentdelen av infisert bladflate av hver av de 4 behandlete blader. Aktiviteten i % ble beregnet ved anvendelse avABBOTT-formelen:
Resultatene av denne evaluering er vist i Tabell III:
C. Bladsystemisk virkning
C- 1: Drueart Muller-Thurgau
PATOGEN: Uncinula necator
TESTPROSEDYRE:
1. Druekutt dyrkes i 8 cm diameter plastpotter i veksthus.
2. Formulerte forbindelser blir påført et ungt fullt utbrettet blad i et band på tvers ved anvendelse av en luftbørste med en 0,5 mm sirkulær dyse ved et lufttrykk på 500 mbar. Bandet sprøytes på den nedre bladoverflate, loddrett på bladaksen ved anvendelse av en pappmaske med en 5-mm bred slisse. Plasseringen av bandet blir merket på den øvre bladoverflate ved anvendelse av en permanent markør og er typisk 4 cm fra bladspissen. Etter applikasjon
blir plantene ikke beveget inntil bandene er tørre.
3. Etter at de behandlete planter har tørket, blir de flyttet til veksthuset og holdt der i 2 dager for å muliggjøre bevegelse av forbindelsene. Plantene blir holdt
med bunnvanning.
4. To dager etter applikasjon blir drueplantene inokulert ved å støve dem med pulver-meldugg-conidier i veksthuset. Sporulerende syke blader fra stamkulturplanter blir børstet med en børste i luften over testplantene slik at conidiene kan sette seg på de øvre bladoverflater av testplantene. Evalueringer gjøres 12-14 dager etter inokulering.
C- 2 Hvete pulver-meldugg (WPM):
VERT: Hvete ( Triticum aestivum L.) sort Kanzler
PATOGEN: Ervsiphe graminis DC. f.sp. tritici E. Marchal
TESTPROSEDYRE:
1. Hvete frø (8/potte) plantes i 8 cm diameter plastpotter i veksthuset.
2. Når det primære blad er fullt utsprunget, skjæres plantene tilbake til fire i hver potte, hvilke merkes med en permanent markør 5 cm nedenfor bladtuppen på den øvre bladoverflate. Således er det to band-behandlete og to ubehandlete
planter i hver potte.
3. En pipette blir anvendt for å påføre 5 pl av formulert forbindelse i et band på den nedre bladoverflate motsatt merket. Applikasjonsbandet bør dekke hele bladbredden. Etter applikasjon blir plantene ikke beveget inntil bandne er
tørre (en halv time eller så senere).
4. Etter at behandlete planter har tørket, blir de flyttet til veksthuset og holdt der i 2 dager for å muliggjøre bevegelse av forbindelsene. Plantene blir holdt med
bunnvanning.
5. To dager etter applikasjon blir plantene inokulert ved å støve dem med pulver-meldugg-conidier i veksthuset. Evalueringer blir gjort 7 - 8 dager etter inokulering. Alternativt blir planter inokulert med Puccinia recondita (hveteblad-rustsopp-patogen) og evalueringer gjort 7-8 dager deretter.
Evaluering
Tre typer bevegelse av forbindelse blir bedømt ved evaluering av sykdom i tre områder av hvert band-behandlet blad.
Translaminar bevegelse: Prosent sykdomsflate blir bedømt for det translaminære band-området (merket område av den øvre bladoverflate direkte motsatt der hvor band ble påført den nedre bladoverflate; bandbredde omtrent 5 mm). Translaminær sykdomskontroll blir deretter beregnet ved anvendelse av den følgende formel:
Fjernbevegelse og nærbevegelse: De fjerntliggende og nærliggende sykdomsfrie soner på den øvre bladoverflate blir målt i mm. Den fjerne retning er fra bandet mot bladspissen og den nærliggende retning er fra bandet mot bladbunnen. Prosenten av den sykdomsfrie soner i forhold til hele avstanden mellom bandet og bladspissen eller -bunnen blir beregnet (for Drue 40 mm lik 100%). Hvis sykdommen er merkbart svakere i det fjernliggende eller nærliggende område, blir dette også bemerket.
FORMULERING OG KONTROLLER:
1. Forbindelsene blir formulert i et løsningsmiddel/overflateaktivt middel-system bestående av 5% aceton og 0,05% Tween 20 i ionefritt vann. Forbindelsene oppløses i aceton før fortynning med Tween vann. Formulerte forbindelser blir fremstilt ved anvendelse av ionefritt vann. Forbindelser blir typisk testet ved
400 ppm.
2. Tre typer kontroller blir inntatt:
Planter band-behandlet med oppløsningsmidlet/overflateaktivt middel-løsning og inokulert (Løsningsmiddel Blank).
Ubehandlete planter som er inokulert (Inokulert kontroll).
Resultatene av denne evaluering er vist i Tabell IV, hvor sykdommene har blitt forkortet som følger:
Hvete pulver-meldugg WPM
Drue pulver-meldugg GPM
Hvete bladrustsopp WLR
5-klor-7-(4-metylpiperidin-1 -yl)-6-(2-klor-6-fluorfenyl)-[1,2,4]triazolo[1,5-a]pyrimidin som er beskrevet i US patent no. 5,593,996 har vært anvendt som standard<2>.
Claims (8)
- Patentkrav: 1. Forbindelse karakterisert ved den generelle formel IhvorR<1> representerer et hydrogenatom eller en metylgruppe, ogR2 representerer et hydrogen atom eller en Ci-Ci0-alkylgruppe,Hal representerer et halogenatom, f.o.m. L1 t.o.m. L5 representerer hver uavhengig et hydrogen- eller halogenatom eller en metyl-, metoksky- eller nitrogruppe.
- 2. Forbindelse ifølge krav 1, karakterisert ved at minst én av L1 og L5 representerer et halogenatom.
- 3. Forbindelse i henhold til hvilken som helst av de foregående krav, kar akterisert ved at minst én av R1 og R2 representerer et hydrogenatom.
- 4. De følgende forbindelser karakterisert ved formell: 5-klor-6-(2-klor-6-fluorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-7-(2,2,2-trifluoretylamino)-6-(2,4,6-trifluorfenyl)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[2-(1,1,1 -trifluor)propylamino]- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[2-(1,1,1 -trifluor)propylamino]- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[2-(1,1,1 -trifluor)propylamino]- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-metylfenyl)-7-[2-(1,1,1-trifluor)propylaminoj- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluorfenyl)-7-[2-(1,1,1-trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-[2-(1,1,1-trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-allylamino]- [1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]- [1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylaminoj-[1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]-[1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2-klorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]- [1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-etylamino]- [1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)amino]-[1,2,4jtriazolo[1,5-ajpyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)am [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)-amino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)amin [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(2-metylpropyl)-amino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluofrenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-metylfenyl)-7-[N-(2,2,2-trifluoretyl)-N-metylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-isopropylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2I6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-isopropylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-isopropylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-isopropylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[N-(2,2,2-trifluoretyl)-N-(1-fenyletyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin S-klor-e^-fluorfenylH-IN.N-di^^^-trifluoretyOamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-metylfenyl)-7-[N,N-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-[NIN-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-ajpyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[N,N-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[N,N-di-(2,2,2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[N,N-di-(2,2)2-trifluoretyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[Nr(2,2,2-trifluoretyl)-N-(1,2-dimetylpropyl)am [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluorfenyl)-7-[Nr(2,2,2-trifluoretyl)-N-(trimetyls [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-brom-5-klorfenyl)-7-[2-(1,1,1 -trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(4-klorfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]py 5-klor-6-(4-bromfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrim 5-klor-6-(4-metoksyfenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]p 5-klor-6-(4-nitrofenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrim 5-klor-6-(2-fluorfenyl)-7-(1-fenyl-2,2,2-trifluoretylamino)- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klor-6-fluorfenyl)-7-[2-(1,1,1 -trifluor)butylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klor-6-fluofrenyl)-7-(1-fenyl-2,2,2-trifluoreytlamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-fluorfenyl)-7-[2-(1,1,1-trifluor)butylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-(1-fenyl-2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4,6-trifluofrenyl)-7-(1-fenyl-2,2,2-trifluore<y>tlamino)-[1,2,4]triazolo[1,5-a]pyrimidin S-klor-e^^.e-trifluorfenyO^-^l, 1,1 -trifluor)butylamino]- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluorfenyl)-7-[2-(1,1,1-trifluor)butylamino]- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-[2-(1,1,1-trifluor)butylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2-klorfenyl)-7-(1-fenyl-2,2,2-trifluoretylamino)- [1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,4-difluofrenyl)-7-(2,2,2-trifluoretylamino)-[1,2,4]triazolo[1,5-a]pyrim 5-klor-6-(2,4,6-trifluorfenyl)-7-[2-(1,1,1-trifluor)-3-metylbutylamino]-[1,2,4]triazolo[1,5-a]pyrimidin 5-klor-6-(2,6-difluor-4-metoksyfenyl)-7-[2-(1,1,1 -trifluor)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidin.
- 5. Fremgangsmåte for fremstilling av en forbindelse med formel I som definert i hvilken som helst av de foregående krav, karakterisert ved at den omfatter behandling av en forbindelse med den generelle formel IIhvor f.o.m. L1 t.o.m. L5 og Hal er som definert i hvilket som helst av de foregående krav;med et amin med den generelle formel IIIhvorR1 og R2 er som definert i hvilket som helst av de foregående krav,M representerer et hydrogenatom eller et fritt eller kompleksert metallatom, hvilket gir en forbindelse med formel I.
- 6. Fungicid preparat, karakterisert ved at det omfatter en bærer og som aktivt middel minst én forbindelse med formel I som definert i hvilket som helst av kravene 1 til 4.
- 7. Metode for bekjempelse av sopp på et voksested,karakterisert ved at den omfatter behandling av voksestedet med en forbindelse med formel I som definert i hvilket som helst av kravene 1 til 4 eller med et preparat som definert i krav 6.
- 8. Anvendelse som et fungicid av en forbindelse med formel I som definert i hvilket som helst av kravene 1 til 4 eller et preparat som definert i krav 6.
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US84332397A | 1997-04-14 | 1997-04-14 | |
PCT/US1998/005615 WO1998046608A1 (en) | 1997-04-14 | 1998-03-23 | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
US15057298A | 1998-09-10 | 1998-09-10 |
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US6559151B2 (en) | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
ATE313544T1 (de) * | 2000-06-13 | 2006-01-15 | Fungicide triazolopyrimid-7-ylidenamine | |
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EP1205540A1 (de) | 2000-11-10 | 2002-05-15 | Evotec OAI AG | Verfahren zur Vitalitätsmessung an Zellen |
WO2002038565A2 (de) * | 2000-11-13 | 2002-05-16 | Basf Aktiengesellschaft | 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen |
EP1341794B1 (en) * | 2000-12-06 | 2004-08-18 | Basf Aktiengesellschaft | Fungicidal 6-(trifluoromethyl-phenyl)-triazolopyrimidines |
NZ528745A (en) * | 2001-04-11 | 2005-03-24 | Basf Ag | 5-halogen-6-phenyl-7-fluoralkylamino-triazolopyrimidines as fungicides and their preparation process |
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DE10121162A1 (de) | 2001-04-30 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
KR100619216B1 (ko) | 2001-07-05 | 2006-09-08 | 바스프 악티엔게젤샤프트 | 살진균성 트리아졸로피리미딘, 이의 제조방법 및 유해진균 방제를 위한 이의 용도 및 상기 화합물을 포함하는조성물 |
JP2005504743A (ja) * | 2001-07-18 | 2005-02-17 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌薬としての置換された6−(2−メトキシ−フェニル)−トリアゾロピリミジン |
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DE3130633A1 (de) * | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
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