PL193553B1 - Pochodne benzamidoksymu, benzamidoksymy, zastosowanie pochodnych benzamidoksymu i środek grzybobójczy - Google Patents
Pochodne benzamidoksymu, benzamidoksymy, zastosowanie pochodnych benzamidoksymu i środek grzybobójczyInfo
- Publication number
- PL193553B1 PL193553B1 PL98339359A PL33935998A PL193553B1 PL 193553 B1 PL193553 B1 PL 193553B1 PL 98339359 A PL98339359 A PL 98339359A PL 33935998 A PL33935998 A PL 33935998A PL 193553 B1 PL193553 B1 PL 193553B1
- Authority
- PL
- Poland
- Prior art keywords
- alkyl
- alkoxy
- formula
- benzamidoxime
- halogen
- Prior art date
Links
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical class ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000000417 fungicide Substances 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 title claims description 45
- 238000000034 method Methods 0.000 title description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- -1 C 1 -C 4 -alkyl Chemical group 0.000 claims description 74
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 4
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 23
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- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 241001480061 Blumeria graminis Species 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 description 3
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- GVQDAEAMBDJZBG-UHFFFAOYSA-N n-[(cyclopropylmethoxyamino)-[2-(difluoromethoxy)-6-fluorophenyl]methylidene]-2-phenylacetamide Chemical compound FC(F)OC1=CC=CC(F)=C1C(NC(=O)CC=1C=CC=CC=1)=NOCC1CC1 GVQDAEAMBDJZBG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OYRIKLVYHTWHCZ-UHFFFAOYSA-N n-cyclohexyl-2,5-dimethylfuran-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC2CCCCC2)=C1C OYRIKLVYHTWHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- QXJKBPAVAHBARF-UHFFFAOYSA-N procymidone Chemical compound O=C1C2(C)CC2(C)C(=O)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-UHFFFAOYSA-N 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- DZYKTVYTGJWVOU-UHFFFAOYSA-M sodium;1,3-bis(2-methylpropyl)naphthalene-2-sulfonate Chemical compound [Na+].C1=CC=C2C(CC(C)C)=C(S([O-])(=O)=O)C(CC(C)C)=CC2=C1 DZYKTVYTGJWVOU-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-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 class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A—HUMAN NECESSITIES
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- 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
- A01N37/52—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 groups, e.g. carboxylic acid amidines
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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- 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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C259/12—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 with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—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 with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
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Abstract
1. Pochodne benzamidoksymu o ogólnym wzorze I w którym R 1 oznacza difluorometyl lub trifluorometyl; R 2 oznacza atom wodoru lub atom fluoru; R 3 oznacza C 1 -C 4 -alkil ewentualnie podstawiony grup a cyjanow a, C 1 -C 4 -chlorowcoalkil, C 1 -C 4 -alkoksy-C 1 -C 4 - -alkil, C 3 -C 6 -alkenyl, C 3 -C 6 -chlorowcoalkenyl, C 3 -C 6 -alkinyl lub C 3 -C 8 -cykloalkilo-C 1 -C 4 -alkil; R 4 oznacza fenylo-C 1 -C 6 -alkil ewentualnie podstawiony w pier scieniu fenylowym jednym lub wi eksz a liczb a podstawników wybranych z grupy obejmuj acej atom chlorowca, C 1 -C 4 -alkil, C 1 -C 4 -chlorowcoalkil, C 1 -C 4 - -alkoksyl i C 1 -C 4 -chlorowcoalkoksyl, albo tienylo-C 1 -C 4 -alkil ewentualnie podstawiony w pier scieniu tienylowym jednym lub wi eksza liczb a podstawników wybranych z grupy obejmuj acej atom chlorowca, C 1 -C 4 -alkil, C 1 -C 4 - -chlorowcoalkil, C 1 -C 4 -alkoksyl i C 1 -C 4 -chlorowcoalkoksyl, albo pirazolo-C 1 -C 4 -alkil ewentualnie podstawiony w pier scieniu pirazolowym jednym lub wi eksza liczb a podstawników wybranych z grupy obejmuj acej atom chlo- rowca, C 1 -C 4 -alkil, C 1 -C 4 -chlorowcoalkil, C 1 -C 4 -alkoksyl i C 1 -C 4 -chlorowcoalkoksyl. PL PL PL
Description
Opis wynalazku
Przedmiotem wynalazku są pochodne benzamidoksymu, benzamidoksymy, zastosowanie pochodnych benzamidoksymu i środek grzybobójczy.
Pochodne benzamidoksymu o działaniu grzybobójczym opisano w JP-A 02/006453, jednak nie były one w pełni zadawalające, szczególnie przy niskich dawkach nanoszenia.
Istniało zatem zapotrzebowanie na nowe pochodne benzamidoksymu o polepszonym działaniu, szczególnie nawet przy niskich dawkach nanoszenia.
Nieoczekiwanie stwierdzono, że takie pożądane działanie wykazują związki zdefiniowane poniżej. Wynalazek dotyczy pochodnych benzamidoksymu o ogólnym wzorze I
w którym 1
R oznacza difluorometyl lub trifluorometyl;
2
R oznacza atom wodoru lub atom fluoru;
3
R oznacza C1-C4-alkil ewentualnie podstawiony grupą cyjanową, C1-C4-chlorowcoalkil, C1-C4-alkoksy-C1-C4-alkil, C3-C6-alkenyl, C3-C6-chlorowcoalkenyl, C3-C6-alkinyl lub C3-C8-cykloalkilo-C1-C4-alkil;
R4 oznacza fenylo-C1-C6-alkil ewentualnie podstawiony w pierścieniu fenylowym jednym lub większą liczbą podstawników wybranych z grupy obejmującej atom chlorowca, C1-C4-alkil, C1-C4-chlorowcoalkil, C1-C4-alkoksyl i C1-C4-chlorowcoalkoksyl, albo tienylo-C1-C4-alkil ewentualnie podstawiony w pierścieniu tienylowym jednym lub większą liczbą podstawników wybranych z grupy obejmującej atom chlorowca, C1-C4-alkil, C1-C4-chlorowcoalkil, C1-C4-alkoksyl i C1-C4-chlorowcoalkoksyl, albo pirazolo-C1-C4-alkil ewentualnie podstawiony w pierścieniu pirazolowym jednym lub większą liczbą podstawników wybranych z grupy obejmującej atom chlorowca, C1-C4-alkil, C1-C4-chlorowcoalkil, C1-C4-alkoksyl i C1-C4-chlorowcoalkoksyl.
Korzystne są związki o wzorze I, w którym R4 oznacza benzyl ewentualnie podstawiony w pierścieniu fenylowym 1-3 podstawnikami wybranymi z grupy obejmującej atom chlorowca, C1-C4-alkil i C1-C4-alkoksyl.
1
Korzystne są związki o wzorze I, w którym R oznacza difluorometyl.
2
Korzystne są związki o wzorze I, w którym R oznacza atom fluoru w pozycji 5 pierścienia fenylowego.
Wynalazek dotyczy również benzamidoksymów o ogólnym wzorze V
w którym R i R mają wyżej podane znaczenie.
Korzystne są związki o wzorze I, w którym R2 oznacza atom fluoru w pozycji 5 pierścienia fenylowego.
Wynalazek dotyczy również benzamidoksymów o ogólnym wzorze VI
PL 193 553 B1
2 3 w którym R , R i R mają wyżej podane znaczenie.
Korzystne są związki o wzorze (VI), w którym R2 oznacza atom fluoru w pozycji 5 fenylu.
Wynalazek dotyczy także zastosowania pochodnych benzamidoksymu o wzorze I zdefiniowanych powyżej do zwalczania szkodliwych grzybów.
Wynalazek dotyczy ponadto środka grzybobójczego zawierającego substancję czynną, nośnik i/lub substancje pomocnicze, przy czym cechą tego środka jest to, że jako substancję czynną zawiera co najmniej jedną pochodną benzamidoksymu o wzorze I zdefiniowaną powyżej w grzybobójczo skutecznej ilości.
Atom chlorowca oznacza atom fluoru, bromu, chloru lub jodu, a zwłaszcza atom fluoru lub chloru.
Inne określenia mają niżej podane przykładowe znaczenia.
- C1-C4-alkil oznacza metyl, etyl, n-propyl, 1-metyloetyl, n-butyl, 1-metylopropyl, 2-metylopropyl lub 1,1-dimetyloetyl, a zwłaszcza etyl;
- C1-C4-chlorowcoalkil oznacza podany powyżej C1-C4-alkil częściowo lub całkowicie podstawiony podstawnikami z grupy obejmującej atom fluoru, atom chloru, atom bromu i/lub atom jodu, np. trichlorometyl, trifluorometyl, 2-fluoroetyl, 2-chloroetyl, 2-bromoetyl, 2,2-difluoroetyl, 2,2,2-trifluoroetyl, 2,2,2-trichloroetyl, 2-fluoropropyl, 3-fluoropropyl, 2-chloropropyl lub 3-chloropropyl, zwłaszcza 2-fluoroetyl lub 2-chloroetyl;
- cyjano-C1-C4-alkil oznacza np. cyjanometyl, 1-cyjanoet-1-yl, 2-cyjanoet-1-yl, 1-cyjanoprop-1-yl, 2-cyjanoprop-1-yl, 3-cyjanoprop-1-yl, 1-cyjanoprop-2-yl lub 2-cyjanoprop-2-yl, szczególnie cyjanometyl lub 2-cyjanoetyl;
- C1-C4-alkoksyl oznacza metoksyl, etoksyl, n-propoksyl, 1-metyloetoksyl, n-butoksyl, 1-metylopropoksyl, 2-metylopropoksyl lub 1,1-dimetyloetoksyl, zwłaszcza metoksyl lub etoksyl;
- C1-C4-alkoksy-C1-C4-alkil oznacza C1-C4-alkil podstawiony wyżej podanym C1-C4-alkoksylem, a więc np. metoksymetyl, etoksymetyl, n-propoksymetyl, (1-metyloetoksy)metyl, n-butoksymetyl, (1-metylopropoksy)metyl, (2-metylopropoksy)metyl, (1,1-dimetyloetoksy)metyl, 2-(metoksy)etyl lub 2-(etoksy)etyl, a zwłaszcza metoksymetyl lub 2-metoksyetyl;
- C3-C6-alkenyl oznacza np. prop-2-en-1-yl, n-buten-4-yl, 1-metyloprop-2-en-1-yl, 2-metyloprop-2-en-1-yl lub 2-buten-1-yl, a zwłaszcza prop-2-en-1-yl;
- C3-C6-chlorowcoalkenyl oznacza podany powyżej C3-C6-alkenyl podstawiony częściowo lub całkowicie podstawnikami z grupy obejmującej atom fluoru, atom chloru i/lub atom bromu, np. 2-chloroallil, 3-chloroallil, 2, 3-dichloroallil lub 3,3-dichloroallil, a zwłaszcza 2-chloroallil;
- C3-C6-alkinyl oznacza np. prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl lub n-but-2-yn-1-yl, a zwłaszcza prop-2-yn-1-yl;
- C3-C8-cykloalkilo-C1-C4-alkil oznacza np. cyklopropylometyl, cyklobutylometyl, cyklopentylometyl, cykloheksylometyl, (cyklopropylo)etyl, 1-(cyklobutylo)etyl, 1-(cyklopentylo)etyl, 1-(cykloheksylo)etyl, 1-(cykloheptylo)etyl, 1-(cyklooktylo)etyl, 2-(cyklopropylo)etyl lub 2-(cyklobutylo)etyl, szczególnie cyklo-pentylometyl;
- fenylo-C1-C6-alkil oznacza np. benzyl, 1-fenyloetyl, 2-fenyloetyl, 1-fenyloprop-1-yl, 2-fenyloprop-1-yl, 3-fenylo-prop-1-yl, a zwłaszcza benzyl lub 2-fenyloetyl;
- tienylo-C1-C4-alkil oznacza np. 2-tienylometyl, 3-tienylometyl lub 2-tienyloetyl;
- pirazolo-C1-C4-alkil oznacza np. 1-pirazolilometyl, 2-pirazolilometyl, 3-pirazolilometyl lub 2-pirazoliloetyl.
1
Szczególnie skuteczne okazały się związki, w których podstawnik R oznacza difluorometyl, podstawnik R3 oznacza cyklopropylometyl, a podstawnik R4 oznacza benzyl, który w pierścieniu fenylowym jest podstawiony jednym do trzech podstawników wybranych z wyżej wymienionych grup, szczególnie jednym do trzech podstawników wybranych z grupy obejmującej atom fluoru, atom chloru, metyl, metoksyl i trifluorometyl.
Szczególnie korzystne są związki o wzorze I, w których R1 - R4 mają znaczenie podane w tabeli 1.
PL 193 553 B1
T a b e l a 1
| Nr | R1 | R2 | R3 | R4 | T.t. [°C] |
| I.1 | CHF2 | H | C2H5 | C6H5-CH2 | olej |
| I.2 | CHF2 | H | C2H5 | 4-CH3O-C6H4-CH2 | olej |
| I.3 | CHF2 | H | CH2-CH=CH2 | C6H5-CH2 | olej |
| I.4 | CHF2 | H | CH2-CECH | C6H5-CH2 | olej |
| I.5 | CHF2 | H | CH2-CECH | 4-CH3O-C6H4-CH2 | olej |
| I.6 | CHF2 | H | cPr | C6H5-CH2 | * |
| I.7 | CHF2 | H | cPr | 4-F-C6H4-CH2 | 75-77 |
| I.8 | CHF2 | H | cPr | 4-CFC6H4-CH2 | 81-83 |
| I.9 | CHF2 | H | cPr | 4-CH3O-C6H4-CH2 | 57-59 |
| I.10 | CHF2 | H | cPr | 2-tienylometyl | olej |
| I.11 | CHF2 | H | cPr | 3-tienylometyl | olej |
| I.12 | CHF2 | 5-F | cPr | C6H5-CH2 | 62-65 |
| I.13 | CHF2 | 5-F | cPr | 4-F-C6H4-CH2 | 64-67 |
| I.14 | CHF2 | 5-F | cPr | 4-CFC6H4-CH2 | 72-75 |
| I.15 | CHF2 | 5-F | cPr | 4-CH3-C6H4-CH2 | 74-76 |
| I.16 | CHF2 | 5-F | cPr | 4-CH3O-C6H4-CH2 | 79-81 |
| I.17 | CHF2 | H | cPr | 4-CH3-C6H4-CH2 | 69-71 |
| I.18 | CHF2 | H | CH2-CECH | 4-F-C6H4-CH2 | 74-76 |
| I.19 | CHF2 | H | C2H5 | 4-F-C6H4-CH2 | olej |
| I.20 | CHF2 | H | CH2-CH=CH2 | 4-F-C6H4-CH2 | olej |
| I.21 | CHF2 | H | CH2-CH=CH2 | 4-CH3O-C6H4-CH2 | olej |
| I.22 | CHF2 | H | CH2-CH(CH3)2 | C6H5-CH2 | 65-67 |
| I.23 | CHF2 | H | CH2-C(CH3)=CH2 | C6H5-CH2 | olej |
* Związek I.6 przebadano w teście opisanym w przykł adzie 12. W powyższej tabeli cPr oznacza cyklopropylometyl.
Pochodne benzamidoksymu o wzorze I wytwarza się poprzez rozszczepienie eterowe fluorowanych benzonitryli o wzorze II, a następnie drogą reakcji otrzymanych benzonitryli III z chlorowcoalkanami CHmFnchlorowiec (m oznacza 0 lub 1, n oznacza 2 lub 3), takich jak CHF2Cl lub CF3I, w środowisku
PL 193 553 B1 alkalicznym (korzystnie w obecności wodorotlenku metalu alkalicznego) prowadzącej do otrzymania benzonitryli IV, po czym drogą reakcji z hydroksyloaminą lub jej solami w roztworze wodnym, korzystnie w wodzie lub w mieszaninie woda/alkanol, ewentualnie w obecności zasady z wytworzeniem benzamidoksymów o wzorze V, które następnie znanym sposobem poddaje się alkilowaniu z wytworzeniem substancji wyjściowych o wzorze VI.
Benzamidoksymy VI można następnie znanym sposobem acylować z użyciem odpowiednich halogenków kwasowych, korzystnie z użyciem odpowiednich chlorków kwasowych przez ogrzewanie w obojętnych rozpuszczalnikach (korzystnie w temperaturze 20 - 100°C).
Szczególnie odpowiednimi obojętnymi rozpuszczalnikami są węglowodory lub etery, a szczególnie korzystne są węglowodory aromatyczne, takie, aby wymienić tylko dwa przykłady, jak toluen lub ksylen.
Na powyższym schemacie R1 oznacza grupę CHmFn, w której m oznacza 0 lub 1, a n oznacza 2 lub 3.
2
Związki pośrednie o wzorze III, w którym R oznacza atom fluoru i związki pośrednie o wzorach IV, V i VI podane na powyższym schemacie reakcji, są nowymi związkami.
Wymienione nowe związki pośrednie zawierające 2 atomy fluoru jako podstawniki wytwarza się z użyciem 2,3-difluoro-6-metoksybenzaldehydu (który może być wytworzony np. sposobem z przykładu 27 w WO 97/03071) jako związku wyjściowego, zgodnie z opisanymi w przykładzie 2 wariantami, do etapu wytworzenia związków o wzorze IV. Następne etapy wytwarzania odpowiednich związków o wzorach V i VI są znane fachowcowi.
Korzystnymi związkami o wzorach IV, V i VI są te, w których R i R (związki VI) mają znaczenie podane powyżej dla związków o wzorze I.
1
Korzystnymi związkami o wzorze IV są związki podane w tabeli 2 (R oznacza CHmFn) oraz związki, w których R2 oznacza 4-F, m = 1, n = 2, albo R2 oznacza H, m = 0, n = 3, albo R2 oznacza 5-F, m = 0, n = 3.
PL 193 553 B1
T a b e l a 2
| Nr | R2 | m | n | NMR (CDCis) ppm |
| IV.1 | H | 1 | 2 | 6,7 t (1H); 7,05-7,2 m (2H); 7,55-7,7 m (1H) |
| IV.2 | 5-F | 1 | 2 | 6,65 t (1H); 7,05-7,2 m (1H); 7,4-7,5 m (1H) |
2
Korzystnymi związkami o wzorze V są związki podane w tabeli 3 oraz związki, w których R oznacza 4-F, m = 1, n = 2, albo R2 oznacza H, m = 0, n = 3, albo R2 oznacza 5-F, m = 0, n = 3.
T a b e l a 3
| Nr | R2 | m | n | NMR (CDCl3) ppm |
| V.1 | H | 1 | 2 | 5,9 s (2H); 7,0-7,2 m (2H); 7,15 t (1H); 7,4-7,55 m (1H) |
| V.2 | 5-F | 1 | 2 | 4,9 s (2H); 6,5 t (1H); 6,95-7,05 m (1H); 7,15-7,3 m (1H); 8,0 s (1H) |
Szczególnie korzystne związki o wzorze VI podano w tabeli 4. Korzystne są również związki, w których R2 oznacza H, R3 oznacza C2H5, CH2-CH=CH2 lub CH2-ChCH, m = 1, n = 2, albo R2 oznacza H, R3 oznacza CH2-ChCH lub c-Pr, m = 0, n = 3, albo R2 oznacza 5-F, R3 oznacza C2H5, CH2-CH=CH2, CH2-ChCH lub c-Pr, m = 1, n = 2.
T a b e l a 4
| Nr | R2 | R3 | m | n | NMR (CDCl3) ppm |
| VI.1 | H | c-Pr | 1 | 2 | 0,3 m (2H); 0,55 m (2H); 1,2 m (2H); 3,9 d (2H); 4,85 s,brd (2H); 6,6 t (1H); 6,85-7,1 m (2H); 7,35-7,45 m (1H) |
| VI.2 | 5-F | c-Pr | 1 | 2 | 0,3 m (2H); 0,55 m (2H); 1,2 m (1H); 3,85 d (2H); 4,9 s,brd (2H); 6,55 t (1H); 7,0-7,1 m (1H); 7,15-7,2 m (1H) |
Związki o wzorze I odznaczają się doskonałą skutecznością przeciw szerokiemu spektrum fitopatogennych grzybów, szczególnie z klasy Ascomycetes, Deuteromycetes, Phycomycetes i Basidiomycetes. Niektóre z nich działają układowo i można je stosować jako środki grzybobójcze w zabiegach na liście i glebę.
Zazwyczaj rośliny opryskuje się lub opyla substancjami czynnymi lub traktuje się substancjami czynnymi nasiona tych roślin.
Formy użytkowe wytwarza się znanymi sposobami np. przez rozprowadzanie substancji czynnej w rozpuszczalnikach i/lub nośnikach, w razie potrzeby z użyciem emulgatorów i dyspergatorów, przy czym w przypadku użycia wody jako rozpuszczalnika można także stosować wraz z nią inne rozpuszczalniki organiczne jako rozpuszczalniki pomocnicze. Jako substancje pomocnicze stosuje się głównie: rozpuszczalniki, takie jak związki aromatyczne (np. ksylen), chlorowane związki aromatyczne (np. chlorobenzeny), parafiny (np. frakcje ropy naftowej), alkohole (np. metanol, butanol), ketony (np. cykloheksanon), aminy (np. etanoloamina, dimetyloformamid) i wodę; nośniki, takie jak mielone minerały naturalne (np. kaoliny, iły, talk, kredę) i mielone minerały syntetyczne (np. wysoko zdyspergowaną krzemionkę, krzemiany); emulgatory, takie jak emulgatory niejonowe i anionowe (np. etery polioksyetylenowe alkoholi tłuszczowych, alkilosulfoniany i arylosulfoniany) i dyspergatory, takie jak ligninowe ługi posiarczynowe i metylocelulozę.
Odpowiednimi substancjami powierzchniowo czynnymi są sole metali alkalicznych, sole metali ziem alkalicznych i sole amonowe aromatycznych kwasów sulfonowych np. kwasu lignino-sulfonowego, kwasu fenolosulfonowego, kwasu naftalenosulfonowego i kwasu dibutylonaftalenosulfonowego, jak również kwasów tłuszczowych, alkilosulfonianów i alkiloarylosulfonianów, alkilosiarczanów, lauryloeteroPL 193 553 B1 siarczanów i siarczanów alkoholi tłuszczowych, jak również sole siarczanowanych heksa-, heptai oktadekanoli lub eterów glikoli i alkoholi tłuszczowych, produkty kondensacji sulfonowanego naftalenu i jego pochodnych z formaldehydem, produkty kondensacji naftalenu lub kwasów naftalenosulfonowych z fenolem i formaldehydem, etery glikolu polioksyetylenowego i oktylofenolu, oksyetylenowany izooktylofenol, oktylofenol lub nonylofenol, etery alkilofenylowe poliglikoli, eter tributylofenylowy poliglikolu, alkiloarylopolieteroalkohole, alkohol izotridecylowy, produkty kondensacji alkoholi tłuszczowych i tlenku etylenu, oksyetylenowany olej rycynowy, etery alkilowe polioksyetylenu lub polioksypropylenu, octan eteru poliglikolu i alkoholu laurylowego, estry sorbitolu, ligninowe ługi posiarczynowe i metyloceluloza.
Proszki, środki do rozsiewania i pyły można wytwarzać przez zmieszanie lub wspólne zmielenie substancji czynnych ze stałym nośnikiem.
Granulaty, np. granulaty powlekane, impregnowane lub jednorodne, można wytwarzać przez związanie substancji czynnych ze stałymi nośnikami. Stałymi nośnikami są np. minerały, takie jak żel krzemionkowy, krzemionki, żele krzemionkowe, krzemiany, talk, kaolin, wapień, wapno, kreda, glinka bolus, less, glina, dolomit, ziemia okrzemkowa, siarczan wapnia, siarczan magnezu, tlenek magnezu, zmielone materiały syntetyczne, nawozy, takie jak siarczan amonu, fosforan amonu, saletra amonowa, moczniki i produkty pochodzenia roślinnego, takie jak mąka zbożowa, mączka z kory drzew, mączka drzewna, mączka ze zmielonych skorup orzechów, sproszkowana celuloza i inne stałe nośniki.
Nowe związki odznaczają się doskonałą skutecznością przeciw szerokiemu spektrum fitopatogennych grzybów, szczególnie z klasy Deuteromycetes, Ascomycetes, Phycomycetes i Basidiomycetes. Niektóre z nich działają układowo i można je stosować jako środki grzybobójcze w zabiegach na liście i glebę.
Związki te mają szczególne znaczenie w zwalczaniu różnorodnych grzybów na wielu różnych roślinach uprawnych, takich jak pszenica, żyto, jęczmień, owies, ryż, kukurydza, darń, bawełna, soja, kawa, trzcina cukrowa, winorośl, owoce południowe i rośliny ozdobne, warzywa, takie jak ogórki, fasole i kabaczki jak również na nasionach tych roślin.
Związki te stosuje się działając na grzyby lub chronione przed atakiem grzybów ziarno, rośliny, materiały lub glebę grzybobójczą skuteczną ilością substancji czynnych.
Nanoszenie można prowadzić przed zarażeniem lub po zarażeniu szkodliwymi grzybami materiałów, roślin lub nasion.
Nowe związki szczególnie nadają się do zwalczania następujących fitopatogennych grzybów:
Erysiphe graminis (mączniak prawdziwy) na zbożach, Erysiphe cichoracearum i Sphaerotheca fuliginea na dyniach, Podosphaera leucotricha na jabłoniach, Uncinula necator na winorośli, gatunków Puccinia na zbożach, gatunków Rhizoctonia na bawełnie i na darni, gatunków Ustilago na zbożach i trzcinie cukrowej, Venturia inaequalis (parch) na jabłoniach, gatunków Helminthosporium na zbożach, Septoria nodorum na pszenicy, Botrytis cinerea (szara pleśń) na truskawkach, winorośli, roślinach ozdobnych i warzywach, Cercospora arachidicola na orzeszkach ziemnych, Pseudocercosporella herpotrichoides na pszenicy i jęczmieniu, Pyricularia oryzae na ryżu, Phytophthora infestans na ziemniakach i pomidorach, gatunków Fusarium i Verticillium na różnych roślinach, Plasmopara viticola na winorośli i gatunków Alternaria na warzywach i drzewach owocowych.
Nowe związki nadają się także do ochrony materiałów (ochrony drewna), np. przeciw Paeciomyces variotii.
Środki grzybobójcze zawierają na ogół 0,1 - 95% wagowych, korzystnie 0,5 - 90% wagowych substancji czynnej.
W zależności od założonego efektu, dawki nanoszenia substancji czynnej wynoszą 0,025 - 2 kg/ha, korzystnie 0,1-1 kg/ha.
W przypadku traktowania nasion stosuje się zazwyczaj substancję czynną w ilości 0,001 - 50 g/kg nasion, korzystnie 0,01 - 10 g/kg nasion.
W postaciach użytkowych środków grzybobójczych związki według wynalazku mogą być obecne także z innymi substancjami czynnymi np. z herbicydami, insektycydami, regulatorami wzrostu roślin, fungicydami, a także z nawozami sztucznymi.
Mieszaniny z fungicydami w wielu przypadkach umożliwiają uzyskanie szerszego spektrum działania grzybobójczego.
Poniższa lista fungicydów, z którymi można stosować związki według wynalazku, stanowi jedynie ilustrację możliwych połączeń i nie narzuca żadnych ograniczeń:
siarka, ditiokarbaminiany i ich pochodne, takie jak dimetyloditiokarbaminian żelaza(III), dimetyloditiokarbaminian cynku, etylenobisditiokarbaminian cynku, etylenobisditiokarbaminian manganu,
PL 193 553 B1 etylenodiaminobisditiokarbaminian manganowo-cynkowy, disiarczki tetrametylotiuramu, kompleks amoniaku i N,N-etylenobisditiokarbaminianu cynku, kompleks amoniaku i N,N'-propylenobisditiokarbaminianu cynku, N,N'-propylenobisditiokarbaminian cynku, disiarczek N,N'-polipropylenobis(tiokarbamoilu);
nitropochodne, takie jak krotonian dinitro(1-metyloheptylo)fenylu, 3,3-dimetyloakrylan 2-sec-butylo-4,6-dinitrofenylu, węglan 2-sec-butylo-4,6-dinitrofenyloizopropylowy, 5-nitroizoftalan diizopropylu;
związki heterocykliczne, takie jak octan 2-heptadecylo-2-imidazoliny, 2,4-dichloro-6-(o-chloroanilino)-s-triazyna, ftalimidofosfonotionian O,O-dietylu, 5-amino-1-[bis(dimetyloamino)fosfinylo]-3-fenylo-1,2,4-triazol, 2,3-dicyjano-1,4-ditioantrachinon, 2-tio-1,3-ditiolo[4,5-b]chinoksalina, 1-(butylokarbamoilo)-2-benzimidazolokarbaminian metylu, 2-metoksykarbonyloaminobenzimidazol, 2-(2-furylo)benzimidazol, 2-(4-tiazolilo)benzimidazol, N-(1,1,2,2-tetrachloroetylotio)tetrahydroftalimid, N-trichlorometylotiotetrahydroftalimid, N-trichlorometylotioftalimid;
N-dichlorofluorometylotio-N',N'-dimetylo-N-fenylosulfonoamid, 5-etoksy-3-trichlorometylo-1,2,3-tiadiazol, 2-tiocyjanatometylotiobenzotiazol, 1,4-dichloro-2,5-dimetoksybenzen, 4-(2-chlorofenylohydrazono)-3-metylo-5-izoksazolon, 1-tlenek pirydyno-2-tiolu, 8-hydroksychinolina lub jej sól z miedzią, 2,3-dihydro-5-karboksyanilido-6-metylo-1,4-oksatyna, 4,4-ditlenek 2,3-dihydro-5-karboksyanilido-6-metylo-1,4-oksatyny, 2-metylo-5,6-dihydro-4H-pirano-3-karboksyanilid, 2-metylofurano-3-karboksyanilid, 2,5-dimetylofurano-3-karboksyanilid, 2,4,5-trimetylofurano-3-karboksyanilid, N-cykloheksylo-2,5-dimetylofurano-3-karboksyamid, N-cykloheksylo-N-metoksy-2,5-dimetylofurano-3-karboksyamid, 2-metylobenzanilid, 2-jodobenzanilid, acetal 2,2,2-trichloroetylowy N-formylo-N-morfoliny, piperazyno-1,4-diylobis-1-(2,2,2-trichloroetylo)formamid, 1-(3,4-dichloroanilino)-1-formyloamino-2,2,2-trichloroetan;
2,6-dimetylo-N-tridecylomorfolina lub jej sole, 2,6-dimetylo-N-cyklododecylomorfolina lub jej sole, N-[3-(p-tert-butylofenylo)-2-metylopropylo]-cis-2,6-dimetylomorfolina, N-[3-(p-tert-butylofenylo)-2-metylopropylo]piperydyna, 1-[2-(2,4-di-chlorofenylo)-4-etylo-1,3-dioksolan-2-yloetylo]-1H-1,2,4-triazol, 1-[2-(2,4-dichlorofenylo)-4-n-propylo-1,3-dioksolan-2-yloetylo]-1H-1,2,4-triazol, N-(n-propylo)-N-(2,4, 6-trichlorofenoksyetylo)-N'-imidazolilomocznik, 1-(4-chlorofenoksy)-3,3-dimetylo-1 -(1 H-1,2,4-triazol-1 -ilo)-2-butanon, (2-chlorofenylo)-(4-chlorofenylo)-5-pirymidynometanol, 5-butylo-2-dimetyloamino-4-hydroksy-6-metylopirymidyna, bis(p-chlorofenylo)-3-pirydynometanol, 1,2-bis(3-etoksykarbonylo-2-tioureido) benzen, 1,2-bis(3-metoksykarbonylo-2-tioureido)benzen, [2-(4-chlorofenylo)etylo]-(1,1-dimetyloetylo)-1H-1,2,4-triazolo-1-etanol, 1-[3-(2-chlorofenylo)-1-(4-fluorofenylo)oksiran-2-ylometylo]-1H-1,2,4-triazol; jak również różne fungicydy, takie jak octan dodecyloguanidyny, 3-[3-(3,5-dimetylo-2-oksycykloheksylo)-2-hydroksyetylo]glutaroimid, heksachlorobenzen, N-(2,6-dimetylofenylo)-N-(2-furo-ilo)-DL-alaninian metylu, DL-N-(2,6-dimetylofenylo)-N-(2'-metoksyacetylo)alanian metylu, N-(2,6-dimetylofenylo)-N-chloroacetylo-D,L-2-aminobutyrolakton, DL-N-(2,6-dimetylofenylo)-N-(fenyloacetylo)alanian metylu, 5-metylo-5-winylo-3-(3,5-di-chlorofenylo)-2,4-diokso-1,3-oksazolidyna, 3-(3,5-dichlorofenylo)-5-metylo-5-metoksymetylo-1,3-oksazolidyno-2,4-dion, 3-(3,5-dichlorofenylo)-1-izopropylokarbamoilohydantoina, N-(3,5-dichlorofenylo)-1,2-dimetylocyklopropano-1,2-dikarboksyimid, 2-cyjano-[N-(etyloaminokarbonylo)-2-metoksyimino]acetamid, 1-[2-(2,4-dichlorofenylo)pentylo]-1H-1,2,4-triazol, alkohol 2,4-difluoro-a-(1H-1,2,4-triazolilo-1-metylo)benzhydrylowy, N-(3-chloro-2,6-dinitro-4-trifluorometylofenylo)-5-trifluorometylo-3-chloro-2-aminopirydyna, 1 -((bis(4-fluorofenylo)metylosililo)metylo)-1 H-1,2,4-triazol, strobiluryny, takie jak E-metoksyimino-[a-(o-toliloksy)-o-tolilo]octan metylu, E-2-{2-[6-(2-cyjanofenoksy)pirydymin-4-yloksy]fenylo}-3-metoksyakrylan metylu, N-metylo-E-metoksyimino-[a-(2,5-dimetyloksy)-o-tolilo]acetamid;
anilinopirymidyny, takie jak N-(4,6-dimetylopirymidyn-2-ylo)anilina, N-[4-metylo-6-(1-propynylo) pirymidyn-2-ylo]anilina, N-(4-metylo-6-cyklopropylopirymidyn-2-ylo)anilina;
fenylopirole, takie jak 4-(2,2-difluoro-1,3-benzodioksol-4-ilo)pirolo-3-karbonitryl;
amidy kwasu cynamonowego, takie jak 3-(4-chlorofenylo)-3-(3,4-dimetoksyfenylo)akryloilomorfolina.
Wynalazek ilustrują poniższe przykłady.
P r z y k ł a d 1
a) 6-Fluoro-2-hydroksybenzonitryl
Porcję 7,8 g 2-metoksy-6-fluorobenzonitrylu i 18,0 g chlorowowodorku pirydyny ogrzewano w atmosferze suchego azotu przez 5 godzin w temperaturze 195°C. Po ochłodzeniu mieszaninę rozdzielono pomiędzy 50 ml wody i 50 ml eteru metylowo-tert-butylowego i fazę organiczną wyekstrahowano
PL 193 553 B1 ml 2N NaOH. Odczyn ekstraktu alkalicznego doprowadzono do pH 5 i następnie ekstrakt dwukrotnie wyekstrahowano porcjami 40 ml eteru metylowo-tert-butylowego. Po odparowaniu rozpuszczalnika otrzymano 4,7 g żądanego produktu w postaci oleju (HPLC: 93%).
NMR(DMSO) ppm: 6,8-6,95 m (2H); 7,5-7,6 m (1H); 11,8 s,br (1H).
b) 2-Difluorometoksy-6-fluorobenzonitryl
Do mieszaniny 10,0 g 2-hydroksy-6-fluorobenzonitrylu, 50 ml 1,2-dimetoksyetanu i 25 ml NaOH (33%) w trakcie mieszania w temperaturze 75°C wprowadzono 6,3 g gazowego chlorodifluorometanu (chłodnicę zwrotną chłodzono suchym lodem) i mieszanie kontynuowano przez 1 godzinę w temperaturze 70 - 75°C. Po ochłodzeniu mieszaninę rozcieńczono 300 ml wody i trzykrotnie wyekstrahowano porcjami 150 ml eteru metylowo-tert-butylowego. Po odparowaniu rozpuszczalnika otrzymano 6,5 g żądanego produktu w postaci oleju.
NMR(CDCl3) ppm: 6,7 t (1H); 7,05-7,20 m (2H); 7,55-7,70 m (1H).
c) 2-Difluorometoksy-6-fluorobenzamidoksym
Mieszaninę 6,4 g 2-difluorometoksy-6-fluorobenzonitrylu i 3,1 g chlorowodorku hydroksyloaminy, 2,6 g węglanu sodu, 7 ml wody i 35 ml etanolu mieszano przez 20 godzin w temperaturze 75°C. Po odparowaniu rozpuszczalnika pozostałość rozdzielono pomiędzy 40 ml 2N HCl i 20 ml octanu etylu. Po oddzieleniu fazy HCl, doprowadzeniu odczynu do pH 7 i trzykrotnym wyekstrahowaniu porcjami 40 ml eteru metylowo-tert-butylowego, rozpuszczalnik odparowano i otrzymano 6,0 g żądanego produktu.
NMR(DMSO) ppm: 5,9 s (2H); 7,0-7,2 m (2H); 7,15 t (1H), 7,4-7,44 m (1H); 9,5 s (1H).
d) O-Cyklopropylometylooksym 2-difluorometoksy-6-fluorobenzamidu
Do roztworu 3,0 g oksymu 2-difluorometoksy-6-fluorobenzamidu w 30 ml dimetyloformamidu (DMF) w temperaturze 0 - 5°C dodano 0,4 g 80% wodorku sodu i w takiej temperaturze całość mieszano przez 3 godziny. Następnie w tej samej temperaturze dodano 1,8 g bromocyklopropylometanu, całość mieszano przez 2 godziny w temperaturze 5°C, a następnie przez noc w temperaturze pokojowej. Mieszaninę wymieszano z 300 ml wody i trzykrotnie wyekstrahowano porcjami 70 ml cykloheksanu. Po odparowaniu cykloheksanu otrzymano 1,9 g żądanego produktu.
NMR(CDCl3) ppm: 0,3 m (2H); 0,55 m (2H); 1,2 m (1H); 3,9 d (2H); 4,85 s,br (2H); 6,6 t (1H); 6,85-7,1 m (2H); 7,35-7,45 m (1H).
e) O-Cyklopropylometylooksym N-fenyloacetylo-2-difluorometoksy-6-fluorobenzamidu (związek l.6 z tabeli 1).
O-Cyklopropylometylooksym 2-difluorometoksy-6-fluorobenzamidu (1,9 g) otrzymany w etapie d) i 1,5 g chlorku kwasu fenylooctowego ogrzewano z 40 ml toluenu przez 20 godzin do temperatury wrzenia w warunkach powrotu skroplin. Po ochłodzeniu dodano 40 ml wody i odczyn mieszaniny reakcyjnej doprowadzono do pH 11. Po odparowaniu rozpuszczalnika i poddaniu pozostałości chromatografii kolumnowej na żelu krzemionkowym z użyciem mieszaniny 99:1 cykloheksanu i octanu etylu jako eluenta, wyodrębniono z fazy toluenowej 1,6 g żądanego produktu o t.t. 58-60°C.
NMR(CDCl3) ppm: 0,2 m (2H); 0,50 m (2H); 1,0 m (1H); 3,9 d (2H); 6,4 t (1H); 6,85-7,0 m (2H); 7,2-7,5 m (6H); 8,5 s (1H).
W analogiczny sposób otrzymano O-allilometylooksym N-fenyloacetylo-2-difluorometoksy-6-fluorobenzamidu (związek l.3. z tabeli 1) w postaci oleju.
P r z y k ł a d 2
Wytwarzanie 2-hydroksy-5,6-difluorobenzonitrylu
a) Wytwarzanie oksymu 2-metoksy-5,6-difluorobenzaldehydu
Do mieszaniny 16,0 g chlorowodorku hydroksyloaminy, 18,9 g octanu sodu i 110 ml 90% wodnego roztworu metanolu, w trakcie mieszania w temperaturze 20 - 25°C wkroplono roztwór 29,4 g 2-metoksy-5,6-difluorobenzaldehydu (według przykładu 27 w WO 97/03071). Po mieszaniu przez 16 godzin, po odparowaniu metanolu, pozostałość rozrobiono na pastę z 250 ml wody, przemyto, wysuszono i otrzymano 28,3 g żądanego produktu o t.t. 199 - 201°C.
b) Wytwarzanie 2-metoksy-5,6-difluorobenzonitrylu
Do zawiesiny 18,7 g produktu otrzymanego według a) w 100 ml toluenu dodano 20 kropli dimetyloformamidu i 16,6 g chlorku tionylu, przy czym uważano aby temperatura mieszaniny reakcyjnej nie była wyższa niż 30°C. Po mieszaniu przez 4 godziny w temperaturze 30°C, toluen i chlorek tionylu odparowano pod zmniejszonym ciśnieniem i otrzymano 16,5 g żądanego produktu w postaci oleju. NMR (CDCl3) ppm: 3,9 s (3H); 6,65-6,75 m (1H); 7,3-7,45 m (1H).
c) Wytwarzanie 2-hydroksy-5,6-difluorobenzonitrylu
PL 193 553 B1
Do roztworu 23,0 g produktu otrzymanego według b) w 70 ml toluenu, w trakcie mieszania w temperaturze 50°C dodano porcjami 21,7 g AlCl3, a następnie całość ogrzewano przez 2 godziny do temperatury wrzenia w warunkach powrotu skroplin. Po ochłodzeniu mieszaninę reakcyjną wlano do 350 ml wody i odczyn mieszaniny doprowadzono do pH 1 z użyciem 2N HCl. Otrzymany w ten sposób surowy produkt wyekstrahowano eterem metylowo-tert-butylowym (2 x 100 ml) i oczyszczono przez rozpuszczenie w 2N NaOH (2 x 80 ml) i zakwaszenie fazy alkalicznej 2N HCl do pH 5. Po ekstrakcji eterem metylowo-tert-butylowym (2 x 80 ml), wysuszeniu i odparowaniu rozpuszczalnika otrzymano 19,9 g żądanego produktu w postaci oleju. NMR (CDCl3) ppm: 6,45 s,brd (1H); 6,7-6,8 m (1H); 7,25-7,4 m (1H).
P r z y k ł a d 3
Sporządzono roztwór 90 części wagowych związku o wzorze I i 10 części wagowych N-metylo-2-pirolidonu do stosowania w postaci bardzo drobnych kropel.
P r z y k ł a d 4
Sporządzono mieszaninę 10 części wagowych związku o wzorze I, 70 części wagowych ksylenu, 10 części wagowych adduktu 8-10 moli tlenku etylenu i 1 mola N-monoetanoloamidu kwasu oleinowego, 5 części wagowych dodecylobenzenosulfonianu wapnia, 5 części wagowych adduktu 40 moli tlenku etylenu i 1 mola oleju rycynowego. Po dokładnym rozprowadzeniu roztworu w wodzie otrzymano dyspersję.
P r z y k ł a d 5
Sporządzono wodną dyspersję 10 części wagowych związku o wzorze I, 40 części wagowych cykloheksanonu, 30 części wagowych izobutanolu, 20 części wagowych adduktu 40 moli tlenku etylenu i 1 mola oleju rycynowego.
P r z y k ł a d 6
Sporządzono wodną dyspersję 10 części wagowych związku o wzorze I, 25 części wagowych cykloheksanolu, 55 części wagowych frakcji ropy naftowej o temperaturze wrzenia 210 - 260°C i 10 części wagowych adduktu 40 moli tlenku etylenu i 1 mola oleju rycynowego.
P r z y k ł a d 7
W młynku młotkowym zmielono mieszaninę 80 części wagowych korzystnie stałego związku o wzorze I, 3 części wagowych diizobutylonaftaleno-2-sulfonianu sodu, 10 części wagowych soli sodowej kwasu ligninosulfonowego z ługu posiarczynowego 7 części wagowych sproszkowanego żelu krzemionkowego. Po dokładnym rozprowadzeniu mieszaniny w wodzie otrzymano ciecz opryskową.
P r z y k ł a d 8
Sporządzono mieszaninę 3 części wagowych związku o wzorze I, według wynalazku, i 97 części wagowych drobnoziarnistego kaolinu. Ten preparat do opylania zawierał 3% wag. substancji czynnej.
P r z y k ł a d 9
Sporządzono mieszaninę 30 części wagowych związku o wzorze I, 62 części wagowych sproszkowanego żelu krzemionkowego i 8 części wagowych oleju parafinowego naniesionego na ten żel krzemionkowy. Dzięki takiemu formułowaniu uzyskano dobrą przyczepność substancji czynnej.
P r z y k ł a d 10
Sporządzono stałą, wodną dyspersję 40 części wagowych związku o wzorze I, 10 części wagowych soli sodowej kondensatu: kwas fenolosulfonowy/mocznik/formaldehyd, 2 części wagowych żelu krzemionkowego i 48 części wagowych wody. Uzyskaną dyspersję można dalej rozcieńczać.
P r z y k ł a d 11
Sporządzono stałą dyspersję w oleju 20 części wagowych związku o wzorze I, 2 części wagowych dodecylobenzenosulfonianu wapnia, 8 części wagowych eteru poliglikolu i alkoholu tłuszczowego, 20 części wagowych soli sodowej kondensatu: kwas fenolosulfonowy/mocznik/formaldehyd i 50 części wagowych parafinowego oleju mineralnego.
P r z y k ł a d 12
Działanie przeciw mączniakowi prawdziwemu na pszenicy
Liście siewek pszenicy gatunku „Fmhgold” wyhodowanych w doniczkach opryskano do spłynięcia wodnym preparatem substancji czynnej przygotowanym z roztworu podstawowego, zawierającym 10% substancji czynnej, 63% cykloheksanonu i 27% emulgatora, a w 24 godziny po wyschnięciu warstewki cieczy opryskowej badane rośliny zarażono zarodnikami mączniaka prawdziwego pszenicy (Erysiphe graminis forma specialis tritici). Badane rośliny umieszczono w szklarni w temperaturze 20 - 22°C i przy względnej wilgotności powietrza 75 - 80%. Po 7 dniach oceniono wizualnie w % nasilenie rozwoju mączniaka jako procentowe porażenie w przeliczeniu na całkowitą powierzchnię liści.
PL 193 553 B1
Rośliny potraktowane preparatem zawierającym 63 ppm substancji czynnej I.3, I.6, I.7, I.8, I.9, I.10, I.11 i I.17 z tabeli 1 nie wykazały porażenia, podczas gdy rośliny nie traktowane wykazały 80% porażenie.
P r z y k ł a d 13
Działanie przeciw mączniakowi prawdziwemu na pszenicy
Liście siewek pszenicy gatunku „Fmhgold” wyhodowanych w doniczkach opryskano do spłynięcia wodnym preparatem substancji czynnej przygotowanym z roztworu podstawowego, zawierającym 10% substancji czynnej, 63% cykloheksanonu i 27% emulgatora, a w 24 godziny po wyschnięciu warstwy cieczy opryskowej badane rośliny zarażono zarodnikami mączniaka prawdziwego pszenicy (Erysiphe graminis forma specialis tritici). Badane rośliny umieszczono w szklarni w temperaturze 20 - 22°C i przy względnej wilgotności powietrza 75 - 80%. Po 7 dniach oceniono wizualnie w % nasilenie rozwoju mączniaka jako procentowe porażenie w przeliczeniu na całkowitą powierzchnię liści.
Rośliny potraktowane substancjami czynnymi o wzorze IV, w którym R2 oznacza H lub 4-F, R1 oznacza CHmFn, gdzie m = 1, n = 2, nie wykazały żadnego porażenia, podczas gdy rośliny nietraktowane wykazały 80% porażenie.
Zastrzeżenia patentowe
1. Pochodne benzamidoksymu o ogólnym wzorze I
Claims (10)
1. Pochodne benzamidoksymu o ogólnym wzorze I w którym 1
R oznacza difluorometyl lub trifluorometyl;
2
R oznacza atom wodoru lub atom fluoru;
3
R oznacza C1-C4-alkil ewentualnie podstawiony grupą cyjanową, C1-C4-chlorowcoalkil, C1-C4-alkoksy-C1-C4-alkil, C3-C6-alkenyl, C3-C6-chlorowcoalkenyl, C3-C6-alkinyl lub C3-C8-cykloalkilo-C1-C4-alkil;
R3 4 5 oznacza fenylo-C1-C6-alkil ewentualnie podstawiony w pierścieniu fenylowym jednym lub większą liczbą podstawników wybranych z grupy obejmującej atom chlorowca, C1-C4-alkil, C1-C4-chlorowcoalkil, C1-C4-alkoksyl i C1-C4-chlorowcoalkoksyl, albo tienylo-C1-C4-alkil ewentualnie podstawiony w pierścieniu tienylowym jednym lub większą liczbą podstawników wybranych z grupy obejmującej atom chlorowca, C1-C4-alkil, C1-C4-chlorowcoalkil, C1-C4-alkoksyl i C1-C4-chlorowcoalkoksyl, albo pirazolo-C1-C4-alkil ewentualnie podstawiony w pierścieniu pirazolowym jednym lub większą liczbą podstawników wybranych z grupy obejmującej atom chlorowca, C1-C4-alkil, C1-C4-chlorowcoalkil, C1-C4-alkoksyl i C1-C4-chlorowcoalkoksyl.
2. Pochodne benzamidoksymu według zastrz. 1, w których R4 oznacza benzyl ewentualnie podstawiony w pierścieniu fenylowym 1-3 podstawnikami wybranymi z grupy obejmującej atom chlorowca, C1-C4-alkil i C1-C4-alkoksyl.
1
3. Pochodne benzamidoksymu według zastrz. 1, w których R1 oznacza difluorometyl.
2
4. Pochodne benzamidoksymu według zastrz. 1, w których R2 oznacza atom fluoru w pozycji 5 pierścienia fenylowego.
5. Benzamidoksymy o ogólnym wzorze V
PL 193 553 B1 w którym R i R mają znaczenie podane w zastrz. 1.
6. Benzamidoksymy według zastrz. 5, w których R2 oznacza atom fluoru w pozycji 5 pierścienia fenylowego.
7. Benzamidoksymy o ogólnym wzorze VI
1 2 3 w którym R , R i R mają znaczenie podane w zastrz. 1.
8. Benzamidoksymy według zastrz. 7, w których R2 oznacza atom fluoru w pozycji 5 fenylu.
9. Zastosowanie pochodnych benzamidoksymu o wzorze I zdefiniowanych w zastrz. 1 do zwalczania szkodliwych grzybów.
10. Środek grzybobójczy zawierający substancję czynną i nośnik i/lub substancje pomocnicze, znamienny tym, że jako substancję czynną zawiera co najmniej jedną pochodną benzamidoksymu o wzorze I zdefiniowaną w zastrz. 1 w grzybobójczo skutecznej ilości.
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| Application Number | Priority Date | Filing Date | Title |
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| DE19741099 | 1997-09-18 | ||
| DE19753519 | 1997-12-03 | ||
| DE19802459 | 1998-01-23 | ||
| PCT/EP1998/005617 WO1999014187A1 (de) | 1997-09-18 | 1998-09-05 | Benzamidoxim-derivat, zwischenprodukte und verfahren zu deren herstellung und deren verwendung als fungizide |
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| PL193553B1 true PL193553B1 (pl) | 2007-02-28 |
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| JPS6434954A (en) * | 1987-02-18 | 1989-02-06 | Hokko Chem Ind Co | Benzenecarboximidamide derivative and agricultural and horticultural fungicide |
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| DE3919435A1 (de) * | 1989-06-14 | 1990-12-20 | Basf Ag | Salicylaldehyd- und salicylsaeurederivate sowie deren schwefelanaloge, verfahren zu ihrer herstellung als herbizide und bioregulatoren |
| EP0490224B1 (de) * | 1990-12-14 | 1996-03-13 | BASF Aktiengesellschaft | Salicylaldehyd- und Salicylsäurederivate sowie deren Schwefelanaloge, Verfahren und Zwischenprodukte zu ihrer Herstellung |
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1998
- 1998-09-05 NZ NZ503594A patent/NZ503594A/en unknown
- 1998-09-05 DE DE59806467T patent/DE59806467D1/de not_active Expired - Fee Related
- 1998-09-05 WO PCT/EP1998/005617 patent/WO1999014187A1/de not_active Ceased
- 1998-09-05 ES ES98947518T patent/ES2188016T3/es not_active Expired - Lifetime
- 1998-09-05 DK DK98947518T patent/DK1017670T3/da active
- 1998-09-05 US US09/508,597 patent/US6420605B1/en not_active Expired - Fee Related
- 1998-09-05 EP EP98947518A patent/EP1017670B1/de not_active Expired - Lifetime
- 1998-09-05 IL IL13479598A patent/IL134795A0/xx not_active IP Right Cessation
- 1998-09-05 PT PT98947518T patent/PT1017670E/pt unknown
- 1998-09-05 BR BR9812515-0A patent/BR9812515A/pt not_active Application Discontinuation
- 1998-09-05 KR KR1020007002819A patent/KR100644301B1/ko not_active Expired - Fee Related
- 1998-09-05 JP JP2000511739A patent/JP2001516740A/ja not_active Withdrawn
- 1998-09-05 TR TR2000/00735T patent/TR200000735T2/xx unknown
- 1998-09-05 HU HU0003467A patent/HUP0003467A3/hu unknown
- 1998-09-05 AT AT98947518T patent/ATE228499T1/de not_active IP Right Cessation
- 1998-09-05 SK SK288-2000A patent/SK284626B6/sk unknown
- 1998-09-05 CN CN98809266A patent/CN1117074C/zh not_active Expired - Fee Related
- 1998-09-05 AU AU94400/98A patent/AU748905B2/en not_active Ceased
- 1998-09-05 CN CNB021558574A patent/CN1246304C/zh not_active Expired - Fee Related
- 1998-09-05 PL PL98339359A patent/PL193553B1/pl unknown
- 1998-09-05 CA CA002304270A patent/CA2304270A1/en not_active Abandoned
- 1998-09-18 AR ARP980104674A patent/AR017122A1/es active IP Right Grant
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2000
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- 2000-03-17 NO NO20001406A patent/NO20001406D0/no not_active Application Discontinuation
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2002
- 2002-03-11 US US10/093,634 patent/US6509501B2/en not_active Expired - Fee Related
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