SE442868B - CYCLOPROPANCARBONIC ACID ANALIDES WITH FUNGICIDE EFFECTS AND THEIR USE IN FUNGICIDES - Google Patents
CYCLOPROPANCARBONIC ACID ANALIDES WITH FUNGICIDE EFFECTS AND THEIR USE IN FUNGICIDESInfo
- Publication number
- SE442868B SE442868B SE7805994A SE7805994A SE442868B SE 442868 B SE442868 B SE 442868B SE 7805994 A SE7805994 A SE 7805994A SE 7805994 A SE7805994 A SE 7805994A SE 442868 B SE442868 B SE 442868B
- Authority
- SE
- Sweden
- Prior art keywords
- furyl
- oxoperhydro
- cyclopropanecarboxylic acid
- anilide
- plants
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 8
- 239000000417 fungicide Substances 0.000 title claims description 5
- 230000000694 effects Effects 0.000 title description 20
- 239000002253 acid Substances 0.000 title description 7
- -1 2-oxoperhydro-3-furyl Chemical group 0.000 claims description 53
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical group OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000000969 carrier Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- FVTSQWATRFFSHH-UHFFFAOYSA-N C1CC1C(=O)N(C2CCOC2=O)C3=CC(=CC=C3)F Chemical group C1CC1C(=O)N(C2CCOC2=O)C3=CC(=CC=C3)F FVTSQWATRFFSHH-UHFFFAOYSA-N 0.000 claims 1
- GJMONPSULDEHGJ-UHFFFAOYSA-N CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C(=CC=C1)C Chemical group CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C(=CC=C1)C GJMONPSULDEHGJ-UHFFFAOYSA-N 0.000 claims 1
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical group ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- OCHYJSATRBHPLB-UHFFFAOYSA-N n-phenylcyclopropanecarboxamide Chemical class C1CC1C(=O)NC1=CC=CC=C1 OCHYJSATRBHPLB-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 23
- 239000002689 soil Substances 0.000 description 17
- 230000002538 fungal effect Effects 0.000 description 10
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- 206010061217 Infestation Diseases 0.000 description 8
- 240000003768 Solanum lycopersicum Species 0.000 description 8
- 230000017074 necrotic cell death Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 240000004713 Pisum sativum Species 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 235000000292 Gouania lupuloides Nutrition 0.000 description 4
- 244000299452 Gouania lupuloides Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 241000233614 Phytophthora Species 0.000 description 3
- 241000918584 Pythium ultimum Species 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- 241000371644 Curvularia ravenelii Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 235000011203 Origanum Nutrition 0.000 description 2
- 240000000783 Origanum majorana Species 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
- IBANRDPEOYZVGW-UHFFFAOYSA-N 3-methyl-1,2,4-thiadiazole Chemical compound CC=1N=CSN=1 IBANRDPEOYZVGW-UHFFFAOYSA-N 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- GJXVERNLEPCRDQ-UHFFFAOYSA-N CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 Chemical compound CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 GJXVERNLEPCRDQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- GKLKISMJWCRVSX-UHFFFAOYSA-N ClC=1C=C(N(C(=O)C2CC2)C2C(OC(C2)C)=O)C=CC1 Chemical compound ClC=1C=C(N(C(=O)C2CC2)C2C(OC(C2)C)=O)C=CC1 GKLKISMJWCRVSX-UHFFFAOYSA-N 0.000 description 1
- WMPNOTQEOFQCQQ-UHFFFAOYSA-N ClC=1C=CC(=C(N(C(=O)C2CC2)C2C(OCC2)=O)C1)OC Chemical compound ClC=1C=CC(=C(N(C(=O)C2CC2)C2C(OCC2)=O)C1)OC WMPNOTQEOFQCQQ-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000233629 Phytophthora parasitica Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
7805994-6 2 - _ R 2 H /C 2 (CHZ) _cH-N-co-cH I n H \ CHZ =o Rl O där R1 betecknar väte eller C1_4-alkyl, R2 fenyl eller en en- kelt eller flerfaldigt, lika eller olika, medelst C1_4-alkyl, C1_4 C1_4-alkyltio, halogen, trifluormetyl, C1_4-alk- oxikarbonyl och/eller cyan substituerad fenylgrupp och n be- -alkoxi, tecknar talet 1. 7805994-6 2 - _ R 2 H / C 2 (CH 2) _cH-N-co-cH I n H \ CHZ = o Rl O wherein R 1 represents hydrogen or C 1-4 alkyl, R 2 represents phenyl or an en- single or multiple, the same or different, by means of C 1-4 alkyl, C1-4 C1-4-alkylthio, halogen, trifluoromethyl, C1-4-alk- oxycarbonyl and / or cyano substituted phenyl group and n -alkoxy, draws the number 1.
Föreningarna enligt uppfinningen har överraskande~vi- sat sig ha en överlägsen verkan gentemot fytopatogena svampar i jämförelse med kända medel med liknande inriktning av verkan och de utmärker sig dessutom genom att de fördrages väl av växter och en tillfredsställande varaktig verkan. Då de dess- utom, i de insatsmängder, som i praktiken kommer i fråga, ej uppvisar fytotoxiska verkningar kan de med fördel användas inom jordbruket och vid trädgârdsskötsel för bekämpning av fytopa- togena svampar.The compounds of the invention have surprisingly sat has a superior effect against phytopathogenic fungi in comparison with known agents with a similar focus of action and they are also distinguished by the fact that they are well tolerated plants and a satisfactory lasting effect. Since they except, in the quantities of stakes which in practice come into question, no exhibit phytotoxic effects, they can be advantageously used within agriculture and horticulture to control phytopathic togena mushrooms.
Föreningarna enligt uppfinningen uppvisar överraskande fungicida egenskaper gentemot skadesvampar, t.ex. bladmögel- svampar.The compounds of the invention surprisingly exhibit fungicidal properties against harmful fungi, e.g. leaf mold mushrooms.
I motsats till kända fungicida medel med enbart före- byggande verkan, t.ex. N-triklormetyltioftalimid (amerikanska patentskrifterna 2 553 770, 2 553 771 och 2 553 776) och mangan- etylenbisditiokarbamat (amerikanska patentskrifterna 2 504 404 och 2 710 822) uppvisar föreningarna enligt uppfinningen ovän- tat dessutom en ytterligare fördel då de har en kurativ och systemisk verkan, och möjliggör därför även bekämpning av sjuk- domsalstrande organismer hos redan angripna växter.In contrast to known fungicides with only building effect, e.g. N-trichloromethylthiophthalimide (American Patents 2,553,770, 2,553,771 and 2,553,776) and manganese ethylene bisdithiocarbamate (U.S. Patents 2,504,404 and 2,710,822), the compounds of the invention exhibit In addition, they have an additional advantage as they have a curative and systemic effect, and therefore also enables the control of judgment-producing organisms in already infested plants.
Bland föreningarna enligt uppfinningen utmärker sig ge- nom en överraskande fungicid verkan särskilt sådana föreningar, där i den allmänna formeln,I 7805994-6 É2 /,.cH (cH2)n-cH-N-co-CH | “\\ H::>L\\ //¶= O CHZ o R1 2 Rl betecknar väte, metyl eller etyl ocn R2 betecknar fenyl, metylfenyl, dimetylfenyl, etylfenyl, isopropylfenyl, metoxi- fenyl, etoxifenyl, metyltiofenyl, fluorfenyl, klorfenyl, brom- fenyl, diklorfenyl, trifluormetylfenyl, nitrofenyl, cyanfenyl, metoxikarbonylfenyl, acetylfenyl.Among the compounds of the invention, by a surprising fungicidal action especially such compounds, where in the general formula, I 7805994-6 É2 / ,.cH (cH2) n-cH-N-co-CH2 “\\ H ::> L \\ // ¶ = O CHZ O R1 2 R 1 represents hydrogen, methyl or ethyl and R 2 represents phenyl, methylphenyl, dimethylphenyl, ethylphenyl, isopropylphenyl, methoxyphenyl phenyl, ethoxyphenyl, methylthiophenyl, fluorophenyl, chlorophenyl, bromophenyl phenyl, dichlorophenyl, trifluoromethylphenyl, nitrophenyl, cyanophenyl, methoxycarbonylphenyl, acetylphenyl.
Man kan använda den verksamma föreningen enbart eller i blandning med åtminstone två verksamma föreningar med olika konstitution bland föreningarna enligt uppfinningen. Om så öds- kas kan man alltefter det önskade ändamålet, tillsätta andra fungicider, nematocider, herbicider eller andra bekämpnings- medel mot sjukdomsalstrande organismer.You can use the active compound only or in admixture with at least two active compounds with different constitution among the compounds of the invention. If so desolate You can, depending on the desired purpose, add others fungicides, nematocides, herbicides or other pesticides agents against disease-causing organisms.
Lämpligen skall man använda de verksamma föreningarna i form av beredningar, t.ex. pulver, ströpuder, granulat, lös- ningar, emulsioner eller suspensioner med tillsättning av fly- tande och/eller fasta bärare eller utspädníngsmedel och even- tuellt av vät-, vidhäftnings-, emulger- och/eller disperger- hjälpmedel. ' . ; Lämpliga flytande bärare är vatten, mineraloljor eller andra organiska lösningsmedel, t.ex. xylen, klorbensen, cyklo- hexanol, dioxan, acetoniril, ättikester, dimetylformamid, iso- foron och dimetylsulfoxid.It is advisable to use the active compounds in the form of preparations, e.g. powders, powders, granules, solvents emulsions or suspensions with the addition of liquid and / or solid carriers or diluents and any possibly by wetting, adhering, emulsifying and / or dispersing aid. '. ; Suitable liquid carriers are water, mineral oils or other organic solvents, e.g. xylene, chlorobenzene, cyclo- hexanol, dioxane, acetoniril, acetic ester, dimethylformamide, iso- foron and dimethyl sulfoxide.
Lämpliga fasta bärare är kalk, kaolin, krita, talk, fullerjord och andra lerhaltiga jordar samt naturlig eller syn- tetisk kiselsyra.Suitable solid carriers are lime, kaolin, chalk, talc, full soils and other clayey soils as well as natural or silicic acid.
Exempel på ytaktiva ämnen är salter av ligninsulfon- syror, salter av alkylerade bensensulfonsyror, sulfonerade syra- amider och salter av desamma, polyetoxilerade aminer och alko- holer.Examples of surfactants are salts of lignin sulfonic acid. acids, salts of alkylated benzenesulfonic acids, sulfonated acids amides and salts of the same, polyethoxylated amines and alcohols holer.
I den mån man ämnar använda de verksamma föreningarna för att beta utsäde kan man även blanda in färgämnen för att göra det betade utsädet lätt synligt. 7805994-6 r Andelen verksam förening eller verksamma föreningar i medlet kan variera inom vida gränser, varvid den rätta koncentra- tionen av de använda föreningarna i medlet bl.a. huvudsakligen beror på i vilken mängd medlet skall användas för jord- eller utsädesbehandling eller för bladbesprutning. Så t.ex. innehål- ler medlen ca l - 80 viktprocent, företrädesvis 20 - 50 vikt- procent verksam förening och ca 99 - 20 viktprocent flytande eller fasta bärare samt eventuellt högst 20 viktprocent ytak- tiva ämnen.To the extent that one intends to use the active associations to graze seeds, you can also mix in dyes to make the grazed seed easily visible. 7805994-6 r Proportion of active association or active associations in the agent can vary widely, with the right concentration of the compounds used in the agent, e.g. mainly depends on the amount of the agent to be used for soil or seed treatment or for foliar spraying. So e.g. containing the agents are about 1-80% by weight, preferably 20-50% by weight. percent active compound and about 99 - 20% by weight liquid or solid carriers and, where appropriate, a maximum of 20% by weight active substances.
De nya föreningarna med den allmänna formeln I kan fram- ställas genom att man bringar en förening med den allmänna for- meln: (CHZ) n-CH-NH-Rz H II “ =o o Rl där Rl, R2 och n har de ovan angivna betydelserna, att reagera med cyklopropankarbonsyraklorid med formeln: Cl-CO-CH \ CH2 i närvaro av en syraacceptor och eventuellt ett lösningsmedel i företrädesvis ekvimolära mängdförhållanden, varefter man iso- lerar den bildade föreningen på i och för sig känt sätt.The new compounds of general formula I can be prepared by bringing an association with the general meln: (CH 2) n -CH-NH-R 2 H II “ = o O Rl where R 1, R 2 and n have the meanings given above, to react with cyclopropanecarboxylic acid chloride of the formula: Cl-CO-CH \ CH2 in the presence of an acid acceptor and possibly a solvent in preferably equimolar proportions, after which the teaches the formed association in a manner known per se.
Såsom syraacceptorer kan man använda organiska baser, t.ex. pyridin, trietylamin eller N,N-dimetylanilin, eller oorga- niska baser, t.ex. hydroxider, oxider och karbonater av alkali- metaller och alkaliska jordartsmetaller, t.ex. natrium, kalium eller kalcium. 7805994-6 r Såsom lösningsmedel kan eventuellt användas eter, tetrahydrofuran, bensen, ättikester med flera. Flytande syra- acceptorer, exempelvis pyridin, kan man samtidigt använda som lösningsmedel.Organic bases can be used as acid acceptors, for example pyridine, triethylamine or N, N-dimethylaniline, or trans- technical bases, e.g. hydroxides, oxides and carbonates of alkali metal metals and alkaline earth metals, e.g. sodium, potassium or calcium. 7805994-6 r As the solvent, ether may optionally be used. tetrahydrofuran, benzene, acetic ester and more. Liquid acid acceptors, such as pyridine, can be used simultaneously as solvent.
Reaktionen utföres lämpligen vid temperaturer mellan -1o° c och 12o° c.The reaction is conveniently carried out at temperatures between -1o ° c and 12o ° c.
Uppfinningen skall i det följande belysas närmare med hjälp av nedanstående framställningsexempel utan att dock vara begränsad till dessa.The invention will be further elucidated in the following using the following preparation examples without, however, being limited to these.
Exempel l Cyklopropankarbonsyra-[N-(2-oxoperhydro-3-furyl)-anilüfl (Förening nr 1) Till en lösning av 10,62 g (0,06 mol) 3-anilinperhydro- furanon-2 i 50 ml pyridin sattes droppvis med omrörning 6,30 g (0,06 mol) cyklopropankarbonsyraklorid vid en inre temperatur av 5 - 100 C. Blandningen omrördes 30 minuter vid rumstempera- tur, varefter den sattes till 200 g vatten/is och omrördes väl.Example 1 Cyclopropanecarboxylic acid [N- (2-oxoperhydro-3-furyl) -anilyl] (Compound No. 1) To a solution of 10.62 g (0.06 mol) of 3-aniline perhydrous furanone-2 in 50 ml of pyridine was added dropwise with stirring 6.30 g (0.06 mol) of cyclopropanecarboxylic acid chloride at an internal temperature of 5 - 100 ° C. The mixture was stirred for 30 minutes at room temperature. turn, after which it was added to 200 g of water / ice and stirred well.
Efter avsugning tvättade man blandningen noggrant med vatten och torkade den i torkskåp. Utbyte: l0,25 (70 % av det teore- tiska). Smp.: 1040 C.After suction, the mixture was washed thoroughly with water and dried it in the drying cabinet. Yield: 10.25 (70% of theory) tiska). Mp: 1040 ° C.
Pâ samma sätt kan man framställa följande föreningar enligt uppfinningen.In the same way, the following compounds can be prepared according to the invention.
Förening Benämning ' Smältpunkt °C, och nr. brytningsindex nå? 2 cyklopropankarbonsyra-[2,6-dietyl- N-(2-oxoperhydro-3-furyl)-anilrfl 102 - 103 3 cyklopropankarbonsyra-[2-metoxi-N- (2-Qxopernyaro-3-furyi)-ani1mfl 175 - 176 4 cyklopropankarbonsyra- [2-metyl-N- (oxoperhydro-3-furyl)-anilid] 108 - 109 cyklopropankarbonsyra-[?,6-dimetyl- N- <2-<>x0perhyar0-3-fury1) -aniliaj 114 - 116 6 cyklopropankarbonsyra-[2,5-dimetyl- N-<2-oxoperhyaro-3-furyl)-anilidl 84 7805994-6 '_ | Förening Benämning III'- Smältpunkt °C , och brytningsindex nz 0 D ll 12 13 14 16 17 18 19 cyklopropankarbonsyra- [3-mety1-N- (2-oxoperhydro-3-furyl) -anilidï cykloprop ankarbon syra- (4 -mety l-N- (2-oxoperhydro-3- furyl) -anílinfl cyklopropankarbonsyra- H3 , 4-dimety1- N- (2-oxope rhydro-3-furyl) -anilicfl cyklopropankarbonsyra- [Z , 3-dimetyl- N- (2-oxoperhydro-3-furyl) -anilicg cykloproparxl: arbon syra-KZ , 4 -dimetyl- N- (2-oxoperhydro-3-furyl) -anilicfl cykl opropankarbon syra- 1:3 , S-dimetyl- N- (2-oxoperhydro-3-furyl) -anilidJ cyklopropankarbonsyra- 1:2 , 4 , G-tri- metyl-N- (2-oxoperhydro-3-furyl) - ani lid] cykloprop ankarbonsyra- [24 -klor-N- (2-oxoperhydro-3-fury1) -anilidl cykllopropankarbonsyra- B-klor-'BI- (2-oxoperhydro-3-fury1) - anilicfl cyklopropankarbonsyra- H4 - isopropy l- N- (2-oxoperhydro-3-furyl) -anilidj cyklopropankarbonsyra- [3-trif1uor- metyl-N- (2-oxoperhydro-3-furyl) - anilidJ cyklopropankarbonsyra- [3-fluo1r-N- (Z-oxoperhydro-B-furyl) -anilidj cyklopropankarbonsyra- f3-brom-N- (Z-oxoperhydro-B-furyl) wanilid] 109 123 99 153 85 103 119 149 99 108 104 89 93 100 86 121 150 1oo - i 110 105 94 7805994-6 7 F _ _ Förening Benämning Smältpunkt °C, och nr. brytningsindex nšo cyklopropankarbonsyra-[2,6-diiso- propyl-N-(2-oxoperhydro-3-furyl)~ annie] 215 - 216 21 cyklopropankarbonsyra-[2-etyl-N- (2-oxoperhydro-3-furyl)-anilié] 103 22 cyklopropankarbonsyra-[4-etyl-N- (2-oxoperhydro-3-furyl) -aniliçfl 107 23 cyklopropankarbonsyra-t¶-metoxi-N- (2-oxoperhydro-3-furyl)-aniliê] 75 24 cyklopropankarbonsyra-[4-brom-N- (2-oxoperhydro-3-furyl)-aniliél 144 ~ 145 cyklopropankarbonsyra-[4-fluor-N- (2-oxoperhydro-3-furyl)-aniliël 138 - 139 26 cyklopropankarbonsyra-[2-etoxí-N- (2-oxoperhydro-3-furyl)-aniliq] 143 - 145 27 cyklopropankarbonsyra-[3-klor-2- metyl-N-(2-oxoperhydro-3-furyl)- anuia] 121 - 124 _ 28 cyklopropankarbonsyra-f5~klor-2- metyl-N-(2-oxoperhydro-3-furyl)- anilia] 114 - 116 29 cykloprøpankarbonsyra-4-metoxi-2- metyl-N-(2-oxoperhydro-3-furyl)- nšoz l,5520 anilid cyklopropankarbonsyra-4-etoxi-N- n2° -1 4579 (2-oxoperhydro-3-furyl)-anilid D ' ' 31 cyklopropankarbonsyra-5-klor-2- metoxi-N-(2-oxoperhydro-3-furyl)- anilid 163 - 164 7805994-6 8 r_ - ' _ Förening Benämning Smältpunkt OC, och nr. - brytningsindex nšo 32 cyklopropankarbonsyra-3-klor-N- (5-metyl-2-oxoperhydro-3-furyl)- anilid 95 - 97 33 cyklopropankarbonsyra-[§-etyl-N- (2-oxoperhydro-3-furyl)-anilid] 69 - 70 34 cyklopropankarbonsyra-[3-cyan-N- (z-oxoperhydro-s-furyl) -anilifl 142 - 143 cyklopropankarbonsyra-fl3-tiometyl- N-(2-oxoperhydro-3-furyl)-anilbå nšo: l,5888 36 cyklopropankarbonsyra-E?,3-dik1or- \ N-(2-oxoperhydro-3-furyl)-anilhâ 136 - 137 37 cyklopropankarbonsyra-C§-klor-N- (5-metyl-2-oxoperhydro-3-furyl)- anilia] 95 - 97 Föreningarna enligt uppfinningen utgör vanligen färg- lösa, luktlösa, kristallina kroppar, som är nästan olösliga i vatten och bensin. I polära organiska lösningsmedel t.ex. - Å aceton, dimetylformamid och dimetylsulfoxid är de däremot myc- ket lättlösliga.Compound Name 'Melting point ° C, and no. refractive index now? 2 cyclopropanecarboxylic acid [2,6-diethyl- N- (2-oxoperhydro-3-furyl) -anilr fl 102 - 103 3 cyclopropanecarboxylic acid [2-methoxy-N- (2-Qxopernyaro-3-furyi) -ani1m fl 175 - 176 4 cyclopropanecarboxylic acid [2-methyl-N- (oxoperhydro-3-furyl) -anilide] 108 - 109 cyclopropanecarboxylic acid - [?, 6-dimethyl- N- <2 - <> x0perhyar0-3-fury1) -aniliaj 114 - 116 6 cyclopropanecarboxylic acid [2,5-dimethyl- N- (2-oxoperhyaro-3-furyl) -anilidine 84 7805994-6 '_ | Association Name III'- Melting point ° C, and refractive index nz 0 D ll 12 13 14 16 17 18 19 cyclopropanecarboxylic acid [3-methyl-N- (2-oxoperhydro-3-furyl) -anilide cyclopropanecarboxylic acid- (4 -methyl-N- (2-oxoperhydro-3-furyl) -aniline fl cyclopropanecarboxylic acid H3,4-dimethyl- N- (2-oxopyrhydro-3-furyl) -anilic fl cyclopropanecarboxylic acid [Z, 3-dimethyl- N- (2-oxoperhydro-3-furyl) -anilicg cycloproparx1: carbonic acid-KZ, 4 -dimethyl- N- (2-oxoperhydro-3-furyl) -anilic fl cyclopropanecarbon acid- 1: 3, S-dimethyl- N- (2-oxoperhydro-3-furyl) -anilideJ cyclopropanecarboxylic acid 1: 2, 4, G-tri- methyl-N- (2-oxoperhydro-3-furyl) - ani lid] cyclopropanecarboxylic acid [24 -chloro-N- (2-oxoperhydro-3-furyl) -anilidine cyclopropanecarboxylic acid- B-chloro-'BI- (2-oxoperhydro-3-furyl) - anilic fl cyclopropanecarboxylic acid- H4 - isopropyl I- N- (2-oxoperhydro-3-furyl) -anilide cyclopropanecarboxylic acid [3-trifluoro- methyl-N- (2-oxoperhydro-3-furyl) - anilidJ cyclopropanecarboxylic acid [3-fluorine-N- (Z-oxoperhydro-β-furyl) -anilide cyclopropanecarboxylic acid f3-bromo-N- (Z-oxoperhydro-β-furyl) wanilide] 109 123 99 153 85 103 119 149 99 108 104 89 93 100 86 121 150 1oo - i 110 105 94 7805994-6 7 F _ _ Compound Name Melting point ° C, and no. refractive index nšo cyclopropanecarboxylic acid [2,6-diiso- propyl-N- (2-oxoperhydro-3-furyl) ~ annie] 215 - 216 21 cyclopropanecarboxylic acid [2-ethyl-N- (2-oxoperhydro-3-furyl) -anilyl] 103 22 cyclopropanecarboxylic acid [4-ethyl-N- (2-oxoperhydro-3-furyl) -aniliço 107 23 cyclopropanecarboxylic acid t-methoxy-N- (2-oxoperhydro-3-furyl) -anilyl] 75 24 cyclopropanecarboxylic acid [4-bromo-N- (2-oxoperhydro-3-furyl) -anilate 144 ~ 145 cyclopropanecarboxylic acid [4-fluoro-N- (2-oxoperhydro-3-furyl) -anilyl 138 - 139 26 cyclopropanecarboxylic acid [2-ethoxy-N- (2-oxoperhydro-3-furyl) -anilyl] 143 - 145 27 cyclopropanecarboxylic acid [3-chloro-2- methyl-N- (2-oxoperhydro-3-furyl) - anuia] 121 - 124 _ 28 cyclopropanecarboxylic acid-f5-chloro-2- methyl-N- (2-oxoperhydro-3-furyl) - anilia] 114 - 116 29 Cyclopropanecarboxylic acid 4-methoxy-2- methyl-N- (2-oxoperhydro-3-furyl) -nose 1, 5520 anilide cyclopropanecarboxylic acid 4-ethoxy-N- n2 ° -1 4579 (2-oxoperhydro-3-furyl) -anilide D " 31 cyclopropanecarboxylic acid 5-chloro-2- methoxy-N- (2-oxoperhydro-3-furyl) - anilide 163 - 164 7805994-6 8 r_ - '_ Compound Name Melting point OC, and no. refractive index nšo 32 cyclopropanecarboxylic acid 3-chloro-N- (5-methyl-2-oxoperhydro-3-furyl) - anilide 95 - 97 33 cyclopropanecarboxylic acid- [§-ethyl-N- (2-oxoperhydro-3-furyl) -anilide] 69-70 34 cyclopropanecarboxylic acid [3-cyano-N- (z-oxoperhydro-s-furyl) -anili fl 142 - 143 cyclopropanecarboxylic acid fl3-thiomethyl- N- (2-oxoperhydro-3-furyl) -anilobenosine: 1,588 36 cyclopropanecarboxylic acid E, 3-dichloro- N- (2-oxoperhydro-3-furyl) -anilhâ 136 - 137 37 cyclopropanecarboxylic acid-C§-chloro-N- (5-methyl-2-oxoperhydro-3-furyl) - anilia] 95 - 97 The compounds of the invention are usually colored loose, odorless, crystalline bodies, which are almost insoluble in water and petrol. In polar organic solvents e.g. - Oh acetone, dimethylformamide and dimethylsulfoxide, on the other hand, are easily soluble.
Utgångsföreningarna för framställning av föreningarna enligt uppfinningen är kända i och för sig eller kan framstäl- las på i och för sig känt sätt.The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared read in a manner known per se.
Följande exempel belyser användningsmöjligheterna för föreningarna enligt uppfinningen.The following examples illustrate the uses for the compounds of the invention.
Exempel 2 Gränskoncentrationsförsök vid bekämpning av Pythium ultimum. -procentiga beredningar i pulverform av de verksamma föreningarna blandades homogent med jord, som var kraftigt in- fekterad av Pythium ultimum. Man fyllde den behandlade jorden f' 7805994-6 på 0,5 liter lerkrukor och sådde utan karenstid i varje kruka frön av märgärta av sorten "Wunder von Kelvedon". Efter 3 veckors odling vid 20 - 240 C fastställde man antalet friska ärtplantor och utförde rotbonityr (l~4).Example 2 Limit concentration tests in the control of Pythium ultimum. -percent formulations in powder form by those active the compounds were mixed homogeneously with soil which was strongly in- affected by Pythium ultimum. The treated soil was filled f ' 7805994-6 on 0.5 liter clay pots and sowed without a waiting period in each pot seeds of marjoram of the variety "Wunder von Kelvedon". After 3 weeks of cultivation at 20 - 240 C the number of healthy was determined pea seedlings and performed root fertilizer (l ~ 4).
De verksamma föreningarna, insatsmängderna och resulta- ten framgår av följande tabell.The active compounds, the amounts of action and the results is shown in the following table.
Förening enligt uppfinningen Cyklopropankarbonsyra- [N- (2-oxoperhydro- 3- furyi)-aniliq cyklopropankarbonsyra- [2,6-dimetyl-N-(2-oxoper- hydro-S-furyl) -anilicfl cyklopropankarbonsyra- fl3-klor-N-(2-oxoperhydro- 3-furyl) -anilidl cyklopropankarbonsyra- fi0-metyl-N-(2-oxoperhydro- 3-furyl) -anilicfl cyklopropankarbonsyra- {2-metoxi-N-(2-oxoperhydro~ 3-furyl)-anilia] Jämförd förening -etoxi-3-triklormetyl- l,2,4-tiadiazol Kontroll I (3 uggregningar) infekterad jord Konc. av den antal rotbonityr verksamma fö- friska (l - 4) reningen i ärtplantor mg/l jord 17 4 17 4 40 18 16 20 4 40 19 19 17 40 17 10 l_ 16 '2- 40 16 4 10 16 40 20 a) l l b) - 7805994-6 Förening enligt Konc. av den antal rotbonityr uppfinningen verksamma fö- friska ( l - 4) reningen i ärtplantor mg/1 jord Kontroll II (3 uggregningar) ångbehandlad jord a) 19 b) 18 c) 18 Rotbonityr: vita rötter utan svampnekros vita rötter, någon svampnekros bruna rötter, viss utveckling av svampnekros\ 4 3 2 lg stark svampnekros, ruttnande rötter N Exemgel 3 Betning av sockerbetor Vägt utsäde av sockerbeta av sorten "Dieckmann-Suprapoly" betades med 20-procentiga beredningar i pulverform av de verk- samma föreningarna. 2 liter lerkrukcr(2O x 20 x 5 cm) fylldes med normal kompostjord (Damping-off), varefter man sådde 100 frön av sockerbeta i varje kruka. Efter 18 dagars odling vid _ 19 - 210 C i växthus fastställde man antalet friska fröplantor.Compound according to the invention Cyclopropanecarboxylic acid [N- (2-oxoperhydro-3- furyi) -aniliq cyclopropanecarboxylic acid [2,6-dimethyl-N- (2-oxoper- hydro-S-furyl) -anilic fl cyclopropanecarboxylic acid fl3-chloro-N- (2-oxoperhydro- 3-furyl) -anilidyl cyclopropanecarboxylic acid fi0-methyl-N- (2-oxoperhydro- 3-furyl) -anilic fl cyclopropanecarboxylic acid {2-methoxy-N- (2-oxoperhydro- ~ 3-furyl) -anilia] Compared association -ethoxy-3-trichloromethyl- 1,2,4-thiadiazole Control I (3 uggregningar) infected soil Conc. of the number of root habitats active healthy (1 - 4) the purification in pea plants mg / l soil 17 4 17 4 40 18 16 20 4 40 19 19 17 40 17 10 l_ 16 '2- 40 16 4 10 16 40 20 a) l l b) - 7805994-6 Association according to Conc. of the number of root habitats fresh active in the invention (1-4) the purification in pea plants mg / 1 soil Control II (3 uggregningar) steam-treated soil a) 19 b) 18 c) 18 Root root: white roots without fungal necrosis white roots, some fungal necrosis brown roots, some development of fungal necrosis \ 4 3 2 lg strong fungal necrosis, rotting roots N Exemgel 3 Pickling of sugar beets Weighted seed of sugar beet of the variety "Dieckmann-Suprapoly" were prepared with 20% powdered formulations of the the same associations. 2 liters of clay jars (2O x 20 x 5 cm) were filled with normal compost soil (Damping-off), after which 100 were sown seeds of sugar beet in each pot. After 18 days of culture at _ 19 - 210 C in greenhouses, the number of healthy seedlings was determined.
De verksamma föreningarna, insatsmängder och resulta- ten framgår av följande tabell. 7805994-6 ll F ' " _ ' » Föreningar enligt Verksam förening Antal friska uppfinningen i g/kg utsäde fröplantor cyklopropankarbonsyra-LN- 0,4 79 (2-oxoperhydro-3-furyl)- 0,8 79 aning] 1,6 75 cyklopropankarbonsyra- 0,4 70 E2,6-dimetyl-N-(2-oxoperhydro- 0,8 76 a-furyn -anilifl 1,6 83 cyklopropankarbonsyra- 0,4 83 Lä-klor-N-(2-oxoperhydro- 0,8 82 z-furyl) -anilicfl 1,6 93 cyklopropankarbonsyra- 0,4 77 \ 3-metyl-N-(2-oxoperhydro- 0,8 7l 3-furyl)-anilid 1,6 85 cyklopropankarbonsyra- 0,4 83 L?-metoxi-N-(2-oxoperhydro- 0,8 87 s-furyl) -aniudl 1,6 sv Jämförelseföreningar -etoxi-3-triklor- 0,4 26 _ metyl-l,2,4-tiadiazol 0,8 44 _ 1,6 53 tetrametyltiuramdisulfid 4,8 21 9,6 50 Kontroll I (3 upprepningar) a) infekterad jord b) c) Kontroll II (3 upprepningar) a) 33 ângbehandlad jord b) 86 c) 81 7805994-6 12 Exempel 4 Verkan av profylaktisk bladbehandling gentemot Plasmo- para viticola på vinplantor i växthus.The active compounds, amounts of input and results is shown in the following table. 7805994-6 ll F '"_'» Associations according to Active Association Number of healthy the invention in g / kg seed seedlings cyclopropanecarboxylic acid-LN-0.4 79 (2-oxoperhydro-3-furyl) - 0.8 79 aning] 1.6 75 cyclopropanecarboxylic acid- 0.4 70 E2,6-dimethyl-N- (2-oxoperhydro- 0.8 76 a-furyn -anili fl 1.6 83 cyclopropanecarboxylic acid- 0.4 83 Lä-chloro-N- (2-oxoperhydro- 0.8 82 z-furyl) -anilic fl 1.6 93 cyclopropanecarboxylic acid - 0.4 77 3-methyl-N- (2-oxoperhydro-0.8 7l 3-furyl) -anilide 1.6 85 cyclopropanecarboxylic acid- 0.4 83 L? -Methoxy-N- (2-oxoperhydro- 0.8 87 s-furyl) -aniudl 1.6 sv Comparative associations -ethoxy-3-trichloro- 0.4 26 _ methyl-1,2,4-thiadiazole 0.8 44 1.6 53 tetramethyltiuram disulfide 4.8 21 9.6 50 Control I (3 repetitions) a) infected soil b) c) Control II (3 repetitions) a) 33 steam treated soil b) 86 c) 81 7805994-6 12 Example 4 Effect of prophylactic foliar treatment on Plasmodic para viticola on vines in greenhouses.
Unga plantor av vin med ca 5 - 8 blad besprutades dropp- våta med föreningarna i angivna koncentrationer. Då sprutbe- läggningen torkat in, besprutade man bladens undersida med en vattensuspension av sporangier av svampen (ca 20.000 per ml).Young seedlings of wine with about 5 - 8 leaves were sprayed drip- wet with the compounds in specified concentrations. When spraying the plant dried in, the underside of the leaves was sprayed with one aqueous suspension of sporangia of the fungus (about 20,000 per ml).
Man inkuberade därefter omedelbart plantorna i växthus vid 22 - 240 C i luft, som var maximalt mättad med vattenånga. Från och med andra dagen återställde man luftfuktigheten för 3 - 4 da- gar till normala värden (ca 30- - 70-procentig mättnad), var- efter man under ytterligare en dag höll atmosfären mättad med vattenånga. Därefter fastställde man för varje blad den pro- centuella andelen svampangripna fläckar och för att fastställa den fungicida verkan uträknade man medelvärdet av varje behand- ling enligt nedanstående formel: 100 ' angrepp på behandlade plantor 100 - = % verkan angrepp på obehandlade plantor 7805994~6 13 m~o_ø mm ïWwflcm|ñfiæuswumuouøæsuwmoxonmvnzuflævmä 1~|nofix|m¿amuwmnonumxcmmonmoaxmu 2 o _ o E. wvfiflcw| Säøwnmkonøanuwmoxo INVazlfiwøvwlm;lmuhwnønnmxfißmonmofixæu mN o _ o oofl Tina: Sïswumvofiwwnnwmoxo INVazvnøflflwlmøImuæmflonumxcmmoumofixæu mNo_o cv wfififlcøl^fl>uøw|m|oHw>nHwmoN0 imo|Z|fi>vw|&@Imnwmaonumxdømonmoflxæu mwo _ o oo mofiüâ.. Soäñzoaonwwflüwmøxø :NVszlflævwaN@|mHæwconHmx:mmoumoHxwu moo _ o ä Wïfiæ- Sæäñålouooouwmoxonï :z |H>moumomwHw|m_m@|mflæw:0Qumx:mmoumoHx>u mNo _ o ooH mäïøm.. Såsïmzouowofimooxo :mv|Z|EonQ|n%lmuæmøonumxcmmonmøflxwu m~o_o oofl ¶åH«fim|ñfimuøuamlouwæsummoxo INV|Z|u05Hm|m@lmuæmfionhmxfimmøumoaxmu om o _ o oo mäfløm- Sñsñåzouwšouwmoxoawo lzufiæuoflwlw_N@|mHMmfi0numxcmm0umofix>o Amflflcwumm EmwxHw> wv fimaoofløflb mummoëwmflm noflwøuucwucom uøñwucwm w .Gßvwunwxw cwmcflcflwmmmfl uwflflnw ummcflflwumm 7805994-6 14 .noucmfimfiflouacox mwmfiwcmswno wa mmwnmcm umflvøwuonmuoofi Hflflu wwamflflwsuwu H Umnxmnwn cmxuw> « Hoo_o Se... mNo~o mNo.o mNo_o 330 ooa oofl oofl on ooa oofl wflflflnml^H>nøw|m1oHUæsuwmoNo|~v lzlnoflxlm lmuæwconumxflmmoumofixmo Uflflfifiwlfiflæhømsmcouflmn |Hwm0x0|Nv1z imuæmnonumxflmmøumøaxav Éwflaflflmzfiaæuømlmlouflænuwmoxoawv|z unoflxflflnm.mwlmnæmnonnmxflmmøumoflxæu @äHflnm|Hflænøwnmnouwæsuwmoxouwv:Z |H>uwEoflv|m@nmnæmconumxcmmoumoflxæo .- @äHfi:m|Aflæuøulmnonøæsnmmoxoxmv |z|cm>o|m@lmnæwconumxcmmoumofixæo mvflflflcmn^Hæn:m|m|oHuæ:Hmmoxo|Nv |2|H>um|n@lmuæmconnmxcmmonmoflxæu ñmcflcwumm Emmxum> æv coflumuucmocom «mHooflufl> mummošmmfim uoëwucwm w fi :mzum> cwmcflacfiummø umflficw nßmcficmnwm 7805994-6 015 Exempel 5 Verkan av profylaktisk bladbehandling gentemot Phytopthora infestans på tomatplantor eller potatisplantor i växthus.The plants were then immediately incubated in greenhouses at 22 - 240 C in air, which was maximally saturated with water vapor. From and with the second day, the humidity was restored for 3 - 4 days to normal values (approx. 30- - 70% saturation), var- after keeping the atmosphere saturated for another day water vapor. Thereafter, for each leaf, the percentage of fungal spots and to determine the fungicidal effect, the mean value of each treatment was calculated. according to the following formula: 100 'infestation of treated plants 100 - =% effect infestation of untreated plants 7805994 ~ 6 13 m ~ o_ø mm ïWw fl cm | ñ fi æuswumuouøæsuwmoxonmvnzu fl ævmä 1 ~ | no fi x | m¿amuwmnonumxcmmonmoaxmu 2 o _ o E. wv fifl cw | Säøwnmkonøanuwmoxo INVazl fi wøvwlm; lmuhwnønnmx fi ßmonmo fi xæu mN o _ o oo fl Tina: Sïswumvo fi wwnnwmoxo INVazvnø flfl wlmøImuæm fl onumxcmmoumo fi xæu mNo_o cv w fififl cøl ^ fl> uøw | m | oHw> nHwmoN0 imo | Z | fi> vw | & @ Imnwmaonumxdømonmo fl xæu mwo _ o oo mo fi üâ .. Soäñzoaonww fl üwmøxø : NVszl fl ævwaN @ | mHæwconHmx: mmoumoHxwu moo _ o ä Wï fi æ- Sæäñålouooouwmoxonï: z | H> moumomwHw | m_m @ | m fl æw: 0Qumx: mmoumoHx> u mNo _ o ooH mäïøm .. Såsïmzouowo fi mooxo : mv | Z | EonQ | n% lmuæmøonumxcmmonmø fl xwu m ~ o_o oo fl ¶åH «fi m | ñ fi muøuamlouwæsummoxo INV | Z | u05Hm | m @ lmuæm fi onhmx fi mmøumoaxmu om o _ o oo mä fl øm- Sñsñåzouwšouwmoxoawo lzu fi æuo fl wlw_N @ | mHMm fi0 numxcmm0umo fi x> o Am flfl cwumm EmwxHw> wv fi maoo fl ø fl b mummoëwm fl m no fl wøuucwucom uøñwucwm w .Gßvwunwxw cwmc fl c fl wmmm fl uw flfl nw ummc flfl wumm 7805994-6 14 .noucm fi m fifl ouacox mwm fi wcmswno wa mmwnmcm um fl vøwuonmuoo fi H flfl u wwam flfl wsuwu H Umnxmnwn cmxuw> « Hoo_o See... mNo ~ o mNo.o mNo_o 330 ooa oo fl oo fl on ooa oo fl w flflfl nml ^ H> nøw | m1oHUæsuwmoNo | ~ v lzlno fl xlm lmuæwconumx fl mmoumo fi xmo U flflfifi wl fifl æhømsmcou fl mn | Hwm0x0 | Nv1z imuæmnonumx fl mmøumøaxav Éw fl a flfl mz fi aæuømlmlou fl ænuwmoxoawv | z uno fl x flfl nm.mwlmnæmnonnmx fl mmøumo fl xæu @ äH fl nm | H fl ænøwnmnouwæsuwmoxouwv: Z | H> uwEo fl v | m @ nmnæmconumxcmmoumo fl xæo .- @ äH fi: m | A fl æuøulmnonøæsnmmoxoxmv | z | cm> o | m @ lmnæwconumxcmmoumo fi xæo mv flflfl cmn ^ Hen: m | m | oHuæ: Hmmoxo | Nv | 2 | H> um | n @ lmuæmconnmxcmmonmo fl xæu ñmc fl cwumm Emmxum> æv co fl umuucmocom «MHoo fl u fl> mummošmm fi m uoëwucwm w fi: mzum> cwmc fl ac fi ummø um flfi cw nßmc fi cmnwm 7805994-6 015 Example 5 Effect of prophylactic foliar treatment against Phytopthora infestance on tomato plants or potato plants in greenhouses.
Unga plantor av tomat med minst 2 utslagna blad eller po- tatisplantor (t.ex. ur ögonsticklingar) minst 10 cm höga bespru- tades droppvåta med föreningarna i angivna koncentrationer.Young tomato plants with at least 2 outstretched leaves or seedlings (eg from eye cuttings) at least 10 cm high sprayed was allowed to drip wet with the compounds at the indicated concentrations.
Då sprutbeläggningen torkat in, besprutade man med en vattensus- pension av 50.000 - 80.000 sporangier av svampen och inkuberade därefter suspensionen i kylskåp ca 2 timmar vid llo C. Man inku- berade plantorna vid högre luftfuktighet och ca 15 - 180 C i växthus och beräknade efter ca 5 dagar den procentuella andelen angripna ytor på bladen. Den fungicida verkan beräknades på föl- jande sätt: 100 ° angrepp på behandlade plantor 100 - = % verkan angrepp på obehandlade plantor Verkan i % gentemot Phytophthora infestans på potatis* Föreningar enligt uppfinningen Koncentration (% verksam förening) 0,005 cyklopropankarbonsyra~[b-(2-oxoper- hyaro-3-fury1)-ani11d] 95 cyklopropankarbonsyra-E?,6-dimetyl-N- 0 (2-oxoperhydro-3-furyl)-anilid] 80 Jämförelseförening manganetylenbisditiokarbamat _ 50 ! Verkan beräknad i förhållande till 100-procentigt angrepp på obehandlade kontrollplantor 7805994-6 16 I' Verkan i % gentemot Phytophthora infestans på tomater* Föreningar enligt uppfinningen Koncentration -- (% verksam förening) 0,005 cyklopropankarbonsyra-Efl-(2-oxo- perhydro-3-furyl) -anilidj 10 0 cyklopropankarbonsyra-K3-metyl-N- (2-oxoperhydro-3-furyl)-anilid] 81 cyklopropankarbonsyra-[3-klor-N-(2- oxoperhydro-3-furyl)-anilidl 91 Jämförelseförening manganetylenbisditiokarbamat 67 \ *Verkan beräknad i förhållande till l00-procentigt angrepp på obehandlade kontrollplantor Exempel 6 Systemisk verkan av jordbehandling gentemot Phytophthora infestans på tomat- eller potatisplantor i växthus.When the spray coating dried in, spray with a water censor. pension of 50,000 - 80,000 sporangia of the fungus and incubated then the suspension in the refrigerator for about 2 hours at 10 ° C. prepared plants at higher humidity and about 15 - 180 C in greenhouse and calculated after about 5 days the percentage infested surfaces on the leaves. The fungicidal effect was calculated on the way: 100 ° infestation of treated plants 100 - =% effect infestation of untreated plants Effect in% on Phytophthora infestans on potatoes * Compounds of the invention Concentration (% active compound) 0.005 cyclopropanecarboxylic acid ~ [b- (2-oxoper- hyaro-3-fury1) -ani11d] 95 cyclopropanecarboxylic acid E, 6-dimethyl-N-O (2-oxoperhydro-3-furyl) -anilide] 80 Comparative association manganethylene bisdithiocarbamate _ 50 ! Effect calculated in relation to 100% attack on untreated control plants 7805994-6 16 IN' Effect in% on Phytophthora infestans on tomatoes * Compounds of the invention Concentration - (% active compound) 0.005 cyclopropanecarboxylic acid E- (2-oxo- perhydro-3-furyl) -anilide cyclopropanecarboxylic acid-K3-methyl-N- (2-oxoperhydro-3-furyl) -anilide] 81 cyclopropanecarboxylic acid [3-chloro-N- (2- oxoperhydro-3-furyl) -anilidine 91 Comparative association manganethylene bisdithiocarbamate 67 \ * Effect calculated in relation to 100% attack on untreated control plants Example 6 Systemic action of soil treatment against Phytophthora infestance on tomato or potato plants in greenhouses.
Man blandade de vägda föreningarna (vikt/volym) med åkerjord, fyllde jorden på krukor och planterade unga tomatf Å plantor med minst 2 utslagna blad eller potatisplantor (t.ex. ur ögonsticklingar) minst 10 cm höga. Efter den önskade förupp- komsttiden (t.ex. efter 4 eller 18 dagar) besprutade man plan- torna med en vattenhaltig suspension innehållande 50.000 - 80.000 sporangier av svampen per ml som ;inkuberats ca 2 timmar i kylskåp vid ll° C. Man inkuberade plantorna vid högre luft- fuktighet och ca l5 - 180 C i växthus och fastställde efter ca dagar den procentuella andelen angripna ytor på bladen. Den fungicida verkan beräknade man på följande sätt: 100 ' angrepp på behandlade plantor 100 “ = % verkan angrepp på obehandlade plantor 7805994-6 17 F Systemisk verkan av jordbehandling gentemot Phytophthora infestans på tomatplantor (vikt aktiv förening/volym) Föreningar ppm aktiv verkan* i % av behandling enligt förening 4 dagar före 18 dagar före uppfinningen inokulering inokulering cyklopropankarbon- 25 89 85 syra- N-(2-oxoperhydro- 3-furyl)-anilid 5 70 89 cyklopropankarbon- 25 92 82 syra-[?,6-dimetyl-N- (2-oxoperhydro-3- 5 40 71 furyD-anilid-I x verkan beräknad i förhållande till loo-preeengit angrepp på obehandlade kontrollplantor.The weighted compounds (weight / volume) were mixed with arable land, filled the soil with pots and planted young tomatoes seedlings with at least 2 sprouted leaves or potato seedlings (e.g. from eye cuttings) at least 10 cm high. After the desired pre- arrival time (eg after 4 or 18 days) the plant was sprayed with an aqueous suspension containing 50,000 - 80,000 sporangia of the fungus per ml incubated for about 2 hours in a refrigerator at 11 ° C. The plants were incubated at higher temperatures. humidity and approx. l5 - 180 C in greenhouses and determined after approx days the percentage of infested areas on the leaves. The fungicidal activity was calculated as follows: 100 'infestation of treated plants 100 “=% effect infestation of untreated plants 7805994-6 17 F Systemic action of soil treatment against Phytophthora infestance on tomato plants (weight active compound / volume) Compounds ppm active activity * in% of treatment according to compound 4 days before 18 days before invention inoculation inoculation cyclopropanecarbon- 89 89 85 acid- N- (2-oxoperhydro- 3-furyl) -anilide 5 70 89 cyclopropanecarbon- 92 92 82 acid - [?, 6-dimethyl-N- (2-oxoperhydro-3- 5 40 71 furyD-anilide-I x effect calculated in relation to loo-preeengit attack on untreated control plants.
Exempel 7 Kurativ verkan av bladbehandling gentemot Phytophthora infestans på tomat- eller potatisplantor i växthus.Example 7 Curative effect of foliar treatment against Phytophthora infestance on tomato or potato plants in greenhouses.
Unga tomatplantor med minst 2 utslagna blad eller pota- tisplantor (t.ex. ur ögonsticklingar) minst 10 cm höga bespru- tades med en vattensuspension innehållande 50.000 - 80.000, _ sporangier av svampen per ml inkuberad ca 2 timmar i kylskåp vid ll° C. Man inkuberade plantorna vid högre luftfuktighet.Young tomato plants with at least 2 sprouted leaves or potatoes plants (eg from eye cuttings) at least 10 cm high sprayed was taken with a water suspension containing 50,000 - 80,000, _ sporangia of the fungus per ml incubated for about 2 hours in the refrigerator at 11 ° C. The plants were incubated at higher humidity.
Efter den önskade föruppkomsttiden besprutade man plantorna droppvåta inom tiden för det latenta svampangreppet med fungi- ciden i den koncentration, som skulle undersökas. Då svampan- grepp påvisats hos de obehandlade kontrollplantorna fastställde man den procentuella andelen angripna ytor av bladen. Den fun- gicida verkan beräknades på följande sätt: 100 ' angrepp på behandlade plantor 100 “ = % verkan angrepp på obehandlade plantor 7805994-6 r Föreningar enligt uppfinningen sprutad aktiv förening % 18 verkan* i % vid behandling före 1 dag efter inokulering inokulering cyklopropankarbon- syra-[N-(2-oxoper- hydro-3-furyl)- anilidl cyklopropankarbon- syra-fl?,6-dimetyl- N-(2-oxoperhydro- s-furylranilifl Jämförelseförening manganetylenbis- ditiokarbamat 0,004 0,004 0,004 100 68 100 60 X verkan beräknad i förhållande till 100-procentigt angrepp på obehandlade kontrollplantor Exempel 8 Verkan vid behandling av korn gentemot Helminthosporium spec; Frön av korn, som angripits av Helminthosporium spec. behandlades med 50 mg verksam förening per 100 g frö. Fröna såd- des därefter i jorden och inkuberades i en klimatkammare vid 150 C. Försöket utvärderades efter 6 veckor, varvid fröplantor- na uppvisade stark minskning av angreppen i jämförelse med plan- tor i en obehandlad kontrollgrupp. 7805994-6 19 föreningar enligt uppfinningen Verkan i % cyklopropankarbonsyra-f4-metyl-N- (2-oxoperhydro-3-furyl)-anilidl 40 cyklopropankarbonsyra-E?,4-dimetyl- N-(2-oxoperhydro-3-furyl)-anilid] 40 cyklopropankarbonsyra-Ä?-etyl-N- (2-oxoperhydro-3-fury1>-aniliq] 40 obehandlade kontrollplantor 0 Exempel 9 Gränskoncentrationsförsök vid bekämpning av Pythium. ultimum. -procentiga beredningar i pulverform av de verksamma föreningarna blandades homogent med jord, som var starkt infek- terad med Pythium ultimum. Man fyllde den behandlade jorden på 0,5 liters lerkrukor och sådde utan karenstid i varje kruka 20 frön av märgärta (Pisum sativum L. convar. medullare Alef.) av sorten "Wunder von Kelvedon". Efter 3 veckors odling vid 20 - 24° C fastställde man antalet friska ärtplantor och utförde rotbonityr (l ~ 4). De verksamma föreningarna, insatsmängderna och resultaten framgår av följande tabell.After the desired pre-emergence period, the plants were sprayed drip wet within the time of the latent fungal attack with fungi the concentration at the concentration to be examined. When the fungus grips detected in the untreated control plants were established one the percentage of infested areas of the leaves. The fun- gicidal effect was calculated as follows: 100 'infestation of treated plants 100 “=% effect infestation of untreated plants 7805994-6 r Associations according to the invention sprayed Active Association % 18 effect * in% on treatment before 1 day after inoculation inoculation cyclopropanecarbon- acid- [N- (2-oxoper- hydro-3-furyl) - anilidl cyclopropanecarbon- acid- fl?, 6-dimethyl- N- (2-oxoperhydro- s-furylranili fl Comparative association manganethylene bis- dithiocarbamate 0.004 0.004 0.004 100 68 100 60 X effect calculated in relation to 100% attack on untreated control plants Example 8 Effect in treating barley against Helminthosporium spec; Seeds of barley, attacked by Helminthosporium spec. was treated with 50 mg of active compound per 100 g of seed. The seeds are sown- was then grounded and incubated in a climate chamber at 150 C. The experiment was evaluated after 6 weeks, with seedlings showed a strong reduction in attacks compared to the planned in an untreated control group. 7805994-6 19 compounds according to the invention Effect in% cyclopropanecarboxylic acid β-methyl-N- (2-oxoperhydro-3-furyl) -anilidel 40 cyclopropanecarboxylic acid E?, 4-dimethyl- N- (2-oxoperhydro-3-furyl) -anilide] 40 cyclopropanecarboxylic acid-N-ethyl-N- (2-oxoperhydro-3-furyl) -aniliq] 40 untreated control plants 0 Example 9 Limit concentration tests in the control of Pythium. ultimum. -percent formulations in powder form by those active the compounds were mixed homogeneously with soil which was highly infectious terad with Pythium ultimum. The treated soil was replenished 0.5 liter clay pots and sowed without waiting time in each pot 20 seeds of marjoram (Pisum sativum L. convar. medullare Alef.) of varieties "Wonders of Kelvedon". After 3 weeks of culture at 20 - At 24 ° C, the number of healthy pea plants was determined and performed rotbonityr (l ~ 4). The active associations, the amounts of contributions and the results are shown in the following table.
Rotbonityr: 4 = vita rötter utan svampnekros = vita rötter, någon svampnekros = bruna rötter, viss utveckling av svamp- nekros l = höggradig svampnekros, ruttnande rötter.Root bone: 4 = white roots without fungal necrosis white roots, some fungal necrosis = brown roots, some development of fungal necrosis l = high-grade fungal necrosis, rotting roots.
*N 3 8 mäflømu Såå 7805994-6 w 3 3 :Toëšflwmoxøfwå»vwalâ fz H ma om |uoHx|m@nøummconumxcmmoumoaxæu « ma ow N S 3 . mBJÉm.. âwhåwTouøwnnwmoxofwo -z N ß ow |Hxoumlwmtmnæmflonnmxcmmonmofixæu w . æfl om o» 3 3 Hfiäcm.. Såøwïmßofimšauwmoxoào å w ma om uuoøfim|w@nmuæwconnmxcmmoumofixæu w ou om v ma ow %øflHflcm:^H»Hsm|m|ouø>:ummoxox~o|z v wa om ušonßxmulmnæmconnmxcmmonmofixho q mfl ow q ON o q . mäflnm.. Swäfilmnøuøænuwmoxnïwo -z v wa om nuoøflu|m@nmuwmnonumxcmmoumofixæo Av 1 HV uoucmfimuum cwwcflcmumm mEEmmxuw> uwuflconuou mxwfiuw amucm :mv >m Uuofi H\mE H .onom øwmnfiasflmmmø umfiflcm mcficmumm 7805994-6 21 w æfl \ Ro _ øuon wmfimcøfiwnmcm w wa An w ma am Axwmumw mømmmummø mv HH fifioupaom H o 6 2% ømuwflšwwnfl A o »Q H H ^m Axmmuww wwmmwnmmø mv H Hflouucom H ofi oæ H w å fipßemnumxoflvflwu H m om |wflQ|N.H|:mHæ»w|cømcm§ m HH om m 3 3 Ein? Sšøwïmaofiøwßnwmoxnïwv Iz 1 | om |u0H¥flw|m_Nlmuæmnonuwxømmoumofixæo w wa ow v 3 3 mëfinw» âïøw..m|øäåfiwmoxonä »z w om o~ |cmæ0|m@lmnæwconuøxømmoumofixmo ^w I HV novcmflmuum cwmcflcwnmm mEEmmxnw> næuflconuou mxmflnw Høucm :mv >m wuon H\mE a .Unna cmmcflcflflmmmfl vmflficm mzficmnmm* N 3 8 mä fl ømu Såå 7805994-6 w 3 3: Toëš fl wmoxøfwå »vwalâ fz H ma om | uoHx | m @ nøummconumxcmmoumoaxæu «Ma ow N S 3. mBJÉm .. âwhåwTouøwnnwmoxofwo -z N ß ow | Hxoumlwmtmnæm fl onnmxcmmonmo fi xæu w. æ fl om o »3 3 H fi äcm .. Såøwïmßo fi mšauwmoxoào å w ma om uuoø fi m | w @ nmuæwconnmxcmmoumo fi xæu w ou om v ma ow% ø fl H fl cm: ^ H »Hsm | m | ouø>: ummoxox ~ o | z v wa om ušonßxmulmnæmconnmxcmmonmo fi xho q m fl ow q ON o q. mä fl nm .. Swä fi lmnøuøænuwmoxnïwo -z v wa om nuoø fl u | m @ nmuwmnonumxcmmoumo fi xæo Av 1 HV uoucm fi muum cwwc fl cmumm mEEmmxuw> uwu fl conuou mxw fi uw amucm: mv> m Uuo fi H \ mE H .onom øwmn fi as fl mmmø um fifl cm mc fi cmumm 7805994-6 21 w æ fl \ Ro _ øuon wm fi mcø fi wnmcm w wa An w ma am Axwmumw mømmmummø mv HH fifi oupaom H o 6 2% ømuw fl šwwn fl A o »Q H H ^ m Axmmuww wwmmwnmmø mv H H fl ouucom H o fi oæ H w å fi pßemnumxo fl v fl wu H m om | w fl Q | N.H |: mHæ »w | cømcm§ m HH om m 3 3 Ein? Sšøwïmao fi øwßnwmoxnïwv Iz 1 | om | u0H ¥ fl w | m_Nlmuæmnonuwxømmoumo fi xæo w wa ow v 3 3 më fi nw »âïøw..m | øäå fi wmoxonä» z w om o ~ | cmæ0 | m @ lmnæwconuøxømmoumo fi xmo ^ w I HV novcm fl muum cwmc fl cwnmm mEEmmxnw> næu fl conuou mxm fl nw Høucm: mv> m wuon H \ mE a .Unna cmmc fl c flfl mmm fl vm flfi cm mz fi cmnmm
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2724786A DE2724786C2 (en) | 1977-05-27 | 1977-05-27 | Cyclopropanecarboxylic acid [N- (2-oxoperhydro-3-furyl) anilide], processes for their preparation and fungicidal agents containing these compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7805994L SE7805994L (en) | 1978-11-28 |
| SE442868B true SE442868B (en) | 1986-02-03 |
Family
ID=6010435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7805994A SE442868B (en) | 1977-05-27 | 1978-05-25 | CYCLOPROPANCARBONIC ACID ANALIDES WITH FUNGICIDE EFFECTS AND THEIR USE IN FUNGICIDES |
Country Status (39)
| Country | Link |
|---|---|
| JP (1) | JPS53147061A (en) |
| AR (1) | AR220710A1 (en) |
| AT (1) | AT360803B (en) |
| AU (1) | AU520353B2 (en) |
| BE (1) | BE867556A (en) |
| BG (1) | BG28688A3 (en) |
| BR (1) | BR7803382A (en) |
| CA (1) | CA1108161A (en) |
| CH (1) | CH633784A5 (en) |
| CS (1) | CS203192B2 (en) |
| CY (1) | CY1163A (en) |
| DD (1) | DD136093A5 (en) |
| DE (1) | DE2724786C2 (en) |
| DK (1) | DK233878A (en) |
| EG (1) | EG13373A (en) |
| ES (1) | ES470195A1 (en) |
| FI (1) | FI68397C (en) |
| FR (1) | FR2392019A1 (en) |
| GB (1) | GB1603730A (en) |
| GR (1) | GR72966B (en) |
| HU (1) | HU184201B (en) |
| IE (1) | IE46923B1 (en) |
| IL (1) | IL54719A (en) |
| IT (1) | IT1096326B (en) |
| KE (1) | KE3241A (en) |
| LU (1) | LU79711A1 (en) |
| MX (1) | MX5224E (en) |
| MY (1) | MY8300210A (en) |
| NL (1) | NL7805404A (en) |
| NO (1) | NO149430C (en) |
| PH (1) | PH15700A (en) |
| PL (1) | PL110646B1 (en) |
| PT (1) | PT68075B (en) |
| RO (1) | RO75072A (en) |
| SE (1) | SE442868B (en) |
| SU (2) | SU727107A3 (en) |
| TR (1) | TR20568A (en) |
| YU (1) | YU40192B (en) |
| ZA (1) | ZA783036B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440780A (en) * | 1979-06-01 | 1984-04-03 | Chevron Research Company | Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones |
| EP0016985A1 (en) * | 1979-03-16 | 1980-10-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Substituted anilides, processes for their preparation, fungicides containing such compounds, and use of such compounds or fungicides in combating plant fungi |
| DE2920435A1 (en) * | 1979-05-19 | 1980-12-04 | Basf Ag | 2-AMINOPROPANAL ACETALS, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS FUNGICIDES AND METHOD FOR THE PRODUCTION OF SUBSTITUTED ANILINES |
| US4599351A (en) * | 1981-08-14 | 1986-07-08 | Chevron Research Company | Fungicidal 3-(N-acyl-N-arylamino) lactones |
| JPS61186735U (en) * | 1985-05-14 | 1986-11-21 |
-
1977
- 1977-05-27 DE DE2724786A patent/DE2724786C2/en not_active Expired
-
1978
- 1978-04-24 FI FI781264A patent/FI68397C/en not_active IP Right Cessation
- 1978-05-09 YU YU1102/78A patent/YU40192B/en unknown
- 1978-05-11 MX MX787079U patent/MX5224E/en unknown
- 1978-05-12 CA CA303,250A patent/CA1108161A/en not_active Expired
- 1978-05-15 PH PH21136A patent/PH15700A/en unknown
- 1978-05-16 IL IL54719A patent/IL54719A/en unknown
- 1978-05-18 NL NL7805404A patent/NL7805404A/en not_active Application Discontinuation
- 1978-05-18 TR TR20568A patent/TR20568A/en unknown
- 1978-05-23 CY CY1163A patent/CY1163A/en unknown
- 1978-05-23 PT PT68075A patent/PT68075B/en unknown
- 1978-05-23 GB GB21326/78A patent/GB1603730A/en not_active Expired
- 1978-05-24 IE IE1029/78A patent/IE46923B1/en unknown
- 1978-05-24 EG EG333/78A patent/EG13373A/en active
- 1978-05-24 AT AT380578A patent/AT360803B/en not_active IP Right Cessation
- 1978-05-24 JP JP6212278A patent/JPS53147061A/en active Granted
- 1978-05-24 PL PL1978207069A patent/PL110646B1/en unknown
- 1978-05-24 ES ES470195A patent/ES470195A1/en not_active Expired
- 1978-05-24 AR AR272308A patent/AR220710A1/en active
- 1978-05-25 LU LU79711A patent/LU79711A1/en unknown
- 1978-05-25 CS CS783406A patent/CS203192B2/en unknown
- 1978-05-25 DD DD78205587A patent/DD136093A5/en unknown
- 1978-05-25 RO RO7894166A patent/RO75072A/en unknown
- 1978-05-25 SE SE7805994A patent/SE442868B/en not_active IP Right Cessation
- 1978-05-25 IT IT23774/78A patent/IT1096326B/en active
- 1978-05-26 SU SU782621053A patent/SU727107A3/en active
- 1978-05-26 BR BR7803382A patent/BR7803382A/en unknown
- 1978-05-26 DK DK233878A patent/DK233878A/en not_active Application Discontinuation
- 1978-05-26 BG BG039862A patent/BG28688A3/en unknown
- 1978-05-26 CH CH580678A patent/CH633784A5/en not_active IP Right Cessation
- 1978-05-26 FR FR7815747A patent/FR2392019A1/en active Granted
- 1978-05-26 SU SU782621101A patent/SU784770A3/en active
- 1978-05-26 HU HU78SCHE646A patent/HU184201B/en unknown
- 1978-05-26 AU AU36529/78A patent/AU520353B2/en not_active Expired
- 1978-05-26 GR GR56344A patent/GR72966B/el unknown
- 1978-05-26 BE BE188101A patent/BE867556A/en not_active IP Right Cessation
- 1978-05-26 NO NO781838A patent/NO149430C/en unknown
- 1978-05-26 ZA ZA00783036A patent/ZA783036B/en unknown
-
1982
- 1982-10-28 KE KE3241A patent/KE3241A/en unknown
-
1983
- 1983-12-30 MY MY210/83A patent/MY8300210A/en unknown
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