NO149430B - CYCLOPROPANCARBOXYLIC ACID ANILIDES WITH FUNGICIDE EFFECT - Google Patents
CYCLOPROPANCARBOXYLIC ACID ANILIDES WITH FUNGICIDE EFFECT Download PDFInfo
- Publication number
- NO149430B NO149430B NO781838A NO781838A NO149430B NO 149430 B NO149430 B NO 149430B NO 781838 A NO781838 A NO 781838A NO 781838 A NO781838 A NO 781838A NO 149430 B NO149430 B NO 149430B
- Authority
- NO
- Norway
- Prior art keywords
- plants
- cyclopropanecarboxylic acid
- soil
- oxoperhydro
- anilide
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 12
- 230000000694 effects Effects 0.000 title description 11
- 239000000417 fungicide Substances 0.000 title description 4
- -1 CYCLOPROPANCARBOXYLIC ACID ANILIDES Chemical class 0.000 title description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 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 description 2
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical group ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OCHYJSATRBHPLB-UHFFFAOYSA-N n-phenylcyclopropanecarboxamide Chemical class C1CC1C(=O)NC1=CC=CC=C1 OCHYJSATRBHPLB-UHFFFAOYSA-N 0.000 claims description 2
- 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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 24
- 239000002689 soil Substances 0.000 description 18
- 239000013543 active substance Substances 0.000 description 17
- 241000233866 Fungi Species 0.000 description 13
- 244000061456 Solanum tuberosum Species 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 7
- 240000003768 Solanum lycopersicum Species 0.000 description 7
- 235000021536 Sugar beet Nutrition 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000233622 Phytophthora infestans Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000003032 phytopathogenic effect Effects 0.000 description 5
- 241000918584 Pythium ultimum Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000002361 compost Substances 0.000 description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 4
- 230000017074 necrotic cell death Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- 241001281803 Plasmopara viticola Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000069 prophylactic effect Effects 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
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 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
- 235000000292 Gouania lupuloides Nutrition 0.000 description 2
- 244000299452 Gouania lupuloides Species 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
- 241000238633 Odonata Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance 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
- VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-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
- 206010002368 Anger Diseases 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
- 241000221785 Erysiphales Species 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
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 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
- 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
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 239000004571 lime Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 231100000208 phytotoxic Toxicity 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Foreliggende oppfinnelse angår nye cyclopropancarboxylsyreanilider med fungicid virkning, som angitt i kravene. The present invention relates to new cyclopropanecarboxylic acid anilides with fungicidal action, as stated in the claims.
Midler med virkning mot fytopatogene sopper er tidligere kjent. Kjente midler av denne type er f.eks. 5-ethoxy-3-triklor-methyl-1,2,4-thiadiazol (US patent 3 260 588 og 3 260 725) og tetramethylthiuramdisulfid (DE patent 6^2 532). Disse midler oppviser imidlertid ikke alltid en tilfredsstillende virkning mot fytopatogene sopper. Agents with action against phytopathogenic fungi are previously known. Known means of this type are e.g. 5-ethoxy-3-trichloro-methyl-1,2,4-thiadiazole (US patent 3,260,588 and 3,260,725) and tetramethylthiuram disulfide (DE patent 6^2,532). However, these agents do not always show a satisfactory effect against phytopathogenic fungi.
Oppgaven ved foreliggende oppfinnelse er å fremskaffe forbindelser med bedre virkning mot fytopatogene sopper. The task of the present invention is to provide compounds with better action against phytopathogenic fungi.
Denne oppgave løses ifølge oppfinnelsen ved forbindelser med den generelle formel: According to the invention, this task is solved by compounds with the general formula:
hvor R^ er hydrogen eller alkyl med 1 - 4 carbonatomer, R2 er en fenylgruppe som eventuelt er substituert én eller flere ganger med .like eller forskjellige substituenter som er alkyl med 1-4 carbonatomer, alkoxy med 1-4 carbonatomer, alkylthio med 1-4 carbonatomer, halogen og/eller cyan. where R^ is hydrogen or alkyl with 1-4 carbon atoms, R2 is a phenyl group which is optionally substituted one or more times with the same or different substituents which are alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1 -4 carbon atoms, halogen and/or cyan.
Forbindelsene ifølge oppfinnelsen er overraskende overlegne over kjente midler med samme virkningsretning ved sin virkning mot fytopatogene sopper, og utmerker seg dessuten ved en god plante-forlikelighet og en tilstrekkelig virkningsvarighet. Da de dessuten ikke virker fytotoksisk i de anvendelsesmengder som i praksis kommer på-tale, kan de derfor med fordel anvendes i landbruket og i haver til bekjempelse av fytopatogene sopper. The compounds according to the invention are surprisingly superior to known agents with the same direction of action in their action against phytopathogenic fungi, and are also distinguished by good plant compatibility and a sufficient duration of action. As they are also not phytotoxic in the application amounts that come to mind in practice, they can therefore be used with advantage in agriculture and in gardens to combat phytopathogenic fungi.
Forbindelsene ifølge oppfinnelsen har fremragende fungicide The compounds according to the invention have excellent fungicidal properties
egenskaper mot skadesopper, som f.eks. falske melduggsopper. properties against harmful fungi, such as false powdery mildew fungi.
I motsetning til den bare forebyggende virkning hos kjente fungicide midler som f.eks. N-triklormethylthiofthalimid In contrast to the mere preventive effect of known fungicidal agents such as e.g. N-trichloromethylthiophthalimide
(U.S. patent 2 553 770, 2 553 771 og 2 553 ;776) og manganethylen-bisdithiocarbamat (U.S. patent 2 504 404 og 2 710 822) oppviser forbindelsene ifølge oppfinnelsen overraskende dessuten den ytter-ligere fordel at de har en kurativ og systemisk virkning og tillater derfor også bekjempelsen av sykdomsbevirkere som allerede er trengt inn i plantene. (U.S. 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) surprisingly, the compounds according to the invention also exhibit the further advantage that they have a curative and systemic effect and therefore also allows the combating of disease agents that have already penetrated the plants.
Av forbindelsene ifølge oppfinnelsen utmerker særlig cyclopropancarboxylsyre-[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilid], cyclopropancarboxylsyre-[3-klor-N-(2-oxoperhydro-3-furyl)-anilid] Of the compounds according to the invention, cyclopropanecarboxylic acid-[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide], cyclopropanecarboxylic acid-[3-chloro-N-(2-oxoperhydro-3-furyl)-anilide] stand out ]
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og cyclopropancarboxylsyre- [ 3-f luor-N- (2-oxoperhydro-3-f uryl),-anilid] seg ved en fremragende fungicid virkning og overtreffer virkestoffer av lignende konstitusjon og vjirkningsretning som forsøksrapporten viser. and cyclopropanecarboxylic acid- [3-fluoro-N-(2-oxoperhydro-3-furyl),-anilide] by an outstanding fungicidal effect and surpasses active substances of similar constitution and direction of action as the test report shows.
Anvendelsen kan enten skje med et virkestoff alene eller med blandinger av minst to konstitusjonsforskjellige virkestoffer av den foreliggende gruppe av forbindelser! Eventuelt kan andre fungicider, nematodicider, herbicider eller andre pestbekjempnings-midler, alt efter den ønskede hensikt, tilsettes. The application can either take place with an active substance alone or with mixtures of at least two constitutionally different active substances from the present group of compounds! Optionally, other fungicides, nematocides, herbicides or other pest control agents can be added, depending on the desired purpose.
Hensiktsmessig anvendes virkestoffene i form av preparater, som f. eks. pulvere, strømidler, granulater', oppløsninger, emul- Appropriately, the active substances are used in the form of preparations, such as e.g. powders, liquids, granules', solutions, emulsions
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sjoner eller suspensjoner, under tilsetning av flytende og/eller faste bærere, hhv. fortynningsmidler og eventuelt fukte-, hefte-, tions or suspensions, with the addition of liquid and/or solid carriers, respectively diluents and possibly wetting, binding,
emulgerings- oa/eller dispergeringshjelpemidler. emulsifying and/or dispersing aids.
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Egnede flytende bærere er vann, mineralolje eller andre organiske oppløsningsmidler, som f.eks. xylen, klorbenzen, cyclo-hexanon, dioxan, acetonitril, eddiksyfeester, dimethylformamid, isoforon og dimethylsulfoxyd.. !, Suitable liquid carriers are water, mineral oil or other organic solvents, such as e.g. xylene, chlorobenzene, cyclohexanone, dioxane, acetonitrile, acetic acid ester, dimethylformamide, isophorone and dimethylsulfoxyd.. !,
Som faste bærere er kalk, kaolin, kritt, talkum, attaclay As solid carriers are lime, kaolin, chalk, talc, attaclay
og andré leirer såvel som naturlige eller syntetiske kiselsyrer egnet. and andré clays as well as natural or synthetic silicic acids are suitable.
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Av overflateaktive stoffer kan f.eks. nevnes: salter av ligninsulfonsyrer, salter av alkylerte benzensulfonsyrer, sulfon-erte syreamider og deres salter, polyethoxylerte aminer og alko-holer . Surface-active substances can e.g. are mentioned: salts of ligninsulfonic acids, salts of alkylated benzenesulfonic acids, sulfonated acid amides and their salts, polyethoxylated amines and alcohols.
Når virkestoffene skal anvendes til frøbeising, kan også farvestoffer tilblandes, for å gi det beisede frø en tydelig synlig farve. When the active ingredients are to be used for seed staining, dyes can also be mixed in to give the stained seed a clearly visible colour.
Mengden av virkestoffet, hhv. virkestoffene i midlet kan variere innen vide grenser, idet den nøyaktige konsentrasjon av det for midlet anvendte virkestoff hovedsakelig avhenger av mengden i hvilken midlet bl.a. anvendes til jord- hhv. frøbehandling eller til bladbesprøytning. Eksempelvis inneholder midlet mellom ca. 1 til 80 vekt%, fortrinnsvis mellom 20 og 50 vekt% virkestoff og ca. 99 til 20 vekt% flytende eller faste bærere samt eventuelt inntil 20 vekt% overflateaktive stoffer. The amount of the active substance, respectively the active substances in the remedy can vary within wide limits, as the exact concentration of the active substance used for the remedy mainly depends on the quantity in which the remedy i.a. used for soil or seed treatment or for foliar spraying. For example, the agent contains between approx. 1 to 80% by weight, preferably between 20 and 50% by weight active substance and approx. 99 to 20% by weight liquid or solid carriers and possibly up to 20% by weight surfactants.
i De nye forbindelser med den generelle formel I kan fremstilles ved at man f eks. omsetter forbindelser med den generelle formel: i The new compounds with the general formula I can be prepared by e.g. reacts compounds with the general formula:
hvor R og er som ovenfor angitt, med cyclopropancarboxylsyre-klorid med formelen: where R and are as indicated above, with cyclopropanecarboxylic acid chloride of the formula:
i nærvær av en syreakseptor og eventuelt et oppløsningsmiddel, fortrinnsvis i ekvimolare mengdeforhold, og isolerer fremgangsmåte-produktene på i og for seg kjent vis. in the presence of an acid acceptor and possibly a solvent, preferably in equimolar quantities, and isolates the process products in a manner known per se.
Som syreakseptorer kan anvendes f.eks. organiske baser som pyridin, triethylamin eller N,N-dimethylanilin, eller uorganiske baser som hydroxyder, oxyder og carbonater av alkali- og jord-alkalimetaller, f.eks. natrium, kalium eller calcium. As acid acceptors can be used e.g. organic bases such as pyridine, triethylamine or N,N-dimethylaniline, or inorganic bases such as hydroxides, oxides and carbonates of alkali and alkaline earth metals, e.g. sodium, potassium or calcium.
Som oppløsningsmidler kan eventuelt anvendes f.eks. ether, tetrahydrofuran, benzen, eddiksyreester og< andre. Flytende syreakseptorer som f.eks. pyridin, kan samtidig anvendes som oppløs-ningsmiddel. As solvents, e.g. ether, tetrahydrofuran, benzene, acetic acid ester and others. Liquid acid acceptors such as pyridine, can simultaneously be used as a solvent.
Reaksjonen utføres hensiktsmessig ved temperaturer fra The reaction is conveniently carried out at temperatures from
-10°C til 120°C. -10°C to 120°C.
De følgende eksempler vil belyse fremstillingen av forbindelsene ifølge oppfinnelsen. The following examples will illustrate the preparation of the compounds according to the invention.
Eksempel 1 Example 1
Cyclopropanc arboxylsyre-[ N-( 2- oxoperhydro- 3- furyl)- anilid] Cyclopropanc carboxylic acid-[ N-(2- oxoperhydro- 3- furyl)- anilide]
( forbindelse nr. 1) (connection no. 1)
Til en oppløsning av 10,62 g (0,06 mol) 3-anilinoperhydro-furanon-2 i 50 ml pyridin tildryppes 6,30 g (0,06 mol) cyclo-propancarboxylsyreklorid ved 5 - 10°C innvendig temperatur under To a solution of 10.62 g (0.06 mol) 3-anilinoperhydrofuranone-2 in 50 ml pyridine, 6.30 g (0.06 mol) cyclopropanecarboxylic acid chloride is added dropwise at an internal temperature of 5 - 10°C under
i in
omrøring. Der omrøres videre i en halv time ved værelsetemperatur, derpå tilsettes 200 g vann/is og omrøres godt . stirring. Stir for half an hour at room temperature, then add 200 g of water/ice and stir well.
Efter avsugning vaskes omhyggelig med vann og tørres i tørre-skap. After vacuuming, wash carefully with water and dry in a drying cabinet.
Utbytte: 10,25 g = 70% av det teoretiske. Smp.: 104°C. Analogt kan de følgende forbindelser ifølge oppfinnelsen frem-st illes: Yield: 10.25 g = 70% of the theoretical. M.p.: 104°C. Analogously, the following compounds according to the invention can be produced:
Forbindelsene ifølge oppfinnelsen er som regel nesten farve-løse, luktløse, krystallinske stoffer, som er nesten uoppløselige i vann og bensin, men som derimot er meget godt oppløselige i polare organiske oppløsningsmidler som f.eks. aceton, dimethylformamid og dimethylsulfoxyd. The compounds according to the invention are usually almost colourless, odourless, crystalline substances, which are almost insoluble in water and petrol, but which, on the other hand, are very soluble in polar organic solvents such as e.g. acetone, dimethylformamide and dimethylsulfoxide.
Utgangsmaterialene for fremstilling av forbindelsen ifølge oppfinnelsen er i og for seg kjente eller kan fremstilles ved kjente fremgangsmåter. The starting materials for producing the compound according to the invention are known per se or can be produced by known methods.
De følgende eksempler tjener til å belyse anvendelsesmulig-hetene for forbindelsene ifølge oppfinnelsen. The following examples serve to illustrate the application possibilities for the compounds according to the invention.
Forsøk 1 Attempt 1
Grensekonsentrasjonsprøve ved bekjempelse av Pythium ultimum Limit concentration test for control of Pythium ultimum
20%-ige pulverformige virkestoffpreparat er ble blandet jevnt med jorden som var sterkt infisert med Pythium ultimum. Den behandlede jord ble fylt i 0,5 1 leirskåler, og uten karenstid ble der i hver skål sådd 20 korn markerter av sorten "Wunder von Kelvedon". Efter en dyrkningstid på 3 uker ved 20-24°C ble antallet av sunne erter bestemt og en rotbedømmelse (1-4) utført. A 20% powdered active ingredient preparation was mixed evenly with the soil which was heavily infected with Pythium ultimum. The treated soil was filled in 0.5 1 clay bowls, and without a withdrawal period, 20 marked grains of the variety "Wunder von Kelvedon" were sown in each bowl. After a cultivation period of 3 weeks at 20-24°C, the number of healthy peas was determined and a root assessment (1-4) was carried out.
Virkestoffer, anvendelsesmengder og resultater er angitt i den efterfølgende tabell. Active substances, application amounts and results are indicated in the following table.
Forsøk 2 Attempt 2
Beising av sukkerroer Pickling of sugar beets
Kalibrerte sukkerroefrø av sorten "Dieckmann-Suprapoly" ble beiset med 20%-ige pulverformige virkestoffpreparater. Leirskåler (20 x 20 x 5 cm) som rommet 2 1 jord, ble fylt med normal kompostjord ("Damping-off"), og i hver skål ble sådd 100 korn sukkerroefrø. Efter en dyrkningstid på 18 dager ved 1Q-21°C i drivhus ble de sunne frøplanter bestemt. Calibrated sugar beet seeds of the variety "Dieckmann-Suprapoly" were stained with 20% powdered active substance preparations. Clay bowls (20 x 20 x 5 cm) containing 2 1 soil were filled with normal compost soil ("Damping-off"), and 100 grains of sugar beet seeds were sown in each bowl. After a cultivation period of 18 days at 1Q-21°C in a greenhouse, the healthy seedlings were determined.
Virkestoffer, påføringsmengder og resultater er angitt i den følgende tabell. Active substances, application amounts and results are indicated in the following table.
F orsøk 3 Attempt 3
i in
I IN
Virkning av profylaktisk bladbehandling mot Plasmopara viticola på vinrankeplanter i drivhus ' Effect of prophylactic foliar treatment against Plasmopara viticola on grapevine plants in greenhouses'
Unge vinrankeplanter med ca. 5 til 8!blad ble besprøytet dryppvåle med den angitte konsentrasjon, efter tørring av sprøyte-belegget ble bladundersiden besprøytet med en vandig oppslemning av sporekapsler av soppen (ca. 20.000 pr. ml) og straks inkubert i drivhus ved 22-24°C og mest mulig vanndampmettet atmosfære. Fra den annen dag ble luftfuktigheten for 3 til 4 dager brakt til-bake til normalhøyde (omtrent 30-70% metning) og derpå i en ytter-ligere dag holdt på vanndampmetning. Derpå ble den prosentuelle del av den soppangrepne flate av hvert blad; notert , og av gjennom-snittet for hver behandling ble den fungicide virkning beregnet som følger: Young vine plants with approx. 5 to 8 leaves were sprayed with drip soap with the indicated concentration, after drying the spray coating, the leaf underside was sprayed with an aqueous slurry of spore capsules of the fungus (approx. 20,000 per ml) and immediately incubated in a greenhouse at 22-24°C and atmosphere saturated with water vapor as much as possible. From the second day, the humidity for 3 to 4 days was brought back to normal height (about 30-70% saturation) and then for a further day kept at water vapor saturation. Then the percentage of the infested area of each leaf was; noted, and from the average for each treatment, the fungicidal effect was calculated as follows:
i in
Forsøk 4 Attempt 4
Virkningen av profylaktisk bladbehandling mot Phytophthora infestans på tomatplanter eller potetplanter i drivhus The effect of prophylactic foliar treatment against Phytophthora infestans on tomato plants or potato plants in greenhouses
Unge tomatplanter med minst 2 utviklede løvblader eller potetplanter (f.eks. av øyenstiklinger) av minst 10 cm høyde ble sprøytet dryppvåte med angitte konsentrasjon, og efter tørring av sprøytebelegget ble de besprøytet med en vandig suspensjon inneholdende 50.OOO - 80.000 sporekapsler av soppen pr. ml og som var inkubert i ca. 2 timer i kjøleskap ved.ll°C. Plantene ble inkubert ved høy luftfuktighet, og ca. 15-18°C i drivhus, og den prosentuelle dei av angrepet bladflate ble bedømt efter ca. 5 dager. Den fungicidé virkning ble beregnet som følger :i Young tomato plants with at least 2 developed leaves or potato plants (e.g. of dragonfly cuttings) of at least 10 cm height were sprayed dripping wet with the indicated concentration, and after drying the spray coating they were sprayed with an aqueous suspension containing 50,000 - 80,000 spore capsules of the fungus per ml and which was incubated for approx. 2 hours in a refrigerator at 11°C. The plants were incubated at high humidity, and approx. 15-18°C in a greenhouse, and the percentage of the affected leaf surface was assessed after approx. 5 days. The fungicidal effect was calculated as follows: i
Forsøk 5 Attempt 5
Systemisk virkning av en jordbehandling mot Phytophthora infestans på tomatplanter eller på potetplanter i drivhus Systemic effect of a soil treatment against Phytophthora infestans on tomato plants or on potato plants in greenhouses
Man blander de avveide stoffer (vekt pr. volum) i åkerjord, fyller jorden i plantepotter og setter unge tomatplanter med minst 2 utviklede løvblader eller potetplanter (f.eks. fra øyenstiklinger) av minst 10 cm høyde. Efter utløpet av den ønskede forpåføringstid (f.eks. efter 4 eller 18 dager) besprøytes plantene med en vandig suspensjon inneholdende 50.000 - 80.000 sporekapsler av soppen pr. ml og inkubert i ca. 2 timer i kjøleskap ved 11°C. Plantene inkuberes ved høy luftfuktighet og ca. 15-18°C i drivhus, og man bedømmer efter ca. 5 dager den prosentuelle del av angrepet bladflate. Den fungicide virkning beregnes som følger: Systemisk virkning av jordbehandling mot Phytophthora infestans på tomatplanter (vekt aktiv forbindelse/volum) You mix the weighed substances (weight per volume) in field soil, fill the soil in plant pots and plant young tomato plants with at least 2 developed leaves or potato plants (e.g. from dragonfly cuttings) of at least 10 cm in height. After the end of the desired pre-application time (e.g. after 4 or 18 days), the plants are sprayed with an aqueous suspension containing 50,000 - 80,000 spore capsules of the fungus per ml and incubated for approx. 2 hours in a refrigerator at 11°C. The plants are incubated at high humidity and approx. 15-18°C in a greenhouse, and you judge by approx. 5 days the percentage of the affected leaf surface. The fungicidal effect is calculated as follows: Systemic effect of soil treatment against Phytophthora infestans on tomato plants (weight of active compound/volume)
Forsøk 6 Attempt 6
Kurerende virkning av en bladbehandling mot Phytophthora infestans på tomatplanter eller på potetplanter i drivhus Curative effect of a foliar treatment against Phytophthora infestans on tomato plants or on potato plants in greenhouses
Unge tomatplanter med minst 2 utviklede løvblader eller potetplanter (f.eks. av øyenstiklinger) på minst 10 cm høyde ble besprøytet med en vandig suspensjon inneholdende 50.000 - 80.000 sporekapsler av soppen pr. ml og inkubert i ca. 2 timer i kjøleskap ved ll°c. Plantene inkuberes ved høy luftfuktighet. Efter utløpet av den ønskede forpåføringstid sprøyter man i løpet av tiden for latent soppangrep plantene dryppvåte med; den konsentrasjon av fungicidet som skal prøves. Efter utbrudd av soppangrep i de ubehandlede kontrollplanter bedømmer man1 den prosentuelle del av angrepet bladflate. Den fungicide virkning beregnes som følger: Young tomato plants with at least 2 developed leaves or potato plants (e.g. from eye cuttings) of at least 10 cm height were sprayed with an aqueous suspension containing 50,000 - 80,000 spore capsules of the fungus per ml and incubated for approx. 2 hours in the refrigerator at 11°C. The plants are incubated at high humidity. After the end of the desired pre-application time, during the time for latent fungal attack, the plants are sprayed while dripping wet with; the concentration of the fungicide to be tested. After the outbreak of fungal attack in the untreated control plants, the percentage of the affected leaf area is assessed. The fungicidal effect is calculated as follows:
Forsøk 7 Attempt 7
Virkning av en behandling av byggfrø mot Helminthosporium spee. Effect of a treatment of barley seed against Helminthosporium spee.
Byggfrø angrepet av Helminthosporium spee. ble behandlet med 50 mg virkestoff pr. 100 g frø. Frøene ble så sådd i jord og inkubert i et klimakammer ved +15°C. ;Forsøket ble bedømt efter 6 uker, idet frøplantene oppviste et sterkt nedsatt angrep sammenlignet med planter i en ubehandlet kontrollgruppe. Barley seed attacked by Helminthosporium spee. was treated with 50 mg of active substance per 100 g of seeds. The seeds were then sown in soil and incubated in a climate chamber at +15°C. The trial was judged after 6 weeks, as the seedlings showed a greatly reduced attack compared to plants in an untreated control group.
Forsøk 8 Attempt 8
Gr ensekonsentrasjonsprøve ved bekjempelse av Pythium ultimum Gr ense concentration test for control of Pythium ultimum
20%-ige pulverformige virkestoffpreparater ble blandet jevnt med jorden, som var sterkt infisert med Pythium ultimum. Den behandlede jord ble fylt i leirskåler som tok 0,5 1 jord, og der ble uten karenstid i hver skål sådd 20 korn markerter (Pisum sativum L. convar. medullare Alef.) av sorten "Wunder von Kelvedon". Efter en dyrkningstid på 3 uker ved 20-24°C ble antallet av sunne erter bestemt og en rot bedømmelse (1-4) ble utført. Virkestoff, anvendelsesmengde og resultat er angitt i den nedenstående tabell. 20% powdered active ingredient preparations were mixed evenly with the soil, which was heavily infected with Pythium ultimum. The treated soil was filled in clay bowls that took 0.5 1 of soil, and in each bowl 20 grain markets (Pisum sativum L. convar. medullare Alef.) of the variety "Wunder von Kelvedon" were sown without a withdrawal period. After a cultivation period of 3 weeks at 20-24°C, the number of healthy peas was determined and a root assessment (1-4) was carried out. The active substance, application amount and result are indicated in the table below.
Rotbedømmelse: 4 = hvite røtter uten soppnekroser; Root assessment: 4 = white roots without fungal necrosis;
3 = hvite røtter, lite soppnekroser; 2 = brune røtter, alt sterkere soppnekroser; 1 = sterke soppnekroser, røtter morknet. 3 = white roots, little fungal necrosis; 2 = brown roots, increasingly stronger fungal necrosis; 1 = severe fungal necrosis, roots darkened.
Forsøksrapport Trial report
Forsøkene ble utført med sukkerbetefrø og potetplanter i The experiments were carried out with sugar beet seeds and potato plants in
drivhus og med drueplanter i utendørsforsøk som angitt nærmere nedenfor. greenhouse and with grape plants in outdoor trials as detailed below.
De spesielle forbindelser som ble prøvet og er identifisert nedenfor ved spesifikke nummere, er følgende: The particular compounds tested and identified below by specific numbers are as follows:
cyclopropancarboxylsyre-[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)- cyclopropanecarboxylic acid-[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-
anilid] = forbindelse nr. 2 anilide] = compound #2
cyclopropancarboxylsyre-[3-klor-N-(2-oxoperhydro-3-furyl)- cyclopropanecarboxylic acid-[3-chloro-N-(2-oxoperhydro-3-furyl)-
anilid] = forbindelse nr. 3 anilide] = compound #3
cyclopropancarboxylsyre-[3-fluor-N-(2-oxoperhydro-3-furyl)- cyclopropanecarboxylic acid-[3-fluoro-N-(2-oxoperhydro-3-furyl)-
anilid] = forbindelse nr. 4 anilide] = compound #4
Med disse forbindelser ifølge oppfinnelsen ble det sammen- With these compounds according to the invention, it was combined
lignet følgende forbindelser fra motholdene: resembled the following compounds from the counterparts:
US patent nr. 3 933 860 og US Patent No. 3,933,860 and
-US patent nr. 4 093 738 svarende til NOP 144 961 - US patent no. 4 093 738 corresponding to NOP 144 961
3-(N-kloracetyl-N-2,6-dimethylfenylamino)-y-butyrolacton 3-(N-chloroacetyl-N-2,6-dimethylphenylamino)-γ-butyrolactone
(US patent nr. 3 933 860 = forbindelse nr. 8) (US Patent No. 3,933,860 = Compound No. 8)
N-(1'-methoxycarbonyl-ethyl)-N-cyclopropylcarbonyl-2,4-dimethyl- N-(1'-methoxycarbonyl-ethyl)-N-cyclopropylcarbonyl-2,4-dimethyl-
anilin (US patent nr. 4 093 738 = forbindelse nr. 67) aniline (US patent no. 4,093,738 = compound no. 67)
N-(1<1->methoxycarbonyl-ethyl)-N-cyclopropylcarbonyl-2,4,6-tri-methylanilin (US patent nr. 4 093 738 = forbindelse nr. 143) N-(1<1->methoxycarbonyl-ethyl)-N-cyclopropylcarbonyl-2,4,6-tri-methylaniline (US Patent No. 4,093,738 = Compound No. 143)
De spesielle forsøk som ble utført, var de følgende: The special tests that were carried out were the following:
Forsøk 9 Attempt 9
I dette forsøk bemerkes det at den ikke fuktede (ikke spesi- In this experiment, it is noted that the non-moistened (not spe-
elt behandlede) kompostjord har en naturlig fungusflora som griper forstyrrende inn i utviklingen av friske frø. Dette bekreftes av kontrollprøve I nedenfor. Behandlingen av jorden med vanndamp ødelegger fungusen og tillater utvikling av en høy prosent av sunne frøplanter, se kontrollprøve II nedenfor. Ved hjelp av forbindelsene ifølge oppfinnelsen kan nesten det samme resultat som i kontrollprøve II erholdes med uforandret, dvs. treated) compost soil has a natural fungus flora that interferes with the development of fresh seeds. This is confirmed by control sample I below. The treatment of the soil with water vapor destroys the fungus and allows the development of a high percentage of healthy seedlings, see control sample II below. With the help of the compounds according to the invention, almost the same result as in control sample II can be obtained with unchanged, i.e.
ikke fuktet kompostjord. not moistened compost soil.
Behandling av sukkerbetefrø Treatment of sugar beet seeds
Standardstørrelser av sukkerbetefrø av merket "Dieckmann-Suprapoly" ble behandlet med de aktive midler angitt nedenfor i form av pulverformige preparater av 20% konsentrasjon. Leirskåler av størrelse 20 x 20 x 5 cm og med et volum på 2 liter jord ble så fylt med ufuktet kompostjord, og 100 sukkerbetefrø ble sådd i hver skål. Skålene ble så underkastet dyrkning i 17 dager ved 22 til 25°C i et drivhus. I forsøkene nedenfor ble sunne frøplanter tellet. Standard sizes of sugar beet seeds of the brand "Dieckmann-Suprapoly" were treated with the active agents indicated below in the form of powdered preparations of 20% concentration. Clay bowls of size 20 x 20 x 5 cm and with a volume of 2 liters of soil were then filled with unmoistened compost soil, and 100 sugar beet seeds were sown in each bowl. The dishes were then cultured for 17 days at 22 to 25°C in a greenhouse. In the experiments below, healthy seedlings were counted.
rr
Helbredende aktivitet ved potetplanter mot Phytophthora infestans Curative activity of potato plants against Phytophthora infestans
I dette forsøk ble der anvendt potetplanter fra "eyebud graf ts". Plantene var minst 100 cm høye. Plantene ble så besprøytet jevnt med en suspensjon som ble holdt i 2 timer ved 11°C. Suspensjonen inneholdt ca. 100.000 sporehus av Phytophthora infestans pr. ml. For å forbedre betingelsene for infeksjon ble plantene så anbrakt i et drivhus i 24 timer i en vanndampmettet atmosfære. In this experiment, potato plants from "eyebud graf ts" were used. The plants were at least 100 cm tall. The plants were then sprayed evenly with a suspension which was kept for 2 hours at 11°C. The suspension contained approx. 100,000 spore houses of Phytophthora infestans per ml. To improve the conditions for infection, the plants were then placed in a greenhouse for 24 hours in a water vapor saturated atmosphere.
Plantene ble derefter sprayet slik at de var dryppvåte med forbindelsene angitt nedenfor. Efter 10 dager ble forholdet av infiserte bladflater bestemt, og på basis av denne bestemmelse ble aktiviteten av behandlingen beregnet ved følgende formel: ,100 • infeksjon av behandlede planter _ ...... 100 - :—■=—.—: A 7—r ri—^ .,r , = % aktivitet The plants were then sprayed so that they were dripping wet with the compounds listed below. After 10 days, the ratio of infected leaf surfaces was determined, and on the basis of this determination, the activity of the treatment was calculated by the following formula: ,100 • infection of treated plants _ ...... 100 - :—■=—.—: A 7—r ri—^ .,r , = % activity
infeksjon av ubehandlede planter infection of untreated plants
De aktive midler ble påført som et 20%-ig pulverformig preparat. The active agents were applied as a 20% powdered preparation.
Resultatene av forsøkene var som følger: The results of the trials were as follows:
Forbindelser Connections
Utendørsforsøk på vinranker infisert med Plasmopara viticola . Unge vinrankeplanter av Gamay-typen som var blitt plantet om våren, fikk lov til å utvikles inntil rankene var ca. 30 cm lange. Plantene ble så delt i grupper på 4 planter hver. Hver gruppe ble sprayet ved 6 gjentatte påføringer med forbindelsene angitt nedenfor i konsentrasjonene som også er angitt, inntil de var nesten dryppvåte. 6 grupper med 4 planter hver fikk stå ubehandlet for sammenligning. Outdoor trials on grapevines infected with Plasmopara viticola. Young vine plants of the Gamay type that had been planted in the spring were allowed to develop until the vines were approx. 30 cm long. The plants were then divided into groups of 4 plants each. Each group was sprayed in 6 repeated applications with the compounds indicated below in the concentrations also indicated until they were almost dripping wet. 6 groups of 4 plants each were left untreated for comparison.
På den følgende dag ble alle planter, dvs. behandlede og ubehandlede planter, forurenset med en spraytåke av en suspensjon av Plasmopara viticola-sporer og ble deretter vætet daglig for å hjelpe på infeksjonen. On the following day, all plants, i.e. treated and untreated plants, were contaminated with a spray mist of a suspension of Plasmopara viticola spores and were then wetted daily to aid in the infection.
Hele fremgangsmåten ble gjentatt i et første forsøk efter 15 og 32 dager og i et annet forsøk bare én gang efter 17 dager. For å bestemme aktiviteten av forbindelsene ble antallet av angrepne blader tellet på to forskjellige dager. Ved denne telling ble bare blader med sporedannende infeksjoner tellet. The entire procedure was repeated in a first trial after 15 and 32 days and in a second trial only once after 17 days. To determine the activity of the compounds, the number of attacked leaves was counted on two different days. In this count, only leaves with spore-forming infections were counted.
De aktive midler ble påført i form av et 20%-ig pulverformig preparat. Forsøkene ble utført i Angers, Frankrike. The active agents were applied in the form of a 20% powdered preparation. The trials were conducted in Angers, France.
Detaljene ved forsøkene er som følger: The details of the trials are as follows:
Første forsøk (behandling gjentatt efter 15 og 32 dager) First attempt (treatment repeated after 15 and 32 days)
Annet forsøk (behandling gjentatt efter 17 dager) Second attempt (treatment repeated after 17 days)
Konklusjoner Conclusions
Det fremgår av ovenstående forsøk at forbindelser ifølge foreliggende oppfinnelse har en forbausende bedre fungicid aktivitet. Forbindelsene er meget aktive både i drivhus og under de strengere betingelser ved utendørs forsøk. Deres aktivitet var profylaktisk såvel som helbredende og var effektiv mot forskjellige typer av fungi. It appears from the above experiments that compounds according to the present invention have a surprisingly better fungicidal activity. The compounds are very active both in greenhouses and under the stricter conditions of outdoor trials. Their activity was prophylactic as well as curative and was effective against different types of fungi.
Sammenligningsforbindelsene anvendt fra motholdene, har i praktisk talt alle tilfelle en betraktelig lavere fungicid virkning . The comparison compounds used from the counters have in practically all cases a considerably lower fungicidal effect.
Claims (4)
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 (3)
| Publication Number | Publication Date |
|---|---|
| NO781838L NO781838L (en) | 1978-11-28 |
| NO149430B true NO149430B (en) | 1984-01-09 |
| NO149430C NO149430C (en) | 1984-04-25 |
Family
ID=6010435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781838A NO149430C (en) | 1977-05-27 | 1978-05-26 | CYCLOPROPANCARBOXYLIC ACID ANILIDES WITH FUNGICIDE EFFECT |
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) | SU784770A3 (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 TR TR20568A patent/TR20568A/en unknown
- 1978-05-18 NL NL7805404A patent/NL7805404A/en not_active Application Discontinuation
- 1978-05-23 PT PT68075A patent/PT68075B/en unknown
- 1978-05-23 CY CY1163A patent/CY1163A/en unknown
- 1978-05-23 GB GB21326/78A patent/GB1603730A/en not_active Expired
- 1978-05-24 AT AT380578A patent/AT360803B/en not_active IP Right Cessation
- 1978-05-24 EG EG333/78A patent/EG13373A/en active
- 1978-05-24 PL PL1978207069A patent/PL110646B1/en unknown
- 1978-05-24 JP JP6212278A patent/JPS53147061A/en active Granted
- 1978-05-24 AR AR272308A patent/AR220710A1/en active
- 1978-05-24 IE IE1029/78A patent/IE46923B1/en unknown
- 1978-05-24 ES ES470195A patent/ES470195A1/en not_active Expired
- 1978-05-25 IT IT23774/78A patent/IT1096326B/en active
- 1978-05-25 LU LU79711A patent/LU79711A1/en unknown
- 1978-05-25 SE SE7805994A patent/SE442868B/en not_active IP Right Cessation
- 1978-05-25 RO RO7894166A patent/RO75072A/en unknown
- 1978-05-25 DD DD78205587A patent/DD136093A5/en unknown
- 1978-05-25 CS CS783406A patent/CS203192B2/en unknown
- 1978-05-26 BG BG7839862A patent/BG28688A3/en unknown
- 1978-05-26 CH CH580678A patent/CH633784A5/en not_active IP Right Cessation
- 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 DK DK233878A patent/DK233878A/en not_active Application Discontinuation
- 1978-05-26 AU AU36529/78A patent/AU520353B2/en not_active Expired
- 1978-05-26 BR BR7803382A patent/BR7803382A/en unknown
- 1978-05-26 SU SU782621101A patent/SU784770A3/en active
- 1978-05-26 SU SU782621053A patent/SU727107A3/en active
- 1978-05-26 ZA ZA00783036A patent/ZA783036B/en unknown
- 1978-05-26 FR FR7815747A patent/FR2392019A1/en active Granted
- 1978-05-26 NO NO781838A patent/NO149430C/en unknown
- 1978-05-26 HU HU78SCHE646A patent/HU184201B/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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