IE46923B1 - Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and use - Google Patents
Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and useInfo
- Publication number
- IE46923B1 IE46923B1 IE1029/78A IE102978A IE46923B1 IE 46923 B1 IE46923 B1 IE 46923B1 IE 1029/78 A IE1029/78 A IE 1029/78A IE 102978 A IE102978 A IE 102978A IE 46923 B1 IE46923 B1 IE 46923B1
- Authority
- IE
- Ireland
- Prior art keywords
- furyl
- oxoperhydro
- cyclopropanecarboxylic acid
- anilide
- compound
- Prior art date
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Cyclopropanecarboxanilides have the following formula in which R1 is hydrogen or C1-C4-alkyl, R2 denotes an aromatic hydrocarbon radical or an aromatic hydrocarbon radical which is substituted one or more times by identical or different substituents comprising C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halogen, trifluoromethyl, nitro, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl and/or cyano, and n denotes the number 1 or 2. The compounds of the formula I are prepared by reacting a cyclopropanecarbonyl chloride with an appropriate 3-anilino-2-perhydrofuran. Fungicides contain, as the active component, at least one new compound of the formula I.
Description
The present invention is concerned with new fungi ci dally active cyclopropanecarboxylic acid anilides, with the use of these compounds for controlling phytopathogenic fungi and also with a process for the manufacture of the new active compounds.
Agents that act against phytopathogenic fungi have already been known.
Agents of this kind known in practice are, for example,
- ethoxy - 3 - trichloromethyl - 1,2,4 - thiadiazole
Τθ (United States Patent Specification Nos. 3,260,588 and
3,260,725) and tetramethylthiuram disulphide (German Patent Specification No. 642, 532). These agents, however, do not always have a satisfactory action against phytopathogenic fungi.
The problem upon which the present invention is based •has been to provide an agent having an outstanding action against phytopathogenic fungi. This problem is now solved in accordance with the present invention by the compounds of the general formula I, as defined below.
-3The present invention provides compounds of the general formula 1
in which
R-| represents a hydrogen atom or an alkyl group containing
1 to 4 carbon atoms,
R2 represents an unsubstituted aromatic hydrocarbon group or an aromatic hydrocarbon group substituted by one or more substituents selected from alkyl groups containing 1 to 4 carbon atoms, alkoxy groups containing
1 to 4 carbon atoms, alkylthio groups containing 1 to 4 carbon atoms, halogen atoms, trifluoromethyl groups, nitro groups, alkoxycarbonyl groups containing 1 to 4 carbon atoms in the alkoxy part, alkylcarbonyl groups containing 1 to 4 carbon atoms in the alkyl part and cyano groups, and n represents 1 or 2.
-4When the substituted aromatic hydrocarbon group represented by R2 contains two or more substituents these substituents may be the same or different.
ί
It is to be understood herein that when the unsubstituted or substituted aromatic hydrocarbon group represented by R contains more than one aromatic ring, these rings may be fused together in the ortho-positions or may be isolated as in for example, biphenyl.
The action of the compounds of the present invention against phytopathogenic fungi is surprisingly superior to that of known agents having the same direction of action and, moreover, these compounds are distinguished by a good plant tolerance and a sufficient duration o.f action. Since, in addition, they do not act phytotoxically when applied in the quantities that come into consideration in practice, they may accordingly be used advantageously in agriculture and in horticulture for controlling phytopathogenic fungi.
The compounds of the present invention have outstanding fungicidal properties against pathogenic fungi, for example false mildew fungi.
In contrast to known fungicidal agents having only a preventive action such as, for example, N-trichloromethyl thiophthalimide
469 23
-5(United States Patent Specifications Nos. 2,553,770, 2,553,771 and 2,553,776) and manganese ethylene bisdithiocarbamate (United States Patent Specifications Nos, 2,504,404 and 2,710,822), the compounds of the present invention surprisingly also have the additional advantage of a curative and systemic action which, therefore, makes it possible also to control pathogenic agents that have already penetrated into the plants.
The present invention accordingly also provides a fungicidal preparation which comprises a compound of the general formula I, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds of the general formula I.
The present invention further provides a method of protecting a living plant against phytopathogenic fungi, wherein the living plant is treated with a compound of the general formula I.
The present invention further provides a method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with a compound of the general formula
I.
The present invention further provides a method of dressing seeds, wherein the seeds are treated with a compound of
69 23
-6the general formula I.
The present invention further provides a pack which comprises a compound of the general formula I together with instructions for its use for controlling phytopathogenic fungi.
The compounds of the present invention that are especially distinguished by an outstanding fungicidal action are those of the general formula I given above in which Rj represents a hydrogen atom or a methyl or ethyl group and Rg represents a phenyl, methylphenyl, dimethylphenyl, ethylphenyl, 1sopropylphenyl, methoxyphenyl ethoxyphenyl, methylthiophenyl, fluorophenyl, chlorophenyl, bromopheny.l, dichlorophenyl, trifl uoromethyl phenyl, nitrophenyl, cyanophenyl, methoxycarbonyl15 phenyl, acetylphenyl or biphenylyl group.
The new active compounds may be applied singly or, alternatively, mixtures of at least two constitutionally different compounds of the general formula I may be applied. If desired, other fungicides, nemato2o cides, herbicides or other types of pest-controlling agents may be added, depending on the purpose.
The active substances are advantageously applied in the form of fungicidal preparations, for example powders,
-7strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents and, if desired, of wetting, adhesive, emulsifying and/or dispersing agents.
Suitable liquid carriers are, for example, water, mineral oils or other organic solvents, for example xylene, chlorobenzene, cyclohexanol, dioxan, acetonitrile, ethyl acetate dimethylformamide, isophorone and dimethyl sulphoxide.
Suitable solid carriers are, for example, lime, kaolin, chalk, talcum, attaclay and other clays as well as natural or synthetic silicic acid.
As surface-active agents there may be mentioned, for example, salts of ligninsulphonic acids, salts of alkylated benzenesulphonic acids, sulphonated acid amides and salts thereof, 15 polyethoxylated amines and alcohols.
When the active substances are to be used for dressing seeds, they may also be admixed with dyestuffs in order to give the dressed seeds a clearly visible colour.
The proportion of active substance(s) in the fungicidal preparations may vary within wide limits, the exact concentration of the active substances used for the preparations being primarily dependent on the quantity in
-8whfch the preparations inter alia are to be used for treating soil or seeds or for spraying leaves. The preparations may contain, for example, approximately 1 to 80% by weight, preferably between 20 and 50% by weight, of active g compound(s), approximately 99 to 20% by weight of liquid or solid carrier and also, if desired, up to 20% by weight of surface-active agent(s).
The new compounds of the general formula I may be produced by the process of the present invention as defined below.
The present invention further provides a process for the manufacture of a compound of the general formula I, wherein a compound of the general formula II (CH2)n--CH-NH-R, ‘2 (II)
R.
in which Rp R2 and n have the meanings given above, is reacted in the presence of an acid-binding agent and, if
46323
-9desired, a solvent with cyclopropanecarboxylic acid chloride of the formula III
The compound of the general formula II of the formula III are preferably used proporti ons.
and the compound in equimolar
As acid-binding agents there may be used, for example, organic bases, for example pyridine, triethylamine or N,Ν-dimethylani1ine, or inorganic bases, for example hydroxides, oxides and carbonates of alkali metals and alkaline earth metals, for example sodium, potassium or calcium.
As a solvent that may optionally be used, there may be mentioned, for example, ether, tetrahydrofuran, benzene or ethyl acetate. Liquid acid-binding agents, for example pyridine, may serve simultaneously as solvents.
The reaction is advantageously carried out at a temperature within the range of from -10°C to 120°C.
The products of the process of the present invention may be isolated in a manner known perse.
6 9 2 3
-10Some specific compounds of the present invention are listed in the following Table.
Compound
No. Name Physical constant
1 Cyclopropanecarboxylic acid [N-(Z-oxoperhydro-3-fury1)anilide]
M.p.: 104°C
Cyclopropanecarboxylic acid [2,5-diethyl-N-(2-oxoperhydro3-furyl)-aniTide]
M.p.: 102-103°C
Cyclopropanecarboxylic acid [2-methoxy-N-(2-oxoperhydro3-furyl)-anilide]
M. p.:175-176°C
Cyclopropanecarboxylic acid [2-methyl-N-(2-oxoperhydro3-furyl)-anilide]
M.p.: 108-109°C
M.p.: Π4-Π6°ε
6 Cyclopropanecarboxylic acid [2,5-dimethyl-N-(2-oxoperhydro3-furylj-anilideJ
Cyclopropanecarboxylic acid [2,6-dimethyl-N-(2-oxoperhydro3-furyl)-ani11 dej
M.p.: 84°C
6 9 3 3
Compound
No. Name
Physical constant
-Il7 Cyclopropanecarboxylic acid £ 3-methyl-N-(2-oxoperhydro5 3-furyl)-ani 1 i de]
M.p.: 109°C
Cyclopropanecarboxylic acid [4-methy1-N-(2-oxoperhydro3-furyl )-ani 1 ide]
M.p.: 123°C
Cyclopropanecarboxylic acid [3,4-dimethy1-N-(2-oxoperhydro-3 furyl)-ani 1 ide]
M.p.: 99-100°C
Cyclopropanecarboxylic acid [2,3-dimethyl-N-(2-oxoperhydro3-furyl) -ani 1 i de]
11 Cyclopropanecarboxylic acid [2 , 4-dimethyl-N-(2-oxoperhydro3-furyl)-aniTide]
M.p.: 153°C
M.p.: 85-86°C
M.p.: 103°C
Cyclopropanecarboxylic acid [3,5-dimethyl-N-(2-oxoperhydr020 3-furyl)-ani1ide]
469 23
-12Compound
No.Name_Physical constant
Cyclopropanecarboxylic acid M.p.: 119-121°C ^2,4,6-tri methyl-N-(2-oxoperhydro-3-furyl )-anilide]
Cyclopropanecarboxylic acid f4-ch^oro-N-(2-oxoperhydro3-furyl )-ani 1 ide]
M.p.: 149-150°C
Cyclopropanecarboxylic acid C 3-ch1oro-N-(2-oxoperhydro3-furyl)-ani1i de]
M.p.: 99-100°C
Cyclopropanecarboxylic acid [4-isopropy!-N-(2-oxoperhydro3-furyl)-ani1i de]
M.p.: 108-110°C
17 - Cyclopropanecarboxylic acid M.p.: 104-105°C £3-trifluoromethyl-N-(2-oxoperhydro -3-f uryl) -ani Tide]
Cyclopropanecarboxylic acid M.p.: 89°C [3-fluoro-N-(2-oxoperhydro3-furyl)-anilide]
6923
Compound
No. Name
Physical constant
-1319 Cyclopropanecarboxylic acid [3-bromo-N-(2-oxoperhydro-3furyl)-ani1i de]
H.p.: 93-94°C
Cyclopropanecarboxylic acid [2,6-di isopropyl-N-(2-oxoperhydro -3-furyl) - ani 1 i de]
M.p.: 215-216UC
Cyclopropanecarboxylic acid [2-ethyl-N-(2-oxoperhydro3-furyl)-ani1ide]
M.p.: 103°C
Cyclopropanecarboxylic acid
C4-ethyl-N-(2-oxoperhydro3-furyl) - an i1i de3
M.p.: 1O7°C 15 23 Cyclopropanecarboxylic acid ^4-methoxy-N-(2-oxoperhydr03-furyl)-anili de}
M.p.: 75°C
M.p.: 144-145°C
Cyclopropanecarboxylic acid f4-bromo-N-(2-oxoperhydro3-furyl)-anilide]
46933
-14Compound
No.
29
Name_Physical
Cyclopropanecarboxylic acid M.p
i.4-fluoro-N-(2-oxoperhydro3-furyl)-anilide]
Cycloprop'anecarboxyl ic acid M.p £2-ethoXy-N-(2-oxoperhydro3-furyl)-anilide]
Cyclopropanecarboxylic acid M.p.
£3-chloro-2-methyl-N-(2-oxoperhydro-3-furyl)-anili de]
Cyclopropanecarboxylic acid M.p.
£5-chloro-2-methyl-N-(2-oxoperhydro-3-furyl)-ani1i de] pn
Cyclopropanecarboxylic acid ηθ £4-methoxy-2-methyl-N-(2oxoperhydro-3-furyl)-ani1i de]
2Ω
Cyclopropanecarboxylic acid n^ £4-ethoxy-N-(2-oxoperhydro3-furyl)-anilide]
Cyclopropanecarboxylic acid M.p.
[5-chloro-2-methoxy-N-(2-oxoperhydro-3-furyl)-anili de] constant .: 138-139°C .: 143-145°C : 121-124°C : 114-116°C = 1.5520 = 1.4579 : 163-164°C
Compound
No.
Name
Physical constant
-1532 Cyclopropanecarboxylic acid [3-chloro-N-(5-methyl-2-oxoperhydro-3-furyl)-ani1ide]
M.p.: 95-97°C
Cyclopropanecarboxylic acid {3-ethyl-N-(2-oxoperhydro3-furyl)-ani1i deJ
M.p.: 69-70°C
Cyclopropanecarboxylic acid [3 -cyano-N-(2-oxoperhydro3-furyl)-ani1i de]
M.p.: 142-143UC
Cyclopropanecarboxylic acid (3-thiomethyl-N-(2-oxoperhydro3-furyl )-ani 1 i de] n^° = 1.5888
36 Cyclopropanecarboxylic acid [2,3-dichloro-N-(2-oxoperhydro3-furyl)-ani1i de]
M.p.: 136-137UC
Cyclopropanecarboxylic acid [3-chloro-N-(5-methy1-2-oxoperhydro-3-furyl)-ani1i de]
M.p.: 95-97°C
The compounds of the present invention are in general almost
469 23
-16colourless, odourless, cystalline substances which are practically Insoluble in water and benzine, but, in contrast, are very readily soluble in polar organic solvents, for example acetone,dimethylformamide and dimethyl sul5 phoxide.
The starting compounds for the manufacture of the compounds of the present invention are known per se or may be produced according to processes known per se.
The following Examples illustrate the invention. Example
1 illustrates the manufacture of the compounds of the present invention and Examples 2 to 9 illustrate the possibilities of application of the compounds of the present invention.
Example 1 15 Cyclopropanecarboxylic acid [N-(2-oxoperhydro3-furyl )-aniTide] (Compound No. 1)
6.30 g (0.06 mole) of cyclopropanecarboxylic acid chloride were added dropwise, at a 5 to 10°C internal
2q temperature, while stirring, to a solution of 10.62 g (0.06 mole) of 3-ani1inoperhydrofuran-2-one in 50 ml of pyridine. The mixture was then stirred for J hour at room temperature and then poured on to 200 g of water/ice and stirred well. After filtering with suction, the mixture
-17was carefully washed with water and dried in a drying cupboard.
Yield: 10.25 g=70% of the theoretical yield; m.p.:104°C Each of the other compounds of the present invention listed in the Table above may be produced in an analogous manner.
Example 2
Limiting Concentration Test in the Control of Pythium Ultimum
In a series of tests 20% pulverulent active substance preparations were mixed uniformly with soil which was severely infected with Pythium ultimum. The treated soil was placed in clay dishes each having a capacity of 0.5 litre and, without a waiting period, 20 marrowfat peas of the Kelvedon Wonder variety were sown in each dish. After a cultivation period of three weeks at 20 to 24°C the number of healthy peas was determined and an assessment (1-4 as defined below) of the roots was carried out.
The active substances used and their application quantities, and also the results, are given in the following Table.
469 23
Infected soil
cn ο
PO CO TO o ω rt CO a a II II II II σ Φ 3 rt G) 3 rt tA σ- € < 3 ro 3 Φ τ 3“ 3 S> ro -□ O < o rt» rt· tA c. ro Φ £ rt rt tA rt 3 3 Φ Φ Φ (A t—t Φ tA o rt (rt 3 3 3 tA -J. rt. rt) O ¢5 O 3 —4 © C o O o ro 3 3 rt rt rt 3 V) IQ w w CA rt 0) w «* tl —j £ Ω tA —4» 3 O rt Φ 3 3* Ω (A IQ O 3 ad» 3* c o Q. rt rt IA Φ Φ 3 rt rt) (A SU c C w cr 3 3 (Q I© 3 «< tu ευ O _□ e (A •j Φ 3 3 o. < Φ Φ << Φ Π n 3 3 3 ro cr cu -s ro O O o tA tA © rt) Φ Φ rt c tA tA (A 3 «. u·
tO ευ
Φ η
-ί ο
Μ
Φ tA ω co ο •Ρ* 4» ·Ρ*
Ξ
ΙΦ (Α
Ο
Χ3
Φ ευ (Λ rt sr φ
<
Φ rt
Ο
Ο
Ο η
φ rt
Ο rt
j.
Ο
3*
Φ rt
3* <<
ευ σ» ω
Φ φ
¢+
Compound according to Active substance Number of Root
-21Example 3
Dressing of Sugarbeet
In a series of tests graded sugarbeet seeds of the variety Dieckmann Suprapoly were dressed with 20% pulverulent active substance preparations. Clay dishes each of 2 litres capacity (20x20x5 cm) were filled with normal compost soil (damping-off) and 100 of the sugarbeet seeds were sown in each dish. After a cultivation period of 18 days at 19 to 21°C in a greenhouse the number of healthy seedlings was determined.
The active substances used and their application
quantities, and also the results, are given in the following Table. Compound according to Active substance Number of healthy seedlings from the invention in g/kg seed 100 seeds Cyclopropanecarboxylic acid 0.4 7-9 £li - (2-oxoperhydro-3-furyl) - 0.8 79 ani 1 i de] 1.6 75 Cyclopropanecarboxylic acid 0.4 70 [2,6-dimethyl-N-(2-oxoper- 0.8 76 hydro-3-furyl)-ani1ide] 1.6 83 Cyclopropanecarboxylic acid 0.4 83 £ 3 -ch1oro-N-(2-oxoperhydro- 0.8 82 3-furyl)-ani1i de] 1.6 93
6 8 2 3
22'
□. rt· H ro art 1* cn 1 > CQ CO 1 Γ! ro o << gj 1 τ—*> GJ Γ3 << w ¢+ ro m ro “b I o -b 1 Π c -ϊ u rt 3 c 3 C 3 art GJ -Ρ» 3 rt ,-5 ro o -s ro o •σ 3 1 O V> ct XJ << ci- XJ 3 ro ct X 3* -5 —· s' -s rt. rt 3* X •b •art O o •art © Q. S’ rt. 1 o 1 X *3 1 art XJ ro << ft) w -5 ft) ft) ft) 1 o —j ct | 3 1 3 3 Z 3 rt rt. rt n rt. s ro rt. 1 ro S’ ft> 5 o rt 1 n art π rt, N rt. 3 rt, •—a CJ rt. ro £) c O n •σ Q. ro -s Ca- j “S •5 —j ar ft) .Φ t e- ro Q O’ OJ ro UJ o o t—» X © 3 o rt. X X o VI o << T3 << o o XJ rt ro art 1 3 ' 3 ro rt. -5 rt. ro “S Ω S’ O rt 3* << 3 << ft) Or ft) fir Π -s n “S rt. o rt, 1 o Ct Ct
ι
IO -ph σ» oo
-< ο ο σ» co -Ρ* cn ro Ο —1 cn ο
ο
Cft ro ro
Q.
W
Compound according to Active substance Number of healthy the invention in g/kg seed seedlings from
6 9 2 3
-23Compound according to the invention
Active substance Number of in g/kg seed healthy seedli ngs from 100 seeds
Control I (3 repetitions)
Infected soil a)
b)
c)
Control II (3 repetitions)
Steamed soil a)
b)
c)
Example 4
Effect of Prophylatic Leaf Treatment against Plasmopara vi ti cola on Vines in a Greenhouse
In a series of tests young vines having approximately 5 to 8 leaves were sprayed until dripping wet with the concentration of active substance indicated in the Table below and, after the spray coating had dried on, were sprayed on the undersides of the leaves with an aqueous suspension of sporangia of the fungus indicated in the heading above (approximately 20,000 per ml), and Immediately incubated in a greenhouse at 22 to 24°C in an atmosphere as saturated with water vapour as possible. From the second day onwards
46823
-24the air humidity was reduced to the normal level for 3 to 4 days (approximately 30 to 70% saturation) and then maintained at water vapour saturation for a further day. The percentage proportion of the surface attacked fay fungi of each leaf was then recorded and the average per treatment was calculated as follows to determine the fungicidal effect:
100 x attack in treated plants
100 = % effect attack in untreated plants hydro-3-fury1)-ani1ide]
-26σ»
CO 1 r-i ro o << CO 1 r—l ft O << CO 1 m ft O «< -b C r—i ro 0 << -h 1 ft “h I ft -b 1 ft -s 1 ft c Φ c “+) mJ c φ aJ << Φ —J “i c+ 0 O T ct O ct 0 << 3· 3 << c Ό kJ 3Γ *3 «—» 3 Ό •—1 0 -s mJ 0 mJ << -J 1 << “5 X 0 *«—' -5 O *M» mJ O OJ mJ O | << σ 1 0 Ό I 1 •3 3 1 •a Ol 1 qj 0> 1 pJ a z QJ «j« z OJ 3 Z s 3 z 3 3 1 3 —J 1 3 1 Φ «J· 1 Φ ul> - z—». Φ —j. z—. φ Z~«» ft J ft M> ro ft CL ro n *4f ro £U «J* ro Oi wJa 1 oj Φ . 1 OJ O. 1 •5 CL 1 CL 0 1 u-J 0 Ύ Φ 0 σ* Φ 0 CT Φ X cr X O’ U4 X o U-f X 0 kJ 0 0 0 O 0 X 0 X •a X •3 X X5 «< Ό << n> << Φ << Φ mJ Φ mJ mJ -5 Ml -J. -5 -J. 3- «J. ΖΓ »J« 3“ ft 3~ O << ft *< ft << << CL CL CL 0» Q. OJ *5 OJ -s QJ “J ft -s ft O ft 0 ft σ «j· O •ala I _J. 1 «1. 1 CL 1 CL CL co CL
ι
O
O 45» ct
3* φ
<
Φ ct
O
ro
CH ro o
ro
Ol
O ro cn
1Λ £
σ*
1Λ ct
SU ft
Λ i?Q
O>
ft <
rt>
Compound according to % Effect against Concentration hydro-3-furyl)-ani1ide]
o o o
O O O |\3 hO ςη tn CM
O o
ΓΌ
Ul c
cr (/) f+ &t
O
Φ &>
o
Γ+
-J· <
Φ o
o n
Φ r+
-S
CD f+
O
46833
Compound according to ^Effect against Concentration.
-29Example 5
Effect of prophylactic leaf treatment against Phytophthora infestans in tomato plants or potato plants in a greenhouse
In a series of tests young tomato plants having at least two developed foliage leaves and potato plants (for example from eye cuttings) at least 10 cm tall were sprayed until dripping wet with the concentration of active substance indicated in the Table below and, after the spray coating had dried on, were sprayed with an aqueous suspension which contained per millilitre 50,000 to 80,000 sporangia of the fungus indicated in the heading above and which had been incubated in a refrigerator at 11°C for approximately 2 hours. The plants were incubated at a high level of air humidity and at approximately 15 to 18°C in a greenhouse and, after approximately 5 days, the percentage proportion of leaf surface that had been attacked was assessed. The fungicidal effect was calculated as follows:
2o 100 x attack in treated plants
100 _ =% effect attack in untreated plants
-30%Effect against Phytophthora infestans in potatoes +)
Concentration (%
Compound according to the active su5stance) invention 0.005
Cyclopropanecarboxylic acid 95 [N-(2-oxoperhydro-3-furyl) anilide]
Cyclopropanecarboxylic acid 80 [2,6-dimethyl-N-(2-oxoperhydro3-fury1)- anilide]
Agent for comparison
Manganeses ethylene bisdithio- 50 carbamate ^Effect against Phytophthora infestans 15 in tomatoes +)
Compound according to Concentration (% the invention actl've substance)
0.005
Cyclopropanecarboxylic acid [N-(2-oxoperhydro-3-furyl)20 anilide]
100
-31%Effect against Phytophthora infestans in tomatoes +)
Compound according to the Concentration (% invention active substance)
I ,
0.005
Cyclopropanecarboxylic acid 81 [3-methyl-N-(2-oxoperhydro-3furyl)-ani1i del
Cyclopropanecarboxylic acid 91 £3-chloro-N-(2-oxoperhydro-310 furyl)-anilidej
Agent for comparison
Manganese ethylene bisdithio- 67 carbamate
+) Effect was calculated on 100% attack in the untreated 15 control.
Example 6
Systemic effect of soil treatment against Phytophthora infestans in tomato plants in a greenhouse
In a series of tests the substances to be tested, which had been 20 weighed out (weight by volume), were mixed with arable soil which was then placed in plant pots, and young tomato
-32plants having at least two developed foliage leaves were placed in these pots. After the desired pre-dose time (for example after 4 or 18 days) had expired, the plants were sprayed with an aqueous suspension which contained per millilitre 50,000 to 80,000 sporangia of the fungus indicated in the heading above and which had been incubated in a refrigerator at 11°C for approximately 2 hours. The plants were incubated .at a. high level of air humidity and at approximately 15 to 18°C in a greenhouse and, after approximately 5 days the percentage proportion of leaf surface that had been attacked was assessed. The fungicidal effect was calculated as follows:100 x attack in treated plants 100 _._-_ =% effect attack in untreated plants rn “b re o
<+ £
0»
V) o
cu o
c fij cf re
CL o
O
O !tu cf cf a* π
TV '3 rf
3* re c
re cu cf re
a.
Ω
O cf
O
-33o
ro tn tn uo o ro «xl 00 —> ro tn iv r”“i o z <<
-j. ι r>
-J. ro o
CL I XJ re o 3 «—> x o
O XJ
XJ CU re 3 fl>
Π << Ο»
CL -5
-5 CT o o
I X co
-b “-1· c o
-i << cu —> o
I CL ro tn σι xj co o kO co co to tn cf o
O O cf XJ 3- Q re c 3
-· CL 3 < a» re n n
cf O
O CL
-<· (Q tn xj c XJ σ- 3 tn cf cu ο» n 3 rf n -j· re < re
-»·
O CL r> a> c << —J ISi Qi cf CT -»· re O -h· 3 O 3 ro rn
-b
-b re o
cf +
o
-b cf
-s re cu cf re
->· co 3
O CL π a» c<< —j ω 0i cf cr -.. n> O -h 3 O re
-i. co <<
-+, tn re cf tn re cf 3
Q> -J.
a
ΙΛ re
-j. -+>
-b re cf O O cf
0> o cf -b O tn
X3 O __| —J. £U —J cf cf W -s re
0i cf re rf
0) to
CU ω
rf io
3“ <<
rf
O
XJ
3“ cf
CT o
-i
CU
46933
-34Example 7
Curative effect of leaf treatment against Phytophthora infestans in tomato plants in a greenhouse
In a series of tests young tomato plants having at least 5 two developed foliage leaves were sprayed with an aqueous suspension which contained per millilitre 50,000 to 80,000 sporangia of the fungus indicated in the heading above and which had been incubated in a refrigerator at 11 °C for approximately 2 hours. The plants were incubated at a high level of air humidity. After the desired pre-dose time Had expired, the plants were sprayed until dripping wet, within the period of latent fungal attack, with the concentration to be tested of the fungicide indicated in the Table below. After the outbreak of fungal attack in the untreated control plants the percentage proportion of leaf surface that had been attacked was assessed. The fungicidal effect was calculated as follows:
100 x attack in treated plants
100 _ =% effect attack in untreated plants
46323
-35cn o
+ O 2 > 3 r—» o ro »—» O ro ro IO *< ro << 3 z *< -s 3 ro CL w n 1 n m cr (Q 3 -5 σ\ -j —I ~b ro ro (+ O 1 o —1. ro O “b 3 3 t CL Ό CL 1 X, ro ro ro “b co —»· -3 ro o -J o (+ V) O t 3 O k-U X o <+ ro ro -s +) ro XJ o XJ c c+ ro XJ ro £ ro o -s 3* 3 ro 3 ro (+ o << << ro -s ro tfl 3 3 —t o 3“ o << •CJ ·-—· 1 ro ro π ro 1 z -s CL “5 ro ro -3 ro I cr “5 cr _j 3 3 o O o o ro t/1 -j. ro X 1 X c O —« 1 << co << —t cr 3 —J. o —J I —-1 ro —1. CL X —1. +) -j. eh ω ro o n c Ω ro CL LJ •σ -s o. mJ. ro ro << ro (+ s a —J D o ΖΓ 1 —j. 3 -I. cl 1 CL
o o
©
Oi
CtCh ro
Λ xo o o ©
o eh . 4* ro o
eh O fl> XJ O
-j. c
3 < (X ro ro (+ o
-»· o o o
3
CL (O eh
O (Λ ΙΛ S-ii
O c > -Ϊ cr o ro v> r+ << f-J· m>l ro ro < cl 3 ro n ro <+ ro ro r+ ro
o.
o o
(+
O o cr m n ro ·+ C -h -b —j o ro ro -3 n <+ ro r+
Ml.
O + 3 ’
O cn cn © co (+
-s —· —i ro 3 ro ο ο. γιο ro 3 c << ro —ι 3 ro ro et<+ -b —I. ¢-+ o ro 3 *5
-36.Example 8
Effect of treatment of barley grains against Helminthosporium spec.
In a series of tests barley grains that had been attacked by 5 Helminthosporium spec, were treated with 50 mg of active substance per 100 g of grains. The grains were then sown in soil and incubated in an air-conditioned chamber at +15°C. The tests were evaluated after 6 weeks and the resulting seedlings exhibited a markedly reduced attack as compared with plants of an untreated control group.
The results are given in the following Table.
Compound according to the invention_%Effect
Cyclopropanecarboxylic acid β - methyl- N-(2oxope rhydro-3-furyl)-anil ide[ 40
15Cyc1opropanecarboxylic acidj2,4 - dimethyl - N - (2oxoperhydro-3-furyl)-anilide[ 40
Cyclopropanecarboxylic acid [4 - ethyl - N - (2oxoperhydro-3-furyl) -anil i de] 40
Untreated control 0
Example 9
Limiting concentration test in the control of
Pythi urn ultimum
In a series of tests 20% pulverulent active substance
-37preparations were mixed uniformly with soil which was severely infected with Pythi urn ultimum. The treated soil was placed in clay dishes each having a capacity of '0.5 litre and, without a waiting period, 20 marrowfat peas (Pisum sativum L. convar. medullare Alef) of the Kelvedon Wonder variety were sown in each dish. After a cultivation period of 3 weeks at 20 to 24°C the number of healthy peas was determined and an assessment (1-4 as defined below) of the roots was carried out.
The active substances used and their application quantities, and also the results are given in the following Table.
469X3 ro -o tn σι
ι COp—f 1 ro o ‘to? wnp ι to«< Wr-o 1 -h ι ro -s 1 o “b I << -b ι ro -h 1 n -b ι n c n —· 30 —· con C -h —— c σ-4 c -b—1 *5 *< o «<3 0 “1 r+ —' -S -4 0 S 5 O •5 -JO *< oj o CL—'XJ k 30 << CXS << 0*0 << C -3 —13 -5 “J O *51 —» Ο Ό —— O -5 --3 -? —Ό 5 O O O 5 O *— X -s *-5 O *--o O •—-5 O 1 1 Ό 1 Ο Ό « «< O 1 Ο XJ 1 1 -CJ 1 Ο xj OJ Z OJ CO 1 Φ OJ | xj OJ I OJ QJ Z OJ 0> 1 0> 3 1 3 1 Z3 3 Z OJ 3 Z3 3 1 3 3 Z3 ro -b 1 Φ 1 3 -j. ι ro -j·**» ro -ι. ι ro —* PO ft C«-^O —*<—ro —j-—. π -J PO ft - »»—. ro 1 OJ -5 tno> -ι. isi n -i. ro o> -j. 1 OJ -4· PO 0> 0.0 S «< ι -s ‘ CL I OJ CL I -j 0.0 -s CL 1 -5 . Φ.Χ Ρu—·© o --3cr χ-^ro o -s *—’x 3 • ΦιΟ 3 >—’χ O . rc.* o· o o ,ro -o X 1 ¢+ X o o O X XJ X O X Φ *< OJ 3<< XJ X Ό «< ro t< O t< «5 -i □ <<-> IPX Φ —» -s —' ro —* S' -*· —I. —J —1. “5 —‘ -j _i. 3 -4. -s -*· << O —· 1 ro 3 -*· 3 ro «< ro 3 n o. «-· ro < ro «< o. «< -s φ CL I CD CL CL OJ Τ 0» CL 0) o n u££ 2. ί o> -s n O ft -s ro 1 -J* ο n O -4» 1 -»· o -4« Q. o o. 1 ·—· 1 Q. o. 1 CX cl 00 4^ Γ\3 οο φ» ro 00 4!» PO CO 4^ PO οο φ* r\3 co -t» ro Ο Ο O o o o O o o o o o oo o o o o 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 tQ tO U3 tQ tQ tQ to tQ to (O to IQ to to to to to to —»—· ro ΓΟ —» —4 m*po—4 co co o to to σι to «*J ·Μ oo to 00 OtOvj to o co 4* -0» -J 4=* PC PO 0» 4* 4* 4!» 4* 4> 4» 4* 4*
a
Ο •σ ro ο
ω
Compound according to Active substance Number of Root the invention concentration in healthy assement
46823
39no
O on
-JNU A 30 O
II II tl II O rt·
3» ω (Λ ft (Λ (Λ ft 3 c+ white roots without fungal necroses; white roots, slight fungal necroses; brown roots, considerably severe fungal necroses severe fungal necroses, mouldy roots (JI o
(/)*-* o )-ιο O r-i3> W_o rf CO O 3 ω o CL ft (Q ι ft 3 “h 3 -*· 3 ft -hv O OJ T rt ft -S rt· r+(3 3 c CO —« 3 ft 5 O ft “5 3“ ft rt- -s I o ft Ό O r+O O -·· 3 *< ex -σ CX ft —» ftft—· O ft -h “S rf CL rf Γ) W O o (Λ -J. >—t -J, —1 ft ft 5 ι 3~σ O rf h (Λ rf -$ ft -J ft O cr ft o 3 0 3 —. o -j. o ft rt- O -i. -5 o 3 —· 3 3 3-3 —j o a (Λ 1/) ft *< Ό --· 1 ft rt· —J ft CLZ1 ft ft -s .ro. I cr 1—^23 -J· 1—>~o ft (Λ ro x O t << —1 3 o —‘ X -«· ro I o o -CJ cr ft ft ~5 n (Λ t i d hydro- oo 4* ro CO 4* ro o cr ft o cr ft ο ο o O O O -----. 3 3 3 3 3 3 (Q (0(0(0 B-l —-1 __1 _l _J —J O 1 CO -Ο LD o o —· o CO CO Jfl* -Ρ» -ft ___ --- I CO LO
Γ+- o
Claims (2)
- CLAIMS 1, A compound of the general formula I in which R-] represents a hydrogen atom or an alkyl group containing 1 to 5 4 carbon atoms, R 2 represents an unsubstituted aromatic hydrocarbon group or an aromatic hydrocarbon group substituted by one or more substituents selected from alkyl groups containing 1 to 4 carbon atoms, alkoxy groups containing 1 to 4 carbon atoms, 10 alkylthio groups containing 1 to 4 carbon atoms, halogen atoms, trifluoromethyl groups, nitro groups, alkoxycarbonyl groups containing 1 to 4 carbon atoms in the alkoxy part, alkylcarbonyl groups containing 1 to 4 carbon atoms in the alkyl part and cyano groups, and 15 H. represents 1 or 2, 469 23 -412. A compound as claimed in claim 1, wherein represents a hydrogen atom or a methyl or ethyl group and R 2 represents a phenyl, methylphenyl, dimethyl phenyl, ethylphenyl, isopropyl phenyl, methoxyphenyl, ethoxyphenyl, methyl thiophenyl, 5 fluorophenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl, nitrophenyl, cyanophenyl, methoxycarbonyl phenyl, acetylphenyl or biphenylyl group. 3. Cyclopropanecarboxylic acidp) - (2- oxoperhydro 3 - furyl) - anilide]. 10 4. Cyclopropanecarboxylic acid[2,6 - diethyl - N - (2 - oxoperhydro - 3 - furyl) - anilide], 5. Cyclopropanecarboxylic acid[l· - methoxy - N - (2oxoperhydro - 3 - furyl) -anilide]. 6. Cyclopropanecarboxylic acid[2 - methyl - N - (2 15 oxoperhydro - 3 - furyl) - anilid]. 7. Cyclopropanecarboxylic acid[2,6 - dimethyl - N - (2 - oxoperhydro - 3 - furyl) - anilide], 8. Cyclopropanecarboxylic acid[2,5 - dimethyl - N - (2oxoperhydro - 3 - furyl) anilide]. 20 9. Cyclopropanecarboxylic acid 3 - methyl - N - (2 46933 -42oxoperhydro - 3 - furyl) anilide] 10. Cyclopropanecarboxylic acid £4 - methyl - N - (2 oxoperhydro -3 - furyl) - anilide] 11. Cyclopropanecarboxylic acid£3, 4 - dimethyl - N 5 (2 - oxoperhydro - 3 - furyl) - anilide] 12. Cyclopropanecarboxylic acidjl·, 3 - dimethyl- N - (2 - oxoperhydro - 3 - furyl) - ani lid]. 13. Cyclopropanecarboxylic acid [2, 4 - dimethyl - N (2 - oxoperhydro - 3 - furyl) - anilidej 10 14. Cyclopropanecarboyxlic acid^3, 5 - dimethyl - N (2 -oxoperhydro - 3 - furyl) - anilide] 16. Cyclopropanecarboxylic acid^2,4, 6 - trimethyl - N (2 - oxoperhydro - 3 - furyl)-ani1id^. 16. Cyclopropanecarboxylic acidj/l - chloro - N - (2 15 oxoperhydro - 3 - furyl) - anilidej. 17. Cyclopropanecarboxylic acid [3 - chloro - N - (2 oxoperhydro - 3 - furyl) - anilidej. 18. Cyclopropanecarboxylic acidJJ - isopropyl - N - (2 oxoperhydro - 3 - furyl) - anilide] 4 6 9 2 3 -4319. Cyclopropanecarboxylic acid £3 - trifluoromethyl N - (2 - oxoperhydro - 3 - furyl) - anilide], 20. Cyclopropanecarboxylic acid£3 - fluoro - N - (2 oxoperhydro - 3 - furyl) - anilide]. 5 21. Cyclopropanecarboxylic acid £3 - bromo - N - (2 oxoperhydro - 3 - furyl) - anilide]. 22. Cyclopropanecarboxylic acid £2, 6 - diisopropyl - N (2 - oxoperhydro - 3 - furyl) - anilide] 23. Cyclopropanecarboxylic acid£2 - ethyl - N 10 (2 - oxoperhydro - 3 - furyl) - anilide]. 24. Cyclopropanecarboxylic acid£4 - ethyl - N - (2 oxoperhydro - 3 - furyl) anilide]. 25. Cyclopropanecarboxylic acid £4 - methoxy- N - (2 oxoperhydro - 3 - furyl) - anilide]. 15 26. Cyclopropanecarboxylic acid £4 - bromo - N - (2 oxoperhydro - 3 - furyl) - anilide]. 27. Cyclopropanecarboxylic acid £4 - fluoro - N - (2 oxoperhydro - 3 - furyl) - anilide]. 28. Cyclopropanecarboxylic acid[2 - ethoxy - N - (2 20 oxoperhydro - 3 - furyl) - anilide]. 4βθ8 3 -4429. Cyclopropanecarboxylic acid £3 - chloro - 2 - methyl -N (2 - oxoperhydro - 3 - furyl) - anilide]. 30. Cyclopropanecarboxylic acid £5 - chi oro - 2 methyl - N - (2 - oxoperhydro - 3 - furyl) - anilide] 5 31. Cyclopropanecarboxylic acid [4 - methoxy - 2 methyl - N - (2 - oxoperhydro - 3 - furyl) anilide] 32. Cyclopropanecarboxylic acid £4 - ethoxy - N (2 - oxoperhydro - 3 - furyl) - anilide]. 10 33. Cyclopropanecarboxylic acid£s - chloro - 2 methoxy - N - (2 - oxoperhydro - 3 - furyl) - anilide]. 34. Cyclopropanecarboxylic acid£3 - chloro - N - (5 methyl - 2 - oxoperhydro - 3 - furyl) - anilidej. 35. Cyclopropanecarboxylic acid£3 - ethyl - N -.(2 15 oxoperhydro - 3 - furyl) - anil ide]. 36. Cyclopropanecarboxylic acid£3 - cyano - N (2 - oxoperhydro - 3 - furyl) - anilide]. 37. Cyclopropanecarboxylic acid£3 - thiomethyl - N (2 - oxoperhydro - 3 - furyl) - anilidej. -4538. Cyclopropanecarboxyl ic acid£2, 3 - dichloro - N - (2 - oxoperhydro - 3 - furyl) - anilide]. 39. Cycl opropanecarboxyl i c acid £3 - chloro - N - (5 - methyl - 2 - oxoperhydro - 3 - furyl) g anilide], 40. A process for the manufacture of a compound as claimed in Claim 1, wherein a compound ofthe general formula II (II) in which Rp R z and ji have the meanings given above, 10 is reacted in the presence of an acid-binding agent with cyclopropanecarboxylic acid chloride of the formula III (III), -4641. A process as claimed in claim 40, wherein the reaction is carried out in the presence of a solvent. 42. A process as claimed in claim 40 or 41, wherein the compound of the general formula II and the compound ofthe 5 formula III are used in equimolar proportions. 43. A process as claimed in claim 40, conducted substantially as described herein. 44. A process as claimed in claim 40, conducted substantially as described in Example 1 herein. 10 45. A fungicidal preparation which comprises a compound of the general formula I given in claim 1, in which Rp Rg and n^ have the meanings given in claim 1, in admixture or conjunction with a suitable carrier. 46. A fungicidal preparation which comprises a compound 15 as claimed in claim 2, in admixture or conjunction with a suitable carrier. 47. A fungicidal preparation which comprises the compound claimed In any one of claims 3 to 39, in admixture or conjunction with a suitable carrier. 20 48. A preparation as claimed in any one of claims 45 to 4 6 9 2 3 -4747, which is in the form of a powder, a strewable preparation, granules, a solution, an emulsion or a suspension. 49. A preparation as claimed in any one of claims 5 45 to 48, containing a single compound of the general formula I in an amount of approximately 1 to 80% by weight. 50. A preparation as claimed in any one of claims 45 to 48, containing two or more compounds of the 10 general formula I in a total amount of approximately 1 to 80% by weight. 51. A preparation as claimed in any one of claims 45 to 50, which also contains a single surfaceactive agent in an amount of up to 20% by ]5 weight. 52. A preparation as claimed in any one of claims 45 to 50, which also contains two or more surfaceactive agents in a total amount of up to 20% by weight.
- 2. O 53. A preparation as claimed in any one of claims 45 to 52, which also contains a dyestuff. -4854. Any one of the fungicidal preparations as claimed in claim 45 and substantially as described in Examples 2, 3. , 5 and 7 herein. 55. Any one of the fungicidal preparations as claimed g in claim 45 and substantially as described in Examples 4. And 9 herein. 56. A method of protecting a living plant against phytopathogenic fungi, wherein the living plant is treated with a compound of the general formula I given in claim 1θ 1, in which Rp Rg and £ have the meanings given in claim 1. 57. A method as claimed in claim 56, wherein the living plant is treated with a compound as claimed in claim 2. 58. A method as claimed in claim 56, wherein the living 15 plant is treated with the compound claimed in any one of claims 3 to 39. 59. A method as claimed in claim 56, wherein the living plant is treated with a fungicidal preparation as claimed in any one of claims 45 to 52, 54 and 55. 20 60. A method as claimed in claim 56, conducted substantially as described in Example 4 herein. 46323 -4961. A method as claimed in claim 56, conducted substantially as described in Example 5 or 7 herein. 62. A method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with 5. A compound of the general formula I given in Claim 1, in which Rp R 2 and ji have the meanings given in claim 1. 63. A method as claimed in claim 62, wherein the crop area is treated with a compound as claimed in claim 2. 64. A method as claimed in claim 62, wherein the 6. 10 crop area is treated with the compound claimed in any one of claims 3 to 39. 65. A method as claimed in claim 62, wherein the crop area is treated with a fungicidal preparation as claimed in any one of claims 45 to 52, 54 and 55. 66. A method as claimed in claim 62, conducted substantially as described in Example 2 or 6 herein. 67. A method as claimed in claim 62,. conducted substantially as described in Example 9 herein. 68. A method of dressing seeds, wherein the seeds 20 are treated with a compound of the general formula I 46933 -50in which Rp Rg and n have the meanings given in claim 1. 69. A method as cl aimed in cl aim 68, wherein the seeds are treated with a compound as claimed in claim 2. I 5 70. A method as claimed in claim 68, wherein the seeds are treated with the compound claimed in any one of claims 3 to 39. 71. A method as claimed in claim 68, wherein the seeds are treated with a fungicidal preparation as 10 claimed in any one of claims 45 to 55, 72. A method as claimed in claim 68, conducted substantially as described in Example 3 herein. 73. A method as claimed in claim 68, conducted substantially as described in Example 8 herein. 7. 15 74. A pack which comprises a compound of the general formula 1 given in claim 1, in which Rp Rg and £ have the meanings given in claim 1, together with instructions for its use for controlling phytopathogenic fungi. 8. 20 75, A pack as claimed in claim 74, wherein the compound -51of the general formula I is a compound as claimed in claim 2. 76. A pack as claimed in claim 74, wherein the compound of the general formula I is the compound claimed in 5 any one of claims 3 to 39.
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 |
|---|---|
| IE781029L IE781029L (en) | 1978-11-27 |
| IE46923B1 true IE46923B1 (en) | 1983-11-02 |
Family
ID=6010435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1029/78A IE46923B1 (en) | 1977-05-27 | 1978-05-24 | Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and use |
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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