DK156753B - FUNGICIDE AGENT CONTAINING A MIXTURE OF ((1,2-ETHAN-DIYLBIS (CARBAMODITHIOATO)) (2 -)) - MANGANE AND A PYRIMIDINE METHANOL, AND PROCEDURES FOR REDUCING FUNGUS INFECTIONS IN CORN CROPS - Google Patents

FUNGICIDE AGENT CONTAINING A MIXTURE OF ((1,2-ETHAN-DIYLBIS (CARBAMODITHIOATO)) (2 -)) - MANGANE AND A PYRIMIDINE METHANOL, AND PROCEDURES FOR REDUCING FUNGUS INFECTIONS IN CORN CROPS Download PDF

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Publication number
DK156753B
DK156753B DK391378AA DK391378A DK156753B DK 156753 B DK156753 B DK 156753B DK 391378A A DK391378A A DK 391378AA DK 391378 A DK391378 A DK 391378A DK 156753 B DK156753 B DK 156753B
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Prior art keywords
mixture
carbamodithioato
diylbis
mangane
ethan
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DK391378AA
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Danish (da)
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DK391378A (en
DK156753C (en
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Antoine Casanova
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Lilly Industries Ltd
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A01N47/14Di-thio analogues thereof

Description

DK 156753BDK 156753B

Den foreliggende opfindelse angâr et fungicidt middel til anvendel-se ved plantebeskyttelse samt en fremgangsmâde til behandling af frp af kornsorter til reduktion af forekomsten eller graden af fungusinfek-tioner i de deraf dyrkede afgrpder.The present invention relates to a fungicidal agent for use in plant protection, and to a method of treating seeds of cereals to reduce the incidence or degree of fungal infections in the crops grown there.

5 Det fungicide middel ifplge opfindelsen er ejendommeligt ved, at det bestâr af eller indeholder en kombination af [[l,2-ethandiylbis[car-bamodithioato]](2-)]-mangan og en pyrimidinmethanol med formlen (I): x 10 à N—. ^ (OH-ohThe fungicidal agent of the invention is characterized in that it consists of or contains a combination of [[1,2-ethanediyl bis [carbamodithioato]] (2 -)] - manganese and a pyrimidine methanol of formula (I): x 10 à N—. ^ (OH-oh

Kf—/ IKf— / I

15 /VxCl15 / VxCl

(oT(oT

hvori X er chlor eller fluor.wherein X is chlorine or fluorine.

[[l,2-ethandiylbis[carbamodithioato]](2-)]-mangan er en kendt for-20 bindelse (se U.S.A. patentskrift nr. 2.504.404 og 2.710.822), som har det generiske navn "Maneb". Pyrimidinmethanolerne med formlen (I) er og-sâ kendte, og de kan fremstilles ved den i U.S.A. patentskrift nr.[[1,2-Ethanediylbis [carbamodithioato]] (2 -)] - manganese is a known compound (see U.S. Patent Nos. 2,504,404 and 2,710,822) bearing the generic name "Maneb". The pyrimidine methanol of formula (I) is also known and can be prepared by that of U.S.A. patent specification no.

1.218.623 beskrevne fremgangsmâde. Forbindelsen med formlen (I), hvori X betegner fluor, foretrækkes.1,218,623. The compound of formula (I) wherein X represents fluorine is preferred.

25 Det hidtil ukendte middel ifplge den foreliggende opfindelse er overraskende effektivt til regulering eller bekæmpelse af fungusinfek-tioner i kornsorter. Det er særligt aktivt, nâr det anvendes som en frp-dressing, idet det regulerer mange betydningsfulde sygdomme, hvoriblandt de efterfplgende er et repræsentativt udvalg: 30 1. Svadomme hos bva (Hordeum vulgare)The novel agent of the present invention is surprisingly effective in controlling or controlling fungal infections in cereals. It is particularly active when used as a FRP dressing, as it regulates many significant diseases, including the following is a representative selection: 30 1. Swim Diseases in BVA (Hordeum vulgare)

Pyrenophora araminea Cochliobolus sativus Calonectria nivalis 35 Typhula incarhata Ervsiphe qraminis 2. Svadomme hos havre (Avena sativa)Pyrenophora araminea Cochliobolus sativus Calonectria nivalis 35 Typhula incarhata Ervsiphe qraminis 2. Sweat in oats (Avena sativa)

Pvrenophora avenae 2Pvrenophora avenae 2

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3. Svadomme hos hvede3. Sweat in wheat

Cercosporel1 a herpotrichoidesCercosporel1 and herpotrichoides

Tilletia spp.Tilletia spp.

Calonectria nivalis 5 Leptosphaeri a nodorum I et andet aspekt af opfindelsen tilvejebringes der fplgelig en fremgangsmàde til behandling af frp af kornsorter til reduktion af fore-komsten eller graden af fungusinfektioner i de deraf dyrkede kornaf-10 grpder, hvilken fremgangsmàde er ejendommelig ved, at frpene af korn-sorterne tilfpres det ovenfor definerede hidtil ukendte middel.Calonectria nivalis 5 Leptosphaeri a nodorum In another aspect of the invention, there is thus provided a method for treating seeds of cereals to reduce the incidence or degree of fungal infections in the crops grown therein, which method is characterized by the fact that of the cereal varieties was added to the aforementioned novel agent.

Skpnt det hidtil ukendte middel fortrinsvis ânvendes i form af en frpbehandling, er der ogsâ opnâet gunstige resultater ved foliartilfpr-sel af det hidtil ukendte middel pâ et hvilket som helst tidspunkt i 15 perioden fra afgrpdefremkomst og til hpst, idet den aktuelle behand-lingshyppighed og -varighed bestemmes af graden af den aktuelle eller forventede sygdom. Komponenterne i midiet kan tilfpres sekventielt eller samtidig til afgrpden, som skal behandles.Although the novel agent is preferably used in the form of a preparative treatment, favorable results have also been obtained by foil application of the novel agent at any time during the period from crop emergence to harvest, with the current treatment frequency and duration is determined by the degree of the current or expected disease. The components of the waist may be applied sequentially or simultaneously to the crop to be treated.

Pyrimidinmethanolen tilfpres fortrinsvis frpene i en mængde pâ 0,05 20 til 0,8 g/kg frp, særligt foretrukket 0,1 g/kg frp for hvede og 0,2 g/kg frp for byg, mens "Maneb" fortrinsvis tilfpres i en mængde pâ 0,2 - 1,6 g/kg frp, særligt foretrukket omkring 0,8 g/kg frp. Et foretrukket vægt-forhold mellem pyrimidinmethanolen og "Maneb" er fra 1:2 til 1:32, fortrinsvis 1:4 til 1:8.The pyrimidine methanol is preferably applied to the seeds in an amount of 0.05 to 0.8 g / kg of seed, particularly preferably 0.1 g / kg of seed for wheat and 0.2 g / kg of seed for barley, while "Maneb" is preferably sealed in an amount of 0.2 - 1.6 g / kg frp, particularly preferably about 0.8 g / kg frp. A preferred weight ratio of the pyrimidine methanol to "Maneb" is from 1: 2 to 1:32, preferably 1: 4 to 1: 8.

25 Det hidtil ukendte middel ifplge opfindelsen ânvendes fortrinsvis i form af et fungicidpræparat omfattende pyrimidinmethanolen og "Maneb" i* · forbindelse med en ikke-fytotoksisk, inert bærer derfor.The novel agent of the invention is preferably used in the form of a fungicide composition comprising the pyrimidine methanol and "Maneb" in association with a non-phytotoxic inert carrier.

Sàdanne fungicidpræparater kan omfatte fra 5-90 vægt procent aktive komponenter og vil sædvanligvis være i form af et befugteligt 30 pulver eller pudder.Such fungicide preparations may comprise from 5 to 90% by weight of active components and will usually be in the form of a wettable powder or powder.

Befugtelige pulvere eller puddere omfatter en intim blanding af de aktive komponenter, en eller flere inerte bærere og passende overflade-aktive mîdler. Den inerte bærer kan være udvalgt blandt forskellige former for attapulgitler, montmorillonitler, diatoméjord, kaolin, glim-35 mer, talkum og rensede silikater. Effektive overfladeaktive midler kan findes blandt de sulfonerede ligniner, naphthalensulfonaterne og de kon-denserede naphthalensulfonater, alkylsuccinaterne, alkylbenzensulfonat-erne, alkylsulfaterne og de non-ioniske overfladeaktive midler, sâsomWettable powders or powders comprise an intimate mixture of the active components, one or more inert carriers and suitable surface-active agents. The inert carrier may be selected from various forms of attapulgitles, montmorillonitels, diatomaceous earth, kaolin, glimmers, talc and purified silicates. Effective surfactants can be found among the sulfonated lignins, the naphthalene sulfonates and the condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzenesulfonates, the alkyl sulfates, and the nonionic surfactants, such as

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3 ethylenoxidadditionsforbindelser af phénol. Anvendt til frdbehandling vil midlerne if0lge opfindelsen ogsâ fortrinsvis omfatte et klæbemiddel til at binde midlet til frdene, et pigment til at vise om en særlig portion frd er blevet behandlet eller ej, et insekticid og et fugle-5 afvisningsmiddel.3 ethylene oxide addition compounds of phenol. Used for treating the wound, the compositions of the invention will also preferably comprise an adhesive for bonding the agent to the veins, a pigment to indicate whether a particular portion of the seed has been treated or not, an insecticide and a bird rejection agent.

Til illustration af befugtelige pulvere indenfor opfindelsens ram-mer kan anfores pulvere med fplgende sammensætning:For illustration of wettable powders within the scope of the invention, powders of the following composition may be provided:

Befugtelige pulvere 10 VægtprocentWettable powders 10% by weight

Pyrimidinmethanol 2-20 "Maneb" 15 - 50Pyrimidine Methanol 2-20 "Maneb" 15 - 50

Insekticid 0-40Insecticide 0-40

Fugleafvisningsmiddel 0-30 15 Befugtningsmiddel/-ler 2-10Bird repellent 0-30 15 Wetting agent (s) 2-10

Dispergeringsmiddel 0-10Dispersant 0-10

Antisammenbagningsmiddel 1-10Anti-caking agent 1-10

Klæbemiddel 0-5Adhesive 0-5

Pigment 0-10 20 Inert(e) materiale(r) til 100Pigment 0-10 20 Inert material (s) to 100

Til illustration af pudderpræparater af værdi i forbindelse med opfindelsen kan anf0res præparater med fdlgende sammensætning: 25 Pudder VægtprocentFor illustration of powder compositions of value in connection with the invention, compositions having the following composition may be given: 25 Powder Weight percent

Pyrimidinmethanol 2-20 "Maneb” 15 - 50Pyrimidine Methanol 2-20 "Maneb" 15 - 50

Insekticid 0-40 30 Fugleafvisningsmiddel 0-25Insecticide 0-40 30 Bird repellent 0-25

Overfladeaktivt middel/-ler 0-10 01 ie 0 - 10Surfactant (s) 0-10 01 ie 0 - 10

Pigment 0 - 10Pigment 0 - 10

Inert(e) materiale(r) til 100Inert material (s) to 100

De efterf0lgende specifikke eksempler er anfdrt til yderligere illustration af opfindelsen. I disse eksempler repræsenterer CCPM for-bindelsen a-(2-chlorphenyl)-a-(4-chlorphenyl)-5-pyrimidinmethanol og 35The following specific examples are given for further illustration of the invention. In these examples, the CCPM represents the compound α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidine methanol and 35

DK 156753 BDK 156753 B

4 CFPM forbindelsen a-(2-chlorphenyl)-a-(4-fl uorphenyl)-5-pyrimidin- methanol. Eksemplerne 1-3 illustrerer udfprelsesformer af befugtelige pulvere, mens eksemplerne 4 og 5 angâr pudderpræparater.The 4 CFPM compound α- (2-chlorophenyl) -α- (4-fluorophenyl) -5-pyrimidine-methanol. Examples 1-3 illustrate embodiments of wettable powders, while Examples 4 and 5 pertain to powder formulations.

5 Eksempel 1 Væatprocent CFPM 8 "Maneb" 32Example 1 Watt Percent CFPM 8 "Maneb" 32

Natri umal f aol efinsulfonat 5 10 Natriumligninsulfonat 5Sodium aluminum finsulfonate 5 Sodium lignin sulfonate 5

Siliciumoxid 5Silica 5

Kaolin 45Kaolin 45

Eksempel 2 15 Væatprocent CFPM 6,5 "Maneb" 26,5 "Lindan" 16,5Example 2 15 wt% CFPM 6.5 "Maneb" 26.5 "Lindan" 16.5

Natriumalkylarylsuifonat 2 20 Siliciumoxid 1,5Sodium alkylaryl sulfonate 2 Silica 1.5

Polyvinylpyrrolidon 1Polyvinylpyrrolidone 1

Kaoli n 46Kaoli n 46

Eksempel 3 25 Væatprocent CCPM 6,5 "Maneb" 26,5 "Lindan" 16,5Example 3 25 Wt% CCPM 6.5 "Maneb" 26.5 "Lindan" 16.5

Anthraquinon 16,5 30 Natrium-N-alkyl-N-palmitoyltaurat 5Anthraquinone 16.5 Sodium N-alkyl-N-palmitoyl taurate 5

Natriumligninsulfonat 5Sodium lignin sulfonate 5

Siliciumoxid 5Silica 5

Permanent rddt 4Permanent rddt 4

Kaolin 15 7 "Lindan" er det generiske navn for a-l,2,3,4,5,6-hexachlorcyclohexan.Kaolin 15 7 "Lindan" is the generic name for α-1,2,3,4,5,6-hexachlorocyclohexane.

35 *1 535 * 1 5

DK 156753BDK 156753B

I ovenstâende eksempler 1-3 reduceres storrelsen af de aktive kom-ponenter pâ konventionel mâde, og de blandes derefter med de andre kom-ponenter i konventionelt blandingsudstyr. Blandingen formaies derefter i en fluidumenergimplle til en partikelst0rrelse i intervallet fra 1-10 5 jum. Blandingen genblandes derefter og afluftes for emballering.In the above Examples 1-3, the size of the active components is reduced in the conventional manner and then mixed with the other components in conventional mixing equipment. The mixture is then molded into a fluid energy bulb to a particle size in the range of 1-10 µm. The mixture is then re-mixed and de-aerated for packaging.

Eksempel 4 Væatprocent CFPM 10 10 "Maneb" 40 "IOW" motorolie 1Example 4 Watt Percent CFPM 10 10 "Maneb" 40 "IOW" Engine Oil 1

Rpdt jernoxid 5Rpdt iron oxide 5

Talkum 44 15 Eksempel 5 Væqtprocent CCPM 20 "Maneb" 40Talc 44 15 Example 5 Weight percent CCPM 20 "Maneb" 40

Alkylphénolethylenoxyd-kondensat 4 20 Permanent rodt 4Alkylphenolethylene oxide condensate 4 20 Permanent root 4

Talkum 27 I eksemplerne 4 og 5 reduceres partikelstorrelsen af de aktive kom-ponenter pâ konventionel mâde, og de blandes derefter med andre kompo-25 nenter, idet olien eller det overfladeaktive middel sprojtes ind i blandingen. Blandingen formai es derefter til parti kler med storrelse fra 5 til 50 μπι. Blandingen genblandes og afluftes for emballering.Talc 27 In Examples 4 and 5, the particle size of the active components is reduced by conventional means and then mixed with other components as the oil or surfactant is injected into the mixture. The mixture is then molded into batches of size from 5 to 50 μπι. The mixture is remixed and deaerated for packaging.

Præparatet fra eksempel 1 gav, som det fremgâr af nedenstâende for-sogsrapport, en synergistisk virkning ved anvendelse som frdbehandlings-30 middel i forbindelse med regulering af Septoria (Leptosohaeria nodorum) hos hvede.The preparation of Example 1, as shown in the test report below, gave a synergistic effect when used as a treating agent for the regulation of Septoria (Leptosohaeria nodorum) in wheat.

ForsQqsrapport 35 Testmetode og resultaterTest report 35 Test method and results

Tre fungicide formuleringer fremstilledes ved blanding af de neden-for anforte ingredienser efterfulgt af formaling i en fluidumenergimolle 6Three fungicidal formulations were prepared by mixing the ingredients listed below followed by grinding in a fluid energy mole 6

DK 156753BDK 156753B

til opnâelse af en partikelstprrelse i intervallet fra 1 til 10 pi.to obtain a particle size in the range of 1 to 10 µl.

Formuler!ηα IFormulas ηα I

Inarediens__Væqtdele 5 CFPM 8 "Maneb" 32Inner service__ Weight parts 5 CFPM 8 "Maneb" 32

Natriumalfaolefinsulfonat 5Sodium alpha olefin sulfonate 5

Natrium!igninsulfonat 5Sodium ignin sulfonate 5

Siliciumoxid 5 10 Kaolin 45Silica 5 10 Kaolin 45

Formulering IIFormulation II

Ingrediens_:_Væqtdele CFPM 8 15 "Maneb" 0Ingredient _: _ Weight Parts CFPM 8 15 "Maneb" 0

Natriumalfaolefinsulfonat 5Sodium alpha olefin sulfonate 5

Natrium!igninsulfonat 5Sodium ignin sulfonate 5

Siliciumoxid 5Silica 5

Kaolin 45 20Kaolin 45 20

Formulering IIIFormulation III

Ingrediens_Væqtdel e CFPM 0 "Maneb" 32 25 Natriumalfaolefinsulfonat 5Ingredient_ Weight CFPM 0 "Maneb" 32 25 Sodium alpha olefin sulfonate 5

Natrium!igninsulfonat 5Sodium ignin sulfonate 5

Siliciumoxid 5Silica 5

Kaolin 45 30 Som det ses indeholder formulering I CFPM og "Maneb" i overensstem-melse med opfindelsen, mens formuleringerne II og III er identiske med formulering I bortset fra, at henholdsvis "Maneb" og CFPM er udeladt.Kaolin 45 30 As seen, formulation I contains CFPM and "Maneb" in accordance with the invention, while formulations II and III are identical to formulation I except that "Maneb" and CFPM are omitted, respectively.

Ovennævnte formuler!nger blandedes derefter hver især intimt med hvedefrd injiceret med "Septoria" (Leptosphaeria nodorum) til en dosis 35 af CFPM pâ 0,2 g pr. kg frd og/eller en dosis af "Maneb" pâ 0,8 g pr. kg frp. Frpene udsâedes derefter pâ konventionel mâde i drivhuset. Senere foretoges en bestemmelse af procenten af sygdomsfrie raske planter med folgende resultater:The above formulations were then intimately mixed with wheat fruit injected with "Septoria" (Leptosphaeria nodorum) to a dose of CFPM of 0.2 g per gram. kg of fruit and / or a dose of "Maneb" of 0.8 g per day. kg frp. The seeds are then seeded in a conventional manner in the greenhouse. Later, a percentage of disease-free healthy plants was determined with the following results:

Claims (2)

15 Patentkrav15 Patent claims 1. Fungicidt middel til anvendelse ved plantebeskyttelse, KENDETEGNET ved, AT det bestâr af eller indeholder en kombination af [[1,2- ethan-diylbis[carbamodithioato]] (2-)]-mangan og en pyrimidinmethanol med formlen (I): X " ·Φ (O/ ? — oh (i) 25 \—/ i Cl (ΟΓ hvori X er chlor eller fluor.1. Fungicide for use in plant protection, CHARACTERIZED in that it consists of or contains a combination of [[1,2-ethane-diylbis [carbamodithioato]] (2 -)] - manganese and a pyrimidine methanol of formula (I): X "· Φ (O /? - oh (i) 25 \ - / i Cl (ΟΓ wherein X is chlorine or fluorine. 2. Fremgangsmâde til behandling af fr0 af kornsorter til reduktion af forekomsten eller graden af fungusinfektioner i de deraf dyrkede korn-afgrpder, KENDETEGNET ved, AT fr0ene af kornsorterne tilfpres et fungicidt middel if0lge krav 1. 352. A method for treating seeds of cereals to reduce the incidence or degree of fungal infections in the crops grown therein, characterized in that the seeds of the cereals are applied to a fungicidal agent according to claim 1. 35
DK391378A 1977-09-07 1978-09-05 FUNGICIDE AGENT CONTAINING A MIXTURE OF ((1,2-ETHAN-DIYLBIS (CARBAMODITHIOATO)) (2 -)) - MANGANE AND A PYRIMIDINE METHANOL, AND PROCEDURES FOR REDUCING FUNGUS INFECTIONS IN CORN CROPS DK156753C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3725177 1977-09-07
GB37251/77A GB1597363A (en) 1977-09-07 1977-09-07 Fungicidal combinations

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DK391378A DK391378A (en) 1979-03-08
DK156753B true DK156753B (en) 1989-10-02
DK156753C DK156753C (en) 1990-02-26

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FI (1) FI61608C (en)
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IT1143721B (en) * 1977-12-01 1986-10-22 Sipcam Spa FUNGICIDAL COMPOSITION FOR THE FIGHT AGAINST PLANT DISEASES

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GB1561634A (en) * 1975-10-29 1980-02-27 Lilly Industries Ltd Fungicidal compositions

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ZA784883B (en) 1979-08-29
FI61608B (en) 1982-05-31
IT1106132B (en) 1985-11-11
IL55441A0 (en) 1978-10-31
DK391378A (en) 1979-03-08
JO983B1 (en) 1979-12-01
GR63167B (en) 1979-09-26
BE870237A (en) 1979-03-05
DK156753C (en) 1990-02-26
AU526357B2 (en) 1983-01-06
ATA647578A (en) 1980-07-15
DE2838575A1 (en) 1979-03-08
BR7805811A (en) 1979-04-24
AR218330A1 (en) 1980-05-30
SE447441B (en) 1986-11-17
NO783044L (en) 1979-03-08
FR2402409A1 (en) 1979-04-06
SE7809387L (en) 1979-03-08
CH634462A5 (en) 1983-02-15
PL209466A1 (en) 1979-06-04
SU816390A3 (en) 1981-03-23
IE781685L (en) 1979-03-07
IN149680B (en) 1982-03-13
NO147091C (en) 1983-02-02
CA1090247A (en) 1980-11-25
FI782685A (en) 1979-03-08
NL7809096A (en) 1979-03-09
DE2838575C2 (en) 1988-06-01
DD138593A5 (en) 1979-11-14
PL111723B1 (en) 1980-09-30
FI61608C (en) 1982-09-10
BG32111A3 (en) 1982-05-14
FR2402409B1 (en) 1983-04-22
GB1597363A (en) 1981-09-09
NZ188229A (en) 1981-05-01
NO147091B (en) 1982-10-25
AT361248B (en) 1981-02-25
PH14333A (en) 1981-05-29
IE47245B1 (en) 1984-01-25
UA6333A1 (en) 1994-12-29
JPS5452727A (en) 1979-04-25
AU3961678A (en) 1980-03-13
CS207667B2 (en) 1981-08-31
TR20300A (en) 1981-01-07
HU180831B (en) 1983-04-29
MX5503E (en) 1983-09-05
ES473293A1 (en) 1979-10-16
IT7850962A0 (en) 1978-09-04

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