LU81096A1 - FUNGICIDAL COMPOSITION AND METHOD FOR FUNGICIDAL TREATMENT OF CULTIVATED PLANTS - Google Patents
FUNGICIDAL COMPOSITION AND METHOD FOR FUNGICIDAL TREATMENT OF CULTIVATED PLANTS Download PDFInfo
- Publication number
- LU81096A1 LU81096A1 LU81096A LU81096A LU81096A1 LU 81096 A1 LU81096 A1 LU 81096A1 LU 81096 A LU81096 A LU 81096A LU 81096 A LU81096 A LU 81096A LU 81096 A1 LU81096 A1 LU 81096A1
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- compound
- formula
- fungicidal
- composition
- fungicidal composition
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- 239000000203 mixture Substances 0.000 title claims description 34
- 230000000855 fungicidal effect Effects 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000470 constituent Substances 0.000 claims description 12
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
- 208000031888 Mycoses Diseases 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 claims description 5
- 206010017533 Fungal infection Diseases 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 150000003230 pyrimidines Chemical class 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 2
- 241000196324 Embryophyta Species 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 5
- 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 5
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- -1 alkylsuccinates Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 239000011717 all-trans-retinol Substances 0.000 description 2
- 235000019169 all-trans-retinol Nutrition 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 231100001184 nonphytotoxic Toxicity 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001294 alanine derivatives Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N47/00—Biocides, 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
- A01N47/08—Biocides, 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
Landscapes
- 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
i f 1 ti f 1 t
La présente invention porte sur une composition fongicide et un procédé, pour le traitement d'infections fongiques de plantes cultivées.The present invention relates to a fungicidal composition and method for the treatment of fungal infections of cultivated plants.
L'invention porte particulièrement sur une composition fongicide contenant comme premier constituant à activité fongicide, un dérivé tria-2 zoie ou pyrimidine de la formule :The invention relates particularly to a fungicidal composition containing as a first constituent with fungicidal activity, a 2-zoy or pyrimidine derivative of the formula:
N—jTN — jT
G IAG IA
ÎT x Cl I ou /-\ K —\ÎT x Cl I or / - \ K - \
10 Cl-—/ \-O-CH-CO-C(CH^)^ / \- C-OH10 Cl -— / \ -O-CH-CO-C (CH ^) ^ / \ - C-OH
\=/ N -=/ I(a) ^ | I(b) 15\ = / N - = / I (a) ^ | I (b) 15
XX
dans laquelle X représente le chlore ou le fluor et comme second constituant à activité fongicide, un composé de formule : 20 OU, CH | ^ ,CH - C00CH 0 0 Y i iiin which X represents chlorine or fluorine and as a second constituent with fungicidal activity, a compound of formula: 20 OR, CH | ^, CH - C00CH 0 0 Y i ii
- LA OU C H NECNHCCCN- WHERE C H NECNHCCCN
Y 2 5 IIY 2 5 II
CO - R NOCHCO - R NOCH
CH_, * 25 3CH_, * 25 3
Il(a) II(b) dans laquelle R représente fur-2-yle ou -CE^OCH^, ces constituants étant associés avec un ou plusieurs supports inertes n on-ph y t ot oxi qu e s.II (a) II (b) in which R represents fur-2-yl or -CE ^ OCH ^, these constituents being associated with one or more inert supports n on-ph y t ot oxi qu e s.
2q Tous les composés prémentionnés sont des composés connus et peuvent être préparés par des techniques bien définies dans la littérature. Le triazole de formule l(a) est décrit dans le brevet des Etats-Unis 3 912 752,· les pyrïmidines de formule l(b) sont décrites dans le brevet britannique 1 218 623 j tandis que les dérivés alanïnes de formule Il(a) 23 sont décrites dans le brevet britannique 1 448 810 et dans le brevet belge 827 671 et que le dérivé d'urée de formule Il(b) est décrit dans le brevet jbritannique 1 470 7^0.2q All of the above-mentioned compounds are known compounds and can be prepared by techniques well defined in the literature. The triazole of formula l (a) is described in United States patent 3,912,752, · the pyrimidines of formula l (b) are described in British patent 1,218,623 d while the alanine derivatives of formula II (a ) 23 are described in British Patent 1,448,810 and in Belgian Patent 827,671 and that the urea derivative of formula II (b) is described in British Patent 1,470,7 ^ 0.
Üt* ' » 2 »Üt * '»2»
Les combinaisons des constituants actifs prémentionnés dans la composition fongicide indiquée, sont nouvelles et il est apparu qu'elles son | particulièrement efficaces pour maîtriser et combattre les infections fongiques des plantes cultivées- Elles sont surtout intéressantes dans 5 le traitement d'une grande variété de plantes cultivées pouvant subir des | atteintes fongiques, telles que les céréales et les haricots et fèves, et en particulier les plantes pouvant subir des atteintes d'oïdium et de mildiou de la vigne de même que de mildiou de la pomme de terre, ces plantes étant par exemple des vignes, des cucurbitacées ou du tabac pouva 10 subir des attaques par des microorganismes du type oomycètes et érysipha-cées.The combinations of active constituents mentioned in the indicated fungicidal composition are new and have been found to be | particularly effective in controlling and combating fungal infections of cultivated plants. They are especially useful in the treatment of a wide variety of cultivated plants which may be subject to | fungal damage, such as cereals and beans and beans, and in particular plants which can suffer from powdery mildew and downy mildew of the vine as well as downy mildew of the potato, these plants being for example vines, cucurbits or tobacco could be attacked by microorganisms of the oomycetes and erysiphace type.
La présente invention porte également sur un procédé de traitement d'infections fongiques des plantes, en particulier des vignes, qui compor * te l'application auxdites plantes d'une quantité fongicide efficace de la 15 composition fongicide prémentionnée.The present invention also relates to a method of treating fungal infections of plants, in particular of vines, which comprises the application to said plants of an effective fungicidal amount of the above-mentioned fungicidal composition.
Pour la mise en oeuvre de ce procédé, la composition fongicide peut être appliquée par voie foliaire ou par arrosage du sol, en fonction de 1 Ü plante à traiter, à n’importe quel moment compris entre l'émergence et la ï 1 récolte. La Quantité et la fréquence de l'application seront déterminées i I 20 suivant l'importance ou l'importance probable de la maladie fongique et, I ainsi qu'il est bien connu par les spécialistes, en fonction de l’âge et de l'état de la plante. Cependant, une caractéristique de l'invention et I . un avantage particulier de celle-ci est la fréquence réduite du traitemerFor the implementation of this process, the fungicidal composition can be applied by foliar or by watering the soil, depending on the plant to be treated, at any time between emergence and harvest. The amount and frequency of application will be determined i I 20 according to the importance or probable importance of the fungal disease and, I as is well known by specialists, depending on the age and l state of the plant. However, a feature of the invention and I. a particular advantage of this is the reduced frequency of treatment
Ipar exemple un traitement seulement toutes les deux à trois semaines pour 25 le mildiou de la vigne ce qui entraîne une réduction importante des fraie f de main d'oeuvre.For example, a treatment only every two to three weeks for downy mildew of the vine, which results in a significant reduction in labor spawning.
• ! , ί Un dérivé de pyrzmidine préféré pour une application foliazre, par ; I 1 exemple pour le traitement des vignes, est un composé dans lequel X reprl 1 f sente le chlore- Cependant, lorsque l'application de la composition de i i 30 l'invention est destinée à être effectuée à l'aide d'un arrosage du sol,•! , ί A preferred pyrzmidine derivative for foliazre application, by; I 1 example for the treatment of vines, is a compound in which X represents 1 chlorine- However, when the application of the composition of ii 30 the invention is intended to be carried out using a sprinkler of the ground,
; , il est apparu que le dérivé des pyrimidines de formule I dans lequel X; , it appeared that the pyrimidine derivative of formula I in which X
- représente le fluor est particulièrement efficace.- represents fluorine is particularly effective.
Ainsi qu'on a indiqué précédemment, les compositions de la présente invention sont utilisées en application foliaire ou en arrosage du sol.As indicated above, the compositions of the present invention are used as a foliar application or as a soil spray.
35 Pour les arrosages du sol, les composés de formule l(a) et l(b) sont de ^ préférence appliqués en des quantités de 50 à 500 g par hectare, tandis Il Gue les composés de formule Il(a) sont de préférence appliqués en des ” 7îv _____ - i. i _ ar\r\ A -z ____i j r 4 „4 i -----,4. A,, ' .2 „ 3 formule I(a) ou l(b) au composé de formule Il(a) dans de telles compositions, peut de préférence être compris dans un rapport pondéral de 1 : 1 à 1 : 60.For soil watering, the compounds of formula l (a) and l (b) are preferably applied in amounts of 50 to 500 g per hectare, while the compounds of formula II (a) are preferably applied in ”7îv _____ - i. i _ ar \ r \ A -z ____i j r 4 „4 i -----, 4. A ,, '.2 „3 formula I (a) or l (b) to the compound of formula II (a) in such compositions, may preferably be included in a weight ratio of 1: 1 to 1: 60.
Lorsqu'on a recours à une application foliaire, le composé de for-5 mule l(a) est de préférence appliqué à raison de 10 à 500 g par hectare, tandis que le composé de formule l(b) est de préférence appliqué à raison de 10 à 100 g par hectare. Le composé de formule Il(a) est de préférence appliqué à raison de 100 à 2-500 g par hectare. Dans ces circonstances, le composé de formule Il(b) est de préférence appliqué à raison de 50 à 10 500 g/hectare. Par conséquent, le rapport pondéral des composés de formule I aux composés de formule II dans les compositions servant à une application foliaire est de préférence compris entre 5 ’ 1 à 1 : 250.When a foliar application is used, the compound of formula 5 (a) is preferably applied at a rate of 10 to 500 g per hectare, while the compound of formula l (b) is preferably applied to 10 to 100 g per hectare. The compound of formula II (a) is preferably applied at a rate of 100 to 2-500 g per hectare. Under these circumstances, the compound of formula II (b) is preferably applied at a rate of 50 to 10,500 g / hectare. Consequently, the weight ratio of the compounds of formula I to the compounds of formula II in the compositions used for foliar application is preferably between 5 ′ 1 to 1: 250.
Le composé de formule II(b) est de préférence utilisé en combinaison avec un autre fongicide tel que par exemple zineb ou mancozeb, tel qu'il 15 est indiqué dans le brevet britannique 1 Il convient de noter que de tels fongicides complémentaires sont utilisés à approximativement la moitié de leur dose normale et que le composé de formule II(b) n'est pas compatible avec des composés qui augmentent l'alcalinité.The compound of formula II (b) is preferably used in combination with another fungicide such as for example zineb or mancozeb, as indicated in British patent 1. It should be noted that such complementary fungicides are used approximately half their normal dose and that the compound of formula II (b) is not compatible with compounds which increase alkalinity.
En vue de simplifier la fabrication, le stockage et le transport, 20 la composition contenant les composés de formules I et II sera normalement produite sous forme concentrée prévue pour être diluée par de l'eau à la concentration nécessaire qui permette d'obtenir facilement les taux d'application mentionnés ci-dessus. De telles compositions concentrées peuvent contenir de 0,5 à 90 %, de préférence 5 à 90 % en poids des constituants 25 actifs associés avec un ou plusieurs supports non phytotoxiques inertes.In order to simplify manufacture, storage and transport, the composition containing the compounds of formulas I and II will normally be produced in concentrated form intended to be diluted with water to the necessary concentration which allows easy obtaining. application rates mentioned above. Such concentrated compositions can contain from 0.5 to 90%, preferably 5 to 90% by weight of the active constituents associated with one or more inert non-phytotoxic carriers.
Ces compositions se présenteront de préférence sous forme de poudres ou jjoussièresmouillables, de suspensions aqueuses, de concentrats émulsifia-v blés ou de granulés. Les compositions concentrées sont prévues pour subir une dilution appropriée par de l'eau avant leur utilisation. Cette forma-30 tion d'une dispersion aqueuse peut être réalisée dans n'importe quel réservoir de pulvérisation classique prévu à cet effet. Il convient de noter que les compositions diluées que l'on produit ainsi sont des compositions relevant de l'invention dans lesquelles un ou la totalité du support non phytotoxique inerte est constitué par de l'eau.These compositions will preferably be in the form of wettable powders or dust, aqueous suspensions, emulsifiable concentrates or granules. The concentrated compositions are intended to undergo an appropriate dilution with water before their use. This formation of an aqueous dispersion can be carried out in any conventional spray tank provided for this purpose. It should be noted that the diluted compositions which are thus produced are compositions falling within the scope of the invention in which one or all of the inert non-phytotoxic support consists of water.
55 Les poudres ou poussières mouillables comportent un mélange intime des constituants ci ctifs, d'un ou plusieurs supports et d'un agent tensio-I actif convenable. Le support inerte peut être choisi parmi les argiles <3e>» d 'attapulgite, les argiles de montmorillonite, les terres de diatomées, k les kaolins, les micas, les talcs et les silicates purifiés. Des agents tensio-actifs efficaces peuvent être choisis parmi les lignines sulfonates, les naphtaienes-sulfonates et les naphtalènes-sulfonates condensés, les alkylsuccinates, les alkylbenzènes sulfonates, les sulfates d'alkyle et 5 les agents tensio-actifs non ioniques tels que les composés d'addition d'oxyde d'éthylène sur le phénol.55 The wettable powders or dust comprise an intimate mixture of the active constituents, one or more carriers and a suitable active surfactant. The inert support can be chosen from attapulgite clays, montmorillonite clays, diatomaceous earths, kaolin, micas, talcs and purified silicates. Effective surfactants can be selected from lignin sulfonates, naphthaene sulfonates and condensed naphthalene sulfonates, alkylsuccinates, alkylbenzene sulfonates, alkyl sulfates and nonionic surfactants such as compounds of addition of ethylene oxide to the phenol.
; A titre d'illustration de poudres mouillables relevant de l'inventioi t ; on peut citer celles correspondant à la composition suivante : } I Poudres mouillables f * ' ' % en poids : ; 10 --- | Composé de formule I 1 à 10; By way of illustration of wettable powders relating to the invention; mention may be made of those corresponding to the following composition:} I Wettable powders f * ''% by weight:; 10 --- | Compound of formula I 1 to 10
Composé de formule II 5 à 60Compound of formula II 5 to 60
Agent(s) tensio-actif(s) 0 à 10Surfactant (s) 0 to 10
Agent de dispersion 0 à 10 15 Agent antimotant 0 à 15Dispersing agent 0 to 10 15 Antimotoring agent 0 to 15
Support(s) inerte(s) pour amener à 100 L'invention sera encore illustrée par les exemples sans caractère limitatif qui suivent.Inert medium (s) for bringing to 100 The invention will be further illustrated by the following non-limiting examples.
i Le composé de formule I(b) où X est le chlore est connu sous 20 le nom fenarimol, tandis que le composé correspondant dans lequel X est le fluor est connu sous le nom de nuarimol. De manière similaire, le l composé de formule l(a) est appelé triadimefon. Dans les exemples ci- » dessous, le composé de formule Il(a) dans lequel S est fur-2-yle est re- i| présenté par la lettre "A", tandis que le composé de formule Il(a) dans l| 23 lequel R est -CH OCH est représenté par "B" et le composé de formule Il(b !| d 5 par "C".The compound of formula I (b) where X is chlorine is known as fenarimol, while the corresponding compound in which X is fluorine is known as nuarimol. Similarly, the l compound of formula l (a) is called triadimefon. In the examples below, the compound of formula II (a) in which S is fur-2-yl is re- i | presented by the letter "A", while the compound of formula Il (a) in l | 23 which R is -CH OCH is represented by "B" and the compound of formula II (b! | D 5 by "C".
j? Exemples 1 à 10 - ” j; , On a préparé les poudres mouillables suivantes : ·! i (1) % en poids 30 Composé A . 25 ! '· i| Fenarimol 5,0 I ïj? Examples 1 to 10 - ”j; , The following wettable powders have been prepared: ·! i (1)% by weight 30 Compound A. 25! '· I | Fenarimol 5.0 I ï
Lauryl-sulfate de sodium *f,0 ! î( * j| Lignine-sulfonate de sodium 3,0 !ï . , μ- Silice précipités 8,0 ,, 55 Arsile kaolin jusqu'à 100,0 ! i! / t ii i ' 5 (2) % en poidsSodium lauryl sulfate * f, 0! î (* j | Sodium lignin sulfonate 3.0! ï., μ- Silica precipitated 8.0 ,, 55 Arsile kaolin up to 100.0! i! / t ii i '5 (2)% by weight
Composé A 50,0Compound A 50.0
Nuarimol 2,5Nuarimol 2.5
Dioctyl-sulfosuccinate de sodium 5,0 5 Lignine sulfonatée 2,0Sodium dioctyl sulfosuccinate 5.0 5 Lignin sulfonate 2.0
Terre de diatornée jusqu'à 100,0 (3) /3 en poidsDiatomaceous earth up to 100.0 (3) / 3 by weight
Composé B 40,0Compound B 40.0
Fenarimol 4,0 10 Alkyl-phényl éthoxylé 3,0Fenarimol 4.0 10 Alkyl-phenyl ethoxylate 3.0
Lignine-suifonate de sodium 5,0Sodium lignin-sulfonate 5.0
Silicoaluminate de sodium hydraté 4,0Hydrated sodium silicoaluminate 4.0
Talc jusqu'à 100,0 (4) % en poids 15 Nuarimol 2,0Talc up to 100.0 (4)% by weight 15 Nuarimol 2.0
Composé B 40,0Compound B 40.0
Alkylnaphtalène-sulfonate de sodium 8,0Sodium alkylnaphthalene sulfonate 8.0
Silice 3,0Silica 3.0
Kaolin jusqu'à 100,0 20 (5) % en poids C omp os é C 36,0Kaolin up to 100.0 20 (5)% by weight C omposed C 36.0
Fenarimol 6,0Fenarimol 6.0
Alkyl-éther-sulfate de sodium 4,0Sodium alkyl ether sulfate 4.0
Lignine-suifonate de sodium 3,0 25 Silice 7,0Sodium lignin-sulfonate 3.0 25 Silica 7.0
Attapulgite jusqu'à 100,0 (6) % en poids t C omp osêC 6,0Attapulgite up to 100.0 (6)% by weight t C omp osêC 6.0
Fenarimol 1,0 30 Zineb 50,0Fenarimol 1.0 30 Zineb 50.0
Sel de sodium d'acides naphtalène-sulfoniques condensés 3,0Sodium salt of condensed naphthalene sulfonic acids 3.0
Lignine-suifonate de sodium 4,0Sodium lignin-sulfonate 4.0
Silicoaluminate de sodium hydraté 8,0 35 Montraorillonite · jusqu'à 100,0 (7f) % eu poids / Composé C 3,0 5ijp Fenarimol 0,5 i · 6 i ) « î Kanc ozeb 3610 ^ Poudre de lessive sulfitique 2,0Sodium silicoaluminate hydrated 8.0 35 Montraorillonite · up to 100.0 (7f)% w / weight / Compound C 3.0 5ijp Fenarimol 0.5 i · 6 i) “Kanc ozeb 3610 ^ Sulfitic washing powder 2, 0
Lauryl-sulfate de sodium 5,0Sodium lauryl sulfate 5.0
Silice 6,0 I 5 Kaolin jusqu'à 100,0 (8) % en poidsSilica 6.0 I 5 Kaolin up to 100.0 (8)% by weight
Composé A 40,0 i Triadimefon 10,0Compound A 40.0 i Triadimefon 10.0
Nonyl-phénol éthoxylê 5,0 j 10 Lignine-suifonate de sodium. 2,0Nonyl-phenol ethoxylate 5.0 to 10 Sodium lignin-sulfonate. 2.0
Silice 4,0Silica 4.0
Talc ' jusqu'à 100,0 (9) % en poidsTalc 'up to 100.0 (9)% by weight
Composé B 50,0 I 15 Triadimefon 10,0 l Lauryl-sulfate de sodium 2,0 1 Sel de sodium d'acides naphtalène-sulfoniques condensés 4,0Compound B 50.0 I 15 Triadimefon 10.0 l Sodium lauryl sulfate 2.0 1 Sodium salt of condensed naphthalene sulfonic acids 4.0
Silice précipitée 6,0Precipitated silica 6.0
Kaolin jusqu'à 100,0 20 (10) en poidsKaolin up to 100.0 20 (10) by weight
Composé C 30,0Compound C 30.0
Triadimefon 10,0Triadimefon 10.0
Dioctyl-sulfosuccinate de sodium 3,0 . Lignine sulfonatée 4,0 I25 Silicoaluminate de sodium hydraté 8,0Sodium dioctyl sulfosuccinate 3.0. Sulfonated lignin 4.0 I25 Sodium hydricoaluminate hydrate 8.0
Attapulgite jusqu'à 100,0Attapulgite up to 100.0
Dans chacun des exemples précités, les constituants actifs sont ' soigneusement mélangés avec les excipients ou supports indiqués dans des installations de mélange classiques. Le mélange est de plus broyé à un f 50 broyeur à énergie fluidique jusqu'à une granulométrie de 1 à 10 microns, I et finalement le mélange est à nouveau mélangé et désaéré avant l'emballa | _ Les compositions décrites dans les exemples 1, 3 5 à 10 sont prévues pour une application foliaire tandis que les compositions u€o exemples 2 et 4 sont intéressantes comme arrosage du sol.In each of the above examples, the active constituents are carefully mixed with the excipients or carriers indicated in conventional mixing plants. The mixture is further ground in a f 50 fluid energy mill to a particle size of 1 to 10 microns, I and finally the mixture is again mixed and deaerated before packaging. _ The compositions described in examples 1, 3 5 to 10 are intended for foliar application while the compositions u € o examples 2 and 4 are useful as watering the soil.
35 Exemple 11 I L'exemple qui suit est destiné à illustrer l'activité syneîÊ-Ç.Ue35 Example 11 I The following example is intended to illustrate the syneîÊ-Ç.Ue activity
f typique que l'on observe lorsque les combinaisons de l’invention sO-Zf typical that is observed when the combinations of the invention sO-Z
7 utilisées pour agir sur des organismes fongiques-7 used to act on fungal organisms-
Des solutions de fenarimol dans l'eau sont préparées à une concentration de 10 et 20 parts par million et des solutions de composé B sont préparées à une concentration de 50 et 100 parts par million. Elles sont 5 appliquées séparément et ensemble à des plants de haricots Pinto de 11 jours. Un traitement unique consiste en une pulvérisation de 3 pots, chaque pot contenant deux plants.Fenarimol solutions in water are prepared at a concentration of 10 and 20 parts per million and solutions of compound B are prepared at a concentration of 50 and 100 parts per million. They are applied separately and together to 11 day Pinto bean plants. A single treatment consists of a spray of 3 pots, each pot containing two plants.
Lorsque les plants ont séchés, ils sont inoculés avec une suspension de spores de rouille de feuilles de haricots et incubés pendant 48 heures 10 dans une chambre humide froide.When the plants have dried, they are inoculated with a suspension of bean leaf rust spores and incubated for 48 hours in a cold humid room.
Le pourcentage d'effet sur la maladie a été noté comme suit : FENARIMOL COMPOSE B Pourcentage -—----—--- d'effet de la (concentré (pourcentage (concentré (pourcentage combinaison de 15 p.p.m. d'effet sur p.p.m. d'effet sur fenarimol et deThe percentage effect on the disease was noted as follows: FENARIMOL COMPOUND B Percentage --—----—--- of the (concentrate (percentage (concentrate (percentage combination of 15 ppm effect on ppm) effect on fenarimol and
la maladie la maladie) composé Bdisease disease) compound B
10 35 50 6 62 10 35 100 29 85 20 77 50 6 95 20 20 77 100 29 9610 35 50 6 62 10 35 100 29 85 20 77 50 6 95 20 20 77 100 29 96
Analysés par l'équation "Colby" bien connue (voir Ueeds, 15, 20-22 (1967), les résultats-ci-dessus indiquent clairement que dans des conditions par ailleurs identiques de l'essai, le mélange de l’invention met en évidence un effet de synergie.Analyzed by the well-known "Colby" equation (see Ueeds, 15, 20-22 (1967), the above results clearly indicate that under otherwise identical conditions of the test, the mixture of the invention provides highlight a synergistic effect.
ÀAT
Claims (8)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1282478 | 1978-04-01 | ||
| GB1282478 | 1978-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU81096A1 true LU81096A1 (en) | 1980-10-08 |
Family
ID=10011816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU81096A LU81096A1 (en) | 1978-04-01 | 1979-03-29 | FUNGICIDAL COMPOSITION AND METHOD FOR FUNGICIDAL TREATMENT OF CULTIVATED PLANTS |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPS54132233A (en) |
| AR (4) | AR225414A1 (en) |
| AT (1) | AT364196B (en) |
| AU (1) | AU527924B2 (en) |
| BE (1) | BE875198A (en) |
| BG (4) | BG31470A3 (en) |
| BR (1) | BR7901929A (en) |
| CA (1) | CA1128854A (en) |
| CH (1) | CH638079A5 (en) |
| CS (4) | CS217976B2 (en) |
| DD (1) | DD143552A5 (en) |
| DE (1) | DE2912491A1 (en) |
| DK (4) | DK126779A (en) |
| EG (1) | EG13864A (en) |
| ES (1) | ES479135A1 (en) |
| FR (4) | FR2422332A1 (en) |
| GB (1) | GB2077591B (en) |
| GR (1) | GR67710B (en) |
| HU (2) | HU182518B (en) |
| IE (1) | IE47941B1 (en) |
| IL (1) | IL56963A (en) |
| IN (1) | IN149760B (en) |
| IT (1) | IT1120402B (en) |
| LU (1) | LU81096A1 (en) |
| NL (1) | NL7902435A (en) |
| NO (4) | NO147202C (en) |
| NZ (1) | NZ190062A (en) |
| PL (4) | PL122824B1 (en) |
| PT (1) | PT69407A (en) |
| RO (2) | RO80251A (en) |
| SE (4) | SE446811B (en) |
| SU (1) | SU1311600A3 (en) |
| TR (1) | TR20289A (en) |
| ZA (1) | ZA791494B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS217976B2 (en) | 1978-04-01 | 1983-02-25 | Lilly Industries Ltd | Fungicide means |
| DE3326664A1 (en) * | 1982-07-29 | 1984-02-02 | Lilly Industries Ltd., London | Fungicidal agent and process for its preparation |
| EP0645084B1 (en) * | 1993-09-24 | 1996-07-31 | BASF Aktiengesellschaft | Fungicidal mixtures |
| PL224139B1 (en) | 2014-08-01 | 2016-11-30 | Ekobenz Spółka Z Ograniczoną Odpowiedzialnością | Fuel blend, particularly for engines with spark ignition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912752A (en) * | 1972-01-11 | 1975-10-14 | Bayer Ag | 1-Substituted-1,2,4-triazoles |
| OA04979A (en) * | 1974-04-09 | 1980-11-30 | Ciba Geigy | New aniline derivatives useful as microbicidal agents and their preparation process. |
| GB1561634A (en) * | 1975-10-29 | 1980-02-27 | Lilly Industries Ltd | Fungicidal compositions |
| DE2552967A1 (en) * | 1975-11-26 | 1977-06-08 | Bayer Ag | FUNGICIDALS |
| GB1559820A (en) * | 1975-12-09 | 1980-01-30 | Lilly Industries Ltd | Fungicidal compositions |
| GB1581527A (en) * | 1976-08-18 | 1980-12-17 | Lilly Industries Ltd | Fungicidal formulations |
| CS217976B2 (en) | 1978-04-01 | 1983-02-25 | Lilly Industries Ltd | Fungicide means |
-
1979
- 1979-03-23 CS CS802269A patent/CS217976B2/en unknown
- 1979-03-23 CS CS802270A patent/CS217977B2/en unknown
- 1979-03-23 CS CS802271A patent/CS217978B2/en unknown
- 1979-03-28 AR AR275965A patent/AR225414A1/en active
- 1979-03-28 AU AU45485/79A patent/AU527924B2/en not_active Ceased
- 1979-03-28 SE SE7902780A patent/SE446811B/en not_active IP Right Cessation
- 1979-03-28 DK DK126779A patent/DK126779A/en not_active Application Discontinuation
- 1979-03-28 CA CA324,339A patent/CA1128854A/en not_active Expired
- 1979-03-28 GR GR58713A patent/GR67710B/el unknown
- 1979-03-28 FR FR7907805A patent/FR2422332A1/en active Granted
- 1979-03-28 EG EG190/79A patent/EG13864A/en active
- 1979-03-28 IL IL56963A patent/IL56963A/en unknown
- 1979-03-29 BG BG045203A patent/BG31470A3/en unknown
- 1979-03-29 CS CS792108A patent/CS221251B2/en unknown
- 1979-03-29 ZA ZA791494A patent/ZA791494B/en unknown
- 1979-03-29 BE BE6/46792A patent/BE875198A/en not_active IP Right Cessation
- 1979-03-29 LU LU81096A patent/LU81096A1/en unknown
- 1979-03-29 BR BR7901929A patent/BR7901929A/en unknown
- 1979-03-29 BG BG043056A patent/BG31364A3/en unknown
- 1979-03-29 BG BG045204A patent/BG31471A3/en unknown
- 1979-03-29 JP JP3768479A patent/JPS54132233A/en active Pending
- 1979-03-29 DE DE19792912491 patent/DE2912491A1/en not_active Ceased
- 1979-03-29 PT PT69407A patent/PT69407A/en unknown
- 1979-03-29 IN IN307/CAL/79A patent/IN149760B/en unknown
- 1979-03-29 NL NL7902435A patent/NL7902435A/en not_active Application Discontinuation
- 1979-03-29 TR TR20289A patent/TR20289A/en unknown
- 1979-03-29 BG BG045202A patent/BG31469A3/en unknown
- 1979-03-29 CH CH290179A patent/CH638079A5/en not_active IP Right Cessation
- 1979-03-30 IT IT48541/79A patent/IT1120402B/en active
- 1979-03-30 SU SU792748355A patent/SU1311600A3/en active
- 1979-03-30 HU HU79LI338A patent/HU182518B/en unknown
- 1979-03-30 AT AT0239679A patent/AT364196B/en not_active IP Right Cessation
- 1979-03-30 RO RO79102292A patent/RO80251A/en unknown
- 1979-03-30 RO RO7997081A patent/RO75492A/en unknown
- 1979-03-30 GB GB8112001A patent/GB2077591B/en not_active Expired
- 1979-03-30 DD DD79211922A patent/DD143552A5/en unknown
- 1979-03-30 NZ NZ190062A patent/NZ190062A/en unknown
- 1979-03-30 NO NO791074A patent/NO147202C/en unknown
- 1979-03-30 ES ES479135A patent/ES479135A1/en not_active Expired
- 1979-03-30 HU HU83114A patent/HU189633B/en unknown
- 1979-03-31 PL PL1979230914A patent/PL122824B1/en unknown
- 1979-03-31 PL PL1979230915A patent/PL123456B1/en unknown
- 1979-03-31 PL PL1979230916A patent/PL122819B1/en unknown
- 1979-03-31 PL PL1979214575A patent/PL119526B1/en unknown
- 1979-06-29 FR FR7916982A patent/FR2424701A1/en active Granted
- 1979-06-29 FR FR7916985A patent/FR2424702A1/en active Granted
- 1979-06-29 FR FR7916986A patent/FR2424703A1/en active Granted
- 1979-08-08 IE IE665/79A patent/IE47941B1/en unknown
-
1981
- 1981-08-06 AR AR286356A patent/AR227933A1/en active
- 1981-08-06 AR AR286355A patent/AR227932A1/en active
- 1981-08-06 AR AR286354A patent/AR228962A1/en active
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1982
- 1982-06-30 NO NO822278A patent/NO148768C/en unknown
- 1982-06-30 NO NO822277A patent/NO148766C/en unknown
- 1982-06-30 NO NO822279A patent/NO148767C/en unknown
-
1984
- 1984-02-22 SE SE8400977A patent/SE8400977D0/en not_active Application Discontinuation
- 1984-02-22 SE SE8400978A patent/SE8400978L/en not_active Application Discontinuation
- 1984-02-22 SE SE8400976A patent/SE454399B/en not_active IP Right Cessation
-
1988
- 1988-03-04 DK DK120588A patent/DK120588D0/en not_active Application Discontinuation
- 1988-03-04 DK DK120688A patent/DK120688D0/en not_active Application Discontinuation
- 1988-03-04 DK DK120788A patent/DK120788D0/en unknown
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