GB2049672A - Herbicidally Active N-(2- propynyl)-carbanilic acid (3- aliphatic Hydrocarbon-oxy-or thiocarbonylaminophenyl) Esters and Their Manufacture and Use - Google Patents
Herbicidally Active N-(2- propynyl)-carbanilic acid (3- aliphatic Hydrocarbon-oxy-or thiocarbonylaminophenyl) Esters and Their Manufacture and Use Download PDFInfo
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- GB2049672A GB2049672A GB8010810A GB8010810A GB2049672A GB 2049672 A GB2049672 A GB 2049672A GB 8010810 A GB8010810 A GB 8010810A GB 8010810 A GB8010810 A GB 8010810A GB 2049672 A GB2049672 A GB 2049672A
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- compound
- general formula
- propynyl
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- ester
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- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
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- 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)
Abstract
Novel compounds of the general formula I <IMAGE> (wherein R represents C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl and X represents O or S) and their manufacture. The compounds have a herbicidal action, especially a selective herbicidal action, and accordingly may be made up with suitable carriers into herbicidal preparations and may be used for protecting living plants and crop areas against weeds.
Description
SPECIFICATION
Herbicidally Active N-(2-propynyl)-carbanilic Acid (3-aliphatic Hydrocarbon-oxy- or thiocarbonylaminophenyl) Esters and Their Manufacture and Use
The present invention is concerned with new N-(2-propynyl)-carbanilic acid (3-aliphatic hydrocarbonoxy- or -thio-carbonylaminophenyl) esters, with processes for the manufacture of these compounds and also with their use as herbicidal agents, especially selective herbicidal agents.
The herbicidal action of carbanilic acid (3-alkoxycarbonylaminophenyl) esters and diurethanes is already known (German Patent Specification No. 1,567,1 15).
These compounds have a sufficient selectivity only in beta beet crops. Furthermore, these compounds exhibit large gaps in activity.
The problem upon which the present invention is based has been to provide a weed-controlling agent which furthermore acts against weeds that are difficult to control, especially accompanied by a complete tolerability towards important agricultural crops. This problem is solved according to the present invention by the compounds of the general formula I, as defined below.
The present invention accordingly provides compounds of the general formula I
in which R represents a C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl group and X represents an oxygen or sulphur atom.
The compounds of the present invention surprisingly exhibit a greater selective herbicidal action than do known constitutionally analogous compounds having the same direction of action.
A further technically more important advantage of the compounds of the present invention lies in their practical use, as they can be used as new herbicides against those resistant weeds and a secondary flora that can no longer be adequately controiled by the herbicides known in practice owing to the development of a resistance by the weeds.
The compounds of the present invention are distinguished by a broad leaf-herbicidal action. They can be used for controlling dicotyledonous weeds. The compounds control by the post-emergence methods weeds in arable land, for example Stellaria media Matricaria chamonilla, Lamium amplexicaule, Centaurea cyanus, A maran tus retroflexus, Solanum saccharoides, Escholtzia californica, Ipomoea purpurae, Searia italica and other weeds.
For controlling seed weeds there are generally used application quantities within the range of from 1 kg to 5 kg of active substance per hectare. In this way the characterized active substances are surprisingly selective in commercial plant crops, for example cotton, potatoes, maize, wheat and rice.
When two or more compounds of the general formula I are used, the range of 1 to 5 kg refers of course to the total application quantities of these compounds.
The present invention accordingly also provides a herbicidal 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 weeds, wherein the area in the vicinity of 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 weeds, wherein the crop area is treated with a compound of the 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 as a herbicide.
The compounds of the present invention may be used either singly or in the form of mixtures with one another or with other active substances. If desired, other plant-protecting agents and/or pesticides may be added, depending on the desired aim.
If a broadening of the range of action is intended, other herbicides may also be added. As suitable herbicidally-active co-components there may be mentioned, for example, active substances from the groups of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxylic acids and aryloxycarboxylic acids, hydrazides, amides, nitriles and esters of such carboxylic acids, carbamic acid esters, thiocarbamic acid esters, ureas, 2,3,6- trichlorobenzyloxyisopropanol, thiocyanate-containing agents and other additives. Among other additives there are to be understood, for example, nonphytotoxic additives which are capable of producing, with herbicides, a synergistic increase in action, for example wetting agents, emulsifiers, solvents and oily additives.
The active compounds of the present invention or mixtures containing them are advantageously used in the form of herbicidal preparations, for example powders, strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents and, if desired, of surface-active agents, for example wetting, adhesive, emulsifying and/or dispersing agents.
Suitable liquid carriers are, for example, water, aliphatic hydrocarbons, aromatic hydrocarbons, for example benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide and dimethyl formamide, and also mineral oil fractions.
Suitable solid carriers are, for example, mineral earths, for example tonsil, silica gel, talcum, kaolin, attaclay, limestone and silicic acid, and vegetable products, for example meals.
As surface-active agents there may be mentioned, for example, calcium lignin sulphonate, polyoxyethylene-alkylphenol ethers, naphthalenesulphonic acids and salts thereof, phenolsulphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates and also substituted benzenesulphonic acids and salts thereof.
The proportion of the active substance or substances in the various herbicidal preparations may vary within wide limits. For example, the preparations may contain approximately 5 to 95% by weight of active substance(s), approximately 95 to 5% by weight of liquid or solid carrier and also, if desired, up to 20% by weight of surface-active agent(s).
The active compounds may be applied in the usual manner, for example with water as carried in quantities of spray liquor of approximately 50 to 1000 litres per hectare. It is also possible to apply the active compounds by the so-called low-volume and ultra-low-volume methods as well as to apply them in the form of so-called microgranules.
Among the compounds of the present invention that are distinguished by an outstanding selective herbicidal action there should be mentioned more especially those of the general formula I in which R represents a methyl, ethyl, isopropyl, allyl, propynyl, isobutyl, sec.-butyl, sec.-butenyl or sec.butynyl group and X represents an oxygen or sulphur atom.
The new compounds of the general formula I may be manufactured, for example, by the process of the present invention, as defined below.
The present invention accordingly further provides a process for the manufacture of the compounds of the general formula I, wherein
a) a compound of the general formula
in which R and X have the meanings given above, is reacted with N-(2-propynyl)-aniline of the formula
in the presence of an acid acceptor, for example with the addition of an excess of the amine or of an inorganic base, for example a sodium hydroxide solution, sodium carbonate or potassium carbonate, or a tertiary organic base, for example triethylamine, or
b) a compound of the general formula
in which R and X have the meanings given above, is reacted in the presence of a tertiary organic base, for example triethylamine or pyridine, or is reacted in the form of an aikali salt thereof with N-phenyl-N (2-propynyl)-carbamoyl chloride of the formula
each reaction of variant (b) being carried out at a temperature within the range of from 0 to 1000C.
The compounds of the general formula I formed by the variant (a) or (b) may be isolated in the usual manner.
The compounds of the present invention are soluble in, for example, isophorone, cyclohexanone, acetone, tetrahydrofuran, dimethylformamide and dimethyl sulphoxide and sparingly soluble in, for example, water, benzene and toluene.
The following Examples illustrate the invention. Example 1 illustrates the manufacture of the compounds of the present invention and Examples 2 and 3 iliustrate the possible ways of using the compounds of the present invention, the compounds in Examples 2 and 3 being used in the form of preparations thereof.
Example 1
N-(2-Propynyl)-carbanilic Acid (3-methoxycarbonylaminophenyl) Ester
Into a solution of 39.4 g (0.3 mole) of N-(2-propynyl)-aniline in 75 ml of ethyl acetate were introduced dropwise, while stirring and cooling to 8 to 120C, a solution of 68.7 g (0.3 mole) of chloroformic acid (3-methoxycarbonylaminophenyl) ester in 1 50 ml of ethyl acetate and simultaneously a solution of 41.4 g (0.3 mole) of potassium carbonate in 150 ml of water. Stirring was continued for 30 minutes at 1 OOC, and then the organic phase was separated and, with the addition of ice, washed with dilute hydrochloric acid and water. After drying the mixture with magnesium sulphate it was concentrated by evaporation under reduced pressure, and then 500 ml of isopropyl ether were added, whereupon the reaction product crystallized out.
Yield: 67.9 g=69.8% of the theoretical yield.
Melting point: 10400.
The following compounds of the present invention may be prepared in an analogous manner.
Physical
Name ofthe compound constant
N-(2-Propynyl)-carbanilic acid [3-(methylthio-carbonylamino)-phenyl]
ester M.p.: 1300C N-(2-Propynyl)-carbanilic acid [3-(ethylthio-carbonylamino)-phenyl] ester M.p.: 990C
N-(2-Propynyl)-carbanilic acid [3-(2-propynyloxycarbonylamino)-phenyl]
ester M.p.: 1180C N-(2-Propynyl)-carbanilic acid [3-(2-methylpropoxycarbonylamino)- phenyl] ester M.p.: 1080C
N-(2-Propynyl)-carbanilic acid (3-ethoxycarbonylaminophenyl) ester M.p.: 101 to 1030C
N-(2-Propynyl)-carbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester M.p.: 78--790C N-(2-Propynyl)-carbanilic acid [3-(1-methyl-2- propenyloxycarbonylamino)-phenyl] ester M.p.: 96--970C Example 2
In a series of tests carried out in a greenhouse, the compounds of the present invention listed in the Table below were each sprayed in the form of an aqueous emulsion or suspension by the postemergence method at a rate of application of 5 kg of active substance per hectare in 500 litres of wate per hectare, on to Solanum and Brassica as the test plants.
Three weeks after the treatment the results thereof were evaluated and expressed by a numerical scale having the values 0, 1, 2, 3 and 4, the value 0 at one end of the scale representing no action and the value 4 at the other end representing destruction of the plant.
The results show that in general destruction of the plants was achieved.
Compound of the invention Solanum Brassica N-(2-Propynyl)-carbanilic acid 4 4 [3-( methylthio-carbonylamino)- phenyl] ester
N-(2-Propynyl)-carbanilic acid 4 4 [3-(ethylthio-ca rbonylamino)- phenyl] ester
N-(2-Propynyl)-carbanilic acid 4 4
[3-(2-propynyloxycarbonyl
amino)-phenyl] ester
N-(2-Propynyl)-carbanilic acid 4 4
[3 -(2-methyl propoxycarbonyl
amino)-phenyl] ester
N-(2-Propynyl)-carbanilic acid 4 4
(3-ethoxycarbonylaminophenyl)
ester
N-(2-Propynyl)-carbanilic acid 4 4
[3-( 1 -methylethoxycarbonyl- amino)-phenyl] ester
N-(2-Propynyl)-carbanilic acid 4 4
[3-( 1 -methyl-2-propenyloxy
carbonylamino)-phenyl] ester
Untreated O 0
O=no action 4=destruction of the plant
Example 3
In a series of tests carried out in a greenhouse, the plants listed in the Table below were treated after their emergence with the compound of the present invention and the known compound used for
comparison, in each case in the form of an aqueous emulsion applying 1 kg of active substance per
hectare in 500 litres of water per hectare. For this purpose, the aqueous emulsion was in each case
sprayed uniformly over the plants.
Three weeks after the treatment the results thereof were evaluated and expressed by a numerical
scale extending from 0 to 10, the value 0 representing total destruction of the plant and the value 10
representing no damage.
The compound of the present invention exhibited an outstanding selective herbicidal action, whereas the known compound did not.
F .. 3 F . ca Compound of the invention 2 > 0 E N-(2-Propynyl)-carbanilic acid 10 10 10 0 0 1 0 7 4 (3-ethoxycarbonyla minophenyl) ester Agent for comparison according to German Patent Specification No. 1,567,151. 3-Methoxycarbonylaminophenyl-N- 1 8 7 5 8 4 2 8 5 (3'-methylphenyl) carbamate Untreated 10 10 10 10 10 10 10 10 10 0=total destruction 10=no damage
Claims (41)
1. A compound of the general formula I
in which R represents a C1-C4-alkyl, C3-C4-a Ikenyl or C3-C4-alkynyl group and X represents an oxygen or sulphur atom.
2. A compound as claimed in claim 1 , wherein R represents a methyl, ethyl, isopropyl, allyl, propynyl, isobutyl, sec.-butyl, sec.-butenyl or sec.-butynyl group and X represents an oxygen or sulphur atom.
3. N-(2-Propynyl)-carbanilic acid (3-methoxycarbonylaminophenyl) ester.
4. N-(2-Propynyl)-carbanilic acid [3-(methylthiocarbonylamino)-phenyl] ester.
5. N-(2-Propynyl)-carbanilic acid [3-(ethylthiocarbonylamino)-phenyl] ester.
6. N-(2-Propynyl)carbanilic acid t3-(2-propynyloxycarbonylamino)-phenyl]ester.
7. N-(2-Propynyl)-carbanilic acid [3-(2-methylpropoxycarbonylamino)-phenyl] ester.
8. N-(2-Propynyl)-carbanilic acid (3-ethoxycarbonylaminophenyl) ester.
9. N-(2-Propynyl)-carbanilic acid [3-( 1 -methylethoxycarbonylamino)-phenyl] ester.
1 0. N-(2-Propynyl)-carbanilic acid [3-(1 -methyl-2-propenyloxycarbonylamino)-phen ester.
11. A process for the manufacture of a compound of the general formula I given in claim 1, in which R and X have the meanings given in claim 1 , wherein a) a compound of the general formula
in which R and X have the meanings given above, is reacted in the presence of an acid acceptor with N (2-propynyl)-aniline of the formula
u
b) a compound of the general formula
in which R and X have the meanings given above, is reacted in the presence of a tertiary organic base or is reacted in the form of an alkali salt thereof with N-phenyl-N-(2-propynyl)-carbamoyl chloride of the formula
each reaction of variant (b) being carried out at a temperature within the range of from 0 to 1000C.
12. A process as claimed in claim 11, conducted substantially as described herein.
13. A process as claimed in claim 11, conducted substantially as described in Example 1 herein.
14. A herbicidal preparation which comprises a compound of the general formula I given in claim 1, in which R and X have the meanings given in claim 1, in admixture or conjunction with a suitable carrier.
1 5. A herbicidal preparation which comprises a compound as claimed in claim 2, in admixture or conjunction with a suitable carrier.
1 6. A herbicidal preparation which comprises the compound claimed in any one of claims 3 to 10, in admixture or conjunction with a suitable carrier.
1 7. A preparation as claimed in any one of claims 14 to 16, which is in the form of a powder, a strewable preparation, granules, a solution, an emulsion or a suspension.
18. A preparation as claimed in any one of claims 14 to 1 7, containing a single compound of the general formula i.
1 9. A preparation as claimed in any one of claims 14 to 17, containing two or more compounds of the general formula I.
20. A preparation as claimed in any one of claims 14 to 19, which also contains one or more active substances selected from plant-protecting agents, pesticides and herbicides other than compounds of the general formula
21. A preparation as claimed in any one of claims 14 to 20, wherein the total amount present of active substance or substances is approximately 5 to 95% by weight.
22. A preparation as claimed in any one of claims 14 to 21, containing a single surface-active agent in an amount of up to 20% by weight.
23. A preparation as claimed in any one of claims 14 to 21, containing two or more surfaceactive agents in a total amount of up to 20% by weight.
24. Any one of the herbicidal preparations as claimed in claim 14 and substantially as described in Examples 2 and 3 herein.
25. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a compound of the general formula I given in claim 1, in which R and X have the meanings given in claim 1.
26. A method as claimed in claim 25, wherein the area is treated with a compound as claimed in claim 2.
27. A method as claimed in claim 25, wherein the area is treated with a compound claimed in any one of claims 3 to 10.
28. A method as claimed in claim 25, wherein the area is treated with a herbicidal preparation as claimed in any one of claims 14 to 24.
29. A method as claimed in any one of claims 25 to 28, wherein a single compound of the general formula I is used for the treatment in an amount within the range of from 1 to 5 kg per hectare.
30. A method as claimed in any one of claims 25 to 28, wherein two or more compounds of the general formula I are used for the treatment in a total amount within the range of from 1 to 5 kg per hectare.
31. A method as claimed in claim 25, conducted substantially as described in Example 3 herein.
32. A method of protecting a crop area against weeds, wherein the crop area is treated with a compound of the general formula I given in claim 1, in which R and X have the meanings given in claim
1.
33. A method as claimed in claim 32, wherein the crop area is treated with a compound as claimed in claim 2.
34. A method as claimed in claim 32, wherein the crop area is treated with the compound claimed in any one of claims 3 to 10.
35. A method as claimed in claim 32, wherein the crop area is treated with a herbicidal preparation as claimed in any one of claims 14 to 24.
36. A method as claimed in any one of claims 32 to 35, wherein a single compound of the general formula I is used for the treatment in an amount within the range of from 1 to 5 kg per hectare.
37. A method as claimed in any one of claims 32 to 35, wherein two or more compounds of the general formula I are used for the treatment in a total amount within the range of from 1 to 5 kg per hectare.
38. A method as claimed in any one of claims 32 to 37, wherein the crop is a cotton, potato, maize, wheat or rice crop.
39. A pack which comprises a compound of the general formula I given in claim 1, in which R and
X have the meanings given in claim 1, together with instructions for its use as a herbicide.
40. A pack as claimed in claim 39, wherein the compound of the general formula lisa compound as claimed in claim 2.
41. A pack as claimed in claim 39, wherein the compound of the general formula I is the compound claimed in any one of claims 3 to 10.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913975 DE2913975A1 (en) | 1979-04-05 | 1979-04-05 | N- (2-PROPINYL) -CARBANILIC ACID- (3-ALKOXY- AND ALKYLTHIOCARBONYLAMINO-PHENYL) -ESTERS, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDES CONTAINING THEM |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2049672A true GB2049672A (en) | 1980-12-31 |
| GB2049672B GB2049672B (en) | 1983-03-09 |
Family
ID=6067686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8010810A Expired GB2049672B (en) | 1979-04-05 | 1980-03-31 | Herbicidally active n-(2-propynyl)-carbanilic acid-(3-aliphatic hydrocarbon-oxy-or-thiocarbonylaminophenyl) esters and their manufacture and use |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5819672B2 (en) |
| AR (1) | AR224521A1 (en) |
| AT (1) | AT365896B (en) |
| AU (1) | AU535374B2 (en) |
| BE (1) | BE882627A (en) |
| BG (1) | BG34897A3 (en) |
| BR (1) | BR8002009A (en) |
| CA (1) | CA1125301A (en) |
| CH (1) | CH645344A5 (en) |
| CS (1) | CS209949B2 (en) |
| DD (1) | DD149996A5 (en) |
| DE (1) | DE2913975A1 (en) |
| EG (1) | EG14317A (en) |
| ES (1) | ES8107172A1 (en) |
| FI (1) | FI800832A (en) |
| FR (1) | FR2453142A1 (en) |
| GB (1) | GB2049672B (en) |
| GR (1) | GR67206B (en) |
| HU (1) | HU181764B (en) |
| IL (1) | IL59736A (en) |
| IN (1) | IN154011B (en) |
| IT (1) | IT1148780B (en) |
| MA (1) | MA18803A1 (en) |
| MX (1) | MX6017E (en) |
| NL (1) | NL8001638A (en) |
| PH (1) | PH17275A (en) |
| PL (1) | PL123694B1 (en) |
| PT (1) | PT71032A (en) |
| RO (1) | RO79220A (en) |
| SE (1) | SE8002183L (en) |
| SU (1) | SU925248A3 (en) |
| TR (1) | TR20575A (en) |
| YU (1) | YU76180A (en) |
| ZA (1) | ZA802032B (en) |
| ZW (1) | ZW7980A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6014760U (en) * | 1983-07-09 | 1985-01-31 | フランスベッド株式会社 | Pine tress device |
| JPS6074668U (en) * | 1983-10-28 | 1985-05-25 | フランスベッド株式会社 | pine tress |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2413933A1 (en) * | 1974-03-20 | 1975-09-25 | Schering Ag | DIURETHANE WITH SELECTIVE HERBICIDAL EFFECT |
| DE2557552C2 (en) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethanes and herbicidal agents containing these compounds as active ingredients |
| DE2650796A1 (en) * | 1976-11-03 | 1978-05-11 | Schering Ag | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM |
| DE2651526A1 (en) * | 1976-11-09 | 1978-05-18 | Schering Ag | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM |
-
1979
- 1979-04-05 DE DE19792913975 patent/DE2913975A1/en not_active Withdrawn
-
1980
- 1980-03-18 FI FI800832A patent/FI800832A/en not_active Application Discontinuation
- 1980-03-19 YU YU00761/80A patent/YU76180A/en unknown
- 1980-03-19 NL NL8001638A patent/NL8001638A/en not_active Application Discontinuation
- 1980-03-20 SE SE8002183A patent/SE8002183L/en not_active Application Discontinuation
- 1980-03-25 IN IN217/DEL/80A patent/IN154011B/en unknown
- 1980-03-26 CH CH238480A patent/CH645344A5/en not_active IP Right Cessation
- 1980-03-27 CS CS802160A patent/CS209949B2/en unknown
- 1980-03-28 PT PT71032A patent/PT71032A/en unknown
- 1980-03-28 SU SU802901453A patent/SU925248A3/en active
- 1980-03-31 MX MX808729U patent/MX6017E/en unknown
- 1980-03-31 IL IL59736A patent/IL59736A/en unknown
- 1980-03-31 GB GB8010810A patent/GB2049672B/en not_active Expired
- 1980-04-01 BR BR8002009A patent/BR8002009A/en unknown
- 1980-04-01 CA CA348,942A patent/CA1125301A/en not_active Expired
- 1980-04-02 AT AT0180680A patent/AT365896B/en not_active IP Right Cessation
- 1980-04-02 ES ES490256A patent/ES8107172A1/en not_active Expired
- 1980-04-02 GR GR61616A patent/GR67206B/el unknown
- 1980-04-02 AR AR280534A patent/AR224521A1/en active
- 1980-04-02 BG BG8047214A patent/BG34897A3/en unknown
- 1980-04-03 HU HU80818A patent/HU181764B/en unknown
- 1980-04-03 ZA ZA00802032A patent/ZA802032B/en unknown
- 1980-04-03 IT IT21168/80A patent/IT1148780B/en active
- 1980-04-03 DD DD80220215A patent/DD149996A5/en unknown
- 1980-04-03 ZW ZW79/80A patent/ZW7980A1/en unknown
- 1980-04-03 TR TR20575A patent/TR20575A/en unknown
- 1980-04-03 BE BE0/200112A patent/BE882627A/en not_active IP Right Cessation
- 1980-04-03 AU AU57150/80A patent/AU535374B2/en not_active Ceased
- 1980-04-03 PL PL1980223231A patent/PL123694B1/en unknown
- 1980-04-04 JP JP55043644A patent/JPS5819672B2/en not_active Expired
- 1980-04-04 FR FR8007670A patent/FR2453142A1/en active Granted
- 1980-04-04 RO RO80100727A patent/RO79220A/en unknown
- 1980-04-04 MA MA18998A patent/MA18803A1/en unknown
- 1980-04-05 EG EG207/80A patent/EG14317A/en active
- 1980-04-07 PH PH23863A patent/PH17275A/en unknown
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