CA1100403A - Fungicide - Google Patents
FungicideInfo
- Publication number
- CA1100403A CA1100403A CA298,647A CA298647A CA1100403A CA 1100403 A CA1100403 A CA 1100403A CA 298647 A CA298647 A CA 298647A CA 1100403 A CA1100403 A CA 1100403A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- formula
- nitrogen atom
- alkyl radical
- oxygen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A fungicide containing as an active ingredient the compounds with the general formula 1 (1) where:
X is a halide or methyl sulphate ion with "n" equal 1 or 2, R1 and R2 are alkyl radicals with 1-4 carbon atoms, R3 is an alkyl radical with 1-4 carbon atoms or cyclohexyl radical, R4 is an alkyl radical with 1-18 carbon atoms, or R2 and R3 together with the nitrogen atom form a ring with formula 2 (2) where:
W is an oxygen atom, methylene group or a nitrogen atom substituted as in formula 3 (3) where:
R1 and R4 have the above moaning, U and Y are hydrogen atoms or methyl groups, Z is a hydrogen atom, or Y and Z together are an oxygen atom.
The agent containing as active compounds with the general formula 1, where the substituents have the above meaning, have strong, also systemic, action towards fungi, especially of the Alternaria and Phytophthora genera.
A fungicide containing as an active ingredient the compounds with the general formula 1 (1) where:
X is a halide or methyl sulphate ion with "n" equal 1 or 2, R1 and R2 are alkyl radicals with 1-4 carbon atoms, R3 is an alkyl radical with 1-4 carbon atoms or cyclohexyl radical, R4 is an alkyl radical with 1-18 carbon atoms, or R2 and R3 together with the nitrogen atom form a ring with formula 2 (2) where:
W is an oxygen atom, methylene group or a nitrogen atom substituted as in formula 3 (3) where:
R1 and R4 have the above moaning, U and Y are hydrogen atoms or methyl groups, Z is a hydrogen atom, or Y and Z together are an oxygen atom.
The agent containing as active compounds with the general formula 1, where the substituents have the above meaning, have strong, also systemic, action towards fungi, especially of the Alternaria and Phytophthora genera.
Description
This invention relates to a fungicide containing as active agent the compo~mds with the general formula 1 Rl - / R2 (Xe )n (1) For control of pathogenic fungi of the Alternaria and especially of the Phytophthora genera, it is known to use agents containing such active substances as dithiocarbamates~ copper compounds, organo-tin compounds and others.
Among the above, most frequently used is mankozeb (a complex of ethylene-bis-dithiocarbamic acid manganese salt with zinc ions), copper oxychloride, and phentin acetateO
The above agents control fungi of the Phytophthora and Alternaria genera; however neither of them is a systemic agent.
Preventive use of copper oxychloride requires application of very high doses (about 8 kg/ha~ phentin aceta~e, as all organotin fungicides, is highly toxic to all mammals; whilst zineb and mankozeb have relatively short protective activity. Further, these fungicides are also no~ soluble in water. Water solubility is another important factor, as spore ~ermination takes place in water. Also, as the above compounds are not systemic agents, . .,:
they do~not prevent infection o-f leaves newl~ developed after fungicide a :application.
Unexpectedly, it has been found that compounds wi~h the general formula 1, where:
Rl ~ / R2 ~X )n (1) X is a halide or methyl sulphate ion with "n" equal 1 or 2, ~1 and R2 are a~yl radicals with 1-4 carbon atoms, .
~ ' -1-R3 is an alkyl radical with 1-4 carbon atoms or a cyclohexyl radical, R4 is an alkyl radical with 1-18 carbon atoms, or R2 and R3 together with the nitrogen atom form a ring with the formula 2 /~ , N W (2) sr z ..
where:
W is an oxygen atom, methylene group or a nitrogen atom substltuted as in formula 3 ~ N ~ Rl (3) ~ C~l2~0-R4 lo where: .
R1 and R4 have the above meaning, ~ ~-U and Y are hydrogen atoms or methyl groups, :
Z is a hydrogen atom or Y and Z are together an oxygen atom;
have strong~ and also systemic, action towards fungi, especially of the Alternaria and Phytophthora genera.
The agent, according to the present invention, containing as an active substance compounds with the general for~ula 1, may also contain known additives such as~mineral or organic carriers, thinners or solvents, : -surface-actlve substances, buffers and adherents.
Effectiveness of the agents according to the yresent invention ~has been tested during biological studies m vitro on the following fungi:
Alternaria tenuis, Botrytis cinerea and Aspergillus niger Results are given in Table 1.
'~ .
Among the above, most frequently used is mankozeb (a complex of ethylene-bis-dithiocarbamic acid manganese salt with zinc ions), copper oxychloride, and phentin acetateO
The above agents control fungi of the Phytophthora and Alternaria genera; however neither of them is a systemic agent.
Preventive use of copper oxychloride requires application of very high doses (about 8 kg/ha~ phentin aceta~e, as all organotin fungicides, is highly toxic to all mammals; whilst zineb and mankozeb have relatively short protective activity. Further, these fungicides are also no~ soluble in water. Water solubility is another important factor, as spore ~ermination takes place in water. Also, as the above compounds are not systemic agents, . .,:
they do~not prevent infection o-f leaves newl~ developed after fungicide a :application.
Unexpectedly, it has been found that compounds wi~h the general formula 1, where:
Rl ~ / R2 ~X )n (1) X is a halide or methyl sulphate ion with "n" equal 1 or 2, ~1 and R2 are a~yl radicals with 1-4 carbon atoms, .
~ ' -1-R3 is an alkyl radical with 1-4 carbon atoms or a cyclohexyl radical, R4 is an alkyl radical with 1-18 carbon atoms, or R2 and R3 together with the nitrogen atom form a ring with the formula 2 /~ , N W (2) sr z ..
where:
W is an oxygen atom, methylene group or a nitrogen atom substltuted as in formula 3 ~ N ~ Rl (3) ~ C~l2~0-R4 lo where: .
R1 and R4 have the above meaning, ~ ~-U and Y are hydrogen atoms or methyl groups, :
Z is a hydrogen atom or Y and Z are together an oxygen atom;
have strong~ and also systemic, action towards fungi, especially of the Alternaria and Phytophthora genera.
The agent, according to the present invention, containing as an active substance compounds with the general for~ula 1, may also contain known additives such as~mineral or organic carriers, thinners or solvents, : -surface-actlve substances, buffers and adherents.
Effectiveness of the agents according to the yresent invention ~has been tested during biological studies m vitro on the following fungi:
Alternaria tenuis, Botrytis cinerea and Aspergillus niger Results are given in Table 1.
'~ .
-2-E~feCtiVeneSS Of agentS With the gen~ra1 Or~U1a 1 ~ _ ~
! COnCentratiOn COnCentratiOn inhibiting SPOre inh1biting R R R R germinatiO~ in 1inear mYCe1~a NO 1 2 ;3 4 X n RPm _ gr A1terna- BOtrYtiS ASPergi1-nUaSte Ciner ea 1US niger
! COnCentratiOn COnCentratiOn inhibiting SPOre inh1biting R R R R germinatiO~ in 1inear mYCe1~a NO 1 2 ;3 4 X n RPm _ gr A1terna- BOtrYtiS ASPergi1-nUaSte Ciner ea 1US niger
3 -CH3 -CH3 -CH3 -C4H9 C1 1 1000 1000 20
4 -CH3 -CH3 -CH3 -C6H13 C1 1 1000 1000 2
5 -C~l3 -CH3 -CH3 -C7H1S C1 1 1000 1000 2
6 -CH3 -CH3 -CH3 -C8H17 C1 1 100C 1000 ~
7 -CH3 -CH3 -C~H3 -C9H19 C1 1 1000 1000 2 0 ~ 1
8 -CH3 -CH3 -CH3 -C10H21 C1 1 1100 100 2 -CH3 -CH3 -CH3 -C12H25 C1 1 10 +10 2 11 -CH3 -CH2-CH2-CH2- C16H33 C1 1 -~10 10 -~2000 13 ¦-CH3 -CM2(CH2)3CH2 -C12H25 C1 1 10 2000 14 ¦-CH3 -CH2(CH2)3CH2 ~ -C1~H37 C1 1 +10 2000 ~ __ . - _ _ .... ~ ~ ..
; ~ Known~ referenCe fUngiCide Z1neb 100 100 2CO
~ ma~ko~eb _~ lOC 2(10 :
: ~
~ .
Exam~le I
50 parts by weight of dodecyloxymethyl-trimethylamine chloride, 40 parts by weight of mineral carrier (kieselguhr), 2 parts by weight of wetting agent -~ 8 parts by weight of dispersing agent ~waste calcium sulphite liquor) were mixed. The fungicide was tested in concentrations of the active compound 0.1% and 0.01~ and effectiveness compared to a known fungicide (mankozeb). Investigations were carried out on tomato seedlings in the 5-6 leaves phase, spraying plants with the tested substance and infecting afterwards with a suspension of Phytophthora infestans spores.
The percent of infected plants were then evaluated in comparison to unsprayed plants (controls) after 6 daysO Results are given in Table 2.
Effectiveness of the agent obtained in Example I against potato blight~Phytophthora infestans) . ~ ,. .
Fungicide Concentration in ~ Percent of infected plants ~
. .. .. _ _ Age~t as in 0.01 25.8 Example I 0.1 0.0 ~ _ _ . . . _ manko~eb 0.01 34.1 0.1 9.0 ' _ ~ .
Check (without _ 100 0 the preparate) _ .
~ .. ~ _ . _ __ _ '.. :, ' -~: ~
10 parts by weight of dodecyloxymethyl trimethylamine chloride, 0.3 parts by weight of alkylarylpolyglycol ether, 89.7 parts by weight of . . .
dlstilled water, were mixed~
The fungicide has been studied for systemic activity in comparison to a k~lown ~stemic funglclde - carbenda~ime tN-(2-benzimida~ole)-carbamic acid methyl ester~ and a known preventive agent (mankozeb).
The agent in example II~`and reference fungicides were diluted with distilled water to concentrations of l.0~ O.l and 0.01%. Roots of bean seedlings were submerged in the solutions for 24 hours. Next, the sprouts were cut into l cm fragments. The fragments, by five, were next placed in Petri dishes with an agar-potato nutrient infected with Aspergillus niger spores. Mycelia growth inhibition zone around the fragments was measured after 4 days. Results are given in Table 3.
TABL~ 3 Systemic activity of the agent wikh general formula l.
. ,,,,,, ~ _ Diameter of Aspergillus niger mycelia growth Average zone of Tested Concentration inhibition zone around growth inhibition agent in % the fragment in mm in mm _ _ _ 2- _ _ _ _ -Agent as l.0 7 9 5 7 9 7.4 in Example O.l 5 O 5 5 O 3.2 II O.Ol 0 0 0 0 0 0~0 Carbenda- l.0 6 5 9 5 7 6.4 zime O.l 6 5 5 0 6 4.4 0.01 O O O O O 0.0 , _ , _ . __ _ _ _ ' ":' Mankozeb l.0 O O O O O 0.0 0.1 O O O O O 0.0 0.01 O O O O O 0.0 . _ _ , _ __. _ _ . --i Check with water _ 0 0 0 I 0 0 0.0 _ _ _ _ _ : I _ _ .: _ Tl Le obtained results testify thak the age nt according to the present invention, penetrates through~the roots ~o bean sprouts, similarly as the known systemic fungiclde - carbendazime. Thus systemlc action of the invented agent has been confirmed.
An advantage of the agent, according to the present invention, besides high effectiveness is its systemic activity, not confirmed until :
now in known fungicides controlling fungi of the Alternaria and Phytophthora genera Also an important advantage of *he agent~according~to *he presént , .
~ 5-invention is its low toxicity to mammals and very good solubility in water, simplifying application.
:' ,..
~ '`:' , , , ~, :
,~ :
.
~i~
; ~ Known~ referenCe fUngiCide Z1neb 100 100 2CO
~ ma~ko~eb _~ lOC 2(10 :
: ~
~ .
Exam~le I
50 parts by weight of dodecyloxymethyl-trimethylamine chloride, 40 parts by weight of mineral carrier (kieselguhr), 2 parts by weight of wetting agent -~ 8 parts by weight of dispersing agent ~waste calcium sulphite liquor) were mixed. The fungicide was tested in concentrations of the active compound 0.1% and 0.01~ and effectiveness compared to a known fungicide (mankozeb). Investigations were carried out on tomato seedlings in the 5-6 leaves phase, spraying plants with the tested substance and infecting afterwards with a suspension of Phytophthora infestans spores.
The percent of infected plants were then evaluated in comparison to unsprayed plants (controls) after 6 daysO Results are given in Table 2.
Effectiveness of the agent obtained in Example I against potato blight~Phytophthora infestans) . ~ ,. .
Fungicide Concentration in ~ Percent of infected plants ~
. .. .. _ _ Age~t as in 0.01 25.8 Example I 0.1 0.0 ~ _ _ . . . _ manko~eb 0.01 34.1 0.1 9.0 ' _ ~ .
Check (without _ 100 0 the preparate) _ .
~ .. ~ _ . _ __ _ '.. :, ' -~: ~
10 parts by weight of dodecyloxymethyl trimethylamine chloride, 0.3 parts by weight of alkylarylpolyglycol ether, 89.7 parts by weight of . . .
dlstilled water, were mixed~
The fungicide has been studied for systemic activity in comparison to a k~lown ~stemic funglclde - carbenda~ime tN-(2-benzimida~ole)-carbamic acid methyl ester~ and a known preventive agent (mankozeb).
The agent in example II~`and reference fungicides were diluted with distilled water to concentrations of l.0~ O.l and 0.01%. Roots of bean seedlings were submerged in the solutions for 24 hours. Next, the sprouts were cut into l cm fragments. The fragments, by five, were next placed in Petri dishes with an agar-potato nutrient infected with Aspergillus niger spores. Mycelia growth inhibition zone around the fragments was measured after 4 days. Results are given in Table 3.
TABL~ 3 Systemic activity of the agent wikh general formula l.
. ,,,,,, ~ _ Diameter of Aspergillus niger mycelia growth Average zone of Tested Concentration inhibition zone around growth inhibition agent in % the fragment in mm in mm _ _ _ 2- _ _ _ _ -Agent as l.0 7 9 5 7 9 7.4 in Example O.l 5 O 5 5 O 3.2 II O.Ol 0 0 0 0 0 0~0 Carbenda- l.0 6 5 9 5 7 6.4 zime O.l 6 5 5 0 6 4.4 0.01 O O O O O 0.0 , _ , _ . __ _ _ _ ' ":' Mankozeb l.0 O O O O O 0.0 0.1 O O O O O 0.0 0.01 O O O O O 0.0 . _ _ , _ __. _ _ . --i Check with water _ 0 0 0 I 0 0 0.0 _ _ _ _ _ : I _ _ .: _ Tl Le obtained results testify thak the age nt according to the present invention, penetrates through~the roots ~o bean sprouts, similarly as the known systemic fungiclde - carbendazime. Thus systemlc action of the invented agent has been confirmed.
An advantage of the agent, according to the present invention, besides high effectiveness is its systemic activity, not confirmed until :
now in known fungicides controlling fungi of the Alternaria and Phytophthora genera Also an important advantage of *he agent~according~to *he presént , .
~ 5-invention is its low toxicity to mammals and very good solubility in water, simplifying application.
:' ,..
~ '`:' , , , ~, :
,~ :
.
~i~
Claims (3)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A fungicidal composition comprising a compound of the general formula 1 (1) where:
X is a halide or methyl sulphate ion with "n" equal 1 or 2, R1 and R2 are alkyl radicals with 1-4 carbon atoms, R3 is an alkyl radical with 1-4 carbon atoms or a cyclo-hexyl radical, R4 is an alkyl radical with 1-18 carbon atoms, or R2 and R3 together with the nitrogen atom form a ring with formula 2 (2) where:
W is an oxygen atom, methylene group or a nitrogen atom substituted as in formula 3 (3) where:
R1 and R4 have above meaning, U and Y are hydrogen atoms or methyl groups, Z is a hydrogen atom, or y and Z together are an oxygen atom, together with an agriculturally acceptable carrier.
X is a halide or methyl sulphate ion with "n" equal 1 or 2, R1 and R2 are alkyl radicals with 1-4 carbon atoms, R3 is an alkyl radical with 1-4 carbon atoms or a cyclo-hexyl radical, R4 is an alkyl radical with 1-18 carbon atoms, or R2 and R3 together with the nitrogen atom form a ring with formula 2 (2) where:
W is an oxygen atom, methylene group or a nitrogen atom substituted as in formula 3 (3) where:
R1 and R4 have above meaning, U and Y are hydrogen atoms or methyl groups, Z is a hydrogen atom, or y and Z together are an oxygen atom, together with an agriculturally acceptable carrier.
2. A composition according to claim 1 wherein the active compound is dodecyloxymethyl trimethylamine chloride.
3. A method of combatting fungi which comprises applying to a habitat thereof an effective amount of a composition as claimed in claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PLP-196611 | 1977-03-11 | ||
| PL19661177A PL106181B1 (en) | 1977-03-11 | 1977-03-11 | FUNGICIDE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100403A true CA1100403A (en) | 1981-05-05 |
Family
ID=19981386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA298,647A Expired CA1100403A (en) | 1977-03-11 | 1978-03-10 | Fungicide |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS53139723A (en) |
| AT (1) | AT357373B (en) |
| BE (1) | BE864781A (en) |
| BG (1) | BG28550A3 (en) |
| BR (1) | BR7801516A (en) |
| CA (1) | CA1100403A (en) |
| CH (1) | CH635226A5 (en) |
| CS (1) | CS194199B2 (en) |
| DD (1) | DD134474A5 (en) |
| DE (1) | DE2810066C2 (en) |
| ES (1) | ES467744A1 (en) |
| FR (1) | FR2382858A1 (en) |
| GB (1) | GB1602871A (en) |
| HU (1) | HU180800B (en) |
| NL (1) | NL171117C (en) |
| PL (1) | PL106181B1 (en) |
| RO (1) | RO75147A (en) |
| SU (1) | SU701515A3 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3424681A1 (en) * | 1984-07-05 | 1986-02-06 | Fa. Anton Zahoransky, 7868 Todtnau | Brush manufacturing machine |
| DD263686B1 (en) * | 1985-07-05 | 1990-08-08 | Inst Pflanzenschutzforschung | FUNGICIDAL AGENTS |
| JP2006036652A (en) * | 2004-07-22 | 2006-02-09 | Sanko Kagaku Kogyo Kk | Method for producing ionic liquid and new onium salt |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE704388C (en) * | 1931-10-07 | 1941-03-29 | Hydrierwerke Akt Ges Deutsche | Process for the production of quaternary ammonium compounds |
| DE755155C (en) * | 1939-05-26 | 1951-11-29 | Zschimmer & Schwarz Chem Fab D | Process for the production of mosquito repellent socks |
| DE1225663B (en) * | 1962-03-02 | 1966-09-29 | Hoechst Ag | Stabilization of water-soluble, surface-active quaternary alkoxymethyl-trialkyl-ammonium halides |
| CH509970A (en) * | 1966-03-26 | 1971-07-15 | Bayer Ag | Process for the preparation of quaternary ammonium salts |
| US3626011A (en) * | 1968-07-26 | 1971-12-07 | Scm Corp | {62 -dialkylaminoalkyl ethers and thioethers |
| US3681462A (en) * | 1969-07-31 | 1972-08-01 | Scm Corp | Dialkylaminoalkyl acetylenic ethers |
| US3842179A (en) * | 1971-03-11 | 1974-10-15 | Scm Corp | Anti-microbial diaralkylaminoalkyl ethers and process for protecting plants |
| JPS49100224A (en) * | 1973-01-29 | 1974-09-21 |
-
1977
- 1977-03-11 PL PL19661177A patent/PL106181B1/en unknown
-
1978
- 1978-03-08 DE DE19782810066 patent/DE2810066C2/en not_active Expired
- 1978-03-09 AT AT170778A patent/AT357373B/en not_active IP Right Cessation
- 1978-03-10 CH CH370878A patent/CH635226A5/en not_active IP Right Cessation
- 1978-03-10 GB GB960778A patent/GB1602871A/en not_active Expired
- 1978-03-10 CA CA298,647A patent/CA1100403A/en not_active Expired
- 1978-03-10 ES ES467744A patent/ES467744A1/en not_active Expired
- 1978-03-10 FR FR7807073A patent/FR2382858A1/en active Granted
- 1978-03-10 BE BE185840A patent/BE864781A/en unknown
- 1978-03-10 SU SU782589398A patent/SU701515A3/en active
- 1978-03-10 JP JP2758278A patent/JPS53139723A/en active Pending
- 1978-03-10 BG BG7838986A patent/BG28550A3/en unknown
- 1978-03-10 HU HUII000260 patent/HU180800B/en unknown
- 1978-03-10 NL NL7802629A patent/NL171117C/en not_active IP Right Cessation
- 1978-03-10 DD DD20411378A patent/DD134474A5/en unknown
- 1978-03-10 CS CS152578A patent/CS194199B2/en unknown
- 1978-03-11 RO RO7893475A patent/RO75147A/en unknown
- 1978-03-13 BR BR7801516A patent/BR7801516A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH635226A5 (en) | 1983-03-31 |
| AT357373B (en) | 1980-07-10 |
| DE2810066C2 (en) | 1984-12-20 |
| PL106181B1 (en) | 1979-11-30 |
| DE2810066A1 (en) | 1978-09-21 |
| ES467744A1 (en) | 1979-09-01 |
| GB1602871A (en) | 1981-11-18 |
| DD134474A5 (en) | 1979-03-07 |
| BR7801516A (en) | 1978-10-10 |
| HU180800B (en) | 1983-04-29 |
| NL7802629A (en) | 1978-09-13 |
| PL196611A1 (en) | 1978-09-25 |
| JPS53139723A (en) | 1978-12-06 |
| RO75147A (en) | 1980-11-30 |
| SU701515A3 (en) | 1979-11-30 |
| ATA170778A (en) | 1979-11-15 |
| BE864781A (en) | 1978-07-03 |
| BG28550A3 (en) | 1980-05-15 |
| FR2382858B1 (en) | 1981-12-18 |
| NL171117C (en) | 1983-02-16 |
| NL171117B (en) | 1982-09-16 |
| CS194199B2 (en) | 1979-11-30 |
| FR2382858A1 (en) | 1978-10-06 |
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