CA1095043A - Pentadienone hydrazone derivatives as insecticides - Google Patents
Pentadienone hydrazone derivatives as insecticidesInfo
- Publication number
- CA1095043A CA1095043A CA320,617A CA320617A CA1095043A CA 1095043 A CA1095043 A CA 1095043A CA 320617 A CA320617 A CA 320617A CA 1095043 A CA1095043 A CA 1095043A
- Authority
- CA
- Canada
- Prior art keywords
- test
- insecticides
- cup
- hydrazone derivatives
- mortality
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/18—Nitrogen atoms not forming part of a nitro radical with hetero atoms attached to said nitrogen atoms, except nitro radicals, e.g. hydrazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
1,5-bis(.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)-,4,pentadien-3-one (1,4,5,6-tetrahydro-2-pyrimidinyl)-hydrazone useful as insecticides.
1,5-bis(.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)-,4,pentadien-3-one (1,4,5,6-tetrahydro-2-pyrimidinyl)-hydrazone useful as insecticides.
Description
lO9S043 This invention relates to 1,5-bis (~ trifluoro-p-tolyl)-1,4-pentadien-3-one (1,4,5,6-tetrahydro-2-pyrimidyl)-hydrazone and its use as an insecticide.
The compounds of this invention are represen~ed by the following formula:
~ ~ NH-N=C(CH=CH ~ 3 2 They are useful as insecticides, especially for the control of fire ants and cockroaches. In one aspect the invention provides a method for controlling insects comprising contacting the insects, their habitat, breeding grounds or feed with an insecticidally effective amount of a compound of the formula:
H
H ~ NH-N=C(CH=CH _ ~ CF3)2 Pentadien-3-one substituted amido hydrazones are described in U.S.
Patent No. 3,878,201 (1975) as anti-malarial and anti-tubercular agents for warm-blooded animals.
The following examples illustrate the invention.
Preparation of 1,5-bis (~ -trifluoro-p-tolyl)-1,4-pentadien-3-one(1,4,5,6-___ tetrahydro-2-pyrimidinyl)hydrazone ( 3 ~ CH=CH-)2C=0 + EI-H2N- ~
_ N
(F3C -~J'~r CH=CH-)2C=N-N ~ ~
27.7 Grams (0.075 mol) of 1,5-bis (~ -trifluoro-p-tolyl-1,4-pentadien-3-one and 18.0 grams (.75 mol) of 1,4,5,6-tetrahydropyridinium-2-ylhydrazine hydro-iodide were rea~ted together in refluxing isopropanol for 3 to 4 hours. Theisopropanol was stripped away leaving a pale yellow solid which was washed thoroughly with ether. The yellow solid was ~ ' stirxed with 2Q0 ml of ether and 50 ml of saturated sodium carbonate. After 15 minutes, the e~her layer was dried and concentrated leaving a bright yellow solid weighing 25.0 grams (72% theory). A small sample was recrystallized from 0CH3/
hexane giving a bright yellow solid with melting point 196-Analyses calculated for N4F6C23H20: C, 59 N, 12.02. Found: C, 58.55; ~, 4.53; N, 12.00.
German Cockroach Bait Toxicant Test - [Blatella Germanica (Linnaeus)]
Test Procedure ~, .. . .
Tests were conducted in cages 20.32 cm in diameter and 6.35 cm in height. The circular side was made of stain-less steel which supported a piece of glass 20.32 cm in dia-meter for the bottom. The cages were capped with 16-mesh copper wire screen lids. One hundred, 25, and 6.25 mg of technical compound were added to five grams of creamy peanut butter in a plastic cup (inside dimensions of 8mm high and 30 mm in diameter) to yield final concentrations of 2.0, O.5, and 0.125%, respectively. The mixtures were each stirred for two minutes. One cup of treated bait plus one cup of untreat-ed lab chow (five grams) to serve as a choice of ~ood, a 100 ml water wick, and 20 adult male German cockroaches were placed in each cage. The cages were held at approximately 27C. and 35% R. H. for mortality counts.
Data obtained are reported in the table below.
~095~43 ~E LE
EVALUATION OF PENTADIENONE HYDRAZONES AS INSECTICIDES
PERCENT MORTALITY
German Cockroaches 11 - Day Mortality Structure 2.0% 0.5~ 0.125%
lQ0 100 100 (F3C ~ 32 C 43 H
. . .
Imported Fire ~nt Bait Toxicant Test~ ( ~ invicta Buren) Test Procedure Tests were conducted in 30 ml disposable plastic medicine cups (40 mm ID at the top, tapering to 32 mm ID at the bottom, 38 mm high). A hole (6 mm diam.) was drilled through the bottom of each cup and a layer of plaster of Paris and builders' cement (9:1 ratio) was poured over the bottom.
The plaster mixture covers the hole and acts as a wick to draw up water when the cup is placed on a saturated 1/4" foam pad. The cups were placed in a tray and covered by another tray inverted to prevent rapid evaporation of water ~rom the - foam pad. Moisture is necessary to keep the humidity in the the cups high and thereby prevent dessiccation of the ants.
3o ~095043 The cement is added to make a hard mixture through which the ants cannot tunnel and escape.
Twenty worker ants from field-collected colonies were placed in each test chamber about 24 hours preceding start of the test. This pretreatment holding period allows time for recovery of the ants from handling and for orientation to the containers.
Candidate chemicals were dissolved directly in the food ma~erial; e.g., soybean oil. The toxic solution was offered to the ants on cotton swabs saturatéd with the material and placed in the test chamber in small vial caps.
Preliminary tests were conducted at concentrations of 1.0, 0.1, and-0.01 percent.
The ants were allowed to feed as desired on the toxic bait for 24 hours. After this exposure period, the toxicant was removed from the chamber and the ants remained without food for an additional 24 hours. At the end of this time new vial caps containing cotton swabs saturated with soybean oil were placed in the chamber and left for the remainder of the test period. Knockdown and mortality cou~ts were made at intervals of 1, 2, 3, 6, 8, 10 and 14 days following initial exposure. Each test consisted of 3 repli-cations. Room temperature was maintained at 75+~ F. Data are reported in the table below.
~09S043 TABLE II
EVALUATION OF PENTADIENONE HYDRAZONES AS INSECTICIDES
PFRCENT MORTALITY
Red Imported Fire Ant 14 - Day Mortality 0S Structure 1.0~ 0.1%
(F3C- ~ CH-C~)2C~N-NH ~ 69 100 H
The insecticidal activity of the compound of this invention is demonstrated by the following tests, wherein pentadienone hydrazones are evaluated against test insect species at rates of from 10 to 1000 ppm~ Test ~ormulations and procedures used for evaluation are as ollows:
Test Formulations.
-A. 100 Milligrams of the test material is weighed, placed in a funnel-o~er a 113 g narrow-mouth bottle, and rinsed into the bottle with a 35 ml ~coop of acetone, followed by a scoop of water and another scoop of acetone to yield 1000 ppm in 65% acetone. If the material is not soluble, it is broken up with a glass rod and used as a suspension.
B This st~ck solution ("A") is used to make 300 ppm solutions or suspensions by pipetting 30 ml of "A" into a bottle containing 70 ml of 50% acetone to yield 300 ppm.
-4a_ 1~9S(~43 Further dilutions in 50% acetone are made as required.
C. Tests requiring 10 ppm acetone solutions: 1 ml of "A"
is pipetted into 99 ml of acetone to yield 10 ppm.
Additional dilutions are made using 50~ acetone a~
required.
Initial Tests Tobacco Budworm - [Heliothis virescens (Fabricus)l, -A cotton plant with two true leaves expanded is dipped for 3 seconds with agitation in 300 ppm solution. A
1.27 cm to 1.91 cm square of cheesecloth with about 50 to 100 budworm eggs 0-24 hours old is also dipped in the test solu-tion and placed on a leaf of the cotton plant, all being placed in the hood to dry. The leaf with the treated budworm eggs is removed from the plant and placed in a 226 g Dixie cup with a wet 5 cm piece of dental wick and covered with a lid. The other leaf is placed in a similar cup with a wick and a piece of cheesecloth infested with 50-100 newly hatched larvae is added before covering the cup with a lid.
After 3 days at 80E', 50~ r.h., observations of egg hatch are made, as well as kill of newly hatched larvae, any inhihition of feeding, or interference of any sort with normal development.
Secondary T_sts Tobacco Budworm - [Heliothis virenscens ~Fabricus)] - ~hird Instar -Three cotton plants with just expanded cotyledons are dipped in 1000 ppm solution and placed in the hood to dry. When dry, each cotyledon i8 cut in half, and 10 are each placed in a 28 g plastic medicine cup containing a 1.25 cm dental wick saturated with water and one third-instar budworm larva is added. The cup is capped and held for 3 days at 80F, 50% r.h., after which mortality counts are made. Compounds killing more than 75% of the larvae are further tested.
Cabbage Looper - ~Trichoplusia nl (H~bner)] - Third Instar -A true leaf of a cotton plant is dipped into the test solution, agitated for 3 seconds, and removed to dry in an exhaust hood. When dry, the leaf is placed in a 9.0 cm petri dish with moist filter paper on the bottom. Ten third instar larvae are added and the lid placed on the dish.
~lortality counts are made after 3 days at 80~F and 50 +
10% r.h. Compounds killing more than 75~ of the loopers are further tested.
Southern Armyworm - Spodoptera eridania (Cramer) Sieva lima bean plants pruned back to two expanded 3 to 4 inches primary leaves are dipped 3 seconds with agitation in the treatment solutions and then set in a hood to dry. After the leaves are dry they are excised, and each excised leaf is placed in a 4-inch petri dish containing a piece of moist filter paper and ten third-instar Southern armyworm larvae approximately 3/8 of an inch long. The petri dishes are covered and placed in a holding room for 2 days at a temperature of 80F. and 50% relative humidity.
Mortality counts are made after 2 days.
Seven days after the plants are treated, leaves are again excised and the test procedure repeated. Mortality of armyworms occurring in this test demonstrates the residual activity of the compounds on the treated leaves.
Data obtained are reported in the Table below.
~095043 ~ ~ ~: g . o :~ ~3~ ~ ~
The compounds of this invention are represen~ed by the following formula:
~ ~ NH-N=C(CH=CH ~ 3 2 They are useful as insecticides, especially for the control of fire ants and cockroaches. In one aspect the invention provides a method for controlling insects comprising contacting the insects, their habitat, breeding grounds or feed with an insecticidally effective amount of a compound of the formula:
H
H ~ NH-N=C(CH=CH _ ~ CF3)2 Pentadien-3-one substituted amido hydrazones are described in U.S.
Patent No. 3,878,201 (1975) as anti-malarial and anti-tubercular agents for warm-blooded animals.
The following examples illustrate the invention.
Preparation of 1,5-bis (~ -trifluoro-p-tolyl)-1,4-pentadien-3-one(1,4,5,6-___ tetrahydro-2-pyrimidinyl)hydrazone ( 3 ~ CH=CH-)2C=0 + EI-H2N- ~
_ N
(F3C -~J'~r CH=CH-)2C=N-N ~ ~
27.7 Grams (0.075 mol) of 1,5-bis (~ -trifluoro-p-tolyl-1,4-pentadien-3-one and 18.0 grams (.75 mol) of 1,4,5,6-tetrahydropyridinium-2-ylhydrazine hydro-iodide were rea~ted together in refluxing isopropanol for 3 to 4 hours. Theisopropanol was stripped away leaving a pale yellow solid which was washed thoroughly with ether. The yellow solid was ~ ' stirxed with 2Q0 ml of ether and 50 ml of saturated sodium carbonate. After 15 minutes, the e~her layer was dried and concentrated leaving a bright yellow solid weighing 25.0 grams (72% theory). A small sample was recrystallized from 0CH3/
hexane giving a bright yellow solid with melting point 196-Analyses calculated for N4F6C23H20: C, 59 N, 12.02. Found: C, 58.55; ~, 4.53; N, 12.00.
German Cockroach Bait Toxicant Test - [Blatella Germanica (Linnaeus)]
Test Procedure ~, .. . .
Tests were conducted in cages 20.32 cm in diameter and 6.35 cm in height. The circular side was made of stain-less steel which supported a piece of glass 20.32 cm in dia-meter for the bottom. The cages were capped with 16-mesh copper wire screen lids. One hundred, 25, and 6.25 mg of technical compound were added to five grams of creamy peanut butter in a plastic cup (inside dimensions of 8mm high and 30 mm in diameter) to yield final concentrations of 2.0, O.5, and 0.125%, respectively. The mixtures were each stirred for two minutes. One cup of treated bait plus one cup of untreat-ed lab chow (five grams) to serve as a choice of ~ood, a 100 ml water wick, and 20 adult male German cockroaches were placed in each cage. The cages were held at approximately 27C. and 35% R. H. for mortality counts.
Data obtained are reported in the table below.
~095~43 ~E LE
EVALUATION OF PENTADIENONE HYDRAZONES AS INSECTICIDES
PERCENT MORTALITY
German Cockroaches 11 - Day Mortality Structure 2.0% 0.5~ 0.125%
lQ0 100 100 (F3C ~ 32 C 43 H
. . .
Imported Fire ~nt Bait Toxicant Test~ ( ~ invicta Buren) Test Procedure Tests were conducted in 30 ml disposable plastic medicine cups (40 mm ID at the top, tapering to 32 mm ID at the bottom, 38 mm high). A hole (6 mm diam.) was drilled through the bottom of each cup and a layer of plaster of Paris and builders' cement (9:1 ratio) was poured over the bottom.
The plaster mixture covers the hole and acts as a wick to draw up water when the cup is placed on a saturated 1/4" foam pad. The cups were placed in a tray and covered by another tray inverted to prevent rapid evaporation of water ~rom the - foam pad. Moisture is necessary to keep the humidity in the the cups high and thereby prevent dessiccation of the ants.
3o ~095043 The cement is added to make a hard mixture through which the ants cannot tunnel and escape.
Twenty worker ants from field-collected colonies were placed in each test chamber about 24 hours preceding start of the test. This pretreatment holding period allows time for recovery of the ants from handling and for orientation to the containers.
Candidate chemicals were dissolved directly in the food ma~erial; e.g., soybean oil. The toxic solution was offered to the ants on cotton swabs saturatéd with the material and placed in the test chamber in small vial caps.
Preliminary tests were conducted at concentrations of 1.0, 0.1, and-0.01 percent.
The ants were allowed to feed as desired on the toxic bait for 24 hours. After this exposure period, the toxicant was removed from the chamber and the ants remained without food for an additional 24 hours. At the end of this time new vial caps containing cotton swabs saturated with soybean oil were placed in the chamber and left for the remainder of the test period. Knockdown and mortality cou~ts were made at intervals of 1, 2, 3, 6, 8, 10 and 14 days following initial exposure. Each test consisted of 3 repli-cations. Room temperature was maintained at 75+~ F. Data are reported in the table below.
~09S043 TABLE II
EVALUATION OF PENTADIENONE HYDRAZONES AS INSECTICIDES
PFRCENT MORTALITY
Red Imported Fire Ant 14 - Day Mortality 0S Structure 1.0~ 0.1%
(F3C- ~ CH-C~)2C~N-NH ~ 69 100 H
The insecticidal activity of the compound of this invention is demonstrated by the following tests, wherein pentadienone hydrazones are evaluated against test insect species at rates of from 10 to 1000 ppm~ Test ~ormulations and procedures used for evaluation are as ollows:
Test Formulations.
-A. 100 Milligrams of the test material is weighed, placed in a funnel-o~er a 113 g narrow-mouth bottle, and rinsed into the bottle with a 35 ml ~coop of acetone, followed by a scoop of water and another scoop of acetone to yield 1000 ppm in 65% acetone. If the material is not soluble, it is broken up with a glass rod and used as a suspension.
B This st~ck solution ("A") is used to make 300 ppm solutions or suspensions by pipetting 30 ml of "A" into a bottle containing 70 ml of 50% acetone to yield 300 ppm.
-4a_ 1~9S(~43 Further dilutions in 50% acetone are made as required.
C. Tests requiring 10 ppm acetone solutions: 1 ml of "A"
is pipetted into 99 ml of acetone to yield 10 ppm.
Additional dilutions are made using 50~ acetone a~
required.
Initial Tests Tobacco Budworm - [Heliothis virescens (Fabricus)l, -A cotton plant with two true leaves expanded is dipped for 3 seconds with agitation in 300 ppm solution. A
1.27 cm to 1.91 cm square of cheesecloth with about 50 to 100 budworm eggs 0-24 hours old is also dipped in the test solu-tion and placed on a leaf of the cotton plant, all being placed in the hood to dry. The leaf with the treated budworm eggs is removed from the plant and placed in a 226 g Dixie cup with a wet 5 cm piece of dental wick and covered with a lid. The other leaf is placed in a similar cup with a wick and a piece of cheesecloth infested with 50-100 newly hatched larvae is added before covering the cup with a lid.
After 3 days at 80E', 50~ r.h., observations of egg hatch are made, as well as kill of newly hatched larvae, any inhihition of feeding, or interference of any sort with normal development.
Secondary T_sts Tobacco Budworm - [Heliothis virenscens ~Fabricus)] - ~hird Instar -Three cotton plants with just expanded cotyledons are dipped in 1000 ppm solution and placed in the hood to dry. When dry, each cotyledon i8 cut in half, and 10 are each placed in a 28 g plastic medicine cup containing a 1.25 cm dental wick saturated with water and one third-instar budworm larva is added. The cup is capped and held for 3 days at 80F, 50% r.h., after which mortality counts are made. Compounds killing more than 75% of the larvae are further tested.
Cabbage Looper - ~Trichoplusia nl (H~bner)] - Third Instar -A true leaf of a cotton plant is dipped into the test solution, agitated for 3 seconds, and removed to dry in an exhaust hood. When dry, the leaf is placed in a 9.0 cm petri dish with moist filter paper on the bottom. Ten third instar larvae are added and the lid placed on the dish.
~lortality counts are made after 3 days at 80~F and 50 +
10% r.h. Compounds killing more than 75~ of the loopers are further tested.
Southern Armyworm - Spodoptera eridania (Cramer) Sieva lima bean plants pruned back to two expanded 3 to 4 inches primary leaves are dipped 3 seconds with agitation in the treatment solutions and then set in a hood to dry. After the leaves are dry they are excised, and each excised leaf is placed in a 4-inch petri dish containing a piece of moist filter paper and ten third-instar Southern armyworm larvae approximately 3/8 of an inch long. The petri dishes are covered and placed in a holding room for 2 days at a temperature of 80F. and 50% relative humidity.
Mortality counts are made after 2 days.
Seven days after the plants are treated, leaves are again excised and the test procedure repeated. Mortality of armyworms occurring in this test demonstrates the residual activity of the compounds on the treated leaves.
Data obtained are reported in the Table below.
~095043 ~ ~ ~: g . o :~ ~3~ ~ ~
Claims (2)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A compound of the formula:
2. A method for controlling insects comprising contacting the insects, their habitat, breeding grounds or feed with an insecticidally effective amount of a compound of the formula:
.
.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/883,755 US4163102A (en) | 1977-05-02 | 1978-03-06 | 1,5-BIS(α,α,α-TRIFLUORO-P-TOLYL)-1,4-PENTADIEN-3-ONE (1,4,5,6-TETRAHYDRO-2-PYRIMIDINYL)HYDRAZONES |
| US883,755 | 1978-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1095043A true CA1095043A (en) | 1981-02-03 |
Family
ID=25383275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA320,617A Expired CA1095043A (en) | 1978-03-06 | 1979-01-31 | Pentadienone hydrazone derivatives as insecticides |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS54125686A (en) |
| AR (1) | AR220738A1 (en) |
| AU (1) | AU524933B2 (en) |
| BR (1) | BR7900995A (en) |
| CA (1) | CA1095043A (en) |
| DE (1) | DE2908651A1 (en) |
| ES (1) | ES478340A1 (en) |
| FR (1) | FR2419287A2 (en) |
| GR (1) | GR72462B (en) |
| IT (1) | IT1163965B (en) |
| PH (1) | PH14266A (en) |
| ZA (1) | ZA79181B (en) |
| ZM (1) | ZM779A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2995163C (en) | 2016-03-16 | 2019-04-23 | Komatsu Ltd. | Dump truck |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3878201A (en) * | 1971-04-05 | 1975-04-15 | American Cyanamid Co | 1,5-Bis substituted-1,4-pentadien-3-one substituted amidinohydrazone salts and method of preparing the same |
| ZA74933B (en) * | 1973-03-01 | 1974-12-24 | American Cyanamid Co | Product and process for preparing 1-substituted amidinohydrazone salts |
| US4087525A (en) * | 1975-12-08 | 1978-05-02 | American Cyanamid Company | Pentadienone hydrazones as insecticides |
| JPS595503B2 (en) * | 1976-02-27 | 1984-02-04 | 東レ株式会社 | fiber package |
| JPS5439056A (en) * | 1977-08-29 | 1979-03-24 | American Cyanamid Co | Pentadienone hydrazone and pesticidal method using same |
| JPS6216921A (en) * | 1985-07-12 | 1987-01-26 | Matsushita Electric Ind Co Ltd | Intermittent transfer device |
-
1979
- 1979-01-16 ZA ZA00790181A patent/ZA79181B/en unknown
- 1979-01-22 AU AU43563/79A patent/AU524933B2/en not_active Expired
- 1979-01-23 ZM ZM7/79A patent/ZM779A1/en unknown
- 1979-01-31 CA CA320,617A patent/CA1095043A/en not_active Expired
- 1979-02-05 AR AR275406A patent/AR220738A1/en active
- 1979-02-16 BR BR7900995A patent/BR7900995A/en unknown
- 1979-02-27 GR GR58496A patent/GR72462B/el unknown
- 1979-02-28 FR FR7905244A patent/FR2419287A2/en active Granted
- 1979-02-28 PH PH22240A patent/PH14266A/en unknown
- 1979-03-05 IT IT48212/79A patent/IT1163965B/en active
- 1979-03-06 DE DE19792908651 patent/DE2908651A1/en not_active Ceased
- 1979-03-06 JP JP2520179A patent/JPS54125686A/en active Pending
- 1979-03-06 ES ES478340A patent/ES478340A1/en not_active Expired
-
1988
- 1988-10-18 JP JP63260694A patent/JPH029868A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR7900995A (en) | 1979-11-20 |
| ES478340A1 (en) | 1979-11-16 |
| JPS54125686A (en) | 1979-09-29 |
| JPH029868A (en) | 1990-01-12 |
| ZA79181B (en) | 1979-12-27 |
| ZM779A1 (en) | 1979-12-21 |
| IT1163965B (en) | 1987-04-08 |
| AU524933B2 (en) | 1982-10-14 |
| FR2419287A2 (en) | 1979-10-05 |
| FR2419287B2 (en) | 1983-11-10 |
| IT7948212A0 (en) | 1979-03-05 |
| GR72462B (en) | 1983-11-10 |
| DE2908651A1 (en) | 1979-09-20 |
| AR220738A1 (en) | 1980-11-28 |
| PH14266A (en) | 1981-04-23 |
| AU4356379A (en) | 1979-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |