CA1072443A - 2,6-dichloropyridine-4-carboxylic acid hydrazide for combatting microorganisms - Google Patents
2,6-dichloropyridine-4-carboxylic acid hydrazide for combatting microorganismsInfo
- Publication number
- CA1072443A CA1072443A CA252,367A CA252367A CA1072443A CA 1072443 A CA1072443 A CA 1072443A CA 252367 A CA252367 A CA 252367A CA 1072443 A CA1072443 A CA 1072443A
- Authority
- CA
- Canada
- Prior art keywords
- phytopathogenic
- microorganisms
- parts
- carboxylic acid
- dichloropyridine
- 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
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Abstract
2,6-DICHLOROPYRIDINE-4-CARBOXYLIC ACID
HYDRAZIDE FOR COMBATTING MICROORGANISMS
Abstract of the Disclosure Composition containing as active ingredient 2,6-dichloro-pyridine-4-carboxylic acid hydrazide of formula I
(I)
HYDRAZIDE FOR COMBATTING MICROORGANISMS
Abstract of the Disclosure Composition containing as active ingredient 2,6-dichloro-pyridine-4-carboxylic acid hydrazide of formula I
(I)
Description
~7Z~43 The pr~sent invention relates to a composition for combatting phy~opathogenic microorganisms, which composition contains as active ingredient 2,6-dichloropyridine~4-carboxylic acid hydrazide of formula I
CONHN~12 ~ (I), / ~N-' ~
Cl Cl as well as to the use of this compound for combatting phytopathogenic microorganisms. Pyridine-4-carboxylic acid can also be termed isonicotinic acid.
The compound of formula I and its use in human medicine are known (see, e.g., Monatshefte fur Chemie, 36 (1915~, 737 or Bull. 19549 1430).
It has now been found that, surprisingly, the said compound exhibits a high activity against phytopathogenic microorganisms.
The compound of formula I is thus suitable for combatting phytopathogenic fungi, particularly however phytopathogenic bacteria. The term phytopathogenic fungi embraces, for example, fungi of the genera: ~rysiphe, Phytophthora or Venturia. As phytopathogenic bacteria, there can be mentioned, ........ ..
'72~3 inter alia, members of the genera Pseudomonas, e.g. PseLIdomonas tomata, Pseudomonas Lachrymans, Pseudomonas phaseolicola, Pseudomonas tacabi and Pseudomonas syringae, Xanthomonas, e.g. Xanthomonas oryzae, Xanthomonas vesicatoria, Xanthomonas phaseoli, Xanthomonas campestri and Xanthomonas citri, as well as Erwinia and Coryne~acterium.
A special property of the compound of formula I is its systemic action against phytopathogenic bacteria, i.e. its capacity to translocate in a plant to a site of infection that is remote from the point of appli-cation. The compound can thus be absorbed from the treated soil by the roots of a plant and then conveyed to the site of infection.
Accordingly, the present invention provides a method for com-batting phytopathogenic microorganisms which comprises contacting such microorganisms with an effective amount of the compound of Formula (I).
The invention also provides a composition for combatting phytopathogenic microorganisms which comprises a compound of Formula (I) in an amount of 0.1 to 95% by weight of the composition, together with a herbicidally non-toxic carrier or diluent selected from solid diluents or carriersJ
liquefied aerosol propellants, and liquid carriers or diluents containing a surface active agent.
~e compound can be used on crops of useful plants such as cereals, maize, potatoes, rice, vegetables, grape vines, ornamental plants, fruit, and so forth.
In order to adapt it to suit given circumstances and natur-ally to widen its sphere of action, the compound of formula ~I) can be used together with other suitable pesticides, such as fungicides, insecticides or acaricides, or with active substances influencing plant growth.
~,~"-:, .
,'. , ` . ~ ' '~ .: ' :
7'~4~3 Example for production of_the active substance 20.6 g of 2,6-dichloropyridine-4-carboxylic acid methyl ester (0.1 mole) was heated with 4~.0 g of 100% hydrazine (0.15 mole~, or with 74 ml of approx. 65% hydrazine hydrate, diluted with 100 ml of water, for 2 hours at 70 - 80~C and subsequently for a further 2 hours at 80 - 90C. After eooling, the resulting crystal suspension was filtered off with suction and washed with cold water; m.p. 182 -184C. Reerystallisation from the approx. 10-fold amount of ethanol yielded 2~6-dichloropyridine-4-earboxylic acid hydrazide having a melting point of 183 - 184C. Lit.: m.p. 184C (Hans Meyer and eo-workers, Monateshefte f~r Chemie 36 (1915), 737).
The eompound of formula I is used aceording to the invention together with suitable earriers and/or other additives. Suitable carriers and additives may be solid or liquid, and they correspond to the substances common in formulation practice, sueh as natural or regenerated mineral ~0 substances, solvents, diluents, extenders~ surfaetants, disporsing agents, wetting agents, adhesives, thickeners, binders or fertilisers. Such compositions are produeed in a manner known per se by the in~imate mixing and grinding of the eonsti~uents.
.
,. . . .
~7'~ ~ ~3 For application, the compound of formula I can be in the followin~ Eorms:
solid preparations:- dusts, scattering agents, pellets or granulates (coated granulates, imprëgnated granulates and homogeneous granulates);
liquid pre~arations:-a) water-dispersible active-substance concentrates:
wettable powders, pastes, emulsions or solution concentrates;
b) solutions: aerosols.
The content of active substance in the above-described compositions ls between 0.1 and 95 per cent by weight. The active substance of formula I can be formulated, e.g., as follows:
Dusts:
The following substances are used to prepare a) a 5%
dust and b) a 2% dust:
a) 5 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 95 parts of talcum, b) 2 parts of 2,6-dichloropyridine-4-carboxylic acid, 1 part of highly dispersed silicic acid, 97 parts of talcum.
. ~....................... , .. ~, . . ... .. . . . .
.
' ' : ' ' ' '.
.. ..
4~3 The ac~ive substance is mixed and ground with the carriers and can be applied in this form by dusting.
Granulate The following substances are used to produce a 5% granulate:
5 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 0.25 part of epichlorohydrin, 0.25 part of cetyl polyglycol ether 9 3.50 parts of polyethylene glycol, 91 parts of kaolin (particle size 0.3 - 0.8 mm).
The active subs~ance is mixed with epichlorohydrin and the mixture is dissolved with 6 parts of acetone; the polyethylene glycol and cetyl polyglycol ether are then added. The solution obtained in this manner is sprayed onto kaolin and the acetone is subsequently evaporated off in vacuo. A microgranulate of this kind is particularly suitable for treatment of the soil.
Wettable powders The following constituents are used to produce a) a 70%, b) a 40%, c) and d) a 25% and e) a 10% wettable powder:
a) 70 parts of 2,6~dichloropyridine-4-carboxylic acid hydrazi.de, parts of sodium dibutyl-napthalene sulphonate~
- -.
~7;~3 3 parts of naphthalenesulphonic acid/phenol-sulphonic acid/formaldehyde condensate 3:2:1, parts of kaolin, 12 parts of Champagne chalk;
b~ 40 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, parts of sodium lignin sulphonate, 1 part of sodium dibutyl-naphthalene sulphonate 9 54 parts of silicic acid;
c) 25 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 4.5 parts of calcium lignin sulphonate, 1.9 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), lS 1.~ parts of sodium dibu~yl naphthalene sulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalk, 28.1 parts of kaolin;
d) 25 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide,
CONHN~12 ~ (I), / ~N-' ~
Cl Cl as well as to the use of this compound for combatting phytopathogenic microorganisms. Pyridine-4-carboxylic acid can also be termed isonicotinic acid.
The compound of formula I and its use in human medicine are known (see, e.g., Monatshefte fur Chemie, 36 (1915~, 737 or Bull. 19549 1430).
It has now been found that, surprisingly, the said compound exhibits a high activity against phytopathogenic microorganisms.
The compound of formula I is thus suitable for combatting phytopathogenic fungi, particularly however phytopathogenic bacteria. The term phytopathogenic fungi embraces, for example, fungi of the genera: ~rysiphe, Phytophthora or Venturia. As phytopathogenic bacteria, there can be mentioned, ........ ..
'72~3 inter alia, members of the genera Pseudomonas, e.g. PseLIdomonas tomata, Pseudomonas Lachrymans, Pseudomonas phaseolicola, Pseudomonas tacabi and Pseudomonas syringae, Xanthomonas, e.g. Xanthomonas oryzae, Xanthomonas vesicatoria, Xanthomonas phaseoli, Xanthomonas campestri and Xanthomonas citri, as well as Erwinia and Coryne~acterium.
A special property of the compound of formula I is its systemic action against phytopathogenic bacteria, i.e. its capacity to translocate in a plant to a site of infection that is remote from the point of appli-cation. The compound can thus be absorbed from the treated soil by the roots of a plant and then conveyed to the site of infection.
Accordingly, the present invention provides a method for com-batting phytopathogenic microorganisms which comprises contacting such microorganisms with an effective amount of the compound of Formula (I).
The invention also provides a composition for combatting phytopathogenic microorganisms which comprises a compound of Formula (I) in an amount of 0.1 to 95% by weight of the composition, together with a herbicidally non-toxic carrier or diluent selected from solid diluents or carriersJ
liquefied aerosol propellants, and liquid carriers or diluents containing a surface active agent.
~e compound can be used on crops of useful plants such as cereals, maize, potatoes, rice, vegetables, grape vines, ornamental plants, fruit, and so forth.
In order to adapt it to suit given circumstances and natur-ally to widen its sphere of action, the compound of formula ~I) can be used together with other suitable pesticides, such as fungicides, insecticides or acaricides, or with active substances influencing plant growth.
~,~"-:, .
,'. , ` . ~ ' '~ .: ' :
7'~4~3 Example for production of_the active substance 20.6 g of 2,6-dichloropyridine-4-carboxylic acid methyl ester (0.1 mole) was heated with 4~.0 g of 100% hydrazine (0.15 mole~, or with 74 ml of approx. 65% hydrazine hydrate, diluted with 100 ml of water, for 2 hours at 70 - 80~C and subsequently for a further 2 hours at 80 - 90C. After eooling, the resulting crystal suspension was filtered off with suction and washed with cold water; m.p. 182 -184C. Reerystallisation from the approx. 10-fold amount of ethanol yielded 2~6-dichloropyridine-4-earboxylic acid hydrazide having a melting point of 183 - 184C. Lit.: m.p. 184C (Hans Meyer and eo-workers, Monateshefte f~r Chemie 36 (1915), 737).
The eompound of formula I is used aceording to the invention together with suitable earriers and/or other additives. Suitable carriers and additives may be solid or liquid, and they correspond to the substances common in formulation practice, sueh as natural or regenerated mineral ~0 substances, solvents, diluents, extenders~ surfaetants, disporsing agents, wetting agents, adhesives, thickeners, binders or fertilisers. Such compositions are produeed in a manner known per se by the in~imate mixing and grinding of the eonsti~uents.
.
,. . . .
~7'~ ~ ~3 For application, the compound of formula I can be in the followin~ Eorms:
solid preparations:- dusts, scattering agents, pellets or granulates (coated granulates, imprëgnated granulates and homogeneous granulates);
liquid pre~arations:-a) water-dispersible active-substance concentrates:
wettable powders, pastes, emulsions or solution concentrates;
b) solutions: aerosols.
The content of active substance in the above-described compositions ls between 0.1 and 95 per cent by weight. The active substance of formula I can be formulated, e.g., as follows:
Dusts:
The following substances are used to prepare a) a 5%
dust and b) a 2% dust:
a) 5 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 95 parts of talcum, b) 2 parts of 2,6-dichloropyridine-4-carboxylic acid, 1 part of highly dispersed silicic acid, 97 parts of talcum.
. ~....................... , .. ~, . . ... .. . . . .
.
' ' : ' ' ' '.
.. ..
4~3 The ac~ive substance is mixed and ground with the carriers and can be applied in this form by dusting.
Granulate The following substances are used to produce a 5% granulate:
5 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 0.25 part of epichlorohydrin, 0.25 part of cetyl polyglycol ether 9 3.50 parts of polyethylene glycol, 91 parts of kaolin (particle size 0.3 - 0.8 mm).
The active subs~ance is mixed with epichlorohydrin and the mixture is dissolved with 6 parts of acetone; the polyethylene glycol and cetyl polyglycol ether are then added. The solution obtained in this manner is sprayed onto kaolin and the acetone is subsequently evaporated off in vacuo. A microgranulate of this kind is particularly suitable for treatment of the soil.
Wettable powders The following constituents are used to produce a) a 70%, b) a 40%, c) and d) a 25% and e) a 10% wettable powder:
a) 70 parts of 2,6~dichloropyridine-4-carboxylic acid hydrazi.de, parts of sodium dibutyl-napthalene sulphonate~
- -.
~7;~3 3 parts of naphthalenesulphonic acid/phenol-sulphonic acid/formaldehyde condensate 3:2:1, parts of kaolin, 12 parts of Champagne chalk;
b~ 40 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, parts of sodium lignin sulphonate, 1 part of sodium dibutyl-naphthalene sulphonate 9 54 parts of silicic acid;
c) 25 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 4.5 parts of calcium lignin sulphonate, 1.9 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), lS 1.~ parts of sodium dibu~yl naphthalene sulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalk, 28.1 parts of kaolin;
d) 25 parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide,
2.5 parts of isooctylphenoxy-poly~xyethylene ethanol, 1.7 parts o Champagne chalk/hydroxyethyl cellulose mixture (1~
8.3 parts of sodium aluminium silicate, - . - . ~ .
, , ... . . '~ . :
.
. . . , ,: ~ .
.
~ 7 Z ~ 3 16.5 par~s o~ kieselguhr, 46 parts of kaolin;
e) 10 parts of 2,6-dichloropyridine 4-carboxylic acid hydrazide,
8.3 parts of sodium aluminium silicate, - . - . ~ .
, , ... . . '~ . :
.
. . . , ,: ~ .
.
~ 7 Z ~ 3 16.5 par~s o~ kieselguhr, 46 parts of kaolin;
e) 10 parts of 2,6-dichloropyridine 4-carboxylic acid hydrazide,
3 parts of a mix~ure o the sodium salts of saturated fatty alcohol sulphates, parts of naphthalenesulphonic acid/formaldehyde condensate, 82 parts of kaolin.
The active substance is intimately mixed in suitable mixers with the additives, and the mixture is then ground in the appropriate mills and rollers. Wettable powders are obtained having excellent wetting and suspension properties 3 which powders can be diluted with water to give suspensions of the desired concentration and which can be used, in particular, for leaf application.
Emulsifiable concentrate . . . _ _ . _ _ The following substances are used to produce a 25%
emulsifiable concentrate-parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 2.5 parts of epoxidised vegetable oil, parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture, ' ' , ' ' - .
.
,. . .
.
~ 0~7Z ~ ~3 parts of dimethy].formamide, 57.5 parts of xylene.
It is possible to produce from this concentrate, by dilution with water, emulsions of the desired concentration, which are particularly suitable for leaf application.
The following Examples serve to further illustrate the invention without limiting the scope thereof.
~7 Z ~ ~3 F.xample 1 Action against Pseudomonas lachrymans on cucumbers and against Xanthomonas vesicatoria on paprika . .. ~
a) Residual act on Young cucumber and paprika plants were sprayed until dripping wet with the active substance in the form of a spray liquor with a content of active substance of 1000 ppm.
One day after this application, the plants were infested by spraying of the underside of the primary leaves with suspensions of-the respective bacteria, and then incubated for 8 days at 22C with 95% relative humidity. An evaluation was made after this period of time on-the basis of the number of typical disease spots.
b) Systemic action Young cucumber and paprika plants were watered with the lS active substance in ~he form of a suspension of the active substance (concentration 100 ppm relative to the pot soil~. One day after this application, the plants were inested by spraying of the underside of the primary leaves with suspensions of the respective bacte~ria, and incubation was subsequently carried out for 8 days at 22C with 95%
relative h~nidity. After this period of time, the evaluation was made on the basis of the number of typical disease spots.
~7~
The compouncl of formula I exhihited in the case of the mentioned bacteria a good action (less than 20% infestation compared with untreated but infested control plants).
Example 2 Action a~ainst Venturia inaequalis on Malus sylvestris Apple cuttings having fresh shoots 10-20 cm long were sprayed with a spray liquor (0.06% of active substance) produced from a wettable powder of the active substance.
The treated plants were sprayed after 24 hours with a conidiospore suspension of the fungus. The plants were then subjected to an incubation treatment for 5 days at 90-100% relative humidity, and were afterwards left to stand for a further 10 days in a greenhouse at 20-24C.
The scab infestation was assessed 15 days after infestation.
The compound of formula I exhibited in this test a good action (less than 20% infestation compared with untreated hut infested control plants).
The active substance is intimately mixed in suitable mixers with the additives, and the mixture is then ground in the appropriate mills and rollers. Wettable powders are obtained having excellent wetting and suspension properties 3 which powders can be diluted with water to give suspensions of the desired concentration and which can be used, in particular, for leaf application.
Emulsifiable concentrate . . . _ _ . _ _ The following substances are used to produce a 25%
emulsifiable concentrate-parts of 2,6-dichloropyridine-4-carboxylic acid hydrazide, 2.5 parts of epoxidised vegetable oil, parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture, ' ' , ' ' - .
.
,. . .
.
~ 0~7Z ~ ~3 parts of dimethy].formamide, 57.5 parts of xylene.
It is possible to produce from this concentrate, by dilution with water, emulsions of the desired concentration, which are particularly suitable for leaf application.
The following Examples serve to further illustrate the invention without limiting the scope thereof.
~7 Z ~ ~3 F.xample 1 Action against Pseudomonas lachrymans on cucumbers and against Xanthomonas vesicatoria on paprika . .. ~
a) Residual act on Young cucumber and paprika plants were sprayed until dripping wet with the active substance in the form of a spray liquor with a content of active substance of 1000 ppm.
One day after this application, the plants were infested by spraying of the underside of the primary leaves with suspensions of-the respective bacteria, and then incubated for 8 days at 22C with 95% relative humidity. An evaluation was made after this period of time on-the basis of the number of typical disease spots.
b) Systemic action Young cucumber and paprika plants were watered with the lS active substance in ~he form of a suspension of the active substance (concentration 100 ppm relative to the pot soil~. One day after this application, the plants were inested by spraying of the underside of the primary leaves with suspensions of the respective bacte~ria, and incubation was subsequently carried out for 8 days at 22C with 95%
relative h~nidity. After this period of time, the evaluation was made on the basis of the number of typical disease spots.
~7~
The compouncl of formula I exhihited in the case of the mentioned bacteria a good action (less than 20% infestation compared with untreated but infested control plants).
Example 2 Action a~ainst Venturia inaequalis on Malus sylvestris Apple cuttings having fresh shoots 10-20 cm long were sprayed with a spray liquor (0.06% of active substance) produced from a wettable powder of the active substance.
The treated plants were sprayed after 24 hours with a conidiospore suspension of the fungus. The plants were then subjected to an incubation treatment for 5 days at 90-100% relative humidity, and were afterwards left to stand for a further 10 days in a greenhouse at 20-24C.
The scab infestation was assessed 15 days after infestation.
The compound of formula I exhibited in this test a good action (less than 20% infestation compared with untreated hut infested control plants).
Claims (11)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method for combatting phytopathogenic microorganisms which comprises contacting such microorganisms with an effective amount of 2,6-dichloropyridine-4-carboxylic acid hydrazide of formula I
(I)
(I)
2. A method according to claim 1 wherein the phytopathogenic micro-organisms are phytopathogenic bacteria.
3. A method according to claim 1 wherein the phytopathogenic micro-organisms are phytopathogenic fungi.
4. A method according to claim 1 wherein the phytopathogenic micro-organisms are fungi of the genera Erysiphe, Phytophthora or Venturia.
5. A method according to claim 1 wherein the phytopathogenic micro-organisms are bacteria of the genera Pseudomonas, Xanthomonas, Erwinia or Corynebacterium.
6. A method according to claim 1, 2 or 3 wherein the foliage of plants infected or subject to infection with said pathogenic microorganisms is treated with said hydrazide.
7. A method according to claim 1, 2 or 3 wherein the soil in which plants infected or subject to infection with said pathogenic microorganisms are growing, is treated with said hydrazide.
8. A composition for combatting phytopathogenic microorganisms which comprises a compound of Formula (I) defined in claim 1 in an amount of 0.1 to 95% by weight of the composition, together with a herbicidally non-toxic carrier or diluent selected from solid diluents or carriers, liquefied aerosol propellants, and liquid carriers or diluents containing a surface active agent.
9. A composition according to claim 8 in the form of a dust, scattering agent, pellet or granulate.
10. A composition according to claim 8 in the form of a water-dispersible concentrate.
11. A composition according to claim 8 in the form of a solution in an aerosol propellant.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH619175A CH608341A5 (en) | 1975-05-14 | 1975-05-14 | Method of controlling phytopathogenic bacteria |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072443A true CA1072443A (en) | 1980-02-26 |
Family
ID=4305691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA252,367A Expired CA1072443A (en) | 1975-05-14 | 1976-05-12 | 2,6-dichloropyridine-4-carboxylic acid hydrazide for combatting microorganisms |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS51142539A (en) |
| CA (1) | CA1072443A (en) |
| CH (1) | CH608341A5 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4959096A (en) * | 1988-03-25 | 1990-09-25 | Ciba-Geigy Corporation | Compositions for protecting plants against disease |
| US4966908A (en) * | 1988-03-21 | 1990-10-30 | Ciba-Geigy Corporation | Isonicotinic acid amides for protecting plants against disease |
| US4980355A (en) * | 1988-03-09 | 1990-12-25 | Ciba-Geigy Corporation | Compositions for protecting plants against disease |
-
1975
- 1975-05-14 CH CH619175A patent/CH608341A5/en not_active IP Right Cessation
-
1976
- 1976-05-12 CA CA252,367A patent/CA1072443A/en not_active Expired
- 1976-05-14 JP JP5519976A patent/JPS51142539A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980355A (en) * | 1988-03-09 | 1990-12-25 | Ciba-Geigy Corporation | Compositions for protecting plants against disease |
| US5112840A (en) * | 1988-03-09 | 1992-05-12 | Ciba-Geigy Corporation | Compositions for protecting plants against disease |
| US4966908A (en) * | 1988-03-21 | 1990-10-30 | Ciba-Geigy Corporation | Isonicotinic acid amides for protecting plants against disease |
| US4959096A (en) * | 1988-03-25 | 1990-09-25 | Ciba-Geigy Corporation | Compositions for protecting plants against disease |
Also Published As
| Publication number | Publication date |
|---|---|
| CH608341A5 (en) | 1979-01-15 |
| JPS51142539A (en) | 1976-12-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |