Claims
- 1. Compounds of the formula I ##STR10## wherein R.sub.1 represents C.sub.1 -C.sub.4 -alkyl, alkyl(C.sub.1 -C.sub.4)-carbonyl or halogenoalkyl(C.sub.1 -C.sub.3)-carbonyl as well as salts thereof with organic and inorganic acids.
- 2. A compound according to claim 1 which is N-(2,6-dichloropyridine-4-carboxylic acid)-N'-sec-butyl hydrazide.
- 3. A compound according to claim 1 which is N-(2,6-dichloropyridine-4-carboxylic acid)-N'-trichloroacetyl-hydrazide.
- 4. A compound according to claim 1 which is N-(2,6- dichloropyridine-4-carboxylic acid)-N'-isobutylcarbonyl-hydrazide.
- 5. A microbicidal and plant-growth regulating composition comprising as active substance an amount effective for one or both of said purposes of a compound as claimed in claim 1 together with a suitable carrier therefor.
- 6. A microbicidal and plant-growth regulating composition comprising as active substance an amount effective for one or both of said purposes of a compound as claimed in claim 2 together with a suitable carrier therefor.
- 7. A microbicidal and plant-growth regulating composition comprising as active substance an amount effective for one or both of said purposes of a compound as claimed in claim 3 together with a suitable carrier therefor.
- 8. A microbicidal and plant-growth regulating composition comprising as active substance an amount effective for one or both of said purposes of a compound as claimed in claim 4 together with a suitable carrier therefor.
- 9. A method for combatting phytopathogenic microorganisms which comprises applying thereto or to the locus thereof a microbicidally effective amount of a compound as claimed in claim 1.
- 10. A method for combatting phytopathogenic microorganisms which comprises applying thereto or to the locus thereof a microbicidally effective amount of a compound as claimed in claim 2.
- 11. A method for combatting phytopathogenic microorganisms which comprises applying thereto or to the locus thereof a microbicidally effective amount of a compound as claimed in claim 3.
- 12. A method for combatting phytopathogenic microorganisms which comprises applying thereto or to the locus thereof a microbicidally effective amount of a compound as claimed in claim 4.
- 13. A method for advantageously regulating plant growth which comprises applying thereto or to the locus thereof an amount effective in regulating plant growth of a compound as claimed in claim 1.
- 14. A method for advantageously regulating plant growth which comprises applying thereto or to the lucus thereof an amount effective in regulating plant growth of a compound as claimed in claim 2.
- 15. A method as claimed in claim 9 wherein the microorganisms to be combatted are phytopathogenic bacteria.
- 16. A method as claimed in claim 10 wherein the microorganisms to be combatted are phytopathogenic bacteria.
- 17. A method as claimed in claim 11 wherein the microorganisms to be combatted are phytopathogenic bacteria.
- 18. A method as claimed in claim 12 wherein the microorganisms to be combatted are phytopathogenic bacteria.
Priority Claims (2)
| Number |
Date |
Country |
Kind |
| 06192/75 |
May 1975 |
CHX |
|
| 04148/76 |
Apr 1976 |
CHX |
|
CROSS REFERENCE
This application is a continuation in part of Ser. No. 685,594, filed May 12, 1976 and which is now abandoned.
The present invention relates to pyridine-4-carboxylic acid hydrazides, as well as to compositions and processes for combatting phytopathogenic microorganisms and for regulating plant growth.
The compounds of the invention correspond to formula I ##STR2## wherein R.sub.1 represents C.sub.1 -C.sub.4 -alkyl, alkyl(C.sub.1 -C.sub.4)-carbonyl or halogenoalkyl(C.sub.1 -C.sub.3)-carbonyl.
The invention also embraces salts of these compounds with organic and inorganic acids.
Pyridine-4-carboxylic acid can also be termed iso-nicotinic acid.
By alkyl or as alkyl-moiety of another substituent are meant, depending on the number of given carbon atoms, the following groups: methyl, ethyl, propyl or butyl as well as isomers thereof iso-propyl, iso-, sec.- or tert.-butyl.
Halogen denotes fluorine, chlorine, bromine or iodine.
Suitable salt-forming acids are, for example, hydrohalic acids, e.g. hydrochloric acid, hydrobromic acid or hydriodic acid, hydrofluoboric acid, nitric acid, phosphoric acid, thio- or dithiophosphoric acid, sulphuric acid, methanesulphonic acid, acetic acid, haloacetic acids, propionic acid, halopropionic acids, butyric acid, lactic acid, stearic acid, oxalic acid, tartaric acid, maleic acid or benzoic acid.
The compounds of formula I may be produced by one of the following schematically represented methods: ##STR3## WHEREIN R.sub.1 is as defined under formula I, and
The aforementioned reactions may be performed in the presence or absence of solvents which are inert to the reactants and which are customarily used in such reactions. Suitable solvents are, for example: alcohols such as methanol or ethanol; ethers such as diethyl ether, dioxane or glycol monomethyl ether, as well as hydrocarbons such as benzene, toluene, petroleum ether, etc.
The remaining reaction conditions also correspond to those of similar known processes e.g.:
The salts may also be produced by methods known per se. Compounds similar to those of the instant invention are described in BULL.SOC.CHIM.FRANCE (1954) pp 1430-43 and HELV.CHIM.ACTA 38 pp 1033-46 (1955).
The compounds of formula I can be used for combatting various phytopathogenic microorganisms. Thus, for example, some of the compounds of formula I are effective against phytopathogenic fungi. In particular, however, they are suitable for controlling phytopathogenic bacteria.
The term phytopathogenic fungi embraces, for example, fungi of the genera Phytophthora or Venturia.
As phytopathogenic bacteria, there can be mentioned, inter alia, members of the genera Pseudomonas, e.g. Pseudomonas tomato, Pseudomonas lachrymans, Pseudomonas phaseolicola, Pseudomonas tabaci and Pseudomonas syringae, Xanthomonas, e.g. Xanthomonas oryzae, Xanthomonas vesicatoria, Xanthomonas phaseoli, Xanthomonas campestri and Xanthomonas citri, as well as Erwinia and Corynebacterium.
A special property of the compounds of formula I is their systemic action against phytopathogenic parasites, i.e. their ability to undergo translocation in a plant to a site of infection that is remote from the point of application. After treatment of the soil, such a compound can thus be absorbed by the roots of a plant and conveyed to the site of infection.
The compounds can be used on useful crops such as cereals, maize, potatoes, rice, vegetables, grape vines, ornamental plants, fruit, and so forth.
A number of the compounds of formula I possess the property of advantageously regulating or modifying plant growth. It is thus possible, inter alia, to prevent therewith excessive undesirable growth, such as grasses along the verges of highways, on river banks, etc., or of side shoots (suckers) on tobacco plants.
The compounds of formula I may also be used to influence the abscission of various fruits, particularly of citrus fruits.
In order to adapt them to suit given circumstances and also to broaden their sphere of action, the compounds of formula I may be used together with other suitable pesticides, such as bactericides, fungicides, insecticides or acaricides, or with other active substances influencing plant growth.
The compounds of formula I can be used on their own or together with suitable carriers and/or additives. Suitable carriers and additives may be solid or liquid, and correspond to substances common in formulation practice, such as natural or regenerated mineral substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders or fertilisers. Such compositions are produced in a manner known per se by the intimate mixing and grinding of their constituent parts.
For application, the compounds of formula I can be used in the following forms:
Solid Preparations
Liquid Preparations
The content of active substance in the above-described compositions is between 0.1 and 95% by weight. The active substances of formula I can be formulated, e.g., as follows:
The following substances are used in the preparation of (a) a 5% dust and (b) a 2% dust:
The active substances are mixed and ground with the carriers and can be applied in this form by dusting.
The following substances are used to produce a 5% granulate:
The active substance is mixed with epichlorohydrin, and the mixture is dissolved in 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 subsequently evaporated off in vacuo. A microgranulate of this kind is particularly suitable for application to the soil.
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 Active Substance, 5 parts of sodium dibutyl-naphthalene sulphonate, 3 parts of naphthalenesulphonic acid/phenol- sulphonic acid/formaldehyde condensate 3:2:1, 10 parts of kaolin, 12 parts of Champagne chalk;b) 40 parts of Active Substance, 5 parts of sodium lignin sulphonate, 1 part of sodium dibutyl-naphthalene sulphonate, 54 parts of silicic acid;c) 25 parts of N-(2,6-dichloropyridine-4-carboxylic acid)-N'-sec-butyl-hydrazide, 4.5 parts of calcium lignin sulphonate, 1.9 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), 1.5 parts of sodium dibutyl naphthalene sulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalk, 28.1 parts of kaolin;d) 25 parts of Active Substance, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), 8.3 parts of sodium aluminum silicate, 16.5 parts of kieselguhr, 46 parts of kaolin;e) 10 parts of Active Substance, 3 parts of a mixture of the sodium salts of saturated fatty alcohol sulphates, 5 parts of naphthalenesulphonic acid/formaldehyde condensate, 82 parts of kaolin.______________________________________
The active substances are intimately mixed in suitable mixers with the additives, and the mixture is then ground in appropriate mills and rollers. Wettable powders are obtained having excellent wetting and suspension properties, which powders can be diluted with water to give suspensions of the desired concentration and which can be used, in particular, for leaf application.
The following substances are used to produce a 25% emulsifiable concentrate:
It is possible to produce from this concentrate, by dilution with water, emulsions of the desired concentration, which are particularly suitable for leaf application.
US Referenced Citations (2)
| Number |
Name |
Date |
Kind |
| 2703322 |
Fox |
Mar 1955 |
|
| 3040061 |
Bloom et al. |
Jun 1962 |
|
Foreign Referenced Citations (4)
| Number |
Date |
Country |
| 1080206 |
Dec 1954 |
FRX |
| 389983 |
Jul 1965 |
CHX |
| 711756 |
Jul 1954 |
GBX |
| 729967 |
May 1955 |
GBX |
Non-Patent Literature Citations (7)
| Entry |
| Parravicini et al., Chem. Abstracts 84, 1976, p. 30831, parag. 30825z. |
| Isler et al., Fasciculus, IV (1955), No. 18, pp. 1033-1047. |
| Seydel et al., Congress of Chemotherapy Report. |
| Palat et al., Chemical Abstracts, vol. 73 (1970), 128, 151z. |
| Palat et al., Chemi1al Abstracts, vol. 72 (1970), 55, 198n. |
| Isler et al., Helv. Chim Acta, vol. 38 (1955), pp. 1033-1046. |
| Libermann et al., Bull. Soc. Chim France (1954), pp. 1430-1443. |
Continuation in Parts (1)
|
Number |
Date |
Country |
| Parent |
685594 |
May 1976 |
|
Patent Grant
4137067
