Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
  • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide

Definitions

• the present invention relates to and has for its objects the provision for a particular new synergistic combination of zinc propylene-1,2-bis-dithiocarbamate and N- trichlorornethylthiophthalimide, both of which are known, which combination possesses outstanding fungicidal properties, active compositions in the form of synergistic mixtures of such two compounds with solid and liquid dispersible carrier vehicles, and methods for using such two compounds synergistically in a new way especially for combating fungi, with other and further objects becoming apparent from a study of the within specification and accompanying examples.
• N-trichloromethylthiophthalimide can be used for the control of phytopathogenic fungi.
• This active compound also has attained a considerable importance in practice. For example, it too is used with good results against downy mildew fungi.
• This compound also has the disadvantage that it possesses only a weak fungicidal activity against Botrytis.
• Botrytis is very difficult to control fungistatically with chemical agents.
• compositions which comprise syngergistic mixture combinations of the two active compounds: zinc propylene-1,Z-bis-dithiocarbamate having the formula ICC and N-trichloromethylthiophthalimide having the formula N-scon o II preferably in a weight ratio of substantially between about 1:0.25 and 1:2, possess especially broad and selective fungicidal activity.
• the fungicidal effectiveness of this combination of said two active compounds is much higher than the sum of the activities of the individual active compounds.
• a genuine synergistic effect is therefore present.
• a great advantage of the combination is that it acts both against the normal phytopathogenic fungi and also against the Botrytis species which are usually particularly difiicult to control.
• the weight ratio of the two compounds in the synergistic compositions can be varied within certain ranges.
• the composition mixture contains 0.25-2, for example 0.5-2, preferably 0.7-1.5, parts by weight of N-trichloromethylthiophthalimide (IIa) to 1 part by weight of zinc propylene-1,2-bis-dithiocarbamate (Ia).
• compositions show a synergistic fungicidal effect in the case of phytopathogenic fungi, but in particular on Botrytis species.
• compositions can therefore be used for the control of phytopathogenic fungi, preferably for the control of Botrytis species. Particularly important in practice is the control of plant diseases which are caused by Botrytis, and plant diseases which occur at the same time and are caused by other phytopathogenic fungi.
• the instant synergistic compositions are suitable for example both for the control of Botrytis cinerea and Plasmopam viticola.
• Botrytis 4 cinerea may infest all parts of the vine. Most important economically are the infestation of the berries (berry rot) and grape stems (common grey mould). At the time of vine blossom, the fungus may also infest the young grapes (inflorescence Botrytis) and cause considerable damage as a result.
• Botrytis diseases also occur in fruit cultivation, for example in strawberries; in ornamental plant cultivation, for example in all bulbous plants; in vegetable cultivation, for example in onions; and in coffee cultivation, and the like.
• synergistic mixture combinations of active compounds to be used according to the instant invention can be utilized, if desired, in the form of the usual formulations or compositions with diluents or extenders, i.e.,- dispersible carrier vehicles, such as solutions, emulsions, suspension, ernulifiable concentrates, spray powders, pastes, soluble powders, dusting agent, ganulates, etc.
• diluents or extenders i.e.,- dispersible carrier vehicles, such as solutions, emulsions, suspension, ernulifiable concentrates, spray powders, pastes, soluble powders, dusting agent, ganulates, etc.
• dispersible liquid diluent carriers such as aromatic hydrocarbons (for instance, benzene, tolene, xylene, etc.), halogenated, especially chlorinated, aromatic hydrocarbons (for instance, chlorobenzenes), paraflins (for instance, petroleum fractions), chlorinated aliphatic hydrocarbons (for instance, methylene chloride, etc.), alcohols (for instance, methanol, ethanol, propanol, butanol, etc.), amines (for instance, ethanolamine, etc.), ethers, etheralcohols (for instance, glycol monomethyl ether, etc.) amides (for instance, dimethyl formamide, etc.), sulfoxides (for instance, dimethyl sulfoxide, etc.), ketones (for instance, acetone, etc.), and water; as well as dispersible finely divided solid carriers, such as ground natural minerals (for instance, kaolins,
• the synergistic mixture of active compounds according to the instant invention may be employed alone or in the form of overall extended mixtures with such solid or liquid dispersible carrier vehicles and/or with other known compartible active agents, especially plant protection agents, such as other fungicides, herbicides, insecticides, bactericides, etc., if desired, or in the form of particular dosage preparations for specific application made therefrom, such as solutions, emulsions, suspensions, powders, pastes, and granulate which are thu ready for use, e.g. for application to agricultural crops such as in viticulture.
• plant protection agents such as other fungicides, herbicides, insecticides, bactericides, etc.
• particular dosage preparations for specific application made therefrom such as solutions, emulsions, suspensions, powders, pastes, and granulate which are thu ready for use, e.g. for application to agricultural crops such as in viticulture.
• compositions which comprise extended mixtures of a dispersible carrier vehicle such as (1) a dispersible carrier solid, or (2) a dispersible carrier liqiud preferably including a carrier vehicle assistant, e.g., surface-active agent, such as an emulsifying agent and/or a dispersing agent, and a combined total amount of the synergistic mixture of active compounds which is effective for the purpose in question and which is generally about 0.0l95%, and preferably 0.0395%, by weight of the overall extended mixture.
• a dispersible carrier vehicle such as (1) a dispersible carrier solid, or (2) a dispersible carrier liqiud preferably including a carrier vehicle assistant, e.g., surface-active agent, such as an emulsifying agent and/or a dispersing agent, and a combined total amount of the synergistic mixture of active compounds which is effective for the purpose in question and which is generally about 0.0l95%, and preferably 0.0395%, by weight of the overall extended
• the present invention contemplates methods of selectively controlling or combating fungi, especially Botrytis species, which comprises applying to at least one of (a) such fungi and (b) their habitat, i.e. the locus to 'be protected, a fungicidally effective amount of the particular synergistic mixture of said two active compounds of the invention alone or together in an overall mixture with a carrier vehicle as noted above.
• the instant formulations or compositions are applied in the usual manner, for instance by spraying, atomizing, vaporizing, scattering, dusting, watering, sprinkling, pouring, and the like.
• synergistic mixture of said two active compounds is used, i.e. applied, in a combined total amount of substantially between about 0.0110, preferably 1.53.0, kilograms per hectare, regardless of the presence or absence of the carrier vehicle and/or other compatible active agents.
• concentration of the particular synergistic mixture of said two active compounds utilized in admixture with the carrier vehicle will depend upon the intended application, and such concentration may be varied within fairly wide limits. Therefore, in special cases, it is possible to go above or below the aforementioned concentration ranges.
• EXAMPLE 1 Botrytis test The ready-to-use preparations of the particular active compound or synergistic mixture were prepared by diluting with water a concentrate of such active compound or synergistic mixture (i.e. consisting of 70% of active compound or synergistic combination of active compounds [zinc propylene-1,2-bis-dithiocarbamate (Ia) and N- trichloromethylthiophthalimide (IIa)] in the ratio of 110.7, 26% of silicic acid powder as inert material, 2.5% of lignin sulfate as protective colloid and 1.5% of alkylaryl surfonate as adhesive) until the desired active compound concentration was reached.
• a concentrate of such active compound or synergistic mixture i.e. consisting of 70% of active compound or synergistic combination of active compounds [zinc propylene-1,2-bis-dithiocarbamate (Ia) and N- trichloromethylthiophthalimide (IIa)] in the ratio
• Vines were sprayed with these aqueous preparations of the given active compound or compounds 8 times (at an interval of 2 weeks in each case), during the entire vegetation period, that is during the season from the middle of May until the middle of September.
• control plots were also established which were not active compound treated.
• EXAMPLE 2 lings is determined as a percentage of the untreated but also inoculated control plants Fusicladlum test a le scab Protective pp 1 0% means no infestation; 100% means that the infes- Parts by Wt. 0 tatlon is exactly as great as in the case of the control Solvent, acetone 4-7 plants.
• Emulsifier, alkylaryl polyglycol ether The particular active compounds, the concentrations f Water ch actlve compounds and the results obtai d can be The amount of the particular active compound or seen from the following Table 2:.
• Young apple seedlings in the 4-6 leaf stage are sprayed with the particular spray liquid until dripping wet.
• the plants remain in a greenhouse for 24 hours at C. and at a relative atmospheric humidity of 70%. They are then inoculated with an aqueous conidium suspension of the apple scab organism (Fusicladium dendriticum and incubated for 18 hours in a humidity chamber at 18-20 C. and at a relative atmospheric humidity of 100%.
• the total concentration of active compounds in the combination are the same as the individual concentrations of active compounds when used alone rather than in combination.
• the effectiveness of the combinations should lie between that of the less effective individual component and that of the effective individual component.
• the combination of active compounds according to the invention has an effectiveness which lies far above the effectiveness of the most effective individual component.
• synergistic mixture combinations of the foregoing compounds contemplated by the present invention possess the desired strong fungicidal properties, with regard to a broad spectrum of activity, as well as a comparatively low toxicity toward warm-blooded creatures and a concomitantly low phytotoxicity, enabling such synergistic mixture of compounds to be used with correspondingly favorable compatibility with warm-blooded creatures and plants for more effective control and/or elimination of fungi by application of such synergistic mixture of compounds to such fungi and/ or their habitat.
• Synergistic fungicidal composition which comprises a mixture of zinc propylene-1,2-bis-dithiocarbamate having the formula CH NH([l/S s and N-trichloromethylthiophthalimide having the formula N-SCCla in a ratio by weight of substantially between about 1:0.25-2.
• composition according to claim 1 wherein said mixture is in the form of an overall mixture with a dispersible carrier vehicle, in which the first said mixture is present in a fungicidally effective amount.
• composition according to claim 3 wherein the combined content of said dithiocarbamate and said phthalimide in the first mixture is substantially between about 8 0.01 and by weight of the overall mixture with said dispersible carrier vehicle.
• composition according to claim 4 wherein said carrier vehicle is selected from the group consisting of (l) a dispersible finely divided carrier solid and (2) a dispersible carrier liquid containing a surface-active agent selected from the group consisting of anionic emulsifying agents, nonionic emulsifying agents, dispersing agents, and mixtures thereof.
• Method for combating fungi which comprises applying to at least one of (a) such fungi and (b) their habitat, a fungicidally effective amount of a fungicidal composition containing a mixture according to claim 1.
• said carrier vehicle is selected from the group consisting of (l) a dispersible finely divided carrier solid and (2) a dispersible carrier liquid containing a surface-active agent selected from the group consisting of anionic emulsifying agents, nonionic emulsifying agents, dispersing agents, and mixtures thereof.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=7104269

Family Applications (1)

Country Status (13)

Cited By (1)

Citations (2)

• 1966
  • 1966-12-20 DE DE19661542890 patent/DE1542890A1/de active Pending
• 1967
  • 1967-10-25 CH CH1491867A patent/CH488395A/de not_active IP Right Cessation
  • 1967-10-30 IL IL6728856A patent/IL28856A/xx unknown
  • 1967-11-14 BG BG008880A patent/BG15730A3/bg unknown
  • 1967-11-16 GB GB52160/67A patent/GB1148140A/en not_active Expired
  • 1967-12-01 US US687116A patent/US3472936A/en not_active Expired - Lifetime
  • 1967-12-12 NL NL6716893A patent/NL6716893A/xx unknown
  • 1967-12-15 GR GR670138289A patent/GR38289B/el unknown
  • 1967-12-18 BE BE708139D patent/BE708139A/xx unknown
  • 1967-12-19 ES ES348415A patent/ES348415A1/es not_active Expired
  • 1967-12-20 AT AT1150167A patent/AT275240B/de active
  • 1967-12-20 FR FR1549782D patent/FR1549782A/fr not_active Expired
• 1969
  • 1969-12-31 MY MY1969407A patent/MY6900407A/xx unknown

Patent Citations (2)

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