FUNGICIDAL COMPOSITIONS

Abstract: The invention relates to fungicidal compositions com­ prising copper oxyquinolate in combination with certain thiazoles which are applied as seed dressing and intended to prevent fungal attack on seeds.

Description: FUNGICIDAL COMPOSITIONS This invention is concerned with fungicidal compositions, for instance fungicidal compositions which are applied as seed dressing and intended to prevent fungal attack on seeds. According to the present invention there is provided a fungicidal composition comprising copper oxyquinolate in combination with a thiazole of the formula EMI1.1 wherein R and R1 may be the same or different and are hydrogen or C1-C8 alkyl. Preferably, R and R1 are C1-C4 alkyl, and most preferably R and R1 are methyl. A composition in accordance with the present invention may be used as a fungicide and is particularly useful when applied to seeds. Thus a composition according to the present invention provides a seed dressing with a wide spectrum of activity, together with enhanced or synergistic activity against at least certain fungi. For the control of phytopathogenic fungi on seed (e.g. Calonectria nivalis, Pyrenophora graminea, Tilletia caries, Ustilago avenae Septoria nodorum, Telletia foetida, Ustilago hordei, Ustilago nigra, Urocystis occulata, Pyrenophora avenae, Cochliobolus savitus) materials containing mercury are mainly used. However, these materials possess the disadvantage of toxicity to warm blooded animals. Other less toxic materials are not satisfactory on account of their narrow spectrum of activity. A cotnposition of the present invention in the form of a seed dressing is less toxic than mercury containing dressings and is suitable for agricultural, gardening and forestry use. The composition may include further ingredients such as other fungicides. Furthermore, the composition may be used together with one or more additional pesticidal materials such as insecticides (for instance organochlorine compounds such as Lindane, organophosphoric esters such as Diazinon, Isazofos, and Thiofanox and carbamates such as Carbofuran, Mercaptodimethar, and Bendiocarb) and repellants (such as anthraquinone, thicanthraquinone, Benzathrone, Ziram and diphenylguanidine) to protect the seeds against pests such as insects and birds. When compared with traditional mercury containing Universal seed dressings, the compositions in accordance with the present invention possess a wider spectrum of activity (e.g. control of Ustilago nuda, Ustilago tritici, Typhula incarnata, Phynchosporium secalis, Erysiphe graminis and a higher degree of activity against any other seed pathogens (e.g. Pyrenophora avenae Cochliobolus sativus). The composition of the present invention may include one or more carrier materials such as the minerals talc, kaolin, bentonite and barytes, stickers such as Spindeloil, ethylene glycol and polyvinylacetate. A composition may include pigments such as iron oxide and Rubin Toner. A composition in accordance with the present invention in the form of a powder may be formulated by mixing together all the dry materials, including the carrier and additives until a homogenous mixture is formed. The stickers are then added and the whole mixed again until the mixture becomes homogenous. In the case of a liquid formulation, organic solvents such as xylene, dimethyl formamide, ethylene glycol and methanol and cyclohexane are used as diluting agents and mixed together with surface active agents (Calcium Dodecylbenzenesulphonate, polyglycolether and Arylpolyether alcohols) as well as a dye (e.g. Rhodamine and methylviolet). Preferably the weight ratio of compound I to copper oxyquinolate is from 1.25 to 7.5 or preferably from 1.25 to 3.75. A composition in accordance with the present invention is preferably applied to seed such that the amounts of the active compound applied per 100 kg. of seed is as follows: Copper oxyquinolate from 5 to 50 gm a.i. Compound I frown 10 to 80 gm a.i. More preferably the amounts are as follows: Copper oxyquinolate from 5 to 35 gm a.f. Compound 1 from 35 to 50 gm a.i. Compositions in accordance with the present invention may be applied to the seeds of, for instance, rye, wheat, barley and oats. The present invention also provides a method of protecting seeds against fungi, the method comprising applying to the seeds a composition in accordance with the invention. An example of the invention will now be described, the seed treatment method being carried out in accordance with the BBA guidelines 4-1.1 (!2arch 1974) Ehle, H., Frohbeyer, P.E., Reinhard, H. and Roder, K. (1974), "Preliminary guidelines for the testing of seed dressings against cereal diseases", March 1974, published by BBA, Messeweg 11/12 3300 Braunschweig. In this example, Compound I is 2,4 -dimethyl-5-carboxanilidothiazole , Example Spring wheat cv. Tinmo was artificially infected with dry spores of Tilletia caries at a rate of 2g of spores per kg of wheat seed. The inoculated seed was treated with the seed treatments at various rates. These wettable powder formulations were diluted with water and applied to the seed by spraying a fine mist of liquid seed treatment using a de Vilbiss [trademark] compressed air powered spray gun, on to a measured quantity of seed and shaking the seed and chemical in a bottle for 5 minutes. All formulations in addition to active ingredient contained wetting and dispersing agents, pigments, kaolin and white oil. All formulations were diluted with water to keep a constant rate of application volume of 400 ml/100kg seed. The seed was drilled into open ground, on a clay loam soil type, using a tractor mounted Oyjord Seed Drill. Plot size was l.6m x 5 m with four replications, all treatments were fully randomized. Assessment of disease was carried out by taking 100 randomly selected heads per plot and examining for disease thus establishing the infection level. Compositions and results are summarized in Table 1. Results show the enhanced effectiveness of Compound I when it is used in a mixture with copper oxyquinolate, particularly when Compound I is used at the lower of the two concentrations. The results obtained with formulations 9, 10 and 11 were analysed by comparing them with the results obtained by the use of Compound I or copper oxyquinolate alone and the theoretical percentage control by a mixture of Compound I and copper oxyquinolate was calculated. It can be seen that the presence of copper oxyquinolate gives a synergistic enhancement to the effectiveness of Compound I, the degree of enhancement being of great significance having regard to the requirements in many countries for control which is either 100% effective or very close to 1002 effective. G696 SYNERGY RESULTS G696 Observed Additive Observed Calculated % Control (mean%) Control (mean%) ControlÚ Xê Yê Et IMAZ 95.7 12.496.2375*@ 95.7 0 95.7* 95.7 16.75 96.42025* 63.7 12.5 68.2375* 63.7 0 63.7* 63.7 16.75 69.78025* PROCHLORAZ 95.7 50.9 97.8887 95.7 70.2 98.7186 95.7 80.8 99.1744 63.7 50.9 82.1767* 63.7 70.2 89.1826 63.7 80.8 93.0304 TBZ 95.7 6.6 95.9838 95.7 12.5 96.2375 95.7 44.5 97.6135 63.7 6.6 66.0958* 63.7 12.5 68.2375 63.7 44.5 79.8535* CGA G4251 95.774.4 98.8992* 95.7 93.6 99.7248001 95.7 97.85 99.90755 63.7 74.4 90.7072* 63.7 93.6 97.6768* 63.7 97.85 99.21955* CuOxy 95.7 65.85 98.53155* 95.7 74.4 98.8992 95.7 80.8 99.1744* 63.7 65.85 87.60355* 63.7 74.4 90.7072* 63.7 80.8 93.0304* 1. Based on observed mean Z of individual components of mixture. 2. X and Y are from means for two tests. 3. Et= X + Y - () 4. * = synergy TABLE 1 FORMULATION 1 2 3 4 5 6 7 8 9 10 11 Compound I, g 75 37.5 - - - 75 75 75 37.5 37.5 37.5 CuOQ(1), g - - 10 20 30 10 20 30 10 20 30 Control % (2) 95.7 63.9 80.8 100 97.9 100 100 95.7 95.7 Theoretical(3) Control % - - - - - 98.5 98.9 99.2 87.6 90.7 93.0 I/CuOQ(5) - - - - - 7.5 3.75 2.5 3.75 1.875 1.25 REMARKS (1) Copper Oxyquinolate (2) Observed Mean % control for 2 field trials. (3)from Colby Formula (4) Untreated control Mean % infected 47.5% (5) Weight ratio

Claims: CLAIMS: 1. A fungicidal composition characterised in that it comprises a thiazole having the formula EMI9.1 wherein R and R1 may be the same or different and are hydrogen or C1-C8 alkyl; and copper oxyquinolate. 2. A composition according to claim 1 characterised in that R and R1 are hydrogen or C1-C4 alkyl. 3. A composition according to claim 1 or claim 2 characterised in that R and R1 are methyl. 4. A composition according to any of the preceding claims characterised in that the thiazole/copper oxyquinolate weight ratio is 16/1 - 1/5. 5. A composition according to claim 4 characterised in that said weight ratio is 1/1 - 10/1. 6. A composition according to claim 5 characterised in that said weight ratio is 1.25 - 3.75/1. 7. A method of treating seeds subject or liable to fungal attack characterised in that the method comprises applying a fungicidal amount of a composition as claimed in claim 1.

Inventors: BARTLETT, DIGBY H.
Applicants: UNIROYAL LIMITED
Application year: 1985
Main classification: A01N43
IPC codes: A01N43, A01N59, A01N55