# Patent

## Title
Use of nabumetone or 6-methoxynaphthyl acetic acid for the treatment of

## Abstract

This application is a continuation of application Ser. No. 08/002,399 filed Jan. 13, 1993, abandoned.

## Background
This invention relates to phytosanitary compositions of the type containing an oxynil and at least one substance liquid at ambient temperature.

The invention also relates to a process for applying these compositions.

In the context of the invention, the term "oxynil" is understood to apply generally to hydroxybenzonitriles, including 4-hydroxy-3,5-dibromobenzonitrile or bromoxynil ou and 4-hydroxy-3,5-diiodobenzonitrile or ioxynil, their salts and their esters.

Phytosanitary compositions containing oxynils as selective herbicides are already known.

It is also known that, in addition to the use of herbicides, the complete treatment of plants often requires the use of insecticides, fungicides, growth regulators or any other pesticide. In overall terms, this corresponds on the one hand to a very significant consumption of chemical products by the agriculturalist and hence to an increase in the retail price of cultivated plants, and also to an accumulation in the cultivated soils of those chemical products, which presents pollution and environmental problems, and on the other hand to a loss of time for agriculturalists who have to successively apply as many treatments as necessary to their plants.

Now, after extensive studies, Applicants have succeeded in developing preparations for the treatment of plants, which are less onerous and easier to use, in the form of a phytosanitary composition which is characterized in that it contains a combination of an oxynil and at least one substance selected from the group comprising insecticides, fungicides, growth regulators, pesticides and/or herbicides selected from the group comprising S-alkyl- and S-benzyl-thiolcarbamates, chloracetanides, and herbicides selected from the group consisting of butamifos, cinmethylin, clethodim, isopropalin, olomazone, dalepen, tebutame, sulfosate, methyl (R)-2(7-(2-chloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyloxy)-2-naphthyl oxy) propionate and (+)-tetrahydrofurfuryle (R)-2-4-(6-chloro-quinoxaline-2-yloxy)phenoxy! propanoate, fluazifop-butyl and sethoxydime, this substance which is liquid at ambient temperature being intended to keep the oxynil in the liquid state at the application site, if necessary after it has been brought into the liquid state, with the proviso that, in cases where the substance is a herbicide consisting of

an S-benzyl-thiolcarbamate selected from the group consisting of thiobencarbe, orbencarbe, thiocarbazil, prosulfocarbe and esprocarbe, the ratio of S-benzyl-thiolcarbamate to ioxynil is below 2.5,

fluazifop-butyl or fluazifop-p-butyl, the ratio fluazifop-butyl to oxynil or fluazifop-p-butyl to oxynil is above 0.7,

sethoxydime, the ratio sethoxydime to oxynil is below 0.4.

It has been found that, in the case of this phytosanitary composition containing a combination of an oxynil used in a dose in which, on its own, it shows little, if any, activity and at least one of the above-mentioned substances liquid at room temperature, a synergistic effect is surprisingly and unexpectedly developed between the oxynil and the substance liquid at ambient temperature.

In the context of the invention, a pesticide is understood to be any chemical product used in agriculture other than herbicides, insecticides, fungicides and growth regulators, such as for example a bactericide or a herbicide antidote.

In cases where the substance liquid at ambient temperature is a herbicide, not only is the herbicidal effect of the oxynil potentiated, it may even be completed by the activity of the other herbicide used as the substance liquid at ambient temperature. Accordingly, the spectrum of activity of the herbicidal composition according to the invention can be broadened and a complete herbicidal treatment of this type can thus be applied in a single step to the plant to be treated.

In cases where the substance liquid at ambient temperature combined with the oxynil is an insecticide, a fungicide, a growth regulator or any other pesticide, the herbicidal effect of the oxynil is always potentiated by the substance which may also have an effect of its own. Accordingly, phytosanitary compositions of this type perform a dual function on the plants to be treated: herbicide-insecticide, herbicide-fungicide, herbicide-growth regulator or herbicide-pesticide, depending on the substance liquid at ambient temperature which is combined with the oxynil. A single application of this type of composition enables the plant to be subjected to a double treatment at any time.

The combination with an oxynil of a mixture of at least two substances, of which at least one is liquid at ambient temperature, to obtain a phytosanitary composition according to the invention having at least a triple effect on the plants to be treated is also possible providing the substances used are chemically compatible with one another.

The expression "substance liquid at ambient temperature" is understood to mean that the substance has a melting point of or below 30.degree. C.

The phytosanitary compositions according to the invention contain 48 to 450 g/l oxynil and may be formulated as:

concentrated suspensions,

emulsifiable concentrates,

aqueous emulsions,

true solutions,

oily emulsions.

In addition to the combination of an oxynil and at least one substance liquid at ambient temperature, the phytosanitary composition according to the invention may comprise one or more ionic or nonionic surfactants and a diluent.

The surfactants may be selected from the nonionic and anionic surfactants listed in the annual publication (North American Edition et International Edition) edited by McCutcheon's Division MC Publishing Company and relating to "Emulsifiers & Detergents" or in the index of surfactants published by B. Parant in D.T.A. (France).

The nonionic surfactants suitable for use in accordance with the invention are those obtainable by the condensation of one or more mols ethylene and/or propylene oxide with short-chain or fatty alcohols, alkylphenols, fatty amines, fatty amides, polystyrylphenols.

The anionic surfactants include alkylarylsulfonates in the form of alkali metal salts, alkaline earth metal salts or alkanolamines, soaps, phosphoric esters of the nonionic surfactants mentioned above, polynaphthylmethane-polysulfonates and their alkylated derivatives, lignosulfonates and polymers containing several carboxylic functions.

The diluent is selected from the group consisting of water, acetophenone, cyclohexanone, isophorone, toluene, xylene, dimethyl-sulfoxide (or DMSO). It is emphasized that, where they are liquid, the anionic or nonionic surfactants may also serve as diluents.

The phytosanitary composition according to the invention may also comprise such additives as protective agents, penetration agents, stabilizers, volatility reducing agents, sequestrants, colourants and corrosion inhibitors. It should be noted that, in certain cases, these additives may also serve as diluents.

The phytosanitary composition according to the invention may be prepared from a liquid concentrate using the diluents mentioned above.

It is of advantage to start from a self-emulsifiable concentrate containing a combination of an oxynil and at least one of the above-mentioned substances liquid at ambient temperature dissolved in an emulsifier or in a solvent. By preparing the phytosanitary composition from such a concentrate by addition of water, a ready-to-use liquid product according to the invention is obtained.

Finally, the invention also relates to the use of the ready-to-use sprays containing the active constituent(s) in the concentration required to obtain biological results.

The process for applying the phytosanitary compositions according to the invention is characterized in that the phytosanitary compositions are applied to the plant to be treated by spraying in a quantity sufficient to distribute 48 to 450 grams oxynil per hectare of treated plants.

The phytosanitary composition according to the invention may be applied to the soil by conventional techniques using, for example, hand pump sprayers, power sprayers or pre-pressurized sprayers equipped with application distributors or nozzles well known to the expert.

The products or groups of products from which the substances liquid at ambient temperature intended to keep the oxynil in the liquid state at the application site, if necessary after it has been brought into the liquid state, are selected and the dosages in which they are used for the application of the phytosanitary compositions according to the invention are described in the following; these products or groups of products are herbicides, insecticides, fungicides, growth regulators and pesticides.

The substances liquid at ambient temperature which form part of the composition according to the invention are designated hereinafter either by their chemical names or by their common names; in the latter case, the corresponding chemical names can be found in "The Pesticide Manual", Ninth Edition, published by The British Crop Protection Council.

The herbicides are selected from:

the S-benzyl-thiolcarbamates comprising thiobencarbe, orbencarbe, thiocarbazil, prosulfocarbe and esprocarbe used for the preparation of the phytosanitary compositions according to the invention in such a quantity that the ratio of herbicide to ioxynil is below 2.5,

the S-alkyl-thiolcarbamates comprising EPTC, pebulate, cycloate, butylate, vernolate, diallate, triallate and molinate used for the preparation of the phytosanitary compositions according to the invention in a concentration of 200 a 970 g/l and used at the application site in quantities of 10 to 2000 g/ha and preferably in quantities of 50 to 1000 g/ha,

the chloracetanilides comprising acetochlore, butachlore, butenachlore, metolachlore and pretilachlore used for the preparation of phytosanitary compositions according to the invention in a concentration of 200 to 970 g/l and used at the application site in quantities of 10 to 2000 g/ha and preferably in quantities of 50 to 1000 g/ha,

butamifos, cinmethylin, clethodim, isopropalin, clomazone, dalapen, tebutame, sulfosate, methyl (R)-2(7-(2-chloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyloxy)-2-naphthyl oxy) propionate and (+)-tetrahydrofurfuryle (R)-1-4-(6-chloro-quinoxaline-2-yloxy)phenoxy! propanoate used for the preparation of phytosanitary compositions according to the invention in a concentration of 40 to 800 g/l and used at the application site in quantities of 10 to 2000 g/ha and preferably in quantities of 50 to 1000 g/ha,

fluazifop-butyl or fluazifop-p-butyl used for the preparation of phytosanitary compositions according to the invention in such a quantity that the ratio fluazifop-butyl to oxynil or fluazifop-p-butyl to oxynil is above 0.7 and used et the application site in quantities of 50 to 275 g/ha,

sethoxydime used for the preparation of phytosanitary compositions according to the invention in such a quantity that the ratio of sethoxydime to oxynil is below 0.4 and used at the application site in a quantity of 50 to 275 g/ha.

The insecticides are selected from:

the pyrethrinoids comprising allethrine, resmethrine, cyhalothrine, cyphenothrine, permethrine, empenthrine, cycloprothrine, flucythrinate, fluvalinate, fenvalerate and their natural or synthetic isomers used for the preparation of the phytosanitary compositions according to the invention in a concentration of 1 to 500 g/l and used at the application site in quantities of 5 to 200 g/ha and preferably in quantities of 10 to 100 g/ha,

organophosphorus compounds comprising cadusafos, chlorfenvinphos, cyanophos, demethon-S-methyl, diazinon, dichlorvos, dicrotophos, disulfoton, edifenphos, ethion, ethoprophos, etrimphos, fenitrothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isazofos, isofenphos, isoxathion, malathion, mecarbam, mephosfolan, naled, omethoate, oxydemeton-methyl, methacrifos, mevinphos, parathion, phenthoate, phorate, phosphamidon, phoxime, piperophos, pirimiphos, profenofos, propaphos, propetamphos, prothiofos, pyraclofos, sulfotep, sulprofos, terbufos, thiometon and triazophos in the form of their various esters, particularly methyl and ethyl esters, used for the preparation of the phytosanitary compositions according to the invention in a concentration of 10 to 1000 g/l and used at the application site in quantities of 10 to 1000 g/ha and preferably in quantities of 50 to 500 g/ha,

benfuracarbe, carbosulfan, furathiocarbe and propargite, used for the preparation of the phytosanitary compositions according to the invention in a concentration of 100 to 800 g/l and used at the application site in quantities of 10 to 1000 g/ha and preferably in quantities of 50 to 500 g/ha,

The fungicides are selected from:

etridiazole, fenpropidine, fenpropimorphe, tridemorphe, iprobenfos, propiconazole, tetraconazole and pyrifenox, used for the preparation of the phytosanitary compositions according to the invention in a concentration of 50 to 750 g/l and used at the application site in quantities of 5 to 1000 g/ha and preferably in quantities of 10 to 750 g/ha,

The growth regulators are selected from:

etacelasil, heptopargil and hydrazinoethanol used for the preparation of the phytosanitary compositions according to the invention in a concentration of 200 to 800 g/l and used at the application site in quantities of 10 to 2000 g/ha and preferably in quantities of 50 to 1000 g/ha.

The pesticides include:

methoprene, dimethylphthalate, diethyltoluamide and fluxofenim used for the preparation of the phytosanitary compositions according to the invention in a concentration of 40 to 1000 g/l and used at the application site in quantities of 10 to 1000 g/ha and preferably in quantities of 50 to 500 g/ha.

The following examples, which are intended to enable the invention to be better understood without limiting it in any way, are given purely by way of illustration in conjunction with advantageous embodiments.

A phytosanitary composition according to the invention was prepared in the form of an emulsifiable concentrate containing

192 g/l of ioxynil octanoate and

480 g/l of prosulfocarbe

and was applied by spraying in a quantity of 0.5 l/ha to plants of Chenopodium album, Galium aparine and Veronica sp. in pots, at the 3 to 4 leaf stage in the doses indicated in Table I.

The herbicidal effect of the composition on the treated species was evaluated after 21 days.

The results of this test are set out in Table I.

The expression "Expected Results" is used to denote the percentage destruction of the plants calculated by addition of the effect of oxynil applied on its own (x) on the one hand and the effect of the substance liquid at ambient temperature applied on its own (Y) on the other hand, taking into account their respective application doses, in accordance with the following formula: ##EQU1## where X and Y represent the percentages destruction of the treated plants observed in relation to an untreated control for which the destruction of the plants is considered as being 0%, the observation being made 21 days after the treatment.

The expression "Results obtained" is used to denote the percentage destruction of the treated plants obtained in relation to an untreated control for which the destruction of the plants is considered as being 0%.

There is a synergistic effect between the oxynil and the substance liquid at ambient temperature which are present in combination in the phytosanitary compositions according to the invention whenever the results obtained are better than the expected results. ______________________________________ Results obtained (%) after individual application of the Expected Results constituents of the results  obtained composition  (%)      (%) ______________________________________ Ioxynil octanoate 96        0        96     96 (g/ha) Prosulfocarbe (g/ha) 0        240      240    240 Chenopodium album 15        0        15     100 Galium aparine 35        10       42     55 Veronica sp. 50        0        50     75 ______________________________________

It can be seen from this Table that a synergistic effect is developed between the ioxynil octanoate and the prosulfocarbe.

Three phytosanitary compositions according to the invention were prepared in the form of emulsifiable concentrates of which the respective formulations are shown in Table II below: ______________________________________ Bromoxynil octanoate Prosulfocarbe (g/l)       (g/l) ______________________________________ Composition 1 100           240 Composition 2 200           240 Composition 3 200           480 ______________________________________

Each of these compositions was applied by spraying in a quantity of 1 1/ha to plants of Chenopodium album and Galium aparine in pots at the 3 to 4 leaf stage in the doses indicated in Table III.

The herbicidal effect of composition 1 on Chenopodium album and on Galium aparine and the herbicidal effects of compositions 2 and 3 on Chenopodium album alone were evaluated after 21 days.

The results of these tests are set out in Table III.

The "Expected results" end "Results obtained" are as defined in Example 1. __________________________________________________________________________ Results obtained (%) after individual application of the Expected results Results obtained constituents of the (%) for the (%) for the composition 1  2  3  1  2  3 __________________________________________________________________________ Bromoxynil octanoate 100 200 0  0  100 200 200 100 200 200 (g/ha) Prosulfocarbe (g/ha) 0  0  240 480 240 240 480 240 240 480 Chenopodium album 0  55 0  5  0  55 57 70 95 100 Galium aparine 40 75 10 13 46 -- --* 70 -- -- __________________________________________________________________________ *indicates that the test was not carried out on the species or in the doses in question

It can be seen from this Table that a synergistic effect is developed between the bromoxynil octanoate and the prosulfocarbe.

Four phytosanitary compositions according to the invention were prepared in the form of emulsifiable concentrates of which the respective formulations are shown in Table IV. ______________________________________ Ioxynil octanoate Diallate (g/l)     (g/l) ______________________________________ Composition 1  192         200 Composition 2  192         400 Composition 3   96         400 Composition 4   48         400 ______________________________________

Each of these compositions was applied by spraying in a quantity of 0.5, 1, l and 2 l/ha, respectively, to plants of Chenopodium album, Galium aparine and Matricarla inodora in pots at the 3 to 4 leaf stage in the doses indicated in Table V.

The herbicidal select of each of the compositions on the treated species was evaluated after 21 days.

The results of these tests are set out in Table V.

The "Expected results" and "Results obtained" are as defined in Example 1. __________________________________________________________________________ Results obtained (%) after individual Expected results Results obtained application of the (%) for the (%) for the constituents of the compositions compositions composition   1  2  3  4  1  2  3  4 __________________________________________________________________________ Ioxynil octanoate 96 0  0  0  0  96 96 96 96 96 96 96 96 (g/ha) Diallate (g/ha) 0 100 200 400 800 100 200 400 800 100 200 400 800 Chenopodium album 40 0  0  0  0  40 40 40 40 55 95 100 100 Galium aparine 60 5  10 5  5  62 64 62 62 85 80 85 93 Matricaria inodora 20 0  0  0  0  20 20 20 20 45 40 35 30 __________________________________________________________________________

It can be seen from this Table that a synergistic effect is developed between the ioxynil octanoate and the diallate.

Four phytosanitary compositions according to the invention were prepared in the form of emulsifiable concentrates of which the respective formulations are shown in Table VI. ______________________________________ Bromoxynil octanoate Molinate (g/l)       (g/l) ______________________________________ Composition 1 192           400 Composition 2 96            400 Composition 3 48            400 Composition 4 48            800 Composition 5 192           400 Composition 6 96            400 Composition 7 48            400 ______________________________________ Compositions 1 to 4 were applied by spraying in quantities of 0.25, 0.5, and 1 l/ha, respectively, to plants of Amaranthus sp. in pots and Compositions 2 to 7 were applied by spraying in quantities of 0.5, 1, 1, 0.5, 1 and 2 l/ha, respectively, to plants of Chenopodium album and on Galium aparine in pots at the 3 to 4 leaf stage in the doses indicated in Table VII.

The herbicidal effect of each of these compositions on the treated species was evaluated after 21 days.

The results of these tests are set out in Tables VII A and VII B.

The "Expected results" and "Results obtained" are as defined in Example 1. ______________________________________ Results obtained (%) after individual application of the constituents of each composition ______________________________________ Bromoxynil octanoate (g/ha) 48    96    0    0    0    0 Molinate (g/ha) 0     0     100  200  400  800 Amaranthus sp.  55    --    0    0    0    0 Chenopodium album 0     0     --   0    0    0 Galium aparine  25    30    --   0    0    0 ______________________________________ __________________________________________________________________________ Expected results (%) Results obtained (%) for the compositions for the compositions 1  2  3  4  5  6  7  1  2  3  4  5  6  7 __________________________________________________________________________ Bromoxynil ocatanoate 48 48 48 48 96 96 96 48 48 48 48 96 96 96 (g/ha) Molinate (g/ha) 100 200 400 800 200 400 800 100 200 400 800 200 400 800 Amaranthus sp. 55 55 55 55 -- -- -- 75 70 75 75 -- -- -- Chenopodium album -- 0  0  0  0  0  0  -- 15 60 60 30 55 85 Galium aparine -- 25 25 25 30 30 30 -- 35 83 90 50 50 70 __________________________________________________________________________

It can be seen from this Table that a synergistic effect is developed between the bromoxynil octanoate and the molinate.

Three phytosanitary compositions according to the invention were prepared in the form of emulsifiable concentrates of which the respective formulations are shown in Table VIII. ______________________________________ Bromoxynil octanoate Metolachlore (g/l)       (g/l) ______________________________________ Composition 1 192           480 Composition 2 96            480 Composition 3 64            640 Composition 4 32            640 Composition 5 192           240 ______________________________________ Compositions 1 and 2 were applied by spraying in quantities of 0.25 and 0.5 l/ha, respectively, to plants of Galium aparine in pots, Compositions 3 and 4 were applied by spraying in quantities of 0.75 and 1.5 l/ha, respectively, to plants of Solanum nigrum and on Matricaria inodora in pots and Compositions 3, 4 and 5 were applied by spraying in quantities of 0.75, 1.5 and 0.5 l/ha, respectivelly, to plants of Chenopodium album and Veronica sp. at the 3 to 4 leaf stage in the doses indicated in Table IX.

The herbicidal effect of each of these compositions on the treated species was evaluated after 21 days.

The results of these tests are set out in Tables IX A and IX B.

The "Expected results" and "Results obtained" are as defined in Example 1. ______________________________________ Results obtained (%) after individual application of the constituents of each composition ______________________________________ Bromoxynil octanoate (g/ha) 48    96    0    0    0    0 Metolachlore (g/ha) 0     0     120  240  480  960 Galium aparine  25    --    0    5    --   -- Solanum nigrum  25    --    --   --   0    0 Chenopodium album 5     7     0    --   5    5 Matricaria inodora 5     --    --   --   5    5 Veronica sp.    20    25    7    --   7    15 ______________________________________ __________________________________________________________________________ Expected results (%) Results obtained (%) for the compositions for the compositions 1  2  3  4  5  1  2  3  4  5 __________________________________________________________________________ Bromoxynil octonoate 48 48 48 48 96 48 48 48 48 96 (g/ha) Metolachlore (g/ha) 120 240 480 960 120 120 240 480 960 120 Galium aprine 25 29 -- -- -- 45 45 -- -- -- Solanum nigrum -- -- 25 25 -- -- -- 40 50 -- Chenopodium album -- -- 10 10 7  -- -- 95 100 97 Matricaria inodora -- -- 10 10 -- -- -- 40 60 -- Veronica sp. -- -- 26 32 30 -- -- 95 90 97 __________________________________________________________________________

It can be seen from this Table that a synergistic effect is developed between the bromoxynil octanoate and the metolachlore.

A phytosanitary composition according to the invention was prepared in the form of emulsifiable concentrate containing:

96 g/l ioxynil octanoate and

124 g/l of fluazifop-p-butyl

and was applied by spraying in a quantity of 0.5 l/ha to plants of Galium aparine and Solanum nitrum in pots at the 3 to 4 leaf stage in the doses indicated in Table X.

The herbicidal effect of this composition on the treated species was evaluated after 21 days.

The results of these tests are Set out in Table X.

The "Expected results" and "Results obtained" are as defined in Example 1. ______________________________________ Results obtained (%) after individual application of the Expected constituents of the results  Results obtained composition (%)      (%) ______________________________________ Ioxynil octanote 48       0       48     48 (g/ha) Fluazifop-p-butyl 0       62      62     62 (g/ha) Galium aparine 20       5       24     45 Solanum nigrum 55       0       55     85 ______________________________________

It can be seen from this Table that a synergistic effect is developed between the ioxynil octanoate and the fluazifop-p-butyl.

Four phytosanitary compositions according to the invention were prepared in the form of emulsifiable concentrates of which the respective formulations are shown in Table XI. ______________________________________ Bromoxynil octanoate Pirimiphos- (g/l)       methyl (g/l) ______________________________________ Composition 1 360            75 Composition 2 360           150 Composition 3 320           267 Composition 4 240           400 ______________________________________

Each of these compositions was applied by spraying in quantities of 0.67, 0.67, 0.75 and 1 l/ha, respectively, to plants of Stellaria media and Taraxacum officinale in pots at the 3 to 4 leaf stage in the doses indicated in Table XII.

The herbicidal effect of each composition on the treated species was evaluated after 21 days.

The results of these tests are set out in Table XII.

The "Expected results" and "Results obtained" are as defined in Example 1. __________________________________________________________________________ Results obtained (%) after individual Expected results Results obtained application of the (%) for the (%) for the constituents of the compositions compositions composition    1  2  3  4  1  2  3  4 __________________________________________________________________________ Bromoxynil 240 0  0  0  0  240 240 240 240 240 240 240 240 octanoate (g/ha) Pirimiphos-methyl 0  50 100 200 400 50 100 200 400 50 100 200 400 (g/ha) Stellaria media 10 0  0  0  0  10 10 10 10 25 30 35 25 Taraxacim officinale 55 0  0  0  0  55 55 55 55 75 78 75 80 __________________________________________________________________________

It can be seen from this Table that a synergistic effect is developed between the bromoxynil octanoate end the pirimiphos-methyl.

Eleven phytosanitary compositions according to the invention were prepared in the form of emulsifiable concentrates of which the respective formulations are shown in Table XIII. ______________________________________ Ioxynil octanoate Fenpropimorphe (g/l)     (g/l) ______________________________________ Composition 1 150         470 Composition 2 75         470 Composition 3 40         500 Composition 4 240         375 Composition 5 120         375 Composition 6 80         500 Composition 7 48         600 Composition 8 360         282 Composition 9 240         375 Composition 10 160         500 Composition 11 96         600 ______________________________________ compositions 1, 2 and 3 were applied by spraying in quantities of 0.2, 0. and 0.75 l/ha, respectively, to plants of Solanum nigrum in pots, compositions 1, 2, 8 and 10 were applied by spraying in quantities of 0.2 0.4, 0.33 and 0.75 l/ha, respectively, to plants of Galium aparine in pots, compositions 4, 5, 6 and 7 were applied by spraying in quantities of 0.25 0.5, and 0.75 and 1.25 l/ha, respectively, to plants of Chenopodium album in pots, compositions 4, 8, 9, 10 and 11 were applied by spraying in quantites of 0.25, 0.33, 0.5, 0.75 and 1.25 l/ha, respectively, to plants of Matricari inodora in pots, compositions 8, 9 and 10 were applied by spraying in quantities of 0.33, 0.5, and 0.75 l/ha, respectively, to plants of Taraxacum officinale in pots and compositions 8, 9, 10 and 11 were applied by spraying in quantites of 0.33, 0.5, 0.7 and 1.25 l/ha, respectively, to plants of Daucus carota in pots, at the 3 to 4 leaf stage in the doses indicated in Tables XIV A, XI B and XIV C.

The herbicidal effect of each of the compositions on the treated species was evaluated after 21 days.

The results of these tests are set out in Tables XIV A, XIV B end XIV C.

The "Expected results" and "Results obtained" are as defined in Example 1. ______________________________________ Results obtained (%) after individual application of the constituents of each composition ______________________________________ Ioxynil octanoate (g/ha) 30    60    120  0   0    0    0 Fenpropimorphe (g/ha) 0     0     0    94  187  375  750 Solanum nigrum 30    --    --   0   0    3    -- Galium aparine 20    --    35   3   3    10   -- Chenopodium album --    0     --   0   0    3    5 Matricaria inodora --    30    25   8   5    8    5 Taraxacum officinale --    --    15   0   0    0    -- Daucus carota  --    --    50   0   0    3    5 ______________________________________ __________________________________________________________________________ Expected results (%) for the compositions 1 2  3  4 5  6  7  8  9  10 11 __________________________________________________________________________ Ioxynil octanoate 30 30 30 60 60 60 60 120 120 120 120 (g/ha) Fenpropimorphe (g/ha) 94 187 375 94 187 375 750 94 187 375 750 Solanum nigrum 30 30 32 -- -- -- -- -- -- -- -- Galium aparine 22 22 -- -- -- -- -- 37 -- 42 -- Chenopodium album -- -- -- 0 0  3  5  -- -- -- -- Matricaria inodora -- -- -- 36 -- -- -- 31 29 31 29 Taraxacum officinale -- -- -- -- -- -- -- 15 15 15 -- Daucus carota -- -- -- -- -- -- -- 50 50 52 53 __________________________________________________________________________ __________________________________________________________________________ Results obtained (%) for the compositions 1 2  3  4 5  6  7  8  9  10 11 __________________________________________________________________________ Ioxynil octanoate 30 30 30 60 60 60 60 120 120 120 120 (g/ha) Fenpropimorphe (g/ha) 94 187 375 94 187 375 750 94 187 375 750 Solanum nigrum 45 40 65 -- -- -- -- -- -- -- -- Galium aparine 35 35 -- -- -- -- -- 55 -- 65 -- Chenopodium album -- -- -- 10 45 83 90 -- -- -- -- Matricaria inodora -- -- -- 55 -- -- -- 70 70 80 85 Taraxacum officinale -- -- -- -- -- -- -- 40 35 55 -- Daucus carota -- -- -- -- -- -- -- 65 70 70 75 __________________________________________________________________________

It can be seen from this Table that a synergistic effect is developed between the ioxynil octanoate and the fenpropimorphe.

Eight phytosanitary compositions according to the invention were prepared in the form of emulsifiable concentrates of which the respective formulations are shown in Table XV. ______________________________________ Ioxynil octanoate .lambda.-cyhalothrin (g/l)     (g/l) ______________________________________ Composition 1 240         25 Composition 2 240         50 Composition 3 240         100 Composition 4 120         100 Composition 5 240         12.5 Composition 6 240         25 Composition 7 240         50 Composition 8 240         100 ______________________________________ Compositions 1 to 4 were applied by spraying in quantities of 0.25, 0.25, 0.25 and 0.5 l/ha, respectively, to plants of Chenopodium album, Matricaria inodora and Solanum nigrum in pots, each composition 5 to 8 was applied by spraying in quantity of 0.5 l/ha t plants of Galium aparine in pots, and each of compositions 7 and 8 was applied by spraying in a quantity of 0.5 l/ha to plants of Taraxacum officinale and Veronica sp. in pots at the 3 to 4 leaf stage in the doses indicated in Tables XVI A, XVI B and XVI C.

The herbicidal effect of each composition on the treated species was evaluated after 21 days.

The results of these tests are set out in Tables XVI A, XVI B and XVI C.

The "Expected results" end "Results obtained" are as defined in Example 1. ______________________________________ Results obtained (%) after individual application of the constituents of each composition ______________________________________ Ioxynil octanoate (g/ha) 60    120     0    0     0    0 .lambda.-cyhalothrin (g/ha) 0     0      6.25 12.5  25   50 Chenopodium album 8    --      0    0     0    0 Matricaria inodora 20    --      0    0     0    0 Solanum nigrum 45    --      0    0     0    0 Galium aparine --    25      0    0     0    0 Taraxacum officinale --    25      0    0     0    0 Veronica sp. --    55      0    0     0    0 ______________________________________ ______________________________________ Expected results (%) for the compositions 1    2      3     4   5    6    7    8 ______________________________________ Ioxynil octanoate 60     60     60  60  120  120  120  120 (g/ha) .lambda.-Cyhalothrin 6.25   12.5   25  50  6.25 12.5 25   50 (g/ha) Chenopodium album 8      8      8   8   --   --   --   -- Matricaria inodora 20     20     20  20  --   --   --   -- Solanum nigrum 45     45     45  45  --   --   --   -- Galium aparine --     --     --  --  25   25   25   25 Taraxacum  --     --     --  --  --   --   25   25 officinale Veronica sp. --     --     --  --  --   --   55   55 ______________________________________ ______________________________________ Results obtained (%) for the compositions 1    2      3     4   5    6    7    8 ______________________________________ Ioxynil octanoate 60     60     60  60  120  120  120  120 (g/ha) .lambda.-Cyhalothrin 6.25   12.5   25  50  6.25 12.5 25   50 Chenopodium album 18     20     25  50  --   --   --   -- Matricaria inodora 20     35     45  50  --   --   --   -- Solanum nigrum 60     70     75  85  --   --   --   -- Galium aparine --     --     --  --  35   40   45   45 Taraxacum  --     --     --  --  --   --   50   45 officinale Veronica sp. --     --     --  --  --   --   70   75 ______________________________________

It can be seen from this Table that a synergistic effect is developed between the ioxynil octanoate and the .lambda.-cynalothrin.

Eighteen phytosanitary compositions according to the invention were prepared; seven of these compositions contained only one of the above two constituents and the nine other comprised the two constituents in the form of emulsifiable concentrates of which the respective formulations are shown in Table XVII. ______________________________________ Ioxynil octanoate Sulfosate (g/hl)    (g/hl) ______________________________________ Composition 1   0           60 Composition 2   0          120 Composition 3   0          240 Composition 4   0          480 Composition 5  30           0 Composition 6  30           60 Composition 7  30          120 Composition 8  30          240 Composition 9  60           0 Composition 10 60           60 Composition 11 60          120 Composition 12 60          240 Composition 13 60          480 Composition 14 120          0 Composition 15 120          60 Composition 16 120         120 Composition 17 120         240 Composition 18 120         480 ______________________________________

The above-mentioned compositions were applied by spraying to plants in pots of the following group: Ambrosia, Brassica, Chenopodium, Daucus, Galium, Matricaria, Rumex, Solanum, Stellaria, Taraxacum.

The percentages destruction are observed after 22 days. These results are recorded in Table XVIIA. __________________________________________________________________________ Plants Results (%) obtained with the compositions tested 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 __________________________________________________________________________ Ambrosia 25 30 65 75 25 35 40 45 45 55 90 90 95 65 100 85 85 90 Brassica 10 20 10 30 20 30 35 45 45 60 60 70 70 60 75 80 83 85 Chenopodium 0 20 60 90 75 70 50 60 60 60 60 80 95 65 75 80 90 90 Daucus 5 0 20 78 20 70 83 83 45 80 95 95 200 70 100 100 100 100 Galium 8 10 20 50 20 35 35 50 45 55 60 65 83 55 80 80 80 85 Matricaria 30 35 65 93 25 95 80 98 70 80 95 95 98 70 95 100 100 100 Rumex  55 50 60 80 35 45 55 65 50 70 75 85 90 70 65 80 85 93 Solanum 20 25 60 65 40 40 60 60 78 75 80 70 95 70 95 80 95 85 Stellaria 35 55 70 93 13 55 85 65 20 83 88 90 98 60 55 80 85 95 Taraxacum 60 60 70 85 20 45 50 60 45 88 85 98 100 55 100 95 98 100 Average 25 31 50 74 29 52 57 63 50 71 79 84 92 64 84 86 90 92 __________________________________________________________________________

The excellent properties of the compositions according to the invention result from the examination of this Table.

With respect to two of the above-mentioned plants, i.e. Daucus carota and Matricaria inodora, the "Expected results" (defined in example 1) and "Results obtained" were compared; the recorded results are collected in Table XVII B. ______________________________________ Plants       Compositions applied tested       6     7     8   10  11  12  15  16   17 ______________________________________ Daucus "Expected 25    20  36  48  43  56  --  --   -- carota results" (%) "Results  70    83  83  80  95  95  --  --   -- obtained" (%) Matricaria "Expected 48    51  73  --  --  --  79   81   89 inodora results" (%) "Results  95    80  98  --  --  --  95  100  100 obtained" (%) ______________________________________

The examination of the results collected in this Table shows that it exists an important synergistic effect for Daucus carota and Matricaria inodora. The better synergistic effects are obtained with low doses of the two products.

## Claims

1. A liquid phytosanitary composition to be applied by spraying onto plants consisting essentially of a diluent and of a solution of a liquid active composition, said liquid active composition consisting essentially of an oxynil and at least one active substance liquid at ambient temperature capable of dissolving and maintaining therein the oxynil in the liquid state after application on said plants, the said substance being selected from the group consisting of herbicides, the said herbicides being selected from the group consisting of S-alkyl-thiolcarbamates, chloracetanilides, butamifos, cinmethylin, clethodim, isopropalin, clomazone, dalapon, tebutame, sulfosate, methyl (R)-2-7-(2-chloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyloxy)-2-naphthy loxy! propionate and (+) -tetrahydrofurfuryle (R) -2-4-(6-chloro-quinoxaline-2-yloxy ) phenoxy! propanoate.

2. A liquid phytosanitary composition according to claim 1, containing 48 to 450 grams oxynil per liter.

3. A liquid phytosanitary composition according to one of claims 1 and 2, wherein the S-alkyl-thiolcarbamate is selected from the group consisting of EPTC, pebulate, cycloate, butylate, vernolate, diallate, triallate and molinate.

4. A liquid phytosanitary composition according to one of claims 1 and 2, wherein the chloracetanilide is selected from the group consisting of acetochlore, butachlore, butenachlore, metolachlore and pretilachlore.

5. A process for applying a herbicidal treatment to a plant, comprising spraying on the plant to be treated a quantity sufficient to supply 48 to 450 grams oxynil per hectare of the treated plants, of a liquid phytosanitary active composition consisting essentially of a diluent and of a solution of a liquid active composition, said liquid active composition consisting essentially of an oxynil and at least one substance liquid at ambient temperature capable of dissolving and maintaining therein the oxynil in the liquid state after application on said plants, the said substance being selected from the group consisting of herbicides, the said herbicides being selected from the group comprising S-alkyl-thiolcarbamates, chloracetanilides, butamifos, cinmethylin, clethodim, isopropalin, clomazone, dalapon, tebutame, sulfosate, methyl (R)-2-7-(2-chloro-.alpha.,.alpha.,.alpha.-tri-fluoro-p-tolyloxy)-2-naphth yloxy! propionate and (+)-tetra-hydrofurfuryle (R)-2-4-(6-chloro-quinoxaline-2-yloxy)phenoxy! propanoate.