GB2340397A

GB2340397A - Synergistic herbicidal compositions

Info

Publication number: GB2340397A
Application number: GB9918964A
Authority: GB
Inventors: Hisayuki Hoshi
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 1998-08-12
Filing date: 1999-08-11
Publication date: 2000-02-23
Anticipated expiration: 2019-08-11
Also published as: FR2782246A1; DE19937814A1; JP2000063215A; GB9918964D0; GB2340397B

Abstract

Herbicidal compositions comprise a 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl C<SB>1-5</SB> non-cyclic hydrocarbyl ether and isopropyl 5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-chloro-4-fluorobenzoate as synergistic active ingredients.

Description

2340397 HERBICIDAL COMPOSITIONS

Field of the Invention

The instant invention relates to herbicidal compositions, methods of controlling weeds, and uses of compounds for a herbicide.

Background of the Invention

At present, there are many types of weeds that can be controlled by utilizing herbicidal compositions. There also are weeds that additionally occupy an extended growing season. For these reasons, numerous herbicides are commercially available and are widely used to control such weeds. However, herbicidal compositions that do not cause phytotoxicity to crops and which posses a high herbicidal activity and broad herbicidal spectrum are desirous.

2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cl-5 non-cyclic hydrocarbyl ether compounds and isopropyl 5-[4-bromo-1methyl-5 (trifluoromethyl)- I H-pyrazol-3-yll-2-chloro-4-fluorobenzoate are known to posses a herbicidal activity.

Summary of the Invention

The instant invention provides herbicidal compositions possessing a broad herbicidal spectrum. In this regard, the herbicidal compositions of the instant invention can control weeds which typically outbreak in cultivated or non- cultivated fields, and

1 more particularly weeds which are usually problematic in wheat, barley, rye, or oats fields, or the like.

The instant invention further provides herbicidal compositions possessing an excellent herbicidal activity. As such, the herbicidal compositions of the instant invention can be herbicidally active at a low dosage thereof The compositions of the instant invention can also be herbicidally active by providing a synergistic herbicidal activity which is unexpectedly superior to that exhibited from separately utilizing a 2chloro-4-fluoro-5(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cl-5 noncyclic hydrocarbyl ether compound or isopropyl 5-[4-bromo-1-methyl-5(trifluoromethyl)- 1 H-pyrazol-3-yl]-2-chloro-4-fluorobenzoate as an active herbicidal ingredient of a composition.

Furthermore, the instant invention provides methods of controlling weeds which typically outbreak in cultivated or non-cultivated fields. Preferably, such methods of the instant invention use the inventive herbicidal compositions on the weeds or on the soil of said fields.

In order to fulfill such properties, the instant invention provides a herbicidal composition typically comprising a 2-chloro-4-fluoro-5-(4methyl-5-trifluoromethyl3-pyridazinon-2-y1) phenyl Cl-s non-cyclic hydrocarbyl ether compound and isopropyl 5 - [4-bromo- 1 -methyl- 5 -(tri fluoromethyl)- 1 H-pyrazol-3 -yl]-2 -chloro-4- fluorobenzoate, as well as a method of utilizing said compounds. Further, the instant invention also provides herbicidal uses of 2-chloro-4-fluoro5-(4-methyl-5trifluoromethyl-3-pyridazinon-2-yl) phenyl C1-5 non-cyclic hydrocarbyl ether compound and isopropyl 5 - [4-bromo- 1 -methyl -5(trifluoromethyl)- 1 H-pyrazol-3 -yll 2-chloro-4-fluorobenzoate.

2 Detailed Description of the Invention

Hereinafter, isopropyl 5-[4-bromo-1-methyl-5-(trifluoromethyl)-IH-pyrazol3- yl]-2-chloro-4-fluorobenzoate is referred to as "fluazolate". Fluazolate is a compound disclosed in WO 92/06962.

A herbicidal composition of the instant invention typically comprises a 2 chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cps non cyclic hydrocarbyl ether compound and fluazolate. A weight to weight ratio of the 2 chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cl-s non cyclic hydrocarbyl ether compound to fluazolate, in the herbicidal compositions of the instant invention, typically depends on the type of objective weed to be controlled by using said herbicidal compositions, and the situation and condition of utilizing said herbicidal compositions. Even if so, it is preferable in the herbicidal compositions of the instant invention to have the weight to weight ratio of the 2-chloro- 4-fluoro-5-(4 methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl C1-5 non-cyclic hydrocarbyl ether compound to fluazolate at about from L0.05 to 1:500.

2-chloro-4-fluoro-5-(4-methyl-S-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cl-s non-cyclic hydrocarbyl ether compounds which are utilized in the inventive herbicidal compositions are typically encompassed by the following formula (I):

(1) F 0 CH3 Y cl N CF3 0-1- X _j N 0 R 3 wherein R represents a Cl-5 non-cyclic hydrocarbyl group. Preferably, said 2-chloro-4fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cl-s non-cyclic hydrocarbyl ether compounds have R in formula (1) represent a C1-5 alkyl, C2-5 alkenyl, C2-s alkynyl group, or the like, and most preferably, a group provided in the following Table 1.

TABLE 1

R Compound Code 2-propynyl A 1 -methyl-2-propynyl B allyl c 1-methylaily] D ethyl E isopropyl F The compound code provides letter codes which are used herein to designate a 2 chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cl-s non cyclic hydrocarbyl ether compound which comprises the corresponding R group.

2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl Cl-s non cyclic hydrocarbyl ether compounds which are utilized in the instant invention may be produced according to the disclosure of WO 97/07104.

The herbicidal compositions of the instant invention are typically formulated as emulsifiable concentrates, wettable powders, suspensible concentrates, granules, or the like, but are not limited thereto. The formulations of the inventive herbicidal compositions typically comprise the 2-chloro-4-fluoro-5-(4-methyl-5- trifluoromethyl- 3-pyridazinon-2-yl) phenyl Cl-s non-cyclic hydrocarbyl ether compound and fluazolate, in a combined amount of from about 0.5 to 90% by weight, and preferably about 1 to 80% by weight, wherein said weight percentages are based on the total weight of the provided herbicidal composition. Further, such formulations of the inventive herbicidal 4 compositions can also contain a solid or liquid carrier therein, and may further contain a surfactant or other formulation auxiliary which is useful in producing one of the inventive herbicidal compositions. In such cases, the formulations of the inventive compositions may be formulated by mixing the above components. For example, a herbicidal composition may be produced by formulating the 2-chloro4- fluoro-5-(4methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl CI-5 non- cyclic hydrocarbyl ether compound into a suitable formulation, formulating fluazolate into a second suitable formulation, and mixing said 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3pyridazinon-2-yl) phenoxyacetate ester compound formulation and said second formulation together.

Examples of solid carriers which can be utilized in the herbicidal compositions of the instant invention usually include small granules or powders. Preferably, such small granules or powders which are utilized in the herbicidal compositions of the instant invention include clays such as kaolinite, diatomaceous earth, synthetic hydrated silicon oxide, Fubasami clay, bentonite and acid clay, talc, other inorganic minerals such as sericite, powdered quartz, powdered sulfur, activated carbon and calcium carbonate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride and urea, or the like.

Examples of liquid carriers which can be utilized in the herbicidal compositions of the instant invention usually include water, alcohols such as methanol and ethanol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aromatic hydrocarbons such as toluene, xylene, ethylbenzene and methylnaphthalene, nonaromatic hydrocarbons such as hexane, cyclohexane and kerosine, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and isobutylonitrile, ethers such as dioxane and diisopropyl ether, acid amides such as dimethylfonnamide and dimethylacetamide, halogenated hydrocarbons such as dichloroethane and trichloroethylene, and the like, but are not limited thereto.

Examples of surfactants which maybe utilized in the herbicidal compositions of the instant invention usually include alkylsulfate esters, alkylsulfonate salts, alkylarylsulfonate salts, alkyl aryl ethers and polyoxyethylene derivatives thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives, and the like, but are not limited thereto.

Examples of the other formulation auxiliaries which may be utilized in the herbicidal compositions of the instant invention usually include adhesive and/or dispersing agents, stabilizers, and the like, but are not limited thereto. More specific examples of said adhesive and/or dispersing agents usually include casein, gelatin, lignm derivatives, bentonite, polysaccharides such as powdered starch, gum arabic, cellulose derivatives and alginic acid, synthetic water-soluble polymers such as polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acid, and the like. More specific examples of the stabilizers usually include PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4methyoxyphenol and/or 3-tert-butyl-4-methyoxyphenol), vegetable oils, mineral oils, fatty acids, fatty acid esters, and the like.

If so desired, the herbicidal compositions of the instant invention may further comprise other well known herbicides, so that the herbicidal activity thereof is enhanced. Further, the herbicidal compositions of the instant invention may also optionally comprise insecticides, acaricides, bacteriocides, fungicides, plant growth regulators, fertilizers, safeners, soil conditioners, and the like, if additional functions are desirous therefor.

6 A herbicidal method of the instant invention typically comprises utilizing a 2chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon2-yl) phenyl C1-5 noncyclic hydrocarbyl ether compound and fluazolate on the objective weed(s) or on soil which is in a locus of where a control of a weed or weeds is desirous. Preferably, the methods of the instant invention utilize such compounds by applying the inventive herbicidal compositions to such locations.

The herbicidal effect resulting from utilizing or applying a 2-chloro-4fluoro5-(4-methyl-5-tdfiuoromethyl-3-pyTidazinon-2-yl) phenyl Cl-5 noncyclic hydrocarbyl ether compound and fluazolate in the methods of the instant invention typically depends on the amount of the utilized inventive composition, the time of utilization, weather condition(s), formulation form(s), location(s) of utilization, objective weed(s) or the like, or a combination thereof Further, when such compounds are utilized to benefit crops, the combined amount of said compounds utilized in the inventive methods may also depend on the type of objective crop that benefits from the utilization thereof is Even if so, the 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3- pyridazinon-2-yl) phenyl Cl-s non-cyclic hydrocarbyl ether compound and fluazolate are preferably utilized in the inventive methods at a dosage of from about 1 to 1 000g per 1 ha.

Such utilization of the inventive herbicidal compositions in the methods of the instant invention can be in various types of locations. Since the herbicidal compositions of the instant invention possess a herbicidal activity against various types of weeds, the methods of the instant invention can utilize the inventive herbicidal compositions in non-cultivated fields. Examples of said non-cultivated fields include training facilities, open fields, woodlands, boundaries of railroad tracks, and the like. Further, since the inventive herbicidal compositions additionally possess a selectivity which selectively controls weeds without causing phytotoxicity to crops, the methods 7 of the instant invention can also utilize the inventive herbicidal compositions in cultivated fields. Examples of said cultivated fields include the standard cultivated field, a cultivated field which is non- tillaged, horticultural fields such as orchards, and the like. However, such cases in which the methods of the instant invention utilize the inventive herbicidal compositions in cultivated fields, should not cause problematic phytotoxicity to crops, when crops are present, and especially to crops such as barleys, wheats, ryes, oats, corns or the like.

It should be noted that the methods of the instant invention are not limited to such locations, since it is well known that weeds may emerge in additional locations in which the inventive herbicidal compositions would be applicable.

Examples of the weeds controllable with the herbicidal methods of the instant invention include Dicotyledoneae plants such as Common chickweed (Stellaria media), Cleavers (Galium aparine), Persian speedwell (Veronica persica), Ivyleaf speedwell (Veronica hederifolia), Field pansy (Viola arvensis), Wild pansy (Viola tricolor),

Purple deadnettle (Lamium purpureum), Henbit (Lamium amplexicaure), Shepherdspurse (Capsella bursa-pastoris), Annual sowthistle (Sonchus oleraceus), Corn poppy (Papaver rhoeas), Scentless chamomile (Matricaria inodora), Wild chamomile (Matricaria chamomilla), Wild mustard (Sinapsis arvensis), Field forgetme-not (Myosotis arvensis), Wild buckwheat (Polygonm convolvulus), Common lambsquarters (Chenopodium album), Kochia (Kochia scoparia), Smooth pigweed (Amaranthus hybridus) and Redroot pigweed (Amaranthus retrofexus), Monocotyledoneae such as Barnyardgrass (Echinochloa crus-galli), Green foxtail (Setaria viridis), Giant foxtail (Setariajaveri), Annual bluegrass (Poa annua), Blackgrass (Alopecurus myosuroides), Italian ryegrass (Lolium mulliflorum), Downy brome(Bromus tectorum) and Wild oat (Avenafatua), and the like.

8 The methods of the instant invention may optionally utilize a formulated inventive herbicidal composition by diluting the provided formulation of the inventive herbicidal composition with water. For example, the methods of the instant invention may dilute emulsifiable concentrates, wettable powders, suspensible concentrates or the like, of the inventive herbicidal compositions by diluting such formulations with 100 to 1000 liters of water, in order to treat I ha of a locus in which a control of weeds is desirous.

Examples

Hereinafter, the instant invention is further described by providing the following examples, but it is to be understood that the instant invention is not limited by the following examples.

Formulation Example I One (1) part by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 25 parts by weight of fluazolate, 3 parts by weight of calcium ligninsulfonate, 2 parts by weight of sodium laurylsulfate and 69 parts by weight of synthetic hydrated silicon oxide are well pulverized and mixed, to achieve a wettable powder formulation of the instant invention.

Formulation Example 2 Ten (10) parts by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 40 parts by weight of fluazolate, 3 parts by weight of calcium ligninsulfonate, 2 parts by weight of sodium laurylsulfate and 45 9 parts by weight of synthetic hydrated silicon oxide are well pulverized and mixed, to achieve a wettable powder formulation of the instant invention.

Formulation Example 3 One-tenth (0. 1) part by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 50 parts by weight of fluazolate, 3 parts by weight of calcium ligninsulfonate, 2 parts by weight of sodium laurylsulfate and 44.9 parts by weight of synthetic hydrated silicon oxide are well pulverized and mixed, to achieve a wettable powder formulation of the instant invention.

Formulation Example 4 One (1) part by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 50 parts by weight of fluazolate, 3 parts by weight of polyoxyethylene sorbitan monolaurate, 3 parts by weight of CMC (carboxyinethyl cellulose) and 43 parts by weight of water are mixed and pulverized until the particle diameter thereof is 5 microns or less, to achieve a suspensible concentrate formulation of the instant invention.

Formulation Example 5 One-tenth (0. 1) part by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 30 parts by weight of fluazolate, 3 parts by weight of polyoxyethylene sorbitan monolaurate, 3 parts by weight of CMC (carboxymethyl cellulose) and 63.9 parts by weight of water are mixed and pulverized until the particle diameter thereof is 5 microns or less, to achieve a suspensible concentrate formulation of the instant invention.

Formulation Example 6 Four (4) parts by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 16 parts by weight of fluazolate, 3 parts by weight of polyoxyethylene sorbitan monolaurate, 3 parts by weight of CMC (carboxyinethyl cellulose) and 74 parts by weight of water are mixed and pulverized until the particle diameter thereof is 5 microns or less, to achieve a suspensible concentrate formulation of the instant invention.

Formulation Example 7 One (1) part by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 9 parts by weight of fluazolate, 14 parts by weight of polyoxyethylenest)"I phenyl ether, 6 parts by weight of calcium dodecylbenzenesulfonate, 3 5 parts by weight of xylene, and 3 5 parts by weight of cyclohexane are well mixed, to achieve an emulsiflable concentrate forTnulation of the instant invention.

Formulation Example 8 One (1) part by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, 7 parts by weight of fluazolate, 2 parts by weight of synthetic hydrated silicon oxide, 2 parts by weight of calcium lignin sulfonate, 30 parts by weight of bentonite and 60 parts by weight of kaolin clay, are well pulverized and mixed, to achieve a mixture. Water is added to the mixture and the mixture is then granulation dried, to achieve a granule formulation of the instant invention.

Formulation Example 9 Into 40 parts by weight of an aqueous solution of 10% polyvinyl alcohol, 0. 5 parts by weight of Compound A, Compound B, Compound C, Compound D, Compound E, or Compound F, and 4.5 parts by weight of fluazolate are added thereto, and are emulsification dispersed in a homogenizer until the average particle diameter thereof is 10 micrometers or less. Subsequently, 55 parts by weight of water is added thereto, to achieve a concentrated emulsion of the instant invention.

Standards of scores The herbicidal activity of a herbicidal composition and the pbytotoxicity caused thereby were evaluated in the following test examples at I I levels, using the indices of 0 to 10, i.e., shown by"O", "1", "2", "Y', 'W', "5", "6", "7", "8", 6499% or"10". Said indices provide numerical scores that ascend with the level of herbicidal activity or phytotoxicity. In scoring the herbicidal activity of a provided herbicidal composition, a score of "10" means that the test plants died completely or their germination or growth were completely inhibited and a score of "0" means that there was no or little difference in the degree of germination or growth between treated plants to untreated plants at the time of examination. Similarly, in scoring the phytotoxicity of a provided herbicidal composition, a low score means that the phytotoxicity is at a level which is practically not a problem, and a high score means that the phytotoxicity is at an unacceptable level.

Test Example I Plastic pots in which the bottom surface thereof had an area of 246cm 2 and which had a depth of 12.5cm, were filled with upland soil and seeded with wheat, 12 Scentless chamomile (Matricaria inodora), and Persian speedwell (Veronica persica), respectively. The plastic pots containing wheat were given 15 days to grow in a greenhouse. The plastic pots containing Scentless chamomile and the plastic pots containing Persian speedwell were given 22 days to grow in a greenhouse.

An emulsifiable concentrate of fluazolate was formulated by mixing 20 parts by weight of fluazolate, with 3 parts by weight of polyoxyethylene styryl phenyl ether, 2 parts by weight of calcium dodecylbenzenesulfonate and 75 parts by weight of xylene.

A suspensible concentrate of Compound A was formulated by mixing 5 parts by weight of Compound A, with 2 parts by weight of alkylaryl ether, 1 part by weight of xanthan gum, 10 parts by weight of propylene glycol, 1 part by weight of a silicon-type emulsion and 81 parts of water, and then wet pulverizing the achieved mixture until the particle diameter thereof was 2 microns or less.

The emulsifiable concentrate of fluazolate, the suspensible concentrate of Compound A, a mixture containing the emulsifiable concentrate of fluazolate and the is suspensible concentrate of Compound A were diluted with water. The resulting diluted compositions are shown in Table 2. Each of the diluted compositions was then uniformly sprayed, respectively, onto the wheat, Scentless chamomile, and Persian speedwell by using a small sprayer. After such applications of said compositions, the wheat, the Scentless chamomile, and the Persian speedwell were placed in a greenhouse for 18 days. The herbicidal activity of said compositions (which relates to the Scentless chamomile and Persian speedwell), as well as the phytotoxicity of said compositions (which relates to the wheat), were then examined in accordance to the above standards of scores. The results are shown in Table 2.

13 Table 2

Dosage Phytotoxicity Herbicidal Activity Tested Compositions (g/1 ha) Wheat Scentless chamomile Persian speedwell Compound A 1.25 0 3 2 Fluazolate 5 0 2 5 ound A + fluazolate 1.25+5 1 9 9 Test Example 2 5 Plastic pots in which the bottom surface thereof had an area of 246cm 2 and which had a depth of 14cm were each filled with upland soil and seeded with wheat and Wild oat (Avenafatua), to achieve soil samples. An emulsifiable concentrate of fluazolate was formulated by mixing 10 parts by weight of fluazolate, with 3 parts by weight of polyoxyethylene styryl phenyl ether, 2 10 parts by weight of calcium dodecylbenzenesulfonate and 85 parts by weight of xylene. A suspensible concentrate of Compound A was formulated by mixing 5 parts by weight of Compound A, with 2 parts by weight of alkylaryl ether, I part by weight of xanthan gum, 10 parts by weight of propylene glycol, I part by weight of a silicon-type emulsion and 81 parts by weight of water, and then wet pulverizing the achieved 15 mixture until the particle diameter thereof was 2 microns or less.

The emulsifiable concentrate of fluazolate, the suspensible concentrate of Compound A, a mixture containing the emulsifiable concentrate of fluazolate and the suspensible concentrate of Compound A were diluted with water. The resulting diluted compositions are shown in Table 3. Each of the diluted compositions was then uniformly sprayed onto said soil samples containing the wheat and the Wild oat by using a small sprayer. After each of the soil samples was sprayed with one of the provided compositions, said soil samples containing the wheat and the Wild oat were 14 placed in a greenhouse for 27 days. The herbicidal activity of said compositions (which relates to the Wild oat), as well as the phytotoxicity of said compositions (which relates to the wheat), were then examined in accordance to the above standards of scores. The results are shown in Table 3.

Table 3

Test Example 3 Plastic pots in which the bottom surface thereof had an area of 246cm 2 and which had a depth of 14cm were each filled with upland soil and seeded with wheat and Cleavers (Galium aparine), to achieve soil samples.

An emulsifiable concentrate of fluazolate was formulated by mixing 10 parts by weight of fluazolate, with 3 parts by weight of polyoxyethylene styryl phenyl ether, 2 parts by weight of calcium dodecylbenzenesulfonate and 85 parts by weight of xylene.

A suspensible concentrate of Compound A was formulated by mixing 5 parts by weight of Compound A, with 2 parts by weight of alkylaryl ether, I part by weight of xanthan gum, 10 parts by weight of propylene glycol, I part by weight of a silicon-type emulsion and 81 parts by weight of water, and then wet pulverizing the achieved mixture until the particle diameter thereof was 2 microns or less.

The emulsifiable concentrate of fluazolate, the suspensible concentrate of Compound A, a mixture containing the emulsifiable concentrate of fluazolate and the Tested Compounds Dosage Phytotoxicity Herbicidal activity (g/1 ha) Wheat Wild Oat Compound A 5 0 2 Fluazolate 44 0 3 Compound A + Fluazolate 5+44 1 7 suspensible concentrate of Compound A were diluted with water. The resulting diluted compositions are shown in Table 4. Each of the diluted compositions was then uniformly sprayed onto said soil samples containing the wheat and Cleavers by using a small sprayer. After each of the soil samples was sprayed with one of the provided compositions, said soil samples containing the wheat and Cleavers were placed in a greenhouse for 27 days. The herbicidal activity of said compositions (which relates to the Cleavers), as well as the phytotoxicity of said compositions (which relates to the wheat), were then examined in accordance to the above standards of scores. The results are shown in Table 4.

Table 4

Tested Compounds Dosage Phytotoxicity Herbicidal activity (g/1 ha) Wheat Cleavers Compound A 11 0 4 Fluazolate 22 0 0 Compound A + Fluazolate 11 +22 1 8 The above scores that result from Test examples 1, 2 and 3 evidence that the herbicidal compositions of the instant invention provide a superior and synergistic herbicidal activity, as well as a safety, which relate to crops, by averting phytotoxicity thereto.

16

Claims

1. A herbicidal composition comprising as active ingredients:

(i) a 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) 5 phenyl C,-, non-cyclic hydrocarbyl ether and (ii) isopropyl 5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)2chloro-4-fluorobenzoate.

2. A composition according to claim 1, wherein the weight to weight ratio of the 102-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl C,-, non-cyclic hydrocarbyl ether to the isopropyl 5-(4-bromo-1-methyl5trifluoromethyl-IH-pyrazol-3-yl)-2-chloro-4-fluorobenzo ate is from L0. 05 to 1:500.

3. A method for controlling weeds at a locus comprising applying to the weeds or to the locus an effective amount of a 2-chloro-4-fluoro-5-(4-methyl-5- trifluoromethyl-3-pyridazinon-2-yl) phenyl C,-, non-cyclic hydrocarbyl ether and isopropyl 5-(4-bromo-1-methyl-5-trifluoromethyl-IH-pyrazol-3yl)-2-chloro-4fluorobenzoate.

4. A method according to claim 3, which is conducted in a wheat, barley, rye or oats field.

5. A method according to claim 3 or 4, wherein the application rate of the 2chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl C,., non- cyclic hydrocarbyl ether and the isopropyl 5-(4-bromo-1-methyl-5trifluoromethylIH-pyrazol-3-yl)-2-chloro-4-fluorobenzoate is from 1 to 1000g per 1 ha.

6. Use of a 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon2yl) phenyl C 1-5 non-cyclic hydrocarbyl ether and isopropyl 5-(4-bromo- 1 -methyl-5- trifluoromethyl- 1 H-pyrazol-3-yl)-2-chloro-4-fluorobenzoate together as a herbicide.

7. A herbicidal product comprising:

(i) a 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl) phenyl C,., non-cyclic hydrocarbyl ether and (ii) isopropyl 5-(4-bromo-1-methyl-5-trifluoromethyl-IH-pyrazol-3-yl)-2chloro-4-fluorobenzoate, for simultaneous, separate or sequential use in controlling weeds.

8. A composition according to claim 1 substantially as hereinbefore described in any one of Formulation Examples 1 to

9. 10 9. A method according to claim 3 substantially as hereinbefore described in any one of Test Examples 1 to 3.

10. Use according to claim 6 substantially as hereinbefore described in any one of Test Examples 1 to 3.