Herbicidal composition and weeding method

Abstract: The present invention relates to a herbicidal composition containing as active ingredients at least one organophosphorus compound and 3-substituted phenylpyrazole derivative of the general formula (I): [wherein R is -Y¹R³, -Y²CH(R⁴)CO-OR⁵, -COOCH(R⁴)CO-Y¹R⁵ or -COOR⁶ (R³, R⁴, R⁵, R⁶, Y¹ and Y² are specified groups), R¹ is a lower alkyl group, R² is a hydrogen atom, a lower alkyl group or a lower haloalkyl group, X¹ and X², which may be the same or different, are halogen atoms, Y is -O-, -S-, -SO- or -SO₂-, and n is zero or 1]; and a weeding method using said composition.

Description: This invention relates to a herbicidal composition containing as active ingredients at least one organophosphorous compound, selected from the group consisting of N-(phosphonomethyl)glycine or a salt thereof, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or a salt thereof, and 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or a salt thereof, and a 3-substituted phenylpyrazole derivative represented by the general formula (I): wherein R is -Y 1 R 3 (wherein R 3 is a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group, and Y 1 is -O- or -S-), -Y 2 CH(R 4 )CO-OR 5 (wherein R 4 is a hydrogen atom or a lower alkyl group, R 5 is a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group, and Y 2 is -O-, -S- or -NH-), -COOCH(R 4 )CO-Y 1 R 5 (wherein R 4 , R 5 and Y 1 are as defined above), or -COOR 6 (wherein R 6 is a lower alkyl group, a lower alkenyl group or a lower alkynyl group), R 1 is a lower alkyl group, R 2 is a hydrogen atom, a lower alkyl group or a lower haloalkyl group, X 1 and X 2 , which may be the same or different, are halogen atoms, Y is -O-, -S-, -SO- or -SO 2 -, and n is zero or 1; and a weeding method using said composition. Furthermore, this invention relates to a herbicidal composition comprising as active ingredients at least one organophosphorous compound, selected from the group consisting of N-(phosphonomethyl)glycine or a salt thereof, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or a salt thereof, and 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or a salt thereof, and a 3-substituted phenylpyrazole derivative represented by the general formula (I): wherein R 1 is CH 3 , R is OCH 2 CH 2 = CH 2 , R 2 is CHF 2 , X 1 and X 2 are each Cl, Y is NH and n is 1, and to a herbicidal composition comprising as active ingredients at least one organophosphorous compound, selected from the group consisting of N-(phosphonomethyl)glycine or a salt thereof, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or a salt thereof, and 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or a salt thereof, and a 3-substituted phenylpyrazole derivative represented by the general formula (I): wherein R 1 is CH 3 , R is OCH 2 C ≡ CH, R 2 is CHF 2 , X 1 and X 2 are each Cl, Y is NH and n is 1, and to weeding methods using said compositions. The 3-substituted phenylpyrazole derivative of the general formula (I) is a compound described in JP-A-3163063, corresponding to EP-A-361114,and JP-A-4211065 and were found to be useful as a herbicide. JP-A-4059706 and JP-A-3246204 disclose herbicidal compositions comprising the following 3-substituted phenylpyrazole derivative, wherein R is a lower alkyl group and X is halogen, in combination with a sulphonylurea, phenylurea or phenoxy-fatty acid compound as active ingredients. These compositions are especially used for eradicating weeds from cereals, such as wheat or barley. The organophosphorus compound used in the present invention is a well-known herbicide, for example, N-(phosphonomethyl)glycine or a salt thereof which are described in JP-A-4739538 and JP-A-5795994, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine described in Japanese Patent Post-examined Publication No. 57-26564, or 4-[hydroxy(methyl)-phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine described in Japanese Patent Post-examined Publication No. 59-23282. The organophosphorus compounds are foliage applied herbicides widely used as non-selective herbicides, which may also be combined with other herbicidal compounds, such as 3-chloro-2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5,6,7-tetrahydro-2H-indazole, as disclosed in EP-A-232504, certain oxazolidinedione derivatives, as disclosed in EP-A-350880, or oxyfluorofen type herbidcides as disclosed in EP-A-143547. However, the organophosphorus compounds exhibit initial effect slowly and are not sufficiently effective against herbaceous weeds in developed leaf stage or reproduction stage. Therefore, there is an eager desire for the advent of a herbicide which exhibits herbicidal effect soon after application and has a sufficient herbicidal effect also on the herbaceous weeds in developed leaf stage or reproductive stage. For solving these problems the present invention providers a herbicidal composition comprising as active ingredients at least one organophosphorus compound selected from the group consisting of N-(phosphonomethyl)glycine or a salt thereof, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or a salt thereof, and 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or a salt thereof and a 3-substituted phenylpyrazole derivative of the above general formula (I), wherein the organophosphorus compound is contained in an amount of 0.01 to 1,000 parts by weight per part by weight of the 3-substituted phenylpyrazole derivative of the general formula (I). This composition exhibits fast-acting properties and a wide weed control spectrum and moreover brings about an excellent synergistic effect at a dosage required when each of the compounds is used alone. Further, the present invention provides a weeding method comprising applying the herbicidal composition of the present invention in a dosage chosen in the range of 1 g to 5 kg (in terms of the active ingredients of the composition) per 10 area for controlling indesirable weeds. In the following the drawings are briefly described. Fig. 1 is a graph showing the synergistic effect of a herbicidal composition (containing compound 19 and compound B) of the present invention by isobole analysis. Fig. 2 is a graph showing the synergistic effect of a herbicidal composition (containing compound 19 and compound C) of the present invention by isobole analysis. The present invention is now described in more detail. Examples of the compound of the general formula (I) are given in Table 1. The herbicidal organophosphorus compound is according do the present invention, selected from the group consisting of N-(phosphonomethyl)glycine or salts thereof, such as the N-(phosphonomethyl)glycine isopropylammonium salt (hereinafter referred to as "compound A") or the N-(phosphonomethyl)glycine trimethyl-sulfonium salt (hereinafter referred to as "compound B"); 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or salts thereof, such as the 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine ammonium salt (hereinafter referred to as "compound C"); 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or salts thereof, such as the 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine sodium salt (hereinafter referred to as "compound D"). For applying the herbicidal composition of the present invention, it may be prepared into suitable forms according to an ordinary manner for preparation of agrochemicals, depending on purposes. For example, said composition is blended with one or more materials selected from the group consisting of solid carriers, liquid carriers and surfactants, and optionally adjuvants; and prepared into a preparation form, such as water dispersible granules, a wettable powder, dust, a suspension concentrate or a soluble concentrate. The active ingredients of the herbicidal composition of the present invention are blended, depending on the type of formulation, in the following range: the proportion of organophosphorus compound is 0.01 to 1,000 parts by weight, preferably 1 to 500 parts by weight, per part by weight of 3-substituted phenylpyrazole derivative of the general formula (I). The herbicidal composition of the present invention is useful as a non-selective herbicidal composition. The composition has fast-acting property which the organophosphorus compound does not have, by virtue of the simultaneous use of the 3-substituted phenylpyrazole derivative and the organophosphorus compound, and moreover the composition permits reduction of the dosage because the simultaneous use brings about a synergistic effect which cannot be expected when each of the two agents is used alone. The herbicidal composition of the present invention is useful particularly as a non-selective herbicide. The composition can be used, for example, for controlling weeds emerging in non-crop lands, such as roads, building sites, railbeds, parks and playgrounds, and ground covering weeds in orchards, managed forests, forests or tame forests. Furthermore, the composition can be used also as a weed management agent for levees of paddy fields and a clean up herbicide for fallow fields, and upland fields before planting. The composition is effective in controlling, for example, dicotyledons such as asiatic dayflower (Commelina communis), tufted knotweed (Polygonum longisetum), sweet scabious (Erigeron annuus), horseweed (Erigeron canadensis), shepherd's purse (Capsella bursa-pastoris), pale persicaria (Polygonum lapathifolium), livid amaranth (Amaranthus lividus), cudweed (Gnaphalium affine), three seeded copper leaf (Acalypha australis), slender amaranth (Amaranthus varidis) and chickweed (Stellaria media); gramineous weeds, such as large crabgrass (Digitaria adscendens), barnyard grass (Echinochloa crus-galli), annual bluegrass (Poa annua) and water foxtail (Alopecurus aequalis); and perennial weeds, such as curly dock (Rumex juponicus), mugwort (Artemisia princeps), field horsetail (Equisetum arvense), asiatic plantain (Plantago asiatica), philadelphia fleabane (Erigeron philadelphicus), dandelion (Taraxacum officinale), cogon grass (Imperata cylindrica), eulalia grass (Miscanthus sinensis) and sorrel vine (Cayratia japonica). The present invention is applicable not only to the above places and weeds but also to all places and objective weeds for controlling undesirable weeds. Although the herbicidal composition of the present invention is applied preferably during the early-post emergence or vegetative growth stage of weeds, its application time is not limited to these periods. The dosage of the herbicidal composition of the present invention may be chosen in the range of 1 to 5,000 g (in terms of the active ingredients) per 10 ares. EXAMPLES Typical examples of the present invention are described below. In the examples, parts are all by weight. Example 1 Compound 19 0.2 part Compound C 18.5 parts Genapol® LRD 20.0 parts Glauber's salt 20.0 parts Clay 16.3 parts Bentonite 10.0 parts Hydrated silicic acid 10.0 parts Calcium ligninsulfonate 5.0 parts Total 100.0 parts Granular wettable powder was prepared by mixing the predetermined amounts of compound 19, compound C, Glauber's salt, clay, bentonite and hydrated silicic acid uniformly, placing the resulting mixed powder in a fluidized-bed granulator, and spraying the mixed powder with an aqueous solution containing the predetermined amounts of Genapol® LRD and calcium ligninsulfonate, followed by granulation and drying. Example 2 Compound 19 0.2 part Compound C 18.5 parts Pluronic® L-64 5.0 parts Sodium alkylbenzensulfonate 2.0 parts Methylnaphtalene 10.0 parts Water 64.3 parts Total 100.0 parts An aqueous suspension concentrate was prepared by mixing the predetermined amounts of compound 19 and methylnaphthalene to obtain a solution, adding compound C, Pluronic® L-64, Sodium alkylbenzensulfonate and water to the solution, and mixing them uniformly by means of a high-speed agitator. Example 3 Compound 19 0.2 part Compound B 38.0 parts Pluronic® L-64 5.0 parts Sodium alkylbenzenesulfonate 2.0 parts Methylnaphtalene 10.0 parts Water 44.8 parts Total 100.0 parts An aqueous suspension concentrate was prepared by mixing the predetermined amounts of compound 19 and methylnaphthalene to obtain a solution, adding compound B, Pluronic® L-64, sodium alkylbenzenesulfonate and water to the solution, and mixing them uniformly by means of a high-speed agitator. Example 4 Compound 19 0.2 part Compound C 18.5 parts Hitenol No. 8 (trade name) 3.0 parts Calcium ligninsulfonate 3.0 parts Carplex #80 (trade name) 5.0 parts Clay 70.3 parts Total 100.0 parts A wettable powder was prepared by mixing uniformly and grinding the above ingredients. Example 5 Compound 19 0.2 part Compound B 38.0 parts Hitenol No. 8 (trade name) 3.0 parts Calcium ligninsulfonate 3.0 parts Carplex #80 (trade name) 5.0 parts Clay 50.8 parts Total 100.0 parts A wettable powder was prepared by mixing uniformly and grinding the above ingredients. Test Example 1 Synergistic-effect test on compositions of the present invention A pot with a diameter of 12 cm and a height of 11 cm was filled with upland soil (sandy loam) and seeded with barnyard grass ( Echinochloa crus-galli ) so as to adjust the depth of covering soil to 0.5 cm, and the barnyard grass was grown in a greenhouse. When the barnyard grass was grown to a leaf stage of 3 and a height of 10 cm in a test co-using compound B or a leaf stage of 5 and a height of 15 cm in a test co-using compound C, a predetermined amount of each herbicidal composition of the present invention was diluted with water and the dilution was sprayed from above uniformly on the whole surfaces of the stem and leaves in a spray volume of 1,000 liters per hectare by the use of a small-sized sprayer. On the 10th day after the spraying, the degree of growth of the above-ground part of surviving barnyard grass plants was visually judged in the range of zero (ineffective) to 100 (complete kill) by comparison with that on the untreated plot. The test results obtained in the composition of compound 19 and B or compound 19 and C are shown in Table 2 and Table 3, respectively. The above results are shown in the drawings for facilitating the understanding. Fig. 1 shows a constant-effect curve drawn on the basis of the herbicidal effect on barnyard grass shown in Table 2 in the test example. The axis of abscissa refers to the amount (g/ha) of compound 19 as active ingredient and the axis of ordinate to the amount (g/ha) of compound B as active ingredient. The expected ED 90 isobole of additive effect is shown in the broken line and ED 90 isobole of the combination between compound 19 and compound B obtained in practice is shown in the solid line. Similarly, the synergistic effect of the herbicidal composition (containing compound 19 and compound C) of the present invention is shown in Fig. 2. As shown in Fig. 1 and Fig. 2, the herbicidal compositions of the present invention have synergistic effect clearly.

Claims: A herbicidal composition comprising as active ingredients at least one organophosphorous compound, selected from the group consisting of N-(phosphonomethyl)glycine or a salt thereof, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or a salt thereof, and 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or a salt thereof, and a 3-substituted phenylpyrazole derivative represented by the general formula (I): wherein R is -Y 1 R 3 wherein R 3 is a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group, and Y 1 is -O- or -S-, -Y 2 CH(R 4 )CO-OR 5 wherein R 4 is a hydrogen atom or a lower alkyl group, R 5 is a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkenyl group or a lower alkynyl group and Y 2 is -O-, -S- or -NH, -COOCH(R 4 )CO-Y 1 R 5 wherein R 4 , R 5 and Y 1 are as defined above, or -COOR 6 wherein R 6 is a lower alkyl group, a lower alkenyl group or a lower alkynyl group, R 1 is a lower alkyl group, R 2 is a hydrogen atom, a lower alkyl group or a lower haloalkyl group, X 1 and X 2 , which may be the same or different, are halogen atoms, Y is -O-, -S-, -SO- or -SO 2 -, and n is zero or 1, wherein the organophosphorus compound is contained in an amount of 0,01 to 1,000 parts by weight per part by weight of the 3-substituted phenylpyrazole derivative of the general formula (I). A herbicidal composition comprising as active ingredients at least one organophosphorous compound, selected from the group consisting of N-(phosphonomethyl)glycine or a salt thereof, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or a salt thereof, and 4-[hydroxy(methyl)-phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or a salt thereof, and a 3-substituted phenylpyrazole derivative represented by the general formula (I): wherein R 1 is CH 3 , R is OCH 2 CH 2 = CH 2 , R 2 is CHF 2 , X 1 and X 2 are each Cl, Y is NH and n is 1. A herbicidal composition comprising as active ingredients at least one organophosphorous compound, selected from the group consisting of N-(phosphonomethyl)glycine or a salt thereof, 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine or a salt thereof, and 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine or a salt thereof, and a 3-substituted phenylpyrazole derivative represented by the general formula (I): wherein R 1 is CH 3 , R is OCH 2 C ≡ CH, R 2 is CHF 2 , X 1 and X 2 are each Cl, Y is NH and n is 1. A method for controlling weeds which comprises applying the herbicidal composition of any one of claims 1 to 3 in a dosage chosen in the range of 1 g to 5 kg (in terms of the active ingredients of the composition) per 10 ares for controlling undesirable weeds.

Inventors: KONNO TAKAMICHI, MABUCHI TSUTOMU, NAKATANI MOTOKATSU, KONNO, TAKAMICHI, MABUCHI, TSUTOMU, NAKATANI, MOTOKATSU
Applicants: NIHON NOHYAKU CO LTD, NIHON NOHYAKU CO., LTD.
Application year: 1993
Main classification: A01N57
IPC codes: A01N57, A01N43