Australian Patents Act 1990 - Regulation 3.2 ORIGINAL COMPLETE SPECIFICATION STANDARD PATENT Invention Title Method of controlling weeds The following statement is a full description of this invention, including the best method of performing it known to me/us: 5102 S34184 BACKGROUND OF THE INVENTION Field of the Invention 5 [0001] The present invention relates to a method of controlling weeds. Description of the Related Art 10 [00021 Flumioxazin is known as an effective herbicide in order to control weeds. Prior Art Literature 15 [0003] Non-Patent Literatures Non-Patent Literature 1: Crop Protection Handbook, vol. 97 (2011) Meister Publishing Company, ISBN: 1-892829-23-1) 20 SUMMARY OF THE INVENTION [0004] It is an obj ect of the present invention to provide a method of controlling weeds having high herbicidal effect. [00051 25 The inventor of the present invention have made earnest 1 a S34184 studies to find a method of controlling weeds having high herbicidal effect and, as a result, found that flumioxazin constituted of a crystal having a specific crystal form exhibits high herbicidal effect against weeds. This finding has led to 5 completion of the present invention. The present invention is as follows. [0006] [1] A method of controlling weeds in a crop field, land under perennial crops, or non-crop land, the method comprising 10 applying an effective amount of crystal of flumioxazin which is one or more selected from the group consisting of 1 st crystal, 2rd crystal, 3rd crystal, 4th crystal, 5 Lh crystal, 6 th crystal and 7' crystal, each of the crystals showing a powder X-Ray diffraction 15 pattern which has diffraction peaks with 29 values (o) shown in the corresponding right column of Table 1, 2 534184 Table 1 26 value() lt crystal 7.5+0.1, 11.9+0.1, 15.3±0.1 2 nd crystal 8.7±0.1, 9.4±0.1, 14.7+0.1, 18.8+0.1 3rd crystal 7.7+0.1, 10.9+0.1, 13.5 0.1, 14.6+0-1, 15.0+0,1 4th crystal 7.70.1, 10.7+0.1, 13.40.1, 14.3+0.1, 14.8+0.1 5 th crystal 5.5+0.1, 10.3+0.1, 10.9+0.1, 13.2+0.1 6th crystal 7.7+0.1, 8.6±0.1, 11.0+0.1, 13.2±0.1, 14.7+0.1, 15.1±0.1, 7 t crystal 14.5±0.1, 18.7+0.1 to soil where the weeds are grown or to be grown, or weeds. [0007] [2] The method according to [1] , wherein the crop field 5 is a field for soybean, peanut, common bean, pea, corn, cotton, wheat, rice, sunflower, potato, sugar cane, or vegetable. [0008] A wide range of weeds can be controlled by the method of controlling weeds of the present invention. 10 DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS [0009] A method of controlling weeds of the present invention (hereinafter referred to as the method of the present invention" 15 includes applying an ef fective amount of crystal of flumioxazin which shows apowderX-Raydiffractionpatternhaving diffraction 3 S34184 peaks with 20 values (0) shown in Table 1 above (hereinafter referred to as 1 st crystal of flumioxazin, 2 "' crystal of rd Lb flumioxazin, 3r crystal of flumioxazin, 4 crystal of flumioxazin, 5 tb crystal of flumioxazin, 6 Lh crystal of 5 flumioxazin and 7 th crystal of flumioxazin, respectively) to soil where weeds are grown or to be grown, or weeds in a crop field, land under perennial crops, or non-crop land. [0010] Generally, the substances to be used for herbicides or the 10 like are required to have high purity. Furthermore, required are to maintain their crystal form during the heating treatment step or the like steps for formulation, to show physical and chemical properties advantageous on the productions of, formulations, and to maintain their properties for long-term 15 storage. [0011] The 1 st crystal of flumioxazin, 2 nd crystal of flumioxazin, 3 crystalofflumioxazin, 4 'crystalofflumioxazin, 5 crystal of flumioxazin, 6 t crystal of flumioxazin and 7 th crystal of 20 flumioxazin (hereinafter, referred to as lt crystal of flumioxaxin to 7 Lb crystal of flumioxaxin) used in the method of the present invention can be produced by the methods disclosed in Example and modified methods thereof. [0012] 25 The 1e crystal of flumioxaxin to 7 crystal of flumioxaxin 4 S34184 in the present invention can be obtained, for example, by conducting the following steps. [0013] First, a starting material is dissolved in an organic 5 solvent to obtain a solution which contains flumioxazin at the concentration generally in the range of 2mg to 200mg, preferably in the range of 5 mg to 120 mg, per ml of the solvent, and setting the temperature of the obtained solution generally within the range of 40 0 C to 800C, preferably within the range of 500C to 10 75 0 C. [0014] Then, the heated solution may be heated to rapidly volatilizing its solvent, for example by dropping the solution onto the heated glass plate or the like to form and isolate 15 crystals. [0015] The heated solvent is preferably cooled to its temperature generally from about 0 Cto less than 25oC, preferably from about 100C to 25C to form a crystal. Preferably the step of cooling 20 the heated solution is gradually conducted, specifically by lowering the solution preferably at SoC to 15C per hour, more preferably at around 10 0 C per hour. Water or other solvent at the same temperature as that of the heated solution can be added to the solution before cooling for easily forming crystals. 25 After cooling the solution, the cooled solution is maintained 5 S34184 at the lowered temperature to form a crystal. The time of maintenance for the solution depends on the scale, temperature or other conditions of the solution, which can be arbitrarily determined. 5 [00161 The crystals of the present invention can be collected inaknownmanner, for example, by filtration, by concentration, by centrifugation or by decantation. The crystal may be washed with an appropriate solvent, if necessary. The crystal may be 10 subjected to the method comprising the above-mentioned steps or slurry filtration for improving its purity or quality. [0-017] It is possible to use, as the starting material for producing the crystal of the present invention, a solution or 15 asuspensionof flumioxazin, oramixture containing flumioxazin. It is also possible to use a solution or a suspension of asynthetic reaction crude product containing flumioxazin. [0018] The organic solvent to be used for the crystallization 20 includes alcohols such as methanol, 2-methoxyethanol, 2-ethoxyethanol, ethers such as tetrahydrofuran, acetone, 1,4-dioxane, halogenated hydrocarbons such as chloroform, 1, 2-dichloroethane or chlorobenzene, and aromatic hydrocarbons such as xylene or toluene. 25 [00191 6 S34184 It is also possible to use seed crystals in crystallization for producing the crystal of the present invention. In that case, it is preferred to use crystals having a crystal form to be prepared. The amount of seed crystals to be added is 5 preferably from 0.0005 parts by weight to 0.02 parts by weight, and more preferably from 0.001 part by weight to 0.01 part by weight, based on 1 part by weight of flumioxazin. The crystals of the present invention may be a solvate or a non-solvate. 10 [0020] When a specific hydrophilic organic solvent is used as a crystallization solvent, the obtained crystals are sometimes crystals of a solvate. The crystals of a non-solvate can be obtained by heating to dry the crystals of a solvate under reduced 15 pressure. [0021] The degree of drying of the crystals can be determined by analytical means such as gas chromatography. [0022] 20 It is also possible to determine the purity of the crystal form of the crystal by subj ecting the crystal to the powder X-ray diffraction measurement such as CuKa rays diffraction analysis, followed by analyzing the obtained diffraction pattern about the presence or absence of dif fraction peaks peculiar to crystal 25 of a solvate, and the height of the peaks. 7 S34184 [0023] The crystal of the present invention can be produced with high purity, can remain unchanged in crystal form even after a heat treating step for formulation, can also exhibit physical 5 and chemical properties which are more advantageous for the production of a formulation, and can maintain such properties even after being stored for a long period. [0024] The method of controlling weeds of the present invention 10 (hereinafter referred to as the method of the present invention) can be attained by applying the one or more crystals selected from the group consisting of 1 SL crystal of flumioxazin to 7th crystal of flumioxazin to soil where weeds are grown or to be grown, or weeds. 15 A wide range of weeds in a crop field, land under perennial crops, or non-crop land where usual tillage cultivation or non-tillage cultivation is carried out, can be controlled by the method of controlling weeds of the present invention. [00251 20 Examples of the crop f ield in the present invention include fields forfoodcrops suchas soybean, corn, cotton, wheat, barley, rye, triticale, rice, peanut, commonbean, limabean, azukibean, cowpeas, mung bean, black lentil, scarlet runner bean, vigna umbellate, moth bean, tepary bean, broad bean, pea, garbanzo 25 bean, lentil, lupine, pigeon pea, and potato; forage crops such 8 S34184 as sorghum, oat, and alfalfa; industrial crops such as sugar beet, sunflower, rapeseed, and sugar cane; and garden crops including vegetables. Examples of the vegetables to which the present invention is applied include Solanaceae vegetables (for 5 example, eggplant, tomato, green pepper, bell pepper, and hot pepper) ; Cucurbitaceae vegetables (for example, cucumber, pumpkin, zucchini, watermelon, and melon); Cruciferous vegetables (for example, Japanese radish, turnip, horse radish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, 10 and cauliflower) ; Compositae vegetables (for example, burdock, garland chrysanthemum, artichoke, and lettuce) ; Liliaceae vegetables (forexample, Welshonion, onion, garlic, asparagus); Umbelliferae vegetables (carrot, parsley, celery, and parsnip) ; Chenopodiaceae vegetables (for example, spinach and Swiss 15 chard) ; Labiatae vegetables (for example, Japanese mint, mint, basil, and lavender) ; strawberry; sweet potato; yam; and aroid. [0026] Also, the crop fields in the present invention include fields for cultivating so-called biomass crops such as Jatropha 20 curcas, switchgrass, Miscanthus, Arundo, reed canarygrass, bluestem, Erianthus, napier grass, and Spartina, used to produce oil and fats or alcohols for fuels used in heat engines. [0027] Themethodof the present invention is particularly applied 25 as a method efficiently controlling weeds in fields for 9 S34184 cultivating soybean, peanut, common bean, pea, corn, cotton, wheat, rice, sunflower, potato, sugar cane, orvegetables among the above crop fields. [0028] 5 When the method of the present invention is applied to a field for sugar cane, stem fragments cut so as to have one stalk may be used as the stem fragment of sugar cane, or stem fragments having a size of 2 cm to 15 cm may be used in the cultivationof sugarcane. Sugarcane cultivationmethods using 10 such stem fragments are publicly known (WO09/000398, W009/000399, W009/000400, W009/000401, andWO09/000402) andcarriedout under .the brand name of Plene (trademark), £0029] Examples of the land under perennial crops in the present 15 invention include orchards, tea gardens, mulberry gardens, coffee plantations, banana gardens, coconut gardens, flower/tree gardens, flower/tree fields, seeding fields, breeding f arms, woodlands, and garden parks. Examples of f ruit trees in the present invention include kernel fruits (for example, 20 apples, European pears, Japanese pears, Chinese quince, and Quinces) , stone fruits (forexample, peaches, plums, nectarines, Japanese apricots, cherries, apricots, and prunes) , citruses (Citrus unshiu, oranges, lemons, limes, and grapefruits) , nut trees (for example, Japanese chest nuts, walnuts, hazel nuts, 25 almonds, pistachios, cashew nuts, and macadamia nuts) , berry 10 S34184 fruits (for example, blueberries, cranberries, blackberries, and raspberries) , grapes, permissions, olives, and loquats. [0030] The method of the present invention is applied as a method 5 of efficiently controlling weeds, particularly, in orchards. [0031] Examples of the non-crop land include playgrounds, vacant lands, railroad sides, parks, car parks, roadsides, river beds, areas underpowercables, housing sites, andsites for factories. 10 [0032] In the present invention, any type of crop may be used as the crops cultivated in crop field without any particular limitationinsofaras itisavarietyusuallycultivatedascrops. This variety of plants includes plants to which resistance 15 toprotoporphyrinogenIXoxidase inhibitors such as flumioxazin; 4-hydroxyphenylpyrubic acid dioxygenase inhibitors such as isoxaflutole; acetolactate synthase inhibitors such as imazethapyr and thifensulfuron-methyl; acetyl-CoA carboxylase inhibitors such as sethoxydim; 20 5-enolpyruvylshikimate-3-phosphoric acid synthase inhibitors such as glyphosate; glutamine synthetase inhibitors such as glufosinate; auxin type herbicides such as 2,4-D and dicamba; and herbicides such as bromoxynil are imparted by classical breeding methods or genetic modification technologies. 25 [0033] 11 S34184 As examples of crops to which resistance has been imparted by classical breeding methods, corn resistant to imidazolinone type acetolactate synthase inhibitory herbicides such as imazethapyr is given and has already been commercially available 5 under the trade name of Clearfield (trademark). Examples of such crops include STS soybeans resistant to sulfonylurea type acetolactate synthase inhibitory herbicides such as thifensulfuron-methyl. Similarly, examples of a plant to which resistance to an acetyl CoA carboxylase inhibitor such as trione 10 oxime-based or aryloxyphenoxypropionic acid-based herbicide has been imparted by classical breeding methods include SR corn. Examples of a plant to which resistance has been imparted by genetic modification technologies include corn, soybeans and cotton resistant to glyphosate, and they have already been 15 commercially available under the trade names of RoundupReady (registered trade mark), Agrisure (registered trademark) GT, Cly-Tol (registered trademark) and the like. Similarly, there arecorn, soybeans and cotton resistant to glufosinate by genetic modification technologies, and they have already been 20 commercially available under the trade names of LibertyLink (registered trademark) and the like. There are varieties of corn and soybeans under the trade names of Optimum (registered trademark) and GAT (registered trade mark) , which are resistant to both of glyphosate and ALS inhibitor. Similarly, there are 25 soybeans resistant to imidazolinone type acetolactate synthase 12 S34184 inhibitors by genetic modification technologies, and they have been developed under the name of Cultivance. Similarly, there is cotton resistant to bromoxynil by genetic modification technologies, and this has already been commercially available 5 under the trade name of BXN (registered trademark) . Similarly, there is a variety of soybean sold under the trade name of RoundupReady (registered trademark) 2 Xtend as a soybean resistant to both of glyphosate and dicamba by genetic modif ication technologies. Similarly, there has beendeveloped 10 cotton resistant to both of glyphosate and dicamba by genetic modification technologies. A gene encoding aryloxyalkanoate dioxygenase may be introduced to produce a crop which becomes resistant to phenoxy acid type herbicides such as 2,4-D, MCPA, dichlorprop and 15 mecoprop, and aryloxyphenoxypropionic acid type herbicides such as quizalofop, haloxyfop, fluazifop, diclofop, fenoxaprop, metamifop, cyhalofop and clodinafop (Wright et al. 2010: Proceedings of National Academy of Science, 107 (47): 20240-20245). Cultivars of soybean and cotton, which show the 20 resistance to 2,4-D, have been developed under the brand of Enlist. [0034] A gene encoding a 4 -hydroxyphenyl pyruvic acid dioxygenase (hereinafter referred to as HPPD) inhibitor, the gene having 25 resistance to HPPD, may be introduced to create a plant resistant 13 S34184 to a HPPD inhibitor (US2004/0058427) . A gene capable of synthesizing homogentisic acid which is a product of HPPD in a separate metabolic pathway even if HPPD is inhibited by a HPPD inhibitor is introduced, with the result that a plant having 5 resistance to the HPPD inhibitor can be created (WO02/036787). A gene expressing excess HPPD may be introduced to produce HPPD in such an amount as not to adversely affect the growth of plants even in the presence of a HPPD inhibitor, with the result that a plant having resistance to the HPPD inhibitor can be created 10 (W096/38567) . Besides introduction of the gene expressing excess HPPD, a gene encoding prephenate dehydrogenase is introduced in order to increase the yield of p-hydroxyphenyl pyruvic acid which is a substrate of HPPD to create a plant having resistance to the HPPD inhibitor (Rippert P et, al., 2004 15 Engineering plant shikimate pathway for production of tocotrienol and improving herbicide resistance. Plant Physiol. 134: 92-100). [0035] Examples of a method of producing crops resistant to 20 herbicides include, other than the above, the gene introducing methods described in W098/20144, W02002/46387, and US2005/0246800. [0036] The above crops include, for example, crops which can 25 synthesize selective toxins and the like known as the genus 14 S34184 Bacillus by using genetic modification technologies. Examples of the toxins developed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; 6-endotoxins such as 5 CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl, Cry9C, Cry34, and Cry35ab derived from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3, and VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins, 10 andneurotoxins specific to insects; filamentous fungus toxins; plant lectins; agglutinin; trypsin inhibitors, serine protease inhibitors, and protease inhibitors such as patatin, cystatin, and papain inhibitors; ribosome inactivatingproteins (RIP) such as lysine, corn-RIP, abrin, luf in, saporin, and bryodin; steroid 15 metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptors; stilbene 20 synthase; bibenzyl synthase; chitinase; and glucanase. The toxins expressed in these transgenic plants include hybrid toxins, partially deficient toxins and modified toxins which derive from 5-endotoxin proteins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl, Cry9C, Cry34Ab and 25 Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3 and 15 S34184 VIP3A. The hybrid toxins are created by new combinations of domains having dif ferent proteins by using genetic modif ication technologies. As the partially defective toxins, CrylAb in which part of the amino acid sequences is missing is known. In 5 the modified toxin, one or more of amino acids of a natural type toxin is replaced. Examples of these toxins and genetically modified plants capable of synthesizing these toxins are describedin, forexample, EP-A-0374753, W093/07278, W095/34656, EP-A-0427529, EP-A-451878, and WO 03/052073. Resistance to 10 noxious insects belonging to order Coleoptera, order Diptera, and order Lepidoptera is imparted to plants by toxins contained in these genetically modified plants. Also, genetically modified plants which contain one or more insecticidal genes resistant to harmful insects and develop 15 one or more toxins have been already known and some of these plantshavebeenputonthemarket. Examples of thesegenetically modified plants include YieldGard (registered trademark) (corn variety expressing CrylAb toxin), YieldGard Rootworm (registered trademark) (corn variety expressing Cry3Bbl toxin), 20 YieldGard Plus (registered trademark) (corn variety expressing CrylAb and Cry3Bbl toxins) , Herculex I (registered trademark) (corn variety expressing phosphinothricin N-acetyltransferase (PAT) for imparting resistance to a CrylFa2 toxin and glufosinate), NatureGard (registered trademark), AGRISURE 25 (registeredtrademark) CBAdvantage (Btllcornborer (CB) trait), 16 S34184 Protecta (registered trademark); and the like. Also, genetically modified cotton which contains one or more insecticidal genes resistant to harmful insects and develops one or more toxins has been already known and some of cotton 5 have been put on the market. Examples of these genetically modified cotton include BollGard (registered trademark) (cotton variety expressing CrylAc toxin), BollGard (registered trademark) II (cotton variety expressing CrylAc and Cry2Ab toxins), BollGard (registered trademark) III (cotton variety 10 expressing CrylAc, Cry2Ab and VIP3A toxins) , VipCot (registered trademark) (cotton variety expressing VIP3A and CrylAb toxins), WideStrike (registered trademark) (cotton variety expressing CrylAc and CrylF toxins) and the like. Examples of the plant used in the present invention also 15 include plants such as soybeans into which a Ragl (Resistance Aphid Gene 1) gene is introduced to impart resistance to an aphid. The plants to be used in the present invention include those provided with resistance to nematodes by using a classical breedingmethod or genetic modification technologies. Examples 20 of the genetic modification technologies used to provide the resistance to nematodes include RNAi. [0037] The above crops include those to which the ability to produce antipathogenic substances having a selective effect is 25 impartedusing genetic modification technologies. Forexample, 17 S34184 PR proteins are known as an example of the antipathogenic substance (PRPs, EP-A-0392225) . Such antipathogenic substances and genetically modified plants producing these antipathogenic substances are described in, for example, 5 EP-A-0392225, WO 95/33818, and EP-A-0353191. Examples of the antipathogenic substances developed in such genetically modified plants include ion channel inhibitors such as a sodium channel inhibitor and calcium channel inhibitor (KP1, KP4, and KP6 toxins produced by virus are known) ; stilbene synthase; 10 bibenzyl synthase; chitinase; glucanase; PR protein; antipathogenic substances produced by microorganisms such as peptide antibiotics, antibiotics having a heteroring, and a protein factor (referred to as a plant disease resistant gene and described in WO 03/000906) relating to plant disease 15 resistance. The above crops include plants to which useful traits such as an oil component reformation and amino acid-content reinforcingtraitaregivenbygeneticmodificationtechnologies. Examples of these plants include VISTIVE (trademark) (low 20 linolenic soybean having a reduced linolenic content), high-lysine (high oil) corn (corn having an increased lysine or oil content) and the like. Moreover, the above crops include stuck varieties obtained by combining two or more useful traits such as the above classical 25 herbicide trait or herbicide resistant gene, gene resistant to 18 S34184 insecticidal noxious insects, antipathogenic substance-producing gene, oil component reformation, and amino acid-content reinforcing trait, and allergen reduction trait. [0038] 5 As the weeds which can be controlled by the method of the present invention, the following examples are given. [0039] Weeds of the family Urticaceae: Urtica urens; weeds of the family Polygonaceae: Polygonum convolvulus, 10 Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Polygonum longisetum, Polygonum aviculare, Polygonum arenastrum, Polygonum cuspidatum, Rumex japonicas, Rumex crispus, Rumex obtusifolius, and Rumex acetosa; weeds of the family Portulacaceae: Portulaca oleracea; 15 weeds of the family Caryophyllaceae: Stellaria media, Cerastium holosteoides, Cerastium glomeratum, Spergula arvensis, and Silene gallica; weeds of the family Molluginaceae: Mollugo verticillata; weeds of the family Chenopodiaceae: Chenopodium album, 20 Chenopodium ambrosioides, Kochia scoparia, Salsola kali, and Atriplex spp.; [0040] weeds of the familyAmaranthaceae: Amaranthus retroflexus, Amaranthus viridis, Amaranthus lividus, Amaranthus spinosus, 25 Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, 19 S34184 Amaranthus patulus, Amaranthus tuberculatos, Amaranthus blitoides, Amaranthus deflexus, Amaranthus quitensis, Alternanthera philoxeroides, Alternanthera sessilis, and Alternanthera tenella; 5 weeds of the family Papaveraceae: Papaver rhoeas and Argemone mexicana; weeds of the family Brassicaceae: Raphanus raphanistrum, Raphanus sativus, Sinapis arvensis, Capsella bursa-pastoris, Brassica juncea, Brassica campestris, Descurainia pinnata, 10 Rorippa islandica, Rorippa sylvestris, Thlaspi arvense, Myagrum rugosum, Lepidium virginicum, and Coronopus didymus; weeds of the family Capparaceae: Cleome affinis; [0041] weeds of the family Fabaceae: Aeschynomene indica, 15 Aeschynomene rudis, Sesbania exaltata, Cassia obtusifolia, Cassia occidentalis, Desmodium tortuosum, Desmodium adscendens, Trifolium repens, Pueraria lobata, Vicia angustifolia, Indigofera hirsute, Indigofera truxillensis, and Vigna sinensis; 20 weeds of the family Oxalidaceae: Oxalis corniculata, Oxalis strica, and Oxalis oxyptera; weeds of the family Geraniaceae: Geranium carolinense and Erodium cicutarium; weeds of the family Euphorbiaceae: Euphorbia helioscopia, 25 Euphorbia maculate, Euphorbia humistrata, Euphorbia esula, 20 S34184 Euphorbia heterophylla, Euphorbia brasiliensis, Acalypha australis, Croton glandulosus, Croton lobatus, Phyllanthus corcovadensis, and Ricinus communis; [0042] 5 weeds of the family Malvaceae: Abutilon theophrasti, Sida rhombiforia, Sidacordifolia, Sidaspinosa, Sidaglaziovii, Sida santaremnensis, Hibiscus trionum, Anoda cristata, and Malvastrum coromandelianum; weeds of the family Sterculiaceae: Waltheria indica; 10 weeds of the family Violaceae: Viola arvensis, and Viola tricolor; weeds of the family Cucurbitaceae: Sicyos angulatus, Echinocystis lobata, and Momordica charantia; weeds of the family Lythraceae: Lythrum salicaria; 15 weeds of the familyApiaceae: Hydrocotyle sibthorpioides; weeds of the family Sapindaceae: Cardiospermum halicacabum; weeds of the family Primulaceae: Anagallis arvensis; weeds of the family Asclepiadaceae: Asclepias syriaca and 20 Ampelamus albidus; weeds of the family Rubiaceae: Galium aparine, Galium spurium var. echinospermon, Spermacoce latifolia, Richardia brasiliensis, and Borreria alata; [0043] 25 weeds of the family Convolvulaceae: Ipomoea nil, Ipomoea 21 S34184 hederacea, Ipomoea purpurea, Ipomoea hederacea var. integriuscula, Ipomoea lacunose, Ipomoea triloba, Ipomoea acuminate, Ipomoea hederifolia, Ipomoea coccinea, Ipomoea quamoclit, Ipomoea grandifolia, Ipomoea aristolochiafolia, 5 Ipomoea cairica, Convolvulus arvensis, Calystegia hederacea, Calystegia japonica, Merremia hedeacea, Merremia aegyptia, Merremia cissoids, and Jacquemontia tamnifolia; weeds of the family Boraginaceae: Myosotis arvensis; weeds of the family Lamiaceae: Lamium purpureum, Lamium 10 amplexicaule, Leonotis nepetaefolia, Hyptis suaveolens, Hyptis lophanta, Leonurus sibiricus, and Stachys arvensis; [0044] weeds of the familySolanaceae: Daturastramonium, Solanum nigrum, Solanum americanum, Solanum ptycanthum, Solanum 15 sarrachoides, Solanum rostratum, Solanum aculeatissimum, Solanum sisymbriifolium, Solanum carolinense, Physalis angulata, Physalis subglabrata, and Nicandra physaloides; weeds of the family Scrophulariaceae: Veronica hederaefolia, Veronica persica, and Veronica arvensis; 20 weeds of the family Plantaginaceae: Plantago asiatica; [00451 weeds of the family Asteraceae: Xanthium pensylvanicum, Xanthium occidentale, Helianthus annuus, Matricaria chamomilla, Matricaria perforate, Chrysanthemum segetum, Matricaria 25 matricarioides, Artemisia princeps, Artemisia vulgaris, 22 S34184 Artemisiaverlotorum, Solidago altissima, Taraxacum of ficinale, Galinsoga ciliate, Galinsoga parviflora, Senecio vulgaris, Senecio brasiliensis, Senecio grisebachii, Conyza bonariensis, Conyza Canadensis, Ambrosia artemisiaefolia, Ambrosia trifida, 5 Bidens pilosa, Bidens frondosa, Bidens subalternans, Cirsium arvense, Cirsium vulgare, Silybum marianum, Carduus nutans, Lactuca serriola, Sonchus oleraceus, Sonchus asper, Wedelia glauca, Melampodium perfoliatum, Emilia sonchifolia, Tagetes minuta, Blainvillea latifolia, Tridax procumbens, Porophyllum 10 ruderale, Acanthospermum australe, Acanthospermum hispidum, Cardiospermum halicacabum, Ageratum conyzoides, Eupatorium perfoliatum, Eclipta alba, Erechtites hieracifolia, Gamochaeta spicata, Gnaphalium spicatum, Jaegeria hirta, Parthenium hysterophorus, Siegesbeckia orientalis, and Soliva sessilis; 15 [0046] weeds of the family Liliaceae: Allium canadense and Allium vineale; weeds of the family Commelinaceae: Commelina communis, Commelina bengharensis, and Commelina erecta; 20 [0047] weeds of the family Poaceae: Echinochloa crus-galli, Setaria viridis, Setaria faberi, Setaria glauca, Setaria geniculata, Digitaria ciliaris, Digitaria sanguinalis, Digitaria horizontalis, Digitaria insularis, Eleusine indica, 25 Poa annua, Alospecurus aequalis, Alopecurusmyosuroides, Avena 23 S34184 fatua, Sorghum halepense, Sorghum vulgare, Agropyron repens, Lolium multiflorum, Lolium perenne, Lolium rigidum, Bromus secalinus, Bromus tectorum, Hordeum jubatum, Aegilops cylindrica, Phalaris arundinacea, Phalaris minor, Apera 5 spica-venti, Panicum dichotomiflorum, Panicum texanum, Panicum maximum, Brachiaria platyphylla, Brachiaria ruziziensis, Brachiaria plantaginea, Brachiaria decumbens, Brachiaria brizantha, Brachiariahumidicola, Cenchrus echinatus, Cenchrus pauciflorus, Eriochloa villosa, Pennisetum setosum, Chloris 10 gayana, Eragrostis pilosa, Rhynchelitrum repens, Dactyloctenium aegyptium, Ischaemum rugosum, Oryza sativa, Paspalum notatum, .Paspalummaritimum, Pennisetum clandestinum, Pennisetum setosum, and Rottboellia cochinchinensis; [00481 15 weeds of the f amily Cyperaceae: Cyperus microiria, Cyperus iria, Cyperus odoratus,.Cyperus rotundus, Cyperus esculentus, and Kyllinga gracillima; and weeds of the family Equisetaceae: Equisetum arvense and Equisetum palustre. 20 [0049] In the method of the present invention, the one or more crystals selected from the group consisting of 1't crystal of flumioxazin to 7t crystal of flumioxazin is usually mixed with a solid carrier, liquid carrier, or the like and, according to 25 the need, formulated with surfactants and other preparation aids 24 S34184 into preparat ions such as an emulsion, water-dispersible powder, suspension, and granule. These preparations each contain the one or more crystals selected from the group consisting of 1 ,L crystal of flumioxazin to 7 th crystal.of flumioxazin in an amount 5 of usually 0.05 to 90% by weight and preferably 0.1 to 80% by weight. [0050] In the method of the present invention, examples of the solid carrier used for formulating the one or more crystals 10 selected from the group consisting of 1 crystal of flumioxazin to 7 th crystal of flumioxazin into preparations include microparticles and granules of compounds such as clays (for example, Kaolinite, diatomaceous earth, synthetic water-containing silicon oxide, Fubasami clay, bentonite, and 15 acidclay), talc, otherinorganicminerals (forexample, sericite, quartz powder, sulfur powder, activated carbon, and calcium carbonate), and chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, and urea), andexamplesof the liquidcarrier include water, alcohols 20 (for example, methanol and ethanol), ketones (for example, acetone, methyl ethyl ketone, and cyclohexanone), aromatic hydrocarbons (for example, toluene, xylene, ethylbenzene, and methylnaphthalene), non-aromatic hydrocarbons (hexane, cyclohexane, and kerosene), esters (for example, ethyl acetate 25 and butyl acetate), nitriles (for example, acetonitrile and 25 S34184 isobutyronitrile), ethers (for example, dioxane and diisopropyl ether), acid amides (for example, dimethylformamide and dimethylacetamide) , and halogenated hydrocarbons (for example, dichloroethane and trichloroethylene). 5 [0051] In the method of the present invention, examples of the surfactant used for formulating the one ormore crystals selected from the group consisting of IY crystal of flumioxazin to 7 th crystal of flumioxazin into preparations include alkyl sulfates, 10 alkyl sulfonates, alkylaryl sulfonates, alkyl aryl ethers and polyoxyethylene products thereof, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. Examples of the other preparation aids include binders and dispersants such as casein, gelatin, polysaccharides (for 15 example, starch, gumarabic, cellulose derivatives, andalginic acid) , lignin derivatives, bentonite, synthetic water-soluble polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acids), and stabilizers such as PAP (acidic isopropyl phosphate) , BHT (2, 6-tert-butyl-4-methylphenol) , BHA 20 (2-/3-tert-butyl-4-methoxyphenol) , vegetable oil, mineral oil, fatty acid, and fatty acid ester. [0052] Theoneormore crystals selected from the group consisting of 14 crystal of flumioxazin to 7 th crystal of flumioxazin 25 formulated into a preparation in this manner may be sprayed on 26 S34184 soil or plant body either as it is, or after it is made into a dilute solution by diluting it with water or the like. In the method of the present invention, other herbicides are further mixed with the one or more crystals selected from the group 5 consisting of 1t crystal of flumioxazin to 7 th crystal of flumioxazin for use, so that an increase in herbicidal effect is expected. Also, the one or more crystals selected from the group consisting of 1 st crystal of flumioxazin to 7 th crystal of flumioxazin may be further used together with, for example, 10 insecticides, germicides, plantgrowthregulators, fertilizers, and soil conditioners. [0053] The amount of the one or more crystals selected from the group consisting of 1 st crystal of flumioxazin to 7 t" crystal 15 of flumioxazin to be used in the method of the present invention is usually 2 to 10000 g, preferably 5 to 5000 gin terms of compound amount/ha though this differs depending on weather conditions, preparation form, time of use, methodof use, place of use, weeds tobe controlled, and object crop. When the one or more crystals 20 selected from the group consisting of 1 st crystal of flumioxazin to 7 th crystal of flumioxazin is used in the form of emulsion, water-dispersible powder, suspension, or the like, a specified amount of the emulsion, water-dispersible powder, suspension, or the like is usually diluted with 100 to 2000 L/ha for use. 25 Also, when the one or more crystals selected from the group 27 S34184 consisting of 1 st crystal of flumioxazin to 7' crystal of flumioxazin is used to perform stem leaves treatment of weeds, adjuvants are added to the dilute solution of the one or more crystals selected from the group consisting of 1 SL crystal of 5 flumioxazin to 7th crystal of flumioxazin in order to increase the herbicidal effect against weeds. [0054] In the method of the present invention, weeds or places where weeds are expected to grow are treated with the one or 10 more crystals selected from the group consisting of 1 SL crystal of flumioxazin to 7 crystal of flumioxazin. Examples of the treatment of weeds include treatment of weeds themselves and treatment of soil after weeds grow. The treatment of the place where weeds are expected to grow includes treatment of the surface 15 of soil before weeds grow. [0055] The following aspects are given as examples of the treatment method in the method of the present invention: a method in which the flumioxazin solution is sprayed on. 20 the surface of soil before crops are sowed and before weeds grow; a method in which the flumioxazin solution is sprayed on the surface of soil before crops are sowed and after weeds grow; a method in which the flumioxazin solution is sprayed on weeds before crops are sowed and after the weeds grow; 25 a method in which the flumioxazin solution is sprayed on 28 S34184 the surface of soil after crops are sowed but before they germinate, and before weeds grow; a method in which the flumioxazin solution is sprayed on the surface of soil after crops are sowedbut before they germinate, 5 and after weeds grow; a method in which the flumioxazin solution is sprayed on weeds after crops are sowed but before they germinate, and after the weeds grow; a method in which the flumioxazin solution is sprayed on 10 the surface of soil in the presence of crops before germination of weeds; a method in which the flumioxazin solution is sprayed on the surface of soil in the presence of crops after weeds grow; and/or 15 a method in which the flumioxazin solution is sprayed on the surface of soil in the presence of crops after germination of the weeds. Examples 20 [0056] Hereinbelow, the present invention will be described in detailbywayof examples, but the present invention is not limited to these examples. [0057) 25 [Production Example] 29 S34184 Production Examples of l' crystal of flumioxazin to 7th crystal of flumioxazin used in the method of the present invention will be shown below, The powder X-ray diffraction patterns of the obtained crystals 5 were measured by X'Pert Pro MPD (manufactured by PANalytical B.V., Netherland) at a scanning range from 2.00 to 40.00 (20) using CuKx rays (40 kV, 30 mA). [00581 Production Example 1 10 Flumioxazin (100 mg) was dissolved in 2-methoxyethanol at 60 0 C so as to adjust its concentration to 16.8 mg/mL. Then 10 times volumes of water relative to the volume of 2-methoxyethanol were heated to 600C and gradually added to the obtained solution. The obtained mixture was gradually cooled 15 to 20 0 C at the rate of 10 0 C per hour and then left to stand, followed by filtrating it to collect crystals. The pattern of the obtained crystals had the peaks with 20 values as shown in Table 2 to find them 1 3t crystals of flumioxazin. 20 Table 2 20 value (0) d value (A) Relative intensity (%) 7.5 11.7774 22.5 11.9 7.4308 61.9 15.3 5.8241 11.0 The 1 crystals of flumioxazin were obtained by the same method as mentioned above except that methanol or 2-ethoxyethanol was 30 S34184 used instead of 2-methoxyethanol. [0059] Production Example 2 Flumioxazin (100 mg) was dissolved in tetrahydrofuran 5 [THF] at 600C so as to adjust its concentration to 51.0 mg/mL. The obtained mixture was gradually dropped onto a glass plate heated at 100 0 C to rapidly volatilize its solvent therefrom, to obtain crystals. The pattern of the obtained crystals had the peaks with 10 28 values as shown in Table 3 to find them 2 nd crystals of flumioxazin Table 3 20 value (0) d value (A) Relative intensity (%) 8.7 10.1555 20.4 9.4 9.4007 43.5 14.7 6.0211 62.0 18.8 4.7162 100.0 The 2 nd crystals of flumioxazin were obtained by the same method as mentioned above except that acetone was used instead of THF. 15 The crystals were obtained by adding methanol instead of THF to flumioxazin, gradually cooling to 20 0 C, followed by leaving it to stand. [0060] Production Example 3 20 Flumioxazin (100 mg) was dissolved in 1, 2-dichloroethane at 60 0 C so as to adjust its concentration to 50.9 mg/mL. Then 31 S34184 the obtained solution was gradually cooled to 20 0 C at the rate of 100C per hour and then left to stand, followed by blow its solvent with nitrogen gas to obtain crystals. The pattern of the obtained crystals had the peaks with 5 20 values as shown in Table 4 to find them 3 rd crystals of flumioxazin Table 4 26 value (0) d value (A) Relative intensity (% 7.7 11.4720 100.0 10.9 8.1102 21.5 13 . 5 6.5535 41.1 14 . 6 6.0621 9. 5 15.0 5.9013 12.6 The 3 r crystals of flumioxazin were obtained by the same method 10 as mentioned above except that chlorobenzene was used instead of 1,2-dichloroethane. [0061] Production Example 4 Flumioxazin (100 mg) was dissolved in toluene at 60oC so 15 as to adjust its concentration to 13.3 mg/mL. Then the obtained solution was gradually cooled to 20aC at the rate of 100C per hour and then left to stand, followed by blow its solvent with nitrogen gas to obtain crystals. The pattern of the obtained crystals had the peaks with 20 28 values as shown in Table 5 to find them 4 th crystals of flumioxazin. 32 S34184 Table 5 20 value (0) d value (A) Relative intensity (%) 7.7 5.9013 100.0 10.7 8,2613 13.9 13.4 6.6022 25.5 14.3 6.1886 4.6 14.8 5.9806 6.8 [00623 Production Example 5 5 Flumioxazin (100 mg) was dissolved in xylene at 60 0 C so as to adjust its concentration to 10.0 mg/mL. Then the obtained solution was gradually cooled to 20 0 C at the rate of 10 0 C per hour and then left to stand, followed by blow its solvent with nitrogen gas at 20 0 C to obtain crystals. 10 The pattern of the obtained crystals had the peaks with 29 values as shown in Table 6 to find them 5 th crystals of flumioxazin. Table 6 20 value (0) d value (A) Relative intensity (%) 5.5 16.0548 23.1 10.3 8.5812 68.2 10.9 8.1102 29.7 13.2 6.7018 37.6 15 [0063] Production Example 6 Flumioxazin (100 mg) was dissolved in chloroform at 60 0 C 33 S34184 so as to adjust its concentration to 102. 8 mg/mL. The chloroform solution was added gradually to 10 times volumes of heptane relative to the volume of chloroform at 600C. The obtained mixture was gradually cooled to 200C at the rate of 100C per 5 hour and then left to stand, followed by filtrating it to collect crystals. The pattern of the obtained crystals had the peaks with 29 values as shown in Table 7 to find them 6 th crystals of f lumioxaz in. 10 Table 7 29 value (0) d value (A) Relative intensity (%) 7.7 11.4720 100.0 8.6 10.2733 5.8 11.0 8.0367 14.4 13.2 6.7018 6.7 14.7 6.0211 7.4 15.1 5.8625 9.2 The 6th crystals of flumioxazin were obtained by the same method as mentioned above except that THE was used instead of chlorof orm. 15 The solution obtained by adding 2 times volumes of THF relative to the volume of chloroform toflumioxazin instead of chloroform, was added to 10 times volumes of water relative to the volume of THF and gradually cooled to 200C, followed by leaving it to stand. 20 The crystals were obtained by adding THE, 1,4-dioxaneorpyridine 34 S34184 instead of chloroform to flumioxazin and, gradually cooling to 200C, followed by concentrating it. [0064] Production Example 7 5 Flumioxazin (100 mg) was dissolved in 1, 4-dioxane at 60OC soas toadjust itsconcentration to50.9mg/mL. The l,4-dioxane solution was added gradually to 10 times volumes of water relative to the volume of 1, 4 - dioxane at 6 0 0 C. The obtained mixture was gradually cooled to 200C at the rate of 10OC per hour and then 10 left to stand, followed by filtrating it to collect crystals. The pattern of the obtained crystals had the peaks with 20 values as shown in Table 8 to find them 7 th crystals of flumioxazin. 15 Table 8 20 value () d value (A) Relative intensity (%-) 14.5 6.1037 15.6 18.7 4.7412 36.4 The 7 th crystals of flumioxazin were obtained by the same method as mentioned above except that heptane was used instead of water. [00651 20 [Preparation Examples] Preparation Examples will be shown below. Here, theparts represent parts by weight. [0066] 35 S34184 Preparation Example 1 One or more crystals selected from the group consisting of 1' crystal of flumioxazin to 7 th crystal of flumioxazin (10 parts), polyoxyethylene sorbitan monooleate (3 parts), CMC 5 (carboxymethyl cellulose) ( 3 parts) , and water (84 parts) are mixed with one another and the mixture is wet -milled to the extent that it has a grain size of 5 micrometer or less to obtain a suspension. [0067] 10 Preparation Example 2 One or more crystals selected from the group consisting of 1 st crystal of flumioxazin to 7 th crystal of flumioxazin (1 part) , polyoxyethylene sterylphenyl ether (14 parts) , calcium dodecylbenzenesulfonate (6 parts), xylene (30 parts), and 15 N,N-dimethylformamide (49 parts) are mixed with one another to obtain an emulsion. [0068] Preparation Example 3 One or more crystals selected from the group consisting 20 of 14 crystal of flumioxazin to 7th crystal of flumioxazin (10 parts), sodium laurylsulfate (2 parts), and synthetic water-containing silicon oxide (88 parts) are mixed with one another to obtain a water-dispersible powder. [0069] 25 [Test Examples] 36 S34184 In Test Examples, the herbicidal effect is evaluated as follows. [Herbicidal effect] In the evaluationof the herbicidal effect, thegermination 5 orgrowthconditionof eachtest weed ina treatedarea is compared with that in an untreated area and when there is no or almost no difference in germination or growth condition between the treated area and the untreated area at the time of investigation, the case is given "0", and when the test plant perfectly withers 10 and dies, or the germination or growth of the plant is perfectly restricted at the time of investigation, the case is given "100" , thereby grading each sample between 0 to 100. [0070] Test Example 1 15 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 st crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. Af ter 15 days, cotton seeds are sowed. This pot is placed 20 inagreenhouse. The herbicidal effect is examined 15 days after the cotton seeds are sowed. [0071] Test Example 2 Cotton seeds are sowed in a cultivated field. Weed stem 25 andleavesaredirectlytreatedwithoneormorecrystals selected 37 S34184 from the group consisting of 1 "t crystal of flumioxazin to 7 crystal of flumioxazin at a dose of 25, 50, 100, 200, or 400 g/ha in the condition of the cotton main stem being lignified at a length of 15 cm from the surface of the ground 30 days after 5 these seeds are sowed. The herbicidal effect is examined 28 days after the treatment, [0072] Test Example 3 A pot is filled with soil and weeds are sowed, and the 10 surface of the soil is uniformly treated with one or more crystals selected from the group consisting of l" crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 7 days, soybean seeds are sowed. This pot is placed inagreenhouse. Theherbicidal effect is examined 15 days after 15 the soybean seeds are sowed.
[0073] Test Example 4 A pot is filled with soil and soybean seeds and weed seeds are sowed. On the day of sowing, the surface of the soil is 20 uniformly treated with one or more crystals selected from the group consisting of 1 l crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. This pot is placed in a greenhouse. The herbicidal effectis examined 15 days after the seeds are sowed. 25 [00741 38 S34184 Test Example 5 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1'l crystal of flumioxazin 5 to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 7 days, corn seeds are sowed. This pot is placed inagreenhouse. Theherbicidal effect is examined IS days after the corn seeds are sowed. [0075] 10 Test Example 6 A pot is filled with soil and corn seeds and weed seeds are sowed. On the day of sowing, the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 't crystal of flumioxazin to 7 th crystal 15 of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the seeds are sowed. [0076] Test Example 7 20 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one ormore crystals selected from the group consisting of ' crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 15 days, wheat seeds are sowed. This pot is placed 25 inagreenhouse. The herbicidal effect is examined 15 days after 39 S34184 the wheat seeds are sowed. [0077] Test Example 8 A pot is filled with soil and weeds are sowed, and the 5 surface of the soil isuniformly treatedwithoneormore crystals selected from the group consisting of 1 " crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After15days, tomato seeds are sowed. Thispotisplaced inagreenhouse. The herbicidal effect is examined 15 days after 10 the tomato seeds are sowed. [0078) Test Example 9 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more crystals 15 selected from the group consisting of 1 't crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 15 days, eggplant seeds are sowed. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the eggplant seeds are sowed. 20 [0079] Test Example 10 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1" crystal of flumioxazin 25 to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 40 S34184 g/ha. After 15 days, bell pepper seeds are sowed. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the bell pepper seeds are sowed. [0080] 5 Test Example 11 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 't crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, 200, 10 or400g/ha. Afterl5days, sugarcanestemfragmentsareplanted. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days af ter the sugar cane stem fragments are planted. [0081] Test Example 12 15 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 't crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 15 days, common bean seeds are sowed. This pot 20 is placed in a greenhouse. The herbicidal effect is examined 15 days after the common bean seeds are sowed. [0082] Test Example 13 A pot is filled with soil and weeds are sowed, and the 25 surface of the soil isuniformly treatedwithoneormore crystals 41 S34184 selected from the group consisting of 1 't crystal of f lumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 15 days, rice seeds are sowed. This pot is placed inagreenhouse. The herbicidal effect is examined 15 days after 5 the rice seeds are sowed. [0083] Test Example 14 A pot is filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more crystals 10 selected from the group consisting of lst crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 15 days, rapeseeds are sowed. This pot is placed inagreenhouse. The herbicidal effect is examined 15 days after the rapeseeds are sowed. 15 {0084] Test Example 15 Sugarcane stem fragments are sowed in a cultivated field. After the stem fragments are planted, the stem leaves of weeds are treated directly with one or more crystals selected from 20 the group consisting of 1t crystal of flumioxazin to 7 crystal of flumioxazin at a dose of 25, 50, 100, 200, or 400 g/ha when the plant height of the sugarcane becomes 60 cm or higher. The herbicidal effect is examined 28 days after the treatment. [0085] 25 Test Example 16 42 S34184 A pot is filled with soil and peanut seeds and weed seeds are sowed. On the day of sowing, the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 st crystal of flumioxazin to 7 crystal 5 of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the seeds are sowed. [00861 Test Example 17 10 A pot is filled with soil and common bean seeds and weed seeds are sowed. On the day of sowing, the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1' crystal of flumioxazin to 7th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. This pot 15 is placed in a greenhouse. The herbicidal effect is examined 15 days after the seeds are sowed. [0087] Test Example 18 A pot is filled with soil and pea seeds and weed seeds 20 are sowed. On the day of sowing, the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 't crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. This pot is placed in a greenhouse. The herbicidal effect is examined 25 15 days after the seeds are sowed. 43 S34184 [0088]8 Test Example 19 A pot is filled with soil and sunflower seeds and weed seeds are sowed. On the day of sowing, the surface of the soil 5 is uniformly treated with one or more crystals selected from the group consisting of 1 s crystal of flumioxazin to 7th crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the seeds are sowed. 10 [00891 Test Example 20 A pot is filled with soil, and weed seeds are sowed and sugarcane stem fragments are planted. On the day of sowing and planting, the surface of the soil is uniformly treated with one 15 or more crystals selected from the group consisting of 1' crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 25, 50, 100, 200, or 400 g/ha. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the sowing and planting. 20 [0090] Test Example 21 A pot is filled with soil, and weed seeds are sowed and potato tubers are planted. On the day of sowing and planting, the surface of the soil is uniformly treated with one or more 25 crystals selected from the group consisting of 1 S' crystal of 44 S34184 flumioxazin to 7 th crystal of flumioxazin at a dose of 12.5, 25, 50, or 100 g/ha. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the sowing and planting. 5 [0091] Test Example 22 A pot is filled with soil and onion seeds and weed seeds are sowed. This pot is placed in a greenhouse. When the onion grows 2 to 6 leaves, the surface of the soil and the stem leaves 10 of the weeds are uniformly treated with one or more crystals selected from the group consisting of 1 't crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 12.5, 25, 50, or 100 g/ha. The herbicidal effect is examined 15 days after the treatment. 15 [0092] Test Example 23 A pot is filled with soil, and weed seeds are sowed and garlic bulbs are planted. On the day of sowing and planting, the surface of the soil is uniformly treated with one or more 20 crystals selected from the group consisting of 1 st crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 50, 100, 200, or 400 g/ha. This pot is placed in a greenhouse. The herbicidal effect is examined 15 days after the sowing and planting. 25 [0093] 45 S34184 Test Example 24 A pot is filled with soil and sunflower seeds and weed seeds are sowed. This pot is placed in a greenhouse. When the sunflower grows 2 to 6 leaves, the surface of the soil and the 5 stem leaves of the weeds are uniformly treated with one or more crystals selected from the group consisting of 1 st crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 12.5, 25, 50, or 100 g/ha. The herbicidal effect is examined 15 days after the treatment. 10 [0094] Test Example 25 A pot is filled with soil and wheat seeds and weed seeds are sowed. This pot is placed in a greenhouse. When the wheat grows 2 to 6 leaves, the surface of the soil and the stem leaves 15 of the weeds are uniformly treated with one or more crystals selected from the group consisting of 1 't crystal of flumioxazin to 7 th crystal of flumioxazin at a dose of 12.5, 25, 50, or 100 g/ha. The herbicidal effect is examined 15 days after the treatment. 20 [0095] Test Example 26 The surface of soil in a cultivated field where grape, Citrus unshiu, peach, and almond are cultivated is uniformly treated with one or more crystals selected from the group 25 consisting of 1"' crystal of flumioxazin to 7tb crystal of 46 S34184 flumioxazin at a dose of 1, 5, 10, 50, 100, 150, 500, 750, or 1000 g/ha. The herbicidal effect is examined 28 days after the treatment. [0096] 5 According to the present invention, a wide range of weeds can be controlled in a crop field, land under perennial crops, or a non-crop land. [0097] Throughout this specification and the claims which follow, 10 unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. 15 [0098] The reference in this specification to any prior publication (or information derived from it) , or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication 20 (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates. 47